Design, Synthesis, and Fungicidal Evaluation of Novel N-Methoxy Pyrazole-4-Carboxamides as Potent Succinate Dehydrogenase Inhibitors

Succinate dehydrogenase (SDH, EC 1.3.5.1, also known as complex II) has been recognized as one of the most promising targets of fungicides. Here, based on the binding mode of pydiflumetofen with SDH, the carbon-carbon double bond was introduced into the chemical of pydiflumetofen and then produced the target compounds 6a-6o. The enzymatic inhibitory activity and structure-activity relationship (SAR) study showed that the 2-position and 4-position in terminal benzene were positive to increasing activity. Furthermore, fungicidal activity results in greenhouses indicated that compound 6o showed good control effects against wheat powdery mildew (WPM), cucumber powdery mildew (CPM), and southern corn rust (SCR), showing its broad-spectrum property. Especially, compound 6o exhibited 95 and 75% control effects against CPM and SCR at 6.25 mg/L, respectively, which are better than pydiflumetofen (80% control effects against CPM and 15% against SCR), indicating its potency that is worthy of further development.