Synthesis, Insecticidal Activity and 3D-QSAR Studies on Diacylhydrazine Derivatives Containing Furan

22 novel diacylhydrazine derivatives containing furan were synthesized by the reaction of 5-substituted phenyl-2-furoyl chloride with substituted benzohydrazide in anhydrous dichloromethane under reflux. Their structures were confirmed by IR, H-1 NMR spectra and elemental analysis. The preliminary bioassay showed all the title compounds exhibited larvicidal activity to the Aphis fabae. At the concentration of 0.05%, compounds Ia, Ib and Ic showed 81.8%, 58.4% and 52.2% larvicidal activity to Aphis fabae respectively. The compound Ia could induce aphid larvae premature, abnormal, and lethal larval molt and poorer fecundity of adults. Most of the title compounds showed low activity to Mythimna separate, Tetranychus urticae and Culex pipiens pallens at the concentration of 0.1%, 0.05% and 0.001%. Comparative molecular field analysis (CoMFA) method was applied to the study on the three-dimensional quantitative structure activity relationship (3D-QSAR) of target compounds. Influence of the different grids on different force field with different kinds of charge form was evaluated and finally a reasonable model with predictive ability was obtained from the investigation (q(2)=0.518, r(2)=0.936). The contour maps based on the analysis of steric and electrostatic CoMFA coefficients could not only explain the relationship between the structures and bioactivity, but also lead to the insight into the further design of highly active compounds.