Synthesis, Crystal Structure and Fungicidal Activity of Novel 1,5-Diaryl-3-benzoyloxy-1H-pyrazoles

Yuan-Yuan Liu; Yi Li; Hong-Jun Zhu; Kai Chen; Bin Huang; Ya-Ping Yang

doi:10.14233/ajchem.2014.16460

Issue

Vol. 26 No. 15 (2014): Vol 26 Issue 15

Issue Published : July 16, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Crystal Structure and Fungicidal Activity of Novel 1,5-Diaryl-3-benzoyloxy-1H-pyrazoles

https://doi.org/10.14233/ajchem.2014.16460

Yuan-Yuan Liu

Department of Chemical and Pharmaceutical Engineering, Southeast University ChengXian College, Nanjing 210088, P.R. China; These authors contribute to this work equally

Yi Li

College of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009, P.R. China;These authors contribute to this work equally

Hong-Jun Zhu

Department of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, P.R. China

Kai Chen

Department of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, P.R. China

Bin Huang

Department of Chemical and Pharmaceutical Engineering, Southeast University ChengXian College, Nanjing 210088, P.R. China

Ya-Ping Yang

Department of Chemical and Pharmaceutical Engineering, Southeast University ChengXian College, Nanjing 210088, P.R. China

Corresponding Author(s) : Yuan-Yuan Liu

liuyuanyuan1985419@163.com

Asian Journal of Chemistry, Vol. 26 No. 15 (2014): Vol 26 Issue 15
Article Published : July 19, 2014

Abstract

Seven novel 1,5-diaryl-3-benzoyloxy-1H-pyrazoles (2a-2g) were prepared by the DCC condensation of 1,5-diaryl-1H-pyrazol-3-ols (1a-1g) with benzoic acid. Their structures were characterized by elemental analysis, IR, ¹H NMR and mass spectral data. The structure of 5-(3,4-dimethoxyphenyl)-1-phenyl-3-benzoyloxy-1H-pyrazole (2d) was also determined by single crystal X-ray diffraction analysis. Bioassay results indicated that the compounds 5-(4-fluorophenyl)-1-phenyl-3-benzoyloxy-1H-pyrazole (2f) and 1,5-diphenyl-3-benzoyloxy-1H-pyrazole (2a) exhibited excellent-to-medium fungicidal activity against Sclerotinia sclerotiorum at a dosage of 10 μg/mL. The structure-activity relationships (SAR) were also discussed

Keywords

Fungicidal activity Crystal structure 1,5-Diaryl-3-benzoyloxy-1H-pyrazoles Structure-activity relationships

Liu, Y.-Y., Li, Y., Zhu, H.-J., Chen, K., Huang, B., & Yang, Y.-P. (2014). Synthesis, Crystal Structure and Fungicidal Activity of Novel 1,5-Diaryl-3-benzoyloxy-1H-pyrazoles. Asian Journal of Chemistry, 26(15), 4883–4886. https://doi.org/10.14233/ajchem.2014.16460

Download Citation

References

R. Stierl, M. Scherer, W. Schrof and E.J. Butterfield, BCPC Conf - Pests Dis., 1, 261 (2000).
E. Ammermann, G. Lorenz, K. Schelberger, B. Mueller, R. Kirstgen and H. Sauter, BCPC Conf - Pests Dis., 2, 541 (2000).
R. Stierl, M. Merk, W. Schrof and E.J. Butterfield, BCPC Conf - Pests Dis., 3, 859 (2000).
Y.H. Li, R. Liu, Z.W. Yan, X.N. Zhang and H.J. Zhu, Bull. Korean Chem. Soc., 31, 3341 (2010); doi:10.5012/bkcs.2010.31.11.3341.
H.J. Zhu, H. Shi, H.S. Jia, Y.F. Li, G.L. Song, H.H. Liu, Y.F. Sun and J.T. Wang, CN Patent 101284815 (2008).
T. Konno, K. Kuriyama, H. Hamaguchi and O. Kajihara, BCPC Conf. Pests Dis., 1, 71 (1990).
Y. Miura, T. Mabuchi, M. Kajioka and I. Yanai, European Patent 361114 (1990).
Y.Y. Liu, H. Shi, Y.F. Li and H.J. Zhu, J. Heterocycl. Chem., 47, 897 (2010); doi:10.1002/jhet.424.
Y.Y. Liu, G.K. He, K. Chen, Y.F. Li and H.J. Zhu, J. Heterocycl. Chem., 49, 897 (2012).
Y.Y. Liu, H. Shi, G.K. He, G.L. Song and H.J. Zhu, HeIv. Chim. Acta, 95, 1645 (2012); doi:10.1002/hlca.201100509.
A. Kocabalkanli, O. Ates and G. Otuk, Farmaco, 56, 975 (2001); doi:10.1016/S0014-827X(01)01158-2.
K.M. Rajkotia and P.H. Parsania, J. Indian Chem. Soc., 75, 524 (1998).
G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.
C. Picard, N. Arnaud and P. Tisnes, Synthesis, 1471 (2001); doi:10.1055/s-2001-16076.
Y. Nagao, W.M. Dai, M. Ochiai, S. Tsukagoshi and E. Fujita, J. Org. Chem., 55, 1148 (1990); doi:10.1021/jo00291a012.
M.C. Duriez, T. Pigot, C. Picard, L. Cazaux and P. Tisnes, Tetrahedron, 48, 4347 (1992); doi:10.1016/S0040-4020(01)80444-0.
L. Cazaux, M.C. Duriez, C. Picard and P. Tisnes, Tetrahedron Lett., 30, 1369 (1989); doi:10.1016/S0040-4039(00)99467-X.

References

R. Stierl, M. Scherer, W. Schrof and E.J. Butterfield, BCPC Conf - Pests Dis., 1, 261 (2000).

E. Ammermann, G. Lorenz, K. Schelberger, B. Mueller, R. Kirstgen and H. Sauter, BCPC Conf - Pests Dis., 2, 541 (2000).

R. Stierl, M. Merk, W. Schrof and E.J. Butterfield, BCPC Conf - Pests Dis., 3, 859 (2000).

Y.H. Li, R. Liu, Z.W. Yan, X.N. Zhang and H.J. Zhu, Bull. Korean Chem. Soc., 31, 3341 (2010); doi:10.5012/bkcs.2010.31.11.3341.

H.J. Zhu, H. Shi, H.S. Jia, Y.F. Li, G.L. Song, H.H. Liu, Y.F. Sun and J.T. Wang, CN Patent 101284815 (2008).

T. Konno, K. Kuriyama, H. Hamaguchi and O. Kajihara, BCPC Conf. Pests Dis., 1, 71 (1990).

Y. Miura, T. Mabuchi, M. Kajioka and I. Yanai, European Patent 361114 (1990).

Y.Y. Liu, H. Shi, Y.F. Li and H.J. Zhu, J. Heterocycl. Chem., 47, 897 (2010); doi:10.1002/jhet.424.

Y.Y. Liu, G.K. He, K. Chen, Y.F. Li and H.J. Zhu, J. Heterocycl. Chem., 49, 897 (2012).

Y.Y. Liu, H. Shi, G.K. He, G.L. Song and H.J. Zhu, HeIv. Chim. Acta, 95, 1645 (2012); doi:10.1002/hlca.201100509.

A. Kocabalkanli, O. Ates and G. Otuk, Farmaco, 56, 975 (2001); doi:10.1016/S0014-827X(01)01158-2.

K.M. Rajkotia and P.H. Parsania, J. Indian Chem. Soc., 75, 524 (1998).

G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.

C. Picard, N. Arnaud and P. Tisnes, Synthesis, 1471 (2001); doi:10.1055/s-2001-16076.

Y. Nagao, W.M. Dai, M. Ochiai, S. Tsukagoshi and E. Fujita, J. Org. Chem., 55, 1148 (1990); doi:10.1021/jo00291a012.

M.C. Duriez, T. Pigot, C. Picard, L. Cazaux and P. Tisnes, Tetrahedron, 48, 4347 (1992); doi:10.1016/S0040-4020(01)80444-0.

L. Cazaux, M.C. Duriez, C. Picard and P. Tisnes, Tetrahedron Lett., 30, 1369 (1989); doi:10.1016/S0040-4039(00)99467-X.

Issue

Vol. 26 No. 15 (2014): Vol 26 Issue 15

Synthesis, Crystal Structure and Fungicidal Activity of Novel 1,5-Diaryl-3-benzoyloxy-1H-pyrazoles

Corresponding Author(s) : Yuan-Yuan Liu

Abstract

Keywords

Full Article

Download Citation

References

Table Of Contents