Citation: Wen-Rui LIU, Xue-Wen HUA, Sha ZHOU, Feng-Ying YUAN, Gui-Qing WANG, Yi LIU, Xiao-Ran XING. Design, Synthesis and Biological Activity of N-Sulfonyl Aromatic Amide Derivatives[J]. Chinese Journal of Structural Chemistry, ;2021, 40(5): 666-674. doi: 10.14102/j.cnki.0254–5861.2011–2991 shu

Design, Synthesis and Biological Activity of N-Sulfonyl Aromatic Amide Derivatives

a.
College of Agriculture, Liaocheng University, Liaocheng 252000, China
b.
Collaborative Innovation Center of Zhejiang Province for Green Pesticide, School of Forestry and Bio-technology, Zhejiang A & F University, Hangzhou 311300, China
c.
Liaocheng Center for Disease Control and Prevention, Liaocheng 252000, China

Corresponding author: Xue-Wen HUA, huaxuewen@lcu.edu.cn Gui-Qing WANG, wangguiqing@lcu.edu.cn
Received Date: 24 September 2020
Accepted Date: 23 October 2020

Fund Project: the National Natural Science Foundation of China 32001929the Natural Science Foundation of Shandong Province ZR2017BC053the Innovation and Entrepreneurship Training Program for College Students of Liaocheng University CXCY2020Y116

Figures(4)

Fifteen novel N-sulfonyl aromatic amide derivatives were designed and synthesized, and the structures were characterized by ¹H- and ¹³C-NMR, EA and HRMS. The crystal structures of compounds I-8 and I-9 were obtained from X-ray diffraction: I-8 is of triclinic system, M_r = 372.35, space group P2₁/n with a = 7.9151(10), b = 8.5637(11), c = 12.2022(15) Å, β = 86.865(2)º, V = 807.09(18) Å³, Z = 2, F(000) = 384, D_c = 1.532 g/cm³, the final R = 0.0408 and wR = 0.1068 for 2836 unique reflections with 2435 observed ones (I > 2σ(I)). I-9 belongs to triclinic system, M_r = 407.39, space group P2₁/n, with a = 8.4911(8), b = 8.6053(9), c = 14.5808(15) Å, β = 77.1190(10)º, V = 995.44(17) Å³, Z = 2, F(000) = 416, D_c = 1.359 g/cm³, the final R = 0.0567 and wR = 0.1779 for 3475 unique reflections with 2392 observed ones (I > 2σ(I)). The preliminary bioassay results indicated that the target compounds showed weak nematicidal activity, while compound I-5 displayed good fungicidal activity against Colletotrichum capsici with the inhibition rate of 61.7%.
- heterocyclic amide,
- synthesis,
- crystal structure,
- fungicidal activity,
- nematicidal activity
1. [1]
  Liu, M.; Khan, A.; Wang, Z. F.; Liu, Y.; Yang, G. J.; Deng, Y.; He, N. Y. Aptasensors for pesticide detection. Biosens. Bioelectron. 2019, 130, 174−184. doi: 10.1016/j.bios.2019.01.006
2. [2]
  Chen, G. B.; Wang, P. E. Electroanalytical methods for detecting pesticides in agricultural products: a review and recent developments. Int. J. Eletrochem. Sci. 2020, 2700−2712.
3. [3]
  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
4. [4]
  Lucas, J. A.; Hawkins, N. J.; Fraaije, B. A. The evolution of fungicide resistance. Adv. Appl. Microbiol. 2015, 90, 29−92.
5. [5]
  Rabelo, M. M.; Paula-Moraes, S. V.; Pereira, E. J. G.; Siegfried, B. D. Contrasting susceptibility of lepidopteran pests to diamide and pyrethroid insecticides in a region of overwintering and migratory intersection. Pest Manag. Sci. 2020, DOI: 10.1002/ps.5984.
6. [6]
  Liu, N.; Zhong, H.; Tu, J.; Jiang, Z. G.; Jiang, Y. J.; Jiang, Y.; Jiang, Y. Y.; Li, J.; Zhang, W. N.; Wang, Y.; Sheng, C. Q. Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors. Eur. J. Med. Chem. 2018, 143, 1510−1523. doi: 10.1016/j.ejmech.2017.10.043
7. [7]
  Oyama, T.; Takahashi, S.; Yoshimori, A.; Yamamoto, T.; Sato, A.; Kamiya, T.; Abe, H.; Abe, T.; Tanuma, S. Discovery of a new type of scaffold for the creation of novel tyrosinase inhibitors. Bioorg. Med. Chem. 2016, 24, 4509−4515. doi: 10.1016/j.bmc.2016.07.060
8. [8]
  Robertson, G. R.; Rouch, M. G. Use of the succinate dehydrogenase inhibitor fluopyram for controlling blackleg in Brassicaceae species. US patent, 20180228155. 2018-08-16.
9. [9]
  Veloukas, T.; Karaoglanidis, G. S. Biological activity of the succinate dehydrogenase inhibitor fluopyram against Botrytis cinerea and fungal baseline sensitivity. Pest Manag. Sci. 2012, 68, 858−864. doi: 10.1002/ps.3241
10. [10]
  Hungenberg, H.; Fürsch, H.; Rieck, H.; Hellwege, E. Use of fluopyram for controlling nematodes in crops and for increasing yield. US patent, 20130253018. 2013-09-26.
11. [11]
  Kearn, J.; Ludlow, E.; Dillon, J.; O'Connor, V.; Holden-Dye, L. Fluensulfone is a nematicide with a mode of action distinct from anticholinesterases and macrocyclic lactones. Pestic. Biochem. Phys. 2014, 109, 44−57. doi: 10.1016/j.pestbp.2014.01.004
12. [12]
  Slomczynska, U.; South, M. S.; Bunkers, G. J.; Edgecomb, D.; Wyse-Pester, D.; Selness, S.; Ding, Y. W.; Christiansen, J.; Ediger, K.; Miller, W.; Charumilind, P.; Hartmann, G.; Williams, J.; Dimmic, M.; Shortt, B.; Haakenson, W.; Wideman, A.; Crawford, M.; Hresko, M.; McCarter, J. Tioxazafen: a new broad-spectrum seed treatment nematicide. ACS Sym. Ser. 2015, 1204, 129−147.
13. [13]
  Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L. Synthesis, nematocidal activity and SAR study of novel difluoromethylpyrazole carboxamide derivatives containing flexible alkyl chain moieties. Eur. J. Med. Chem. 2016, 125, 881−889.
14. [14]
  Cheng, L.; Zhao, W.; Shen, Z. H.; Xu, T. M.; Wu, H. K.; Peng, W. L.; Liu, X. H. Synthesis, nematicidal activity and docking study of novel pyrazole-4-carboxamide derivatives against Meloidogyne incognita. Lett. Drug Des. Discov. 2019, 16, 29−35.
15. [15]
  Lahm, G. P.; Deangelis, A. J.; Campbell, M. J. Nematocidal heterocyclic amides. WO patent, 2017116646 2017-07-06.
16. [16]
  Chen, J. X.; Chen, Y. Z.; Gan, X. H.; Song, B. J.; Hu, D. Y.; Song, B. A. Synthesis, nematicidal evaluation, and 3D-QSAR analysis of novel 1, 3, 4-oxadiazole-cinnamic acid hybrids. J. Agric. Food Chem. 2018, 66, 9616−9623. doi: 10.1021/acs.jafc.8b03020
17. [17]
  Chen, J. X.; Gan, X. H.; Yi, C. F.; Wang, S. B.; Yang, Y. Y.; He, F. C.; Hu, D. Y.; Song, B. A. Synthesis, nematicidal activity, and 3D-QSAR of novel 1, 3, 4-oxadiazole/thiadiazole thioether derivatives. Chin. J. Chem. 2018, 36, 939−944. doi: 10.1002/cjoc.201800282
18. [18]
  Bellandi, P.; Gusmeroli, M.; Sargiotto, C.; Bianchi, D. Heterocyclic trifluoroalkenyl compounds having a nematocidal activity, their agronomic compositions and use thereof. WO patent, 2017002100 2017-01-05.
19. [19]
  Schouteden, N.; Lemmens, E.; Stuer, N.; Curtis, R.; Panis, B.; Waele, D. Direct nematicidal effects of methyl jasmonate and acibenzolar-S-methyl against Meloidogyne incognita. Nat. Prod. Res. 2017, 31, 1219−1222. doi: 10.1080/14786419.2016.1230111
20. [20]
  Liu, X. H.; Qiao, L.; Zhai, Z. W.; Cai, P. P.; Cantrell, C. L.; Tan, C. X.; Weng, J. Q.; Han, L.; Wu, H. K. Novel 4-pyrazole carboxamide derivatives containing flexible chain motif: design, synthesis and antifungal activity. Pest Manag. Sci. 2019, 75, 2892−2900. doi: 10.1002/ps.5463
21. [21]
  Hua, X. W.; Liu, N. N.; Fan, Z. J.; Zong, G. N.; Ma, Y.; Lei, K.; Yin, H.; Wang, G. Q. Design, synthesis and biological activity screening of novel amide derivatives containing aromatic thioether group. Chin. J. Org. Chem. 2019, 39, 2581−2588.
22. [22]
  Hua, X. W.; Liu, W. R.; Su, Y. Y.; Liu, X. H.; Liu, J. B.; Liu, N. N.; Wang, G. Q.; Jiao, X. Q.; Fan, X. Y.; Xue, C. M.; Liu, Y.; Liu, M. Studies on the novel pyridine sulfide containing SDH based heterocyclic amide fungicide. Pest Manag. Sci. 2020, 76, 2368−2378.
23. [23]
  Hua, X. W.; Liu, N. N.; Zhou, S.; Zhang, L. L.; Yin, H.; Wang, G. Q.; Fan, Z. J.; Ma, Y. Design, synthesis, and biological activity of novel aromatic amide derivatives containing sulfide and sulfone substructures. Engineering 2020, 6, 553−559. doi: 10.1016/j.eng.2019.09.011
24. [24]
  Fan, Z. J.; Yang, Z. K.; Zhang, H. K.; Mi, N.; Wang, H.; Cai, F.; Zuo, X.; Zheng, Q. X.; Song, H. B. Synthesis, crystal structure, and biological activity of 4-methyl-1, 2, 3-thiadiazole-containing 1, 2, 4-triazolo[3, 4-b][1, 3, 4]thiadiazoles. J. Agric. Food Chem. 2010, 58, 2630−2636.
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沈阳化工大学材料科学与工程学院沈阳 110142