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J Agric Food Chem. 2018 Dec 19;66(50):13303-13309. doi: 10.1021/acs.jafc.8b04594. Epub 2018 Dec 6.

Stereoselective Separation of the Fungicide Bitertanol Stereoisomers by High-Performance Liquid Chromatography and Their Degradation in Cucumber.

Author information

1
Department of Pesticide Science, College of Plant Protection, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application , Nanjing Agricultural University , Nanjing 210095 , China.

Abstract

Bitertanol is a widely used triazole fungicide and consists of four stereoisomers. A new high-performance liquid chromatography (HPLC) method was developed for simultaneous analysis of the four stereoisomers in apple, pear, tomato, cucumber, and soil. The mechanism of separation was explained with molecular docking and effects of thermodynamic parameters on the resolution. The absolute configuration and optical rotation of four stereoisomers were confirmed by X-ray diffraction and HPLC tandem circular dichroism, respectively. A good linearity ( R2 ≥ 0.999) was obtained for four stereoisomers in all matrix-matched calibration curves in the range of 0.02-10 mg/L. The mean recoveries of four stereoisomers in five matrices ranged from 74.6% to 101.0% with an intraday and interday relative standard deviation from 0.6% to 9.9%. Stereoselective degradation of bitertanol in cucumber was observed: (1 R,2 S)-bitertanol and (1 R,2 R)-bitertanol were preferentially degraded with enantiomeric fraction values from 0.5 to 0.43 at 7 d and 0.42 at 5 d, respectively. This research provides a useful tool for the analysis of bitertanol stereoisomers.

KEYWORDS:

X-ray diffraction; bitertanol; chiral separation; stereoselective degradation

PMID:
30495953
DOI:
10.1021/acs.jafc.8b04594
[Indexed for MEDLINE]

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