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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.

期刊论文 2024-09-01 DOI: 10.1016/j.cbpc.2024.109941 ISSN: 1532-0456

Continued application of new chiral fungicide mefentrifluconazole (MFZ) increases its risk to soil ecosystem. However, the toxicity of MFZ enantiomers to soil fauna and whether stereoselectivity exists remains poorly elucidated. Based on multilevel toxicity endpoints and transcriptomics, we investigated the negative effects of racemic, R-(-)-, and S-(+)-MFZ on Eisenia fetida. After exposure to S-(+) configuration at 4 mg/kg for 28 day, its reactive oxygen species levels were elevated by 15.4% compared to R-(-) configuration, inducing enantiospecific oxidative stress and transcriptional aberrations. The S-(+) isomer induced more severe cell membrane damage and apoptosis than the R-(-) isomer, and notably, the selectivity of apoptosis is probably dominated by the mitochondrial pathway. Mechanistically, differential mitochondrial stress lies in: S-(+) isomer specifically upregulated mitochondrial cellular component compared to R-(-) isomer and identified more serious mitochondrial fission. Furthermore, S-(+) conformation down -regulated biological processes associated with ATP synthesis and metabolism, with specific inhibition of mitochondrial respiratory electron transport chain complex I and IV activity resulting in more severe electron flow disturbances. These ultimately mediated enantioselective ontogenetic process disorders, which were supported at phenotypic (weight loss), genetic, and protein (reverse modulate TCTP and Sox2 expression) levels. Our findings offer an important reference for elucidating the enantioselective toxicological mechanism of MFZ in soil fauna.

期刊论文 2024-03-15 DOI: 10.1016/j.jhazmat.2024.133585 ISSN: 0304-3894
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