RU2374222C1 - Hydrobromide 3-[n-(3-carboxypropylene)benzylamino]-4-hydroxy-n-benzylbutaneamide, exhibiting growth-stimulating activity on wheat seeds - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: described is hydrobromide 3-[N-(3-carboxypropylene)benzylamino]-4-hydroxy-N-benzylbutaneamide, which exhibits growth-stimulating activity on wheat seeds. The invention is aimed at obtaining a new compound for use in agriculture as a germination activator for wheat seeds.

EFFECT: obtaining a new compound which widens the range of substances with growth-regulating properties, along with indolebutyric acid derivatives, which improves sowing qualities of seeds.

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Description

The invention relates to a new biologically active compound - hydrobromide 3- [N- (3-carboxypropylene) benzylamino] -4-hydroxy-N-benzyl-butanamide of the formula 1:

which can be used in agriculture as a stimulator of germination of seeds of winter wheat.

The specified compound, its chemical and biological properties are not known in the literature.

The closest technical solution in structure is 3-benzylamino-4-hydroxy-M-benzylbutanamide of the formula 2:

which is described earlier [1. Muzychenko G.F., Badovskaya L.A., Kulnevich V.G. and other N-alkylamides of 3- (N-alkyl- or benzyl) amino-4-hydroxybutanoic acid, showing acaricidal action, and.with. 841258 (USSR), 1981]. Gibberellin, one of the most well-known stimulators of seed germination, a natural phytohormone that has a positive effect on the growth processes of the seedling, was taken as an analogue in its growth-regulating properties. However, gibberellin is an expensive product of microbiological synthesis and inaccessible [2. Muromtsev G.S. et al. Fundamentals of chemical regulation of plant growth and productivity. - M .: Agropromizdat, 1987. - p. 33-80; 3. Leonova T.G., Muromtsev G.S. Gibberellins in agriculture // S.-kh. Biology, 1991. No. 5. S.154-168); 4. Deeva B.P., Sheleg Z.I., Sanko N.V. Selective effect of chemical growth regulators on plants. Minsk: Science and Technology, 1988. - 253 p.].

The technical result of the present invention is to obtain a new compound, promising for the chemistry of biologically active compounds, expanding the range of substances with growth-regulating properties in a series of synthetic analogs of auxin - derivatives of indolylbutyric acid, which allows to improve the sowing quality of seeds and to obtain more viable seedlings.

This is achieved by the synthesis of a new compound not previously described - 3- [N- (3-carboxypropylene) benzylamino] -4-hydroxy-N-benzylbutanamide hydrobromide of formula 1, which exhibits the properties of an activator of germination of seeds of winter wheat. A compound of formula 1 is prepared by reacting 3-benzylamino-4-hydroxy-N-benzylbutanamide with α-bromobutyric acid.

The synthesized compound is identified by the combination of elemental analysis data and the results of physicochemical analysis methods.

It was experimentally established that compound 1 exhibits the properties of an activator of wheat seed germination.

The invention is illustrated by the following examples.

Example 1

Preparation of 3-N- (3-carboxypropylene) benzylamino] -4-hydroxy-N-benzylbutanamide hydrobromide (1)

With gentle warming, 4.42 g of 3-benzylamino-4-hydroxy-N-benzylbutanamide and 2.48 g of α-bromobutyric acid were dissolved in 100 cm ^{3 of} ethyl acetate, boiled for 1 h and left overnight. A viscous precipitate was obtained, which was dissolved in ethanol and reprecipitated with sulfuric ether. The colorless precipitate formed was filtered off and washed on the filter with sulfur solution. 3.17 (46%) of the compound of formula 1 were isolated.

Calculated,%: C 55.75%; H, 6.19%; N, 6.19%; Br 17.70%.

Found. %: C 55.92%; H 6.15%; N, 6.21%; Br 17.53%. C ₂₁ H ₂₈ N ₂ O ₄ Br.

IR spectrum, liquid paraffin (ν, cm ^-1 ): 3440, 3175, 3080, 3060, 3030, 2700, 1755, 1710, 1640, 1575.

Example 2

Growth-regulating activity of 3- [N- (3-carboxypropylene) benzylamino] -4-hydroxy-N-benzylbutanamide hydrobromide (1)

The growth-regulating activity of compound 1 and its effect on the sowing quality of seeds was determined by model methods of modified laboratory screening on seeds of winter wheat of the variety Deja.

In the course of studies, the optimal growth-activating concentration of compound 1 was determined, its effect on the sowing qualities of winter wheat seeds (germination energy, length and mass of the shoot and root system of seedlings).

To study the growth-regulating activity, the claimed substance and structural analogue were previously dissolved in DMSO and then water. Gibberellin was used as an analogue in properties, and compound 2 was used as an analogue in structure and properties. Water served as an absolute control.

Seeds were soaked in aqueous solutions of the preparations for 18 hours. Then the seeds were germinated in rolls of filter paper at a temperature of 20-22 ° C. The experiment was repeated three times. In each repetition, 50 pieces of seeds were used.

The optimal growth-promoting concentration of the compound was judged by the totality of such indicators as germination energy, length and dry weight of seedlings and their potential productivity.

The results of determining the optimal concentration of the compound and their effect on the sowing quality of the seeds are shown in table 1.

Studies have established that the tested compound 1 exhibits the properties of an activator of germination of wheat seeds.

Compound 1 in the optimal growth-promoting dose with a mass fraction of 0.0005% activates the growth of seedlings, increasing the seed germination energy by 4%, the length of the shoot of 7-day-old seedlings by 51.2%, the root length of the seedlings by 58.6%, and their mass - by 52.6 and 42.0%, respectively, significantly surpassing control and analogues in structure and action. At lower concentrations, the degree of activity decreases; at higher concentrations, it does not increase.

Thus, the inventive compound 3- [N- (3-carboxypropylene) benzylamino] -4-hydroxy-N-benzylbutanamide hydrobromide of the formula 1 is an effective activator of wheat seed germination and can be used in agricultural practice as a means to improve the sowing quality of seeds wheat and increase viability of seedlings.

Claims (1)

3- [N- (3-carboxypropylene) benzylamino] -4-hydroxy-N-benzylbutanamide hydrobromide of the formula

showing the properties of a stimulator of germination of wheat seeds.