Abstract
The diamide insecticides show exceptional activity against Lepidoptera insects via activation of ryanodine receptors(RyRs).In the present study,a series of anthranilic diamides containing a fluoroaniline moiety were designed,synthesized,and evaluated for insecticidal potency.Most titled compounds exerted moderate to remarkably high activity against Mythimna separata,Plutella xylostella,and Spodoptera frugiperda.The insecticidal activity of compound II 1 and II ac against M.separata was 26.7 and 26.7% at 0.1 mg L~(-1),respectively,equivalent to that of chlorantraniliprole(0.1 mg L~(-1),30.0%).Compounds II 1,II y,and II z exhibited 8.0-,1.8-,and 4.7-fold higher potency than chlorantraniliprole against P.xylostella,respectively,as compared with their LC_(50)s.Compounds II k and II aa showed good insecticidal activity against S.frugiperda with LC_(50) of 0.56 and 0.46 mg L~(-1),respectively,comparable to that of the commercial insecticide chlorantraniliprole with LC_(50) of 0.31 mg L.Calcium imaging experiments indicated RyRs as the action target.Molecular docking suggested a higher binding energy of 8.647 kcal/mol between II 1 and the M.separata RyR than the 7.820 kcal/mol between chlorantraniliprole and the M.separata RyR.Meanwhile,the docking results of II 1 with mutated P.xylostella RyR at site G4946E showed that II 1 could have a good inhibition effect on the resistant P.xylostella.The density functional theory calculations suggested the importance of the fluoroaniline moiety in potency.Those novel anthranilic diamides containing a fluorinated aniline moiety are good insecticidal candidates.
NSTL