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

Abstract

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.