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Synthesis and antibacterial activity of oxime ester derivatives containing 1,2,4-triazole or 1,3,4-oxadiazole moiety

Chemical Papers volume 71, pages 1953–1960 (2017)Cite this article

Abstract

A series of oxime ester derivatives containing 1,2,4-triazole or 1,3,4-oxadiazole moiety were designed and synthesized, and their antibacterial activities in vitro against Xanthomonas axonopodis pv. citri (Xac) and Xanthomonas oryzae pv. oryzae (Xoo) were evaluated. The bioassays showed that all the title compounds exhibit potent antibacterial activity against Xac and Xoo. In particular, the compounds 4a, 5a, 5b, 5c, 5d, 5h and 5i exhibited remarkable antibacterial activity against Xoo, with the EC50 values ranging from 15.15 to 49.34 μg/mL, which were superior to that of bismerthiazol (92.61 μg/mL). This study indicated that oxime ester derivatives containing 1,2,4-triazole or 1,3,4-oxadiazole moiety may be used as potential alternative templates in the search for novel antibacterial agents.

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Acknowledgements

The authors gratefully acknowledge the National Nature Science Foundation of China (No. 21462012), the Special Fund for Outstanding Scientific and Technological Candidates of Guizhou Province (No. 201535) and the Innovation Fund for Graduate Student of Guizhou University (No. 2016076).

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Author notes

  1. Xiaobin Wang and Xinmin Zhong contributed equally to this work.

Authors and Affiliations

  1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, 550025, Guiyang, China

    Xiaobin Wang, Xinmin Zhong, Xuesong Zhu, Qin Li, Juping Zhang, Xianghui Ruan & Wei Xue

  2. Institute of Plant Protection and Soil Fertilizer, Hubei Academy of Agricultural Science, Wuhan, 430076, China

    Hua Wang

Authors
  1. Xiaobin Wang
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  2. Xinmin Zhong
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  3. Xuesong Zhu
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  4. Hua Wang
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  5. Qin Li
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  6. Juping Zhang
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  7. Xianghui Ruan
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  8. Wei Xue
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Correspondence to Wei Xue.

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Wang, X., Zhong, X., Zhu, X. et al. Synthesis and antibacterial activity of oxime ester derivatives containing 1,2,4-triazole or 1,3,4-oxadiazole moiety. Chem. Pap. 71, 1953–1960 (2017). https://doi.org/10.1007/s11696-017-0189-5

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  • DOI: https://doi.org/10.1007/s11696-017-0189-5

Keywords

  • 1,2,4-Triazole
  • 1,3,4-Oxadiazole
  • Oxime ester
  • Antibacterial activity