Diastereoselective metabolism of a novel cis-nitromethylene neonicotinoid paichongding in aerobic soils.
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. (14)C-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 diastereoselective/epimer-selective persistence in all soils except an acidic clay 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 (14)C and MS may be used as an effective tool to understand the environmental processes and risks of other man-made chiral compounds.
Institute of Nuclear Agricultural Sciences, Zhejiang University , Hangzhou 310029, China.
Qiuguo
Q
Fu
Jianbo
J
Zhang
Xiaoyong
X
Xu
Haiyan
H
Wang
Wei
W
Wang
Qingfu
Q
Ye
Zhong
Z
Li
D000332:Aerobiosis; D053961:Azabicyclo Compounds / Q000737:chemistry / Q000378:metabolism*; D001673:Biodegradation, Environmental; D007306:Insecticides / Q000737:chemistry / Q000378:metabolism*; D011725:Pyridines / Q000737:chemistry / Q000378:metabolism*; D012988:Soil Microbiology; D012989:Soil Pollutants / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism
D053961:Azabicyclo Compounds; D007306:Insecticides; D011725:Pyridines; D012989:Soil Pollutants; C588015:paichongding