2,4-dimorpholino-6-substituted sim triazine as poststimulation of wheat seeds

 

(57) Abstract:

Describes 2,4-dimorpholino-6-substituted SIM triazine used as poststimulation seed germination and increase the length of hypocotyl and root of wheat germ. They are of high growth stimulating activity even at high dilutions, which dramatically reduces consumption, according to the current matter and improves the environment. table 1.

The invention relates to chemistry and agriculture, particularly to substituted 1,3,5-triazines as promoters prorostania seeds.

Known application of indolyl-3-acetic acid (IAA) structure

used as a stimulant for germination of seeds auxinic activity type, as well as to stimulate rooting of fruit and stone fruit plants by soaking in an aqueous solution for 1 and 6 h, respectively [see plant growth Regulators./Edited by C. C. of Sheveluch. - M.: Agropromizdat, 1990, 192 S.]. Disadvantages of application of IAA are relatively high cost (240 thousand rubles per kg on 10.12.02,), narrow range recommended for seed treatment and relatively low stimulize 2 cyanomethylene-4,6-bis-alkyl(dialkyl)amino-SIM-triazine, structure

where R, R1, R2and R3=N, CH3WITH2H5and ISO-C3H7the same or different,

which are used as herbicides to inhibit the growth of wheat and wild oat [see centuries Dovlatyan, K. A., Eliasen. The synthesis of pesticides. 2 Cyanomethylene-4,6-bis-alkyl(dialkyl)amino-SIM-triazine and some of their transformation. - Arm. chem. J., 1971, T. 24, No. 4, S. 354-361]. Use them as poststimulation unknown.

Technical solution to the problem is to increase the length of hypocotyl and roots of seedlings of wheat and expansion of the range used poststimulation.

This object is achieved by obtaining a number of new derivatives of 1,3,5-triazine-2,4-bis(morpholin)-6-[(amino-('- oxyimino)ethyloxy]-sym-triazine and 2,4-bis(morpholin)-6-(3-oxocarboxylate-sym-triazine structure

which can be used as an effective poststimulation prorostania seeds and increasing the length of hypocotyl and root of wheat germ.

The novelty of the claimed proposal is seen in the fact that there are new derivatives of 2,4-disubstituted SIM-triazines as poststimulation germination of wheat seeds, which allows uwaki (110-4wt.%) the dilutions that dramatically reduces consumption by DV and improves the environment. They are also relatively easy and cheap source are synthesized, which reduces their value.

At the same time declared 2,4-disubstituted SIM triazine get known method the interaction of the corresponding 6-cyanomethylene-4,6-dimorpholino-SIM-triazine with hydroxylamine or acid hydrolysis of the specified cyanomethylphosphonate in solution, in water, boiling the mixture in the first case and at a temperature of 20C in the case of acid synthesis [see centuries Dovlatyan, K. A., Eliasen. The synthesis of pesticides. 2 Cyanomethylene-4,6-bis-alkyl(dialkyl)amino-SIM-triazine and some of their transformation. -Arm. chem. J., 1971, T. 24, No. 4, S. 354-361]. Source chloride (4,6-dimorpholino-1,3,5-triazine-2-yl)ammonium synthesis cyanomethylphosphonate get known method [see A. A., Cesnik, S. N. Mickle, W. S.), V. N. Zaplishny. The synthesis and transformations of Quaternary trimethylammonium salts of 2-chloro-4,6-disubstituted 1,3,5-triazine in some reactions SN.-CHC, 2002, No. 2, S. 197-203].].

Used organic solvents before use purified by known methods [see A. Gordon, R. Ford. Satellite chemist. M: Peace. 1976. -541 C.].

Examples of performance stated suggestions are presented below.

Example 1. 2 Cyanoethoxy-4,6-bis(morpholin)-1,3,5-triazine (CTMT) and 2,4-bis(morpholin)-6-[(-amino-'-oxyimino)ethyloxy]-sym-triazine (AGAT). In the flask is prepared cyanochlorous a mixture of 2 ml of water, 0.56 g (8,7 mmol) of potassium cyanide and 0.65 g (8,7 mmol) of 40% aqueous formalin solution. To the mixture under stirring at a temperature not higher than +5 ° C, was added dropwise a solution of 2 g (5.8 mmol) chloride (4,6-dimorpholino-1,3,5-triazine-2-yl)trimethylammonium in 5 ml of water. The reaction mixture was stirred 2 h at 20 ° C and diluted with 20 ml of cold water. The resulting white flakes filtered off, washed thoroughly with water to the absence of chlorine ion in the wash water and dried at 50-60C. Obtain 1.19 g (75%) CTMT in the form of a white powder with so pl. 155-C, insoluble in water and soluble in alcohol, acetone, methylene chloride and other polar organic solvents.

Found,%: C 51,13; N 6,09; N 27,60. C13H18N6O. Calculated,%: C 50,97; N. Of 5.92; N 27,44.

X , cm-1(group): 2340 cf. (CN);1580, 1540 S. (C=C, C=N - t. and cyanurates cycle.); 1210, 1170 S. (C-O-C).

DMR , M. D. (group): 5.02 (2H, OCH22. To the mixture was added a solution of 0.5 g (1.7 mmol) CTMT in 20 ml of ethanol and refluxed for 6 hours, the Solvent is distilled off in a water jet vacuum to dryness, the residue is washed with water (320 ml) and dried at 50-60C. After purification by crystallization from ethanol obtain 0.55 g (95%) target AGAT in the form of a white crystalline powder with so pl. 224-C, insoluble in water and soluble in polar organic solvents.

Found, %: C 46,19; N 6,37; N 29,08. C13H21N7O4. Calculated, %: 46,01; N 6,24; N 28,89.

X , cm-1(group): 3410, 3250 D. ush.Wed, (NH2and HE); 1660 cf. (C=N);1580, 1540 S. (C=C, C=N - t. and cyanurates cycle.);

DMR , M. D. (group): 9.12 (1H ush.s, HE); 5.67 (2H, NH2); 4.62 (2H, O-CH2); 3.55-3.75 (M m, N2+ CO2).

Mol. ion (mass by a spectroscope) 339.

Example 2. 2,4-Bis(morpholyl)-6--oxycarbonate-sym-triazine (ACMT). To 1 g (3.3 mmol) obtained in example 1 and finely ground 2-cyanomethylene-4,6-dimorpholino-SIM-triazine (CTMT) was added 3.5 ml of conc. hydrochloric acid and incubated the mixture for 0.5 h at a temperature of 20C. Then, under stirring at the same temperature, the reaction mixture was alkalinized 40% aqueous solution of the Ute at 50-60C. Get 0,46 g (70%) target OCMT in the form of a white powder with so pl. 186-C, insoluble in water and soluble in alcohol, acetone, methylene chloride and other polar organic solvents.

Found,%: C 48,15; N The 6.06; N 21,68. C13H19N5O5. Calculated,%: C 47,99; N. Of 5.89;N 21,53.

X , cm-1(group): 3400-3260 ush.(HEacids); S.(C=O);

1600,1580,1540 C. (C=C, C=N - t. and cyanurates cycle.);

DMR , M. D. (group): 12.70-12.80 (1H ush.s, - COOH); 4.62 (2H, OCH2COOH); 3.60-3.75 (M m, NCH2+ COMorpholyl).

Mol. ion (mass by a spectroscope) 325.

Example 3. 2,4-Bis(morpholyl)-6--oxycarbonate-sym-triazine (ACMT). Under conditions analogous to example 2, of the same amounts original CTMT and conc. HCl, with the only difference that the order of addition of the original return, and the process of peremeshivanija increase to 1 h, the gain of 0.42 g (64%) OCMT in the form of a white powder, all constants which meet those for ACMT in example 2.

Example 4. 2,4-Bis(morpholin)-6-[(-amino-'-oxyimino)ethyloxy]-sym-triazine (AGAT). Under conditions analogous to example 1, from the same source and quantities in the same order they were added, with the only difference that the process of boiling is increased to 10 example 1.

Synthesized 2,4-dimorpholino-6-substituted SIM triazine used as poststimulation seeds and wheat germ.

While they prepare aqueous solutions of the concentrations of 0.01 and 0.0001 wt.% and carry out the preplant wheat seeds by soaking seeds in water solution triazolyl-triazine corresponding concentrations within 1 h For comparison using an aqueous solution of IAA at a concentration of 0.001 wt.%. Due to the poor solubility in water, the original 2-substituted 1,3,5-triazine and IAA pre “podrastet” in a small amount of alcohol. As a control, use the variant with the seed treatment with water.

The use of 2,4-dimorpholino-6-substituted SIM-triazines as a growth promoter in wheat is illustrated by the following examples.

Example 5. After soaking in the working solution (or water, in the case of the control) for 1 h, the seeds were dried for 24 h in an air-convection mode at 20 ° C and were germinated in a Petri dish on constantly moistened filter paper (25 pcs. per option in five replications) at a temperature of 25±1C for 10 days. After 10 days of conducting measurements of root length and hypocotyl (1i), which is P>The obtained data were averaged, and the mean root length and hypocotyl, and the relative increase of these indicators relative to control % were brought to the table (see the table at the end of the description).

As can be seen from this table that the application of the proposed 2,4-dimorpholino-6-substituted SIM-triazines as poststimulation of wheat seeds leads to the following results.

If AGAT, its use as poststimulatory in concentrations of 0.01 and 0.0001 wt.% increases the length of the hypocotyl in accordance with the control 40-46% (57-60 instead of 41 mm), while the application of known poststimulatory IAA increases this ratio in comparison with control only 4.2% (42,7 instead of 41 mm). At the same time root length increased by 10-19% (95-102 instead of 86 mm), while the application of IAA increases this figure is only 3.5-6% (89,0-to 91.1 instead of 86 mm).

If OCMT, its use as poststimulatory in concentrations of 0.01 and 0.0001 wt.% increases the length of the hypocotyl in comparison with the control 27-49% (52-61 instead of 41 mm), while the application of known poststimulatory IAA increases this ratio in comparison with control only 4.2% (42,7 instead of the and increases this figure is only 3.5-6% (89,0-to 91.1 instead of 86 mm).

The claimed compounds are highly stimulating activity and large (of 0.0001 wt.%) the dilutions at which known heteroauxin increase the length of the hypocotyl no stimulare, and root-only 3.5%. Unlike peristediinae industrial synthesis of IAA claimed compounds are obtained in a single stage, from readily available and relatively inexpensive source.

Thus, the use of the claimed 2,4-dimorpholino-6-substituted SIM-triazines as poststimulation can increase the length of roots and hypocotyls of seedlings of wheat, as well as to reduce costs and to expand the range of known poststimulation.

2,4-Dimorpholino-6-substituted SIM triazine structure

as poststimulation seeds and wheat germ.

 

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