Citation: 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 shu

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

Department of Applied Chemistry, China Agricultural University, Beijing 100193

Corresponding author: Wang Ming'an, wangma@cau.edu.cn
Received Date: 17 June 2019
Revised Date: 8 July 2019
Available Online: 1 December 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21772229)the National Natural Science Foundation of China 21772229

Figures(6)

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.
- pyrazole-4-carboxamide,
- tertiary alcohol moiety,
- synthesis,
- fungicidal activity
1. [1]
  Zhang, Y.; Chen, Z.; Nie, J.; Zhang, F. G.; Ma, J. A. J. Org. Chem. 2019, 84, 7148. doi: 10.1021/acs.joc.9b00819
2. [2]
  Zhang, A.; Yue, Y.; Yang, J.; Shi, J.; Tao, K.; Jin, H.; Hou, T. J. Agric. Food Chem. 2019, 67, 5008. doi: 10.1021/acs.jafc.9b00151
3. [3]
  Zhang, A.; Zhou, J.; Tao, K.; Hou, T.; Jin, H. Bioorg. Med. Chem. Lett. 2018, 28, 3042. doi: 10.1016/j.bmcl.2018.08.001
4. [4]
  Walter, H.; Lamberth, C.; Corsi, C. Monatsh. Chem. 2018, 149, 791. doi: 10.1007/s00706-017-2101-y
5. [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. doi: 10.1016/j.ejmech.2018.02.036
6. [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. doi: 10.3390/molecules21010068
7. [7]
  Du, S.; Tian, Z.; Yang, D.; Li, X.; Li, H.; Jia, C.; Che, C.; Wang, M.; Qin, Z. Molecules 2015, 20, 8395. doi: 10.3390/molecules20058395
8. [8]
  Sun, J.; Zhou, Y. Molecules 2015, 20, 4383. doi: 10.3390/molecules20034383
9. [9]
  Wu, J.; Wang, J.; Hu, D.; He, M.; Jin, L.; Song, B. Chem. Central J. 2012, 6, 51. doi: 10.1186/1752-153X-6-51
10. [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. doi: 10.3390/molecules15107075
11. [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. doi: 10.1080/10286020.2013.879121
12. [12]
  Maneerat, W.; Phakhodee, W.; Ritthiwigrom, T.; Cheenpracha, S.; Promgool, T.; Yossathera, K.; Laphookhieo, S. Fitoterapia 2012, 83, 1110. doi: 10.1016/j.fitote.2012.04.026
13. [13]
  Hitesh, V.; Motwani, M. D. R.; Luke, R.; Odell, A. H.; Mats, L. Eur. J. Med. Chem. 2015, 90, 462. doi: 10.1016/j.ejmech.2014.11.036
14. [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. doi: 10.1007/s00425-018-2840-y
15. [15]
  Li, X.; Han, X.; He, M.; Xiao, Y.; Qin, Z. Bioorg. Med. Chem. Lett. 2017, 26, 5936.
16. [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).
17. [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).
18. [18]
  Zhao, Y.; Tang, B.; Guan, A. Y.; Wang, W. W.; Zhang, Z. H.; Wang, M. A. Synthesis 2017, 49, 4663. doi: 10.1055/s-0036-1588463
19. [19]
  Tang, B.; Guan, A. Y.; Zhao, Y.; Jiang, J. Z.; Wang, M. A.; Zhou, L. G. Chin. J. Chem. 2017, 35, 1133. doi: 10.1002/cjoc.201600794
20. [20]
  Liu, B.; Han, J. T.; Tang, B.; Wang, M. A. Chin. J. Org. Chem. 2014, 34, 1442 (in Chinese).
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
3. [3]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
4. [4]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
5. [5]
  Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
6. [6]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
7. [7]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
8. [8]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
9. [9]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
10. [10]
  Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
11. [11]
  Xinghai Li , Zhisen Wu , Lijing Zhang , Shengyang Tao . Machine Learning Enables the Prediction of Amide Bond Synthesis Based on Small Datasets. Acta Physico-Chimica Sinica, 2025, 41(2): 100010-. doi: 10.3866/PKU.WHXB202309041
12. [12]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
13. [13]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
14. [14]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
15. [15]
  Yuxin CHEN , Yanni LING , Yuqing YAO , Keyi WANG , Linna LI , Xin ZHANG , Qin WANG , Hongdao LI , Wenmin WANG . Construction, structures, and interaction with DNA of two Sm^Ⅲ₄ complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1141-1150. doi: 10.11862/CJIC.20240258
16. [16]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
17. [17]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
18. [18]
  Jianyu Qin , Yuejiao An , Yanfeng Zhang . In Situ Assembled ZnWO₄/g-C₃N₄ S-Scheme Heterojunction with Nitrogen Defect for CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408002-. doi: 10.3866/PKU.WHXB202408002
19. [19]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
20. [20]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(855)
HTML views(125)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142