Targeted Synthesis of Anthranilic Diamides Insecticides Containing Trifluoroethoxyl Phenylpyrazole

Abstract

A series of novel anthranilic diamides analogues(9a–9t) containing trifluoroethoxyl pyrazole moiety was designed and synthesized and their insecticidal bioactivities against Mythimna separata(Walker, M. separata) and Plutellaxylostella (P. xylostella) were evaluated. The structures of the title compounds were confirmed by ¹H NMR, ¹³C NMR and HRMS. Preliminary insecticidal activities showed that some of the title compounds possessed good to excellent bioactivities towards M. separata and P. xylostella. Compounds 9c and 9t exhibited 100% mortality rate against M. separate at 0.2 mg/L. For the P. xylostella, the synthesized compounds(9c–9e, 9i and 9o) showed 70%, 80%, 75 %, 65% and 60% insecticidal activities at 1×10⁻⁶ mg/L, respectively, higher than that of chlorantraniliprole(0). Based on excellent insecticidal activities, the mode of the action was tested by the calcium-imaging technique, the results of which demonstrated that the novel compounds shared the same target with chlorantraniliprole. The binding pose of the most active compound 9t in RyRs of P. xylostella was predicted by molecular docking, which showed that compound 9t interacted with the residues Glu140(A) and His147(A) via hydrogen bond.

Keywords

Trifluoroethoxylphenylpyrazole / Anthranilic diamide derivative / Insecticidal bioactivity / Mode of the action / Molecular docking

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