文献类型：期刊文献

英文题名：Diastereoselective Metabolism of a Novel Cis-Nitromethylene Neonicotinoid Paichongding in Aerobic Soils

作者：Fu, Qiuguo[1];Zhang, Jianbo[1];Xu, Xiaoyong[2];Wang, Haiyan[1];Wang, Wei[1];Ye, Qingfu[1];Li, Zhong[2]

机构：[1]Zhejiang Univ, Inst Nucl Agr Sci, Hangzhou 310029, Zhejiang, Peoples R China;[2]E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China

年份：2013

卷号：47

期号：18

起止页码：10389

外文期刊名：ENVIRONMENTAL SCIENCE & TECHNOLOGY

收录：;EI(收录号：20133916772105);WOS:【SCI-EXPANDED(收录号:WOS:000330096000040)】；

基金：This research was financially supported by the National Natural Science Foundation of China (No. 11175155), National High Technology Research and Development Program of China (863 Program, No. 2013AA065202), and Chinese Ministry of Agriculture Foundation (No. 201103007).

语种：英文

外文关键词：Nitrogen removal - Stereoselectivity

摘要：Many pesticides are chiral but used as racemic mixtures, even though their stereoisomers are often degraded stereoselectively in soils. Evaluation of degradation of chiral compounds is mostly focused on the enantioselectivity rather than diastereoselectivity/epimer preferences. In this study, we explored the diastereoselective transformation of paichongding (IPP), a novel chiral neonicotinoid with broad-spectrum insecticidal activity, to several degradation intermediates in different soils. RC-Labeling coupled with LC-MS/MS and high resolution MS were used to track residues of IPP and identify major transformation metabolites. The stereoisomers of IPP known as 5R, 7R-IPP (RR-IPP), 5S, 7S-IPP (SS-IPP), 5S, 7R-IPP (SR-IPP), and 5R, 7S-IPP (RS-IPP) showed diastereoselec-tive/epimer-selective persistence in all soils except an acidic day soil. Moreover, IPP was transformed to a range of degradation intermediates (M1-M6), which also showed significant diastereoselective and soil preferential formation. Depropylation, nitrosylation, denitration, demethylation, dehydroxylation, and ketonization contributed to IPP transformation. The diastereoselective degradation of the parent compound and formation of incomplete intermediates implies that diastereomers/epimers should be regarded as different chemicals. The approach of coupling C-14 and MS may be used as an effective tool to understand the environmental processes and risks of other man-made chiral compounds.