Design,Synthesis and Nematicidal and Fungicidal Activities of 8-Chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine Oxadiazole Thioether Derivatives
In order to discover new compounds with high nematicidal and fungicidal activity,22 8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine oxadiazole thioether derivatives were designed and synthesized,and the structures of all target com-pounds were confirmed by 1H NMR,13C NMR and high-resolution mass spectra(HRMS).The results of nematicidal activity test showed that all the target compounds possessed certain toxic activity against Caenorhabditis elegans(second-stage juve-niles)at the concentration of 100 mg/L.The LC50 of 2-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-yl)-5-((2-fluoro-benzyl)thio)-1,3,4-oxadiazole(6j),2-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-yl)-5-((2-chlorobenzyl)thio)-1,3,4-oxadiazole(6m),2-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-yl)-5-((2-cyanobenzyl)thio)-1,3,4-oxadiazole(6q),2-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-yl)-5-((3-methoxybenzyl)thio)-1,3,4-oxadiazole(6s)and 2-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-yl)-5-((4-methoxybenzyl)thio)-1,3,4-oxadiazole(6t)against C.elegans were 48.10,34.94,52.87,48.32 and 37.62 mg/L,respectively,which were superior than that of fosthiazate(79.28 mg/L).The results of fungicidal activity test showed that 2-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-yl)-5-((2-bromoethyl)thio)-1,3,4-oxadiazole(6d)had good inhibitory activity against Rhizoctonia solani.The ECso value of compound 6d was 7.22 mg/L,which was superior to that of fluopyram(110.02 mg/L).At the concentration of 100 and 200 mg/L,the protective effects of compound 6d against rice sheath blight were 85.5％and 92.1％,and the curative effects were 59.2％and 79.0％.The target compounds synthesized in this study have certain nematocidal and fungicidal activities,which can provide new ideas for the design and synthesis of imidazo[1,2-a]pyridine derivatives,and have reference significance for exploring the bioactivity diver-sity of imidazo[1,2-a]pyridine derivatives.
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