Synthesis, characterization and insect growth regulating study of beta-alanine substituted sulfonamide derivatives as juvenile hormone mimics

Abstract

A series of β-alanine substituted sulfonamide compounds (6a-6h) as juvenile hormone analogs (JHAs) has been synthesized. The structures of the synthesized compounds have been confirmed by FT-IR, 1H and 13C NMR spectroscopy and ESI-MS (high-resolution mass spectra [HRMS]) techniques. Biological screening of the synthesized analogs has been performed on the fifth larval instar of Galleria mellonella. JH activity of the compounds (6a-6h) has been tested at various concentrations and compared with commercially used JHAs pyriproxyfen (1), fenoxycarb (2). Compound N-methyl-N-phenyl-3-(p-tolylsulfonylamino)propanamide (6d) exhibited better activity among all the tested compounds with LC50 and LC90 values of 0.16 and 0.52 mg/mL, respectively. To understand the structure–activity relationship (SAR), quantum chemical descriptors have been calculated using density functional theory (DFT) method. Toxicity prediction has been performed using the absorption, distribution, metabolism, excretion and toxicity (ADMET) tool. The compounds are proposed to be nontoxic, eco-friendly and biodegradable.