Chinese Journal of Organic Chemistry >
Synthesis and Fungicidal Activity of Difluoromethy Substituted Carboxamide Derivatives
Received date: 2014-06-13
Revised date: 2014-09-22
Online published: 2014-10-22
Supported by
Supported by the Key Innovation Team of Science and Technology in Zhejiang Province (No. 2010R50018), and the Project supported by the National Key Technologies R&D Program (No. 2011BAE06B03-01).
In the course of discovering novel fungicidal lead compounds with high activity and safety, 13 new difluoromethyl substituted carboxamide derivatives were designed and synthesized according to the principle of bioactive substructure combination. Their structures were confirmed by 1H NMR, MS and HRMS. The fungicidal activities of these compounds were evaluated. Preliminary bioassay showed that most of the title compounds showed good fungicidal activity at 200 mg/L.
Key words： isoxazole; pyrazole amides; synthesis; fungicidal activity
Liu Tingting , Ni Yun , Zhong Liangkun , Huang Hongying , Hu Weiqun , Xu Tianming , Tan Chengxia . Synthesis and Fungicidal Activity of Difluoromethy Substituted Carboxamide Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(2) : 422 -427 . DOI: 10.6023/cjoc201406017
[1] Liu, X. H.; Zhao, W. G.; Wang, B. L.; Li, Z. M. Res. Chem. Intermed. 2012, 28, 1999.
[2] Tong, J. Y.; Shi, Y. X.; Liu, X. H.; Sun, N. B.; Li, B. J. Chin. J. Org. Chem. 2012, 32, 2373 (in Chinese). (童建颖, 石延霞, 刘幸海, 孙娜波, 李宝聚, 有机化学, 2012, 32, 2373.)
[3] Su, N. N.; Li, Y.; Yu, S. J.; Zhang, X.; Liu, X. H.; Zhao, W. G. Res. Chem. Intermed. 2013, 39, 759.
[4] Tong, J. Y.; Wu, H. K.; Sun, N. B.; Liu, X. H. Chin. J. Struct. Chem. 2013, 32, 607.
[5] Hu, L.-M.; Li, X.-S.; Chen, Z.-Y.; Liu, Z.-J. Chin. J. Org. Chem. 2003, 23, 1131 (in Chinese). (胡利明, 李学恕, 陈致远, 刘钊杰, 有机化学, 2003, 23, 1131.)
[6] (a) Xe, F.; Liu, T.-T.; Yang, G.; Yuan, J.; Kong, X.-L.; Xu, T.-M.; Tan, C.-X. Chin. J. Org. Chem. 2013, 33, 2596 (in Chinese). (谢峰, 刘婷婷, 杨果, 袁静, 孔小林, 许天明, 谭成侠, 有机化学, 2013, 33, 2596.)
(b) Ma, Q.-S.; Liu, X.-H.; Weng, J.-Q.; Li, Y.-S.; Zhang, M.; Zhang, X.-Y.; Tan, C.-X. Chin. J. Org. Chem. 2013, 33, 1749 (in Chinese). (马青森, 刘幸海, 翁建全, 李永曙, 张旻, 张向阳, 谭成侠, 有机化学, 2013, 33, 1749.)
[7] Ohuchi, S.; Okada, S. JP 10338589, 1998 [Chem. Abstr. 1998, 130, 120912y].
[8] Liu, C.-L. Pesticide 1998, 37(8), 1 (in Chinese). (刘长令, 农药, 1998, 37(8), 1.)
[9] Doyle, F. P.; J. C.; Long, A. A. W.; Nayler, J. H. C.; Stove, E. R. J. Am. Chem. Soc. 1963, 85, 5845.
[10] Kang, Y. K.; Shin, K. J.; Yoo, K. H.; Seo, K. J.; Hong, C. Y.; Lee, C. S.; Park, S. Y.; Kim, D. T.; Park, S. W. Bioorg. Med. Chem. Lett. 2000, 10, 95.
[11] Josef, E.; Harald, W.; Camilla, C.; Hans, T. WO 2007065661, 2007 [Chem. Abstr. 2007, 147, 72747].
[12] Dunkel, R.; Beeck, S.; Greul, J. N.; Wachendorf-Neumann, U.; Dahmen, P.; Voerste, A. WO 2008014905, 2008 [Chem. Abstr. 2008, 148, 239197].
[13] Stierli, D.; Taylor, J. J.; Walter, H.; Worthington, P. A.; Rajan, R. WO 2007141009, 2007 [Chem. Abstr. 2007, 148, 55044].
[14] Stierli, D.; Taylor, J. J.; Walter, H.; Worthington, P. A. WO 2007134799, 2008 [Chem. Abstr. 2008, 148, 168714].
[15] EP 1997808, 2008 [Chem. Abstr. 2008, 150, 5730].
[16] (a) Du, G.-J.; Chen, D.-L.; Lu, R.-J.; Wang, X.-J.; Yan, M. Chin. J. Org. Chem. 2009, 29, 1576 (in Chinese). (杜光剑, 陈东亮, 卢锐炯, 王晓军, 鄢明, 有机化学, 2009, 29, 1576.)
(b) Zhou, Y.-L.; Shen, S.-W.; Liu, F.-M. Chin. J. Org. Chem. 2010, 30, 1343 (in Chinese). (周英雷, 沈松伟, 刘方明, 有机化学, 2010, 30, 1343.)
[17] Hu, W.-Q.; Zhu, W.-G.; Chen, D.-H. Chin. J. Pestic. Sci. 2007, 9, 240 (in Chinese). (胡伟群, 朱卫刚, 陈定花, 农药学学报, 2007, 9, 240.)
[18] Stierli, D.; Walter, H.; Rajan, R. WO 2009127726, 2009 [Chem. Abstr. 2009, 151, 470195].
/
| 〈 |
|
〉 |
