Enantioselective degradation, abiotic racemization, and chiral transformation of triadimefon in soils

Environmental Science and Technology

Volumn 45, Issue 7, 2011, Pages 2797-2803

  Li, Zhaoyang ^a   Zhang, Yanchuan ^a   Li, Qiaoling ^a   Wang, Weixiao ^a   Li, Jingyin ^a  

^a HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC SOILS; ALKALINE SOILS; CARBONYL GROUPS; CONFIGURATIONAL STABILITY; ENANTIOPURE; ENANTIOSELECTIVE ANALYSIS; ENANTIOSELECTIVE DEGRADATION; ENVIRONMENTAL FATE; PH-DEPENDENT; RED SOILS; TRIAZOLE FUNGICIDES; YELLOW SOIL;

ALKALINITY; ANIMALS; CHIRALITY; DEGRADATION; ENANTIOMERS; ENANTIOSELECTIVITY;

SOILS;

DRUG METABOLITE; TRIADIMEFON; TRIADIMENOL;

ACID SOIL; DEGRADATION; ENVIRONMENTAL FATE; ENVIRONMENTAL RISK; FUNGICIDE; PH; RACEMIZATION; RED SOIL; SOIL CHEMISTRY; TRANSFORMATION;

ABIOTIC STRESS; ALKALINITY; ARTICLE; BIODEGRADATION; CHEMICAL COMPOSITION; CHIRALITY; CONCENTRATION (PARAMETERS); ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PARTICLE SIZE; RACEMIC MIXTURE; RACEMIZATION; RISK FACTOR; SOIL ACIDITY; SOIL ANALYSIS; SOIL MOISTURE; SOIL POLLUTION; STEREOISOMERISM;

FUNGICIDES, INDUSTRIAL; ISOMERISM; MOLECULAR STRUCTURE; SOIL; SOIL POLLUTANTS; TRIAZOLES;

BAODING; CHINA; HEBEI; HUBEI; WUHAN;

ANIMALIA;

EID: 79953245988     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es103830z     Document Type: Article

References (28)

1. Lewis, D. L.; Garrison, A. W.; Wommack, K. E.; Whittemore, A.; Steudler, P. S.; Melillo, J. Influence of environmental changes on degradation of chiral pesticides in soils Nature 1999, 401, 898-901 (Pubitemid 29518954)
2. Müller, T. A.; Kohler, H-P. E. Chirality of pollutants-effects on metabolism and fate Appl. Microbiol. Biot. 2004, 64, 300-316
3. Xu, P.; Liu, D. H.; Diao, J. L.; Lu, D. H.; Zhou, Z. Q. Enantioselective acute toxicity and bioaccumulation of benalaxyl in earthworm (Eisenia fedtia) J. Agric. Food Chem. 2009, 57, 8545-8549
4. Genualdi, S. A.; Simonich, S. L.; Primbs, T. K.; Bidleman, T. F.; Jantunen, L. M.; Ryoo, K. S.; Zhu, T. Enantiomeric signatures of organochlorine pesticides in Asian, trans-pacific, and western U.S. air masses Environ. Sci. Technol. 2009, 43, 2806-2811
5. Singh, N. Factors affecting triadimefon degradation in soils J. Agric. Food Chem. 2005, 53, 70-75 (Pubitemid 40066472)
6. Petrovic, 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 (Pubitemid 23169124)
7. Garcia, G.; Kirchhoff, J.; Grossmann, F. Formation and degradation of triadimenol after the use of triadimefon in a wheat monoculture J. Environ. Sci. Health, Part B 1991, 26, 427-436
8. 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 investigating the stereoselective transformation of triadimefon in rainbow trout Chirality 2010, 22, 183-192
9. Deas, A. H. B.; Garter, 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. Physiol. 1986, 26, 10-21 (Pubitemid 16056351)
10. Gasztonyi, M. The diastereoisomeric ratio in the triadimenol produced by fungal metabolism of triadimefon, and its role in fungicidal selectivity Pestic. Sci. 1981, 12, 433-438
11. Burden, R. S.; Carter, G. A.; Clark, T.; Cooke, D. T.; Croker, S. J.; Deas, A. H. B.; Hedden, P.; James, C. S.; Lenton, J. R. Comparative activity of the enantiomers of triadimenol and paclobutrazol as inhibitors of fungal growth and plant sterol and gibberellin biosynthesis Pestic. Sci. 1987, 21, 253-267
12. International Programme on Chemical Safety: Pesticide residues in food-1981. Available at http://www.inchem.org/documents/jmpr/jmpmono/v81pr32. htm.
13. Moser, V. C.; Macphail, R. C. Neurobehavioral effect of triadimefon, a triazole fungicide, in male and female rats Neurotoxicol. Teratol. 1989, 11, 285-293 (Pubitemid 19184118)
14. 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, New Orleans, LA, 2009; pp 296 - 297.
15. World Health Organization. Evaluations 2004, Part II-Toxicological WHO pesticide residues in food; WHO: Geneva, Switzerland, 2006.
16. Bromilow, R. H.; Evans, A. A.; Nicholls, P. H. Factors affecting degradation rates of five triazole fungicides in two soil types. 1. Laboratory incubations Pestic. Sci. 1999, 55, 1129-1134 (Pubitemid 30010272)
17. US Environmental Protection Agency. Reregistration eligibility decision for triadimefon and tolerance reassessment for triadimenol; EPA: Washington, DC, 2006.
18. Kahle, M.; Buerge, I. J.; Hauser, A.; Müller, M. D.; Poiger, T. Azole fungicides: Occurrence and fate in wastewater and surface waters Environ. Sci. Technol. 2008, 42, 7191-7200
19. Wu, Y. S.; Lee, H. K.; Li, S. F. Y. Simultaneous chiral separation of triadimefon and triadimenol by sulfated β-cyclodextrin-mediated capillary electrophoresis Electrophoresis 2000, 21 (8) 1611-1619 (Pubitemid 30340986)
20. Li, Z. Y.; Zhang, Y. C.; Li, Q. L.; Wang, W. X.; Li, J. Y. Study on chiral separation and enantiomerization of triazole pesticides Chin. J. Anal. Chem. 2010, 38, 237-240
21. Li, Z. Y.; Zhang, Z. C.; Zhou, Q. L.; Gao, R. Y.; Wang, Q. S. Fast and precise determination of phenthoate and its enantiomeric ratio in soil by the matrix solid-phase dispersion method and liquid chromatography J. Chromatogr., A 2002, 977, 17-25
22. Li, Z. Y.; Zhang, Z. C.; Zhang, L.; Leng, L. Isomer- and enantioselective degradation and chiral stability of fenpropathrin and fenvalerate in soil Chemosphere 2009, 76, 509-516
23. Clark, T.; Wong, W. W. C.; Vogeler, K. Comparative fate in soil of enantiomers of triadimenol when applied individually to barley seed Pestic. Sci. 1991, 33, 447-453
24. Li, Z. Y.; Wu, T.; Li, Q. L.; Zhang, B. Z.; Wang, W. X.; Li, J. Y. Characterization of racemization of chiral pesticides in organic solvents and water J. Chromatogr., A 2010, 1217, 5718-5723
25. Nellos, M. G.; Qin, S.; Larive, C.; Schlenk, D.; Gan, J. Epimerization of cypermethrin stereoisomers in alcohols J. Agric. Food Chem. 2009, 57, 6938-6943
26. Liu, W. P.; Qin, S. J.; Gan, J. Y. Chiral stability of synthetic pyrethroid insecticides J. Agric. Food Chem. 2005, 53, 3814-3820
27. Qin, S.; Gan, J. Abiotic enantiomerization of permethrin and cypermethrin: Effects of organic solvents J. Agric. Food Chem. 2007, 55, 5734-5739 (Pubitemid 47092951)
28. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry. Part A. Structure and Mechanisms; Springer-Verlag: Berlin, 2007; pp 579 - 619.