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Sample records for triazole conazole fungicide

  1. Effects of Conazole Fungicides on Spontaneous Activity in Neural Networks

    Science.gov (United States)

    Hexaconazole (HEX), Tetraconazole (TET), Fluconazole (FLU), and Triadimefon (TRI) are conazole fungicides, used to control powdery mildews on crops, and as veterinary and clinical treatments. TRI, a demethylation inhibitor, is neurotoxic in vivo, and previous in vitro experiments...

  2. Discrimination of tumorigenic triazole conazoles from phenobarbital by transcriptional analyses of mouse liver gene expression

    Science.gov (United States)

    Conazoles are fungicides used to control fungal growth in environmental settings and to treat humans with fungal infections. Mouse hepatotumorigenic conazoles display many of the same hepatic toxicologic responses as the mouse liver carcinogen phenobarbital (PB): constitutive and...

  3. Predictive value of cell assays for developmental toxicity and embryotoxicity of conazole fungicides

    DEFF Research Database (Denmark)

    Sørensen, Karin Dreisig; Taxvig, Camilla; Kjærstad, Mia Birkhøj

    2013-01-01

    in reasonably good agreement with available in vivo effects. Ketoconazole and epoxiconazole are the most potent embryotoxic compounds, whereas prochloraz belongs to the most potent developmental toxicants. In conclusion, a rough prediction of the ranking of these conazole fungicides for in vivo toxicity data...

  4. Conazoles

    Directory of Open Access Journals (Sweden)

    Jan Heeres

    2010-06-01

    Full Text Available This review provides a historical overview of the analog based drug discovery of miconazole and its congeners, and is focused on marketed azole antifungals bearing the generic suffix “conazole”. The antifungal activity of miconazole, one of the first broad-spectrum antimycotic agents has been mainly restricted to topical applications. The attractive in vitro antifungal spectrum was a starting point to design more potent and especially orally active antifungal agents such as ketoconazole, itraconazole, posaconazole, fluconazole and voriconazole. The chemistry, in vitro and in vivo antifungal activity, pharmacology, and clinical applications of these marketed conazoles has been described.

  5. Analysis of the mutations inducedd by conazole fungicides in vivo

    Science.gov (United States)

    The mouse liver tumorigenic conazo1e fungicides triadimefon and propiconazo1e have previously been shown to be in vivo mouse liver mutagens in the Big Blue" transgenic mutation assay when administered in feed at tumorigenic doses, whereas the nontumorigenic conazo1e myc1obutani1 ...

  6. EFFECT OF CONAZOLE FUNGICIDES ON REPRODUCTIVE DEVELOPMENT IN THE FEMALE RAT

    Science.gov (United States)

    Three triazole fungicides were evaluated for effects on female rat reproductive development. Rats were exposed via feed to propiconazole (P) (100, 500, or 2500 ppm), myclobutanil (M) (100, 500, or 2000 ppm), or triadimefon (T) (100, 500, or 1800 ppm) from gestation day 6 to postn...

  7. SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF NEW 1,2,4- TRIAZOLES, MANNICH BASES, CONAZOLES, AND FLUOROQUINOLONES

    Directory of Open Access Journals (Sweden)

    Şule CEYLAN

    2016-09-01

    Full Text Available Abstract: Triazoles are heterocyclic compounds which have been of interest in the development of novel compounds with antidepressant, anti-inflammatory, analgesic, antibacterial, antimycobacterial, antifungal, antiviral, anticancer, and other activities. In this article, a series of fluorine- and piperazine-containing some novel biologically active 1,2,4-triazole-3-one derivatives were synthesized by the Mannich reaction of triazole intermediates. The structures for novel synthesized compounds were elucidated using elemental analysis and FT IR, 13C NMR, 1H NMR, EI MS techniques. These compounds were investigated in vitro for their antimicrobial properties and several compounds have fungicidal activity against Candida albicans and Saccharomyces cerevisiae. And also some of the compounds exhibited excellent activity on Mycobacterium smegmatis, a nonpigmented fast-rising mycobacterium, at the concentration of <1 μg/mL is better than standard drug streptomycin.

  8. Factors influencing activity of triazole fungicides towards Botrytis cinerea.

    NARCIS (Netherlands)

    Stehmann, C.; Waard, de M.A.

    1996-01-01

    The activity of triazole fungicides towards Botrytis cinerea was investigated in vitro (radial growth on fungicide-amended agar) and in vivo (foliar-sprayed tomato plants and dip-treated grapes). In both tests the benzimidazoles, benomyl and thiabendazole, and the dicarboximides, iprodione and

  9. Triazole fungicide tebuconazole disrupts human placental trophoblast cell functions.

    Science.gov (United States)

    Zhou, Jinghua; Zhang, Jianyun; Li, Feixue; Liu, Jing

    2016-05-05

    Triazole fungicides are one of the top ten classes of current-use pesticides. Although exposure to triazole fungicides is associated with reproductive toxicity in mammals, limited information is available regarding the effects of triazole fungicides on human placental trophoblast function. Tebuconazole (TEB) is a common triazole fungicide that has been extensively used for fungi control. In this work, we showed that TEB could reduce cell viability, disturb normal cell cycle distribution and induce apoptosis of human placental trophoblast cell line HTR-8/SVneo (HTR-8). Bcl-2 protein expression decreased and the level of Bax protein increased after TEB treatment in HTR-8 cells. The results demonstrated that this fungicide induced apoptosis of trophoblast cells via mitochondrial pathway. Importantly, we found that the invasive and migratory capacities of HTR-8 cells decreased significantly after TEB administration. TEB altered the expression of key regulatory genes involved in the modulation of trophoblast functions. Taken together, TEB suppressed human trophoblast invasion and migration through affecting the expression of protease, hormones, angiogenic factors, growth factors and cytokines. As the invasive and migratory abilities of trophoblast are essential for successful placentation and fetus development, our findings suggest a potential risk of triazole fungicides to human pregnancy. Copyright © 2016 Elsevier B.V. All rights reserved.

  10. Triazole fungicide tebuconazole disrupts human placental trophoblast cell functions

    Energy Technology Data Exchange (ETDEWEB)

    Zhou, Jinghua [Key Laboratory of Environmental Remediation and Ecological Health, Ministry of Education, Zhejiang University, Hangzhou 310058 (China); Zhang, Jianyun [Research Center for Air Pollution and Health, College of Environmental and Resource Sciences, Zhejiang University, Hangzhou 310058 (China); Li, Feixue [Zhejiang Key Laboratory of Organ Development and Regeneration, Institute of Developmental and Regenerative Biology, College of Life and Environmental Sciences, Hangzhou Normal University, Hangzhou 310036 (China); Liu, Jing, E-mail: jliue@zju.edu.cn [Key Laboratory of Environmental Remediation and Ecological Health, Ministry of Education, Zhejiang University, Hangzhou 310058 (China); Research Center for Air Pollution and Health, College of Environmental and Resource Sciences, Zhejiang University, Hangzhou 310058 (China)

    2016-05-05

    Highlights: • Tebuconazole (TEB) inhibited the proliferation of human placental trophoblasts. • TEB changed cell cycle distribution of G1 and G2 phases of trophoblasts. • TEB induced apoptosis of trophoblasts via mitochondrial pathway. • TEB decreased the invasive and migratory capacities of trophoblasts. • TEB altered the mRNA levels of key regulatory genes in trophoblasts - Abstract: Triazole fungicides are one of the top ten classes of current-use pesticides. Although exposure to triazole fungicides is associated with reproductive toxicity in mammals, limited information is available regarding the effects of triazole fungicides on human placental trophoblast function. Tebuconazole (TEB) is a common triazole fungicide that has been extensively used for fungi control. In this work, we showed that TEB could reduce cell viability, disturb normal cell cycle distribution and induce apoptosis of human placental trophoblast cell line HTR-8/SVneo (HTR-8). Bcl-2 protein expression decreased and the level of Bax protein increased after TEB treatment in HTR-8 cells. The results demonstrated that this fungicide induced apoptosis of trophoblast cells via mitochondrial pathway. Importantly, we found that the invasive and migratory capacities of HTR-8 cells decreased significantly after TEB administration. TEB altered the expression of key regulatory genes involved in the modulation of trophoblast functions. Taken together, TEB suppressed human trophoblast invasion and migration through affecting the expression of protease, hormones, angiogenic factors, growth factors and cytokines. As the invasive and migratory abilities of trophoblast are essential for successful placentation and fetus development, our findings suggest a potential risk of triazole fungicides to human pregnancy.

  11. Triazole fungicide tebuconazole disrupts human placental trophoblast cell functions

    International Nuclear Information System (INIS)

    Zhou, Jinghua; Zhang, Jianyun; Li, Feixue; Liu, Jing

    2016-01-01

    Highlights: • Tebuconazole (TEB) inhibited the proliferation of human placental trophoblasts. • TEB changed cell cycle distribution of G1 and G2 phases of trophoblasts. • TEB induced apoptosis of trophoblasts via mitochondrial pathway. • TEB decreased the invasive and migratory capacities of trophoblasts. • TEB altered the mRNA levels of key regulatory genes in trophoblasts - Abstract: Triazole fungicides are one of the top ten classes of current-use pesticides. Although exposure to triazole fungicides is associated with reproductive toxicity in mammals, limited information is available regarding the effects of triazole fungicides on human placental trophoblast function. Tebuconazole (TEB) is a common triazole fungicide that has been extensively used for fungi control. In this work, we showed that TEB could reduce cell viability, disturb normal cell cycle distribution and induce apoptosis of human placental trophoblast cell line HTR-8/SVneo (HTR-8). Bcl-2 protein expression decreased and the level of Bax protein increased after TEB treatment in HTR-8 cells. The results demonstrated that this fungicide induced apoptosis of trophoblast cells via mitochondrial pathway. Importantly, we found that the invasive and migratory capacities of HTR-8 cells decreased significantly after TEB administration. TEB altered the expression of key regulatory genes involved in the modulation of trophoblast functions. Taken together, TEB suppressed human trophoblast invasion and migration through affecting the expression of protease, hormones, angiogenic factors, growth factors and cytokines. As the invasive and migratory abilities of trophoblast are essential for successful placentation and fetus development, our findings suggest a potential risk of triazole fungicides to human pregnancy.

  12. Triazole Fungicides Can Induce Cross-Resistance to Medical Triazoles in Aspergillus fumigatus

    Science.gov (United States)

    Karawajczyk, Anna; Schaftenaar, Gijs; Kema, Gert H. J.; van der Lee, Henrich A.; Klaassen, Corné H.; Melchers, Willem J. G.; Verweij, Paul E.

    2012-01-01

    Background Azoles play an important role in the management of Aspergillus diseases. Azole resistance is an emerging global problem in Aspergillus fumigatus, and may develop through patient therapy. In addition, an environmental route of resistance development has been suggested through exposure to 14α-demethylase inhibitors (DMIs). The main resistance mechanism associated with this putative fungicide-driven route is a combination of alterations in the Cyp51A-gene (TR34/L98H). We investigated if TR34/L98H could have developed through exposure to DMIs. Methods and Findings Thirty-one compounds that have been authorized for use as fungicides, herbicides, herbicide safeners and plant growth regulators in the Netherlands between 1970 and 2005, were investigated for cross-resistance to medical triazoles. Furthermore, CYP51-protein homology modeling and molecule alignment studies were performed to identify similarity in molecule structure and docking modes. Five triazole DMIs, propiconazole, bromuconazole, tebuconazole, epoxiconazole and difenoconazole, showed very similar molecule structures to the medical triazoles and adopted similar poses while docking the protein. These DMIs also showed the greatest cross-resistance and, importantly, were authorized for use between 1990 and 1996, directly preceding the recovery of the first clinical TR34/L98H isolate in 1998. Through microsatellite genotyping of TR34/L98H isolates we were able to calculate that the first isolate would have arisen in 1997, confirming the results of the abovementioned experiments. Finally, we performed induction experiments to investigate if TR34/L98H could be induced under laboratory conditions. One isolate evolved from two copies of the tandem repeat to three, indicating that fungicide pressure can indeed result in these genomic changes. Conclusions Our findings support a fungicide-driven route of TR34/L98H development in A. fumigatus. Similar molecule structure characteristics of five triazole DMIs

  13. Triazole fungicides can induce cross-resistance to medical triazoles in Aspergillus fumigatus.

    Directory of Open Access Journals (Sweden)

    Eveline Snelders

    Full Text Available BACKGROUND: Azoles play an important role in the management of Aspergillus diseases. Azole resistance is an emerging global problem in Aspergillus fumigatus, and may develop through patient therapy. In addition, an environmental route of resistance development has been suggested through exposure to 14α-demethylase inhibitors (DMIs. The main resistance mechanism associated with this putative fungicide-driven route is a combination of alterations in the Cyp51A-gene (TR(34/L98H. We investigated if TR(34/L98H could have developed through exposure to DMIs. METHODS AND FINDINGS: Thirty-one compounds that have been authorized for use as fungicides, herbicides, herbicide safeners and plant growth regulators in The Netherlands between 1970 and 2005, were investigated for cross-resistance to medical triazoles. Furthermore, CYP51-protein homology modeling and molecule alignment studies were performed to identify similarity in molecule structure and docking modes. Five triazole DMIs, propiconazole, bromuconazole, tebuconazole, epoxiconazole and difenoconazole, showed very similar molecule structures to the medical triazoles and adopted similar poses while docking the protein. These DMIs also showed the greatest cross-resistance and, importantly, were authorized for use between 1990 and 1996, directly preceding the recovery of the first clinical TR(34/L98H isolate in 1998. Through microsatellite genotyping of TR(34/L98H isolates we were able to calculate that the first isolate would have arisen in 1997, confirming the results of the abovementioned experiments. Finally, we performed induction experiments to investigate if TR(34/L98H could be induced under laboratory conditions. One isolate evolved from two copies of the tandem repeat to three, indicating that fungicide pressure can indeed result in these genomic changes. CONCLUSIONS: Our findings support a fungicide-driven route of TR(34/L98H development in A. fumigatus. Similar molecule structure

  14. Triazole fungicides can induce cross-resistance to medical triazoles in Aspergillus fumigatus.

    Science.gov (United States)

    Snelders, Eveline; Camps, Simone M T; Karawajczyk, Anna; Schaftenaar, Gijs; Kema, Gert H J; van der Lee, Henrich A; Klaassen, Corné H; Melchers, Willem J G; Verweij, Paul E

    2012-01-01

    Azoles play an important role in the management of Aspergillus diseases. Azole resistance is an emerging global problem in Aspergillus fumigatus, and may develop through patient therapy. In addition, an environmental route of resistance development has been suggested through exposure to 14α-demethylase inhibitors (DMIs). The main resistance mechanism associated with this putative fungicide-driven route is a combination of alterations in the Cyp51A-gene (TR(34)/L98H). We investigated if TR(34)/L98H could have developed through exposure to DMIs. Thirty-one compounds that have been authorized for use as fungicides, herbicides, herbicide safeners and plant growth regulators in The Netherlands between 1970 and 2005, were investigated for cross-resistance to medical triazoles. Furthermore, CYP51-protein homology modeling and molecule alignment studies were performed to identify similarity in molecule structure and docking modes. Five triazole DMIs, propiconazole, bromuconazole, tebuconazole, epoxiconazole and difenoconazole, showed very similar molecule structures to the medical triazoles and adopted similar poses while docking the protein. These DMIs also showed the greatest cross-resistance and, importantly, were authorized for use between 1990 and 1996, directly preceding the recovery of the first clinical TR(34)/L98H isolate in 1998. Through microsatellite genotyping of TR(34)/L98H isolates we were able to calculate that the first isolate would have arisen in 1997, confirming the results of the abovementioned experiments. Finally, we performed induction experiments to investigate if TR(34)/L98H could be induced under laboratory conditions. One isolate evolved from two copies of the tandem repeat to three, indicating that fungicide pressure can indeed result in these genomic changes. Our findings support a fungicide-driven route of TR(34)/L98H development in A. fumigatus. Similar molecule structure characteristics of five triazole DMIs and the three medical triazoles

  15. Gene Expression Profiling in Liver and Testis of Rats to Characterize the Toxicity of Triazole Fungicides

    Science.gov (United States)

    Four triazole fungicides were studied using toxicogenomic techniques to identify potential mechanisms of action. Adult male Sprague-Dawley rats were dosed for 14 days by gavage with fluconazole, myclobutanil, propiconazole, or triadimefon. Following exposure, serum was collected ...

  16. USING PHARMACOKINETIC DATA TO INTERPRET METABOLOMIC CHANGES IN CD-1 MICE TREATED WITH TRIAZOLE FUNGICIDES

    Science.gov (United States)

    Triazoles are a class of fungicides widely used in both pharmaceutical and agricultural applications. These compounds elicit a variety of toxic effects including disruption of normal metabolic processes such as steroidogenesis. Metabolomics is used to measure dynamic changes in e...

  17. Evolution of cross-resistance to medical triazoles in Aspergillus fumigatus through selection pressure of environmental fungicides.

    Science.gov (United States)

    Zhang, Jianhua; van den Heuvel, Joost; Debets, Alfons J M; Verweij, Paul E; Melchers, Willem J G; Zwaan, Bas J; Schoustra, Sijmen E

    2017-09-27

    Resistance to medical triazoles in Aspergillus fumigatus is an emerging problem for patients at risk of aspergillus diseases. There are currently two presumed routes for medical triazole-resistance selection: (i) through selection pressure of medical triazoles when treating patients and (ii) through selection pressure from non-medical sterol-biosynthesis-inhibiting (SI) triazole fungicides which are used in the environment. Previous studies have suggested that SI fungicides can induce cross-resistance to medical triazoles. Therefore, to assess the potential of selection of resistance to medical triazoles in the environment, we assessed cross-resistance to three medical triazoles in lineages of A. fumigatus from previous work where we applied an experimental evolution approach with one of five different SI fungicides to select for resistance. In our evolved lines we found widespread cross-resistance indicating that resistance to medical triazoles rapidly arises through selection pressure of SI fungicides. All evolved lineages showed similar evolutionary dynamics to SI fungicides and medical triazoles, which suggests that the mutations inducing resistance to both SI fungicides and medical triazoles are likely to be the same. Whole-genome sequencing revealed that a variety of mutations were putatively involved in the resistance mechanism, some of which are in known target genes. © 2017 The Author(s).

  18. Gene expression profiling in liver and testis of rats to characterize the toxicity of triazole fungicides

    International Nuclear Information System (INIS)

    Tully, Douglas B.; Bao Wenjun; Goetz, Amber K.; Blystone, Chad R.; Ren, Hongzu; Schmid, Judith E.; Strader, Lillian F.; Wood, Carmen R.; Best, Deborah S.; Narotsky, Michael G.; Wolf, Douglas C.; Rockett, John C.; Dix, David J.

    2006-01-01

    Four triazole fungicides were studied using toxicogenomic techniques to identify potential mechanisms of action. Adult male Sprague-Dawley rats were dosed for 14 days by gavage with fluconazole, myclobutanil, propiconazole, or triadimefon. Following exposure, serum was collected for hormone measurements, and liver and testes were collected for histology, enzyme biochemistry, or gene expression profiling. Body and testis weights were unaffected, but liver weights were significantly increased by all four triazoles, and hepatocytes exhibited centrilobular hypertrophy. Myclobutanil exposure increased serum testosterone and decreased sperm motility, but no treatment-related testis histopathology was observed. We hypothesized that gene expression profiles would identify potential mechanisms of toxicity and used DNA microarrays and quantitative real-time PCR (qPCR) to generate profiles. Triazole fungicides are designed to inhibit fungal cytochrome P450 (CYP) 51 enzyme but can also modulate the expression and function of mammalian CYP genes and enzymes. Triazoles affected the expression of numerous CYP genes in rat liver and testis, including multiple Cyp2c and Cyp3a isoforms as well as other xenobiotic metabolizing enzyme (XME) and transporter genes. For some genes, such as Ces2 and Udpgtr2, all four triazoles had similar effects on expression, suggesting possible common mechanisms of action. Many of these CYP, XME and transporter genes are regulated by xeno-sensing nuclear receptors, and hierarchical clustering of CAR/PXR-regulated genes demonstrated the similarities of toxicogenomic responses in liver between all four triazoles and in testis between myclobutanil and triadimefon. Triazoles also affected expression of multiple genes involved in steroid hormone metabolism in the two tissues. Thus, gene expression profiles helped identify possible toxicological mechanisms of the triazole fungicides

  19. METABOLOMIC EVALUATION OF RAT LIVER AND TESTIS TO CHARACTERIZE THE TOXICITY OF TRIAZOLE FUNGICIDES

    Science.gov (United States)

    The effects of two triazole fungicides, myclobutanil and triadimefon, on endogenous rat metabolite profiles in blood serum, liver, and testis was assessed using proton nuclear magnetic resonance (1H-NMR) spectroscopy. Adult male Sprague-Dawley rats were dosed daily by gavage for...

  20. GENE EXPRESSION PROFILING IN THE LIVER OF CD-1 MICE TO CHARACTERIZE THE HEPATOTOXICITY OF TRIAZOLE FUNGICIDES

    Science.gov (United States)

    Four triazole fungicides used in agricultural or pharmaceutical applications were examined for hepatotoxic effects in mouse liver. Besides organ weight, histopathology, and cytochrome P450 (CYP) enzyme induction, DNA microarrays were used to generate gene expression profiles and ...

  1. Determination of acid dissociation constants of triazole fungicides by pressure assisted capillary electrophoresis

    Czech Academy of Sciences Publication Activity Database

    Konášová, Renáta; Jaklová Dytrtová, Jana; Kašička, Václav

    2015-01-01

    Roč. 1408, Aug 21 (2015), s. 243-249 ISSN 0021-9673 R&D Projects: GA ČR(CZ) GA13-17224S; GA ČR GP13-21409P Institutional support: RVO:61388963 Keywords : triazole fungicides * acid dissociation constant * pK(a) * capillary electrophoresis * ionic mobility Subject RIV: CB - Analytical Chemistry, Separation Impact factor: 3.926, year: 2015

  2. Biological activity of triazole fungicides towards Botrytis cinerea

    NARCIS (Netherlands)

    Stehmann, C.

    1995-01-01

    Botrytis cinerea Pers. ex Fr., the causal agent of grey mould, is one of the most ubiquitous plant pathogens. The fungus is of high economic importance in various major crops and during transport and storage of agricultural products. Protectant fungicides such as

  3. Two azole fungicides (carcinogenic triadimefon and non-carcinogenic myclobutanil) exhibit different hepatic cytochrome P450 activities in medaka fish

    International Nuclear Information System (INIS)

    Lin, Chun-Hung; Chou, Pei-Hsin; Chen, Pei-Jen

    2014-01-01

    Highlights: • We assess ecotoxicological impact of azole fungicides in the aquatic environment. • Carcinogenic and non-carcinogenic azoles show different CYP activities in medaka. • We compare azole-induced CYP expression and carcinogenesis between fish and rodents. • Liver CYP-enzyme induction is a key event in conazole-induced tumorigenesis. • We suggest toxicity evaluation methods for azole fungicides using medaka fish. - Abstract: Conazoles are a class of imidazole- or triazole-containing drugs commonly used as fungicides in agriculture and medicine. The broad application of azole drugs has led to the contamination of surface aquifers receiving the effluent of municipal or hospital wastewater or agricultural runoff. Several triazoles are rodent carcinogens; azole pollution is a concern to environmental safety and human health. However, the carcinogenic mechanisms associated with cytochrome P450 enzymes (CYPs) of conazoles remain unclear. We exposed adult medaka fish (Oryzias latipes) to continuous aqueous solutions of carcinogenic triadimefon and non-carcinogenic myclobutanil for 7 to 20 days at sub-lethal or environmentally relevant concentrations and assessed hepatic CYP activity and gene expression associated with CYP-mediated toxicity. Both triadimefon and myclobutanil induced hepatic CYP3A activity, but only triadimefon enhanced CYP1A activity. The gene expression of cyp3a38, cyp3a40, pregnane x receptor (pxr), cyp26b, retinoid acid receptor γ1 (rarγ1) and p53 was higher with triadimefon than myclobutanil. As well, yeast-based reporter gene assay revealed that 4 tested conazoles were weak agonists of aryl hydrocarbon receptor (AhR). We reveal differential CYP gene expression with carcinogenic and non-carcinogenic conazoles in a lower vertebrate, medaka fish. Liver CYP-enzyme induction may be a key event in conazole-induced tumorigenesis. This information is essential to evaluate the potential threat of conazoles to human health and fish

  4. Two azole fungicides (carcinogenic triadimefon and non-carcinogenic myclobutanil) exhibit different hepatic cytochrome P450 activities in medaka fish

    Energy Technology Data Exchange (ETDEWEB)

    Lin, Chun-Hung [Department of Agricultural Chemistry, National Taiwan University, Taipei, Taiwan (China); Chou, Pei-Hsin [Department of Environmental Engineering, National Cheng-Kung University, Tainan, Taiwan (China); Chen, Pei-Jen, E-mail: chenpj@ntu.edu.tw [Department of Agricultural Chemistry, National Taiwan University, Taipei, Taiwan (China)

    2014-07-30

    Highlights: • We assess ecotoxicological impact of azole fungicides in the aquatic environment. • Carcinogenic and non-carcinogenic azoles show different CYP activities in medaka. • We compare azole-induced CYP expression and carcinogenesis between fish and rodents. • Liver CYP-enzyme induction is a key event in conazole-induced tumorigenesis. • We suggest toxicity evaluation methods for azole fungicides using medaka fish. - Abstract: Conazoles are a class of imidazole- or triazole-containing drugs commonly used as fungicides in agriculture and medicine. The broad application of azole drugs has led to the contamination of surface aquifers receiving the effluent of municipal or hospital wastewater or agricultural runoff. Several triazoles are rodent carcinogens; azole pollution is a concern to environmental safety and human health. However, the carcinogenic mechanisms associated with cytochrome P450 enzymes (CYPs) of conazoles remain unclear. We exposed adult medaka fish (Oryzias latipes) to continuous aqueous solutions of carcinogenic triadimefon and non-carcinogenic myclobutanil for 7 to 20 days at sub-lethal or environmentally relevant concentrations and assessed hepatic CYP activity and gene expression associated with CYP-mediated toxicity. Both triadimefon and myclobutanil induced hepatic CYP3A activity, but only triadimefon enhanced CYP1A activity. The gene expression of cyp3a38, cyp3a40, pregnane x receptor (pxr), cyp26b, retinoid acid receptor γ1 (rarγ1) and p53 was higher with triadimefon than myclobutanil. As well, yeast-based reporter gene assay revealed that 4 tested conazoles were weak agonists of aryl hydrocarbon receptor (AhR). We reveal differential CYP gene expression with carcinogenic and non-carcinogenic conazoles in a lower vertebrate, medaka fish. Liver CYP-enzyme induction may be a key event in conazole-induced tumorigenesis. This information is essential to evaluate the potential threat of conazoles to human health and fish

  5. Triazole fungicides and the selection of resistance to medical triazoles in the opportunistic mould Aspergillus fumigatus

    NARCIS (Netherlands)

    Verweij, P.E.; Kema, G.H.; Zwaan, B.; Melchers, W.J.G.

    2013-01-01

    Azole resistance is an emerging problem in the opportunistic mould Aspergillus fumigatus. The triazoles are the most important agents for the management of Aspergillus diseases in humans. Selection for acquired resistance may occur in the hospital setting through exposure to high doses of azoles

  6. Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities

    Directory of Open Access Journals (Sweden)

    Adilson Vidal Costa

    2017-10-01

    Full Text Available The synthesis of a series of 1,2,3-triazoles using glycerol as starting material is described. The key step in the preparation of these triazolic derivatives is the copper(I-catalyzed azide-alkyne cycloaddition (CuAAC, also known as click reaction, between 4-(azidomethyl-2,2-dimethyl-1,3-dioxolane (3 and different terminal alkynes. The eight prepared derivatives were evaluated with regard to their fungicide, phytotoxic and cytotoxic activities. The fungicidal activity was assessed in vitro against Colletotrichum gloeosporioides, the causative agent of papaya anthracnose. It was found that the compounds 1-(1-((2,2-dimethyl-1,3-dioxolan-4-ylmethyl-1H-1,2,3-triazol-4-yl-cyclo-hexanol (4g and 2-(1-((2,2-dimethyl-1,3-dioxolan-4-ylmethyl-1H-1,2,3-triazol-4-ylpropan-2-ol (4h demonstrated high efficiency in controlling C. gloeosporioides when compared to the commercial fungicide tebuconazole. The triazoles did not present any phytotoxic effect when evaluated against Lactuca sativa. However, five derivatives were mitodepressive, inducing cell death detected by the presence of condensed nuclei and acted as aneugenic agents in the cell cycle of L. sativa. It is believed that glycerol derivatives bearing 1,2,3-triazole functionalities may represent a promising scaffold to be explored for the development of new agents to control C. gloeosporioides.

  7. Triazole fungicides can induce cross-resistance to medical triazoles in Aspergillus fumigatus.

    OpenAIRE

    Snelders, E.; Camps, S.M.T.; Karawajczyk, A.; Schaftenaar, G.; Kema, G.H.; Lee, H.A.L. van der; Klaassen, C.H.; Melchers, W.J.G.; Verweij, P.E.

    2012-01-01

    BACKGROUND: Azoles play an important role in the management of Aspergillus diseases. Azole resistance is an emerging global problem in Aspergillus fumigatus, and may develop through patient therapy. In addition, an environmental route of resistance development has been suggested through exposure to 14alpha-demethylase inhibitors (DMIs). The main resistance mechanism associated with this putative fungicide-driven route is a combination of alterations in the Cyp51A-gene (TR(34)/L98H). We invest...

  8. Triazole Fungicides Inhibit Zebrafish Hatching by Blocking the Secretory Function of Hatching Gland Cells.

    Science.gov (United States)

    De la Paz, Javiera F; Beiza, Natalia; Paredes-Zúñiga, Susana; Hoare, Misque S; Allende, Miguel L

    2017-04-04

    In animals, hatching represents the transition point from a developing embryo to a free-living individual, the larva. This process is finely regulated by many endogenous and environmental factors and has been shown to be sensitive to a variety of chemical agents. It is commonly evaluated in bioassays in order to establish the effects of different agents on early development and reproductive capabilities in fish and other aquatic animals. In fish, the breakdown of the chorion is achieved by the secretion of choriolysin by hatching gland cells (HGCs) into the perivitelline space (PVS), coupled with spontaneous movements of the developing larva. In this work, we used zebrafish to assay the effects of a family of widely used agrochemicals-triazoles Triadimefon (FON), Triadimenol (NOL) and free triazole (1,2,4-T)-on hatching success. We found a strong inhibition of hatching by triazole exposure which was correlated with morphological changes and a reduction in the secretory function of the HGCs. As a consequence, the release of choriolytic enzymes by HGCs was reduced. We also found that HGC secretion reduction after exposure to FON can be rescued by co-incubation with a dopamine D2 receptor antagonist but not by antagonists of the D1-like receptors. This suggests a specific pathway through which this family of fungicides may be impairing a critical event in the fish life cycle.

  9. Synthesis and application of a novel molecularly imprinted polymer-coated stir bar for microextraction of triazole fungicides in soil.

    Science.gov (United States)

    Hu, Yuling; Li, Jiawei; Li, Gongke

    2011-05-01

    The preparation, characteristics and application of a sorptive stir bar coated with molecularly imprinted polymer (MIP) using triadimefon as the template molecule are described here. Raw glass capillary was coated with MIP through chemical bonding. The synthesis method was effective and reproducible with the batch-to-batch RSD within 7.8%. Scanning electron micrographs of the stir bar revealed a highly porous coating with average thickness of 15 μm. The synthesized stir bar was proved to be highly stable in most of the solvent for use. Extraction performance showed the fabricated stir bar has excellent molecular recognition abilities for triadimefon and the structure-related compounds, such as triadimenol, diniconazole, flutriafol, hexaconazole, tebuconazole, paclobutrazol and uniconazole, and thus can be applied for simultaneous determination of these triazole fungicides from complex samples by coupling with high-performance liquid chromatography. The variables that influence extraction were optimized with 10.0 μg/L standard solutions of triazole fungicides, and the analytical method was established for the determination of triazole fungicides in soil. The detection limits were in the range of 0.14-0.34 μg/L, and the recoveries were from 86.7 to 114.6% for spiked soil sample. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  10. Gene expression profiling in the liver of CD-1 mice to characterize the hepatotoxicity of triazole fungicides

    International Nuclear Information System (INIS)

    Goetz, Amber K.; Bao, Wenjun; Ren, Hongzu; Schmid, Judith E.; Tully, Douglas B.; Wood, Carmen; Rockett, John C.; Narotsky, Michael G.; Sun, Guobin; Lambert, Guy R.; Thai, S.-F.; Wolf, Douglas C.; Nesnow, Stephen; Dix, David J.

    2006-01-01

    Four triazole fungicides used in agricultural or pharmaceutical applications were examined for hepatotoxic effects in mouse liver. Besides organ weight, histopathology, and cytochrome P450 (CYP) enzyme induction, DNA microarrays were used to generate gene expression profiles and hypotheses on potential mechanisms of action for this class of chemicals. Adult male CD-1 mice were exposed daily for 14 days to fluconazole, myclobutanil, propiconazole, or triadimefon at three dose levels by oral gavage. Doses were based on previous studies that resulted in liver hypertrophy or hepatotoxicity. All four triazoles caused hepatocyte hypertrophy, and all except triadimefon increased relative liver/body weight ratios at the middle and high dose levels. CYP enzyme activities were also induced by all four triazoles at the middle and high doses as measured by the dealkylations of four alkoxyresorufins, although some differences in substrate specificity were observed. Consistent with this common histopathology and biochemistry, several CYP and xenobiotic metabolizing enzyme (XME) genes were differentially expressed in response to all four (Cyp2d26 and Cyp3a11), or three of the four (Cyp2c40, Cyp2c55, Ces2, Slco1a4) triazoles. Differential expression of numerous other CYP and XME genes discriminated between the various triazoles, consistent with differences in CYP enzyme activities, and indicative of possible differences in mechanisms of hepatotoxicity or dose response. Multiple isoforms of Cyp1a, 2b, 2c, 3a, and other CYP and XME genes regulated by the nuclear receptors constitutive androstane receptor (CAR) and pregnane X receptor (PXR) were differentially expressed following triazole exposure. Based on these results, we expanded on our original hypothesis that triazole hepatotoxicity was mediated by CYP induction, to include additional XME genes, many of which are modulated by CAR and PXR

  11. Quantitative changes in endogenous DNA adducts correlate with conazole mutagenicity and tumorigenicity in mouse liver.**

    Science.gov (United States)

    We have previously shown that the conazole fungicides triadimefon and propiconazole, which are tumorigenic in mouse liver, are in vivo mouse liver mutagens in the Big Blue" transgenic mutation assay when administered in feed at tumorigenic doses. The nontumorigenic conazole myclo...

  12. Quantitative changes in endogenous DNA adducts correlate with conazole mutagenicity and tumorigenicity in mouse liver.

    Science.gov (United States)

    We have previously shown that the conazole fungicides triadimefon and propiconazole, which are tumorigenic in mouse liver, are in vivo mouse liver mutagens in the Big Blue" transgenic mutation assay when administered in feed at tumorigenic doses. The nontumorigenic conazole myclo...

  13. Combination Effects of (TriAzole Fungicides on Hormone Production and Xenobiotic Metabolism in a Human Placental Cell Line

    Directory of Open Access Journals (Sweden)

    Svenja Rieke

    2014-09-01

    Full Text Available Consumers are exposed to multiple residues of different pesticides via the diet. Therefore, EU legislation for pesticides requires the evaluation of single active substances as well as the consideration of combination effects. Hence the analysis of combined effects of substances in a broad dose range represents a key challenge to current experimental and regulatory toxicology. Here we report evidence for additive effects for (triazole fungicides, a widely used group of antifungal agents, in the human placental cell line Jeg-3. In addition to the triazoles cyproconazole, epoxiconazole, flusilazole and tebuconazole and the azole fungicide prochloraz also pesticides from other chemical classes assumed to act via different modes of action (i.e., the organophosphate chlorpyrifos and the triazinylsulfonylurea herbicide triflusulfuron-methyl were investigated. Endpoints analysed include synthesis of steroid hormone production (progesterone and estradiol and gene expression of steroidogenic and non-steroidogenic cytochrome-P-450 (CYP enzymes. For the triazoles and prochloraz, a dose dependent inhibition of progesterone production was observed and additive effects could be confirmed for several combinations of these substances in vitro. The non-triazoles chlorpyrifos and triflusulfuron-methyl did not affect this endpoint and, in line with this finding, no additivity was observed when these substances were applied in mixtures with prochloraz. While prochloraz slightly increased aromatase expression and estradiol production and triflusulfuron-methyl decreased estradiol production, none of the other substances had effects on the expression levels of steroidogenic CYP-enzymes in Jeg-3 cells. For some triazoles, prochloraz and chlorpyrifos a significant induction of CYP1A1 mRNA expression and potential combination effects for this endpoint were observed. Inhibition of CYP1A1 mRNA induction by the AhR inhibitor CH223191 indicated AhR receptor dependence this

  14. Combination effects of (tri)azole fungicides on hormone production and xenobiotic metabolism in a human placental cell line.

    Science.gov (United States)

    Rieke, Svenja; Koehn, Sophie; Hirsch-Ernst, Karen; Pfeil, Rudolf; Kneuer, Carsten; Marx-Stoelting, Philip

    2014-09-17

    Consumers are exposed to multiple residues of different pesticides via the diet. Therefore, EU legislation for pesticides requires the evaluation of single active substances as well as the consideration of combination effects. Hence the analysis of combined effects of substances in a broad dose range represents a key challenge to current experimental and regulatory toxicology. Here we report evidence for additive effects for (tri)azole fungicides, a widely used group of antifungal agents, in the human placental cell line Jeg-3. In addition to the triazoles cyproconazole, epoxiconazole, flusilazole and tebuconazole and the azole fungicide prochloraz also pesticides from other chemical classes assumed to act via different modes of action (i.e., the organophosphate chlorpyrifos and the triazinylsulfonylurea herbicide triflusulfuron-methyl) were investigated. Endpoints analysed include synthesis of steroid hormone production (progesterone and estradiol) and gene expression of steroidogenic and non-steroidogenic cytochrome-P-450 (CYP) enzymes. For the triazoles and prochloraz, a dose dependent inhibition of progesterone production was observed and additive effects could be confirmed for several combinations of these substances in vitro. The non-triazoles chlorpyrifos and triflusulfuron-methyl did not affect this endpoint and, in line with this finding, no additivity was observed when these substances were applied in mixtures with prochloraz. While prochloraz slightly increased aromatase expression and estradiol production and triflusulfuron-methyl decreased estradiol production, none of the other substances had effects on the expression levels of steroidogenic CYP-enzymes in Jeg-3 cells. For some triazoles, prochloraz and chlorpyrifos a significant induction of CYP1A1 mRNA expression and potential combination effects for this endpoint were observed. Inhibition of CYP1A1 mRNA induction by the AhR inhibitor CH223191 indicated AhR receptor dependence this effect.

  15. Tolerance of triazole-based fungicides by biocontrol agents used to control Fusarium head blight in wheat in Argentina.

    Science.gov (United States)

    Palazzini, J M; Torres, A M; Chulze, S N

    2018-02-25

    Fusarium head blight (FHB) caused by Fusarium graminearum species complex is a devastating disease that causes extensive yield and quality losses to wheat around the world. Fungicide application and breeding for resistance are among the most important tools to counteract FHB. Biological control is an additional tool that can be used as part of an integrated management of FHB. Bacillus velezensis RC 218, Brevibacillus sp. RC 263 and Streptomyces sp. RC 87B were selected by their potential to control FHB and deoxynivalenol production. The aim of this work was to test the tolerance of these biocontrol agents to triazole-based fungicides such as Prothioconazole, tebuconazole and metconazole. Bacterial growth was evaluated in Petri dishes using the spread plating technique containing the different fungicides. Bacillus velezensis RC 218 and Streptomyces sp. RC 87B showed better tolerance to fungicides than Brevibacillus sp. RC 263. Complete growth inhibition was observed at concentrations of 20 μg ml -1 for metconazole, 40 μg ml -1 for tebuconazole and 80 μg ml -1 for prothioconazole. The results obtained indicate the possibility of using these biocontrol agents in combination with fungicides as part of an integrated management to control FHB of wheat. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.

  16. Extraction of triazole fungicides in environmental waters utilizing poly (ionic liquid)-functionalized magnetic adsorbent.

    Science.gov (United States)

    Liu, Cheng; Liao, Yingmin; Huang, Xiaojia

    2017-11-17

    This work prepared a new poly (ionic liquid)-functionalized magnetic adsorbent (PFMA) for the extraction of triazole fungicides (TFs) in environmental waters prior to determination by high performance liquid chromatography/diode array detection (HPLC-DAD). A polymerizable ionic liquid, 1-methyl-3-allylimidazolium bis(trifluoromethylsulfonyl)imide was employed to copolymerize with divinylbenzene on the surface of modified magnetite to fabricate the PFMA. The morphology, spectroscopic and magnetic properties of the new adsorbent were investigated by different techniques. A series of key parameters that influence the extraction performance including the amount of PFMA, desorption solvent, adsorption and desorption time, sample pH value and ionic strength were optimized in detail. Under the optimum conditions, the prepared PFMA could extract targeted TFs effectively and quickly under the format of magnetic solid-phase extraction (MSPE). Satisfactory linearities were achieved in the range of 0.1-200.0μg/L for triadimenol and 0.05-200.0μg/L for other TFs with good coefficients of determination above 0.99 for all analytes. The limits of detection (S/N=3) and limits of quantification (S/N=10) for TFs were in the range of 0.0050-0.0078μg/L and 0.017-0.026μg/L, respectively. Environmental waters including lake, river and well waters were used to demonstrate the applicability of developed MSPE-HPLC-DAD method, and satisfactory recoveries and repeatability were obtained. Copyright © 2017 Elsevier B.V. All rights reserved.

  17. Effect on enzymes and histopathology in earthworm (Eisenia foetida) induced by triazole fungicides.

    Science.gov (United States)

    Gao, Minling; Song, Wenhua; Zhang, Jinyang; Guo, Jing

    2013-05-01

    Earthworms are an ideal biological model in toxicity assays and environment monitoring studies, especially for the toxicity of pesticides on soil ecosystem. However, There are very little data on the toxicity of triazoles on earthworms despite the fact that such data are critical in assessing their fate and potential toxic effects in soil organisms. To address this issue, earthworms were exposed to triazoles (triadimefon, triadimenol, difenoconazole and propiconazole) to study biochemical and histopathological examination. The results showed protein content significantly increased in treatment of difenoconazole compared to control. There were no significant differences between controls and triadimefon treated groups, while the glutathione peroxidase (GSH-Px) activity is significantly lower than control. Other triazoles also had an inhibitory effect on GSH-Px activity at higher concentration. The histopathological examination showed the epidermis and the epidermis cell of earthworm was ruined at lower triazoles concentration. The arrangement of smooth muscle layer disordered, and some cell disintegrated with concentration increasing of pesticides. Cell pyknosis, cytoplasm deep stained, nucleus concentrations were observed in the treated group with propiconazole. Copyright © 2013 Elsevier B.V. All rights reserved.

  18. Synthesis and application of imidazolium-based ionic liquids as extraction solvent for pretreatment of triazole fungicides in water samples.

    Science.gov (United States)

    Yang, Jiale; Fan, Chen; Kong, Dandan; Tang, Gang; Zhang, Wenbing; Dong, Hongqiang; Liang, You; Wang, Deng; Cao, Yongsong

    2018-02-01

    Five novel ionic liquids (ILs), 1,3-dibutylimidazolium bromide [BBMIm][Br], 1-pentyl-3-butylimidazolium bromide [BPMIm][Br], 1-hexyl-3-butylimidazolium bromide [BHMIm][Br], 1,1'-(butane-1,4-diyl)bis(3-butylimidazolium) bromide [C 4 (BMIm) 2 ][Br 2 ], and 1,1'-(butane-1,4-diyl)bis(3-methylimidazolium) bromide [C 4 (MIm) 2 ][Br 2 ], were prepared and used in situ to react with bis(trifluoromethane)sulfonamide lithium salt to extract the myclobutanil, tebuconazole, cyproconazole, and prothioconazole from water samples. The results showed that mono-cationic ILs had much better recovery than dicationic ILs, and mono-imidazolium IL bearing butyl groups at N-1 and N-3 sites had the best recovery. When the length of the alkyl substituent group was more than four carbons at N-3 site, the recovery decreased with increase of alkyl chain length of 1-butylimidazolium IL. The extraction efficiency order of triazoles from high to low was [BBMIm][Br], [BPMIm][Br], [BHMIm][Br], [BMIm][Br] (1-butyl-3-methylimidazolium bromide), [C 4 (BMIm) 2 ]Br 2 , [C 4 (MIm) 2 ]Br 2 . An in situ ionic liquid dispersive liquid-liquid microextraction combined with ultrasmall superparamagnetic Fe 3 O 4 was established as a pretreatment method for enrichment of triazole fungicides in water samples by using the synthetic [BBMIm][Br] as the cationic IL and used to detect analytes followed by high-performance liquid chromatography. Under the optimized conditions, the proposed method showed a good linearity within a range of 5-250 μg L -1 , with the determination coefficient (r 2 ) varying from 0.998 to 0.999. High mean enrichment factors were achieved ranging from 187 to 323, and the recoveries of the target analytes from real water samples at spiking levels of 10.0, 20.0, and 50.0 μg L -1 were between 70.1% and 115.0%. The limits of detection for the analytes were 0.74-1.44 μg L -1 , and the intra-day relative standard deviations varied from 5.23% to 8.65%. The proposed method can be further applied

  19. Data from: Evolution of cross-resistance to medical triazoles in Aspergillus fumigatus through selection pressure of environmental fungicides

    NARCIS (Netherlands)

    Zhang, J.; Heuvel, van den Joost; Debets, A.J.M.; Verweij, Paul E.; Melchers, Willem J.G.; Zwaan, B.J.; Schoustra, S.E.

    2017-01-01

    Resistance to medical triazoles in Aspergillus fumigatus is an emerging problem for patients at risk of aspergillus diseases. There are currently two presumed routes for medical triazole-resistance selection: (i) through selection pressure of medical triazoles when treating patients and (ii) through

  20. Evolution of cross-resistance to medical triazoles in Aspergillus fumigatus through selection pressure of environmental fungicides

    NARCIS (Netherlands)

    Zhang, Jianhua; Heuvel, van den Joost; Debets, Fons; Verweij, Paul E.; Melchers, Willem J.G.; Zwaan, Bas J.; Schoustra, Sijmen E.

    2017-01-01

    Resistance to medical triazoles in Aspergillus fumigatus is an emerging problem for patients at risk of aspergillus diseases. There are currently two presumed routes for medical triazole-resistance selection: (i) through selection pressure of medical triazoles when treating patients and (ii)

  1. Evolution of cross-resistance to medical triazoles in Aspergillus fumigatus through selection pressure of environmental fungicides

    NARCIS (Netherlands)

    Zhang, J.; Heuvel, J. van den; Debets, A.J.; Verweij, P.E.; Melchers, W.J.G.; Zwaan, B.J.; Schoustra, S.E.

    2017-01-01

    Resistance to medical triazoles in Aspergillus fumigatus is an emerging problem for patients at risk of aspergillus diseases. There are currently two presumed routes for medical triazole-resistance selection: (i) through selection pressure of medical triazoles when treating patients and (ii) through

  2. Covalent Bonding of Metal-Organic Framework-5/Graphene Oxide Hybrid Composite to Stainless Steel Fiber for Solid-Phase Microextraction of Triazole Fungicides from Fruit and Vegetable Samples.

    Science.gov (United States)

    Zhang, Shuaihua; Yang, Qian; Wang, Wenchang; Wang, Chun; Wang, Zhi

    2016-04-06

    A hybrid material of the zinc-based metal-organic framework-5 and graphene oxide (metal-organic framework-5/graphene oxide) was prepared as a novel fiber coating material for solid-phase microextraction (SPME). The SPME fibers were fabricated by covalent bonding via chemical cross-linking between the coating material metal-organic framework-5/graphene oxide and stainless steel wire. The prepared fiber was used for the extraction of five triazole fungicides from fruit and vegetable samples. Gas chromatography coupled with microelectron capture detector (GC-μECD) was used for quantification. The developed method gave a low limit of detection (0.05-1.58 ng g(-1)) and good linearity (0.17-100 ng g(-1)) for the determination of the triazole fungicides in fruit and vegetable samples. The relative standard deviations (RSDs) for five replicate extractions of the triazole fungicides ranged from 3.7 to 8.9%. The method recoveries for spiked fungicides (5, 20, and 50 ng g(-1)) in grape, apple, cucumber, celery cabbage, pear, cabbage, and tomato samples were in the range of 85.6-105.8% with the RSDs ranging from 3.6 to 11.4%, respectively, depending on both the analytes and samples. The metal-organic framework-5/graphene oxide coated fiber was stable enough for 120 extraction cycles without a significant loss of extraction efficiency. The method was suitable for the determination of triazole fungicides in fruit and vegetable samples.

  3. Electrochemical degradation of triazole fungicides in aqueous solution using TiO2-NTs/SnO2-Sb/PbO2 anode: Experimental and DFT studies

    International Nuclear Information System (INIS)

    Han, Weiqing; Zhong, Congqiang; Liang, Linyue; Sun, Yunlong; Guan, Ying; Wang, Lianjun; Sun, Xiuyun; Li, Jiansheng

    2014-01-01

    Triazole fungicides (TFs) are toxic and bio-refractory contaminants widely spread in environment. This study investigated electrochemical degradation of TFs in aqueous solution at TiO 2 -NTs/SnO 2 -Sb/PbO 2 anode with particular attention to the effect of molecular structure. Three TFs with triazole ring in one biologically treated water including tricyclazole (TC), 1H-1,2,4-triazole (Tz) and propiconazole (PPC) were selected as the target compounds. Results of bulk electrolysis showed that degradation of all TFs was fit to a pseudo first-order equation. The three compounds were degraded with the following sequence: PPC > TC> Tz in terms of their rates of oxidation. Quantum chemical calculation using the density function theory (DFT) method was combined with experimental results to describe the degradation sequence of TFs. Atom charge was calculated by DFT method and active sites of TFs were identified respectively. Analysis of intermediates by GC-MS and LC-(ESI)-MS/MS showed agreement with calculation results. In addition, the acute toxicity of TC and PPC treated solution significantly decreased after treatment by electrochemical oxidation

  4. TOXICOGENOMIC STUDY OF TRIAZOLE FUNGICIDES AND PERFLUOROALKYL ACIDS IN RAT LIVERS ACCURATELY CATEGORIZES CHEMICALS AND IDENTIFIES MECHANISMS OF TOXICITY

    Science.gov (United States)

    Toxicogenomic analysis of five environmental chemicals was performed to investigate the ability of genomics to predict toxicity, categorize chemicals, and elucidate mechanisms of toxicity. Three triazole antifungals (myclobutanil, propiconazole, and triadimefon) and two perfluori...

  5. Is the amphibian X. laevis WEC a good alternative method to rodent WEC teratogenicity assay? The example of the three triazole derivative fungicides Triadimefon, Tebuconazole, Cyproconazole.

    Science.gov (United States)

    Di Renzo, Francesca; Bacchetta, Renato; Bizzo, Andrea; Giavini, Erminio; Menegola, Elena

    2011-09-01

    The aim of the present work is the assessment of teratogenic effects of three triazole-derived fungicides (Triadimefon, FON, Tebuconazole, TEBU, Cyproconazole, CYPRO) on rat and Xenopus laevis embryos cultured in vitro. Rat embryos, exposed to FON 31.25-250μM, CYPRO 31.25-62.5μM and to TEBU 62.5-250μM, showed specific malformations (fusions) at the level of the first and second branchial arches, with a concentration-dependent increase of severity of malformative pictures. After immunostaining, the ectomesenchyme has been identified as the target tissue. X. laevis larvae showed, at the same concentrations, specific malformations at the level of cartilaginous element derived from the first and second branchial arch ectomesenchyme. This work indicates the three tested triazoles as teratogenic both in rodents and in amphibian, inducing ectomesenchymal abnormalities, and suggests, at least for this class of molecules, the X. laevis method as adequate alternative model for teratogenic screening. Copyright © 2011 Elsevier Inc. All rights reserved.

  6. Estimation of modern range of fungicides and scope of their application in agriculture of Ukraine as component of state social and hygienic monitoring

    Directory of Open Access Journals (Sweden)

    Vavrinevych O.P.

    2013-12-01

    Full Text Available The analysis of the range of pesticides, including fungicides, authorized for use in Ukraine and the scope of their application during 1999 - 2012 years was carried out. Statistical research methods were used in the analysis, evaluation of the results was car¬ried out in terms of the rate of growth and increase. It was determined that in the range structure of pesticides, authorized for use in Ukraine the largest share accounted for herbicides. Part of the herbicides was 43,8±0,95% on average over the period from 1999 to 2012. The share of fungicides was 28,6±1,1%, insecticides - 20,3±0,78%, plant growth regulators - 7,4±0,59%. Mixed fungicides are the largest part of fungicides in the structure of the range (26,3-39,3%, the number of its had increased by 542% over 13-year period. Prior to 2003 there was a slight increase in the number of mixed fungicides, growth rate was 0-8,3% since 2006, its rate of increase has averaged 53% every 2 years. Triazoles and conazoles (14,9-31,4%, benzimidazoles, imidazoles (9,8-14,7%, carbamates, dithiocarbamates (3,1-13,8%, inorganic compounds (6,1-11,1% containing one active ingredient in formulation were the most common among the fungicides. The growth rate of strobilurin fungicides was 900%, triazoles – 550%, benzimidazoles, imidazoles – 400%, inorganic compounds – 243%, aniline-pyrimidines – 200%, pyrimidines, pyridines, pyrroles – 67%, dithiocarbamic and carbamic acid derivatives – 50%, phthalimides, phenylsulfamides, amides – 43%.

  7. [Cumulative risk assessment for consumers of agricultural crops polluted with one chemical class pesticide residues (case of triazole fungicides)].

    Science.gov (United States)

    Koval'chuk, N M; Omel'chuk, S T

    2011-01-01

    Different indices of cumulative risk assessment of combination of residues of pesticides which may simultaneously be present in raw agricultural crops, based on toxic evaluation of such combination have been presented. Risk for population health due to consumption of raw agricultural crops with triazole residues is acceptable on hazard index, point of departure index and cumulative risk index, exceeds allowable level on criterion "total margin of exposure".

  8. Endocrine disruptive effects in vitro of conazole antifungals used as pesticides and pharmaceutical

    DEFF Research Database (Denmark)

    Kjærstad, Mia Birkhøj; Taxvig, Camilla; Nellemann, Christine Lydia

    2010-01-01

    Widely used conazole antifungals were tested for endocrine disruptive effects using a panel of in vitro assays. They all showed endocrine disrupting potential and ability to act via several different mechanisms. Overall the imidazoles (econazole, ketoconazole, miconazole, prochloraz) were more...... inhibition of enzymes involved in the conversion of progesterone to testosterone. Prochloraz was most potent followed by econazole~miconazole>ketoconazole>tebuconazole>epoxiconazole>propiconazole. In the MCF-7 cell proliferation assay, the conazoles showed anti-estrogenic effect, including aromatase...... inhibition, since they inhibited the response induced by both 17β-estradiol (miconazole>econazole~ketoconazole>prochloraz>tebuconazole>epoxiconazole>propiconazole) and testosterone (econazole>miconazole>prochloraz>ketoconazole>tebuconazole>epoxiconazole>propiconazole). The triazoles were anti...

  9. Trace determination of five triazole fungicide residues in traditional Chinese medicine samples by dispersive solid-phase extraction combined with ultrasound-assisted dispersive liquid-liquid microextraction and UHPLC-MS/MS.

    Science.gov (United States)

    Ma, Shuping; Yuan, Xucan; Zhao, Pengfei; Sun, Hong; Ye, Xiu; Liang, Ning; Zhao, Longshan

    2017-08-01

    A novel and reliable method for determination of five triazole fungicide residues (triadimenol, tebuconazole, diniconazole, flutriafol, and hexaconazol) in traditional Chinese medicine samples was developed using dispersive solid-phase extraction combined with ultrasound-assisted dispersive liquid-liquid microextraction before ultra-high performance liquid chromatography with tandem mass spectrometry. The clean up of the extract was conducted using dispersive solid-phase extraction by directly adding sorbents into the extraction solution, followed by shaking and centrifugation. After that, a mixture of 400 μL trichloromethane (extraction solvent) and 0.5 mL of the above supernatant was injected rapidly into water for the dispersive liquid-liquid microextraction procedure. The factors affecting the extraction efficiency were optimized. Under the optimum conditions, the calibration curves showed good linearity in the range of 2.0-400 (tebuconazole, diniconazole, and hexaconazole) and 4.0-800 ng/g (triadimenol and flutriafol) with the regression coefficients higher than 0.9958. The limit of detection and limit of quantification for the present method were 0.5-1.1 and 1.8-4.0 ng/g, respectively. The recoveries of the target analytes ranged from 80.2 to 103.2%. The proposed method has been successfully applied to the analysis of five triazole fungicides in traditional Chinese medicine samples, and satisfactory results were obtained. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  10. Fast and robust direct immersion solid phase microextraction coupled with gas chromatography-time-of-flight mass spectrometry method employing a matrix compatible fiber for determination of triazole fungicides in fruits.

    Science.gov (United States)

    Silva, Érica A Souza; Lopez-Avila, Viorica; Pawliszyn, Janusz

    2013-10-25

    A fast and robust method was developed for the determination of ten triazole fungicides in fruit samples using direct immersion solid-phase microextraction coupled to gas chromatography with time-of-flight mass spectrometry detection (DI-SPME-GC-ToFMS). In this work, a newly developed concept of solid-phase microextraction (SPME) sorbent, which allows for direct immersion extraction in complex food matrices, has been applied in the analysis of 10 triazole fungicides in grapes and strawberries pulps. Potential factors affecting the extraction efficiency were investigated and optimized, including extraction temperature, sample pH, and ionic strength, agitation speed, extraction and desorption times. Under optimized conditions, the method was linear for over 4 orders of magnitude in concentration, with linear regression coefficients (R(2)) greater than 0.99 for all test compounds in both matrices. Method reproducibility, as determined by analysis of spiked grapes and strawberries, was better than ±20%. The limits of quantitation objective (LOQs) ranged from 0.25 to 5 ng g(-1) for both matrices, well below the maximum residues levels allowed for those compounds in both matrices. The method was successfully applied in the analysis of commercial samples of grapes and strawberries. Finally, the new SPME method was compared to a modified version of t QuEChERS AOAC method: the limits of quantitation reached by SPME were at least one order of magnitude lower than those achieved by the QuEChERS method, whereas precision and accuracy were comparable for both methods. Copyright © 2013 Elsevier B.V. All rights reserved.

  11. Identification of isolates of the plant pathogen Leptosphaeria maculans with resistance to the triazole fungicide fluquinconazole using a novel In Planta assay.

    Directory of Open Access Journals (Sweden)

    Angela P Van de Wouw

    Full Text Available Leptosphaeria maculans is the major pathogen of canola (oilseed rape, Brassica napus worldwide. In Australia, the use of azole fungicides has contributed to the 50-fold increase in canola production in the last 25 years. However, extensive application of fungicides sets the stage for the selection of fungal populations with resistance. A high-throughput in planta assay was developed to allow screening of thousands of isolates from multiple populations. Using this screen, isolates were identified with decreased sensitivity to the fungicide fluquinconazole when applied at field rates as a protective seed dressing: these isolates cause significantly larger lesions on cotyledons and true leaves and increased disease severity at plant maturity. This increased in planta resistance was specific to fluquinconazole, with no cross resistance to flutriafol or tebuconazole/prothioconazole. In a limited set of 22 progeny from a cross between resistant and susceptible parents, resistance segregated in a 1:1 ratio, suggesting a single gene is responsible. A survey of 200 populations from across canola growing regions of Australia revealed fungicide resistance was present in 15% of the populations. Although in vitro analysis of the fungicide resistant isolates showed a significant shift in the average EC50 compared to the sensitive isolates, this was not as evident as the in planta assays. The development of this novel, high-throughput in planta assay has led to the identification of the first fungicide resistant L. maculans isolates, which may pose a threat to the productivity of the Australian canola industry.

  12. Effects of a triazole fungicide and a pyrethroid insecticide on the decomposition of leaves in the presence or absence of macroinvertebrate shredders.

    Science.gov (United States)

    Rasmussen, Jes Jessen; Monberg, Rikke Juul; Baattrup-Pedersen, Annette; Cedergreen, Nina; Wiberg-Larsen, Peter; Strobel, Bjarne; Kronvang, Brian

    2012-08-15

    Previously, laboratory experiments have revealed that freely diluted azole fungicides potentiate the direct toxic effect of pyrethroid insecticides on Daphnia magna. More ecologically relevant exposure scenarios where pesticides are adsorbed have not been addressed. In this study we exposed beech leaves (Fagus sylvatica) to the azole fungicide propiconazole (50 or 500 μg L(-1)), the pyrethroid insecticide alpha-cypermethrin (0.1 or 1 μg L(-1)) or any combination of the two for 3h. Exposed leaves were transferred to aquaria with or without an assemblage of macroinvertebrate shredders, and we studied treatment effects on rates of microbial leaf decomposition, microbial biomass (using C:N ratio as a surrogate measure) and macroinvertebrate shredding activity during 26 days post-exposure. Microbial leaf decomposition rates were significantly reduced in the propiconazole treatments, and the reduction in microbial activity was significantly correlated with loss of microbial biomass (increased C:N ratio). Macroinvertebrate shredding activity was significantly reduced in the alpha-cypermethrin treatments. In addition, the macroinvertebrate assemblage responded to the propiconazole treatments by increasing their consumption of leaf litter with lower microbial biomass, probably to compensate for the reduced nutritional quality of this leaf litter. We found no interaction between the two pesticides on macroinvertebrate shredding activity, using Independent Action as a reference model. In terms of microbial leaf decomposition rates, however, alpha-cypermethrin acted as an antagonist on propiconazole. Based on these results we emphasise the importance of considering indirect effects of pesticides in the risk assessment of surface water ecosystems. Copyright © 2012 Elsevier B.V. All rights reserved.

  13. 14C-labeling of a novel fungicide

    International Nuclear Information System (INIS)

    Nakatsuka, Iwao; Kanamaru, Hiroshi; Kamada, Takeshi; Kawahara, Kazuo; Yoshitake, Akira

    1986-01-01

    A novel fungicide, (-) (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol (S-3308 L) and its three optically active stereoisomers were labeled with carbon-14 at the triazole ring for use in the metabolic and environmental fate studies. (author)

  14. Is the emergence of fungal resistance to medical triazoles related to their use in the agroecosystems? A mini review

    OpenAIRE

    Ribas e Ribas, A?cha Daniela; Spolti, Pierri; Del Ponte, Emerson Medeiros; Donato, Katarzyna Zawada; Schrekker, Henri; Fuentefria, Alexandre Meneghello

    2016-01-01

    Abstract Triazole fungicides are used broadly for the control of infectious diseases of both humans and plants. The surge in resistance to triazoles among pathogenic populations is an emergent issue both in agriculture and medicine. The non-rational use of fungicides with site-specific modes of action, such as the triazoles, may increase the risk of antifungal resistance development. In the medical field, the surge of resistant fungal isolates has been related to the intensive and recurrent t...

  15. Is the emergence of fungal resistance to medical triazoles related to their use in the agroecosystems? A mini review

    Directory of Open Access Journals (Sweden)

    Aícha Daniela Ribas e Ribas

    Full Text Available Abstract Triazole fungicides are used broadly for the control of infectious diseases of both humans and plants. The surge in resistance to triazoles among pathogenic populations is an emergent issue both in agriculture and medicine. The non-rational use of fungicides with site-specific modes of action, such as the triazoles, may increase the risk of antifungal resistance development. In the medical field, the surge of resistant fungal isolates has been related to the intensive and recurrent therapeutic use of a limited number of triazoles for the treatment and prophylaxis of many mycoses. Similarities in the mode of action of triazole fungicides used in these two fields may lead to cross-resistance, thus expanding the spectrum of resistance to multiple fungicides and contributing to the perpetuation of resistant strains in the environment. The emergence of fungicide-resistant isolates of human pathogens has been related to the exposure to fungicides used in agroecosystems. Examples include species of cosmopolitan occurrence, such as Fusarium and Aspergillus, which cause diseases in both plants and humans. This review summarizes the information about the most important triazole fungicides that are largely used in human clinical therapy and agriculture. We aim to discuss the issues related to fungicide resistance and the recommended strategies for preventing the emergence of triazole-resistant fungal populations capable of spreading across environments.

  16. Is the emergence of fungal resistance to medical triazoles related to their use in the agroecosystems? A mini review.

    Science.gov (United States)

    Ribas E Ribas, Aícha Daniela; Spolti, Pierri; Del Ponte, Emerson Medeiros; Donato, Katarzyna Zawada; Schrekker, Henri; Fuentefria, Alexandre Meneghello

    Triazole fungicides are used broadly for the control of infectious diseases of both humans and plants. The surge in resistance to triazoles among pathogenic populations is an emergent issue both in agriculture and medicine. The non-rational use of fungicides with site-specific modes of action, such as the triazoles, may increase the risk of antifungal resistance development. In the medical field, the surge of resistant fungal isolates has been related to the intensive and recurrent therapeutic use of a limited number of triazoles for the treatment and prophylaxis of many mycoses. Similarities in the mode of action of triazole fungicides used in these two fields may lead to cross-resistance, thus expanding the spectrum of resistance to multiple fungicides and contributing to the perpetuation of resistant strains in the environment. The emergence of fungicide-resistant isolates of human pathogens has been related to the exposure to fungicides used in agroecosystems. Examples include species of cosmopolitan occurrence, such as Fusarium and Aspergillus, which cause diseases in both plants and humans. This review summarizes the information about the most important triazole fungicides that are largely used in human clinical therapy and agriculture. We aim to discuss the issues related to fungicide resistance and the recommended strategies for preventing the emergence of triazole-resistant fungal populations capable of spreading across environments. Copyright © 2016 Sociedade Brasileira de Microbiologia. Published by Elsevier Editora Ltda. All rights reserved.

  17. Synthesis of [triazole-3(5)-14C]-propiconazole stereoisomers

    International Nuclear Information System (INIS)

    Hadjidemetriou, D.; Loeffler, R.T.

    1992-01-01

    A preparation of all four stereoisomers of the fungicide and sterol biosynthesis inhibitor propiconazole (1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole), labelled with [ 14 C] in the triazole ring, is described. (author)

  18. Quantitative changes in endogenous DNA damage correlate with conazole mutagenicity and tumorigenicity.

    Science.gov (United States)

    The mouse liver tumorigenic conazolefungicides triadimefon and propiconazole have previously been shown to be in vivo mouse liver mutagens in the Big Blue" transgenic mutation assay when administered in feed at tumorigenic doses, whereas the nontumorigenic conazole myclobutanil w...

  19. The toxicity of the fungicide Propiconazole to soil flagellates

    DEFF Research Database (Denmark)

    Ekelund, Flemming; Westergaard, Kamma; Søe, Dorthe

    2000-01-01

    We investigated the effects of the ergosterol-inhibiting fungicide, propiconazole {1-[[2-(2,4-dichlorphenyl) - 4 - propyl - 1,3 - dioxolan - 2 - yl]methyl] - 1H - 1,2,4 triazole; Tilt}, on mixed natural populations of bacterivorous and fungivorous flagellates in soil and on single species...... of bacterivorous flagellates in liquid culture. The fungicide affected a mixed natural population of fungivorous flagellates less than the population of bacterivorous flagellates. Our results indicated that the effects of propiconazole on flagellates are direct toxic effects and not effects mediated via their food...

  20. Efficient Synthesis and Bioactivity of Novel Triazole Derivatives.

    Science.gov (United States)

    Hu, Boyang; Zhao, Hanqing; Chen, Zili; Xu, Chen; Zhao, Jianzhuang; Zhao, Wenting

    2018-03-21

    Triazole pesticides are organic nitrogen-containing heterocyclic compounds, which contain 1,2,3-triazole ring. In order to develop potential glucosamine-6-phosphate synthase (GlmS) inhibitor fungicides, forty compounds of triazole derivatives were synthesized in an efficient way, thirty nine of them were new compounds. The structures of all the compounds were confirmed by high resolution mass spectrometer (HRMS), ¹H-NMR and 13 C-NMR. The fungicidal activities results based on means of mycelium growth rate method indicated that some of the compounds exhibited good fungicidal activities against P. CapasiciLeonian , Sclerotinia sclerotiorum (Lib.) de Bary, Pyricularia oryzae Cav. and Fusarium oxysporum Schl. F.sp. vasinfectum (Atk.) Snyd. & Hans. at the concentration of 50 µg/mL, especially the inhibitory rates of compounds 1-d and 1-f were over 80%. At the same time, the preliminary studies based on the Elson-Morgan method indicated that the compounds exhibited some inhibitory activity toward glucosamine-6-phosphate synthase (GlmS). These compounds will be further studied as potential antifungal lead compounds. The structure-activity relationships (SAR) were discussed in terms of the effects of the substituents on both the benzene and the sugar ring.

  1. Differential triazole sensitivity among members of the Fusarium graminearum species complex infecting barley grains in Brazil

    Science.gov (United States)

    Fusarium head blight (FHB) is an important disease of small grains and is caused mainly by members of the Fusarium graminearum species complex (FGSC). Barley growers in Brazil rely on fungicides, especially triazoles, to suppress the disease and limit mycotoxin contamination of grain. Information on...

  2. Changes in carbohydrate metabolism by triazole growth regulators in cassava (Manihot esculenta Crantz); effects on tuber production and quality.

    Science.gov (United States)

    Gomathinayagam, Muthiah; Jaleel, Cheruth Abdul; Lakshmanan, G M Alagu; Panneerselvam, Rajaram

    2007-09-01

    We have evaluated the ability of two triazole growth regulators, viz. triadimefon (TDM) and hexaconazole (HEX), in the enhancement of tuber production and quality in cassava (Manihot esculenta Crantz) through their effects on carbohydrate metabolism. One litre of 20 mg(-1) TDM and 15 mg(-1) HEX solution per plant were used for the treatments and groundwater was given to control plants. Triazole treatments reduced plant height and leaf area, but increased fresh and dry weights. Plants treated with TDM showed an increased net assimilation rate, which is followed by HEX and control plants. Triazole compounds increased the relative growth rate of cassava after 200 DAP, i.e. in the phase of tuber enlargement. Triazole compounds increased the starch and other carbohydrate contents and carbohydrate metabolising enzyme activities. From the results of this study, it can be concluded that these triazoles can significantly enhance the tuber production and quality by affecting the starch metabolism, apart from their fungicidal properties.

  3. Triazole Susceptibilities in Thermotolerant Fungal Isolates from Outdoor Air in the Seoul Capital Area in South Korea.

    Directory of Open Access Journals (Sweden)

    Seungeun Lee

    Full Text Available Emerging fungi resistant to triazoles are a concern because of the increased use of medical triazoles and exposure to agricultural triazoles. However, little is known about the levels of triazole susceptibility in outdoor airborne fungi making it difficult to assess the risks of inhalation exposure to airborne, antifungal-resistant fungi. This study examined triazole susceptibilities of the airborne thermotolerant fungi isolated from the ambient air of the Seoul Capital Area of South Korea. We used impactor air sampling with triazole-containing nutrient agar plates as the collection substrates to screen for airborne fungal isolates based on their triazole susceptibilities. This study estimated that 0.17% of all the culturable fungi belong to the pathogenic thermotolerant taxa, among which each isolate of Aspergillus niger and Aspergillus tubingensis showed a minimum inhibitory concentration (MIC of 2 μg/mL or greater for itraconazole. Their concentration in air was 0.4 CFU/m3. Seven human pathogenic Paecilomyces variotii isolates had MICs of 32 μg/mL or greater and lower than 2 μg/mL for the agricultural fungicide tebuconazole and the medical triazole itraconazole, respectively. Though the concentration was low, our results confirm the presence of airborne fungi with high MICs for itraconazole in ambient air. Inhalation is an important exposure route because people inhale more than 10 m3 of air each day. Vigilance is preferred over monitoring for the emergence of triazole-resistant fungal pathogens in ambient outdoor air.

  4. Triazole Susceptibilities in Thermotolerant Fungal Isolates from Outdoor Air in the Seoul Capital Area in South Korea

    Science.gov (United States)

    Lee, Seungeun; Xu, Siyu; Bivila, Chemmeri Padasseri; Lee, Hyeyoung; Park, Myung Soo; Lim, Young Woon; Yamamoto, Naomichi

    2015-01-01

    Emerging fungi resistant to triazoles are a concern because of the increased use of medical triazoles and exposure to agricultural triazoles. However, little is known about the levels of triazole susceptibility in outdoor airborne fungi making it difficult to assess the risks of inhalation exposure to airborne, antifungal-resistant fungi. This study examined triazole susceptibilities of the airborne thermotolerant fungi isolated from the ambient air of the Seoul Capital Area of South Korea. We used impactor air sampling with triazole-containing nutrient agar plates as the collection substrates to screen for airborne fungal isolates based on their triazole susceptibilities. This study estimated that 0.17% of all the culturable fungi belong to the pathogenic thermotolerant taxa, among which each isolate of Aspergillus niger and Aspergillus tubingensis showed a minimum inhibitory concentration (MIC) of 2 μg/mL or greater for itraconazole. Their concentration in air was 0.4 CFU/m3. Seven human pathogenic Paecilomyces variotii isolates had MICs of 32 μg/mL or greater and lower than 2 μg/mL for the agricultural fungicide tebuconazole and the medical triazole itraconazole, respectively. Though the concentration was low, our results confirm the presence of airborne fungi with high MICs for itraconazole in ambient air. Inhalation is an important exposure route because people inhale more than 10 m3 of air each day. Vigilance is preferred over monitoring for the emergence of triazole-resistant fungal pathogens in ambient outdoor air. PMID:26405807

  5. Strong lethality and teratogenicity of strobilurins on Xenopus tropicalis embryos: Basing on ten agricultural fungicides

    International Nuclear Information System (INIS)

    Li, Dan; Liu, Mengyun; Yang, Yongsheng; Shi, Huahong; Zhou, Junliang; He, Defu

    2016-01-01

    Agricultural chemical inputs have been considered as a risk factor for the global declines in amphibian populations, yet the application of agricultural fungicides has increased dramatically in recent years. Currently little is known about the potential toxicity of fungicides on the embryos of amphibians. We studied the effects of ten commonly used fungicides (four strobilurins, two SDHIs, two triazoles, fludioxonil and folpet) on Xenopus tropicalis embryos. Lethal and teratogenic effects were respectively examined after 48 h exposure. The median lethal concentrations (LC50s) and the median teratogenic concentrations (TC50s) were determined in line with actual exposure concentrations. These fungicides except two triazoles showed obvious lethal effects on embryos; however LC50s of four strobilurins were the lowest and in the range of 6.81–196.59 μg/L. Strobilurins, SDHIs and fludioxonil induced severe malformations in embryos. Among the ten fungicides, the lowest TC50s were observed for four strobilurins in the range of 0.61–84.13 μg/L. The teratogenicity shared similar dose–effect relationship and consistent phenotypes mainly including microcephaly, hypopigmentation, somite segmentation and narrow fins. The findings indicate that the developmental toxicity of currently-used fungicides involved with ecologic risks on amphibians. Especially strobilurins are highly toxic to amphibian embryos at μg/L level, which is close to environmentally relevant concentrations. - Highlights: • Effects of ten agricultural fungicides were tested on Xenopus tropicalis embryos. • Strobilurin fungicides showed strong lethal and teratogenic effects on embryos. • Lowest LC50 and TC50 were observed for strobilurins in ten fungicides. • μg/L level of toxic concentrations for strobilurins was environmentally relevant. • Teratogenicity shared similar dose–effect relationship and main phenotypes. - Strobilurins induced strong lethality and teratogenicity on Xenopus

  6. Annual Fungicide Loadings

    Data.gov (United States)

    U.S. Environmental Protection Agency — Pesticides, Herbicides, Fungicides...etc, are used for a variety of purposes, including control of household, lawn, and garden pests; for control of mosquitoes and...

  7. Peptides of the constant region of antibodies display fungicidal activity.

    Directory of Open Access Journals (Sweden)

    Luciano Polonelli

    Full Text Available Synthetic peptides with sequences identical to fragments of the constant region of different classes (IgG, IgM, IgA of antibodies (Fc-peptides exerted a fungicidal activity in vitro against pathogenic yeasts, such as Candida albicans, Candida glabrata, Cryptococcus neoformans, and Malassezia furfur, including caspofungin and triazole resistant strains. Alanine-substituted derivatives of fungicidal Fc-peptides, tested to evaluate the critical role of each residue, displayed unaltered, increased or decreased candidacidal activity in vitro. An Fc-peptide, included in all human IgGs, displayed a therapeutic effect against experimental mucosal and systemic candidiasis in mouse models. It is intriguing to hypothesize that some Fc-peptides may influence the antifungal immune response and constitute the basis for devising new antifungal agents.

  8. Fate of triazoles in softwood upon environmental exposure.

    Science.gov (United States)

    Kukowski, Klara; Martinská, Veronika; Sedgeman, Carl A; Kuplic, Paige; Kozliak, Evguenii I; Fisher, Stephen; Kubátová, Alena

    2017-10-01

    Determining the fate of preservatives in commercial wood products is essential to minimize their losses and improve protective impregnation techniques. The fate of triazole fungicides in ponderosa pine wood was investigated in both outdoor and controlled-environment experiments using a representative triazole, tebuconazole (TAZ), which was accompanied by propiconazole (PAZ) in selected experiments. The study was designed to mimic industrial settings used in window frame manufacturing. To investigate the TAZ fate in detail, loosely and strongly bound fractions were differentiated using a multi-step extraction. The loosely bound TAZ fraction extracted through two sonications accounted for 85± 5% of the total TAZ, while the strongly bound TAZ was extracted only with an exhaustive Soxhlet extraction and corresponded to the remaining 15± 5%. A significant fraction (∼80%) of the original TAZ remained in the wood despite a six-month exposure to harsh environmental conditions, maintaining wood preservation and assuring minimal environmental impact. Depletion of loosely bound TAZ was observed from cross-sectional surfaces when exposed to rain, high humidity and sunlight. Water leaching was deemed to be the major route leading to triazole losses from wood. Leaching rate was found to be slightly higher for TAZ than for PAZ. The contribution of bio-, photo- and thermal degradation of triazoles was negligible as both PAZ and TAZ sorbed in wood remained intact. Triazole evaporation was also found to be minor at the moderate temperature (20-25 °C) recorded throughout the outdoor study. Copyright © 2017 Elsevier Ltd. All rights reserved.

  9. Triazole Fungicides Can Induce Cross-Resistance to Medical Triazoles in Aspergillus fumigatus

    NARCIS (Netherlands)

    Snelders, E.; Camps, S.M.T.; Karawajczyk, A.; Schaftenaar, G.; Kema, G.H.J.; Lee, van der H.A.; Klaassen, C.H.; Melchers, W.J.G.; Verweij, P.E.

    2012-01-01

    Background Azoles play an important role in the management of Aspergillus diseases. Azole resistance is an emerging global problem in Aspergillus fumigatus, and may develop through patient therapy. In addition, an environmental route of resistance development has been suggested through exposure to

  10. Triazole fungicides can induce cross-resistance to medical triazoles in Aspergillus fumigatus.

    NARCIS (Netherlands)

    Snelders, E.; Camps, S.M.T.; Karawajczyk, A.; Schaftenaar, G.; Kema, G.H.; Lee, H.A.L. van der; Klaassen, C.H.; Melchers, W.J.G.; Verweij, P.E.

    2012-01-01

    BACKGROUND: Azoles play an important role in the management of Aspergillus diseases. Azole resistance is an emerging global problem in Aspergillus fumigatus, and may develop through patient therapy. In addition, an environmental route of resistance development has been suggested through exposure to

  11. Association between virulence and triazole tolerance in the phytopathogenic fungus Mycosphaerella graminicola.

    Directory of Open Access Journals (Sweden)

    Lina Yang

    Full Text Available Host resistance and synthetic antimicrobials such as fungicides are two of the main approaches used to control plant diseases in conventional agriculture. Although pathogens often evolve to overcome host resistance and antimicrobials, the majority of reports have involved qualitative host - pathogen interactions or antimicrobials targeting a single pathogen protein or metabolic pathway. Studies that consider jointly the evolution of virulence, defined as the degree of damage caused to a host by parasite infection, and antimicrobial resistance are rare. Here we compared virulence and fungicide tolerance in the fungal pathogen Mycosphaerella graminicola sampled from wheat fields across three continents and found a positive correlation between virulence and tolerance to a triazole fungicide. We also found that quantitative host resistance selected for higher pathogen virulence. The possible mechanisms responsible for these observations and their consequences for sustainable disease management are discussed.

  12. Sensitivity of Fusarium culmorum to triazoles: impact of trichothecene chemotypes, oxidative stress response and genetic diversity.

    Science.gov (United States)

    Hellin, Pierre; Scauflaire, Jonathan; Van Hese, Viviane; Munaut, Françoise; Legrève, Anne

    2017-06-01

    Fusarium culmorum is a fungal pathogen occurring worldwide on various weeds and important crops. Triazoles have been shown to be the most effective fungicide for managing Fusarium spp., but little is known about their specific activity on F. culmorum. The sensitivity of 107 F. culmorum strains to triazoles was assessed using microtitre plate assays. The EC 50 values ranged from 0.14 to 1.53 mg L -1 for tebuconazole and from 0.25 to 2.47 mg L -1 for epoxiconazole. Cross-resistance to both azoles was found (r = 0.61). F. culmorum appeared to be significantly more sensitive than F. graminearum or F. cerealis. No increase in the mean EC 50 was observed over time, which might be related to an unfavourable fitness cost, measured here as fungal growth. On average, nivalenol-producing strains of F. culmorum were significantly more resistant than deoxynivalenol-producing strains. The relationship between resistance and chemotype-dependent adaptation to oxidative stress was investigated, but remained unclear. No link between inter-simple sequence repeat (ISSR) genetic diversity and triazole resistance could be established. Fungicide use might not be a driving force in the evolution of F. culmorum, and the benefit of a resistance trait probably does not outweigh its costs. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

  13. Prediction of Mutagenicity, Carcinogenicity, Developmental Toxicity, and Skin Sensitisation with CAESAR Program for a Set of Conazoles

    OpenAIRE

    Bolčič-Tavčar, Mateja; Vračko, Marjan

    2012-01-01

    This article presents models to predict mutagenicity, carcinogenicity, developmental toxicity, and skin sensitisation for a set of 27 conazoles. The predictions were performed with the program package CAESAR, which is available on the Internet. The CAESAR programs were developed to support the European Community Regulation on chemicals and their safe use (REACH) and follow the OECD principles for (Q)SAR models used for regulatory purposes. The programs provide a number of information, includi...

  14. Disruption of quercetin metabolism by fungicide affects energy production in honey bees (Apis mellifera).

    Science.gov (United States)

    Mao, Wenfu; Schuler, Mary A; Berenbaum, May R

    2017-03-07

    Cytochrome P450 monooxygenases (P450) in the honey bee, Apis mellifera , detoxify phytochemicals in honey and pollen. The flavonol quercetin is found ubiquitously and abundantly in pollen and frequently at lower concentrations in honey. Worker jelly consumed during the first 3 d of larval development typically contains flavonols at very low levels, however. RNA-Seq analysis of gene expression in neonates reared for three days on diets with and without quercetin revealed that, in addition to up-regulating multiple detoxifying P450 genes, quercetin is a negative transcriptional regulator of mitochondrion-related nuclear genes and genes encoding subunits of complexes I, III, IV, and V in the oxidative phosphorylation pathway. Thus, a consequence of inefficient metabolism of this phytochemical may be compromised energy production. Several P450s metabolize quercetin in adult workers. Docking in silico of 121 pesticide contaminants of American hives into the active pocket of CYP9Q1, a broadly substrate-specific P450 with high quercetin-metabolizing activity, identified six triazole fungicides, all fungal P450 inhibitors, that dock in the catalytic site. In adults fed combinations of quercetin and the triazole myclobutanil, the expression of five of six mitochondrion-related nuclear genes was down-regulated. Midgut metabolism assays verified that adult bees consuming quercetin with myclobutanil metabolized less quercetin and produced less thoracic ATP, the energy source for flight muscles. Although fungicides lack acute toxicity, they may influence bee health by interfering with quercetin detoxification, thereby compromising mitochondrial regeneration and ATP production. Thus, agricultural use of triazole fungicides may put bees at risk of being unable to extract sufficient energy from their natural food.

  15. Disruption of quercetin metabolism by fungicide affects energy production in honey bees (Apis mellifera)

    Science.gov (United States)

    Mao, Wenfu; Schuler, Mary A.; Berenbaum, May R.

    2017-01-01

    Cytochrome P450 monooxygenases (P450) in the honey bee, Apis mellifera, detoxify phytochemicals in honey and pollen. The flavonol quercetin is found ubiquitously and abundantly in pollen and frequently at lower concentrations in honey. Worker jelly consumed during the first 3 d of larval development typically contains flavonols at very low levels, however. RNA-Seq analysis of gene expression in neonates reared for three days on diets with and without quercetin revealed that, in addition to up-regulating multiple detoxifying P450 genes, quercetin is a negative transcriptional regulator of mitochondrion-related nuclear genes and genes encoding subunits of complexes I, III, IV, and V in the oxidative phosphorylation pathway. Thus, a consequence of inefficient metabolism of this phytochemical may be compromised energy production. Several P450s metabolize quercetin in adult workers. Docking in silico of 121 pesticide contaminants of American hives into the active pocket of CYP9Q1, a broadly substrate-specific P450 with high quercetin-metabolizing activity, identified six triazole fungicides, all fungal P450 inhibitors, that dock in the catalytic site. In adults fed combinations of quercetin and the triazole myclobutanil, the expression of five of six mitochondrion-related nuclear genes was down-regulated. Midgut metabolism assays verified that adult bees consuming quercetin with myclobutanil metabolized less quercetin and produced less thoracic ATP, the energy source for flight muscles. Although fungicides lack acute toxicity, they may influence bee health by interfering with quercetin detoxification, thereby compromising mitochondrial regeneration and ATP production. Thus, agricultural use of triazole fungicides may put bees at risk of being unable to extract sufficient energy from their natural food. PMID:28193870

  16. Microwave Assistant Synthesis, Antifungal Activity and DFT Theoretical Study of Some Novel 1,2,4-Triazole Derivatives Containing Pyridine Moiety

    Directory of Open Access Journals (Sweden)

    Guo-Xiang Sun

    2014-05-01

    Full Text Available In order to investigate the biological activity of novel 1,2,4-triazole compounds, seventeen novel 1,2,4-triazole derivatives containing pyridine moiety were synthesized under microwave assistant condition by multi-step reactions. The structures were characterized by 1H NMR, MS and elemental analyses. The target compounds were evaluated for their fungicidal activities against Stemphylium lycopersici (Enjoji Yamamoto, Fusarium oxysporum. sp. cucumebrium, and Botrytis cinerea in vivo, and the results indicated that some of the title compounds displayed excellent fungicidal activities. Theoretical calculation of the title compound was carried out with B3LYP/6-31G (d,p. The full geometry optimization was carried out using 6-31G (d,p basis set, and the frontier orbital energy, atomic net charges were discussed, and the structure-activity relationship was also studied.

  17. Fluorescence of Hydroxyphenyl-Substituted "Click" Triazoles.

    Science.gov (United States)

    Meisner, Quinton J; Accardo, Joseph V; Hu, Guoxiang; Clark, Ronald J; Jiang, De-En; Zhu, Lei

    2018-03-22

    The structural and optical properties of hydroxyphenyl-substituted-1,2,3-triazole molecules ("click" triazoles) are described. "Click" triazoles are prepared from the copper(I)-catalyzed azide-alkyne cycloaddition reactions. The alkyne-derived C4 substituent of a "click" triazole engages in electronic conjugation more effectively with the triazolyl core than the azide-derived N1 substituent. Furthermore, triazolyl group exerts a stronger electron-withdrawing effect on the N1 than the C4 substituent. Therefore, the placement of an electron-donating group at either C4 or N1 position and the presence or the absence of an intramolecular hydrogen bond (HB) have profound influences on the optical properties of these compounds. The reported "click" triazoles have fluorescence quantum yields in the range of 0.1-0.3 and large apparent Stokes shifts (8000-13 000 cm -1 ) in all tested solvents. Deprotonation of "click" triazoles with a C4 hydroxyphenyl group increases their Stokes shifts; while the opposite (or quenching) occurs to the triazoles with an N1 hydroxyphenyl substituent. For the triazoles that contain intramolecular HBs, neither experimental nor computational results support a model of excited state intramolecular proton transfer (ESIPT). Rather, the excited state internal (or intramolecular) charge transfer (ICT) mechanism is more suitable to explain the fluorescence properties of the hydroxyphenyl-substituted "click" triazoles; specifically, the large Stokes shifts of these compounds.

  18. Strobilurin fungicides induce changes in photosynthetic gas exchange that do not improve water use efficiency of plants grown under conditions of water stress.

    Science.gov (United States)

    Nason, Mark A; Farrar, John; Bartlett, David

    2007-12-01

    The effects of five strobilurin (beta-methoxyacrylate) fungicides and one triazole fungicide on the physiological parameters of well-watered or water-stressed wheat (Triticum aestivum L.), barley (Hordeum vulgare L.) and soya (Glycine max Merr.) plants were compared. Water use efficiency (WUE) (the ratio of rate of transpiration, E, to net rate of photosynthesis, A(n)) of well-watered wheat plants was improved slightly by strobilurin fungicides, but was reduced in water-stressed plants, so there is limited scope for using strobilurins to improve the water status of crops grown under conditions of drought. The different strobilurin fungicides had similar effects on plant physiology but differed in persistence and potency. When applied to whole plants using a spray gun, they reduced the conductance of water through the epidermis (stomatal and cuticular transpiration), g(sw), of leaves. Concomitantly, leaves of treated plants had a lower rate of transpiration, E, a lower intercellular carbon dioxide concentration, c(i), and a lower net rate of photosynthesis, A(n), compared with leaves of control plants or plants treated with the triazole. The mechanism for the photosynthetic effects is not known, but it is hypothesised that they are caused either by strobilurin fungicides acting directly on ATP production in guard cell mitochondria or by stomata responding to strobilurin-induced changes in mesophyll photosynthesis. The latter may be important since, for leaves of soya plants, the chlorophyll fluorescence parameter F(v)/F(m) (an indication of the potential quantum efficiency of PSII photochemistry) was reduced by strobilurin fungicides. It is likely that the response of stomata to strobilurin fungicides is complex, and further research is required to elucidate the different biochemical pathways involved. Copyright (c) 2007 Society of Chemical Industry.

  19. Effect of prothioconazole-based fungicides on Fusarium head blight, grain yield and deoxynivalenol accumulation in wheat under field conditions

    Directory of Open Access Journals (Sweden)

    Miriam HAIDUKOWSKI

    2012-05-01

    Full Text Available The effect of triazole-based treatments on Fusarium head blight (FHB, grain yields and the accumulation of deoxynivalenol (DON in harvested wheat kernels was evaluated by means of twenty multi-site field experiments performed during five consecutive growing seasons (from 2004‒2005 to 2008‒2009 in Italy. Fungicide treatments were carried out on different cultivars of common wheat (cv. Serio, Blasco, Genio and Savio and durum wheat (cv. Orobel, Saragolla, San Carlo, Levante, Duilio, Karur and Derrik after artificial inoculation with a mixture of toxigenic Fusarium graminearum and F. culmorum strains. The application of fungicides containing prothioconazole (Proline® or Prosaro® at the beginning of anthesis (BBCH 61 resulted in a consistent reduction of FHB disease severity (by between 39 and 93% and DON levels in wheat kernels (by between 40 and 91% and increased wheat yields (from 0.4 to 5.6 t ha-1, average 2.2 t ha-1, as compared to the untreated/inoculated control. Fungicides containing tebuconazole (Folicur® SE and cyproconazole plus prochloraz (Tiptor® Xcell showed a reduced effectiveness compared with prothioconazole-based treatments. All fungicide treatments were more effective in reducing DON and increasing grain yields of common wheat than durum wheat. Results showed that the application of fungicides containing prothioconazole at the beginning of anthesis provided a strong reduction of FHB disease, allowing both an increase in grain yields and a considerable reduction of DON content in wheat kernels.

  20. Elimination of fungicides in biopurification systems: Effect of fungal bioaugmentation on removal performance and microbial community structure.

    Science.gov (United States)

    Murillo-Zamora, Sergio; Castro-Gutiérrez, Víctor; Masís-Mora, Mario; Lizano-Fallas, Verónica; Rodríguez-Rodríguez, Carlos E

    2017-11-01

    Bioaugmentation with ligninolytic fungi represents a potential way to improve the performance of biomixtures used in biopurification systems for the treatment of pesticide-containing agricultural wastewater. The fungus Trametes versicolor was employed in the bioaugmentation of a biomixture to be used in the simultaneous removal of seven fungicides. Liquid cultures of the fungus were able to remove tebuconazole, while no evidence of carbendazim, metalaxyl and triadimenol depletion was found. When applied in the biomixture, the bioaugmented matrix failed to remove all the triazole fungicides (including tebuconazole) under the assayed conditions, but was efficient to eliminate carbendazim, edifenphos and metalaxyl (the latter only after a second pesticide application). The re-addition of pesticides markedly increased the elimination of carbendazim and metalaxyl; nonetheless, no clear enhancement of the biomixture performance could be ascribed to fungal bioaugmentation, not even after the re-inoculation of fungal biomass. Detoxification efficiently took place in the biomixture (9 d after pesticide applications) according to acute tests on Daphnia magna. DGGE-analysis revealed only moderate time-divergence in bacterial and fungal communities, and a weak establishment of T. versicolor in the matrix. Data suggest that the non-bioaugmented biomixture is useful for the treatment of fungicides other than triazoles. Copyright © 2017 Elsevier Ltd. All rights reserved.

  1. Towards the identification and quantification of candidate metabolites of tebuconazole fungicide.

    Science.gov (United States)

    El Azhari, Najoi; Dermou, Eftychia; Botteri, Lucio; Lucini, Luigi; Karas, Panagiotis; Karpouzas, Dimitris; Tsiamis, George; Martin-Laurent, Fabrice; Trevisan, Marco; Rossi, Riccardo; Ferrari, Federico

    2017-04-01

    Tebuconazole belongs to the family of triazole fungicides, used for crop protection and human health applications. In the environment, the dissipation of the parent molecule leads to the formation of metabolites that are of unknown identity or toxicity. In order to identify and determine the putative identity of those metabolites and their po- tential toxicity, a quadrupole time-of-flight (Q-TOF) approach is often used. Q-SAR ap- proaches help to predict their toxicity by comparing them to a known database of mole- cules with known properties. All together the information on the candidate by-products may help to select relevant sub-set of metabolites for further quantification by LC or GC coupled with MS. It is thereby possible to select putative toxic compounds for further quanti- fication using chemical analysis. Previous work allowed the identification of potential metabolites of tebuconazole. Triazole, triazolyl acetic acid and p-chlorophenol were suspected to result from the decomposition of tebuconazole. Tebuconazole degradation kinetics was followed for 125 days by quanti- fying the dissipation of the parent molecule and the emergence of the three candidate metabolites by LC/MS for tebuconazole, triazol and triazolyl acetate and by GC/MS for p- chlorophenol. The data allowed the proposition of several metabolic pathways.

  2. Reduced Fungicide Dose in Cereals

    DEFF Research Database (Denmark)

    Jørgensen, Lise Nistrup; Ørum, Jens Erik

    2017-01-01

    Often the fungicide rates that European farmers apply are lower than the labelled rates. The use of ‘adjusted appropriate rates’ is mainly driven by results from field trials showing sufficient control and better net yield responses compared to full rates. The optimal rate depends on several fact...

  3. Reduced fungicide dose in cereals

    DEFF Research Database (Denmark)

    Jørgensen, Lise Nistrup; Ørum, Jens Erik

    2017-01-01

    Often the fungicide rates that European farmers apply are lower than the labelled rates. The use of ‘adjusted appropriate rates’ is mainly driven by results from field trials showing sufficient control and better net yield responses compared to full rates. The optimal rate depends on several fact...

  4. FUNGICIDES IN SECOND HARVEST CORN: CERCOSPORIOSE CONTROL AND BLOTCH, PRODUCTIVITY, ECONOMIC RETURN AND GRAIN QUALITY

    Directory of Open Access Journals (Sweden)

    P. Rezende

    2017-10-01

    Full Text Available Os objetivos desse trabalho foram avaliar a eficiência de The aim of this study was evaluate efficacy fungicides to control cercospora leaf spot (Cercospora zeae-maydis and helminthosporium leaf blight (Exserohilumturcicum, productivity, economic returns and quality of grain of corn culture of second crop in Farm Bandeirantes at Feliz Natal/MT. The treatments evaluated were: pyraclostrobina+epoxiconazol (0,7 L ha-1, trifloxistrobina+protioconazol (0,3L ha-1, azoxistrobina+cyproconazol(0,3 L ha-1, azoxystrobina (0,25 L ha-1, trifloxistrobina+ciproconazol (0,2 L ha-1 and control. Theapplicationof products occurred when corn was with 55 days, with a high propelled sprayer. The experimental design was a randomized block, with 6 treatments and 3 replications. The severity of each disease was visually determined through periodic analyses and ten plants were marked in each repetition, which were evaluated during the entire crop cycle. The data of severity obtained were used to calculate the area under disease progress curve (AUDPC. It was also obtained the production per ha, the economic return (R$ ha-1 and physiological quality of grain was evaluated by germination tests and accelerated aging of the grains. All treatments had significant difference compared to the control sample in controlling cercospora leaf spot about the control of helminthosporiumleat blight, the fungicides trifloxystrobin+prothioconazol and trifloxystrobin+cyproconazol were not efficient, and the fungicides pyraclostrobina+epoxiconazol, azoxystrobina, azoxistrobina+cyproconazol were efficient. The treatments that had major production are from the group of triazoles+strobilurine and the fungicide pyraclostrobin+epoxyconazol showed greater economic viability. Not were differences among fungicides, and neither of the treatments compared to control, in germination and accelerated aging tests, showing that the grains have good quality characteristics

  5. Synthesis and Biological Activities of Some Novel (E-Alpha-(methoxyiminobenzeneacetate Derivatives with Modified 1,2,4-Triazole Moiety

    Directory of Open Access Journals (Sweden)

    Xianyou Wang

    2014-01-01

    Full Text Available To find new strobilurin analogues with high activity against resistant pathogens, a series of (E-α-(methoxyiminobenzeneacetate derivatives containing 1,2,4-triazole Schiff base side chain were designed and synthesized. Their structures were confirmed by IR, 1H NMR, and 13C NMR, ESI-HRMS, or elemental analyses. Bioassays indicated that most of the target compounds showed moderate to good fungicidal activities against Rhizoctonia solani, Botrytis cinerea Pers., Fusarium graminearum, Cotton rhizoctoniosis, and Blumeria graminis. For example, compounds 6g and 6j exhibited promising antifungal activity against Rhizoctonia solani, Botrytis cinerea Pers., and Fusarium graminearum. Compounds 6c, 6l, and 6m had higher fungicidal activities against Blumeria graminis at the concentration of 50 µg/mL; inhibitory rate is 91.41%, 92.13%, and 91.77%, respectively.

  6. Fenarimol, a Pyrimidine-Type Fungicide, Inhibits Brassinosteroid Biosynthesis

    Directory of Open Access Journals (Sweden)

    Keimei Oh

    2015-07-01

    Full Text Available The plant steroid hormone brassinosteroids (BRs are important signal mediators that regulate broad aspects of plant growth and development. With the discovery of brassinoazole (Brz, the first specific inhibitor of BR biosynthesis, several triazole-type BR biosynthesis inhibitors have been developed. In this article, we report that fenarimol (FM, a pyrimidine-type fungicide, exhibits potent inhibitory activity against BR biosynthesis. FM induces dwarfism and the open cotyledon phenotype of Arabidopsis seedlings in the dark. The IC50 value for FM to inhibit stem elongation of Arabidopsis seedlings grown in the dark was approximately 1.8 ± 0.2 μM. FM-induced dwarfism of Arabidopsis seedlings could be restored by brassinolide (BL but not by gibberellin (GA. Assessment of the target site of FM in BR biosynthesis by feeding BR biosynthesis intermediates indicated that FM interferes with the side chain hydroxylation of BR biosynthesis from campestanol to teasterone. Determination of the binding affinity of FM to purified recombinant CYP90D1 indicated that FM induced a typical type II binding spectrum with a Kd value of approximately 0.79 μM. Quantitative real-time PCR analysis of the expression level of the BR responsive gene in Arabidopsis seedlings indicated that FM induces the BR deficiency in Arabidopsis.

  7. Early life exposure to a rodent carcinogen propiconazole fungicide induces oxidative stress and hepatocarcinogenesis in medaka fish

    Energy Technology Data Exchange (ETDEWEB)

    Tu, Tzu-Yi; Hong, Chwan-Yang [Department of Agricultural Chemistry, College of Bio-Resources and Agriculture, National Taiwan University, Taipei, Taiwan (China); Sasado, Takao [Laboratory of Bioresources, National Institute for Basic Biology, Okazaki (Japan); Kashiwada, Shosaku [Research Center for Life and Environmental Sciences, Department of Life Sciences, the Toyo University, Gunma (Japan); Chen, Pei-Jen, E-mail: chenpj@ntu.edu.tw [Department of Agricultural Chemistry, College of Bio-Resources and Agriculture, National Taiwan University, Taipei, Taiwan (China)

    2016-01-15

    Highlights: • Propiconazole initiates ROS-induced oxidative stress and damage in medaka fish. • Early life exposure to propiconazole increases incidence of hepatocarcionogensis in p53{sup −/−} medaka. • Oxidative stress and CYP induction involved in p53 regulation are key events in propiconazole-induced hepatotumorigenesis. • Propiconazole-induced toxic response in medaka is compatible with that in rodents. - Abstract: Conazole pollution is an emerging concern to human health and environmental safety because of the broad use of conazole fungicides in agriculture and medicine and their frequent occurrence in aquifers. The agricultural pesticide propiconazole has received much regulatory interest because it is a known rodent carcinogen with evidence of multiple adverse effects in mammals and non-targeted organisms. However, the carcinogenic effect and associated mechanism of propiconazole in fish under microgram-per-liter levels of environmental-relevant exposure remains unclear. To explore whether early life of propiconzaole exposure would induce oxidative stress and latent carcinogenic effects in fish, we continuously exposed larvae of wild type or p53{sup −/−} mutant of medaka fish (Oryzias latipes) to propiconazole (2.5–250 μg/L) for 3, 7, 14 or 28 days and assessed liver histopathology and/or the oxidative stress response and gene expression during exposure and throughout adulthood. Propiconazole dose-dependently induced reactive oxygen species (ROS) level, altered homeostasis of antioxidant superoxide dismutase, catalase and glutathione S-transferase and caused lipid and protein peroxidation during early life exposure in wild type medaka. Such exposure also significantly upregulated gene expression of the cytochrome P450 CYP1A, but marginally suppressed that of tumor suppressor p53 in adults. Furthermore, histopathology revealed that p53{sup −/−} mutant medaka with early life exposure to propiconazole showed increased incidence of

  8. Fungicide impacts on photosynthesis in crop plants.

    Science.gov (United States)

    Petit, Anne-Noëlle; Fontaine, Florence; Vatsa, Parul; Clément, Christophe; Vaillant-Gaveau, Nathalie

    2012-03-01

    Fungicides are widely used to control pests in crop plants. However, it has been reported that these pesticides may have negative effects on crop physiology, especially on photosynthesis. An alteration in photosynthesis might lead to a reduction in photoassimilate production, resulting in a decrease in both growth and yield of crop plants. For example, a contact fungicide such as copper inhibits photosynthesis by destroying chloroplasts, affecting photosystem II activity and chlorophyll biosynthesis. Systemic fungicides such as benzimidazoles, anilides, and pyrimidine are also phytotoxic, whereas azoles stimulate photosynthesis. This article focuses on the available information about toxic effects of fungicides on photosynthesis in crop plants, highlighting the mechanisms of perturbation, interaction, and the target sites of different classes of fungicides. © Springer Science+Business Media B.V. 2012

  9. Endocrine-disrupting activities in vivo of the fungicides tebuconazole and epoxiconazole

    DEFF Research Database (Denmark)

    Taxvig, Camilla; Hass, Ulla; Petersen, Marta Axelstad

    2007-01-01

    The triazole fungicides tebuconazole and epoxiconazole were investigated for reproductive toxic effects after exposure during gestation and lactation. Rats were dosed with epoxiconazole (15 or 50 mg/kg bw/day) or tebuconazole (50 or 100 mg/kg bw/day) during pregnancy from gestational day (GD) 7...... 13 or PND 16, and semen quality was assessed in adults. Both tebuconazole and epoxiconazole affected reproductive development in the offspring after exposure in utero. Both compounds virilized the female offspring as shown by an increased AGD PND 0. Furthermore, tebuconazole had a feminizing effect...... on male offspring as shown by increased nipple retention. This effect was likely caused by the reduced testosterone levels seen in male fetuses. Tebuconazole increased the testicular concentrations of progesterone and 17 alpha-hydroxyprogesterone in male fetuses, indicating a direct impact on the steroid...

  10. Theoretical insight into the stabilization of triazole fungicides via their interactions with dications

    Czech Academy of Sciences Publication Activity Database

    Jaklová Dytrtová, Jana; Fanfrlík, Jindřich; Norková, Renáta; Jakl, M.; Hobza, Pavel

    2014-01-01

    Roč. 359, Feb 1 (2014), s. 38-43 ISSN 1387-3806 R&D Projects: GA ČR GP13-21409P; GA ČR GBP208/12/G016 Institutional support: RVO:61388963 Keywords : ESI-MS * DFT * tebuconazole * zinc * cadmium * complex Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 1.972, year: 2014

  11. BIOACCUMULATION AND BIOTRANSFORMATION OF CHIRAL TRIAZOLE FUNGICIDES IN RAINBOW TROUT (ONCORHYNCHUS MYKISS)

    Science.gov (United States)

    There are very little data on the bioaccumulation and biotransformation of current-use pesticides (CUPs) despite the fact that such data are critical in assessing their fate and potential toxic effects in aquatic organisms. To help address this issue, juvenile rainbow trout (Onco...

  12. Impact of fungicides on weed growth

    Directory of Open Access Journals (Sweden)

    Nordmeyer, Henning

    2014-02-01

    Full Text Available The study has shown that fungicides influence the growth of weeds. The competition against crops will be substantially reduced. Bioassays in a climate chamber variation in temperature as well as different lightning phases and microplot trials under semi field levels were carried out to investigate the influence of fungicides on weed growth. Selected weed species (Alopecurus myosuroides, Viola arvensis, Galium aparine, Stellaria media, Lamium purpureum have been examined with different dose rates of fungicides (Adexar, Bravo 500, Diamant, Crupozin flüssig. Weed species showed a different sensitivity. There were leaf discoloration, contractions and growth inhibition. In some cases using common practise dose rates of fungicides more than 70% growth inhibition could be estimated 14 days after application in comparison to the untreated control. Effects were much stronger in bioassays than in semi field trials.

  13. Identification of new metabolic pathways in the enantioselective fungicide tebuconazole biodegradation by Bacillus sp. 3B6.

    Science.gov (United States)

    Youness, Mohamed; Sancelme, Martine; Combourieu, Bruno; Besse-Hoggan, Pascale

    2018-02-24

    The use of triazole fungicides in various fields ranging from agriculture to therapy, can cause long-term undesirable effects on different organisms from various environmental compartments and lead to resistance phenomena (even in humans) due to their extensive use and persistence. Their occurrence in various water bodies has increased and tebuconazole, in particular, is often detected, sometimes in high concentration. Only a few bacterial and fungal strains have been isolated and found to biotransform this fungicide, described as not easily biodegradable. Nevertheless, the knowledge of efficient degrading-strains and metabolites potentially formed could improve bioremediation process and global overview of risk assessment. Therefore, a broad screening of microorganisms, isolated from various environmental compartments or from commercially-available strain collections, allowed us to find six bacterial strains able to biotransform tebuconazole. The most efficient one was studied further: this environmental strain Bacillus sp. 3B6 biotransforms the fungicide enantioselectively (ee = 18%) into two hydroxylated metabolites, one of them being transformed in its turn to alkene by a biotic dehydration reaction. This original enantioselective pathway shows that racemic pesticides should be treated by the environmental risk assessment authorities as a mixture of two compounds because persistence, biodegradation, bioaccumulation and toxicity often show chiral dependence. Copyright © 2018 Elsevier B.V. All rights reserved.

  14. Triazole resistance surveillance in Aspergillus fumigatus.

    Science.gov (United States)

    Resendiz Sharpe, Agustin; Lagrou, Katrien; Meis, Jacques F; Chowdhary, Anuradha; Lockhart, Shawn R; Verweij, Paul E

    2018-04-01

    Triazole resistance is an increasing concern in the opportunistic mold Aspergillus fumigatus. Resistance can develop through exposure to azole compounds during azole therapy or in the environment. Resistance mutations are commonly found in the Cyp51A-gene, although other known and unknown resistance mechanisms may be present. Surveillance studies show triazole resistance in six continents, although the presence of resistance remains unknown in many countries. In most countries, resistance mutations associated with the environment dominate, but it remains unclear if these resistance traits predominately migrate or arise locally. Patients with triazole-resistant aspergillus disease may fail to antifungal therapy, but only a limited number of cohort studies have been performed that show conflicting results. Treatment failure might be due to diagnostic delay or due to the limited number of alternative treatment options. The ISHAM/ECMM Aspergillus Resistance Surveillance working group was set up to facilitate surveillance studies and stimulate international collaborations. Important aims are to determine the resistance epidemiology in countries where this information is currently lacking, to gain more insight in the clinical implications of triazole resistance through a registry and to unify nomenclature through consensus definitions.

  15. Clonal expansion and emergence of environmental multiple-triazole-resistant Aspergillus fumigatus strains carrying the TR₃₄/L98H mutations in the cyp51A gene in India.

    Directory of Open Access Journals (Sweden)

    Anuradha Chowdhary

    Full Text Available Azole resistance is an emerging problem in Aspergillus which impacts the management of aspergillosis. Here in we report the emergence and clonal spread of resistance to triazoles in environmental Aspergillus fumigatus isolates in India. A total of 44 (7% A. fumigatus isolates from 24 environmental samples were found to be triazole resistant. The isolation rate of resistant A. fumigatus was highest (33% from soil of tea gardens followed by soil from flower pots of the hospital garden (20%, soil beneath cotton trees (20%, rice paddy fields (12.3%, air samples of hospital wards (7.6% and from soil admixed with bird droppings (3.8%. These strains showed cross-resistance to voriconazole, posaconazole, itraconazole and to six triazole fungicides used extensively in agriculture. Our analyses identified that all triazole-resistant strains from India shared the same TR(34/L98H mutation in the cyp51 gene. In contrast to the genetic uniformity of azole-resistant strains the azole-susceptible isolates from patients and environments in India were genetically very diverse. All nine loci were highly polymorphic in populations of azole-susceptible isolates from both clinical and environmental samples. Furthermore, all Indian environmental and clinical azole resistant isolates shared the same multilocus microsatellite genotype not found in any other analyzed samples, either from within India or from the Netherlands, France, Germany or China. Our population genetic analyses suggest that the Indian azole-resistant A. fumigatus genotype was likely an extremely adaptive recombinant progeny derived from a cross between an azole-resistant strain migrated from outside of India and a native azole-susceptible strain from within India, followed by mutation and then rapid dispersal through many parts of India. Our results are consistent with the hypothesis that exposure of A. fumigatus to azole fungicides in the environment causes cross-resistance to medical triazoles. The

  16. In vivo sensitivity reduction of Puccinia triticina races, causal agent of wheat leaf rust, to DMI and QoI fungicides

    Directory of Open Access Journals (Sweden)

    Gisele da Silva Arduim

    2012-12-01

    Full Text Available Experiments were carried out to determine in vivo the IC50 and the IC90 for demethylation-inhibitor fungicides (DMIs, triazoles and quinone outside inhibitors (QoIs, strobilurins to the five most frequent races of Puccinia triticina in 2007 growing season in Southern Brazil. The tests were done in a greenhouse with wheat seedlings. DMI fungicides were tested at the concentrations, in mg/L, 0.0; 0.02; 0.2; 2.0; 20.0; 100.0 and 200.0, and QoIs at the concentrations 0.0; 0.0001; 0.001; 0.01; 0.1; 1 and 10.0 mg of active ingredient/L water. Fungicides were preventively applied at 24 hours before the inoculation of seedlings with the fungal spores. The effect of treatments was assessed based on the number of uredia/cm². The lowest IC50 (inhibitory concentration for DMI fungicides determined for MCG-MN, sensitive race, ranged from 0.33 to 0.91 mg/L, while the highest values for MDP-MR, MDT-MR, MDK-MR, MFH-HT races, varied from 9.63 to 85.64 mg/L (suspected insensitivity. QoI fungicide presented an IC50 varying from 0.0018 to 0.14 mg/L. The sensitivity reduction factor for DMIs varied from 8.8 to 238.8, and for QoIs from 0.3 to 1.5 mg/L. Sensitivity reduction was confirmed for the races MDP-MR, MDT-MR, MDK-MR, MFH-HT to DMIs, as well as their sensitivity to QoI fungicides.

  17. Effect of fungicides on Wyoming big sagebrush seed germination

    Science.gov (United States)

    Robert D. Cox; Lance H. Kosberg; Nancy L. Shaw; Stuart P. Hardegree

    2011-01-01

    Germination tests of Wyoming big sagebrush (Artemisia tridentata Nutt. ssp. wyomingensis Beetle & Young [Asteraceae]) seeds often exhibit fungal contamination, but the use of fungicides should be avoided because fungicides may artificially inhibit germination. We tested the effect of seed-applied fungicides on germination of Wyoming big sagebrush at 2 different...

  18. Synthesis of (C-14-Triazol)-paclobutrazol

    International Nuclear Information System (INIS)

    Ji Guijun; Cao Guoyin

    1990-01-01

    1-p-chlorophenyl-2-(5-C-14)-1,2,4-triazol-1-yl-1, 4-dimethyl-pentan-3-01(Paclobutrazol) (1) was labelled by phase transfering method. The procedure involved the interaction of (5-C-14)-1,2,4-triazol with 1-chloropinacolone in ethyl acetate to produce (C-14)-triazotylpinacolone (2). Then, (C-14)-triazotylpinacolone was reacted with p-chlorobenzyl halide to produce (C-14)-triazolyl ketone in benzene (3), and finally (C-14)-triazolyl ketone was reduced by NaBH 4 in methanol to give C-14-Paclobutrazol. Chemical yield was 52%, radio-chemical yield was 20.9%. HPLC and TLC analysis of the final product in methanol solution showed the radiochemical purity to be not less than 99%

  19. A pesticide paradox: fungicides indirectly increase fungal infections.

    Science.gov (United States)

    Rohr, Jason R; Brown, Jenise; Battaglin, William A; McMahon, Taegan A; Relyea, Rick A

    2017-12-01

    There are many examples where the use of chemicals have had profound unintended consequences, such as fertilizers reducing crop yields (paradox of enrichment) and insecticides increasing insect pests (by reducing natural biocontrol). Recently, the application of agrochemicals, such as agricultural disinfectants and fungicides, has been explored as an approach to curb the pathogenic fungus, Batrachochytrium dendrobatidis (Bd), which is associated with worldwide amphibian declines. However, the long-term, net effects of early-life exposure to these chemicals on amphibian disease risk have not been thoroughly investigated. Using a combination of laboratory experiments and analysis of data from the literature, we explored the effects of fungicide exposure on Bd infections in two frog species. Extremely low concentrations of the fungicides azoxystrobin, chlorothalonil, and mancozeb were directly toxic to Bd in culture. However, estimated environmental concentrations of the fungicides did not reduce Bd on Cuban tree frog (Osteopilus septentrionalis) tadpoles exposed simultaneously to any of these fungicides and Bd, and fungicide exposure actually increased Bd-induced mortality. Additionally, exposure to any of these fungicides as tadpoles resulted in higher Bd abundance and greater Bd-induced mortality when challenged with Bd post-metamorphosis, an average of 71 d after their last fungicide exposure. Analysis of data from the literature revealed that previous exposure to the fungicide itraconazole, which is commonly used to clear Bd infections, made the critically endangered booroolong frog (Litoria booroolongensis) more susceptible to Bd. Finally, a field survey revealed that Bd prevalence was positively associated with concentrations of fungicides in ponds. Although fungicides show promise for controlling Bd, these results suggest that, if fungicides do not completely eliminate Bd or if Bd recolonizes, exposure to fungicides has the potential to do more harm than

  20. SYNTHESIS AND FUNGICIDAL ACTIVITY OF ACETYL ...

    African Journals Online (AJOL)

    a

    large varieties of new sulfur based crop protection chemicals in development around the world. [14, 15]. Methods ... sulfur fission viz, the resonance – stabilized benzyl (or isomeric tropylium) cation [19]. The elimination of ... two well – established fungicides so as to compare their activities with those of compounds 1(a. – d).

  1. Fungicide and insecticide residues in rice grains

    Directory of Open Access Journals (Sweden)

    Gustavo Mack Teló

    2017-01-01

    Full Text Available The objective of this study was to analyse residues of fungicides and insecticides in rice grains that were subjected to different forms of processing. Field work was conducted during three crop seasons, and fungicides and insecticides were applied at different crop growth stages on the aerial portion of the rice plants. Azoxystrobin, difenoconazole, propiconazole, tebuconazole, and trifloxystrobin fungicides were sprayed only once at the R2 growth stage or twice at the R2 and R4 growth stages; cypermethrin, lambda-cyhalothrin, permethrin, and thiamethoxam insecticides were sprayed at the R2 growth stage; and permethrin was sprayed at 5-day intervals from the R4 growth stage up to one day prior to harvest. Pesticide residues were analysed in uncooked, cooked, parboiled, polished and brown rice grains as well as rice hulls during the three crop seasons, for a total of 1458 samples. The samples were analysed by gas chromatography with electron capture detection (GC-ECD using modified QuEChERS as the extraction method. No fungicide or insecticide residues were detected in rice grain samples; however, azoxystrobin and cypermethrin residues were detected in rice hull samples.

  2. Screening Phytophthora rubi for fungicide resistance

    Science.gov (United States)

    Preliminary results from the survey for fungicide resistance in Phytophthora were reported at the 2016 Washington Small Fruit Conference. Phytophthora was isolated from diseased plants in 28 red raspberry fields and tested against mefenoxam, the active ingredient of Ridomil. Most isolates were ident...

  3. Design and selection of triazole-based compounds with high ...

    Indian Academy of Sciences (India)

    ... phase, energetic properties, and thermal stabilities of triazole derivatives. The results show that the properties are associated with the different substituents and substitution positions in the parent ring. The symmetric structures and hyperconjugation systems both contribute to the thermal stabilities of the triazole derivatives.

  4. Stereo- and regio-selective one-pot synthesis of triazole-based unnatural amino acids and β- amino triazoles

    Science.gov (United States)

    Synthesis of triazole based unnatural amino acids and β-amino triazole has been described via stereo and regioselective one-pot multi-component reaction of sulfamidates, sodium azide, and alkynes under MW conditions. The developed method is applicable to a broad substrate scope a...

  5. 1,2,3-Triazole and its derivatives. Development of methods for the formation of the triazole ring

    International Nuclear Information System (INIS)

    Krivopalov, Victor P; Shkurko, Oleg P

    2005-01-01

    Data on the synthetic routes to substituted 1,2,3-triazoles, including those containing functional groups, based on cyclisation of various nitrogen compounds published during the last 15 years are described. Examples of using new triazole derivatives in agrochemistry, medicine and engineering are given.

  6. Prevalence and mechanism of triazole resistance in Aspergillus fumigatus in a referral chest hospital in Delhi, India and an update of the situation in Asia

    Directory of Open Access Journals (Sweden)

    Anuradha eChowdhary

    2015-05-01

    Full Text Available Aspergillus fumigatus causes varied clinical syndromes ranging from colonization to deep infections. The mainstay of therapy of Aspergillus diseases is triazoles but several studies globally highlighted variable prevalence of triazole resistance, which hampers the management of aspergillosis. We studied the prevalence of resistance in clinical A. fumigatus isolates during 4 years in a referral Chest Hospital in Delhi, India and reviewed the scenario in Asia and the Middle East. Aspergillus species (n=2117 were screened with selective plates for azole resistance. The isolates included 45.4% A. flavus, followed by 32.4% A. fumigatus, 15.6% Aspergillus species and 6.6% A. terreus. Azole resistance was found in only 12 (1.7% A. fumigatus isolates.These triazole resistant A. fumigatus (TRAF isolates were subjected to (a calmodulin and β tubulin gene sequencing (b in vitro antifungal susceptibility testing against triazoles using CLSI M38-A2 (c sequencing of cyp51A gene and real-time PCR assay for detection of mutations and (d microsatellite typing of the resistant isolates. TRAF harbored TR34/L98H mutation in 10 (83.3% isolates with a pan-azole resistant phenotype. Among the remaining 2 TRAF isolates, one had G54E and the other had three non-synonymous point mutations. The majority of patients were diagnosed as invasive aspergillosis followed by allergic bronchopulmonary aspergillosis and chronic pulmonary aspergillosis. The Indian TR34/L98H isolates had a unique genotype and were distinct from the Chinese, Middle East and European TR34/L98H strains. This resistance mechanism has been linked to the use of fungicide azoles in agricultural practices in Europe as it has been mainly reported from azole naïve patients. Reports published from Asia demonstrate the same environmental resistance mechanism in A. fumigatus isolates from two highly populated countries in Asia i.e., China and India and also from the neighboring Middle East.

  7. Rust Inhibitor And Fungicide For Cooling Systems

    Science.gov (United States)

    Adams, James F.; Greer, D. Clay

    1988-01-01

    Mixture of benzotriazole, benzoic acid, and fungicide prevents growth of rust and fungus. Water-based cooling mixture made from readily available materials prevents formation of metallic oxides and growth of fungi in metallic pipes. Coolant remains clear and does not develop thick sludge tending to collect in low points in cooling systems with many commercial rust inhibitors. Coolant compatible with iron, copper, aluminum, and stainless steel. Cannot be used with cadmium or cadmium-plated pipes.

  8. Bibliometric analysis of literature on antifungal triazole resistance: 1980 - 2015.

    Science.gov (United States)

    Sweileh, Waleed M; Sawalha, Ansam F; Al-Jabi, Samah; Zyoud, Sa'ed H

    2017-03-01

    Triazole antifungal agents play an important role in the treatment of a wide range of fungal infections. Little is known about antifungal triazole drug resistance when compared to antibiotic resistance. Therefore, this study was carried out to give a bibliometric overview of literature on triazole antifungal drug resistance. Keywords related to triazole drug class and resistance were used in a search query in the Scopus search engine. The time span was set from 1980 to 2015. Data pertaining to growth of publications, the most active countries and institutions, the most cited articles, and mapping of molecular mechanisms of resistance were analyzed. A total of 1648 journal articles were retrieved with an average of 20.46 citations per article. Annual growth of triazole resistance showed an increasing pattern during the study period. The United States of America (n=446; 27.06%) ranked first in productivity followed by the United Kingdom (UK) (n=176; 10.68%), and China (n=133; 8.07%). Radboud University Nijmegen Medical Centre (n=69, 4.19%) in the Netherlands ranked first in productivity, while the journal Antimicrobial Agents and Chemotherapy ranked first (n=255; 15.47%) in publishing articles on triazole resistance. Mapping mechanisms of resistance showed that efflux pump and mutations in target enzyme are major mechanisms described in resistance to triazoles. There was a growth of publications on triazole resistance in the past two decades with the bulk of publications on triazole resistance in Candida species. The data presented here will serve as baseline information for future comparative purposes.

  9. A novel triazole-based fluorescent chemosensor for Zinc ions

    International Nuclear Information System (INIS)

    Gusev, Alexey N.; Shul’gin, Victor F.; Meshkova, Svetlana B.; Smola, Sergey S.; Linert, Wolfgang

    2014-01-01

    This work describes the preparation of novel triazole-based heterocycles and their properties concerning UV–vis absorption and fluorescence emission with and without the presence of metal ions. It is shown that this compound can be used to determine Zn 2+ ion with high selectivity. Therefore, the new compounds are recommended as possible species for the development of new fluorescent probes for the detection of Zn 2+ cation. - Highlights: • Luminescence spectra of Zn(III) complex using triazole ligands were characterized. • New Triazole based ligands exhibiting fluorescence are reported. • Selectivity concerning Zn-ions is established

  10. Inhibition of copper dissolution in water solutions of triazoles

    Science.gov (United States)

    Kuznetsov, Yu. I.; Agafonkina, M. O.; Andreeva, N. P.

    2014-04-01

    The influence of the chemical structure of certain triazoles on the inhibition of copper dissolution in water solutions at pH 7.40 is studied by electrochemical and ellispometric means. It is established that adsorption of the studied triazoles on copper at potential E = 0.0 V relative to a normal hydrogen electrode is polymolecular, the first layer is described by the Frumkin equation with values of the free adsorption of energy values (-Δ G {a/0}) = 50.5-70.1 kJ/mol. In addition, possible orientations of triazole molecules with respect to a surface of oxidized copper are revealed.

  11. A novel triazole-based fluorescent chemosensor for Zinc ions

    Energy Technology Data Exchange (ETDEWEB)

    Gusev, Alexey N., E-mail: galex0330@gmail.com [Taurida National V.I. Vernadsky University, Simferopol 295007 (Russian Federation); Shul’gin, Victor F. [Taurida National V.I. Vernadsky University, Simferopol 295007 (Russian Federation); Meshkova, Svetlana B.; Smola, Sergey S. [A.V. Bogatsky Physico-chemical Institute of the National Academy of Sciences of Ukraine, Odessa 65080 Ukraine (Ukraine); Linert, Wolfgang, E-mail: wolfgang.linert@tuwien.ac.at [Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163, A-1060 Vienna (Austria)

    2014-11-15

    This work describes the preparation of novel triazole-based heterocycles and their properties concerning UV–vis absorption and fluorescence emission with and without the presence of metal ions. It is shown that this compound can be used to determine Zn{sup 2+} ion with high selectivity. Therefore, the new compounds are recommended as possible species for the development of new fluorescent probes for the detection of Zn{sup 2+}cation. - Highlights: • Luminescence spectra of Zn(III) complex using triazole ligands were characterized. • New Triazole based ligands exhibiting fluorescence are reported. • Selectivity concerning Zn-ions is established.

  12. Alternative fungicides for the leather industry: application in various processes

    OpenAIRE

    Cuadros Domènech, Sara; Manresa Presas, Mª Angels; Font Vallès, Joaquim; Puig Vidal, Rita; Marsal Monge, Agustí

    2012-01-01

    Increasingly stringent environmental legislation and indispensable use of fungicides in the tanning industry obliges tanners to adapt their processes to alternative technologies with lower environmental impact, including the search for new fungicide systems that comply with those rules. The fungicidal capacities of alternative compounds diiodomethyl p-tolylsulfone (DIMPTS), 3-iodo- 2-propynyl N-butylcarbamate (IPBC) and thiabendazole / 2-thiazol-4-yl-1H-benzo imidazole(TBZ) were compared t...

  13. How Biotransformation Influences Toxicokinetics of Azole Fungicides in the Aquatic Invertebrate Gammarus pulex.

    Science.gov (United States)

    Rösch, Andrea; Anliker, Sabine; Hollender, Juliane

    2016-07-05

    Biotransformation is a key process that can greatly influence the bioaccumulation potential and toxicity of organic compounds. In this study, biotransformation of seven frequently used azole fungicides (triazoles: cyproconazole, epoxiconazole, fluconazole, propiconazole, tebuconazole and imidazoles: ketoconazole, prochloraz) was investigated in the aquatic invertebrate Gammarus pulex in a 24 h exposure experiment. Additionally, temporal trends of the whole body internal concentrations of epoxiconazole, prochloraz, and their respective biotransformation products (BTPs) were studied to gain insight into toxicokinetic processes such as uptake, elimination and biotransformation. By the use of high resolution tandem mass spectrometry in total 37 BTPs were identified. Between one (ketoconazole) and six (epoxiconazole) BTPs were identified per parent compound except for prochloraz, which showed extensive biotransformation reactions with 18 BTPs detected that were mainly formed through ring cleavage or ring loss. In general, most BTPs were formed by oxidation and conjugation reactions. Ring loss or ring cleavage was only observed for the imidazoles as expected from the general mechanism of oxidative ring openings of imidazoles, likely affecting the bioactivity of these BTPs. Overall, internal concentrations of BTPs were up to 3 orders of magnitude lower than that of the corresponding parent compound. Thus, biotransformation did not dominate toxicokinetics and only played a minor role in elimination of the respective parent compound, with the exception of prochloraz.

  14. Acute toxicity and bioconcentration of fungicide tebuconazole in zebrafish (Danio rerio).

    Science.gov (United States)

    Andreu-Sánchez, Oscar; Paraíba, Lourival C; Jonsson, Claudio M; Carrasco, José M

    2012-02-01

    This research work investigated the bioconcentration of tebuconazole [(±)-α-[2-(4-chlorophenyl)ethyl]-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol] fungicide in zebrafish (Danio rerio) under laboratory conditions and a first-order kinetic pesticide dissipation in the water. The concentrations of tebuconazole fitted to an equivalent nonlinear kinetic type model which allowed the calculation of the following parameters: bioconcentration factor (38.80 L kg(-1) ), time to reach maximum fish concentration (6 days), maximum concentration in fish (0.0075 μg mg(-1) ), half-life in fish (24 days) and time needed for the fish to eliminate 95% of the maximum concentration (105 days). These calculations permitted the establishment of theoretical reference limit values for human consumption of fish and the establishment of safe limits for the water pesticide concentration. The data would also be useful in safe strategies associated with fishery activities that are conducted in aquatic regions close to crops using tebuconazole. The information will contribute to enlarge the tebuconazole toxicokinetics database of aquatic organisms. Copyright © 2011 Wiley Periodicals, Inc.

  15. Recent Trends in Studies on Botanical Fungicides in Agriculture

    Directory of Open Access Journals (Sweden)

    Mi-Young Yoon

    2013-03-01

    Full Text Available Plants are attacked by various phytopathogenic fungi. For many years, synthetic fungicides have been used to control plant diseases. Although synthetic fungicides are highly effective, their repeated use has led to problems such as environmental pollution, development of resistance, and residual toxicity. This has prompted intensive research on the development of biopesticides, including botanical fungicides. To date, relatively few botanical fungicides have been registered and commercialized. However, many scientists have reported isolation and characterization of a variety of antifungal plant derivatives. Here, we present a survey of a wide range of reported plant-derived antifungal metabolites.

  16. Triazoles: a valuable insight into recent developments and biological activities.

    Science.gov (United States)

    Sahu, Jagdish K; Ganguly, Swastika; Kaushik, Atul

    2013-09-01

    In recent years, heterocyclic compounds, analogs, and derivatives have attracted strong interest due to their useful biological and pharmacological properties. The small and simple triazole nucleus is present in compounds aimed at evaluating new entities that possess anti-microbial, anti-tumor, antitubercular, anti-convulsant, anti-depressant, antimalarial, and anti-inflammatory activities. Triazoles display a broad range of biological activities and are found in many potent, biologically active compounds, such as trazodone (antidepressant drug), rizatriptan (antimigrane drug), hexaconazole (antifungal drug) and alprazolam (hyptonic, sedative and tranquilizer drug). So far, modifications of the triazole ring have proven highly effective with improved potency and lesser toxicity. The present review highlights the recently synthesized triazoles possessing important biological activities. Copyright © 2013 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.

  17. Design, synthesis, in silico and in vitro antimicrobial screenings of novel 1,2,4-triazoles carrying 1,2,3-triazole scaffold with lipophilic side chain tether

    OpenAIRE

    Aouad, Mohamed Reda; Mayaba, Mariem Mohammed; Naqvi, Arshi; Bardaweel, Sanaa K.; Al-blewi, Fawzia Faleh; Messali, Mouslim; Rezki, Nadjet

    2017-01-01

    Background 1,2,4-Triazoles and 1,2,3-triazoles have gained significant importance in medicinal chemistry. Results This study describes a green, efficient and quick solvent free click synthesis of new 1,2,3-triazole-4,5-diesters carrying a lipophilic side chain via 1,3-dipolar cycloaddition of diethylacetylene dicarboxylate with different surfactant azides. Further structural modifications of the resulting 1,2,3-triazole diesters to their corresponding 1,2,4-triazole-3-thiones via multi-step s...

  18. Animal Models for Studying Triazole Resistance in Aspergillus fumigatus.

    Science.gov (United States)

    Lewis, Russell E; Verweij, Paul E

    2017-08-15

    Infections caused by triazole-resistant Aspergillus fumigatus are associated with a higher probability of treatment failure and mortality. Because clinical experience in managing these infections is still limited, mouse models of invasive aspergillosis fulfill a critical void for studying treatment regimens designed to overcome resistance. The type of immunosuppression, the route of infection, the timing of antifungal administration, and the end points used to assess antifungal activity affect the interpretation of data from these models. Nevertheless, these models provide important insights that help guide treatment decisions in patients with triazole-resistant invasive aspergillosis. Animal models confirmed that a high triazole minimal inhibitory concentration corresponded with triazole treatment failure and that the efficacy of other classes of drugs, such as the polyenes and echinocandins, was not affected by the presence of triazole resistance mutations. Furthermore, the feasibility of triazole dose escalation, combination therapy, and prophylaxis were explored as strategies to overcome resistance. © The Author 2017. Published by Oxford University Press for the Infectious Diseases Society of America. All rights reserved. For permissions, e-mail: journals.permissions@oup.com.

  19. Development of biodegradable fungicide by radiation

    International Nuclear Information System (INIS)

    Lee, Young Jeun; Kim, Dong Sub

    2010-01-01

    To develop the fungicide which is biodegradable and alternative to chemical pesticide that has an side effect of environmental pollution, Mutant induction of the enhanced antifungal activity was studied by using radiation. Characteristics and structure of antifungal biomaterials derived from these mutants were analysed. Sixteen antifungal microbes were isolated and 4 antifungal activity enhanced mutants were induced by using radiation. P. lentimorbus WJ5a17 had 41% higher antifungal activity than the wild type. Two biomaterials related to the antifungal activity from the above mutant were isolated and purified

  20. Development of biodegradable fungicide by radiation

    International Nuclear Information System (INIS)

    Lee, Young Keun; Kim, Dong Sub

    2011-01-01

    To develop the fungicide which is biodegradable and alternative to chemical pesticide that has an side effect of environmental pollution, Mutant induction of the enhanced antifungal activity was studied by using radiation. Characteristics and structure of antifungal biomaterials derived from these mutants were analysed. Two biomaterials related to the antifungal activity from the above mutant were isolated and purified. Microbial pesticide were manufactured in combination of various additives. Antiphytopathogenic effects were proven by pot experiment and It was promising to prevent pepper, Chinese cabbage and radish from anthrax, phytophthora and root rot

  1. Development of biodegradable fungicide by radiation

    International Nuclear Information System (INIS)

    Lee, Youngkeun; Kim, Dongsub

    2012-03-01

    To develop the fungicide which is biodegradable and alternative to chemical pesticide that has an side effect of environmental pollution, Mutant induction of the enhanced antifungal activity was studied by using radiation. Characteristics and structure of antifungal biomaterials derived from these mutants were analysed. Two biomaterials related to the antifungal activity from the above mutant were isolated and purified. Microbial pesticide were manufactured in combination of various additives. Antiphytopathogenic effects were proven by field test and it was promising to prevent Chinese cabbage and radish from phytophthora and root rot

  2. Development of biodegradable fungicide by radiation

    Energy Technology Data Exchange (ETDEWEB)

    Lee, Young Keun; Kim, Dong Sub [KAERI, Daejeon (Korea, Republic of)

    2011-01-15

    To develop the fungicide which is biodegradable and alternative to chemical pesticide that has an side effect of environmental pollution, Mutant induction of the enhanced antifungal activity was studied by using radiation. Characteristics and structure of antifungal biomaterials derived from these mutants were analysed. Two biomaterials related to the antifungal activity from the above mutant were isolated and purified. Microbial pesticide were manufactured in combination of various additives. Antiphytopathogenic effects were proven by pot experiment and It was promising to prevent pepper, Chinese cabbage and radish from anthrax, phytophthora and root rot

  3. Development of biodegradable fungicide by radiation

    Energy Technology Data Exchange (ETDEWEB)

    Lee, Youngkeun; Kim, Dongsub

    2012-03-15

    To develop the fungicide which is biodegradable and alternative to chemical pesticide that has an side effect of environmental pollution, Mutant induction of the enhanced antifungal activity was studied by using radiation. Characteristics and structure of antifungal biomaterials derived from these mutants were analysed. Two biomaterials related to the antifungal activity from the above mutant were isolated and purified. Microbial pesticide were manufactured in combination of various additives. Antiphytopathogenic effects were proven by field test and it was promising to prevent Chinese cabbage and radish from phytophthora and root rot.

  4. Oxidation of 3-amino-1,2,3-triazoles to 3-nitro-1,2,4-triazoles by sodium perborate

    International Nuclear Information System (INIS)

    Tolstyakov, V.V.; Pevzner, M.S.

    1997-01-01

    Practicability of sodium perborate application for oxidizing certain 3(5)-amino-1,2,4-triazoles into the revelant nitrocompounds has been studied. It is shown that the use of sodium perborate-glacial acetic acid mixture permits preparing 3-nitro-1,2,4-triazoles, however, stricter oxidation conditions are required (great excess of oxidant, higher temperature) than in case of benzene series compounds case of benzene series compounds

  5. Palladium-Catalyzed C-H Arylation of 1,2,3-Triazoles.

    Science.gov (United States)

    Zhang, Chengwei; You, Lin; Chen, Chuo

    2016-09-22

    Palladium(II) acetate, in combination with triphenylphosphine, catalyzes direct arylation of 1,4-disubstituted 1,2,3-triazoles effectively. This C-H arylation reaction provides facile access to fully substituted triazoles with well-defined regiochemistry.

  6. In vitro screening of fungicides and antagonists against Sclerotium ...

    African Journals Online (AJOL)

    A study was conducted in the microbiology laboratory of Plant Pathology Department, Bangabandhu Sheikh Mujibur Rahman Agricultural University, Gazipur, during 2010 to 2011 to control Sclerotium rolfsii with fungicides and Trichoderma harzianum. Six fungicides namely Provax-200, Bavistin, Ridomil, Dithane M-45, ...

  7. Coating with fungicide and different doses of fertilizer in vinhatico ...

    African Journals Online (AJOL)

    Thus, the aim of this study was to evaluate and identify the physical and physiological quality of mahogany seeds that are coated with fertilizer and fungicide. The treatments were: seed coating with sand + lime + fungicide with different doses of fertilizers. The seeds were evaluated in the laboratory and in a greenhouse.

  8. A model for fungicide applications in winter wheat

    DEFF Research Database (Denmark)

    Ørum, Jens Erik; Pinnschmidt, Hans; Jørgensen, Lise Nistrup

    2006-01-01

    A statistical prediction of the opitamal fungicide dose and strategy based on expert knowledge and 5 yers' trial data from Denmark......A statistical prediction of the opitamal fungicide dose and strategy based on expert knowledge and 5 yers' trial data from Denmark...

  9. Detoxification of copper fungicide using EDTA-modified cellulosic ...

    African Journals Online (AJOL)

    Pesticides are poisons and can be particularly dangerous when misused or carelessly disposed. The detoxification of a copper fungicide (KOCIDE 101) using maize cob, a cellulosic material, was studied. Based on copper as the active agent (after a sorption period of 1 h), the concentration of the fungicide reduced from an ...

  10. Export papaya post-harvest protection by fungicides and the ...

    African Journals Online (AJOL)

    Thiabendazole-treated fruits did not rot 21 days after treatment and this fungicide was the most satisfactory with detected residues lower than the European Union's 2000/48/EC guideline. Key Words: Post-harvest, papaya, fungicides, phytotoxic, thiabendazole, residues maximal limit. African Journal of Biotechnology ...

  11. Oral Toxicity of Agro-Fungicides: Tilt (Propiconazole), Bayleton ...

    African Journals Online (AJOL)

    Introduction: The hazard use of pesticides, emergence of many diseases with high prevalence e.g (cancer, kidney failure and hepatic problems) urged the need for research on fungicides which are continuously received by human in Sudan via fruit and vegetables. Objective: To detect the toxicity of these fungicides in ...

  12. Sensitivity of Colletotrichum acutatum Isolates to Selected Fungicides

    Directory of Open Access Journals (Sweden)

    Barbora Jílková

    2015-01-01

    Full Text Available Laboratory tests of six isolates of the pathogen Colletotrichum acutatum from different host plants demonstrated the varying sensitivity of pathogen with regard to mycelium growth and conidial germination after treatment with seven fungicides containing various active ingredients. None of the evaluated isolates was tolerant to the selected active ingredients in the fungicides. In tests of mycelium growth sensitivity, isolates from lupin and strawberry were most frequently identified as the most sensitive of all evaluated fungicides. The safflower isolate, on the other hand, most frequently exhibited the lowest reaction to fungicides. Differences in conidial germination of individual isolates were not detected in fungicides with the active ingredients dithianon, folpet and mancozeb, for which inhibition reached 100% in almost all isolates. The most significant differences in sensitivity among individual isolates were recorded in fungicides with the active ingredients azoxystrobin and metiram. In the case of the fungicide with active ingredient azoxystrobin, the highest inhibitory effect was achieved in the safflower isolate and the lowest in the white lupin isolate. After treatment with the fungicide with active ingredient metiram, the lowest germination rate was recorded in isolates from safflower and strawberry and the highest in isolates from hypericum and lupin.

  13. Pathogenicity and fungicide sensitivity of the causal agent of ...

    African Journals Online (AJOL)

    The pathogenicity of the fungus and its cross-infection potential were determined on mango, avocado, papaya and banana fruits. The sensitivity of the pathogen to fungicides was determined by assessing radial mycelial growth on potato dextrose agar (PDA) amended with nine different fungicides (Bendazim, Funguran, ...

  14. Human lysozyme has fungicidal activity against nasal fungi.

    Science.gov (United States)

    Woods, Charmaine M; Hooper, David N; Ooi, Eng H; Tan, Lor-Wai; Carney, A Simon

    2011-01-01

    The cationic antimicrobial peptide lysozyme is the most prevalent innate immune protein in nasal secretions but there is a paucity of research regarding its role in paranasal sinus disease. Lysozyme is generally regarded as an antibacterial agent; however, some data suggest activity toward yeast. This study was designed to determine if lysozyme displays fungicidal activity toward fungi commonly identified in patients with chronic rhinosinusitis (CRS) or fungal sinusitis. Using a colony-forming unit assay the fungicidal activity of lysozyme (0, 0.5, 5, and 50 micromolar; 0- to 7-hour treatment) was tested against strains of Aspergillus fumigatus, the yeast Candida albicans, and other fungi commonly identified in mucin of patients with CRS. Fungi cultured directly from the mucin of two CRS patients were also tested to determine if they were resistant to the fungicidal activity of lysozyme. The fungicidal effect of lysozyme was both concentration and time dependent. After 7-hour treatment lysozyme (5 micromolar) had >80% fungicidal activity against A. fumigatus, Penicillium sp., Acremonium sp., C. albicans, and Candida parapsilosis. The fungicidal activity of lysozyme toward Alternaria alternata could not be determined. Lysozyme was also fungicidal toward the clinical isolates A. fumigatus and Aspergillus terreus cultured from the mucin of CRS patients. Lysozyme displays fungicidal activity toward many fungi commonly identified in patients with CRS, as well as clinical fungi isolates cultured from the mucin of CRS patients. Additional studies are required to determine the regulation of lysozyme in CRS.

  15. Protective, curative and eradicative activities of fungicides against grapevine rust

    Directory of Open Access Journals (Sweden)

    Francislene Angelotti

    2014-01-01

    Full Text Available The protective, eradicative and curative activities of the fungicides azoxystrobin, tebuconazole, pyraclostrobin+metiram, and ciproconazole against grapevine rust, were determined in greenhouse. To evaluate the protective activity, leaves of potted ´Niagara´ (Vitis labrusca vines were artificially inoculated with an urediniospore suspension of Phakopsora euvitis four, eight or forteen days after fungicidal spray; and to evaluate the curative and eradicative activities, leaves were sprayed with fungicides two, four or eight days after inoculation. Disease severity was assessed 14 days after each inoculation. All tested fungicides present excellent preventive activity against grapevine rust; however, tebuconazole and ciproconazole provide better curative activity than azoxystrobin and pyraclostrobin+metiram. It was observed also that all tested fungicides significantly reduced the germination of urediniospore produced on sprayed leaves.

  16. Effect of gamma radiation on ''in vitro''' efficiency of fungicides

    International Nuclear Information System (INIS)

    Menten, J.O.M.; Oliveira, G.C.X.

    1984-01-01

    The activity of 60 Co gamma radiation on eight fungicides used in post-harvesting treatment of agricultural products, was studied. Rhizoctonia solani was used in biological test as indicator-fungus. The fungicides were submitted to gamma radiation doses of O (control), 1, 10, 100, 1000 and 10.000 kR, samples of the fungicides were added to the PSA culture media to obtain 0, 1, 10 and 100 ppm concentrations of the active component of each product and of each radiation dose. The ED 50 (concentration of fungicide necessary to cause 50% radial reduction of the fungic mycelium) of each fungicide in the different gamma radiation doses was determined. (M.A.C.) [pt

  17. Facile synthesis and stereo-resolution of chiral 1,2,3-triazoles.

    Science.gov (United States)

    Shi, Ye; Ye, Xiaohan; Gu, Qiang; Shi, Xiaodong; Song, Zhiguang

    2015-05-21

    We describe herein the first facile synthesis of chiral triazoles through side chain functionalization. Readily available C-vinyl triazoles were used as starting materials, followed by sequential epoxidation, rearrangement and reduction to give the corresponding hydroxyl-triazoles. The CalB lipase catalyzed kinetic resolution gave enantiomerically pure (>99% ee) chiral triazoles in excellent yield. These new chiral TAs were also successfully applied as ligands in asymmetric addition of diethylzinc to aldehydes.

  18. Enantioselective determination of triazole fungicide tebuconazole in vegetables, fruits, soil and water by chiral liquid chromatography/tandem mass spectrometry.

    Science.gov (United States)

    Li, Yuanbo; Dong, Fengshou; Liu, Xingang; Xu, Jun; Li, Jing; Kong, Zhiqiang; Chen, Xiu; Zheng, Yongquan

    2012-01-01

    A novel and sensitive method was developed for the determination of tebuconazole enantioselectively using reversed-phase LC-MS/MS. The separation and determination were performed using on an amylose-based chiral stationary phase, a Lux 3u Amylose-2 column (150 mm×2.0 mm), under isocratic conditions at 0.3 mL/min flow rate. A series of chiral stationary phases were investigated and the effect of mobile phase composition on the enantioseparation was discussed. Parameters including the matrix effect, linearity, precision, accuracy and stability were evaluated. Under optimal conditions, the overall mean recoveries for two enantiomers from the soil, tomato, cucumber, pear and apple samples were 79.3-101.1% with 2.8-11.5% intra-day relative standard deviations (RSDs) and 4.1-8.6% inter-day RSDs at 5, 25 and 50 μg/kg levels; the mean enantiomer recoveries from the water samples were 89.6-101.9% with 3.3-10.2% intra-day RSDs and 5.1-7.7% inter-day RSDs at 0.25, 0.5 and 2.5 μg/kg levels. The limits of detection (LODs) for all enantiomers in tomato, cucumber, pear, apple, soil and water were less than 0.6 μg/kg, whereas the limit of quantification (LOQ) did not exceed 2.0 μg/kg. The results indicate that this proposed method is convenient and reliable for the enantioselective determination of tebuconazole enantiomers in foods and environment samples. Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim.

  19. Selective solid-phase extraction based on molecularly imprinted technology for the simultaneous determination of 20 triazole pesticides in cucumber samples using high-performance liquid chromatography-tandem mass spectrometry.

    Science.gov (United States)

    Zhao, Fengnian; She, Yongxin; Zhang, Chao; Cao, Xiaolin; Wang, Shanshan; Zheng, Lufei; Jin, Maojun; Shao, Hua; Jin, Fen; Wang, Jing

    2017-10-01

    A selective analytical method for the simultaneous determination of 20 triazole fungicides and plant growth regulators in cucumber samples was developed using solid-phase extraction with specific molecularly imprinted polymers (MIPs) as adsorbents. The MIPs were successfully prepared by precipitation polymerization using triadimefon as the template molecule, methacrylic acid as the functional monomer, trimethylolpropane trimethacrylate as the crosslinker, and acetonitrile as the porogen. The performance and recognition mechanism for both the MIPs and non-molecularly imprinted polymers were evaluated using adsorption isotherms and adsorption kinetics. Liquid chromatography-tandem quadrupole mass spectrometry was used to identify and quantify the target analytes. The solid-phase extraction using the MIPs was rapid, convenient, and efficient for extraction and enrichment of the 20 triazole pesticides from cucumber samples. The recoveries obtained at three concentration levels (1, 2, and 10μgL -1 ) ranged from 82.3% to 117.6% with relative standard deviations of less than 11.8% (n=5) for all analytes. The limits of detection for the 20 triazole pesticides were all less than 0.4μgL -1 , and were sufficient to meet international standards. Copyright © 2017 Elsevier B.V. All rights reserved.

  20. Fungicidal properties of two saponins from Capsicum frutescens and the relationship of structure and fungicidal activity.

    Science.gov (United States)

    De Lucca, A J; Boue, S; Palmgren, M S; Maskos, K; Cleveland, T E

    2006-04-01

    Two steroidal saponins have been purified from cayenne pepper (Capsicum frutescens). Both have the same steroidal moiety but differ in the number of glucose moieties: the first saponin has four glucose moieties (molecular mass 1081 Da) and the second contains three glucose moieties (molecular mass 919 Da). Solubility in aqueous solution is less for the saponin containing three glucose moieties than for the one containing four glucose moieties. The larger saponin was slightly fungicidal against the nongerminated and germinating conidia of Aspergillus flavus, A. niger, A. parasiticus, A. fumigatus, Fusarium oxysporum, F. moniliforme, and F. graminearum, whereas, the second saponin (molecular mass 919 Da) was inactive against these fungi. Results indicate that the absence of one glucose molecule affects the fungicidal and aqueous solubility properties of these similar molecules.

  1. Chemosensitization of plant pathogenic fungi to agricultural fungicides.

    Directory of Open Access Journals (Sweden)

    Vitaly eDzhavakhiya

    2012-03-01

    Full Text Available A common consequence of using agricultural fungicides is the development of resistance by fungal pathogens, which undermines reliability of fungicidal effectiveness. A potentially new strategy to aid in overcoming or minimizing this problem is enhancement of pathogen sensitivity to fungicides, or chemosensitization. Chemosensitization can be accomplished by combining a commercial fungicide with a certain non- or marginally fungicidal substance at levels where, alone, neither compound would be effective. Chemosensitization decreases the probability of the pathogen developing resistance, reduces the toxic impact on the environment by lowering effective dosage levels of toxic fungicides, and improves efficacy of antifungal agents. The present study shows that the antifungal activity of azole and strobilurin fungicides can be significantly enhanced through their co-application with certain natural or synthetic products against several economically important plant pathogenic fungi. Quadris (azoxystrobin combined with thymol at a non-fungitoxic concentration produced much higher growth inhibition of Bipolaris sorokiniana, Phoma glomerata, Alternaria sp. and Stagonospora nodorum than the fungicide alone. The effect of Dividend (difenoconazole applied with thymol significantly enhanced antifungal activity against B. sorokiniana and S. nodorum. Folicur (tebuconazole combined with 4-hydroxybenzaldehyde (4-HBA, 2,3-dihydroxybenzaldehyde or thymol significantly inhibited growth of A. alternata, at a much greater level than the fungicide alone. In addition, co-application of Folicur and 4-HBA resulted in a similar enhancement of antifungal activity against Fusarium culmorum. Lastly, we discovered that metabolites in the culture liquid of F. sambucinum biocontrol isolate FS-94 also had chemosensitizing activity, increasing S. nodorum sensitivity to Folicur and Dividend.

  2. Nucleosides of 4-methylthio-1,2,3-triazol-5-yl-carboxylic acid derivatives

    International Nuclear Information System (INIS)

    Shingarova, I.D.; Yartseva, I.V.; Preobrazhenskaya, M.N.

    1987-01-01

    2-β-D-Ribofuranosyl-4-methylthio-5-methoxycarbonyl-1,2,3-triazole was obtained by fusing 4-methylthio-5-methoxycarbonyl-1,2,3-triazole together with tetraacyl-D-ribofuranose, followed by deacylation, and its amide and hydrazide were prepared. The structures of the new nucleosides were established by converting them into known 2-nucleosides of 1,2,3-triazol-4-yl-carboxylic acid derivatives. By comparing PMR spectra with previously reported PMR spectra for the isomeric 1- and 2-nucleosides of 1,2,3-triazol-4-yl-carboxylic acid derivatives, the synthesized nucleosides could be assigned to 2-substituted triazoles

  3. Influence of agronomic conditions on the efficacy of different fungicides applied to wheat at heading: effect on flag leaf senescence, Fusarium head blight attack, grain yield and deoxynivalenol contamination

    Directory of Open Access Journals (Sweden)

    Massimo Blandino

    2011-10-01

    Full Text Available A series of field experiments has been conducted in North West Italy over a period of 3 years to evaluate the effect of fungicide applications on common wheat yield and safety, combined with different agronomic conditions (high: a susceptible variety to FHB planted in an untilled field; low: a medium tolerant variety to FHB planted in a ploughed field for Fusarium head blight (FHB infection risk. A azole mixture (prochloraz + epoxiconazole, applied at heading, was compared in each year and for each agronomic condition with a triazole with high activity against F. graminearum and F. culmorum (metconazole, a strobilurin-azole mixture with elevated action to control leaf diseases and delay leaf senescence (azoxystrobin + prochloraz and an untreated control. The following parameters were analyzed: flag leaf greenness, grain yield, test weight, thousand kernel weight (TKW, FHB incidence and severity and deoxynivalenol (DON contamination. The results of this research, conducted over three years with different meteorological conditions, underline the important link between fungicide efficacy and environmental and agronomic conditions that can influence fungal disease pressure. The fungicide effect on the control of FHB and the increase in flag leaf longevity and grain yield were greater with an increase in the disease pressure. On the other hand, the DON contamination was reduced by the fungicide to a greater extent in the low risk agronomic and environmental conditions compared to the high risk ones. Prochloraz + epoxiconazole showed a lower efficacy in reducing DON contamination compared to metconazole, particularly in the higher FHB pressure conditions. No significant differences were observed between the azole mixture and the strobilurin-azole mixture for flag leaf greenness, grain yield, test weight or TKW. This study provides useful information that can be used to evaluate, in naturally-infected field conditions, the effect of a fungicide

  4. Substituted 4-hydroxy-1,2,3-triazoles

    DEFF Research Database (Denmark)

    Pippione, Agnese C.; Dosio, Franco; Ducime, Alex

    2015-01-01

    Bioisosterism and scaffold hopping are two widely used approaches in medicinal chemistry for the purpose of lead optimization. The study highlights the physicochemical properties of the 4-hydroxy-1,2,3-triazole scaffold, a less investigated heterocyclic system. Synthetic strategies to obtain...... different N-substituted 4-hydroxy-1,2,3-triazole isomers are presented, and their role as possible isosteres of the carboxylic acid is discussed. The aim is to use this system to modulate the acidic moieties present in lead compounds and, at the same time, to regiodirect substituents in set directions......, through targeted substitution on the three nitrogen atoms of the triazole ring. Through this approach, compounds having enhanced binding affinity, will be sought. Two examples of bioisosteric applications of this moiety are presented. In the first example, a classical bioisosteric approach mimicking...

  5. Antibactericidal effect of some substituted-1, 2, 4-triazole derivatives

    International Nuclear Information System (INIS)

    Singh, R.J.

    2011-01-01

    The syntheses of a series of some substituted-1, 2, 4-triazole derivatives are described. The reaction of sodium salt of a-sulphonated of stearic acid hydrazide (1) with carbon disulphide in alcoholic KOH yielded the corresponding sodium 1-(4-amino-5-mercapto-4H-[1, 2, 4]-triazol-3yl)-heptadecane-1-sulfonate (2). The reaction of compound (2) with urea, chloroacetyl chloride, chloroacetaldehyde and phenacyl bromides yielded the substituted 1, 2, 4-triazole derivatives (3), (4), (5) and (6) respectively. All the synthesized compounds were characterized by IR, PMR, Mass spectral data and elemental analyses. All newly synthesized compounds have been assayed for their antibacterial activities against S. aureus, E. coli, B. subtilis and P. aeruginosa. (author)

  6. Regioselectivity in the Thermal Rearrangement of Unsymmetrical 4-Methyl-4H-1,2,4-triazoles to 1-Methyl-1H-1,2,4-triazoles

    Directory of Open Access Journals (Sweden)

    Per H.J. Carlsen

    2001-11-01

    Full Text Available The rearrangement of 4-methyl-3,5-diaryl-4H-1,2,4-triazoles to the corresponding 1-methyl-3,5-diaryl-1H-1,2,4-triazoles showed regioselectivity comparable to that observed for the alkylation of 3,5-diaryl-1H-1,2,4-triazoles. This lends support to a proposed mechanism for the rearrangement that involves consecutive nucleophilic displacements steps.

  7. Thermal Rearrangement of Allyl Substituted Unsymmetric 4H-1,2,4-Triazoles to the Corresponding 1H-1,2,4-triazoles

    OpenAIRE

    Jørgensen, Kåre B.; Olsen, Ragnhild B.; Carlsen, Per H.J.

    2001-01-01

    A series of neat 4-(2-alkenyl) substituted 5-methyl-3-phenyl-4H-1,2,4-triazoles were thermolyzed at 320 oC producing a rearrangement products, of which the regioisomeric 1- and 2-substituted triazoles were the main products. The group migrations were rationalized in terms of consecutive SN2-type reactions. This mechanism was supported by a study of the alkylations of the triazoles which gave similar product mixtures. 4-(2-alkenyl) substituted 3-phenyl-4H-1,2,4-triazoles, on the other hand, ga...

  8. Thermal Rearrangement of Allyl Substituted Unsymmetric 4H-1,2,4-Triazoles to the Corresponding 1H-1,2,4-triazoles

    Directory of Open Access Journals (Sweden)

    Per H.J. Carlsen

    2001-04-01

    Full Text Available A series of neat 4-(2-alkenyl substituted 5-methyl-3-phenyl-4H-1,2,4-triazoles were thermolyzed at 320 oC producing a rearrangement products, of which the regioisomeric 1- and 2-substituted triazoles were the main products. The group migrations were rationalized in terms of consecutive SN2-type reactions. This mechanism was supported by a study of the alkylations of the triazoles which gave similar product mixtures. 4-(2-alkenyl substituted 3-phenyl-4H-1,2,4-triazoles, on the other hand, gave predominantly elimination products.

  9. Synthesis and Antitumor Activity of Triazole-Containing Sorafenib Analogs

    Directory of Open Access Journals (Sweden)

    Wenjing Ye

    2017-10-01

    Full Text Available Using a highly effective binuclear Cu complex as the catalyst, the 1,3-dipolar cycloaddition reactions between 16 alkynes and two azides were successfully performed and resulted in the production of 25 new triazole-containing sorafenib analogs. Several compounds were evaluated as potent antitumor agents. Among them, 4-(4-(4-(3-fluorophenyl-1H-1,2,3-triazol-1-ylphenoxy-N-methylpicolinamide (8f potently suppressed the proliferation of HT-29 cancer cells by inducing apoptosis and almost completely inhibited colony formation at a low micromolar concentration.

  10. Design, synthesis, and in vitro evaluation of novel antifungal triazoles.

    Science.gov (United States)

    Xie, Fei; Ni, Tingjunhong; Zhao, Jing; Pang, Lei; Li, Ran; Cai, Zhan; Ding, Zichao; Wang, Ting; Yu, Shichong; Jin, Yongsheng; Zhang, Dazhi; Jiang, Yuanying

    2017-05-15

    Twenty-nine novel triazole analogues of ravuconazole and isavuconazole were designed and synthesized. Most of the compounds exhibited potent in vitro antifungal activities against 8 fungal isolates. Especially, compounds a10, a13, and a14 exhibited superior or comparable antifungal activity to ravuconazole against all the tested fungi. Structure-activity relationship study indicated that replacing 4-cyanophenylthioazole moiety of ravuconazole with fluorophenylisoxazole resulted in novel antifungal triazoles with more effectiveness and a broader-spectrum. Copyright © 2017 Elsevier Ltd. All rights reserved.

  11. Profitability of fungicide use decisions among cocoa farmers in south ...

    African Journals Online (AJOL)

    CRIN) recommended fungicide use rate with profit maximization objective of Nigerian cocoa farmers. To achieve this research objective, a cross-sectional survey of cocoa farmers in four local government areas (LGAs) each in Osun and Ondo ...

  12. Federal Insecticide, Fungicide, and Rodenticide Act Section 18 Database

    Data.gov (United States)

    U.S. Environmental Protection Agency — Section 18 of Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) authorizes EPA to allow an unregistered use of a pesticide for a limited time if EPA...

  13. Tetrazole and triazole as bioisosteres of carboxylic acid: discovery of diketo tetrazoles and diketo triazoles as anti-HCV agents.

    Science.gov (United States)

    Song, Wu-Hui; Liu, Ming-Ming; Zhong, Dong-Wei; Zhu, Ye-lin; Bosscher, Mike; Zhou, Lu; Ye, De-Yong; Yuan, Zheng-Hong

    2013-08-15

    A series of diketo tetrazoles and diketo triazoles were designed and synthesized as bioisosteres of α,γ-diketo acid, the active site inhibitor of HCV (Hepatitis C virus) polymerase NS5B. Among the synthesized compounds, 4-(4-fluorobenzyloxy)phenyl diketo triazole (30) exhibited anti-HCV activity with an EC50 value of 3.9 μM and an SI value more than 128. The reduction of viral protein and mRNA levels were also validated, supporting the anti-HCV activity of compound 30. These results provide convincing evidence that the diketo tetrazoles and diketo triazoles can be developed as bioisosteres of α,γ-diketo acid to exhibit potent inhibitory activity against HCV. Copyright © 2013 Elsevier Ltd. All rights reserved.

  14. Combination of solvent extractants for dispersive liquid-liquid microextraction of fungicides from water and fruit samples by liquid chromatography with tandem mass spectrometry.

    Science.gov (United States)

    Pastor-Belda, Marta; Garrido, Isabel; Campillo, Natalia; Viñas, Pilar; Hellín, Pilar; Flores, Pilar; Fenoll, José

    2017-10-15

    A multiresidue method was developed to determine twenty-five fungicides belonging to three different chemical families, oxazoles, strobilurins and triazoles, in water and fruit samples, using dispersive liquid-liquid microextraction (DLLME) and liquid chromatography/tandem mass spectrometry (LC-MS 2 ). Solid-liquid extraction with acetonitrile was used for the analysis in fruits, the extract being used as dispersant solvent in DLLME. Since some of the analytes showed high affinity for chloroform and the others were more efficiently extracted with undecanol, a mixture of both solvents was used as extractant in DLLME. After evaporation of CHCl 3 , the enriched phase was analyzed. Enrichment factors in the 23-119 and 12-60 ranges were obtained for waters and fruits, respectively. The approach was most sensitive for metominostrobin with limits of quantification of 1ngL -1 and 5ngkg -1 in waters and fruits, respectively, while a similar sensitivity was attained for tebuconazole in fruits. Recoveries of the fungicides varied between 86 and 116%. Copyright © 2017 Elsevier Ltd. All rights reserved.

  15. Identification and quantification of metabolites of the fungicide tebuconazole in human urine.

    Science.gov (United States)

    Mercadante, R; Polledri, E; Scurati, S; Moretto, A; Fustinoni, S

    2014-11-17

    Tebuconazole (TEB) is a fungicide used in agriculture; the objective of this work was to identify and quantify TEB metabolites in human urine. Samples from seven vineyard workers exposed to TEB were submitted to liquid chromatography interfaced with a triple quadrupole mass spectrometer, equipped with an electron spray source, and a linear ion trap to gain a profile of candidate metabolites. Based on the presence of the ion m/z 70 in the MS/MS spectra, which corresponds to protonated triazole (a specific moiety of TEB), and the isotopic pattern of the molecular ions, typical of molecules with one chlorine atom, hydroxyl and carboxyl derivatives of TEB, that is, TEB-OH and TEB-COOH, were identified as major metabolites, both as free molecules and as glucuronide (Glc) conjugates. The mean molar fractions were 0.67, 0.13, 0.13, and 0.07 for TEB-O-Glc, TEB-OH, TEB-COO-Glc, and TEB-COOH. Urine samples were submitted to hydrolysis with β-glucuronidase, and the free compounds were quantified in the presence of deuterated TEB (TEB-d6) as the internal standard (IS), by multiple reaction monitoring (MRM) mode. The assay was linear in the ranges of 0.2-600 μg/L and 0.1-240 μg/L for TEB-OH and TEB-COOH, respectively; precision, accuracy, and the limit of quantification (LOQ) were <3.1%, 98-103%, and 0.3 μg/L for both analytes. An evaluation of matrix effects showed that the use of TEB-d6 controlled these sources of bias. The urinary levels of TEB-OH and TEB-COOH in specimens collected from farmers exposed to TEB ranged from 10 to 473 and from 3 to 159 μg/L, respectively.

  16. Bis(4H-1,2,4-triazol-3-yldisulfane

    Directory of Open Access Journals (Sweden)

    Dongsheng Liu

    2008-01-01

    Full Text Available The title compound, C4H4N6S2, was synthesized by the reaction of 3-mercapto-1H-1,2,4-triazole with sodium hydroxide in ethanol. The molecule possesses a crystallographically imposed twofold axis. Intermolecular N—H...N hydrogen bonds link the molecules into chains along the c axis.

  17. Detection of Polish clinical Aspergillus fumigatus isolates resistant to triazoles

    DEFF Research Database (Denmark)

    Nawrot, Urszula; Kurzyk, Ewelina; Arendrup, Maiken Cavling

    2018-01-01

    We studied the presence of triazole resistance of 121 Aspergillus fumigatus clinical isolates collected in two Polish cities, Warsaw and Wrocław, to determine if resistance is emerging in our country. We identified five itraconazole resistant isolates (4.13%) carrying the TR34/L98H alteration in ...

  18. Efficient Synthesis of 1-Sulfonyl-1,2,3-triazoles

    Science.gov (United States)

    Raushel, Jessica; Fokin, Valery V.

    2010-01-01

    An efficient room temperature method for the synthesis of 1-sulfonyl-1,2,3-triazoles from in situ generated copper(I) acetylides and sulfonyl azides is described. Copper(I) thiophene-2-carboxylate (CuTC) catalyst produces the title compounds under both non-basic anhydrous and aqueous conditions in good yields. PMID:20931987

  19. Animal Models for Studying Triazole Resistance in Aspergillus fumigatus

    NARCIS (Netherlands)

    Lewis, R.E.; Verweij, P.E.

    2017-01-01

    Infections caused by triazole-resistant Aspergillus fumigatus are associated with a higher probability of treatment failure and mortality. Because clinical experience in managing these infections is still limited, mouse models of invasive aspergillosis fulfill a critical void for studying treatment

  20. Novel Triazole Hybrids of Betulin: Synthesis and Biological Activity Profile.

    Science.gov (United States)

    Bębenek, Ewa; Jastrzębska, Maria; Kadela-Tomanek, Monika; Chrobak, Elwira; Orzechowska, Beata; Zwolińska, Katarzyna; Latocha, Małgorzata; Mertas, Anna; Czuba, Zenon; Boryczka, Stanisław

    2017-11-01

    Betulin derivatives containing a 1,2,3-triazole ring possess a wide spectrum of biological activities, including antiviral, anticancer, and antibacterial activity. A series of novel triazoles were prepared by the 1,3-dipolar cycloaddition reaction between the alkyne derivatives of betulin and organic azides. The chemical structures of the obtained compounds were defined by ¹H and 13 C NMR, IR, and high-resolution mass spectrometry (HR-MS) analysis. The target triazoles were screened for their antiviral activity against DNA and RNA viruses. The cytotoxic activity of the obtained compounds 5a - k and 6a - h was determined using five human cancer cell lines (T47D, MCF-7, SNB-19, Colo-829, and C-32) by a WST-1 assay. The bistriazole 6b displayed a promising IC 50 value (0.05 μM) against the human ductal carcinoma T47D (500-fold higher potency than cisplatin). The microdilution method was applied for an evaluation of the antimicrobial activity of all of the compounds. The triazole 5e containing a 3'-deoxythymidine-5'-yl moiety exhibited antibacterial activity against two gram-negative bacteria vz. Klebsiella pneumoniae and Escherichia coli (minimal inhibitory concentration (MIC) range of 0.95-1.95 μM).

  1. Design and selection of triazole-based compounds with high ...

    Indian Academy of Sciences (India)

    Density functional theory (DFT) was used to study the molecular geometries, electronic structures, heats of formation in gas phase and in condensed phase, energetic properties, and thermal stabilities of triazole derivatives. The results show that the properties are associated with the different substituents and substitution ...

  2. Novel Triazole Hybrids of Betulin: Synthesis and Biological Activity Profile

    Directory of Open Access Journals (Sweden)

    Ewa Bębenek

    2017-11-01

    Full Text Available Betulin derivatives containing a 1,2,3-triazole ring possess a wide spectrum of biological activities, including antiviral, anticancer, and antibacterial activity. A series of novel triazoles were prepared by the 1,3-dipolar cycloaddition reaction between the alkyne derivatives of betulin and organic azides. The chemical structures of the obtained compounds were defined by 1H and 13C NMR, IR, and high-resolution mass spectrometry (HR-MS analysis. The target triazoles were screened for their antiviral activity against DNA and RNA viruses. The cytotoxic activity of the obtained compounds 5a–k and 6a–h was determined using five human cancer cell lines (T47D, MCF-7, SNB-19, Colo-829, and C-32 by a WST-1 assay. The bistriazole 6b displayed a promising IC50 value (0.05 μM against the human ductal carcinoma T47D (500-fold higher potency than cisplatin. The microdilution method was applied for an evaluation of the antimicrobial activity of all of the compounds. The triazole 5e containing a 3′-deoxythymidine-5′-yl moiety exhibited antibacterial activity against two gram-negative bacteria vz. Klebsiella pneumoniae and Escherichia coli (minimal inhibitory concentration (MIC range of 0.95–1.95 μM.

  3. Pendant triazole ring assisted mesogen containing side chain liquid ...

    Indian Academy of Sciences (India)

    Two series of click chemistry assisted alkoxymethyl-1H-[1,2,3]-triazol-1-yl containing sidechain liquid-crystalline polymethacrylates were synthesized by free radical polymerization technique. Mesogen was linked to backbone through various spacer units. Monomers and polymers were characterized by FT-IR, 1H and ...

  4. Design and selection of triazole-based compounds with high ...

    Indian Academy of Sciences (India)

    128, No. 8, August 2016, pp. 1223–1236. c Indian Academy of Sciences. DOI 10.1007/s12039-016-1117-x. Design and selection of triazole-based compounds with high energetic properties and stabilities. GUOZHENG ZHAO. ∗. , JIANFENG JIA and HAISHUN WU. School of Chemistry and Materials Science, Shanxi Normal ...

  5. Risk assessment on the impact of environmental usage of triazoles on the development and spread of resistance to medical triazoles in Aspergillus species

    NARCIS (Netherlands)

    Kleinkauf, N.; Verweij, P.E.; Arendrup, M.C.; Donnelly, P.J.; Cuenca-Estrella, M.; Fraaije, B.; Melchers, W.J.G.; Adriaenssens, N.; Kema, G.H.J.; Ullmann, A.; Bowyer, P.; Denning, D.W.

    2013-01-01

    In recent years, triazole resistance in human Aspergillus diseases appears to have been increasing in several European countries. However, current data on the prevalence of resistance are based on a small number of studies which are only available from a few European countries. If present, triazole

  6. EQCM and XPS analysis of 1,2,4-triazole and 3-amino-1,2,4-triazole as copper corrosion inhibitors in chloride solution

    International Nuclear Information System (INIS)

    Finšgar, Matjaž

    2013-01-01

    Highlights: •3-Amino-1,2,4-triazole is a more effective inhibitor than 1,2,4-triazole. •Reasons for the differences in inhibition effectiveness are discussed. •1,2,4-Triazole surface layer growth is faster compared to 3-amino-1,2,4-triazole. •The 1,2,4-triazole surface layer on Cu is thicker compared to 3-amino-1,2,4-triazole. -- Abstract: In this study, the influence of the amino functional group in the 1,2,4-triazole at position C3 (the 3-amino-1,2,4-triazole compound), on the surface layer formation and surface chemistry of these two Cu corrosion inhibitors is explored. Special attention is devoted to the orientation of these two molecules and the way they bond to the Cu surface. With the aim of obtaining electrochemical quartz crystal microbalance and X-ray photoelectron spectroscopy measurements, the article discusses why differences in the corrosion inhibition effectiveness of these two molecules exist. Moreover, the thicknesses of the inhibitor surface layers formed on the Cu are determined

  7. In vitro sensitivity of Fusarium graminearum isolates to fungicides

    Directory of Open Access Journals (Sweden)

    Aveline Avozani

    2014-09-01

    Full Text Available Head blight of wheat is a disease of global importance. In Brazil, it can cause damage of up to 27%. As resistant cultivars are not available yet, short-term disease control relies on the use of fungicides. The first step to reach effective management is to identify potent fungicides. In vitro experiments were conducted to determine the inhibitory concentration 50% (IC50 for mycelial growth or conidial germination, according to the chemical group of fungicides, of five Fusarium graminearum isolates of different origins. The following demethylation inhibitor (DMI fungicides were tested: epoxiconazole, cyproconazole, metconazole, prochloraz, protioconazole and tebuconazole. In addition, azoxystrobin, kresoxim-methyl, pyraclostrobin and trifloxystrobin were included in the study, representing Quinone outside inhibitor fungicides (QoI, as well as a tubulin synthesis inhibitor, carbendazim and two ready mixtures, trifloxystrobin + tebuconazole or trifloxistrobin + prothioconazole. DMI's showed lower IC50 values compared to the QoI's. For the five tested isolates, in the overall mean, IC50 considering mycelial growth ranged for DMI's from 0.01 mg/L (metconazole, prochloraz and prothioconazole to 0.12 mg/L (cyproconazole and considering conidial germination for QoI's from 0.21 mg/L (azoxystrobin to 1.33 mg/L (trifloxystrobin. The IC50 for carbendazim was 0.07 mg/L. All tested isolates can be considered sensitive to the studied DMI's, although certain differences in sensitivity could be detected between the isolates originating from one same state.

  8. “Click”-Capture, ROMP, Release: Facile Triazolation Utilizing ROMP-derived Oligomeric Phosphates

    Science.gov (United States)

    Long, Toby R.; Faisal, Saqib; Maity, Pradip K.; Rolfe, Alan; Kurtz, Ryan; Klimberg, Sarra V.; Najjar, Muhammad-Rabbie; Basha, Fatima Z.; Hanson, Paul R.

    2011-01-01

    Soluble, high-load ROMP-derived oligomeric triazole phosphates (OTP) are reported for application as efficient triazolating reagents of nucleophilic species. Utilizing a “Click”-capture, ROMP, release protocol, the efficient and purification free, direct triazolation of N-, O- and S-nucleophilic species was successfully achieved. A variety of OTP derivatives were rapidly synthesized as free-flowing solids on multi-gram scale from commercially available materials. PMID:21434675

  9. Highly N2-Selective Palladium-Catalyzed Arylation of 1,2,3-Triazoles

    Science.gov (United States)

    Ueda, Satoshi; Su, Mingjuan; Buchwald, Stephen L.

    2012-01-01

    Highly N2-selective arylation of 4,5-unsubstituted and 4-substituted 1,2,3-triazoles was achieved for the first time by Pd/L1 catalyst system. A wide range of N2-aryl-1,2,3-triazoles were prepared from aryl bromides, chlorides and triflates with excellent (95–99%) N2-selectivity. DFT calculations suggest that formation of N2-arylated 1,2,3-triazoles is favored kinetically. PMID:21853510

  10. (1-Phenyl-1H-1,2,3-triazol-4-ylmethyl pyridine-3-carboxylate

    Directory of Open Access Journals (Sweden)

    Zakirjon Karimov

    2010-07-01

    Full Text Available In the title compound, C15H12N4O2, the dihedral angle between the planes of the nicotinoyloxy fragment and triazole ring is 88.61 (5°. The dihedral angle between the planes of triazole and benzene rings is 16.54 (11°. The crystal structure is stabilized by intermolecular C—H...N, C—H...O and C—H...π(triazole hydrogen bonds and aromatic π–π stacking interactions between the benzene and triazole rings [centroid–centroid distance = 3.895 (1 Å

  11. Effect of Preexposure to Triazoles on Susceptibility and Virulence of Rhizopus oryzae.

    Science.gov (United States)

    Bellanger, Anne-Pauline; Albert, Nathaniel D; Lewis, Russell E; Walsh, Thomas J; Kontoyiannis, Dimitrios P

    2015-12-01

    Triazole prophylaxis has become the norm in patients with hematological malignancies. Breakthrough infections caused by Mucorales during triazole prophylaxis remain a challenging problem. We found that preexposure of Rhizopus oryzae to antifungal triazoles (fluconazole, voriconazole, posaconazole, and itraconazole) did not modify the in vitro susceptibility of Rhizopus oryzae to posaconazole. In contrast, preexposure of Rhizopus to triazoles was associated with the enhanced in vitro susceptibility of R. oryzae to amphotericin B. Preexposure to posaconazole did not alter the virulence of R. oryzae in the fly model of mucormycosis. Copyright © 2015, American Society for Microbiology. All Rights Reserved.

  12. 1, 2, 3 - Triazoles as key frameworks in drug discovery & metal catalysis

    OpenAIRE

    Irastorza Epelde, Aitziber

    2018-01-01

    356 p. La tesis se enmarca dentro de la química de los 1H-1,2,3-triazoles y sus sales de N-alquil-triazolio. El trabajo realizado contempla los siguientes objetivos:1.- Sintetizar y estudiar los 1H-1,2,3-triazoles como plantillas moleculares de fármacos reguladores de [Ca2+] intraplasmático en músculo esquelético2.- Transformar triazoles 1,4-disustituidos en 1,5-disustituidos via N-desalquilación regiocontrolada de sales de triazolio3.- Desarrollar nuevos 1,2,3-triazoles como agentes direc...

  13. Cyclic compounds of tetracoordinated boron from 5-amino-1,2,4-triazole and aromatic nitriles

    International Nuclear Information System (INIS)

    Dorokhov, V.A.; Amamchyan, A.R.; Bochkareva, M.N.; Teslya, I.A.; Starikova, Z.A.

    1987-01-01

    New cyclic compounds of tetracoordinated boron - dialkylboryl-[(1,2,4-triazole-5-yl)-amidinate] from 5-amino-1,2,4-triazole, aromatic nitriles and trialkylborane have been synthesized. It is shown that in dialkylboryl derivatives of 5-amino-1,2,4-triazole forming crystalline dimers, R 2 B (R=Pr, Bu) groups are bonded to circular nitrogen atoms. The X-ray diffraction method was used to determine crystalline and molecular structures of dipropylboryl-[(1,2,4-triazole-5-yl)benzamidinate

  14. Nanosulfur: A Potent Fungicide Against Food Pathogen, Aspergillus niger

    Science.gov (United States)

    Choudhury, Samrat Roy; Nair, Kishore K.; Kumar, Rajesh; Gogoi, Robin; Srivastava, Chitra; Gopal, Madhuban; Subhramanyam, B. S.; devakumar, C.; Goswami, Arunava

    2010-10-01

    Elemental sulfur (S0), man's oldest eco-friendly fungicide for curing fungal infections in plants and animals, is registered in India as a non-systemic and contact fungicide. However due to its high volume requirement, Indian agrochemical industry and farmers could not effectively use this product till date. We hypothesize that intelligent nanoscience applications might increase the visibility of nanosulfur in Indian agriculture as a potent and eco-safe fungicide. Sulfur nanoparticles (NPs) were synthesized bottom-up via a liquid synthesis method with average particle size in the range of 50-80 nm and the shapes of the NPs were spherical. A comparative study of elemental and nano-sulfur produced has been tested against facultative fungal food pathogen, Aspergillus niger. Results showed that nanosulfur is more efficacious than its elemental form.

  15. Nanosulfur: A Potent Fungicide Against Food Pathogen, Aspergillus niger

    International Nuclear Information System (INIS)

    Choudhury, Samrat Roy; Goswami, Arunava; Nair, Kishore K.; Kumar, Rajesh; Gopal, Madhuban; Devakumar, C.; Gogoi, Robin; Srivastava, Chitra; Subhramanyam, B. S.

    2010-01-01

    Elemental sulfur (S 0 ), man's oldest eco-friendly fungicide for curing fungal infections in plants and animals, is registered in India as a non-systemic and contact fungicide. However due to its high volume requirement, Indian agrochemical industry and farmers could not effectively use this product till date. We hypothesize that intelligent nanoscience applications might increase the visibility of nanosulfur in Indian agriculture as a potent and eco-safe fungicide. Sulfur nanoparticles (NPs) were synthesized bottom-up via a liquid synthesis method with average particle size in the range of 50-80 nm and the shapes of the NPs were spherical. A comparative study of elemental and nano-sulfur produced has been tested against facultative fungal food pathogen, Aspergillus niger. Results showed that nanosulfur is more efficacious than its elemental form.

  16. Design and synthesis of 1H-1,2,3-triazoles derived from econazole as antitubercular agents.

    Science.gov (United States)

    Kim, Suhyun; Cho, Sang-Nae; Oh, Taegwon; Kim, Pilho

    2012-11-15

    Econazole has been known to be active against Mycobacterium tuberculosis. We have designed and synthesized 1H-1,2,3-triazoles derived from econazole as antitubercular agents. The majority of triazole derivatives have been prepared by microwave-assisted click chemistry. It turned out that all of the prepared triazoles had no antifungal activities. However, most of the hydroxy-triazoles (6a and 10) apparently turned out to have antitubercular activities. Overall, hydroxy-triazoles 10 were more active than their corresponding ether-triazoles 11. While the MIC value of hydroxy-triazole 10d was as good as econazole (16 μg/mL), the MIC value of 10a was two-fold more active than econazole, suggesting that this 1H-1,2,3-triazole scaffold (3) could be further optimized to develop Mtb specific agents. Copyright © 2012 Elsevier Ltd. All rights reserved.

  17. Enantiopure 1,4,5-trisubstituted 1,2,3-triazoles from carbohydrates: applications of organoselenium chemistry.

    Science.gov (United States)

    Bhaumik, Atanu; Samanta, Supravat; Pathak, Tanmaya

    2014-08-01

    A wide range of stable vinyl selenone-modified furanosides has been synthesized for the first time. These 2π-partners undergo 1,3-dipolar cycloaddition reactions with a wide range of organic azides to afford enantiopure trisubstituted triazoles. Furanosyl rings opened up during triazole synthesis to generate polyfunctionalized molecules, ready to undergo further transformations. This strategy is one of the most convenient methods for the synthesis of enantiopure 1,4,5-trisubstituted 1,2,3-triazoles where the chiral components are attached to C-4 or C-5 position of triazole ring. These triazoles are formed in a regioselective manner, and several pairs of regioisomeric triazoles have also been synthesized. The approach affords densely functionalized triazoles, which are amenable to further modifications because of the presence of aldehyde and hydroxyl groups. This powerful and practical route adds to the arsenals of chemists and biologists interested in the synthesis and applications of triazoles.

  18. Control of sugar beet powdery mildew with strobilurin fungicides

    Directory of Open Access Journals (Sweden)

    Karaoglanidis George S.

    2006-01-01

    Full Text Available Powdery mildew, caused by Erysiphe betae is a major foliar disease of sugar beet in areas with dry and relatively warm weather conditions throughout the world. In the present study, four fungicides belonging to the relatively new class of strobilurin fungicides, azoxystrobin, kresoxim-methyl pyraclostrobin and trifloxystrobin were evaluated in three different application doses (100, 150 and 200 mg a.i. ha–1 during 2003-2004 for the control of the disease. Among the four strobilurin fungicides tested trifloxystrobin and kresoxim-methyl were the most effective with control efficiency values higher than 94% compared to the control treatment even when applied at lower application dose of 100 mg a.i. ha–1. Azoxystrobin and pyraclostrobin showed a poor to modest activity against the disease even when applied at the highest application dose of 200 μg a.i. ha–1. Disease severity, in terms of AUDPC values was significantly correlated to decreased root yield, while no significant correlation existed among disease severity and sugar content of the roots or sucrose yield. In addition, the efficiency of tank mixtures of four strobilurin fungicides applied at 100 μg a.i. ha–1 with two sterol demethylation - inhibiting fungicides (DMIs, difenoconazole and cyproconazole applied at 62.5 and 25 mg a.i. ha–1, respectively, was evaluated. The mixtures of azoxystrobin and pyraclostrobin with either difenoconazole or cyproconazole provided a better control efficiency compared to the single application of each mixture partner, while the tank mixtures of trifloxystrobin and kresoxim-methyl with either difenoconazole or cyproconazole provided a better control efficiency compared to single application of difenoconazole or cyproconazole and similar control efficiency compared to the efficiency obtained by single application of the strobilurin fungicides.

  19. Acaricide, fungicide and drug interactions in honey bees (Apis mellifera.

    Directory of Open Access Journals (Sweden)

    Reed M Johnson

    Full Text Available BACKGROUND: Chemical analysis shows that honey bees (Apis mellifera and hive products contain many pesticides derived from various sources. The most abundant pesticides are acaricides applied by beekeepers to control Varroa destructor. Beekeepers also apply antimicrobial drugs to control bacterial and microsporidial diseases. Fungicides may enter the hive when applied to nearby flowering crops. Acaricides, antimicrobial drugs and fungicides are not highly toxic to bees alone, but in combination there is potential for heightened toxicity due to interactive effects. METHODOLOGY/PRINCIPAL FINDINGS: Laboratory bioassays based on mortality rates in adult worker bees demonstrated interactive effects among acaricides, as well as between acaricides and antimicrobial drugs and between acaricides and fungicides. Toxicity of the acaricide tau-fluvalinate increased in combination with other acaricides and most other compounds tested (15 of 17 while amitraz toxicity was mostly unchanged (1 of 15. The sterol biosynthesis inhibiting (SBI fungicide prochloraz elevated the toxicity of the acaricides tau-fluvalinate, coumaphos and fenpyroximate, likely through inhibition of detoxicative cytochrome P450 monooxygenase activity. Four other SBI fungicides increased the toxicity of tau-fluvalinate in a dose-dependent manner, although possible evidence of P450 induction was observed at the lowest fungicide doses. Non-transitive interactions between some acaricides were observed. Sublethal amitraz pre-treatment increased the toxicity of the three P450-detoxified acaricides, but amitraz toxicity was not changed by sublethal treatment with the same three acaricides. A two-fold change in the toxicity of tau-fluvalinate was observed between years, suggesting a possible change in the genetic composition of the bees tested. CONCLUSIONS/SIGNIFICANCE: Interactions with acaricides in honey bees are similar to drug interactions in other animals in that P450-mediated detoxication

  20. Acaricide, fungicide and drug interactions in honey bees (Apis mellifera).

    Science.gov (United States)

    Johnson, Reed M; Dahlgren, Lizette; Siegfried, Blair D; Ellis, Marion D

    2013-01-01

    Chemical analysis shows that honey bees (Apis mellifera) and hive products contain many pesticides derived from various sources. The most abundant pesticides are acaricides applied by beekeepers to control Varroa destructor. Beekeepers also apply antimicrobial drugs to control bacterial and microsporidial diseases. Fungicides may enter the hive when applied to nearby flowering crops. Acaricides, antimicrobial drugs and fungicides are not highly toxic to bees alone, but in combination there is potential for heightened toxicity due to interactive effects. Laboratory bioassays based on mortality rates in adult worker bees demonstrated interactive effects among acaricides, as well as between acaricides and antimicrobial drugs and between acaricides and fungicides. Toxicity of the acaricide tau-fluvalinate increased in combination with other acaricides and most other compounds tested (15 of 17) while amitraz toxicity was mostly unchanged (1 of 15). The sterol biosynthesis inhibiting (SBI) fungicide prochloraz elevated the toxicity of the acaricides tau-fluvalinate, coumaphos and fenpyroximate, likely through inhibition of detoxicative cytochrome P450 monooxygenase activity. Four other SBI fungicides increased the toxicity of tau-fluvalinate in a dose-dependent manner, although possible evidence of P450 induction was observed at the lowest fungicide doses. Non-transitive interactions between some acaricides were observed. Sublethal amitraz pre-treatment increased the toxicity of the three P450-detoxified acaricides, but amitraz toxicity was not changed by sublethal treatment with the same three acaricides. A two-fold change in the toxicity of tau-fluvalinate was observed between years, suggesting a possible change in the genetic composition of the bees tested. Interactions with acaricides in honey bees are similar to drug interactions in other animals in that P450-mediated detoxication appears to play an important role. Evidence of non-transivity, year-to-year variation

  1. Mode of action of the phenylpyrrole fungicide fenpiclonil in Fusarium sulphureum

    NARCIS (Netherlands)

    Jespers, A.B.K.

    1994-01-01

    In the last few decades, plant disease control has become heavily dependent on fungicides. Most modem fungicides were discovered by random synthesis and empirical optimization of lead structures. In general, these fungicides have specific modes of action and meet modem enviromnental

  2. Fungicide residue identification and discrimination using a conducting polymer electronic-nose

    Science.gov (United States)

    Alphus D. Wilson

    2013-01-01

    The identification of fungicide residues on crop foliage is necessary to make periodic pest management decisions. The determination of fungicide residue identities currently is difficult and time consuming using conventional chemical analysis methods such as gas chromatography-mass spectroscopy. Different fungicide types produce unique electronic aroma signature...

  3. Stable Hemiaminals with a Cyano Group and a Triazole Ring

    Directory of Open Access Journals (Sweden)

    Anna Kwiecień

    2014-07-01

    Full Text Available Under neutral conditions the reactions between 4-amino-1,2,4-triazole and cyano-substituted benzaldehyde derivatives yield stable hemiaminals. Addition of small amounts of acid catalyst promotes further step of dehydration resulting in formation of Schiff bases. Four new hemiaminals and the corresponding imines have been obtained. The molecular stability of the hemiaminal intermediates results from both the 1,2,4-triazole moiety and electron withdrawing substituents on the phenyl ring, so no further stabilisation by intramolecular interaction is required. Hemiaminal molecules possess stereogenic centres on carbon and nitrogen atoms. The chirality of these centres is strongly correlated with the conformation of the molecules due to heteroatom hyperconjugation effects.

  4. Synthesis of carbon-14 analogue of 1,5 diaryl-5-[14C]-1,2,3-triazoles

    International Nuclear Information System (INIS)

    Matloubi, Hojatollah; Shafiee, Abbas; Saemian, Nader; Shirvani, Gholamhossein; Daha, Fariba Johari

    2004-01-01

    Two 1,2,3-triazole anticonvulsants, 1-(4-methylsulfone-phenyl)-5-(4-methyl-phenyl)-1,2,3-triazole and 1-(4-methylsulfone-phenyl)-5-phenyl-1,2,3-triazole, both labeled with carbon-14 in the 5-position were prepared from para-tolunitrile-[cyano- 14 C] and benzonitrile-[cyano- 14 C], respectively

  5. Imidazole and Triazole Coordination Chemistry for Antifouling Coatings

    Directory of Open Access Journals (Sweden)

    Markus Andersson Trojer

    2013-01-01

    Full Text Available Fouling of marine organisms on the hulls of ships is a severe problem for the shipping industry. Many antifouling agents are based on five-membered nitrogen heterocyclic compounds, in particular imidazoles and triazoles. Moreover, imidazole and triazoles are strong ligands for Cu2+ and Cu+, which are both potent antifouling agents. In this review, we summarize a decade of work within our groups concerning imidazole and triazole coordination chemistry for antifouling applications with a particular focus on the very potent antifouling agent medetomidine. The entry starts by providing a detailed theoretical description of the azole-metal coordination chemistry. Some attention will be given to ways to functionalize polymers with azole ligands. Then, the effect of metal coordination in azole-containing polymers with respect to material properties will be discussed. Our work concerning the controlled release of antifouling agents, in particular medetomidine, using azole coordination chemistry will be reviewed. Finally, an outlook will be given describing the potential for tailoring the azole ligand chemistry in polymers with respect to Cu2+ adsorption and Cu2+→Cu+ reduction for antifouling coatings without added biocides.

  6. Synthesis of Deuterated 1,2,3-Triazoles

    Science.gov (United States)

    Akula, Hari K.; Lakshman, Mahesh K.

    2012-01-01

    The copper-catalyzed azide–alkyne cycloaddition (CuAAC) is a highly effective method for the selective incorporation of deuterium atom into the C-5 position of the 1,2,3-triazole structure. Reactions of alkynes and azides can be conveniently carried out in a biphasic medium of CH2Cl2/D2O, using the CuSO4/Na ascorbate system. The mildness of the method renders it applicable to substrates of relatively high complexity, such as nucleosides. Good yields and high levels of deuterium incorporation were observed. A reaction conducted in equimolar H2O and D2O showed 2.7 times greater incorporation of hydrogen atom as compared to deuterium. This is consistent with the H+ and D+ ion concentrations in H2O and D2O, respectively. With appropriately deuterated precursors, partially to fully deuterated triazoles were assembled where the final deuterium atom was incorporated in the triazole-forming step. PMID:23016757

  7. Regioselectivity in the Thermal Rearrangement of Unsymmetrical 4-Methyl-4H-1,2,4-triazoles to 1-Methyl-1H-1,2,4-triazoles

    OpenAIRE

    Gautun, Odd R.; Carlsen, Per H.J.

    2001-01-01

    The rearrangement of 4-methyl-3,5-diaryl-4H-1,2,4-triazoles to the corresponding 1-methyl-3,5-diaryl-1H-1,2,4-triazoles showed regioselectivity comparable to that observed for the alkylation of 3,5-diaryl-1H-1,2,4-triazoles. This lends support to a proposed mechanism for the rearrangement that involves consecutive nucleophilic displacements steps. This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and repr...

  8. Chemical Modification of Poly(vinylacetylene) and Synthesis of Poly(1,2,3-triazole)s

    International Nuclear Information System (INIS)

    Wang, Lian Jun; Wang, Le Yong; Liao, Shan

    2011-01-01

    A series of new polymers containing 1,2,3-triazoles were synthesized and their structures and properties were characterized by FT-IR, 1 H NMR, TGA, DSC and GPC. The results showed that the polymers modified by alkyl groups had good solubility, thermal stability and reasonable molecular weights. It was also demonstrated that the properties of fluorine-containing polymers were seriously affected by fluorine atoms with hydrophobic and chemical proof properties

  9. impact of fungicide applications for late blight management on ...

    African Journals Online (AJOL)

    IMPACT OF FUNGICIDE APPLICATIONS FOR LATE BLIGHT. MANAGEMENT ON HUCKLEBERRY YIELDS IN CAMEROON. D. A. FONTEM, A.T. SONGWALANG, J.E. BERINYUY and R.R. SCHIPPERS l. Faculty of Agriculture, University of Dschang, Box 208, Dschang, Cameroon l~orticultural Development Services LLP, ...

  10. Field evaluatin of seed-dressing fungicides bavistin,benlate ...

    African Journals Online (AJOL)

    Field evaluatin of seed-dressing fungicides bavistin,benlate, Fernasan-D and apron plus 50 Ds for the control of seed-borne pathogens of rice ( Oryzae Saliva L ) associated with the three varieties faro 12, faro 15 and faro 29 of rice.

  11. Detoxification of copper fungicide using EDTA-modified cellulosic ...

    African Journals Online (AJOL)

    STORAGESEVER

    2009-02-04

    Feb 4, 2009 ... detoxification of a copper fungicide (KOCIDE 101) using maize cob, a cellulosic material, was studied. Based on copper as the active agent (after a ... Made from CuSO4 and lime. Used as a spray. Copper oxychloride ..... feasible when there is contact between the maize cob and the Cu(II) ions. Therefore ...

  12. Evaluation of two organosynthetic fungicides, for the control of ...

    African Journals Online (AJOL)

    ... of Pisum stativum L. Results indicated that the two fungicides inhibited Ersiphe polygoni DC. Conidia germination and diseases index to various degrees in vitro, depending on the concentration applied. Results showed an increase in yield of treated seeds as compared to control. Plant Products Research Journal Vol.

  13. Fungicidal and bactericidal properties of bisabolol and dragosantol

    Science.gov (United States)

    a-bisabolol, a natural plant sesquiterpene alcohol, and dragosantol, a racemic mixture of synthetic bisabolol, were studied for their fungicidal properties separately against the nongerminated and germinating conidia of several species of Aspergillus and Fusarium which are problems in agriculture an...

  14. Comparison of three fungicide spray advisories for lettuce downy mildew

    NARCIS (Netherlands)

    Wu, B.M.; Subbarao, K.V.; Bruggen, van A.H.C.; Koike, S.T.

    2001-01-01

    Lettuce growers in coastal California have relied mainly on protective fungicide sprays to control downy mildew. Thus, timing of sprays before infection is critical for optimal results. A leaf-wetness-driven, infection-based advisory system, previously developed, did not always perform

  15. impact of fungicide applications for late blight management on ...

    African Journals Online (AJOL)

    budgeting. Benefit-cost ratio, defined as the number of times the fungicide control cost was recouped from the value for the increased yield, was calculated as: ... sub-plots. Analysis of variance (ANOVA) unsprayed sub-plots. Analysis of variance revealed highly significant (P < 0.001) differences (ANOVA) revealed highly ...

  16. Effects of phosphorus fertilization and seed dressing fungicide on ...

    African Journals Online (AJOL)

    Study on the effect of phosphorus fertilization and seed dressing fungicide on occurrence of pea aphid, Acyrthosiphon pisum and yield of lentil was conducted at Debre Zeit and Chefe Donsa for six consecutive years. Lentil genotypes Alemaya and ILL-7664 were sown at the rate of 60kg/ha on 2m wide and 4m long plots.

  17. Effect of benzimidazole fungicides and calcium chloride on ...

    African Journals Online (AJOL)

    SERVER

    2007-06-04

    Jun 4, 2007 ... Botrytis cinerea (Besri and Diatta, 1985; Hmouni et al.,. 1996). It is very likely that the repetitive uses of these systemic fungicides and their persistence during long periods of conservation (Ben Arie, 1975; Prusky, 1985) have led to considerable selective pressure on both species. Moreover, the single site ...

  18. Evaluation studies of some medicinal plant extracts and fungicides ...

    African Journals Online (AJOL)

    Evaluation studies of some medicinal plant extracts and fungicides against Alternaria solani. S Phalisteen, S Ishaq, K Amardeep, J Arif, S Sami. Abstract. Alternaria is a polyphagus fungus that occurs frequently on dead and decaying organic material and is responsible for causing leaf spot disease. In Indian subcontinent ...

  19. Sensitivity of Botrytis cinerea isolates against some fungicides used ...

    African Journals Online (AJOL)

    During August 2004 and 2005, isolates of Botrytis cinerea were collected from table and wine grapes in the Trakya region, Turkey. They were tested for sensitivity to cyprodinil+fludioxonil, fenhexamid, procymidone, pyrimethanil and tebuconazole under laboratory conditions. Fungicide sensitivity tests showed that B. cinerea ...

  20. Effects of Variety and Fungicidal Rate on Cercospora Leaf Spots ...

    African Journals Online (AJOL)

    A field study was carried out at the University of Maiduguri Teaching and Research Farm during the 2006, 2007 and 2008 cropping seasons to evaluate the effects of variety and fungicidal rate on Cercospora leaf spot disease of groundnut. The experimental design used was Randomized Complete Block Design (RCBD) ...

  1. Fungicide, antibiotic, heavy metal resistance and salt tolerance of ...

    African Journals Online (AJOL)

    user

    2011-03-28

    Mar 28, 2011 ... All of the rhizobial isolates showed resistance to the antibiotic (µg ml-1); streptomycin sulphate ... Using fungicides for crop diseases control in legume fields has contributed to increasing yield ..... on growth of Rhizobium japonicum and symbiotically grown soybean in soil under laboratory conditions. Prot.

  2. Theoretical studies on a series of 1,2,4-triazoles derivatives as ...

    Indian Academy of Sciences (India)

    military and space applications.1,2 Explosives con- taining triazole rings have the advantages of less molecular weight, high nitrogen content and density, good thermal stability, low impact sensitivity and large explosive volume, so that they can be used as outstand- ing explosives. Triazoles and their derivatives have also.

  3. Intercountry Transfer of Triazole-Resistant Aspergillus fumigatus on Plant Bulbs

    NARCIS (Netherlands)

    Dunne, K.; Hagen, F.; Pomeroy, N.; Meis, J.F.G.M.; Rogers, T.R.

    2017-01-01

    We investigated whether plants imported to Ireland from the Netherlands might harbor triazole-resistant Aspergillus fumigatus. Samples of plant bulbs were positive for triazole-resistant A. fumigatus with CYP51A mutations. We hypothesize that this represents a route for intercountry transfer of an

  4. Synthesis of a New Class of Triazole-Linked Benzoheterocycles via 1,3-Dipolar Cycloaddition

    Energy Technology Data Exchange (ETDEWEB)

    Barbosa, Fernanda C.G.; Oliveira, Ronaldo N. de, E-mail: ronaldonoliveira@dq.ufrpe.b [Universidade Federal Rural de Pernambuco (LSCB/UFRPE), Recife, PE (Brazil). Dept. de Quimica. Lab. de Sintese de Compostos Bioativos

    2011-07-01

    A new series of 1,2,3-triazole derivatives have been synthesized from phthalimides and terminal alkynes in the presence of a catalytic amount of CuI. The present protocol affords 1,2,3-triazoles in moderate to good yields (44-89%). (author)

  5. Palladium-Catalyzed C–H Arylation of 1,2,3-Triazoles

    Science.gov (United States)

    Zhang, Chengwei; You, Lin; Chen, Chuo

    2016-01-01

    Palladium(II) acetate, in combination with triphenylphosphine, catalyzes direct arylation of 1,4-disubstituted 1,2,3-triazoles effectively. This C–H arylation reaction provides facile access to fully substituted triazoles with well-defined regiochemistry. PMID:27669198

  6. Magnetic susceptibility of complex compounds of rhenium with 1.2.4-triazole

    International Nuclear Information System (INIS)

    Avetikyan, G.B.; Amindzhanov, A.A.; Gagieva, S.Ch.; Kotegov, K.V.

    1991-01-01

    Present article is devoted to magnetic susceptibility of complex compounds of rhenium with 1.2.4-triazole. The thermal transformations of chloride-1.2.4-triazole rhenium complexes were studied by means of static magneto chemistry and thermal differential analysis methods.

  7. Mesogenic copper (II) complexes with [1, 2, 3]-triazole-based ...

    Indian Academy of Sciences (India)

    The first mesogenic Cu(II) complex with [1,2,3]-triazole-based bidentate Schiff bases with flexible terminal alkyl chain, CnH2n+1 (even parity of n = 10-18) has been successfully synthesized. The heterocyclic triazole core was introduced into the target compound through the click reaction between azidoalkane and propargyl ...

  8. Synthesis of a New Class of Triazole-Linked Benzoheterocycles via 1,3-Dipolar Cycloaddition

    International Nuclear Information System (INIS)

    Barbosa, Fernanda C.G.; Oliveira, Ronaldo N. de

    2011-01-01

    A new series of 1,2,3-triazole derivatives have been synthesized from phthalimides and terminal alkynes in the presence of a catalytic amount of CuI. The present protocol affords 1,2,3-triazoles in moderate to good yields (44-89%). (author)

  9. Complex compounds of rhenium with 4-amino-1.2.4-triazole

    International Nuclear Information System (INIS)

    Amindzhanov, A.A.; Gagieva, S.Ch.

    1991-01-01

    Present article is devoted to complex compounds of rhenium with 4-amino-1.2.4-triazole. The complex compounds of rhenium with 4-amino-1.2.4-triazole were synthesized. The composition and structure of obtained complexes was determined by means of various methods.

  10. New 1,2,3-Triazole Iminosugars Derivatives Using Click Chemistry

    Directory of Open Access Journals (Sweden)

    Chahrazed Benhaoua

    2012-01-01

    Full Text Available The click concept refers ease, efficient, and the selective chemicals transformations. In this study, a novel regiospecific copper (I-catalyzed 1, 3-dipolar of terminal alkynes to azide provided a practicable synthetic pathway of triazole iminosugars derivatives. A series of new triazole-pyrrolidinols are reported in good yield.

  11. Triazole-pyridine ligands: a novel approach to chromophoric iridium arrays

    NARCIS (Netherlands)

    Juríček, M.; Felici, M.; Contreras-Carballada, P.; Lauko, J.; Bou, S.R.; Kouwer, P.H.J.; Brouwer, A.M.; Rowan, A.E.

    2011-01-01

    We describe a novel modular approach to a series of luminescent iridium complexes bearing triazole-pyridine-derived ligands that were conveniently prepared by using "click" chemistry. One, two or three triazole-pyridine units were effectively built into the heteroaromatic macromolecule using

  12. Synthesis and Fungicidal Activity of β-Carboline Alkaloids and Their Derivatives

    Directory of Open Access Journals (Sweden)

    Zhibin Li

    2015-07-01

    Full Text Available A series of β-Carboline derivatives were designed, synthesized, and evaluated for their fungicidal activities in this study. Several derivatives electively exhibited fungicidal activities against some fungi. Especially, compound F5 exhibited higher fungicidal activity against Rhizoctonia solani (53.35% than commercial antiviral agent validamycin (36.4%; compound F16 exhibited high fungicidal activity against Oospora citriaurantii ex Persoon (43.28%. Some of the alkaloids and their derivatives (compounds F4 and F25 exhibited broad-spectrum fungicidal activity. Specifically, compound F4 exhibited excellent high broad-spectrum fungicidal activity in vitro, and the curative and protection activities against P. litchi in vivo reached 92.59% and 59.26%, respectively. The new derivative, F4, with optimized physicochemical properties, obviously exhibited higher activities both in vitro and in vivo; therefore, F4 may be used as a new lead structure for the development of fungicidal drugs.

  13. Leaching of two fungicides in spent mushroom substrate amended soil: Influence of amendment rate, fungicide ageing and flow condition.

    Science.gov (United States)

    Álvarez-Martín, Alba; Sánchez-Martín, María J; Ordax, José M; Marín-Benito, Jesús M; Sonia Rodríguez-Cruz, M

    2017-04-15

    A study has been conducted on the leaching of two fungicides, tebuconazole and cymoxanil, in a soil amended with spent mushroom substrate (SMS), with an evaluation of how different factors influence this process. The objective was based on the potential use of SMS as a biosorbent for immobilizing pesticides in vulnerable soils, and the need to know how it could affect the subsequent transport of these retained compounds. Breakthrough curves (BTCs) for 14 C-fungicides, non-incubated and incubated over 30days, were obtained in columns packed with an unamended soil (S), and this soil amended with SMS at rates of 5% (S+SMS5) and 50% (S+SMS50) under saturated and saturated-unsaturated flows. The highest leaching of tebuconazole (>50% of the total 14 C added) was found in S when a saturated water flow was applied to the column, but the percentage of leached fungicide decreased when a saturated-unsaturated flow was applied in both SMS-amended soils. Also a significant decrease in leaching was observed for tebuconazole after incubation in the column, especially in S+SMS50 when both flows were applied. Furthermore, cymoxanil leaching was complete in S and S+SMS when a saturated flow was applied, and maximum peak concentrations were reached at 1pore volume (PV), although BTCs showed peaks with lower concentrations in S+SMS. The amounts of cymoxanil retained only increased in S+SMS when a saturated-unsaturated flow was applied. A more relevant effect of SMS for reducing the leaching of fungicide was observed when cymoxanil was previously incubated in the column, although mineralization was enhanced in this case. These results are of interest for extending SMS application on the control of the leaching of fungicides with different physicochemical characteristics after different ageing times in the soil and water flow conditions applied. Copyright © 2017 Elsevier B.V. All rights reserved.

  14. Sensitivity of Phakopsora pachyrhizi (soybean rust) isolates to fungicides and the reduction of fungal sporulation based on fungicide and timing of application

    Science.gov (United States)

    Soybean rust is a damaging foliar fungal disease of soybean in many soybean-growing areas throughout the world. Strategies to manage soybean rust include the use of foliar fungicides. Fungicides types, the rate of product application, and the number and timing of applications are critical components...

  15. Synthesis, biological activities and SAR studies of new 3-substitutedphenyl-4-substitutedbenzylideneamino-1,2,4-triazole Mannich bases and bis-Mannich bases as ketol-acid reductoisomerase inhibitors.

    Science.gov (United States)

    Wang, Bao-Lei; Zhang, Li-Yuan; Liu, Xing-Hai; Ma, Yi; Zhang, Yan; Li, Zheng-Ming; Zhang, Xiao

    2017-12-15

    A series of new 3-substitutedphenyl-4-substitutedbenzylideneamino-1,2,4-triazole Mannich bases and bis-Mannich bases were synthesized through Mannich reaction with high yields. Their structures were confirmed by means of IR, 1 H NMR, 13 C NMR and elemental analysis. The preliminary bioassay indicated that compounds 7g, 7h and 7l exhibited potent in vitro inhibitory activities against ketol-acid reductoisomerase (KARI) with K i value of (0.38 ± 0.25), (6.59 ± 2.75) and (8.46 ± 3.99) μmol/L, respectively, and were comparable with IpOHA. They could be new KARI inhibitors for follow-up research. Some of the title compounds also exhibited obvious herbicidal activities against Echinochloa crusgalli and remarkable in vitro fungicidal activities against Physalospora piricola and Rhizoctonia cerealis. The SAR of the compounds were analyzed, in which the molecular docking revealed the binding mode of 7g with the KARI, and the 3D-QSAR results provided useful information for guiding further optimization of this kind of structures to discover new fungicidal agents towards Rhizoctonia cerealis. Copyright © 2017 Elsevier Ltd. All rights reserved.

  16. Aluminum Dimer Containing Bulky 1,2,3-Triazolate Ligand

    Directory of Open Access Journals (Sweden)

    Issam Kobrsi

    2014-01-01

    Full Text Available The first molecular aluminum 1,2,3-triazolato complex was synthesized bearing a bulky 1,2,3-triazolate ligand. Oligomers and polymers were avoided due to the bulkiness and noncoordinating nature of the substituents. The novel Al2N4 ring formed contains symmetrical Al-N bond distances unexpectedly having asymmetric Al-N-N angles of 144.55(15° and 115.83(14°. This asymmetry demonstrates the effect of the steric hindrance of the ligand.

  17. Synthesis of new 1,2,3-triazol-carbohydrates

    Directory of Open Access Journals (Sweden)

    Bruna M. Guimarães

    2012-06-01

    Full Text Available The reaction of a mixture of 1-azide-glycopyranoside (1 and appropriate alkynes (2a-e, in the presence of CuI/Et3N as catalyst system, and acetonitrile as solvent, provided the glycoside triazoles (3a-e in moderate-to-excellent yields (60-93%. We observed that the reactivity of the alcohols decreased due to steric hindrance (prim>sec>terc. Furthermore, the use of ultrasound irradiation was favorable to furnish the desired products with excellent yields and a shorter reaction time, except for the compound (3e.      

  18. Fungicidal activity of silver nanoparticles against Alternaria brassicicola

    Science.gov (United States)

    Gupta, Deepika; Chauhan, Pratima

    2016-04-01

    This work highlighted the fungicidal properties of silver nanoparticles against Alternaria brassicicola. Alternaria brassicicola causes Black spot of Cauliflower, radish, cabbage, kale which results in sever agricultural loss. We treat the synthesised silver nanoparticles (AgNPs) of 10, 25, 50, 100 and 110 ppm concentrations against Alternaria brassicicola on PDA containing Petri dish. We calculated inhibitory rate (%) in order to evaluate the antifungal efficacy of silver nanoparticles against pathogens. Treatment with 100ppm AgNPs resulted in maximum inhibition of Alternaria brassicicola i.e.92.2%. 110ppm of AgNPS also shows the same result, therefore 100ppm AgNPs was treated as optimize concentration. AgNPs effectively inhibited the growth of a Alternaria brassicicola, which suggests that AgNPs could be used as fungicide in plant disease management. Further research and development are necessary to translate this technology into plant disease management strategies.

  19. Fungicide Efficacy in Peach Rusty Spot Control in Serbia

    Directory of Open Access Journals (Sweden)

    Nenad Dolovac

    2010-01-01

    Full Text Available Rusty Spot has long been known as a harmful peach disease in many parts of the world. During the past several years, rusty spot infection of the late-maturing peach cultivars (Summerset, Suncrest, Fayette and O’Henry caused significant yield losses in Serbia.Although the etiology of the disease is still unknown, there are numerous studies attempting to set a strategy for its control and recommend appropriate chemical and other peach protection methods. However, because of specific environmental conditions in Serbia, recommended protection method using repeated fungicide treatments, starting from petal fall, did not prove to be efficient and the rate of infection in some susceptible peach cultivars reached 100%. In 2003 and 2004 a field trial was conducted in order to test the efficacy of fungicides (a.i. kresoxim-methyl, flusilazole and sulfur for the efficient control of Rusty Spot epidemics. The trial was carried out under conditions of natural infection on the peach cv. Summerset at the locality of Bela Crkva, Serbia. In the ntreated control plots,high disease incidence was recorded with the percentage of affected fruit surface ranging from 33.5% in the first, up to the 35.4% in the second year of the trail. Among fungicides included in the trial, kresoxim-methyl proved to be the most efficient (90.25% in the first and 91.12% in the second year of the trial, flusilazole exhibited lower efficacy (87.28% and 80.61%, respectively while sulfur was the least efficient 82.33% and 80.30%, respectively. Determination of the most efficient fungicide for the peach rusty spot control in Serbia provides basic nformation for further investigations which will include optimization of treatment terms, as well as additional agro-technical control measures.

  20. Radioisotopes and fungicide research- present status and future prospects

    International Nuclear Information System (INIS)

    Chatrath, M.S.

    1996-01-01

    The developments in pesticides and radioisotopes fields were so near to each other that at a very early stage in this history, both became linked together and their usefulness was recognised for faster development. The purpose of this communication is to illustrate the present status these techniques in fungicide research by drawing suitable examples and also to bring out the directions in which future research will be going with the aid of these tools. 72 refs

  1. Bibliometric analysis of literature on antifungal triazole resistance: 1980 – 2015

    Science.gov (United States)

    Sweileh, Waleed M.; Sawalha, Ansam F.; Al-Jabi, Samah; Zyoud, Sa’ed H.

    2017-01-01

    Background Triazole antifungal agents play an important role in the treatment of a wide range of fungal infections. Little is known about antifungal triazole drug resistance when compared to antibiotic resistance. Therefore, this study was carried out to give a bibliometric overview of literature on triazole antifungal drug resistance. Methods Keywords related to triazole drug class and resistance were used in a search query in the Scopus search engine. The time span was set from 1980 to 2015. Data pertaining to growth of publications, the most active countries and institutions, the most cited articles, and mapping of molecular mechanisms of resistance were analyzed. Results A total of 1648 journal articles were retrieved with an average of 20.46 citations per article. Annual growth of triazole resistance showed an increasing pattern during the study period. The United States of America (n=446; 27.06%) ranked first in productivity followed by the United Kingdom (UK) (n=176; 10.68%), and China (n=133; 8.07%). Radboud University Nijmegen Medical Centre (n=69, 4.19%) in the Netherlands ranked first in productivity, while the journal Antimicrobial Agents and Chemotherapy ranked first (n=255; 15.47%) in publishing articles on triazole resistance. Mapping mechanisms of resistance showed that efflux pump and mutations in target enzyme are major mechanisms described in resistance to triazoles. Conclusion There was a growth of publications on triazole resistance in the past two decades with the bulk of publications on triazole resistance in Candida species. The data presented here will serve as baseline information for future comparative purposes. PMID:28331838

  2. Radiotracer studies of fungicide residues in food plants

    International Nuclear Information System (INIS)

    1990-04-01

    Agricultural fungicides are chemicals used on seeds, crops and in soils throughout the growing season. Fungicide treatments may lead to various levels of chemical residues in food commodities. Primary emphasis has been placed on ethylenebisdithiocarbamates (EBDCs), an important group of agrofungicides used in preparations for spraying or dusting major crops such as apples, pears, broccoli, cabbages, egg plants, cauliflower, grapes, lettuce, peppers, celery, cucumbers and tomatoes. Treatments with EBDCs result in terminal residues containing ethylenthiourea (ETU). This is a toxicologically significant decomposition product which has attracted considerable attention in recent years due to indications of its potential goitrogenic and carcinogenic properties. In recognition of the need for a coordinated examination of ETU levels in food, particularly under tropical conditions, the program of radiotracer techniques as a tool for studying fungicide residue problems on food was initiated in 1984. In current studies, three EBDCs, maneb, zineb and mancozeb from different manufacturers in different countries were analysed. This report describes the model protocols (Annexes I, II and III) as they were set up for determination of residues in commodities and soil, using radiotracer and conventional chromatographic techniques . In the 16 papers presented in this report C 14 -labelled EBDCs are determined in plants, vegetables, and soils, before and after cooking, as a function of time and of other agricultural parameters. Refs, figs and tabs

  3. Synthesis, Antibacterial and Antifungal Activity of 4-Substituted-5-Aryl-1,2,4-Triazoles

    Directory of Open Access Journals (Sweden)

    Aleksandra Buzarovska

    2001-09-01

    Full Text Available A few 4-allyl/amino-5-aryl-1,2,4-triazoles were synthesized and tested for antibacterial and antifungal effects against Escherichia coli, Bacillus subtilis, Salmonella enteritidis, Staphylococcus aureus, Aspergillus niger and Candida albicans. 4-Allyl-5-aryl-1,2,4-triazoles were obtained by the oxidative cyclization of the appropriate 1-substituted-4-allylthiosemicarbazides and 4-amino-5-aryl-1,2,4-triazoles were obtained by cyclization of the potassium salts of appropriately substituted dithiocarbazinic acids with hydrazine hydrate. The new synthesized compounds were characterized using IR, 1H- NMR, 13C-NMR and UV spectral data together with elemental analysis.

  4. Post-influenzal triazole-resistant aspergillosis following allogeneic stem cell transplantation.

    Science.gov (United States)

    Talento, Alida Fe; Dunne, Katie; Murphy, Niamh; O'Connell, Brian; Chan, Grace; Joyce, Eimear Ann; Hagen, Ferry; Meis, Jacques F; Fahy, Ruauri; Bacon, Larry; Vandenberge, Elisabeth; Rogers, Thomas R

    2018-03-23

    Influenza virus infection is now recognised as a risk factor for invasive pulmonary aspergillosis (IPA). Delays in diagnosis contribute to delayed commencement of antifungal therapy. Additionally, the emergence of resistance to first-line triazole antifungal agents puts emphasis on early detection to prevent adverse outcomes. We present 2 allogeneic stem cell transplant patients who developed IPA due to triazole-resistant Aspergillus fumigatus following influenza infection. We underline the challenges faced in the management of these cases, the importance of early diagnosis and need for surveillance given the emergence of triazole-resistance. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.

  5. Synthesis of Thiadiazoles and 1,2,4-Triazoles Derived from Cyclopropane Dicarboxylic Acid

    Directory of Open Access Journals (Sweden)

    M. Aouad

    2005-09-01

    Full Text Available New heterocyclic derivatives of cyclopropane dicarboxylic acid comprising thiadiazole and 1,2,4-triazole moieties are reported. Reaction of 1,1-cyclopropane dicarboxylic acid (1 with thiosemicarbazide and phosphorous oxychloride resulted in 1,1-bis (2-amino-1,3,4-thiadiazol-5- ylcyclopropane (2. Cyclopropane dicarboxylic acid thiosemicarbazide (6 was converted into 1,1-bis(3-thio-4H-1,2,4-triazol-5-yl cyclo- propane (7 by ring closure in an alkaline medium. The thiadiazole 2 and the triazole 7 were converted into a variety of derivatives.

  6. Synthesis, crystal structures and spectral characterization of chiral 4-R-1,2,4-triazoles

    Science.gov (United States)

    Gural'skiy, Il'ya A.; Reshetnikov, Viktor A.; Omelchenko, Irina V.; Szebesczyk, Agnieszka; Gumienna-Kontecka, Elzbieta; Fritsky, Igor O.

    2017-01-01

    1,2,4-triazoles attract attention as actively used medications and ligands for constructing coordination architectures. In this paper we describe four optically active 4-substituted 1,2,4-triazoles that have been prepared by Bayer's synthesis from the corresponding aliphatic chiral amines. This approach tends to be universal towards different triazoles and permits to conserve a homochirality of substrates. Novel asymmetric molecules have been characterized by spectroscopic techniques and their structures have been retrieved from the single crystal X-ray analysis. Chiro-optical studies of these heterocycles have been made by means of circular dichroism spectroscopy.

  7. Backbone-Fluorinated 1,2,3-Triazole-Containing Dipeptide Surrogates

    DEFF Research Database (Denmark)

    Engel-Andreasen, Jens; Wellhöfer, Isabelle; Wich, Kathrine

    2017-01-01

    The 1,2,3-triazole moiety can be incorporated as a peptide bond bioisostere to provide protease resistance in peptidomimetics. Herein, we report the synthesis of peptidomimetic building blocks containing backbone-fluorinated 1,4-disubstituted 1,2,3-triazole moieties. Synthetic protocols...... for the preparation of various Xaa-Gly dipeptide surrogates in the form of Xaa-ψ[triazole]-F2Gly building blocks were established, and selected examples were introduced into the endogenous peptide opioid receptor ligand Leu-enkephalin as a model compound....

  8. Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives

    Directory of Open Access Journals (Sweden)

    Priscila López-Rojas

    2018-01-01

    Full Text Available A new series of coumarin-1,2,3-triazole conjugates with varied alkyl, phenyl and heterocycle moieties at C-4 of the triazole nucleus were synthesized using a copper(I-catalysed Huisgen 1,3-dipolar cycloaddition reaction of corresponding O-propargylated coumarin (3 or N-propargylated coumarin (6 with alkyl or aryl azides. Based on their minimal inhibitory concentrations (MICs against selected microorganisms, six out of twenty-six compounds showed significant antibacterial activity towards Enterococcus faecalis (MIC = 12.5–50 µg/mL. Moreover, the synthesized triazoles show relatively low toxicity against human erythrocytes.

  9. Curative and eradicant action of fungicides to control Phakopsora pachyrhizi in soybean plants

    Directory of Open Access Journals (Sweden)

    Erlei Melo Reis

    Full Text Available ABSTRACT Experiments were carried out in a growth chamber and laboratory to quantify the curative and eradicant actions of fungicides in Asian soybean rust control. The experiments were conducted with the CD 214 RR cultivar, assessing the following fungicides, separately or in association, chlorothalonil, flutriafol, cyproconazole + trifloxystrobin, epoxiconazole + pyraclostrobin, cyproconazole + azoxystrobin, and cyproconazole + picoxystrobin. The fungicides were applied at four (curative and nine days after inoculation (eradicant treatment. Treatments were evaluated according to the density of lesions and uredia/cm2, and the eradicant treatment was assessed based on the necrosis of lesions/uredia and on uredospore viability. Except for the fungicide chlorothalonil, there was curative action of latent/virtual infections by the fungicides. Penetrant fungicides that are absorbed have curative and eradicant action to soybean rust.

  10. Assessing predictive uncertainty in comparative toxicity potentials of triazoles.

    Science.gov (United States)

    Golsteijn, Laura; Iqbal, M Sarfraz; Cassani, Stefano; Hendriks, Harrie W M; Kovarich, Simona; Papa, Ester; Rorije, Emiel; Sahlin, Ullrika; Huijbregts, Mark A J

    2014-02-01

    Comparative toxicity potentials (CTPs) quantify the potential ecotoxicological impacts of chemicals per unit of emission. They are the product of a substance's environmental fate, exposure, and hazardous concentration. When empirical data are lacking, substance properties can be predicted. The goal of the present study was to assess the influence of predictive uncertainty in substance property predictions on the CTPs of triazoles. Physicochemical and toxic properties were predicted with quantitative structure-activity relationships (QSARs), and uncertainty in the predictions was quantified with use of the data underlying the QSARs. Degradation half-lives were based on a probability distribution representing experimental half-lives of triazoles. Uncertainty related to the species' sample size that was present in the prediction of the hazardous aquatic concentration was also included. All parameter uncertainties were treated as probability distributions, and propagated by Monte Carlo simulations. The 90% confidence interval of the CTPs typically spanned nearly 4 orders of magnitude. The CTP uncertainty was mainly determined by uncertainty in soil sorption and soil degradation rates, together with the small number of species sampled. In contrast, uncertainty in species-specific toxicity predictions contributed relatively little. The findings imply that the reliability of CTP predictions for the chemicals studied can be improved particularly by including experimental data for soil sorption and soil degradation, and by developing toxicity QSARs for more species. © 2013 SETAC.

  11. Medicinal attributes of 1,2,3-triazoles: Current developments.

    Science.gov (United States)

    Dheer, Divya; Singh, Virender; Shankar, Ravi

    2017-04-01

    1,2,3-Triazoles are important five-membered heterocyclic scaffold due to their extensive biological activities. This framework can be readily obtained in good to excellent yields on the multigram scale through click chemistry via reaction of aryl/alkyl halides, alkynes and NaN 3 under ambient conditions. It has been an emerging area of interest for many researchers throughout the globe owing to its immense pharmacological scope. The present work aims to summarize the current approaches adopted for the synthesis of the 1,2,3-triazole and medicinal significance of these architectures as a lead structure for the discovery of drug molecules such as COX-1/COX-2 inhibitors (celecoxib, pyrazofurin), HIV protease inhibitors, CB1 cannabinoid receptor antagonist and much more which are in the pipeline of clinical trials. The emphasis has been given on the major advancements in the medicinal prospectus of this pharmacophore for the period during 2008-2016. Copyright © 2017 Elsevier Inc. All rights reserved.

  12. Phytotoxicity: An Overview of the Physiological Responses of Plants Exposed to Fungicides

    Directory of Open Access Journals (Sweden)

    Maria Celeste Dias

    2012-01-01

    Full Text Available In the last decades, the use of fungicides in agriculture for fungi diseases control has become crucial. Fungicide research has produced a diverse range of products with novel modes of action. However, the extensive use of these compounds in the agriculture system raises public concern because of the harmful potential of such substances in the environment and human health. Moreover, the phytotoxic effects of some fungicides are already recognized but little is known about the impact of these compounds on the photosynthetic apparatus. This paper presents a comprehensive overview of the literature considering different classes of fungicides and their effects on plant physiology, with particular emphasis on photosynthesis.

  13. In vivo sensitivity of Phakopsora pachyrhizi to DMI and QoI fungicides

    Directory of Open Access Journals (Sweden)

    Erlei Melo Reis

    2015-03-01

    Full Text Available In in vivo experiments the sensitivity of 18 isolates of Phakopsora pachyrhizi from several regions of Brazil to IDM fungicides (cyproconazole, epoxiconazole and tebuconazole and an IQE (pyraclostrobin were evaluated. The assessments were based on leaflet uredia density. Inhibitory concentration (IC50 and sensitivity reduction factor were determined for all fungicide x strain interactions. Tebuconazole sensitivity reduction was detected for most fungus isolates. In contrast, there was no fungicide shift in sensitivity of the fungus to pyraclostrobin. We conclude that the control failure of soybean rust found in some farms is due to the reduced sensitivity of the fungus to the IDM fungicide and that it remains sensitive to pyraclostrobin.

  14. Direct access to triazole-olefins through catalytic cycloaddition of azides to unsaturated aldehydes.

    Science.gov (United States)

    Li, Wenjun; Jia, Qianfa; Du, Zhiyun; Wang, Jian

    2013-10-03

    In situ formed dienamines as HOMO-raising dipolarophiles react with azides to afford the corresponding triazole-olefins in good to excellent yields via a catalytic inverse-electron-demand 1,3-dipolar cycloaddition process.

  15. Rhodium-Catalyzed Enantioselective Cyclopropanation of Olefins with N-Sulfonyl 1,2,3-Triazoles

    Science.gov (United States)

    Chuprakov, Stepan; Kwok, Sen Wai; Zhang, Li; Lercher, Lukas; Fokin, Valery V.

    2009-01-01

    N-Sulfonyl 1,2,3-triazoles readily form rhodium(II) azavinyl carbenes, which react with olefins to produce cyclopropanes with excellent diastereo- and enantioselectivity and in high yield. PMID:19928917

  16. Hydrogen-Bonding Interactions in Luminescent Quinoline-Triazoles with Dominant 1D Crystals

    Directory of Open Access Journals (Sweden)

    Shi-Qiang Bai

    2017-09-01

    Full Text Available Quinoline-triazoles 2-((4-(diethoxymethyl-1H-1,2,3-triazol-1-ylmethylquinoline (1, 2-((4-(m-tolyl-1H-1,2,3-triazol-1-ylmethylquinoline (2 and 2-((4-(p-tolyl-1H-1,2,3-triazol-1-ylmethylquinoline (3 have been prepared with CuAAC click reactions and used as a model series to probe the relationship between lattice H-bonding interaction and crystal direction of growth. Crystals of 1–3 are 1D tape and prism shapes that correlate with their intermolecular and solvent 1D lattice H-bonding interactions. All compounds were thermally stable up to about 200 C and blue-green emissive in solution.

  17. Molecular simulation, quantum chemical calculations and electrochemical studies for inhibition of mild steel by triazoles

    International Nuclear Information System (INIS)

    Khaled, K.F.

    2008-01-01

    The inhibition performance of three triazole derivatives on mild steel in 1 M HCl were tested by weight loss, potentiodynamic polarization and electrochemical impedance spectroscopy (EIS). The adsorption behavior of these molecules at the Fe surface was studied by the molecular dynamics simulation method and the quantum chemical calculations. Results showed that these compounds inhibit the corrosion of mild steel in 1 M HCl solution significantly. Molecular simulation studies were applied to optimize the adsorption structures of triazole derivatives. The iron/inhibitor/solvent interfaces were simulated and the charges on the inhibitor molecules as well as their structural parameters were calculated in presence of solvent effects. Aminotriazole was the best inhibitor among the three triazole derivatives (triazole, aminotriazole and benzotriazole). The adsorption of the inhibitors on the mild steel surface in the acid solution was found to obey Langmuir's adsorption isotherm

  18. Mode of Action for Reproductive and Hepatic Toxicity Inferred from a Genomic Study of Triazole Antifungals

    Science.gov (United States)

    The mode of action for the reproductive toxicity of triazole antifungals have been previously characterized by an observed increased in serum testosterone, hepatotoxicity, and reduced insemination and fertility indices. In order to refine our mechanistic understanding of these m...

  19. Studies on some complexes of zirconium(IV) with substituted triazoles having thioamide group

    International Nuclear Information System (INIS)

    Sharma, R.N.; Pandey, R.N.

    1993-01-01

    Some air stable zirconium (IV) complexes with physiologically active substituted triazoles such as 3-(4-pyridyl)-4-phenyl-1,2,4-triazole-5-thione (PyPtTH), 4-amino-3-methyl-5-mercapto-s-triazole (AmMTH) and 1,2,4-triazole-3(5)-thiol (tTH) containing thioamide group have been prepared and characterised on the basis of various physico-chemical methods. All complexes have been isolated in ethanolic media and found to be diamagnetic in nature. In some cases the deprotonation of thiol tautomeric form of ligand occurs at pH = 8. The systematic shifts of all four thioamide bands are studied thoroughly and bonding through thione as well as thiol sulphur has been assigned. An octahedral structure for all complexes have been tentatively assigned. (author). 22 refs., 2 tabs., 1 fig

  20. Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles with Nitriles

    Science.gov (United States)

    Horneff, Tony; Chuprakov, Stepan; Chernyak, Natalia

    2009-01-01

    Stable and readily available 1-sulfonyl triazoles are converted to the corresponding imidazoles in good to excellent yields via a rhodium(II)-catalyzed reaction with nitriles. Rhodium iminocarbenoids are proposed intermediates. PMID:18855475

  1. 1,2,3-Triazoles from carbonyl azides and alkynes: filling the gap.

    Science.gov (United States)

    Haldón, Estela; Álvarez, Eleuterio; Nicasio, M Carmen; Pérez, Pedro J

    2014-08-18

    Electron deficient azides are challenging substrates in CuAAC reactions. Particularly, when N-carbonyl azides are applied the formation of N-carbonyl triazoles has not yet been observed. We report herein the first example of this class of reaction, with a copper-based system that efficiently enables the synthesis of N-carbamoyl 1,2,3-triazoles by [3+2] cycloaddition of N-carbamoyl azides and alkynes.

  2. Reactions of certain acids with ammoniac 1,2,4-triazole complexes of rhenium (5)

    International Nuclear Information System (INIS)

    Amindzhanov, A.A.; Gagieva, S.Ch.

    1991-01-01

    The process of interaction of formic, acetic, hydrofluoric and sulfuric acids with ammoniac-1,2,4-triazole complexes of rhenium (5) was studied. The complexes [Re 2 O 3 (OH) 2 L 2 X 2 (H 2 O) 2 ], where X=CH 3 COO, HCOO, F; L=1,2,4-triazole, and [Re 2 O 2 (SO 4 ) 3 L 2 (H 2 O) 2 ] were synthesized. The properties of the complexes prepared were characterized by physicochemical methods

  3. Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited.

    Science.gov (United States)

    Krasiński, Antoni; Fokin, Valery V; Sharpless, K Barry

    2004-04-15

    After revisiting earlier works reporting the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles via the addition of bromomagnesium acetylides to azides, much improved yields of the products were obtained for a wide array of azides and alkynes. The intermediates of that reaction can be trapped with different electrophiles to regioselectively form 1,4,5-trisubstituted 1,2,3-triazoles. [reaction: see text

  4. Transannulation of 1-Sulfonyl-1,2,3-Triazoles with Heterocumulenes

    Science.gov (United States)

    Chuprakov, Stepan; Kwok, Sen Wai; Fokin, Valery V.

    2013-01-01

    Readily available 1-mesyl-1,2,3-triazoles are efficiently converted into a variety of imidazolones and thiazoles by Rh(II)-catalyzed denitrogenative reactions with isocyanates and isothiocyanates, respectively. The proposed triazolediazoimine equilibrium results in the formation of highly reactive azavinyl metal-carbenes, which react with heterocumulenes causing an apparent swap of 1,2,3-triazole core for another heterocycle. PMID:23477345

  5. Synthesis and Biological Activity of Substituted Urea and Thiourea Derivatives Containing 1,2,4-Triazole Moieties

    Science.gov (United States)

    2013-03-19

    Biological Activity of Substituted Urea and Thiourea Derivatives Containing 1,2,4- Triazole Moieties Bedia Kocyigit-Kaymakcioglu 1,*, Ahmet Ozgur Celen...of novel thiourea and urea derivatives containing 1,2,4- triazole moieties were synthesized and evaluated for their antifungal and larvicidal activity... Triazole derivatives 3a–e and 4a–e were synthesized by reacting thiocarbohydrazide with thiourea and urea compounds 1a–e and 2a–e, respectively

  6. Triazole induced concentration-related gene signatures in rat whole embryo culture.

    Science.gov (United States)

    Robinson, Joshua F; Tonk, Elisa C M; Verhoef, Aart; Piersma, Aldert H

    2012-09-01

    Commonly used as antifungal agents in agriculture and medicine, triazoles have been shown to cause teratogenicity in a diverse set of animal models. Here, we evaluated the dose-dependent impacts of flusilazole, cyproconazole and triadimefon, on global gene expression in relation to effects on embryonic development using the rat whole embryo culture (WEC) model. After 4 h exposure, we identified changes in gene expression due to triazole exposure which preceded morphological alterations observed at 48 h. In general, across the three triazoles, we observed similar directionality of regulation in gene expression and the magnitude of effects on gene expression correlated with the degree of induced developmental toxicity. Significantly regulated genes included key members of steroid/cholesterol and retinoic acid metabolism and hindbrain developmental pathways. Direct comparisons with previous studies suggest that triazole-gene signatures identified in the WEC overlap with zebrafish and mouse, and furthermore, triazoles impact gene expression in a similar manner as retinoic acid exposures in rat embryos. In summary, we further differentiate pathways underlying triazole-developmental toxicity using WEC and demonstrate the conservation of these response-pathways across model systems. Copyright © 2012 Elsevier Inc. All rights reserved.

  7. ZINClick: a database of 16 million novel, patentable, and readily synthesizable 1,4-disubstituted triazoles.

    Science.gov (United States)

    Massarotti, Alberto; Brunco, Angelo; Sorba, Giovanni; Tron, Gian Cesare

    2014-02-24

    Since Professors Sharpless, Finn, and Kolb first introduced the concept of "click reactions" in 2001 as powerful tools in drug discovery, 1,4-disubstituted-1,2,3-triazoles have become important in medicinal chemistry due to the simultaneous discovery by Sharpless, Fokin, and Meldal of a perfect click 1,3-dipolar cycloaddition reaction between azides and alkynes catalyzed by copper salts. Because of their chemical features, these triazoles are proposed to be aggressive pharmacophores that participate in drug-receptor interactions while maintaining an excellent chemical and metabolic profile. Surprisingly, no virtual libraries of 1,4-disubstituted-1,2,3-triazoles have been generated for the systematic investigation of the click-chemical space. In this manuscript, a database of triazoles called ZINClick is generated from literature-reported alkynes and azides that can be synthesized within three steps from commercially available products. This combinatorial database contains over 16 million 1,4-disubstituted-1,2,3-triazoles that are easily synthesizable, new, and patentable! The structural diversity of ZINClick ( http://www.symech.it/ZINClick ) will be explored. ZINClick will also be compared to other available databases, and its application during the design of novel bioactive molecules containing triazole nuclei will be discussed.

  8. A biological evaluation on in vitro radiosensitization of nitro-triazole derivatives

    International Nuclear Information System (INIS)

    Li Wuling; Zhang Wensheng; Yang Xinhai

    1997-01-01

    Objective: To assess the radiosensitization of nitro-triazole derivatives and elucidate the structure-activity relationships within this group of compounds. Method: The partition coefficient (p), reduction potential (E 1/2 ), cytotoxicity and sensitization activity were determined by HPLC, polarography and colony formation, respectively. Results: It was found that among these 22 derivatives, two compounds were more efficient than MISO, and other three were of the same efficiency as MISO was in radiosensitizing hypoxic cells, the rest showed poor radiosensitizing properties. As 2-nitroimidazoles, the radiosensitizing activity of a 3-nitro-triazole derivative correlates with its electron affinity, determined as E 1/2 , half-wave reduction potential. The greater is the electron affinity i.e. the more positive the E 1/2 , the greater is the radiosensitizing efficiency. The value of E 1/2 , partition coefficient p value and cytotoxicity of a nitro-triazole derivative are influenced by the structure and chemical properties of the substituent at N 1 or 5 position of triazole ring. The nitro-triazoles examined show only limited differential hypoxic: aerobic toxicity. Conclusion: Although the nitro-triazole derivation are not viable hypoxia-mediated cytotoxins, the radiosensitization of some of them should be studied thoroughly

  9. Conversion of the fungicide, ziram in rice plants

    International Nuclear Information System (INIS)

    Kumarasamy, R.; Raghu, K.

    1976-01-01

    Zinc dimethyldithiocarbamate (ziram) is a toliar fungicide used for the control of the blast disease of rice caused by Pyricularia oryzae, and is also used for the control of the plant diseases in crops like groundnut, cotton, etc. Since there is lack of data on the conversion products of this fungicide. This investigation was carried out. The results of the author's recent studies with 35 S-labelled ziram in rice seedlings were reported. The 35 S-Labelled ziram (specific activity 1.5 m Ci/m mole) was sprayed on the rice seedlings of 25 days old. At different intervals of time, the seedlings were removed, washed thoroughly, cut into pieces, and extracted with 80% ethanol. By the method described in ''K. Raghu et al., Origin and fate of chemical residents in food, agriculture and fisheries, I.A.E.A., Vienna, 1975, pp. 137-148,'' the segments corresponding to the standards of dimethyl dithio carbamate-alanine (DDCA), DDC-glucoside (DDCG), thiazolidine-2-thione-4-carbamic acid (TTCA), unidentified divolent fungicide (X), and ziram were cut out and the radioactivity was counted in cocktail D scintillation fluid using an LS-100 Beckmann liquid scintillation counter. It is indeed interesting to note that ziram is converted in plant tissues into dimethyldithiocarbamate derivatives like DDCG, DDCA, TTCA and X within 24 hr after spraying. The amounts of these derivatives varied in the course of sampling up to 8 days after spraying. Further studies are needed as to the quantitative nature of these products, but the present report clearly demonstrates the formation of these conversion products in the rice leaves treated with ziram. (Kobatake, H.)

  10. Low-airflow drying of fungicide-treated shelled corn

    International Nuclear Information System (INIS)

    Peterson, W.H.; Benson, P.W.

    1993-02-01

    Approved fungicides inhibit mold growth in shelled corn and allow for longer, natural-air drying. The longer drying periods permit lower than-normal airflows and smaller power units, thus reducing electrical demands on utilities in corn-producing states. Researchers placed approximately 67 m 3 (1900 bu) of one variety of shelled corn at approximately 24% moisture in each of five equally sized storage bins. They partitioned each bin vertically and filled one half of each bin with fungicide-treated corn and one half with untreated corn. Each of four bins used a different airflow. A fifth bin used the lowest of the four airflows but was equipped to capture and use solar energy. All corn dried rapidly with resulting good quality. The percentage of damaged kernels was significantly higher for untreated than for treated corn. The energy required for the lowest airflow system was approximately one half of that required for the higher, more traditional airflows. Because of lower-than-normal airflows, the electrical demand on the utility is approximately one fourth as great as that imposed when the higher, more traditional natural-air systems are used. The 1991 corn growing and drying seasons were unusual in central Illinois, the site of the study. Both harvest and drying occurred several weeks ahead of schedule. Additional work is needed to verify that findings hold true during more-normal Midwest corn growing and drying seasons; the investigators predict that they will. It should be noted that the fungicide used in this study has not yet been approved for widespread use in drying corn

  11. A novel triazole-based cationic gemini surfactant: synthesis and effect on corrosion inhibition of carbon steel in hydrochloric acid

    International Nuclear Information System (INIS)

    Qiu Lingguang; Xie Anjian; Shen Yuhua

    2005-01-01

    A triazole-based cationic gemini surfactant, 3,5-bis(methylene octadecyl dimethylammonium chloride)-1,2,4-triazole (18-triazole-18) has been synthesized, and its effect on corrosion inhibition of A 3 steel in 1 M HCl has been studied using the weight-loss method. The result showed that 18-triazole-18 acted as an excellent inhibitor in 1 M HCl. It was found that the adsorption mechanism of 18-triazole-18 on the steel surface in acid medium was quite different from that of cationic gemini surfactants containing dimethylene as a spacer, as well as that of conventional cationic single-chained surfactants, which is due to unique molecular structure of 18-triazole-18. 18-Triazole-18 may be adsorbed on the steel surface in acid medium through a maximum of four atoms or groups, i.e., the two nitrogen atoms of triazole ring and two quaternary ammonium head groups. Four regions of surfactant concentration could be divided to illustrate the adsorption of 18-triazole-18 on the steel surface, and four different adsorption mechanisms may take place in different regions of surfactant concentration

  12. Gas-Phase Tautomerism in the Triazoles and Tetrazoles: A Study by Photoelectron Spectroscopy and ab Initio Molecular Orbital Calculations

    Science.gov (United States)

    Palmer, Michael H.; Simpson, Isobel; Wheeler, J. Ross

    1981-11-01

    The photoelectron spectra of the tautomeric 1,2,3,- and 1,2,4-triazole and 1,2,3,4-tetrazole systems have been compared with the corresponding N-methyl derivatives. The dominant tautomers in the gas phase have been identified as 2 H-1,2,3-triazole, 1 H-1,2,4-triazole and 2H-tetrazole. Full optimisation of the equilibrium geometry by ab initio molecular orbital methods leads to the same conclusions, for relative stability of the tautomers in each of the triazoles, but the calculations wrongly predict the tetrazole tautomerism.

  13. Dimensional modulation and magnetic properties of triazole- and bis(triazole)-based copper(II) coordination polymers tuned by aromatic polycarboxylates

    International Nuclear Information System (INIS)

    Zhang, Ju-Wen; Zhao, Wei; Lu, Qi-Lin; Luan, Jian; Qu, Yun; Wang, Xiu-Li

    2014-01-01

    Five new metal–organic coordination polymers ([Cu 3 (μ 2 -OH) 2 (atrz) 2 (nph) 2 (H 2 O) 2 ]·2H 2 O) n (1), ([Cu 2 (μ 3 -OH)(atrz)(1,2,4-btc)]·2H 2 O) n (2), ([Cu 2 (μ 3 -OH)(atrz)(1,2,4-btc)(H 2 O)]·H 2 O) n (3), [Cu(dth) 0.5 (nph)(H 2 O)] n (4) and [Cu(dth)(Hnip) 2 ] n (5) [atrz=4-amino-1,2,4-triazole, dth=N,N'-di(4H-1,2,4-triazole)hexanamide, H 2 nph=3-nitrophthalic acid, 1,2,4-H 3 btc=1,2,4-benzenetricarboxylic acid and H 2 nip=5-nitroisophthalic acid] were hydrothermally synthesized and structurally characterized. Polymer 1 shows a one-dimensional (1D) chain. Polymers 2 and 3 exhibit similar tetranuclear Cu II 4 cluster-based three-dimensional (3D) frameworks with the same components. Polymer 4 possesses a 3D framework with a 4 12 ·6 3 -pcu topology. Polymer 5 displays a 3D framework with a 4 4 ·6 10 ·8-mab topology. The magnetic properties of 1–4 were investigated. - Graphical abstract: Five triazole-based copper(II) polymers modulated by polycarboxylates were synthesized. Bis-triazole-bis-amide ligand and polycarboxylates play important roles in tuning dimensionality of polymers. Magnetic properties of polymers were investigated. - Highlights: • Five triazole- and bis(triazole)-based copper(II) coordination polymers tuned by aromatic polycarboxylates were obtained. • The aromatic polycarboxylates have an important influence on the dimensionality of five polymers. • The magnetic properties of four polymers were investigated

  14. Reduced fungicide doses in cereals: Which parameters to consider?

    DEFF Research Database (Denmark)

    Jørgensen, Lise Nistrup

    2015-01-01

    , the pathogen, disease pressure and timing of treatments. Certain diseases are known to require higher input (40- 75% rates) for achieving satisfactory control – this is the case for Septoria leaf blight, Rhynchosporium net blotch and Fusarium head blight, whereas most rust diseases generally have been found...... to be controlled successfully at rates down to quarter rates. Fungicides, in general, show highly variable dose responses for specific diseases, which is important to know when specific advice is given. Preventive treatments generally require less input compared with treatments during the latent period or later...

  15. FUNGICIDAL PROPERTIES OF ARTEMISIA AROMATIC PLANTS TOWARDS FUSARIUM OXYSPORUM

    Directory of Open Access Journals (Sweden)

    Ivashchenko Iryna Vіctorovna

    2015-08-01

    Full Text Available The article establishes the fungicidal activity of water extracts of Artemisia maritimа L., Artemisia austriaca Jacq., under the concentration of 100, 50 and 25 mg/ml on dry matter with regard to the phytopathogenic mushroom Fusarium oxysporum. It also shows the fungistatic influence of extract of Artemisia dracunculus L. under concentration 25 and 50 mg/ml, fungicidal – under 100 mg/ml. Concerning Artemisia abrotanum L., the slow growth of mushroom is observed under the concentration 25 mg/ml, fungicidal effect – under 50 and 100 mg/ml. The paper provides the information on the component composition of ethereal oil and phenolic compounds of Artemisia maritimа, Artemisia austriaca, Artemisia abrotanum, Artemisia dracunculus, cultivated in Zhytomyr Polissya. The chief ingredients of ethereal oil which is synthesized by the plant of Artemisia abrotanum are 1,8-cineole (30.44% and camphor (31.92%. A high 1,8-cineole and camphor content determines antimicrobial properties of the plants. Amount of phenolic compounds in the air-dry raw Artemisia abrotanum is 2.98 percent. By the method of highly efficient solution chromatography (HESChr in the grass of Artemisia abrotanum we have detected 23 phenolic compounds, of which we identified such flavonoids as rutin, luteolin-7-glycoside as well as caffeic, chlorogenic and isochlorogenic acids. The main compounds of ethereal oil of Artemisia austriaca are trans-verbenole (30.77 %, pinocarvone (10.77 % and sabinilacetate (18.16 %. In the grass of Artemisia austriaca we have detected 31 phenolic compounds, of which we identified such flavonoids as rutin, apigenin, quercetin-bioside and the following acids: caffeic, chlorogenic, and isochlorogenic. Amount of phenolic compounds in the air-dry raw Austrian wormwood is 27.25 mg / g (2.73 %. The main component of ethereal oil of Artemisia dracunculus is methyleugenol (94.65 %. We have discovered 31 phenolic compounds in the grass of linear-leaved wormwood

  16. An evaluation of some fungicides in the management of fruit and leaf ...

    African Journals Online (AJOL)

    Four fungicide treatments viz Ben late (Benomyl), Cupravit (Copper oxychloride), Dithane M45 (Mancozeb), and Ben late alternated with Dithane M45 were applied to control Phaeoramularia angolensis in a block of the variety "Valencia" in the citrus orchard at Kiige, Uganda. No fungicide was applied to the control. Benlate ...

  17. Efficacy and economics of fungicide spray in the control of late blight ...

    African Journals Online (AJOL)

    The chemical control started immediately after the first disease symptom was observed (41days after crop emergence) and chemical control was repeated after every 7 days for contact fungicides and 21 days for preventive fungicide. In 1997 AL-624 and Tolcha received 4 -5 and 2 applications, respectively, of the protectant ...

  18. Fungicidal effect of 15 disinfectants against 24 fungal contaminants commonly found in bread and cheese manufacturing

    DEFF Research Database (Denmark)

    Bundgaard-Nielsen, Kirsten; Nielsen, Per Væggemose

    1996-01-01

    .0 % formaldehyde, 0.1 % potassium hydroxide, 3.0 % hydrogen peroxide or 0.3 % peracetic acid were ineffective as fungicides. The fungicidal effect of quaternary ammonium compounds and chlorine compounds showed great variance between species and among the 6 tested isolates of Penicillium roqueforti var. roqueforti...

  19. Fungicide resistance phenotypes in Botrytis cinerea populations from blueberries in California and Washington

    Science.gov (United States)

    Gray mold caused by Botrytis cinerea is a major postharvest disease of blueberries grown in the Central Valley of California (CA) and western Washington State (WA). Understanding fungicide- resistant phenotypes of B. cinerea is important to the development of preharvest fungicide programs for contro...

  20. Effects of azole fungicides on the function of sex and thyroid hormones

    DEFF Research Database (Denmark)

    Kjærstad, Mia Birkhøj; Andersen, Helle Raun; Taxvig, Camilla

    Azole-fungicides are frequently used in Denmark. Epoxiconazole, propiconazole, and tebuconazole had endocrine disrupting properties in cell based assays. In rats, epoxiconazole and tebuconazole increased gestational length, maternal progesterone level, and masculinized female-offspring. Besides, ......, tebuconazole caused feminization of male-offspring. Similar effects were previously demonstrated for prochloraz. The results indicate that azole-fungicides in general have endocrine disrupting properties....

  1. Alleviation of fungicide-induced phytotoxicity in greengram [Vigna radiata (L.) Wilczek] using fungicide-tolerant and plant growth promoting Pseudomonas strain

    OpenAIRE

    Ahemad, Munees; Khan, Mohammad Saghir

    2012-01-01

    This study was designed to explore beneficial plant-associated rhizobacteria exhibiting substantial tolerance against fungicide tebuconazole vis-à-vis synthesizing plant growth regulators under fungicide stressed soils and to evaluate further these multifaceted rhizobacteria for protection and growth promotion of greengram [Vigna radiata (L.) Wilczek] plants against phytotoxicity of tebuconazole. Tebuconazole-tolerant and plant growth promoting bacterial strain PS1 was isolated from mustard (...

  2. Emerging resistance against different fungicides in Lasiodiplodia theobromae, the cause of mango dieback in Pakistan

    Directory of Open Access Journals (Sweden)

    Rehman ur Ateeq

    2015-01-01

    Full Text Available Dieback of mango caused by Lasiodiplodia theobromae is among several diseases responsible for low crop production in Pakistan. To further complicate the issue, resistance in L. theobromae is emerging against different fungicides. L. theobromae was isolated from diseased samples of mango plants collected from various orchards in the Multan District. The efficacy of different fungicides viz. copper oxychloride, diethofencarb, pyrachlostrobin, carbendazim, difenoconazole, mancozeb, and thiophanate-methyl was evaluated in vitro using a poison food technique. Thiophanate-methyl at all concentrations was found to be the most effective among five systemic fungicides against L. theobromae, followed by carbendazim, difenoconazole and diethofencarb. The fungicides, i.e., thiophanate-methyl, difenoconazole, carbendazim and diethofencarb showed maximum efficacy with increasing concentration. The isolates of L. theobromae showed some resistance development against the tested fungicides when compared with previous work. These investigations provide new information about chemical selection for the control of holistic disease in mango growing zones of Pakistan.

  3. Sustained release of fungicide metalaxyl by mesoporous silica nanospheres

    International Nuclear Information System (INIS)

    Wanyika, Harrison

    2013-01-01

    The use of nanomaterials for the controlled delivery of pesticides is nascent technology that has the potential to increase the efficiency of food production and decrease pollution. In this work, the prospect of mesoporous silica nanoparticles (MSN) for storage and controlled release of metalaxyl fungicide has been investigated. Mesoporous silica nanospheres with average particle diameters of 162 nm and average pore sizes of 3.2 nm were prepared by a sol–gel process. Metalaxyl molecules were loaded into MSN pores from an aqueous solution by a rotary evaporation method. The loaded amount of metalaxyl as evaluated by thermogravimetric analysis was about 14 wt%. Release of the fungicide entrapped in the MSN matrix revealed sustained release behavior. About 76 % of the free metalaxyl was released in soil within a period of 30 days while only 11.5 and 47 % of the metalaxyl contained in the MSN carrier was released in soil and water, respectively, within the same period. The study showed that MSN can be used to successfully store metalaxyl molecules in its mesoporous framework and significantly delay their release in soil

  4. Design, Synthesis and Fungicidal Activities of Some Novel Pyrazole Derivatives

    Directory of Open Access Journals (Sweden)

    Xue-Ru Liu

    2014-09-01

    Full Text Available In order to discover new compounds with good fungicidal activities, 32 pyrazole derivatives were designed and synthesized. The structures of the target compounds were confirmed by 1H-NMR, 13C-NMR, and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS, and their fungicidal activities against Botrytis cinerea, Rhizoctonia solani Kuhn, Valsa mali Miyabe et Yamada, Thanatephorus cucumeris (Frank Donk, Fusarium oxysporum (S-chl f.sp. cucumerinum Owen, and Fusarium graminearum Schw were tested. The bioassay results indicated that most of the derivatives exhibited considerable antifungal activities, especially compound 26 containing a p-trifluoromethyl- phenyl moiety showed the highest activity, with EC50 values of 2.432, 2.182, 1.787, 1.638, 6.986, and 6.043 μg/mL against B. cinerea, R. solani, V. mali, T. cucumeris, F. oxysporum, and F. graminearum, respectively. Moreover, the activities of compounds such as compounds 27–32 were enhanced by introducing isothiocyanate and carboxamide moieties to the 5-position of the pyrazole ring.

  5. Dipping Strawberry Plants in Fungicides before Planting to Control Anthracnose

    Directory of Open Access Journals (Sweden)

    Myeong Hyeon Nam

    2014-03-01

    Full Text Available Anthracnose crown rot (ACR, caused by Colletotrichum fructicola, is a serious disease of strawberry in Korea. The primary inoculums of ACR were symptomless strawberry plants, plant debris, and other host plants. To effectively control anthracnose in symptomless transplanted strawberries, it is necessary to use diseasefree plants, detect the disease early, and apply a fungicide. Therefore, in 2010 and 2011, we evaluated the efficacy of pre-plant fungicide dips by using strawberry transplants infected by C. fructicola for the control of anthracnose. Dipping plants in prochloraz-Mn for 10 min before planting was most effective for controlling anthracnose in symptomless strawberry plants and resulted in more than 76% control efficacy. Azoxystrobin showed a control efficacy of over 40%, but plants treated with pyraclostrobin, mancozeb and iminoctadine tris showed high disease severity. The control efficacy of the dip treatment with prochloraz-Mn did not differ with temperature and time. Treatment with prochloraz-Mn for more than an hour caused growth suppression in strawberry plants. Therefore, the development of anthracnose can be effectively reduced by dipping strawberry plants for 10 min in prochloraz-Mn before planting.

  6. FUNGICIDE APPLICATION FOR MAINTAINING POSTHARVEST QUALITY IN TOMATO FRUITS

    Directory of Open Access Journals (Sweden)

    D. M. Vani

    2014-07-01

    Full Text Available Tomato fruits are usually consumed soon after harvest, however, as they are mainly comprised of water, and its walls are fragile, facilitates the emergence of diseases, making necessary the use of preventive measures in the field in order to reduce incidence of disease. The objective is then to evaluate the effect of foliar application of fungicides on the final quality of tomato fruits in postharvest. There were 13 applications of foliar fungicides Azoxystrobin+Cyproconazol and Boscalida, 7 applications Tebuconazol+Trifoxistrobin and 17 applications of Propamocarb+Fluopicolide (Control. We analyzed the incidence of Fusarium sp. in fruits, decay percentage of fruit weight (g and Brix. For incidence of Fusarium sp. in fruits, treatments Tebuconazol+Trifoxistrobin and Azoxistrobin+Ciproconazol reduced by 14.3%, the pathogen in fruits. There was a decrease of 82% in the deterioration of fruits treated with Tebuconazol+Trifoxistrobin and 91% in those treated with Azoxistrobin+Ciproconazol. As for the weight gain, treatments Tebuconazol+Trifoxistrobin, Boscalida and Azoxistrobin+Ciproconazol reduced the weight gain in 8.12%, 20.8% and 38.8%, respectively, compared to the control. ° Brix values of fruits treated with Tebuconazol+Trifoxistrobin and Boscalida were higher than those treated with Azoxistrobin+Ciproconazol and Control (Propamocarb+Fluopicolide. It is concluded that the treatment carried out with Tebuconazol+Trifoxistrobin afforded the greatest benefits in maintaining the tomato fruits in harvest.

  7. Sustained release of fungicide metalaxyl by mesoporous silica nanospheres

    Energy Technology Data Exchange (ETDEWEB)

    Wanyika, Harrison, E-mail: hwanyika@gmail.com [Jomo Kenyatta University of Agriculture and Technology, Department of Chemistry (Kenya)

    2013-08-15

    The use of nanomaterials for the controlled delivery of pesticides is nascent technology that has the potential to increase the efficiency of food production and decrease pollution. In this work, the prospect of mesoporous silica nanoparticles (MSN) for storage and controlled release of metalaxyl fungicide has been investigated. Mesoporous silica nanospheres with average particle diameters of 162 nm and average pore sizes of 3.2 nm were prepared by a sol-gel process. Metalaxyl molecules were loaded into MSN pores from an aqueous solution by a rotary evaporation method. The loaded amount of metalaxyl as evaluated by thermogravimetric analysis was about 14 wt%. Release of the fungicide entrapped in the MSN matrix revealed sustained release behavior. About 76 % of the free metalaxyl was released in soil within a period of 30 days while only 11.5 and 47 % of the metalaxyl contained in the MSN carrier was released in soil and water, respectively, within the same period. The study showed that MSN can be used to successfully store metalaxyl molecules in its mesoporous framework and significantly delay their release in soil.

  8. Vacuole-targeting fungicidal activity of amphotericin B

    Directory of Open Access Journals (Sweden)

    Akira eOgita

    2012-03-01

    Full Text Available Invasive fungal infections are recognized as major threats to patients with immune depression as well as those with cancer chemotherapy. Amphotericin B (AmB, a classical antifungal agent with a polyene macrolide structure, is widely used for the control of serious fungal infections. However, the clinical use of this antibiotic is limited by the treatment-associated side effects and the appearance of resistant strains. AmB lethality has been generally elucidated by the alteration of plasma membrane ion permeability due to its specific binding to plasma membrane ergosterol. While, the recent studies with Saccharomyces cerevisiae and Candida albicans reveals the vacuole disruptive action as another cause of AmB lethality on the basis of its marked amplification in combination with allicin, an allyl sulfur compound from garlic. Indeed, AmB causes a serious structural damage to the vacuole membrane at a lethal concentration, and even at a non-lethal concentration in combination with allicin. Such an enhancement effect of allicin is dependent on an inhibition of ergosterol-trafficking from the plasma membrane to the vacuole membrane, which is considered to be a cellular response to protect against the vacuole membrane disintegration. Allicin can also decrease the minimum fungicidal concentration of AmB against the pathogenic fungi C. albicans and Aspergillus fumigatus, as is the case of S. cerevisiae. The synergistic fungicidal activities of AmB and allicin may have significant implications in the development of the vacuole-targeting chemotherapy against fungal infections.

  9. Four triazole-bridging coordination polymers containing (m-phenol)-1,2,4-triazole: Syntheses, structures and properties of fluorescence and magnetism

    International Nuclear Information System (INIS)

    Liu Bing; Guo Guocong; Huang Jinshun

    2006-01-01

    Four triazole-bridging coordination complexes, [Zn 4 (ptr) 2 (SO 4 ) 3 (μ 3 -OH) 2 (H 2 O) 4 ] n (1), [Hg(CN) 2 (ptr)] n (2), [Hg(Cl) 2 (ptr)] n (3), and [Cu 2 (μ 2 -ptr) 2 (μ 2 -F) 2 ] n (SiF 6 ) n .2nH 2 O (4), were synthesized with (m-phenol)-1,2,4-triazole (ptr). Compounds 1-4 with extended structures of 4-substituted 1,2,4-triazole are rarely reported. The layered structure of 1 can be regarded as constructed from the 2-D inorganic backbone of SO 4 2- (2) anions bridging [Zn 4 (μ 3 -OH) 2 (H 2 O) 2 ] 6- subunits with the ptr ligands anchoring to both sides of backbone. Compounds 2 and 3 are the first mercury(II) complexes with 4-substituted 1,2,4-triazole, which feature the ptr ligand acting as a bidentate ligand bridging the Hg(II) atoms to form arciform -Hg-ptr-Hg-ptr chains. The structure of 4 is constructed from the F atoms bridging Cu atoms in symmetrical μ 2 -coordination mode to form a zigzag cationic chain with each ptr ligand bridging a pair of Cu atom on the both sides, resulting in a nonplanar 5-membered [Cu 2 N 2 F] ring. Fluorescent properties of 1-4 were characterized and the magnetic property of 4 shows antiferromagnetic interaction between the copper(II) ions. - Four triazole-bridging coordination complexes, [Zn 4 (ptr) 2 (SO 4 ) 3 (μ 3 -OH) 2 (H 2 O) 4 ] n (1), [Hg(CN) 2 (ptr)] n (2), [Hg(Cl) 2 (ptr)] n (3) and [Cu 2 (μ 2 -ptr) 2 (μ 2 -F) 2 ] n (SiF 6 ) n .2nH 2 O (4), were synthesized with (m-phenol)-1,2,4-triazole (ptr). Compounds 1-4 with extended structures of 4-substituted 1,2,4-triazole are rarely reported

  10. Solid-phase synthesis of NH-1,2,3-triazoles using 4,4′- bismethoxybenzhydryl azide

    DEFF Research Database (Denmark)

    Cohrt, Anders Emil O'Hanlon; Le Quement, Sebastian Thordal; Nielsen, Thomas Eiland

    2014-01-01

    Readily available 4,4′-bismethoxybenzhydryl azide was found to be a useful building block for the synthesis of NH-1,2,3-triazoles through copper(I)-catalyzed cycloaddition reactions with solid-supported terminal alkynes, followed by acid-mediated deprotection. Peptide-containing NH-1,2,3-triazoles...

  11. Preparation and Antibacterial Properties of Substituted 1,2,4-Triazoles

    Directory of Open Access Journals (Sweden)

    Ionuţ Ledeţi

    2015-01-01

    Full Text Available Background. Both 1,2,3- and 1,2,4-triazoles are nowadays incorporated in numerous antibacterial pharmaceutical formulations. Aim. Our study aimed to prepare three substituted 1,2,4-triazoles and to evaluate their antibacterial properties. Materials and Methods. One disubstituted and two trisubstituted 1,2,4-triazoles were prepared and characterised by physical and spectroscopic properties (melting point, FTIR, NMR, and GC-MS. The antibacterial properties were studied against three bacterial strains: Staphylococcus aureus (ATCC 25923, Escherichia coli (ATCC 25922, and Pseudomonas aeruginosa (ATCC 27853, by the agar disk diffusion method and the dilution method with MIC (minimal inhibitory concentration determination. Results. The spectroscopic characterization of compounds and the working protocol for the synthesis of the triazolic derivatives are described. The compounds were obtained with 15–43% yields and with high purities, confirmed by the NMR analysis. The evaluation of biological activities showed that the compounds act as antibacterial agents against Staphylococcus aureus (ATCC 25923, while being inactive against Escherichia coli (ATCC 25922 and Pseudomonas aeruginosa (ATCC 27853. Conclusions. Our results indicate that compounds containing 1,2,4-triazolic moiety have great potential in developing a wide variety of new antibacterial formulations.

  12. Activity of two different triazoles in a murine model of paracoccidioidomycosis Actividad de dos triazoles diferentes en un modelo murino de paracoccidioidomicosis

    Directory of Open Access Journals (Sweden)

    Susana Restrepo

    1992-04-01

    Full Text Available A new orally absorbable triazole (Schering 39304 with a long serum half-life in man (60 hours, was tried in a murine model of progressive paracoccidioidomycosis and compared with itraconazole, another triazole which has proven effective in this mycosis. Only 15% of the infected, untreated mice survived while 53 to 75% of the animals receiving itraconazole survived. Mice treated with Schering 39304 exhibited higher (86 - 100% survival rates. Statistically, the 5 mg/kg Sch 39304 was superior to the 50 mg/kg itraconazole dose. Lung cultures showed that 20 mg/kg/day of Sch achieved sterilization of the infectious foci. These results indicate that the new triazole will have a place in the treatment of paracoccidioidomycosisUn nuevo derivado triazólico Schering 39304 que tiene una vida promedio prolongada (60 horas, asi como otro triazol (itraconazole de eficacia comprobada en la paracoccidioidomicosis, fueron ensayados en un modelo murino. Se encontró que solo sobrevivían el 15% de los animales infectados no tratados; del grupo tratado con Itrazonazol sobrevivieron el 53% de los que recibieron 20 mg/kg/dia y el 86% de aquellos con 50 mg/kg/dia. De los ratones que recibieron Sch 39304 sobrevivieron el 86% de los tratados con la dosis baja (5 mg/kg y el 100% con la dosis mayor (20 mg/kg. Se encontraron diferencias estadísticamente significativas entre esta última droga y el itraconazol. Además, los cultivos de pulmón mostraron que solo Sch 39304 a la dosis alta, era capaz de erradicar el hongo de los tejidos. Estos resultados indican que tal triazol tendrá importancia en el tratamiento de la paracoccidioidomicosis humana

  13. The rising threat of fungicide resistance in plant pathogenic fungi: Botrytis as a case study.

    Science.gov (United States)

    Hahn, Matthias

    2014-10-01

    The introduction of site-specific fungicides almost 50 years ago has revolutionized chemical plant protection, providing highly efficient, low toxicity compounds for control of fungal diseases. However, it was soon discovered that plant pathogenic fungi can adapt to fungicide treatments by mutations leading to resistance and loss of fungicide efficacy. The grey mould fungus Botrytis cinerea, a major cause of pre- and post-harvest losses in fruit and vegetable production, is notorious as a 'high risk' organism for rapid resistance development. In this review, the mechanisms and the history of fungicide resistance in Botrytis are outlined. The introduction of new fungicide classes for grey mould control was always followed by the appearance of resistance in field populations. In addition to target site resistance, B. cinerea has also developed a resistance mechanism based on drug efflux transport. Excessive spraying programmes have resulted in the selection of multiresistant strains in several countries, in particular in strawberry fields. The rapid erosion of fungicide activity against these strains represents a major challenge for the future of fungicides against Botrytis. To maintain adequate protection of intensive cultures against grey mould, strict implementation of resistance management measures are required as well as alternative strategies with non-chemical products.

  14. Effects of Fungicides, Time of Application, and Application Method on Control of Sclerotinia Blight in Peanut

    Directory of Open Access Journals (Sweden)

    Jason E. Woodward

    2015-01-01

    Full Text Available Field studies were conducted from 2007 to 2010 to evaluate the response of peanut cultivars to different fungicides, application timings, and methods. Overall, fungicides reduced Sclerotinia blight incidence and increased pod yields when applied to susceptible and partially resistant cultivars. Disease suppression was greater when full fungicide rates were applied preventatively; however, yields between fungicide treated plots were similar. Lower levels of disease and higher yields were achieved with the partially resistant cultivar Tamrun OL07 compared to the susceptible cultivars Flavor Runner 458 and Tamrun OL 02. Despite possessing improved resistance Tamrun OL07 responded to all fungicide applications. While similar levels of disease control were achieved with broadcast or banded applications made during the day or at night, the yield response for the different application methods was inconsistent among years. A negative relationship (slope = −73.8; R2=0.73; P<0.01 was observed between final disease incidence ratings and yield data from studies where a fungicide response was observed. These studies suggest that both boscalid and fluazinam are effective at controlling Sclerotinia blight in peanuts. Alternative management strategies such as nighttime and banded applications could allow for lower fungicide rates to be used; however, additional studies are warranted.

  15. Population density of Beauveria bassiana in soil under the action of fungicides and native microbial populations

    Directory of Open Access Journals (Sweden)

    Flávia Barbosa Soares

    2017-08-01

    Full Text Available This study investigated whether populations of naturally-occurring soil bacteria, fungi and actinomycetes influence the effect of fungicides on the survival and growth of Beauveria bassiana. The toxicity of methyl thiophanate, pyraclostrobin, mancozeb and copper oxychloride at the recommended doses was analyzed in culture medium and in soil inoculated with fungus at various time points after addition of fungicides. All fungicides completely inhibited the growth and sporulation of B. bassiana in the culture medium. The fungicides were less toxic in soil, emphasizing the action of the microbial populations, which interfered with the toxic effects of these products to the fungus. Actinomycetes had the greatest influence on the entomopathogen, inhibiting it or degrading the fungicides to contribute to the survival and growth of B. bassiana in soil. Native populations of fungi and bacteria had a smaller influence on the population density of B. bassiana and the action of fungicides towards entomopathogen. The toxic effect of the fungicides was greater when added to the soil one hour before or after inoculation than at 48h after inoculation.

  16. Spread of Botrytis cinerea Strains with Multiple Fungicide Resistance in German Horticulture

    Science.gov (United States)

    Rupp, Sabrina; Weber, Roland W. S.; Rieger, Daniel; Detzel, Peter; Hahn, Matthias

    2017-01-01

    Botrytis cinerea is a major plant pathogen, causing gray mold rot in a variety of cultures. Repeated fungicide applications are common but have resulted in the development of fungal populations with resistance to one or more fungicides. In this study, we have monitored fungicide resistance frequencies and the occurrence of multiple resistance in Botrytis isolates from raspberries, strawberries, grapes, stone fruits and ornamental flowers in Germany in 2010 to 2015. High frequencies of resistance to all classes of botryticides was common in all cultures, and isolates with multiple fungicide resistance represented a major part of the populations. A monitoring in a raspberry field over six seasons revealed a continuous increase in resistance frequencies and the emergence of multiresistant Botrytis strains. In a cherry orchard and a vineyard, evidence of the immigration of multiresistant strains from the outside was obtained. Inoculation experiments with fungicide-treated leaves in the laboratory and with strawberry plants cultivated in the greenhouse or outdoors revealed a nearly complete loss of fungicide efficacy against multiresistant strains. B. cinerea field strains carrying multiple resistance mutations against all classes of site-specific fungicides were found to show similar fitness as sensitive field strains under laboratory conditions, based on their vegetative growth, reproduction, stress resistance, virulence and competitiveness in mixed infection experiments. Our data indicate an alarming increase in the occurrence of multiresistance in B. cinerea populations from different cultures, which presents a major threat to the chemical control of gray mold. PMID:28096799

  17. Spread of Botrytis cinerea Strains with Multiple Fungicide Resistance in German Horticulture.

    Science.gov (United States)

    Rupp, Sabrina; Weber, Roland W S; Rieger, Daniel; Detzel, Peter; Hahn, Matthias

    2016-01-01

    Botrytis cinerea is a major plant pathogen, causing gray mold rot in a variety of cultures. Repeated fungicide applications are common but have resulted in the development of fungal populations with resistance to one or more fungicides. In this study, we have monitored fungicide resistance frequencies and the occurrence of multiple resistance in Botrytis isolates from raspberries, strawberries, grapes, stone fruits and ornamental flowers in Germany in 2010 to 2015. High frequencies of resistance to all classes of botryticides was common in all cultures, and isolates with multiple fungicide resistance represented a major part of the populations. A monitoring in a raspberry field over six seasons revealed a continuous increase in resistance frequencies and the emergence of multiresistant Botrytis strains. In a cherry orchard and a vineyard, evidence of the immigration of multiresistant strains from the outside was obtained. Inoculation experiments with fungicide-treated leaves in the laboratory and with strawberry plants cultivated in the greenhouse or outdoors revealed a nearly complete loss of fungicide efficacy against multiresistant strains. B. cinerea field strains carrying multiple resistance mutations against all classes of site-specific fungicides were found to show similar fitness as sensitive field strains under laboratory conditions, based on their vegetative growth, reproduction, stress resistance, virulence and competitiveness in mixed infection experiments. Our data indicate an alarming increase in the occurrence of multiresistance in B. cinerea populations from different cultures, which presents a major threat to the chemical control of gray mold.

  18. Consequences of co-applying insecticides and fungicides for managing Thrips tabaci (Thysanoptera: Thripidae) on onion.

    Science.gov (United States)

    Nault, Brian A; Hsu, Cynthia L; Hoepting, Christine A

    2013-07-01

    Insecticides and fungicides are commonly co-applied in a tank mix to protect onions from onion thrips, Thrips tabaci Lindeman, and foliar pathogens. Co-applications reduce production costs, but past research shows that an insecticide's performance can be reduced when co-applied with a fungicide. An evaluation was made of the effects of co-applying spinetoram, abamectin and spirotetramat with commonly used fungicides, with and without the addition of a penetrating surfactant, on onion thrips control in onion fields. Co-applications of insecticides with chlorothalonil fungicides reduced thrips control by 25-48% compared with control levels provided by the insecticides alone in three of five trials. Inclusion of a penetrating surfactant at recommended rates with the insecticide and chlorothalonil fungicide did not consistently overcome this problem. Co-applications of insecticides with other fungicides did not interfere with thrips control. Co-applications of pesticides targeting multiple organisms should be examined closely to ensure that control of each organism is not compromised. To manage onion thrips in onion most effectively, insecticides should be applied with a penetrating surfactant, and should be applied separately from chlorothalonil fungicides. © 2012 Society of Chemical Industry.

  19. Evaluation of fungicides and biopesticides for the control of fusarium wilt of tomato

    International Nuclear Information System (INIS)

    Akhtar, T.; Iftikhar, Y.

    2017-01-01

    Fusarium wilt is highly destructive soil borne pathogen in tomato. Current study was carried out to evaluate commercially available fungicides and bio-fungicides in-vitro and in-vivo, for their efficacy against Fusarium oxysporum f.sp. lycopersici. Firstly four fungicides were evaluated under laboratory conditions. Three promising fungicides, two biopesticides and Trichoderma harzianum were further applied both in greenhouse and field experiments. During in-vitro studies PDA amended with fungicides with different treatments at the rate 1% almost completely inhibited the growth of Fol with varying degree of success whereas Nativo being the most effective treatment with 98% reduction in growth as compared to control. Nativo significantly reduced the disease incidence (32.75 %) at concentration of 1%. While Poly-beta-hydroxyl-butyric-acid effectively promoted the tomato growth. Maximum reduction in disease (30.14 %) was expressed by Nativo followed by Teagro (25.06 %) under field conditions. Nativo was found to be the most effective fungicide for management of Fol both In vitro and In vivo. Further field evaluations of the fungicides are required. (author)

  20. Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse.

    Science.gov (United States)

    Kim, Moo-Key; Choi, Gyung-Ja; Lee, Hoi-Seon

    2003-03-12

    Fungicidal activity of Curcuma longa rhizome-derived materials against Botrytis cineria, Erysiphe graminis, Phytophthora infestans, Puccinia recondita, Pyricularia oryzae, and Rhizoctonia solani was tested using a whole plant method in vivo. It was compared with synthetic fungicides and four commercially available compounds derived from C. longa. The response varied with the tested plant pathogen. At 1000 mg/L, the hexane extract of C. longa showed fungicidal activities against E.graminis, P. infestans, and R. solani, and the ethyl acetate extract of C. longa showed fungicidal activities against B. cineria, P. infestans, Pu. recondita, and R. solani. Curcumin was isolated from the ethyl acetate fraction using chromatographic techniques and showed fungicidal activities against P. infestans, Pu. recondita, and R. solani with 100, 100, and 63% control values at 500 mg/L and 85, 76, and 45% control values at 250 mg/L, respectively. In the test with components derived from C. longa, turmerone exhibited weak activity against E. graminis, but no activity was observed from treatments with borneol, 1,8-cineole, sabinene, and turmerone. In comparison, potent fungicidal activity with chlorothalonil against P. infestans at 50 mg/L and dichlofluanid against B. cinerea at 50 mg/L was exhibited. These results may be an indication of at least one of the fungicidal actions of curcumin derived from C. longa.

  1. Pd-catalyzed regioselective arylation on the C-5 position of N-aryl 1,2,3-triazoles.

    Science.gov (United States)

    Yamajala, K Durga Bhaskar; Patil, Mahendra; Banerjee, Shaibal

    2015-03-20

    We herein report a highly efficient method for the arylation at the C-5 position of N-aryl 1,2,3-triazoles via a direct palladium catalyzed arylation reaction. The optimal reaction conditions required a combination of Pd(OAc)2 and tris(o-tolyl)phosphine as catalyst, and Cs2CO3 as the base under inert atmosphere. A variety of C-5 substituted N-aryl 1,2,3-triazoles were prepared using these conditions with yields in the 70-88% range. Regioselective C-5 arylations were also performed on 1,4-disubstituted 1,2,3-triazoles. The regioselectivity in triazole substitution at the C-5 position was confirmed by single crystal XRD. In addition, computational investigations of key steps of the catalytic cycle using the density functional theory have provided a rationalization to the selective C-5 arylation of N-aryl 1,2,3-triazoles.

  2. Gender and Species-Mediated Differences in the In Vitro Metabolism of Triadimefon by Rodent Hepatic Microsomes

    Science.gov (United States)

    Understanding how metabolism kinetics differ between genders and species is important in developing informative pharmacokinetic models and accurately assessing risk. Metabolism of the conazole fungicide Triadimefon (TDN) was studied in hepatic microsomes of SD rats and CD-1 mice...

  3. Fungicide application method’ and the interpretation of mycorrhizal fungus insect indirect effects

    Science.gov (United States)

    Laird, Robert A.; Addicott, John F.

    2008-09-01

    Mycorrhizal fungi, by altering their host plant's physiology, can have indirect effects on insect herbivores. The 'fungicide application method' is a common approach used to investigate the indirect effects of mycorrhizal fungi on insects. This approach works by using initially mycorrhizal plants, and then generating a subset of these plants that are free of mycorrhizal fungi by applying fungicide to their roots. When insect feeding-bioassays are conducted using the resulting mycorrhizal and non-mycorrhizal plants, differences in insect performance are typically attributed to differences in mycorrhizal colonization per se, rather than the application of the fungicide. Thus, the fungicide application method relies on the assumption that there is no direct toxicity of the fungicide on the focal insect species, and no indirect effects on the focal insect resulting from effects of the fungicide on the host plant or on non-target soil micro-organisms. We tested this critical assumption by feeding Zygogramma exclamationis (Chrysomelidae) larvae on non-mycorrhizal Helianthus annuus (Asteraceae) plants whose roots were treated with a solution of the fungicide benomyl or with a distilled water control. Larvae fed on benomyl-treated plants had reduced survival, lower relative growth rate, and lower food conversion efficiency, compared to larvae fed on control plants. Hence, fungicides applied to roots can affect herbivorous insect performance even in the absence of the possibility of mycorrhizal fungi-mediated effects. We recommend caution when using fungicide application and suggest that selective inoculation is a preferable method of generating mycorrhizal and non-mycorrhizal plants when studying mycorrhizal fungi-insect indirect effects.

  4. Additive and synergistic antiandrogenic activities of mixtures of azol fungicides and vinclozolin

    Energy Technology Data Exchange (ETDEWEB)

    Christen, Verena [University of Applied Sciences and Arts Northwestern Switzerland, School of Life Sciences, Gründenstrasse 40, CH-4132 Muttenz (Switzerland); Crettaz, Pierre [Federal Office of Public Health, Division Chemical Products, 3003 Bern (Switzerland); Fent, Karl, E-mail: karl.fent@fhnw.ch [University of Applied Sciences and Arts Northwestern Switzerland, School of Life Sciences, Gründenstrasse 40, CH-4132 Muttenz (Switzerland); ETH Zürich, Department of Environmental System Sciences, Institute of Biogeochemistry and Pollution Dynamics, Universitätsstrasse 16, CH-8092 Zürich (Switzerland)

    2014-09-15

    Objective: Many pesticides including pyrethroids and azole fungicides are suspected to have an endocrine disrupting property. At present, the joint activity of compound mixtures is only marginally known. Here we tested the hypothesis that the antiandrogenic activity of mixtures of azole fungicides can be predicted by the concentration addition (CA) model. Methods: The antiandrogenic activity was assessed in MDA-kb2 cells. Following assessing single compounds activities mixtures of azole fungicides and vinclozolin were investigated. Interactions were analyzed by direct comparison between experimental and estimated dose–response curves assuming CA, followed by an analysis by the isobole method and the toxic unit approach. Results: The antiandrogenic activity of pyrethroids deltamethrin, cypermethrin, fenvalerate and permethrin was weak, while the azole fungicides tebuconazole, propiconazole, epoxiconazole, econazole and vinclozolin exhibited strong antiandrogenic activity. Ten binary and one ternary mixture combinations of five antiandrogenic fungicides were assessed at equi-effective concentrations of EC{sub 25} and EC{sub 50}. Isoboles indicated that about 50% of the binary mixtures were additive and 50% synergistic. Synergism was even more frequently indicated by the toxic unit approach. Conclusion: Our data lead to the conclusion that interactions in mixtures follow the CA model. However, a surprisingly high percentage of synergistic interactions occurred. Therefore, the mixture activity of antiandrogenic azole fungicides is at least additive. Practice: Mixtures should also be considered for additive antiandrogenic activity in hazard and risk assessment. Implications: Our evaluation provides an appropriate “proof of concept”, but whether it equally translates to in vivo effects should further be investigated. - Highlights: • Humans are exposed to pesticide mixtures such as pyrethroids and azole fungicides. • We assessed the antiandrogenicity of

  5. Chemical management in fungicide sensitivity of Mycosphaerella fijiensis collected from banana fields in México.

    Science.gov (United States)

    Aguilar-Barragan, Alejandra; García-Torres, Ana Elisa; Odriozola-Casas, Olga; Macedo-Raygoza, Gloria; Ogura, Tetsuya; Manzo-Sánchez, Gilberto; James, Andrew C; Islas-Flores, Ignacio; Beltrán-García, Miguel J

    2014-01-01

    The chemical management of the black leaf streak disease in banana caused by Mycosphaerella fijiensis (Morelet) requires numerous applications of fungicides per year. However this has led to fungicide resistance in the field. The present study evaluated the activities of six fungicides against the mycelial growth by determination of EC50 values of strains collected from fields with different fungicide management programs: Rustic management (RM) without applications and Intensive management (IM) more than 25 fungicide application/year. Results showed a decreased sensitivity to all fungicides in isolates collected from IM. Means of EC50 values in mg L(-1) for RM and IM were: 13.25 ± 18.24 and 51.58 ± 46.14 for azoxystrobin, 81.40 ± 56.50 and 1.8575 ± 2.11 for carbendazim, 1.225 ± 0.945 and 10.01 ± 8.55 for propiconazole, 220 ± 67.66 vs. 368 ± 62.76 for vinclozolin, 9.862 ± 3.24 and 54.5 ± 21.08 for fludioxonil, 49.2125 ± 34.11 and 112.25 ± 51.20 for mancozeb. A molecular analysis for β-tubulin revealed a mutation at codon 198 in these strains having an EC50 greater than 10 mg L(-1) for carbendazim. Our data indicate a consistency between fungicide resistance and intensive chemical management in banana fields, however indicative values for resistance were also found in strains collected from rustic fields, suggesting that proximity among fields may be causing a fungus interchange, where rustic fields are breeding grounds for development of resistant strains. Urgent actions are required in order to avoid fungicide resistance in Mexican populations of M. fijiensis due to fungicide management practices.

  6. Chemical management in fungicide sensivity of Mycosphaerella fijiensis collected from banana fields in México

    Science.gov (United States)

    Aguilar-Barragan, Alejandra; García-Torres, Ana Elisa; Odriozola-Casas, Olga; Macedo-Raygoza, Gloria; Ogura, Tetsuya; Manzo-Sánchez, Gilberto; James, Andrew C.; Islas-Flores, Ignacio; Beltrán-García, Miguel J.

    2014-01-01

    The chemical management of the black leaf streak disease in banana caused by Mycosphaerella fijiensis (Morelet) requires numerous applications of fungicides per year. However this has led to fungicide resistance in the field. The present study evaluated the activities of six fungicides against the mycelial growth by determination of EC50 values of strains collected from fields with different fungicide management programs: Rustic management (RM) without applications and Intensive management (IM) more than 25 fungicide application/year. Results showed a decreased sensitivity to all fungicides in isolates collected from IM. Means of EC50 values in mg L−1 for RM and IM were: 13.25 ± 18.24 and 51.58 ± 46.14 for azoxystrobin, 81.40 ± 56.50 and 1.8575 ± 2.11 for carbendazim, 1.225 ± 0.945 and 10.01 ± 8.55 for propiconazole, 220 ± 67.66 vs. 368 ± 62.76 for vinclozolin, 9.862 ± 3.24 and 54.5 ± 21.08 for fludioxonil, 49.2125 ± 34.11 and 112.25 ± 51.20 for mancozeb. A molecular analysis for β-tubulin revealed a mutation at codon 198 in these strains having an EC50 greater than 10 mg L−1 for carbendazim. Our data indicate a consistency between fungicide resistance and intensive chemical management in banana fields, however indicative values for resistance were also found in strains collected from rustic fields, suggesting that proximity among fields may be causing a fungus interchange, where rustic fields are breeding grounds for development of resistant strains. Urgent actions are required in order to avoid fungicide resistance in Mexican populations of M. fijiensis due to fungicide management practices. PMID:24948956

  7. Chemical management in fungicide sensivity of Mycosphaerella fijiensis collected from banana fields in México

    Directory of Open Access Journals (Sweden)

    Alejandra Aguilar-Barragan

    2014-01-01

    Full Text Available The chemical management of the black leaf streak disease in banana caused by Mycosphaerella fijiensis (Morelet requires numerous applications of fungicides per year. However this has led to fungicide resistance in the field. The present study evaluated the activities of six fungicides against the mycelial growth by determination of EC50 values of strains collected from fields with different fungicide management programs: Rustic management (RM without applications and Intensive management (IM more than 25 fungicide application/year. Results showed a decreased sensitivity to all fungicides in isolates collected from IM. Means of EC50 values in mg L-1 for RM and IM were: 13.25 ± 18.24 and 51.58 ± 46.14 for azoxystrobin, 81.40 ± 56.50 and 1.8575 ± 2.11 for carbendazim, 1.225 ± 0.945 and 10.01 ± 8.55 for propiconazole, 220 ± 67.66 vs. 368 ± 62.76 for vinclozolin, 9.862 ± 3.24 and 54.5 ± 21.08 for fludioxonil, 49.2125 ± 34.11 and 112.25 ± 51.20 for mancozeb. A molecular analysis for β-tubulin revealed a mutation at codon 198 in these strains having an EC50 greater than 10 mg L-1 for carbendazim. Our data indicate a consistency between fungicide resistance and intensive chemical management in banana fields, however indicative values for resistance were also found in strains collected from rustic fields, suggesting that proximity among fields may be causing a fungus interchange, where rustic fields are breeding grounds for development of resistant strains. Urgent actions are required in order to avoid fungicide resistance in Mexican populations of M. fijiensis due to fungicide management practices.

  8. Sertraline demonstrates fungicidal activity in vitro for Coccidioides immitis

    Directory of Open Access Journals (Sweden)

    Simon Paul

    2016-07-01

    Full Text Available Coccidioidomycosis causes substantial morbidity in endemic areas. Disseminated coccidioidomycosis is an AIDS defining condition and treatment often requires lifelong antifungal therapy. Sertraline, a widely used serotonin-reuptake inhibitor anti-depressant, has demonstrated activity against Candida and Cryptococcus sp. both in vitro and in vivo. To evaluate if sertraline has activity against Coccidioides, the minimal inhibitory concentration (MIC and minimal fungicidal concentration (MFC of sertraline for four clinical isolates of C. immitis were determined. Sertraline was observed to have an MIC range of 4–8 µg/ml and MFC also of 4–8 µg/ml for Coccidioides. These MIC and MFC results for C. immitis are similar to those reported for Cryptococcus sp. suggesting sertraline may potentially have utility for the treatment of coccidioidomycosis.

  9. Azole Fungicides as Synergists in the Aquatic Environment

    DEFF Research Database (Denmark)

    Bjergager, Maj-Britt Andersen

    hazard.This PhD thesis evaluates the role of the so called azole fungicides as synergists in the aquaticenvironment through an assessment of the effect of sorption, time and azole concentration on theoccurrence and magnitude of synergistic interactions with pyrethroid insecticides towards...... the aquaticcrustacean Daphnia magna in both laboratory experiments and natural-like environments. In the PhDthesis, synergy is defined as happening in mixtures where either EC50 values decrease more than two-foldbelow the prediction by the model of Concentration Addition (horizontal assessment of synergy) or wherethe...... in stormwater runoff ordrain water and in the aquatic environment, the pesticides mainly occur in sorbed form. Sorption istraditionally considered to limit bioaccessibility and toxicity of hydrophobic compounds, hence,synergistic interactions may be limited in natural environments compared to laboratory studies...

  10. Endocrine disrupting properties in vivo of widely used azole fungicides

    DEFF Research Database (Denmark)

    Taxvig, Camilla; Vinggaard, Anne; Hass, Ulla

    2008-01-01

    The endocrine-disrupting potential of four commonly used azole fungicides, propiconazole, tebuconazole, epoxiconazole and ketoconazole, were tested in two short-term in vivo studies. Initially, the antiandrogenic effects of propiconazole and tebuconazole (50, 100 and 150 mg/kg body weight/day each......) were examined in the Hershberger assay. In the second study, pregnant Wistar rats were dosed with propiconazole, tebuconazole, epoxiconazole or ketoconazole (50 mg/kg/day each) from gestational day (GD) 7 to GD 21. Caesarian sections were performed on dams at GD 21. Tebuconazole and propiconazole...... demonstrated no antiandrogenic effects at doses between 50 and 150 mg/kg body weight/day in the Hershberger assay. In the in utero exposure toxicity study, ketoconazole, a pharmaceutical to treat human fungal infections, decreased anogenital distance and reduced testicular testosterone levels, demonstrating...

  11. Persistence behaviour of fungicide tebuconazole in a viticulture application.

    Science.gov (United States)

    Kundu, Chiranjit; Goon, Arnab; Bhattacharyya, Anjan

    2014-04-01

    Dissipation pattern and risk assessment of tebuconazole in grapes was studied following two application rates (250 and 500 mL ha(-1)) under tropical humid climatic condition of West Bengal during 2009-2010. Residues of tebuconazole were confirmed by liquid chromatography-mass spectrometry. The average recoveries were found 87.53 % and 89.67 % for grapes and cropped soil respectively. Following the first order kinetics the fungicide dissipates in grapes with a half-life (T1/2) value ranges between 2.62 and 2.86 days irrespective of seasons and doses. No residues of tebuconazole were detected in harvest grapes and soil samples which refers that, tebuconazole does not possess any background contamination property in grapes. So it may be concluded from the study that tebuconazole does not possess any toxicological property when applied at the recommended dose.

  12. C–H Bonds as Ubiquitous Functionality: Preparation of Multiple Regioisomers of Arylated 1,2,4-Triazoles via C–H Arylation

    Science.gov (United States)

    Joo, Jung Min; Guo, Pengfei

    2013-01-01

    We describe a general approach for the synthesis of complex aryl 1,2,4-triazoles. The electronic character of the C–H bonds and the triazole ring allows for the regioselective C–H arylation of 1-alkyl and 4-alkyl triazoles under catalytic conditions. We have also developed the SEM- and THP-switch as well as trans-N-alkylation, which enable sequential arylation of the triazole ring to prepare 3,5-diaryltriazoles. This straightforward strategy provides rapid access to a variety of arylated 1,2,4-triazoles and well complements existing cyclization methods. PMID:23276283

  13. Aggregative stability of fungicidal nanomodifier based on zinc hydrosilicates

    Science.gov (United States)

    Grishina, Anna; Korolev, Evgeniy

    2018-03-01

    Currently, there is a strong need of high performance multi functional materials in high-rise construction. Obviously, such materials should be characterized by high strength; but for interior rooms biosafety is important as well. The promising direction to obtain both high strength and maintain biosafety in buildings and structures is to manage the structure of mineral binders by means of fungicidal nanomodifier based on zinc hydrosilicates. In the present work the aggregative stability of colloidal solutions of zinc hydrosilicates after one year of storage was studied. It has been established that the concentration of iron (III) hydroxide used to prepare the precursor of zinc hydrosilicates has a significant effect on the long-term aggregative stability: as the concentration of iron (III) hydroxide increases, the resistance of the fungicidal nanomodifier increases. It was found that, despite the minimal concentration of nano-sized zinc hydrosilicates (0.028%), the colloidal solution possesses a low long-term aggregative stability; while in the initial period (not less than 14 days) the colloidal solution of the nanomodifier is aggregatively stable. It is shown that when the ratio in the colloidal solution of the amount of the substance CH3COOH / SiO2 = 0.43 is reached, an increase in the polymerization rate is observed, which is the main cause of low aggregative stability. Colloidal solutions containing zinc hydrosilicates synthesized at a concentration of iron (III) hydroxide used to produce a precursor equal to 0.7% have a long-term aggregative stability and do not significantly change the reduced particle. Such compositions are to be expediently used for the nanomodifying of building composites in order to control their structure formation and to create conditions that impede the development of various mycelial fungi.

  14. Enzymatic basis for fungicide removal by Elodea canadensis.

    Science.gov (United States)

    Dosnon-Olette, Rachel; Schröder, Peter; Bartha, Bernadett; Aziz, Aziz; Couderchet, Michel; Eullaffroy, Philippe

    2011-07-01

    Plants can absorb a diversity of natural and man-made toxic compounds for which they have developed diverse detoxification mechanisms. Plants are able to metabolize and detoxify a wide array of xenobiotics by oxidation, sugar conjugation, glutathione conjugation, and more complex reactions. In this study, detoxification mechanisms of dimethomorph, a fungicide currently found in aquatic media were investigated in Elodea canadensis. Cytochrome P450 (P450) activity was measured by an oxygen biosensor system, glucosyltransferases (GTs) by HPLC, glutathione S-transferases (GSTs), and ascorbate peroxidase (APOX) were assayed spectrophotometrically. Incubation of Elodea with dimethomorph induced an increase of the P450 activity. GST activity was not stimulated by dimethomorph suggesting that GST does not participate in dimethomorph detoxification. In plants exposed to dimethomorph, comparable responses were observed for GST and APOX activities showing that the GST was more likely to play a role in response to oxidative stress. Preincubation with dimethomorph induced a high activity of O- and N-GT, it is therefore likely that both enzymes participate in the phase II (conjugation) of dimethomorph detoxification process. For the first time in aquatic plants, P450 activity was shown to be induced by a fungicide suggesting a role in the metabolization of dimethomorph. Moreover, our finding is the first evidence of dimethomorph and isoproturon activation of cytochrome P450 multienzyme family in an aquatic plant, i.e., Elodea (isoproturon was taken here as a reference molecule). The detoxification of dimetomorph seems to proceed via hydroxylation, and subsequent glucosylation, and might yield soluble as well as cell wall bound residues.

  15. The fungicide mancozeb induces toxic effects on mammalian granulosa cells

    Energy Technology Data Exchange (ETDEWEB)

    Paro, Rita [Department of Health Sciences, University of L' Aquila, Via Vetoio, L' Aquila (Italy); Tiboni, Gian Mario [Department of Medicine and Aging, Section of Reproductive Sciences, University “G. D' Annunzio”, Chieti-Pescara (Italy); Buccione, Roberto [Tumor Cell Invasion Laboratory, Consorzio Mario Negri Sud, Santa Maria Imbaro, Chieti (Italy); Rossi, Gianna; Cellini, Valerio [Department of Health Sciences, University of L' Aquila, Via Vetoio, L' Aquila (Italy); Canipari, Rita [Department of Anatomy, Histology, Forensic Medicine and Orthopedics, Section of Histology and Embryology, School of Pharmacy and Medicine, “Sapienza” University of Rome, Rome (Italy); Cecconi, Sandra, E-mail: sandra.cecconi@cc.univaq.it [Department of Health Sciences, University of L' Aquila, Via Vetoio, L' Aquila (Italy)

    2012-04-15

    The ethylene-bis-dithiocarbamate mancozeb is a widely used fungicide with low reported toxicity in mammals. In mice, mancozeb induces embryo apoptosis, affects oocyte meiotic spindle morphology and impairs fertilization rate even when used at very low concentrations. We evaluated the toxic effects of mancozeb on the mouse and human ovarian somatic granulosa cells. We examined parameters such as cell morphology, induction of apoptosis, and p53 expression levels. Mouse granulosa cells exposed to mancozeb underwent a time- and dose-dependent modification of their morphology, and acquired the ability to migrate but not to proliferate. The expression level of p53, in terms of mRNA and protein content, decreased significantly in comparison with unexposed cells, but no change in apoptosis was recorded. Toxic effects could be attributed, at least in part, to the presence of ethylenthiourea (ETU), the main mancozeb catabolite, which was found in culture medium. Human granulosa cells also showed dose-dependent morphological changes and reduced p53 expression levels after exposure to mancozeb. Altogether, these results indicate that mancozeb affects the somatic cells of the mammalian ovarian follicles by inducing a premalignant-like status, and that such damage occurs to the same extent in both mouse and human GC. These results further substantiate the concept that mancozeb should be regarded as a reproductive toxicant. Highlights: ► The fungicide mancozeb affects oocyte spindle morphology and fertilization rate. ► We investigated the toxic effects of mancozeb on mouse and human granulosa cells. ► Granulosa cells modify their morphology and expression level of p53. ► Mancozeb induces a premalignant-like status in exposed cells.

  16. Efficiency of Elite Fungicide for Control of Pistachio Gummosis

    Directory of Open Access Journals (Sweden)

    Mohammad Moradi

    2017-05-01

    Full Text Available Several species of Phytophthora cause crown and root rot diseases of herbaceous and woody plants. Crown and root rot of pistachio trees cause significant damages in infected orchards. The effect of foliar application with Elite (fosetyl-Al in 2 and 2.5 g/l was evaluated in greenhouse experiments. The frequency of mortality, fresh and dry weight of roots and shoots, height, intensity of crown root colonization using CAMA-PARP medium was determined. Under greenhouse experiments, foliar application with Elite increased height, fresh and dry weight of shoots and root either in inoculation with and without Phytophthora drechsleri. The effects of Elite were more pronounced in roots, which increased the fresh and dry weight of root 1.3 and 2.5 times compared to those not sprayed with Elite, respectively. On the other hand, the application of Elite before or on the day of inoculation significantly reduced the frequency of mortality, which ranged from 35 to 90% (P ≤ 0.01. Crown and root colonization of pistachio seedling was affected by both the concentration of Elite and reduced the frequency of crown and root colonization of seedling. When fungicide and pathogen were applied at the same time, the frequency of colonization reduced to 18% and 36% for 2 and 2.5 g/l, respectively, and 43% and 60% when seedlings were treated with fungicide before P. drechsleri inoculations. The highest effect was seen in foliar application of Elite seven days before inoculation in 2.5 g/l. Further investigations have been conducted to understand the effect of Elite in infected trees as well as modeling of Elite application via soil drench, foliar application or trunk injection.

  17. Field efficacy of different fungicide mixtures in control of net blotch on barley

    Directory of Open Access Journals (Sweden)

    Stepanović Miloš

    2016-01-01

    Full Text Available Seven fungicide mixtures (epoxiconazol + metconazole, boscalid + epoxiconazole, pyraclostrobin + epoxiconazole, prothioconazole + tebuconazole, picoxistrobin + cyproconazole, azoxystrobin + cyproconazole and spiroxamine + tebuconazole + triadimenol were evaluated for control of net blotch of barley caused by Drechslera teres, as well as yield losses, over the 2010 and 2011 growing seasons. Two applications of the fungicide combination pyraclostrobin + epoxiconazole at the rate of 1.0 l ha-1 were the most effective treatment in controlling the disease and improving yield in both experimental years. Treatments with the fungicide mixtures epoxiconazol + metconazole and spiroxamine + tebuconazole + triadimenol showed the least effectiveness in disease control, as well as yield increase.

  18. Allenols versus Allenones: Rhodium-Catalyzed Regiodivergent and Tunable Allene Reactivity with Triazoles.

    Science.gov (United States)

    Alcaide, Benito; Almendros, Pedro; Cembellín, Sara; Martínez Del Campo, Teresa; Palop, Guillermo

    2017-10-04

    2-Pyrrolines and 6-oxo-hexa-2,4-dienals have been prepared through the divergent reactions of 1-benzenesulfonyl-4-aryl-1,2,3-triazoles with functionalized allenes. The rhodium-catalyzed reactions between allenols and 1-benzenesulfonyl-4-aryl-1,2,3-triazoles yielded 2-pyrrolines. This transformation is compatible with the presence of aliphatic, aromatic, heterocyclic, amide, and halogen functional groups. Interestingly, a reactivity switch took place when the allene-tethered alcohol substrate was replaced by its ketone counterpart. When the rhodium-catalyzed reaction of 1-benzenesulfonyl-4-phenyl-1,2,3-triazole was performed with allenones, acyclic 6-oxo-hexa-2,4-dienals were stereoselectively formed as (2Z,4E) isomers. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  19. Facile diverted synthesis of pyrrolidinyl triazoles using organotrifluoroborate: discovery of potential mPTP blockers.

    Science.gov (United States)

    Jung, Sun hwa; Choi, Kihang; Pae, Ae Nim; Lee, Jae Kyun; Choo, Hyunah; Keum, Gyochang; Cho, Yong Seo; Min, Sun-Joon

    2014-12-21

    This article describes the rapid and diversified synthesis of pyrrolidinyl triazoles for the discovery of mitochondrial permeability transition pore (mPTP) blockers. The 1,3-dipolar cycloaddition of ethynyl trifluoroborate with azidopyrrolidine produced a key intermediate, triazolyl trifluoroborate 4, which subsequently underwent a Suzuki-Miyaura coupling reaction to afford a series of 1,4-disubstituted triazoles 2. Subsequent biological evaluation of these derivatives indicated 2ag and 2aj as the most potent mPTP blockers exhibiting excellent cytochrome P450 (CYP) stability when compared to the previously reported oxime analogue 1. The present work clearly demonstrates that a 1,2,3-triazole can be used as a stable oxime surrogate. Furthermore, it suggests that late-stage diversification through coupling reactions of organotrifluoroborates is suitable for the rapid discovery of biologically active molecules.

  20. A convenient synthesis and screening of benzosuberone bearing 1,2,3-triazoles against Mycobacterium tuberculosis.

    Science.gov (United States)

    Sajja, Yasodakrishna; Vanguru, Sowmya; Jilla, Lavanya; Vulupala, Hanmanth Reddy; Bantu, Rajashaker; Yogeswari, Perumal; Sriram, Dharmarajan; Nagarapu, Lingaiah

    2016-09-01

    A series of benzosuberone bearing 1,2,3-triazoles were rationally designed and alkyl/aryl groups appended on 1,2,3-triazole derivatives 5a-o were synthesized using click chemistry and evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (ATCC27294). Compounds 5h (MIC: 3.125μg/mL) and 5l, 5m, 5o (MIC: 6.25μg/mL) exhibited promising hits. This is the first Letter on the synthesis and in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv of benzosuberone alkyl/aryl groups appended on 1,2,3-triazole derivatives. Copyright © 2016 Elsevier Ltd. All rights reserved.

  1. Doenças foliares e o controle por fungicidas na produtividade e qualidade de grãos de trigo Foliar diseases and control by fungicides on yield and quality of wheat grains

    Directory of Open Access Journals (Sweden)

    Lucas Navarini

    2012-12-01

    -quality wheat. The results also showed that diseases compromise the remobilization of nitrogen from leaves to grains. The differences between strobilurins and triazoles were evident in the control of leaf spot and leaf rust, in which triazole fungicides were more effective in controlling the leaf spot complex, when compared to strobilurins. However, effective control of wheat leaf rust was provided by strobilurins. The phenological stages of elongation and emission of spikes are critical times for the chemical control of leaf spot under conditions of monoculture. In addition, the fungicide application after flowering is essential for the appropriate management of leaf rust.

  2. Toxicogenomic effects common to triazole antifungals and conserved between rats and humans

    International Nuclear Information System (INIS)

    Goetz, Amber K.; Dix, David J.

    2009-01-01

    The triazole antifungals myclobutanil, propiconazole and triadimefon cause varying degrees of hepatic toxicity and disrupt steroid hormone homeostasis in rodent in vivo models. To identify biological pathways consistently modulated across multiple timepoints and various study designs, gene expression profiling was conducted on rat livers from three separate studies with triazole treatment groups ranging from 6 h after a single oral gavage exposure, to prenatal to adult exposures via feed. To explore conservation of responses across species, gene expression from the rat liver studies were compared to in vitro data from rat and human primary hepatocytes exposed to the triazoles. Toxicogenomic data on triazoles from 33 different treatment groups and 135 samples (microarrays) identified thousands of probe sets and dozens of pathways differentially expressed across time, dose, and species - many of these were common to all three triazoles, or conserved between rodents and humans. Common and conserved pathways included androgen and estrogen metabolism, xenobiotic metabolism signaling through CAR and PXR, and CYP mediated metabolism. Differentially expressed genes included the Phase I xenobiotic, fatty acid, sterol and steroid metabolism genes Cyp2b2 and CYP2B6, Cyp3a1 and CYP3A4, and Cyp4a22 and CYP4A11; Phase II conjugation enzyme genes Ugt1a1 and UGT1A1; and Phase III ABC transporter genes Abcb1 and ABCB1. Gene expression changes caused by all three triazoles in liver and hepatocytes were concentrated in biological pathways regulating lipid, sterol and steroid homeostasis, identifying a potential common mode of action conserved between rodents and humans. Modulation of hepatic sterol and steroid metabolism is a plausible mode of action for changes in serum testosterone and adverse reproductive outcomes observed in rat studies, and may be relevant to human risk assessment.

  3. Triazol-substituted titanocenes by strain-driven 1,3-dipolar cycloadditions

    Directory of Open Access Journals (Sweden)

    Andreas Gansäuer

    2014-07-01

    Full Text Available An operationally simple, convenient, and mild strategy for the synthesis of triazole-substituted titanocenes via strain-driven 1,3-dipolar cycloadditions between azide-functionalized titanocenes and cyclooctyne has been developed. It features the first synthesis of titanocenes containing azide groups. These compounds constitute ‘second-generation’ functionalized titanocene building blocks for further synthetic elaboration. Our synthesis is modular and large numbers of the complexes can in principle be prepared in short periods of time. Some of the triazole-substituted titanocenes display high cyctotoxic activity against BJAB cells. Comparison of the most active complexes allows the identification of structural features essential for biological activity.

  4. Reactivity of N-(1,2,4-Triazolyl)-Substituted 1,2,3-Triazoles

    Science.gov (United States)

    Zibinsky, Mikhail

    2011-01-01

    Synthetically useful rhodium(II) carbenes were obtained from N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles and Rh(II) carboxylates. The electron-withdrawing 1,2,4-triazolyl group reveals heretofore unknown reactivity of non-sulfonyl 1,2,3-triazoles, which exhibit reactivity of diazo compounds. The resulting carbenes provide ready asymmetric access to secondary homoaminocyclopropanes (80-95% ee, dr > 20:1) via reactions with olefins and also engage in efficient transannulation reactions with nitriles. PMID:21848347

  5. The thermodynamic properties of Fe(II) complexes with 1,2,4-triazoles

    Science.gov (United States)

    Berezovskii, G. A.; Pishchur, D. P.; Shakirova, O. G.; Lavrenova, L. G.

    2009-11-01

    The temperature dependences of the heat capacities at 106-330 K of the monoligand Fe(NH2trz)3I2 ( I) and mixed-ligand Fe(Htrz)0.3(NH2trz)2.7SiF6 · H2O ( II) complexes (Htrz is 1,2,4-triazole, and NH2trz is 4-amino-1,2,4-triazole) were studied by adiabatic vacuum calorimetry. The 1A1 ⇔ 5T2 spin transition was observed in these compounds. The thermodynamic parameters of phase transitions in I and II were determined.

  6. Synthesis and antimicrobial evaluation of cationic low molecular weight amphipathic 1,2,3-triazoles.

    Science.gov (United States)

    Bakka, Thomas A; Strøm, Morten B; Andersen, Jeanette H; Gautun, Odd R

    2017-03-01

    A library of 28 small cationic 1,4-substituted 1,2,3-triazoles was prepared for studies of antimicrobial activity. The structures addressed the pharmacophore model of small antimicrobial peptides and an amphipathic motif found in marine antimicrobials. Eight compounds showed promising antimicrobial activity, of which the most potent compound 10b displayed minimum inhibitory concentrations of 4-8μg/mL against Streptococcus agalacticae, Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, and Enterococcus faecalis. The simple syntheses and low degree of functionalization make these 1,4-substituted 1,2,3-triazoles interesting for further optimizations. Copyright © 2017 Elsevier Ltd. All rights reserved.

  7. Metal-Free Three-Component Domino Approach to Phosphonylated Triazolines and Triazoles.

    Science.gov (United States)

    Ahamad, Shakir; Kant, Ruchir; Mohanan, Kishor

    2016-01-15

    An efficient, three-component domino reaction between aldehydes, amines, and the Bestmann-Ohira reagent is reported that enables a general, mild, and straightforward access to 1,4,5-trisubstituted 1,2,3-triazolines and triazoles. The reaction proceeds through a domino-condensation/1,3-dipolar cycloaddition sequence to afford the triazoline derivatives with excellent diastereoselectivity. Moreover, when both amine and aldehyde employed for this reaction are aromatic, a spontaneous oxidation afforded 1,4,5-trisubstituted triazoles in moderate yields.

  8. Synthesis and Fungicidal activity of some sulphide derivatives of O-Ethyl-N-substituted phenylcarbamates

    International Nuclear Information System (INIS)

    Imeokparia, F.A.

    2006-01-01

    Monosulphides of O-ethyl-N-substituted phenylcarbamates were prepared by the reaction between O-ethyl-N-substituted phenylcarbamates and sulphur dichloride, while the corresponding disulphides were prepared by the reaction between O-ethyl-N-substituted phenylcarbamates and sulphur monochloride. The synthesized compounds were characterized by elemental analysis, thin layer chromatography (TLC), Fourier-transform infrared, and /sup 1/H and /sup 13/C nuclear magnetic resonance spectroscopic techniques. In vitro fungicidal assay of these sulphides against Fusarium oxysporum, Aspergillus niger, Aspergillus flavus and Rhizopus stolonifer showed that they had Greater fungicidal activity than their parent carbamates. The synthesized sulphides were more active towards A. Niger and A. flavus. Unlike the parent carbamates, the type of substituents attached to the aromatic nucleus of these sulphides had little or no effect on their fungicidal activity as there was insignificant variation in the fungicidal activity of the monosulphide and the disulphide derivatives of O-ethyl-N-substituted phenylcarbamates. (author)

  9. The effect of selected fungicides on survival of Agrobacterium tumefaciens in various kinds of soils

    Directory of Open Access Journals (Sweden)

    Stanisław Barczyński

    2013-12-01

    Full Text Available The effect of 10 fungicides on survival of A. tumefaciens in various types of soils was studied. In fertile, nonsterile soil Dithane M-45 (mancozeb, Euparen 50 WP (tolyfluanid, Kaptan 50 WP (captan and Ridomil Gold 80 WP (metalaxyl at concentration of 1000 ppm showed the highest antibacterial activity. Similar trends in activity of these fungicides occurred in fertile, sterile soil, however a little lower in case of Kaptan and Euparen. In most of investigated soils Befran 25 SL (imimnoctadyne, Syllit 65 WP (dodine and Thiram Granulfo 80 WG (thiram increased bacteria number. In sandy acidic soil (pH 3,5 all tested fungicides totally eliminated bacteria. On the other hand in sandy neutral soil only Dithane, Euparen, Kaptan and Ridomil showed such activity. Ten fold decrease of fungicides concentration generally did not influence Kaptan and Ridomil effectiveness but it decreased the activity of Dithane and Euparen.

  10. Yield of Potato as Influenced by Crop Sanitation and Reduced Fungicidal Treatments

    Directory of Open Access Journals (Sweden)

    Fontem, DA.

    1995-01-01

    Full Text Available The effects of crop sanitation and reduced sprays of "Ridomil plus®" (12 % metalaxyl + 60 % cuprous oxide on the control of potato (Solanum tuberosum late blight caused by Phytophthora infestans were evaluated in two field experiments in 1993 in Dschang, Cameroon. In the first experiment, sanitation (five weekly removals of blighted leaves and two fungicidal treatments were initiated from first symptoms. In the second experiment, both fungicidal sprays were made at varying rates. Marketable yields increased by 50 % in sanitation-treated plots, by 94 % in plots sprayed with Ridomil plus (2.24 kg a. i./ha, or by 55 % in those exposed to both control methods. The fungicide equivalence of the sanitation treatment was two sprays of Ridomil plus at 0.76 kg a. i./ha. These results suggest that proper removal of diseased leaves or reduced fungicidal protection may be an effective late blight control method in potato farming.

  11. Efficacy of Strobilurin-related and Multi-site Fungicide Mixtures Against Apple Scab

    Directory of Open Access Journals (Sweden)

    Emil Rekanović

    2007-01-01

    Full Text Available The efficacy of several fungicide mixtures in controlling Venturia inaequalis in apple was evaluated in field trials. The efficacies of Flint Plus (trifloxystrobin + captan and Tercel (pyraclostrobin+ dithianon in comparison with standard fungicides Zato 50-WG (trifloxystrobin and Stroby + Delan (kresoxim-methyl + dithianon were tested in the localities Mihajlovac, Radmilovac and Landol in 2004 and 2005. Both tested fungicides exhibited high efficacy in controlling apple scab. There were significant differencies in the efficacies of Flint Plus (91.3-98.5% and Zato 50-WG (68.2% and 78.4%; and Tercel (88.7-93.5% and Stroby + Delan (77.9% and 82.1%. Our experiments showed that the investigated fungicide mixtures arehighly effective against V. inaqeulais, even under high disease pressure.

  12. Synthesis and Evaluation of Essential Oil-Derived β-Methoxyacrylate Derivatives as High Potential Fungicides

    Directory of Open Access Journals (Sweden)

    Haihuan Su

    2017-05-01

    Full Text Available Essential oils (EOs are plant-derived aroma compounds with a wide range of biological activity, but their actions are slow, and they are typically unstable to light or heat, difficult to extract and so on. To find highly potential fungicides derived from natural EOs, a series of essential oil-based β-methoxyacrylate derivatives have been designed and synthesized. The target compounds have been screened for their potential fungicidal activity against eleven species of plant pathogen fungi, including Alternaria alternata, Phomopsis adianticola, Pestalotiopsis theae, Sclerotinia sclerotiorum, etc. Compared with intermediates I, the parent essential oils and azoxystrobin, almost all of essential oil-based β-methoxyacrylate derivatives exhibited significantly better fungicidal activity. Further investigation revealed that some compounds showed remarkable inhibitory activities against Pestalotiopsis theae, Phomopsis adianticola, Sclerotinia sclerotiorum and Magnapothe grisea at different concentrations in contrast to the commercial product azoxystrobin. Compound II-8 exhibited particularly significant fungicidal activity.

  13. Effects of Sublethal Fungicides on Mutation Rates and Genomic Variation in Fungal Plant Pathogen, Sclerotinia sclerotiorum.

    Directory of Open Access Journals (Sweden)

    B Sajeewa Amaradasa

    Full Text Available Pathogen exposure to sublethal doses of fungicides may result in mutations that may represent an important and largely overlooked mechanism of introducing new genetic variation into strictly clonal populations, including acquisition of fungicide resistance. We tested this hypothesis using the clonal plant pathogen, Sclerotinia sclerotiorum. Nine susceptible isolates were exposed independently to five commercial fungicides with different modes of action: boscalid (respiration inhibitor, iprodione (unclear mode of action, thiophanate methyl (inhibition of microtubulin synthesis and azoxystrobin and pyraclostrobin (quinone outside inhibitors. Mycelium of each isolate was inoculated onto a fungicide gradient and sub-cultured from the 50-100% inhibition zone for 12 generations and experiment repeated. Mutational changes were assessed for all isolates at six neutral microsatellite (SSR loci and for a subset of isolates using amplified fragment length polymorphisms (AFLPs. SSR analysis showed 12 of 85 fungicide-exposed isolates had a total of 127 stepwise mutations with 42 insertions and 85 deletions. Most stepwise deletions were in iprodione- and azoxystrobin-exposed isolates (n = 40/85 each. Estimated mutation rates were 1.7 to 60-fold higher for mutated loci compared to that expected under neutral conditions. AFLP genotyping of 33 isolates (16 non-exposed control and 17 fungicide exposed generated 602 polymorphic alleles. Cluster analysis with principal coordinate analysis (PCoA and discriminant analysis of principal components (DAPC identified fungicide-exposed isolates as a distinct group from non-exposed control isolates (PhiPT = 0.15, P = 0.001. Dendrograms based on neighbor-joining also supported allelic variation associated with fungicide-exposure. Fungicide sensitivity of isolates measured throughout both experiments did not show consistent trends. For example, eight isolates exposed to boscalid had higher EC50 values at the end of the

  14. Occurrence and persistence of fungicides in bed sediments and suspended solids from three targeted use areas in the United States

    Science.gov (United States)

    Smalling, Kelly L.; Reilly, Timothy J.; Sandstrom, Mark W.; Kuivila, Kathryn

    2013-01-01

    To document the environmental occurrence and persistence of fungicides, a robust and sensitive analytical method was used to measure 34 fungicides and an additional 57 current-use pesticides in bed sediments and suspended solids collected from areas of intense fungicide use within three geographic areas across the United States. Sampling sites were selected near or within agricultural research farms using prophylactic fungicides at rates and types typical of their geographic location. At least two fungicides were detected in 55% of the bed and 83% of the suspended solid samples and were detected in conjunction with herbicides and insecticides. Six fungicides were detected in all samples including pyraclostrobin (75%), boscalid (53%), chlorothalonil (41%) and zoxamide (22%). Pyraclostrobin, a strobilurin fungicide, used frequently in the United States on a variety of crops, was detected more frequently than p,p′-DDE, the primary degradate of p,p′-DDT, which is typically one of the most frequently occurring pesticides in sediments collected within highly agricultural areas. Maximum fungicide concentrations in bed sediments and suspended solids were 198 and 56.7 μg/kg dry weight, respectively. There is limited information on the occurrence, fate, and persistence of many fungicides in sediment and the environmental impacts are largely unknown. The results of this study indicate the importance of documenting the persistence of fungicides in the environment and the need for a better understanding of off-site transport mechanisms, particularly in areas where crops are grown that require frequent treatments to prevent fungal diseases.

  15. Avoidance behaviour and survival of two annelid oligochaetes exposed to two fungicides

    OpenAIRE

    Bart, Sylvain

    2016-01-01

    The use of pesticides in crop fields may have negative effects on soil biodiversity. Earthworms and enchytraeids are annelid oligochaetes involved in the evolution of soil organic matter and structure at different complementary scales. This study focused on the impact of two pesticides, an organic fungicide widely used to protect cereal crops in conventional agriculture and copper, a fungicide widely used in organic agriculture on fruit trees, vine or solanaceae to prevent spore germination. ...

  16. Effects of azole fungicides on the function of sex and thyroid hormones

    DEFF Research Database (Denmark)

    Kjærstad, Mia Birkhøj; Andersen, Helle Raun; Taxvig, Camilla

    Resumé: Azole-fungicides are frequently used in Denmark. Epoxiconazole, propiconazole, and tebuconazole had endocrine disrupting properties in cell based assays. In rats, epoxiconazole and tebuconazole increased gestational length, maternal progesterone level, and masculinized female-offspring. B......-offspring. Besides, tebuconazole caused feminization of male-offspring. Similar effects were previously demonstrated for prochloraz. The results indicate that azole-fungicides in general have endocrine disrupting properties...

  17. Sensitivity of Colletotrichum gloeosporioides Isolates from Diseased Avocado Fruits to Selected Fungicides in Kenya

    Directory of Open Access Journals (Sweden)

    Stanley Kirugo Kimaru

    2018-01-01

    Full Text Available Colletotrichum gloeosporioides is a serious postharvest pathogen of avocado fruits worldwide. Kenya lacks any registered fungicides for the management of the disease. Nevertheless, farmers commonly use commercially available fungicides such as Bayleton 25WP (Triadimefon 250 g/Kg, Milraz 76WP (Propineb 70% and Cymoxanil 6%, and Copper oxychloride 500WP for disease management. The efficacy of these fungicides against C. gloeosporioides is not known. The purpose of this study was therefore to test the inhibitory effect of these fungicides against 46 C. gloeosporioides isolates from avocado fruits collected from varieties grown at different agroecological zones in Murang’a County, a popular avocado-growing region in Kenya. Mycelial growth rate and sporulation for each isolate were measured in vitro on PDA plates amended with different concentrations of the fungicides. Plates were arranged in a completely randomized design with three replications per treatment. All fungicides were effective in vitro but there were significant differences in sensitivity among isolates. Bayleton had the highest mycelial inhibition followed by Milraz, while copper oxychloride had the lowest mycelial inhibition rates, ranging from 81% to 88%. However, copper oxychloride was more effective in inhibiting sporulation. The inhibitory effect of each fungicide was concentration-dependent, where twice the recommended concentration had the highest inhibitory effect, followed by the recommended concentration. Our results show that the fungicides used by farmers against C. gloeosporioides, the causal agent for anthracnose, are effective. We, however, recommend further field tests in different avocado-growing areas so as to validate their efficacy against various isolates and under different environments.

  18. Solubility Report of 1-Methyl-3,5-Dinitro-1H-1,2,4-Triazole (MDNT) and 2-Methyl-4,5-Dinitro-2H-1,2,3-Triazole 1-Oxide (MDNTO) for Co-Crystallization Screen

    Science.gov (United States)

    2015-11-01

    UNCLASSIFIED AD-E403 705 Technical Report ARMET-TR-15028 SOLUBILITY REPORT OF 1-METHYL-3,5-DINITRO-1H-1,2,4-TRIAZOLE (MDNT) AND...DATES COVERED (From – To) Jan. 2014 through Sept. 2014 4. TITLE AND SUBTITLE SOLUBILITY REPORT OF 1-METHYL-3,5-DINITRO-1H-1,2,4- TRIAZOLE (MDNT...13. SUPPLEMENTARY NOTES 14. ABSTRACT Solubilities of 1-methyl-3,5-dinitro-1H-1,2,4-triazole (MDNT) and 2-methyl-4,5-dinitro-2H-1,2,3

  19. Comparative efficacy of different fungicides against fusarium wilt of chickpea (cicer arietinum l.)

    International Nuclear Information System (INIS)

    Maitlo, S.A.

    2014-01-01

    Fusarium wilt caused by Fusarium oxysporum f. sp. ciceris (Foc) is the most serious and widespread disease of chickpea, causing a 100% loss under favorable conditions. Fourteen fungicides were evaluated against wilt pathogen In vitro with five different concentrations ranging from 1-10000 ppm. Among these only Carbendazim and Thiophanate-methyl was found as the most effective at all used concentrations. Other fungicides like Aliette, Nativo, Hombre-excel and Dividend star were found to be moderately effective. Whereas, remaining fungicides were ineffective against the targeted pathogen. Generally, a positive co-relation was observed between increasing concentrations of the tested fungicides and inhibition of Foc. Based on In vitro results Carbendazim, Thiophanate-methyl, Aliette, Dividend-star, Hombre-excel, Score and Nativo were selected for pot and field experiments. The higher concentrations of the few fungicides completely inhibited the pathogen as well as found to be phytotoxic and suppressed the plant growth while lower concentrations promoted the growth of chickpea plants. On over all bases, the Carbendazim and Thiophanate-methyl, followed by Aliette and Nativo were more effective in reducing the impact of pathogen as well as enhancing the plant growth in greenhouse experiment. Under field conditions, all fungicides except Score remarkably decreased the disease development and subsequently increased the plant growth as well as grain yield as compared to untreated plants. (author)

  20. Effects of Fungicide Treatment on Free Amino Acid Concentration and Acrylamide-Forming Potential in Wheat.

    Science.gov (United States)

    Curtis, Tanya Y; Powers, Stephen J; Halford, Nigel G

    2016-12-28

    Acrylamide forms from free asparagine and reducing sugars during frying, baking, roasting, or high-temperature processing, and cereal products are major contributors to dietary acrylamide intake. Free asparagine concentration is the determining factor for acrylamide-forming potential in cereals, and this study investigated the effect of fungicide application on free asparagine accumulation in wheat grain. Free amino acid concentrations were measured in flour from 47 varieties of wheat grown in a field trial in 2011-2012. The wheat had been supplied with nitrogen and sulfur and treated with growth regulators and fungicides. Acrylamide formation was measured after the flour had been heated at 180 °C for 20 min. Flour was also analyzed from 24 (of the 47) varieties grown in adjacent plots that were treated in identical fashion except that no fungicide was applied, resulting in visible infection by Septoria tritici, yellow rust, and brown rust. Free asparagine concentration in the fungicide-treated wheat ranged from 1.596 to 3.987 mmol kg -1 , with a significant (p fungicide treatment, the increases in acrylamide ranging from 2.7 to 370%. Free aspartic acid concentration also increased, whereas free glutamic acid concentration increased in some varieties but decreased in others, and free proline concentration decreased. The study showed disease control by fungicide application to be an important crop management measure for mitigating the problem of acrylamide formation in wheat products.

  1. Esterase isozymes patterns of grape vine (Vitis vinifera L. are altered in response to fungicide exposure

    Directory of Open Access Journals (Sweden)

    Gleice Ribeiro Orasmo

    2015-10-01

    Full Text Available Current analysis characterizes the effect of different fungicides often applied for pest control on a-and b-esterase patterns of four economically important table-wine grape cultivars (Italia, Rubi, Benitaka and Brasil of Vitis vinifera. The a- and b-esterase patterns in bud leaves of the cultivars were assessed by native PAGE analysis. Cabrio Top® compound inhibited Est-2, Est-5, Est-6, Est-7, Est-8, Est-9 and Est-10 carboxylesterases, whereas Est-4, Est-11, Est-12, Est-13, Est-14 acetylesterases and Est-16 carboxylesterase were detected as weakly stained bands. Carboxylesterases and acetylesterases were also detected as weakly stained bands when exposed to fungicides Orthocide 500®, Positron Duo® and Folicur PM®. No changes in a- and b-esterase patterns were reported when the vines were exposed to the fungicides Rovral SC®, Kumulus DF®, Curzate M®, Score® or Cuprogarb 500®. The evidence of functional changes in carboxylesterase and acetylesterase levels in current study is a warning to grape producers on the dangers inherent in the indiscriminate use of potent and modern fungicides extensively used in agriculture. The inhibition effect of fungicides on esterase isozyme molecules seems to be independent of the fungicide chemical.

  2. Control Efficacy of Fungicide Injection on Oak Wilt in the Field

    Directory of Open Access Journals (Sweden)

    Su-Yeon Son

    2014-12-01

    Full Text Available Oak wilt caused by Raffaelea quercus-mongolicae was first noticed in South Korea in 2004 and, ever since, its distribution and damage have been increasing. To screen a fungicide effective for oak wilt control by tree injection, laboratory and field experiments were conducted. Ten fungicides and one antibiotic were examined in vivo for their effectiveness in restricting the growth of R. quercus-mongolicae and R. quercivora (Japanese oak wilt pathogen isolates. To the Korean isolates of R. quercus-mongolicae, chlorothalonil showed the highest fungicidal effects, followed by benomyl and propiconazole. To the Japanese one, propiconazole was highest in the fungicidal effectiveness, followed by benomyl and bitertanol. Propiconazole was selected for field-testing of its control efficacy because it showed good fungicidal effects in vitro and systemic activity. The control efficacy in the field was 87.5% in the first year of injection and 66.7% in the second year, indicating the fungicidal effects last at least over one year.

  3. New α-Methylene-γ-Butyrolactone Derivatives as Potential Fungicidal Agents: Design, Synthesis and Antifungal Activities

    Directory of Open Access Journals (Sweden)

    Yongling Wu

    2016-01-01

    Full Text Available In consideration of the fact that the α-methylene-γ-butyrolactone moiety is a major bio-functional group in the structure of carabrone and possesses some agricultural biological activity, forty-six new ester and six new ether derivatives containing α-methylene-γ-butyrolactone moieties were synthesized, and their fungicidal activities against Colletotrichum lagenarium and Botrytis cinerea were investigated. Most of the synthesized compounds showed moderate to significant fungicidal activity. Among them, halogen atom-containing derivatives showed better activity than others, especially compounds 6a,d which exhibited excellent fungicidal activity against C. lagenarium, with IC50 values of 7.68 and 8.17 μM. The structure-activity relationship (SAR analysis indicated that ester derivatives with electron-withdrawing groups on the benzene ring showed better fungicidal activity than those with electron-donating groups. A quantitative structure-activity relationship (QSAR model (R2 = 0.9824, F = 203.01, S2 = 0.0083 was obtained through the heuristic method. The built model revealed a strong correlation of fungicidal activity against C. lagenarium with the molecular structures of these compounds. These results are expected to prove helpful in the design and exploration of low toxicity and high efficiency α-methylene-γ-butyrolactone-based fungicides.

  4. Assessing the impact of fungicide enostroburin application on bacterial community in wheat phyllosphere.

    Science.gov (United States)

    Gu, Likun; Bai, Zhihui; Jin, Bo; Hu, Qing; Wang, Huili; Zhuang, Guoqiang; Zhang, Hongxun

    2010-01-01

    Fungicides have been used extensively for controlling fungal pathogens of plants. However, little is known regarding the effects that fungicides upon the indigenous bacterial communities within the plant phyllosphere. The aims of this study were to assess the impact of fungicide enostroburin upon bacterial communities in wheat phyllosphere. Culture-independent methodologies of 16S rDNA clone library and 16S rDNA directed polymerase chain reaction with denaturing gradient gel electrophoresis (PCR-DGGE) were used for monitoring the change of bacterial community. The 16S rDNA clone library and PCR-DGGE analysis both confirmed the microbial community of wheat plant phyllosphere were predominantly of the gamma-Proteobacteria phyla. Results from PCR-DGGE analysis indicated a significant change in bacterial community structure within the phyllosphere following fungicide enostroburin application. Bands sequenced within control cultures were predominantly of Pseudomonas genus, but those bands sequenced in the treated samples were predominantly strains of Pantoea genus and Pseudomonas genus. Of interest was the appearance of two DGGE bands following fungicide treatment, one of which had sequence similarities (98%) to Pantoea sp. which might be a competitor of plant pathogens. This study revealed the wheat phyllosphere bacterial community composition and a shift in the bacterial community following fungicide enostroburin application.

  5. Synthesis and evaluation of 1-alkyl-4-phenyl-[1,2,3]-triazole derivatives as antimycobacterial agent

    International Nuclear Information System (INIS)

    Gallardo, Hugo; Conte, Gilmar; Bryk, Fernando; Lourenco, Maria Cristina S.; Costa, Marilia S.; Ferreira, Vitor F.

    2007-01-01

    Fourteen small molar mass 1-alkyl-4-phenyl-[1,2,3]-triazole derivatives were prepared using a straightforward and efficient method for the regioselective synthesis of [1,2,3]-triazoles and the compounds were screened for antimycobacterial activity against multiple-drug-resistant strains of Mycobacterium tuberculosis H37Rv. The synthetic methodology consisted of a Cu(I)-catalyzed 1,3-dipolar cycloaddition of aryl azides to terminal arylacetylenes (click-reaction). Six [1,2,3]-triazoles were found to be more active against M. tuberculosis than the positive control ethambutol. (author)

  6. Synthesis of 1H-1,2,3-triazoles and study of their antifungal and cytotoxicity activities.

    Science.gov (United States)

    da Silva, Iara F; Martins, Prisicila R C; da Silva, Emanuelly G; Ferreira, Sabrina B; Ferreira, Vitor F; da Costa, Karen Regina C; de Vasconcellos, Marne C; Lima, Emerson S; da Silva, Fernando de C

    2013-12-01

    We report herein the results of antifungal activity of fifteen 1,2,3-triazoles against Candida albicans, Candida krusei, Candida parapsilosis, Candida kefyr, Candida tropicalis, Candida dubliniensis, Tricophyton rubrum, Microporum canis and Aspergillus niger. All of the 1,2,3-triazoles were prepared from 1,3-dipolar cyclizations between aryl azides and alkynes catalyzed by Cu(I), and several of the compounds exhibited antifungal activity with low cytotoxicity. The results demonstrated the potential and importance of developing new 1,2,3-triazoles compounds with antifungal activity.

  7. Study using 1 H and 13 V NMR of 3-aryl-s-triazole benzoate azole type compounds and intermediaries

    International Nuclear Information System (INIS)

    Garske, Jose Emilio L.; Bacha, Catarina T.M.; Schenkel, Eloir Paulo

    1991-01-01

    Approximately 62% of the compounds used for medical purposes are heterocyclic, and are distributed as follows: 95% containing hydrogen, 28% containing sulfur and 18% containing oxygen in the structural composition. Some triazole-s-triazole type hetero aromatic systems and intermediaries, such as 1-aryl hydrazides exhibited bactericide, anti inflammatory and fungi stat activities. All the triazoles are are obtained synthetically, and are not found in the Nature. The proton and carbon-13 spectra of the non usual I, II and III compounds that we obtained are discussed in this work

  8. Last Generation Triazoles for Imported Eumycetoma in Eleven Consecutive Adults

    Science.gov (United States)

    Crabol, Yoann; Poiree, Sylvain; Bougnoux, Marie-Elisabeth; Maunoury, Christophe; Barete, Stéphane; Zeller, Valérie; Arvieux, Cédric; Pineau, Samuel; Amazzough, Karima; Lecuit, Marc; Lanternier, Fanny; Lortholary, Olivier

    2014-01-01

    Background Optimal management of eumycetoma, a severely debilitating chronic progressive fungal infection of skin, disseminating to bone and viscera, remains challenging. Especially, optimal antifungal treatment and duration are ill defined. Methodology/Principal Findings We conducted a monocentric retrospective study of 11 imported cases of eumycetoma treated by voriconazole or posaconazole for at least 6 months. Response to treatment was assessed through evolution of clinical and magnetic resonance imaging (MRI). (1→3) ß-D-glucan (BG) and positron emission tomography using [18F] fluorodeoxyglucose (PET/CT) results were also assessed. Identified species were Fusarium solani complex (n = 3); Madurella mycetomatis, (n = 3), and Exophiala jeanselmei, (n = 1). Moreover, two coelomycetes and one phaeohyphomycetes strains without species identification were retrieved. Serum BG and PET/CT were abnormal in 7/8 and 6/6 patients tested, respectively. Patients received last generation azoles for a mean duration of 25.9±18 months. Complete response (major clinical and MRI improvement) was observed in 5/11 patients, partial response (minor MRI improvement or stable MRI findings) in 5 and failure (MRI evidence of disease progression) in one, with a 73±39 [6–132] months mean follow-up. Relapse occurred in 2 patients after treatment discontinuation. Optimal outcome was associated with fungal species, initiation of last generation triazole therapy (<65 months since first symptoms), negative serum BG and PET/CT normalization. Conclusions/Significance MRI, PET/CT and serum BG appear as promising tools to assess optimal time of antifungal treatment for eumycetoma. PMID:25299610

  9. Design, synthesis, and fungicidal activity of novel carboxylic acid amides represented by N-benzhydryl valinamode carbamates.

    Science.gov (United States)

    Du, Xiu-Jiang; Bian, Qiang; Wang, Hong-Xue; Yu, Shu-Jing; Kou, Jun-Jie; Wang, Zhi-Peng; Li, Zheng-Ming; Zhao, Wei-Guang

    2014-08-07

    Carboxylic acid amide (CAA) fungicides are an important class of agricultural fungicide with oomycete activity and low toxicity toward mammalian cells. To find CAA analogues with high activity against resistant pathogens, a series of substituted N-benzhydryl valinamide carbamate derivatives were designed and synthesized by introducing substituted aromatic rings into valinamide carbamate leads. Bioassays showed that some title compounds exhibited very good in vitro fungicidal activity against Phytophthora capsici and in vivo fungicidal activities against Pseudoperonospora cubensis. Topomer CoMFA was performed to explore the structure-activity relationship on the basis of the in vitro data. The dimethoxy substituted aromatic analogue 9e was found to display higher in vitro fungicidal activity against Phytophthora capsici than iprovalicarb but lower activity than mandipropamid, and higher in vivo fungicidal activity against Pseudoperonospora cubensis than dimethomorph at a dosage of 6.25 μg mL(-1).

  10. Photoreduction of chlorothalonil fungicide on plant leaf models.

    Science.gov (United States)

    Monadjemi, S; El Roz, M; Richard, C; Ter Halle, A

    2011-11-15

    Photodegradation is seldom considered at the surface of vegetation after crop spraying. Chlorothalonil, a broad-spectrum foliar fungicide with a very widespread use worldwide, was considered. To represent the waxy upper layer of leaves, tests were performed within thin paraffin wax films or in n-heptane. Laser flash photolysis together with steady-state irradiation in n-heptane allowed the determination of the photodegradation mechanisms Chlorothalonil ability to produce singlet oxygen was measured; noteworthy its efficiency is close to 100%. Additionally, chlorothalonil photodegradation mainly proceeds through reductive dechlorination. In these hydrophobic media, a radical mechanism was evidenced. Photochemical tests on wax films under simulated solar light show that formulated chlorothalonil is more reactive than pure chlorothalonil. The field-extrapolated half-life of photolysis on vegetation was estimated to 5.3 days. This value was compared to the half-lives of penetration and volatilization available in the literature. It appears that chlorothalonil dissipation from crops is ruled by both photodegradation and penetration. The relative importance of the two paths probably depends on meteorological factors and on physicochemical characteristics of the crop leaf cuticle.

  11. Dissipation of the fungicide hexaconazole in oil palm plantation.

    Science.gov (United States)

    Maznah, Zainol; Halimah, Muhamad; Ismail, Sahid; Idris, Abu Seman

    2015-12-01

    Hexaconazole is a potential fungicide to be used in the oil palm plantation for controlling the basal stem root (BSR) disease caused by Ganoderma boninense. Therefore, the dissipation rate of hexaconazole in an oil palm agroecosystem under field conditions was studied. Two experimental plots were treated with hexaconazole at the recommended dosage of 4.5 g a.i. palm(-1) (active ingredient) and at double the recommended dosage (9.0 g a.i. palm(-1)), whilst one plot was untreated as control. The residue of hexaconazole was detected in soil samples in the range of 2.74 to 0.78 and 7.13 to 1.66 mg kg(-1) at the recommended and double recommended dosage plots, respectively. An initial relatively rapid dissipation rate of hexaconazole residues occurred but reduced with time. The dissipation of hexaconazole in soil was described using first-order kinetics with the value of coefficient regression (r (2) > 0.8). The results indicated that hexaconazole has moderate persistence in the soil and the half-life was found to be 69.3 and 86.6 days in the recommended and double recommended dosage plot, respectively. The results obtained highlight that downward movement of hexaconazole was led by preferential flow as shown in image analysis. It can be concluded that varying soil conditions, environmental factors, and pesticide chemical properties of hexaconazole has a significant impact on dissipation of hexaconazole in soil under humid conditions.

  12. Fungicidal effect of bacteriocins harvested from Bacillus spp.

    Directory of Open Access Journals (Sweden)

    Adetunji, V. O.

    2013-01-01

    Full Text Available Aims: This study investigated the ability of bacteriocins isolated from Bacillus spp. (Bacillus species to inhibit fourdifferent yeast isolates obtained from common food products (nono, yoghurt, ogi and cheese commonly consumed byNigerians with minimal heat treatment.Methodology and results: Forty-five Bacillus spp. was isolated and identified from common food products usingcultural, morphological, physiological and biochemical characteristics. These isolates were tested for antimicrobialactivity against Salmonella enteritidis (3, Micrococcus luteus (1 and Staphylococcus aureus (2. Eight bacteriocinproducing strains were identified from an over- night broth culture centrifugated at 3500 revolutions for five minutes.Fungicidal effects of these bacteriocins were tested against four yeast strains using the Agar Well Diffusion method. Thebacteriocins produced wide zones of inhibition ranging from 5.9±0.000 to 24.00±0.000 mm against the 4 yeast strainstested. There was a significant difference (at p<0.05 between the yeast organisms and the bacteriocins from theBacillus spp.Conclusion, significance and impact of study: The study reveals the antifungal property of bacteriocins from Bacillusspp. and serves therefore as a base for further studies in its use in the control of diseases and extension of shelf-life ofproducts prone to fungi contamination.

  13. Evolution of ergosterol biosynthesis inhibitors as fungicidal against Candida.

    Science.gov (United States)

    Ahmad, Aijaz; Khan, Amber; Manzoor, Nikhat; Khan, Luqman A

    2010-01-01

    Azoles target the ergosterol synthesizing enzyme lanosterol 14alpha-demethylase and are a widely applied class of antifungal agents. Unfortunately azoles are generally fungistatic, and resistance to fluconazole is emerging in several fungal pathogens. In contrast to the increasing number of agents for the treatment of invasive fungal infections, discoveries of new antifungal agents with therapeutic value in dermatomycoses are reported only rare. Attention has been drawn to the antimicrobial activity of plants and their active principles due to the challenge of growing incidences of drug-resistant pathogens. Eugenol and methyl eugenol were reported to possess antimycotic properties. To further explore the antifungal activity of these compounds, in vitro studies were conducted on various Candida isolates. Insight studies to mechanism suggested that both eugenol and methyl eugenol exerts their antifungal activity by targeting sterol biosynthesis. Furthermore, it was also observed that additional methyl group to eugenol increases its antifungal activity. The observed fungicidal characteristics of both eugenol and methyl eugenol indicate that both the compounds might be promising antifungal agents defining a new class of antimycotics.

  14. Interactions among cooling, fungicide and postharvest ripening temperature on peaches

    Energy Technology Data Exchange (ETDEWEB)

    Fernandez-Trujillo, J. Pablo; Cano, Antonio; Artes, Francisco [Postharvest and refrigeration Lab., Dept. of Food Science and Technology, CEBAS-CSIC, Murcia (Spain)

    2000-07-01

    Peach fruit (Prunus persica L. cv. 'Miraflores') harvested at the firm-ripe stage, treated or not with 2 g l{sup -1} iprodione, were cooled or not at 1{sup o}C and ripened at 15 or 20{sup o}C and 95% RH for 10 days. During ripening, weight loss, fungal development and changes in quality parameters (firmness, soluble solids content, titratable acidity, pH and ground and flesh color), and carbon dioxide and ethylene production were monitored. Cooling alone or combined with iprodione avoided Rhizopus nigricans decay during ripening at either ripening temperatures. A skin damage not previously reported on fungicide treated peach was observed at 20{sup o}C. Cooled fruit ripened at 15{sup o}C showed an anomalous respiration rate and ethylene production after the climacteric peak, a loss of firmness and a drop in titratable acidity after 7 days of storage, and reduced endo-polygalacturonase activity in presence of continuous pectinmethylesterase activity during the first week. Cooling before ripening at 20{sup o}C led to the best flavor without excessive total losses. These results helped in the optimization of warming cycles during cold storage used to avoid chilling injuries development on peaches. (Author)

  15. Hydrogen peroxide as a fungicide for fish culture

    Science.gov (United States)

    Dawson, V.K.; Rach, J.J.; Schreier, Theresa M.

    1994-01-01

    Antifungal agents are needed to maintain healthy stocks of fish in the intensive culture systems currently employed in fish hatcheries. Malachite green has been the most widely used antifungal agent; however, its potential for producing teratology in animals and fish precludes further use in fish culture. Preliminary studies at the National Fisheries Research Center, La Crosse, WI, USA (La Crosse Center) indicate that hydrogen peroxide is effective for control of Saprolegnia sp. fungus on incubating eggs of rainbow trout. It is also effective against a wide variety of other organisms such as bacteria, yeasts, viruses, and spores, and has been proposed as a treatment for sea lice on salmon. Hydrogen peroxide and its primary decomposition products, oxygen and water, are not systemic poisons and are considered environmentally compatible. In response to a petition from the La Crosse Center, the U.S. Food and Drug Administration (FDA) recently classified hydrogen peroxide as a 'low regulatory priority' when used for control of fungus on fish and fish eggs. Preliminary tests conducted at the La Crosse Center suggest that prophylactic treatments of 250 to 500 ppm (based on 100% active ingredient) for 15 minutes every other day will inhibit fungal infections on healthy rainbow trout (Oncorhynchus mykiss) eggs. This treatment regime also seems to inhibit fungal development and increase hatching success among infected eggs. Efficacy and safety of hydrogen peroxide as a fungicide for fish are currently being evaluated.

  16. Immunomodulatory effects of the fungicide Mancozeb in agricultural workers

    International Nuclear Information System (INIS)

    Corsini, Emanuela; Birindelli, Sarah; Fustinoni, Silvia; De Paschale, Gioia; Mammone, Teresa; Visentin, Sara; Galli, Corrado L.; Marinovich, Marina; Colosio, Claudio

    2005-01-01

    Available data suggest that ethylenebisdithiocarbamates (EBDCs) may have immunomodulatory effects. This study aimed to investigate the immunological profile of farmers exposed to Mancozeb, an EBDC fungicide, through the determination of several serum, cellular, and functional immune parameters. Twenty-six healthy subjects entered the study, 13 vineyards exposed to Mancozeb and 13 unexposed controls. Exposure was assessed through the determination of ethylentiourea (ETU) in urine. Complete and differential blood count, serum immunoglobulins, complement fractions, autoantibodies, lymphocyte subpopulations, proliferative response to mitogens, natural killer (NK) activity, and cytokine production were measured. Post-exposure samples showed ETU urine concentration significantly higher than pre-exposure and control groups. A significant increase in CD19+ cells, both percentage and absolute number, and a significant decrease in the percentage of CD25+ cells were found in post-exposure samples compared to controls. A statistically significant increase in the proliferative response to phorbol myristate acetate plus ionomycin (PMA + ionomycin) was observed in the post-exposure group compared to controls and baseline, while a significant reduction in LPS-induced TNF-α release in post-exposure samples was observed. Overall, our results suggest that low-level exposure to Mancozeb has slight immunomodulatory effects, and point out a method adequate to reveal immune-modifications in workers occupationally exposed to potential immunotoxic compounds, based on a whole blood assay

  17. Screening the efficient biological prospects of triazole allied mixed ligand metal complexes

    Science.gov (United States)

    Utthra, Ponnukalai Ponya; Kumaravel, Ganesan; Raman, Natarajan

    2017-12-01

    Triazole appended mixed ligand complexes (1-8) of the general formula [ML (bpy/phen)2]Cl2, where M = Cu(II), Co(II), Ni(II) and Zn(II), L = triazole appended Schiff base (E)sbnd N-(4-nitrobenzylidene)-1H-1,2,4-triazol-3-amine and bpy/phen = 2,2‧-bipyridine/1,10-phenanthroline, have been synthesized. The design and synthesis of this elaborate ligand has been performed with the aim of increasing stability and conjugation of 1,2,4 triazole, whose Schiff base derivatives are known as biologically active compounds thereby exploring their DNA binding affinity and other biological applications. The compounds have been comprehensively characterized by elemental analysis, spectroscopic methods (IR, UV-Vis, EPR, 1H and 13C NMR spectroscopy), ESI mass spectrometry and magnetic susceptibility measurements. The complexes were found to exhibit octahedral geometry. The complexes 1-8 were subjected to DNA binding techniques evaluated using UV-Vis absorption, CV, CD, Fluorescence spectroscopy and hydrodynamic measurements. Complex 5 showed a Kb value of 3.9 × 105 M-1. The DNA damaging efficacy for the complexes was observed to be high compared to the ligand. The antimicrobial screening of the compounds against bacterial and fungal strains indicates that the complexes possess excellent antimicrobial activity than the ligand. The overall biological activity of the complexes with phen as a co-ligand possessed superior potential than the ligand.

  18. Investigation on silver complexes of novel 1,2,3-triazole linked ...

    Indian Academy of Sciences (India)

    Abstract. The novel derivatives of 1,2,3-triazole linked crown ethers were investigated towards silver(I) ion coordination. The NMR measurements in deuterated methanol in different ratios of ligand and silver cation were studied. The experiments were performed in order to examine the way of binding Ag(I) ion by the ...

  19. Silver complexes of 1, 2, 4-triazole derived N-heterocyclic carbenes ...

    Indian Academy of Sciences (India)

    }+ Cl− [R = Et (1b), -Pr (2b)] of /-functionalized N-heterocyclic carbenes derived from 1,2,4-triazoles are reported. The silver complexes, 1b and 2b, have been synthesized from the reaction of the /-functionalized triazolium chloride salts ...

  20. Di(1H-benzo[d][1,2,3]triazol-1-yl)methane

    Indian Academy of Sciences (India)

    Abstract. An efficient Pd-catalysed Sonogashira coupling reaction was achieved in the absence of copper and amine with inorganic base using phosphene-free, air stable di(1H-benzo[d][1,2,3]triazol-1-yl)methane as ligand. The cross coupling of electron-rich, electron-defficient and hindered aryl halides with terminal ...

  1. Synthesis of divinyl derivatives of 5-substituted 1,2,4-triazole-3-thiones

    International Nuclear Information System (INIS)

    Trzhtsinskaya, B.V.; Rudakova, E.V.; Afonin, A.V.; Pertsikov, B.Z.; Mansurov, Yu.A.; Aksenov, V.P.

    1987-01-01

    The authors have previously described the synthesis of two divinyl derivatives of unsubstituted triazolethione. In order to expand the range of such compounds, they studied the reaction of 5-methyl- (I), 5-phenyl- (II), and 5-α-furyl-1,2,4-triazole-3-thione (III) with acetylene. Triazoles (I) and (III) in the presence of alkali add one acetylene molecule. An increase in the reaction time yields the product of the addition of two acetylene molecules to (I) in yields up to 50%. The substitution of the alkaline catalyst by CuCl facilitates the formation of divinyl derivatives. However, the use of CuCl in this case led to a decrease in the yield of the desired product. N-Vinyl-3-vinylthio-5-methyl-1,2,4-triazoles were obtained in yields up to 64% in the presence of cadmium acetate. On the other hand, the use of CuCl as the catalyst facilitates the synthesis of N-vinyl-3-vinylthio-5-phenyl- and N-vinyl-3-vinylthio-5-α-furyl-1,2,4-triazoles

  2. Investigation on silver complexes of novel 1, 2, 3-triazole linked ...

    Indian Academy of Sciences (India)

    The novel derivatives of 1,2,3-triazole linked crown ethers were investigated towards silver(I) ion coordination. The NMR measurements in deuterated methanol in different ratios of ligand and silver cation were studied. The experiments were performed in order to examine the way of binding Ag(I) ion by the selected ligands.

  3. A Practical Methylation Procedure for (1H)-1,2,4-Triazole (Preprint)

    Science.gov (United States)

    2007-06-01

    precooled solution of the sodio -intermediate, while maintaining the temperature using both an external cooling bath and the electrophile’s rate of...the iodomethane/ sodio -triazole reaction mixture for 72 hours at 45 °C gave a crude reaction mixture essentially identical to the 19 hour variant. A

  4. Synthesis and extended activity of triazole-containing macrocyclic protease inhibitors

    DEFF Research Database (Denmark)

    Pehere, A.D.; Pietsch, M.; Gütschow, M.

    2013-01-01

    Peptide-derived protease inhibitors are an important class of compounds with the potential to treat a wide range of diseases. Herein, we describe the synthesis of a series of triazole- containing macrocyclic protease inhibitors pre-organized into a b-strand conformation and an evaluation...

  5. Click synthesis of 1, 4-disubstituted-1, 2, 3-triazoles catalysed by ...

    Indian Academy of Sciences (India)

    Abstract. A CuO-CeO2 nanocomposite in the presence of amberlite-supported azide has been used for the click synthesis of 1,4-disubstituted-1,2,3-triazoles in good yields. This catalyst can be reused several times without any significant decrease in the catalytic activity.

  6. Di (1-benzo [][1, 2, 3] triazol-1-yl) methane: An efficient ligand for ...

    Indian Academy of Sciences (India)

    An efficient Pd-catalysed Sonogashira coupling reaction was achieved in the absence of copper and amine with inorganic base using phosphene-free, air stable di(1-benzo[][1,2,3]triazol-1-yl)methane as ligand. The cross coupling of electron-rich, electron-defficient and hindered aryl halides with terminal alkynes ...

  7. Microwave-Assisted Synthesis of Some 1H-1,2,4-Triazol-3-one ...

    African Journals Online (AJOL)

    NICO

    ester, hydrazide, oxadiazole and acetic acid derivatives of. 1,2,4-triazol-3-one by using microwave irradiation and conven- tional heating. Our research group has ..... 1 equiv. of. NaOH in absolute ethanol for 4 h. Then, the mixture was cooled at room temperature , poured into cold water and acidified to. pH 5 with conc. HCl.

  8. Supramolecular Corrals on Surfaces Resulting from Aromatic Interactions of Nonplanar Triazoles

    DEFF Research Database (Denmark)

    Jethwa, Siddharth; Kolsbjerg, Esben Leonhard; Vadapoo, Sundar Raja

    2017-01-01

    are observed using high-resolution scanning tunneling microscopy, and the energetic driving forces for their formation are elucidated using density functional theory calculations and Monte Carlo simulations. The individual corrals involve between 11 and 18 molecules bound through triazole moieties to a ring...

  9. Possible environmental origin of resistance of Aspergillus fumigatus to medical triazoles

    NARCIS (Netherlands)

    Snelders, Eveline; Huis In 't Veld, Robert A. G.; Rijs, Anthonius J. M. M.; Kema, Gert H. J.; Melchers, Willem J. G.; Verweij, Paul E.

    2009-01-01

    We reported the emergence of resistance to medical triazoles of Aspergillus fumigatus isolates from patients with invasive aspergillosis. A dominant resistance mechanism was found, and we hypothesized that azole resistance might develop through azole exposure in the environment rather than in

  10. Possible environmental origin of resistance of Aspergillus fumigatus to medical triazoles.

    NARCIS (Netherlands)

    Snelders, E.; Huis In 't Veld, R.A.; Rijs, A.J.M.M.; Kema, G.H.; Melchers, W.J.G.; Verweij, P.E.

    2009-01-01

    We reported the emergence of resistance to medical triazoles of Aspergillus fumigatus isolates from patients with invasive aspergillosis. A dominant resistance mechanism was found, and we hypothesized that azole resistance might develop through azole exposure in the environment rather than in

  11. Acyl hydrazides and triazoles as novel inhibitors of mammalian cathepsin B and cathepsin H.

    Science.gov (United States)

    Raghav, Neera; Singh, Mamta

    2014-04-22

    In the past decade, the work on the identification of small molecular weight compounds as inhibitors of cysteine proteases has been in focus. In this direction, we here present the facile microwave assisted synthesis of some acyl hydrazides and triazoles, followed by their evaluation as protease inhibitors and inhibitory studies on cathepsin B and cathepsin H, two significant lysosomal cysteine proteases. The compounds were characterized by (1)H NMR, (13)C NMR, Mass and IR spectral data. The compounds which were found inhibitory to endogenous proteolysis in liver homogenate at pH 5.0 were further studied for determination of inhibition type and Ki values on purified cathepsin B and cathepsin H. The maximum inhibitory effect was exerted by 3-(3'-nitrophenyl)-5-(3'-nitrophenyl)-4-amino-1,2,4-triazoles (2c), 3-(4'-chlorophenyl)-5-(4'-chloro phenyl)-4-amino-1,2,4-triazoles (2h), 3-(3'-aminophenyl)-5-(3'-aminophenyl)-4-amino-1,2,4-triazoles (2i) and 4-methoxybenzohydrazide (1b). Copyright © 2014 Elsevier Masson SAS. All rights reserved.

  12. Triazole induced concentration-related gene signatures in rat whole embryo culture

    NARCIS (Netherlands)

    Robinson, J.F.; Tonk, E.C.M.; Verhoef, A.; Piersma, A.H.

    2012-01-01

    Commonly used as antifungal agents in agriculture and medicine, triazoles have been shown to cause teratogenicity in a diverse set of animal models. Here, we evaluated the dose-dependent impacts of flusilazole, cyproconazole and triadimefon, on global gene expression in relation to effects on

  13. Possible Environmental Origin of Resistance of Aspergillus fumigatus to Medical Triazoles

    NARCIS (Netherlands)

    Snelders, E.; Veld, R.; Rijs, A.; Kema, G.H.J.; Melchers, W.J.G.; Verweij, P.E.

    2009-01-01

    We reported the emergence of resistance to medical triazoles of Aspergillus fumigatus isolates from patients with invasive aspergillosis. A dominant resistance mechanism was found, and we hypothesized that azole resistance might develop through azole exposure in the environment rather than in

  14. Transition Metal-Free Catalytic Synthesis of 1,5-Diaryl-1,2,3-Triazoles

    Science.gov (United States)

    Kwok, Sen W.; Fotsing, Joseph R.; Fraser, Rebecca J.; Rodionov, Valentin O.; Fokin, Valery V.

    2010-01-01

    1,5-Diarylsubstituted 1,2,3-triazoles are formed in high yield from aryl azides and terminal alkynes in DMSO in the presence of catalytic tetraalkyl ammonium hydroxide. The reaction is experimentally simple, does not require a transition-metal catalyst, and is not sensitive to atmospheric oxygen and moisture. PMID:20825167

  15. Design and synthesis of triazole-based peptidomimetics of a PSD-95 PDZ domain inhibitor

    DEFF Research Database (Denmark)

    Bach, Anders; Pedersen, Thomas B.; Strømgaard, Kristian

    2016-01-01

    PSD-95 PDZ domains are biologically important and promising drug targets. Here, we discover a triazole-based peptidomimetic, 10, by ‘click chemistry’. Compound 10 inhibits the PDZ2/GluN2B interaction with affinity similar to tripeptide SAV and better than current small-molecules. Thus, 10...

  16. Formation of passivating layers by 1,2,4-triazole derivatives on copper in aqueous solutions

    Science.gov (United States)

    Kuznetsov, Yu. I.; Shikhaliev, Kh. S.; Agafonkina, M. O.; Andreeva, N. P.; Semiletov, A. M.; Chirkunov, A. A.; Potapov, A. Yu.; Solov'ev, V. E.

    2017-12-01

    Ellipsometry and electrochemical measurements are used to study the adsorption of some substituted 1,2,4-triazoles on copper and their effect on dissolution of copper in aqueous buffer solutions at pH 7.4. It is found that the adsorption of triazole compounds on copper is polymolecular at potential E = 0.0 V, in relation to a normal hydrogen electrode. The first layer is described by the Temkin equation with free adsorption energy (-Δ G a 0) = 55.2-76.3 kJ/mol and an energy heterogeneity factor that varies from 0.91 to 2.5. The maximum value of -Δ G a 0 is found for an acid and a hydrogen sulfide corrosion inhibitor that is a mixture of triazole derivatives. The same inhibitor is the one least sensitive to the energy heterogeneity of the surface of a copper electrode, due to its high chemical reactivity and ability to be adsorbed on different active sites. This inhibitor is likely chemisorbed on copper and forms an ultrathin coating in an aqueous solution that is vastly superior to similar coatings produced by the familiar corrosion inhibitors of triazole group compounds in protecting against atmospheric corrosion.

  17. Triazole-containing N-acyl homoserine lactones targeting the quorum sensing system in Pseudomonas aeruginosa

    DEFF Research Database (Denmark)

    Hansen, Mette Reimert; Jakobsen, Tim H.; Bang, Claus Gunnar

    2015-01-01

    the pathogenesis and antibiotic tolerance of a bacterial biofilm. To identify the structural elements important for antagonistic or agonistic activity against the Pseudomonas aeruginosa LasR protein, we report the synthesis and screening of new triazole-containing mimics of natural N-acyl homoserine lactones...

  18. Intramolecular Transannulation of Alkynyl Triazoles via Alkyne-Carbene Metathesis Step: Access to Fused Pyrroles

    Science.gov (United States)

    Shi, Yi; Gevorgyan, Vladimir

    2013-01-01

    An intramolecular Rh-catalyzed transannulation reaction of alkynyl triazoles has been developed. This method allows efficient construction of various 5,5-fused pyrroles, including tetrahydropyrrolo and spiro systems. The method demonstrates excellent functional group compatibility. A rhodium carbene-alkyne metathesis mechanism is proposed for this transformation. PMID:24093728

  19. Investigation on silver complexes of novel 1,2,3-triazole linked ...

    Indian Academy of Sciences (India)

    The novel derivatives of 1,2,3-triazole linked crown ethers were investigated towards silver(I) ion coordination. The NMR measurements in deuterated methanol in different ratios of ligand and silver cation were studied. The experiments were performed in order to examine the way of binding Ag(I) ion by the selected ligands.

  20. A triazole derivative as a new acid-base indicator | Numan Bulut ...

    African Journals Online (AJOL)

    1,2,4-triazole-5-on (BPNBAT), soluble in acetonitrile:water (1:4), was developed. The estimation of pH is possible either from the position of the absorption maxima or from the absorbance intensity at a constant wavelength. This feature allowed ...

  1. Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation

    Directory of Open Access Journals (Sweden)

    Rezki Nadjet

    2017-09-01

    Full Text Available The present study describes an efficient and ecofriendly, ultrasound, one-pot click cycloaddition approach for the construction of a novel series of 1,4-disubstituted-1,2,3-triazoles tethered with fluorinated 1,2,4-triazole-benzothiazole molecular conjugates. It involved three-component condensation of the appropriate bromoacetamide benzothiazole, sodium azide and 4-alkyl/aryl-5-(2-fluorophenyl-3-(prop-2-ynylthio-1,2,4-triazoles 4a-e through a Cu(I-catalyzed 1,3-dipolar cycloaddition reaction. This approach involves in situ generation of azidoacetamide benzothiazole, followed by condensation with terminal alkynes in the presence of CuSO4/Na-ascorbate in aqueous DMSO under both conventional and ultrasound conditions. Some of the designed 1,2,3-triazole conjugates 6a-o were recognized for their antimicrobial activity against some bacterial and fungal pathogenic strains.

  2. Synthesis of N-(5-(Substitutedphenyl-4,5-dihydro-1H-pyrazol-3-yl-4H-1,2,4-triazol-4-amine from 4-Amino-4H-1,2,4-triazole

    Directory of Open Access Journals (Sweden)

    Ashvin D. Panchal

    2011-01-01

    Full Text Available N-(4H-1,2,4-Triazol-4-ylacetamide (2 were prepared by reaction of 4-amino-4H-1,2,4-triazole (1 with acetyl chloride in dry benzene. It has been reacted with various aromatic aldehyde to afford 3-(substitutedphenyl-N-(4H-1,2,4-triazol-4-ylacrylamide (3a-e. The synthesis of N-(5-substitutedphenyl-4,5-dihydro-1H-pyrazol-3-yl-4H-1,2,4-triazol-4-amine (4a-e is achieved by the cyclisation of 3a-e with hydrazine hydrate in ethanol. The structures of synthesized compounds were characterized by 1H NMR and IR spectroscopic studies. The purity of the compounds was checked by thin layer chromatography.

  3. Ring Transformation of Heterocycles Transformation of 4,5-Dihydro-5,5-Dimethyl-H-1,2,4-Triazoles Into 5-Methyl-H-1,2,4-Triazoles

    International Nuclear Information System (INIS)

    Awadallah, A.

    2001-01-01

    Reaction of 1-aryl-3-acetyl-4,5-dihydro-5,5-dimethyl-1H-1,2,4-triazoles(3) with acetyl chloride or acetic anhydride is found to give the ring transformation product 1-aryl-3-acetyl-5-methyl-1H-1,2,4-triazoles (4) instead of the expected N-acetyl derivative (5). This ring transformation is believed to start with N-acylation of the dihydrotriazole (3) to form the corresponding N-acetyl derivative (5), which extrudes the actone via a four-membered ring intermediate (6) and recyclizes to the aromatic triazole (4) suggesting the conversion sequence (3)→(5)→(6)→(4). It is Also found that. The triazoles 4 can be prepared directly via a one put reaction between nitrilimines and acetaldoximes . (Author) 8 refs., 4 Sches

  4. Synthesis of 5-aryl-4-(2-acetylaminobenzoyl)-1,2,3-triazoles with the 15N isotope at the terminal positions of the triazole rings and the tautomeric composition

    International Nuclear Information System (INIS)

    Kurkovskaya, L.N.; Velezheva, V.S.; Sorokina, I.K.; Dmitrevskaya, L.I.; Zhil'nikov, V.G.

    1988-01-01

    A mixture of 4-(2-acetylaminobenzoyl)-5-phenyl(p-cumenyl)-1- 15 N,2,3- and 4-(2-acetylaminobenzoyl)-5-phenyl(p-cumenyl)-1,2,3- 15 N-triazoles was obtained from 1-acetyl-2-arylmethylene-3-indolinones and Na 15 N 3 with the label at the terminal position. The tautomeric composition of the mixture, which corresponds to a state of equilibrium between the 2H and 3H forms of the triazole ring, was established by 1 H (at low temperatures) and 15 N NMR spectroscopy. The 4-(2-acetylaminobenzoyl)-5-aryl-1,2,3-triazoles are acylated at the sterically less hindered position 2 of the triazole ring

  5. Efficient atropodiastereoselective access to 5,5'-bis-1,2,3-triazoles: studies on 1-glucosylated 5-halogeno 1,2,3-triazoles and their 5-substituted derivatives as glycogen phosphorylase inhibitors.

    Science.gov (United States)

    Goyard, David; Chajistamatiou, Aikaterini S; Sotiropoulou, Anastasia I; Chrysina, Evangelia D; Praly, Jean-Pierre; Vidal, Sébastien

    2014-04-25

    Whereas copper-catalyzed azide-alkyne cycloaddition (CuAAC) between acetylated β-D-glucosyl azide and alkyl or phenyl acetylenes led to the corresponding 4-substituted 1-glucosyl-1,2,3-triazoles in good yields, use of similar conditions but with 2 equiv CuI or CuBr led to the 5-halogeno analogues (>71 %). In contrast, with 2 equiv CuCl and either propargyl acetate or phenyl acetylene, the major products (>56 %) displayed two 5,5'-linked triazole rings resulting from homocoupling of the 1-glucosyl-4-substituted 1,2,3-triazoles. The 4-phenyl substituted compounds (acetylated, O-unprotected) and the acetylated 4-acetoxymethyl derivative existed in solution as a single form (d.r.>95:5), as shown by NMR spectroscopic analysis. The two 4-phenyl substituted structures were unambiguously identified for the first time by X-ray diffraction analysis, as atropisomers with aR stereochemistry. This represents one of the first efficient and highly atropodiastereoselective approaches to glucose-based bis-triazoles as single atropisomers. The products were purified by standard silica gel chromatography. Through Sonogashira or Suzuki cross-couplings, the 1-glucosyl-5-halogeno-1,2,3-triazoles were efficiently converted into a library of 1,2,3-triazoles of the 1-glucosyl-5-substituted (alkynyl, aryl) type. Attempts to achieve Heck coupling to methyl acrylate failed, but a stable palladium-associated triazole was isolated and analyzed by (1)H NMR and MS. O-Unprotected derivatives were tested as inhibitors of glycogen phosphorylase. The modest inhibition activities measured showed that 4,5-disubstituted 1-glucosyl-1,2,3-triazoles bind weakly to the enzyme. This suggests that such ligands do not fit the catalytic site or any other binding site of the enzyme. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  6. Synthesis of Some New 1,3,4-Thiadiazole, Thiazole and Pyridine Derivatives Containing 1,2,3-Triazole Moiety

    Directory of Open Access Journals (Sweden)

    Nadia A. Abdelriheem

    2017-02-01

    Full Text Available In this study, 1-(5-Methyl-1-(p-tolyl-1H-1,2,3-triazol-4-ylethan-1-one, was reacted with Thiosemicarbazide, alkyl carbodithioate and benzaldehyde to give thiosemicarbazone, alkylidenehydrazinecarbodithioate and 3-phenylprop-2-en-1-one-1,2,3-triazole derivatives. The 1,3,4-thiadiazole derivatives containing the 1,2,3-triazole moiety were obtained via reaction of alkylidenecarbodithioate with hydrazonoyl halides. Also, hydrazonoyl halides were reacted with thiosemicarbazone and pyrazolylthioamide to give 1,3-thiazoles derivatives. Subsequently, 3-phenyl2-en-1-one was used to synthesize substituted pyridines and substituted nicotinic acid ester. The latter was converted to its azide compound which was reacted with aromatic amines and phenol to give substituted urea and phenylcarbamate containing 1,2,3-triazole moiety. The newly synthesized compounds were established by elemental analysis, spectral data and alternative synthesis whenever possible.

  7. Duplex and Triplex Formation of Mixed Pyrimidine Oligonucleotides with Stacking of Phenyl-triazole Moieties in the Major Groove

    DEFF Research Database (Denmark)

    Andersen, Nicolai Krog; Døssing, Holger; Jensen, Frank

    2011-01-01

    5-(1-Phenyl-1,2,3-triazol-4-yl)-2'-deoxycytidine was synthesized from a modified CuAAC protocol and incorporated into mixed pyrimidine oligonucleotide sequences together with the corresponding 5-(1-phenyl-1,2,3-triazol-4-yl)-2'-deoxyuridine. With consecutive incorporations of the two modified...... nucleosides, improved duplex formation with a complementary RNA and improved triplex formation with a complementary DNA duplex were observed. The improvement is due to π-π stacking of the phenyl-triazole moieties in the major groove. The strongest stacking and most pronounced positive influence on thermal...... stability was found in between the uridine analogues or with the cytidine analogue placed in the 3' direction to the uridine analogue. Modeling indicated a different orientation of the phenyl-triazole moieties in the major groove to account for the difference between the two nucleotides. The modified...

  8. Analgesic Activity of Some 1,2,4-Triazole Heterocycles Clubbed with Pyrazole, Tetrazole, Isoxazole and Pyrimidine

    OpenAIRE

    Gajanan Khanage, Shantaram; Raju, Appala; Baban Mohite, Popat; Bhanudas Pandhare, Ramdas

    2013-01-01

    Purpose: In the present study in vivo analgesic activity of some previously synthesized 1,2,4-triazole derivatives containing pyrazole, tetrazole, isoxazole and pyrimidine ring have been evaluated. Methods: Acetic acid induced writhing method and Hot plate method has been described to study analgesic activity of some 1,2,4-triazole derivatives containing pyrazole, tetrazole, isoxazole and pyrimidine as a pharmacological active lead. Results: Thirty six different derivatives con...

  9. Design, synthesis and biological evaluation of tacrine-1,2,3-triazole derivatives as potent cholinesterase inhibitors

    DEFF Research Database (Denmark)

    Wu, Gaochan; Gao, Yun; Kang, Dongwei

    2018-01-01

    We report herein the design and synthesis of a series of 11 novel tacrine-1,2,3-triazole derivatives via a Cu(i)-catalyzed alkyne-azide 1,3-dipolar cycloaddition (CuAAC) reaction. The newly synthesized compounds were evaluated for their inhibition activity against Electrophorus electricus...... (SAR) and molecular modeling studies may provide valuable insights into the design of better tacrine-triazole analogues with potential therapeutic applications for AD....

  10. Sequential decarboxylative azide–alkyne cycloaddition and dehydrogenative coupling reactions: one-pot synthesis of polycyclic fused triazoles

    Directory of Open Access Journals (Sweden)

    Kuppusamy Bharathimohan

    2014-12-01

    Full Text Available Herein, we describe a one-pot protocol for the synthesis of a novel series of polycyclic triazole derivatives. Transition metal-catalyzed decarboxylative CuAAC and dehydrogenative cross coupling reactions are combined in a single flask and achieved good yields of the respective triazoles (up to 97% yield. This methodology is more convenient to produce the complex polycyclic molecules in a simple way.

  11. Oxidative alkylation of azoles. 1. Reaction of N-chloro-3-nitro-1,2,4-triazoles with methyl iodide

    International Nuclear Information System (INIS)

    Pevzner, M.S.; Kurunkov, A.A.; Trubitsin, A.E.

    1994-01-01

    By the methods of chemical analysis, IR and NMR spectroscopy it has been ascertained that interaction of methyl iodide with N-chloro-3-nitro- and 5-methyl-3-nitro-1,2,4-triazols results in iodine isolation and formation of a mixture of compounds: nonsubstituted in terms of nitrogen 3-nitro-1,2,4-triazols, N-mono- and N,N-dimethylated derivatives and products of their further transformations (1,4-dimethyl-5-triazolons)

  12. Tautomeric equilibrium and hydrogen shifts in tetrazole and triazoles: Focal-point analysis and ab initio limit

    Science.gov (United States)

    Balabin, Roman M.

    2009-10-01

    High-level ab initio electronic structure calculations, including extrapolations to the complete basis set (CBS) limit, were performed, and highly precise relative energies of five-member N-heterocycles were determined. Nitrogen-containing heterocycles studied included tautomers of tetrazole (CH2N4) and triazoles (C2H3N3). Valence focal-point analysis of 1H-tetrazole, 2H-tetrazole, 5H-tetrazole, 1H-1,2,3-triazole, 2H-1,2,3-triazole, 1H-1,2,4-triazole, and 4H-1,2,4-triazole and a number of transition state (TS) calculations were performed, using energy values determined by CCSD(T)/aug-cc-pVTZ, MP3/aug-cc-pVQZ, and MP2/aug-cc-pV5Z. An accuracy of 0.10-0.25 kcal mol-1 (35-87 cm-1) was obtained for comparison of tautomer energy differences. Relative CCSD(T)/CBS energies of 2.07, 3.98, and 6.25 kcal mol-1 for 1H-tetrazole, 1H-1,2,3-triazole, and 4H-1,2,4-triazole, respectively, were calculated. Use of electron correlation methods resulted in markedly different convergence behaviors for triazole and tetrazole tautomers. Similarly, differences in convergence were observed for TSs with respect to corresponding minima structures. It was confirmed that the MP2 method predicts an acyclic structure for 5H-tetrazole. The same was not observed for the corresponding TS geometry. Comparison with density functional theory (B3LYP) and model chemistry methods (CBS-4M and CBS-QB3) is reported.

  13. Development of a novel multiplex DNA microarray for Fusarium graminearum and analysis of azole fungicide responses

    Directory of Open Access Journals (Sweden)

    Deising Holger B

    2011-01-01

    Full Text Available Abstract Background The toxigenic fungal plant pathogen Fusarium graminearum compromises wheat production worldwide. Azole fungicides play a prominent role in controlling this pathogen. Sequencing of its genome stimulated the development of high-throughput technologies to study mechanisms of coping with fungicide stress and adaptation to fungicides at a previously unprecedented precision. DNA-microarrays have been used to analyze genome-wide gene expression patterns and uncovered complex transcriptional responses. A recently developed one-color multiplex array format allowed flexible, effective, and parallel examinations of eight RNA samples. Results We took advantage of the 8 × 15 k Agilent format to design, evaluate, and apply a novel microarray covering the whole F. graminearum genome to analyze transcriptional responses to azole fungicide treatment. Comparative statistical analysis of expression profiles uncovered 1058 genes that were significantly differentially expressed after azole-treatment. Quantitative RT-PCR analysis for 31 selected genes indicated high conformity to results from the microarray hybridization. Among the 596 genes with significantly increased transcript levels, analyses using GeneOntology and FunCat annotations detected the ergosterol-biosynthesis pathway genes as the category most significantly responding, confirming the mode-of-action of azole fungicides. Cyp51A, which is one of the three F. graminearum paralogs of Cyp51 encoding the target of azoles, was the most consistently differentially expressed gene of the entire study. A molecular phylogeny analyzing the relationships of the three CYP51 proteins in the context of 38 fungal genomes belonging to the Pezizomycotina indicated that CYP51C (FGSG_11024 groups with a new clade of CYP51 proteins. The transcriptional profiles for genes encoding ABC transporters and transcription factors suggested several involved in mechanisms alleviating the impact of the fungicide

  14. Sterol-inhibiting fungicide impacts on soil microbial ecology in Atlantic Coastal Plain soils

    Science.gov (United States)

    White, P. M.; Potter, T. L.; Strickland, T. C.

    2008-12-01

    Seventy-five percent of the peanuts (Arachus hypogaia) produced in the United States are grown in the Atlantic Coastal Plain region. Portions of this area, including Alabama and Georgia, exhibit a subtropical climate that promotes soil-borne plant fungal diseases. Most fields receive repeated fungicide applications during the growing season to suppress the disease causing organisms, such as Sclerotium rolfsii, Rhizoctonia solani, and Cylindrocladium parasiticum. Information regarding fungicide effects on the soil microbial community, with components principally responsible for transformation and fate of fungicides and other soil-applied pesticides, is limited. The objectives of the study were to assess soil microbial community response to (1) varying rates of the sterol-inhibiting fungicide tebuconazole (0, single application, season max, 2x season max), and (2) field rates of the sterol-inhibitors cyproconazole, prothioconazole, tebuconazole, and flutriafol, and thiol-competitor chlorothalonil. The sterol-inhibitors exhibited different half lives, as listed in the FOOTPRINT database, ranging from 1300 d. Chlorothalonil was chosen because it is the most frequently applied fungicide to peanut. Shifts in the fungi, gram positive and gram negative bacteria, were monitored during the experiments using phospholipid fatty acid (PLFA) profiles. Ergosterol levels and pesticide decay rates were also monitored to evaluate the effectiveness of the fungicide and soil residence time, respectively. In the rate study, the highest rate of tebuconazole reduced the fungal biomarker 18:2ω6,9c to 2.6 nmol g-1 dry soil at 17 d, as compared to the control (4.1 nmol g-1 dry soil). However, levels of the fungal PLFA biomarker were similar regardless of rate at 0 and 32 d. The gram negative bacterial PLFA mole percent was greater at 17 d for the two highest rates of tebuconazole, but was similar at 0 and 32 d. Gram positive and fungal mole percents were not affected at any time point

  15. Effectiveness of Different Classes of Fungicides on Botrytis cinerea Causing Gray Mold on Fruit and Vegetables

    Directory of Open Access Journals (Sweden)

    Joon-Oh Kim

    2016-12-01

    Full Text Available Botrytis cinerea is a necrotrophic pathogen causing a major problem in the export and post-harvest of strawberries. Inappropriate use of fungicides leads to resistance among fungal pathogens. Therefore, it is necessary to evaluate the sensitivity of B. cinerea to various classes of fungicide and to determine the effectiveness of different concentrations of commonly used fungicides. We thus evaluated the effectiveness of six classes of fungicide in inhibiting the growth and development of this pathogen, namely, fludioxonil, iprodione, pyrimethanil, tebuconazole, fenpyrazamine, and boscalid. Fludioxonil was the most effective (EC₅₀ < 0.1 μg/ml, and pyrimethanil was the least effective (EC₅₀ = 50 μg/ml, at inhibiting the mycelial growth of B. cinerea. Fenpyrazamine and pyrimethanil showed relatively low effectiveness in inhibiting the germination and conidial production of B. cinerea. Our results are useful for the management of B. cinerea and as a basis for monitoring the sensitivity of B. cinerea strains to fungicides.

  16. Control of Fusarium head blight of winter wheat by artificial and natural infection using new fungicides

    Directory of Open Access Journals (Sweden)

    Olga Treikale

    2012-12-01

    Full Text Available In Latvia, climatic factors are influential in spreading of Fusarium head blight of cereals caused by Fusarium species. The most significant factor affecting the incidence of the disease in winter wheat is hightened temperature at the time of wheat anthesis. Field trials for the control of the disease in winter wheat were done in 2003-2004 using new fungicides applied at various rates by natural infection and artificial inoculation. Three species of causative agents: Fusarium avenaceum var. herbarum, F. gibbosum, F. culmorum were collected from infected seeds of wheat and used for inoculation of experimental plots at the concentration 106 conidia ml-1 (1:1:1 at the stage of full anthesis. Effective control of the disease was obtained through application of new fungicides with different active ingredient: Prosaro 250 EC (tebuconazole 125 G, prothioconazole 125 G L-1, Input 460 EC (spiroxamine 300 G, prothioconazole 160 G L-1. In conditions of artificial infection by severe attack of Fusarium spp. the application of fungicides containing tebuconazole at T3 gave significant influence on yield of winter wheat through plumpness of grains increase. High efficacy of fungicides against leaf infection with Erysiphe graminis and Drechslera tritici-repentis was also in the trial achieved. Application of fungicide containing cyproconazole and trifloxystrobin at T1 in the trial 2004 gave good control of Septoria tritici, E. graminis and D. triticirepentis.

  17. Compatibility of insecticides and fungicides with the zoophytophagous mirid predator Nesidiocoris tenuis.

    Science.gov (United States)

    Ziaei Madbouni, Mohammad Ali; Samih, Mohammad Amin; Qureshi, Jawwad A; Biondi, Antonio; Namvar, Peyman

    2017-01-01

    Nesidiocoris tenuis (Reuter) (Hemiptera: Miridae) is an effective predator of multiple pests of vegetable crops, such as thrips, mites, aphids, whiteflies, leafminers. It is mass-reared and released for augmentative biocontrol programs mainly aimed at controlling whiteflies and Tuta absoluta (Meyrick) (Lepidoptera: Gelechiidae) in greenhouses and open field. We evaluated the lethal and sublethal toxicity upon N. tenuis adults of label doses of three insecticides (pyriproxyfen, spirotetramat, cypermethrin) and seven fungicides (benomyl, chlorothalonil, copper oxychloride, cyazofamid, fluopicolide + propamocarb hydrochloride (FPH), penconazol, trifloxystrobin) commonly used in various crops. Two exposure routes were tested: (i) contact with dry residues of insecticides or fungicides on tomato sprouts and (ii) multiple exposure to these chemicals via topical sprays on adults which foraged on treated sprouts; and fed on treated eggs of Ephestia kuehniella (Zeller) (Lepidoptera: Pyralidae) simultaneously. Mortality and reproductive capacity were investigated as indicators of lethal and sublethal effects on N. tenius. The tested insecticides and fungicides were all classified as harmless when predator was exposed only to the dry residues of each. However, the multiple exposure to either cypermethrin, benomyl, chlorothalonil, copper oxychloride or trifloxystrobin caused significant mortality of N. tenuis adults. Cypermethrin also significantly reduced its reproductive capacity. Interestingly, N. tenuis produced a higher number of progeny when exposed to fungicides penconazol and FPH in both exposure scenarios. Overall, findings suggest that the two insecticides, pyriproxyfen and spirotetramat but not cypermethrin, and all tested fungicides can be considered compatible with N. tenuis.

  18. Synthesis of Triazole Derivatives of Levoglucosenone As Promising Anticancer Agents: Effective Exploration of the Chemical Space through retro-aza-Michael//aza-Michael Isomerizations.

    Science.gov (United States)

    Tsai, Yi-Hsuan; Borini Etichetti, Carla M; Di Benedetto, Carolina; Girardini, Javier E; Martins, Felipe Terra; Spanevello, Rolando A; Suárez, Alejandra G; Sarotti, Ariel M

    2018-03-08

    The design and synthesis of biomass-derived triazoles and the in vitro evaluation as potential anticancer agents are described. The discovery of base-catalyzed retro-aza-Michael//aza-Michael isomerizations allowed the exploration of the chemical space by affording novel types of triazoles, difficult to obtain otherwise. Following this strategy, 2,4-disubstituted 1,2,3-triazoles could be efficiently obtained from the corresponding 1,4-disubstituted analogues.

  19. Novel compounds of 4-amino-1,2,4-triazole with dicarboxylic acids – crystal structures, vibrational spectra and non-linear optical properties

    Czech Academy of Sciences Publication Activity Database

    Matulková, Irena; Němec, I.; Teubner, K.; Němec, P.; Mička, Z.

    2008-01-01

    Roč. 886, 1-3 (2008), s. 46-60 ISSN 0022-2860 Institutional research plan: CEZ:AV0Z40400503 Keywords : 4-Amino-1,2,4-triazole * 4-Amino-1,2,4-triazol-1-ium chloride * 4-Amino-1,2,4-triazol-1-ium hydrogen oxalate Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 1.594, year: 2008

  20. Are 1,4- and 1,5-disubstituted 1,2,3-triazoles good pharmacophoric groups?

    Science.gov (United States)

    Massarotti, Alberto; Aprile, Silvio; Mercalli, Valentina; Del Grosso, Erika; Grosa, Giorgio; Sorba, Giovanni; Tron, Gian Cesare

    2014-11-01

    Over the last decade, 1,2,3-triazoles have received increasing attention in medicinal chemistry thanks to the discovery of the highly useful and widely applicable 1,3-dipolar cycloaddition reaction between azides and alkynes (click chemistry) catalyzed by copper salts and ruthenium complexes. After a decade of medicinal chemistry research on 1,2,3-triazoles, we feel that the time is ripe to demonstrate the real ability of this heterocycle to participate in important and pivotal binding interactions with biological targets while maintaining a good pharmacokinetic profile. In this study, we retrieved and analyzed X-ray crystal structures of complexes between 1,2,3-triazoles and either proteins or DNA to understand the pharmacophoric role of the triazole. Furthermore, the metabolic stability, the capacity to inhibit cytochromes, and the contribution of 1,2,3-triazoles to the overall aqueous solubility of compounds containing them have been analyzed. This information should furnish fresh insight for medicinal chemists in the design of novel bioactive molecules that contain the triazole nucleus. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  1. Organocatalytic synthesis and sterol 14alpha-demethylase binding interactions of enantioriched 3-(1H-1,2,4-triazol-1-yl)butyl benzoates.

    Science.gov (United States)

    Ming, Zhi-Hui; Xu, Sheng-Zhen; Zhou, Lei; Ding, Ming-Wu; Yang, Jiao-Yan; Yang, Shao; Xiao, Wen-Jing

    2009-07-15

    1H-1,2,4-Triazole reacted with 2-butenal in the presence of diaryl prolinol silyl ether 3 and benzonic acid to give 3-(1H-1,2,4-triazol-1-yl)butanal 4, which was subsequently reduced and then treated with various acyl chloride to generate enantioriched 3-(1H-1,2,4-triazol-1-yl)butyl benzoates 6. Some of triazoles 6 exhibited strong binding interactions with the cytochrome P450-dependent sterol 14alpha-demethylase (CYP51). For example, compound (R)-6f showed the best binding activity with K(d) 0.3381 microM.

  2. A structural comparison of some amine- and thione-substituted triazoles

    Science.gov (United States)

    Sen, Ashok K.; Singh, Rajkumar Noren; Handa, Ram N.; Dubey, Surendra N.; Squattrito, Philip J.

    1998-10-01

    A series of amine- and thione-substituted triazoles have been synthesized and their structures determined by single-crystal X-ray diffraction methods. The compounds differ in the identity of the amine- and alkyl-substituents on the triazole ring. Crystal data for 4-furfuralideneamino-3-methyl-4,5-dihydro-1 H-1,2,4-triazole-5-thione, C 8H 8N 4OS: triclinic, space group P1¯, Z=2, a=10.490(2) Å, b=10.700(2) Å, c=4.2185(8) Å, α=92.68(2)°, β=90.17(2)°, γ=92.61(1)°, V=472.5(1) Å3, R( F)=0.040 for 151 variables and 1056 observations ( I>3 σ( I)); 4-furfuralideneamino-3-ethyl-4,5-dihydro-1 H-1,2,4-triazole-5-thione, C 9H 10N 4OS: triclinic, space group P1¯, Z=2, a=8.366(3) Å, b=9.296(2) Å, c=7.953(2) Å, α=113.72(2)°, β=108.54(3)°, γ=84.94(3)°, V=536.3(3) Å3, R( F)=0.037 for 136 variables and 1126 observations ( I>3 σ( I)); 4-furfuralideneamino-3-propyl-4,5-dihydro-1 H-1,2,4-triazole-5-thione, C 10H 12N 4OS: triclinic, space group P1¯, Z=2, a=9.149(3) Å, b=9.177(2) Å, c=8.045(4) Å, α=110.11(2)°, β=114.52(3)°, γ=86.44(2)°, V=574.5(4) Å3, R( F)=0.040 for 145 variables and 1414 observations ( I>3 σ( I)); 4-(2-acetylpyridyleneamino)-3-ethyl-4,5-dihydro-1 H-1,2,4-triazole-5-thione, C 11H 13N 5S: triclinic, space group P1¯, Z=2, a=7.736(3) Å, b=11.752(4) Å, c=7.219(2) Å, α=93.68(3)°, β=106.26(3) Å, γ=91.04(3)°, V=628.3(4) Å3, R( F)=0.043 for 154 variables and 1224 observations ( I>3 σ( I)). The molecules show substantial variations in conformation as well as in crystal packing. The differences in molecular structure are discussed in terms of the potential of the molecules to act as bidentate ligands towards metal ions.

  3. TENACITY AND PERSISTENCE OF COPPER FUNGICIDES IN CITRUS SEEDLINGS UNDER SIMULATED RAINFALL

    Directory of Open Access Journals (Sweden)

    ANTONIO EDUARDO FONSECA

    2016-01-01

    Full Text Available The amount of fungicide that adheres to the leaf during spraying and the amount that remain on the leaf after weathering are the main factors that defines the amount of active residue on the leaf surface to effectively control plant pathogens. Thus, the objective of this work was to evaluate the tenacity and persistence of copper in citrus seedling leaves under simulated rainfall in Jaboticabal, State of São Paulo, Brazil. The evaluated variables were copper content, solution retention, surface tension and drop spectrum. A significant and inversely proportional linear relationship to drops <100 μm was found. The percentage of copper retained in leaves of citrus seedlings with copper fungicides of suspension concentrate (SC formulations after simulated rainfall was greater than 80%. Copper fungicides of SC formulations presented the lowest surface tension, allowing greater tenacity and persistence of copper on seedlings of citrus leaves after simulated rainfall and increased contact between the drops and leaf surface.

  4. In vitro Determination of Fungicide Inhibitory Concentration for Phakopsora pachyrhizi isolates

    Directory of Open Access Journals (Sweden)

    Bianca Moura

    2016-06-01

    Full Text Available ABSTRACT In vitro assays were preformed to obtain the IC50 of eight fungicides against Phakopsora pachyrhizi isolates from Passo Fundo, RS, Ponta Grossa, PR, and Primavera do Leste, MT. Different concentrations of the fungicides were added to Petri dishes containing soybean leaf extract agar medium. One milliliter of P. pachyrhizi uredospore suspension at the concentration of 3.0 x 104 uredospores/mL was added to each dish for subsequent viability quantification. Only pyraclostrobin and the mixture trifloxystrobin + prothioconazole showed IC50 values inferior to 1.0 mg/L for all tested isolates, demonstrating high fungitoxicity. There was not loss of sensitivity to any of the tested fungicides.

  5. Community composition of target vs. non-target fungi in fungicide treated wheat

    DEFF Research Database (Denmark)

    Knorr, Kamilla; Jørgensen, Lise Nistrup; Justesen, Annemarie Fejer

    2012-01-01

    of three fungicides. The fungal composition in bulked leaf samples and individual leaves was studied by deep amplicon 454 pyrosequencing targeting the internal transcribed spacer-1 (ITS1) region of the ribosomal DNA. Amount of yellow rust in individual samples was quantified by qPCR. Pyrosequencing......Fungicide treatments are common control strategies used to manage fungal pathogens in agricultural fields, however, effects of treatments on the composition of total fungal communities, including non-target fungi, in the phyllosphere is not well known. Yellow rust (Puccinia striiformis) is a common...... in an amount of yellow rust below detection level. Fungal diversity was stable across treatments whereas the relative abundance of individual OTUs was affected by fungicide treatment....

  6. Environmental fate of fungicides and other current-use pesticides in a central California estuary

    Science.gov (United States)

    Smalling, Kelly L.; Kuivila, Kathryn; Orlando, James L.; Phillips, Bryn M.; Anderson, Brian S.; Siegler, Katie; Hunt, John W.; Hamilton, Mary

    2013-01-01

    The current study documents the fate of current-use pesticides in an agriculturally-dominated central California coastal estuary by focusing on the occurrence in water, sediment and tissue of resident aquatic organisms. Three fungicides (azoxystrobin, boscalid, and pyraclostrobin), one herbicide (propyzamide) and two organophosphate insecticides (chlorpyrifos and diazinon) were detected frequently. Dissolved pesticide concentrations in the estuary corresponded to the timing of application while bed sediment pesticide concentrations correlated with the distance from potential sources. Fungicides and insecticides were detected frequently in fish and invertebrates collected near the mouth of the estuary and the contaminant profiles differed from the sediment and water collected. This is the first study to document the occurrence of many current-use pesticides, including fungicides, in tissue. Limited information is available on the uptake, accumulation and effects of current-use pesticides on non-target organisms. Additional data are needed to understand the impacts of pesticides, especially in small agriculturally-dominated estuaries.

  7. Effect of nozzle type on the fungicide efficacy for fusarium head blight suppression on wheat

    Directory of Open Access Journals (Sweden)

    Šterbik Ildiko R.

    2017-01-01

    Full Text Available Effect of fungicide treatments on Fusarium head blight (FHB and grain yield of wheat depending on application technique i.e. use of different nozzle types, was evaluated in the study. Nozzles types TJ 11004, Albuz ATR 8004 and Arag TFA 11004 were used for application of systemic fungicide Duett Ultra (0.5 l/ha. FHB intensity (% was determined on the basis of a visual assessment of the number of infected heads and the perecentage of the disease symptoms on the individual head. Differences in grain yield between the treated variants, as well as between the treated and untreated variants, were determined after hand threshing. The lowest percentage of FHB development in wheat and the highest yield were recorded in variants where fungicides were applied by nozzle type ATR 8004. Application technique directly affects the reduction of fusarium head blight in wheat and indirectly it also reduces yield loss.

  8. Influence of new generation fungicides on Saccharomyces cerevisiae growth, grape must fermentation and aroma biosynthesis.

    Science.gov (United States)

    Noguerol-Pato, R; Torrado-Agrasar, A; González-Barreiro, C; Cancho-Grande, B; Simal-Gándara, J

    2014-03-01

    The influence of ten new generation fungicides (ametoctradin, benthiavalicarb-isopropyl, boscalid, cyazofamid, dimethomorph, fenhexamid, kresoxim-methyl, mepanipyrim, metrafenone, and pyraclostrobin) on the fermentative activity of Saccharomyces cerevisiae yeast was initially evaluated in pasteurised red must. The presence of ametoctradin, dimethomorph and mepanipyrim seemed to affect sugars-to-ethanol yield in the stationary phase. The same fermentation experiments were carried out for these three fungicides in ecological red must from Vitis vinifera cv. Tempranillo. When ecological must was unfiltered, the fermentative activity of yeasts was unaffected by the presence of these selected fungicides. However, when ecological must was filtered beforehand, a slight decrease of biomass and ethanol production (in terms of biomass-to-ethanol yield and sugars-to-ethanol yield, respectively), as well as a decrease in fruity aroma, were registered with respect to the control wine. Copyright © 2013 Elsevier Ltd. All rights reserved.

  9. Effect of Maize Hybrid and Foliar Fungicides on Yield Under Low Foliar Disease Severity Conditions.

    Science.gov (United States)

    Mallowa, Sally O; Esker, Paul D; Paul, Pierce A; Bradley, Carl A; Chapara, Venkata R; Conley, Shawn P; Robertson, Alison E

    2015-08-01

    Foliar fungicide use in the U.S. Corn Belt increased in the last decade; however, questions persist pertaining to its value and sustainability. Multistate field trials were established from 2010 to 2012 in Illinois, Iowa, Ohio, and Wisconsin to examine how hybrid and foliar fungicide influenced disease intensity and yield. The experimental design was in a split-split plot with main plots consisting of hybrids varying in resistance to gray leaf spot (caused by Cercospora zeae-maydis) and northern corn leaf blight (caused by Setosphaera turcica), subplots corresponding to four application timings of the fungicide pyraclostrobin, and sub-subplots represented by inoculations with either C. zeae-maydis, S. turcica, or both at two vegetative growth stages. Fungicide application (VT/R1) significantly reduced total disease severity relative to the control in five of eight site-years (P<0.05). Disease was reduced by approximately 30% at Wisconsin in 2011, 20% at Illinois in 2010, 29% at Iowa in 2010, and 32 and 30% at Ohio in 2010 and 2012, respectively. These disease severities ranged from 0.2 to 0.3% in Wisconsin in 2011 to 16.7 to 22.1% in Illinois in 2010. The untreated control had significantly lower yield (P<0.05) than the fungicide-treated in three site-years. Fungicide application increased the yield by approximately 6% at Ohio in 2010, 5% at Wisconsin in 2010 and 6% in 2011. Yield differences ranged from 8,403 to 8,890 kg/ha in Wisconsin 2011 to 11,362 to 11,919 kg/ha in Wisconsin 2010. Results suggest susceptibility to disease and prevailing environment are important drivers of observed differences. Yield increases as a result of the physiological benefits of plant health benefits under low disease were not consistent.

  10. Potential of Cerbera odollam as a bio-fungicide for post-harvest pathogen Penicilium digitatum

    Science.gov (United States)

    Singh, Harbant; Yin-Chu, Sue; Al-Samarrai, Ghassan; Syarhabil, Muhammad

    2015-05-01

    Postharvest diseases due to fungal infection contribute to economic losses in agriculture industry during storage, transportation or in the market. Penicillium digitatum is one of the common pathogen responsible for the postharvest rot in fruits. This disease is currently being controlled by synthetic fungicides such as Guazatine and Imazalil. However, heavy use of fungicides has resulted in environmental pollution, such as residue in fruit that expose a significant risk to human health. Therefore, there is a strong need to develop alternatives to synthetic fungicide to raise customer confidence. In the current research, different concentrations (500 to 3000 ppm) of ethanol extract of Cerbera odollam or commonly known as Pong-pong were compared with Neem and the controls (Positive control/Guazatine; Negative control/DMSO) for the anti-fungicide activity in PDA media contained in 10 cm diameter Petri dishes, using a modification of Ruch and Worf's method. The toxicity (Lc50) of the C.odollam extract was determined by Brine-shrimp test (BST). The results of the research indicated that crude extraction from C.odollam showed the highest inhibition rate (93%) and smallest colony diameter (0.63 cm) at 3000 ppm in vitro compared with Neem (inhibition rate: 88%; colony diameter: 1.33 cm) and control (Positive control/Guazatine inhibition rate: 79%, colony diameter: 1.9 cm; Negative control/DMSO inhibition rate: 0%, colony diameter: 9.2 cm). C.odollam recorded Lc50 value of 5 µg/ml which is safe but to be used with caution (unsafe level: below 2 µg/ml). The above anti-microbial activity and toxicity value results indicate that C.odollam has a potential of being a future bio-fungicide that could be employed as an alternative to synthetic fungicide.

  11. Using epidemiological principles to explain fungicide resistance management tactics: why do mixtures outperform alternations?

    Science.gov (United States)

    Elderfield, James A; Lopez Ruiz, Fran; van den Bosch, Frank; Cunniffe, Nik J

    2018-01-29

    Whether fungicide resistance management is optimised by spraying chemicals with different modes of action as a mixture (i.e. simultaneously) or in alternation (i.e. sequentially) has been studied by experimenters and modellers for decades. However results have been inconclusive. We use previously-parameterised and validated mathematical models of wheat septoria leaf blotch and grapevine powdery mildew to test which tactic provides better resistance management, using the total yield before resistance causes disease control to become economically-ineffective ("lifetime yield") to measure effectiveness. We focus on tactics involving the combination of a low-risk and a high-risk fungicide, and the case in which resistance to the high-risk chemical is complete (i.e. in which there is no partial resistance). Lifetime yield is then optimised by spraying as much low-risk fungicide as is permitted, combined with slightly more high-risk fungicide than needed for acceptable initial disease control, applying these fungicides as a mixture. That mixture rather than alternation gives better performance is invariant to model parameterisation and structure, as well as the pathosystem in question. However if comparison focuses on other metrics, e.g. lifetime yield at full label dose, either mixture or alternation can be optimal. Our work shows how epidemiological principles can explain the evolution of fungicide resistance, and also highlights a theoretical framework to address the question of whether mixture or alternation provides better resistance management. It also demonstrates that precisely how spray tactics are compared must be given careful consideration.

  12. Combinations of fungicide and cultural practices influence the incidence and impact of fusiform rust in slash pine plantations

    Science.gov (United States)

    James D. Haywood; Allan E. Tiarks

    1994-01-01

    Slash pine was grown in central Louisiana under four levels of culture with or without repeated sprayings of the systematic fungicide triadimefon for protection against fusiform rust. The eight treatment combinations were: (1)no fungicide, weed control, or fertilizer; (2)weeded; (3)weeded, applied inorganic fertilizer, and bedded before planting; (4)weeded, bedded,...

  13. Rainfall thresholds as support for timing fungicide applications in the control of potato late blight in Ecuador and Peru

    DEFF Research Database (Denmark)

    Kromann, Peter; Taipe, Arturo; Perez, Willmer G.

    2009-01-01

    Accumulated rainfall thresholds were studied in seven field experiments conducted in Ecuador and Peru for their value in timing applications of fungicide to control potato late blight, caused by Phytophthora infestans. Fungicide regimes based on accumulated rainfall thresholds ranging from 10 to 70...

  14. Effect of fungicides and biocontrol agents on inoculum production and persistence of Phytophthora ramorum on nursery hosts

    Science.gov (United States)

    Steve Tjosvold; David Chambers; Gary Chastagner; Marianne. Elliott

    2013-01-01

    Once Phytophthora ramorum is introduced into a nursery on a host, its local spread and establishment is primarily dependent on sporangia and zoospore production. Nursery operators commonly use fungicides to prevent the establishment of Phytophthora –caused diseases, although current research only supports the use of fungicides...

  15. Baseline sensitivity to fluopyram and fungicide resistance phenotypes of botrytis cinerea populations from table grapes in california

    Science.gov (United States)

    Gray mold caused by Botrytis cinerea is a major postharvest disease of table grapes grown in the Central Valley of California. Understanding fungicide-resistant phenotypes of B. cinerea is important to the development of pre-harvest fungicide programs for control of postharvest gray mold. Baseline s...

  16. Evaluation of fungicides for the control of Botryosphaeria protearum on Protea magnifica in the Western Cape Province of South Africa

    NARCIS (Netherlands)

    Denman, S.; Crous, P.W.; Sadie, A.; Wingfield, M.J.

    2004-01-01

    A range of fungicides was tested in vitro for their effect on mycelial inhibition. Selected products showing potential for disease control were then further tested under field conditions. The most effective fungicides in the in vitro tests were tebuconazole, benomyl, prochloraz me, iprodione and

  17. Fungicide sensitivity of Tapesia yallundae populations collected from 15 wheat fields in the Western Cape of South Africa

    NARCIS (Netherlands)

    Ntushelo, K.; Crous, P.W.

    2004-01-01

    In the Western Cape province of South Africa, eyespot disease (Tapesia yallundae) of wheat is primarily controlled by fungicide applications. Previous studies have shown, however, that isolates of T. yallundae vary in their response to fungicides. In the present study, 20 isolates from each of 15

  18. Antiandrogenic effects in vitro and in vivo of the fungicide prochloraz

    DEFF Research Database (Denmark)

    Vinggaard, Anne Marie; Nellemann, Christine; Dalgaard, Majken

    2002-01-01

    The commonly used imidazole fungicide prochloraz was tested for antiandrogenic effects in vitro and in vivo. Prochloraz, but not the metabolites 2,4,6-trichlorophenoxyacetic acid or 2,4,6-trichlorophenol, inhibited the R1881-induced response in an androgen receptor reporter gene assay. In the Her......The commonly used imidazole fungicide prochloraz was tested for antiandrogenic effects in vitro and in vivo. Prochloraz, but not the metabolites 2,4,6-trichlorophenoxyacetic acid or 2,4,6-trichlorophenol, inhibited the R1881-induced response in an androgen receptor reporter gene assay...

  19. Effects of the hydrogen potential and fungicide treatment on Pitaya seed germination

    OpenAIRE

    Ortiz, Thiago Alberto; Moritz, Aline; Oliveira, Mariana Alves de; Takahashi, Lúcia Sadayo Assari

    2015-01-01

    The objective of the present study was to evaluate pitaya seed germination under different hydrogen potentials, with or without fungicide treatment. A completely randomized design was employed under a 3 x 13 x 2 factorial scheme, corresponding to three pitaya species (white pitaya, pitaya hybrid I, pitaya hybrid II), thirteen hydrogen potentials (3.0, 3.5, 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5, 8.0, 8.5, and 9.0) and two fungicide conditions (presence and absence), with four replications. Th...

  20. The effect of foliar fungicides on the mycoflora of seeds of Triticum aestivum

    Directory of Open Access Journals (Sweden)

    Janusz Błaszkowski

    2014-08-01

    Full Text Available The effect of three foliar fungicides. i.e., Bayloton 25 WP, Dithane M-45, and Funaben K. on the mycoflora associated with the seeds of spring Triticum aestivum cv. Kolibri cultivated in the field was investigated. The fungicide which highly reduced the number of both fungal colonies and species was Funaben K. Of the fungi most frequently occurring. Only Funaben K applied on the seeds reduced the proportion of seeds with Alternaria alternata, Cladosporium spp.. and Septoria nodorum. In contrast. seeds from plants traeted with Funaben K harboured significantly more colonies of non-sporulating fungi.

  1. Differences in sensitivity between earthworms and enchytraeids exposed to two commercial fungicides.

    Science.gov (United States)

    Bart, Sylvain; Laurent, Céline; Péry, Alexandre R R; Mougin, Christian; Pelosi, Céline

    2017-06-01

    The use of pesticides in crop fields may have negative effects on soil Oligochaeta Annelida, i.e., earthworms and enchytraeids, and thus affect soil quality. The aim of this study was to assess the effects of two commercial fungicide formulations on the earthworm Aporrectodea caliginosa and the enchytraeid Enchytraeus albidus in a natural soil. The fungicides were Cuprafor micro® (copper oxychloride), commonly used in organic farming, and Swing Gold® (epoxiconazole and dimoxystrobin), a synthetic fungicide widely used in conventional farming to protect cereal crops. Laboratory experiments were used to assess the survival, biomass loss and avoidance behaviour. No lethal effect was observed following exposure to the copper fungicide for 14 days, even at 5000mgkg -1 of copper, i.e. 650 times the recommended dose (RD). However, a significant decrease in biomass was observed from 50mgkg -1 of copper (6.5 times the RD) for A. caliginosa and at 5000mgkg -1 of copper (650 times the RD) for E. albidus. These sublethal effects suggest that a longer period of exposure would probably have led to lethal effects. The EC50 avoidance for the copper fungicide was estimated to be 51.2mgkg -1 of copper (6.7 times the RD) for A. caliginosa, and 393mgkg -1 of copper (51 times the RD) for E. albidus. For the Swing Gold® fungicide, the estimated LC50 was 7.0 10 -3 mLkg -1 (6.3 times the RD) for A. caliginosa and 12.7 10 -3 mLkg -1 (11.0 times the RD) for E. albidus. No effect on biomass or avoidance was observed at sublethal concentrations of this synthetic fungicide. It was concluded that enchytraeids were less sensitive than earthworms to the two commercial fungicides in terms of mortality, biomass loss and avoidance behaviour. Therefore we discuss the different strategies possibly used by the two Oligochaeta species to cope with the presence of the pesticides were discussed, along with the potential consequences on the soil functions. Copyright © 2017 Elsevier Inc. All rights

  2. Aerobic Oxidative Cycloaddition of α-Chlorotosylhydrazones with Arylamines: General Chemoselective Construction of 1,4-Disubstituted and 1,5-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions.

    Science.gov (United States)

    Bai, Hui-Wen; Cai, Zhong-Jian; Wang, Shun-Yi; Ji, Shun-Jun

    2015-06-19

    A novel synthetic approach toward 1,4-disubstituted 1,2,3-triazoles and 1,5-disubstituted 1,2,3-triazoles by aerobic oxidative cycloaddition of α-chlorotosylhydrazone with primary aryl amine has been developed. Significantly, the reaction proceeds smoothly to afford 1,4-disubstituted 1,2,3-triazoles and 1,5-disubstituted 1,2,3-triazoles under catalyst-free, metal-free, azide-free, and peroxide-free conditions.

  3. Design, synthesis, and antifungal activities of novel triazole derivatives containing the benzyl group

    Directory of Open Access Journals (Sweden)

    Xu K

    2015-03-01

    Full Text Available Kehan Xu,1,* Lei Huang,1,* Zheng Xu,2 Yanwei Wang,1,3 Guojing Bai,1 Qiuye Wu,1 Xiaoyan Wang,1 Shichong Yu,1 Yuanying Jiang1 1School of Pharmacy, Second Military Medical University, Shanghai, 2Shanghai Changzheng Hospital, Second Military Medical University, Shanghai, 3Number 422 Hospital of PLA, Zhanjiang, People’s Republic of China *These authors contributed equally to this work Abstract: In previous studies undertaken by our group, a series of 1-(1H-1,2,4-triazole-1-yl-2-(2,4-difluorophenyl-3-substituted-2-propanols (1a–r, which were analogs of fluconazole, was designed and synthesized by click chemistry. In the study reported here, the in vitro antifungal activities of all the target compounds were evaluated against eight human pathogenic fungi. Compounds 1a, 1q, and 1r showed the more antifungal activity than the others. Keywords: triazole, synthesis, antifungal activity, CYP51

  4. Synthesis, antiproliferative and antimicrobial activity of new Mannich bases bearing 1,2,4-triazole moiety.

    Science.gov (United States)

    Popiołek, Łukasz; Rzymowska, Jolanta; Kosikowska, Urszula; Hordyjewska, Anna; Wujec, Monika; Malm, Anna

    2014-12-01

    Abstract This study presents the synthesis, antiproliferative and antimicrobial evaluation of a new series of Mannich base derivatives containing 1,2,4-triazole system. New compounds were prepared by the reaction of 4,5-disubstituted 1,2,4-triazole-3-thiones with formaldehyde and various amines. The structures of the prepared compounds were confirmed by means of (1)H NMR, (13)C NMR and elemental analyses. Twelve compounds were evaluated for their in vitro antiproliferative activities against six chosen cancer cell lines. All synthesized compounds were screened for their in vitro antimicrobial activity by using the agar dilution technique. For 17 potentially active compounds, their antibacterial activity was confirmed on the basis of MIC (minimal inhibitory concentration) by broth microdilution method using the reference Gram-positive and Gram-negative bacterial strains.

  5. Experimental and theoretical studies on electrochemical synthesis of poly(3-amino-1,2,4-triazole)

    Energy Technology Data Exchange (ETDEWEB)

    Mert, Basak Dogru, E-mail: bdogru@cu.edu.tr [Cukurova University, Science and Letters Faculty, Chemistry Department, 01330 Balcal Latin-Small-Letter-Dotless-I , Adana (Turkey); Mert, M. Erman; Kardas, Guelfeza; Yaz Latin-Small-Letter-Dotless-I c Latin-Small-Letter-Dotless-I , Birguel [Cukurova University, Science and Letters Faculty, Chemistry Department, 01330 Balcal Latin-Small-Letter-Dotless-I , Adana (Turkey)

    2012-10-01

    Highlights: Black-Right-Pointing-Pointer The poly(3-amino-1,2,4-triazole) was electrochemically synthesized. Black-Right-Pointing-Pointer The homogeneous, colorful polymer has higher thermal and electrochemical stability. Black-Right-Pointing-Pointer The correlation was observed between experimental and theoretical data. - Abstract: The electrochemical synthesis of poly(3-amino-1,2,4-triazole) (PATA) on the platinum (Pt) electrode was achieved in ammonium oxalate solution by cyclic voltammetry technique. The conductivity of film was measured with four probe technique, the surface morphology was monitored with atomic force microscopy (AFM) and characterization was achieved by Fourier transform infrared spectroscopy (FT-IR) and UV-vis spectroscopy techniques. The thermal stability of polymer has also been investigated by the means of thermogravimetric analysis (TGA). The electrochemical stability of Pt/PATA was investigated in different buffer solutions. The quantum theoretical calculations employed and some parameters (dipole moment, E{sub HOMO}, E{sub LUMO}) were determined.

  6. Colorimetric sensing of iodide based on triazole-acetamide functionalized gold nanoparticles

    International Nuclear Information System (INIS)

    Lee, I-Lin; Sung, Yi-Ming; Wu, Shu-Pao; Wu, Chien-Hou

    2014-01-01

    We have modified gold nanoparticles (AuNPs) with triazole acetamide to obtain a material for the sensitive and selective colorimetric determination of iodide. The functionalized AuNPs were prepared by a reductive single chemical step using a Cu(I)-catalyzed click reaction. The presence of iodide ions induces the aggregation of these AuNPs and results in a color change from wine-red to purple. The iodide-induced aggregation can be detected visually with bare eyes, but also by photometry. The detection limit is as low as 15 nM. The method displays excellent selectivity for iodide over other anions due to the selective interaction with the amido groups of the triazole. The method was applied to the determination of iodide in spiked lake waters. (author)

  7. Synthesis, In Vitro Biological Evaluation, and Molecular Docking of New Triazoles as Potent Antifungal Agents.

    Science.gov (United States)

    Li, Xiang; Liu, Chao; Tang, Sheng; Wu, Qiuye; Hu, Honggang; Zhao, Qingjie; Zou, Yan

    2016-01-01

    Based on the structure of the active site of CYP51 and the structure-activity relationships of azole antifungal compounds that we designed in a previous study, a series of 1-{1-[2-(substitutedbenzyloxy)ethyl]-1H-1,2,3-triazol-4-yl}-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ols (6a-n) were designed and synthesized utilizing copper-catalyzed azide-alkyne cycloaddition. Preliminary antifungal tests against eight human pathogenic fungi in vitro showed that all the title compounds exhibited excellent antifungal activities with a broad spectrum in vitro. Molecular docking results indicated that the interaction between the title compounds and CYP51 comprised π-π interactions, hydrophobic interactions, and the narrow hydrophobic cleft. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  8. Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids

    Directory of Open Access Journals (Sweden)

    Morten Grøtli

    2009-12-01

    Full Text Available A versatile method for the synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives starting from easily accessible naturally occurring D-or L-amino acids as chiral synthons is described. The amino acids were converted into azido alcohols, followed by copper catalyzed [3+2] cycloaddition reactions between the azido alcohols and methyl propiolate and subsequent ester aminolysis with primary and secondary amines furnished the target compounds, which were obtained in excellent yields with no racemization. Docking of selected target compounds shows that the chiral 1,4-disubstituted-1,2,3-triazoles derivatives has the potential of mimicking the binding mode of known purine analogues.

  9. Reaction of 1,2,4-triazole-3-thiones with 1-chloro-2,3-epoxypropane

    International Nuclear Information System (INIS)

    Trzhtsinskaya, B.V.; Kositsyna, E.I.; Pertsikov, B.Z.; Rudakova, E.V.; Voronov, V.K.; Skvortsova, G.G.

    1987-01-01

    Addition of 1-chloro-2,3-epoxypropane to 1,2,4-triazole-3-thiones depending on the ratio of the reactants leads to the formation of 3-(1-chloro-2-hydroxypropyl)-3-(1-chloro-2-hydroxypropylthio)-1,2,4-triazoles. 3-Hydroxy-1,2,4-triazolo[2,3-b] tetrahydro-1,3-triazines have been synthesized by intramolecular cyclization of the monoadducts. IR spectra were recorded on a Specord 75-IR instrument as a thin layer, in KBr pellets, an in chloroform solution; PMR spectra were recorded on a Tesla BS-497 instrument (100 MHz) at 20 0 C in CD 3 OD with TMS as internal standard

  10. Assessment of Solvent-Induced Nitrogen Shielding Variations of Triazole Systems

    Science.gov (United States)

    Witanowski, M.; Sicinska, W.; Biedrzycka, Z.; Grabowski, Z.; Webb, G. A.

    High-precision 14N NMR shieldings are reported for all of the possible N-methyl triazoles in a variety of solvents. A large difference is observed in the effects of solvent on the shieldings of the pyrrole-type and pyridine-type nitrogen atoms in such systems. This difference largely arises from solvent-to-solute hydrogen-bonding effects for the latter type of nitrogen atom. For these two types of nitrogen atoms in triazoles, solvent polarity effects induce changes in the shieldings in opposite directions: this is corroborated by shielding calculations using the solvaton model. Solvent-to-solute hydrogen-bonding effects are larger than those due to solvent polarity and permit the assessment of the basicities of nonequivalent nitrogenous sites; these appear to parallel the analogous basicities with respect to protonation.

  11. Intra-annual trends of fungicide residues in waters from vineyard areas in La Rioja region of northern Spain.

    Science.gov (United States)

    Herrero-Hernández, Eliseo; Pose-Juan, Eva; Sánchez-Martín, María J; Andrades, M Soledad; Rodríguez-Cruz, M Sonia

    2016-11-01

    The temporal trends of fungicides in surface and ground water in 90 samples, including both surface waters (12) and ground waters (78) from an extensive vineyard area located in La Rioja (Spain), were examined between September 2010 and September 2011. Fungicides are used in increasing amounts on vines in many countries, and they may reach the water resources. However, few data have been published on fungicides in waters, with herbicides being the most frequently monitored compounds. The presence, distribution and year-long evolution of 17 fungicides widely used in the region and a degradation product were evaluated in waters during four sampling campaigns. All the fungicides included in the study were detected at one or more of the points sampled during the four campaigns. Metalaxyl, its metabolite CGA-92370, penconazole and tebuconazole were the fungicides detected in the greatest number of samples, although myclobutanil, CGA-92370 and triadimenol were detected at the highest concentrations. The highest levels of individual fungicides were found in Rioja Alavesa, with concentrations of up to 25.52 μg L -1 , and more than 40 % of the samples recorded a total concentration of >0.5 μg L -1 . More than six fungicides were positively identified in a third of the ground and surface waters in all the sampling campaigns. There were no significant differences between the results obtained in the four sampling campaigns and corroborated a pattern of diffuse contamination from the use of fungicides. The results confirm that natural waters in the study area are extremely vulnerable to contamination by fungicides and highlight the need to implement strategies to prevent and control water contamination by these compounds.

  12. The effect of the Falcon 460 EC fungicide on soil microbial communities, enzyme activities and plant growth.

    Science.gov (United States)

    Baćmaga, Małgorzata; Wyszkowska, Jadwiga; Kucharski, Jan

    2016-10-01

    Fungicides are considered to be effective crop protection chemicals in modern agriculture. However, they can also exert toxic effects on non-target organisms, including soil-dwelling microbes. Therefore, the environmental fate of fungicides has to be closely monitored. The aim of this study was to evaluate the influence of the Falcon 460 EC fungicide on microbial diversity, enzyme activity and resistance, and plant growth. Samples of sandy loam with pH KCl 7.0 were collected for laboratory analyses on experimental days 30, 60 and 90. Falcon 460 EC was applied to soil in the following doses: control (soil without the fungicide), dose recommended by the manufacturer, 30-fold higher than the recommended dose, 150-fold higher than the recommended dose and 300-fold higher than the recommended dose. The observed differences in the values of the colony development index and the eco-physiological index indicate that the mixture of spiroxamine, tebuconazole and triadimenol modified the biological diversity of the analyzed groups of soil microorganisms. Bacteria of the genus Bacillus and fungi of the genera Penicillium and Rhizopus were isolated from fungicide-contaminated soil. The tested fungicide inhibited the activity of dehydrogenases, catalase, urease, acid phosphatase and alkaline phosphatase. The greatest changes were induced by the highest fungicide dose 300-fold higher than the recommended dose. Dehydrogenases were most resistant to soil contamination. The Phytotoxkit test revealed that the analyzed fungicide inhibits seed germination capacity and root elongation. The results of this study indicate that excessive doses of the Falcon 460 EC fungicide 30-fold higher than the recommended dose to 300-fold higher than the recommended dose) can induce changes in the biological activity of soil. The analyzed microbiological and biochemical parameters are reliable indicators of the fungicide's toxic effects on soil quality.

  13. Aquatic Toxicity of 3-Nitro-1,2,4-Triazol-5-One

    Science.gov (United States)

    2009-09-01

    8RLAX1, U.S. Army Center for Health Promotion and Preventive Medicine , Directorate of Toxicology. The work was started in November 2008 and completed in...NITRO-l,2,4-TRIAZOL-5-ONE 1. INTRODUCTION The U. S. Army Center for Health Promotion and Preventive Medicine (USACHPPM), Directorate of Toxicology...Laboratory for Ecotoxicology , Institute for inland water management and waste water treatment: Lelystad, The Netherlands, 1982. 16. Army

  14. Triazole: a unique building block for the construction of functional materials.

    Science.gov (United States)

    Juríček, Michal; Kouwer, Paul H J; Rowan, Alan E

    2011-08-21

    Over the past 50 years, numerous roads towards carbon-based materials have been explored, all of them being paved using mainly one functional group as the brick: acetylene. The acetylene group, or the carbon-carbon triple bond, is one of the oldest and simplest functional groups in chemistry, and although not present in any of the naturally occurring carbon allotropes, it is an essential tool to access their synthetic carbon-rich family. In general, two strategies towards the synthesis of π-conjugated carbon-rich structures can be employed: (a) either the acetylene group serves as a building block to access acetylene-derived structures or (b) it serves as a synthetic tool to provide other, usually benzenoid, structures. The recently discovered copper-catalysed azide-alkyne cycloaddition (CuAAC) reaction, however, represents a new powerful alternative: it transforms the acetylene group into a five-membered heteroaromatic 1H-1,2,3-triazole (triazole) ring and this gives rise to new opportunities. Compared with all-carbon aromatic non-functional rings, the triazole ring possesses three nitrogen atoms and, thus, can serve as a ligand to coordinate metals, or as a hydrogen bond acceptor and donor. This Feature Article summarises examples of using the triazole ring to construct conjugation- and/or function-related heteroaromatic materials, such as tuneable multichromophoric covalent ensembles, macrocyclic receptors or responsive foldamers. These recent examples, which open a new sub-field within organic materials, started to appear only few years ago and represent "a few more bricks" on the road to carbon-rich functional materials. This journal is © The Royal Society of Chemistry 2011

  15. Association constants of modified humic acids with biocides of the triazole series: Cyproconazole and tebuconazole

    Science.gov (United States)

    Mal'Tseva, E. V.; Yudina, N. V.; Chaikovskaya, O. N.; Nechaev, L. V.

    2011-09-01

    The interaction of humic acids with biocides of triazoles in dependence on the concentration of components in solutions was investigated by spectrofluorimetry. The complex behavior of intermolecular interactions between biocides and humic acids, including donor-acceptor and hydrophobic bonds, was established. The effect of conditions of mechanochemical modification of humic acids and pH on the efficiency of interaction with biocides is shown.

  16. Synthesis of N-substituted phthalimidoalkyl 1,2,3-triazoles via click chemistry

    Directory of Open Access Journals (Sweden)

    Moara T. da Silva

    2012-06-01

    Full Text Available In the present work, we have developed a facile procedure for synthesis of new N-phthalimidoalkyl 1H-1,2,3-Triazoles (1-4(a-h using DMF, 10 mol% CuI, Et3N and ultrasound energy at room temperature. This protocol furnished 28 new compounds in 20 to 30 min of reaction and moderate-to-excellent yields (64-94%.

  17. Spectrophotometric determination of palladium with 5-mercapto-1,2,4-triazol

    International Nuclear Information System (INIS)

    Mishovicj, D.J.; Golubovicj, B.V.; Gligorijevicj, Zh.V.

    1976-01-01

    5-Mercapto-1,2,4-triazol is proposed as reagent for spectrophotometric detn of Pd. The reagent gives with Pd ions a yellow soln. The detn. is carried out at pH 12 and 380 nm. The concn. range where Beer's law applies is between 2.4 and 11.8mg/1. The color of the complex is unstable and the detn. has to be done immediately after reagent addition. Interferences of other ions were not investigated

  18. Computational Studies on Nitro Derivatives of 1-Hydroxy-1,2,4-triazole

    Science.gov (United States)

    Singh, Hariji; Mukherjee, Uttama; Shankar Saini, Ravi

    2012-07-01

    Thermodynamic properties and energetics of the nitro derivatives of 1-hydroxy-1,2,4-triazole, viz. 1-hydroxy-3-nitro-1,2,4-triazole (A), 1-hydroxy-5-nitro-1,2,4-triazole (B), and 1-hydroxy-3,5-dinitro-1,2,4-triazole (C), are considered for a detailed computational study during the present investigation using a density functional theory B3LYP/6-311G(d,p) method as implemented in the Gaussian 03 suite of programs. Heats of formation and other thermodynamic properties for all of the compounds considered were determined. Studies revealed that these compounds possess the requisite properties for use as high-density energetic materials. Detonation velocity (D) and detonation pressure (P) of the title compounds were evaluated using the Kamlet-Jacobs method based on the crystal densities calculated at the DFT(B3LYP)/6-311G(d,p) level incorporating the electrostatic interaction. Calculation showed that these compounds yielded a detonation pressure and detonation velocity in the range of 27-35 GPa and ∼8 km/s, respectively, at loading densities of 1.60-1.90 g/cm3. The calculated values are comparable to the values determined for powerful commercial explosives such as Research Department Explosive (RDX) (34.10 GPa, 8.75 km/s, 1.80 g/cm3), High Melting Explosive (HMX) (39.00 GPa, 9.11 km/s, 1.89 g/cm3), and Trinitrotoluene (TNT) (21.00 GPa, 6.93 km/s, 1.64 g/cm3).

  19. Synthesis and Reactivity of Sulfamoyl Azides and 1-Sulfamoyl-1,2,3-triazoles

    Science.gov (United States)

    Culhane, Jeffrey C.

    2011-01-01

    Sulfamoyl azides are readily generated from secondary amines and a novel sulfonyl azide transfer agent, 2,3-dimethyl-1H-imidazolium triflate. They react with alkynes in the presence of CuTC catalyst forming 1-sulfamoyl-1,2,3-triazoles. The latter are shelf-stable progenitors of rhodium azavinyl carbenes, versatile reactive intermediates that, among other reactions, readily and asymmetrically add to olefins. PMID:21812453

  20. SERS enhancement of silver nanoparticles prepared by a template-directed triazole ligand strategy.

    Science.gov (United States)

    Kashmery, Heba A; Thompson, David G; Dondi, Ruggero; Mabbott, Samuel; Graham, Duncan; Clark, Alasdair W; Burley, Glenn A

    2015-08-21

    Two advances in the development of a one-pot method to prepare silver nanoparticles (AgNPs) using the Tollens' reagent are described. First, a template-directed process of AgNP synthesis using resorcinol triazole ligands bearing two pendent galactose sugars is shown. Second, the conversion of these AgNPs into SERS nanotags is demonstrated using malachite green isothiocyanate as the Raman reporter molecule.

  1. Nickel complexes with "click"-derived pyridyl-triazole ligands: weak intermolecular interactions and catalytic ethylene oligomerisation.

    Science.gov (United States)

    Schweinfurth, David; Su, Cheng-Yong; Wei, Shi-Chao; Braunstein, Pierre; Sarkar, Biprajit

    2012-11-07

    The ligands 1-(cyclohexyl)-4-(2-pyridyl)-1,2,3-triazole (1), 1-(2,6-diisopropylphenyl)-4-(2-pyridyl)-1,2,3-triazole (2), 1-(4-butoxyphenyl)-4-(2-pyridyl)-1,2,3-triazole (3) and 1-(methyl)-4-(2-pyridyl)-1,2,3-triazole (4) were synthesized by the Cu(I) catalyzed "Click" reaction between 2-pyridylacetylene and the corresponding azides. The ligands were then reacted with NiBr(2)·3H(2)O to generate the complexes (1)(2)NiBr(2) (1a), (2)(2)NiBr(2) (2a), (3)(2)NiBr(2) (3a) and (4)(2)NiBr(2) (4a). Structural characterization of 1a confirmed the mononuclear and distorted octahedral environment around the Ni(II) center, with the pyridyl-triazole ligands coordinating in a bis-chelating fashion. Bond length analysis inside the 1,2,3-triazole ring shows a short N=N double bond that is flanked by two longer C-N and N-N bonds pointing to the existence of "azo" character in the ring. The highly polar five-membered 1,2,3-triazole ring makes its C-H bond acidic, and these bonds participate in an extended weak intermolecular C-H···Br interactions with the Br-groups of neighboring molecules, resulting in a 3-D network. The nickel complexes with these "Click" ligands were tested as pre-catalysts for ethylene oligomerization, and the complexes showed moderate activity in that reaction with good selectivity towards C4 oligomers.

  2. Synthesis, antitumor activity, and cytotoxicity of 4-substituted 1-benzyl-5-diphenylstibano-1H-1,2,3-triazoles.

    Science.gov (United States)

    Yamada, Mizuki; Takahashi, Tsutomu; Hasegawa, Mai; Matsumura, Mio; Ono, Kanna; Fujimoto, Ryota; Kitamura, Yuki; Murata, Yuki; Kakusawa, Naoki; Tanaka, Motohiro; Obata, Tohru; Fujiwara, Yasuyuki; Yasuike, Shuji

    2018-01-15

    Trisubstituted 5-organostibano-1H-1,2,3-triazoles (3a-f) were synthesized by the Cu-catalyzed azide-alkyne cycloaddition of various ethynylstibanes (1) with benzylazide (2) in the presence of CuBr (5 mol%) under aerobic conditions. The reaction of 5-stibanotriazoles with HCl afforded C5-unsubstituted 1,2,3-triazoles (4a-f). The antitumor activity of trisubstituted 5-organostibano-1H-1,2,3-triazoles (3a-f) and their 5-unsubstituted 1,2,3-triazoles (4a-f) were evaluated in several tumor cell lines. All 5-stibanotriazoles (3a-f) exerted an excellent antitumor activity. On the contrary, 5-unsubstituted 1,2,3-triazoles (4a-f) without a diphenylantimony group in the molecule exhibited very low antitumor activity compared with 5-stibanotriazoles (3a-f). In compounds of both the series, the substituted 4-butyl group appeared to decrease antitumor activity. However, results suggested that organometal (antimony) in the molecule was required for greater antitumor activity. In addition, all 5-stibanotriazoles (3a-f), but not all 5-unsubstituted 1,2,3-triazoles (4a-f), exhibited cytotoxicity in normal vascular endothelial cells derived from bovine aorta. Among the compounds (3b-e) that exhibited excellent antitumor activity, those with 4-methylphenyl (3b) and 1-cyclohexenyl (3e) showed relatively low cytotoxicity to vascular endothelial cells. Together, these results suggest that trisubstituted 5-organostibano-1H-1,2,3-triazoles, including compounds 3b and 3e, may serve as potential anticancer therapeutic drugs in the future. Copyright © 2017 Elsevier Ltd. All rights reserved.

  3. Synthesis of new triazole arotinoids analogues via "Click Chemistry" with potential anticancer activity

    Directory of Open Access Journals (Sweden)

    Mariana A. A. Aleixo

    2012-06-01

    Full Text Available Retinoids are  a  class  of  natural  and  synthetic  vitamin A analogues structurally related to all-trans-retinoic acid (ATRA. This class of compounds can inhibit cell proliferation and induce differentiation and apoptosis of cells, and several are used in cancer therapy. Using the concept of bioisosterism, new triazole analogues were designed from the molecular modification of the potent derivative arotinoid AM580. This compound has an amide grouping which is a bioisostere of 1,2,3-triazole ring. Through "Click Chemistry” approach, triazole analogues were obtained by reaction of Huisgen 1,3-dipolar cycloaddition between aryl azides and terminal acetylene, previously synthesized. The reagents used were CuI, triethylamine and mixture of ethanol:water. The first compound synthesized showed anticancer activity, while the second proved to be inactive. The molecular docking results showed that both compounds have high affinity for the retinoid RARα receptor (related to anticancer activity, but probably the second compound has antagonist activity on this receptor.

  4. New compounds hybrids 1h-1,2,3-triazole-quinoline against Plasmodium falciparum.

    Science.gov (United States)

    Boechat, Núbia; Ferreira, Maria de Lourdes G; Pinheiro, Luiz C S; Jesus, Antônio M L; Leite, Milene M M; Júnior, Carlos C S; Aguiar, Anna C C; de Andrade, Isabel M; Krettli, Antoniana U

    2014-09-01

    Malaria is one of the most prevalent parasitic diseases in the world. The global importance of this disease, current vector control limitations, and the absence of an effective vaccine make the use of therapeutic antimalarial drugs the main strategy to control malaria. Chloroquine is a cost-effective antimalarial drug with a relatively robust safety profile, or therapeutic index. However, chloroquine is no longer used alone to treat patients with Plasmodium falciparum due to the emergence and spread of chloroquine-resistant strains, which have also been reported for Plasmodium vivax. However, the activity of 1,2,3-triazole derivatives against chloroquine-sensitive and chloroquine-resistant strains of P. falciparum has been reported in the literature. To enhance the anti-P. falciparum activity of quinoline derivatives, we synthesized 11 new quinoline-1H-1,2,3-triazole hybrids with different substituents in the 4-positions of the 1H-1,2,3-triazole ring, which were assayed against the W2-chloroquine-resistant P. falciparum clone. Six compounds exhibited activity against the P. falciparum W2 clone, chloroquine-resistant, with IC50 values ranging from 1.4 to 46 μm. None of these compounds was toxic to a normal monkey kidney cell line, thus exhibiting good selectivity indexes, as high 351 for one compound (11). © 2014 John Wiley & Sons A/S.

  5. Triazole-curcuminoids: A new class of derivatives for 'tuning' curcumin bioactivities?

    Science.gov (United States)

    Caprioglio, Diego; Torretta, Simone; Ferrari, Maila; Travelli, Cristina; Grolla, Ambra A; Condorelli, Fabrizio; Genazzani, Armando A; Minassi, Alberto

    2016-01-15

    Curcumin is a unique blend of pharmacophores responsible for the pleiotropy of this natural pigment. In the present study we have replaced the 1,3-dicarbonyl moiety with a 1,2,3-triazole ring to furnish a new class of triazole-curcuminoids as a possible strategy to generate new compounds with different potency and selectivity compared to curcumin. We obtained a proof-of-principle library of 28 compounds tested for their cytotoxicity (SY-SY5Y and HeLa cells) and for their ability to inhibit NF-κB. Furthermore, we also generated 1,3-dicarbonyl curcuminoids of selected click compounds. Triazole-curcuminoids lost their ability to be Michael's acceptors, yet maintained some of the features of the parent compounds and disclosed new ones. In particular, we found that some compounds were able to inhibit NF-κB without showing cytotoxicity, while others, unlike curcumin, activated NF-κB signalling. This validates the hypothesis that click libraries can be used to investigate the biological activities of curcumin as well as generate analogs with selected features. Copyright © 2015 Elsevier Ltd. All rights reserved.

  6. Theoretical study of an energetic material di-1H-1,3,4-triazole derivatives

    Directory of Open Access Journals (Sweden)

    Hua Zhou

    2014-12-01

    Full Text Available Computations by density functional theory (DFT method are performed on a series of di-1H-1,3,4-triazole derivatives with different substituents and linkages. The heat of formation (HOF is predicted by the designed isodesmic reactions. The predicted results reveal that –N3 and –NN– groups are effective structural units for increasing the HOF values of the di-1H-1,3,4-triazole derivatives. The HOMO–LUMO gap is affected by the substituents and linkage groups. Detonation performance is evaluated using the Kamlet–Jacobs approach based on the calculated density and HOF. The results indicate that –NO2, –NF2, –NH–, –NH–NH– and –NN– groups are helpful for enhancing the detonation properties of di-1H-1,3,4-triazole derivatives. The bond dissociation energy and bond order of the weakest bonds are analyzed to investigate their stability. It is observed that the –CH2–, –CH2–CH2– and –CHCH– groups are effective structural units for improving the stabilities of these derivatives. Considering the detonation performance and the stability, five compounds are screened as the potential candidates for high energy density materials.

  7. α-Methylation enhances the potency of isoprenoid triazole bisphosphonates as geranylgeranyl diphosphate synthase inhibitors.

    Science.gov (United States)

    Matthiesen, Robert A; Varney, Michelle L; Xu, Pauline C; Rier, Alex S; Wiemer, David F; Holstein, Sarah A

    2018-01-15

    Disruption of protein geranylgeranylation via inhibition of geranylgeranyl diphosphate synthase (GGDPS) represents a novel therapeutic strategy for a variety of malignancies, especially those characterized by excessive protein secretion such as multiple myeloma. Our work has demonstrated that some isoprenoid triazole bisphosphonates are potent and selective inhibitors of GGDPS. Here we present the synthesis and biological evaluation of a new series of isoprenoid triazoles modified by incorporation of a methyl group at the α-carbon. These studies reveal that incorporation of an α-methyl substituent enhances the potency of these compounds as GGDPS inhibitors, and, in the case of the homogeranyl/homoneryl series, abrogates the effects of olefin stereochemistry on inhibitory activity. The incorporation of the methyl group allowed preparation of a POM-prodrug, which displayed a 10-fold increase in cellular activity compared to the corresponding salt. These studies form the basis for future preclinical studies investigating the anti-myeloma activity of these novel α-methyl triazole bisphosphonates. Copyright © 2017 Elsevier Ltd. All rights reserved.

  8. Synthesis and Antimicrobial Activities of Some New 1,2,4-Triazole Derivatives

    Directory of Open Access Journals (Sweden)

    Hakan Bektaş

    2010-04-01

    Full Text Available Some novel 4,5-disubstituted-2,4-dihydro-3H-1,2,4-triazol-3-one (3, 6, 8, 9 derivatives and or 3-(4-methylphenyl[1,2,4]triazolo[3,4-b][1,3]benzoxazole (5 were synthesized from the reaction of various ester ethoxycarbonylhydrazones (1a-e with several primary amines. The synthesis of 4-amino-5-(4-chlorophenyl-2-[(5-mercapto-1,3,4-oxadiazol-2-ylmethyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (13 was performed starting from 4-Amino-5-(4-chlorophenyl-2,4-dihydro-3H-1,2,4-triazol-3-one (2 by four steps; then 13 was converted to the corresponding Schiff base (14 by using 4-methoxybenzaldehyde. Finally, two Mannich base derivatives of 14 were obtained by using morpholine or methyl piperazine as amine component. All newly synthesized compounds were screened for their antimicrobial activities and some of which were found to possess good or moderate activities against the test microorganisms.

  9. Equilibrium studies of ternary systems containing some selected transition metal ions, triazoles and aromatic carboxylic acids

    Energy Technology Data Exchange (ETDEWEB)

    Khalil, Mohamed Magdy; Radalla, Abd-Elatty; Qasem, Fatma; Khaled, Rehab [Beni-Suef University, Beni-Suef (Egypt)

    2014-01-15

    Solution equilibria of the binary and ternary complex systems of the divalent transition metal ions Cu{sup 2+}, Ni{sup 2+}, Zn{sup 2+}, and Co{sup 2+} with 1,2,4-triazole (TRZ), 3-mercapto-1,2,4-triazole (TRZSH), and 3-amino-1,2,4-triazole (TRZAM) and aromatic carboxylic acids (phthalic, anthranilic, salicylic, and 5-sulfosalicylic acid) have been studied pH-metrically at (25.0±0.1) .deg. C, and a constant ionic strength I=1x10{sup -1} mol L{sup -1} NaNO{sub 3} in an aqueous medium. The potentiometric titration curves show that binary and ternary complexes of these ligands are formed in solution. The stability constants of the different binary and ternary complexes formed were calculated on the basis of computer analysis of the titration data. The relative stability of the different ternary complex species is expressed in terms of Δ log K values, log X and R. S.% parameters. The effect of temperature of the medium on both the proton-ligand equilibria for TRZAM and phthalic acid and their metal-ligand equilibria with Cu{sup 2+}, Ni{sup 2+}, and Co{sup 2+} has been studied along with the corresponding thermodynamic parameters. The complexation behavior of ternary complexes is ascertained using conductivity measurements. In addition, the formation of ternary complexes in solution has been confirmed by using UV-visible spectrophotometry.

  10. Distinct effects of novel naphtoquinone-based triazoles in human leukaemic cell lines.

    Science.gov (United States)

    Coulidiati, Tangbadioa H; Dantas, Bruna B; Faheina-Martins, Glaucia V; Gonçalves, Juan C R; do Nascimento, Wilson S; de Oliveira, Ronaldo N; Camara, Celso A; Oliveira, Eduardo J; Lara, Aline; Gomes, Eneas R; Araújo, Demetrius A M

    2015-12-01

    The aim of this study was to investigate the cytotoxic effect of new 1,4-naphthoquinone- 1,2,3-triazoles, named C2 to C8 triazole derivatives, towards human cancer cell lines. The effect on cell viability was assessed by MTT and propidium iodide assays. The cytotoxic effect of C2 and C3 in K562 and HL-60 cells were analyzed by flow cytometry, DNA fragmentation and reactive oxygen species (ROS) production. Western blot and q-PCR procedures were also performed. C2 and C3 inhibited both K562 and HL-60 cells growth in a concentration-dependent manner. C2 presented the highest cytotoxic activity with an IC50 of approximately 14 μm and 41 μm for HL-60 and K562 cells, respectively, while being less toxic to normal peripheral blood monocyte cells. Both derivatives induced cellular changes in HL-60 cells, characteristic of apoptosis, such as mitochondrial membrane depolarization, phosphatidylserine externalization, increasing sub-G1 phase, DNA fragmentation, downregulating Bcl-2 protein and upregulating Bax protein. In K562 cells, C2 and C3 induced S-phase arrest of cell cycle, which was associated with upregulation of p21. The effect of these derivatives in HL-60 cells can be related to the ROS intracellular level. Taken together our results showed that C2 and C3 triazole derivatives presented the best potential for drug design. © 2015 Royal Pharmaceutical Society.

  11. Synthesis and biological evaluation of novel isoxazoles and triazoles linked 6-hydroxycoumarin as potent cytotoxic agents.

    Science.gov (United States)

    Shakeel-u-Rehman; Masood-ur-Rahman; Tripathi, Vijay K; Singh, Jasvinder; Ara, Tabassum; Koul, Surrinder; Farooq, Saleem; Kaul, Anupurna

    2014-09-01

    A new series of diverse isoxazoles and triazoles linked 6-hydroxycoumarin (1) were synthesized using click chemistry approach. All the derivatives were subjected to 3-(4,5-dimethylthiazol-yl)-diphenyl tetrazoliumbromide (MTT) cytotoxicity screening against a panel of five different human cancer cell lines viz. prostate (PC-3), colon (HCT-116 and Colo-205), leukemia (HL-60) and lung (A-549) to check their cytotoxic potential. Interestingly, among the tested molecules, some of the analogs displayed better cytotoxic activity than the parent 6-hydroxycoumarin (1). Of the synthesized isoxazoles, compounds 10 and 13 showed the best activity with IC50 of 8.2 and 13.6 μM against PC-3 cancer cell line, while as, among the triazoles, compounds 23 and 25 were the most active with the IC50 of 10.2 and 12.6 μM against A-549 cancer cell line. The other derivatives showed almost comparable activity with that of the parent molecule. The present study resulted in identification of ortho substituted isoxazole and triazole derivatives of 6-hydroxycoumarin as effective cytotoxic agents against prostate (PC-3) and lung (A-549) cancer cell lines, respectively. Copyright © 2014 Elsevier Ltd. All rights reserved.

  12. DFT studies on tautomerism of C5-substituted 1,2,3-triazoles

    Science.gov (United States)

    Ozimiński, Wojciech P.; Dobrowolski, Jan Cz.; Mazurek, Aleksander P.

    2003-06-01

    DFT (B3PW91/6-311++G**), ab initio (HF/6-311++G**), and single point CCSD(T)/6-311++G**//B3PW91/6-311++G** calculations were performed to investigate the stability and tautomerism of the C5-substituted 1,2,3-triazoles. Three different tautomers are possible for the substituted 1,2,3-triazoles: N1-H, N2-H, and N3-H. For all the substituents applied, the most stable is the N2-H tautomer. Out of the two less stable tautomers, N1-H and N3-H, the -F, -CFO, -CH 3, -CHO, -Cl, -CN, -CONH 2, -NH 2, -NO 2, and -OH substituents stabilize the N3-H tautomer, whereas only the -BH 2, -BF 2, and -COOH substituents stabilize the N1-H form. The relative stability of the C5-substituted 1,2,3-triazoles tautomerism is strongly influenced by the possibility for intramolecular interactions (both attractive and repulsive) between substituent and protons located either at N1 or N3 atom. For all the molecules studied, the Gibbs free energy at 0 and 298 K was estimated, too.

  13. Antivenom Effects of 1,2,3-Triazoles against Bothrops jararaca and Lachesis muta Snakes

    Science.gov (United States)

    Domingos, Thaisa F. S.; Moura, Laura de A.; Carvalho, Carla; Campos, Vinícius R.; Jordão, Alessandro K.; Cunha, Anna C.; Ferreira, Vitor F.; de Souza, Maria Cecília B. V.; Sanchez, Eladio F.; Fuly, André L.

    2013-01-01

    Snake venoms are complex mixtures of proteins of both enzymes and nonenzymes, which are responsible for producing several biological effects. Human envenomation by snake bites particularly those of the viperid family induces a complex pathophysiological picture characterized by spectacular changes in hemostasis and frequently hemorrhage is also seen. The present work reports the ability of six of a series of 1,2,3-triazole derivatives to inhibit some pharmacological effects caused by the venoms of Bothrops jararaca and Lachesis muta. In vitro assays showed that these compounds were impaired in a concentration-dependent manner, the fibrinogen or plasma clotting, hemolysis, and proteolysis produced by both venoms. Moreover, these compounds inhibited biological effects in vivo as well. Mice treated with these compounds were fully protected from hemorrhagic lesions caused by such venoms. But, only the B. jararaca edema-inducing activity was neutralized by the triazoles. So the inhibitory effect of triazoles derivatives against some in vitro and in vivo biological assays of snake venoms points to promising aspects that may indicate them as molecular models to improve the production of effective antivenom or to complement antivenom neutralization, especially the local pathological effects, which are partially neutralized by antivenoms. PMID:23710441

  14. Effects of current-use fungicides and their mixtures on the feeding and survival of the key shredder Gammarus fossarum.

    Science.gov (United States)

    Zubrod, J P; Baudy, P; Schulz, R; Bundschuh, M

    2014-05-01

    Fungicides are frequently applied in agriculture and are subsequently detected in surface waters in total concentrations of up to several tens of micrograms per liter. These concentrations imply potential effects on aquatic communities and fundamental ecosystem functions such as leaf litter breakdown. In this context, the present study investigates sublethal and lethal effects of organic (azoxystrobin, carbendazim, cyprodinil, quinoxyfen, and tebuconazole) and inorganic (three copper (Cu)-based substances and sulfur) current-use fungicides and their mixtures on the key leaf-shredding invertebrate Gammarus fossarum. The feeding activity of fungicide-exposed gammarids was quantified as sublethal endpoint using a static (organic fungicides; 7 d test duration) or a semi-static (inorganic fungicides; 6 d test duration with a water exchange after 3 d) approach (n=30). EC50-values of organic fungicides were generally observed at concentrations resulting in less than 20% mortality, with the exception of carbendazim. With regard to feeding, quinoxyfen was the most toxic organic fungicide, followed by cyprodinil, carbendazim, azoxystrobin, and tebuconazole. Although all tested organic fungicides have dissimilar (intended) modes of action, a mixture experiment revealed a synergistic effect on gammarids' feeding at high concentrations when using "independent action" as the reference model (∼35% deviation between predicted and observed effect). This may be explained by the presence of a synergizing azole fungicide (i.e. tebuconazole) in this mixture. Furthermore, lethal concentrations of all Cu-based fungicides assessed in this study were comparable amongst one another. However, they differed markedly in their effective concentrations when using feeding activity as the endpoint, with Cu-sulfate being most toxic, followed by Cu-hydroxide and Cu-octanoate. In contrast, sulfur neither affected survival nor the feeding activity of gammarids (up to ∼5 mg/L) but reduced Cu

  15. [Hydrogen bis(1,2,4-triazole] 1,2,4-triazolium bis(3-carboxy-4-hydroxybenzenesulfonate 1,2,4-triazole disolvate

    Directory of Open Access Journals (Sweden)

    Ming-qiang Qiu

    2010-08-01

    Full Text Available The title compound, C2H4N3+·[H(C2H3N32]+·2C7H5O6S−·2C2H3N3, consists of two types of 1,2,4-triazole monocation, one protonated at the 2-site lying across a twofold axis and the other protonated at the 4-site with the H atom disordered over a center of symmetry, a 5-sulfosalicylate anion and a neutral 1,2,4-triazole molecule. The component ions are linked into a three-dimensional network by a combination of N—H...O, N—H...N, O—H...O, O—H...N, C—H...O and C—H...N hydrogen bonds. In addition, benzene–benzene π–π interactions of 3.942 (2 Å [interplanar spacing = 3.390 (2 Å] and C—O...π (3.331 Å interactions are observed.

  16. Proposal for a unified nomenclature for target-site mutations associated with resistance to fungicides.

    Science.gov (United States)

    Mair, Wesley; Lopez-Ruiz, Francisco; Stammler, Gerd; Clark, William; Burnett, Fiona; Hollomon, Derek; Ishii, Hideo; Thind, Tarlochan S; Brown, James Km; Fraaije, Bart; Cools, Hans; Shaw, Michael; Fillinger, Sabine; Walker, Anne-Sophie; Mellado, Emilia; Schnabel, Guido; Mehl, Andreas; Oliver, Richard P

    2016-08-01

    Evolved resistance to fungicides is a major problem limiting our ability to control agricultural, medical and veterinary pathogens and is frequently associated with substitutions in the amino acid sequence of the target protein. The convention for describing amino acid substitutions is to cite the wild-type amino acid, the codon number and the new amino acid, using the one-letter amino acid code. It has frequently been observed that orthologous amino acid mutations have been selected in different species by fungicides from the same mode of action class, but the amino acids have different numbers. These differences in numbering arise from the different lengths of the proteins in each species. The purpose of the present paper is to propose a system for unifying the labelling of amino acids in fungicide target proteins. To do this we have produced alignments between fungicide target proteins of relevant species fitted to a well-studied 'archetype' species. Orthologous amino acids in all species are then assigned numerical 'labels' based on the position of the amino acid in the archetype protein. © 2016 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry. © 2016 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

  17. Effects of Artea, a systemic fungicide, on the antioxidant system and ...

    African Journals Online (AJOL)

    The present work is aimed at the study of Artea (a systemic fungicide) effects on durum wheat (Triticum durum L. CV. Hard GTA). Seeds were grown in a medium containing 25, 50, 75 and 100 ppm of Artea under controlled conditions. Roots of eight day old were used to determine the enzymatic activities of catalase, ...

  18. Evaluation of certain fungicides for the control of tar spot disease of ...

    African Journals Online (AJOL)

    The present study evaluated the favourable conditions as well as the effectiveness of fungicides in controlling the disease. Ben/ate, Dithane M-45 and Polyram-Combi at the rates of 1.0, 1. 5 and l. 5 gil of water respectively either totally or almost completely controlled the disease when aerial parts of the vines were sprayed ...

  19. Effect of mulch and different fungicide spray regimes on yield of ...

    African Journals Online (AJOL)

    Treatment factors comprised two varieties (main plot factor), mulching/number of mulching (subplot factor) and three fungicide spray regimes (sub subplot factor). Results showed that the spray regimes: farmers' practice (FP), Integrated Pests Management (IPM) based on pests scouting, sprays based on manufacturers' ...

  20. Effect of foliar application of fungicides on incidence and severity of ...

    African Journals Online (AJOL)

    Three fungicides were evaluated for their efficacy in controlling leaf spot disease in Roselle induced by Coniella musaiaensis in a randomized compete block design experiment in 2003 at Abeokuta, (7015'N, 3025'E) a transition zone in South Western Nigeria. The experiment was replicated three times and repeated in ...

  1. Reaction kinetics and mechanisms of organosilicon fungicide flusilazole with sulfate and hydroxyl radicals.

    Science.gov (United States)

    Mercado, D Fabio; Bracco, Larisa L B; Arques, Antonio; Gonzalez, Mónica C; Caregnato, Paula

    2018-01-01

    Flusilazole is an organosilane fungicide used for treatments in agriculture and horticulture for control of diseases. The reaction kinetics and mechanism of flusilazole with sulfate and hydroxyl radicals were studied. The rate constant of the radicals with the fungicide were determined by laser flash photolysis of peroxodisulfate and hydrogen peroxide. The results were 2.0 × 10 9 s -1 M -1 for the reaction of the fungicide with HO and 4.6 × 10 8  s -1  M -1 for the same reaction with SO 4 - radicals. The absorption spectra of organic intermediates detected by laser flash photolysis of S 2 O 8 2- with flusilazole, were identified as α-aminoalkyl and siloxyl radicals and agree very well with those estimated employing the time-dependent density functional theory with explicit account for bulk solvent effects. In the continuous photolysis experiments, performed by photo-Fenton reaction of the fungicide, the main degradation products were: (bis(4-fluorophenyl)-hydroxy-methylsilane) and the non-toxic silicic acid, diethyl bis(trimethylsilyl) ester, in ten and twenty minutes of reaction, respectively. Copyright © 2017. Published by Elsevier Ltd.

  2. Analysis of Fungicide Sensitivity and Genetic Diversity among Colletotrichum Species in Sweet Persimmon.

    Science.gov (United States)

    Gang, Geun-Hye; Cho, Hyun Ji; Kim, Hye Sun; Kwack, Yong-Bum; Kwak, Youn-Sig

    2015-06-01

    Anthracnose, caused by Colletotrichum gloeosporioides (C. gloeosporioides; Teleomorph: Glomerella cingulata), is the most destructive disease that affects sweet persimmon production worldwide. However, the biology, ecology, and genetic variations of C. gloeosporioides remain largely unknown. Therefore, in this study, the development of fungicide resistance and genetic diversity among an anthracnose pathogen population with different geographical origins and the exposure of this population to different cultivation strategies were investigated. A total of 150 pathogen isolates were tested in fungicide sensitivity assays. Five of the tested fungicides suppressed mycelial pathogen growth effectively. However, there were significant differences in the sensitivities exhibited by the pathogen isolates examined. Interestingly, the isolates obtained from practical management orchards versus organic cultivation orchards showed no differences in sensitivity to the same fungicide. PCR-restriction fragment length polymorphism (RFLP) analyses were performed to detect internal transcribed spacer regions and the β-tubulin and glutamine synthetase genes of the pathogens examined. Both the glutamine synthetase and β-tubulin genes contained a complex set of polymorphisms. Based on these results, the pathogens isolated from organic cultivation orchards were found to have more diversity than the isolates obtained from the practical management orchards.

  3. Analysis of Fungicide Sensitivity and Genetic Diversity among Colletotrichum Species in Sweet Persimmon

    Directory of Open Access Journals (Sweden)

    Geun-Hye Gang

    2015-06-01

    Full Text Available Anthracnose, caused by Colletotrichum gloeosporioides (C. gloeosporioides; Teleomorph: Glomerella cingulata, is the most destructive disease that affects sweet persimmon production worldwide. However, the biology, ecology, and genetic variations of C. gloeosporioides remain largely unknown. Therefore, in this study, the development of fungicide resistance and genetic diversity among an anthracnose pathogen population with different geographical origins and the exposure of this population to different cultivation strategies were investigated. A total of 150 pathogen isolates were tested in fungicide sensitivity assays. Five of the tested fungicides suppressed mycelial pathogen growth effectively. However, there were significant differences in the sensitivities exhibited by the pathogen isolates examined. Interestingly, the isolates obtained from practical management orchards versus organic cultivation orchards showed no differences in sensitivity to the same fungicide. PCR-restriction fragment length polymorphism (RFLP analyses were performed to detect internal transcribed spacer regions and the β-tubulin and glutamine synthetase genes of the pathogens examined. Both the glutamine synthetase and β-tubulin genes contained a complex set of polymorphisms. Based on these results, the pathogens isolated from organic cultivation orchards were found to have more diversity than the isolates obtained from the practical management orchards.

  4. Evaluation of fungicides to protect pruning wounds from Botryosphaeriaceae species infections on almond trees

    Directory of Open Access Journals (Sweden)

    Diego OLMO

    2017-05-01

    Full Text Available In vitro efficacy of ten fungicides was evaluated against four Botryosphaeriaceae spp. (Diplodia seriata, Neofusicoccum luteum, N. mediterraneum and N. parvum associated with branch cankers on almond trees. Cyproconazole, pyraclostrobin, tebuconazole, and thiophanate-methyl were effective for the inhibition of mycelial growth of most of these fungi. An experiment on 3-year-old almond trees evaluated boscalid, mancozeb, thiophanate-methyl, pyraclostrobin and tebuconazole for preventative ability against infections caused by the four pathogens. Five months after pruning and fungicide application, lesion length measurements and isolation percentages showed no significant differences among the four pathogens after they were inoculated onto the trees, and also between the two inoculation times tested (1 or 7 d after fungicide application. Thiophanate-methyl was the most effective fungicide, resulting in the shortest lesion lengths and the lowest isolation percentages from artificially inoculated pruning wounds. This chemical is therefore a candidate for inclusion in integrated disease management, to protect pruning wounds from infections caused by species of Botryosphaeriaceae. This study represents the first approach to development of chemical control strategies for the management of canker diseases caused by Botryosphaeriaceae fungi on almond trees. 

  5. Evaluation of fungicides for the control of false smut of rice caused ...

    African Journals Online (AJOL)

    Benomyl, Copper Oxychloride, Iprodione, Thiabendazole (TBZ) and Mancozeb were evaluated both in the laboratory and field study in 1994, for the control of false smut of rice caused by Ustilaginoidea virens (Cooke) Tak. in upland rice in Edo State, Nigeria. In the laboratory the fungicides were evaluated at three ...

  6. Activation of stress signalling pathways enhances tolerance of fungi to chemical fungicides and antifungal proteins.

    Science.gov (United States)

    Hayes, Brigitte M E; Anderson, Marilyn A; Traven, Ana; van der Weerden, Nicole L; Bleackley, Mark R

    2014-07-01

    Fungal disease is an increasing problem in both agriculture and human health. Treatment of human fungal disease involves the use of chemical fungicides, which generally target the integrity of the fungal plasma membrane or cell wall. Chemical fungicides used for the treatment of plant disease, have more diverse mechanisms of action including inhibition of sterol biosynthesis, microtubule assembly and the mitochondrial respiratory chain. However, these treatments have limitations, including toxicity and the emergence of resistance. This has led to increased interest in the use of antimicrobial peptides for the treatment of fungal disease in both plants and humans. Antimicrobial peptides are a diverse group of molecules with differing mechanisms of action, many of which remain poorly understood. Furthermore, it is becoming increasingly apparent that stress response pathways are involved in the tolerance of fungi to both chemical fungicides and antimicrobial peptides. These signalling pathways such as the cell wall integrity and high-osmolarity glycerol pathway are triggered by stimuli, such as cell wall instability, changes in osmolarity and production of reactive oxygen species. Here we review stress signalling induced by treatment of fungi with chemical fungicides and antifungal peptides. Study of these pathways gives insight into how these molecules exert their antifungal effect and also into the mechanisms used by fungi to tolerate sub-lethal treatment by these molecules. Inactivation of stress response pathways represents a potential method of increasing the efficacy of antifungal molecules.

  7. Comparative Assessment of the Effect of Synthetic and Natural Fungicides on Soil Respiration

    Directory of Open Access Journals (Sweden)

    Joanna D’Arc Felício

    2012-03-01

    Full Text Available As toxic pesticide residues may persist in agricultural soils and cause environmental pollution, research on natural fungicides to replace the synthetic compounds is currently increasing. The effect of the synthetic fungicide chlorothalonil and a natural potential fungicide on the soil microbial activity was evaluated here by the substrate-induced respiration by addition of glucose (SIR, as bioindicator in two soils (Eutrophic Humic Gley—GHE and Typic Eutroferric Chernosol—AVEC. The induced soil respiration parameter was followed during 28 days after soil treatment either with chlorathalonil (11 µg·g−1, or the methanolic fraction from Polymnia sonchifolia extraction (300 µg·g−1, and 14C-glucose (4.0 mg and 5.18 Bq of 14C-glucose g−1. The 14C-CO2 produced by the microbial respiration was trapped in NaOH (0.1 M which was changed each two hours during the first 10 h, and 1, 3, 5, 7, 14 and 28 days after the treatments. The methanolic fraction of the plant extract inhibited (2.2% and stimulated (1.8% the respiration of GHE and AVEC, respectively, but the synthetic chlorothalonil caused 16.4% and 2.6% inhibition of the respiration, respectively of the GHE and AVEC soils. As the effects of the natural product were statistically small, this bioindicator indicates that the methanolic fraction of the Polymnia sonchifolia extract, which has fungicide properties, has no environmental effects.

  8. Effects of artea, a systemic fungicide, on the antioxidant system and ...

    African Journals Online (AJOL)

    The present work aimed at the study of the effects of Artea, a systemic azole fungicide, on durum Wheat (Triticum durum L. cv. GTA dur). Seeds were grown in a medium containing respectively 25, 50, 75 and 100 ppm of Artea under controlled conditions. Roots of eight-day-old plants were used to determine catalase, ...

  9. The fungicidal properties of the carbon materials obtained from chitin and chitosan promoted by copper salts

    Energy Technology Data Exchange (ETDEWEB)

    Ilnicka, Anna, E-mail: annakucinska@o2.pl; Walczyk, Mariusz; Lukaszewicz, Jerzy P.

    2015-07-01

    Renewable raw materials chitin and chitosan (N-deacetylated derivative of chitin) were subjected to action of different copper modifiers that were carbonized in the atmosphere of the N{sub 2} inert gas. As a result of the novel manufacturing procedure, a series of carbon materials was obtained with developed surface area and containing copper derivatives of differentiated form, size, and dispersion. The copper modifier and manufacturing procedure (concentration, carbonization temperature) influence the physical–chemical and fungicide properties of the carbons. The received carbons were chemically characterized using several methods like low-temperature adsorption of nitrogen, X-ray diffraction analysis, scanning electron microscopy, cyclic voltammetry, elemental analysis, and bioassay. Besides chemical testing, some biological tests were performed and let to select carbons with the highest fungicidal activity. Such carbons were characteristic of the specific form of copper derivatives occurring in them, i.e., nanocrystallites of Cu{sup 0} and/or Cu{sub 2}O of high dispersion on the surface of carbon. The carbons may find an application as effective contact fungistatic agents in cosmetology, medicine, food industry, etc. - Highlights: • The novel manufacturing procedure yields new functional carbon materials. • Two biopolymers chitin and chitosan can undergo copper(II) ion modification. • The Cu-modified carbon materials exhibit high fungicidal activity. • The fungicidal activity results from the presence of Cu{sup 0} and Cu{sub 2}O nano-crystallites.

  10. Management of resistance to the fungicide fenpropimorph in Erysiphe graminis f.sp tritici

    NARCIS (Netherlands)

    Engels, A.J.G.

    1998-01-01

    In the last three decades, plant disease control has become heavily dependent on fungicides. This practice increased yield significantly but had also negative side-effects on the environment. In many countries, integrated control programs have been initiated in order to reduce pesticide use

  11. Control of clavicipitaceous anamorphic endophytes with fungicides, aerated steam and supercritical fluid CO2-seed extraction

    Science.gov (United States)

    A. Dan Wilson; Donald G. Lester; Brian K. Luckenbill

    2008-01-01

    The effects of soil drenches with systemic fungicides on viability of clavicipitaceous anamorphic endophytes, non-choke inducing endosymbiotic fungi of the genus Neotyphodium that systemically infect grasses, were tested in endophyte-infected seedlings of Hordeum brevisubulatum subsp. violaceum, Lolium perenne...

  12. Fungicides efficiency on wheat diseases control in response to the application with different spray nozzles

    Directory of Open Access Journals (Sweden)

    Felipe Rafael Garcés Fiallos

    2011-12-01

    Full Text Available This study aimed to evaluate the efficiency of fungicides to leaf control diseases of wheat, when applied to different models of spray nozzles. The experiment was conducted in a randomized block design with four replicates of factorial (4 x 3+1. Data were subjected to analysis of variance and means compared by Tukey test at 5% probability. The fungicides used were: Opera® (pyraclostrobin+epoxiconazole 0.75 L.ha-1 , Opera® 0.75 L.ha-1 +Folicur® (tebuconazole 0.3 L.ha-1 , Priori Xtra® (azoxystrobin+cyproconazole 0.3 L.ha-1 , Priori Xtra® 0.3 L.ha-1 +Tilt® (propiconazole 0.3 L.ha-1 . These fungicides were applied with three models of spray nozzles jet planes: XR 11 001 (fine drop, AIRMIX 11,001 (average drop and AVI 11,001 (coarse drop. We evaluated the incidence and severity (damage per plant leaf of yellow spot (Drechslera tritici-repentis, spot blotch (Bipolaris sorokiniana, leaf rust (Puccinia triticina and grain yield (kg.ha-1 culture. The results show that the application of fungicides for control of leaf diseases in wheat resulted in increases in grain yield, and yield higher values were observed with the application of Opera®, using the XR 11001.

  13. Phenotypical and Molecular Characterisation of Fusarium circinatum: Correlation with Virulence and Fungicide Sensitivity

    Directory of Open Access Journals (Sweden)

    Martin Mullett

    2017-11-01

    Full Text Available Fusarium circinatum, causing pine pitch canker, is one of the most damaging pathogens of Pinus species. This study investigated the use of phenotypical and molecular characteristics to delineate groups in a worldwide collection of isolates. The groups correlated with virulence and fungicide sensitivity, which were tested in a subset of isolates. Virulence tests of twenty isolates on P. radiata, P. sylvestris and P. pinaster demonstrated differences in host susceptibility, with P. radiata most susceptible and P. sylvestris least susceptible. Sensitivity to the fungicides fludioxonil and pyraclostrobin varied considerably between isolates from highly effective (half-maximal effective concentration (EC50 < 0.1 ppm to ineffective (EC50 > 100 ppm. This study demonstrates the potential use of simply acquired phenotypical (cultural, morphological and molecular metrics to gain a preliminary estimate of virulence and sensitivity to certain fungicides. It also highlights the necessity of including a range of isolates in fungicide tests and host susceptibility assays, particularly of relevance to tree breeding programmes.

  14. In vitro sensitivity reduction of Fusarium graminearum to DMI and QoI fungicides

    Directory of Open Access Journals (Sweden)

    Aveline Avozani

    2014-12-01

    Full Text Available In Brazil, Fusarium head blight (FHB affecting wheat can cause up to 39.8% damage. Resistant cultivars are not available yet; thus, short-term disease control relies on the use of fungicides. The first step to improve control is to monitor fungal populations that are sensitivity to chemicals in order to achieve efficient FHB management. In vitro experiments were conducted to evaluate the inhibitory concentration (IC50 of fungicides for both mycelial growth and conidial germination of ten Fusarium graminearum isolates. The following demethylation inhibitor (DMI fungicides were tested: metconazole, prothioconazole and tebuconazole. In addition, pyraclostrobin and trifloxystrobin were included, representing QoI fungicides, as well as three co-formulations containing metconazole + pyraclostrobin, prothioconazole + trifloxystrobin, and tebuconazole + trifloxystrobin. For mycelial growth, the overall mean IC50 of isolates was: metconazole 0.07, prothioconazole 0.1, and tebuconazole 0.19 mg/L. For the co-formulations, it was: prothioconazole + trifloxystrobin 0.08, tebuconazole + trifloxystrobin 0.12, and metconazole + pyraclostrobin 0.14 mg/L. Regarding spore germination inhibition, IC50 for prothioconazole + trifloxystrobin was 0.06, for tebuconazole + trifloxystrobin, 0.12 mg/L, for QoI alone pyraclostrobin, was 0.09, and for trifloxystrobin, 0.28 mg/L. There was a sensitivity shift among isolates and the highest fungitoxicity to F. graminearum was confirmed for prothioconazole, metconazole and tebuconazole .

  15. Determination of fungicide resistance in Botrytis cinerea from strawberry in the Central Coast Region of California

    Science.gov (United States)

    A study was conducted in 2013 to investigate the occurrence of fungicide resistance in Botrytis cinerea populations in California’s northern strawberry growing region; specifically in Watsonville and Salinas. In mid-May, 59 samples consisting of a single diseased fruit or plant part with gray mold s...

  16. Sensitivity reduction in Blumeria graminis f. sp. hordei to triadimenol fungicide applied as barley seed treatment

    Directory of Open Access Journals (Sweden)

    Erlei Melo Reis

    2013-12-01

    Full Text Available Experiments were carried out in a growth chamber with controlled temperature and photoperiod to test two populations of Blumeria graminis f. sp. hordei from Guarapuava, Paraná State, and Passo Fundo, Rio Grande do Sul State, Brazil. Treatments consisted in application of the fungicide triadimenol (Baytan 150 SC® at three rates of its commercial formulation: 150, 250, 350 mL/100 Kg barley seeds. The experiments were conducted separately in a growth chamber for each population, adopting the same temperature and photoperiod. For inoculation, pots containing barley seedlings colonized by the fungus were placed among the plots. After emergence of the first symptoms, the disease severity was assessed at two-day intervals. The experiments were repeated twice for each fungus population. Data were expressed as area under the disease progress curve and as powdery mildew control by comparing the severity after the fungicide treatments to that of control. Data were subjected to analysis of variance and regression analysis; the area under the disease progress curve was also calculated. Comparing the data obtained in the present study with those reported in the literature and the control, the maximum value of 26.1% is considered insufficient to prevent the damages caused by the disease. The control response to the fungicide rate was significant. We can conclude that there was a reduction in the sensitivity of both B. graminis f.sp. hordei populations to the fungicide triadimenol, which explains the control failure observed in barley farms.

  17. Evaluating fungicide sensitivity of regional Blumeria graminis f.sp. tritici populations in the United States

    Science.gov (United States)

    Blumeria graminis f.sp. tritici (Bgt), cause of wheat powdery mildew, has a high likelihood of developing fungicide resistance because of the large quantity of spores produced along with the mixed mode of reproduction. Additionally, once reduced sensitivity appears in a population it can influence n...

  18. The effect of fungicide dose on the composition of laboratory populations of barley powdery mildew

    DEFF Research Database (Denmark)

    O'Hara, R.B.; Nielsen, B.J.; Østergård, Hanne

    2000-01-01

    The effect of the use of different doses of the fungicide fenpropimorph on populations of barley powdery mildew Blumeria (Erysiphe) graminis f. sp. hordei was investigated in a laboratory selection experiment. A sample from the Danish aerial population of powdery mildew was split into populations...

  19. Effect of equation pro and kema zed fungicides on cellulase and ...

    African Journals Online (AJOL)

    Two fungicides (equation pro and kema zed) were added to the medium in five doses (50,100, 200, 300 and 400 ppm active ingredient) to investigate the chemical control of cellulase and pectinase enzymes produced by some plant pathogens of broad bean. Alternaria alternata, Alternaria citri, Alternaria and Cochliobolus ...

  20. Synthesis and fungicidal properties of 2,4-diaza-1,3,5 ...

    African Journals Online (AJOL)

    The preparation of 2,4-diaza-1,3,5-pentanetrione compounds were described. The fungicidal effects of these compounds on the mycelial growth of the isolate, Phoma eupyrena were carried out by in vitro experiment. The results show that the response to treatment depended not only on the concentration of the compounds ...

  1. Fate and distribution of pyrimethanil, metalaxyl, dichlofluanid and penconazol fungicides from treated grapes intended for winemaking.

    Science.gov (United States)

    Vaquero-Fernández, L; Sanz-Asensio, J; López-Alonso, M; Martínez-Soria, M T

    2009-02-01

    Tempranillo grapes were immersed in solutions of pyrimethanil, metalaxyl, dichlofluanid and penconazol fungicides at different concentrations for several different times. Determinations of the fungicide residues was carried out by GC-NPD, with an additional confirmation by GC-MS. The percentage absorption was determined as well as the distribution between surface, skin and pulp of the grapes. The percentage absorption ranged from 7.2 to 85.5%. These values depended on the time the grapes were in contact with the fungicide solutions. Residues were mainly found in skins, with percentages in skins ranging from 66.3 to 90.3% of total residues. In pulp, these values ranged from 3.5 to 31.0%. The overall methodology was applied to the determination of pyrimethanil in Tempranillo grapes treated with the recommended doses, respecting the safety period. Pyrimethanil residues found in treated grapes were higher in the skin. In grapes collected within the safety period (21 days), the levels found for fungicide residues were below maximum residues levels.

  2. Effect of fungicide on the development of wheat stem rust and yield ...

    African Journals Online (AJOL)

    Stem rust caused by Puccinia graminis f.sp tritici Erik. & E. Henn. is a highly destructive disease of wheat (Triticum aestivum L.). The effects of fungicide application on stem rust (Puccinia graminis tritici) epidemics and yield of three bread wheat varieties varying in reaction to the disease were studied in two major wheat ...

  3. Comparison of human health risks resulting from exposure to fungicides and mycotoxins via food

    NARCIS (Netherlands)

    Muri, S.D.; Voet, van der H.; Boon, P.E.; Klaveren, van J.D.; Bruschweiler, B.

    2009-01-01

    The interest in holistic considerations in the area of food safety is increasing. Risk managers may face the problem that reducing the risk of one compound may increase the risk of another compound. An example is the potential increase in mycotoxin levels due to a reduced use of fungicides in crop

  4. Investigations on organic fungicides; V. Chemical constitution and fungistatic activity of aliphatic bisdithiocarbamates and isothiocyanates

    NARCIS (Netherlands)

    Klöpping, H.L.; Kerk, G.J.M. van der

    1951-01-01

    In this paper, the investigations on the relations of structure to antifungal activity of sulphur compounds described in the previous publication of this series are extended to bisdithiocarbamates and isothiocyanates. The most active sulphur fungicide described in the literature so far, disodium

  5. Design, Synthesis and Fungicidal Activity of 2-Substituted Phenyl-2-oxo-, 2-Hydroxy- and 2-Acyloxyethylsulfonamides

    Directory of Open Access Journals (Sweden)

    Minlong Wang

    2017-05-01

    Full Text Available Sulfonyl-containing compounds, which exhibit a broad spectrum of biological activities, comprise a substantial proportion of and play a vital role, not only in medicines but also in agrochemicals. As a result increasing attention has been paid to the research and development of sulfonyl derivatives. A series of thirty-eight 2-substituted phenyl-2-oxo- III, 2-hydroxy- IV and 2-acyloxyethylsulfonamides V were obtained and their structures confirmed by IR, 1H-NMR, and elemental analysis. The in vitro and in vivo bioactivities against two Botrytis cinerea strains, DL-11 and HLD-15, which differ in their sensitivity to procymidone, were evaluated. The in vitro activity results showed that the EC50 values of compounds V-1 and V-9 were 0.10, 0.01 mg L−1 against the sensitive strain DL-11 and 3.32, 7.72 mg L−1 against the resistant strain HLD-15, respectively. For in vivo activity against B. cinerea, compound V-13 and V-14 showed better control effect than the commercial fungicides procymidone and pyrimethanil. The further in vitro bioassay showed that compounds III, IV and V had broad fungicidal spectra against different phytopathogenic fungi. Most of the title compounds showed high fungicidal activities, which could be used as lead compounds for further developing novel fungicidal compounds against Botrytis cinerea.

  6. Screening conventional fungicides...control of blister rust on sugar pine in California

    Science.gov (United States)

    Clarence R. Quick

    1967-01-01

    After 5 years, 4 of 14 fungicides tested showed varying pr of development into satisfactory direct control of blister rust. Little promise of systemic control was found. Trees treated were second-growth sugar pine in a mixed conifer forest in eastern Shasta County, California, where blister rust has been intensifying for many years. Most trees received basal-stem...

  7. Assessing effects of the fungicide tebuconazole to heterotrophic microbes in aquatic microcosms

    NARCIS (Netherlands)

    Dimitrov, M.R.; Kosol, Sujitra; Smidt, H.; Brink, van den P.J.; Wijngaarden, van R.P.A.; Brock, T.C.M.; Maltby, L.

    2014-01-01

    Aquatic ecological risk assessment of fungicides in Europe under Regulation 1107/2009/EC does not currently assess risk to non-target bacteria and fungi. Rather, regulatory acceptable concentrations based on ecotoxicological data obtained from studies with fish, invertebrates and primary producers

  8. Development and persistence of resistance to fungicides in Sphaerotheca fuliginea in cucumbers in the Netherlands

    NARCIS (Netherlands)

    Schepers, H.T.A.M.

    1985-01-01

    Ergosterol biosynthesis inhibitors (EBIs) have a remarkably broad spectrum of antifungal activity. They belong to the commercial fungicides which exhibit the highest activity known to date. Resistance to EBIs was found in vitro, but the level of resistance and the decreased fitness of resistant

  9. Application of Copper Solid Amalgam Electrode for Determination of Fungicide Tebuconazole

    Czech Academy of Sciences Publication Activity Database

    Nováková, Kateřina; Navrátil, Tomáš; Jaklová Dytrtová, Jana; Chýlková, J.

    2013-01-01

    Roč. 8, č. 1 (2013), s. 1-16 ISSN 1452-3981 R&D Projects: GA ČR GAP206/11/1638; GA ČR(CZ) GAP208/12/1645 Institutional support: RVO:61388955 ; RVO:61388963 Keywords : tebuconazole * fungicide * copper solid amalgam electrode Subject RIV: CG - Electrochemistry Impact factor: 1.956, year: 2013

  10. Phyto-fungicides: Structure activity relationships of the thymol derivatives against Rhizoctonia solani

    Science.gov (United States)

    Thymol, the key component of thyme oil and its derivatives were evaluated for their structure activity relationship as fungicide against Rhizoctonia solani. Since plant based chemicals are considered as “Generally Recognized as Safe” (GRAS) chemicals, there is a great potential to use phytochemicals...

  11. Synthesis of 1-(4-methylsulfone-phenyl)-5-(4-fluoro-phenyl)-5-[14C]-1,2,3- triazole and 1-(4-sulfonamide-phenyl)-5-(4-fluoro-phenyl)-5-[14C]-1,2,3- triazole as novel carbon-14 anticonvulsant

    International Nuclear Information System (INIS)

    Saemian, N.; Shirvani, G.; Matloubi, H.

    2006-01-01

    Two 1,2,3-triazole anticonvulsants, 1-(4-methylsulfone-phenyl)-5-(4-fluoro-phenyl)-5-[ 14 C]-1,2,3-triazole and 1-(4-sulfonamide-phenyl)-5-(4- fluoro-phenyl)-5-[ 14 C]-1,2,3-triazole, both labeled with carbon-14 in the 5-position were prepared from para-fluoro-benzonitrile-[cyano- 14 C]. (author)

  12. Reactivity of C-Amino-1,2,4-triazoles toward Electrophiles: A Combined Computational and Experimental Study of Alkylation by Halogen Alkanes.

    Science.gov (United States)

    Chernyshev, Victor M; Vlasova, Anna G; Astakhov, Alexander V; Shishkina, Svitlana V; Shishkin, Oleg V

    2015-01-02

    A combination of computational and experimental methods was used to examine the structure-reactivity relationships in the reactions of C-amino-1H-1,2,4-triazoles with electrophiles. The global nucleophilicity of 3-amino- and 3,5-diamino-1H-1,2,4-triazoles was predicted to be higher than that of 5-amino-1H-1,2,4-triazoles. Fukui functions and molecular electrostatic potential indicate that reactions involving an amino group should occur more easily for the 3-amino- than for the 5-amino-1H-1,2,4-triazoles. Increasing electrophile hardness should increase the probability of attack at the N-4 atom of the triazole ring, whereas increasing softness should enhance the probability of attack at the N-2 atom and 3-NH2 group. Calculated transition state energies of model SN2 reactions and experimental studies showed that quaternization of 1-substituted 3-amino- and 3,5-diamino-1H-1,2,4-triazoles by many alkyl halides proceeds with low selectivity and can involve the N-2 and N-4 atoms as well as the 3-NH2 group as reaction centers. A new method for the selective synthesis of 1,4-disubstituted 3-amino- and 3,5-diamino-1,2,4-triazoles based on quaternization of readily available 1-substituted 3-acetylamino-1,2,4-triazoles with subsequent removal of the acetyl protecting group by acid hydrolysis was developed.

  13. Traceless Azido Linker for the Solid-Phase Synthesis of NH-1,2,3-Triazoles via Cu-Catalyzed Azide-Alkyne Cycloaddition Reactions

    DEFF Research Database (Denmark)

    Cohrt, Anders Emil; Jensen, Jakob Feldthusen; Nielsen, Thomas Eiland

    2010-01-01

    A broadly useful acid-labile traceless azido linker for the solid-phase synthesis of NH-1,2,3-triazoles is presented. A variety of alkynes were efficiently immobilized on a range of polymeric supports by Cu(I)-mediated azide-alkyne cycloadditions. Supported triazoles showed excellent compatibility...

  14. IR luminescence of mixed-ligand complexes of Nd(III), Yb(III), and Er(III) with dibenzoylmethane and 1,2,4-triazoles

    Science.gov (United States)

    Meshkova, S. B.; Kiriyak, A. V.; Gusev, A. N.; Nischimenko, G. A.; Shul'gin, V. F.

    2012-11-01

    The synthesis and photoluminescence spectra of mixed-ligand complexes of Nd(III), Yb(III), and Er(III) with dibenzoylmethanate anion as the principal ligand and functionalized 1,2,4-triazoles and spacer bis-triazoles as ancillary ligands were described.

  15. Substitution of terminal amide with 1H-1,2,3-triazole: Identification of unexpected class of potent antibacterial agents.

    Science.gov (United States)

    Bi, Fangchao; Ji, Shengli; Venter, Henrietta; Liu, Jingru; Semple, Susan J; Ma, Shutao

    2018-03-01

    3-Methoxybenzamide (3-MBA) derivatives have been identified as novel class of potent antibacterial agents targeting the bacterial cell division protein FtsZ. As one of isosteres for the amide group, 1,2,3-triazole can mimic the topological and electronic features of the amide, which has gained increasing attention in drug discovery. Based on these considerations, we prepared a series of 1H-1,2,3-triazole-containing 3-MBA analogues via isosteric replacement of the terminal amide with triazole, which had increased antibacterial activity. This study demonstrated the possibility of developing the 1H-1,2,3-triazole group as a terminal amide-mimetic element which was capable of both keeping and modulating amide-related bioactivity. Surprisingly, a different action mode of these new 1H-1,2,3-triazole-containing analogues was observed, which could open new opportunities for the development of antibacterial agents. Copyright © 2018 Elsevier Ltd. All rights reserved.

  16. Studies on triazole derivatives as inhibitors for the corrosion of muntz metal in acidic and neutral solutions

    International Nuclear Information System (INIS)

    Berchmans, L. John; Sivan, V.; Iyer, S. Venkata Krishna

    2006-01-01

    The influence of few triazole derivatives namely, 4-amino-5-mercapto-3-methyl 1,2,4 triazole (AMMT), 4-amino-5-mercapto-3-methyl 1,2,4 triazole (AMET) and 4-amino-5-mercapto-3-propyl 1,2,4 triazole (AMPT) on the corrosion behavior of muntz metal (60Cu-40Zn) in acidic and neutral solutions has been studied using weight loss measurements and potentiodynamic polarization methods. Surface morphological examinations such as UV spectral analysis, XRD and SEM have also been carried out to understand the mechanism of inhibition of corrosion. All the triazoles derivatives are found to inhibit the corrosion of muntz metal very effectively in both the acidic and neutral solutions. Polarization measurements clearly show that the inhibitors behave as mixed type in neutral medium and are predominantly cathodic nature in acidic solutions. UV spectra, XRD and Scanning Electron Microscopic studies clearly reveal the formation of a strongly adsorbed film on the metal surface, which is responsible for the inhibition of corrosion in both the media. From the above studies, it can be concluded that the inhibition of corrosion by these compounds is due to a chmisorption process. Among these compounds, AMPT is found to offer better corrosion inhibition than the other compounds

  17. Colonies of Bumble Bees (Bombus impatiens Produce Fewer Workers, Less Bee Biomass, and Have Smaller Mother Queens Following Fungicide Exposure

    Directory of Open Access Journals (Sweden)

    Olivia M. Bernauer

    2015-06-01

    Full Text Available Bees provide vital pollination services to the majority of flowering plants in both natural and agricultural systems. Unfortunately, both native and managed bee populations are experiencing declines, threatening the persistence of these plants and crops. Agricultural chemicals are one possible culprit contributing to bee declines. Even fungicides, generally considered safe for bees, have been shown to disrupt honey bee development and impair bumble bee behavior. Little is known, however, how fungicides may affect bumble bee colony growth. We conducted a controlled cage study to determine the effects of fungicide exposure on colonies of a native bumble bee species (Bombus impatiens. Colonies of B. impatiens were exposed to flowers treated with field-relevant levels of the fungicide chlorothalonil over the course of one month. Colony success was assessed by the number and biomass of larvae, pupae, and adult bumble bees. Bumble bee colonies exposed to fungicide produced fewer workers, lower total bee biomass, and had lighter mother queens than control colonies. Our results suggest that fungicides negatively affect the colony success of a native bumble bee species and that the use of fungicides during bloom has the potential to severely impact the success of native bumble bee populations foraging in agroecosystems.

  18. Relationship between IC50 determined in vitro/in vivo and the fungicide rate used in the Field

    Directory of Open Access Journals (Sweden)

    Erlei Melo Reis

    2015-03-01

    Full Text Available Published data containing fungicide concentrations that control 50% (IC50 of a given fungus were analyzed. In the analysis we considered: (i the IC50 determined in vitro and in vivo for a given fungicide and for a specific fungus; (ii the concentration (g/ha of active ingredient for the fungicide indicated to control a specific disease in the field; (iii water volume of 120/L used in the spray; (iv the fungicide a.i. concentration (mg/L in 120 L volume; (v and the ratio of the concentration used in the field with that determined in the laboratory. The analysis were performed by using IC50 data for DMIs, QoIs, a carbamate and a benzimidazol against the following fungi Bipolaris sorokiniana, Drechslera tritici-repentis, D. siccans, Fusarium graminearum, Puccinia triticina, Exserohilum turcicum, Phakopsora pachyrhizi and Corynespora cassiicola. The fungicide concentrations sprayed in the field were 33.9 (D. siccans and trifloxystrobin to 500,000.0 (E. turcicum and iprodione times higher than that determined in the laboratory. It was concluded that the IC50 was not related to the concentration used in the field and therefore should be used to compare the power among fungicides and to monitor the fungal sensitivity shift towards fungicides

  19. Efficacy of Combined Formulations of Fungicides with Different Modes of Action in Controlling Botrytis Gray Mold Disease in Chickpea

    Directory of Open Access Journals (Sweden)

    M. H. Rashid

    2014-01-01

    Full Text Available Botrytis gray mold (BGM caused by Botrytis cinerea Pers. Ex. Fr. is an extremely devastating disease of chickpea (Cicer arietinum L. and has a regional as well as an international perspective. Unfortunately, nonchemical methods for its control are weak and ineffective. In order to identify an effective control measure, six fungicides with different modes of action were evaluated on a BGM susceptible chickpea variety BARIchhola-1 at a high BGM incidence location (Madaripur in Bangladesh for three years (2008, 2009, and 2010. Among the six fungicides tested, one was protectant [Vondozeb 42SC, a.i. mancozeb (0.2%], two systemic [Bavistin 50 WP, a.i. carbendazim (0.2%, and Protaf 250EC, propiconazole (0.05%], and three combination formulations [Acrobat MZ690, dimethomorph 9% + mancozeb 60%, (0.2%; Secure 600 WG, phenomadone + mancozeb (0.2%; and Companion, mancozeb 63% + carbendazim 12% (0.2%]. The results showed superiority of combination formulations involving both protectant and systemic fungicides over the sole application of either fungicide separately. Among the combination fungicides, Companion was most effective, resulting in the lowest disease severity (3.33 score on 1–9 scale and the highest increase (38% of grain yield in chickpea. Therefore, this product could be preferred over the sole application of either solo protectant or systemic fungicides to reduce yield losses and avoid fungicide resistance.

  20. Efficacy of combined formulations of fungicides with different modes of action in controlling botrytis gray mold disease in chickpea.

    Science.gov (United States)

    Rashid, M H; Hossain, M Ashraf; Kashem, M A; Kumar, Shiv; Rafii, M Y; Latif, M A

    2014-01-01

    Botrytis gray mold (BGM) caused by Botrytis cinerea Pers. Ex. Fr. is an extremely devastating disease of chickpea (Cicer arietinum L.) and has a regional as well as an international perspective. Unfortunately, nonchemical methods for its control are weak and ineffective. In order to identify an effective control measure, six fungicides with different modes of action were evaluated on a BGM susceptible chickpea variety BARIchhola-1 at a high BGM incidence location (Madaripur) in Bangladesh for three years (2008, 2009, and 2010). Among the six fungicides tested, one was protectant [Vondozeb 42SC, a.i. mancozeb (0.2%)], two systemic [Bavistin 50 WP, a.i. carbendazim (0.2%), and Protaf 250EC, propiconazole (0.05%)], and three combination formulations [Acrobat MZ690, dimethomorph 9% + mancozeb 60%, (0.2%); Secure 600 WG, phenomadone + mancozeb (0.2%); and Companion, mancozeb 63% + carbendazim 12% (0.2%)]. The results showed superiority of combination formulations involving both protectant and systemic fungicides over the sole application of either fungicide separately. Among the combination fungicides, Companion was most effective, resulting in the lowest disease severity (3.33 score on 1-9 scale) and the highest increase (38%) of grain yield in chickpea. Therefore, this product could be preferred over the sole application of either solo protectant or systemic fungicides to reduce yield losses and avoid fungicide resistance.

  1. Evaluation of some fungicides on mycorrhizal symbiosis between two Glomus species from commercial inocula and Allium porrum L. seedlings

    Energy Technology Data Exchange (ETDEWEB)

    Hernandez-Dorrego, A.; Mestre Pares, J.

    2010-07-01

    This paper reports the effect of twenty-five commonly used fungicides in agriculture on two arbuscular mycorrhizal fungi (AMF) present in commercial products of ATENS, S.L.: Glomus intra radices (Schenck and Smith) and Glomus mosseae [(Nicol. and Gerd.) Gerdemann and Trappe], forming the symbiosis with leek plants. Systemic fungicides (Aliette, Beltanol, Caddy 10, Forum, Moncut, Ortiva, Previcur, Ridomil Gold MZ, Ridomil Gold SL, Rubigan, Sinthane, Stroby, Swich, Tachigarem, Teldor, Topas 10 EC, Frupica) and non systemic fungicides (Daconil 75%, Ditiver, Euparem, INACOP, Octagon, Parmex, Terrazole and Metaram), started to be applied to soil and leaves at recommended concentrations and frequencies 4 weeks after transplant and AMF inoculation. The effect of the fungicides was assessed by comparing treated and untreated plants that were inoculated with the AMF through quantification of root mycorrhizal colonization. Among the fungicides applied to the soil, Octagon, Ditiver, Parmex and Metaram virtually eliminated the mycorrhizal symbiosis in treated plants, while the mycorrhizal colonization was not affected by the soil treatment with Beltanol, INACOP and Previcur. Three fungicides of foliar recommended application: Rubigan, Frupica, and Sinthane, strongly inhibited mycorrhizal colonization, but Aliette, Forum, Teldor, Swich and Ortiva, did not seem to reduce it substantially. In addition, the work describes the individual effect of each fungicide applied on both, foliage and soil. (Author) 29 refs.

  2. Probabilities for profitable fungicide use against gray leaf spot in hybrid maize.

    Science.gov (United States)

    Munkvold, G P; Martinson, C A; Shriver, J M; Dixon, P M

    2001-05-01

    ABSTRACT Gray leaf spot, caused by the fungus Cercospora zeae-maydis, causes considerable yield losses in hybrid maize grown in the north-central United States and elsewhere. Nonchemical management tactics have not adequately prevented these losses. The probability of profitably using fungicide application as a management tool for gray leaf spot was evaluated in 10 field experiments under conditions of natural inoculum in Iowa. Gray leaf spot severity in untreated control plots ranged from 2.6 to 72.8% for the ear leaf and from 3.0 to 7.7 (1 to 9 scale) for whole-plot ratings. In each experiment, fungicide applications with propiconazole or mancozeb significantly reduced gray leaf spot severity. Fungicide treatment significantly (P fungicide applications. For one application, the probability ranged from approximately 0.06 to more than 0.99, and exceeded 0.50 in six of nine scenarios (specific experiment/hybrid). The highest probabilities occurred in the 1995 experiments with the most susceptible hybrid. Probabilities were almost always higher for a single application of propiconazole than for two applications. These results indicate that a single application of propiconazole frequently can be profitable for gray leaf spot management in Iowa, but the probability of a profitable application is strongly influenced by hybrid susceptibility. The calculation of probabilities for positive net returns was more informative than mean separation in terms of assessing the economic success of the fungicide applications.

  3. Thrombin-induced rabbit platelet microbicidal protein is fungicidal in vitro.

    Science.gov (United States)

    Yeaman, M R; Ibrahim, A S; Edwards, J E; Bayer, A S; Ghannoum, M A

    1993-03-01

    Platelet microbicidal protein (PMP) is released from platelets in response to thrombin stimulation. PMP is known to possess in vitro bactericidal activity against Staphylococcus aureus and viridans group streptococci. To determine whether PMP is active against other intravascular pathogens, we evaluated its potential fungicidal activity against strains of Candida species and Cryptococcus neoformans. Anionic resin adsorption and gel electrophoresis confirmed that the fungicidal activity of PMP resided in a small (approximately 8.5-kDa), cationic protein, identical to previous studies of PMP-induced bacterial killing (M.R. Yeaman, S.M. Puentes, D.C. Norman, and A.S. Bayer, Infect. Immun. 60:1202-1209, 1992). When assayed over a 180-min period in vitro, the susceptibilities of these fungi to PMP varied considerably. Generally, Candida albicans strains (mean survival, 33.5% +/- 6.9% [n = 6]) as well as isolates of Candida glabrata (mean survival, 50.8% +/- 2.9% [n = 2]) were the most susceptible to killing by PMP, while Candida guillermondii and Candida parapsilosis were relatively resistant to PMP-induced killing. Compared with C. albicans, C. neoformans was relatively resistant to the fungicidal activity of PMP, with a mean survival among the isolates studied of 77.4% +/- 12.4% (n = 6). Against C. albicans, PMP-induced fungicidal activity was time dependent (range, 0 to 180 min), PMP concentration dependent (range, 10 to 150 U/ml), and inversely related to the fungal inoculum (range, 5 x 10(3) to 1 x 10(5) CFU/ml). Scanning electron microscopy of PMP-exposed C. albicans and C. neoformans cells revealed extensive surface damage and collapse, suggesting that the site of PMP fungicidal action may directly or indirectly involve the fungal cell envelope.

  4. Disease control by chemical and biological fungicides in cultivated mushrooms: button mushroom, oyster mushroom and shiitake

    Directory of Open Access Journals (Sweden)

    Ivana Potočnik

    2015-12-01

    Full Text Available The most commonly cultivated basidiomycetes worldwide and in Serbia are button mushroom (Agaricus bisporus, oyster mushroom (Pleurotus sp. and shiitake (Lentinus edodes. Production of their fruiting bodies is severely afflicted by fungal, bacterial, and viral pathogens that are able to cause diseases which affect yield and quality. Major A. bisporus fungal pathogens include Mycogone perniciosa, Lecanicillium fungicola, and Cladobotryum spp., the causal agents of dry bubble, wet bubble, and cobweb disease, respectively. Various Trichoderma species, the causal agents of green mould, also affect all three kinds of edible mushrooms. Over the past two decades, green mould caused by T. aggressivum has been the most serious disease of button mushroom. Oyster mushroom is susceptible to T. pleurotum and shiitake to T. harzianum. The bacterial brawn blotch disease, caused by Pseudomonas tolaasii, is distributed globally. Disease control on mushroom farms worldwide is commonly based on the use of fungicides. However, evolution of pathogen resistance to fungicides after frequent application, and host sensitivity to fungicides are serious problems. Only a few fungicides are officially recommended in mushroom production: chlorothalonil and thiabendazol in North America and prochloraz in the EU and some other countries. Even though decreased sensitivity levels of L. fungicola and Cladobotryum mycophilum to prochloraz have been detected, disease control is still mainly provided by that chemical fungicide. Considering such resistance evolution, harmful impact to the environment and human health, special attention should be focused on biofungicides, both microbiological products based on Bacillus species and various natural substances of biological origin, together with good programs of hygiene. Introduction of biofungicides has created new possibilities for crop protection with reduced application of chemicals.

  5. Click-assembling triazole membrane on copper surface via one-step or two-steps and their corrosion inhibition performance

    Science.gov (United States)

    Wang, Yizhen; Yu, Yinzhe; Zhang, Jie; Gao, Lixin; Feng, Likui; Zhang, Daquan

    2018-01-01

    Triazole membrane was prepared on copper surface via one-step or two-steps click chemistry reaction of azide and alkyne compounds. Fourier transforms infrared spectroscopy (FT-IR) suggests the formation of triazole membrane on copper surface through both of one-step and two-steps click-assembling. The electrochemical results indicate that the protection efficiency of triazole click-assembling membrane forming via one-step is better than that for two-steps. The surface film on copper via one-step click-assembling is mainly composed of the triazole membrane. As for two-steps click-assembling, the triazole membrane is mainly produced in the defect of the alkyne inhibition film.

  6. Effect of quinoline based 1,2,3-triazole and its structural analogues on growth and virulence attributes of Candida albicans.

    Science.gov (United States)

    Irfan, Mohammad; Alam, Shadab; Manzoor, Nikhat; Abid, Mohammad

    2017-01-01

    Candida albicans, along with some other non-albicans Candida species, is a group of yeast, which causes serious infections in humans that can be both systemic and superficial. Despite the fact that extensive efforts have been put into the discovery of novel antifungal agents, the frequency of these fungal infections has increased drastically worldwide. In our quest for the discovery of novel antifungal compounds, we had previously synthesized and screened quinoline containing 1,2,3-triazole (3a) as a potent Candida spp inhibitor. In the present study, two structural analogues of 3a (3b and 3c) have been synthesized to determine the role of quinoline and their anti-Candida activities have been evaluated. Preliminary results helped us to determine 3a and 3b as lead inhibitors. The IC50 values of compound 3a for C. albicans ATCC 90028 (standard) and C. albicans (fluconazole resistant) strains were 0.044 and 2.3 μg/ml, respectively while compound 3b gave 25.4 and 32.8 μg/ml values for the same strains. Disk diffusion, growth and time kill curve assays showed significant inhibition of C. albicans in the presence of compounds 3a and 3b. Moreover, 3a showed fungicidal nature while 3b was fungistatic. Both the test compounds significantly lower the secretion of proteinases and phospholipases. While, 3a inhibited proteinase secretion in C. albicans (resistant strain) by 45%, 3b reduced phospholipase secretion by 68% in C. albicans ATCC90028 at their respective MIC values. Proton extrusion and intracellular pH measurement studies suggested that both compounds potentially inhibit the activity of H+ ATPase, a membrane protein that is crucial for various cell functions. Similarly, 95-97% reduction in ergosterol content was measured in the presence of the test compounds at MIC and MIC/2. The study led to identification of two quinoline based potent inhibitors of C. albicans for further structural optimization and pharmacological investigation.

  7. Occurrence and Environmental Effects of Boscalid and Other Fungicides in Three Targeted Use Areas in the United States

    Science.gov (United States)

    Reilly, T. J.; Smalling, K. L.; Wilson, E. R.

    2011-12-01

    Fungicides are typically used to control the outbreak of persistent, historically significant plant diseases like late blight (caused by Phytophthora infestans and responsible for the Irish Potato famine of 1846) and newer plant diseases like Asian Soy Rust, both of which are potentially devastating if not controlled. Of the more than 67,000 pesticide products currently registered for use in the United States, over 3,600 are used to combat fungal diseases. Although they are widely used, relatively little is known about the fate and potential secondary effects of fungicides in the aquatic environment. Even less is known about the fate and environmental occurrence of recently registered fungicides including boscalid, which was first registered for use in the US in 2003. Unlike most other pesticides, multiple fungicides are typically applied as a prophylactic crop protectant upwards of ten times per season (depending upon conditions and crop type), but at lower application rates than herbicides or insecticides. This difference in usage increases the likelihood of chronic exposure of aquatic ecosystems to low concentrations of fungicides. Using a newly developed analytical method, the U.S. Geological Survey measured 33 fungicides in surface water and shallow groundwater in three geographic areas of intense fungicide use across the US. Sampling sites were selected near or within farms using prophylactic fungicides at rates and types typical of the crop type and their geographic location. At least one fungicide was detected in 75% of the surface waters (n=60) and 58% of the groundwater (n=12) samples. Twelve fungicides were detected in surface- and groundwater including boscalid (72%), azoxystrobin (51%), pyraclostrobin (40%), chlorothalonil (38%) and pyrimethanil (28%). Boscalid was the most frequently detected pesticide and has not been previously documented in the aquatic environment. In this study, an average of 44% of the pesticide concentration in a water sample

  8. DESIGN, SYNTHESIS AND ANTICANCER ACTIVITY OF SOME NOVEL 1,2,4-TRIAZOLES CARRYING BIOLOGICALLY ACTIVE SULFONAMIDE MOIETIES.

    Science.gov (United States)

    Ghorab, Mostafa M; Alsaid, Mansour S; Al-Dosari, Mohammed

    2016-09-01

    Thirteen novel 1, 2, 4-triazoles incorporating a biologically active sulfonamide moieties 1-13 were designed and synthesized. The structures of the prepared compounds were elucidated on the basis of elemental analyses, IR, 'H-NMR, "C-NMR and mass spectral data. All the newly synthesized compounds were evaluated for their in vino anticancer activity against various cancer cell lines. The corresponding triazole carrying a biologically active free sulfonamide with unsubstituted phenyl ring 1 and triazole bearing sulfonamide with dimethylpyrimidine 11 were the most potent in this study which showed higher activity than the reference drug 2',7'-dichlorofluorescein (DCF). Cytotoxic screening of the tested compounds could offer an encouraging framework in the field that may lead to the discovery of potent anticancer activity.

  9. Multicomponent Synthesis and Evaluation of New 1,2,3-Triazole Derivatives of Dihydropyrimidinones as Acidic Corrosion Inhibitors for Steel.

    Science.gov (United States)

    González-Olvera, Rodrigo; Román-Rodríguez, Viridiana; Negrón-Silva, Guillermo E; Espinoza-Vázquez, Araceli; Rodríguez-Gómez, Francisco Javier; Santillan, Rosa

    2016-02-22

    An efficient one-pot synthesis of 1,2,3-triazole derivatives of dihydropyrimidinones has been developed using two multicomponent reactions. The aldehyde-1,2,3-triazoles were obtained in good yields from in situ-generated organic azides and O-propargylbenzaldehyde. The target heterocycles were synthesized through the Biginelli reaction in which the aldehyde-1,2,3-triazoles reacted with ethyl acetoacetate and urea in the presence of Ce(OTf)₃ as the catalyst. The corrosion inhibition of steel grade API 5 L X52 in 1 M HCl by the synthesized compounds was investigated using the electrochemical impedance spectroscopy technique. The measurements revealed that these heterocycles are promising candidates to inhibit acidic corrosion of steel.

  10. Pseudo-four component synthesis of mono- and di-benzylated-1,2,3-triazoles derived from aniline.

    Science.gov (United States)

    Mendoza-Espinosa, Daniel; Negron-Silva, Guillermo E; Lomas-Romero, Leticia; Gutierrez-Carrillo, Atilano; Santillán, Rosa

    2013-12-20

    The pseudo-four component click synthesis of dibenzylated 1,2,3-triazoles derived from aniline is reported. The cycloaddition of sodium azide to N-(prop-2-ynyl)-benzenamine (I) in the presence of equimolar amounts of p-substituted benzyl derivatives, yields a mixture of mono- and dibenzylated 1,2,3-triazoles. When two equivalents of the benzyl derivative are added to the multicomponent reaction, the selective preparation of the dibenzylated compounds is achieved. The reactivity of the aniline N-H bond in monobenzylated 1,2,3-triazoles was tested by treatment with one equivalent of a p-substituted benzyl chloride at 40 °C, rendering the dibenzylated derivatives quantitatively.

  11. Multicomponent Synthesis and Evaluation of New 1,2,3-Triazole Derivatives of Dihydropyrimidinones as Acidic Corrosion Inhibitors for Steel

    Directory of Open Access Journals (Sweden)

    Rodrigo González-Olvera

    2016-02-01

    Full Text Available An efficient one-pot synthesis of 1,2,3-triazole derivatives of dihydropyrimidinones has been developed using two multicomponent reactions. The aldehyde-1,2,3-triazoles were obtained in good yields from in situ-generated organic azides and O-propargylbenzaldehyde. The target heterocycles were synthesized through the Biginelli reaction in which the aldehyde-1,2,3-triazoles reacted with ethyl acetoacetate and urea in the presence of Ce(OTf3 as the catalyst. The corrosion inhibition of steel grade API 5 L X52 in 1 M HCl by the synthesized compounds was investigated using the electrochemical impedance spectroscopy technique. The measurements revealed that these heterocycles are promising candidates to inhibit acidic corrosion of steel.

  12. 1,2,3-Triazole/MWCNT conjugates as filler for gelcoat nanocomposites: new active antibiofouling coatings for marine application

    International Nuclear Information System (INIS)

    Iannazzo, Daniela; Pistone, Alessandro; Visco, Annamaria; Galtieri, Giovanna; Galvagno, Signorino; Giofrè, Salvatore V; Romeo, Roberto; Romeo, Giovanni; Cappello, Simone; Bonsignore, Martina; Denaro, Renata

    2015-01-01

    A polyester-based gelcoat nanocomposite was synthesized by using as nanofiller multi-walled carbon nanotubes (MWCNTs) conjugated with a biocidal 1,2,3-triazole to be used as a new eco-friendly antibiofouling coating. 1,2,3-Triazole/MWCNT conjugates containing differently substituted 1,2,3-triazoles have been synthesized and characterized by physical, chemical, and morphological analyses. Ecotoxicological studies, performed on marine organisms belonging to different evolutive classes, provided information about the choice of the more interesting nanofiller. The synthesized gelcoat nanocomposite showed a significant improvement in the wet ability with respect to the Gelcoat alone. Preliminary biological tests performed on the nanocomposite revealed great biocidal properties, thus providing new opportunities to develop an effective antibiofouling coating. (paper)

  13. Synthesis of new 3,5-disubstituted-1,2,4-triazoles and evaluation of antibacterial, antiurease and antioxidant activities

    International Nuclear Information System (INIS)

    Gumrukcuoglu, N.; Sokmen, B.B.; Ugras, S.

    2016-01-01

    Acylhydrazone 2 was synthesized by the condensation of iminoester hydrochloride 1 with acyl hydrazine. The treatment of acylhydrazone with hydrazine hydrate afforded 4-amino-3,5-dialkyl-1,2,4- triazole 3. The treatment of compound 3 with various aromatic aldehydes resulted in the formation of 4-arylidenamino-3,5-dialkyl-1,2,4-triazoles 4a-c. Sodium borohydride reduction of 4-arylidenamino derivatives afforded 4-alkylamino-3,5-dialkyl-1,2,4- triazoles 5a-c. The obtained products were identified by FTIR, /sup 1/H-NMR, /sup 13/C-NMR, Mass spectroscopic and elemental analysis. A series of compounds were evaluated for their, antibacterial, antiurease, antioxidant activities. The results showed that the synthesized new compounds had effective antibacterial, antioxidant, antiurease activities. (author)

  14. Synthesis and antimicrobial evaluation of 1,4-disubstituted 1,2,3-triazoles with aromatic ester functionality

    Directory of Open Access Journals (Sweden)

    C.P. Kaushik

    2016-11-01

    Full Text Available A series of 1,4-disubstituted 1,2,3-triazoles having p-substituted aromatic ester functionality were synthesized via Cu(I catalysed click reaction between p-substituted benzoic acid prop-2-ynyl esters and aralkyl azides. The synthesized triazoles were characterized by IR, 1H NMR, 13C NMR and mass spectral techniques. These compounds were evaluated for their antimicrobial activity against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, Mycobacterium tuberculosis, Candida albicans, Aspergillus niger and Aspergillus flavus by two fold serial dilution method. Some of the synthesized 1,4-disubstituted 1,2,3-triazoles possess comparable or even better antibacterial, antitubercular and antifungal activities than reference drugs against tested bacterial, mycobacterial and fungal strains, respectively.

  15. New synthesis of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, nanomolar inhibitors of glycogen phosphorylase.

    Science.gov (United States)

    Kun, Sándor; Bokor, Éva; Varga, Gergely; Szőcs, Béla; Páhi, András; Czifrák, Katalin; Tóth, Marietta; Juhász, László; Docsa, Tibor; Gergely, Pál; Somsák, László

    2014-04-09

    O-Perbenzoylated 5-(β-D-glucopyranosyl)tetrazole was reacted with N-benzyl carboximidoyl chlorides to give the corresponding 4-benzyl-3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles. Removal of the O-benzoyl and N-benzyl protecting groups by base catalysed transesterification and catalytic hydrogenation, respectively, furnished a series of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles with aliphatic, mono- and bicyclic aromatic, and heterocyclic substituents in the 5-position. Enzyme kinetic studies revealed these compounds to inhibit rabbit muscle glycogen phosphorylase b: best inhibitors were the 5-(4-aminophenyl)- (Ki 0.67 μM) and the 5-(2-naphthyl)-substituted (Ki 0.41 μM) derivatives. This study uncovered the C-glucopyranosyl-1,2,4-triazoles as a novel skeleton for nanomolar inhibition of glycogen phosphorylase. Copyright © 2014 Elsevier Masson SAS. All rights reserved.

  16. Synthesis of tetrazole-13C and 1,2,4-triazole-1,2-15N2

    International Nuclear Information System (INIS)

    Rowlett, R.S.; Klysa, Thomas; Shiraki, W.W.

    1990-01-01

    We report here the syntheses of tetrazole- 13 C and 1,2,4-triazole-1,2- 15 N 2 by simple, one-step procedures using common, commercially available, isotopically-labeled starting materials. Tetrazole- 13 C is conveniently prepared from K 13 CN and NaN 3 in 70% yield, almost twice the best reported yield for (unlabeled) tetrazole by similar synthetic methods. 1,2,4-triazole-1,2- 15 N 2 was synthesized in 35% yield from hydrazine- 15 N 2 sulphate and 1,3,5-triazine. From 15 N-NMR we determined that 15 N was specifically incorporated into the 1 and 2 positions of the triazole ring. (author)

  17. Synthesis and evaluation of novel triazoles and mannich bases functionalized 1,4-dihydropyridine as angiotensin converting enzyme (ACE) inhibitors.

    Science.gov (United States)

    Kumbhare, Ravindra M; Kosurkar, Umesh B; Bagul, Pankaj K; Kanwal, Abhinav; Appalanaidu, K; Dadmal, Tulshiram L; Banerjee, Sanjay Kumar

    2014-11-01

    A series of novel diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate embedded triazole and mannich bases were synthesized, and evaluated for their angiotensin converting enzyme (ACE) inhibitory activity. Screening of above synthesized compounds for ACE inhibition showed that triazoles functionalized compounds have better ACE inhibitory activity compared to that of mannich bases analogues. Among all triazoles we found 6 h, 6 i and 6 j to have good ACE inhibition activity with IC50 values 0.713 μM, 0.409 μM and 0.653 μM, respectively. Among mannich bases series compounds, only 7c resulted as most active ACE inhibitor with IC50 value of 0.928 μM. Copyright © 2014. Published by Elsevier Ltd.

  18. 1,2,3-Triazole/MWCNT conjugates as filler for gelcoat nanocomposites: new active antibiofouling coatings for marine application

    Science.gov (United States)

    Iannazzo, Daniela; Pistone, Alessandro; Visco, Annamaria; Galtieri, Giovanna; Giofrè, Salvatore V.; Romeo, Roberto; Romeo, Giovanni; Cappello, Simone; Bonsignore, Martina; Denaro, Renata; Galvagno, Signorino

    2015-11-01

    A polyester-based gelcoat nanocomposite was synthesized by using as nanofiller multi-walled carbon nanotubes (MWCNTs) conjugated with a biocidal 1,2,3-triazole to be used as a new eco-friendly antibiofouling coating. 1,2,3-Triazole/MWCNT conjugates containing differently substituted 1,2,3-triazoles have been synthesized and characterized by physical, chemical, and morphological analyses. Ecotoxicological studies, performed on marine organisms belonging to different evolutive classes, provided information about the choice of the more interesting nanofiller. The synthesized gelcoat nanocomposite showed a significant improvement in the wet ability with respect to the Gelcoat alone. Preliminary biological tests performed on the nanocomposite revealed great biocidal properties, thus providing new opportunities to develop an effective antibiofouling coating.

  19. The electronic states of 1,2,4-triazoles: A study of 1H- and1-methyl-1,2,4-triazole by vacuum ultraviolet photoabsorption and ultraviolet photoelectron spectroscopy and a comparison with ab initio configuration interaction computations

    DEFF Research Database (Denmark)

    Palmer, Michael H.; Camp, Philip J.; Hoffmann, Søren Vrønning

    2012-01-01

    The first vacuum ultraviolet absorption spectrum of a 1,2,4-triazole has been obtained and analyzed in detail, with assistance from both an enhanced UV photoelectron spectroscopic study and ab initio multi-reference multi-root configuration interaction procedures. For both 1H- and 1-methyl-1......,2,4-triazoles, the first ionization energy bands show complex vibrational structure on the low-energy edges of otherwise unstructured bands. Detailed analysis of these bands confirms the presence of three ionized states. The 6–7 eV VUV spectral region shows an unusual absorption plateau, which is interpreted...

  20. 1-[(1-Benzyl-1H-1,2,3-triazol-4-ylmethyl]indoline-2,3-dione

    Directory of Open Access Journals (Sweden)

    Fatima-Zahrae Qachchachi

    2014-05-01

    Full Text Available In the title compound, C18H14N4O2, the triazole ring makes dihedral angles of 77.32 (8 and 75.56 (9°, respectively, with the indoline residue and the terminal phenyl group. In the crystal, molecules are linked by C—H...N hydrogen bonds into tapes parallel to the b axis. The tapes are linked together by π–π interactions between triazole rings [inter-centroid distance = 3.4945 (9 Å].