Chinese Journal of Organic Chemistry >
Design, Synthesis and Biological Activities of Novel Trifluoromethylated Phthalic Acid Diamides Derivatives
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).
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.
Key words: fluorine; phthalic acid diamides; synthesis; insecticidal activity
Zhou Sha , Zhang Xiulan , Wei Wei , Liu Jingbo , Xiong Lixia , Yang Na , Li Zhengming . Design, Synthesis and Biological Activities of Novel Trifluoromethylated Phthalic Acid Diamides Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(7) : 1424 -1428 . DOI: 10.6023/cjoc201401023
[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.
/
〈 |
|
〉 |