Study on stereoselective bioactivity, acute toxicity, and degradation in cucurbits and soil of chiral fungicide famoxadone.

Abstract

The chiral pesticide famoxadone is mainly applied to control fungal diseases on fruiting vegetables. The fungicidal activity, ecotoxicological effects, and degradation behavior of famoxadone enantiomers are less well known. In this study, a systemic assessment of the stereoselectivity of famoxadone was performed in cucurbits and soil. Famoxadone enantiomers presented distinct inhibitory activities among different fungal species. The bioactivities of R-(-)-famoxadone were 2.7-178 times higher than S-(+)-famoxadone toward five phytopathogens. Based on the obtained LC50 values, famoxadone was super toxic to Eisenia foetida (E. foetida). Moreover, the acute toxicity of R-(-)-famoxadone presented 167 times greater to E. foetida than that of S-(+)-famoxadone, indicating that R-(-)-famoxadone showed higher bioactivity toward target organisms and non-target organisms than S-(+)-famoxadone. In addition, a simple high-performance liquid chromatography (HPLC) method was established to determine the stereoselective degradation of famoxadone in two species of cucurbits (cucumber and chieh-qua) and in field soil. The half-life values of famoxadone degradation were from 5.4 to 14.1days, indicating that famoxadone was easily degraded. Additionally, no stereoselective degradation was found in cucurbits and soil. The results may provide promising implications for comprehensive environmental and ecological risk assessments of famoxadone.