Structural and biological studies on beta – alanine substituted Sulfonamide derivatives: A new class of Juvenile hormone mimics as insect growth regulators

Abstract

A series of naphthyl-sulfonamide juvenile hormone analogs has been synthesized through one-pot synthesis route using thionyl chloride as an activating agent for carboxylic functional group. The structures of synthesized compounds with general formula C10H7-SO2NH-(CH2)2CON-R1R2 have been confirmed by FT-IR, 1HNMR , 13CNMR , and ESI-MS techniques. The insect growth regulating property of all the synthesized compounds as juvenile hormone analogs (JHAs) has been studied against yellow fever mosquito, Aedes aegypti and tobacco cutworm, Spodoptera litura. The bioassay results demonstrate that the synthesized compounds exhibit insect growth regulating activity in comparison to standard JHAs. The IE50 and IE90 values of B4 are 0.08 and 6.62 ppm, respectively for inhibition of Aedes aegypti and the LC50 and LC90 values of B3 are 11.03 and 45.36 ppm, respectively for Spodoptera litura. Notably, the compounds B3 and B4 showed enhanced efficacy at lower concentrations. Additionally, density functional theory (DFT) technique is used to predict the chemical reactivity and toxicity of the synthesized JHAs in comparison to pyriproxyfen. Further, the DNA-binding study of synthesized JHAs has been carried out using UV–vis spectroscopy for toxicity assessment against DNA and the binding constant values in the range 102 – 103 suggest lower toxicity of all the synthesized molecules in comparison to PYR. All the synthesized JHAs show IGR action and exhibit better reactivity and reduced toxicity as compared to the commercial in use IGRs.