Novel herbicide flusulfinam: absolute configuration, enantioseparation, enantioselective bioactivity, toxicity and degradation in paddy soils
Shiling Liu, Xiaoli Li, Junqi Zhu, Liying Liang, Heng Zhang, Ying Liao, J. Li, Lian Lei, Huihua Tan, Feng Zhao
Abstract
Abstract BACKGROUND Flusulfinam, a novel chiral herbicide, effectively controls Echinochloa crusgalli and Digitaria sanguinalis in paddy fields, indicating significant potential for practical agricultural applications. However, limited information is available on flusulfinam from a chiral perspective. A comprehensive evaluation of the enantiomeric levels of flusulfinam was performed. RESULTS Two enantiomers, R‐ (+)‐ and S‐ (−)‐flusulfinam, were separately eluted using a Chiralcel OX‐RH column. The bioactivity of R ‐flusulfinam against the two was 1.4–3.1 fold that of Rac ‐flusulfinam against two weed species. R ‐flusulfinam toxicity to Danio rerio larvae and Selenastrum capricornutumwere was 0.8‐ and 3.0‐fold higher than Rac ‐flusulfinam, respectively. Degradation experiments were conducted using soil samples from four Chinese provinces. The findings indicated that S ‐flusulfinam (half‐life T 1/2 = 40.8 days) exhibits preferential degradation than R ‐flusulfinam ( T 1/2 = 46.2–57.8 days) in the soils of three provinces. Under anaerobic conditions, soil from Anhui exhibited preferential degradation of R ‐flusulfinam ( T 1/2 = 46.2 days) over S ‐flusulfinam ( T 1/2 = 63 days). Furthermore, two hydrolysis products of flusulfinam (M299 and M100) are proposed for the first time. CONCLUSION The enantioselective bioactivity, toxicity and degradation of flusulfinam were investigated. Our findings indicate that R ‐flusulfinam is an extremely effective and low‐toxicity enantiomer for the tested species. The soil degradation test indicated that the degradation of flusulfinam was accelerated by higher organic matter content and lower soil pH. Furthermore, microbial communities may play a crucial role in driving the enantioselective degradation processes. This study lays the groundwork for the systematic evaluation of flusulfinam from an enantiomeric perspective. © 2024 Society of Chemical Industry.