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The synthesis of 6-(tert-butyl)-8-fluoro-2,3-dimethylquinoline carbonate derivatives and their antifungal activity against Pyricularia oryzae

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Abstract

A series of novel 6-(tert-butyl)-8-fluoro-2,3-dimethylquinoline carbonate derivatives were designed and synthesized. Bioassay results showed that some of them exhibited good activity against Pyricularia oryzae (P. oryzae). It was found that the compound 5q (benzyl (6-(tert-butyl)-8-fluoro-2,3-dimethylquinolin-4-yl) carbonate) possessed good activity against P. oryzae whatever protective activity (10 mg∙L–1) or curative activity (25 mg∙L–1), which was better than that of control tebufloquin. In addition, the frontier molecular orbit results revealed that the compound held higher activity against P. oryzae when the total energy was low and the ClogP was high, which may provide useful information for further design novel fungicides.

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Acknowledgements

This work was supported financially by Zhejiang Provincial Natural Science Foundation of China (No. LY16C140007) and Research Institute Special Program of Department of Science and Technology of Zhejiang Province (No. 2015F50030).

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Authors and Affiliations

  1. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, China

    Long Cheng, Hongke Wu & **nghai Liu

  2. Zhejiang Base of National Southern Pesticide Research Centre, Zhejiang Research Institute of Chemical Industry, Hangzhou, 310023, China

    Long Cheng, Ruirui Zhang & Tianming Xu

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  1. Long Cheng
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  2. Ruirui Zhang
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  3. Hongke Wu
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  4. **nghai Liu
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Correspondence to **nghai Liu or Tianming Xu.

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Cheng, L., Zhang, R., Wu, H. et al. The synthesis of 6-(tert-butyl)-8-fluoro-2,3-dimethylquinoline carbonate derivatives and their antifungal activity against Pyricularia oryzae. Front. Chem. Sci. Eng. 13, 369–376 (2019). https://doi.org/10.1007/s11705-018-1734-7

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  • DOI: https://doi.org/10.1007/s11705-018-1734-7

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