Non-stereoselective transformation of the chiral insecticide cycloxaprid in aerobic soil

Cycloxaprid (CYC) is one of the most effective neonicotinoid insecticides and is proposed to be a replacement of imidacloprid that has caused concerns over non-targeted resistance and ecological toxicity worldwide. The present study was performed with the ¹⁴C-labeled racemic CYC and its two enantiomers in aerobic soil. Racemic CYC and the enantiomers 1S2R-CYC and 1R2S-CYC underwent non-stereoselective degradation in the three soils tested. During the incubation period, CYC was transformed into three achiral degradation products which displayed varying degradation kinetics dependent upon soil properties. The soil properties were found to significantly influence the CYC metabolite profiles. The fastest degradation occurred in loamy soil, whereas the slowest reactions occurred in acidic clay soil. The primary transformation of CYC included cleavage of the oxabridged seven-member ring and C−N between chloropyridinylmethyl and imidazalidine ring, carboxylation of the alkene group, and hydroxylation of imidazolidine ring. The results shed light on understanding of CYC degradation and provided useful information for applications and environmental assessments of chiral pesticides. - Highlights: • Cycloxaprid degraded very quickly in aerobic soils. • Three degradation intermediates were identified by ¹⁴C labeling and LC-QTOF-MS/MS. • No stereoselective degradation was observed for cycloxaprid isomers. • We clarified soil-specific changes of CYC intermediates over time.