Design, synthesis, herbicidal activity, and the molecular docking study of novel diphenyl ether derivatives as protoporphyrinogen IX oxidase inhibitors

• Published in: Journal of molecular structure 2022-06, Vol.1258, p.132670, Article 132670
• Main Authors: Zhao, Li-Xia, Peng, Jian-Feng, Hu, Jia-Jun, Zou, Yue-Li, Yin, Min-Lei, Wang, Zhi-Xin, Gao, Shuang, Fu, Ying, Ye, Fei
• Format: Article
• Language: English
• Subjects: Diphenyl ether derivatives; Field trial; Greenhouse herbicidal activity; Molecular docking; PPO
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2022.132670

•The molecular docking of all synthesized target compounds is helpful to study the mechanism of the compound and explain its structure-activity relationship.•Field experiments were conducted on compound H7 to further determine whether it can be used as a potential herbicide to control weeds in the field•The inhibitory activity (IC50) of all target compounds on corn PPO was determined Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is an important herbicide target. In this study, a series of novel diphenyl ethers derivatives with 2-pyrrolidone structure were developed as PPO inhibitors. Thereinto, compound H7 (IC50 = 0.0262 mg/L) has better PPO enzyme inhibitory activity than commercial herbicide oxyfluorfen (IC50 = 0.0426 mg/L). Greenhouse herbicidal activity experiments exhibited that even under the condition of 37.5 g ai/ha, H7 still had excellent broad-spectrum herbicidal activity. Moreover, rice, peanut, and cotton had strong tolerance to H7 at 300 g ai/ha. Field trial showed that H7 had comparable herbicidal activity to oxyfluorfen. These experimental results indicated that H7 could be developed as a novel PPO Inhibitor candidate for weed control in the field.