Ethyl-3-amino-9h-benzo[d]-pyrrolo-[1,2 a]imidazol-2-carboxylate, showing astragulus and anti-stress activity

 

(57) Abstract:

The invention relates to organic chemistry and agriculture. Describes ethyl-3-amino-N-benzo[d]-pyrrolo-[1,2 a]imidazol-2-carboxylate of the formula

,

showing astragulus and anti-stress activity. The technical result is obtained a new connection, promising chemistry of biologically active substances obtained synthetically, for use in agriculture as growth regulators and anti-stress drugs. table 2.

The invention relates to the field of agriculture and chemistry of biologically active substances, to a new biologically active compound from a number of condensed heterocyclic compounds of the formula I

exhibiting the properties of activator germination of winter wheat varieties Polovinka.

The specified connection is representative of a new heterocyclic system and its chemical and biological properties in the literature is unknown.

To the closest analogs in the structure of the claimed compounds can be attributed Dibazol - (2-benzyl-benzimidazole) - medical drug that has sosudorasshiratuyu the Ivanskii Century. And. Chemistry of heterocyclic compounds. - M.: Higher school, 1978. - 559 S.; Mashkovsky M. D. Medicines. - M.: Medicine, 1987. - 576 S.].

As similar properties known gibberellins, are widely used to activate germination.

However, gibberellin costly products of microbiological synthesis and inaccessible. Its use causes irrational waste of plastic substances [Muromtsev, S. and other foundations of chemical regulation of growth and productivity of plants. M: Agropromizdat, - 1987. - S. 33-80].

The present invention is to obtain a new connection, promising chemistry of biologically active substances and expand the Arsenal of biologically active substances obtained synthetically, for use in agriculture as growth regulators and anti-stress drugs.

This is achieved by synthesis of ethyl-3-amino-N-benzo[d]-pyrrolo-[1,2 a]imidazol-2-carboxylate, a new not previously described compounds exhibiting the properties of activator germination of winter wheat varieties Polovinka.

Compound I was obtained by reaction of alkylation of ethyl ether nitrile malonic acid chloromethylthiazole in Pris is I in the chemical industry.

The invention is illustrated by the following examples.

Example 1.

Obtaining the synthesis of ethyl-3-amino-N-benzo[d]-pyrrolo-[1,2 a]imidazol-2-carboxylate

In a flat-bottomed flask was placed 13.8 g (0.1 mol)2CO3150 ml of dimethyl sulfoxide (DMSO) and heated to 40-50°With the added 5,65 g (0.05 mol) of ethyl ether nitrile malonic acid. After 10 minutes from a dropping funnel was bury solution 8,32 g (0.05 mol) of chloromethylthiazole in 20 ml of DMSO within half an hour. The reaction was carried out 5 h (TLC control). Then the reaction mixture was poured into cold water, acidified with a solution of 10% hydrochloric acid to pH=6, was filtered light yellow crystals. The yield of compound I was 9.7 g (79.8 per cent). TPL=185-186°C.

Elemental analysis for C13H13TO3ABOUT2(243).

Calculated (%): 64,19, N Of 5.34, N 17,30, 13,17. Found (%): 64,15, Lower Than The 5.37 N, N 17,40, O 13,08.

An NMR spectrum1H (DMSO-d6), (, memorial plaques): 1,50...of 1.64 (t, 3H, CH3), 4,42...4,66 (square, 2H, CH2), and 5.5 (s, 1H, NH); 6,9 (s, 1H, CH); 7,05...7,21 (m, 4H, HPh); 7,27 (c, 2H, NH2).

X , cm-1: 3250, 3460 (NH2), 1700 (C=0), 1610,1600 (C=C).

Example 2.

The study astragalina and anti-stress activity of ethyl-3-the compounds of formula I and of similar structure Dibazol studied in seeds of winter wheat varieties Polovinka.

The inventive compound of formula I and a similar structure Dibazol used in an aqueous solution with a mass fraction 0,01%, 0,005%, 0,001%, 0,0005% and 0.0001%, similar to properties of gibberellin in the form of an aqueous solution with a mass fraction of 0.001% by pre-sowing seed soaking for 18 hours At quality control taken seeds treated with water. Each sample used for 50 PCs of seeds. Experiment was repeated three times.

Seeds were germinated for 7 days in rolls of filter paper. About the activity of the compounds of formula I to be judged by the influence on seed germination, height of sprouts, length of roots of seedlings, and their mass and potential productivity. The research results are summarized in tables 1 and 2.

Tests conducted on seeds of winter wheat varieties Polovinka has allowed to establish that all tested compounds in the concentration range of 0.01 and 0.0001 wt.% exhibit the properties of growth stimulants.

Dibazol in optimal growth stimulating dose of 0.0001 wt.% increases the germination energy by 6%, the length of the cane system 7-days-old seedlings - by 16.3%, the length of roots seedling - 23.2% and their weight - 17.5 and 18.8% respectively in comparison with control (0.1 wt.% an aqueous solution of DMSO).

In conditions of water stress tested compounds remain active growth and synthetic processes, activating the growth of cane system of seedlings and contributing to the regeneration of roots.

Dibazol in optimal postactivity concentration of 0.0005 wt.% increases the height of the seedlings 32.2%, length of roots - 20.8% and the weight by 35.3 and 21.4% respectively in comparison with control (0.1 wt.% an aqueous solution of DMSO).

The claimed connection in optimal postactivity concentration of 0.0005 wt.% increases the length of the cane system of seedlings 33.9%, length of roots - 28.3%, their mass - 29.4 and 53,6% respectively compared to control.

Thus, the claimed connection to its effectiveness is not inferior to similar in structure and properties, exhibiting the properties of highly effective stimulator of growth and increases the resistance of seedlings of winter wheat varieties Polovinka to water stress, and therefore, can be used in arid areas to improve seed winter wheat.

Ethyl-3-amino-N-benzo[d]-pyrrolo-[1,2]IME.



 

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