Notes

Synthesis, Crystal Structure and Biological Activity of α-(5-Chloro- 3-trifluoromethyl-1-phenylpyrazol-4-carbonyloxy)-α- arylmethyl Phosphonates

  • Liang Ying ,
  • He Hongwu ,
  • He Haifeng ,
  • Yang Ziwen
Expand
  • a Hubei Biopesticide Engineering Research Center, Hubei Academy of Agricultural Science, Wuhan 430064;
    b Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079

Received date: 2012-01-04

  Revised date: 2012-03-12

  Online published: 2012-04-27

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 20772042, 31000867).

Abstract

Fourteen novel α-(substituted pyrazol-4-carbonyloxy)-α-arylmethyl phosphonates 7a7n were synthesized from the intermediates 5-chloro-3-trifluoromethyl-1-phenylpyrazol-4-carbonyl chloride (4) and α-hydroxyl-α-arylmethyl phos- phonates (6). All compounds synthesized were identified by 1H NMR, IR spectra and elemental analysis, and the structure of 7j was further determined by X-ray single crystal diffraction method. The preliminary bioassay indicated that some compounds showed moderate fungicidal and herbicidal activities.

Cite this article

Liang Ying , He Hongwu , He Haifeng , Yang Ziwen . Synthesis, Crystal Structure and Biological Activity of α-(5-Chloro- 3-trifluoromethyl-1-phenylpyrazol-4-carbonyloxy)-α- arylmethyl Phosphonates[J]. Chinese Journal of Organic Chemistry, 2012 , 32(08) : 1513 -1518 . DOI: 10.6023/cjoc1201041

References

[1] Kluger, R.; Pike, D. C. J. Am. Chem. Soc. 1977, 99, 4504.

[2] Baillie, A. C.; Wright, K.; Wright, B. J.; Earnshaw, C. G. Pestic. Biochem. Physiol. 1988, 30, 103.

[3] Eto, M. Biosci. Biotechnol. Biochem. 1997, 61, 1.

[4] He, H. W.; Liu, Z. J. Chin. J. Org. Chem. 2001, 21, 878 (in Chinese).(贺红武, 刘钊杰, 有机化学, 2001, 21, 878.)

[5] Chen, T.; Shen, P.; Li, Y. J.; He, H. W. J. Fluorine Chem. 2006, 127, 291.

[6] Chen, T.; Shen, P.; Li, Y. J.; He, H. W. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 2135.

[7] He, H. W.; Chen, T.; Li, Y. J. J. Pestic. Sci. 2007, 32, 42.

[8] Wang, T.; He, H. W.; Miao, F. M. Chin. J. Org. Chem. 2009, 29, 1152 (in Chinese).(王涛, 贺红武, 缪方明, 有机化学, 2009, 29, 1152.)

[9] Peng, H.; Wang, T.; Xie, P.; Chen, T.; He, H. W.; Wan, J. J. Agric. Food Chem. 2007, 55, 1871.

[10] He, H. W.; Yuan, J. L.; Peng, H.; Chen, T.; Shen, P.; Wan, S. Q.; Li, Y. J.; Tan, H. L.; He, Y. H.; He, J. B.; Li, Y. J. Agric. Food Chem. 2011, 59, 4801.

[11] Mohareb, R. M.; Azia, S. I.; Abdel-Sayed, N. I. Synth. Commun. 1993, 58, 947.

[12] Boullet, F. T.; Foucaud, A. Synthesis 1982, 916.

[13] Evans, D. A.; Hurst, K. M.; Tabaks, J. M. J. Am. Chem. Soc. 1978, 100, 3467.

[14] Wang, T.; He, H. W. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 2081.

[15] Li, G. H.; Yang, H. Chin. J. Org. Chem. 2008, 28, 1918 (in Chinese).(李国华, 杨红, 有机化学, 2008, 28, 1918.)
Outlines

/