Novel N-nitroacetamide derivatives derived from 2,4-D: Design, synthesis, bioevaluation, and prediction of mechanism of action

•The novel N-nitroacetamides derived from 2,4-D have been conveniently obtained.•The novel N-nitroacetamides derivatives exhibited good herbicidal activities.•In vitro inhibition activities and molecular docking indicated that these compounds might target AHAS enzyme.

A series of novel N-nitroacetamides derived from 2,4-dichlorophenoxyacetic acid (2,4-D, a important plant growth regulator) have been conveniently obtained via multi-step reactions including oxidation, bromination, nitration, chlorination, and acylation reactions. All the structures of newly prepared compounds were thoroughly characterized by satisfied IR, 1H NMR, and 13C NMR spectrums. The herbicidal activity and plant growth regulating activities of target compounds were also assessed. The preliminary bioassay results showed that these novel N-nitroacetamide derivatives exhibited good herbicidal activity against both dicotyledonous and monocotyledonous weeds. Meanwhile, some of the target compounds displayed high plant growth regulating activity against Rice at the dosage of 0.1 mg/L. The further in vitro inhibition activity against acetohydroxyacid synthase (AHAS) enzyme and molecular docking indicated that AHAS might be the primary target site for these newly synthesized compounds.

Graphical abstractA series of novel N-nitroacetamides derivatives targeting AHAS enzyme have been obtained and evaluated, and some of the target compounds displayed good activities at the dosage of 0.1 mg/L.Figure optionsDownload full-size imageDownload as PowerPoint slide