Sixteen novel 2-(1H-benzimidazol-2-yl)-5-substituted phenyl-1,3,4-oxadiazoles and 2-(1H-benzimidazol-2-yl)-5-substituted phenylamino-1,3,4-oxadiazoles were synthesized from benzimidazole-2-carboxylic acid, hydrazine hydrate, substituted phenyl isothiocyanate and substituted benzoic acid by multi-step reactions. The target compounds were evaluated for their antifungal activities against Botrytis cinerea and Sclerotinia sclerotiorum, and the results indicated that three target compounds displayed excellent antifungal activities against Botrytis cinerea, with EC 50 values of 2.55, 6.34 and 5.12 μg/mL, respectively, even higher than that of carbendazim.