Design, synthesis and fungicidal activities evaluation of N-(thiazol-4-ylmethyl) benzenesulfonamide derivatives

A series of N- (thiazol-4-ylmethyl) benzenesulfonamide derivatives were designed, synthesized, and characterized by 1 H NMR, 13 C NMR, and HRMS. The evaluation of fungicidal activities against Fusarium oxysporum ( F. oxysporum ), Sclerotinia sclerotiorum ( S. sclerotiorum ), Botrytis cinerea ( B. cinerea ), Colletotrichum fragariae ( C. fragariae ), Alternaria alternata ( A. alternata ), Penicillium digitatum ( P. digitatum ), Curvularia lunata ( C. lunata ), and Curvularia mebaldsii ( C. mebaldsii ) for the target compounds was carried out. The results indicated that this series of compounds were sensitive to C. lunata , B. cinerea , and S. sclerotiorum . Especially, 2,4-dichloro- N- ((2-phenylthiazol-4-yl)methyl)benzenesulfonamide ( 5c ) exhibited the best bioactivities against C. lunata , B. cinerea , and S. sclerotiorum with EC 50 value of 20.8 mg/L (52.3 μM), 24.6 mg/L (61.8 μM), and 9.5 mg/L (23.9 μM), respectively, which has equivalent or superior fungicidal activity to commercial products hymexazol. Furthermore, the structure–activity relationship was given, which might be contribution to the design and discovery of N- (thiazol-4-ylmethyl)benzenesulfonamide derivatives as novel fungicide.