Chinese Journal of Organic Chemistry >
Synthesis and Fungicidal Activities of 2-Benzylsulfonyl-5-methyl- 1,2,4-triazolo[1,5-a]pyrimidine-7-oxoacetohydrazone Derivatives
Received date: 2012-03-16
Revised date: 2012-05-15
Online published: 2012-06-04
Supported by
Project supported by the Governor’s Foundation for Excellent Talents of Science, Technology & Education of Guizhou Province (No. 200817).
Twenty four novel 2-benzylsulfonyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-7-oxoacetohydrazone derivatives 5a～5x were synthesized by utilization of 2-benzylthio-5-methyl-7-hydroxyl-1,2,4-triazolo[1,5-a] pyrimidine as starting material. All the target compounds were characterized by 1H NMR, IR, MS and elemental analysis. The preliminary bioassay indicated that the inhibition rates of 4-methoxybenzaldehyde N-[2-benzylsulfonyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine]- 7-oxoacetohydrazone (5k), 2-choro-5-nitrobenzaldehyde N-[2-benzylsulfonyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine]-7- oxoacetohydrazone (5p) and cinnamaldehyde N-[2-benzylsulfonyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine]-7-oxoaceto- hydrazone (5s) against Botrytis cinerea reached above 70% at the concentration of 50 μg/mL.
Xiong Qizhong , Liu Junhu , Lin Xuanfu , Bao Xiaoping . Synthesis and Fungicidal Activities of 2-Benzylsulfonyl-5-methyl- 1,2,4-triazolo[1,5-a]pyrimidine-7-oxoacetohydrazone Derivatives[J]. Chinese Journal of Organic Chemistry, 2012 , 32(10) : 1951 -1957 . DOI: 10.6023/cjoc1203162
[1] Chen, Q.; Zhu, X.-L.; Jiang, L.-L.; Liu, Z.-M.; Yang, G.-F. Eur. J. Med. Chem. 2008, 43, 595.
[2] Chen, Q.; Liu, Z.-M.; Chen, C.-N.; Jiang, L.-L.; Yang, G.-F. Chem. Biodivers. 2009, 6, 1254.
[3] Long, D.-Q.; Wang, Y.-G.; Li, D.-J.; Wang, F.-J. Chin. J. Org. Chem. 2005, 25, 1498 (in Chinese).
(龙德清, 汪焱钢, 李德江, 王锋尖, 有机化学, 2005, 25, 1498.)
[4] Tang, W.; Shi, D.-Q. J. Heterocycl. Chem. 2010, 47, 162.
[5] Zhang, N.; Ayral-Kaloustian, S.; Nguyen, T.; Hernandez, R.; Beyer, C. Bioorg. Med. Chem. Lett. 2007, 17, 3003.
[6] Zhai, X.; Jiang, N.; Zhang, K.-L.; Bao, F.; Gong, P. Chin. Chem. Lett. 2009, 20, 1179.
[7] Linton, M. A.; Gonzalez, J.; Li, H.; Tatlock, J.; Jewell, T.; Johnson, S.; Drowns, M.; Patel, L.; Blazel, J.; Ornelas, M. Synthesis 2010, 4015.
[8] Deev, S. L.; Yasko, M. V.; Karpenko, I. L.; Korovina, A. N.; Khandazhinskaya, A. L.; Andronova, V. L.; Galegov, G. A.; Shestakova, T. S.; Ulomskii, E. N.; Rusinov, V. L.; Chupakhin, O. N.; Kukhanova, M. K. Bioorg. Chem. 2010, 38, 265.
[9] Yang, C.; Yang, S.; Song, B.-A.; Hu, D.-Y.; Chen, H.-J.; Xue, W.; Jin, L.-H.; Wu, J.; Xu, W.-M.; Bai, S. Chin. J. Org. Chem. 2010, 30, 1327 (in Chinese).
(杨超, 杨松, 宋宝安, 胡德禹, 陈红军, 薛伟, 金林红, 吴剑, 徐维明, 柏松, 有机化学, 2010, 30, 1327.)
[10] Li, Y.; Li, M.; Chai, B.-S.; Liu, C.-L. Agrochemicals 2006, 45, 697 (in Chinese).
(李洋, 李淼, 柴宝山, 刘长令, 农药, 2006, 45, 697.)
[11] Li, T.-G.; Liu, J.-P.; Han, J.-T.; Fu, B.; Wang, D.-Q.; Wang, M.-A. Chin. J. Org. Chem. 2009, 29, 898 (in Chinese).
(李太公, 刘建平, 韩金涛, 傅滨, 王道全, 王明安, 有机化学, 2009, 29, 898.)
[12] Wang, T.; Xue, S.-J. Chem. Reag. 2000, 22, 339 (in Chinese).
(王涛, 薛思佳, 化学试剂, 2000, 22, 339.)
[13] He, S.-Y.; Chen, J.-L.; Yang, R.; Wu, W.-T.; Zhao, J.-S.; Shi, Q.-Z.; Wang, R.-X. Chin. J. Org. Chem. 2003, 23, 1387 (in Chinese).
(何水样, 陈军利, 杨锐, 武望婷, 赵建社, 史启祯, 王汝贤, 有机化学, 2003, 23, 1387.)
[14] Zhou, Z.-Z.; Chen, Q.; Yang, G.-F. Chin. J. Org. Chem. 2008, 28, 1385 (in Chinese).
(周中振, 陈琼, 杨光富, 有机化学, 2008, 28, 1385.)
[15] Wei, T.-B.; Zhang, Z.-R.; Shi, H.-X.; Cui, W.-H.; Zhang, Y.-M. Chin. J. Org. Chem. 2008, 28, 145 (in Chinese).
(魏太保, 张治仁, 师海雄, 崔文辉, 张有明, 有机化学, 2008, 28, 145.)
[16] Yang, G.-F.; Liu, Z.-M.; Lu, A.-H.; Zhuang, N.-B. Acta Chim. Sinica 2001, 59, 594 (in Chinese).
(杨光富, 刘祖明, 陆爱红, 庄农波, 化学学报, 2001, 59, 594.)
[17] Chen, Q.; Long, D.-Q.; Cheng, J.; Li, J.; Liu, Z.-M.; Yang, G.-F. Chem. J. Chin. Univ. 2006, 27, 454 (in Chinese).
(陈琼, 龙德清, 程靖, 李晶, 刘祖明, 杨光富, 高等学校化学学报, 2006, 27, 454.)
[18] Yang, Z.-P.; Shan, S. Chin. J. Org. Chem. 2003, 23, 363 (in Chinese).
(杨振平, 单尚, 有机化学, 2003, 23, 363.)
[19] 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.)
/
| 〈 |
|
〉 |
