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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 10, pp 956–963 | Cite as

Synthesis and fungicidal activity of monocyclic and fused 1,2,3-triazolium-5-olates

  • Inna S. Khazhieva
  • Pavel M. Demkin
  • Oleg S. Eltsov
  • Yulia I. Nein
  • Tatiana A. Kalinina
  • Zhi-Jin Fan
  • Lai Chen
  • Bin Zhao
  • Tatiana V. GlukharevaEmail author
  • Yuri Yu. Morzherin
Article
  • 38 Downloads

4-Acetyl-3-(2-aryl-2-oxoethyl)-1-phenyl-1Н-1,2,3-triazol-3-ium-5-olates, as well as 4-hydroxy-, 4-acetoxy-, and 4-amino derivatives of 2,6-diaryl-2H-[1,2,3]triazolо[1,5-а]pyridin-8-ium-3-olates were synthesized and tested for fungicidal activity against 9 strains of phytopathogenic fungi. Some compounds were identified that significantly inhibited the growth of one or several fungal strains. It was found that 4-acetyl-3-[2-(4-chlorophenyl)-2-oxoethyl]-1-phenyl-1Н-1,2,3-triazol-3-ium-5-olate had the best antifungal properties with the median effective concentration in the range of 2.28–47.75 μg/ml.

Keywords

enamines pyridinium 1,2,3-triazoles 1,2,3-triazolium-5-olates crotonic condensation antifungal properties fungicidal activity phytopathogenic fungi 

Notes

This work received financial support from the Russian Science Foundation (grant No. 16-16-04022).

1Н and 13С NMR spectra were acquired at the Laboratory of Complex Investigations and Expert Evaluation of Organic Materials, Collective Use Center of the Ural Federal University.

Supplementary material

10593_2018_2380_MOESM1_ESM.pdf (5.2 mb)
ESM 1 (PDF 5302 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Inna S. Khazhieva
    • 1
  • Pavel M. Demkin
    • 1
  • Oleg S. Eltsov
    • 1
  • Yulia I. Nein
    • 1
  • Tatiana A. Kalinina
    • 1
  • Zhi-Jin Fan
    • 2
    • 3
  • Lai Chen
    • 2
  • Bin Zhao
    • 2
  • Tatiana V. Glukhareva
    • 1
    Email author
  • Yuri Yu. Morzherin
    • 1
  1. 1.Ural Federal University named after the first President of Russia B. N. YeltsinYekaterinburgRussia
  2. 2.State Key Laboratory of Organoelement ChemistryNankai UniversityTianjinP. R. China
  3. 3.National Collaborative Innovation Center of Chemical Science and EngineeringNankai UniversityTianjinP. R. China

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