Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (07): 1114-1121. Previous Articles     Next Articles

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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 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 Published:2011-02-25
  • Contact: Wen-Gui DUAN E-mail:dwg118@gxu.edu.cn

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