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Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 12: 3574 - 3582

DOI: https://doi.org/10.6023/cjoc201906017

Synthesis and Fungicidal Activity of Novel Pyrazole-4-carbox-amide Compounds Containing Tertiary Alcohol Moiety

  • Geng Rui ,
  • Zhao Yu ,
  • Li Yihao ,
  • Liu Xinlei ,
  • Wang Ming'an
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  • Department of Applied Chemistry, China Agricultural University, Beijing 100193

Received date: 2019-06-17

  Revised date: 2019-07-08

  Online published: 2019-08-01

Supported by

Project supported by the National Natural Science Foundation of China (No. 21772229).

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Abstract

A series of novel pyrazole-4-carboxamide compounds were designed and synthesized through introducing a tertiary alcohol moiety into the C-3 position of the pyrazole ring based on the chracteristics of pyrazole-4-carboxamide fungicides and natural products with a tertiary alcohol moiety. Their structures were characterized by 1H NMR, 13C NMR, HR-ESI-MS data and X-ray diffraction. The preliminary bioassay results indicated that some of these compounds exhibit certain fungicidal activities against tested phytopathogens at the concentration of 100 µg/mL. N-(2-Fluorophenyl)-3-(1-hydroxycyclohexyl)-1,5-dimethyl-1H-pyrazole-4-carboxamide (B1) and N-(thiazol-2-yl)-3-(1-hydroxycyclohexyl)-1,5-dimethyl-1H-pyrazole-4-carbo-xamide (B10) have EC50 values of 76.3 and 71.9 µg/mL against Pythium aphanidermatum. B10 has an EC50 value of 85.4 µg/mL against Phytophthora capsici, respectively.

Key words： pyrazole-4-carboxamide; tertiary alcohol moiety; synthesis; fungicidal activity

Cite this article

Geng Rui , Zhao Yu , Li Yihao , Liu Xinlei , Wang Ming'an . Synthesis and Fungicidal Activity of Novel Pyrazole-4-carbox-amide Compounds Containing Tertiary Alcohol Moiety[J]. Chinese Journal of Organic Chemistry, 2019 , 39(12) : 3574 -3582 . DOI: 10.6023/cjoc201906017

References

[1] Zhang, Y.; Chen, Z.; Nie, J.; Zhang, F. G.; Ma, J. A. J. Org. Chem. 2019, 84, 7148.
[2] Zhang, A.; Yue, Y.; Yang, J.; Shi, J.; Tao, K.; Jin, H.; Hou, T. J. Agric. Food Chem. 2019, 67, 5008.
[3] Zhang, A.; Zhou, J.; Tao, K.; Hou, T.; Jin, H. Bioorg. Med. Chem. Lett. 2018, 28, 3042.
[4] Walter, H.; Lamberth, C.; Corsi, C. Monatsh. Chem. 2018, 149, 791.
[5] Yan, Z.; Liu, A.; Huang, M.; Liu, M.; Pei, H.; Huang, L.; Yi, H.; Liu, W.; Hu, A. Eur. J. Med. Chem. 2018, 149, 170.
[6] Mu, J. X.; Shi, Y. X.; Yang, M. Y.; Sun, Z. H.; Liu, X. H.; Li, B. J.; Sun, N. B. Molecules 2016, 21, 68.
[7] Du, S.; Tian, Z.; Yang, D.; Li, X.; Li, H.; Jia, C.; Che, C.; Wang, M.; Qin, Z. Molecules 2015, 20, 8395.
[8] Sun, J.; Zhou, Y. Molecules 2015, 20, 4383.
[9] Wu, J.; Wang, J.; Hu, D.; He, M.; Jin, L.; Song, B. Chem. Central J. 2012, 6, 51.
[10] Yang, Y.; Jiang, J. Z.; Qimei, L. B.; Yan, X. J.; Zhao, J. X.; Yuan, H. Z.; Qin, Z. H.; Wang, M. A. Molecule 2010, 15, 7075.
[11] Zhao, J.; Dong, H. B.; Yang, M. Y.; Du, J.; Jiang, J. Z.; Wang, M. A. J. Asian Nat. Prod. Res. 2014, 16, 312.
[12] Maneerat, W.; Phakhodee, W.; Ritthiwigrom, T.; Cheenpracha, S.; Promgool, T.; Yossathera, K.; Laphookhieo, S. Fitoterapia 2012, 83, 1110.
[13] Hitesh, V.; Motwani, M. D. R.; Luke, R.; Odell, A. H.; Mats, L. Eur. J. Med. Chem. 2015, 90, 462.
[14] Hernandez-Altamirano, J. M.; Largo-Gosens, A.; Martinez-Rubio, R.; Pereda, D.; Alvarez, J. M.; Acebes, J. L.; Encina, A.; Garcia-Angulo, P. Planta 2018, 247, 987.
[15] Li, X.; Han, X.; He, M.; Xiao, Y.; Qin, Z. Bioorg. Med. Chem. Lett. 2017, 26, 5936.
[16] Zhao, Y.; Tang, B.; Liu, X. L.; Li, W. Z.; Huang, M. Y.; Wang, M. A. Chin. J. Org. Chem. 2017, 37, 975(in Chinese). (赵宇, 汤博, 刘鑫磊, 李婉祯, 黄铭一, 王明安, 有机化学, 2017, 37, 975.)
[17] Zhao, Y.; Guan, A. Y.; Li, W. Z.; Wang, W. W.; Liu, X. L.; Wang, M. A. Chin. J. Org. Chem. 2019, 39, 1344(in Chinese). (赵宇, 关爱莹, 李婉祯, 王卫伟, 刘鑫磊, 王明安, 有机化学, 2019, 39, 1344.)
[18] Zhao, Y.; Tang, B.; Guan, A. Y.; Wang, W. W.; Zhang, Z. H.; Wang, M. A. Synthesis 2017, 49, 4663.
[19] Tang, B.; Guan, A. Y.; Zhao, Y.; Jiang, J. Z.; Wang, M. A.; Zhou, L. G. Chin. J. Chem. 2017, 35, 1133.
[20] Liu, B.; Han, J. T.; Tang, B.; Wang, M. A. Chin. J. Org. Chem. 2014, 34, 1442(in Chinese). (刘斌, 韩金涛, 汤博, 王明安, 有机化学, 2014, 34, 1442.)
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