Stereoselective bioaccumulation and dissipation of pyrisoxazole in earthworm-soil microcosm

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

doi:10.1016/j.scitotenv.2022.158472

Stereoselective bioaccumulation and dissipation of pyrisoxazole in earthworm-soil microcosm

Sci Total Environ. 2022 Dec 15:852:158472. doi: 10.1016/j.scitotenv.2022.158472. Epub 2022 Sep 6.

Authors

Tao Cang¹, Ziyang Diao², Shanshan Di¹, Zhenzhen Liu¹, Zhiwei Wang¹, Huiyu Zhao¹, Hao Xu¹, Chenghui Zhang³, Peipei Qi⁴, Xinquan Wang⁵

Affiliations

¹ State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products, Key Laboratory of Detection for Pesticide Residues and Control of Zhejiang, Institute of Quality and Standard of Agro-products, Zhejiang Academy of Agricultural Sciences, Hangzhou 310021, PR China; Agricultural Ministry Key Laboratory for Pesticide Residue Detection, Hangzhou 310021, PR China.
² State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products, Key Laboratory of Detection for Pesticide Residues and Control of Zhejiang, Institute of Quality and Standard of Agro-products, Zhejiang Academy of Agricultural Sciences, Hangzhou 310021, PR China; Agricultural Ministry Key Laboratory for Pesticide Residue Detection, Hangzhou 310021, PR China; College of Food Science & Engineering, Hainan University, No. 158 Renmin Avenue, Haikou, 570100, PR China.
³ College of Food Science & Engineering, Hainan University, No. 158 Renmin Avenue, Haikou, 570100, PR China.
⁴ State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products, Key Laboratory of Detection for Pesticide Residues and Control of Zhejiang, Institute of Quality and Standard of Agro-products, Zhejiang Academy of Agricultural Sciences, Hangzhou 310021, PR China; Agricultural Ministry Key Laboratory for Pesticide Residue Detection, Hangzhou 310021, PR China. Electronic address: qipeipei@zaas.ac.cn.
⁵ State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products, Key Laboratory of Detection for Pesticide Residues and Control of Zhejiang, Institute of Quality and Standard of Agro-products, Zhejiang Academy of Agricultural Sciences, Hangzhou 310021, PR China; Agricultural Ministry Key Laboratory for Pesticide Residue Detection, Hangzhou 310021, PR China. Electronic address: wangxinquan212@163.com.

PMID: 36075432
DOI: 10.1016/j.scitotenv.2022.158472

Abstract

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 bioaccumulation 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 existence 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 study played a positive role in guiding the development of environmentally friendly pesticides and provided database for the environmental and biological risk assessment of pyrisoxazole.

Keywords: Absolute configuration; Earthworms; LC-Q-TOF/MS; Pyrisoxazole stereoisomers; Stereoselective bioaccumulation.

MeSH terms

Animals
Bioaccumulation
Cellulose
Fungicides, Industrial* / analysis
Oligochaeta*
Pesticides* / analysis
Soil / chemistry
Stereoisomerism

Substances

Soil
Fungicides, Industrial
Pesticides
Cellulose