SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 8: 2491 - 2501

DOI: https://doi.org/10.6023/cjoc202004011

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

  • Tang Xianjun ,
  • Lu Xingliang ,
  • Yang Dan ,
  • Zhang Min ,
  • Xiong Yongtong ,
  • Wu Qinglai ,
  • Li Junkai
Expand
  • School of Agriculture, Yangtze University, Jingzhou, Hubei 434025

Received date: 2020-04-07

  Revised date: 2020-04-28

  Online published: 2020-05-15

Supported by

Project supported by the National Key Research and Development Program of China (No. 2018YFD200500), and the National Natural Science Foundation of China (No. 31672069).

Fold

Abstract

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.

Key words： phenazine-1-carboxylic acid; fungicidal activity; synthesis; natural product

Cite this article

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

References

[1] Zubrod, J. P.; Bundschuh, M.; Arts, G.; Brühl, C. A.; Imfeld, G.; Knäbel, A.; Payraudeau, S.; Rasmussen, J. J.; Rohr, J.; Scharmüller, A.; Smalling, K.; Stehle, S.; Schulz, R.; Schäfer, R. B. Environ. Sci. Technol. 2019, 53, 7.
[2] Jeschke, P. Pest Manage. Sci. 2015, 72, 3.
[3] Senior, I. J.; Hollomon, D. W.; Loeffler, R. S. T.; Baldwin, B. C. J. Pestic. Sci.1995, 45, 1.
[4] Mounkoro, P.; Michel, T.; Benhachemi, R.; Surpateanu, G.; Iorga, B. I.; Fisher, N. Meunier, B. Pest Manage. Sci. 2019, 75, 8.
[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] Abbott, W. S. J. Econ. Entomol. 1925, 18, 2.
[7] Sparks, T. C.; Hahn, D. R.; Garizi, N. V. Pest Manage. Sci. 2017, 73, 4.
[8] Copping, L. G.; Duke, S. O. Pest Manage. Sci. 2007, 63, 6.
[9] Pillmoor, J. B.; Wright, K.; Terry, A. S. J. Pestic. Sci. 1993, 39, 2.
[10] Zhu, X.; Wu, Q. L.; Li, J. K. Chin. J. Org. Chem. 2019, 39, 10(in Chinese). (朱祥, 吴清来, 李俊凯, 有机化学, 2019, 39, 10.)
[11] Laursen, J. B.; Nielsen, J. Chem. Rev. 2004, 104, 3.
[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] Palchykovska, L. G.; Vasylchenko, O. V.; Platonov, M. O.; Kostina, V. G. Biopolym. Cell 2012, 28, 6.
[14] Rewcastle, G. W.; Denny, W. A.; Baguley, B. C. J. Med. Chem. 1987, 18, 47.
[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] Mavrodi, D. V.; Ksenzenko, V. N.; Bonsall, R. F.; Cook, R. J.; Boronin, A. M.; Thomashow, L. S. J. Bacteriol. 1998, 180, 9.
[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] 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.
[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] Niu, J. F.; Chen, J.; Xu, Z. H.; Zhu, X.; Wu, Q. L.; Li, J. K. Bioorg. Med. Chem. Lett. 2016, 26, 22.
[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] 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.
[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] 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] Zhu, X.; Yu, L. H.; Hsiang, T.; Huang, D.; Xu, Z.; Wu, Q.; Du, X.; Li, J. Pest Manage. Sci. 2019, 75, 12.
[26] Lee, J. K.; Park, S. H.; Lee, E. Y.; Kim, Y. J.; Kyung, K. S. J. Agric. Food Chem. 2004, 52, 24.
[27] Lamberth, C. Heterocycles 2006, 68, 36.
[28] Burden, R. S.; Cooke, D. T.; Carter, G. A. Phytochemistry 1989, 20, 49.
[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] Hossain, M. Z.; Goto, T. Food Anal Methods 2015, 8, 4.
Options
Outlines

/

〈 〉