Citation: Yu Shi, Zhao-Sheng Zhang, Jiang Shao, Chen Fu, Lan-Tu Xiong, Zhao-Dong Li, Zi-Ning Cui. Photoinduced palladium-catalyzed 1,3-diene-selective fluoroalkylamination compounds as potential bactericidal agent against Xanthomonas oryzae pv. oryzae[J]. Chinese Chemical Letters, ;2024, 35(1): 108794. doi: 10.1016/j.cclet.2023.108794 shu

Photoinduced palladium-catalyzed 1,3-diene-selective fluoroalkylamination compounds as potential bactericidal agent against Xanthomonas oryzae pv. oryzae

Yu Shi ^{a, b, 1} ,
Zhao-Sheng Zhang ^{a, 1} ,
Jiang Shao ^{a, 1} ,
Chen Fu ^a ,
Lan-Tu Xiong ^a ,
Zhao-Dong Li ^{c, *,} ,
Zi-Ning Cui ^{a, *,}

a.
National Key Laboratory of Green Pesticide, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, College of Plant Protection, South China Agricultural University, Guangzhou 510642, China
b.
Henry Fok School of Biology and Agriculture, Shaoguan University, Shaoguan 512005, China
c.
College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China

scaulizhaodong@scau.edu.cn

ziningcui@scau.edu.cn

Received Date: 13 June 2023
Revised Date: 6 July 2023
Accepted Date: 9 July 2023
Available Online: 12 July 2023

Figures(9)

A series of photoinduced palladium-catalyzed 1,3-diene-selective fluoroalkylamination derivatives was rationally synthesized based on diversity-oriented synthesis via cross coupling of 1,3-dienes, amines and fluoroalkyl iodides. The reaction featured good function group tolerance and a broad substrate scope, which could be extended to the late-stage modification of bioactive molecules. Bactericidal activity of all the compounds against Xanthomonas oryzae pv. oryzae (Xoo) was evaluated. Among them, compound E14 showed significant activity against Xanthomonas oryzae pv. oryzae (Xoo) with half maximal effective concentration (EC₅₀) value of 6.61 µmol/mL. In pot experiments, the results showed that E14 could control rice bacterial blight with protective and curative efficiencies of 37.5% and 63.2% at 200 µg/mL, respectively. Additionally, a plausible mechanism for antibacterial behavior of E14 was proposed by electron microscopy, flow cytometry, reactive oxygen species detection, and biofilm assay. In current work, it can promote the development of photoinduced palladium-catalyzed 1,3-diene-selective fluoroalkyl amination compounds as prospective antibacterial agent bearing an intriguing mode of action.
- 1,3-Diene-selective fluoroalkylamination derivatives,
- Xanthomonas oryzae pv. oryzae,
- Antibacterial activity,
- Electron microscopy,
- Reactive oxygen,
- Flow cytometry
1. [1]
  S. Jiang, M. He, X.W. Xiang, et al., J. Agric. Food Chem. 67 (2019) 11867–11876. doi: 10.1021/acs.jafc.9b04085
2. [2]
  S.Q. An, N. Potnis, M. Dow, et al., FEMS Microbiol. Rev. 44 (2020) 1–32. doi: 10.1093/femsre/fuz024
3. [3]
  S. Zhao, C. Xiao, J. Wang, et al., J. Agric. Food Chem. 68 (2020) 14204–14211. doi: 10.1021/acs.jafc.0c06363
4. [4]
  Z. Xu, S. Wang, L. Liu, et al., Plant Dis. 104 (2020) 2764–2767. doi: 10.1094/pdis-12-19-2724-a
5. [5]
  Y.L. Zhao, X. Huang, L.W. Liu, et al., J. Agric. Food Chem. 67 (2019) 7512–7525. doi: 10.1021/acs.jafc.9b02036
6. [6]
  P.K. Bangalore, S.K. Vagolu, R.K. Bollikanda, et al., J. Nat. Prod. 83 (2020) 26–35. doi: 10.1021/acs.jnatprod.9b00475
7. [7]
  J. Shi, N. Luo, M. Ding, et al., Chin. Chem. Lett. 31 (2020) 434–438. doi: 10.1016/j.cclet.2019.06.037
8. [8]
  Y. Teng, Y. Qin, D. Song, et al., Bioorg. Med. Chem. Lett. 30 (2020) 126850. doi: 10.1016/j.bmcl.2019.126850
9. [9]
  W. Fu, Z. Li, X. Shao, Adv. Agrochem. 2 (2023) 142–153. doi: 10.1016/j.aac.2023.04.002
10. [10]
  J. Cardoso, A.A. Souza, M. Vieira, Planta 256 (2022) 84. doi: 10.1007/s00425-022-03994-0
11. [11]
  P. Li, L. Shi, M.N. Gao, et al., Bioorg. Med. Chem. Lett. 25 (2015) 481–484. doi: 10.1016/j.bmcl.2014.12.038
12. [12]
  P. Li, P. Tian, Y. Chen, et al., Pest Manag. Sci. 74 (2018) 844–852. doi: 10.1002/ps.4762
13. [13]
  P.Y. Wang, H.S. Fang, W.B. Shao, et al., Bioorg. Med. Chem. Lett. 27 (2017) 4294–4297. doi: 10.1016/j.bmcl.2017.08.040
14. [14]
  K. Muller, C. Faeh, F. Diederich, Science 317 (2007) 1881–1886. doi: 10.1126/science.1131943
15. [15]
  C. Dalvit, A. Vulpetti, J. Med. Chem. 62 (2019) 2218–2244. doi: 10.1021/acs.jmedchem.8b01210
16. [16]
  E. Vitaku, D.T. Smith, J.T. Njardarson, J. Med. Chem. 57 (2014) 10257–10274. doi: 10.1021/jm501100b
17. [17]
  N.J. Adamson, S.J. Malcolmson, ACS Catal. 10 (2020) 1060–1076. doi: 10.1021/acscatal.9b04712
18. [18]
  Y. Xiong, X. Ma, G. Zhang, Org. Lett. 21 (2019) 1699–1703. doi: 10.1021/acs.orglett.9b00252
19. [19]
  Y. Zhu, W. Dong, W. Tang, Adv. Agrochem. 1 (2022) 125–138.
20. [20]
  P. Chuentragool, D. Kurandina, V. Gevorgyan, Angew. Chem. 131 (2019) 11710–11722. doi: 10.1002/ange.201813523
21. [21]
  K.P.S. Cheung, S. Sarkar, V. Gevorgyan, Chem. Rev. 122 (2022) 1543–1625. doi: 10.1021/acs.chemrev.1c00403
1. [1]
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2. [2]
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16. [16]
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17. [17]
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18. [18]
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19. [19]
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