RESUMO
The chiral fungicide prothioconazole (PTZ) is extensively employed in agricultural practices, prompting serious concern due to its environmental impact. PTZ is prone to undergo metabolism, leading to the formation of chiral prothioconazole-desthio (dPTZ) in the environment. However, limited knowledge exists regarding its enantioselective behavior and toxicity towards invertebrate organisms in soil ecosystems. In this study, R-(-)- and S-(+)- PTZ enantiomers were individually synthesized, and their stereoselective toxicity effects on earthworms (E. foetida) were studied in artificial soil under environmentally relevant concentration exposures. The results showed a significant accumulation of dPTZ in earthworms, surpassing the levels of PTZ. Moreover, the concentration of S-(-)- dPTZ in earthworms was notably higher than that of R-(+)- dPTZ after exposure, reaching peak levels on day 14. Concurrently, oxidative stress induced by S-(+)- PTZ enantiomers in earthworms exhibited a substantial increase compared to R-(-)- enantiomers on day 14, indicating a higher ecological risk associated with the former in non-target organisms. Transcriptome analysis unveiled distinct impacts on earthworm physiology. S-(+)-PTZ exposure significantly affected energy metabolism, immune responses and digestive systems. In contrast, R-(-)-PTZ exposure influenced the synthesis of carbohydrates, proteins, and lipids. These insights contribute to understanding the complex interactions between PTZ enantiomers and soil-dwelling organisms, providing a scientific foundation for advancing the application of high efficiency, low toxicity PTZ monomer pesticides.