Enantioselectivity in environmental risk assessment of modern chiral pesticides

Environmental Pollution

Volumn 158, Issue 7, 2010, Pages 2371-2383

  Ye, Jing ^a   Zhao, Meirong ^b   Liu, Jing ^a   Liu, Weiping ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Chiral pesticides; Ecotoxicology; Environmental safety; Pollutants

Indexed keywords

ECOLOGY; ENANTIOSELECTIVITY; PESTICIDES; POLLUTION;

ECO-TOXICOLOGY; ECOLOGICAL RISKS; ENVIRONMENTAL POLLUTANTS; ENVIRONMENTAL RISK ASSESSMENT; ENVIRONMENTAL SAFETY; NON-TARGET ORGANISM; POLLUTANTS; SYNTHETIC PYRETHROIDS;

RISK ASSESSMENT;

PESTICIDE;

CHEMISTRY; ENVIRONMENTAL MONITORING; METHODOLOGY; REVIEW; RISK ASSESSMENT; STEREOISOMERISM;

ENVIRONMENTAL MONITORING; PESTICIDES; RISK ASSESSMENT; STEREOISOMERISM;

EID: 77956221414     PISSN: 02697491     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.envpol.2010.03.014     Document Type: Review

References (69)

1. Armstrong, D.W., Reid, G.L., Hilton, M.L., Chang, C.D., 1993. Relevance of enantio-meric separations in environmental science. Environmental Pollution 79, 51-58.
2. Buerge, I.J., Poiger, T., Muller, M.D., Buser, H.R., 2003. Enantioselective degradation of metalaxyl in soils: Chiral preference changes with soil pH. Environmental Science & Technology 37, 2668-2674.
3. Buser, H.R., Muller, M.D., 1995. Environmental behavior of acetamide pesticide stereoisomers. 1. Stereo- and enantioselective determination using chiral high-resolution gas chromatography and chiral high-performance liquid chroma-tography. Environmental Science & Technology 29, 2023-2030.
4. Buser, H.R., Poiger, T., Muller, M.D., 2000. Changed enantiomer composition of metolachlor in surface water following the introduction of the enantiomerically enriched product to the market. Environmental Science & Technology 34, 2690-2696.
5. Cai, X.Y., Liu, W.P., Sheng, G.Y., 2008. Enantioselective degradation and ecotoxicity of the chiral herbicide diclofop in three freshwater alga cultures. Journal of Agricultural and Food Chemistry 56, 2139-2146.
6. Chen, S.W., Liu, W.P., 2008. Toxicity of chiral pesticide Rac-Metalaxyl and R-Met-alaxyl to Daphnia magna. Bulletin of Environmental Contamination and Toxicology 81, 531-534.
7. Chen, S.W., Liu, W.P., 2009. Enantioselective degradation of metalaxyl in anaerobic activated sewage sludge. Bulletin of Environmental Contamination and Toxicology 82, 327-331.
8. Chen, Z.M., Wang, Y.H., 1996. Chromatographic methods for the determination of pyrethrin and pyrethroid pesticide residues in crops, foods and environmental samples. Journal of Chromatography A 754, 367-395.
9. Crosby, D.G., 1998. Environmental Toxicology and Chemistry. Oxiford University, New York.
10. Garrison, A.W., 2006. Probing the enantioselectivity of chiral pesticides. Environmental Science & Technology 40, 16-23.
11. Garrison, A.W., Schmitt, P., Martens, D., Kettrup, A., 1996. Enantiomeric selectivity in the environmental degradation of dichlorprop as determined by high performance capillary electrophoresis. Environmental Science & Technology 30,2449-2455.
12. Hegeman, W.J.M., Laane, R., 2002. Enantiomeric enrichment of chiral pesticides in the environment. Reviews of Environmental Contamination and Toxicology 173, 85-116.
13. Jianmongkol, S., Berkman, C.E., Thompson, CM., Richardson, R.J., 1996. Relative potencies of the four stereoisomers of isomalathion for inhibition of hen brain acetylcholinesterase and neurotoxic esterase in vitro. Toxicology and Applied Pharmacology 139, 342-348.
14. Jin, Y.X., Chen, R.J., Sun, L.W., Wang, W.Y., Zhou, L., Liu, W.P., Fu, Z.W., 2009. Enan-tioselective induction of estrogen-responsive gene expression by permethrin enantiomers in embryo-larval zebrafish. Chemosphere 74,1238-1244.
15. Jin, Y.X., Wang, W.Y., Xu, C, Fu, Z.W., Liu, W.P., 2008. Induction of hepatic estrogen-responsive gene transcription by permethrin enantiomers in male adult zebrafish. Aquatic Toxicology 88, 146-152.
16. Jones, W.J., Mazur, C.S., Kenneke, J.F., Garrison, A.W., 2007. Enantioselective microbial transformation of the phenylpyrazole insecticide fipronil in anoxic sediments. Environmental Science & Technology 41, 8301-8307.
17. Kallenborn, R., Huhnerfuss, H., Konig, W.A., 1991. Gas-chromatographic separation of the enantiomers of organic marine pollutants .2. Enantioselective metabolism of (+/- )-alpha-1,2,3,4,5,6-hexachlorocyclohexane in organs of the eider duck. Angewandte Chemie-International Edition in English 30, 320-321.
18. Konwick, B.J., Fisk, A.T., Garrison, A.W, Avants, J.K., Black, M.C., 2005. Acute enantioselective toxicity of fipronil and its desulfinyl photoproduct to Ceriodaphnia dubia. Environmental Toxicology and Chemistry 24, 2350-2355.
19. Kurihara, N., Miyamoto, J., 1998. Chirality in Agrochemicals. John Wiley & Sons, Chichester.
20. Leicht, W, Fuchs, R., Londershausen, M., 1996. Stability and biological activity of cyfluthrin isomers. Pesticide Science 48, 325-332.
21. Lewis, D.L., Garrison, A.W, Wommack, K.E., Whittemore, A., Steudler, P., Melillo, J., 1999. Influence of environmental changes on degradation of chiral pollutants in soils. Nature 401, 898-901.
22. Lin, K., Zhou, S.S., Xu, C, Liu, W.P., 2006. Enantiomeric resolution and biotoxicity of methamidophos. Journal of Agricultural and Food Chemistry 54, 8134-8138.
23. Lin, K.D., Liu, W.P., Li, L., Gan, J., 2008. Single and joint acute toxicity of isocarbophos enantiomers to Daphnia magna. Journal of Agricultural and Food Chemistry 56, 4273-4277.
24. Lin, K.D., Zhang, F., Zhou, S.S., Liu, W.P., Gan, J., Pan, Z.Y, 2007. Stereoisomeric separation and toxicity of the nematicide fosthiazate. Environmental Toxicology and Chemistry 26, 2339-2344.
25. Liu, D.H., Wang, P., Zhu, W.D., Gu, X., Zhou, W.F., Zhou, Z.Q., 2008a. Enantioselective degradation of fipronil in Chinese cabbage (Brassiea pekinensis). Food Chemistry 110, 399-405.
26. Liu, H.G., Xu, L.H., Zhao, M.R., Liu, W.P., Zhang, C, Zhou, S.S., 2009. Enantiomer-specific, bifenthrin-induced apoptosis mediated by MAPK signalling pathway in Hep G2 Cells. Toxicology 261, 119-125.
27. Liu, H.G., Zhao, M.R., Zhang, C, Ma, Y, Liu, W.P., 2008b. Enantioselective cytotoxicity of the insecticide bifenthrin on a human amnion epithelial (FL) cell line. Toxicology 253, 89-96.
28. Liu, H.J., Xiong, M.Y, 2009. Comparative toxicity of racemic metolachlor and S-metolachlor to Chlorella pyrenoidosa. Aquatic Toxicology 93,100-106.
29. Liu, H.J., Ye, W.H., Zhan, X.M., Liu, W.P., 2006a. A comparative study of rac- and S-metolachlor toxicity to Daphnia magna. Ecotoxicology and Environmental Safety 63, 451-455.
30. Liu, W.P., Gan, J.J., Lee, S.J., Werner, I., 2004. Isomer selectivity in aquatic toxicity and biodegradation of cypermethrin. Journal of Agricultural and Food Chemistry 52, 6233-6238.
31. Liu, W.P., Gan, J.J., Qin, S., 2005a. Separation and aquatic toxicity of enantiomers of synthetic pyrethroid insecticides. Chirality 17, S127-S133.
32. Liu, W.P., Gan, J.Y, Lee, S., Werner, I., 2005b. Isomer selectivity in aquatic toxicity and biodegradation of bifenthrin and permethrin. Environmental Toxicology and Chemistry 24,1861-1866.
33. Liu, W.P., Gan, J.Y, Schlenk, D., Jury, W.A., 2005c. Enantioselectivity in environmental safety of current chiral insecticides. Proceedings of the National Academy of Sciences of the United States of America 102, 701-706.
34. Liu, W.P., Lin, K.D., Gan, J.Y, 2006b. Separation and aquatic toxicity of enantiomers of the organophosphorus insecticide trichloronate. Chirality 18, 713-716.
35. Liu, W.P., Qin, S.J., Gan, J.Y, 2005d. Chiral stability of synthetic pyrethrold insecticides. Journal of Agricultural and Food Chemistry 53, 3814-3820.
36. Ma, Y, Chen, L.H., Lu, X.T., Chu, H.D., Xu, C, Liu, W.P., 2009a. Enantioselectivity in aquatic toxicity of synthetic pyrethroid insecticide fenvalerate. Ecotoxicology and Environmental Safety 72,1913-1918.
37. Ma, Y, Liu, W.P., Wen, Y.Z., 2006. Enantioselective degradation of rac-metolachlor and S-metolachlor in soil. Pedosphere 16, 489-494.
38. Ma, Y, Xu, C, Wen, Y.Z., Liu, W.P., 2009b. Enantioselective separation and degradation of the herbicide Dichlorprop Methyl in sediment. Chirality 21,480-483.
39. Marucchini, C, Zadra, C, 2002. Stereoselective degradation of metalaxyl and met-alaxyl-M in soil and sunflower plants. Chirality 14, 32-38.
40. McKone, T.E., Castorina, R., Harnly, M.E., Kuwabara, Y, Eskenazi, B., Bradman, A., 2007. Merging models and biomonitoring data to characterize sources and pathways of human exposure to organophosphorous pesticides in the salinas Valley of California. Environmental Science & Technology 41, 3233-3240.
41. Miyamoto, J., 1976. Degradation, metabolism and toxicity of synthetic pyrethroids. Environmental Health Perspectives 14,15-28.
42. Miyamoto, J., Kaneko, H., Okuno, Y., 1986. A Novel Lipophilic Cholesterol Ester Conjugate from Fenvalerate, Xenobiotic Conjugation Chemistry. American Chemical Society, Washington, DC, pp. 268-281.
43. Miyazaki, A., Nakamura, T., Kawaradani, M., Marumo, S., 2002. Resolution and biological activity of both enantiomers of methamidophos and acephate. Journal of Agricultural and Food Chemistry 36, 835-837.
44. Miyazaki, A., Nakamura, T., Marumo, S., 1985. Chiral metabolism of achiral prop-aphos into (R)s-(+)-propaphos sulfoxide in rice plants. Journal of Pesticide Science 10, 727-728.
45. Nigg, H.N., Knaak, J.B., 2000. Blood cholinesterases as human biomarkers of organophosphorus pesticide exposure. Reviews of Environmental Contamination and Toxicology 163, 29-111.
46. Nillos, M.G., Lin, K., Gan, J., Bondarenko, S., Schlenk, D., 2009. Enantioselectivity in fipronil aquatic toxicity and degradation. Environmental Toxicology and Chemistry 28, 1825-1833.
47. 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., 2007. Toxicity of fipronil and its enantiomers to marine and freshwater non-targets. Journal of Environmental Science and Health Part B-Pesticides Food Contaminants and Agricultural Wastes 42, 471-480.
48. Qian, H.F., Hu, H., Mao, Y., Ma, J., Zhang, A.P., Liu, W.P., Fu, Z.W., 2009. Enantiose-lective phytotoxicity of the herbicide imazethapyr in rice. Chemosphere 76, 885-892.
49. Qin, S.J., Budd, R., Bondarenko, S., Liu, W.P., Gan, J.Y., 2006. Enantioselective degradation and chiral stability of pyrethroids in soil and sediment. Journal of Agricultural and Food Chemistry 54, 5040-5045.
50. Sakata, S., Mikami, N., Yamada, H., 1992. Degradation of pyrethroid optical isomers in soils. Journal of Pesticide Science 17, 169-180.
51. Tan, H.H., Cao, Y.S., Tang, T., Qian, K., Chen, W.L., Li, J.Q., 2008. Biodegradation and chiral stability of fipronil in aerobic and flooded paddy soils. Science of the Total Environment 407, 428-437.
52. Wang, L.M., Liu, W.P., Yang, C.X., Pan, Z.Y., Gan, J.Y., Xu, C., Zhao, M.R., Schlenk, D., 2007. Enantioselectivity in estrogenic potential and uptake of bifenthrin. Environmental Science & Technology 41, 6124-6128.
53. Wang, Y.-S., Tai, K.-T., Yen, J.-H., 2004. Separation, bioactivity, and dissipation of enantiomers of the organophosphorus insecticide fenamiphos. Ecotoxicology and Environmental Safety 57, 346-353.
54. Wen, Y.Z., Yuan, Y.L., Shen, C.S., Liu, H.J., Liu, W.P., 2009. Spectroscopic investigations of the chiral interactions between lipase and the herbicide dichlorprop. Chirality 21, 396-401.
55. Williams, A., 1995. Opportunities for Chiral Agrochemicals, Symposium on Chirality in Crop Protection Chemistry. John Wiley & Sons Ltd, London, England, pp. 3-9.
56. Wilson, W.A., Konwick, B.J., Garrison, A.W., Avants, J.K., Black, M.C., 2008. Enan-tioselective chronic toxicity of fipronil to Ceriodaphnia dubia. Archives of Environmental Contamination and Toxicology 54, 36-43.
57. Xu, C., Wangj, J.J., Liu, W.P., Sheng, G.D., Tu, Y.J., Ma, Y., 2008a. Separation and aquatic toxicity of enantiomers of the pyrethroid insecticide lambda-cyhalothrin. Environmental Toxicology and Chemistry 27, 174-181.
58. Xu, C., Zhao, M.R., Liu, W.P., Chen, S.W., Gan, J.Y., 2008b. Enantioselectivity in zebrafish embryo toxicity of the insecticide acetofenate. Chemical Research in Toxicology 21, 1050-1055.
59. Ye, J., Wu, J., Liu, W.P., 2009a. Enantioselective separation and analysis of chiral pesticides by high-performance liquid chromatography. Trac-trends in Analit-ical Chemistry 28, 1148-1163.
60. Ye, J., Zhang, Q., Zhang, A.P., Wen, Y.Z., Liu, W.P., 2009b. Enantioselective effects of chiral herbicide diclofop acid on rice Xiushui 63 seedlings. Bulletin of Environmental Contamination and Toxicology 83, 85-91.
61. Yen, J.-H., Tsai, C.-C., Wang, Y.-S., 2003. Separation and toxicity of enantiomers of organophosphorus insecticide leptophos. Ecotoxicology and Environmental Safety 55, 236-242.
62. Zhan, X.M., Liu, H.J., Miao, Y.G., Liu, W.P., 2006. A comparative study of rac- and S-metolachlor on some activities and metabolism of silkworm, Bombyx mori L. Pesticide Biochemistry and Physiology 85, 133-138.
63. Zhao, M.R., Wang, C., Liu, K.K., Sun, L.W., Li, L., Liu, W.P., 2009. Enantioselectivity in chronic toxicology and accumulation of the synthetic pyrethroid insecticide bifenthrin in Daphnia magna. Environmental Toxicology & Chemistry 28, 1475-1479.
64. Zhao, M.R., Liu, W.P., 2009. Enantioselectivity in the immunotoxicity of the insecticide acetofenate in an in vitro model. Environmental Toxicology & Chemistry 28, 578-585.
65. Zhou, Q.Y., Xu, C., Zhang, Y.S., Liu, W.P., 2009a. Enantioselectivity in the phytotox-icity of herbicide imazethapyr. Journal of Agricultural and Food Chemistry 57, 1624-1631.
66. Zhou, S.S., Lin, K.D., Li, L., Jin, M.Q., Ye, J., Liu, W.P., 2009b. Separation and toxicity of salithion enantiomers. Chirality.
67. Zhou, S.S., Lin, K.D., Yang, H.Y., Li, L., Liu, W.P., Li, J., 2007. Stereoisomeric separation and toxicity of a new organophosphorus insecticide chloramidophos. Chemical Research in Toxicology 20, 400-405.
68. Zhou, S.S., Wang, L.M., Li, L., Liu, W.P., 2009c. Stereoisomeric separation and bioassay of a new organophosphorus compound, O, S-dimethyl- N-(2,2,2-tri-chloro-1-methoxyethyl)phosphoramidothioate: Some implications for chiral switch. Journal of Agricultural and Food Chemistry 57, 6920-6926.
69. Zhou, Y., Li, L., Lin, K., Zhu, X.P., Liu, W.P., 2009d. Enantiomer separation of triazole fungicides by high-performance liquid chromatography. Chirality 21, 421-427.