RU2438311C1 - 3-piperidinyl-4-benzosulphamide butyrolactone, having rhizogenic activity on winter wheat seeds - Google Patents

Abstract

FIELD: chemistry. ^ SUBSTANCE: invention relates to agriculture. 3-piperidinyl-4-benzosulphamide butyrolactone of formula has rhizogenic activity on winter wheat seeds. ^ EFFECT: invention enables to increase activity of the agent. ^ 2 ex, 1 tbl

Description

The invention relates to a new biologically active compound - 3-piperidinyl-4-benzenesulfamidobutyrolactone of the formula 1:

which can be used in agriculture as a stimulator of root formation on seeds of winter wheat.

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

The closest technical solution in structure and action is 6-sulfophenyl-4-oxo-3-oxa-6-azabicyclo [3.1.1] hexane (2) - the starting material for the claimed compound of formula 1, as well as the known growth regulator for cereals crotonolactone [1. Kazakova V.N., Polievktova E.T. The rules of application and the effectiveness of new regulators of plant growth and development // Chemistry in Agriculture, 1987, vol. XXV, No. 8, pp. 37-40].

Gibberellin, one of the most well-known stimulators of seed germination, a natural phytohormone, which has a positive effect on the growth processes of the seedling, was taken as an analogue in its stimulating effect. 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 V.P., Sheleg Z.I., Sanko N.V. Selective effect of chemical growth regulators on plants. Minsk: Science and Technology, 1988. - 253 p .; 5. Vakulenko VV Growth Regulators // Plant Protection and Quarantine, 2004. No. 1. S.24-26].

The objective of the invention is the synthesis of a new biologically active compound exhibiting the properties of a root stimulant on the seeds of winter wheat.

The technical result of the present invention is the expansion of the range of substances exhibiting the properties of the root stimulant on the seeds of winter wheat.

This is achieved by the synthesis of a new previously undescribed compound - 3-piperidinyl-4-benzenesulfamidobutyrolactone of formula 1, which exhibits the properties of a root formation stimulator on winter wheat seeds. A compound of formula 1 is prepared by reacting 6-sulfophenyl-4-oxo-3-oxa-6-azabicyclo [3.1.1] hexane (2) with piperidine. The synthesized compound is identified by the combination of elemental analysis data and the results of physicochemical analysis methods.

It was experimentally found that compound 1 exhibits root-forming activity on seeds of winter wheat.

The invention is illustrated by the following examples.

Example 1

Preparation of 3-piperidinyl-4-benzenesulfamidobutyrolactone (1)

In a round-bottom flask, 1.0 g of 6-sulfophenyl-4-oxo-3-oxa-6-azabicyclo [3.1.0] hexane and 3 cm ^{3 of} piperidine are dissolved in 20 cm ^{3 of} ethanol, refluxed for 0.5 h and left overnight until compound 2 was completely consumed (TLC control). After removal of ethanol and excess piperidine, the resulting solid residue was purified by recrystallization from ethyl acetate. The yield of 0.9 g (70%) of the target product. T. pl. 134-135 ° C.

Calculated,%: C 55.56%; H 6.17%; N, 8.64%; S 8.88%.

Found,%: C 55.70%; H, 6.14%; N, 8.72%; S 8.65%. C ₁₅ H ₂₀ N ₂ O ₄ S.

IR spectrum, liquid paraffin (ν, cm ^-1 ): ν (S = O) 1100, ν (SO ₂ ) 1330, 1160, ν (C = O) 1745.

1 H-NMR spectrum (CF ₃ COOH), ppm: 8.45 (1H, -NH-SO ₂ ), 7.0 (5H, -C ₆ H ₅ ), 4.28 (2H, -CH ₂ C = O), 4.18 (2H, —CH—), 2.82 (4H, —CH ₂ —N), 1.49 (6H, —CH ₂ -).

Example 2

Growth-promoting activity of 3-piperidinyl-4-benzenesulfa-midobutyrolactone (1)

The growth-promoting activity of root formation of compound 1 was determined by model methods of modified laboratory screening on seeds of winter wheat of the Batko variety.

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

To study the growth-regulating activity, the claimed substance and structural analogue were previously dissolved in dimethyl sulfoxide (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-stimulating concentration of the compound was judged by the totality of such indicators as germination energy, length and dry weight of the roots of seedlings.

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 the root stimulator of the formation of wheat seeds.

Compound 1 in the optimal growth-stimulating root formation dose with a mass fraction of 0.0005% activates the growth of seedlings, increasing the germination energy of seeds of winter wheat by 10%, the length of the roots of seedlings by 38.2%, and their mass by 76.7%, significantly exceeding control and analogues in structure and action. At lower concentrations, the degree of activity of compound 1 decreases; at higher concentrations, it does not increase.

Thus, the claimed compound 3-piperidinyl-4-benzene-sulfamidobutyrolactone of formula 1 is an effective growth stimulator of root formation of seeds of winter wheat and can be used in agricultural practice as a means to improve the sowing qualities of wheat seeds and increase the viability of seedlings.

Table 1 The influence of growth regulators on root formation in Batko wheat seeds Experience option The concentration of the solution,% Germination energy,% Length cm Air dry weight, mg root ± to control root ± to control The control - 90 10.6 4.7 Control (DMSO DMSO solution) 0.01 87 8.9 -16.0 4.3 -8.5 Gibberellin 0.001 93 11.1 4.7 5.1 8.5 Crotonolactone 0.005 93 11.7 10,4 5,6 19.1 Compound 2 0.01 90 7.9 -11.2 4.3 - 0.005 90 11.0 23.6 5.3 23.3 0.001 90 10.9 22.5 5,0 16.3 0,0005 97 11.5 29.2 5.8 34.9 0.0001 93 11,2 25.8 5.1 18.6 Compound 1 0.01 83 9.9 11,2 5,0 16.3 0.005 93 11.7 31.5 5.3 23.3 0.001 93 11.9 33.7 5.5 27.9 0,0005 97 12.3 38,2 7.6 76.7 0.0001 93 11,2 25.8 5.9 37,2

Claims (1)

3-piperidinyl-4-benzenesulfamidobutyrolactone of the formula

,
showing root-forming activity on the seeds of winter wheat.