| Abstract: | Imines, synthesised by the reaction of sec-butylamine (SBA, 2-amino-butane) with pentan-2-one, heptan-2-one, octan-2-one, undecan-2-one, benzaldehyde and 2-furaldehyde, were evaluated as vapour-phase treatments to prevent the infection of oranges by Penicillium digitatum. All the imines provided decay control equivalent to SBA when they were introduced into the fruit container at a rate equivalent to 16.4 mg SBA litre?1 air volume. The carbonyl compound component of the imines, tested alone at a five-fold higher rate, did not reduce fruit decay. All the imines were stable in the gaseous state in dry air. The imines of pentan-2-one and undecan-2-one were hydrolysed rapidly in a humid environment, indicating that their action against P. digitatum was due to the release of SBA into the atmosphere around the fruit. The instability of the imines of the aliphatic ketones makes them unsuitable as generators of SBA in packages. The imines derived from benzaldehyde and 2-furaldehyde were stable in moist air, but were hydrolysed to a significant degree on moist filter paper, especially at pH < 7. These aromatic imines were absorbed from the atmosphere by the fruit and were hydrolysed rapidly in water, and in a buffer solution that represented the environment in fresh injuries on fruit. Apparently all the imines tested generated SBA in the fruit environment, and this SBA accumulated at potential infection sites, where it prevented the development of decay. |
