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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (06): 1065-1070. 上一篇    下一篇

研究简报

2-取代硫醚-5-(5,7-二甲基-1,2,4-三唑并[1,5-a]嘧啶基)-1,3,4-噁二唑/噻二唑类化合物的合成及生物活性

龙德清*,a，汪焱钢b，唐传球a，李德江a，王锋尖a   

  1. (a郧阳师范高等专科学校化学系 丹江口 442700)
    (b华中师范大学化学学院 武汉 430079)
  • 收稿日期:2007-07-16 修回日期:2007-11-14 发布日期:2008-06-26
  • 通讯作者: 龙德清

Synthesis and Biological Activities of 2-Alkylthio-5-(5,7-dimethyl- 1,2,4-triazolo[1,5-a]pyrimidine-5-yl)-1,3,4-oxadiazole/ 1,3,4-thiadiazole Derivatives

LONG De-Qing*,a, WANG Yan-Gangb, TANG Chuan-Qiua
LI De-Jianga, WANG Feng-Jiana   

  1. (a Department of Chemistry, Yunyang Teachers College, Danjiangkou 442700)
    (b College of Chemistry, Central China Normal University, Wuhan 430079)
  • Received:2007-07-16 Revised:2007-11-14 Published:2008-06-26
  • Contact: LONG De-Qing

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以5-氨基-1H-1,2,4-三唑-3-羧酸乙酯为起始原料, 设计合成了11个新型的2-取代硫醚-5-(5,7-二甲基-1,2,4-三唑并[1,5-a]嘧啶基)-1,3,4-噁二唑类化合物(5)和6个新型的2-取代硫醚-5-(5,7-二甲基-1,2,4-三唑并[1,5-a]嘧啶基)-1,3,4-噻二唑类化合物(8). 通过1H NMR, MS和元素分析对所合成的化合物进行了结构表征. 初步的生物活性测试结果表明, 所合成的化合物均表现出不同程度的除草及杀菌活性, 其中化合物5k和8f的活性最好, 在50 mg/L浓度下对水稻纹枯病菌的抑制率达90%以上.

关键词: 生物活性, 1,2,4-三唑并[1,5-a]嘧啶, 合成, 1,3,4-噁二唑, 联杂环, 1,3,4-噻二唑

Eleven novel 2-alkylthio-5-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-5-yl)-1,3,4-oxadiazole derivatives (5) and six novel 2-alkylthio-5-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-5-yl)-1,3,4-thia- diazole derivatives (8) have been designed and synthesized by using 5-amino-3-ethoxycarbonyl-1H-1,2,4- tri-azole as a starting material. All compounds synthesized were confirmed by 1H NMR, MS spectra and elemental analyses. Preliminary bioassay indicates that some compounds display herbicidal ac-tivity and excellent fungicidal activity to some extent, and among them the compounds 5k and 8f b> exhibit higher than 90% inhibition effect against Rhizoctonia solani in dosage of 50 mg/L.

Key words: 1,3,4-oxadiazole, synthesis, 1,3,4-thiadiazole, linked biheterocycle, biological activity, 1,2,4-triazolo[1,5-a]pyrimidine