6-methyl-8-methoxymethyl-3-phenylisoxazole[3',4':4,5]thieno-[2, 3-b]pyridine, showing growth regulating and anti-stress activity

 

(57) Abstract:

The invention relates to new biologically active chemical substance, namely 6-methyl-8-methoxymethyl-3-phenylisoxazole[3', 4': 4,5]thieno[2,3-b]pyridine of formula 1, showing the growth regulating and anti-stress activity. The technical result - the creation of new biologically active substances used in agriculture as restoreultra, antistreaming drugs. table 2.

The invention relates to new biologically active chemical substance from a number analyoung heterocyclic compounds of the formula I,

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showing property to activate the germination of wheat seeds.

6-Methyl-8-methoxymethyl-3-phenylisoxazole[3', 4':4,5]thieno[2,3-b]-pyridine (I) is representative of a new heterocyclic system.

To the closest analogs in the structure of the claimed compounds can be classified as 4-hydroxymethyl-6-methyl-2-chloronicotinate potassium, exhibiting the properties of activator germination of seeds of agricultural crops (compound IV) [A. S. 1711459 from 08.10.91,].

As similar properties known gibberellins, are widely used to activate prolastin what their causes irrational waste of plastic substances [Muromtsev, S. and other foundations of chemical regulation of growth and productivity of plants. - Moscow: Agropromizdat, 1987. - S. 33-80].

The present invention is to expand the Arsenal of biologically active substances obtained synthetically, for their application in agriculture as postregulation and antitussive drugs.

This is achieved by using the compound 6-methyl-8-methoxymethyl-3-phenylisoxazole[3', 4':4,5]thieno[2,3-b]pyridine (I) by pre-sowing treatment of seeds.

The way to obtain 6-methyl-8-methoxymethyl-3-phenylisoxazole[3', 4': 4,5] thieno[2,3-b]pyridines known in the literature [Vaselin C. K., Kaygorodova E. A., Krapivin D. New heteroaromatic system - isoxazole[3',4':4,5]thieno[2,3-b]pyridine Chemistry of heterocycle. connections. - 2000. - 4. - S. 565-566].

The compound (I) received during the decomposition reaction of 3-azido-2-benzoyl-6-methyl-4-ethoxymethylene[2,3-b]pyridine (II) in m-xylene.

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The claimed substance receive a two-step synthesis of 3-amino-6-methyl-4-methoxymethyl-2-benzoylamino [2,3-b] pyridine.

The process consists of the following stages:

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3 Azido-2-benzoyl-6-methyl-4-ethoxymethylene[2,3-b]pyridine (II).

1,69 g (0,005 mol) of a substance III was dissolved in 12 is not up to +5...+8oAnd slowly, in small portions made solution of 0.48 g (to 0.007 mol) of sodium nitrite in 2 ml of water. Was stirred for 20 min, then neutralize the excess of nitric acid urea (control ikramullah paper) and added dropwise during 10 min was injected solution and 0.46 g (to 0.007 mol) of sodium azide in 2 ml of water. Continued stirring for one hour. Then the reaction mass was slowly poured into the water with finely crushed ice. The residue azide II was separated, washed on the filter with cold water until neutral wash water, dried over concentrated sulfuric acid. Yield 74%, Tpl.=117 115...oC (with decomposition).

Elemental analysis for C17H14N4O2S (338,39)

Found: 60,45; N 4,19; N 16,52;

Calculated: 60,34; N 4,17; N 16,56.

Range PMR (DMSO-d6): to 2.65 (3H, s, CH3), of 3.54 (3H, s, och3), to 4.87 (2H, s, och2), 7,41 (1H, s, HRu), 7,45...7,83 (5H, m, HPH), X , cm-1:2210 (N3). 1625 (C=0).

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stage 2

6-Methyl-8-methoxymethyl-3-phenylisoxazole[3', 4': 4,5]thieno[2,3-b]pyridine (I).

1,69 g (0,005 mol) of compound (II) was boiled in 30 ml of m-xylene for 30 minutes then the solution was cooled to room temperature, diluted with 40 ml of Gex the air. Was purified by recrystallization from DMF. Yield 81%, Tpl.=183...184oC.

Elemental analysis for C17H14N2O2S (310,38)

Found: 65,93; N 4,50; N 9,07;

Calculated: 65,79; N 4,55; N 9,03.

Range PMR (DMSO-d6): to 2.65 (3H, s, CH3), of 3.54 (3H, s, och3), to 4.87 (2H, s, och2), 7,41 (1H, s, HRu), 7,45. . .7,83 (5H, m, HPh). UIFmax() : 212(4,33), 221(4,26), 245(4,19), 254(4,18), 288(4,53), 335(3,90).

The invention is illustrated by the following examples:

Example 1. Astragalina and anti-stress activity of 6-methyl-8-methoxymethyl-3-phenylisoxazole[3',4':4,5]-thieno[2,3-b]pyridine.

Astragulus and anti-stress activity of compound I was determined model by laboratory screening seeds of winter wheat varieties Rufus.

Determined optimal postactivity concentration of compound I, its influence on the sowing qualities of seeds, growth of seedlings, the accumulation of dry mass, potential productivity and sustainability of seedlings to water stress.

As similar properties used gibberellins, as similar in structure - 4-hydroxymethyl-6-methyl-2-chloronicotinate potassium.

Compound I was used as the water races the Okha solubility of compound I was pre-dissolved in DMSO.

Seeds were soaked in aqueous solutions of drugs for 18 hours Then the seeds were germinated in Petri dishes for three days at a temperature of 20-22oC. Next half of germinated seeds in each sample were subjected to water stress by drying them for hours and then germination continued in rolls of filter paper. Experiment was repeated three times. In each replication were used for 50 seeds.

About optimal postactivity concentration of the compound I to be judged by the aggregate indicators such as germination, length and dry weight of seedlings and their potential productivity.

The research results are summarized in table. 1.

From the data presented in table 1, shows that the connection I in the studied concentration range of 0.005-0,00005% activates the growth of cane system of seedlings and in doses 0,0025-0,005 increases the accumulation of biomass in aboveground parts and roots of seedlings.

As follows from the table. 1, the connection I in the optimal dose 0,0025% increases the height of the seven-day seedlings 61.6%, mass by 79.2%, root mass by 49.3% in comparison with control (a 0.01% aqueous solution of DMSO). At the same time similar properties gibberellins in optimal is icepay the length of the roots, increasing their mass by 8.9% in comparison with the control. Similar in structure 4-hydroxymethyl-6-methyl-3-cyano-2-chloronicotinate potassium optimal dose of 0.001% increases the length of the seedlings on 18,85%, the mass of 17.8%, the length of the roots of 1.2%, root mass by 5.8% compared to control.

Thus, the claimed matter in the concentration range 0,0025-0,0005% improves sowing qualities of seeds of winter wheat and optimal dose 0,0025% excels in its growth activity similar in structure and prototype.

The effects of the claimed compound I on the stability of winter wheat seedlings to water stress are given in table. 2.

In the optimal dose of 0,00025% connection I contributes to maintaining growth and synthetic processes in the cells. At this concentration the connection I better regeneration of the root system of seedlings subjected to water stress, which manifests itself in increasing root length by 29.8%, of their weight of 27.5%, while the similar properties of gibberellins in optimal dose reduces the length of the roots by 9.7% while increasing their weight by 9.4%, while similar in structure 4-hydroxymethyl-6-methyl-3-cyano-2-chloronicotinate potassium optimal dose of 0.001% increases the length of the roots 24.1%, and lotkov of winter wheat to water stress and on the whole more efficient than counterparts in structure and properties.

6-Methyl-8-methoxymethyl-3-phenylisoxazole[3', 4': 4,5] thieno[2,3-b] pyridine, showing growth regulating and anti-stress activity of the formula I



 

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