Design and synthesis of novel hydrocarbylidene nitrohydrazinecarboximidamides against aphids based on natural product galegine

Abstract

A series of novel hydrocarbylidene nitrohydrazinecarboximidamides were designed and synthesized using an insecticidal natural product Galegine as a lead compound. The bioassay results show that the target compounds exhibited moderate to good insecticidal activities against Hyalopterus pruni Geoffroy at a concentration of 200 mg/L, and most compounds show excellet insecticidal activities against Aphis gossypii Glover. In particular, compounds IIc-01, IIc-03, IIe-02 and IIf-01 show the equal activities to a commercial pesticide Imidacloprid with their LC50 values are 0.21 mg/L, 0.27 mg/L, 0.12 mg/L and 0.24 mg/L, respectively, and compounds IIc-02 and IIe-05 show 10 times insecticidal activities as much as Imidacloprid with their LC50 values both are 0.02 mg/L. Structure–activity relationship and 3D-QSAR analyses indicate that the introduction of fluorine atom is useful for increasing the insecticidal activity of target compounds.