Synthesis and antifungal evaluation of a series of maleimides

Authors

  • Xiao-Long Chen,

    Corresponding author
    1. Institute of Fermentation Engineering, College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou, China
    • Correspondence to: Xiao-Long Chen, Institute of Fermentation Engineering, College of Biological and Environmental Engineering, Zhejiang University of Technology, 18 Chaowang Road, Hangzhou 310014, China. E-mail: Richard_chen@zjut.edu.cn

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  • Li-Jun Zhang,

    1. Institute of Fermentation Engineering, College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou, China
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  • Fu-Ge Li,

    1. Institute of Fermentation Engineering, College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou, China
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  • Yong-Xian Fan,

    1. Institute of Fermentation Engineering, College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou, China
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  • Wei-Ping Wang,

    1. Institute of Vegetables and Flowers, Chinese Academy of Agricultural Sciences, Beijing, China
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  • Bao-Ju Li,

    1. Institute of Vegetables and Flowers, Chinese Academy of Agricultural Sciences, Beijing, China
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  • Yin-Chu Shen

    1. Institute of Fermentation Engineering, College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou, China
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Abstract

BACKGROUND

Maleimides, both natural and synthesised, have good biological activities. In a continuous effort to discover new maleimides with good antifungal activities, the authors have synthesised a series of 3,4-dichloro-, 3-methyl and non-substituted maleimides based on previous studies. The compounds were biologically evaluated against the fungal pathogen Sclerotinia sclorotiorum.

RESULTS

Of the 63 compounds evaluated, 25 compounds had interesting inhibitory potency with EC50 < 10 µg mL−1. N-(3,5-Dichlorophenyl)-3,4-dichloromaleimide (EC50 = 1.11 µg mL−1) and N-octyl-3-methylmaleimide (EC50 = 1.01 µg mL−1) were more potent than the commercial fungicide dicloran (EC50 = 1.72 µg mL−1). The results showed that compounds exhibiting log P values within the range 2.4–3.0 displayed the best results in terms of fungicidal activity, and this seemed, therefore, to be the optimum range for this physicochemical parameter.

CONCLUSION

The present work demonstrates that some maleimides can be used as potential lead compounds for developing novel antifungal agents against S. sclerotiorum. © 2014 Society of Chemical Industry

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