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

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RESEARCH ARTICLE

Study on stereoselective bioactivity, acute toxicity, and degradation in cucurbits and soil of chiral fungicide famoxadone Meng Wang 1,2 & Zerong Ji 1 & Jiabin Xu 1 & Chenghui Zhang 2,3 & Ye Yang 1 & Xiaoyu Liang 1,2

&

Yu Zhang 1,2

Received: 23 July 2020 / Accepted: 23 November 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020

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 14.1 days, 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. Keywords Famoxadone . Stereoselectivity . Bioactivity . Acute toxicity . Degradation

Introduction The number of chiral pesticides increased rapidly with the development of environmentally friendly pesticides in the past few decades (Garrison 2006; Liu et al. 2005). About 30% of the active ingredients in currently registered pesticides contain chiral structure (Zhou et al. 2009). The enantiomers of chiral pesticides with identical physicochemical properties display

Responsible Editor: Zhihong Xu * Xiaoyu Liang [email protected] * Yu Zhang [email protected] 1

College of Plant Protection, Hainan University, Haikou 570228, China

2

Laboratory of Quality and Safety Risk Assessment for Agro-products (Haikou), Ministry of Agriculture, Haikou, China

3

College of Food science and Engineering, Hainan University, Haikou 570228, China

different environmental fates, bioassay activities, and toxicities (Ye et al. 2010; Zhou et al. 2010). So the chiral pesticides may contain both low- and high-toxic enantiomers, with the latter being harmful to non-target organisms (Zhang et al. 2012). The stereoselective characteristics of these pesticides should be determined for accurate risk assessment and application of the regulation