RU2405769C1 - N-butyl-3-butyltosylamino-4-hydroxybutanamide, activating winter wheat seed germination and increasing restance of seedlings to water stress - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: there is described M-butyl-3-butyltosylamino-4-hydroxybutanamide of formula 1

, which can be used in agriculture as a winter wheat seed germination activator, which has anti-stress activity (high resistance of winter wheat seedlings to water stress).

EFFECT: obtaining a novel biologically active compound of formula 1, which widens the range of substances with growth regulation properties, having anti-stress activity (high resistance of winter wheat seedlings to water stress) in the family of indole butyric acid derivatives.

2 tbl, 2 ex

Description

The invention relates to a new biologically active compound - N-butyl-3-butyltosylamino-4-hydroxybutanamide of the formula 1:

which can be used in agriculture as an activator of germination of seeds of winter wheat, exhibiting anti-stress activity (increasing the resistance of winter wheat seedlings to water stress).

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

The closest technical solution in structure is 3-butylamino-4-hydroxy-N-butylbutanamide (hydroxyaminoamide) of 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, exhibiting acaricidal action. A.S. USSR 841258, 1981]. Gibberellin, one of the most famous seed germination stimulants, natural phytohormone, was taken as an analogue in 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, p. 154-168; 4. Deeva V.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 expand the range of substances with growth-regulating and anti-stress properties.

This is achieved by the synthesis of a new compound not previously described - N-butyl-3-butyltosylamino-4-hydroxybutanamide of formula 1, which exhibits the properties of an activator of seed germination of winter wheat, which has anti-stress activity (which increases the resistance of winter wheat seedlings to water stress).

A compound of formula 1 is prepared by reacting 3-butylamino-4-hydroxy-N-butylbutanamide (hydroxyaminoamide) with tosyl chloride in acetonitrile using calcium carbonate as a catalyst.

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

It has been experimentally established that compound 1 exhibits the properties of an activator of wheat seed germination, which has anti-stress activity (increasing the resistance of winter wheat seedlings to water stress).

The invention is illustrated by the following examples.

Example 1

Obtaining N-butyl-3-butyltosylamino-4-hydroxybutanamide (1)

With gentle heating, 0.46 g (2 mmol) of 3-butylamino-4-hydroxy-N-butylbutanamide was dissolved in 15 ml of acetonitrile, 0.55 g (4 mmol) of potash K ₂ CO ₃ and 0.4 g were successively added with stirring. (2.2 mmol) of toluenesulfonic acid chloride TsCl, stirred at room temperature for 5 hours, filtered, the filtrate was left in the refrigerator overnight. A precipitate was obtained, which was dissolved in ethanol and reprecipitated with sulfuric ether. The precipitated colorless crystals were filtered off and washed on the filter with sulfuric ether. 0.61 g (80%) of the compound of formula 1 were isolated. Mp = 98 ° C.

Calculated,%: C 59.38; H 8.33; N, 7.29; S 8.33.

Found.%: C 59.50; H, 8.30; N, 7.33; S 8.26.

C ₁₉ H ₃₂ N ₂ SO ₄ .

PMR spectrum (δ ppm) was recorded in CDCl ₃ , TMS standard:

6.05-6.08 (br.s) NH; 3.40-3.43 (broad s.) OH; 4.22-4.26 (m) CH; 7.69-7.71 (d) 4H Ar.

IR spectrum, liquid paraffin (ν, cm ^-1 ): 3440, 3380, 3010, 1620, 1580, 1530, 1370, 1180.

Example 2

Growth-regulating and anti-stress (resistance of seedlings to drying) activity of N-butyl-3-butyltosylamino-4-hydroxybutanamide (1)

The growth-regulating and anti-stress (resistance of seedlings to drying) 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.

The studies determined the optimal growth-regulating concentration of compound 1, its effect on the sowing qualities of winter wheat seeds (germination energy, length and mass of the shoot and root system of seedlings), growth and accumulation of dry mass in seedlings when grown under normal conditions and under the influence of a stress factor (drying seedlings).

To study the growth-regulating and anti-stress activity, the claimed substance and structural analogue were previously dissolved in DMSO and then in water. Gibberellin was used as an analogue in properties, compound 2 was used as an analogue in structure and properties. Water served as an absolute control, DMSO water solution with a mass fraction of 0.01% was used as control.

Seeds were soaked in aqueous solutions of the preparations for 18 hours. Then the seeds were germinated in Petri dishes on wet filter paper for three days at a temperature of 20-22 ° C.

To detect anti-stress activity, half of the three-day-old seedlings were dried for one hour. Then, the germination of all seeds was continued in rolls of filter paper for four days. The experiment was repeated three times. In each repetition, 50 pieces of seeds were used.

The optimal growth-promoting concentration and growth-regulating activity of the compound was judged by the totality of such indicators as germination energy, length, 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 seeds are shown in table 1. The results of the effect on the resistance of winter wheat seedlings of the variety Deja to water stress (drying of seedlings) are given in table 2.

Studies have established that the tested compound 1 exhibits the properties of an activator of germination of wheat seeds, which has anti-stress activity (resistance of seedlings to drying).

Compound 1 in the range of studied concentrations exhibits the properties of a growth promoter, in the optimal dose with a mass fraction of 0.001% increases the seed germination energy by 16%, the height of 7-day-old seedlings - by 39.6%, the length of the roots of seedlings - by 18.5%, and their mass - by 16.3 and 7.9%, respectively, not inferior in effectiveness to analogues in structure and action. At lower and higher concentrations, the degree of activity decreases.

Compound 1 in the range of studied concentrations exhibits anti-stress activity, in the optimal concentration with a mass fraction of 0.0001% increases the height of seedlings by 19.0%, the length of the roots by 20.9% and their weight by 75.0 and 72.2 %, respectively, not inferior in effectiveness to analogues in structure and action.

Thus, the claimed compound N-butyl-3-butyltosylamino-4-hydroxybutanamide of the formula 1 is an effective activator of germination of wheat seeds with anti-stress activity (resistance of seedlings to drying), and may find application in agricultural practice as a means to improve sowing qualities wheat seeds, increasing the viability of seedlings and plant resistance to water stress.

Claims (1)

N-butyl-3-butyltosylamino-4-hydroxybutanamide of formula 1

activating the germination of seeds of winter wheat and increasing the resistance of seedlings to water stress.