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Synthesis and Fungicidal Activity of (1Z, 3Z)-4,4-Dimethyl-1-substitutedphenyl-2-(1H-1,2,4-triazol-1-yl)-pent-1-en -3-one O-[2,4-dimethylthiazole(or 4-methyl-1,2,3-thiadiazole)]-5-carbonyl Oximes

  作者 MAO HUIYU; SONG HONG; SHI DEQING  
  选自 期刊  Journal of Heterocyclic Chemistry;  卷期  2012年49-3;  页码  511-515  
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[摘要]A series of novel (Z)-1-tert-butyl (or phenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone O-[2,4-dimethylthiazole (or 4-methyl-1,2,3-thiadiazole) -5-carbonyl] oximes 5a5c and (1Z, 3Z)-4,4-dimethyl-1-substitutedphenyl-2-(1H-1,2,4-triazol-1-yl)-pent-1-en-3-one O-[2,4-dimethylthiazole (or 4-methyl-1,2,3-thiadiazole)-5-carbonyl] oximes 6a6e were synthesized by the condensations of (Z)-1-tert-butyl (or phenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone oximes 3 or (1Z, 3Z)-4,4-dimethyl-1-substitutedphenyl-2-(1H-1,2,4-triazol-1-yl)-pent-1-en-3-one oximes 4 with 2,4-dimethylthiazole-5-carbonyl chloride or 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride in the basic condition. Their structures were confirmed by IR, 1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays showed the title compounds 5 and 6 exhibited moderate to good fungicidal activities. For example, compound 6c possessed 86.4% inhibition against Fusarium oxysporum, and compound 6b exhibited 86.4 and 100% inhibition against Fusarium oxysporum and Cercospora arachidicola Hori at the concentration of 50 mg/L, respectively.

 
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