Synthesis of ammonium salts of some carboxylic acids with amines and their potential as bioregulators
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Date
2009
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Punjab Agricultural University, Ludhiana
Abstract
The present study includes the synthesis of seventy-one new ammonium salts and their potential as plant growth regulators. The tertiary amines were prepared from different aldehydes by Leuckart’s reaction and through the formation of glycidyl ester of epichlorohydrin with different 3-aryl prop-2-en-oic acids and 2-aryloxy ethanoate, which in turn were prepared by Knoevenagel reaction on different aldehydes and Williamson synthesis on various phenols, respectively. The products obtained after each step were characterized by chemical (TLC) and spectroscopic methods like NMR and IR. Cinnamic acids and Phenoxyacetic acids were synthesized from different benzaldehydes (4-Cl, 3-NO2, 2- NO2, 4-OCH3, H) and phenols (2-Cl, 4-Cl, 4-NO2, 4-Cl-3-CH3 and 2,4-di Cl). The ammonium salts were prepared by reacting these synthesized tertiary amines and other amines i.e. ethanolamine, diethylamine, piperidine with equimolar ratio of synthesized acids. For the preparation of bis-quaternary ammonium salts, maleic acid and fumaric acid were first converted into their dichloride by reacting with thionyl chloride, which were then quaternized with synthesized tertiary amines. Testing of biological activity was performed by using different concentrations of newly synthesized ammonium salts and their effect on seed germination and seedling growth of rice (Oryza sativa, PR-114) under laboratory conditions at 28±2º was studied. An effort to establish structure activity relationship (SAR) was made on the basis of the data obtained from the biological activity. All the compounds were found to possess plant growth retardant activity.
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