吡唑腙及其噁二唑衍生物合成和抑菌活性

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

利用Vilsmeier-Haak反应得到取代-4-甲酰基吡唑中间体;将其与芳氧乙酰肼反应,合成5个吡唑腙类化合物3。再将其进行关环反应,制得5个含吡唑环和噁二唑环的双杂环化合物4。化合物3和4的结构均经IR、1H NMR、MS和元素分析并确证。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50 mg/L时,化合物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作用(>70%),其中化合物4d、4e对棉花立枯病菌的抑制率大于95%。

The active intermediate substitution-4-formacyl pyrazole was obtained from benzene hydrazone via the Vilsmeier-Haak reaction.Then it reacted with 4-substituted aryloxyacetyl hydrazine to form compounds 3.Finally Bis-heterocyclic compounds 4 were synthesized via cyclic reaction.All the 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.Compounds 3 and 4 underwent a preliminary test of antibacterial activity against Fusarium oxyaporium,Verticillium dahliae,Rhizoctonia solani,Pychium aphanidermatum,Alternaria solani,Sclerotinia sclerotiorum.The results show that the inhibiting rates of the bis-heterocyclic compounds 4 are higher than those of the pyrazole hydrazones 3 obviously.Compounds 3d and 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 inh.ibitory activities（〉70%） against these six germs and compounds 4d and 4e showed inhibitory activities（〉95%） against Rhizoctonia solani.