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4-Aryl-substituted 1-aminonaphthalene-2-carbonitriles and 3-phenyl-1-oxo-1H-indene-2-carbonitriles were prepared in a two--step synthesis from appropriate carbonyl compounds and were evaluated in vitro for growth-inhibiting activity against some phytopathogenic fungi: Fusarium culmorum, Penicillium expansum, Botrytis cinerea and Alternaria species. The results were compared with the activity of a commercial fungicide - captan. The highest fungistatic activity was revealed by 1-amino-4-phenylnaphthalene-2-carbonitrile. An efficient synthesis of 1-amino-4-arylnaphthalene-2-carbonitriles involves condensation of diarylacetaldehydes or 1,1-diarylacetones with malonodinitrile and cyclization of the obtained aryl-ylidenemalonodinitriles in concentrated sulfuric acid. The benzannulation reaction is accompanied by a quasi-aromatic rearrangement. The indenone derivatives were synthesized in the same manner from substituted benzophenones. As the formation of five-membered ring during the cyclization of diarylmethylidenemalonodinitriles was less effective, the rearrangement was not observed.
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Tom
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20--25
Opis fizyczny
Bibliogr. 11 poz., tab.
Twórcy
autor
autor
autor
autor
autor
autor
- Department of Organic Chemistry, Jagiellonian University, Ingardena 3, 30-060 Kraków, Poland, kozik@chemia.uj.edu.pl
Bibliografia
- Abbott, W. S. 1925. A method of computing the effectiveness of an insecticide. Journal of Economic Entomology 18: 265-267.
- Borecki, Z. 1984. Fungicides Applied in Plant Protection (in Polish). 173 p. PWN, Warsaw, Poland.
- Borecki, Z. 1996. Studies on Plant Diseases (in Polish). 369 p. PWRiL, Warsaw, Poland.
- Campaigne, E., D. Mais, E. M. Yokley. 1974. A new synthesis of ylidenemalonodinitriles. Synthetic Communications 4: 379-388.
- Campaigne, E., S. W. Schneller. 1976. Cyclization of ylidenemalonodinitriles. Synthesis: 705-716.
- Davey, M. H., V. Y. Lee, R. D. Miller, T. J. Marks. 1999. Synthesis of aryl nitroso derivatives by tert-butyl hypochlorite oxidation in homogeneous media. Intermediates for the preparation of high-hyperpolarizability chromophore skeletons. Journal of Organic Chemistry 64: 4976-4979.
- Kiraly, Z., Z. Klement, F. Salymosy, J. Vörüs. 1977. Phytopathology - Selection of Research Methods (in Polish). 456 p. PWRiL, Warsaw, Poland.
- Kozik, B., J. Wilamowski, M. Góra, J. J. Sepioł. 2006. Novel synthesis of α-arylnaphthalenes from diphenylacetaldehydes and 1,1-diphenylacetones. Tetrahedron Letters 47: 3435-3438.
- Kulig, E., Z. J. Burgieł, J. Wilamowski, J. J. Sepioł. 2002. Derivatives and analogues of 1-aminonaphthalene-2-carbonitriles as a new group of potential fungicides. Pesticides 1-4: 27-34.
- Ong, B. S., B. Keoshkerian. 1984. 11,11,12,12-Tetracyanoanthraquinodimethane. Journal of Organic Chemistry 49: 5002-5003.
- Wilamowski, J., E. Kulig, J. J. Sepioł, Z. J. Burgieł. 2001. Synthesis and in vitro antifungal activity of 1-amino-3,4-dialkylnaphthalene-2-carbonitriles and their analogues. Pest Management Science 57: 625-632.
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Bibliografia
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bwmeta1.element.baztech-article-BAR0-0062-0057