Full Papers

Synthesis and Bioactivities of Novel 1-Phenyl-3-Methyl-5-Aryloxy-1H-Pyrazole-4- Carbaldehyde-O-((2-Chloropyridin-5-yl)methyl)oximes

  • Dai Hong ,
  • Shi Lei ,
  • Zhang Hai-Jun ,
  • Li Yong-Qiang ,
  • Fang Jian-Xin ,
  • Shi Yu-Jun
Expand
  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
    b Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071

Received date: 2012-01-29

  Revised date: 2012-03-05

  Online published: 2012-04-11

Supported by

Project supported by the National Natural Science Foundation of China (No. 21102077), the Science and Technology Projects Fund of Nantong City (Nos. K2010016, AS2010005, AS2011011), and the Science Foundation of Nantong University (Nos. 09Z010, 09C001).

Abstract

Fourteen novel pyrazole oxime ether derivatives containing a 2-chloro-5-methyl pyridyl ring were synthesized by the reaction of 1-phenyl-3-methyl-5-aryloxy-1H-pyrazole-4-carbaldehyde oximes with 2-chloro-5-chloromethyl pyridine. The structures of all new compounds were confirmed by 1H NMR, 13C NMR spectra and elemental analysis. Preliminary bioassay results indicated that some compounds exhibited certain fungicidal and plant growth regulatory activities.

Cite this article

Dai Hong , Shi Lei , Zhang Hai-Jun , Li Yong-Qiang , Fang Jian-Xin , Shi Yu-Jun . Synthesis and Bioactivities of Novel 1-Phenyl-3-Methyl-5-Aryloxy-1H-Pyrazole-4- Carbaldehyde-O-((2-Chloropyridin-5-yl)methyl)oximes[J]. Chinese Journal of Organic Chemistry, 2012 , 32(06) : 1060 -1066 . DOI: 10.6023/cjoc1201292

References

[1] Liu, C. L. Chin. J. Pestic. 2009, 48(1), 60 (in Chinese).(刘长令, 农药, 2009, 48(1), 60.)
[2] Ge, Q. J.; Chen, L. Z.; Du, X. H. Chin. J. Org. Chem. 2011, 31,1510 (in Chinese).(葛前建, 陈列忠, 杜晓华, 有机化学, 2011, 31, 1510.)
[3] Zhao, P. L.; Wang, F.; Zhang, M. Z.; Liu, Z. M.; Huang, W.; Yang,G. F. J. Agric. Food Chem. 2008, 56, 10767.  
[4] Sun, Y. F.; Li, Y. Q.; Ling, Y.; Yu, H. L.; Yang, S. X.; Yang, X. L.Chin. J. Org. Chem. 2011, 31, 1425 (in Chinese).(孙玉凤, 李永强, 凌云, 宇红莲, 杨绍祥, 杨新玲, 有机化学,2011, 31, 1425.)
[5] 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.  
[6] Gao, Y. L.; Lin, X. F.; Han, F. F.; Bao, X. P. Chin. 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.)
[7] An, Y.; Wei, W.; Mou, P. P.; Jia, Jin. Y.; Lü, J. Z.; Chen, X. Chin.J. Org. Chem. 2010, 30, 1726 (in Chinese).(安悦, 魏魏, 牟萍萍, 贾金英, 吕建州, 陈欣, 有机化学, 2010,30, 1726.)
[8] Raphy, G.; Gingrll, M.; Hawkins, D. W. WO 93/25535, 1993 [Chem. Abstr. 1993, 121, 280635c].  
[9] Li, Y. X.; Ling, L.; Chen, Q. Chin. J. Org. Chem. 2011, 31, 306 (inChinese).(李元祥, 林龙, 陈琼, 有机化学, 2011, 31, 306.)
[10] Rizk, H. F.; EI-Badawi, M. A.; Ibrahim, S. A.; EI-Borai, M. A.Chin. J. Chem. 2011, 29, 1451.
[11] Rashad, A. E.; Hegab, M. I.; Abdel-Megeid, R. E.; Micky, J. A.;Abdel-Megeid, F. M. E. Bioorg. Med. Chem. 2008, 16, 7102.  
[12] Lang, Y. C.; Bai, Y. L. Modern Agrochem. 2006, 5(5), 6 (in Chinese).(郎玉成, 柏亚罗, 现代农药, 2006, 5(5), 6.)
[13] Caboni, P.; Sammelson, R. E.; Casida, J. E. J. Agric. Food Chem.2003, 51, 7055.  
[14] Philip, L. G.; Paul, S. T. WO 2003015519, 2003 [Chem. Abstr.2003, 138, 200332].
[15] Hughes, K. A.; Lahm, G. P. WO 2004067528, 2004 [Chem. Abstr.2004, 141, 190786].
[16] Liu, J.; Xie, H. P.; Song, B. A.; Hu, D. Y.; Yang, S.; Jin, L. H.;Xue, W.; Wu, J.; Xu, W. M. Chin. J. Org. Chem. 2010, 30, 1347 (inChinese).(刘杰, 谢化鹏, 宋宝安, 胡德禹, 杨松, 金林红, 薛伟, 吴剑,徐维明, 有机化学, 2010, 30, 1347.)
[17] Xiao, L.X.; Shi, D. Q. Chin. J. Org. Chem. 2010, 30, 85 (in Chinese).(肖琳霞, 石德清, 有机化学, 2010, 30, 85.)
[18] Liu, J. B.; Tao, W. F.; Hu, Y.; Dai, H.; Fang, J. X. Chin. J. Org.Chem. 2006, 26, 1566 (in Chinese).(刘建兵, 陶伟峰, 胡燕, 戴红, 方建新, 有机化学, 2006, 26,1566.)
[19] Jo, Y. W.; Im, W. B.; Rhee, J. K.; Shim, M. J.; Kim, W. B.; Choi,E. C. Bioorg. Med. Chem. 2004, 12, 5909.  
[20] Singh, P.; Kaur, P.; Luxami, V.; Kaur, S.; Kumar, S. Bioorg. Med.Chem. 2007, 15, 2386.  
[21] Tian, Z. Z.; Shao, X. S.; Li, Z.; Qian, X. H.; Huang, Q. C. J. Agric.Food Chem. 2007, 55, 2288.  
[22] Finkelstein, B. L.; Martz, M. A.; Strock, C. J. Pestic. Sci. 1997, 50,319.  
[23] Kiriyama, K.; Itazu, Y.; Kagabu, S. J. Pest. Sci. 2003, 28, 8.  
[24] Mu, C.-W.; Qin, Z.-H. Modern Agrochem. 2003, 2(2), 1 (in Chinese).(慕长伟, 覃兆海, 现代农药, 2003, 2(2), 1.)
[25] Mu, C.-W.; Qin, Z.-H. Modern Agrochem. 2003, 2(3), 4 (in Chinese).(慕长伟, 覃兆海, 现代农药, 2003, 2(3), 4.)
[26] Sun R. F.; Lü, M. Y.; Chen, L.; Li, Q. S.; Song, H. B.; Bi, F. C.;Huang, R. Q.; Wang, Q. M. J. Agric. Food Chem. 2008, 56, 11376.  
[27] Luo, Y. P.; Gong, Q.; Chen, Q.; Yang, G. F. Chin. J. Org. Chem.2008, 28, 1561 (in Chinese).(骆炎平, 龚青, 陈琼, 杨光富, 有机化学, 2008, 28, 1561.)
[28] 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.)
[29] Sun, N. B.; Shen, D. L.; Tan, C. X.; Weng, J. Q.; Cong, S.; Fu, H.Chin. J. Org. Chem. 2008, 28, 713 (in Chinese).(孙娜波, 沈德隆, 谭成侠, 翁建全, 丛杉, 傅昊, 有机化学,2008, 28, 713.)
[30] Yan, M.; Shi, D. Q. Chin. J. Org. Chem. 2008, 28, 736 (in Chinese).(严曼, 石德清, 有机化学, 2008, 28, 736.)
[31] Bai, K.; Yao, C. P.; Chen, Q.; Shen, C.; Pei, W. Chin. J. Org.Chem. 2010, 30, 1255 (in Chinese). (拜堃, 姚彩萍, 陈青, 沈忱, 裴文, 有机化学, 2010, 30, 1255.)
[32] Lee, L. F.; Schleppnik, F. M.; Schneider, R. W.; Campbell, D. H. J.Heterocycl. Chem. 1990, 27, 243.  
[33] Takaishi, H.; Hamaguchi, H.; Nishimura, A.; Yanaka, K. JP62053969, 1987 [Chem. Abstr. 1987, 107, 115585].
[34] Liu, J. B.; Li, L. C.; Dai, H.; Liu, Z.; Fang, J. X. J. Organomet.Chem. 2006, 691, 2686.  
[35] Jin, Z.; Hu, Y.; Huo, A. H.; Tao, W. F.; Shao, L.; Liu, J. B.; Fang,J. X. J. Organomet. Chem. 2006, 691, 2340.  
Outlines

/