新型含酰基脲桥和硫脲桥的苯双酰胺类似物的合成及生物活性
收稿日期: 2014-09-05
修回日期: 2014-10-30
网络出版日期: 2014-11-27
基金资助
国家重点基础研究发展计划(973计划, No. 2010CB126106)、国家自然科学基金(Nos. 31370039, 21272129)、国家科技攻关计划(No. 2011BAE06B05)、高等学校博士学科点专项科研基金(No. 20110031110017)资助项目.
Synthesis and Biological Activities of Novel Analogues of Phthalamide Containing Acylurea and Acylthiourea
Received date: 2014-09-05
Revised date: 2014-10-30
Online published: 2014-11-27
Supported by
Project supported by the National Basic Research Program of China (973 Program, No. 2010CB126106), the National Natural Science Foundation of China (Nos. 31370039, 21272129), the National Key Technologies R&D Program (No. 2011BAE06B05), and the Specialized Research Fund for the Doctorial Program of Higher Education (No. 20110031110017).
陈有为 , 万莹莹 , 刘巧霞 , 刘敬波 , 熊丽霞 , 于淑晶 , 李正名 . 新型含酰基脲桥和硫脲桥的苯双酰胺类似物的合成及生物活性[J]. 有机化学, 2015 , 35(4) : 882 -889 . DOI: 10.6023/cjoc201409005
In order to find novel and efficient insecticides targeting at the ryanodine receptor, a series of novel compounds containing acylurea and acylthiourea, referring to moieties of flubendiamide and diflubenzuron, were designed and synthesized. Their structures were characterized by 1H NMR, HRMS and X-ray diffraction. The insectical activities showed that the introducing of acylurea and acylthiourea bridges decreased the acitivity. Compound 7d showed 50% activity at the concentration of 10 mg/L. In addtion, some structures showed moderate antifungal activities. Compound 8f displayed 75.0%, 87.5% and 84.6% antifungal activities against Botryosphaeria dothidea, Rhizoctonia cerealis and Fusarium fujikuroi.
[1] Pan, L.; Chen, Y. W.; Liu, Z.; Li, Y. H.; Li, Z. M. Chin. J. Org. Chem. 2013, 33, 542 (in Chinese).
(潘里, 陈有为, 刘卓, 李永红, 李正名, 有机化学, 2013, 33, 542.)
[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, 33, 2373.)
[3] Tan, C. X.; Shi, Y. X.; Weng, J. Q.; Liu, X. H.; Zhao, W. G.; Li, B. J. J. Heterocycl. Chem., 2014, 51, 690.
[4] Zhang, L. J.; Yang, M. Y.; Sun, Z. H.; Tan, C. X.; Weng, J. Q.; Wu, H. K.; Liu, X. H. Lett. Drug Des. Discovery 2014, 11, 1107.
[5] Ogawa, Y. Crit. Rev. Biochem. Mol. Biol. 1994, 29, 229.
[6] Dong, W. L.; Xu, J. Y.; Liu, X. H.; Zhao, W. G.; Li, Z. M.. Chin. J. Pest. Sci. 2008, 10, 178.
[7] Sattelle, D. B.; Cordova, D.; Cheek, T. R. Invertebr. Neurosci. 2008, 8, 107.
[8] Feng, Q.; Liu, Z. L.; Wang, M. Z.; Xiong, L. X.; Yu, S. J.; Li, Z. M. Chem. J. Chin. Univ. 2011, 32, 74.
[9] Chen, Y. W.; Li, Y. X.; Pan, L.; Liu, J. B. Wang, Y. Y.; Chen, W.; Xiong, L. X. Yang, N.; Song, H. B.; Li, Z. M. Bioorg. Med. Chem. 2014, 22, 6366.
[10] Tohnishi, M.; Nakao, H.; Kohno, E.; Nishida, T.; Furuya, T.; Shimizu, T.; Seo, A.; Sakata, K.; Fujioka, S.; Kano, H. EP 919542, 1999 [Chem. Abstr. 1999, 131, 31808].
[11] Liu, C. L. Agrochemicals 2005, 44(11), 527 (in Chinese).
(刘长令, 农药, 2005, 44(11), 527.)
[12] Li, Y.; Li, M.; Cai, B. S. Agrochemicals 2006, 45(10), 697 (in Chinese).
(李洋, 李淼, 柴宝山, 农药, 2006, 45(10), 697.)
[13] Chen, Y. W.; Wang, B. L.; Guo, Y. J.; Zhou, Y. Y.; Pan, L.; Xiong, L. X.; Yu, S. J.; Li, Z. M. Chem. Res. Chin. Univ. 2014, 30, 98.
[14] Zhang, X. L.; Li, Y. X., Ma, J. L.; Zhu, H. W.; Wang, B. L.; Mao, M. Z.; Xiong, L. X..; Li, Y. Q.; Li, Z. M. Bioorg. Med. Chem. 2014, 22, 186.
[15] Julius, J. J. Agric. Food. Chem. 1980, 28(l), 2.
[16] Wellinga. J. Agric. Food. Chem. 1973, 21(2), 345.
[17] Lin, J.; Yan, S. J.; Yang, L. J.; Li, J. F.; Liu, F. C. Chin. J. Org. Chem. 2005, 25, 304 (in Chinese).
(林军, 严胜骄, 杨丽娟, 李俊峰, 刘复初, 有机化学, 2005, 25, 304.)
[18] Lahm, G. P.; Selby, T. P.; Frendenberger, J. H.; Stevenson, T. M.; Myers, B. J.; Seburyamo, G.; Smith, B. K.; Flexner, L.; Clark, C. E.; Cordova, D.; Bioorg. Med. Chem. Lett. 2005, 15, 4898.
[19] 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.
[20] O'sullivan, A C.; Lutz, W. J.; AndreRobson, M. J. Smith, S. WO 2006024523, 2006 [Chem. Abstr. 2006, 144, 292427].
[21] Ikeda, E.; Maeda, K.; Furukawa, Y.; Takii, S. WO 2005030699, 2005 [Chem. Abstr. 2005, 142, 373562].
[22] Liu, X. H.; Weng, J. Q.; Tan, C. X. J. Chem. 2013, 2013, 306361.
[23] Liu, X. H.; Sun, Z. H.; Yang, M. Y.; Tan, C. X.; Weng, J. Q.; Zhang, Y. G.; Ma, Y. Chem. Biol. Drug Des. 2014, 84, 342.
[24] Liu, X. H.; Weng, J. Q.; Tan, C. X.; Liu, H. J. Acta Crystallogr. 2012, E68, O493.
[25] Tong, J. Y.; Wu, H. K.; Sun, N. B.; Liu, X. H. Chin. J. Struct. Chem. 2013, 32, 607.
[26] Liu, X. H.; Xu, X. Y.; Tan, C. X.; Weng, J. Q.; Xin, J. H.; Chen, J. Pest Manage. Sci. 2015, 71(2), 292.
[27] Srikanth, L.; Usha, N.; Ramesh, J.; Raghunandan, N.; Venkateshwar, R. J.; Raj, M. K. Pharm. Chem. 2010, 2(4), 231.
[28] Sohail, S.; Naghmana, R.; Peter, G. J.; Muhammad, A.; Rizwan, H. Eur. J. Med. Chem. 2010, 45, 1323.
[29] Siddiqui, N.; Ahsan, W. Eur. J. Med. Chem. 2010, 45, 1536.
[30] Feng, M. L.; Li, Y. F.; Zhu, H. J.; Liang, Z.; Xi, B. B.; Ni, J. P. J. Agric. Food Chem. 2010, 58, 10999.
[31] Feng, M. L.; Li, Y. F.; Zhu, H. J.; Zhao, L.; Xi, B. B.; Ni, J. P. J. Agric. Food Chem. 2010, 58, 10999.
[32] Lin, T.; Zhao, D. J.; Mao, C. H.; Wu, D. X.; Yang, B. Fine Chem. Interm. 2010, 40, 29.
[33] Wang, B. L.; Ma, Y.; Xiong, L. X.; Li, Z. M. Chin. J. Chem. 2012, 30, 815.
[34] Chen, N. C. Bioassay Technology for Pestcides, Beijing Agricultural University Press, Beijing, 1991, p. 161 (in Chinese).
(陈春年, 农药生物技术测定, 北京农业大学出版社, 北京, 1991, p. 161.)
[35] Jiang, W. T.; Hu, F. Z.; Gu, H. Liu, C.; Wei, N. X.; Wan, L.; Ren, S. Z.; Wang, J. T.; Xu, F. B. Chin. J. Org. Chem. 2014, 34, 774 (in Chinese).
(姜文涛, 胡方中, 顾 翰, 刘传, 魏乃翔, 万蕾, 任士钊, 王俊婷, 徐凤波, 有机化学, 2014, 34, 774.)
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