Activity and metabolism of cyano-oxime derivatives in various strains of Botrytis cinerea |
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| Authors: | Frédérique Tellier Abel Carlin-Sinclair Jean-Claude Cherton |
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| Institution: | a Unité de Phytopharmacie et Médiateurs chimiques, INRA, route de saint Cyr, 78026 Versailles Cedex, France
b Département de Chimie, SIRCOB EP CNRS 102, Université de Versailles, 45 avenue des Etats-Unis, 78001 Versailles, France |
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| Abstract: | The fungitoxicity of cymoxanil, 4 cyano-oxime analogs (in which the acetylurea group was replaced with various groups: amide, ester, propargyl, and cyanomethyl-amide), and 2 cymoxanil-metabolites was studied against various strains of Botrytis cinerea. The fungicidal effect was measured on germ-tube elongation and mycelial growth. Cymoxanil and the analogs bearing the amide and ester groups showed the best anti-botrytis activity. The strains studied can be classified into 3 groups according to the germ-tube sensitivity to cyano-oximes. These groups fitted well with the 3 phenotypes of sensitivity to cymoxanil previously characterized in our laboratory: CyaS1 (highly sensitive phenotype); CyaS2 (moderately sensitive phenotype); and CyaR (tolerant phenotype). The bio-transformations of all the cyano-oximes were monitored in the culture-medium of the different strains using HPLC- and IP-HPTLC-methods. HPLC-studies showed that cymoxanil and the analogs bearing the groups amide and ester were quickly metabolized in the culture-medium of the CyaS1 strain. Moreover, these studies allowed us to correlate disappearance of these cyano-oximes, to their fungicidal activity towards the CyaS1 strain. This suggests that cyano-oximes and particularly cymoxanil are probably activated in a fungitoxic compound. IP-HPTLC-studies strengthened the precedent results and allowed us to correlate disappearance of cyano-oximes studied with appearance of two acids metabolites of hydrolysis. These metabolites could be the actual active-principles. |
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| Keywords: | Cyano-oximes Cymoxanil Fungitoxicity Botrytis cinerea Bio-transformation Activation |
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