Isomer- and enantioselective degradation and chiral stability of fenpropathrin and fenvalerate in soils

Chemosphere

Volumn 76, Issue 4, 2009, Pages 509-516

  Li, Zhaoyany ^a   Zhang, Zhichao ^b   Zhang, Ling ^b   Leng, Lian ^b  

^a HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

Enantioselectivity; Fenpropathrin; Fenvalerate; Fenvaleric acid; Racemization

Indexed keywords

ALKALINITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERS; METABOLITES; STEREOCHEMISTRY;

CONFIGURATIONALLY; DEGRADATION PROCESS; ENANTIOSELECTIVE DEGRADATION; FENPROPATHRIN; FENVALERATE; METHANOL-BUFFER SOLUTIONS; PYRETHROID INSECTICIDE; RACEMIZATION;

SOILS;

FENPROPATHRIN; FENVALERATE; FENVALERIC ACID; METHANOL; UNCLASSIFIED DRUG;

DEGRADATION; FENVALERATE; INCUBATION; LIQUID CHROMATOGRAPHY; METABOLITE; METHANOL; PH; RACEMIZATION; SOIL POLLUTION;

ALKALINITY; ARTICLE; CHIRALITY; DEGRADATION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INCUBATION TIME; ISOMER; PH; RACEMIZATION; SOIL ANALYSIS;

EID: 67349112371     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2009.03.015     Document Type: Article

References (32)

1. Ahmad I., and Crawford G. Trace residue analysis of the herbicide chlorsulfuron in soil by gas-chromatography-electron capture detection. J. Agric. Food Chem. 38 (1990) 138-141
2. Bordajandi L.R., Abad E., and González M.J. Occurrence of PCBs, PCDD/Fs, PBDEs and DDTs in Spanish breast milk: enantiomeric fraction of chiral PCBs. Chemosphere 70 (2008) 567-575
3. Bradbury S.P., Symonik D.M., Coats J.R., and Atchison G.J. Toxicity of fenvalerate and its constituent isomers to the Fathead Minnow, Pimephales Promelas, and Bluegill, Lepomis macrochirus. Bull. Environ. Contam. Toxicol. 38 (1987) 727-735
4. Buser H.R., and Müller M.D. Occurrence and transformation reactions of chiral and achiral phenoxyalkanoic acid herbicides in lakes and rivers in Switzerland. Environ. Sci. Technol. 32 (1998) 626-633
5. Dondi M., Flieger M., Olsovska J., Polcaro C.M., and Sinibaldi M. High-performance liquid chromatography study of the enantiomer separation of chrysanthemic acid and its analogous compounds on terguride-based stationary phase. J. Chromatogr. A 859 (1999) 133-142
6. Huang T.B., Huang S.G., Kuang C.Y., Wu B.G., and Zhou J.X. Determination of fenvalerate stereoisomers on the chiral stationary phase by high-performance liquid chromatography. Chin. J. Anal. Chem. 19 (1991) 282-285 (in Chinese)
7. International Organization for Standardization (ISO), 1984. Pesticides and other agrochemicals - Common names. ISO 1750:1981/Draft Addendum 5, Geneva, Switzerland.
8. Jin Y.X., Chen R.J., Sun L.W., Wang W.Y., Zhou L., Liu W.P., and Fu Z.W. Enantioselective induction of estrogen-responsive gene expression by permethrin enantiomers in embryo-larval zebrafish. Chemosphere 74 (2009) 1238-1244
9. Kaufman D.D., Russell B.A., Helling C.S., and Kayser A.J. Movement of cypermethrin, decamethrin, permethrin, and their degradation products in soil. J. Agric. Food Chem. 29 (1981) 239-245
10. Koichi, A., Isamu, N., Yukio, S., Kiyoshi, K., 1979. α-cyano-3-phenoxybenzyl, 2,2,3,3-tetramethylcyclopropanecarboxylate insecticides and acaricides. Jpn. Kokai Tokyo Koho JP 7913056.
11. Lee P.W., Powell W.R., Stearns S.M., and McConnell O.J. Comparative aerobic soil metabolism of fenvalerate isomers. J. Agric. Food Chem. 35 (1987) 384-387
12. Leicht W., Fuchs R., and Londershausen M. Stability and biological activity of cyfluthrin isomers. Pestic. Sci. 48 (1996) 325-332
13. Lewis D.L., Garrison A.W., Wommack K.E., Whittemore A., Steudler P.S., and Melillo J. Influence of environmental changes on degradation of chiral pesticides in soils. Nature 401 (1999) 898-901
14. Li Z.Y., Zhang Z.C., Zhou Q.L., Gao R.Y., and 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 977 (2002) 17-25
15. Li Z.Y., Zhang Z.C., Zhou Q.L., Wang Q.S., and Gao R.Y. Stereo- and enantioselective determination of pesticides in soil by using achiral and chiral liquid chromatography in combination with matrix solid-phase dispersion. J. AOAC Int. 86 (2003) 521-528
16. Li Z.Y., Zhang Z.C., Leng L., and Zhang L. Chiral separation of pyrethroid pesticides and fenvaleric acid. Chin. J. Anal. Lab. 11 (2006) 11-14 (in Chinese)
17. Liu W.P., and Gan J.J. Separation and analysis of diastereomers and enantiomers of cypermethrin and cyfluthrin by gas chromatography. J. Agric. Food Chem. 52 (2004) 755-761
18. Liu W.P., Gan J.Y., Schlenk D., and Jury W.A. Enantioselectivity in environmental safety of current chiral insecticides. Proc. Natl. Acad. Sci. USA 102 (2005) 701-706
19. Liu W.P., Qin S.J., and Gan J.Y. Chiral stability of synthetic pyrethroid insecticides. J. Agric. Food Chem. 53 (2005) 3814-3820
20. Maguire R.J. Chemical and photochemical isomerization of deltamethrin. J. Agric. Food Chem. 38 (1990) 1613-1617
21. Monkiedje A., Zuehlke S., Maniepi S.J.N., and Spiteller M. Elimination of racemic and enantioenriched metalaxyl based fungicides under tropical conditions in the field. Chemosphere 69 (2007) 655-663
22. Müller M.D., and 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. 31 (1997) 1953-1959
23. Müller T.A., and Kohler H.-P.E. Chirality of pollutants - effects on metabolism and fate. Appl. Microbiol. Biot. 64 (2004) 300-316
24. Ohkawa H., Nambu K., Inui H., and Miyamoto J. Metabolic fate of fenvalerate (sumicidin) in soil and by soil microorganisms. J. Pestic. Sci. 3 (1978) 129-141
25. Perschke H., and Hussain M. Chemical isomerization of deltamethrin in alcohols. J. Agric. Food Chem. 40 (1992) 686-690
26. Qin S.J., and Gan J.Y. Abiotic enantiomerization of permethrin and cypermethrin: effects of organic solvents. J. Agric. Food Chem. 55 (2007) 5734-5739
27. Roberts T.R., and Standen M.E. Degradation of the pyrethroid insecticide WL41706, (±)-α-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate, in soils. Pestic. Sci. 8 (1977) 600-610
28. Robson M., and Harrad S. Chiral PCB signatures in air and soil: implications for atmospheric source apportionment. Environ. Sci. Technol. 38 (2004) 1662-1666
29. Romero E., Matallo M.B., Peňa A., Sánchez-Rasero F., Schmitt-Kopplin P., and Dios G. Dissipation of racemic mecoprop and dichlorprop and their pure R-enantiomers in three calcareous soils with and without peat addition. Environ. Pollut. 111 (2001) 209-215
30. Sakata A., Mikami N., and Yamada H. Degradation of pyrethroid optical isomers in soils. J. Pestic. Sci. 17 (1992) 169-180
31. Schulz R., and Liess M. Toxicity of fenvalerate to caddisfly larvae: chronic effects of 1-vs. 10-h pulse-exposure with constant doses. Chemosphere 41 (2000) 1511-1517
32. Vetter W., Smalling K.L., and Maruya K.A. Interpreting nonracemic ratios of chiral organochlorines using naturally contaminated fish. Environ. Sci. Technol. 35 (2001) 4444-4448