Citation: Zhao Yu, Liu Xinlei, Li Yihao, Xu Leichuan, Su Yanhao, Jiang Jiazhen, Wang Ming'an. Synthesis and Unexpected Insecticidal Activity of (E)-3-(1-Imino-ethyl)-5, 5-disubstituted-4-(methylamino)furan-2(5H)-one[J]. Chinese Journal of Organic Chemistry, ;2020, 40(8): 2547-2554. doi: 10.6023/cjoc202004050 shu

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

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

Corresponding author: Wang Ming'an, wangma@cau.edu.cn
Received Date: 29 April 2020
Revised Date: 10 May 2020
Available Online: 27 May 2020
Fund Project: the National Natural Science Foundation of China 21772229Project supported by the National Natural Science Foundation of China (No. 21772229)

Figures(4)

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.
1. [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. [2]
  Pham, T. T.; Chen, X.; Sohnel, T.; Yan, N.; Sperry, J. Green Chem. 2020, 22, 1978. doi: 10.1039/D0GC00208A
3. [3]
  Cotos, L.; Donzel, M.; Elhabiri, M.; Davioud-Charvet, E. Chem.-Eur. J. 2020, 26, 3314. doi: 10.1002/chem.201904220
4. [4]
  Tang, B.; Yang, M. Y.; Zhao, Y.; Kong, L. Q.; Wang, W. W.; Wang, M. A. Molecules 2015, 20, 13740. doi: 10.3390/molecules200813740
5. [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).
6. [6]
  Tang, B.; Guan, A. Y.; Zhao, Y.; Jiang, J. Z.; Wang, M. A.; Zhou, L. G. Chin. J. Chem. 2017, 35, 1133. doi: 10.1002/cjoc.201600794
7. [7]
  Zhao, Y.; Tang, B.; Guan, A. Y.; Wang, W. W.; Zhang, Z. H.; Wang, M. A. Synthesis 2017, 49, 4663. doi: 10.1055/s-0036-1588463
8. [8]
  Zhao, Y.; Liu, X. L.; Wang, W. W.; Geng, R.; Wang, M. A. Synthesis 2018, 50, 4055. doi: 10.1055/s-0037-1609548
9. [9]
  Guan, A. Y.; Zhao, Y.; Wang, W. W.; Liu, X. L.; Wang, M. A. Chin. J. Org. Chem. 2018, 38, 2767(in Chinese).
10. [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).
11. [11]
  Geng, R.; Zhao, Y.; Li, Y. H.; Liu, X. L.; Wang, M. A. Chin. J. Org. Chem. 2019, 39, 3574(in Chinese).
12. [12]
  Zhao, Y.; Liu, X. L.; Wang, W. W.; Geng, R.; Wang, M. A. Chin. J. Org. Chem. 2020, 40, 694(in Chinese).
13. [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. [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. [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).
16. [16]
  Xie, Y.; Huang, Z.; Yan, H.; Li, J.; Ye, L.; Che, L.; Tu, S. Chem. Biol. Drug Des. 2015, 85, 743. doi: 10.1111/cbdd.12460
17. [17]
  Zan, N.; Zhang, Y.; Zhang, S.; Liu, S.; Jiang, L. Chin. J. Org. Chem. 2017, 37, 2767(in Chinese).
18. [18]
  Zhang, W.; Wu, A.; Xu, H.; Mo, Y.; Chen, J.; Shen, L. Helv. Chim. Acta 2016, 99, 696. doi: 10.1002/hlca.201600133
19. [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. doi: 10.1021/acs.jafc.6b05580
20. [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. doi: 10.1021/acs.jafc.7b03898
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