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Synthesis, crystal structure and antimicrobial activity of 2-((2-(4-(1H-1,2,4-triazol-1-yl)phenyl)quinazolin-4-yl)oxy)-N-phenylacetamide derivatives against phytopathogens

  • Zhijiang Fan
  • Jun Shi
  • Na Luo
  • Xiaoping Bao
Original Article
  • 21 Downloads

Abstract

A total of eighteen 2-((2-(4-(1H-1,2,4-triazol-1-yl)phenyl)quinazolin-4-yl)oxy)-N-phenylacetamide derivatives were designed and synthesized, via hybrid pharmacophore approach. Among these compounds, chemical structure of compound 4a was unambiguously confirmed by means of single-crystal X-ray diffraction analysis. All the compounds were evaluated in vitro for their inhibition activity against several important phytopathogenic bacteria and fungi in agriculture. The obtained results indicated that several compounds demonstrated potent antibacterial activity against Xanthomonas oryzae pv. oryzae (Xoo). For example, compounds 4c, 4g and 4q had EC50 values of 35.0, 36.5 and 32.4 µg/mL toward this bacterium, respectively, around 1.5 times more active than commercial bactericide bismerthiazol (EC50 = 89.8 µg/mL). Additionally, compounds 4j and 4p were found to display comparable antifungal activity against Gloeosporium fructigenum at 50 µg/mL, to commercial fungicide hymexazol. Finally, the relationships between antibacterial activities and molecular structures of this class of compounds were discussed in detail.

Graphical abstract

Keywords

Quinazoline 1,2,4-Triazole Amide Synthesis Antimicrobial activity 

Notes

Acknowledgements

This work was financially supported by Young Top-Notch Talent Support Program of Guizhou Provincial Education Department (No. 2018038) and National Natural Science Foundation of China (No. 21362003).

Supplementary material

11030_2018_9896_MOESM1_ESM.doc (6.5 mb)
Supplementary material 1 (DOC 6625 kb)

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Copyright information

© Springer Nature Switzerland AG 2018

Authors and Affiliations

  1. 1.State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine ChemicalsGuizhou UniversityGuiyangPeople’s Republic of China

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