Characterization of Diastereo- and Enantioselectivity in Degradation of Synthetic Pyrethroids in Soils

Permethrin (PM), cypermethrin (CP), and cyfluthrin (CF) are three important synthetic pyrethroids, which contain two, four, and four enantiomeric pairs (diastereomers) and thus have four, eight, and eight stereoisomers, respectively. In this study, the stereo‐ and enantioselective degradation of PM,...

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Published in:Chirality (New York, N.Y.) N.Y.), 2016-01, Vol.28 (1), p.72-77
Main Authors: Li, Shaotong, Li, Zhaoyang, Li, Qiaoling, Zhao, Jiahe, Li, Sen
Format: Article
Language:English
Subjects:
Biodegradation, Environmental
Chirality
Chromatography, High Pressure Liquid
cyfluthrin
cypermethrin
Degradation
diastereomer
Dissipation
enantiomer
Enantiomers
enantioselective degradation
High performance liquid chromatography
Insecticides - chemistry
Molecular Structure
Nitriles - chemistry
permethrin
Pyrethrins - chemistry
Selectivity
Soil - chemistry
Soils
Stereoisomerism
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Summary:Permethrin (PM), cypermethrin (CP), and cyfluthrin (CF) are three important synthetic pyrethroids, which contain two, four, and four enantiomeric pairs (diastereomers) and thus have four, eight, and eight stereoisomers, respectively. In this study, the stereo‐ and enantioselective degradation of PM, CP, and CF in a Shijiazhuang alkaline yellow soil and a Wuhan acidic red soil were studied in detail by a combination of achiral and chiral high‐performance liquid chromatography (HPLC). The results showed that PM, CP, and CF degraded faster in Shijiazhuang soil than in Wuhan soil, and the dissipation rate followed an order of PM > CF > CP in both soils. The three pyrethroids exhibited similar diastereomer selectivity, while CP and CF showed higher enantioselectivity than PM. Moreover, the trans‐diastereomers degraded faster, and showed higher enantioselectivity than the corresponding cis‐diastereomers. For PM, the enantiomer 1S‐trans‐PM degraded most rapidly in both soils. As for CP and CF, the highest enantioselectivity was observed for diastereomer trans‐3, and the insecticidally active enantiomer 1R‐trans‐αS degraded fastest among the 8 CP or CF stereoisomers in both soils. In addition, the Wuhan acidic soil displayed higher diastereomer and enantiomer selectivity than the Shijiazhuang alkaline soil for the three pyrethroids. Further incubation of CF in an alkaline‐treated Wuhan soil showed that the dissipation rate greatly increased and the diastereo‐ and enantioselectivity significantly decreased after the alkaline treatment process. Chirality 28:72–77, 2016. © 2015 Wiley Periodicals, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.22544