Citation: Tang Xianjun, Lu Xingliang, Yang Dan, Zhang Min, Xiong Yongtong, Wu Qinglai, Li Junkai. Synthesis and Fungicidal Activities of Novel Tertiary Alcohol Ergosterol Biosynthesis Inhibitors Based on Phenazine-1-carboxylic Acid[J]. Chinese Journal of Organic Chemistry, ;2020, 40(8): 2491-2501. doi: 10.6023/cjoc202004011 shu

Synthesis and Fungicidal Activities of Novel Tertiary Alcohol Ergosterol Biosynthesis Inhibitors Based on Phenazine-1-carboxylic Acid

School of Agriculture, Yangtze University, Jingzhou, Hubei 434025

Corresponding author: Wu Qinglai, wql106@163.com Li Junkai, junkaili@sina.com
Received Date: 7 April 2020
Revised Date: 28 April 2020
Available Online: 11 May 2020
Fund Project: The National Key Research and Development Program of China 2018YFD200500The National Natural Science Foundation of China 31672069Project supported by the National Key Research and Development Program of China (No. 2018YFD200500), and the National Natural Science Foundation of China (No. 31672069)

Figures(5)

During our previous research using natural product phenazine-1-carboxylic acid as the lead compound to develop new pesticides, the phenazine-1-methanol had been found to exhibit excellent fungicidal activity. According to the above fact, a new class of phenazine-1-aryl(5-pyrimidine)methanol derivatives were designed and synthesized by using phenazine-1-methanol as a secondary lead compound, and referring to ergosterol biosynthesis inhibitor fenarimol. The bio-assays showed that compounds 6a~6p displayed moderate fungicidal activities against Thanatephorus cucumeris and Phytophthora capsici. An interesting result is that the fungicidal activities of some of the target compounds against Phenazine-1-carboxylic-Acid (PCA) specific spectrum Thanatephorus cucumeris are greatly reduced, while against fenarimol characteristic spectrum wheat powdery mildew (Erysiphe graminis) retain moderate or strong control effects. The above bio-assays results indicated the mode of action of compounds 6a~6p may be different from that of PCA, but similar to fenarimol. Therefore, further ergosterol biosynthesis inhibition experiment proved that the target compounds had the same mode of action as commercially available fungicide fenarimol.
- phenazine-1-carboxylic acid,
- fungicidal activity,
- synthesis,
- natural product
1. [1]
  Zubrod, J. P.; Bundschuh, M.; Arts, G.; Brühl, C. A.; Imfeld, G.; Knä bel, A.; Payraudeau, S.; Rasmussen, J. J.; Rohr, J.; Scharmüller, A.; Smalling, K.; Stehle, S.; Schulz, R.; Schä fer, R. B. Environ. Sci. Technol. 2019, 53, 7.
2. [2]
  Jeschke, P. Pest Manage. Sci. 2015, 72, 3.
3. [3]
  Senior, I. J.; Hollomon, D. W.; Loeffler, R. S. T.; Baldwin, B. C. J. Pestic. Sci.1995, 45, 1. doi: 10.1002/ps.2780450102
4. [4]
  Mounkoro, P.; Michel, T.; Benhachemi, R.; Surpateanu, G.; Iorga, B. I.; Fisher, N. Meunier, B. Pest Manage. Sci. 2019, 75, 8.
5. [5]
  Belkheiri, N.; Bouguerne, B.; Bedos-Belval, F.; Duran, H.; Bemis, C.; Salvayre, R.; Negre-Salvayre, A.; Baltas, M. Eur. J. Med. Chem. 2010, 45, 7.
6. [6]
  Abbott, W. S. J. Econ. Entomol. 1925, 18, 2. doi: 10.1093/jee/18.1.2
7. [7]
  Sparks, T. C.; Hahn, D. R.; Garizi, N. V. Pest Manage. Sci. 2017, 73, 4.
8. [8]
  Copping, L. G.; Duke, S. O. Pest Manage. Sci. 2007, 63, 6.
9. [9]
  Pillmoor, J. B.; Wright, K.; Terry, A. S. J. Pestic. Sci. 1993, 39, 2.
10. [10]
  Zhu, X.; Wu, Q. L.; Li, J. K. Chin. J. Org. Chem. 2019, 39, 10(in Chinese).
11. [11]
  Laursen, J. B.; Nielsen, J. Chem. Rev. 2004, 104, 3.
12. [12]
  Ge, Y. H.; Pei, D. L.; Zhao, Y. H.; Li, W. W.; Wang, S. F.; Xu, Y. Q. Curr. Microbiol. 2007, 54, 4.
13. [13]
  Palchykovska, L. G.; Vasylchenko, O. V.; Platonov, M. O.; Kostina, V. G. Biopolym. Cell 2012, 28, 6.
14. [14]
  Rewcastle, G. W.; Denny, W. A.; Baguley, B. C. J. Med. Chem. 1987, 18, 47.
15. [15]
  Spicer, J. A.; Gamage, S. A.; Rewcastle, G. W.; Finlay, G. J.; Bridewell, D. J. A.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 2000, 43, 7.
16. [16]
  Mavrodi, D. V.; Ksenzenko, V. N.; Bonsall, R. F.; Cook, R. J.; Boronin, A. M.; Thomashow, L. S. J. Bacteriol. 1998, 180, 9.
17. [17]
  Ma, Z. W.; Shen, X. M.; Hu, H. B.; Wang, W.; Peng, H. S.; Xu, P.; Zhang, X. H. J. Bacteriol. 2012, 194, 13.
18. [18]
  Zhu, X.; Yu, L. H.; Zhang, M.; Xu, Z. H.; Yao, Z. L.; Wu, Q. L.; Du, X. Y.; Li, J. K. Chem. Cent. J. 2018, 12, 10. doi: 10.1186/s13065-018-0385-6
19. [19]
  Ye, L.; Zhang, H. Y.; Xu, H.; Zou, Q.; Cheng, C.; Dong, D. X.; Xu, Y. Q.; Li, R. X. Bioorg. Med. Chem. Lett. 2010, 20, 24.
20. [20]
  Niu, J. F.; Chen, J.; Xu, Z. H.; Zhu, X.; Wu, Q. L.; Li, J. K. Bioorg. Med. Chem. Lett. 2016, 26, 22.
21. [21]
  Xiong, Z. P.; Niu, J. F.; Liu, H.; Xu, Z. H.; Li, J. K.; Wu, Q. L. Bioorg. Med. Chem. Lett. 2017, 27, 9.
22. [22]
  Krishnaiah, M.; De, Almeida, N. R.; Udumula, V.; Song, Z. C.; Chhonker, Y. S.; Abdelmoaty, M. M.; Do Nascimento, V. A.; Murry, D. J.; Conda-Sheridan, M. Eur. J. Med. Chem. 2018, 143, 1. doi: 10.1016/j.ejmech.2017.11.012
23. [23]
  Lu, X. L.; Zhu, X. Y.; Zhang, M.; Wu, Q. L.; Xu, Z. H.; Zhou, X. D.; Li, J. K. Nat. Prod. Res. 2019, 33, 15.
24. [24]
  Qin, C.; Yu, D. Y.; Zhou, X. D.; Zhang, M.; Wu, Q. L.; Li, J. K. J. Asian Nat. Prod. Res. 2019, 21, 6.
25. [25]
  Zhu, X.; Yu, L. H.; Hsiang, T.; Huang, D.; Xu, Z.; Wu, Q.; Du, X.; Li, J. Pest Manage. Sci. 2019, 75, 12.
26. [26]
  Lee, J. K.; Park, S. H.; Lee, E. Y.; Kim, Y. J.; Kyung, K. S. J. Agric. Food Chem. 2004, 52, 24.
27. [27]
  Lamberth, C. Heterocycles 2006, 68, 36.
28. [28]
  Burden, R. S.; Cooke, D. T.; Carter, G. A. Phytochemistry 1989, 20, 49.
29. [29]
  He, L. M.; Cui, K. D.; Ma, D. C.; Shen, R. P.; Huang, X. P.; Jiang, J. G.; Mu, W.; Liu, F. Plant Dis. 2017, 101, 7.
30. [30]
  Hossain, M. Z.; Goto, T. Food Anal Methods 2015, 8, 4.
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]
  Tao Yang , Kaijiao Duan , Siyu Li , Jing Wei , Qingdi Yang , Qian Wang . A Comprehensive and Innovative Chemical Experimental Teaching: Extraction and Identification of Tea Polyphenols from Pu'er Tea and the Application in Hand Cream Making. University Chemistry, 2024, 39(8): 270-275. doi: 10.3866/PKU.DXHX202312040
5. [5]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
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]
  Hexing SONG , Zan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe³⁺ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402
8. [8]
  Lijuan Wang , Yuping Ning , Jian Li , Sha Luo , Xiongfei Luo , Ruiwen Wang . Enhancing the Advanced Nature of Natural Product Chemistry Laboratory Courses with New Research Findings: A Case Study of the Application of Berberine Hydrochloride in Photodynamic Antimicrobial Films. University Chemistry, 2024, 39(11): 241-250. doi: 10.12461/PKU.DXHX202403017
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
14. [14]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
15. [15]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
16. [16]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
17. [17]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
18. [18]
  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
19. [19]
  Yihui Song , Shangshang Qin , Kai Wu , Chengyun Jin , Bin Yu . 生物化学在高水平创新型药学人才培养中的交叉融合应用——以去甲基化酶LSD1抑制剂的活性评价为例. University Chemistry, 2025, 40(6): 341-352. doi: 10.12461/PKU.DXHX202406018
20. [20]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(1776)
HTML views(350)

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