State Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China.
J Agric Food Chem. 2024 Jun 12;72(23):12946-12955. doi: 10.1021/acs.jafc.4c00272. Epub 2024 May 29.
Protoporphyrinogen IX oxidase (PPO, EC 1.3.3.4) is one of the most important targets for the discovery of green herbicides. In order to find novel PPO inhibitors with a higher herbicidal activity, a series of novel -phenyltriazinone derivatives containing oxime ether and oxime ester groups were designed and synthesized based on the strategy of pharmacophore and scaffold hopping. Bioassay results revealed that some compounds showed herbicidal activities; especially, compound exhibited broad-spectrum and excellent 100% herbicidal effects to , , , , , and at a concentration of 37.5 g a.i./ha, which were comparable to trifludimoxazin. PPO (PPO) enzyme inhibitory assay indicated that showed an excellent enzyme inhibitory activity with a value of 32.14 nM, which was similar to that of trifludimoxazin (31.33 nM). Meanwhile, compound revealed more safety for crops (rice, maize, wheat, peanut, soybean, and cotton) than trifludimoxazin at a dose of 150 g a.i./ha. Moreover, molecular docking and molecular dynamics simulation further showed that has a very strong and stable binding to PPO. It indicated that can be used as a potential PPO inhibitor and herbicide candidate for application in the field.
原卟啉原氧化酶（PPO，EC 1.3.3.4）是发现绿色除草剂的最重要目标之一。为了找到具有更高除草活性的新型 PPO 抑制剂，我们基于药效团和骨架跃迁的策略，设计并合成了一系列含有肟醚和肟酯基团的新型 -苯基三嗪酮衍生物。生物测定结果表明，一些化合物表现出除草活性；特别是，化合物 在 37.5 g a.i./ha 的浓度下，对 、 、 、 、 和 表现出广谱和优异的 100%除草效果，与三氟啶磺隆相当。PPO（PPO）酶抑制试验表明，化合物 表现出优异的酶抑制活性，值为 32.14 nM，与三氟啶磺隆（31.33 nM）相似。同时，化合物 在 150 g a.i./ha 的剂量下对水稻、玉米、小麦、花生、大豆和棉花等作物的安全性高于三氟啶磺隆。此外，分子对接和分子动力学模拟进一步表明，化合物 与 PPO 具有很强且稳定的结合。这表明 可以用作潜在的 PPO 抑制剂和除草剂候选物，可应用于田间。
