Citation: Zi-Hui YANG, Qing-Song LIU, Yue SUN, Xue-Bao SUN, Wen GU. Synthesis, Crystal Structure and Anti-fungal/Anti-oomycete Activity of New Pyrazole-benzene Carboxamide Derivatives[J]. Chinese Journal of Structural Chemistry, ;2022, 41(3): 220325. doi: 10.14102/j.cnki.0254-5861.2011-3360 shu

Synthesis, Crystal Structure and Anti-fungal/Anti-oomycete Activity of New Pyrazole-benzene Carboxamide Derivatives

Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China

Corresponding author: Wen GU, njguwen@163.com
Received Date: 11 September 2021
Accepted Date: 10 October 2021

Fund Project: the National Natural Science Foundation of China 31770616the Natural Science Foundation for Colleges and Universities in Jiangsu Province 17KJA220002

Figures(4)

Four novel pyrazole-benzene carboxamide derivatives 2a~2d were synthesized and characterized by NMR, HRMS spectral method and X-ray diffraction analysis, and were further conducted for screening the anti-fungal/anti-oomycete activity. Compound 2d crystallizes as monoclinic space group P2₁/c with a = 42.260(4), b = 5.3751(4), c = 8.0129(9) Å, β = 92.958(10)°, V = 1817.7(3) Å³, Z = 4, M_r = 385.41, D_c = 1.408 Mg/m³, S = 1.087, μ = 0.773 mm^-1, F(000) = 808, the final R = 0.0763 and wR = 0.2136 for 2657 observed reflections (I > 2σ(I)). The preliminary antifungal assay indicates that the title compounds show fair to excellent antifungal/anti-oomycete activity toward four plant fungi and two crop oomycetes. Among them, compound 2b exhibits the strongest in vitro anti-B. cinerea effects (EC₅₀ = 1.61 mg/L). In vivo test presents compound 2b displays considerable protective and curative effects to tomato fruits infected by B. cinerea. These results indicate that compound 2b would be potential fungicides leads for further development.
- pyrazole-benzene carboxamide,
- crystal structure,
- antifungal activity,
- anti-oomycete activity
1. [1]
  Jain, A.; Sarsaiya, S.; Wu, Q.; Lu, Y.; Shi, J. A review of plant leaf fungal diseases and its environment speciation. Bioengineered 2019, 10, 409–424. doi: 10.1080/21655979.2019.1649520
2. [2]
  Fisher, M. C.; Henk, D. A.; Briggs, C. J.; Brownstein, J. S.; Madoff, L. C.; McCraw, S. L.; Gurr, S. J. Emerging fungal threats to animal, plant and ecosystem health. Nature 2012, 484, 186–194. doi: 10.1038/nature10947
3. [3]
  Lamour, K. H.; Stam, R.; Jupe, J.; Huitema, E. The oomycete broad-host-range pathogen Phytophthora capsici. Mol. Plant Pathol. 2012, 13, 329–337. doi: 10.1111/j.1364-3703.2011.00754.x
4. [4]
  Lee, H. B.; Kim, Y.; Kim, J. C.; Choi, G. J.; Park, S. H.; Kim, C. J.; Jung, H. S. Activity of some aminoglycoside antibiotics against true fungi, phytophthora and pythium species. J. Appl. Microbiol. 2005, 99, 836–843. doi: 10.1111/j.1365-2672.2005.02684.x
5. [5]
  Meitz, J. C.; Linde, C. C.; Thompson, A.; Langenhoven, S.; McLeod, A. Phytophthora capsici on vegetable hosts in South Africa: distribution, host range and genetic diversity. Australas Plant Pathol. 2010, 39, 431–439. doi: 10.1071/AP09075
6. [6]
  Gevens, A. J.; Donahoo, R. S.; Lamour, K. H.; Hausbeck, M. K. Characterization of phytophthora capsici causing foliar and pod blight of snap bean in michigan. Plant Dis. 2008, 92, 201. doi: 10.1094/PDIS-92-2-0201
7. [7]
  Veloukas, T.; Leroch, M.; Hahn, M.; Karaoglanidis, G. S. Detection and molecular characterization of boscalid-resistant Botrytis cinerea isolates from Strawberry. Plant Dis. 2011, 95, 1302–1307. doi: 10.1094/PDIS-04-11-0317
8. [8]
  Panebianco, A.; Castello, I.; Cirvilleri, G.; Perrone, G.; Epifani, F.; Ferrara, M.; Polizzi, G.; Walters, D. R.; Vitale, A. Detection of botrytis cinerea field isolates with multiple fungicide resistance from table grape in Sicily. Crop Prot. 2015, 77, 65–73. doi: 10.1016/j.cropro.2015.07.010
9. [9]
  Wang, W.; Zhang, S.; Wang, J. H.; Wu, F. R.; Wang, T.; Xu, G. Bioactivity-guided synthesis accelerates the discovery of 3-(iso)quinolinyl-4-chromenones as potent fungicide candidates. J. Agric. Food Chem. 2021, 69, 491–500. doi: 10.1021/acs.jafc.0c06700
10. [10]
  Liu, X. H.; Yu, W.; Min, L. J.; Wedge, D. E.; Tan, C. X.; Weng, J. Q.; Wu, H. K.; Cantrell, C. L.; Bajsa-Hischel, J.; Hua, X. W.; Duke, S. O. Synthesis and pesticidal activities of new quinoxalines. J. Agric. Food Chem. 2020, 68, 7324–7332. doi: 10.1021/acs.jafc.0c01042
11. [11]
  Cheng, L.; Zhang, R. R.; Wu, H. K.; Xu, T. M.; Liu, X. H. The synthesis of 6-(tertbutyl)-8-fluoro-2, 3-dimethylquinoline carbonate derivatives and their antifungal activity against pyricularia oryzae. Front. Chem. Sci. Eng. 2019, 13, 369–376. doi: 10.1007/s11705-018-1734-7
12. [12]
  Fu, Q.; Cai, P. P.; Cheng, L.; Zhong, L. K.; Tan, C. X.; Shen, Z. H.; Han, L.; Liu, X. H. Synthesis and herbicidal activity of novel pyrazole aromatic ketone analogs as HPPD inhibitor. Pest Manag. Sci. 2020, 76, 868–879. doi: 10.1002/ps.5591
13. [13]
  Welsch, M. E.; Snyder, S. A.; Stockwell, B. R. Privileged scaffolds for library design and drug discovery. Curr. Opin. Chem. Biol. 2010, 14, 347–361. doi: 10.1016/j.cbpa.2010.02.018
14. [14]
  Wang, H.; Zhai, Z. W.; Shi, Y. X.; Tan, C. X.; Weng, J. Q.; Han, L.; Li, B. J.; Liu, X. H. Novel trifluoromethylpyrazole acyl urea derivatives: synthesis, crystal structure, fungicidal activity and docking study. J. Mol. Struct. 2018, 1171, 631–638. doi: 10.1016/j.molstruc.2018.06.050
15. [15]
  Jin, T.; Zhai, Z. W.; Han, L.; Weng, J. Q.; Tan, C. X.; Liu, X. H. Synthesis, crystal structure, docking and antifungal activity of a new pyrazole acylurea compound. Chin. J. Struct. Chem. 2018, 37, 1259–1264.
16. [16]
  Sun, N. B.; Zhai, Z. W.; Shen, Z. H.; Weng, J. Q.; Tan, C. X.; Liu, X. H.; Han, L. Synthesis, crystal structure and antifungal activity of N-((2, 6-difluorophenyl)carbamoyl)-1, 3-dimethyl-1H-pyrazole-4-carboxamide. Chin. J. Struct. Chem. 2017, 36, 1667–1672.
17. [17]
  Sun, N. B.; Shen, Z. H.; Zhai, Z. W.; Wu, H. K.; Weng, J. Q.; Tan, C. X.; Liu, X. H. Design, synthesis, fungicidal activity and docking study of acyl urea derivatives containing pyrazole moiety. Chin. J. Org. Chem. 2017, 37, 2044–2049. doi: 10.6023/cjoc201702003
18. [18]
  Zhao, W.; Shen, Z. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. Synthesis and nematocidal activity of novel pyrazole carboxamide derivatives against Meloidogyne incognita. Lett. Drug Des. Discov. 2017, 14, 323–329. doi: 10.2174/1570180813666160930164327
19. [19]
  Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. Synthesis, characterization, nematocidal activity and docking study of novel pyrazole-4-carboxamide derivatives. Chin. J. Struct. Chem. 2017, 36, 423–428.
20. [20]
  Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Yuan, J.; Yang, G.; Xu, T. M.; Peng, W. L. Synthesis, nematocidal activity and docking study of novel chiral 1-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives. Bioorg. Med. Chem. Lett. 2016, 26, 3626–3628. doi: 10.1016/j.bmcl.2016.06.004
21. [21]
  Zhao, W.; Shen, Z. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. Synthesis, nematocidal activity and docking study of novel chiral 1-(3-chloropyridin-2-yl)-3-(difluoromethyl)-1H-pyrazole-4-carboxamide derivatives. J. Heterocycl. Chem. 2017, 54, 1751–1756. doi: 10.1002/jhet.2753
22. [22]
  Liang, P. B.; Shen, S.; Xu, Q.; Wang, S. M.; Jin, S. H.; Lu, H. Z.; Dong, Y. H. Design, synthesis biological activity, and docking of novel fluopyram derivatives containing guanidine group. Bioorg. Med. Chem. 2021, 115846.
23. [23]
  Xiao, L. L.; Yu, L.; Li, P.; Chi, J. Y.; Tang, Z. F.; Li, J.; Tan, S. M.; Wang, X. D. Design, synthesis, and bioactivity evaluation of new thiochromanone derivatives containing a carboxamide moiety. Molecules 2021, 26, 4391. doi: 10.3390/molecules26154391
24. [24]
  Chen, J. X.; Yi, C. F.; Wang, S. B.; Wu, S. K.; Li, S. Y.; Hu, D. Y.; Song, B. A. Novel amide derivatives containing 1, 3, 4-thiadiazole moiety: design, synthesis, nematocidal and antibacterial activities. Bioorg. Med. Chem. Lett. 2019, 29, 1203–1210. doi: 10.1016/j.bmcl.2019.03.017
25. [25]
  Cheng, Y. N.; Jiang, Z. H.; Sun, L. S.; Su, Z. Y.; Zhang, M. M.; Li, H. L. Synthesis of 1, 2, 4-triazole benzoyl arylamine derivatives and their high antifungal activities. Eur. J. Med. Chem. 2020, 200, 112463. doi: 10.1016/j.ejmech.2020.112463
26. [26]
  Sun, X. L.; Ji, Z. M.; Wei, S. P.; Ji, Z. Q. Design, synthesis and herbicidal activity of 5-cyclopropyl-N-phenylisoxazole-4-carboxamides. J. Mol. Struct. 2020, 1220, 128628. doi: 10.1016/j.molstruc.2020.128628
27. [27]
  Khallaf, A.; Wang, P.; Liu, H.; Zhuo, S. P.; Zhu, H. J. 1, 2, 4-Oxadiazole ring-containing pyridylpyrazole-4-carboxamides: synthesis and evaluation as novel insecticides of the anthranilic diamide family. J. Heterocycl. Chem. 2020, 57, 1981–1992. doi: 10.1002/jhet.3927
28. [28]
  Sheldrick, G. M. SHELXT-2018/2 and SHELXL-2018/3, programs for the solution and refining of crystal structures. University of Göttingen, Germany 2018.
29. [29]
  Yang, D. Y.; Zhao, B.; Fan, Z. J.; Yu, B.; Zhang, N. L.; Li, Z. M.; Zhu, Y. L.; Zhou, J. H.; Kalinina, T. A.; Glukhareva, T. V. Synthesis and biological activity of novel succinate dehydrogenase inhibitor derivatives as potent fungicide candidates. J. Agric. Food Chem. 2019, 67, 13185–13194. doi: 10.1021/acs.jafc.9b05751
30. [30]
  Wu, Q.; Zhao, B.; Fan, Z.; Guo, X.; Yang, D.; Zhang, N.; Yu, B.; Zhou, S.; Zhao, J.; Chen, F. Discovery of novel piperidinyl-thiazole derivatives as broad-spectrum fungicidal candidate. J. Agric. Food Chem. 2019, 67, 1360–1370. doi: 10.1021/acs.jafc.8b06054
31. [31]
  Wang, M. L.; Rui, P.; Liu, C. X.; Du, Y.; Qin, P. W.; Qi, Z. Q.; Ji, M. S.; Li, X. H.; Cui, Z. N. Design, synthesis and fungicidal activity of 2-substituted phenyl-2-oxo-, 2-hydroxyand 2-acyloxyethylsulfonamides. Molecules 2017, 22, 738. doi: 10.3390/molecules22050738
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