This study describes the synthesis and reversibility of Schiff bases from chitosan and bioactive compounds, and their application in the antifungal packaging of fruit. Imine bonds between primary amine groups of chitosan and carbonyl groups of antifungal aldehydes were synthesised and their reversibility was assayed in an aqueous medium under different acidic conditions. The mechanism of action of the dynamers is based on the hydrolysis of imine bond and the release of the active agent. The new films were effective at inhibiting the growth of Penicillium expansum and Botrytis cinerea, and their effectivity depended on the degree of hydrolysis achieved which was greater when the bonds were hydrolysed in a mild acidic medium. A double bottom cylindrical tray was used for the responsive antimicrobial packaging of blackberries. The package extended shelf-life of berries from 3 to 12 days without causing phytotoxic effects on the fruit being safe for human consumption.