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Synthesis of novel quinazolin-4(3H)-one derivatives containing the 7-oxo-1,2,4-triazolo[1,5-a]pyrimidine moiety as effective agricultural bactericides against the pathogen Xanthomonas oryzae pv. oryzae

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Abstract

A series of novel quinazolin-4-one derivatives (7a–7n) bearing the 7-oxo-1,2,4-triazolo[1,5-a]pyrimidine moiety were designed, synthesized and evaluated for their inhibition activities against phytopathogenic bacteria and fungi in vitro. All of the target compounds were fully characterized through \(^{1}\hbox {H}\) NMR, \(^{13}\hbox {C}\) NMR, HRMS and IR spectra. Among these compounds, the structure of compound 7e was unambiguously confirmed via single-crystal X-ray diffraction analysis. The turbidimetric assays indicated that compounds 7b, 7d, 7g, 7k and 7n exhibited much more potent inhibition activities against the pathogen Xanthomonas oryzae pv. oryzae (Xoo), relative to control Bismerthiazol. Moreover, antibacterial activities of compounds 7j, 7k and 7n against the pathogen Xanthomonas axonopodis pv. citri (Xac) were comparable to that of control Bismerthiazol. As for the pathogen Ralstonia solanacearum (Rs), only compounds 7g and 7i demonstrated inhibition activities similar to control Thiadiazole-copper. Moreover, this class of compounds did not display inhibition activity against three fungi tested. The above findings indicated that quinazolin-4-one derivatives containing the 7-oxo-1,2,4-triazolo[1,5-a]pyrimidine moiety have a potential as promising candidates for the development of new and more efficient agricultural bactericides.

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Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (No. 21362003) and the Agricultural Research Projects of Guizhou Province (No. 20093010).

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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, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025, China

    Huan Du, Zhijiang Fan, Lan Yang & ** Bao

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  1. Huan Du
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  2. Zhijiang Fan
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  3. Lan Yang
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  4. ** Bao
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Correspondence to ** Bao.

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11030_2017_9782_MOESM1_ESM.doc

Supplementary data The original spectral files (including 1H NMR, 13C NMR and HRMS) of intermediates 5 & 6as well as target compounds 7a-7n can be found in this section. 294 bytes

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Du, H., Fan, Z., Yang, L. et al. Synthesis of novel quinazolin-4(3H)-one derivatives containing the 7-oxo-1,2,4-triazolo[1,5-a]pyrimidine moiety as effective agricultural bactericides against the pathogen Xanthomonas oryzae pv. oryzae . Mol Divers 22, 1–10 (2018). https://doi.org/10.1007/s11030-017-9782-3

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