Journal of Agricultural and Food Chemistry, volume 69, issue 11, pages 3289-3297

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

Publication typeJournal Article
Publication date2021-03-12
scimago Q1
SJR1.114
CiteScore9.9
Impact factor5.7
ISSN00218561, 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.
Found 
Found 

Top-30

Journals

2
4
6
8
10
12
14
2
4
6
8
10
12
14

Publishers

2
4
6
8
10
12
14
16
2
4
6
8
10
12
14
16
  • We do not take into account publications without a DOI.
  • Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
  • Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.
Share
Cite this
GOST | RIS | BibTex | MLA
Found error?