Synthesis and Antifungal Activity of Novel Benzimidazol-2-ylcyanoketone Oxime Ethers Containing Morpholine Moiety

doi:10.6023/cjoc201504018

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (10): 2229-2233.DOI: 10.6023/cjoc201504018 Previous Articles Next Articles

Notes

含吗啉环的2-苯并咪唑基氰基甲酮肟醚的合成及杀菌活性

曲智强, 李付博, 邢程远, 姜林

山东农业大学化学与材料科学学院泰安 271018

收稿日期:2015-04-13 修回日期:2015-05-29 发布日期:2015-06-04
通讯作者: 姜林 E-mail:jiangl@sdau.edu.cn
基金资助:
山东省科技发展计划(No. 2013GZX20109)资助项目.

Synthesis and Antifungal Activity of Novel Benzimidazol-2-ylcyanoketone Oxime Ethers Containing Morpholine Moiety

Qu Zhiqiang, Li Fubo, Xing Chengyuan, Jiang Lin

College of Chemistry and Material Science, Shandong Agricultural University, Taian 271018

Received:2015-04-13 Revised:2015-05-29 Published:2015-06-04
Supported by:
Project supported by the Science and Technology Development Plan of Shandong Province (No. ZR2013GZX20109).

1. Synthesis and Antifungal Activity of Novel Benzimidazol-2-ylcyanoketone Oxime Ethers Containing Morpholine Moiety.PDF(622KB)

Abstract

A series of benzimidazol-2-ylcyanoketone oxime ethers containing morpholine moiety (4a～4h) were synthesized from 2-benzimidazolyl acetonitrile, sodium nitrite, chloroacetyl morpholine and haloalkane/benzyl chloride via sequential reactions of oximation, substitution and etherification. The structures of the target compounds were elucidated by IR, NMR, MS, and elemental analysis. All the target compounds were tested for in vitro antifungal activities against Botrytis cinerea and Sclerotinia sclerotiorum by the mycelium growth rate test, and the results indicated that some compounds displayed higher antifungal activity as compared to carbendazim, among which the compounds containing 4-fluorobenzyl or 4-chlorobenzyl moiety (4e, 4f) have excellent activity.

Key words: oxime ether, benzimidazole, morpholine, antifungal activity

Cite this article

Qu Zhiqiang, Li Fubo, Xing Chengyuan, Jiang Lin. Synthesis and Antifungal Activity of Novel Benzimidazol-2-ylcyanoketone Oxime Ethers Containing Morpholine Moiety[J]. Chin. J. Org. Chem., 2015, 35(10): 2229-2233.

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[1] Fu, C.; Pei, J.; Ning, Y.; Liu, M.; Shan, P.; Liu, J.; Li, Y.; Hu, F.; Zhu, Y.; Yang, H.; Zou, X. Pest Manage. Sci. 2014, 70, 1207.
[2] Dai, H.; Yu, H. B.; Liu, J. B.; Qin, X.; Wang, T. T.; Zhang, X.; Qin, Z. F.; Fang, J. X. Chin. J. Org. Chem. 2013, 33, 1104 (in Chinese). (戴红, 于海波, 刘建兵, 秦雪, 王婷婷, 张欣, 秦振芳, 方建新, 有机化学, 2013, 33, 1104.)
[3] Babazadeh-Qazijahani, M.; Badali, H.; Irannejad, H.; Afsarian, M. H.; Emami. S. Eur. J. Med. Chem. 2014, 76, 264.
[4] Jiang, L. L.; Chen, C. N.; Zhou, Y. F.; Chen, Q.; Yang, G. F. Chin. J. Org. Chem. 2009, 29, 1392 (in Chinese). (江黎黎, 陈超南, 周延菲, 陈琼, 杨光富, 有机化学, 2009, 29, 1392.)
[5] Gannarapu, M. R.; Vasamsetti, S. B.; Punna, N.; Royya, N. K.; Pamulaparthy, S. R.; Nanubolu, J. B.; Kotamraju, S.; Banda, N. Eur. J. Med. Chem. 2014, 75, 143.
[6] Chen, Y.; Wang, Z. B.; Zhang, X.; Xia, L. J.; Gong, H. Y.; Zhao, H. J.; Xue, W. Chin. J. Org. Chem. 2014, 34, 1662 (in Chinese). (陈玉, 王忠波, 张贤, 夏丽娟, 龚华玉, 赵洪菊, 薛伟, 有机化学, 2014, 34, 1662.)
[7] Chakravarti, B.; Akhtar, T.; Rai, B.; Yadav, M.; Siddiqui, J. A.; Dwivedi, S. K. D.; Thakur, R.; Singh, A. K.; Chattopadhyay, N.; Kumar, A. J. Med. Chem. 2014, 57, 8010.
[8] Xiao, Y.; Yan, X.; Xu, Y.; Huang, J.; Yuan, H.; Liang, X.; Zhang, J.; Wang, D. Pest Manage. Sci. 2013, 69: 814.
[9] Liu, A.; Wang, X.; Chen, C.; Pei, H.; Mao, C.; Wang, Y.; He, H.; Huang, L.; Liu, X.; Hu, Z.; Ou, X.; Huang, M.; Yao, J. Pest Manage. Sci. 2009, 65, 229.
[10] Liu, W.; He, K.; Li, Z.; Wang, X. Chemistry 2008, 71, 523 (in Chinese). (刘卫东, 何奇喜, 李仲英, 王晓光, 化学通报, 2008, 71, 523.)
[11] Shi, Y.; Yuan, L.; Zhang, Y.; Li, B. Chin. J. Pestic. Sci. 2007, 9, 126 (in Chinese). (石延霞, 袁莉萍, 张一宾, 李宝聚, 农药学学报, 2007, 9, 126.)
[12] Chen, L.; Wei, N.; Gao, J.; Zhou, W. Chin. J. Pestic. Sci. 2011, 13, 448 (in Chinese). (陈岚, 魏宁宁, 高洁, 周文明, 农药学学报, 2011, 13, 448.)
[13] Chen, X.; Yuan, H.; Qin, Z.; Qi, S.; Sun, L. Chin. J. Pestic. Sci. 2007, 9, 229 (in Chinese). (陈小霞, 袁会珠, 覃兆海, 齐淑华, 孙丽鹏, 农药学学报, 2007, 9, 229.)
[14] Wang, M.; Qu, Z.; Du, D.; Jiang, L. Chin. J. Org. Chem. 2013, 33, 1005 (in Chinese). (王美岩, 曲智强, 杜丹, 姜林, 有机化学, 2013, 33, 1005.)
[15] Zhou, S.; Li, F; Zhang, P.; Jiang, L. Res. Chem. Intermed. 2013, 39, 1735.
[16] Mielczarek, M.; Thomas, R. V.; Ma, C.; Kandemir, H.; Yang X.; Bhadbhade, M.; Black, D. S.; Griffith, R.; Lewis, P. J.; Kumar, N. Bioorg. Med. Chem. 2015, 23, 1763.
[17] Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 2th ed., Trans. by Yao, H.-H., Science Press, Beijing, 1988, p. 107 (in Chinese).
(西尔弗斯坦, R. M.; 巴勒斯, G. C.; 莫里尔, T. C.著, 有机化合物光谱鉴定, (第二版), 姚海文译, 科学出版社, 北京, 1988, p. 107.)
[18] Karakurt, A.; Dalkara, S.; Özalp, M.; Özbey, S.; Kendi, E.; Stables, J. P. Eur. J. Med. Chem. 2001, 36, 421.
[19] Song, H. F.; Ding, S. M. Dyestuffs Color 2003, 40, 116 (in Chinese). (宋华付, 丁绍民. 染料与染色, 2003, 40, 116.)
[20] Ilkun, O. T.; Archibald, S. J.; Barnes, C. L.; Gerasimchuk, N.; Biagioni, R.; Silchenko, S.; Gerasimchuk, O. A.; Nemykin, V. N. Dalton Trans. 2008, 42, 5715.
[21] Zhang, X.; Zhang, Y.; Chen, Y.; Zhou, M. Chin. J. Pestic. Sci. 2008, 10, 41 (in Chinese). (张晓, 张艳军, 陈雨, 周明国, 农药学学报, 2008, 10, 41.)

含吗啉环的2-苯并咪唑基氰基甲酮肟醚的合成及杀菌活性

Synthesis and Antifungal Activity of Novel Benzimidazol-2-ylcyanoketone Oxime Ethers Containing Morpholine Moiety

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