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Synthesis and fungicidal activity of imidazole dicyanamide ionic liquids

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Abstract

Three 1-alkyl-3-methylimidazolium dicyanamide ([Cnmim][N(CN)2]) ionic liquids were synthesized through anion-exchange reaction and characterized by FT-IR, 1H-NMR and 13C-NMR spectroscopy and by differential scanning calorimetry. Their determined solubilities in common solvents of different polarity and surface tension were proved to be related to the length of their alkyl side chain. In antifungal toxicity screening, 1-decyl-3-methylimidazolium dicyanamide, [C10mim][N(CN)2], was tested against five common agricultural fungi, Valsa mali, Pythium aphanidermatum, Rhizoctonia solani, Phytophthora capsici and Alternaria solani. Since [C10mim][N(CN)2] exhibited an excellent effect on Valsa mali with a 100% inhibition rate, this fungus was selected for structure–activity relationship studies. Comparing the effect of the alkyl chain in [Cnmim][N(CN)2] revealed that imidazolium cations with longer carbon chains had better fungicidal activity. On the other hand, anions may also have influence on the fungicidal activity, but the factor and causes need further studies.

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  1. Department of Applied Chemistry, China Agricultural University, Yuanmingyuan West Road 2#, Haidian District, Beijing, 100193, China

    Jingyu Zhao & Haixiang Gao

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  1. Jingyu Zhao
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  2. Haixiang Gao
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Zhao, J., Gao, H. Synthesis and fungicidal activity of imidazole dicyanamide ionic liquids. Chem. Pap. 77, 101–107 (2023). https://doi.org/10.1007/s11696-022-02333-7

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