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Design and synthesis of potential fungicidal compounds derived from natural products, (-)-menthol and (-)-borneol

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Abstract

Twelve Novel compounds derived from (-)-menthol and (-)-borneol were designed, synthesized, and characterized by 1H NMR, 13C NMR, and HRMS. The fungicidal activities of these novel compounds against Botrytis cinerea, Curvularia lunata, and Alternaria alternata were evaluated. The results indicated that (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 4-(4-((2,4-difluorophenyl)sulfonyl)piperazin-1-yl)-4-oxobutanoate (6d) displayed potential fungicidal activities against B. cinerea and C. lunata. Especially, 6d exhibited IC50 value of 22.9 mg/L against C. lunata, which has higher fungicidal activity than commercial product hymexazol and amicarthiazol. In addition, the superficial structure–activity relationship was discussed. This study may provide a structural template for the design of novel fungicides.

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Acknowledgements

DH thanks Dr. Stephan Handschuh-Wang for the language polishing.

Funding

This work was financially supported by Shenzhen University Top Ranking Project (86000000210).

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Authors and Affiliations

  1. School of Pharmaceutical Sciences, Health Science Center, Shenzhen University, 518060, Shenzhen, PR China

    Tianyuan Zhang, Shumin Zheng, Danling Huang & Yong-Xian Cheng

  2. College of Physics and Optoelectronic Engineering, Shenzhen University, 518060, Shenzhen, PR China

    Tianyuan Zhang

  3. Dalian Academy of Agricultural Sciences, 116036, Dalian, China

    Shuyan You

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  1. Tianyuan Zhang
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Correspondence to Danling Huang or Yong-Xian Cheng.

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Zhang, T., Zheng, S., You, S. et al. Design and synthesis of potential fungicidal compounds derived from natural products, (-)-menthol and (-)-borneol. Med Chem Res 31, 307–315 (2022). https://doi.org/10.1007/s00044-021-02844-0

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  • DOI: https://doi.org/10.1007/s00044-021-02844-0

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