Synthesis and biological activity of novel 1-substituted phenyl(glycosyl)-4-{4-[4,6-dimethoxy)pyrimidin-2-yl] piperazin-1-yl}methyl-1H-1,2,3-triazoles

Abstract

A series of novel 1-substituted phenyl or glycosyl 1,2,3-triazoles was designed and synthesized by azide-alkyne 1,3-dipolar cycloaddition between 4,6-dimethoxy-2-[4-prop-2-ynyl)piperazin-1-yl] pyrimidine and each of different azides catalysed by in situ generated Cu(I). The O-acyl protecting groups on glycosyl 1,2,3-triazoles were removed by triethylamine in wet methanol. Their chemical structures were established on the basis of corresponding ¹H NMR, ¹³C NMR, MS and elemental analysis. The fungicidal activities of target compounds were evaluated in vitro against Fusarium omysporum, Physalospora piricola, Alternaria solani, Phytophthora capsici, Cercospora arachidicola and Gibberella zeae at 50 μg/mL. The bioassay results indicate that some of the compounds exhibited moderate but promising fungicidal activities. In particular, acetylated glucopyranosyl triazole displayed a good fungicidal activity against Physalospora piricola, which is equal to that of the positive control compound chlorothalonil.

Keywords

1H-1,2,3-Triazole / Fungicidal activity / Huisgen cycloaddition reaction / Pyrimidinylpiperzine

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