Chiral Fungicide Famoxadone: Stereoselective Bioactivity, Aquatic Toxicity, and Environmental Behavior in Soils.

Abstract

In this study, the stereoselective bioactivity, acute toxicity, and environmental fate for famoxadone enantiomers were reported for the first time. Five representative pathogens (e.g., Alternaria solani) were used to investigate enantioselective activity, and three non-target organisms (e.g., Selenastrum bibraianum) were used to evaluate acute toxicity. S-Famoxadone was 3.00-6.59 times more effective than R-famoxadone. R-Famoxadone also showed 1.80-6.40 times more toxicity than S-famoxadone toward S. bibraianum and Daphnia magna. The toxicity of R-famoxadone was 100 times more toxic than S-famoxadone toward Danio rerio. Under aerobic conditions, the half-life (t1/2) for famoxadone enantiomer degradation was 46.2-126 days in different soils and the enantiomeric fraction (EF) ranged from 0.435 to 0.470 after 120 days. R-Famoxadone preferentially degraded in three soils, resulting in an enrichment of S-famoxadone. Under anaerobic conditions, t1/2 of famoxadone enantiomers was 62.4-147 days in different soils and the EF ranged from 0.489 to 0.495, indicating that famoxadone enantiomers were not enantioselective. This study will be useful for the environmental and health risk assessments for famoxadone enantiomers.