Chinese Journal of Organic Chemistry >
Synthesis and Fungicidal Activity of 2,5-Disubstituted- 1,3,4-oxadiazole Derivatives
Received date: 2014-03-06
Revised date: 2014-04-03
Online published: 2014-04-15
Supported by
Project supported by the National Program on Key Basic Research Project (973 Program, No. 2010CB126100), the National Natural Science Foundation of China (Nos. 21172090, 31000867) and the Program for Changjiang Scholars and Innovative Research Team in University (No. IRT0953).
A series of new 2,5-disubstituted-1,3,4-oxadiazole derivatives have been designed and synthesized by adding pyridine ring and thiazole ring to the structure of 1,3,4-oxadiazole. The structures of target compounds have been confirmed by 1H NMR, EI-MS, IR spectroscopy and elemental analyses. The structure of 2-[(6-pyridin-3-yl)methylthio]-5-(pyridin-4-yl)- 1,3,4-oxadazole has been determined by single crystal X-ray diffraction. The results of preliminary bioassay indicated that some compounds possess potential fungicidal activities against Fusarium oxyporium, Gibberella zeae, Rhizoctonia solani, Dothiorella gregaria and Colletotrichum gossypii at a dosage of 5.0×10-5 g/mL. The fungicidal activities of 1,3,4-oxadiazole derivatives adding thiazole ring were better than those of those adding pyridine ring.
Key words: 1,3,4-oxadiazole; pyridine ring; thiazole ring; fungicidal activity
Liu Jianchao , Wang Weidong , He Hongwu . Synthesis and Fungicidal Activity of 2,5-Disubstituted- 1,3,4-oxadiazole Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(7) : 1447 -1451 . DOI: 10.6023/cjoc201403013
[1] Gibson, M. S. Tetrahedron 1962, 18, 1377.
[2] Cao, S.; Qian, X. H.; Song, G. H.; Huang, Q. C. J. Fluorine Chem. 2002, 117, 63.
[3] Ishida, H.; Isami, S.; Matsumura, T.; Umehara, H.; Yamashita, Y.; Kajita, J.; Fuse, E.; Kiyoi, H.; Naoe, T.; Akinaga, S.; Shiotsu, U.; Arai, H. Bioorg. Med. Chem. Lett. 2008, 18, 5472.
[4] Zhang, L.-R.; Liu, Z.-J.; Zhang, H.; Sun, J.; Luo, Y.; Zhao, T.-T.; Gong, H.-B. Bioorg. Med. Chem. 2012, 20, 3615.
[5] Patel, N. B.; Purohit, A. C.; Rajani, D. P.; Moo-Puc, R.; Rivera, G. Eur. J. Med. Chem. 2013, 62, 677.
[6] Liu, Z. M.; Yang, G. F.; Qian, X. H. J. Chem. Technol. Biotechnol. 2001, 76, 1154.
[7] Wang, W. Y.; Zhao, W. G.; Li, Z. M. Chem. Res. Chin. Univ. 2004, 20, 543.
[8] Basarab, G. S.; Manchester, J. I.; Bist, S.; Boriack-Sjodin, Dangel, B.; Illingworth, R.; Sherer, B. A.; Sriram, S.; Uria-Nickelsen, M.; Eakin, A. E. J. Med. Chem. 2013, 56, 8712.
[9] Wu, X.; Zhu, C.; Lv, Z.; Wei, C.; Liao, X. Chin. J. Org. Chem. 2011, 31, 824 (in Chinese).
(武现丽, 朱春风, 吕志丹, 魏成事, 廖新成, 有机化学, 2011, 31, 824.)
[10] Khan, M. S.; Gita, C.; Asad, M. M. Indian J. Chem. 2004, 43B, 1302.
[11] Zheng, X. M.; Li, Z.; Wang, Y. L.; Chen, W. D.; Huang, Q. C.; Liu, C. X.; Song, G. H. J. Fluorine Chem. 2003, 123, 163.
[12] Ji, Z.; Liu, F.; Zhang, Z.; Li, F.; Jiang, L. Chin. J. Org. Chem. 2012, 32, 2129 (in Chinese).
(纪增臣, 刘峰, 张泽远, 李付博, 姜林, 有机化学, 2012, 32, 2129.)
[13] Chen, T.; Shen, P.; Li, Y. J.; He, H. W. J. Fluorine Chem. 2006, 127, 291.
[14] Cui, Z.; Li, Y.; Ling, Y.; Huang, J.; Cui, J.; Wang, R.; Yang, X. Eur. J. Med. Chem. 2010, 45, 5576.
[15] Chen, H. S.; Li, Z. M.; Han, Y. F. J. Agric. Food Chem. 2000, 48, 5312.
[16] Burbuliene, M. M.; Jakubkiene, V.; Mekuskiene, G.; Udrenaite, E.; Smicius, R.; Vainilavicius, P. Farmaco 2004, 59, 767.
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