H. Mao, Hong Song, De-Qing Shi
Mar 1, 2013
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Journal
Journal of Heterocyclic Chemistry
Abstract
A series of novel 5-aryl-1-(aryloxyacetyl)-3-(tert-butyl or phenyl)-4-(1H-1,2,4-triazol-1-yl)-4,5-dihydropyrazole 3a–3n were synthesized by the annulation of 2-aryloxyacetohydrazides with 3-aryl-1-t-butyl (or phenyl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-ones (2) in the presence of a catalytic amount of acetic acid. Compounds 2 were obtained by the Knoevenagel reactions of 1-t-butyl (or phenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (1) with aromatic aldehydes in the presence of piperidine. Their structures were confirmed by IR, 1H-NMR, ESI-MS, and elemental analyses. The preliminary bioassay indicated that some compounds displayed moderate to excellent fungicidal activity. For example, compounds 3l, 3m, and 3n possessed 100% inhibition against Cercospora arachidicola Hori at the concentration of 50 mg/L.