SYNTHESIS, CHEMICAL MODIFICATION AND GROWTH-STIMULATING ACTIVITY OF N-BENZYLMETHYLAMINE AND INDOLINE DERIVATIVES

Abstract

One of the main tasks of organic chemistry is the development of targeted synthesis of synthetic and natural biologically active substances. The chemistry of dithiocarbamic compounds opens up wide possibilities for solving this problem. There is a strong interest in dithiocarbamic acids due to a wide range of their biological activity (anticancer, antifungal, antibacterial, anti-Alzheimer's, anti-tuberculosis, growth-stimulating, root-forming, etc.). The purpose of this study is the synthesis of biologically active substances in the series of element(N-,O-,S-,F-,Cl-)organic compounds based on N-benzylmethylamine and indoline, the determination of the structure and biological activity of the synthesized compounds. The initial sodium dithiocarbamates were synthesized by the reaction of N-benzylmethylamine and indoline with carbon disulfide in the presence of potassium hydroxide at room temperature in the yields 92 and 52%. Acylation of the studied sodium benzyl(methyl)carbamodithioate and sodium indoline-1-carbodithioate was carried out. The acylation of the studied sodium benzyl(methyl)carbamodithioate and sodium indoline-1-carbodithioate proceeds in chloroform with acid chlorides and leads to the formation of the corresponding derivatives of aromatic and heterocyclic dithiocarbamic acid thioanhydrides in the yields 58-85%. The structure of the synthesized compounds was identified on the basis of elemental analysis and IR spectra, ¹Н and ¹³С NMR spectroscopy and two-dimensional NMR COZY (¹H-¹H) and HMQC (¹H-¹³C) spectra. Laboratory study of growth-stimulating activity of new biologically active compounds on laboratory germination and germination energy of wheat and soybean seeds was carried out. The best results were achieved when wheat seeds were treated with sodium indoline-1-carbodithioate and benzyl(methyl)carbamothio-4-fluorobenzoic thioahydride at 0.001% concentration. Germination energy and laboratory seed germination were 100% and 100%, and for the KN-2 standard - 80% and 90%, respectively. As a result of the research, it was found that seed treatment with new synthesized preparations intensively stimulates the growing and germination of wheat shoots in comparison with the control (water) and the standard KN-2 (Akpinol).