Application of n1-[2-hydroxy(phenyl)-4-metoxymethyl-6-methylthieno[2,3-b]pyridine-3-yl]pentamide as agent for activation of wheat seeds growing out

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to application of N1-[2-hydroxy(phenyl)-4-metoxymethyl-6-methylthieno[2,3-b]pyridine-3-yl]pentamide of formula as agent for activation of wheat seeds growing out.

EFFECT: enhanced assortment of biologically active compounds.

1 tbl, 2 ex

 

The invention relates to agriculture and to the chemistry of biologically active substances, namely the use of biologically active N1-[2-hydroxy(phenyl)methyl-4-methoxymethyl-6-methylthieno[2,3-b]pyridine-3-yl]pentanolide formula I

as a means to activate the germination of wheat seeds and aims to improve seed quality of wheat seeds.

Used the heterocyclic compound is a substance and its chemical properties are described in the literature [Catalog Name: Ambinter Stock Screening Collection, CAS Registry No. 900017-39-2, 03.07.2005].

To the closest analogs in the structure of the substances applied as a means to activate germination may be attributed 4,6-dimethyl-3-(1H-1-pyrrolyl)thieno[2,3-b]pyridine-2-carboxylate potassium salt (compound II)

[RF patent №2231527, IPC 7 C07D 495/04, 01N 43/90 Kaygorodova EA and other Substituted 3-(1H)-1-pyrrolyl)thieno[2,3-b]pyridine showing astragulus and anti-stress activity. from 27.06.2004. - Bull. No. 18].

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

However, the gibberellin - expensive drug microbiological synthesis and inaccessible. Its use causes irrational waste of plastic substances [Muromtsev G.S. and other Fundamentals of chemical regular and the growth and productivity of plants. M: Agropromizdat, 1987. - Pp.33-80].

The technical result is the expansion of the range of biologically active substances by applying the compounds of formula I as a means to improve seed wheat.

This is achieved by the fact that the applied substance of the formula I as a means to activate the germination of wheat seeds.

N1-[2-hydroxy(phenyl)methyl-4-methoxymethyl-6-methylthieno [2,3-b]pyridine-3-yl]pentanone obtained from 3-amino-4-methoxymethyl-6-methylthieno[2,3-b]pyridine-2-yl-phenylmethanone [Vukasin, Iagaiganognia, Shivering, Gdeen. Synthesis and properties of substituted isoxazole[3',4':4,5]thieno[2,3-b]pyridines // Chemistry of heterocycle. connections. - 2004. No. 3. - S-473] in two stages:

The compound obtained identified the sum of the data of elemental analysis, IR and NMR1N spectroscopy

The invention is illustrated by the following examples.

Example 1. Obtaining N1-[2-hydroxy(phenyl)methyl-4-methoxymethyl-6-methylthieno [2,3-b] pyridine-3-yl] pentanolide

N1-(2-benzoyl-4,6-dimethylthieno[2,3-b]pyridine-3-yl)pentanone obtained by acylation with the acid chloride of n-walerianowo acid in 1,4-dioxane 3-amino-4-methoxymethyl-6-methylthieno[2,3-b]pyridine-2-yl-phenylmethanone by the reaction:

A portion of 3.12 g (0.01 mol) 3-amino-4-methoxymethyl-6-METI the thieno-[2,3-b]pyridine-2-yl-phenylmethanone dissolve when heated in 30 ml of 1,4-dioxane. Make 1.25 ml (0,0105 mol) of veterinaria. The reaction mixture is boiled for 5 h, cooled. The precipitated crystals filtered off, washed with 10 ml diethyl ether, dried in the air. The output of 1.31 g (33%), TPL146-147°C.

An NMR spectrum1H (DMSO-d6, 250 MHz)d, ppm: 0,74 (t, 2H, CH2CH2CH2CH3, J=6,5); 1,01-1,08 (m, 2H, CH2CH2CH2CH3); 1,09-of 1.15 (m, 2H, CH2CH2CH2CH3); is 1.81 (t, 2H,CH2CH2CH2CH3, J=6,5); 2,63 (s, 3H, 6-CH3); of 3.42 (s, 3H, CH2OCH3); to 4.92 (s, 2H,CH2OCH3); the 7.43 (s, 1H, Hpy); the 7.65 (DD, 1H, 4-HArI , J4,3=J4,5=7,9); 7,52 (DD, 2H, 3,5-HArI , J3,2=J5,6=8,0, J=3,4=J5,4=7,9); 7,71 (d, 2H, 2,6-HArI , J2,3=J6,5=8,0); 9,71 (s, 1H, NH).

Found, %: C 66,55; N 6,13; N 7,01. C22H24N2O3S. Calculated, %: C 66,64; N 6,10; N 7,06.

N1-[2-hydroxy(phenyl)methyl-4-methoxymethyl-6-methylthieno [2,3-b]pyridine-3-yl]pentanone get recovery by sodium borohydride in ethanol N1-(2-benzoyl-4,6-dimethylthieno [2,3-b] pyridine-3-yl)pentanolide by the reaction:

To 3,96 g (0.01 mol) of N1-(2-benzoyl-4,6-dimethylthieno[2,3-b]pyridine-3-yl)pentanolide poured 80 ml of ethanol with constant stirring and heated to dissolve the solid phase. Cooled to room temperature and carefully make a fifth h is here estimated number of NaBH 4(0,58 g, 0.015 mol). For 1 h with continuous stirring, add the remaining NaBH4. Then the reaction mixture is heated to 60-70°and maintain this temperature for half an hour. The solution is cooled, the excess NaBH4carefully neutralized by adding small portions, 10 ml of 1 n HCl solution, watching the reaction mixture and preventing the lowering of pH of less than 7. The reaction mixture is poured into 4 liters of cold water, and intensively stirred. The precipitate is filtered off, washed with 400 ml of water and dried in air. Yield 3.50 g (88%)., TPL145-146°C.

An NMR spectrum1H (DMSO-d6, 250 MHz)d, ppm: 0,92 (t, 2H, CH2CH2CH2CH3, J=6.5 Hz); 1,33-of 1.40 (m, 2H, CH2CH2CH2CH3); 1,66-of 1.73 (m, 2H, CH2CH2CH2CH3); 2,32 (t, 2H,CH2CH2CH2CH3, J=6.5 Hz); to 2.55 (s, 3H, 6-CH3); 3,37 (s, 3H, CH2OCH3); 4,79 (d, 1H,CH2Och3I , Jheme=13.3 Hz); 4,74 (d, 1H,CH2Och3I , Jheme=13.3 Hz); to 5.93 (d, 1H,CHOH, J=6,1 Hz); 6.42 per (d, 1H, CHHE, J=6,1 Hz); of 7.25 (s, 1H, Hpy); 7,26 (DD, 1H, 4-HArI , J4,3=J4,5=8.0 Hz); 7,33 (DD, 2H, 3,5-HArI , J3,2=J5,6=8,1 Hz, J3,4=J5,4=8.0 Hz); 7,37 (d, 2H, 2,6-HArI , J2,3=J6,5=8.1 Hz); 9,41 (s, 1H, NH).

Found, %: C 66,42; N 6,55; N 7,02. With22H26N2O3S. Calculated, %: C 66,31; N 6,8; N 7,03.

Example 2. The effect of N1-[2-hydroxy(phenyl)methyl-4-methoxymethyl-6-methylthieno[2,3-b]pyridine-3-yl]pentanolide on seed quality of wheat seeds.

Astragulus activity of compound I and its impact on crop seed quality was determined model by laboratory screening seeds of winter wheat varieties Victory 50.

In the course of study is determined by the optimal astragulus concentration of compound I and its impact on sowing qualities of seeds, growth of seedlings, the accumulation of dry mass, potential productivity.

To study astragalina activity of the test compounds was pre-dissolved in dimethyl sulfoxide and then in the water.

As similar properties used gibberellins, as analogous with the structure of compound II in the form of 0.001 and 0.0001-percentage aqueous solutions, respectively.

Seeds of winter wheat were soaked in aqueous solutions of drugs for 18 h, and then were germinated in Petri dishes on moist filter paper within seven days.

Experiment was repeated three times. In each replication were used for 50 pieces of seeds.

About optimal growth stimulating concentration of compounds was tried on aggregate indicators such as germination, length and dry weight of seedlings.

The results of determining the optimal concentration of the compound I and its impact on sowing qualities of seeds are shown in table 1.

The connection I in the optimal growth stimulating dose of 0.0001 wt.% increases the germination energy by 4%, the length of the cane system 7-day-old seedlings (by 18.4%), length of roots seedling - 12.8% and their weight - 12.7 and 14.5% respectively in comparison with control and on their effectiveness is superior to gibberellin.

Compound II in optimal growth stimulating dose of 0.0001 wt.% increases the length of the cane system 7-days-old seedlings - 1.66% and weight of roots - 3,69% compared to control.

Thus, usage of N1-[2-hydroxy(phenyl)methyl-4-methoxymethyl-6-methylthieno[2,3-b]pyridine-3-yl]pentanolide formula I as a means to activate the germination of wheat seeds in agricultural production.

Table 1.
Influence of growth regulators on seed quality seed winter wheat varieties Win 50
The concentration of the aqueous solution, %Germination, %The length of the sproutWeight sprout
the sproutrootthe sproutroot
Option op is the Cm± to control, %cm± to control, %mg± to control, %mg± to control, %
Control-949,02-7,13-6,55-3,25-
Gibberellins0,001809,869,318,3016,413,72-43,212,16-33,54
The connection I0,01869,121,104,92-31,0of 6.783,512,40-26,15
0,005949,00-0,22a 4.83-32,35,63-14,02,30-29,23
0,001829,383,995,28-25,96,742,903,384,01
0,000594 9,505,325,58-21,7to 6.803,813,6010,77
0,000198for 10.68is 18.408,0412,767,3812,673,72of 14.46
Compound II0,0001949,171,665,00-29,874,03-38,473,373,69
NDSof 0.952,330,220,771,000,27
Pof 0.952,582,39of 13.5815,069,06

The use of N1-[2-hydroxy(phenyl)methyl-4-methoxymethyl-6-methylthieno[2,3-b]pyridine-3-yl]pentanolide formula

as a means to activate the germination of wheat seeds.



 

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