Geng Wang, Zhang Wei, Lei Qiong, Gan Xiuhai
State Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, P. R. China.
J Agric Food Chem. 2025 Mar 19;73(11):6599-6609. doi: 10.1021/acs.jafc.5c00345. Epub 2025 Mar 5.
The discovery of novel protoporphyrinogen IX oxidase (PPO) inhibitors has become a key focus in herbicide development. To explore new PPO inhibitors, a series of -phenylphthalimide derivatives with ether moieties were designed and successfully synthesized. Among these, compound ( = 10.3 nM) exhibited a strong inhibitory effect on PPO, outperforming flumiclorac-pentyl ( = 46.3 nM) and flumioxazin ( = 52.0 nM). It is noted that compounds , , , and showed broad-spectrum herbicidal activity against the tested weeds at 75 g a.i./ha. In addition, results of molecular simulation and density functional theory (DFT) calculations indicated that compound possessed not only a robust hydrogen bond with Arg98 of PPO but also superior chemical reactivity, electrostatic field, and strong polarity. Therefore, compound may be regarded as a promising lead compound for the development of high-efficiency PPO inhibitors.
新型原卟啉原IX氧化酶（PPO）抑制剂的发现已成为除草剂开发的关键重点。为探索新型PPO抑制剂，设计并成功合成了一系列带有醚基的-苯基邻苯二甲酰亚胺衍生物。其中，化合物（IC₅₀ = 10.3 nM）对PPO表现出强烈的抑制作用，优于氟烯草酸戊酯（IC₅₀ = 46.3 nM）和氟草嗪（IC₅₀ = 52.0 nM）。值得注意的是，化合物、、和在75 g a.i./ha剂量下对受试杂草表现出广谱除草活性。此外，分子模拟和密度泛函理论（DFT）计算结果表明，化合物不仅与PPO的Arg98形成了强大的氢键，而且具有优异的化学反应性、静电场和强极性。因此，化合物可被视为开发高效PPO抑制剂的有前景的先导化合物。
