Abstract
Numerous biologically active acids can be transformed into an ionic form in a facile way and combined with appropriate quaternary ammonium cation to improve their application properties or biological activity. This study describes the synthesis of new quaternary ammonium salts with anions of gibberellic acid, a common plant growth regulator from the gibberellin group, or l-tryptophan, an important precursor of auxin biosynthesis. The surface-active tetrapentylammonium ion and natural substances such as acetylcholine, choline, and quinine were the sources of cations. Novel salts of gibberellic acid and l-tryptophan were obtained with high yields exceeding 97% as a result of the metathesis reaction or the neutralization of quaternary ammonium hydroxides. Phase transition temperatures, thermal and chemical stability, and solubility in solvents with different polarities were determined for all obtained salts. On the basis of studies regarding the influence of synthesized salts on the post-harvest longevity and quality of leaves of Convallaria majalis, it was established that the biological activity of the natural plant regulators in most cases was maintained. Therefore, it can be concluded that the conversion of the active substance into the form of a quaternary ammonium salt results in obtaining novel forms of plant growth regulators with favourable physicochemical properties while maintaining the efficacy of the biological active ingredients.Graphic abstract
Highlights
The ageing process of plant organs is the final phase of ontogenesis, during which irreversible changes that result in cell degradation and plant death are initiated [1]
We focused on the synthesis of new plant growth regulators in the form of quaternary ammonium salts
Since the new forms of both active ingredients were expected to possess more favourable physicochemical properties compared to acidic forms of GA3 an l-tryptophan, we evaluated the products’ effect on the prolongation of post-harvest longevity of lily of the valley leaves (C. majalis) to confirm that that the introduction of organic cations does not hinder the biological properties of the active ingredients
Summary
The ageing process of plant organs is the final phase of ontogenesis, during which irreversible changes that result in cell degradation and plant death are initiated [1]. The chemical structures of both gibberellate and l-tryptophanate anions are prone to decomposition, it was important to determine the thermal and chemical stability of the obtained salts. Quaternary ammonium salts (Table 1) with selected organic cations and anions from the group of plant growth regulators (Fig. 1) were obtained using two methods.
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