Synthesis and antifungal activities of novel thiophene-based stilbene derivatives bearing an 1,3,4-oxadiazole unit

Background: Natural stilbenes (especially resveratrol and its derivatives) are well-known phytoalexins that are active against many plant diseases. However, oxidative degradation and low bioavailability limit their exogenous application as fungicides on crops. In this study, a new class of resveratrol-inspired thiophene-based stilbene derivatives bearing an 1,3,4-oxadiazole unit was synthesized and the derivatives' antifungal activities against phytopathogenic fungi were investigated.

Results: The results revealed that compounds 5h and 5j exhibited improved antifungal activity against Botrytis cinerea with median effective concentrations (EC₅₀ ) of 168.5 and 155.4 µg mL^-1 , respectively, which were superior to the EC₅₀ of resveratrol (263.1 µg mL^-1 ). Compound 5j was shown to effectively control disease development in B. cinerea-infected tomatoes in vivo. Notably, considerably abnormal mycelial morphology and increased cell membrane conductivity were observed in the presence of compound 5j.

Conclusion: A new class of thiophene-containing stilbene derivatives was designed and synthesized. Bioassay results showed that compound 5j exhibited promising antifungal activity, suggesting practical potential for fungal disease control. © 2018 Society of Chemical Industry.