Articles

Synthesis and Herbicidal Activities of (E)-7-(4,6-Dimethoxypyrimidin-2-yloxy)-2,3-dihydro-1H-inden-O-substituted-1-ketoxime Derivatives

  • Li Yuanxiang ,
  • Yan Xiaohong ,
  • Chen Dizhao ,
  • Shun Lin
Expand
  • Department of Chemistry and Chemical Engineering, Huaihua University, Huaihua 418008

Received date: 2013-01-22

  Revised date: 2013-02-21

  Online published: 2013-03-06

Supported by

Project supported by the Planned Science and Technology Project of Hunan Province (No. 2012NK3098), the Scientific Research Fund of Hunan Provincial Education Department (No. 11A092) and the Cooperation Demonstration Base Project of Hunan Province College (No.[2010]235).

Abstract

The purpose of the study was looking for the novel compounds with herbicidal activities. Thirteen novel (E)-7-(4,6-dimethoxypyrimidin-2-yloxy)-2,3-dihydro-1H-inden-O-substituted-1-ketoximes were designed and synthesized using phenol as starting material. The structures of synthesized compounds were confirmed by 1H NMR, MS, elemental analysis. And the structure of the target 6h was confirmed further by X-ray techniques. The preliminary bioassay showed that some of them exhibited certain herbicidal activities, for example, the inhibition rates of compounds 6i and 6l were 20%~40% against Echinochloa crusgalli, Digiatra sanguinalis, Setaria viridis, Brassica juncea, Amaranthus retroflexus and Chenopodium album at 150 g/hm2.

Cite this article

Li Yuanxiang , Yan Xiaohong , Chen Dizhao , Shun Lin . Synthesis and Herbicidal Activities of (E)-7-(4,6-Dimethoxypyrimidin-2-yloxy)-2,3-dihydro-1H-inden-O-substituted-1-ketoxime Derivatives[J]. Chinese Journal of Organic Chemistry, 2013 , 33(07) : 1490 -1495 . DOI: 10.6023/cjoc201301052

References

[1] (a) Nezu, Y.; Wada, N.; Yoshida, F.; Miyazawa, T.; Shimizu, T.; Fujita, T. Pestic. Sci. 1998, 52, 343. (b) Yang, G. F.; Liu, H. Y.; Yang, H. Z. Pestic. Sci. 1999, 55, 1143.
[2] Xue, S J.; Zou, J S. Chem. World 2000, 8, 399 (in Chinese). (薛思佳, 邹金山, 化学世界, 2000, 8, 399.)
[3] Li, Y. X.; Liu, Y. C.; Chen, Q. Chin. J. Org. Chem. 2011, 31(12), 2140 (in Chinese). (李元祥, 刘玉超, 陈琼, 有机化学, 2011, 31(12), 2140.)
[4] Tamaru, M.; Kawamura, N.; Sato, M.; Tachikawa, S.; Yoshida, R.; Takabe, F. EP 435170, 1991[Chem. Abstr. 1991, 115, 159183].
[5] Luthy, C.; Obrecht, J. P. WO 9105781, 1991 [Chem. Abstr. 1991, 115, 183367].
[6] (a) Tsukada, T.; Takahashi, M.; Takemoto, T.; Kanno, O.; Yamane, T.; Kawamura, S.; Nishi, T. Bioorg. Med. Chem. Lett. 2010, 20(3), 1004. (b) James, W. B.; John, J. W. Eur. J. Med. Chem. 2010, 45(1), 25.
[7] Tsukada, T.; Kanno, O.; Yamane, T.; Tanaka, J.; Yoshida, T.; Okuno, A.; Shiiki, T.; Takahashi, M.; Nishi, T. Bioorg. Med. Chem. 2010, 18(14), 5346.
[8] Loudon, J. D.; Razdan, R. K. J. Chem. Soc. 1954, 4299.
[9] (a) Cho, H.; Iwama, Y.; Sugimoto, K.; Mori, S.; Tokuyama, H. J. Org. Chem. 2010, 75(3), 627. (b) Wahyuningsih, T. D.; Pchalek, K.; Kumar, N.; Black, D. S. Tetrahedron 2006, 62(26), 6343. (c) Concepción, A.; Raquel, A.; Purificación, C.; Concepción, P. M.; Rafael, P.; Manuel, M. Bioorg. Med. Chem. 2008, 16(19), 8999.
[10] (a) Pakulski, M. M.; Mahato, S. K.; Bosiak, Mariusz. J.; Krzeminski, M. P.; Zaidlewicz, M. Tetrahedron: Asymmetry 2012, 23(9), 716. (b) Upadhayaya, R. S.; Lahore, S. V.; Sayyed, A. Y.; Dixit, S. S.; Shinde, P. D.; Chattopadhyaya, J. Org. Biomol. Chem. 2010, 8, 2180.
[11] Li, Y. X.; Luo, Y. P.; Xi, Z., Niu, C. W.; He, Y. Z.; Yang, G. F. J. Agric. Food Chem. 2006, 54, 9135.
Outlines

/