Abstract:
Twenty-five novel phenylpyrazole-pyrimidinamine and phenylpyrazole-pyrimidinone compounds were designed and synthesized based on the low-energy conformation of fipronil using scaffold hopping strategy. Their structures were confirmed by
1H NMR,
13C NMR and HRMS. The insecticidal activity study indicated that compounds
A5 ,
B1 ,
B4 and
B5 showed 40%-73% mortality to
Plutella xylostella at 500 mg/L. However, the insecticidal activities were still weaker than that of fipronil. The differences in physicochemical properties and binding mode with insectival
γ-aminobutyric acid (GABA) receptor between these compounds and fipronil may be the major factor which reduced the insecticidal activities.