Salts of n-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acids for use as stimulators of plant and fungal growth

Abstract

The present invention relates to novel salts of N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acids of formula (I) wherein the values of the groups are disclosed in the claims, and to the use of said salts as growth stimulators of plants and fungi. The present invention also relates to embodiments of a process for the preparation of an N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acid of formula (I). The technical result is the preparation of novel salts of N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acids of formula (I), which exhibit improved plant growth stimulating agent properties. [Chemical Formula I]

Description

Technical Field

[0001] This invention relates to novel compounds for use in agriculture, particularly for regulating plant growth and development and for stimulating the growth of plants and fungi.

[0002] In particular, these new compounds can be used to optimize plant growth parameters for a variety of crops, such as germination potential, seed germination rate, seedling biometrics, root formation, and yield. Existing technology

[0003] Plant cultivation faces numerous challenges related to extreme temperature fluctuations, water scarcity, and unfavorable regional climatic conditions. In this regard, new methods to stimulate plant growth and development are needed, which can be achieved through the use of synthetic compounds. (Vasin, AV “Use of growth stimulators in corn and barley cultivation” / AVVasin, AVDarmin, VVBrezhnev / / Fodder production / AVVasin, AVDarmin, VVBrezhnev. Breezhnev / / Kormoproizvodstvo (Feed production). - 2009. - No. 2. - P. 17-18; Vasin, VG “Efficiency of the growth stimulator application at corncultivation for grain” / VGVasin, AVDarmin, AVVasin / / Izvestiya Samarskoygosudarstvennoy selskokhozyaistvennoy akademii (Bulletin of Samara State Agricultural Academy). - 2008. - No. 4. - P.)

[0004] 22-24; Ostroshenko, V.V. "Influence of pre-sowing seed treatment with growth stimulators on their sowing qualities" / V.V. Ostroshenko, L.Yu. Ostroshenko / / Vestnik Krasnoyarskogo gosudarstvennogo agrarnogo universiteta (Bulletin of Krasnoyarsk State Agrarian University). - 2011. - №5. - P. 12. - 15; Shishov, A.D. "Determination of growth-stimulating concentrations of new growth regulators and plant stability inducers" / A.D. Shishov, G.L. Matevosyan / / Fundamentalnye issledovaniya (Fundamental Research). - 2005. - №9. - P. 46-47; 16; Sinkov, A.A. "Influence of growth regulators on limitation of abiotic and biotic stresses in the cultivation of winter wheat on chernozem leached southern Non-Black Soil: Cand. of Agricultural Sciences" / A.A. Sinkov. - Saratov, 2011 - 21 p.; "Influence of synthetic growth regulator cytodef and heavy metals on the oxidative status of cucumber plants" / D.I. Bashmakov and [others] / / Fiziologiya rasteniy (Plant Physiology). - 2012. - T. 59, №1. - P. 67-73).

[0005] Patent RU 2485083 C1 describes substituted pyrimidine-5-yl-carboxylic acids of general formula 1, which are similar in structure to the proposed compounds.

[0006] [Chemical Formula 1]

[0007]

[0008] wherein R1+R2 = piperidine, pyrrolidine, morpholine, N-Alk(Ar)piperazine, or R1 = Alk, Ar; R2 = Alk, Ar, or R1 = H, R2 = H, Alk, Ar, Het; R3 = Alk, in particular methyl, Ar, etc., R4 = H. In particular, compounds are described wherein R1+R2 = piperidine, or R1 = hydrogen, R2 = phenyl, 2-benzyl, 2-phenethyl, 4-methylphenyl, benzoxazol-2-yl, benzothiazol-2-yl, 4-methylquinazolin-2-yl; R3 is methyl, R4 is hydrogen. The compounds have growth-regulating activity on deviated velvet (Tagetes patula L).

[0009] The known compounds of formula (1) are prepared according to the following scheme

[0010] [Chemical Formula]

[0011]

[0012] Patent RU 2788114 C1 describes the use of a compound according to the above general formula (1) (wherein R1 = hydrogen, R2 = benzyl, R3 = methyl, R4 = hydrogen) as a growth stimulant for sugar beets.

[0013] Patent RU 2490893 C1 describes a method for stimulating the growth of deviated velvet using a compound according to the above formula (1) (wherein R1 = hydrogen, R2 = benzyl or 2-phenethyl, R3 = methyl);

[0014] Patent RU 2663068 C1 describes a method for stimulating the growth of plant species of the genus Rhododendron L using a compound of formula (1) (wherein R1 = hydrogen, R2 = benzyl, or R1 and R2 together with the nitrogen atom represent piperidine, R3 represents methyl).

[0015] Patent RU 2656393 C1 describes a method for stimulating the growth of plants of the genus Rhododendron using a compound according to the above formula (1) (wherein R1 = hydrogen, R2 = benzyl, or R1 and R2 together with the nitrogen atom represent piperidine, morpholine).

[0016] Patent RU 2659828 C1 describes a method for using a compound of formula (1) (where R1 and R2 together with the nitrogen atom represent piperidine, morpholine, R3 represents methyl) as a growth regulator for annual Salvia splendens.

[0017] Patent RU 2678119 C1 describes the use of a compound of formula (1) (where R1 = hydrogen, R2 = benzyl, or R1 and R2 together with the nitrogen atom represent piperidine, morpholine, R3 is methyl) for stimulating the growth of common tomato (Solarium lycopersicum L).

[0018] However, the known substituted pyrimidine-5-yl-carboxylic acids do not have sufficiently high seed germination rate, yield and plant height, and have a significant drawback - very poor water solubility, which makes dosing and use of these products difficult.

[0019] Patent US 3040047 B1 (Example 17, columns 6, 7) describes a method for preparing a sodium salt (1:1) of 2-(4,5-dimethyl-1H-pyrazol-1-yl)-4-methylpyrimidine carboxylic acid. The method includes adding a solution of sodium hydroxide and ethanol to 2-(4,5-dimethyl-1H-pyrazol-1-yl)-4-methyl-5-carboxyethylpyrimidine. The mixture is boiled, then concentrated to isolate the crystalline sodium salt. The known salt is used as an intermediate for the subsequent preparation of the corresponding acid.

[0020] The salt of the present invention does not contain a 4,5-dimethyl-1H-pyrazol-1-yl group at position 2 of the pyrimidine ring and has a different use for stimulating plant growth. SUMMARY

[0021] TECHNICAL PROBLEM

[0022] The object of the present invention is to improve the physicochemical properties of plant growth stimulants, in particular to improve the solubility and performance in terms of seed germination rate, plant height, weight gain and yield when treating with growth stimulants before sowing the seeds and at any stage of plant development.

[0023] SOLUTION TO THE PROBLEM

[0024] The above technical problem is solved by using a new plant growth stimulant, i.e. a salt of N-substituted 2-amino-4-methylpyrimidine-5-yl-carboxylic acid of general formula (I):

[0025] [Chemical formula I]

[0026]

[0027] where X + is selected from the group of cations Na+ , K + , Li + , 1 / 2Mg 2+ , 1 / 2Ca 2+ , NH4 + , H3N+CH2CH2OH, H3N+CH2CH2CH2OH, HN+(CH2CH2OH)3, H3N+CH2CH2C6H5, or ANH3 + , A2NH2 + , A3NH + ,

[0028] A represents a C1-C 12 alkyl group, a C6-C 12 aryl group, a C5-C 12 heterocyclyl group, a C5-C 12 heteroaryl group, wherein the heterocyclyl and heteroaryl groups contain 1 to 3 heteroatoms selected from N, O, and S,

[0029] wherein each A is optionally substituted with one or more groups independently selected from halo, amino-, thio-.

[0030] The term "alkyl" includes straight chain, branched chain, or cyclic hydrocarbon structures having a chain length of from 1 to 12 carbon atoms, preferably from 1 to 6 carbon atoms, more preferably from 1 to 3 carbon atoms, and combinations thereof.

[0031] The term "aryl" refers to a phenyl, biphenyl, or naphthyl group.

[0032] The term "heteroaryl" alone or in combination, refers to a 5- to 10-membered monocyclic or bicyclic aromatic ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur. Preferably, the term "heteroaryl" refers to a 5- to 10-membered monocyclic or bicyclic aromatic ring containing one nitrogen atom and optionally one additional heteroatom independently selected from oxygen, nitrogen, and sulfur.

[0033] Examples of such heteroaryl groups include furanyl, oxazolyl, isoxazolyl, oxadiazolyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, indolyl, isoindolyl, benzofuranyl, isobenzofuranyl, benzothienyl, indazolyl, benzoimidazolyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl , benzisothiazolyl, benzotriazolyl, benzo[2,1,3]oxadiazolyl, benzo [2,1,3,3]thi diazolyl, benzo[l,2,3,3]thiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, and phthalazinyl.

[0034] In a preferred embodiment, R1 represents methyl, ethyl, propyl; phenyl optionally substituted with one or two substituents selected from methyl, ethyl; methoxy, halogen; and phenyl-(C1-C2)alkyl-.

[0035] In a preferred embodiment, R+R1 together with the nitrogen atom represents pyrrolidine, quinoline, isoquinoline, piperidine, morpholine, or piperazine, optionally substituted with one or two substituents selected from methyl, ethyl, halogen, and phenyl.

[0036] In a preferred embodiment, the cation is Na. + K + Li + 1 / 2Mg 2+ 1 / 2Ca 2+ NH4 + H3N + CH2CH2OH, H3N + CH2CH2CH2OH, H3N + CH2CH2C6H5、HN + (CH2CH2OH)3.

[0037] The salts proposed, their preparation, and their uses in stimulating plant growth were previously unknown.

[0038] The plants can be common tomatoes (Solarium lycopersicum L.), beets, annual glossy sage (salvia glossy), marigolds with abnormal growth, rhododendron species, and so on.

[0039] The N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acid salt of formula (I) is a water-soluble substance whose solution can be used alone or in combination with other substances in the agricultural process for pre-sowing seed treatment, as well as for subsequent application to the soil at different stages of plant and fungal development.

[0040] The N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acid salt of formula (I) is convenient and effective as a plant growth stimulant.

[0041] As salts of N-substituted 2-amino-4-methylpyrimidine-5-carboxylic acids of the formula (I), in particular, salts of 2-(2-phenylethyl)amino-4-methylpyrimidine-5-yl- carboxylic acid, 4-methyl-2-(pyrrolidin-1-yl)pyrimidine-5-yl-carboxylic acid, 4-methyl-2-(N-methylpiperazin-1-yl)pyrimidine-5-yl-carboxylic acid, 4-methyl-2-((4- methoxyphenyl)amino)pyrimidine-5-yl-carboxylic acid, 2-benzylamino-4-methylpyrimidine- 5-yl-carboxylic acid, 2-(3,4-dihydroisoquinolin-2(1 H)-yl)-4-methylpyrimidine-5-yl- carboxylic acid, 4-methyl-2-((2,4-difluorophenyl)amino)pyrimidine-5-yl-carboxylic acid, 4-methyl-2-((4-methylphenyl)amino)pyrimidine-5-yl-carboxylic acid, 4-methyl-2- (morpholin-4-yl)pyrimidine-5-yl-carboxylic acid, 4-methyl-2-(piperidin-1-yl)pyrimidine-5- yl-carboxylic acid, 4-methyl-2-((3-methylphenyl)amino)pyrimidine-5-yl-carboxylic acid, and the like can be used.

[0042] Inventive Effects

[0043] The present study comparatively evaluated the effects of salts of N-substituted 2-amino-4-methylpyrimidine-5-yl-carboxylic acids and the corresponding N-substituted 2-amino-4- methylpyrimidine-5-yl-carboxylic acids on morphological parameters such as seed germination rate, plant yield and plant height, root system.

[0044] The following plants were selected for the study: common tomato (Solarium lycopersicum L) of the variety "Novichok". Seeds of the company "Aelita" (Moscow) were used as material; common eggplant (Solanum melongena L.) of the variety "Lilac"; perennial rhododendron Ledebourg (Rhododendron Ledebourii Pojarc.); marigold (Tagetes patula L.) of the variety "Red Cherry" with abnormal growth; winter wheat (Triticum aestivum L.) of the variety "Alekseich"; potato (Solanum tuberosum) of the variety "Zekura"; sunflower (Helianthus L.) of the variety "Chakinsky 100"; corn hybrid (Zea mays L.) "Mixi"; zucchini (Cucurbita pepo subsp. pepo) of the variety "Tintoretto"; peas (Pisum L.) of the variety "Orlus"; white cabbage (Brassica oleracea L.) of the variety "Podarok"; sweet pepper (Capsicum annuum L.); white double-spore mushroom.

[0045] The technical result is achieved by the fact that 2-(2-phenylethyl)amino-4-methylpyrimidin-5-yl-carboxylic acid, 4-methyl-2-(morpholin-1-yl)pyrimidin-5-yl-carboxylic acid, 4-methyl-2-(N-methylpiperazin-1-yl)pyrimidin-5-yl-carboxylic acid, 2-benzylamino-4-methylpyrimidin-5-yl-carboxylic acid, 4-methyl-2-(piperidin-1-yl)pyrimidin-5-yl-carboxylic acid, 4-methyl-2-((2,4-difluorophenyl)amino)pyrimidin-5-yl-carboxylic acid, 4-methyl-2-((4-methylphenyl)amino)pyrimidin-5-yl-carboxylic acid, 4-methyl-2-(morpholin-4-yl)pyrimidin-5-yl-carboxylic acid, 4-methyl-2-(piperidin-1-yl)pyrimidin-5-yl-carboxylic acid, 2-(3,4-dihydroisoquinolin-2(1 H)-yl)-4-methylpyrimidin-5-yl-carboxylic acid, 4-methyl-2-((3-methylphenyl)amino)pyrimidin-5-yl-carboxylic acid aqueous suspensions are used for a single treatment of the soil at the time of sowing different seeds (or fungi), and are compared with aqueous solutions of the corresponding salts of the acids proposed in the invention. The application rate of the preparations is 0.0002 g / m 2 (2 g / ha). In the control experiment, the crops were irrigated with water. The results of the influence of the preparations are shown in Tables 1 to 13. DETAILED DESCRIPTION

[0046] To study the effect of N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acids and their salts on seed germination, seeds were soaked in a 0.0015% by weight solution for 2 to 18 hours depending on the crop being treated. To control germination, seeds soaked in tap water were used, and in the case of tomatoes, the commercially available growth regulator Epin-extra (produced by the Russian NNPP "NEST M", hereinafter referred to as Epin) was also used, the concentration of which was 0.05% according to the instructions. Three replicates were performed for each test substance and control, each time using 200 seeds or the amount required for field trials.

[0047] Seeds were germinated at 23°C. Seedlings were planted on the 15th day after the start of germination. The germination rate was calculated as the percentage of the ratio of the number of seedlings to the number of seeds used.

[0048] Subsequent experiments were performed according to the method of B.A. Dospekhov ("Methods of field experiment (with the basics of statistical processing of research results)", fifth edition (supplemented and revised), - textbook for higher education / B.A. Dospekhov. - Moscow: Agropromizdat, 1985. - 351 p.) using a split-plot design and setting three replicates or in field trials on multiple plots.

[0049] Data processing and grouping were performed according to the method described in A.P. Kulaichev ("Methods and tools of complex data analysis" / A.P. Kulaichev. - M.: FORUM: INFA-M, 2006. - 512 c.). Statistical processing of results was performed using the package "Stadia".

[0050] Comparison of the average values was performed using the Student's t criterion. Seed germination rate in the control and experimental variants was compared by frequency consistency using the Z statistic. The increase in germination rate, yield, shoot and root height was calculated in percent relative to the control.

[0051] The results of the effect of seed treatment with new compounds of the series of pyrimidine carboxylic acids on seed germination rate, seedling height and yield for different plants and champignon, as well as the results of comparison with the control, are shown in Tables 1 to 13.

[0052] According to Table 1 below, in the case of experiments on tomatoes, Epin was also used as a control. The germination rate of tomato seeds increased insignificantly (2.7%) under the influence of the commercial Epin preparation. The germination rate of seeds treated with 2-amino-4-methylpyrimidin-5-yl-carboxylic acid increased by 3.6 to 4.4%, and the germination rate of seeds treated with a salt of 2-amino-4-methylpyrimidin-5-yl-carboxylic acid increased by 5.6 to 6.9%.

[0053] The height of common tomato seedlings treated with 2-amino-4-methylpyrimidin-5-yl-carboxylic acid at the time of sowing increased by 37.5 to 44.3% relative to the control. In the case of using a salt of 2-amino-4-methylpyrimidin-5-yl-carboxylic acid, the increase in this index was 56.8 to 61.4%. The seedling height increased less significantly (6.8%) in the case of using a commercial Epin preparation relative to the control.

[0054] The maximum increase in yield was observed in experiments using a salt of 2-amino-4-methylpyrimidin-5-yl-carboxylic acid according to the invention, and the increase relative to the control was 44 to 50%.

[0055] The effect of the aforementioned 2-amino-4-methylpyrimidin-5-yl-carboxylic acid and Epin resulted in an increase in yield of 32.1 to 36.9% and 10.7%, respectively.

[0056] Similar correlations were observed for the average fruit weight values. Thus, the average weight of tomato fruits increased by 3.5% under the influence of Epin, the application of 2-amino-4-methylpyrimidin-5-yl-carboxylic acid increased this index by 5.1 to 5.6%, and the increase in the average fruit weight was 9.5 to 12.2% when treated with a salt of 2-amino-4-methylpyrimidin-5-yl-carboxylic acid.

[0057] As shown in Tables 1 to 13, the yield of various crops increased in the range of 7.8 to 61.8% when using 2-amino-4-methylpyrimidin-5-yl-carboxylic acid (this depends on the crop being treated), and the yield of each crop increased significantly higher than the corresponding acid treatment and in the range of 25.1 to 101.8% when using a salt according to the invention (this depends on the crop being treated).

[0058] The increase in seed germination rate under the influence of 2-amino-4-methylpyrimidin-5-yl-carboxylic acid was 0.8 to 14.4%, while for the corresponding salt, the germination rate in each case was higher than the corresponding acid and an increase of 6.6 to 34.6% relative to the control was observed.

[0059] When 2-amino-4-methylpyrimidin-5-yl-carboxylic acid is used, the length of the seedlings is increased by 9.8 to 94.7 %, and when a salt thereof is used, the length of the seedlings is increased by 21.6 to 121.1 %.

[0060] General procedure for the preparation of compounds of formula (I)

[0061] The N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acid or the corresponding ester thereof is interacted with the following substances in equimolar ratio in aqueous medium alone or in aqueous medium mixed with organic solvents: Na, K, Li, Mg, Ca, NH3suitable hydroxide solutions; or carbonates and bicarbonates of Na, K, Li, Mg, Ca, NH3; or aliphatic and aliphatic-aromatic amines. Preferably, the organic solvent is methanol or ethanol or a combination thereof. The interaction is preferably carried out while heating, then the resulting salt is isolated or not.

[0062] Examples

[0063] Example 1. Preparation of the sodium salt of 2-benzylamino-4-methylpyrimidin-5-yl- carboxylic acid.

[0064] To a mixture of 2.43 g (10 mmol) of 2-benzylamino-4-methylpyrimidin-5-yl-carboxylic acid ethyl ester, 10 mL of ethanol and 10 mL of water, 0.41 g (10.25 mmol) of sodium hydroxide in 10 mL of water is added. The reaction mixture is boiled under reflux until a clear solution is formed. The volatile components are evaporated in a rotary evaporator. The sodium salt of 2-benzylamino-4-methylpyrimidin-5-yl-carboxylic acid is finally obtained in quantitative yield.

[0065] Example 2. Preparation of the potassium salt of 4-methyl-2-(piperidin-1-yl)pyrimidin-5-yl- carboxylic acid.

[0066] To a mixture of 2.21 g (10 mmol) of 4-methyl-2-(piperidin-1-yl)pyrimidin-5-yl-carboxylic acid, 5 mL of methanol and 15 mL of water, 1.02 g (10.20 mmol) of potassium bicarbonate in 10 mL of water is added. The reaction mixture is stirred and heated (temperature between 50 °C and 60 °C) until a clear solution is formed. The volatile components are evaporated in a rotary evaporator. The potassium salt of 4-methyl-2-(piperidin-1-yl)pyrimidin-5-yl-carboxylic acid is finally obtained in quantitative yield.

[0067] Example 3. Preparation of the ethanolamine salt of 4-methyl-2-(morpholin-4-yl)pyrimidin-5- yl-carboxylic acid.

[0068] To a mixture of 2.23 g (10 mmol) of 4-methyl-2-(morpholin-4-yl)pyrimidin-5-yl- carboxylic acid, 10 mL of ethanol and 10 mL of water, 0.62 g (10.15 mmol) of monoethanolamine was added. The reaction mixture was stirred and heated (temperature between 50°C and 60°C) until a clear solution was formed. The solution was then cooled to 0°C and kept at this temperature. The precipitate was quickly filtered and washed with cold isopropanol. The monoethanolamine salt of 4-methyl-2-(morpholin-4-yl)pyrimidin-5-yl-carboxylic acid was obtained in 95% yield.

[0069] The physico-chemical properties of the preferred compounds obtained according to the above method are given below.

[0070] The1H and13C NMR spectra were recorded on a Varian Inova 400 instrument. 1 H and 13 C NMR spectra (400 MHz and 100 MHz respectively).

[0071] Example 1. 2-benzylamino-4-methylpyrimidin-5-yl-carboxylic acid sodium salt.

[0072] [Chemical Formula]

[0073]

[0074] Melting temperature > 300°C. 1 H NMR spectrum, DMSO-d6, δ, ppm; J, Hz: 2.58 (3H, s, CH3); 4.52 (2H, d, CH2N, J = 12.0); 7.16-7.28 (1H, m, CH-phenyl); 7.29-7.32 (4H, m, 4CH-phenyl); 7.63 (1H, d, NH, J = 12.0); 8.65 (1H, s, CH-pyrimidine). 13 C NMR spectrum, δ, ppm: 40.5, 44.4, 120.7, 125.8, 127.5, 128.5, 135.6, 141.2, 155.0, 161.7, 170.1.

[0075] Example 2. 2-benzylamino-4-methylpyrimidin-5-yl-carboxylic acid monoethanolamine salt.

[0076] [Chemical Formula]

[0077]

[0078] Amorphous substance. 1H NMR Spectrum, DMSO-d6, δ in ppm; J in Hz: 1.43-1.51 (4H, m, 4CH-piperidine); 1.57-1.62 (2H, m, 2CH-piperidine); 2.56 (3H, s, CH3); 3.70-3.73 (4H, m, 2CH2-piperidine); 8.60 (1H, s, CH-pyrimidine).

[0079] 4.52 (2H, d, CH2N, J = 12.0); 5.19 (1H, br. s, NH3); 7.18-7.22 (1H, m, CH-phenyl); 7.25-7.30 (4H, m, 4CH-phenyl); 7.71 (1H, br. s, NH); 8.58 (1H, s, CH-pyrimidine).

[0080] 4.52 (2H, d, CH2N, J = 12.0); 5.19 (1H, br. s, NH3); 7.18-7.22 (1H, m, CH-phenyl); 7.25-7.30 (4H, m, 4CH-phenyl); 7.71 (1H, br. s, NH); 8.58 (1H, s, CH-pyrimidine). 13 CNMR Spectrum, δ in ppm: 40.5, 42.5, 44.3, 59.5, 119.9, 126.9, 127.5, 128.6, 140.9, 158.7, 161.9, 165.5, 170.1.

[0081] Example 3. 4-Methyl-2-(piperidin-l-yl)pyrimidin-5-yl-carboxylic acid potassium salt.

[0082] [Chemical Formula]

[0083]

[0084] Melting temperature > 300 °C. 1 H NMR Spectrum, DMSO-d6, δ in ppm; J in Hz: 1.43-1.51 (4H, m, 4CH-piperidine); 1.57-1.62 (2H, m, 2CH-piperidine); 2.56 (3H, s, CH3); 3.70-3.73 (4H, m, 2CH2-piperidine); 8.60 (1H, s, CH-pyrimidine). 13 CNMR Spectrum, δ in ppm: 24.8, 24.9, 25.8, 40.5, 40.6, 121.9, 160.3, 160.5, 167.0, 169.1.

[0085] Example 4. 2-((4-Methoxyphenyl)amino)-4-methylpyrimidin-5-yl-carboxylic acid propanolamine salt.

[0086] [Chemical Formula]

[0087]

[0088] Amorphous substance. 1H NMR spectrum, DMSO-d6, δ, ppm; J, Hz: 1.71-1.75 (2H, m, CH2CH2CH2); 2.59 (3H, s, CH3); 2.80-2.84 (2H, m, CH2NH3); 3.48-3.53 (2H, m, CH2OH); 3.73 (3H, s, CH3O); 5.70 (4H, br. s, NH3+ OH); 6.83-6.86 (2H, m, 2CH-aryl); 7.69-7.72 (2H, m, 2CH-aryl); 8.70 (1H, s, CH-pyrimidine); 9.41 (1H, s, NH).

[0089] 13 C NMR spectrum, δ, ppm: 24.5, 31.3, 37.2, 55.8, 58.6, 114.6, 120.9, 134.1, 154.4, 159.3, 160.3, 162.7, 167.1; 169.6.

[0090] Example 5. 4-Methyl-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl-carboxylic acid lithium salt.

[0091] [Chemical Formula]

[0092]

[0093] Melting temperature > 300 °C. 1 H NMR spectrum, DMSO-d6, δ, ppm; J, Hz: 2.36 (4H, br. s, 2CH2-piperazine); 2.44 (3H, s, NCH3); 2.57 (3H, s, CH3); 3.69-3.72 (4H, m, 2CH2-piperazine); 8.62 (1H, s, CH-pyrimidine). 13 C NMR spectrum, δ, ppm: 25.7, 43.4, 51.8, 54.7, 122.1, 160.3, 162.4, 166.8, 169.9.

[0094] Example 6. 4-Methyl-2-((2,4-difluorophenyl)amino)pyrimidin-5-yl-carboxylic acid potassium salt.

[0095] [Chemical Formula]

[0096]

[0097] Melting temperature > 300 °C. 1H NMR spectrum, D20, δ, ppm; J, Hz: 2.33 (3H, s, CH3); 6.77-6.90 (2H, m, CH-aryl); 7.33-7.39 (1H, m, CH-aryl); 8.22 (1H, s, CH-pyrimidine). 13 C NMR spectrum, D20, δ, ppm; J, Hz: 22.5, 104.2 (br. s, J = 25.7), 111.1, 111.3, 122.6, 127.1, 127.2, 158.3, 158.5 and 160.9 (CF), 159.3 and 161.0 (CF), 168.4, 173.5.

[0098] Example 7. 4-Methyl-2-((4-methylphenyl)amino)pyrimidin-5-yl-carboxylic acid sodium salt.

[0099] [Chemical Formula]

[0100]

[0101] Melting temperature > 300 °C. 1 H NMR spectrum, D20, δ, ppm; J, Hz: 2.09 (3H, s, CH3); 2.31 (3H, s, CH3); 6.99 (2H, d, CH-aryl); 7.11 (2H, d, CH-aryl); 8.22 (1H, s, CH-pyrimidine).13C NMR spectrum, D20, δ, ppm: 19.9, 22.7, 121.6, 129.3, 133.9, 135.4, 158.6, 158.9, 168.4, 173.5.

[0102] Example 8. 4-Methyl-2-(phenethylamino)pyrimidin-5-yl-carboxylic acid lithium salt.

[0103] [Chemical Formula]

[0104]

[0105] Melting temperature > 300 °C. 1 H NMR spectrum, D20, δ, ppm; J, Hz: 2.24 (3H, s, CH3); 2.67 (2H, t, CH2, J = 6.6); 3.38 (2H, t, CH2, J = 6.6); 6.86-6.91 (3H, m, CH-aryl);

[0106] 6.94-6.99 (2H, m, CH-aryl); 8.14 (1H, s, CH-pyrimidine). 13C NMR spectrum, D20, δ, ppm: 22.6, 34.6, 42.1, 119.9, 126.2, 128.3, 128.7, 139.2, 158.7, 160.5, 168.5, 173.6.

[0107] Example 9. 4-Methyl-2-(morpholin-4-yl)pyrimidin-5-yl-carboxylic acid ethanolamine salt.

[0108] [Chemical Formula]

[0109]

[0110] The melting temperature is 218 to 221 °C. 1 H NMR spectrum, D20, δ, ppm; J, Hz: 2.33 (3H, s, CH3); 2.89-2.96 (2H, m, CH2N); 3.51-3.67 (10H, m, CH20 + 4CH2-morpholine);

[0111] 7.01-7.17 (2H, m, CH-aryl); 8.26 (1H, s, CH-pyrimidine). 13 C NMR spectrum, D20, δ, ppm: 22.9, 41.2, 44.2, 57.5, 66.2 120.3, 158.4, 160.3, 168.3, 173.9.

[0112] Example 10. 4-Methyl-2-(piperidin-1-yl)pyrimidin-5-yl-carboxylic acid phenethylamine salt.

[0113] [Chemical Formula]

[0114]

[0115] The melting temperature is 139 to 143 °C. 1 H NMR spectrum, D 2 O, δ, ppm; J, Hz: 1.67-1.78 (4H, m, 2 CH2-pyrrolidine); 2.29 (3H, s, CH3); 2.59-2.63 (2H, m, CH2); 2.99-3.08 (2H, ​ m, CH2); 3.12-3.25 (4H, m, CH2NCH2-pyrrolidine); 7.01-7.10 (3H, m, CH-aryl); 7.11-7.17 (2H, m, CH-aryl); 8.17 (1H, s, CH-pyrimidine). 13 C NMR spectrum, D20, δ, ppm: 22.7, 24.6, 32.6, 40.4, 46.8, 118.0, 126.9; 128.4; 128.7; 136.2; 157.9, 158.5; 168.4, 173.6.

[0116] Example 11. 2-(3,4-dihydroisoquinolin-2(lH)-yl)-4-methylpyrimidin-5-yl- carboxylic acid sodium salt.

[0117] [Chemical Formula]

[0118]

[0119] Melting temperature > 300 °C. 1 H NMR spectrum, D20, δ, ppm; J, Hz: 2.32 (3H, s, CH3); 2.58 (2H, t, CH2, J = 5.8); 3.56 (2H, t, CH2, J = 5.8); 4.42 (2H, s, CH2); 6.87-6.98 (4H, m, CH- benzyl); 8.20 (1H, s, CH-pyrimidine). 13 C NMR spectrum, D20, δ, ppm: 23.3, 27.9, 41.8, 45.9, 119.1, 126.1, 126.4, 128.0, 133.0, 134.8, 158.4, 158.6, 159.5, 168.5, 173.7.

[0120] Example 12. 4-methyl-2-((3-methylphenyl)amino)pyrimidin-5-yl-carboxylic acid triethanolamine salt.

[0121] [Chemical Formula]

[0122]

[0123] Amorphous substance. 1 H NMR spectrum, D20, δ, ppm; J, Hz: 2.12 (3H, s, CH3); 2.33 (3H, s, CH3); 2.71-2.76 (6H, m, N(CH2)3); 3.43-3.66 (6H, m, 3CH2OH); 7.03-7.12 (3H, m, CH-aryl); 8.24 (1H, s, CH-pyrimidine). 13 C NMR spectrum, D20, δ, ppm: 20.5, 22.6, 55.5, 58.0, 118.4, 121.9, 122.2, 124.6, 128.9, 138.2, 139.2, 158.3, 158.8, 168.3, 173.5.

[0124] Example 13. 2-benzylamino-4-methylpyrimidin-5-yl-carboxylic acid triethanolamine salt.

[0125] [Chemical Formula]

[0126]

[0127] Amorphous substance. 1 H NMR spectrum, D20, δ, ppm; J, Hz: 2.30 (3H, s, CH3); 2.88-2.93 (6H, m, N(CH2)3); 3.59-3.63 (6H, m, 3CH2OH); 4.36 (2H, s, CH2); 7.14-7.18 (5H, m, CH-aryl); 8.18 (1H, s, CH-pyrimidine). 13 C NMR spectrum, D20, δ, ppm: 22.6, 44.3, 55.4, 56.8, 120.7, 126.9, 127.1, 128.6, 138.8, 158.7, 160.7, 168.6, 173.8.

[0128] The use of the proposed water-soluble plant growth stimulator will allow to simplify the use of N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acid derivatives and increase their efficiency to meet the needs of crop production.

[0129] The seed germination rate, seedling height and root height, yield and average fruit weight of different plant species and mushrooms (Agaricus bisporus) after treatment with salts of 2-amino-4-methylpyrimidin-5-yl-carboxylic acid, as well as comparative data obtained by treatment with the corresponding acid, are given in Tables 1 to 13.

[0130] Seed germination rate, seedling height, yield and average fruit weight of the tomato "Novichok" after treatment with the known 2-amino-4-methylpyrimidin-5-yl-carboxylic acid compared to the corresponding novel salt according to the application.

[0131] [Table 1]

[0132]

[0133]

[0134] Seed germination rate, seedling height, yield and average fruit weight of the common eggplant (Solanum melongena L.) variety "Lilac" after treatment with the known 2-amino-4-methylpyrimidin-5-yl-carboxylic acid compared to the corresponding novel salt according to the application.

[0135] [Table 2]

[0136]

[0137]

[0138] Seed germination rate and seedling height of the perennial Rhododendron Ledebourii Pojarc. after treatment with the known 2-amino-4-methylpyrimidin-5-yl-carbonsäure compared to the corresponding novel salt according to the application.

[0139] [Table 3]

[0140]

[0141]

[0142] Seed germination rate and seedling height of the growth abnormal Tagetes patula L. variety "Red Cherry" after treatment with the known 2-amino-4-methylpyrimidin-5-yl-carbonsäure compared to the corresponding novel salt according to the application.

[0143] [Table 4]

[0144]

[0145] Germination rate, seedling height and yield of the winter wheat (Triticum aestivum L.) variety "Alekseich" after treatment with the known 2-amino-4-methylpyrimidin-5-yl-carbonsäure compared to the corresponding novel salt according to the application.

[0146] [Table 5]

[0147]

[0148] Yield and average fruit weight of the potato (Solanum tuberosum) variety "Zekura" after treatment with the known 2-amino-4-methylpyrimidin-5-yl-carbonsäure compared to the corresponding novel salt according to the application.

[0149] [Table 6]

[0150]

[0151]

[0152] Yield of the sunflower (Helianthus L.) variety "Chakinsky 100" after treatment with the known 2-amino-4-methylpyrimidin-5-yl-carbonsäure compared to the corresponding novel salt according to the application.

[0153] [Table 7]

[0154]

[0155]

[0156] Yield of the corn hybrid (Zea mays L.) variety "Mixi" after treatment with the known 2-amino-4-methylpyrimidin-5-yl-carbonsäure compared to the corresponding novel salt according to the application.

[0157] [Table 8]

[0158]

[0159] Yield and average fruit weight of the pumpkin (Cucurbita pepo subsp. pepo) variety "Tintoretto" after treatment with the known 2-amino-4-methylpyrimidin-5-yl-carbonsäure compared to the corresponding novel salt according to the application.

[0160] [Table 9]

[0161]

[0162] Germination rate and shoot length of the pea (Pisum L.) variety "Orlus" after treatment with the known 2-amino-4-methylpyrimidin-5-yl-carbonsäure compared to the corresponding novel salt according to the application.

[0163] [Table 10]

[0164]

[0165]

[0166] Yield and weight of the curd of the white cabbage (Brassica oleracea L.) variety "Podarok" ("Gift") after treatment with the known 2-amino-4-methylpyrimidin-5-yl-carbonsäure compared to the corresponding novel salt according to the application.

[0167] [Table 11]

[0168]

[0169]

[0170] Yield and fruit weight of the sweet pepper (Capsicum annuum L.) variety "Flamingo" after treatment with the known 2-amino-4-methylpyrimidin-5-yl-carbonsäure compared to the corresponding novel salt according to the application.

[0171] [Table 12]

[0172]

[0173]

[0174] Yield of mushrooms (Bisporus white) after treatment with known 2-amino-4- methylpyrimidin-5-yl-carboxylic acid compared to the corresponding novel salt according to the application.

[0175] [Table 13].

[0176]

[0177] a - significant difference from the control (P < 0.05);

[0178] b - significant difference from the control (P < 0.01);

[0179] c - significant difference from the control (P < 0.001).

Claims

1. A compound which is a salt of N-substituted 2-amino-4-methylpyrimidin-5-yl- carboxylic acid according to general formula (I) ###0001### (I) the heterocyclyl and heteroaryl groups contain 1 to 3 heteroatoms selected from N, O and S, R = hydrogen, R1 = C1-C6 alkyl; R2 = hydrogen, C1-C4 alkyl; R3 = hydrogen, C1-C4 alkyl; R4 = hydrogen, C1-C4 alkyl; R5 = hydrogen, C1-C4 alkyl; R6 = hydrogen, C1-C4 alkyl; R7 = hydrogen, C1-C4 alkyl; R8 = hydrogen, C1-C4 alkyl; R9 = hydrogen, C1-C4 alkyl; R10 = hydrogen, C1-C4 alkyl; R11 = hydrogen, C1-C4 alkyl; R12 = hydrogen, C1-C4 alkyl; R13 = hydrogen, C1-C4 alkyl; R14 = hydrogen, C1-C4 alkyl; R15 = hydrogen, C1-C4 alkyl; R16 = hydrogen, C1-C4 alkyl; R17 = hydrogen, C1-C4 alkyl; R18 = hydrogen, C1-C4 alkyl; R19 = hydrogen, C1-C4 alkyl; R20 = hydrogen, C1-C4 alkyl; R21 = hydrogen, C1-C4 alkyl; R22 = hydrogen, C1-C4 alkyl; R23 = hydrogen, C1-C4 alkyl; R24 = hydrogen, C1-C4 alkyl; R25 = hydrogen, C1-C4 alkyl; R26 = hydrogen, C1-C4 alkyl; R27 = hydrogen, C1-C4 alkyl; R28 = hydrogen, C1-C4 alkyl; R29 = hydrogen, C1-C4 alkyl; R30 = hydrogen, C1-C4 alkyl; R31 = hydrogen, C1-C4 alkyl; R32 = hydrogen, C1-C4 alkyl; R33 = hydrogen, C1-C4 alkyl; R34 = hydrogen, C1-C4 alkyl; R35 = hydrogen, C1-C4 alkyl; R36 = hydrogen, C1-C4 alkyl; R37 = hydrogen, C1-C4 alkyl; R38 = hydrogen, C1-C4 alkyl; R39 = hydrogen, C1-C4 alkyl; R40 = hydrogen, C1-C4 alkyl; R41 = hydrogen, C1-C4 alkyl; R42 = hydrogen, C1-C4 alkyl; R43 = hydrogen, C1-C4 alkyl; R44 = hydrogen, C1-C4 alkyl; R45 = hydrogen, C1-C4 alkyl; R46 = hydrogen, C1-C4 alkyl; R47 = hydrogen, C1-C4 alkyl; R48 = hydrogen, C1-C4 alkyl; R49 = hydrogen, C1-C4 alkyl; R50 = hydrogen, C1-C4 alkyl; R51 = hydrogen, C1-C4 alkyl; R52 = hydrogen, C1-C4 alkyl; R53 = hydrogen, C1-C4 alkyl; R54 = hydrogen, C1-C4 alkyl; R55 = hydrogen, C1-C4 alkyl; R56 = hydrogen, C1-C4 alkyl; R57 = hydrogen, C1-C4 alkyl; R58 = hydrogen, C1-C4 alkyl; R59 = hydrogen, C1-C4 alkyl; R60 = hydrogen, C1-C4 alkyl; R61 = hydrogen, C1-C4 alkyl; R62 = hydrogen, C1-C4 alkyl; R63 = hydrogen, C1-C4 alkyl; R64 = hydrogen, C1-C4 alkyl; R65 = hydrogen, C1-C4 alkyl; R66 = hydrogen, C1-C4 alkyl; R67 = hydrogen, C1-C4 alkyl; R68 = hydrogen, C1-C4 alkyl; R69 = hydrogen, C1-C4 alkyl; R70 = hydrogen, C1-C4 alkyl; R71 = hydrogen, C1-C4 alkyl; R72 = hydrogen, C1-C4 alkyl; R73 = hydrogen, C1-C4 alkyl; R74 = hydrogen, C1-C4 alkyl; R75 = hydrogen, C1-C4 alkyl; R76 = hydrogen, C1-C4 alkyl; R77 = hydrogen, C1-C4 alkyl; R78 = hydrogen, C1-C4 alkyl; R79 = hydrogen, C1-C4 alkyl; R80 = hydrogen, C1-C4 alkyl; R81 = hydrogen, C1-C4 alkyl; R82 = hydrogen, C1-C4 alkyl; R83 = hydrogen, C1-C4 alkyl; R84 = hydrogen, C1-C4 alkyl; R85 = hydrogen, C1-C4 alkyl; R86 = hydrogen, C1-C4 alkyl; R87 = hydrogen, C1-C4 alkyl; R88 = hydrogen, C1-C4 alkyl; R89 = hydrogen, C1-C4 alkyl; R90 = hydrogen, C1-C4 alkyl; R91 = hydrogen, C1-C4 alkyl; R92 = hydrogen, C1-C4 alkyl; R93 = hydrogen, C1-C4 alkyl; R94 = hydrogen, C1-C4 alkyl; R95 = hydrogen, C1-C4 alkyl; R96 = hydrogen, C1-C4 alkyl; R97 = hydrogen, C1-C4 alkyl; R98 = hydrogen, C1-C4 alkyl; R99 = hydrogen, C1-C4 alkyl; R100 = hydrogen, C1-C4 alkyl; R101 = hydrogen, C1-C4 alkyl; R102 = hydrogen, C1-C4 alkyl; R103 = hydrogen, C1-C4 alkyl; R104 = hydrogen, C1-C4 alkyl; R105 = hydrogen, C1-C4 alkyl; R106 = hydrogen, C1-C4 alkyl; R107 = hydrogen, C1-C4 alkyl; R108 = hydrogen, C1-C4 alkyl; R109 = hydrogen, C1-C4 alkyl; R110 = hydrogen, C1-C4 alkyl; R111 = hydrogen, C1-C4 alkyl; R112 = hydrogen, C1-C4 alkyl; R113 = hydrogen, C1-C4 alkyl; R114 = hydrogen, C1-C4 alkyl; R115 = hydrogen, C1-C4 alkyl; R116 = hydrogen, C1-C4 alkyl; R117 = hydrogen, C1-C4 alkyl; R118 = hydrogen, C1-C4 alkyl; R119 = hydrogen, C1-C4 alkyl; R120 = hydrogen, C1-C4 alkyl; R121 = hydrogen, C1-C4 alkyl; R122 = hydrogen, C1-C4 alkyl; R123 = hydrogen, C1-C4 alkyl; R124 = hydrogen, C1-C4 alkyl; R125 = hydrogen, C1-C4 alkyl; R126 = hydrogen, C1-C4 alkyl; R127 = hydrogen, C1-C4 alkyl; R128 = hydrogen, C1-C4 alkyl; R129 = hydrogen, C1-C4 alkyl; R130 = hydrogen, C1-C4 alkyl; R131 = hydrogen, C1-C4 alkyl; R132 = hydrogen, C1-C4 alkyl; R133 = hydrogen, C1-C4 alkyl; R134 = hydrogen, C1-C4 alkyl; R135 = hydrogen, C1-C4 alkyl; R136 = hydrogen, C1-C4 alkyl; R137 = hydrogen, C1-C4 alkyl; R138 = hydrogen, C1-C4 alkyl; R139 = hydrogen, C1-C4 alkyl; R140 = hydrogen, C1-C4 alkyl; R141 = hydrogen, C1-C4 alkyl; R142 = hydrogen, C1-C4 alkyl; R143 = hydrogen, C1-C4 alkyl; R144 = hydrogen, C1-C4 alkyl; R145 = hydrogen, C1-C4 alkyl; R146 = hydrogen, C1-C4 alkyl; R147 = hydrogen, C1-C4 alkyl; R148 = hydrogen, C1-C4 alkyl; R149 = hydrogen, C1-C4 alkyl; R150 = hydrogen, C1-C4 alkyl; R151 = hydrogen, C1-C4 alkyl; R152 = hydrogen, C1-C4 alkyl; R153 = hydrogen, C1-C4 alkyl; R154 = hydrogen, C1-C4 alkyl; R155 = hydrogen, C1-C4 alkyl; R156 = hydrogen, C1-C4 alkyl; R157 = hydrogen, C1-C4 alkyl; R158 = hydrogen, C1-C4 alkyl; R159 = hydrogen, C1-C4 alkyl; R160 = hydrogen, C1-C4 alkyl; R161 = hydrogen, C1-C4 alkyl; R162 = hydrogen, C1-C4 alkyl; R163 = hydrogen, C1-C4 alkyl; R164 = hydrogen, C1-C4 alkyl; R wherein X + is selected from the cations Na + , K + , Li + , ½ Mg 2+ , ½ Ca 2+ , NH4 + , H3N + CH2CH2OH, H3N + CH2CH2CH2OH, HN + (CH2CH2OH)3, H3N + CH2CH2C6H5, or ANH3 + , A2NH2 + , A3NH + , A represents C1-C 12 alkyl, C6-C 12 aryl, C5-C 12 heterocyclyl, C5-C 12 heteroaryl, characterized in that, ​ ​ ​ ​ ​ ​ Alternatively, R+R1 together with a nitrogen atom indicates that it is optionally surrounded by one or more atoms selected from halogens, -(C1-C4)alkyl groups, and C6-C4alkyl groups. 12 Aryl substituents include pyrrolidine, quinoline, isoquinoline, piperidine, morpholine, and piperazine.

2. The compound of claim 1, wherein ​ 3. The compound of claim 1, wherein ​ 4. The compound of claim 1, wherein The cation is Na + , K + , Li + , ½ Mg 2+ , ½ Ca 2+ , NH4 + , H3N + CH2CH2OH, H3N + CH2CH2CH2OH, H3N + CH2CH2C6H5, HN + (CH2CH2OH)3.

5. The compound of claim 1, wherein ​ 6. The compound of claim 5, wherein ​ 7. The compound according to claim 1 selected from the group consisting of sodium salt of 2-benzylamino-4-methylpyrimidin-5-yl-carboxylic acid, potassium salt of 4-methyl-2-(piperidin-1-yl)pyrimidin-5-yl-carboxylic acid, ethanolamine salt of 4-methyl-2-(morpholin-4-yl)pyrimidin-5-yl-carboxylic acid, sodium salt of 2-benzylamino-4-methylpyrimidin-5-yl-carboxylic acid, ethanolamine salt of 2-benzylamino-4-methylpyrimidin-5-yl-carboxylic acid, potassium salt of 4-methyl-2-(piperidin-1-yl)pyrimidin-5-yl-carboxylic acid, propanolamine salt of 2-((4-methoxyphenyl)amino)-4-methylpyrimidin-5-yl-carboxylic acid, lithium salt of 4-methyl-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl-carboxylic acid, potassium salt of 4-methyl-2-((2,4-difluorophenyl)amino)pyrimidin-5-yl-carboxylic acid, sodium salt of 4-methyl-2-((4-methylphenyl)amino)pyrimidin-5-yl-carboxylic acid, lithium salt of 4-methyl-2-(phenethylamino)pyrimidin-5-yl-carboxylic acid, ethanolamine salt of 4-methyl-2-(morpholin-4-yl)pyrimidin-5-yl-carboxylic acid, phenethylamine salt of 4-methyl-2-(piperidin-1-yl)pyrimidin-5-yl-carboxylic acid, sodium salt of 2-(3,4-dihydroisoquinolin-2(1 H)-yl)-4-methylpyrimidin-5-yl-carboxylic acid, triethanolamine salt of 4-methyl-2-((3-methylphenyl)amino)pyrimidin-5-yl-carboxylic acid, and triethanolamine salt of 2-benzylamino-4-methylpyrimidin-5-yl-carboxylic acid.

8. A method of preparing a salt according to any one of claims 1 to 7, comprising contacting N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acid or a corresponding ester thereof with a solution of Na, K, Li, Mg, Ca, NH3 corresponding hydroxide in water and / or an organic solvent; and isolating the resulting salt.

9. The method of claim 8, wherein, The contacting is performed in water and / or an organic solvent selected from ethanol, methanol or a combination thereof.

10. The method of claim 8, wherein, The contacting is performed while heating.

11. A method of preparing a salt according to any one of claims 1 to 7, comprising contacting N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acid or a corresponding ester thereof with a carbonate or bicarbonate salt of Na, K, Li, Mg, Ca, NH3 in water; and isolating the resulting salt.

12. A method of preparing a salt according to any one of claims 1 to 7, comprising contacting N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acid or a corresponding ester thereof with an aliphatic amine and an aromatic amine in water and / or an organic solvent, and isolating the resulting salt.

13. The method of claim 12, wherein, The contacting is performed in water and / or an organic solvent selected from ethanol, methanol or a combination thereof.

14. The method of claim 13, wherein, The contacting is performed while heating.

15. Use of a compound according to any one of claims 1 to 7 for stimulating the growth of plants or fungi.

16. Use according to claim 15, characterized in that, The plant or fungal growth stimulation is selected from the group consisting of stimulating germination vigour, stimulating seed germination rate, stimulating seedling bio- metrics, stimulating root formation and stimulating yield in a variety of crops.

17. Use according to claim 15, characterized in that, The plant growth stimulation is performed at seed treatment before sowing and at any stage of plant development.

18. Use according to claim 15, characterized in that, The plant or fungus is selected from the group consisting of tomato, eggplant, azalea, marigold, wheat, potato, sunflower, maize, zucchini, pea, cabbage, sweet pepper and mushroom.

Images