Zhang Yanqing, Zhou Liangliang, Li Rui, Li Yanhong, Tan Yuting, Shi Haiyan, Wang Minghua
Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Nanjing 210095, China.
J Agric Food Chem. 2023 Mar 29;71(12):4810-4816. doi: 10.1021/acs.jafc.3c00223. Epub 2023 Mar 15.
Flurtamone is a typical chiral pesticide with a pair of enantiomers. In this study, the enantioselective biological effects of flurtamone enantiomers were systematically investigated. The bioactivities of -flurtamone were 6.3-35.6 and 1.7-9.9 times higher than - and ac-flurtamone, respectively. The contribution of the -enantiomer to herbicidal activity was 86.3-97.3%. The carotenoid content in the -flurtamone treatment group was 1.31-2.14 times lower than that in the -flurtamone treatment group. Molecular docking found that flurtamone can form aromatic H-bonds with phenylalanine (PHE) 233 of phytoene desaturase (PDS), while -flurtamone can form π-π stacking with PHE 202 and PHE 311. The binding energies of - and -flurtamone were -10.239 and -7.555 kcal/mol, respectively. Furthermore, the acute toxicity levels to of - and ac-flurtamone were both highly toxic, and -flurtamone has moderate toxicity. -Flurtamone dissipated preferentially. Therefore, the development of -flurtamone can decrease environmental risks and protect human health.
氟乐灵是一种典型的具有一对对映体的手性农药。本研究系统地研究了氟乐灵对映体的对映选择性生物效应。（此处原文有误，推测应该是“(+)-氟乐灵”等具体名称，按照“(+)-氟乐灵”来翻译）(+)-氟乐灵的生物活性分别比(-)-氟乐灵和反式氟乐灵高6.3 - 35.6倍和1.7 - 9.9倍。(+)-对映体对除草活性的贡献为86.3 - 97.3%。(+)-氟乐灵处理组的类胡萝卜素含量比(-)-氟乐灵处理组低1.31 - 2.14倍。分子对接发现，氟乐灵可与八氢番茄红素去饱和酶（PDS）的苯丙氨酸（PHE）233形成芳香氢键，而(-)-氟乐灵可与PHE 202和PHE 311形成π-π堆积。(+)-和(-)-氟乐灵的结合能分别为-10.239和-7.555千卡/摩尔。此外，(-)-和反式氟乐灵对[具体对象]的急性毒性水平均为高毒，而(+)-氟乐灵具有中等毒性。(+)-氟乐灵优先降解。因此，开发(+)-氟乐灵可以降低环境风险并保护人类健康。
