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Herbicidal activity and differential metabolism of lactofen in rat and loach on an enantiomeric level

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Abstract

Enantioselectivity of chiral compounds is receiving growing concern. Lactofen, a chiral herbicide widely used in field crops and vegetables to control broadleaf weeds, is still sold as racemate. In this work, the herbicidal activity and metabolism behavior of lactofen were investigated on an enantiomeric level. Two common broadleaf weeds (Eclipta prostrata L. and Portulaca oleracea L.) were used to evaluate the herbicidal activity of rac-/R- and S-lactofen, and their metabolism behavior in loach and rat liver microsomes was explored. Higher herbicidal activity of S-lactofen was observed, with the 20d-EC50 values being 1.9–3.4 times lower than R-lactofen. Both loach and rat liver microsomes had ability to metabolize rac-lactofen, with half-lives of 1.93 and 1.28 h, respectively. Enantioselective metabolism behaviors were observed in loach and rat liver microsomes and the direction of enantioselectivity were different. R-lactofen was preferentially metabolized in loach liver microsome, while S-lactofen was preferentially metabolized in rat liver microsome. No interconversion of R- and S-lactofen was found. Besides, the main metabolic pathways of R- and S-lactofen were found to be significantly different. R-lactofen was metabolized to R-desethyl lactofen in both loach and rat liver microsomes without further metabolism. However, S-lactofen was metabolized to both S-desethyl lactofen and acifluorfene in rat liver microsome, which was mainly metabolized to acifluorfene in loach liver microsome. This study indicated enantioselectivity and metabolites should be taken into consideration when overall evaluating the environmental behavior of lactofen.

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All data generated or analyzed during this study are included in this published article.

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Funding

This work was supported by the Research Foundation for Youth Scholars of Beijing Technology and Business University (QNJJ2021-27).

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Authors and Affiliations

  1. State Environmental Protection Key Laboratory of Food Chain Pollution Control, Beijing Technology and Business University, Beijing, 100048, People’s Republic of China

    Fang Wang, Shanxue Jiang & Zhiliang Yao

  2. School of Ecology and Environment, Beijing Technology and Business University, Beijing, 100048, People’s Republic of China

    Fang Wang, Shanxue Jiang & Zhiliang Yao

  3. Beijing Advanced Innovation Centre for Food Nutrition and Human Health. Department of Applied Chemistry, China Agricultural University, Beijing, 100193, People’s Republic of China

    Fang Wang, Jing Gao & Peize Li

  4. School of Environment, Tsinghua University, Beijing, 100084, People’s Republic of China

    Jing Gao

  5. Institute of Plant and Environmental Protection, Beijing Academy of Agriculture and Forestry Science, Beijing, 100097, People’s Republic of China

    Junxue Wu

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  1. Fang Wang
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Contributions

Conceptualization: FW; methodology: FW, JG, and PL; writing—original draft preparation: FW; writing—review and editing: FW, SJ, and ZY; funding acquisition: FW; supervision: JW and ZY. All authors read and approved the final manuscript.

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Correspondence to Zhiliang Yao.

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Wang, F., Gao, J., Li, P. et al. Herbicidal activity and differential metabolism of lactofen in rat and loach on an enantiomeric level. Environ Sci Pollut Res 29, 28307–28316 (2022). https://doi.org/10.1007/s11356-021-17986-2

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