Dual-Target Inhibitors─Discovery of Novel Diphenyl-(Thio)ether-Containing Benzoxaborole Derivatives as Potential Antifungal and Herbicidal Agents

LeuRS and PPO are important targets in the development of green pesticides; novel diphenyl-(thio)ether-containing benzoxaborole derivatives were designed and synthesized as novel dual-target enzyme inhibitors; their antifungal activities against six kinds of common plant pathogens in vitro and their herbicidal activities against purslane and barnyard grass were studied. Most of the target compounds showed excellent antifungal activity against six kinds of plant pathogenic fungi in vitro, and this is highlighted by compounds 6c and 6h, both displayed 100.0% inhibition effects against three kinds of the tested plant pathogenic fungi under the concentrations of 50.0 μg/mL, and the EC50 value of compound 6r against Rhizoctonia solani was 0.763 μg/mL, significantly lower than that of boscalid (1.20 μg/mL). In addition, compound 6c was also used in negative control experiments, and the results revealed that compound 6c had no significant effect on the growth of noninfected plants. Meanwhile, most of the compounds also demonstrated promising herbicidal activity, as compounds 6b, 6h, 6m, and 7e showed effective control on purslane and barnyard grass. Beyond that, compound 6s demonstrated certain safety against rape. Enzymatic inhibition experiments further confirmed that compound 7e exhibited remarkable inhibitory activity against NtPPO. Moreover, the molecular docking results between 6c and 7g and tLeuRS and NtPPO further revealed the mechanisms of action for their biological activities. In summary, compounds 6b, 6c, 6h, 7e, and 7g showed excellent antifungal and herbicidal activities and can be further studied as new antifungal and herbicidal agents in the next step.