Synthesis and biological activities of novel trifluoromethylpyridine amide derivatives containing sulfur moieties.

A series of trifluoromethylpyridine amide derivatives containing sulfur moieties (thioether, sulfone and sulfoxide) was designed and synthesized. Their antibacterial activities against Xanthomonas oryzae pv. oryzae ( Xoo ), Ralstonia solanacearum ( R. solanacearum ) and insecticidal activities against P. xylostella were evaluated. Notably, the half-maximal effective concentration (EC 50 ) value of sulfone-containing compound F10 is 83 mg L -1 against Xoo , which is better than that of commercial thiodiazole copper (97 mg L -1 ) and bismerthiazol (112 mg L -1 ). Thioether-containing compounds E1, E3, E5, E6, E10, E11 and E13 showed much higher activities against R. solanacearum with the EC 50 value from 40 to 78 mg L -1 , which are much lower than that of thiodiazole copper (87 mg L -1 ) and bismerthiazol (124 mg L -1 ). Generally, most of the sulfone-containing compounds and sulfoxide-containing compounds showed higher activities against Xoo than that of the corresponding thioether-containing compound, but most of the thioether-containing compounds contributed higher antibacterial activities against R. solanacearum . Furthermore, title compounds E3, E11, E24 and G2 showed good insecticidal activities of 75%, 70%, 70% and 75%, respectively.