Design, Synthesis, and Insecticidal Activity of Novel Isoxazoline Diacylhydrazine Compounds as GABA Receptor Inhibitors

A series
of isoxazoline derivatives containing diacylhydrazine
moieties were designed and synthesized as potential insecticides.
Most of these derivatives exhibited good insecticidal activities against Plutella xylostella, and some compounds exhibited
excellent insecticidal activities against Spodoptera
frugiperda. Especially, D14 showed outstanding
insecticidal activity against P. xylostella (LC50 = 0.37 μg/mL), which was superior to that
of ethiprole (LC50 = 2.84 μg/mL) and tebufenozide
(LC50 = 15.3 μg/mL) and similar to that of fluxametamide
(LC50 = 0.30 μg/mL). Remarkably, the insecticidal
activity of D14 against S. frugiperda (LC50 = 1.72 μg/mL) was superior to that of chlorantraniliprole
(LC50 = 3.64 μg/mL) and tebufenozide (LC50 = 60.5 μg/mL) but lower than that of fluxametamide (LC50 = 0.14 μg/mL). The results of electrophysiological
experiments, molecular docking, and proteomics experiments indicate
that compound D14 acts by interfering with the γ-aminobutyric
acid receptor to control pests.