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

被引:40
作者
Gao, Yingying [1 ]
Zhao, Xuejun [1 ]
Sun, Xiaofang [1 ]
Wang, Zhen [1 ]
Zhang, Jing [1 ]
Li, Lianshan [1 ]
Shi, Haiyan [1 ]
Wang, Minghua [1 ]
机构
[1] Nanjing Agr Univ, Coll Plant Protect, State & Local Joint Engn Res Ctr Green Pesticide, Dept Pesticide Sci, Nanjing 210095, Peoples R China
关键词
oxathiapiprolin; enantioselective; absolute configuration; bioactivity; degradation; PERFORMANCE LIQUID-CHROMATOGRAPHY; ENVIRONMENTAL BEHAVIOR; RESIDUE ANALYSIS; RISK-ASSESSMENT; MODIFIED QUICK; SAFE METHOD; METABOLITES; VEGETABLES; DISSIPATION; ENANTIOMERS;
D O I
10.1021/acs.jafc.0c04163
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
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 degrees 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 bioactivity and reduce the pesticide residues at a lower application rate.
引用
收藏
页码:3289 / 3297
页数:9
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