Abstract
A novel series of amides containing N-pyridylpyrazole were designed and synthesized. All of the compounds were characterized and confirmed by IR, 1H NMR, 13C NMR, MS and elemental analysis. The single crystal structure of 9d was determined by X-ray diffraction. The bioassay tests showed that the title compounds exhibited good insecticidal activities against Mythimna separata Walker, diamondback moth and Laphygma exigua Hübner.
Similar content being viewed by others
References
R. Nauen, Pest Manag. Sci. 62, 690 (2006)
D. Cordova, E.A. Benner, M.D. Sacher, J.J. Rauh, J.S. Sopa, G.P. Lahm, T.P. Selby, T.M. Stevenson, L. Flexner, S. Gutteridge, D.F. Rhoades, L. Wu, R.M. Smith, Y. Tao, Pest Biochem. Physiol. 84, 196 (2006)
U. Ebbinghaus-Kintscher, P. Luemmena, N. Lobitz, T. Schulte, C. Funke, R. Fischer, T. Masaki, N. Yasokawa, M. Tohnishi, Cell Calcium 39, 21 (2006)
M. Tohnishi, H. Nakao, T. Furuya, A. Seo, H. Kodama, K. Tsubata, S. Fujioka, H. Kodama, T. Hirooka, T Nishimatsu. J. Pestic. Sci. 30, 354 (2005)
A.L. Knight, L. Flexner, Pest Manag. Sci. 63, 180 (2007)
D.A. Clark, G.P. Lahm, B.K. Smith, J.D. Barry, D.G. Clagg, Bioorg. Med. Chem. 16, 3163 (2008)
D.B. Sattelle, D. Cordova, T.R. Cheek, Invert. Neurosci. 8, 107 (2008)
Q. Feng, Z.L. Liu, L.X. Xiong, M.Z. Wang, Y.Q. Li, Z.M. Li, J. Agric. Food Chem. 58, 12327 (2010)
G.P. Lahm, D. Cordova, J.D. Barry, Bioorg. Med. Chem. 17, 4127 (2009)
G.P. Lahm, T.P. Selby, J.H. Freudenberger, T.M. Stevenson, B.J. Myers, G. Seburyamo, B.K. Smith, L. Flexner, C.E. Clark, D. Cordova, Bioorg. Med. Chem. Lett. 15, 4898 (2005)
C.J. Fettig, C.J. Hayes, S.R. Mckelvey, S.R. Mori, Pest Manag. Sci. 67, 548 (2011)
G.P. Lahm, T.M. Stevenson, T.P. Selby, J.H. Freudenberger, D. Cordova, L. Flexner, C.A. Bellin, C.M. Dubas, B.K. Smith, K.A. Hughes, J.G. Hollingshaus, C.E. Clark, E.A. Benner, Bioorg. Med. Chem. Lett. 17, 6274 (2007)
W.L. Dong, J.Y. Xu, X.H. Liu, Z.M. Li, B.J. Li, Y.X. Shi, Chem. J. Chinese U. 29, 1990 (2008)
W. L. Dong, X. H. Liu, J. Y. Xu, Z. M. Li, J. Chem. Res.-(S), 530 (2008)
W.L. Dong, J.Y. Xu, X.H. Liu, L.X. Xiong, Z.M. Li, Chin. J. Chem. 27, 579 (2009)
R. Sitsapesan, A. J Williams. J. Membr. Biol. 153, 93 (1996)
R. Shapiro, E.G. Taylor, W.T. Zimmerman, WO 2006062978 (2006)
Z.L. Zhou, S.M. Kher, S.X. Cai, E.R. Whittemore, S.A. Espitia, J.E. Hawkinson, M. Tran, R.M. Woodward, E. Weberb, J.F.W. Keana, Bioorg. Med. Chem. 11, 1769 (2003)
G.P. Lahm, T.P. Selby, T.M. Stevenson, WO 03015519 (2003)
H.J. Liu, J.Q. Weng, C.X. Tan, X.H. Liu, Acta Cryst. E67, o1940 (2011)
X.H. Liu, L. Pan, C.X. Tan, J.Q. Weng, B.L. Wang, Z.M. Li, Pestic. Biochem. Physiol. 101, 143 (2011)
X.H. Liu, L. Pan, J.Q. Weng, C.X. Tan, Li, Y.H., B.L. Wang, Z.M. Li. Mol. Divers. 16, 251 (2012)
C.X. Tan, J.Q. Weng, Z.X. Liu, X.H. Liu, W.G. Zhao, Phosphorus Sulfur Silicon Relat. Elem. 187, 990 (2011)
X.H. Liu, C.X. Tan, J.Q. Weng, H.J. Liu, Acta Cryst. E68, o493 (2012)
C. Fernandez–Fernandez, N. Jagerovic, I. Alkorta, C.M. Maya, L. Infantes, J. Elguero, ARKIVOC 8, 74 (2008)
X.H. Liu, C.X. Tan, J.Q. Weng, Phosphorus Sulfur Silicon Relat. Elem. 186, 558 (2011)
S. Kumar, D. Paul, H. Singh, ARKIVOC 6, 17 (2006)
X.F. Liu, X.H. Liu, Acta Cryst. E67, o202 (2011)
P.Q. Chen, C.X. Tan, J.Q. Weng, X.H. Liu, Asian J. Chem. 24, 2808 (2012)
Y.L. Xue, X.H. Liu, Y.G. Zhang, Asian J. Chem. 24, 1571 (2012)
Y.L. Xue, Y.G. Zhang, X.H. Liu, Asian J. Chem. 24, 3016 (2012)
Y.L. Xue, Y.G. Zhang, X.H. Liu, Asian J. Chem. 24, 5087 (2012)
Acknowledgments
This work was supported financially by the National Natural Science Funds of China (grant No. 21102103), the China Postdoctoral Science Foundation (grant No. 2011M500532).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Dong, WL., Xu, JY., Xiong, LX. et al. Synthesis, structure and insecticidal activity of some novel amides containing N-pyridylpyrazole. J IRAN CHEM SOC 10, 429–437 (2013). https://doi.org/10.1007/s13738-012-0176-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13738-012-0176-2