| Autor: |
El-Saghier AM; Chemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt., Enaili SS; Chemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt.; Chemistry Department, Faculty of Science, Al Zawia University, 16418 Al Zawia, Libya., Abdou A; Chemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt., Alzahrani AYA; Chemistry Department, Faculty of Science and Arts, King Khalid University, Mohail, 61421 Assir, Saudi Arabia., Ben Moussa S; Chemistry Department, Faculty of Science and Arts, King Khalid University, Mohail, 61421 Assir, Saudi Arabia., Gad MA; Research Institute of Plant Protection, Agricultural Research Center, 12619 Giza, Egypt., Kadry AM; Chemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt. |
| Jazyk: |
angličtina |
| Zdroj: |
Journal of agricultural and food chemistry [J Agric Food Chem] 2024 May 22; Vol. 72 (20), pp. 11369-11380. Date of Electronic Publication: 2024 May 10. |
| DOI: |
10.1021/acs.jafc.3c09703 |
| Abstrakt: |
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- N -(4-sulfamoylphenyl)-2-thioxoacetamide 1 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 Spodoptera littoralis (Boisd.). Compounds 3 and 5 had LC 50 values of 6.42 and 6.90 mg/L, respectively. The investigated compounds (from 2 to 11 ) had been undergoing molecular docking investigation for prediction of the optimal arrangement and strength of binding between the ligand (herein, the investigated compounds (from 2 to 11 )) and a receptor (herein, the 2CH5) molecule. The binding affinity within docking score ( S , kcal/mol) ranged between -8.23 (for compound 5 ), -8.12 (for compound 3 ) and -8.03 (for compound 9 ) to -6.01 (for compound 8 ). 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 ( 5 , 3 , and 9 ) 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 E ) of compounds 5 , 3 , and 9 was found to be comparable to that of buprofezin. These findings highlighted the potential and relevance of charge transfer at the molecular level. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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