应用化学 ›› 2009, Vol. 26 ›› Issue (08): 961-965.

• 研究论文 • 上一篇    下一篇

吡唑腙及其双杂环化合物的设计、合成及生物活性

王春灵1,杨金凤2,陈思羽2,李炳奇2*   

  1. (石河子大学1.生命科学学院;2.化学化工学院 石河子 832003)
  • 收稿日期:2008-08-18 修回日期:2008-12-11 出版日期:2009-08-10 发布日期:2009-08-10
  • 通讯作者: 李炳奇,男,教授; E-mail:yjfmht940216@sohu.com; 研究方向:天然有机化学
  • 基金资助:
    石河子大学高层次人才启动资金专项资助项目(RCZX200632)

Design、Synthesis and Biological Activity of Pyrazole Hydrazones and Diheterocyclic Compounds

WANG Chun-Ling1, YANG Jin-Feng2, CHEN Shi-Yu2, LI Bing-Qi2*   

  1. (1.Department of Life Science,Shihezi University,Shihezi;
    2.College of Chemistry and Chemical Engineering,Shihezi University,Shihezi 832003)
  • Received:2008-08-18 Revised:2008-12-11 Published:2009-08-10 Online:2009-08-10

摘要:

利用Vilsmeier-Haak反应得到活性中间体,取代-4-甲酰基吡唑;将其与芳氧乙酰肼反应,合成5个吡唑腙类化合物3,再经关环反应,制得5个吡唑类双杂环化合物4。所有新化合物的结构均经IR,1H NMR,MS和元素分析确证了结构。对新化合物3,4分别进行了棉花枯萎病菌、棉花黄萎病菌、棉花立枯病菌、瓜果腐霉病菌、番茄早疫病菌、向日葵菌核病菌等初步的抑菌活性测试,结果表明,吡唑类双杂环化合物4的抑菌效果明显高于吡唑腙化合物3。在质量浓度为50mg/L时,3d、3e对番茄早疫病菌、向日葵菌核病菌有较好的抑制效果(﹥80%);双杂环化合物4对6种病菌均有明显的抑制效果(﹥70%),其中4d、4e对棉花立枯病菌的抑制率大于95%。

关键词: 吡唑, 噁二唑, 合成, 杀菌活性

Abstract:

The active intermediate that substitution-4-formacyl pyrazole were obtained from benzene hydrazone via the Vilsmeier-Haak reaction. Then they reacted with 4-substituted aryloxyacetyl hydrazine to form the compounds 3. Finally Bis-heterocyclic compound 4 were synthesized via cyclic reaction. All newly synthesized compounds have not been reported and their structures have been established on the basis of IR, 1H NMR, Ms spectral data and elemental analysis. The compound 3,4 conducted a preliminary test of antibacterial activity about Fusarium oxyaporium、Verticillium dahliae、Rhizoctonia solani、Pychium aphanidermatum、Alternaria solani、Sclerotinia sclerotiorum. The results showed that the inhibiting rate of the Bis-heterocyclic compounds 4 higher than the pyrazole hydrazones 3 obviously. Compounds 3d、3e showed good inhibitory activities (﹥80%) against Alternaria solani and Sclerotinia sclerotiorum at a concentration of 50 mg/L. In contrast, Bis-heterocyclic Compounds 4 have obviously inhibitory activities (﹥70%) against these six germ and compounds 4d、4e showed inhibitory activities (﹥95%) against Rhizoctonia solani .

Key words: pyrazole, oxadiazole, synthesis, fungicidal activity

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