Environmental behavior of the chiral triazole fungicide fenbuconazole and its chiral metabolites: Enantioselective transformation and degradation in soils

Environmental Science and Technology

Volumn 46, Issue 5, 2012, Pages 2675-2683

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

^a AGRO ENVIRONMENTAL PROTECTION INSTITUTE   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC SOILS; AEROBIC AND ANAEROBIC CONDITIONS; ALKALINE SOILS; ANAEROBIC CONDITIONS; CHIRAL CENTERS; CONVERTED PRODUCTS; DEGRADATION RATE; ENANTIOSELECTIVE ANALYSIS; ENANTIOSELECTIVE DEGRADATION; ENANTIOSELECTIVE TRANSFORMATION; ENVIRONMENTAL BEHAVIOR; EXPERIMENTAL EVIDENCE; LIQUID CHROMATOGRAPHY-TANDEM MASS SPECTROMETRY; REVERSED PHASE; STEREO-SELECTIVE; TRIAZOLE FUNGICIDES;

BIOMOLECULES; CHIRALITY; DEGRADATION; ENANTIOMERS; ENANTIOSELECTIVITY; FUNGICIDES; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; METABOLITES; NITROGEN COMPOUNDS; STEREOCHEMISTRY; STEREOSELECTIVITY;

SOILS;

FENBUCONAZOLE; FUNGICIDE; UNCLASSIFIED DRUG;

ACID SOIL; ALKALINITY; CONCENTRATION (COMPOSITION); DEGRADATION; ENVIRONMENTAL FATE; FUNGICIDE; METABOLITE; REDOX CONDITIONS; TRANSFORMATION;

AEROBIC BACTERIUM; ANAEROBIC CAPACITY; ARTICLE; BIOTRANSFORMATION; CHEMICAL STRUCTURE; CHIRALITY; CONCENTRATION (PARAMETERS); ENANTIOSELECTIVITY; ENVIRONMENTAL IMPACT ASSESSMENT; PH MEASUREMENT; REVERSED PHASE LIQUID CHROMATOGRAPHY; SOIL DEGRADATION; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

AEROBIOSIS; ANAEROBIOSIS; CHROMATOGRAPHY, LIQUID; ENVIRONMENTAL REMEDIATION; FUNGICIDES, INDUSTRIAL; HALF-LIFE; HYDROGEN-ION CONCENTRATION; KINETICS; MASS SPECTROMETRY; NITRILES; SOIL POLLUTANTS; STEREOISOMERISM; TRIAZOLES;

EID: 84863248553     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es203320x     Document Type: Article

References (32)

1. Conclusion on the peer review of the pesticide risk assessment of the active substance fenbuconazole. EFSA J. 2010, 8, No. 1558.
2. Pesticide Residues in Food-1997: Evaluations Part 1- Residues; FAO Plant Production and Protection Paper; Food and Agriculture Organization of the United Nations: Rome, Italy, 1998; xvii + 846 pp.
3. Laville, N.; Balaguer, P.; Brion, F.; Hinfray, N.; Casellas, C.; Porcher, J. M.; Ait-Aissa, S. Modulation of aromatase activity and mRNA by various selected pesticides in the human choriocarcinoma JEG-3 cell line Toxicology 2006, 228, 98-108
4. Juberg, D. R.; Mudra, D. R.; Hazelton, G. A.; Parkinson, A. The effect of fenbuconazole on cell proliferation and enzyme induction in the liver of female CD1 mice Toxicol. Appl. Pharmacol. 2006, 214, 178-187
5. Dellarco, V. L.; Baetcke, K. A risk assessment perspective: Application of mode of action and human relevance frameworks to the analysis of rodent tumor data Toxicol. Sci. 2005, 86, 1-3
6. Garrison, A. W.; Schmitt, P.; Martens, D.; Kettrup, A. Enantiomeric selectivity in the environmental degradation of dichlorprop as determined by high performance capillary electrophoresis Environ. Sci. Technol. 1996, 30, 2449-2455
7. Williams, A. Opportunities for chiral agrochemicals Pestic. Sci. 1996, 46, 3-9
8. Garrison, A. W. Probing the enantioselectivity of chiral pesticides Environ. Sci. Technol. 2006, 40, 16-23
9. Ye, J.; Zhao, M.; Liu, J.; Liu, W. Enantioselectivity in environmental risk assessment of modern chiral pesticides Environ. Pollut. 2010, 158, 2371-2383
10. Hegeman, W. J. M.; Laane, R. Enantiomeric enrichment of chiral pesticides in the environment Rev. Environ. Contam. Toxicol. 2002, 173, 85-116
11. Liu, W. P.; Gan, J. Y.; Schlenk, D.; Jury, W. A. Enantioselectivity in environmental safety of current chiral insecticides Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 701-706
12. Lewis, D. L.; Garrison, A. W.; Wommack, K. E.; Whittemore, A.; Steudler, P.; Melillo, J. Influence of environmental changes on degradation of chiral pollutants in soils Nature 1999, 401, 898-901
13. Falconer, R. L.; Bidleman, T. F.; Gregor, D. J.; Semkin, R.; Teixeira, C. Enantioselective breakdown of α-hexachlorocyclohexane in a small arctic lake and its watershed Environ. Sci. Technol. 1995, 29, 1297-1302
14. Wiberg, K.; Letcher, R. J.; Sandau, C. D.; Norstrom, R. J.; Tysklind, M.; Bidleman, T. F. The enantioselective bioaccumulation of chiral chlordane and α-HCH contaminants in the polar bear food chain Environ. Sci. Technol. 2000, 34, 2668-2674
15. Muller, M. D.; Buser, H. R. Conversion reactions of various phenoxyalkanoic acid herbicides in soil. 1. Enantiomerization and enantioselective degradation of the chiral 2-phenoxypropionic acid herbicides Environ. Sci. Technol. 1997, 31, 1953-1959
16. 2O/soil system Environ. Sci. Technol. 1997, 31, 1960-1967
17. Schneiderheinze, J.; Armstrong, D.; Berthod, A. Plant and soil enantioselective biodegradation of racemic phenoxyalkanoic herbicides Chirality 1999, 11, 330-337
18. Romero, E.; Matallo, M.; Pena, A.; Sanchez-Rasero, F.; Schmitt-Kopplin, P.; Dios, G. Dissipation of racemic mecoprop and dichlorprop and their pure R-enantiomers in three calcareous soils with and without peat addition Environ. Pollut. 2001, 111, 209-215
19. Buser, H. R.; Muller, M. D.; Poiger, T.; Balmer, M. E. Environmental behavior of the chiral acetamide pesticide metalaxyl: Enantioselective degradation and chiral stability in soil Environ. Sci. Technol. 2002, 36, 221-226
20. Monkiedje, A.; Spiteller, M.; Bester, K. Degradation of racemic and enantiopure metalaxyl in tropical and temperate soils Environ. Sci. Technol. 2003, 37, 707-712
21. Konwick, B. J.; Garrison, A. W.; Black, M. C.; Avants, J. K.; Fisk, A. T. Bioaccumulation, biotransformation, and metabolite formation of fipronil and chiral legacy pesticides in rainbow trout Environ. Sci. Technol. 2006, 40, 2930-2936
22. Jones, W. J.; Mazur, C. S.; Kenneke, J. F.; Garrison, A. W. Enantioselective microbial transformation of the phenylpyrazole insecticide fipronil in anoxic sediments Environ. Sci. Technol. 2007, 41, 8301-8307
23. 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
24. 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
25. Jarman, J. L.; Jones, W. J.; Howell, L. A.; Garrison, A. W. Application of capillary electrophoresis to study the enantioselective transformation of five chiral pesticides in aerobic soil slurries J. Agric. Food Chem. 2005, 53, 6175-6182
26. Perez, S.; Barcelo, D. Applications of LC-MS to quantitation and evaluation of the environmental fate of chiral drugs and their metabolites TrAC, Trends Anal. Chem. 2008, 27, 836-846
27. Qian, M.; Wu, L.; Zhang, H.; Wang, J.; Li, R.; Wang, X.; Chen, Z. Stereoselective determination of famoxadone enantiomers with HPLC-MS/MS and evaluation of their dissipation process in spinach J. Sep. Sci. 2011, 34, 1236-1243
28. Brinch, U. C.; Ekelund, F.; Jacobsen, C. S. Method for spiking soil samples with organic compounds Appl. Environ. Microbiol. 2002, 68, 1808-1816
29. 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
30. Mueller, M. D.; Buser, H. R. Environmental behavior of acetamide pesticide stereoisomers. 2. Stereo- and enantioselective degradation in sewage sludge and soil Environ. Sci. Technol. 1995, 29, 2031-2037
31. Qin, S.; Gan, J. Enantiomeric differences in permethrin degradation pathways in soil and sediment J. Agric. Food Chem. 2006, 54, 9145-9151
32. Wong, C. S. Environmental fate processes and biochemical transformations of chiral emerging organic pollutants Anal. Bioanal. Chem. 2006, 386, 544-558