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Natural products are a source for pesticide or drug discovery. In order to discover lead compounds with high fungicidal or herbicidal activity, new niacinamide derivatives derived from the natural product niacinamide, containing chiral flexible chains, were designed and synthesized. Their structures were confirmed by ¹H NMR, ¹³C NMR and HRMS analysis. The fungicidal and herbicidal activities of these compounds were tested. The fungicidal activity results demonstrated that the compound (<i>S</i>)-2-(2-chloronicotinamido)propyl-2-methylbenzoate (<b>3i</b>) exhibited good fungicidal activity (92.3% inhibition) against the plant pathogen <i>Botryosphaeria berengriana</i> at 50 μg/mL and with an EC₅₀ of 6.68 ± 0.72 μg/mL, which is the same as the positive control (fluxapyroxad). Compound <b>3i</b> was not phytotoxic and could therefore be used as a fungicide on crops. Structure-activity relationships (SAR) were studied by molecular docking simulations with the succinate dehydrogenase of the fungal mitochondrial respiratory chain.