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Synthesis of N-substituted dimethylmaleimides and their antifungal activities against Sclerotinia sclerotiorum

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Abstract

Compounds with maleimide, both natural and synthesized, have good biological activities, especially the antifungal activity. In order to investigate the antifungal activity of dimethylmaleimides, 17 N-substituted dimethylmaleimides were prepared from the reactions of 2,3-dimethyl maleic anhydride and amines using a facile synthetic method in this paper. These compounds were evaluated for antifungal activities against Sclerotinia sclerotiorum by the mycelium growth rate method. They exhibited minimum inhibitory concentrations (MICs) ranging from 0.01–50.0 μg/mL, with N-(2-benzimidazole)-3,4-dimethylmaleimide being the most active one with an MIC of 0.01 μg/mL. The structure and activity relationship on these compounds indicated that the hydrophobicity of the N-substituents is associated with their antifungal activity. Compared to current antifungals, most of N-substituted dimethylmaleimides have a perfect activity for S. sclerotiorum control and low toxicity.

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Acknowledgments

This study received financial support from the National Natural Science Foundation of China (Grant No. 21172198), Major State Basic Research Development Program of China (973 Program) (No. 2010CB126101), and Zhejiang Provincial Key Special Projects (No. 2007C12088).

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Authors and Affiliations

  1. Institute of Fermentation Engineering, College of Biological and Environmental Engineering, Zhejiang University of Technology, No. 18 Chaowang Road, Hangzhou, 310014, People’s Republic of China

    Zhenzhong Shen, Yongxian Fan, Fuge Li, Xiaolong Chen & Yinchu Shen

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  1. Zhenzhong Shen
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  2. Yongxian Fan
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  3. Fuge Li
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  4. Xiaolong Chen
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  5. Yinchu Shen
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Correspondence to Xiaolong Chen.

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Communicated by K.J. Gorman

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Shen, Z., Fan, Y., Li, F. et al. Synthesis of N-substituted dimethylmaleimides and their antifungal activities against Sclerotinia sclerotiorum . J Pest Sci 86, 353–360 (2013). https://doi.org/10.1007/s10340-012-0466-6

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  • DOI: https://doi.org/10.1007/s10340-012-0466-6

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