Zhang Wei, Yang Jinsong, Tang Xianying, Zhang Jiahui, Gan Xiuhai
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. 2025 Jun 18;73(24):14857-14866. doi: 10.1021/acs.jafc.5c00979. Epub 2025 Jun 6.
To continue our development of novel -phenyltriazinone herbicides, a series of -phenyltriazinone derivatives containing 5,6-dihydro-4-1,2-oxazine or oxime fragments were designed and synthesized based on intermediate derivatization approach using ring expansion and ring opening strategies. PPO (PPO) activity assay showed that most of the compounds showed strong inhibition to PPO. Among them, compound ( = 28.9 nM) exhibits good inhibitory effect on PPO comparable to that of triflurazine ( = 30.7 nM). Systematic postemergence herbicidal activity evaluation found that had excellent herbicidal activity, with over 90% control effect on six weed species (, , , , , and ) at 37.5 g a.i./ha. Moreover, it caused only 20-40% damage to rice, maize, peanuts, and wheat at 75-150 g a.i./ha, which was significantly safer than trifludimoxazin (60-100%). Molecular simulations showed that compound formed two hydrogen bonds with Arg98 of PPO. Density functional theory (DFT) calculations indicated that showed high chemical reactivity and electronic chemical potential. The present study demonstrates that compound holds significant potential as a promising PPO inhibitor and it offers a novel approach for the development of efficient and broad-spectrum herbicides through an intermediate derivatization strategy.
为了继续开发新型苯基三嗪酮除草剂，基于环扩张和开环策略的中间体衍生化方法，设计并合成了一系列含有5,6-二氢-4H-1,2-恶嗪或肟片段的苯基三嗪酮衍生物。PPO（原卟啉原氧化酶）活性测定表明，大多数化合物对PPO表现出强烈抑制作用。其中，化合物（IC₅₀ = 28.9 nM）对PPO的抑制效果良好，与氟草敏（IC₅₀ = 30.7 nM）相当。系统的苗后除草活性评估发现，该化合物具有优异的除草活性，在37.5 g a.i./ha剂量下对六种杂草（稗草、马唐、狗尾草、牛筋草、反枝苋和苘麻）的防除效果超过90%。此外，在75 - 150 g a.i./ha剂量下，它对水稻、玉米、花生和小麦仅造成20 - 40%的损伤，比氟丁酰草胺（60 - 100%）明显更安全。分子模拟表明，该化合物与PPO的Arg98形成了两个氢键。密度泛函理论（DFT）计算表明，该化合物具有高化学反应活性和电子化学势。本研究表明，该化合物作为一种有前景的PPO抑制剂具有巨大潜力，并且通过中间体衍生化策略为开发高效广谱除草剂提供了一种新方法。
