Synthesis and Bioactivity of Novel 1-Methyl-3-trifluoromethyl- 5-subsituent-1H-pyrazole-4-carbaldehyde- O-(4-trifluoromethylbenzoyl)oximes

doi:10.6023/cjoc201508028

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (1): 185-190.DOI: 10.6023/cjoc201508028 Previous Articles Next Articles

Notes

1-甲基-3-三氟甲基-5-取代基-1H-吡唑-4-甲醛-O-(4-三氟甲基苯甲酰基)肟的合成与生物活性研究

戴红^a,b, 李宏^c, 金智超^a, 刘文永^a, 肖瑶^a, 何海兵^a, 汪清民^b, 石玉军^a

a 南通大学化学化工学院南通 226019;
b 南开大学元素有机化学国家重点实验室天津 300071;
c 南通丰田化工有限公司南通 226005

收稿日期:2015-08-29 修回日期:2015-10-08 发布日期:2015-10-23
通讯作者: 何海兵, 石玉军 E-mail:hhb3812@163.com;yjshi2015@163.com
基金资助:
国家自然科学基金(Nos. 21202089, 21372135)、江苏省自然科学基金(No. BK20140425)和南通市科技计划(Nos. AS2013004, CP12013002, AS2014011)资助项目.

Synthesis and Bioactivity of Novel 1-Methyl-3-trifluoromethyl- 5-subsituent-1H-pyrazole-4-carbaldehyde- O-(4-trifluoromethylbenzoyl)oximes

Dai Hong^a,b, Li Hong^c, Jin Zhichao^a, Liu Wenyong^a, Xiao Yao^a, He Haibing^a, Wang Qingmin^b, Shi Yujun^a

a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071;
c Nantong Fengtian Chemical Industry Co. Ltd, Nantong 226005

Received:2015-08-29 Revised:2015-10-08 Published:2015-10-23
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21202089, 21372135), the Natural Science Foundation of Jiangsu Province (No. BK20140425), and the Science and Technology Project Fund of Nantong City (Nos. AS2013004, CP12013002, AS2014011).

1. Synthesis and Bioactivity of Novel 1-Methyl-3-trifluoromethyl- 5-subsituent-1H-pyrazole-4-carbaldehyde- O-(4-trifluoromethylbenzoyl)oximes.PDF(790KB)

Abstract

In order to find novel pesticide from pyrazole compounds, a series of new pyrazole derivatives carrying trifluoromethyl benzoyl oxime ester moiety were prepared. The structures of all the title compounds were determined by ¹H NMR, ¹³C NMR, MS and elemental analysis. Preliminary bioassay displayed that most of the target compounds showed certain insecticidal activities at the concentration of 500 μg/mL. When the concentration was reduced to 200 μg/mL, compounds 5b, 5c, 5d, 5i, 5l and 5n were still active against Aphis craccivora with inhibitory values of 90%, 90%, 80%, 80%, 80% and 80%, respectively.

Key words: trifluoromethyl benzoyl, pyrazole, synthesis, biological activity

Cite this article

Dai Hong, Li Hong, Jin Zhichao, Liu Wenyong, Xiao Yao, He Haibing, Wang Qingmin, Shi Yujun. Synthesis and Bioactivity of Novel 1-Methyl-3-trifluoromethyl- 5-subsituent-1H-pyrazole-4-carbaldehyde- O-(4-trifluoromethylbenzoyl)oximes[J]. Chin. J. Org. Chem., 2016, 36(1): 185-190.

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[1] Motoba, K.; Nishizawa, H.; Suzuki, T.; Hamaguchi, H.; Uchida, M.; Funayama, S. Pestic. Biochem. Physiol. 2000, 67, 73.
[2] Lahm, G. P., Selby, T. P.; Lahm, G. P., Freudenberger, J. H.; Stevenson, T. M.; Myers, B. J.; Seburyamo, G.; Smith, B. K.; Flexner, L.; Clark, C. E.; Cordova, D. Bioorg. Med. Chem. Lett. 2005, 15, 4898.
[3] Ouyang, G. P.; Cai, X. J.; Chen, Z.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y.; Zeng, S. J. Agric. Food Chem. 2008, 56, 10160.
[4] Zhao, P. L.; Wang, L.; Zhu, X. L.; Huang, X. Q.; Zhan, C. G.; Wu, J. W.; Yang, G. F. J. Am. Chem. Soc. 2010, 132, 185.
[5] Li, Y. X.; Lin, L.; Chen, Q. Chin. J. Org. Chem. 2011, 31, 306 (in Chinese). (李元祥, 林龙, 陈琼, 有机化学, 2011, 31, 306.)
[6] Dai, H.; Liu, J. B.; Miao, W. K.; Wu, S. S.; Qin, X.; Zhang, X.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2011, 31, 1662 (in Chinese). (戴红, 刘建兵, 苗文科, 吴珊珊, 秦雪, 张欣, 王婷婷, 方建新, 有机化学, 2011, 31, 1662.)
[7] Liang, Y.; He, H. W.; He, H. F.; Yang, Z. W. Chin. J. Org. Chem. 2012, 32, 1513 (in Chinese). (梁英, 贺红武, 何海峰, 杨自文, 有机化学, 2012, 32, 1513.)
[8] El-Moghazy, S. M.; Barsoum, F. F.; Abdel-Rahman, H. M.; Marzouk, A. A. Med. Chem. Res. 2012, 21, 1722.
[9] Sun, N. B.; Tong, J. Y.; Wu, H. K. Chin. J. Org. Chem. 2013, 33, 101 (in Chinese). (孙娜波, 童建颖, 武宏科, 有机化学, 2013, 33, 101.)
[10] 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.)
[11] Selby, T. P.; Lahm, G. P.; Stevenson, T. M.; Hughes, K. A.; Cordova, D.; Annan, I. B.; Barry, J. D.; Benner, E. A.; Currie, M. J.; Pahutski, T. F. Bioorg. Med. Chem. Lett. 2013, 23, 6341.
[12] Guo, C. P.; Peng, Q. L.; Pan, L.; Zhang, D. M.; Chen, H. R. Chin. J. Org. Chem. 2014, 34, 2505 (in Chinese). (国翠平, 彭群龙, 潘龙, 张冬梅, 陈河如, 有机化学, 2014, 34, 2505.)
[13] Xiong, L.; Zhu, X. L.; Shen, Y. Q.; Wishwa, W. K. W. M.; Li, K.; Yang, G. F. Eur. J. Med. Chem. 2015, 95, 424.
[14] Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
[15] Chen, L.; Ou, X. M.; Mao, C. H.; Shang, J.; Huang, R. Q.; Bi, F. C.; Wang, Q. M. Bioorg. Med. Chem. 2007, 15, 3678.
[16] Song, H. J.; Liu, Y. X.; Xiong, L. X.; Li, Y. Q.; Yang, N.; Wang, Q. M. J. Agric. Food Chem. 2013, 61, 8730.
[17] Wang, S. L.; Shi, Y. J.; He, H. B.; Li, Y.; Li, Y.; Dai, H. Chin. Chem. Lett. 2015, 26, 672.
[18] Liu, C. L.; Liu, X. N.; Zhang, H.; Lei, X.; Liu, W. C.; Zhang, L. X.; Li, B.; Man, Y.; Hu, X. Z.; Li, Z. C. CN 1188764, 2000 [Chem. Abstr. 2000, 132, 176977].
[19] Fu, C. R.; Peng, J.; Ning, Y.; Liu, M.; Shan, P. C.; Liu, J.; Li, Y. Q.; Hu, F. Z.; Zhu, Y. Q.; Yang, H. Z.; Zou, X. M. Pest Manage. Sci. 2014, 70, 1207.
[20] Dai, H.; Xiao, Y. S.; Li, Z.; Xu, X. Y.; Qian, X. H. Chin. Chem. Lett. 2014, 25, 1014.
[21] Lü, Q.; Lu, X. T.; Dai, M.; Liu, S. M.; Zhu, W. H.; Du, P.; Lü, L. Chin. J. Org. Chem. 2015, 35, 1260 (in Chinese). (吕强, 芦昕婷, 戴明, 刘世梦, 朱为宏, 杜葩, 吕龙, 有机化学, 2015, 35, 1260.)
[22] Peng, H.; He, H. W. Chin. J. Org. Chem. 2007, 27, 502 (in Chinese). (彭浩, 贺红武, 有机化学, 2007, 27, 502.)
[23] Wang, D.; Wei, Y.; Hao, S. H. Chin. J. Org. Chem. 2015, 35, 1691 (in Chinese). (王栋, 魏艳, 郝双红, 有机化学, 2015, 35, 1691.)
[24] Xu, Y.; Lei, P.; Ling, Y.; Wang, S. W.; Yang, X. L. Chin. J. Org. Chem. 2014, 34, 1118 (in Chinese). (徐炎, 雷鹏, 凌云, 王圣文, 杨新玲, 有机化学, 2014, 34, 1118.)
[25] Lee, L. F.; Schleppnik, F. M.; Schneider, R. W.; Campbell, D. H. J. Heterocycl. Chem. 1990, 27, 243.
[26] Dai, H.; Li, Y. Q.; Du, D.; Qin, X.; Zhang, X.; Yu, H. B.; Fang, J. X. J. Agric. Food Chem. 2008, 56, 10805.
[27] Dai, H.; Shen, Y. F.; Chen, J.; Chen, H. L.; Shen, Y. J. Acta Crystallogr. 2011, E67, o726.
[28] Dai, H.; Miao, W. K.; Wu, S. S.; Qin, X.; Fang, J. X. Acta Crystallogr. 2011, E67, o775.
[29] Hu, W. Q.; Zhu, W. G.; Chen, D. H. Chin. J. Pestic. Sci. 2007, 9, 240 (in Chinese). (胡伟群, 朱卫刚, 陈定花, 农药学学报, 2007, 9, 240.)

1-甲基-3-三氟甲基-5-取代基-1H-吡唑-4-甲醛-O-(4-三氟甲基苯甲酰基)肟的合成与生物活性研究

Synthesis and Bioactivity of Novel 1-Methyl-3-trifluoromethyl- 5-subsituent-1H-pyrazole-4-carbaldehyde- O-(4-trifluoromethylbenzoyl)oximes

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