Kinetics and mechanisms of hydrolysis of dicarboximide fungicides in micellar media

The kinetics of alkaline hydrolysis of the dicarboximide fungicides procymidone, iprodione, vinclozolin, and chlozolinate (1-4, respectively) were investigated in micellar solutions containing various amounts of either sodium dodecyl sulfate (SDS), cetyltrimethylammonium bromide (CTAB), or three non...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 1995-07, Vol.43 (7), p.1948-1953
Main Authors: Villedieu, Jean C, de Savignac, Alain, Calmon, Jean P
Format: Article
Language:English
Subjects:
Biological and medical sciences
FONGICIDE
Fundamental and applied biological sciences. Psychology
FUNGICIDAS
HIDROLISIS
HYDROLYSE
Methods and techniques. Experimental designs. Plant protection equipments
Phytopathology. Animal pests. Plant and forest protection
PROCIMIDONA
PROCYMIDONE
SURFACTANT
SURFACTANTES
VINCHLOZOLINE
VINCLOZOLINA
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Summary:The kinetics of alkaline hydrolysis of the dicarboximide fungicides procymidone, iprodione, vinclozolin, and chlozolinate (1-4, respectively) were investigated in micellar solutions containing various amounts of either sodium dodecyl sulfate (SDS), cetyltrimethylammonium bromide (CTAB), or three nonionic surfactants (two C13 alcohols and a copra amine combined with ethoxyl chains) and compared with the kinetics in aqueous media. For all compounds, the rate constants observed are slightly reduced by the SDS micellar media, showing that reactions essentially take place in the aqueous pseudophase. The CTAB micellar media speed up the hydrolysis rates with small quantities of Br- ions in the medium. As the number of Br- ions increases, the rate of reactions falls. This is characteristic of an ion exchange (OH- and Br-) at the surface of the CTAB micelles. Finally, the presence of nonionic micelles has little influence on the hydrolysis of the fungicides: the reduction in the rate of dicarboximide ring opening is attributed to micelle-substrate association. These results can be explained by means of the pseudophase kinetic model coupled with the mechanisms of hydrolysis of these fungicides in water solution
ISSN:0021-8561
1520-5118
DOI:10.1021/jf00055a035