Synthesis and biological activity of novel hydantoin cyclohexyl sulfonamide derivatives as potential antimicrobial agents in agriculture.

Abstract

Plant disease is one of the most serious problems in agriculture that can damage crops. Chemical fungicides are widely used to control plant diseases, but have led to resistance and a series of environmental problems. It is, therefore, necessary to develop highly effective and eco-friendly antimicrobial compounds with novel structures. A series of novel hydantoin cyclohexyl sulfonamide derivatives were synthesized through an intramolecular condensation reaction. The bioassay results indicated that a majority of the title compounds displayed potent inhibitory activity against Botrytis cinerea, Sclerotinia sclerotiorum and Erwinia carotorora. The in vivo inhibition rate of compound 3h was 91.01% against B. cinerea, which was higher than that of iprodione (84.07%). Compound 3w showed excellent antifungal activity against B. cinerea with a half-maximal effective concentration (EC50 ) of 4.80 μg ml-1 , which is lower than that of iprodione. Compound 3q had an EC50 value of 1.44 μg ml-1 against S. sclerotiorum, which was close to that of iprodione (1.39 μg ml-1 ), and the inhibition rate was also similar to that of iprodione. Compounds 3i and 3w had the best inhibition efficacy against S. sclerotiorum, both on growth of the mycelium and sclerotia and in the greenhouse pot test in vitro. Further study showed that compounds 3h, 3r and 3s have superb antibacterial activity against E. carotorora with EC50 values of 2.65, 4.24 and 4.29 μg ml-1 respectively, and were superior to streptomycin sulfate (5.96 μg ml-1 ). Because of their excellent antifungal and antibacterial activity against B. cinerea, S. sclerotiorum and E. carotorora, these hydantoin cyclohexyl sulfonamide derivatives could be considered as suitable candidates for new antimicrobial agents. © 2021 Society of Chemical Industry.