Enantioselective Detection, Bioactivity, and Degradation of the Novel Chiral Fungicide Oxathiapiprolin

• DOI: 10.1021/acs.jafc.0c04163
• Publication Date: 2021-03-12T20:31:54Z
• Authors: Yingying Gao; Xuejun Zhao; Xiaofang Sun; Zhen Wang; Jing Zhang; Lianshan Li; Haiyan Shi; Minghua Wang
• Keywords: Molecular Docking Simulation; Hydrocarbons, Fluorinated; Tandem Mass Spectrometry; Pyrazoles; Soil Pollutants; Stereoisomerism; 01 natural sciences; Chromatography, High Pressure Liquid; Fungicides, Industrial; 0104 chemical sciences

Oxathiapiprolin is a novel chiral piperidine thiazole isooxazoline fungicide that contains pair of enantiomers. An effective analytical method was established for the enantioselective detection oxathiapiprolin in fruit, vegetable, and soil samples using ultraperformance liquid chromatography-tandem triple quadrupole mass spectrometry. The optimal enantioseparation achieved on Chiralpak IG column at 35 °C acetonitrile 0.1% formic acid aqueous solution (90:10, v/v) as mobile phase. absolute configuration enantiomers identified with elution order R-(−)-oxathiapiprolin S-(+)-oxathiapiprolin by electron circular dichroism spectra. bioactivity 2.49 to 13.30-fold higher than against six kinds oomycetes. molecular docking result illuminated mechanism enantioselectivity bioactivity. glide score (−8.00 kcal/mol) R-enantiomer better binding site Phytophthora capsici S-enantiomer (−7.50 kcal/mol). Enantioselective degradation tomato pepper under field condition investigated indicated preferentially degraded. present study determines about detection, bioactivity, first time. will be choice racemic enhance reduce pesticide residues lower application rate.