Systematic Stereoselectivity Evaluations of Tetramethrin Enantiomers: Stereoselective Cytotoxicity, Metabolism, and Environmental Fate in Earthworms, Soils, Vegetables, and Fruits

Abstract

Tetramethrin is a widely applied type I chiral pyrethroid insecticide that exists as a mixture of four isomers. In the present study, its stereoselective cytotoxicity, bioaccumulation, degradation, and metabolism were investigated for the first time at the enantiomeric level in detail by using a sensitive chiral high-performance liquid chromatography−tandem mass spectroscopy (HPLC-MS/MS) method. Results showed that among rac-tetramethrin and its four enantiomers, the trans (+)-1R,3R-tetramethrin had the strongest inhibition effect on the PC12 cells. In the earthworm exposure trial, the concentration of trans (−)-1S,3Stetramethrin was 0.94−8.92 times in earthworms (cultivated in natural soil) and 1.67−5.01 times (cultivated in artificial soil) higher than trans (+)-1R,3R-tetramethrin, respectively. In the greenhouse experiment, the trans (+)-1R,3R-tetramethrin and cis (+)-1R,3Stetramethrin were preferentially degraded. Furthermore, for rat liver microsome in vitro incubation, the maximum metabolism rate of cis (−)-1S,3R-tetramethrin was 1.50 times higher than its antipodes. Altogether, the aim of this study was to provide a scientific and reasonable reference for the possibility of developing a single enantiomer to replace the application of rac-tetramethrin, which could possess better bioactivity and lower ecotoxicity, and thus permit more reliable and accurate environmental monitoring and risk assessment.