Melamine salt of bis(oxymethyl)phosphinic acid(melafen) as a regulator of growth and development of plants and how you can get


(57) Abstract:

Describes a new connection - melamine salt of bis(oxymethyl) phosphinic acid of the formula I as a regulator of growth and development of plants. It provides a wide range of actions in the plant body, regulating energy processes throughout plant ontogeny. Also describes how you can get it. 2 S. p. f-crystals, 14 tab., 9 table.

The invention relates to heterocyclic chemistry and organo-phosphorus compounds, namely melamine salt of bis(oxymethyl)phosphinic acid of formula I (hereinafter referred to as Melafen") and how you can get it

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The specified connection is a regulator of growth and development of plants and may find application in agriculture and horticulture.

The proposed connection, its properties and the method of obtaining not described in literature.

Of compounds with similar structure to the claimed known salts of melamine with phosphoric acid (U.S. patent N 4080501, publ. 21.03.78, Rehim NP (1978)) [1] , (GDR patent 217516, publ. 16.01.85, Rehim NP (1985)) [2] , used as additives, which impart incombustibility organic materials (paper, wood, plastics and La. The WG Proposal from 23.02, Rehim N (1998)) [3], derived from melamine and ammonium dihydrophosphate, and criminalistical (Application 3342288, Germany. Declared 23.11.83 Rehim NP (1986)) [4], derived from pentatricopeptide Na5P3O4and melamine in the presence of hydrochloric acid. As means for imparting flame resistance of polymeric materials proposed salt dialkylphosphorous acid with melamine (Application 2620119, France. Declared 31.03, Rehim NP (1990)) [5].

It is shown, however, that when heated to 110oC dialkylphosphorous acid (5-7-fold excess) with melamine in the presence of sodium alcoholate to form the products of alkylation (C. C. Orel, B. A., Vovsi, Joh, T. 39, issue.4, 926-927 (1969)) [6]

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In [7] studied the structure of salts of melamine with dealkylation and dialkylphosphorous acids, obtained by boiling the latter with melamine in anhydrous acetone (Zimin, M. G., Fomagin E. C., Zheleznov, L. C., R. Islamov,, Ludovic A. N. Coll., Chemistry and technology. ORGANOMETALLIC compounds and polymers, Kazan, 1987, 4-12) [7].

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Known melamine salt with an organic, in particular dialkylphosphinate, acids (U.S. Pat. 5604080, USA. Declared 27.02.95, Prior. 13.1.95, N 7-019903, Japan, Rehim NP (1998)) [8], which are part potassium and s in the same kind of activity, unknown. All of the above salts of phosphoric and dialkylphosphorous acids with melamine were studied only as flame retardants [1-5, 8] or their useful properties was not studied[6, 7]. Of compounds with close views of activity, we can note the use of technical melamine - structural fragment of the claimed compounds as a stimulator of plant growth (Allan G. G. , Kaszkiewicz Century, Przem. Chem., 1986, 65, N 4, 196-196 (Polska), Rehim 7O501 (1987)) [9], where it is shown that melamine can be a nutritional component for cucumbers. Know the use of phosphorous acid and its salts for presowing treatment of seeds for the prevention of destruction of plant pathogenic fungi used doses which are 1-500 g per 100 kg of seeds (Application 2706736, France. Declared 26.6.93, Rehim OP (1996)) [10] , (Application 2708415, France. Declared 16.6.94, Rehim OP (1996)) [11].

Sol obtained by alkylation of methyl-N-bis(2-oxyethyl)amine by trimethylphosphate"Ataman" (Melnikov N. N., Novozhilov K. C., Belan, S. P. Pesticides and plant growth regulators. A DSS. ed., M. Chemistry, 1995) [12], page 199

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proposed for presowing treatment of seeds at doses of 50 g/ton for increased harvest of root crops.

As plant growth regulators proposed 2-holdem "Gitell" [12, page 55]. The mechanism of action of 2-chloroethylphosphonic acid and many of its derivatives is the emission of ethylene in the metabolism of these compounds in plants (E. Tumanov Century , Chmyr I. M., Dzhilkibaeva, M. Izv. Academy of Sciences of the Kazakh SSR, Ser. Chem., 2 (242), 88-92 (1987)) [13].

As plant growth regulators proposed derivatives of phosphonic and phosphinic acids containing alkyl radical amino acid residues: glyphosate [12, page 56], [13, page 90],

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glufosinate-ammonium [12, page 58], used as herbicides and for the desiccation of potato haulm, sunflower and other crops

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Derived phosphinic acid with amino acid fragments in one of the alkyl radicals "Gasol" [12, page 43],

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obtained by fermentation of Streptomyces hydroscopicus recommended for seed treatment of corn in doses of 0.1 mg/ton.

Most similar in structure and method of obtaining the claimed compound is melamine salt dialkylphosphorous acids [7]. However, it is unknown useful properties.

The aim of the invention is to expand the Arsenal of methods for obtaining melamine salt of bis(oxymethyl)phosphinic acid having the ability Regula, than the currently used drugs [12], comparable in effect and doses of natural hormones.

This goal is achieved by the invention, namely melamine salt of bis(oxymethyl)phosphinic acid and its preparation. The essence of the proposed method of obtaining a melamine salt of bis(oxymethyl)phosphinic acid is in the interaction of melamine with bis(oxymethyl)phosphinic acid in aqueous and aqueous-alcoholic media when heated to 50-100oC. These conditions allow for the dissolution of the reaction product and allow to separate insolubles subsequent filtering. The desired product is released during the cooling of the filtrate and is separated by filtration. The outputs of the product 61-89,5%.

For a better understanding of the invention, specific examples of receipt of the proposed connection and the results of the study as a regulator of growth and development of plants.

EXAMPLE 1. To a suspension of 7.43 g (0.059 mol) of melamine in 100 ml of boiling methanol was added dropwise with vigorous stirring 7.80 g (0.0619 mole, 5% excess with respect to melamine) bis(oxymethyl)phosphinic acid in 50 ml of water. The reaction mixture is boiled for 1 hour and filtered in paracetamol and 60 ml of water. Filtered off the precipitated product, and dried in vacuum at 40-50oC. Get 10,50 gr (61.80%) of product. TPL215-216oC.

Found, %: C 23,69; H Of 6.96; N 32,17; P 11,14.

Calculated C5H13N6P1O40.5 H2O - C 22,99; H OF 5.40; N 32,18; P UP 11,86.

The product contains 92.3% of the basic substance according to NMR data31P with him. shift 35,29 M. D. (standard H3PO4) and 7.73% impurities with him. shift for 33.27 M. D.

EXAMPLE 2. To a suspension of 1.9 g of melamine in 35 ml of methanol was added dropwise with stirring 2.10 g (10% excess) bis(oxymethyl)phosphinic acid in 20 ml of water. The temperature of the reaction mixture increases from 20 to 25oWith and falls voluminous precipitate. When heated the reaction mixture to 65oSkipped the precipitate dissolves. The solution is filtered hot. After 3 hours the precipitation is filtered off, washed on the filter with methanol and dried in vacuum at 40oC. Obtain 3.4 g (89.47%) of product with Tpl.214-215oC. According to NMR data31P content of the main product is 86.9%.

EXAMPLE 3. To a suspension of 5.52 g of melamine in a mixture of 25 ml of water and 6 ml of isopropanol was added dropwise 6.0 grams (10% excess) bis(oxymethyl)phosphinic acid in 25 ml of water at paramasivan is evanie to 70-75oWith dissolves. The reaction mixture is heated 0.5 hour at 90-93oWith and filtered hot. The filtrate is cooled. The precipitated product is filtered, washed on the filter with isopropanol and dried in vacuum at 50-60oC. the product Yield 9.40 g (74.54%). Tpl.215-216oC. According to the potentiometric titration of the content of the main product 98.4%.

EXAMPLE 4. To a suspension of 5.52 g of melamine in 35 ml of water at 70-75oWith stirring was added dropwise 6.0 g of bis(oxymethyl)phosphinic acid in 25 ml of water. The reaction mixture is stirred at this temperature for another 0.5 hour and filtered hot. Precipitated upon cooling the filtrate, the precipitate is filtered off, washed with methanol and dried in vacuum. The yield of 7.80 g (61.85%). Tpl.215-216oC.

The solubility of the drug (Melafen) in water about 2 grams per 100 grams of water and aqueous solutions are stable when stored for years.

Listed below are studies of the impact of Melafen (preparation) on the growth, development, energy intensity of processes, biosynthesis of pigments and other indicators of the unicellular Alga Chlorella. We studied the germination energy, germination of seeds of some crops, fodder and vegetable crops, morphometrics value of spring wheat and winter rye, the seeds were treated with the drug. There are also some indicators of the impact of Melafen on the yield of potatoes grown conventional and meristem methods.

As a test object for study astragulus properties of Melafen was used unicellular Alga Chlorella. The extensive use of this facility to test the physiological activity of the new compounds is explained by the fact that detailed studies of the structural-functional and genetic features of Chlorella cells and their sensitivity to chemical and physical influences.

The Alga Chlorella single cell performs all life functions, and the development cycle is calculated in hours.

First and foremost was detected concentration dependence of the growth of Chlorella cells under the action of the drug. Experienced action of Melafen in a wide range of concentrations

The results presented in Fig.1 shows that the greatest effect on the growth of culture provides the Melafen at a concentration of 110-7-110-8%.

Astragalina activity of the drug is so high that it was comparable with the effect of adenosine triphosphate (ATP) (equal concentrations) on this process (Phi is elsebecause plant responses.

In Fig. 3 presents data on the rate of photosynthesis by Chlorella cells, as measured by the release of oxygen polarographic method.

Indeed, the intensity of photosynthesis of Chlorella in a pilot project was higher than control values. When comparing the influence of ATP and of the drug in the same concentrations on the rate of photosynthesis can be seen in practically the same effect. Using specific inhibitors (Diuron, antimycin A) for acyclic and cyclic photophosphorylation, it was revealed that the drug has a greater effect on cyclic photophosphorylation. Cyclic photophosphorylation is more resistant when the effects of adverse environmental conditions.

One of the reasons stimulating action of the drug on the intensity of photosynthesis is perhaps its influence on the biosynthesis of the pigments of the photosynthetic apparatus.

Table 1 provides data on the content of chlorophyll in Chlorella cells under the influence of the drug.

The amount of chlorophyll in the cells in the advanced options above to 15-17% in comparison with the control. There is a tendency to stimulate the rate of breathing under the influence of the drug. It is evident from Fig. 4 it is seen that proteincontaining.

Integral indicator of the physiological state of plant cells is the rate of heat dissipation, because this indicator reflects the final results of the interaction of all functional systems of the plant organism.

The results of the measurement of heat production by Chlorella cells defined microcalorimeter method shown in Fig. 5. Analysis of thermal images showed that the rate of heat production in a pilot project slightly above control values, which is associated with the activation energy and metabolic processes under the influence of the drug.

The obtained experimental data on the culture of Chlorella was able to conclude that the drug has a wide range of activities and has a high physiological activity comparable with natural growth regulators, with the action of ATP at low concentrations. The drug plays a role of substrate, and the like phytohormones operates in very small quantities, required to run and regulation fiziologicheskii programs.

Further experimental data on the effect of Melafen on some of the vital processes of a number of crops.

About the, fodder and vegetable crops (tables 2-4).

Morphometric characteristics of spring wheat was changed slightly under the action of the drug used in very low concentrations. There is a tendency of increasing the weight of the aerial parts of wheat germ, seeds which were treated with the drug (Fig. 6). In Fig. 7 presents data weight of roots of wheat seedlings. The positive point is that the weight of the roots of the experimental variants significantly higher weight of roots in control variants.

The drug has had a catalytic effect on the process of storing energy (Fig. 8). The rate of photosynthesis was higher up to 30% compared with control, which certainly has a positive effect on metabolic plants. Important and the fact that the drug had an effect on the biosynthesis of pigments at all stages of development of spring wheat.

Changes in the content of the main pigments in leaves of spring wheat under the action of the drug is shown in Fig. 9-11. The amount of chlorophyll "a" was significantly higher in the experimental apparatus, where seeds were treated with solutions of Melafen at a concentration of 10-8%. Also there was an increase in the number of chlorophyll "b". It must be emphasized, who has given his decline.

The amount of carotenoids in embodiments where the processed seeds of Melafen at a concentration of 110-8%, was higher than in the control at the stage of earing, when the control comes a sharp drop in the content of these pigments.

Because chlorophyll, and carotenoids play a protective role in plants, it can be assumed that the Melafen can increase resistance to adverse environmental conditions.

Comparative data breathing intensity and the magnitude of energy losses (Fig. 12) show that the drug regulates energy metabolism of plants of spring wheat, creating a favorable energy balance, increasing the rate of respiration and reducing energy losses.

Ultimately, the positive effect of Melafen on the growth and development of spring wheat on energy and metabolic exchange has led to increased productivity and improved quality of grain that can be seen from the data obtained in the NGO field of Tatarstan, where he conducted field experiments (tables 5, 6).

Experiments were conducted with the culture of rye, seeds which were soaked in solutions of Melafen in the concentration range from 110-6% 110-10%.

Autumn is La overwintering of winter rye. The analysis showed that the sugar content in plants, the seeds of which is treated with Melafen at a concentration of 110-8%, reached at 25.33% against 21.47% in the control. The results showed that the Melafen had an impact on the quantitative content of the main pigments (table. 7).

As spring wheat, the drug is optimized energy balance of the plant rye - breathing intensity was close to control values, and the energy loss (in the form of heat) were 20-40% lower than the control (Fig. 13).

It was found a positive effect of PA yield some vegetable crops. The data shown in Fig. 14.

Pre-treatment of potato tubers with a solution of Melafen at a concentration of 110-8% resulted in increase in yield by 33 kg (8.44%) per hectare.

The drug was used in technology for rapid multiplication of potato meristem. On the positive effect of the drug can be judged according to tables 8, 9.

On the apical stem cuttings of varieties "Beloyarsky early in the processing of Melafen 110-7% and 110-8% an increase in the formation of nodules by 15% compared with the control. The Melafen had an effect on the process of tuberization, commensurate with D. corn, the seeds which were treated with Melafen, showed that the content of crude protein in the silage increased in the experimental apparatus 11%, sugar - by 14.6%, phosphorus by 14.3% compared with the control. There are also improvements in the ratio of organic acid: increases the amount of lactic acid by 15.4% and reduced the content of acetic and propionic acids at 16.7 and 7.1%, respectively.

Obtained on a variety of crops experimental data allow to conclude the following.

1. The Melafen, as phytohormones, has multifunctional actions. The orientation of the physiological and biochemical changes in plants under the influence of drug-like effect of cytokinins on energy and metabolic plants. The Melafen as cytokines, is involved in regulation of physiological processes throughout ontogeny in the regulation of metabolism graduated from the growth of organs, increases the content of pigments, increases the intensity of photosynthesis, increases the speed of photophosphorylation (especially cyclic photophosphorylation), improves energy metabolism of plants.

2. The Melafen affects the germination energy and germination capacity of seeds to increase R> 1. The Melafen is effective at concentrations several orders of magnitude lower than currently used in the world growth regulators.

2. The drug has a high efficiency, increasing eventually yield, quality and nutritional value of agricultural products.

3. A consequence of the extremely low concentrations used for seed treatment, is the production of ecologically clean agricultural products.

4. Synthesis of Melafen is carried out in one stage, and the drug is very inexpensive compared to drugs such purpose.

1. Matamanoa salt bis(oxymethyl)phosphinic acid of the formula I as a regulator of growth and development of plants

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2. A method of obtaining a melamine salt of bis(oxymethyl)phosphinic acid, characterized in that the melamine is subjected to interaction with bis(oxymethyl)phosphinic acid in aqueous or aqueous-alcoholic medium when heated to 50 - 100oWith ensuring the dissolution of the formed reaction product, followed by filtration.


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