| Plant diseases and insect pests caused by fungal has become a global problem for crops protection. Andit’s important to control fungal pathogens.Benzoxazinoids and derivatives have a broad of biological activities which has been widely reported fortheir synthetic method and antiviral bioactive. Triazole compounds, bearing highly efficient, broadspectrum and inward-absorbent, play a great role in fungicide. In this paper, benzoxazinoids has beenmodified in order to explore new potential antifungal drugs by introducing1,2,3-triazole moitety to theirstructure via click reaction. The synthesis and biological activity of the new compounds were also studied.In the synthetic experiment, the result shows that the synthetic method of2H-1,4-benzoxazine-3(4H)-ketone possesses features of high yield, low-cost, short process flow and convenient operation.O-aminophenol, chloroacetyl chloride and potassium carbonate were chosen as the starting materials. Thecompounds were synthesized by two steps at room temperature. After the reaction between the2H-1,4-benzoxazine-3(4H)-ketone and the lawesson reagent in the refluxed toluene for16h, the2H-1,4-benzoxazine-3(4H)-thioketone was obtained. Benzoxazinoids-triazole derivatives were synthesizedby means of "one pot process" at room temperature with2H-1,4-benzoxazine-3(4H)-one, propargylbromide and azide phenyl compounds. The reaction was carried out using CuCl and CH3COONa ascatalyst, using DMF and H2O as solvent (V/V=1:1). Under the optimized reaction conditions,12newcompounds were synthesized.In the antifungal bioactivity experiment, most compounds has an obvious inhibitory against Chili anthraxbacteria and rhizoctonia cerealis vander hoeven. And4-[1-(2-phenyl)-4,5-dihydro-1H-[1,2,3]triazole4-methyl]-4H-1,4-benzooxazine-3(4H)-sulfur has obvious antibacterial activity. The experiment has provedthat1,4-benzoxazinoids containing mercapto group have better antibacterial effect than that containingcarbonyl group. |
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