1,2,3-Triazole amide derivatives containing triazole as a bioisoster of pyrazole were designed according to “bioisoteric replacement” from pyrazole amide fungicide. Seventeen novel 1-substituted-1H- 1,2,3-triazole-4-carboxamide derivatives were quickly synthesized through the copper(I)-catalyzed Huisgen 1,3-dipolar cycloadditions of organic azide compounds and propiolamide, which was synthesized from propiolic acid. With Cu/C as the catalyst and triethylamine as the additive, the coupling product substituted bis-1,2,3-triazole 17 was obtained in a moderate yield when cyclizing intermediate N-(3,4-dimethoxy- phenethyl)propiolamide (4a) and 2-azido-1,1,1-trifluoroethane (14). The structures of the target compounds were confirmed by ¹H NMR spectra, elemental analysis or high resolution mass spectra (HRMS). The investigation of the target compound bioactivities show that, some of them like 6a, 6e, 6k and 6l perform good herbicidal activity at 100 μg/mL, even though they have a poor fungicidal action.

Key words: 1,2,3-triazole, amide, click chemistry, coupling, herbicidal activity