研究论文

含二氟甲基取代的吡唑酰胺类化合物的合成及杀菌活性

  • 刘婷婷 ,
  • 倪芸 ,
  • 钟良坤 ,
  • 黄红英 ,
  • 胡伟群 ,
  • 许天明 ,
  • 谭成侠
展开
  • a 浙江工业大学化学工程学院 杭州 310014;
    b 中化蓝天集团有限公司 浙江省化工研究院有限公司 杭州 310023

收稿日期: 2014-06-13

  修回日期: 2014-09-22

  网络出版日期: 2014-10-22

基金资助

“十二五”国家科技支撑计划(No. 2011BAE06B03-01)、浙江省重点科技创新团队(No. 2010R50018)资助项目.

Synthesis and Fungicidal Activity of Difluoromethy Substituted Carboxamide Derivatives

  • Liu Tingting ,
  • Ni Yun ,
  • Zhong Liangkun ,
  • Huang Hongying ,
  • Hu Weiqun ,
  • Xu Tianming ,
  • Tan Chengxia
Expand
  • a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014;
    b Sinochem Lantian Zhejiang Research Institute of Chemical Industry Co. Ltd, Hangzhou 310023

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).

摘要

为了寻找高效安全的杀菌剂新品种和具有生物活性的新型先导化合物, 根据活性亚结构拼接原理, 将异噁唑和含氟基团引入到吡唑酰胺结构中, 设计了13个未见文献报道的含异噁唑的二氟甲基吡唑酰胺类化合物, 通过1H NMR, MS和HRMS对其结构进行了表征, 并对目标产物进行了初步的生物活性测定. 结果表明, 在剂量为200 mg/L时, 大部分化合物均表现出较高的杀菌活性.

本文引用格式

刘婷婷 , 倪芸 , 钟良坤 , 黄红英 , 胡伟群 , 许天明 , 谭成侠 . 含二氟甲基取代的吡唑酰胺类化合物的合成及杀菌活性[J]. 有机化学, 2015 , 35(2) : 422 -427 . DOI: 10.6023/cjoc201406017

Abstract

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.

参考文献

[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].

文章导航

/