Department of Chemistry, College of Arts and Sciences, Northeast Agricultural University, Harbin 150030, China.
Department of Chemistry, College of Arts and Sciences, Northeast Agricultural University, Harbin 150030, China.
Pestic Biochem Physiol. 2022 Jun;184:105102. doi: 10.1016/j.pestbp.2022.105102. Epub 2022 Apr 22.
Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is a significant target for the discovery of novel bleaching herbicides. Starting from the active fragments of several known commercial herbicides, a series of PPO inhibitors with diphenyl ether scaffolds were designed and synthesized by substructure splicing and bioisosterism methods. The greenhouse herbicidal activity and the PPO inhibitory activity in vitro were measured. The results showed that the novel synthesized compounds have good PPO inhibitory activity, and the IC value against corn PPO ranges from 0.032 ± 0.008 mg/L to 3.245 ± 0.247 mg/L. Among all target compounds, compound P2 showed the best herbicidal activity, with a half inhibitory concentration (IC) of 0.032 ± 0.008 mg/L. In addition, the molecular docking results showed that the benzene ring part of compound P2 can form a π-π stacking with PHE-392, and the trifluoromethyl group and ARG-98 form two hydrogen bonds. Crop safety experiments and cumulative concentration analysis experiments indicated that compound P2 can be used for weed control in rice, wheat, soybean and corn. Therefore, compound P2 can be selected to develop potential lead compounds for novel PPO inhibitors.
原卟啉原氧化酶（PPO，EC 1.3.3.4）是新型漂白除草剂发现的重要靶标。本研究从几种已知商业除草剂的活性片段出发，采用亚结构拼接和生物等排方法设计并合成了一系列具有二苯醚骨架的 PPO 抑制剂。测定了温室除草活性和体外 PPO 抑制活性。结果表明，新型合成化合物具有良好的 PPO 抑制活性，对玉米 PPO 的 IC 值在 0.032±0.008mg/L 至 3.245±0.247mg/L 之间。在所研究的目标化合物中，化合物 P2 表现出最好的除草活性，其半抑制浓度（IC）为 0.032±0.008mg/L。此外，分子对接结果表明，化合物 P2 的苯环部分可与 PHE-392 形成π-π堆积，三氟甲基和 ARG-98 形成两个氢键。作物安全性试验和累积浓度分析试验表明，化合物 P2 可用于水稻、小麦、大豆和玉米田杂草防治。因此，化合物 P2 可被选择用于开发新型 PPO 抑制剂的潜在先导化合物。
