氟氯酮(FLC)是具有四种立体异构体的手性除草剂。本研究系统地评估了FLC的立体选择性,以揭示其四种异构体的选择性环境行为。绝对配置确认,对单子叶和双子叶杂草的立体选择性生物活性的评估,对Daniorerio的毒性,并在FLC的田间条件下进行了马铃薯系统的立体选择性降解。四种FLC立体异构体在超手性S-AD柱上有效分离。FLC的四种立体异构体的绝对构型被证实为(-)-(3S,4S),(+)-(3S,4R),(-)-(3R,4S),和(+)-(3R,4R)-FLC使用单晶X射线衍射。四种立体异构体的活性顺序为(-)-(3S,4S)-FLC>(+)-(3R,4R)-FLC>(+)-(3S,4R)-FLC>(-)-(3R,4S)-FLC,选择性降解速率依次为(-)-(3R,4S)-FLC>(+)-(3R,4R)-FLC>(-)-(3S,4R)-FLC>(+)-(3S,4S)-FLC。异构体的毒性顺序为(-)-(3R,4S)-FLC>(+)-(3R,4R)-FLC>(-)-(3S,4S)-FLC>(+)-(3S,4R)。根据生物活性的结果,毒性,和退化行为评估,含有(3R,4R)-FLC和(3S,4S)-FLC被认为是比外消旋FLC更好的选择,可以提高生物活性并减少使用量。
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.