Stereoselective bioaccumulation and dissipation of pyrisoxazole in earthworm-soil microcosm

文献类型： 外文期刊

第一作者： Cang, Tao

作者： Cang, Tao;Diao, Ziyang;Di, Shanshan;Liu, Zhenzhen;Wang, Zhiwei;Zhao, Huiyu;Xu, Hao;Qi, Peipei;Wang, Xinquan;Cang, Tao;Diao, Ziyang;Di, Shanshan;Liu, Zhenzhen;Wang, Zhiwei;Zhao, Huiyu;Xu, Hao;Qi, Peipei;Wang, Xinquan;Diao, Ziyang;Zhang, Chenghui;Qi, Peipei;Wang, Xinquan

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关键词： Pyrisoxazole stereoisomers; Absolute configuration; Earthworms; LC-Q-TOF; MS; Stereoselective bioaccumulation

期刊名称：SCIENCE OF THE TOTAL ENVIRONMENT （ 影响因子：10.753； 五年影响因子：10.237 ）

ISSN： 0048-9697

年卷期： 2022 年 852 卷

页码：

收录情况： SCI

摘要： Pyrisoxazole is a chiral fungicide with high sterilizing activity to the plant pathogenic bacteria. It has two chiral C atoms, which bring four stereoisomers. The present work was the first time to explore the stereoselective bioaccumu-lation behavior of pyrisoxazole in earthworms by chiral liquid chromatography coupled to quadrupole time-of-flight mass spectrometry (LC-Q-TOF/MS). The absolute configurations of pyrisoxazole stereoisomers were confirmed by circular dichroism (CD) coupled with calculated electronic circular dichroism (ECD) method, and the elution order in Lux Cellulose-3 column was as follows: (-)-3S, 5R-pyrisoxazole, (+)-3R, 5S-pyrisoxazole, (+)-3S, 5S- pyrisoxazole and (-)-3R, 5R-pyrisoxazole. The recoveries of pyrisoxazole stereoisomers in earthworm and soil samples ranged from 80.8 % to 101 % with the RSD lower than 6.3 %. In bioaccumulation progress, (+)-3R, 5S-pyrisoxazole was accumulated preferentially in earthworms, and the bioaccumulation concentrations of high-activity (-)-3S, 5R-pyrisoxazole were the lowest. There were no stereoselective bioaccumulation between (+)-3S, 5S-pyrisoxazole and (-)-3R, 5R-pyrisoxazole, while there was diastereoselectivity between Z-pyrisoxazole and E-pyrisoxazole with higher E-pyrisoxazole concentrations. In the whole bioaccumulation process, the BAF values of (+)-3R, 5S-pyrisoxazole were significantly higher than (-)-3S, 5R-pyrisoxazole, and the BAF values of (-)-3S, 5R-pyrisoxazole were the lowest. The dissipation of pyrisoxazole stereoisomers in the artificial soil was very slow and had no stereoselectivity, and the exis-tence of earthworms had little effects on the dissipation of pyrisoxazole stereoisomers, which indicated that the stereoselective behaviors of pyrisoxazole in earthworms were caused by the stereoselective enrichment and dissipation of earthworms themselves. Taken together, (-)-3S, 5R-pyrisoxazole was recommend as a commercial product. This

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