有机化学 ›› 2020, Vol. 40 ›› Issue (8): 2547-2554.DOI: 10.6023/cjoc202004050 上一篇    下一篇

研究简报

(E)-3-(1-亚胺基乙基)-5,5-二取代-4-甲氨基呋喃-2(5H)-酮的合成及其意外的杀虫活性

赵宇, 刘鑫磊, 李益豪, 许磊川, 苏彦豪, 蒋家珍, 王明安   

  1. 中国农业大学应用化学系 农药创新研究中心 北京 100193
  • 收稿日期:2020-04-29 修回日期:2020-05-10 发布日期:2020-05-29
  • 通讯作者: 王明安 E-mail:wangma@cau.edu.cn
  • 基金资助:
    国家自然科学基金(No.21772229)资助项目.

Synthesis and Unexpected Insecticidal Activity of (E)-3-(1-Imino-ethyl)-5,5-disubstituted-4-(methylamino)furan-2(5H)-one

Zhao Yu, Liu Xinlei, Li Yihao, Xu Leichuan, Su Yanhao, Jiang Jiazhen, Wang Ming'an   

  1. Innovation Center of Pesticide Research, Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2020-04-29 Revised:2020-05-10 Published:2020-05-29
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21772229).

为了提高化合物对植物病原菌的杀菌活性及扩大多样性导向合成策略建立的分子库,以甲氨基替换3-(1-亚胺基乙基)-5,5-二取代-4-苯基呋喃-2(5H)-酮的苯基,设计合成了18个新颖的(E)-3-(1-亚胺基乙基)-5,5-二取代-4-甲氨基呋喃-2(5H)-酮,结构经过1H NMR,13C NMR,HR-ESI-MS表征.(E)-3-(1-(4-甲氧基苄氧亚胺基)乙基)-4-甲氨基-1-氧杂螺[4.5]癸-3-烯-2-酮(5O)还经过X射线衍射表征.生物活性测试结果表明,所有化合物对测试的四种植物病原菌均未显示明显的活体杀菌活性,但是意外地发现多个化合物在600 μg/mL浓度时对桃蚜、粘虫和小菜蛾的致死率均为100%,显示出良好的杀虫活性.

关键词: (E)-3-(1-亚胺基乙基)-5,5-二取代-4-甲氨基呋喃-2(5H)-酮, 多样性导向合成, 肟醚, 杀虫活性

In order to improve the fungicidal activity against phytopathogens and enlarge the constructed molecular library, eighteen novel (E)-3-(1-iminoethyl)-5,5-disubstituted-4-(methylamino)-furan-2(5H)-ones were designed and synthesized based on the diversity-oriented synthesis strategy when the C-4 phenyl group of 3-(1-iminoethyl)-5,5-disubstituted-4-phenylfuran-2(5H)-one was replaced with the methylamino group. Their structures were characterized by 1H NMR, 13C NMR, HR-MS spectral data. The crystal structure of (E)-3-(1-((4-methoxybenzyloxy)imino)ethyl)-4-(methylamino)-1-oxaspiro[4.5]dec-3-en-2-one (5O) was determined by X-ray diffraction analysis. The bioassay results indicated that all compounds did not exhibit significant in vivo fungicidal activities against phytopathogens, but some of them showed good insecticidal activities against Plutella xylostella, Mythimna seprata and Myzus persicae with 100% mortality at the concentration of 600 μg/mL.

Key words: (E)-3-(1-iminoethyl)-5,5-disubstituted-4-(methylamino)furan-2(5H)-one, diversity-oriented synthesis, oxime ether scaffold, insecticidal activity