Stereoselective degradation behavior of the novel chiral antifungal agrochemical penthiopyrad in soil

Penthiopyrad is a chiral carboxamide fungicide with a broad spectrum of fungicidal activity. However, there is no report on the analysis of the enantiomers of penthiopyrad and their environmental behavior. Soil is an important carrier for pesticides to affect the environment. Therefore, this study aimed to investigate the absolute configuration, stereoselective degradation, configuration stability and potential metabolites of this agrochemical in soil under different laboratory conditions. R-(-)-penthiopyrad and S-(+)-penthiopyrad were identified by the electronic circular dichroism method. Regarding the racemic analyte, the degradation half-lives of the stereoisomers ranged from 38.9 to 97.6 days, the S-(+)-stereoisomer degraded preferentially in four types of Chinese soil. However, enantiopure R-(-)-penthiopyrad degraded faster than its antipode, a finding that might be related to the microbial activity in soil. The organic matter (OM) content influenced the stereoselective degradation of rac-penthiopyrad. No configuration conversion was observed in both enantiopure analyte degradation processes. One possible metabolite, 753-A-OH, was detected in the treated soil samples, and the degradation pathway might be a hydroxylation reaction. This is the first report of the absolute configuration of penthiopyrad stereoisomers and the first comprehensive evaluation of the stereoselective degradation of penthiopyrad in Chinese soil. Stereoselective degradation of rac-penthiopyrad was observed in the four types of soil. And the stereoselectivity might be inhibited by OM. This study provides more accurate data to investigate the environmental behavior of penthiopyrad at the stereoisomer level.