Enantioselective degradation in sediment and aquatic toxicity to Daphnia magna of the herbicide lactofen enantiomers

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 4, 2010, Pages 2439-2445

  Diao, Jinling ^a   Xu, Peng ^a   Wang, Peng ^a   Lu, Dahai ^a   Lu, Yuele ^a   Zhou, Zhiqiang ^a  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

Author keywords

Daphnia magna; Enantioselective degradation; Enantioselective toxicity; Lactofen; Metabolites

Indexed keywords

ACIFLUORFEN; DIPHENYL ETHER DERIVATIVE; HERBICIDE; LACTOFEN; NITROBENZOIC ACID DERIVATIVE; WATER;

ANIMAL; ARTICLE; CHEMISTRY; DAPHNIA; DRUG EFFECT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SEDIMENT; STEREOISOMERISM;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DAPHNIA; GEOLOGIC SEDIMENTS; HALOGENATED DIPHENYL ETHERS; HERBICIDES; NITROBENZOATES; STEREOISOMERISM; WATER;

DAPHNIA; DAPHNIA MAGNA;

EID: 77249127951     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf9038327     Document Type: Article

References (37)

1. Herbicide Handbook, 7th ed.; Weed Science Society of America: Champaign, IL, 1994.
2. The Agrochemicals Handbook; Royal Society of Chemistry: Cambridge, U.K., 1991 (as updated).
3. Lv, C. G.; Diao, J. L.; Na, R. S.; Wu, P.; Zhou, Z. Q. Synthesis, resolution, and absolute configuration of metabolites of the chiral herbicide lactofen. Unpublished work, 2008.
4. Coelln, R.; Eue, L.; Schmidt, R. Optically active phenoxybenzoic acid derivatives and their use as herbicides. Ger. Offen. DE 3210055 Al 19830922, 1983.
5. 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.
6. Overmyer, J. P.; Rouse, D. R.; Avants, J. K.; Garrison, A. W.; DeLorenzo, M. E.; Chung, K. W.; Key, P. B.; Wilson, W. A.; Black, M. C. Toxicity of fipronil and its enantiomers to marine and freshwater non-targets. J. Environ. Sci. Health, Part. B 2007, 42, 471-480.
7. Bradbury, S. P.; Symonik, D. M.; Coats, J. R.; Atchison, G. J. Toxicity of fenvalerate and its constituent isomers to the fathead minnow, Pimephales promelas, and bluegill, Lepomis macrochirus. Bull. Environ. Contam. Toxicol. 1987, 38, 727-735.
8. Williams, A. Opportunities for chiral agrochemicals. Pestic. Sci. 1996, 46, 3-9.
9. Rodriguez, O. P.; Muth, G. W.; Berkman, C. E.; Kim, K.; Thompson, C. M. Inhibition of various cholinesterases with the enantiomers of malaoxon. Bull. Environ. Contam. Toxicol. 1991, 58, 171-176.
10. Kodama, S.; Yamamoto, A.; Saitoh, Y.; Matsunaga, A.; Okamura, K.; Kizu, R.; Hayakawa, K. Enantioseparation of vinclozolin by γ-cyclodextrin- modified micellar electrokinetic chromatography. J. Agric. Food Chem. 2002, 50, 1312-1317. (Pubitemid 34194099)
11. Liu, W.; Gan, J.; Schlenk, D.; Jury, W. A. Enantioselectivity in environmental safety of current chiral insecticides, Proc. Natl. Acad. Sci. U.S.A. 1005, 102 (3), 701-706.
12. Konwick, B. J.; Fisk, A. T.; Garrison, A. W.; Avants, J. K.; Black, M. C. Acute enantioselective toxicity of fipronil and its desulfinyl photoproduct to Ceriodaphnia dubia, Environ. Toxicol. Chem. 1005, 24, 2350-2355.
13. Garrison, A. W. Probing the enantioselectivity of chiral pesticides. Environ, Sci. Technol. 1006, 40, 16-23.
14. U.S. Environmental Protection. Agency. Lactofen Summary Document. Registration Review: Initial Docket; Washington, DC, 2007.
15. U.S. Environmental Protection Agency. Drinking Water Exposure Assessment for Lactofen, Updated for Prospective Ground Water (PGW) Monitoring Study; Washington, DC, 2003.
16. Wauchope, R. D.; Buttler, T. M.; Hornsby, A. G.; AugustijnBeckers, P. W. M.; Burt, J. P. SCS/ARS/CES pesticide properties database for environmental decisionmaking. Rev. Environ. Contam. Toxicol. 1992, 123, 1-164.
17. U.S. Environmental Protection Agency. Environmental Fate and Effects Division. Pesticide Environmental Fate One Line Summary: Lactofen; Washington, DC, 1993.
18. U.S. Environmental Protection Agency. Fact Sheet 128: Lactofen; Washington, DC, 1987.
19. 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. (Pubitemid 29518954)
20. Hegeman, W. J. M.; Laane, R. W. P. M. Enantiomeric enrichment of chiral pesticides in the environment. Rev. Environ. Contam. Toxicol. 2002, 173, 85-116.
21. Falconer,R.L.;Bidleman,T.F.;Gregor,D.J.;Semkin,R.;Teixeira,C. Enantioselectivebreakdownofα- hexachlorohexaneinasmallarcticlakeanditswatershed.Environ.Sci.Technol.1995,29, 1297-1302.(Pubitemid26437784)
22. Wiberg, K.; Letcher, R. J.; Sandau, C. D.; Norstrom, R. J.; Tyskind, 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.
23. Müller, M. D.; Poiger, T.; Buser, H. R. Isolation and identification of the metolachlor stereoisomers using high-performance liquid chromatography, Polarimetric measurements, and enantioselective gas chromatography. J. Agric. Food Chem. 2001, 49, 42-49. (Pubitemid 32104486)
24. Buser, H. R.; Müller, D.; Poiger, T.; Balmer, M. E. Environmental behavior of the chiral acetamide pesticide metalaxyl: enantioselective degradation and chiral stability in soil. Environ. Sci. Technol. 2001, 36, 221-226. (Pubitemid 34072628)
25. Monkiedje, A.; Spiteller, M.; Bester, K. Degradation of racemic and enantiopure metalaxyl in tropical and temperate soils. Environ. Sci. Technol. 2003, 37, 707-712. (Pubitemid 36236685)
26. 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.
27. Wang, X. Q.; Jia, G. F.; Qiu, J.; Diao, J. L.; Zhu, W. T.; Lv, C. G.; Zhou, Z. Q. Stereoselective degradation of fungicide benalaxyl in soils and cucumber plants. Chirality 2007, 19, 125-129.
28. Diao, J. L.; Lv, C. G.; Wang, X. Q.; Dang, Z. H.; Zhu, W. T.; Zhou, Z. Q. Influence of soil properties on the enantioselective degradation of the herbicide lactofen in soils. J. Agric. Food. Chem. 2009, 57, 5865-5871.
29. ASTM (American. Society for Testing and Materials). E1116-98, Standard Test Method for Emulsification Characteristics of Pesticide Emulsifiable Concentrates; ASTM International: West Conshohocken, PA, 2002.
30. Organization for Economix Cooperation and Development. Report of the Final Ring Test of the Daphnia magna Reproduction Test; OECD Environmental Health and Safety Publications Series on Testing and Assessment 6; OECD: Paris, France, 1997.
31. Bartram, J., Balance, R., Eds. Water Quality Monitoring - A Practical Guide to the Design and Implementation of Freshwater Quality Studies and Monitoring Programmes; E&.FN Spon: London, U.K., 1996.
32. Zhou, Z. Q.; Wang, P.; Jiang, S. R. The preparation of polysaccharidebased chiral stationary phase and the direct separation of five chiral pesticides and related intermediates, J. Liq. Chromatogr. Relat. Technol. 2003, 26, 2873-2880.
33. Wang, P.; Jiang, S. R.; Liu, D. H.; Zhang, H. J.; Zhou, Z. Q. Enantiomeric resolution of chiral pesticides by high-performance liquid chromatography. J. Agric. Food Chem. 2006, 54, 1577-1583.
34. Lin, K. D.; Liu, W. P.; Li, L.; Gan, J. Single and joint acute toxicity of isocarbophos enantiomers to Daphnia magna. J. Agric. Food Chem. 2008, 56, 4273-4277.
35. Konwick, B. J.; Fisk, A. T.; Garrison, A. W.; Avants, J. K.; Black, M. C. Acute enantioselective toxicity of fipronil and its desulfinyl photoproduct to Ceriodaphnia dubia. Environ. Toxicol Chem. 2005, 24, 2350-2355.
36. Cai, X. Y.; Liu, W. P.; Sheng, G. Y. Enantioselective degradation and ecotoxicity of the chiral herbicide diclofop in three freshwater alga cultures. J. Agric, Food Chem. 2008, 56, 2139-2146.
37. Buser, H. R.; Müller, M.. D. Environmental behavior of acetamide pesticide stereoisomers. 2. Stereo- and enantioselective degradation in sewage sludge and soil. Environ. Sci. Technol. 1995, 29, 2031-2037.