Design, synthesis, and biological activity of novel 1,2,4-oxadiazole derivatives

BACKGROUND: Plant diseases seriously threaten food security, it is urgent to discover efficient and low-risk chemical pesticides. 1,2,4-Oxadiazole derivatives exhibit broad spectrum of agricultural biological activities. For discovering novel molecules with excellent agricultural activities, novel 1,2,4-oxadiazole derivatives were synthesized and evaluated for their agricultural activities. RESULT: Bioassays results showed that the title compounds exhibited moderate nematocidal activity against Meloidogyne incognita and anti-fungal activity to Rhizoctonia solani. It’s worth noting that compounds 5m, 5r, 5u, 5v, 5x and 5y showed strong antibacterial effects on Xanthomonas oryzae pv. oryzae (Xoo), with EC(50) values of 36.25, 24.14, 28.82, 19.44, 25.37 and 28.52 μg/mL, respectively, superior to bismerthiazol (BMT, EC(50) = 77.46 μg/mL) and thiodiazole copper (TDC, EC(50) = 99.31 μg/mL). Compounds 5p, 5u and 5v exhibited excellent antibacterial ability against Xanthomonas oryzae pv. oryzicola (Xoc), with EC(50) values of 31.40, 19.04 and 21.78 μg/mL, respectively, better than that of BMT (EC(50) = 68.50 μg/mL) and TDC (EC(50) = 91.05 μg/mL). In addition, compound 5v exerted moderate antibacterial effects on rice bacterial leaf blight. CONCLUSIONS: Twenty-six novel 1,2,4-oxadiazole derivatives were obtained and their biological activities were evaluated. Compound 5u and 5v exhibited excellent antibacterial activity Xoo and Xoc. These results indicated that 1,2,4-oxadiazole derivatives containing a trifluoromethyl pyridine moiety could be as potential alternative templates for discovering novel antibacterial agents. [Image: see text]