有机化学 ›› 2011, Vol. 31 ›› Issue (07): 1114-1121. 上一篇    下一篇

研究简报

2-取代氨基-5-去氢枞基-1,3,4-噁二唑衍生物的合成及除草活性

莫启进,段文贵*,李行任,黄丹平,罗湛江   

  1. (广西大学化学化工学院 南宁 530004)
  • 收稿日期:2010-08-05 修回日期:2010-12-20 出版日期:2011-07-25 发布日期:2011-02-25
  • 通讯作者: 段文贵 E-mail:dwg118@gxu.edu.cn

Synthesis and Herbicidal Activity of 2-Substituted Amino- 5-dehydroabietyl-1,3,4-oxadiazole Derivatives

MO Qi-Jin, DUAN Wen-Gui, LI Xing-Ren, HUANG Dan-Ping, LUO Zhan-Jiang   

  1. (College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004)
  • Received:2010-08-05 Revised:2010-12-20 Online:2011-07-25 Published:2011-02-25
  • Contact: Wen-Gui DUAN E-mail:dwg118@gxu.edu.cn

以去氢枞酸为原料, 经酰化后与水合肼反应合成去氢枞酰肼3, 再与芳基异硫氰酸酯反应, 得到中间体1-去氢枞酰基-4-取代基氨基硫脲4, 4在Hg(OAc)2/EtOH条件下关环, 合成得到一系列新型2-取代氨基-5-去氢枞基-1,3,4-噁二唑化合物5. 采用IR, MS, 1H NMR, 13C NMR和元素分析等方法对中间体4和目标产物5进行了分析和表征. 初步的除草活性测试表明, 化合物45对油菜的胚根生长以及对稗草的幼苗生长有一定的抑制作用, 其中化合物4d在浓度为100 mg/L时对油菜胚根生长的抑制率达88.2%.

关键词: 去氢枞酸, 1-去氢枞酰基-4-取代基氨基硫脲, 2-取代氨基-5-去氢枞基-1,3,4-噁二唑, 除草活性

Dehydroabietic acid chloride was prepared by the reaction of dehydroabietic acid with thionyl chloride, followed by the reaction of the dehydroabietic acid chloride with hydrazine hydrate to provide dehydroabietacyl hydrazine. A series of target compounds 2-substituted amino-5-dehydroabietyl-1,3,4-oxadiazoles 5 were synthesized by the cyclization of 1-dehydroabietacyl-4-substituted thiosemicarbazides (4) under catalysis of Hg(OAc)2/EtOH. And the intermediates 4 were prepared by the reaction of dehy-droabietacyl hydrazine with aryl isothiocyanates. The intermediates 4 and target compounds 5 were analyzed and characterized by means of IR, MS, 1H NMR, 13C NMR techniques and elemental analysis. The preliminary herbicidal assay showed that all the compounds 4 and 5 exhibited a certain growth inhibition on rape root (Brassica campestris) and barnyard grass (Echinochloa crusgalli (L.)). Among the tested compounds, 4d dis-played 88.2% inhibition on rape root (Brassica campestris) at 100 mg/L concentration in herbicidal tests.

Key words: dehydroabietic acid, 1-dehydroabietacyl-4-substituted thiosemicarbazide, 2-substituted amino-5-dehydroabietyl-1,3,4-oxadiazole, herbicidal activity