高等学校化学学报 ›› 2012, Vol. 33 ›› Issue (07): 1481-1485.doi: 10.3969/j.issn.0251-0790.2012.07.021

• 有机化学 • 上一篇    下一篇

N-[(2-烷氧基)-取代苯乙基]-苯乙酰胺类化合物的合成及生物活性

姚红伟, 崔灿, 李永强, 王力钟, 李正名, 赵卫光   

  1. 南开大学元素有机化学国家重点实验室, 农药国家工程中心, 天津 300071
  • 收稿日期:2011-09-22 出版日期:2012-07-10 发布日期:2012-07-10
  • 通讯作者: 赵卫光, 男, 博士, 研究员, 主要从事农药与有机合成化学研究. E-mail: zwg@nankai.edu.cn E-mail:zwg@nankai.edu.cn
  • 基金资助:

    国家自然科学基金(批准号: 20772069, 21172124)、 国家科技支撑计划项目(批准号: 2011BAE06B05-3)和国家"九七三"计划项目(批准号: 2010CB126105)资助.

Synthesis and Bioactivity of N-(2-Alkoxy-2-substituted phenyl-ethyl)phenyl Amide

YAO Hong-Wei, CUI Can, LI Yong-Qiang, WANG Li-Zhong, LI Zheng-Ming, ZHAO Wei-Guang   

  1. State Key Laboratory of Elemento-Oranic Chemistry, National Pesticide Engineering Research Center, Nankai University, Tianjin 300071, China
  • Received:2011-09-22 Online:2012-07-10 Published:2012-07-10

摘要: 以双炔酰菌胺为模板, 利用"基团反转"原理将酰胺中的羰基和氮原子交换位置, 设计了一系列苯乙酰儿茶酚胺类化合物. 从取代苯乙酮出发, 经过溴代、 胺化、 还原制备2-氨基-1-取代苯乙醇(6), 然后与取代苯乙酸反应制备酰胺(7), 最后经烷基化得到一系列保持氮原子位置不变的N-(2-烷氧基-2-取代苯基乙基)苯乙酰胺类化合物(8). 所有目标化合物均通过核磁共振氢谱、 元素分析或高分辨质谱确认, 并测试了其生物活性. 结果表明, 部分化合物对黄瓜霜霉病具有较好的防治活性, 化合物8k在浓度为100 μg/mL时对黄瓜霜霉防效可达75%. 研究还发现, 该类化合物均对蚜虫具有较好的防治效果.

关键词: 杀菌活性, 杀虫活性, 2-氨基-1-苯乙醇, 苯乙酰胺

Abstract: Mandipropanid is the first mandelamlamide fungicide on the market. A series of novel N-(2-alkoxy-2-substituted phenyl-ethyl) phenyl amide(8) was designed according to exchange the position of NH and C=O from mandipropamid. The target compounds were synthesized from benzene acetic acid and acetophenone(3) by bromination, amination and so on. Their structures were characterized by 1H NMR, elemental analysis or high resolution mass spectra(HRMS). The results of the preliminary biological activity tests show that some of them like compound 8k exhibit good anti-fungal activities against Pseudoperonospora cubenis at 100 μg/mL. The study also finds that these compounds have a certain control on the effect of Tetranychus cinnabarinus.

Key words: Anti-fungal activity, Insecticide activity, 2-Amino-1-phenylethanol, Phenylethyl amide

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