Natural Product-Based Fungicides Discovery: Design, Synthesis and Antifungal Activities of Some Sarisan Analogs Containing 1,3,4-Oxadiazole Moieties

A series of sarisan analogs containing 1,3,4-oxadiazole moieties were synthesized by iodine-mediated oxidative cyclization and screened in vitro for their antifungal activities at 50 μg/mL against five phytopathogenic fungi such as Valsa mali , Curvularia lunata , Alternaria alternate , Fusarium solani and Fusarium graminearum . 1,3,4-Oxadiazole derivatives 7e , 7p , 7r , 7t and 7u exhibited potent and a broad spectrum of antifungal activities against at least three phytopathogenic fungi at the concentration of 50 μg/mL. Especially, compound 7r displayed more potent antifungal activities against five phytopathogenic fungi than the positive control hymexazol. The EC 50 of 7r against V. mali , C. lunata and A. alternate were 12.6, 14.5 and 17.0 μg/mL, respectively. Additionally, some interesting results of structure-activity relationships (SARs) were also observed.