研究论文

新型含三氟甲基取代的邻苯二酰胺衍生物的设计、合成及生物活性研究

  • 周莎 ,
  • 张秀兰 ,
  • 魏巍 ,
  • 刘敬波 ,
  • 熊丽霞 ,
  • 杨娜 ,
  • 李正名
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  • 南开大学元素有机化学研究所 元素有机化学国家重点实验室 天津 300071

收稿日期: 2014-01-14

  修回日期: 2014-03-03

  网络出版日期: 2014-03-13

基金资助

国家重点基础研究发展计划(973计划,No.2010CB126106)、国家科技攻关计划(No.2011BAE06B05)、天津化学化工协同创新中心资助项目.

Design, Synthesis and Biological Activities of Novel Trifluoromethylated Phthalic Acid Diamides Derivatives

  • Zhou Sha ,
  • Zhang Xiulan ,
  • Wei Wei ,
  • Liu Jingbo ,
  • Xiong Lixia ,
  • Yang Na ,
  • Li Zhengming
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  • State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071

Received date: 2014-01-14

  Revised date: 2014-03-03

  Online published: 2014-03-13

Supported by

Project supported by the National Basic Research Program of China (973 Program, No. 2010CB126106), the National Key Technologies R&D Program (No. 2011BAE06B05), and the Collaborative Innovation Center of Chemical Science and Engineering (Tianjin).

摘要

为了寻找高效、对环境友好的先导生物活性结构,设计合成了10个具有双三氟甲基苯胺取代的邻苯二甲酰胺新型衍生物,其结构通过1H NMR,13C NMR,HRMS以及元素分析确认. 初步的生物活性测试结果表明,大部分化合物对小菜蛾和东方粘虫具有一定的杀虫活性. 此结果为邻苯二酰胺类化合物构效关系的研究提供了基础.

本文引用格式

周莎 , 张秀兰 , 魏巍 , 刘敬波 , 熊丽霞 , 杨娜 , 李正名 . 新型含三氟甲基取代的邻苯二酰胺衍生物的设计、合成及生物活性研究[J]. 有机化学, 2014 , 34(7) : 1424 -1428 . DOI: 10.6023/cjoc201401023

Abstract

In order to find efficient, eco-friendly lead compounds, 10 novel phthalic acid diamide derivatives containing two trifluoromethylated aromatic amine moieties were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR, HRMS and elemental analysis. Their insecticidal activities against oriental armyworms and diamondback moths were also evaluated. The preliminary results of biological evaluation showed that most compounds exhibited moderate to high larvicidal activity. These results provided further insights into the relationship between the structures and biological activity.

参考文献

[1] Wang, B. L.; Zhu, H. W.; Ma, Y.; Xiong, L. X.; Li, Y. Q.; Zhao, Y.; Zhang, J. F.; Chen, Y. W.; Zhou, S.; Li, Z. M. J. Agric. Food Chem. 2013, 61, 5483.

[2] Rogers, E. F.; Koniuszy, F. R.; Shavel, J. Jr.; Folkers, K. J. Am. Chem. Soc. 1948, 70, 3086.

[3] Kuna, S.; Heal, R. E. J. Pharmacol. Exp. Ther. 1948, 93, 407.

[4] Procita, L. J. Pharmacol. Exp. Ther. 1958, 123, 296.

[5] Lahm, G. P.; Stevenson, T. M.; Selby, T. P.; Freudenberger, J. H.; Cordova, D.; Flexner, L.; Bellin, C. A.; Dubas, C. M.; Smith, B. K.; Hughes, K. A.; Hollingshaus, J. G.; Clark, C. E.; Benner, E. A. Bioorg. Med. Chem. Lett. 2007, 17, 6274.

[6] Hughes, K. A.; Lahm, G. P.; Selby, T. P.; Stevenson, T. M. WO 2004067528, 2004[Chem. Abstr. 2004, 141, 190786].

[7] Lahm, G. P.; Cordova, D.; Barry, J. D. Bioorg. Med. Chem. 2009, 17, 4127.

[8] Santonastasi, M.; Wehrens, X. H. T. Acta Pharmacol. Sin. 2007, 28, 937.

[9] DuPont Rynaxypyr Insect Control Technical Bulletin: http://www2.dupont.com/Production_Agriculture/en_US/assets/downloads/pdfs/Rynaxypyr_Tech_Bulletin.pdf

[10] (a) Fischer, R.; Funke, C.; Malsam, O.; Löesel, P.; Görgens, U.; Arnold, C.; Tohnishi, M.; Yamaguchi, M.; Harayama, H.; Fujioka, S. WO 2006024412, 2006[Chem. Abstr. 2006, 144, 292428].

(b) Wada, K.; Murata, T.; Shibuya, K.; Shimojo, E. WO 2006133823, 2006[Chem. Abstr. 2006, 146, 62469].

[11] Mochizuki, K.; Inoue, S.; Hatanaka, T. US 2008260440, 2008[Chem. Abstr. 2008, 155, 51563].

[12] Tohnishi, M.; Nakao, H.; Kohno, E.; Nishida, T.; Furuya, T.; Shimizu, T.; Seo, A.; Sakata, K.; Fujioka, S.; Kanno, H. EP 1006107, 2000[Chem. Abstr. 2000, 133, 17278].

[13] Tozai, M.; Morimoto, M.; Fujioka, N.; Seo, A. JP 2001335559, 2001 [Chem. Abstr. 2001, 136, 19945].

[14] Wada, K.; Gomibuchi, T.; Yoneta, Y.; Otsu, Y.; Shibuya, K.; Matsuo, H.; Fischer, R. WO 2004000796, 2003[Chem. Abstr. 2003, 140, 59413].

[15] Harayama, H.; Tohnishi, M.; Morimoto, M.; Fujioka, S. WO 2002094766, 2002[Chem. Abstr. 2002, 137, 384658].

[16] Klaus, M.; Christoph, F.; François, D. Science 2007, 317, 1881.

[17] Marion, D.; Matthias, S. W.; Stefan B. Angew. Chem., Int. Ed. 2011, 50, 11533.

[18] Singh, R. P.; Shreeve, J. M. Tetrahedron 2000, 56, 7613.

[19] Wiehn, M. S.; Vinogradova, E. V.; Togni, A. J. Fluorine Chem. 2010, 131, 951.

[20] Fantasia, S.; Welch, J. M.; Togni, A. J. Org. Chem. 2010, 75, 1779.

[21] Zhang, J. F.; Liu, C.; Ma, Y.; Wang, B. L.; Xiong, L. X.; Yu, S. J.; Li, Z. M. Lett. Drug Des. Discovery 2013, 10, 497.

[22] Zhou, Y. Y.; Feng, Q.; Di, F. J.; Liu, Q. X.; Wang, D. Y.; Chen, Y. W.; Xiong, L. X.; Song, H. B.; Li, Y. X.; Li, Z. M. Bioorg. Med. Chem. 2013, 21, 4968.

[23] Zhang, J. F.; Xu, J. Y.; Wang, B. L.; Li, Y. X.; Xiong, L. X.; Li, Y. Q.; Ma, Y.; Li, Z. M. J. Agric. Food Chem. 2012, 60, 7565.

[24] Wu, M. X.; Zhao, W. W.; Jin, G. Y.; Huang, Q. C.; Cao, S. Chin. J. Chem. 2012, 30, 1310.

[25] Feng, M. L.; Li, Y. F.; Zhu, H. J.; Zhao, L.; Xi, B. B.; Ni, J. P. J. Agric. Food Chem. 2010, 58, 10999.

[26] Tohnishi, M.; Nakao, H.; Furuya, T.; Seo, A.; Kodama, H.; Tsubata, K.; Fujioka, S.; Kodama, H.; Hirooka, T.; Nishimatsu, T. J. Pestic. Sci. 2005, 30, 354.

[27] Dong, W. L.; Xu, J. Y.; Xiong, L. X.; Liu, X. H.; Li, Z. M. Chin. J. Chem. 2009, 27, 579.

[28] Wu, Y. D.; Shen, J. L.; Chen, J.; Lin, X. W.; Li, A. M. Plant Prot. 1996, 5, 3 (in Chinese).

(吴益东, 沈晋良, 陈进, 林祥文, 李爱玫, 植物保护, 1996, 5, 3.)

[29] Busivine, J. R. FAO Plant Production and Protection Paper 21, FAO, Rome, 1980, p. 3.

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