RU2558139C1 - N-benzyl-2-(3-benzyl-2-thiophen-2-yl-1,3-oxazolidyn-4-yl)acetamide, activating germination of winter wheat seeds - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: invention relates to field of organic chemistry, namely to N-benzyl-2-(3-benzyl-2-thiophene-2-yl-1,3-oxazolidyn-4-yl)acetamide of formula 1

.

EFFECT: novel heterocyclic compound, useful as activator of germination of winter wheat seeds is obtained.

1 tbl, 2 ex

Description

The invention relates to chemical science, namely to a new biologically active compound: N-benzyl-2- (3-benzyl-2-thiophen-2-yl-1,3-oxazolidin-4-yl) acetamide of the formula 1,

which can find application in agriculture as an activator of germination of seeds of winter wheat.

The specified compound 1 is not described in the literature, its chemical and biological properties are not previously known.

The closest technical solution to the structure and action is the use of 3-benzylamino-4-hydroxy-N-benzylbutanamide (hydroxyaminoamide) of formula 2 (the starting material for the synthesis of N-benzyl-2- (3-benzyl-2-thiophen-2-yl-1 , 3-oxazolidin-4-yl) acetamide 1) as a plant growth stimulator, including for cereal crops ([1]. Muzychenko GF, Badovskaya LA, Kulnevich VG, etc. N 3- (N-alkyl- or benzyl) amino-4-hydroxybutanoic acid alkylamides exhibiting acaricidal action. A.S. 841258 (USSR), 1981. [2]. Tyukhteneva Z.I., Badovskaya L.A., Tlekhusezh M.A., Nenko NI. Activator p growth of seeds of winter wheat, increasing the resistance of seedlings to water stress. Patent No. 2373709 (RF), 2008.)

In this invention, gibberellin is used as an analogue in action - one of the most famous seed germination stimulants, natural phytohormone. However, gibberellin is an expensive product of microbiological synthesis, and it is also inaccessible ([3]. G. Muromtsev et al. Fundamentals of chemical regulation of plant growth and productivity. - M: Agropromizdat, 1987, P. 33-80. [4] Leonova T.G., Muromtsev G.S. Gibberellins in agriculture // S.-kh. biology, 1991. No. 5, S. 154-168).

The objective of the present invention is to expand the range of substances with growth-regulating properties.

The technical result of the present invention is the creation of N-benzyl-2- (3-benzyl-2-thiophen-2-yl-1,3-oxazolidin-4-yl) acetamide of the formula 1, exhibiting the properties of an activator of germination of seeds of winter wheat.

The technical result is achieved by the synthesis of a new previously undescribed compound - 3-benzyl-4- (N-benzylcarbamoylmethyl) -2-thiophen-2-yl-1,3-oxazolidine 1 and the identification of its properties, activating the germination of seeds of winter wheat.

The compound of formula 1 is obtained by condensation of 3-benzylamino-4-hydroxy-N-benzylbutanamide 2 (hydroxyaminoamide) with thiophene aldehyde at an equimolar reagent ratio and boiling the reaction mixture in chloroform in the presence of p-toluenesulfonic acid and molecular sieves (scheme).

The synthesized compound 1 was 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 germination of seeds of winter wheat.

The invention is illustrated by the following examples.

Example 1

Preparation of N-benzyl-2- (3-benzyl-2-thiophen-2-yl-1,3-oxazolidin-4-yl) acetamide (1)

A mixture of 2.98 g (0.01 mol) of 3-benzylamino-4-hydroxy-N-benzyl-butanamide (2), 1.12 g (0.01 mol) of thiophene aldehyde, 20 g of NaA molecular sieves, 0.02 g of para-toluene sulfonic acid and 50 cm ^{3 of} dry chloroform were boiled until the aldehyde was completely consumed (control — TLC), filtered, the filtrate was evaporated. A precipitate was obtained, which was dissolved in ethanol and reprecipitated with hexane. The precipitated colorless crystals were filtered. 2.94 g (75%) of the compound of formula 1 were isolated. Τ pl. = 90-91 ° C.

Calculated,%: C 70.41; Η 6.12; N, 7.14; S 8.16.

Found,%: C 70.31; H 6.39; N, 7.21; S 8.05.

C ₂₃ H ₂₄ N ₂ SO ₂ .

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

2.36 m (SOSN ₂ ); 3.85 m (N-CH ₂ ); 3.80, 4.10 two dd (2H, NH-CH ₂ ); 6.05-6.08 ears. from. (NH); 4.22-4.28 m (OCH ₂ ); 5.12 s (NCHO); 7.18-7.15 m (10H, Ph); 6.7-6.89 m (3H, = CH).

IR spectrum, liquid paraffin (cm ^-1 ): 3240 ν (NH), 3010 ν (С-Н Ar), 1605 ν (С = O), 1580 ν (С = С Ar), δ (NH) 1530.

Example 2

Growth-regulating activity of N-benzyl-2- (3-benzyl-2-thiophen-2-yl-1,3-oxazolidin-4-yl) acetamide (compound 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 winter wheat seeds of the Batko cultivar.

In the course of the studies, the optimal growth-regulating 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), growth and accumulation of dry mass in seedlings when grown under ordinary conditions.

To study the growth-regulating activity of the claimed substance 1 was previously dissolved in dimethyl sulfoxide (DMSO) and then water. Gibberellin was used as an analogue in properties, compound 2 was used as an analogue in structure and properties. The variant for treating seeds of wheat with gibberellin and an aqueous solution of DMSO was used as a control for seeds with water, and the control for compounds 1 and 2 was a variant with water treatment DMSO solution with a mass fraction of 0.01%.

Seeds were soaked in aqueous solutions of the preparations for 18 hours. Then the seeds were laid out for germination for seven days in moistened rolls of filter paper. The experiment was repeated three times. In each repetition, 50 pieces were used. seed.

The optimal growth-promoting concentration and growth-regulating activity of the compounds was judged by the totality of such indicators as germination energy, length, and air-dry mass of seedlings.

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

Studies have shown that the tested compound 1 in doses with a mass fraction of 0.001 and 0.0001% exhibits the properties of the activator of germination of seeds of winter wheat, increasing the energy of seed germination by 3% compared with the control (DMSO solution) (table 1).

Compound 1 in doses with a mass fraction of 0.001 and 0.0001% exhibits the properties of a growth promoter, activating the growth of wheat seedlings.

In the optimal growth-promoting dose with a mass fraction of 0.0001%, compound 1 increases the seed germination energy by 3%, the height of 7-day-old seedlings by 37.1%, the length of the roots of seedlings by 47.1% and their weight by 84.0 and 28, 9%, respectively, in comparison with the control (DMSO), not inferior in effectiveness to analogues in structure and properties taken in optimal growth-stimulating doses.

Thus, the claimed compound N-benzyl-2- (3-benzyl-2-thiophen-2-yl-1,3-oxazolidin-4-yl) acetamide of the formula 1 is an effective activator of wheat seed germination and may find application in rural practice farms as a means to improve the sowing qualities of wheat seeds.

Claims (1)

N-benzyl-2- (3-benzyl-2-thiophen-2-yl-1,3-oxazolidin-4-yl) acetamide of the formula 1,

activating the germination of seeds of winter wheat.