Enantioselective degradation and transformation of the chiral fungicide prothioconazole and its chiral metabolite in soils.

Prothioconazole is a widely used chiral triazole fungicide. In this work, the enantioselective degradation and transformation of prothioconazole and its chiral metabolite prothioconazole-desthio in five kinds of soils were investigated under native and sterile conditions using reversed phase liquid chromatography tandem mass spectrometry with a Lux-cellulose-1 column. The results showed that an enantioselective degradation was observed with R-prothioconazole preferentially degraded in the five soils and enantiomeric fraction values that ranged from 0.32 to 0.41 under native conditions. Furthermore, the major metabolite prothioconazole-desthio was formed rapidly during prothioconazole dissipation. The prothioconazole-desthio enantiomers were degraded slowly, and there was a slight enantioselectivity with enantiomeric fraction values that ranged from 0.45 to 0.51 in the Nanjing and Jilin soils. Under sterile conditions, prothioconazole and its metabolite enantiomers were more slowly degraded with no enantioselectivity. The result of the incubation experiment with single enantiomers verified that R- and S-prothioconazole were transformed to R- and S-prothioconazole-desthio, respectively. No enantiomerization for prothioconazole and its chiral metabolite was observed. In addition, the excellent correlation between organic matter content and degradation rate indicated that organic matter could promote the degradation of prothioconazole and its metabolite enantiomers. The data in this study provide the experimental evidence of the stereoselective degradation and metabolism of both prothioconazole and its chiral metabolite in the environment.