Synthesis and bioactivity of novel sulfone derivatives containing 2,4-dichlorophenyl substituted 1,3,4-oxadiazole/thiadiazole moiety as chitinase inhibitors

Abstract

The paper reported the synthesis and antifungal properties and mechanism of action of a series of 2-substituted methylthio-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole/thiadiazole and their corresponding sulfones. The preliminary biological test showed these compounds exhibit moderate to good antifungal activity. Particularly, the compounds 7g and 7c inhibited mycelia growth by approximately 50% (EC 50) at 2.6–59.2 μg/mL and 17.2–54.4 μg/mL respectively against nine kinds of fungi. The extent of inhibition induced by 7c on Rhizoctonia solani and underlying mechanism of action were studied in vitro. Docking simulation was performed to position selected compounds into the active site of family 18 chitinases. Variation in d-GlcNAc content and chitinase activity indicated that 7c can act as chitinase inhibitor for controlling fungal pathogens in plants.