Chiral Herbicide Fluorochloridone: Absolute Configuration, Stereoselective Bioactivity, Toxicity, and Degradation in the Potatoes

• Published in: Journal of agricultural and food chemistry Vol. 72; no. 32; pp. 17880 - 17889
• Main Authors: Li, Wei, Zhao, Dong, Chen, Hongyu, Guo, Liangzhi, Wei, Youhai, Weng, Hua, Cheng, Liang, Zhu, Haixia, Guo, Qingyun, Shen, Shuo
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 14.08.2024
• Subjects: Agricultural and Environmental Chemistry; Animals; Herbicides - chemistry; Herbicides - pharmacology; Herbicides - toxicity; Plant Weeds - drug effects; Solanum tuberosum - chemistry; Stereoisomerism; Zebrafish; biotoxicity; HPLC−MS/MS; potatoes; stereoselective degradation; absolute configuration; fluorochloridone stereoisomers
• ISSN: 0021-8561; 1520-5118; 1520-5118
• DOI: 10.1021/acs.jafc.4c03728

Fluorochloridone (FLC) is a chiral herbicide that has four stereoisomers. This study systematically assessed the stereoselectivity of FLC to reveal the selective environmental behavior of its four isomers. Absolute configuration confirmation, evaluation of stereoselective bioactivity toward monocotyledonous and dicotyledonous weeds, toxicity to Danio rerio, and the stereoselective degradation in the potato system under field conditions of FLC were conducted. The four FLC stereoisomers were effectively separated on a superchiral S-AD column. The absolute configurations of the four stereoisomers of FLC were confirmed as (−)-(3S, 4S), (+)-(3S, 4R), (−)-(3R, 4S), and (+)-(3R, 4R)-FLC using single-crystal X-ray diffraction. The activities of the four stereoisomers were in the order of (−)-(3S, 4S)-FLC > (+)-(3R, 4R)-FLC > (+)-(3S, 4R)-FLC > (−)-(3R, 4S)-FLC, and the rate of selective degradation were in the order of (−)-(3R, 4S)-FLC > (+)-(3R, 4R)-FLC > (−)-(3S, 4R)-FLC > (+)-(3S, 4S)-FLC. The toxicity of the isomers were in the order of (−)-(3R, 4S)-FLC > (+)-(3R, 4R)-FLC > (−)-(3S, 4S)-FLC > (+)-(3S, 4R). Based on the results of bioactivity, toxicity, and degradation behavior assessments, the stereoisomer mixture containing (3R,4R)-FLC and (3S,4S)-FLC was concluded to be a better option than racemic FLC for increasing bioactivity and reducing usage.