Structuresa trainingarea dikelola as an intermediate in the synthesis of salts with growth-stimulating activity against plant alfalfa

 

(57) Abstract:

The invention relates to chemistry and agriculture, specifically to a derivative of 1,3,5-triazine of the formula I. the Compound can be used as an intermediate in the synthesis of salts with growth-stimulating activity against plant alfalfa. table 1.

The invention relates to chemistry and agriculture, particularly to substituted 1,3,5-triazine as an intermediate in the synthesis of poststimulation alfalfa.

Known 2-substituted 4,6-bis(4'-carboxyphenoxy)-1,3,5-triazine General formula

< / BR>
where R = OCH3N(C2H5)2, NHC2H5, NHC6H5N(CH2)4O, as curing agents in the composition of the adhesive compositions structural purposes [see A. C. USSR N 836068; B. I., 1981, N 21]. The use of such digisat as poststimulation alfalfa unknown.

Known application indolylacetic acid (IAA) as poststimulatory fruit and berry crops, consisting of pre-soaking seed in 0,001% aqueous solution of IAA for 6 h [see plant growth Regulators - Ed. by C. C. of Sheveluch. - M.: Agropromizdat, 1911, c. Armentia working solution (the necessity of preliminary bodrstvovaniya in alcohol), long-term (6 h) the period of soaking of planting material, relatively low astragalina activity. The ability of IAA to stimulate the growth of alfalfa is unknown.

It is also known the use of 2,2-dimethylhydrazide succinic acid (daminozide) to increase yield and compactness of red clover plants by foliar spraying water 75 - 85% variance wettable powder daminozide [see Regulators of growth and development of plants. -M.: Agropromizdat, 1991, c. 13 is a similar application]. Poor enforcement of daminozide is its insolubility in water, the high cost of DV (dispersion 75 - 85 % concentration), the necessity of special, able to spray a 75% dispersion of the spray units; and also due to the high costs of daminozide the environmental risk of its use and low activity as poststimulatory. The use of daminozide to stimulate growth of alfalfa is unknown.

Technical solution to the problem of increasing the height of regrowth of alfalfa plants after mowing, increasing the mass of 1000 seeds, weight of seeds per plant, as well as improving the germination of seeds obtained from the harvest, is the all right soluble in water, with low costs LW, environmentally safe, does not require the use of special spray units and with higher astragalina activity in relation to plant alfalfa.

This object is achieved by obtaining a new intermediate for the synthesis of salts of serosoderjaschei of decislon: 2-diphenylamino-4,6-bis-[4'-carboxymethylthio] -1,3,5 - triazine of General formula

< / BR>
which can be used as an intermediate in the synthesis of efficient and water-soluble poststimulation alfalfa, which in turn are used for processing vegetative alfalfa in the form of an aqueous solution in a concentration of 0.0001 - 0.01 wt.%.

The novelty of the claimed proposal is seen that a new trainingarea dikelola as an intermediate in the synthesis of salts of serosoderjaschei triazinetrione of decislon that allows you to increase the options regrowth of alfalfa plants after mowing, mass of 1000 seeds and weight of seeds per plant, seed yield and germination of alfalfa seed from harvest. Salts have good solubility in water and high astragalina activity, avoid the use of special spray oborudovalis environment.

At the same time declared decollato get known method the interaction of the corresponding 2,4-dichloro-6-substituted-1,3,5-triazine with an aqueous-alkaline solution of thioglycolic in a molar ratio of 1:2 at a temperature of 20-30oC [see, M. Poghosyan, I. A. Asaturyan, C. N. Zaplishny. Synthesis of 2-methoxy 4,6-bis(p-carboxyphenoxy)-s-triazine and polymers based on it. - Arm. chem.J., 1976, T. 29, N 7, S. 597-601]. The source of 2,4 - dichloro-6-diphenylamino-1,3,5-triazine get known method is the interaction of the aqueous-acetone dispersion of 2,4,6-trichloro-1,3,5 - triazine with an acetone solution of diphenylamine in the presence of sodium carbonate at equimolar ratio source [see, M. Poghosyan, V. A. Pankratov, V. N. Zaplishny, S., Macayan. - Polythiazide. Izd-vo an Arm.SSR, 1987, S. 274].

For comparison astragalina activity industrial use drugs brand "chemically pure" IAA (prototype structure) and Dominatin (prototype).

Examples of performance stated suggestions are presented below.

Example 1. 2 Diphenylamino-4,6-bis-carboxymethylthio-1,3,5-triazine (VCT). A solution of 3,17 g (0.01 mol) of 2,4-dichloro-6-diphenylamino-1,3,5-triazine in 20 ml of acetone under stirring rapidly added to 50 g melkorazdroblennyh the th salts of thioglycolic. To the obtained mixture under stirring and the temperature is slowly added in small portions 1.68 g (0.02 mol) of sodium bicarbonate. Upon completion of the allocation of carbon dioxide and complete homogenization of the reaction mixture is stirred for further 1 h at 10oC and distilled acetone in water-jet vacuum on a boiling water bath. The distillation continued until the reduction of the volume of the reaction mixture by 1/2. The residue is cooled and under stirring and 202oC slowly acidified with hydrochloric acid to pH = 4-5. The resulting white flakes filtered off, washed with water until the absence of chlorine ion in the wash water and dried at 80 - 90oC. Get 3,835 g (89,6%) VCT in the form of a white powder with so pl. 218-220oC, is not soluble in water and most organic solvents, soluble in dioxane, DMF, DMSO, sparingly soluble in acetone and alcohol.

C15H16N4S2O4. Found, %: C 53,10; H 3,50; N 12,89; S Of 14.76.

Calculated, %: C 53,26; H 3,76; N 13,08; S 14,96

X , cm-1(group): 3410-3260 ush.cf. (IT sour.); 1685 cf. (C=O); 1580, 1500, 1485, 1465 (C=C, C=N - t. and cyanurates cycle.).

DMR , M. D. (group): 7,46 - 7.32 m (10H C6H5); is 4.21 (4H S-CH2).

Example 2. Under conditions analogous to example 1, and the same coaccion mixture simultaneously in the form of an aqueous solution get a 3.87 g (90,4%) VCT, appearance, physical and chemical constants, the data of elemental analysis and spectral characteristics of which are identical to those in example 1.

Example 3. 2 Diphenylamino-4,6-bis- [carboxylatomethyl(potassium)]-1,3,5-triazine (KMTC). To a suspension 2,185 g (0,0051 mol) of finely ground DTK in 8 ml of water under stirring and the temperature 201oC added dropwise 3 ml of an aqueous solution containing 0.56 g (0.01 mol) sodium hydroxide. The mixture is stirred for further 0.5 h at the same temperature and filtered. The obtained filtrate with stirring, added dropwise in 30 ml of alcohol, precipitated precipitate is filtered, washed with 2 x 50 ml dry ethanol and dried in vacuum (12 ml) at 50 - 60oC to constant weight. Get 2,288 g (88,8 %) CMTC in the form of a white powder with so different > 258oC, soluble in water and insoluble in common organic solvents.

C19H14N4K2S2O4. Found, %: C 45,05; H 2,62; N 11,25; S 12,59.

Calculated, %: C 45,22; H 2,79; N 11,10; S 12,71.

X , cm-1(group): 1635 - 1625 ush.CL. (COO); 1590 - 1565, 1495, 1445 - 1435 cf., C. (C=C, C=N - t. and cyanurates cycle).

Example 4. 2 Diphenylamino-4,6-bis[carboxylatomethyl(sodium)]-1,3,5-triazine (KMTN). Under conditions analogous to example 2, from the waters, and the target salt visidot the addition of water to the filtrate in 40 ml of acetone, get 2,325 g (96,5%) KMTN in the form of a white powder with so different. > 250oC, soluble in water and insoluble in common organic solvents.

C19H14N4Na2S2O4. Found, %: C 48,12; H Was 2.76; N 11,72; S 13,41.

Calculated, %: C 48,30; H 2,98; N Up 11,86; S 13,57.

X , cm-1(group): 1645-1620 ush.CL. (COO-); 1570, 1495, 1450-1440 cf., C. (C=C, C=N - t. and cyanurates cycle).

Example 5. 2 Diphenylamino-4,6-bis[carboxylatomethyl(ammonium)]-1,3,5 - triazine (CMTA). Under conditions analogous to example 3, from 2,185 g (0,0051 mol) VCT and 1.36 ml of 25% aqueous ammonia containing 0.34 g (0.01 mol) of ammonia, with the only difference that the reaction is carried out at 301oC in 10 ml of water, and the target salt visidot the addition of the filtrate to 50 ml of methanol, get 2,175 g (92.2 per cent) CMT in the form of a white powder with so different. > 230oC, soluble in water and insoluble in common organic solvents.

C19H22N6S2O6. Found, %: C 49,55; H To 4.98; N 18,03; S 13,95.

Calculated, %: C 49,33; H 4,79; N 18,17; S 13,86.

X , cm-1(group): 1650-1635 SL. (COO-); 1590-1575, 1455-1430 ush.with. (C=C, C=N - t. and cyanurates cycle).

P is ve poststimulation comprising means for processing vegetative plants of alfalfa.

When preparing aqueous solutions of tibouchina concentrations of 0.01 and 0.0001 wt. % handle vegetative alfalfa twice by spraying. For comparison, the use aqueous indolylacetic acid (IAA) and the variance of diamide succinic acid (Daminozide) at a concentration of 0.001 and 75 wt.% respectively. As a control, use the variant with two processing plants alfalfa water.

The use of "Diauxie as growth stimulants alfalfa comprising means for pre-treatment of vegetating plants alfalfa is illustrated by the following examples (examples 6-16).

Example 6. On the sowing of Lucerne second year of vegetation mowed plants and weeds to a height of 7 cm from the soil surface and divided into plots with an area of 1 m2. Under each version of the experiment is prepared in 3 plots, which are sprayed by ground sprayers. On the second day after mowing with water, an aqueous solution of IAA (200 l/ha, prototype) or 75% aqueous emulsion of Daminozide (analog) or by means of an aqueous solution of the corresponding variant concentration Tibouchina. The disinfectant or water (all except Daminozide) options, what Logoi solubility in water pre-podrastet in alcohol. After 7 days conduct spot measurements height regrowth on each plot (1kthat compared with the control (1kand determine the amount of regrowth in % according to the formula:

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In the phase of beginning of flowering (botanicare) the processing of all plots look similar to the 1-th processing quantities and concentrations of the prototype and the proposed drug. The weight of 1000 seeds, weight of seeds per plant and yield were determined for treated seeds by the formula:

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Germination is determined for the obtained yield of seeds (25 x 4) which is placed in a Petri dish in constantly moist filter paper and germinated them in a closed Cup with 251oC. On day 7 to determine the content of germinated seeds in % in % of control.

Examples of use of the proposed salt decislon to intensify the growth parameters of alfalfa: to increase plant height, weight of 1000 seeds and weight of seeds per plant, and yield and germination are presented in table (examples 6-16; see the end of the description).

As can be seen from the table data, the application of the proposed structuresa trainingabout decollate as an intermediate in the synthesis of salt - diauxie and the latter for the plants on the 7th day after mowing on 20,15 - 46,49% (13,0 - 15,85 instead 10,82 cm) at the same time spraying the plants with an aqueous solution of known means of IAA and Daminozide increases this parameter only 10,35 and 14,78%, respectively (11,94 and 12,42 cm, respectively).

Weight of 1000 seeds and weight of seeds per plant is increased in comparison with control 3.16-8,42% and results were 23.08-45%, respectively (1,96 - of 2.06 g and 3,20 - 3.77 g instead 1,90 and 2,60 g, respectively); at the same time, treatment with IAA and Daminozide increases these figures only 2,63; 16,15% and 3.05, to 21.15%, respectively.

Seed production of alfalfa increased by 43,19 - 73,24% (3,05 at 3.69 t/ha instead of 2.13 kg/ha); at the same time, treatment with IAA and Daminozide increases these figures only 7,98 and 25,82%, respectively (2,30 and $ 2.68 t/ha, respectively).

Germination of seeds obtained in yield increases in comparison with the control 8,08 - 16,61%, while treatment with IAA and Daminozide increases this rate by only 0.25 and is 5.06%, respectively.

An important advantage of the proposed intermediate for the synthesis of diauxie is to reduce the concentration and flow rate required for the processing means on the basis of tibouchina: 75 wt.% (Daminozide) to 0.01 and 0.0001 wt.% (Tibouchina), and A prior bodrstvovaniya in alcohol (IAA) and the use of direct dissolution in water at ordinary temperature.

Thus, the use of the claimed intermediate for the synthesis of salts of Diauxie as poststimulation allows you to increase height after alfalfa hay harvest, weight of 1000 seeds and weight of seeds per plant, seed production and germination of alfalfa seed to harvest, as well as reduce the costs and simplify the technology of its preparation and use.

Structuresa trainingarea dikelola General formula

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as an intermediate in the synthesis of salts with growth-stimulating activity against plant alfalfa.

 

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