Journal of Agricultural and Food Chemistry, volume 69, issue 11, pages 3289-3297
Enantioselective Detection, Bioactivity, and Degradation of the Novel Chiral Fungicide Oxathiapiprolin
Yingying Gao
1
,
Xuejun Zhao
1
,
Xiaofang Sun
1
,
Zhen Wang
1
,
Jing Zhang
1
,
Lianshan Li
1
,
Haiyan Shi
1
,
Minghua Wang
1
Publication type: Journal Article
Publication date: 2021-03-12
scimago Q1
SJR: 1.114
CiteScore: 9.9
Impact factor: 5.7
ISSN: 00218561, 15205118
General Chemistry
General Agricultural and Biological Sciences
Abstract
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 bioactivity and reduce the pesticide residues at a lower application rate.
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