Chinese Journal of Organic Chemistry >
Synthesis and Fungicidal Activities of Novel Quinazoline Derivatives Containing 1,2,4-Triazole Schiff-Base Unit
Received date: 2012-09-18
Revised date: 2012-11-09
Online published: 2012-11-20
Supported by
Project supported by the Agricultural Science and Technology Foundation of Guizhou Province (No. 20093010).
Using 3-methyl-4-amino-1,2,4-triazole-5-thione, aromatic aldehydes and 4-chloroquinazoline as starting materials, fourteen novel quinazoline derivatives containing 1,2,4-triazole Schiff-base unit were synthesized. The structures of target compounds were fully characterized by IR, 1H NMR, MS and elemental analysis. The preliminary bioassay showed that some compounds possessed certain fungicidal activities. At the concentration of 50 μg/mL, the inhibition rates of compound 6g against F. oxysporium, C. mandshurica and P. infestans were 71%, 72% and 58%, respectively.
Key words： 1,2,4-triazole Schiff-base; quinazoline; synthesis; fungicidal activity
Liu Junhu , Liu Yong , Jian Junyou , Bao Xiaoping . Synthesis and Fungicidal Activities of Novel Quinazoline Derivatives Containing 1,2,4-Triazole Schiff-Base Unit[J]. Chinese Journal of Organic Chemistry, 2013 , 33(02) : 370 -374 . DOI: 10.6023/cjoc201209023
[1] Yang, S.; Li, Z.; Jin, L.-H.; Song, B.-A.; Liu, G.; Chen, J.; Chen, Z.; Hu, D.-Y.; Xue, W.; Xu, R.-Q. Bioorg. Med. Chem. Lett. 2007, 17, 2193.
[2] Chandregowda, V.; Kush, A. K.; Reddy, G. C. Eur. J. Med. Chem. 2009, 44, 3046.
[3] Gao, Y.-L.; Xiong, Q.-Z.; An, R.; Bao, X.-P. Chin. J. Org. Chem. 2011, 31, 1529 (in Chinese). (高元磊, 熊启中, 安锐, 鲍小平, 有机化学, 2011, 31, 1529.)
[4] Liu, G.; Liu, C.-P.; Ji, C.-N.; Sun, L.; Wen, Q.-W. Chin. J. Org. Chem. 2008, 28, 525 (in Chinese). (刘刚, 刘春萍, 纪春暖, 孙琳, 温全武, 有机化学, 2008, 28, 525.)
[5] Panneerselvam, P.; Rather, B. A.; Reddy, D. R. S.; Kumar, N. R. Eur. J. Med. Chem. 2009, 44, 2328.
[6] Ma, Y.; Liu, F.; Yan, K.; Song, B.-A.; Yang, S.; Hu, D.-Y.; Jin, L.-H.; Xue, W. Chin. J. Org. Chem. 2008, 28, 1268 (in Chinese). (马耀, 刘芳, 严凯, 宋宝安, 杨松, 胡德禹, 金林红, 薛伟, 有机化学, 2008, 28, 1268.)
[7] Gao, X.-W.; Cai, X.-J.; Yan, K.; Gao, L.-L.; Wang, H.-Y.; Chen, Z.; Song, B.-A. Chin. J. Org. Chem. 2008, 28, 1785 (in Chinese). (高兴文, 蔡学建, 严凯, 高丽丽, 王和英, 陈卓, 宋宝安, 有机化学, 2008, 28, 1785.)
[8] Almajan, G. L.; Barbuceanu, S. F.; Almajan, E. R.; Draghici, C.; Saramet, G. Eur. J. Med. Chem. 2009, 44, 3083.
[9] Yin, K.; Jiang, L.-H.; Zhou, H.-X.; Huang, Y.; Xiang, J.-G. Chin. J. Org. Chem. 2008, 28, 1016 (in Chinese). (尹凯, 蒋历辉, 周后相, 黄勇, 向建国, 有机化学, 2008, 28, 1016.)
[10] Ma, Z.-H.; Liu, Z.-M.; Chen, Q. Chin. J. Org. Chem. 2008, 28, 1965 (in Chinese). (马忠华, 刘祖明, 陈琼, 有机化学, 2008, 28, 1965.)
[11] Zhao, P.-L.; Zhang, B.; Wang, Y.-Z.; Yang, G.-F. Chin. J. Org. Chem. 2008, 28, 875 (in Chinese). (赵培亮, 章博, 王亚洲, 杨光富, 有机化学, 2008, 28, 875.)
[12] Wang, B.-L.; Liu, X.-H.; Zhang, X.-L.; Zhang, J.-F.; Song, H.-B.; Li, Z.-M. Chem. Biol. Drug. Des. 2011, 78, 42.
[13] Mu, M.-M.; Lu, B.-W.; Lu, J.-R.; Xin, C.-W.; J. D.; Li, J.-F.; Bao, X.-R. Chin. J. Org. Chem. 2012, 32, 1107 (in Chinese). (穆曼曼, 卢博为, 卢俊瑞, 辛春伟, 戢丹, 李建发, 鲍秀荣, 有机化学, 2012, 32, 1107.)
[14] Gao, Y.-L.; Lin, X.-F.; Han, F.-F.; Bao, X.-P. Chin. J. Org. Chem. 2011, 31, 1648 (in Chinese). (高元磊, 林选福, 韩菲菲, 鲍小平, 有机化学, 2011, 31, 1648.)
[15] Liu, G.; Song, B.-A.; Sang, W.-J.; Yang, S.; Jin, L.-H.; Ding, X. Chin. J. Org. Chem. 2004, 24, 1296 (in Chinese). (刘刚, 宋宝安, 桑维均, 杨松, 金林红, 丁雄, 有机化学, 2004, 24, 1296.)
[16] Sun, X.-H.; Tao, Y.; Liu, Y.-F.; Jia, Y.-Q.; Chen, B. Acta Chim. Sinica 2008, 66, 234 (in Chinese). (孙晓红, 陶燕, 刘源发, 贾婴琦, 陈邦, 化学学报, 2008, 66, 234.)
[17] Sun, X.-H.; Tao, Y.; Liu, Y.-F.; Jia, Y.-Q.; Chen, B.; Yang, J.-W. Chin. J. Org. Chem. 2008, 28, 155 (in Chinese). (孙晓红, 陶燕, 刘源发, 贾婴琦, 陈邦, 杨健武, 有机化学, 2008, 28, 155.)
[18] Kong, F.-B.; Gao, Y.-F.; Chen, X.-L.; Li, G.-L.; Chen, J. Guangxi Agric. Sci. 2006, 37, 148 (in Chinese). (孔凡彬, 高扬帆, 陈锡岭, 李广领, 陈军, 广西农业科学, 2006, 37, 148.)
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