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林产化学与工业 ›› 2014, Vol. 34 ›› Issue (3): 73-81.doi: 10.3969/j.issn.0253-2417.2014.03.013

• 研究报告 • 上一篇    下一篇

N-氨乙基萜品烯马来酰亚胺基磺酰胺化合物的合成及抑菌活性

蔺志铎1, 段文贵1, 林桂汕1, 廖静妮1, 赖刚1, 殷宪龙1, 雷福厚2   

  1. 1. 广西大学 化学化工学院, 广西 南宁 530004;
    2. 广西林产 化学与工程重点实验室, 广西 南宁 530006
  • 收稿日期:2013-05-07 出版日期:2014-06-25 发布日期:2014-06-25
  • 通讯作者: 段文贵(1964- ),广西资源人,教授,博士生导师,主要从事天然资源化学和有机合成研究;E-mail:wgduan@gxu.edu.cn。 E-mail:wgduan@gxu.edu.cn
  • 作者简介:蔺志铎(1986- ),男,甘肃凉州人,硕士生,从事天然产物改性及有机合成研究
  • 基金资助:
    国家自然科学基金资助项目(31260164);广西林产化学与工程重点实验室开放基金项目(GXFC11-02);广西大学实验室建设与实验教学改革项目(20120311)

Syntheses and Fungicidal Activities of N-Aminoethyl-terpinene- maleimide-based Sulfamide Compounds

LIN Zhi-duo1, DUAN Wen-gui1, LIN Gui-shan1, LIAO Jing-ni1, LAI Gang1, YIN Xian-long1, LEI Fu-hou2   

  1. 1. College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China;
    2. Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530006, China
  • Received:2013-05-07 Online:2014-06-25 Published:2014-06-25

摘要: α-蒎烯(1)为原料, 经Wagner-Meerwein 重排得α-萜品烯(2), 2与马来酸酐发生Diels-Alder 环加成反应得到α-萜品烯马来酸酐(3),3再与N-芳磺酰基乙二胺(4)反应,合成得到12个新型N-氨乙基萜品烯马来酰亚胺基磺酰胺类化合物(5a~5l)。采用FT-IR、 1H NMR、13C NMR、ESI-MS和元素分析等多种手段对目标产物作了分析表征。初步的生物活性测试表明,目标化合物具有一定的抑菌活性,其中化合物5c(R=3-CH3)在质量浓度为 50 mg/L 时对花生褐斑病菌、番茄早疫病菌、苹果轮纹病菌和小麦赤霉病菌的抑制率分别达68.8%、68.3%、62.3%和53.8%。

关键词: α-蒎烯, N-氨乙基萜品烯马来酰亚胺基磺酰胺, 合成, 抑菌活性

Abstract: α-Pinene (1) was converted into α-terpinene(2) by Wagner-Meerwein rearrangement,followed by Diels-Alder cycloaddtion reaction of 2 with maleic anhydride to obtain α-terpinene-maleic anhydride adduct(3). Then, twelve novel N-aminoethyl-terpinene-maleimide-based sulfamide compounds(5a-5l) were synthesized by the reaction of compound 3 with N-aryl sulfonyl ethylenediamine(4). The target compounds were characterized by means of FT-IR, 1H NMR, 13C NMR, ESI-MS, and elemental analysis. The preliminary bioassay showed that the title compounds exhibited a certain fungicidal activities. Among then, compound 5c(R=3-CH3) had inhibition rates of 68.8%, 68.3%, 62.3% and 53.8% against Cercospora rachidicola, Alternaria solani, Physalospora piricola and Gibberella zeae at the concentration of 50 mg/L, respectively.

Key words: α-pinene, N-aminoethyl-terpinene-maleimide-based sulfamide, synthesis, fungicidal activities

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