Enantioselective bioactivity, toxicity, and degradation in different environmental mediums of chiral fungicide epoxiconazole

Abstract

To clarify the environmental behaviour and bioactivity of epoxiconazole enantiomers, an integrated assessment has been done. The degradation in soil, water, and river-sediments were studied. The toxicity to Chlorella vulgaris and Daphnia magna was also examined. The bioactivity to plant-pathogens and molecular docking to CYP51 were investigated. The obtained results showed that the half-lives of R,S-(+)- and S,R-(-)-epoxiconazole were 38.8 and 21.2 days in Jiangsu soil, 43.2 and 22.7 days in Jiangxi soil, 29.1 and 21.3 days in Jilin soil, 43.5 and 32.7 days in anaerobic Jilin soil, 12.3 and 10.1 days in river sediments, and 33.2 and 9.3 days in river water, respectively. Maximum EF was 0.36 in Yangzi-river water. No enantioselective degradation was found in sterilized conditions. The EC50 to C. vulgaris after 48 h was 27.78 mg L−1, and 18.93 mg L−1 for R,S-(+)-, and S,R-(-)-epoxiconazole, respectively. The LC50 to D. magna was 4.16 mg L−1, and 8.49 mg L-1 for R,S-(+)-, and S,R-(-)-epoxiconazole, respectively. R,S-(+)-epoxiconazole bioactivity was 1.3–7.25 times higher than S,R-(-)-epoxiconazole. In conclusion, R,S-(+)- has higher bioactivity and higher environmental toxicity. In opposite, S,R-(-)- has lower environmental toxicity and lower bioactivity. R,S-(+)-epoxiconazole use is recommended with lower concentrations, which is appropriate for environment safety.