article · Journal of Agricultural and Food Chemistry
Researchers developed a practical synthesis method to produce novel heterocyclic compounds containing a sulfamoyl moiety, yielding 1,3,4-thiadiazole and 1,3,4-thiadiazine derivatives. The chemical structures were verified using elemental and spectral analysis. When evaluated under laboratory conditions against the pest insect Spodoptera littoralis, the compounds demonstrated insecticidal activity, with compounds 3 and 5 exhibiting median lethal concentrations of 6.42 and 6.90 milligrams per litre, respectively. Molecular docking simulations revealed that the compounds bind effectively into the active site of the 2CH5 receptor, indicating potential utility for receptor-targeting development. Furthermore, computational density functional theory analysis showed that the top-performing compounds possessed energy gaps comparable to the standard commercial insecticide buprofezin, confirming relevant charge transfer properties at the molecular level.
The cotton leafworm, Spodoptera littoralis, is a destructive agricultural pest that damages crops and often requires new control strategies. Developing alternative synthetic chemical compounds that target specific insect receptors provides viable candidates for pest management. This research demonstrates how coupling chemical synthesis with computational docking can identify active molecules capable of acting as insect growth regulator analogues.
The findings could inform the development of new active ingredients for agricultural insecticides targeting leafworms. Potential industrial users include agrochemical companies and crop protection formulators. The research represents early-stage laboratory discovery, as the compounds have only undergone chemical synthesis, computational modelling, and initial laboratory toxicity screenings, meaning substantial further testing and safety assessments are required before commercial application.
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In keeping with our investigation, a simple and practical synthesis of novel heterocyclic compounds with a sulfamoyl moiety that can be employed as insecticidal agents was reported. The compound 2-hydrazinyl-<i>N</i>-(4-sulfamoylphenyl)-2-thioxoacetamide <b>1</b> was coupled smoothly with triethylorthoformate or a variety of halo compounds, namely phenacyl chloride, chloroacetyl chloride, chloroacetaldehyde, chloroacetone, 1,3-dichloropropane, 1,2-dichloroethane, ethyl chloroformate, 2,3-dichloro-1,4-naphthoquinone, and chloroanil respectively, which afforded the 1,3,4-thiadiazole and 1,3,4-thiadiazine derivatives. The new products structure was determined using elemental and spectral analysis. Under laboratory conditions, the biological and toxicological effects of the synthetic compounds were also evaluated as insecticides against <i>Spodoptera littoralis</i> (Boisd.). Compounds <b>3</b> and <b>5</b> had LC<sub>50</sub> values of 6.42 and 6.90 mg/L, respectively. The investigated compounds (from <b>2</b> to <b>11</b>) had been undergoing molecular docking investigation for prediction of the optimal arrangement and strength of binding between the ligand (herein, the investigated compounds (from <b>2</b> to <b>11</b>)) and a receptor (herein, the 2CH5) molecule. The binding affinity within docking score (<i>S</i>, kcal/mol) ranged between -8.23 (for compound <b>5</b>), -8.12 (for compound <b>3</b>) and -8.03 (for compound <b>9</b>) to -6.01 (for compound <b>8</b>). These compounds were shown to have a variety of binding interactions within the 2CH5 active site, as evidenced by protein-ligand docking configurations. This study gives evidence that those compounds have 2CH5-inhibitory capabilities and hence may be used for 2CH5-targeting development. Furthermore, the three top-ranked compounds (<b>5</b>, <b>3</b>, and <b>9</b>) and the standard buprofezin were subjected to density functional theory (DFT) analysis. The highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) energy difference (Δ<i>E</i>) of compounds <b>5</b>, <b>3</b>, and <b>9</b> was found to be comparable to that of buprofezin. These findings highlighted the potential and relevance of charge transfer at the molecular level.
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DOI: 10.1021/acs.jafc.3c09703
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