Articles

Synthesis and Fungicidal Activities of 2-Benzylthio(sulfonyl)-5- methyl-7-substituted benzyloxy-1,2,4-triazolo[1,5-a] pyrimidine Derivatives

  • Lin Xuanfu ,
  • Tan Zan ,
  • Liu Yong ,
  • He Yinju ,
  • Bao Xiaoping
Expand
  • Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025

Received date: 2012-08-29

  Revised date: 2012-10-15

  Online published: 2012-10-24

Supported by

Project supported by the Governor’s Foundation for Excellent Talents of Science, Technology & Education of Guizhou Province (No. 200817).

Abstract

Using 2-benzylthio-5-methyl-7-hydroxyl-1,2,4-triazolo[1,5-a]pyrimidine as starting material, twelve novel 2-benzylthio-5-methyl-7-substituted benzyloxy-1,2,4-triazolo[1,5-a]pyrimidine derivatives 5a5l and their sulfonyl analogues 6a6l were synthesized through sequential reactions of etherification and oxidation, respectively. Their structures were characterized by 1H NMR, IR, MS and elemental analysis. The preliminary bioassay indicated that some compounds exhibited certain fungicidal activities, for example, the inhibition rates of compounds 5c, 5k and 5l (50 μg/mL) against Botrytis cinerea were 61%, 69% and 85%, respectively.

Cite this article

Lin Xuanfu , Tan Zan , Liu Yong , He Yinju , Bao Xiaoping . Synthesis and Fungicidal Activities of 2-Benzylthio(sulfonyl)-5- methyl-7-substituted benzyloxy-1,2,4-triazolo[1,5-a] pyrimidine Derivatives[J]. Chinese Journal of Organic Chemistry, 2013 , 33(02) : 353 -358 . DOI: 10.6023/cjoc201208033

References

[1] Chen, Q.; Liu, Z.-M.; Chen, C.-N.; Jiang, L.-L.; Yang, G.-F. Chem. Biodivers. 2009, 6, 1254.

[2] Chen, W.-B.; Jin, G.-Y. Heteroat. Chem. 2003, 14, 607.

[3] Xu, L.; Guo, X.-L.; Yang, L.-M. Chem. Res. Appl. 2010, 22, 475 (in Chinese). (徐莉, 郭秀兰, 杨乐敏, 化学研究与应用, 2010, 22, 475.)

[4] Xiong, Q.-Z.; Lin, X.-F.; Liu, J.-H.; Bi, L.; Bao, X.-P. Chin. J. Org. Chem. 2012, 32, 1255 (in Chinese). (熊启中, 林选福, 刘军虎, 毕亮, 鲍小平, 有机化学, 2012, 32, 1255.)

[5] Zhai, X.; Jiang, N.; Zhang, K.-L.; Bao, F.; Gong, P. Chin. Chem. Lett. 2009, 20, 1179.

[6] Shaaban, M. R.; Saleh, T. S.; Mayhoub, A. S.; Farag, A. M. Eur. J. Med. Chem. 2011, 46, 3690.

[7] Kumar, R. V.; Gopal, K. R.; Kumar, K. V. S. R. J. Heterocycl. Chem. 2005, 42, 1405.

[8] 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.)

[9] 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.)

[10] Shaaban, M. R.; Saleh, T. S.; Mayhoub, A. S.; Mansour, A.; Farag, A. M. Bioorg. Med. Chem. 2008, 16, 6344.

[11] Chen, C.-N.; Chen, Q.; Yang, G.-F. Chin. J. Org. Chem. 2009, 29, 245 (in Chinese). (陈超南, 陈琼, 杨光富, 有机化学, 2009, 29, 245.)

[12] Xiong, Q.-Z.; Liu, J.-H.; Lin, X.-F.; Bao, X.-P. Chin. J. Org. Chem. 2012, 32, 1951 (in Chinese).

(熊启中, 刘军虎, 林选福, 鲍小平, 有机化学, 2012, 32, 1951.)

[13] Yang, Z.-P.; Shan, S. Chin. J. Org. Chem. 2003, 23(suppl.), 363 (in Chinese). (杨振平, 单尚, 有机化学, 2003, 23(增刊), 363.)

[14] Gao, Y.-L.; Lin, X.-F.; Han, F.-F.; Bao, X.-P. C hin. 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.)
Outlines

/