Synthesis and Biological Activity Evaluation of Novel Pyrazole Oxime Ether Derivatives Containing Chlorothiazole Group and Pyrimidine Rings

doi:10.6023/cjoc201408004

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 100-108.DOI: 10.6023/cjoc201408004 Previous Articles Next Articles

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新型含氯代噻唑基团和嘧啶环的吡唑肟醚类衍生物的合成及其生物活性研究

杨亚喆, 林大勇, 傅翠蓉, 邹小毛

南开大学元素有机化学研究所元素有机化学国家重点实验室天津化学化工协同创新中心天津 300071

收稿日期:2014-08-03 修回日期:2014-09-26 发布日期:2014-10-13
通讯作者: 邹小毛 E-mail:xmzou@nankai.edu.cn
基金资助:
国家自然科学基金(Nos. 20772067, 21472102)资助项目.

Synthesis and Biological Activity Evaluation of Novel Pyrazole Oxime Ether Derivatives Containing Chlorothiazole Group and Pyrimidine Rings

Yang Yazhe, Lin Dayong, Fu Cuirong, Zou Xiaomao

State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071

Received:2014-08-03 Revised:2014-09-26 Published:2014-10-13
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20772067, 21472102).

1. Synthesis and Biological Activity Evaluation of Novel Pyrazole Oxime Ether Derivatives Containing Chlorothiazole Group and Pyrimidine Rings.PDF(608KB)

Abstract

On the basis of our previous work, in order to seeking for novel compounds with bioactivities to settle for the resistance problem, two series of novel pyrazole oxime ether derivatives have been designed and synthesized containing chlorothiazole group and pyrimidine rings applying the bioisosterism. Their structures were determined by ¹H NMR, IR, elemental analysis and MS, and their bioactivities were performed. Nearly half of the target compounds of series A with chlorothiazole group exhibited good insecticidal activity against culex pipiens pallens (100%, 5 mg·L^-1), several compounds of series A showed good activity against Aphis laburni Kaltenbach (100%, 200 mg/L) and Tetranychus cinnabarinus (100%, 200 mg/L), and the compounds of series B with pyrimidine rings exhibited certain fungicidal activity.

Key words: pyrazole oxime, chlorothiazole, pyrimidine rings, synthesis, bioactivity

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Yang Yazhe, Lin Dayong, Fu Cuirong, Zou Xiaomao. Synthesis and Biological Activity Evaluation of Novel Pyrazole Oxime Ether Derivatives Containing Chlorothiazole Group and Pyrimidine Rings[J]. Chin. J. Org. Chem., 2015, 35(1): 100-108.

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[1] Park, H. J.; Lee, K.; Park, S. J.; Ahn, B.; Lee, J. C.; Cho, H. Y.; Lee, K. I. Bioorg. Med. Chem. Lett. 2005, 15(13), 3307.
[2] Drabek, J. DE 4200742, 1992 [Chem. Abstr. 1992, 117, 171437].
[3] 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.
[4] Obata, T.; Fujii, K.; Fukuda, Y.; Tsutsumiuchi, K. JP 03240775, 1991 [Chem. Abstr. 1991, 116, 101166].
[5] Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
[6] Zhang, S.; Zeng, X. N.; Luo, Y. Plat Protection 2004, 30, 11 (in Chinese). (张帅, 曾鑫年, 骆悦, 植物保护, 2004, 30, 11.)
[7] Peter, L. Biochim. Biophys. Acta 1998, 1364, 287.
[8] Yang, H. Z.; Li, Q. Agrochemicals 2007, 46, 81 (in Chinese).
(杨会芝, 李庆, 农药, 2007, 46, 81.)
[9] Fujimoto, H.; Mikitani, K.; Meki, N.; Imahase, T.; Nishida, K.; Fujimoto, H.; Mikitani, K.; Takano, H.; Ogasawara, Y.; Tamaki, M. EP 390498, 1990 [Chem. Abstr. 1991, 114, 101986].
[10] Obata, T.; Fujii, K. EP 391685, 1990 [Chem. Abstr. 1991, 114, 101987].
[11] 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.)
[12] Fu, C. R.; Pei, 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.
[13] Kagabu, S. Rev. Toxicol. 1997, 1, 75.
[14] Jia, J. C.; Yuan, J. X.; Fan, Z. J. Agrochemicals 2007, 46, 228 (in Chinese). (贾俊超, 苑建勋, 范志金, 农药, 2007, 46, 228.)
[15] Yokota, T.; Mikata, K.; Nagasaki, H.; Ohta, K. J. Agric. Food Chem. 2003, 51, 7066.
[16] Wu, Q.; Zhang, Q.; Yang, J. C.; Liu, C. L. Agrochemicals 2010, 49, 2 (in Chinese). (伍强, 张茜, 杨吉春, 刘长令, 农药, 2010, 49, 2.)
[17] Qu, F. J.; Lu, Q. S. J. Huaihai Inst. Technol. 2003, 12, 45 (in Chinese). (曲富军, 陆庆松, 淮海工学院学报, 2003, 12, 45.)

新型含氯代噻唑基团和嘧啶环的吡唑肟醚类衍生物的合成及其生物活性研究

Synthesis and Biological Activity Evaluation of Novel Pyrazole Oxime Ether Derivatives Containing Chlorothiazole Group and Pyrimidine Rings

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