Novel 1,3,4-oxadiazole thioether and sulfone derivatives bearing a flexible N-heterocyclic moiety: Synthesis, characterization, and anti-microorganism activity

Abstract

In the search for more efficient and versatile anti-phytopathogen agents, a series of new 1,3,4-oxadiazole thioether/sulfone analogues bearing a flexible N-containing heterocyclic pattern were elaborately prepared, and their bioactivities against plant pathogenic microorganisms were systematically evaluated. Bioassay screening results demonstrated that compounds 32 and 33 significantly inhibited the growth of Xanthomonas oryzae pv. oryzae (Xoo) in vitro (32, EC50 = 5.17 mg L−1; 33, EC50 = 1.19 mg L−1), which were significantly surpass commercial bismerthiazol (BT) and thiodiazole copper (TC). Meanwhile, pot experiments confirmed the prospective applications of compound 33 in managing rice bacterial leaf blight and its good safety toward rice plants. Further studies showed that compound 33 interfered with the formation of bacterial biofilms and inhibited bacterial virulence factors. Furthermore, an in vitro antifungal bioassay showed that compound 32 possessed remarkable growth inhibitory activity against Sclerotinia sclerotiorum (S.s., EC50 = 22.16 mg L−1) and Verticillium dahlia (V.d. EC50 = 32.78 mg L−1). These results all confirmed that the designed 1,3,4-oxadiazole compounds displayed potential for managing plant microbial diseases through targeting dihydrolipoamide S-succinyltransferase (DLST).

Keywords

• 1, 3, 4-oxadiazole derivatives
• Thioether derivatives
• Sulfone derivatives
• Antibacterial activity