Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis, Characterization and Biological Activities of Novel (E)-3-(1-(Alkyloxyamino)ethylidene)-1-alkylpyrrolidine-2,4-dione Derivatives

  • Zhu, Zhao-Yong (Department of Chemistry, College of Science, Nanjing Agricultural University) ;
  • Shi, Qing-Ming (Department of Chemistry, College of Science, Nanjing Agricultural University) ;
  • Han, Bao-Feng (Department of Chemistry, College of Science, Nanjing Agricultural University) ;
  • Wang, Xian-Feng (Department of Chemistry, College of Science, Nanjing Agricultural University) ;
  • Qiang, Sheng (College of Life Science, Nanjing Agricultural University) ;
  • Yang, Chun-Long (Department of Chemistry, College of Science, Nanjing Agricultural University)
  • Received : 2010.05.24
  • Accepted : 2010.07.04
  • Published : 2010.09.20
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Abstract

Twenty novel tetramic acid derivatives (E)-3-(1-(alkyloxyamino)ethylidene)-1-alkylpyrrolidine-2,4-diones were synthesized by the reaction of 3-(1-hydroxyethylidene)pyrrolidine-2,4-diones with O-alkyl hydroxylamines. The title compounds were confirmed by IR, $^1H$ NMR, MS and elemental analysis. The structure of compound 6r was further verified by X-ray diffraction crystallography. The bioassays showed that most of the title compounds exhibited noticeable herbicidal and fungicidal activities.

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References

  1. Pogocki, D.; Ruman, T.; Danilczuk, M.; Danilczuk, M.; Celuch, M.; Wałajtys-Rode, E. Eur. J. Pharm. 2007, 563, 18. https://doi.org/10.1016/j.ejphar.2007.02.038
  2. Nakai, Y.; Tepp, W. H.; Dickerson, T. J.; Johnson, E. A.; Janda, K. D. Bioorg. Med. Chem. 2009, 17, 1152. https://doi.org/10.1016/j.bmc.2008.12.042
  3. Vayias, B. J.; Athanassiou, C. G.; Buchelos, C. Th. Crop Protection 2006, 25, 766. https://doi.org/10.1016/j.cropro.2005.10.011
  4. Varma, J.; Dubey, N. K. Intern. J. Food Microbio. 2001, 68, 207. https://doi.org/10.1016/S0168-1605(01)00506-2
  5. Schobert, R.; Schlenk, A. Bioorg. Med. Chem. 2008, 16, 4203. https://doi.org/10.1016/j.bmc.2008.02.069
  6. Dixon, D. J.; Ley, S. V.; Gracza, T.; Szolcsanyi, P. J. Chem. Soc., Perkin Trans. 1 1999, 839.
  7. Aoki, S.; Higuchi, K.; Ye, Y.; Satari, R.; Kobayashi, M. Tetrahedron 2000, 56, 1833. https://doi.org/10.1016/S0040-4020(00)00092-2
  8. Li, J. Y.; Strobel, G.; Harper, J.; Lobkovsky, E.; Clardy, J. Org. Lett. 2000, 2, 767. https://doi.org/10.1021/ol000008d
  9. Chen, S. G.; Yin, C. Y.; Dai, X. B.; Qiang, S.; Xu, X. M. Biochim. Biophys. Acta 2008, 62, 279. https://doi.org/10.1016/0006-3002(62)90041-0
  10. Gallardo, G. L.; Peña, N. I.; Chacana, P.; Terzolo, H. R.; Cabrera, G. M. World J. Microb. Biotechnol. 2004, 20, 609. https://doi.org/10.1023/B:WIBI.0000043175.23621.8c
  11. Antony, M.; Gupta, K. P.; Janardanan, K. K.; Mehrotra, N. K. Cancer Lett. 1991, 61, 21. https://doi.org/10.1016/0304-3835(91)90072-P
  12. Zhu, Y. Q.; Zou, X. M.; Hu, F. Z.; Yao, C. S.; Liu, B.; Yang, H. Z. J. Agric. Food Chem. 2005, 53, 9566. https://doi.org/10.1021/jf051510l
  13. Zhu, X, J.; Huang, L.; Wang, X. F.; Zhu, Z. Y.; Zheng, X. Q.; Qiang, S.; Yang, C. L. Chi. J. Org. Chem. 2009, 29, 1784.
  14. Liu, A. P.; Wang, X. G.; Ou, X. M.; Huang, M. Z.; Duan, X. S.; Wang, Y. L.; Pang, H. L. New Pesticides 2005, 42(4), 3.
  15. Song, B. A.; Liu, X. H.; Yang, S.; Hu, D. Y.; Jin, L. H.; Zhang, Y. T. Chi. J. Org. Chem. 2005, 25, 507.
  16. Liu, A. P.; Yao, J. R. Chi. J. Pesitic. 2004, 43(5), 196.
  17. Yang, C. L.; Qiang, S.; Huang, L.; Zhang, P.; Zhu, Z. Y. CN Pat. 1817859, 2006.
  18. Du, Z. T.; Qiu, G. R.; Ma, J. Y.; Wu, T. X.; Pan, X. F. Chem. Reagents 2004, 26(2), 117.
  19. Wu, Y. X.; Dai, L. Y. Chi. J. Pestic. 2004, 43(3), 113.
  20. Barkley, J. V.; Markopoulos, J.; Markopoulou, O. J. Chem. Soc. Perkin Trans. 2 1994, 1271.
  21. Zhu, Z. Y.; Wang, X. F.; Meng, F. G.; Li, Q. B.; Zheng, X. Q.; Qiang, S.; Yang, C. L. J. Heterocyclic Chem. 2010, DOI 10.1002/jhet.452.
  22. Luo, Y. P.; Yang, G. F. Bioorg. Med. Chem. 2007, 15, 1716. https://doi.org/10.1016/j.bmc.2006.12.002
  23. Chen, X.; Yang, C. L. J. Agric. Food Chem. 2009, 57, 2441. https://doi.org/10.1021/jf803415z
  24. Wang, X. F.; Si, T. F.; Li, Q. B.; Zhu, Z. Y.; Zhu, X. J.; Qiang, S.; Yang, C. L. Arkivoc 2010, ii, 31.

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