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Synthesis and fungicidal activity of 2-(diphenylmethyl)-3-arylisoxazolidine-5-carboxamides

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Abstract

A series of new 2-(diphenylmethyl)-3-arylisoxazolidine-5-carboxamides have been prepared from aldehydes. A key step was an uncatalyzed stereoselective and regioselective 1,3-dipolar cycloaddition reaction of N-benzylidene-N-diphenylmethyl nitrones with ethyl acrylate. Some of these amides exhibited fungicidal activities against Fusarium culmorum, Phytophthora cactorum, Alternaria alternata, Rhizoctonia solani, Botrytis cinerea, and Blumeria graminis.

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Acknowledgments

This work was supported in part by the Polish Ministry of Science and Higher Education (Grant No. 429/E-142/S/2011), which is gratefully acknowledged.

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Authors and Affiliations

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

    Krzysztof Żelechowski, W. Marek Gołębiewski & Maria Krawczyk

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  1. Krzysztof Żelechowski
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  2. W. Marek Gołębiewski
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  3. Maria Krawczyk
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Correspondence to W. Marek Gołębiewski.

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Żelechowski, K., Gołębiewski, W.M. & Krawczyk, M. Synthesis and fungicidal activity of 2-(diphenylmethyl)-3-arylisoxazolidine-5-carboxamides. Monatsh Chem 146, 1895–1905 (2015). https://doi.org/10.1007/s00706-015-1568-7

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  • DOI: https://doi.org/10.1007/s00706-015-1568-7

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