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2020 , Vol. 40 >Issue 8: 2547 - 2554

DOI: https://doi.org/10.6023/cjoc202004050

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
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  • 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

  网络出版日期: 2020-05-29

基金资助

国家自然科学基金（No.21772229）资助项目.

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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
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  • Innovation Center of Pesticide Research, Department of Applied Chemistry, China Agricultural University, Beijing 100193

Received date: 2020-04-29

  Revised date: 2020-05-10

  Online published: 2020-05-29

Supported by

Project supported by the National Natural Science Foundation of China (No. 21772229).

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摘要

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

本文引用格式

赵宇 , 刘鑫磊 , 李益豪 , 许磊川 , 苏彦豪 , 蒋家珍 , 王明安 . (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[J]. 有机化学, 2020 , 40(8) : 2547 -2554 . DOI: 10.6023/cjoc202004050

Abstract

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

参考文献

[1] (a) Schreiber, S. L. Science 2000, 287, 1964.
(b) Garcia-Castro, M.; Zimmermann, S.; Sankar, M. G.; Kumar, K. Angew. Chem., Int. Ed. 2016, 55, 7586.
(c) Maiti, B.; Chanda, K. RSC Adv. 2016, 6, 50384.
[2] Pham, T. T.; Chen, X.; Sohnel, T.; Yan, N.; Sperry, J. Green Chem. 2020, 22, 1978.
[3] Cotos, L.; Donzel, M.; Elhabiri, M.; Davioud-Charvet, E. Chem.-Eur. J. 2020, 26, 3314.
[4] Tang, B.; Yang, M. Y.; Zhao, Y.; Kong, L. Q.; Wang, W. W.; Wang, M. A. Molecules 2015, 20, 13740.
[5] Zhao, Y.; Tang, B.; Liu, X. L.; Li, W. Z.; Huang, M. Y.; Wang, M. A. Chin. J. Org. Chem. 2017, 37, 975(in Chinese). (赵宇, 汤博, 刘鑫磊, 李婉祯, 黄铭一, 王明安, 有机化学, 2017, 37, 975.)
[6] Tang, B.; Guan, A. Y.; Zhao, Y.; Jiang, J. Z.; Wang, M. A.; Zhou, L. G. Chin. J. Chem. 2017, 35, 1133.
[7] Zhao, Y.; Tang, B.; Guan, A. Y.; Wang, W. W.; Zhang, Z. H.; Wang, M. A. Synthesis 2017, 49, 4663.
[8] Zhao, Y.; Liu, X. L.; Wang, W. W.; Geng, R.; Wang, M. A. Synthesis 2018, 50, 4055.
[9] Guan, A. Y.; Zhao, Y.; Wang, W. W.; Liu, X. L.; Wang, M. A. Chin. J. Org. Chem. 2018, 38, 2767(in Chinese). (关爱莹, 赵宇, 王卫伟, 刘鑫磊, 王明安, 有机化学, 2018, 38, 2767.)
[10] Zhao, Y.; Guan, A. Y.; Li, W. Z.; Wang, W. W.; Liu, X. L.; Wang, M. A. Chin. J. Org. Chem. 2019, 39, 1344(in Chinese). (赵宇, 关爱莹, 李婉祯, 王卫伟, 刘鑫磊, 王明安, 有机化学, 2019, 39, 1344.)
[11] Geng, R.; Zhao, Y.; Li, Y. H.; Liu, X. L.; Wang, M. A. Chin. J. Org. Chem. 2019, 39, 3574(in Chinese). (耿瑞, 赵宇, 李益豪, 刘鑫磊, 王明安, 有机化学, 2019, 39, 3574.)
[12] Zhao, Y.; Liu, X. L.; Wang, W. W.; Geng, R.; Wang, M. A. Chin. J. Org. Chem. 2020, 40, 694(in Chinese). (赵宇, 刘鑫磊, 王卫伟, 耿瑞, 王明安, 有机化学, 2020, 40, 694.)
[13] (a) Rao, Y. S. Chem. Rev. 1976, 76, 625.
(b) Allan, R. D.; Johnston, G. A. R.; Kazlauskas, R.; Tran, H. W. J. Chem. Soc., Perkin Trans 1 1983, 2983.
(c) Gelmi, M. L.; Clerici, F.; Melis, A. Tetrahedron 1997, 53, 1843.
(d) Li, J.; Yang, P.; Yao, M.; Deng, J.; Li, A. J. Am. Chem. Soc. 2014, 136, 16477.
[14] (a) Nauen, R.; Jeschke, P.; Velten, R.; Beck, M. E.; Ebbinghaus-kintscher, U.; Thielert, W.; Wolfel, K.; Hass, M.; Kunz, K.; Raupach, G. Pest Manage. Sci. 2015, 71, 850.
(b) Jeanmart, S.; Edmunds, A. J. F.; Lamberth, C.; Pouliot, M. Bioorg. Med. Chem. 2016, 24, 317.
(c) Chen, X. D.; Seo, M.; Stelinski, L. L. Crop Prot. 2017, 98, 102.
(d) Roditakis, E.; Stavrakaki, M.; Grispou, M.; Achimastou, A.; Waetermeulen, X. V.; Nauen, R.; Tsagkarakou, A. Pest Manage. Sci. 2017, 73, 1574.
[15] Wang, Y.; Zheng, D.; Wang, Y.; Ye, H.; Yao, W.; Ding, Y.; Gu, H.; Feng, X.; Li, L.; Dai, H. Chin. J. Org. Chem. 2019, 39, 2053(in Chinese). (王誉蓉, 郑丹丹, 王杨, 叶浩, 姚炜, 丁颖, 顾海鹰, 冯霞, 李玲, 戴红, 有机化学, 2019, 39, 2053.)
[16] Xie, Y.; Huang, Z.; Yan, H.; Li, J.; Ye, L.; Che, L.; Tu, S. Chem. Biol. Drug Des. 2015, 85, 743.
[17] Zan, N.; Zhang, Y.; Zhang, S.; Liu, S.; Jiang, L. Chin. J. Org. Chem. 2017, 37, 2767(in Chinese). (昝宁宁, 张钰镭, 张帅, 刘思, 姜林, 有机化学, 2017, 37, 2767.)
[18] Zhang, W.; Wu, A.; Xu, H.; Mo, Y.; Chen, J.; Shen, L. Helv. Chim. Acta 2016, 99, 696.
[19] Guan, A. Y.; Liu, C. L.; Chen, W.; Yang, F.; Xie, Y.; Zhang, J. B.; Li, Z. N.; Wang, M. A. J. Agric. Food Chem. 2017, 65, 1272.
[20] Guan, A. Y.; Wang, M. A.; Yang, J. L.; Wang, L. Z.; Xie, Y.; Lan, J.; Liu, C. L. J. Agric. Food Chem. 2017, 65, 10829.
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