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Stereo and Enantioselective Degradation of β-Cypermethrin and β-Cyfluthrin in Soil

Abstract

β-Cypermethrin (β-CP) and β-Cyfluthrin (β-CF) are two important pyrethroid insecticides and both consist of two enantiomeric pairs (diastereomers), i.e. four enantiomers. In this study, the stereo and enantioselective degradation of β-CP and β-CF in a Tianjin alkaline soil was studied in details by a combination of achiral and chiral HPLC. The results showed that for the two pyrethroids, the transdiastereomer was degraded faster than the corresponding cis-diastereomer. β-CP and β-CF were found to be configurationally unstable in this soil, since isomerization between diastereomers was observed during the degradation process. Further enantioselective analysis showed that significant enantioselectivity occurred during the 30 days incubation time. The enantiomeric ratio (ER) values of cis- and transdiastereomers changed from initial ≈1.00 to final 0.79 and 0.55 for β-CP, and to 0.64 and 0.48 for β-CF, respectively. At last, it was found that β-CF was degraded at relatively faster degradation rate and higher enantioselectivity than β-CP. Findings from this study may be used to better understand the chiral profiles of β-CP and β-CF as well as relevant pyrethroid analogues in environment.

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Acknowledgements

This work was supported by National Natural Science Foundation of China (No. 29907002 and 20707005).

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Correspondence to Z. Y. Li.

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Li, Z.Y., Zhang, Z.C., Zhang, L. et al. Stereo and Enantioselective Degradation of β-Cypermethrin and β-Cyfluthrin in Soil. Bull Environ Contam Toxicol 80, 335–339 (2008). https://doi.org/10.1007/s00128-008-9368-y

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Keywords

  • β-Cypermethrin
  • β-Cyfluthrin
  • Stereo and enantioselective degradation
  • Isomerization
  • Enantiomeric ratio