Chinese Journal of Organic Chemistry >
Synthesis and Biological Activity of 2-Methyl-6-chlorobenzene-sulfonylurea Derivatives
Received date: 2015-01-22
Revised date: 2015-02-25
Online published: 2015-07-24
Supported by
Project supported by the National Natural Scinece Foundation of China (No. 21272129) and the National Key Technologies R&D Program (No. 2011BAE06B05).
In order to study the multi-bioactivity of sulfonylurea (SU) derivatives, twelve novel 2-methyl-6-chlorobenzenesul-fonylureas were designed and synthesized according to the commercialized SUs skeletons. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. The title compounds showed good herbicidal activity against dicotyledonous weeds by pot-culture method. For example, the herbicidal activity of 5b, 5i and 5j against Brassica napus, Amaranthus retroflexus was as effective as chlorsulfuron and monosulfuron. The in vitro antifungal test indicated that some of the target compounds exhibited good antifungal activity at the dosage of 50 mg·L-1.
Key words： sulfonylurea; chlorsulfuron; herbicidal activity; antifungal activity
Chen Wei , Wei Wei , Wu Changchun , Li Yuxin , Li Yonghong , Yu Shujing , Li Zhengming . Synthesis and Biological Activity of 2-Methyl-6-chlorobenzene-sulfonylurea Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(7) : 1576 -1581 . DOI: 10.6023/cjoc201501032
[1] Liu, C. L. Encyclopedia of World Pesticide--Herbicide Volume, Chemical Industry Press, Beijing, 2002, pp. 15～73 (in Chinese).(刘长令, 世界农药大全(除草剂卷), 北京, 化学工业出版社, 2002, pp. 15～73.)
[2] Levitt, G. US 4127405, 1978 [Chem. Abstr. 1979, 90, 104022].
[3] Liu, Z. Ph. D. Dissertation, Nankai University, Tianjin, 2013 (in Chinese).(刘卓, 博士论文, 南开大学, 天津 2013.)
[4] George, L. Synthesis and Chemistry of Agrochemicals II, American Chemistry Society, Washington DC, 1991, pp. 16～31.
[5] Guo, W. C. Ph.D. Dissertation, Nankai University, Tianjin, 2008 (in Chinese).(郭万成, 博士论文, 南开大学, 天津 2008.)
[6] Li, Z. M.; Jia, G. F.; Wang, L. X.; Yang, Z. Q.; Lai, C. M. CN 1080116, 1994 [Chem. Abstr. 1994, 121, 29277].
[7] Li, Z. M.; Jia, G. F.; Wang, L. X.; Fan, C. W.; Yang, Z. CN 1106393, 1995 [Chem. Abstr. 1996, 124, 261066].
[8] Li, Z. M.; Ma, Y.; Guddat, L.; Cheng, P. Q.; Wang, J. G.; Pang, S. S.; Dong, Y. H.; Lai, C. M.; Wang, L. X.; Jia, G. F.; Li, Y. H.; Wang, S. H.; Liu, J.; Zhao, W. G.; Wang, B. L. Pest Manage. Sci. 2012, 68, 618.
[9] Zhu, C. Q.; Chen, H. Z.; Liu, M. X.; Wan, X. Z.; Qian, G. H. Pestic. Sci. Admin. 2005, 26, 25 (in Chinese).(祝春强, 陈会柱, 刘明熙, 万贤宗, 钱国华, 农药科学与管理, 2005, 26, 25.)
[10] Liu, J. S.; Kou, J. J.; Liu, G. L. Agrochemicals 2007, 46, 145 (in Chinese).(刘金胜, 寇俊杰, 刘桂龙, 农药, 2007, 46, 145.)
[11] Zhu, H. C. China Plant Prot. 2012, 32, 49 (in Chinese).(朱荷锄, 中国植保导刊, 2012, 32, 49.)
[12] http://www.farmer.com.cn/xwpd/jjsn/201312/t20131212_922500.htm
[13] Chaleff, R. S.; Mauvais, C. J. Science 1984, 224, 1443.
[14] Liu, Z.; Pan, L.; Li, Y. H.; Wang, S. H.; Li, Z. M. Chem. Res. Chin. Univ. 2013, 29, 466.
[15] Lee, Y. T.; Cui, C. J.; Chow, E. W. L.; Pue, N.; Lonhienne, T.; Wang, J. G.; Fraser, J. A.; Guddat, L. W. J. Med. Chem. 2013, 56, 210.
[16] Hoffman, R. V. Org. Synth. 1981, 60, 121.
[17] Sun, X. Y.; Shan, G.; Sun Y. H.; Rao, Y. Angew. Chem., Int. Ed. 2013, 52, 4440.
[18] Liu, Z.; Pan, L.; Yu, S. J.; Li, Z. M. Chem. J. Chin. Univ. 2013, 34, 1868 (in Chinese).(刘卓, 潘里, 于淑晶, 李正名, 高等学校化学学报, 2013, 34, 1868.)
[19] Liu, X. H.; Tan, C. X.; Weng, J. Q. Phosphorus, Sulfur Silicon Relat. Elem. 2011, 186, 552.
[20] Wang, H. X.; Li, F.; Xu, L. P.; Li, Y. H.; Wang, S. H.; Li, Z. M. Chem. J. Chin. Univ. 2010, 31, 64 (in Chinese).(王红学, 李芳, 许丽萍, 李永红, 王素华, 李正名, 高等学校化学学报, 2010, 31, 64.)
[21] Naik, N. H.; Sikder, A. K.; Kusurkar, R. S. Tetrahedron Lett. 2013, 54, 3715.
[22] Pang, H. L.; Yang, J. B.; Huang, C. Q.; Yin, D. L. Fine Chem. Intermed. 2005, 35, 26 (in Chinese).(庞怀林, 杨剑波, 黄超群, 尹笃林, 精细化工中间体, 2005, 35, 26.)
[23] Pan, L.; Liu, Z.; Chen, Y. W.; Li, Y. H.; Li, Z. M. Chem. J. Chin. Univ. 2013, 34, 1416 (in Chinese).(潘里, 刘卓, 陈有为, 李永红, 李正名, 高等学校化学学报, 2013, 34, 1416.)
[24] Kloetzer, W.; Schantl, J. Monatsh. Chem. 1963, 94, 1178.
[25] Brown, D. J.; Teitei, T. Aust. J. Chem. 1965, 18, 559.
[26] Hull, R. J. Chem. Soc. 1957, 4845.
[27] Okuda, N.; Kuniyoshi, I. Yakugaku Zasshi 1962, 82, 1035.
[28] Pficiderer, W.; Lohrmann, R. Chem. Ber. 1961, 94, 2708.
[29] 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.)
[30] Yan, T.; Yu, G. P.; Xiong, L. X.; Yu, S. J.; Wang, S. H.; Li, Z. M. Chem. J. Chin. Univ. 2011, 32, 1750 (in Chinese).(闫涛, 于观平, 熊丽霞, 于淑晶, 王素华, 李正名, 高等学校化学学报, 2011, 32, 1750.)
/
| 〈 |
|
〉 |
