Mechanism of hydantoin ring opening in iprodione in aqueous media

The hydrolysis kinetics of iprodione in alkaline solutions of pH 8.3 to 12 at 25°C have been determined by ultraviolet spectrophotometry. Under these conditions, iprodione leads quantitatively and irreversibly to N-(3,5-dichloroanilinocarbonyl)-N-(isopropylaminocarbonyl)glycine. The reaction is not subject to a general basic catalysis and the rate law takes the form K_obs = K_OH- [OH^?1]. The activation entropy of -77 J mol^?1deg^?1, the value of the kinetic solvent isotope effect k_OH?/k_OD? of 0.79 and the value of 0.60 for the Hammett parameter σ, obtained for the hydrolysis of a series of 3-aryl-N-isopropyl-2,4-dioxoimidazolidine-1-carboxamides are all in agreement with the rate-determining attack by the hydroxyl ion on the carbonyl in the 4-position of the hydantoin ring of the fungicide.