A series of novel pyrazole-4-carboxamides were rationally designed, synthesized, and their structures were characterized by 1H NMR, 13C NMR and HRMS. Preliminary bioassay showed that four compounds 8g, 8j, 8o and 8s exhibited more than 90% and even completed inhibition against Alternaria solani at 100 μg/mL; and 8d displayed 100% inhibition against Fusarium oxysporum at the same concentration. Moreover, 8j exhibited good in vitro fungicidal activity against A. solani with EC50 value of 3.06 μg/mL, and it also displayed completed in vivo protective antifungal activity against A. solani on tomato at 10 mg/L, as boscalid did. The molecular docking results indicated that 8j exhibited the high affinity with SDH protein by H-bond and π-π stacking interactions, which may explain the reasons for its good activities. These data support that compound 8j could be used as a fungicide candidate for further study. A practical method for the synthesis of pyrazole-4-carboxamides were provided and evaluation of their antifungal activities.
Keywords: Fungicidal activity; Molecular docking; Pyrazole carboxamide; Succinate dehydrogenase inhibitor; Synthesis.
© 2020. Springer Nature Switzerland AG.