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

作者：Yingying Gao, Xuejun Zhao, Xiaofang Sun, Zhen Wang, Jing Zhang, Lianshan Li, Haiyan Shi, Minghua Wang · 发表于：Journal of Agricultural and Food Chemistry · 年份：2021 · DOI：10.1021/acs.jafc.0c04163 · 被引用次数：45 · 研究领域：Pesticide Residue Analysis and Safety、Fungal Plant Pathogen Control、Analytical Chemistry and Chromatography

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