Stereoselective transformation of triadimefon to metabolite triadimenol in wheat and soil under field conditions

Journal of Hazardous Materials

Volumn 260, Issue , 2013, Pages 929-936

  Liang, Hongwu ^a,c   Li, Li ^b   Qiu, Jing ^a   Li, Wei ^b   Yang, Shuming ^a   Zhou, Zhiqiang ^c   Qiu, Lihong ^c  

^a AGRO ENVIRONMENTAL PROTECTION INSTITUTE   (China)

^b INSTITUTE OF ZOOLOGY   (China)

^c CHINA AGRICULTURAL UNIVERSITY   (China)

Author keywords

Soil; Stereoselective transformation; Triadimefon; Triadimenol; Wheat

Indexed keywords

ENANTIOSELECTIVE DEGRADATION; FIELD CONDITIONS; FIRST ORDER KINETICS; STEREOSELECTIVE FORMATION; STEREOSELECTIVE TRANSFORMATIONS; TRIADIMEFON; TRIADIMENOL; WHEAT;

AGRICULTURAL CHEMICALS; ENANTIOMERS; ENANTIOSELECTIVITY; FUNGICIDES; METABOLITES; RISK ASSESSMENT; STEREOCHEMISTRY; STEREOSELECTIVITY; TOXICITY;

SOILS;

TRIADIMEFON; TRIADIMENOL;

AGROCHEMICAL; BIODEGRADATION; BIOTRANSFORMATION; FIELD SURVEY; METABOLITE; REACTION KINETICS; SOIL POLLUTION; STRAW; WHEAT;

ARTICLE; CHIRALITY; CONDITIONING; CONTROLLED STUDY; DIASTEREOISOMER; DRUG TRANSFORMATION; ENANTIOMER; FIELD EXPERIMENT; RISK ASSESSMENT; SOIL; STEREOCHEMISTRY; WHEAT;

SOIL; STEREOSELECTIVE TRANSFORMATION; TRIADIMEFON; TRIADIMENOL; WHEAT;

ENVIRONMENTAL REMEDIATION; FUNGICIDES, INDUSTRIAL; KINETICS; MODELS, CHEMICAL; PESTICIDES; RISK ASSESSMENT; SOIL POLLUTANTS; STEREOISOMERISM; TIME FACTORS; TRIAZOLES; TRITICUM;

CHINA;

EID: 84880578599     PISSN: 03043894     EISSN: 18733336     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2013.06.046     Document Type: Article

References (37)

1. Garrison A.W., Avants J.K., Jones W.J. Microbial transformation of triadimefon to triadimenol in soils: selective production rates of triadimenol stereoisomers affect exposure and risk. Environ. Sci. Technol. 2011, 45:2186-2193.
2. Deas A.H.B., Carter G.A., Clark T., Clifford D.R., James C.S. The enantiomeric composition of triadimenol produced during metabolism of triadimefon by fungi. III. Relationship with sensitivity to triadimefon. Pestic. Biochem. Phys. 1986, 26:10-21.
3. Li Z., Zhang Y., Li Q., Wang W., Li J. Enantioselective degradation, abiotic racemization, and chiral transformation of triadimefon in soils. Environ. Sci. Technol. 2011, 45:2797-2803.
4. Dong F., Liu X., Zheng Y., Cao Q., Li C. Stereoselective degradation of fungicide triadimenol in cucumber plants. Chirality 2010, 22:292-298.
5. Konwick B.J., Garrison A.W., Avants J.K., Fisk A.T. Bioaccumulation and biotransformation of chiral triazole fungicides in rainbow trout (Oncorhynchus mykiss). Aquat. Toxicol. 2006, 80:372-381.
6. Kenneke J.F., Ekman D.R., Mazur C.S., Konwick B.J., Fisk A.T., Avants J.K., Garrison A.W. Integration of metabolomics and in vitro metabolism assays for investigating the stereoselective transformation of triadimefon in rainbow trout. Chirality 2010, 22:183-192.
7. Deas A.H.B., Clifford D.R. Metabolism of the 1,2,4-triazolylmethane fungicides, triadimefon, triadimenol, and diclobutrazol by Aspergillus niger (van Tiegh.). Pestic. Biochem. Phys. 1982, 17:120-133.
8. Gasztonyi M. The diastereomeric ratio in the triadimenol produced by fungal metabolism of triadimefon, and its role in fungicidal selectivity. Pestic. Sci. 1981, 12:433-438.
9. Kurihara N., Miyamoto J., Paulson G.D., Zeeh B., Skidmore M.W., Hollingworth R.M., Kuiper H.A. Chirality in synthetic agrochemicals: bioactivity and safety considerations. Pestic. Sci. 1999, 55:219.
10. Kenneke J.F., Mazur C.S., Kellock K.A., Overmyer J.P. Mechanistic approach to understanding the toxicity of the azole fungicide triadimefon to a nontarget aquatic insect and implications for exposure assessment. Environ. Sci. Technol. 2009, 43:5507-5513.
11. Walker Q.D., Lewis M.H., Crofton K.M., Mailman R.B. Triadimefon, a triazole fungicide, induces stereotyped behavior and alters monoamine metabolism in rats. Toxicol. Appl. Pharm. 1990, 102:474-485.
12. Menegola E., Broccia M.L., Di Renzo F., Prati M., Giavini E. In vitro teratogenic potential of two antifungal triazoles: triadimefon and triadimenol. In Vitro Cell Dev. Biol. Anim. 2000, 36:88-95.
13. Crofton K. A structure-activity relationship for the neurotoxicity of triazole fungicides. Toxicol. Lett. 1996, 84:155-159.
14. Edwards D. Reregistration Eligibility Decision for Triadimefon and Tolerence Reassessment for Triadimenol 2006, US Environmental Protection Agency, Washington, DC.
15. Petrovic A.M., Young R.G., Ebel J.G., Lisk D.J. Conversion of triadimefon fungicide to triadimenol during leaching through turfgrass soils. Chemosphere 1993, 26:1549-1557.
16. Singh N. Sorption behavior of triazole fungicides in Indian soils and its correlation with soil properties. J. Agric. Food Chem. 2002, 50:6434-6439.
17. Garcia G., Kirchhoff J., Grossmann F. Formation and degradation of triademinol after the use of triadimefon in a wheat monoculture. J. Environ. Sci. Health B 1991, 26:427-436.
18. Stensvand A., Christiansen A. Investigation on fungicide residues in greenhouse-grown strawberries. J. Agric. Food Chem. 2000, 48:917-920.
19. Crowell S.R., Henderson W.M., Kenneke J.F., Fisher J.W. Development and application of a physiologically based pharmacokinetic model for triadimefon and its metabolite triadimenol in rats and humans. Toxicol. Lett. 2011, 205:154-162.
20. Menegola E., Broccia M.L., Di Renzo F., Massa V., Giavini E. Study on the common teratogenic pathway elicited by the fungicides triazole-derivatives. Toxicol. In Vitro 2005, 19:737-748.
21. Clark T., Vogeler K., Ishikawa I. Comparative metabolism of the enantiomers of triadimenol in barley plants. Brit. Crop Prot. Conf. Pests Dis. 1986, 2:475-482.
22. Clark T., Wong W.W.C., Vogeler K. Comparative fate in soil of the enantiomers of triadimenol when applied individually to barley seed. Pestic. Sci. 1991, 33:447-453.
23. Liang H., Qiu J., Li L., Li W., Zhou Z., Liu F., Qiu L. Stereoselective separation and determination of triadimefon and triadimenol in wheat, straw, and soil by liquid chromatography-tandem mass spectrometry. J. Sep. Sci. 2012, 35:166-173.
24. Otsuka K., Matsumura M., Kim J.-B., Terabe S. On-line preconcentration and enantioselective separation of triadimenol by electrokinetic chromatography using cyclodextrins as chiral selectors. J. Pharmaceut. Biomed. 2003, 30:1861-1867.
25. Harner T., Wiberg K., Norstrom R. Enantiomer fractions are preferred to enantiomer ratios for describing chiral signatures in environmental analysis. Environ. Sci. Technol. 2000, 34:218-220.
26. Wang X., Wang X., Zhang H., Wu C., Wang X., Xu H., Wang X., Li Z. Enantioselective degradation of tebuconazole in cabbage, cucumber, and soils. Chirality 2012, 24:104-111.
27. Wang X., Zhang H., Xu H., Wang X., Wu C., Yang H., Li Z., Wang Q. Enantioselective residue dissipation of hexaconazole in cucumber (Cucumis sativus L.), head cabbage (Brassica oleracea L. var. caulorapa DC.), and soils. J. Agric. Food Chem. 2012, 60:2212-2218.
28. Liang H., Qiu J., Li L., Li W., Zhou Z., Liu F., Qiu L. Stereoselective dissipation of epoxiconazole in grape (Vitis vinifera cv. Kyoho) and soil under field conditions. Chemosphere 2012, 87:982-987.
29. Salama A.K., A.A.A.I-Rokaibah, Al-Ghomiz N.N., Soliman S.A. Persistence of triadimefon residues in vegetable fruits grown in green houses: a study demonstrating hazards of pesticide misuse in Saudi Arabia. J. King Saud. Univ.-Agric. Sci. 1997, 9:177-186.
30. Niu H., Wang Y., Lu Z., Zhang H. Study on residual dynamics of triadimefon in cabbage and soil. J. Jilin Agric. Univ. 2005, 27:209-211.
31. Liu Y., Yang R., Guo Z. Triadimefon WP residue dynamics in rapeseed and soil. Pesticides 2004, 43:559-562.
32. Patil S.G., Nicholls P.H., Chamberlain K., Briggs G.G., Bromilow R.H. Degradation rates in soil of 1-benzyltriazoies and two triazole fungicides. Pestic. Sci. 1988, 22:333-342.
33. Kellock K., Overmyer J., Garrison A.W., Avants J.K. Toxicity of triadimefon racemate and enantiomers to black fly larvae. SETAC North America 30th Annual Meeting 2009, 19-23.
34. Arias-Estévez M., López-Periago E., Martinez-Carballo E., Simal-Gándara J. Carbofuran sorption kinetics by corn crop soils. Bull. Environ. Contam. Toxicol. 2006, 77:267-273.
35. World Health Organization Evaluations 2004, Part II - Toxicological WHO Pesticide Residues in Food 2006, WHO, Geneva, Switzerland.
36. Maya G. The diastereomeric ratio in the triadimenol produced by fungal metabolism of triadimefon, and its role in fungicidal selectivity. Pestic. Sci. 1981, 12:433-438.
37. Garrison A.W. Probing the enantioselectivity of chiral pesticides. Environ. Sci. Technol. 2006, 40:16-23.