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

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.

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 EC₅₀ values of 36.25, 24.14, 28.82, 19.44, 25.37 and 28.52 μg/mL, respectively, superior to bismerthiazol (BMT, EC₅₀ = 77.46 μg/mL) and thiodiazole copper (TDC, EC₅₀ = 99.31 μg/mL). Compounds 5p, 5u and 5v exhibited excellent antibacterial ability against Xanthomonas oryzae pv. oryzicola (Xoc), with EC₅₀ values of 31.40, 19.04 and 21.78 μg/mL, respectively, better than that of BMT (EC₅₀ = 68.50 μg/mL) and TDC (EC₅₀ = 91.05 μg/mL). In addition, compound 5v exerted moderate antibacterial effects on rice bacterial leaf blight.

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.