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Synthesis and fungicidal activity of 2-methylalkyl isonicotinates and nicotinates

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Abstract

Homologs and analogs of 2-methylheptyl isonicotinate (new, natural antifungal and antibacterial antibiotic isolated from Streptomyces sp. 201): racemic 2-methylalkyl isonicotinates 4 and nicotinates 5 and enantiomerically enriched in the R and S isomers, 2-methylpentyl isonicotinate and nicotinate were obtained. Fungistatic activity of the compounds was evaluated. Nicotinates 5a–c show significant activity against phytopathogenic fungi: Fusarium culmorum, Phytophthora cactorum, Rhizoctonia solani. The activity of the enantiomerically enriched compounds was comparable to the activity of racemic ones. There was no significant difference in fungistatic activity between the enantiomerically enriched R and S isomers. Investigated compounds and their oxalates have proven to be active against chalkbrood disease caused by fungal species Ascosphaera apis. The activity of the nicotinates 5a and 5b and oxalates 5a–c against Ascosphaera apis was higher than the activity of oxalic acid itself. Especially high activity was shown for 2-methylbutyl nicotinate 5a and oxalate of 2-methylpentyl nicotinate 5b.

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Acknowledgement

This work was supported by the Polish Ministry of Science and Higher Education 429/E-142/S/2011 and 429/E-142/S/2012. We would like to thank Dr Bożena Adrjan (Laboratory of NMR Spectroscopy, University of Warsaw, Department of Chemistry, Poland) for the electronic versions of the NMR spectra.

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Authors and Affiliations

  1. Institute of Industrial Organic Chemistry, Annopol 6, Warsaw, 03-236, Poland

    Bogumiła Huras, Jerzy Zakrzewski, Maria Krawczyk, Danuta Bombińska, Anna Cieniecka-Rosłonkiewicz & Alicja Michalczyk

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  1. Bogumiła Huras
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  2. Jerzy Zakrzewski
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  3. Maria Krawczyk
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  4. Danuta Bombińska
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  5. Anna Cieniecka-Rosłonkiewicz
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  6. Alicja Michalczyk
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Correspondence to Jerzy Zakrzewski.

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Huras, B., Zakrzewski, J., Krawczyk, M. et al. Synthesis and fungicidal activity of 2-methylalkyl isonicotinates and nicotinates. Med Chem Res 26, 509–517 (2017). https://doi.org/10.1007/s00044-016-1768-7

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