Chiral Separation and Enantioselective Degradation of Vinclozolin in Soils

Abstract

Vinclozolin is a chiral fungicide with potential environmental problems. The chiral separation of the enantiomers and enantioselective degradation in soil were investigated in this work. The enantiomers were separated by high-performance liquid chromatography (HPLC) on Chiralpak IA, IB, and AZ-H chiral columns under normal phase and the influence of the mobile phase composition on the separation was also studied. Complete resolutions were obtained on all three chiral columns under optimized conditions with the same elution order of (+)/(-). The residual analysis of the enantiomers in soil was conducted using accelerate solvent extraction followed by HPLC determination. The recoveries of the enantiomers ranged from 85.7-105.7% with relative standard deviation (SD) of 0.12-3.83%, and the limit of detection (LOD) of the method was 0.013 µg/g. The results showed that the degradations of vinclozolin enantiomers in the soils followed first-order kinetics. Preferential degradation of the (-)-enantiomer was observed only in one soil with the largest |ES| value of 0.047, and no obvious enantioselective degradation was observed in other soils. It was found that the persistence of vinclozolin in soil was related to pH values based on the half-lives. The two enantiomers disappeared about 8 times faster in basic soils than that in neutral or acidic soils.

State-of-the-art and recent developments of immobilized polysaccharide-based chiral stationary phases for enantioseparations by high-performance liquid chromatography (2013–2017)

“…Many papers are aimed to the determination of herbicides [103,104,108,110], insecticides [48,100,97,107,105], fungicides [102,109,106,101,99] or antiviral drugs [98] from many different chemical families, including aryloxyphenoxy propionic acids, pyridines, oxadiazines, phenylpyrazoles, acylalanines, pyrethroids, triazoles, α-aminophosphonates, sulfoxides, etc. have been determinated in environmental or food samples (soil, natural waters, fruits, vegetables, etc.).…”

Enantioselective dissipation of pyriproxyfen in soils and sand

“…Many factors such as soil properties (e.g., pH, clay, and organic carbon), moisture content, mixed use of pesticides, and application times play important roles in pesticide degradation in soil. In our previous study, we found that the degradation rate of pesticides varied in soils with different properties . What's more, the degradation of pesticides with the effect of moisture content was discussed .…”

“…In our previous study, we found that the degradation rate of pesticides varied in soils with different properties. 1 What's more, the degradation of pesticides with the effect of moisture content was discussed. [2][3][4] It is widely recognized that complex interactions also occur between pesticides in mixtures and soils.…”

Direct chiral separations of the enantiomers of phenylpyrazole pesticides and the metabolites by HPLC

“…[19][20][21] In this work, the chiral separations of the enantiomers of three phenylpyrazole pesticides (fipronil, flufiprole, ethiprole) and two fipronil metabolites were studied by CHIRALPAK ® IB chiral column on HPLC. It has been reported that the chiral separations of the enantiomers of vinclozolin, betaxolol, metoprolol, bisoprolol, and bevantolol hydrochloride on CHIRALPAK ® IB have been done by HPLC.…”

“…It has been reported that the chiral separations of the enantiomers of vinclozolin, betaxolol, metoprolol, bisoprolol, and bevantolol hydrochloride on CHIRALPAK ® IB have been done by HPLC. [19][20][21] In this work, the chiral separations of the enantiomers of three phenylpyrazole pesticides (fipronil, flufiprole, ethiprole) and two fipronil metabolites were studied by CHIRALPAK ® IB chiral column on HPLC. The influencing factors such as the mobile phase composition and column temperature on the chiral separations were studied.…”