91-98
Aminofumaric acid derivatives: synthesis and influence on the development of plants
Authors: T.V. Khokhlova, Yu.A. Chertihina, B.Zh. Mutalieva, D.E. Kudasova, K.V. Yanova, A.V. Prosyanik
Number of views: 262
The methods of the synthesis of aminofumaric acid derivatives RO2CCH=C(NH2)CO2R (R=Me, Et, Bu, Dec), MeO2CCH=C(NHR)CO2Me (R=Me, Et, Bu, Oct, Dec, C15H31, Bzl), MeO2CCH=C(NHR)CO2K (R=H, Bu, Oct, Dec), RO2CCH=C(NH2)CONH2 (R=Me, Et) and MeO2CCH=C(NH2)CONHR (R=Me, HOCH2CH2) have been developed. The monosaponification and monoammonolysis of diesters are regiospecific and occur with the participation of -ester group. This is due to low electrophilicity of the -ester group because of its effective conjugation with amino group, which is confirmed by the computational data for dimethyl ester of aminofumaric acid using DFT method (PBE/6-311+G(d,p) in terms of NBO. Screening tests of the growth-regulating activity of the synthesized compounds on the seeds of wheat, alfalfa, beet and buckwheat showed that dimethyl ester of aminofumaric acid and its monoamides at the concentration of 10–4% are the most effective stimulators of root system development. The aminofumaric acid derivatives in high concentrations are retardants. With an increase in the length of the alkyl substituents at the nitrogen and in the ester groups, stimulating properties diminish. The potassium salts of aminofumaric acid promote the development of plant stems and, to a lesser extent, the development of root system.