Synthesis, Herbicidal Activity and Molecular Docking of some New Chloroacetamide Derivatives

Abstract

Four novel chloroacetamide derivatives were synthesized 2-Chloro-N-(2,4-dichlorobenzyl)-N-(3,5dimethylphenyl)acetamide (2), 2-Chloro-N-(2,4dichlorobenzyl)-N-(2,5-dichlorophenyl)acetamide (4), 2-Chloro-N-cinnamyl-N-(4-sulfamoylphenyl)acetamide (6) and 2-chloro-N-(2,5-dichlorophenyl)-N-(2hydroxybenzyl)acetamide ( 8) and evaluated as herbicidal agents against two weed species; Anagallis arvensis as broad leaf weed and Lolium temulentum as a narrow weed in comparison with acetochlor as a standard herbicide. Mass spectra, 1 H-NMR and 13 C-NMR had approved the chemical structures of the synthesized compounds. Depending on the estimation of chlorophyll content, compounds 4 and 2 have been characterized as the most potent, against tested weeds and had EC50 values lower than acetochlor as standard herbicide. In addition, the molecular docking to the active sites of Very Long Chain Fatty Acid Synthase (VLCFAs) as a target enzyme shown that the derivatives gave minimal binding energy and acceptable affinity for the active site.