N-substituted 2-amino-4-methylpyrimidine-5-yl-carboxylic acid salts as plant and fungal growth stimulators

Description

1 / 31 “SALTS OF 2-AMINO-4-METHYLPYRIMIDINE-5-YL-CARBOXYLIC ACIDS SUBSTITUTED AS PLANT GROWTH STIMULATORS AND FUNGI Technical Field

[001] The invention relates to new compounds for use in agriculture, in particular for regulating plant growth and development, and can be used to stimulate action in plants and fungi.

[002] In particular, these new compounds can be used to optimize plant growth parameters, such as germ inactive energy, seed germination, seedling biometrics, root formation and yield for a wide range of crops. Previous Technique

[003] Plant cultivation faces many problems associated with extreme temperature fluctuations, lack of moisture, and adverse climatic conditions in the region. In this sense, new means of stimulating plant growth and development are needed, which can be achieved through the use of synthesized chemical compounds. (Vasin, AV Use of growth stimulators in corn and barley cultivation / AV Vasin, AV Darmin, VV Brezhnev / / Fodder production / AV Vasin, AV Darmin, VV Brezhnev. Brezhnev / / Kormoproizvodstvo (Feed production). 2009. - N2. - P. 17-18; Vasin, VG Efficiency of the growth stimulator application at corn cultivation for grain / VG Vasin, AV Darmin, AV Vasin / / Izvestiya Samarskoy gosudarstvennoy selskokhozyaistvennoy akademii (Bulletin of Samara State Agricultural Academy).Ostroshenko / / Vestnik Krasnoyarskogo gosudarstvennogo agrarnogo universiteta (Bulletin of Krasnoyarsk State Agrarian University). - 2011. N5. - P. 12.-15; Shishov, A.D. Determination of growth-stimulating concentrations of. Petição 870250091259, de 06 / 10 / 2025, pág. 6 / 45 2 / 31 new growth regulators and plant stability inducers I A.D. Shishov, G.L. Matevosyan 11 Fundamentalnye issledovaniya (Fundamental Research). -2005. - N°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 I A.A. Sinkov. - Saratov, 2011 - 21 p.; Influence of synthetic growth regulator cytodef and heavy metals on the oxidative status of cucumber plants I D.l. Bashmakov and [others] / / Fiziologiya rasteniy (Plant Physiology). - 2012. - T. 59, N°1. - P. 67-73).

[004] Patent RU 2485083 C1 describes substituted pyrimidine-5-yl-carboxylic acids of general formula 1, with a structure similar to the proposed compounds. [Chemical Formula I] R2 where Ri + R2 = piperidine, pyrrolidine, morpholine, N-Alk(Ar) piperazine, or R1 = Alk, Ar; R2 = Alk, Ar or Ri = H, R2 = H, Alk, Ar, Het; R3 = Alk, in particular methyl, Ar, etc., R4 = H. In particular, compounds are described where Ri + R2 = piperidine or R1 = hydrogen, R2 = phenyl, 2-benzyl, 2-phenylethyl, 4-methylphenyl, benzoxazol-2-yl, benzothiazol-2-yl, 4-methylquinazol-2-yl; R3 is methyl, R4 is hydrogen. The compounds have growth-regulating activity against deviated velvet mite (Tagetes patula L).

[005] Known compounds of formula (1) were produced according to the following scheme: [Chemical formula] Petition 870250091259, dated 06 / 10 / 2025, page 7 / 45 3 / 31

[006] Patent RU 2788114 C1 describes the use of a compound corresponding to the general formula (1) described above, wherein Ri = hydrogen, R2 = benzyl, R3 = methyl, R4 = hydrogen, as growth stimulators for beetroot.

[007] Patent RU 2490893 C1 describes a method for using compounds corresponding to formula (1) described above, wherein Ri = hydrogen, R2 = benzyl or 2-phenylethyl, R3 = methyl, to stimulate the growth of deviated velvets;

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

[009] Patent RU 2656393 C1 describes a method of using compounds of formula (1) described above, wherein Ri = hydrogen, R2 = benzyl or Ri and R2, together with a nitrogen atom, represent piperidine, morpholine, to stimulate the growth of plants of the genus Rhododendron L.

[010] Patent RU 2659828 C1 describes a method of using compounds of formula (1), wherein Ri and R2, together with a nitrogen atom, represent piperidine, morpholine, and R3 represents methyl, as growth regulators of the annual Salvias splendens.

[011] Patent RU 2678119 C1 describes the use of compounds of formula (1), wherein Ri = hydrogen, R2 = benzyl or Ri and R2, together with an atom of Petition 870250091259, dated 06 / 10 / 2025, page 8 / 45 4 / 31 nitrogen, represent piperidine, morpholine, and R3 is methyl, to stimulate the growth of the common tomato (Solarium lycopersicum L).

[012] However, known substituted pyrimidine-5-yl-carboxylic acids do not exhibit sufficiently high rates of seed germination, yield, and plant height, and have a significant disadvantage of very low water solubility, which makes dosing and use of these products difficult.

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

[014] The salts of the present invention do not contain the 4,5-dimethyl-1Hpyrazol-1-yl group at position 2 of the pyrimidine ring and have a different purpose than stimulating plant growth. Summary of the Invention Technical Problem

[015] The objective of the present invention is to improve the physicochemical properties of plant growth stimulators, in particular, to improve solubility and performance in seed germination, plant height, weight gain and yield when treated with the growth stimulator in the treatment before sowing and at any stage of plant development. Solution to the Problem

[016] The above technical problem is solved by using new plant growth stimulators, namely, N-substituted 2-amino-4-methylpyrimidine-5-ylcarboxylic acid salts of general formula (I): Petition 870250091259, dated 06 / 10 / 2025, page 9 / 45 5 / 31 [Chemical Formula] wherein X+ is selected from among the cations Na+, K+, Li+, % Mg2+, % Ca2+, NHA, H3N+CH2CH2OH, H3N+CH2CH2CH2OH, HN+(CH2CH2QH)3, H3N+CH2CH2C6H5, or ANH3+, A2NH2+, A3NH+, A represents C1-C12-alkyl, C1-C12-aryl, C2-C12-heterocyclyl, C2-C12-heteroaryl, wherein heterocyclyl and heteroaryl contain 1 to 3 heteroatoms selected from N, O and S, wherein each A is optionally substituted by one or more groups independently selected from halogen, amino-, thio-,

[017] The term alkyl includes linear, branched or cyclic hydrocarbon structures and combinations thereof, with a chain length of 1 to 12 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms.

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

[019] The term heteroaryl, used 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 a nitrogen atom and, optionally, an additional heteroatom independently selected from oxygen, nitrogen, and sulfur. Petition 870250091259, dated 06 / 10 / 2025, page 10 / 45 6 / 31

[020] Examples of such heteroaryl groups include furanyl, oxazolyl, isoxazolyl, oxadiazolyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, indolyl, isoindolyl, benzofuranyl, isobenzofuranyl, benzothiophenyl, indazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzoisothiazolyl, benzotriazolyl, benzo[2,1,3]oxadiazolyl, benzo[2,1,3,3]thiadiazolyl, benzo[1,2,3,3]thiadiazolyl, quinolinyl, isoquinolinyl, cinolinyl, quinazolinyl, quinoxalinyl and phthalazinil.

[021] In a preferred embodiment, Ri stands for methyl, ethyl, propyl; phenyl, optionally substituted by one or two substituents selected from methyl, ethyl; methoxy, halogen; and phenyl-(C1-C2)alkyl-.

[022] In a preferred embodiment, R+Ri together with a nitrogen atom represent pyrrolidine, hydroquinoline, hydroisoquinoline, piperidine, morpholine, piperazine, optionally substituted by one or two substituents selected from methyl, ethyl, halogen and phenyl.

[023] In a preferred embodiment, the cation is Na+, K+, Li+,1Λ Mg2+,1Λ Ca2+, NH4+, H3N+CH2CH2OH, H3N+CH2CH2CH2OH, H3N+CH2CH2C6H5, HN+(CH2CH2OH)3.

[024] The proposed salts, their preparation and their use to stimulate plant growth were not previously known.

[025] The plants may be common tomato (Solarium lycopersicum L), sugar beet, annual bright sage, drift sage, plant species of the genus Rhododendron L. and others.

[026] N-substituted 2-amino-4-methylpyrimidine-5-yl-carboxylic acid salts of formula (I) are water-soluble substances whose solutions can be used in agriculture for seed treatment before sowing, as well as for subsequent application to the soil at different stages of plant and fungal development, both individually and in combination with other substances in mixed compositions. Petition 870250091259, dated 06 / 10 / 2025, p. 11 / 45 7 / 31

[027] N-substituted 2-amino-4-methylpyrimidine-5-yl-carboxylic acid salts of formula (I) are convenient and effective for use as plant growth stimulators.

[028] As salts of N-substituted 2-amino-4-pyrimidin-5-carboxylic acid of formula (I), in particular, the following can be used: salts of 2-(2phenylethyl)amino-4-methylpyrimidin-5-yl-carboxylic acid, 4-methyl-2-(pyrrolidin-1-yl)pyrimidin5-yl-carboxylic acid, 4-methyl-2-(N-methylpiperazin-1-yl)pyrimidin-5-yl-carboxylic acid, 4methyl-2-((4-methoxyphenyl)amino)pyrimidin-5-yl-carboxylic acid, 2-benzylamino-4methylpyrimidin-5-yl-carboxylic acid, 2-(3,4-dihydroisoquinolin-2(1) H)-yl)-4methylpyrimidine-5-yl-carboxylic acid, 4-methyl-2-((2,4-difluorophenyl)amino)pyrimidine-5-ylcarboxylic acid, 4-methyl-2-((4-methylphenyl)amino)pyrimidine-5-ylcarboxylic acid, 4-methyl-2-(morpholin-4-yl)pyrimidine-5-ylcarboxylic acid, 4-methyl-2-(piperidin-1-yl)pyrimidine-5-ylcarboxylic acid, 4-methyl-2-((3-methylphenyl)amino)pyrimidine-5-ylcarboxylic acid and others. Effects of the Invention

[029] In the study, the effect of N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acid salts and the corresponding N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acid on morphometric parameters, such as seed germination, yield and plant height, and roots, was comparatively evaluated.

[030] The following plants were selected for the research: common tomato of the Novichok variety (Solarium lycopersicum L.). Seeds from the Aelita company (Moscow) were used as material; common eggplant of the Lilac variety (Solanum melongena L.); perennial rhododendron Ledebourg (Rhododendron Ledebourii Pojarc.); stray velvet (Tagetes patula L.), Red Cherry variety; winter wheat of the Alekseich variety (Triticum aestivum L.); potato of the Zekura variety (Solanum tuberosum); sunflower variety Chakinsky 100 (Helianthus L.); corn hybrid “Mixi” (Zea mays L.); zucchini of the variety of Petition 870250091259, dated 06 / 10 / 2025, p. 12 / 45 8 / 31 Tintoretto (Cucurbita pepo subsp. pepo); peas of the Orlus variety (Pisum L.); white cabbage of the Podarok variety (Brassica oleracea L.); paprika (Capsicum annuum L.); white double-spored mushroom.

[031] The technical result was achieved by a single soil treatment, by sowing different seeds (or fungi), with aqueous suspensions of 2-(2-phenylethyl)amino-4-methylpyrimidine-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-ylcarboxylic acid, 4-methyl-2-(piperidin-1-yl)pyrimidin-5-ylcarboxylic acid, 2-(3,4-dihydroisoquinolin-2(1H)-yl)-4-methylpyrimidin-5-ylcarboxylic acid, 4-methyl-2-((3methylphenyl)amino)pyrimidin-5-ylcarboxylic acid and compared with aqueous solutions of the salts of the corresponding acids proposed by the present invention. The application rate of the preparations was 0.0002 g / m2 (2 g / ha).In the control experiments, the crops were irrigated with water. The results of the effect of the preparations are presented in Tables 1 to 13. Detailed Description of the Modalities

[032] To study the effect of N-substituted 2-amino-4-methylpyrimidin-5-ylcarboxylic acids and their salts on seed germination, seeds were soaked in a 0.0015% by weight solution for an exposure time of 2 to 18 hours, depending on the crop treated. To control germination, seeds soaked in tap water were used and, in the case of tomato, also in the commercial growth regulator Epin-extra (produced by NNPP NEST M, Russia, hereinafter referred to as Epin), at a concentration according to the instructions for use - 0.05%). The experiment was carried out in triplicate for each substance. Petition 870250091259, dated 06 / 10 / 2025, page 13 / 45 9 / 31 of test and control, using 200 seeds each or the quantity needed for field trials.

[033] The seeds were germinated at 23 °C. The seedlings were planted on the 15th day after the start of germination. Germination was calculated as a percentage of the ratio between the number of seedlings and the number of seeds used.

[034] The subsequent experiment was carried out in accordance with BA Dospekhov (Methods of field experiment (with the basics of statistical processing of research results). 5th ed. supplemented and revised. - textbook for higher education / BA Dospekhov. - Moscow: Agropromizdat, 1985. - 351 p.) by the split-plot method in triplicate or in multiple fields in field trials.

[035] The data were processed and grouped according to the method described in the work AP Kulaichev (Methods and tools of complex data analysis / AP Kulaichev. - M.: FORUM: INFA-M, 2006. - 512 c.). The statistical processing of the results was performed using the Stadia software package.

[036] A comparison of mean values ​​was performed using Student's t-test. Seed germination in the control and experimental variants was compared by frequency agreement using Z-statistic. The increase in germination, yield, shoot height, and root height as a percentage relative to the control was calculated.

[037] The results of the effect of seed treatment with new compounds from the pyrimidine carboxylic acid series on seed germination, seedling height, yield of different plants and mushrooms compared with the control are presented in Tables 1 to 13.

[038] According to Table 1 below, in the case of the experiment with tomatoes, Epin was also used as a control. The germination of tomato seeds under the influence of the commercial preparation of Epin increased insignificantly (2.7%). The germination of seeds treated with 2-amino-4-methylpyrimidine-5 acids Petition 870250091259, dated 06 / 10 / 2025, page 14 / 45 10 / 31 yl-carboxylic acid increased from 3.6 to 4.4%, while seed germination after treatment with salts of 2-amino-4-methylpyrimidine-5-yl-carboxylic acids increased from 5.6 to 6.9%.

[039] The height of common tomato seedlings in the sowing treatment with 2-amino-4-methylpyrimidine-5-yl-carboxylic acids increased from 37.5% to 44.3% compared to the control. The increase in this index in the case of the use of salts of 2-amino-4-methylpyrimidine-5-yl-carboxylic acids was from 56.8% to 61.4%. The height of the seedlings in the case of the use of the commercial preparation of Epin increased less significantly (6.8%) compared to the control.

[040] The maximum increase in yield was observed in the experiment using 2-amino-4-methylpyrimidine-5-yl-carboxylic acid salts according to the invention and was 44% to 50% compared to the control.

[041] The action of the previously described 2-amino-4-methylpyrimidine-5-yl-carboxylic acids and Epin resulted in yield increases of 32.1 to 36.9% and 10.7%, respectively.

[042] A similar dependence was observed for the average fruit weight values. Thus, under the influence of Epin, the average weight of tomato fruits increased by 3.5%, the application of 2-amino-4-methylpyrimidine-5-yl-carboxylic acids led to an increase in this indicator of 5.1 to 5.6%, and the increase in the average weight of fruits when treated with salts of 2-amino-4-methylpyrimidine-5-yl-carboxylic acids was 9.5 to 12.2%.

[043] As shown in Tables 1-13, the increase in yield of various crops when using 2-amino-4-methylpyrimidine-5-yl-carboxylic acids ranges from 7.8 to 61.8%, depending on the crop treated, and when using the salts according to the present invention, the increase for each crop is substantially greater than that of the corresponding acid treatment and ranges from 25.1 to 101.8%, depending on the crop treated. Petition 870250091259, dated 06 / 10 / 2025, page 15 / 45 11 / 31

[044] The increase in seed germination under the action of 2-amino4-methylpyrimidine-5-yl-carboxylic acids is 0.8 to 14.4%, while for the corresponding salts it is in each case greater than that of the corresponding acid, with an increase of 6.6 to 34.6% observed in relation to the control.

[045] The length of the seedlings increased by 9.8 to 94.7% when 2-amino-4-methylpyrimidin-5-yl-carboxylic acids were used, and by 21.6 to 121.1% when their salts were used. General procedure for the production of compounds of formula (I)

[046] N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acids or their corresponding esters are subjected to interaction with a solution of the appropriate hydroxide of Na, K, Li, Mg, Ca, NH3; or with carbonates and hydrocarbons of Na, K, Li, Mg, Ca, NH3; or with aliphatic and fatty-aromatic amines, in equimolar ratio, in aqueous medium, alone or in mixture with an organic solvent. Preferably, the organic solvent is methyl alcohol or ethyl alcohol, or a combination thereof. The interaction is preferably carried out under heating, followed by isolation of the resulting salt or without isolation. Examples Experimental Example 1. Preparation of the sodium salt of 2-benzylamino-4-methylpyrimidine-5-ylcarboxylic acid.

[047] To a mixture of 2.43 g (10 mmol) of ethyl ester of 2-benzylamino-4-methylpyrimidine-5-ylcarboxylic acid, 10 mL of ethyl alcohol and 10 mL of water, 0.41 g (10.25 mmol) of sodium hydroxide in 10 mL of water was added. The reaction mixture was brought to a boil under reflux until a clear solution was formed. The volatile components were evaporated in a rotary evaporator. As a result, the sodium salt of 2-benzylamino-4-methylpyrimidine-5-ylcarboxylic acid was obtained in quantitative yield. Experimental Example 2. Preparation of the potassium salt of 4-methyl-2-acid. Petition 870250091259, dated 06 / 10 / 2025, page 16 / 45 12 / 31 (piperidin-1-yl)pyrimidine-5-yl-carboxylic acid

[048] To a mixture of 2.21 g (10 mmol) of 4-methyl-2-(piperidin-1yl)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 was added. The reaction mixture was stirred and heated (temperature 50-60 °C) until a clear solution was formed. The volatile components were evaporated in a rotary evaporator. As a result, the potassium salt of 4-methyl-2-(piperidin-1yl)pyrimidin-5-yl-carboxylic acid was obtained in quantitative yield. Experimental Example 3. Preparation of the ethanolamine salt of 4-methyl-2-(morpholin-4-yl)pyrimidine-5-yl-carboxylic acid

[049] To a mixture of 2.23 g (10 mmol) of 4-methyl-2-(morpholin-4-yl)pyrimidin-5-ylcarboxylic 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 50-60 °C) until a clear solution was formed. The solution was then cooled to 0 °C and held at that temperature. The precipitate was quickly filtered and washed with cold isopropyl alcohol. The ethanolamine salt of 4-methyl-2-(morpholin-4-yl)pyrimidin-5-ylcarboxylic acid was obtained in 95% yield.

[050] The physicochemical characteristics of the preferred compounds obtained according to the methods above are presented below.

[051] The 1H and 13C NMR spectra were recorded on a Varian Inova 400 instrument (400 and 100 MHz, respectively). Example 1. Sodium salt of 2-benzylamino-4-methylpyrimidine-5-ylcarboxylic acid [Chemical formula] Petition 870250091259, dated 06 / 10 / 2025, p. 17 / 45 13 / 31 ch, o

[052] Melting Temperature > 300°C. 1H 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-pyrim.). 13C 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. Example 2. Ethanolamine salt of 2-benzylamino-4-methylpyrimidine-5-ylcarboxylic acid [Chemical formula]

[053] Amorphous substance. 1H NMR spectrum, DMSO-d6, δ, ppm; J, Hz: 2.492.56 (3.9H, m, CH3+DMSO); 2.81 (2H, t, CH2NH3, J=6.0); 3.54-3.57 (3.5H, m, CH2OH+H2O); 4.52 (2H, d, CH2N, J=12.0); 5.19 (1H, s. br., NH3); 7.18-7.22 (1H, m, CH-phenyl); 7.25-7.30 (4H, m, 4CH-phenyl); 7.71 (1H, s. br., NH); 8.58 (1H, s, CH-pirim.). Espectro de13C NMR, δ, 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. Example 3. Potassium salt of 4-methyl-2-(piperidin-1 -yl)pyrimidine-5-ylcarboxylic acid [Fórmula química] Petition 870250091259, 06 / 10 / 2025, pág. 18 / 45 14 / 31 ch3ο

[054] Melting temperature >300°C. Spectro de1H NMR, DMSO-d6, δ, ppm; J, Hz: 1.43-1.51 (4H, m, 4CH-piper.); 1.57-1.62 (2H, m, 2CH-piper.); 2.56 (3H, s, CH3); 3.70-3.73 (4H, m, 2CH2-piper.); 8.60 (1H, s, CH-pirim.). Espectro de13C NMR, δ, ppm: 24.8, 24.9, 25.8, 40.5, 40.6, 121.9, 160.3, 160.5, 167.0, 169.1. Example 4. Propanolamine salt of 2-((4-methoxyphenyl)amino)-4methylpyrimidine-5-yl-carboxylic acid [Fórmula química] O' H3N+CH2CH2CH2OH

[055] Amorphous substance. Spectro de1H NMR, DMSO-d6, δ, ppm; J, Hz: 1,711.75 (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, yes, NH3 + OH); 6.83-6.86 (2H, m, 2CHaril); 7.69-7.72 (2H, m, 2CH-aryl); 8.70 (1H, s, CH-pirim.); 9.41 (1H, s, NH). Espectro de13C NMR, 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. Example 5. Lithium salt of 4-methyl-2-(4-methylpiperazin-1 -yl)pyrimidine-5-ylcarboxylic acid [Fórmula química] Petition 870250091259, 06 / 10 / 2025, pág. 19 / 45 15 / 31

[056] Melting temperature > 300°C. 1H NMR spectrum, DMSO-d6, δ, ppm; J, Hz: 2.36 (4H, br. s, 2CH2-piper.); 2.44 (3H, s, NCH3); 2.57 (3H, s, CH3); 3.69-3.72 (4H, m, 2CH2-piper.); 8.62 (1H, s, CH-pirim.). 13C NMR spectrum, δ, ppm: 25.7, 43.4, 51.8, 54.7, 122.1, 160.3, 162.4, 166.8, 169.9. Example 6. Potassium salt of 4-methyl-2-((2,4-difluorophenyl)amino)pyrimidine-5-yl-carboxylic acid [Chemical formula]

[057] Melting point: > 300°C. 1H NMR spectrum, D2O, δ, ppm; J, Hz: 2.33 (3H, s, CH3); 6.77-6.90 (2H, m, CH-aromatic); 7.33-7.39 (1H, m, CH-aromatic); 8.22 (1H, s, CH-pirim.). 13C NMR spectrum, D2O, δ, ppm; J, Hz: 22.5, 104.2 (s. br., 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. Example 7. Sodium salt of 4-methyl-2-((4-methylphenyl)amino)pyrimidine-5-ylcarboxylic acid [Chemical formula] O'Na+ Petition 870250091259, dated 06 / 10 / 2025, p. 20 / 45 16 / 31

[058] Melting point: > 300°C. 1H NMR spectrum, D2O, δ, ppm; J, Hz: 2.09 (3H, s, CH3); 2.31 (3H, s, CH3); 6.99 (2H, d, CH-aromatic); 7.11 (2H, d, CHaromatic); 8.22 (1H, s, CH-pirim.). 13C NMR spectrum, D2O, δ, ppm: 19.9, 22.7, 121.6, 129.3, 133.9, 135.4, 158.6, 158.9, 168.4, 173.5. Example 8. Lithium salt of 4-methyl-2-(phenethylamino)pyrimidine-5-ylcarboxylic acid [Chemical formula] O'LT

[059] Melting point > 300°C. 1H NMR spectrum, D2O, 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-aromatic); 6.94-6.99 (2H, m, CH-aromatic); 8.14 (1H, s, CH-pyrim.). 13C NMR spectrum, D2O, 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. Example 9. Ethanolamine salt of 4-methyl-2-(morpholin-4-yl)pyrimidine-5-ylcarboxylic acid [Chemical formula] o-ii3n+cii2ci i?oh

[060] Melting point: 218-221 °C. 1H NMR spectrum, D2O, δ, ppm; J, Hz: 2.33 (3H, s, CH3); 2.89-2.96 (2H, m, CH2N); 3.51-3.67 (10H, m, CH2O + 4CH2 Petition 870250091259, dated 06 / 10 / 2025, p. 21 / 45 17 / 31 morphol.); 7.01-7.17 (2H, m, CH-aromatic); 8.26 (1H, s, CH-pyrim.). 13C NMR spectrum, D2O, δ, ppm: 22.9, 41.2, 44.2, 57.5, 66.2, 120.3, 158.4, 160.3, 168.3, 173.9. Example 10. Phenethylamine salt of 4-methyl-2-(piperidin-1-yl)pyrimidine-5-ylcarboxylic acid [Chemical formula] H3N'CH2CH2CsH5

[061] Melting point 139-143°C. 1H NMR spectrum, D2O, δ, ppm; J, Hz: 1.67-1.78 (4H, m, 2CH2-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-aromatic); 7.11-7.17 (2H, m, CH-aromatic); 8.17 (1H, s, CH-pyrim.). 13C NMR spectrum, D2O, 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. Example 11. Sodium salt of 2-(3,4-dihydroisoquinolin-2(1H)-yl)-4-methylpyrimidine-5-yl-carboxylic acid [Chemical formula]

[062] Melting temperature: > 300°C. 1H NMR spectrum, D2O, 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-benzene); 8.20 (1H, s, CH-pyrim.). 13C NMR spectrum, Petition 870250091259, dated 06 / 10 / 2025, page 22 / 45 18 / 31 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. Example 12. Triethanolamine salt of 4-methyl-2-((3methylphenyl)amino)pyrimidine-5-yl-carboxylic acid [Fórmula química]

[063] Amorphous substance. Spectro de1H NMR, D2O, 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-aromatic); 8.24 (1H, s, CH-pirim.). Espectro de13C NMR, D2O, 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. Example 13. Triethanolamine salt of 2-benzylamino-4-methylpyrimidine5-yl-carboxylic acid [Fórmula química] o-hn+(c:ii / :h£c]ii)3

[064] Amorphous substance. 1H NMR spectrum, D2O, 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-aromatic); 8.18 (1H, s, CH-pyrim.). 13C NMR spectrum, D2O, 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. Petition 870250091259, dated 06 / 10 / 2025, p. 23 / 45 19 / 31

[065] The use of the proposed water-soluble plant growth stimulators will simplify the use and increase the efficiency of N-substituted 2-amino-4-methylpyrimidine-5-yl-carboxylic acid derivatives in agricultural production needs.

[066] Seed germination rates, seedling and root height, yield and average fruit weight of different plant and mushroom (champignon) species after treatment with 2-amino-4-methylpyrimidine-5-ylcarboxylic acid salts and comparative data obtained by treatment with the corresponding acids are presented in Tables 1 to 13.

[067] Seed germination, seedling height, yield and average fruit weight of Novichok tomato after treatment with known 2-amino-4-methylpyrimidine-5-yl-carboxylic acids, compared with the corresponding new salts according to the invention. Table 1 Product Name Seed Germination, % Seedling Height on Day 50, mm Yield, kg / m2 Average Fruit Weight, g Increase in Seedling Height compared to Control, % Water (control) 51.3 88 ±2 8.4 ± 1 81.8 ± 1 - Epin 0.05% 54.0 94 ± 2a 9.3 ± 1a 84.7 ± 1b 6.8 2-Benzylamino-4-methylpyrimidin-5-ylcarboxylic acid 55.8 127 ±2b 11.5 ± 2a 86.4 ±2b 44.3 4-Methyl 1-2-((2,4-difluorophenyl)amino)pyrimidin-5-ylcarboxylic acid 55.3 124 ±3b 11.0 ± 1a 85.2 ±2b 40.9 4-Methyl-2-(piperidin-1-yl)pyrimidine-5-ylcarboxylic acid 54.9 121 ±2C 11.1 ±2b 86.0 ±2C 37.5 4-Methyl-2-(phenethylamino)pyrimidine-5-ylcarboxylic acid 54.2 122 ± 3c 11.5 ± 2c 84.9 ± 1b 38.6 Petition 870250091259, dated 06 / 10 / 2025, page 24 / 45 20 / 31 Sodium salt of 2-benzylamino-4-methylipinmyoin-5-ylcarboxylic acid 57.5 142 ±3C 12.6 ±2b 91.8 ±2b 61.4 Ethanolamine salt of 2-benzylamino-4-methylipinmyoin-5-ylcarboxylic acid 58.2 140 ±3C 12.2 ±2b 91.3 ±2C 59.1 Potassium salt of 4-methyl-2-((2,4-difluorophenyl)amino)pyrimidine-5-ylcarboxylic acid 57.2 137 ±2C 12.0 ± 1b 90.2 ± 1c 55.7 Lithium salt of 4-methyl-2-(phenethylamino)pyrimidine-5-ylcarboxylic acid 57.8 141 ± 1b 12.5 ±2C 91.0 ±2b 60.1 Potassium salt of 4-methyl-2-(piperidin-1-yl)pyrimidin-5-yl-carboxylic acid 56.9 138 ± 2 c 12.1 ± 2b 89.6 ± 2b 56.8

[068] Seed germination, seedling height, yield and average fruit weight of common eggplant of the Lilac variety (Solanum melongena L.) after treatment with known 2-amino-4-methylpyrimidine-5-yl-carboxylic acids, in comparison with the corresponding new salts, according to the invention. Table 2 Product Name Seed Germination, % Seedling Height after 50 days, mm Yield, kg / m2 Yield increase compared to control, % Average fruit weight, g Seedling height increase compared to control, % Water (control) 45.3 74 ±2 3.0 ± 1 198 ± 1 2-Benzylamino-4-methylpyrimidine-5-ylcarboxylic acid 62.5 98 ± 2b 4.4 ± 2a 46.7 219 ± 2b 32.4 4-Methyl 1-2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 56.7 104 ± 2b 4.5 ± 2b 50.0 225 ± 2C 40.5 4-Methyl-2-((4-methylphenyl)amino)pyrilic acid 58.9 101 ± 2c 4.5 ± 1b 50.0 221 ± 2b 36.5 Petition 870250091259, dated 06 / 10 / 2025, page 25 / 45 21 / 31 m-idine-5-ylcarboxylic acid Ethanolamine salt of 2-benzylamino-4-methylpyrimidine-5-ylcarboxylic acid 76.1 118 ± 2C 5.0 ±2b 66.7 258 ± 2b 59.4 Lithium salt of 4-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 79.4 115 ± 2C 5.1 ±2C 70.0 261 ± 2b 54.4 Sodium salt of 4-methyl-2-((4-methylphenyl)amino)pyrimidine-5-ylcarboxylic acid 77.6 117 ± 2b 5.0 ± 2c 66.7 262 ± 1b 58.1

[069] Seed germination and seedling height of perennial rhododendrons Ledeburg (Rhododendron Ledebourii Pojarc.) after treatment with known 2-amino-4-methylpyrimidine-5-yl-carboxylic acids, compared with the corresponding novel salts, according to the invention. Table 3 Product Name Seed Germination s, % Seedling Height after 3 months, mm Seedling Height Increase compared to Control, % Seedling Height after 6 months, mm Seedling Height Increase compared to Control, % Water (control) 56.3 19± 1 - 54 ± 1 - 2-Benzylamino-4-methylpyrimidine-5-ylcarboxylic acid 55.9 29 ± 1b 65.5 76 ± 1b 38.2 4-Methyl 1-2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 69.4 37 ± 1b 94.7 75 ± 2b 33.9 4-Methyl-2-(piperidin-1-yl)pyrimidine-5-ylcarboxylic acid 66.8 34 ±2b 78.9 70 ± 1b 29.6 Sodium salt of 2-benzylamino-4- acid 79.2 39 ± 1b 105.3 80 ± 1b 48.1 Petition 870250091259, dated 06 / 10 / 2025, page 26 / 45 22 / 31 Methylpyrimidine-5-ylcarboxylic acid Triethanolamine salt of 2-benzylamino-4-methylpyrimidine-5-ylcarboxylic acid 79.0 41 ± 1b 115.8 81 ± 1c 50.0 Lithium salt of 4-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 78.3 42 ± 1c 121.1 83 ± 2b 53.7 Potassium salt of 4-methyl-2-(piperidin-1-yl)pyrimidine-5-ylcarboxylic acid 81.0 41 ± 1c 115.8 78 ± 1c 44.4

[070] Germination and height of deviated velvet seeds of the variety «Red Cherry» (Tagetes patula L.) after treatment with known 2-amino-4-methylpyrimidine-5-yl-carboxylic acids, in comparison with the corresponding novel salts, according to the invention. Table 4 Product Name Seed Germination, % Seedling Height after 50 days, mm Min Max, cm Seedling Height Increase compared to Control, % Water (control) 35.7 19± 1 16-22 2-((4-methoxyphenyl)amino)-4-methylpyrimidine-5-ylcarboxylic acid 38.2 25 ± 1b 18-28 31.6 4-Methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 43.3 27 ± 1b 19-30 42.1 4-Methyl-2-(piperidin-1-yl)pyrimidine-5-ylcarboxylic acid 44.7 26 ± 2b 18-30 36.8 4-Methyl-2- (phenethylamino)pyrimidine-5-ylcarboxylic acid 39.5 28 ± 1b 19-31 47.4 Lithium salt of 4-methyl2-(phenethylamino)pyrimidine-5-ylcarboxylic acid 49.7 32 ± 1b 25-37 68.4 Propanolamine salt 48.6 33 ± 1b 27-38 73.7 Petition 870250091259, dated 06 / 10 / 2025, page 27 / 45 23 / 31 2-((4-methoxyphenyl)amino)-4-methylpyrimidine-5-ylcarboxylic acid Lithium salt of 4-methyl2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 50.5 32 ± 1c 25-35 68.4 Potassium salt of 4-methyl-2-(piperidin-1-yl)pyrimidine-5-ylcarboxylic acid 47.1 35 ± 1c 28-43 82.2

[071] Germination, height and yield of winter wheat of the variety Alekseich (Triticum aestivum L.) after treatment with known 2-amino-4-methylpyrimidine-5-yl-carboxylic acids, in comparison with the corresponding novel salts, according to the invention. Table 5 Product Name Seed Germination, % Seedling Height 30 days after germination, cm Increase in seedling height compared to control, % Yield, q / ha Increase in yield compared to control, % Water (control) 87.9 37 ± 0.2 58.1 ± 0.1 2-((4-Methoxyphenyl)amino)-4-methylpyrimidine-5-ylcarboxylic acid 88.7 41 ± 0.2b 10.8 70.3 ± 0.1b 21.0 4-Methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 89.3 43 ± 0.2c 16.2 73.6 ± 0.1c 26.7 4-Methyl-2-(piperidin-1 2-((4-methoxyphenyl)amino)-4-methylpyrimidine-5-ylcarboxylic acid propanolamine salt 90.4 42 ± 0.2b 13.5 73.8 ± 0.1b 27.0 Propanolamine salt of 2-((4-methoxyphenyl)amino)-4-methylpyrimidine-5-ylcarboxylic acid 90.8 46 ± 0.2c 24.3 80.4 ± 0.1c 38.4 Petition 870250091259, dated 06 / 10 / 2025, page 28 / 45 24 / 31 Lithium salt of 4-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 93.1 48 ± 0.2c 29.7 83.5 ± 0.1b 43.7 Potassium salt of 4-methyl-2-(piperidin-1-yl)pyrimidine-5-ylcarboxylic acid 96.6 45 ± 0.1c 21.6 85.6 ± 0.1b 47.3

[072] Yield and average fruit weight of Zekura variety potatoes (Solanum tuberosum) after treatment with known 2-amino-4-methylpyrimidine-5-ylcarboxylic acids, compared with the corresponding new salts, according to the invention. Table 6 Product Name Yield, kg / m2 Average Tuber Weight, kg Yield Increase compared to Control, % Water (control) 2.71 ± 0.2 0.064 ± 0.002 2-Benzylamino-4-methylpyrimidine-5-ylcarboxylic acid 2.92 ± 0.2b 0.067 ± 0.002b 7.8 4-Methyl-2-(morpholin-4yl)pyrimidine-5-ylcarboxylic acid 2.91 ± 0.2c 0.067 ± 0.002b 7.4 4-Methyl 1-2-(4-methylpiperazin-1yl)pyrimidine-5-ylcarboxylic acid 2.98 ± 0.2b 0.068 ± 0.002b 10.1 4-Methyl-2-((2,4-difluorophenyl)amino)pyrimidin α-5-yl-carboxylic acid 2.83 ± 0.1b 0.068 ± 0.001b 4.4 Ethanolamine salt of 2-benzylamino-4-methylpyrimidine-5-yl-carboxylic acid 3.41 ± 0.2b 0.071 ± 0.002c 25.8 Potassium salt of 4-methyl-2-((2,4-difluorophenyl)amino)pyrimidin α-5-yl-carboxylic acid 3.36 ± 0.2b 0.070 ± 0.001b 24.0 Ethanolamine salt of 4-methyl-2-(morpholin-4yl)pyrimidine-5-yl-carboxylic acid 3.40 ± 0.2c 0.071 ± 0.001c 25.5 Lithium salt of 4-methyl-2-(4-methylpiperazine-1-) acid - 3.39 ± 0.2b 0.069 ± 0.002 c 25.1 Petition 870250091259, dated 06 / 10 / 2025, page 29 / 45 25 / 31 il)pyrimidine-5-yl-carboxylic acid

[073] Sunflower yield of the Chakinsky 100 variety (Helianthus L.) after treatment with known 2-amino-4-methylpyrimidine-5-yl-carboxylic acids, compared with the corresponding new salts according to the invention. Table 7 Product Name S, ha Yield, q / ha Yield increase compared to control, % Water (control) 5 17.1 ± 0.2 - 2-Benzylamino-4-methylpyrimidine-5-yl-carboxylic acid 5 23.0 ± 0.2b 35.3 4-Methyl 1-2-(4-methylpiperazin-1-yl)pyrimidine-5-yl-carboxylic acid 5 23.9 ± 0.2b 39.8 4-Methyl-2-(piperidin-1-yl)pyrimidine-5-yl-carboxylic acid 5 23.5 ± 0.2b 37.4 Ethanolamine salt of 2-benzylamino-4-methylpyrimidine-5-yl-carboxylic acid 5 25.7 ± 0.2c 50.3 Phenethylamine salt of benzylamino-4-methylpyrimidine-5-yl-carboxylic acid 4-methyl-2-(piperidin-1-yl)pyrimidine-5-ylcarboxylic acid 5 26.2 ± 0.2b 53.2 Lithium salt of 4-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 5 26.8 ± 0.2c 56.7

[074] Yield of the corn hybrid (Zea mays L.) «Mixi» after treatment with known 2-amino-4-methylpyrimidine-5-yl-carboxylic acids, compared with the corresponding new salts, according to the invention. Table 8 Product Name S, ha Dry Clean Grain Yield, q / ha Yield increase compared to control, % Water (control) 15 55 ± 0.3 - 2-Benzylamino-4-methylpyrimidine-5-yl-carboxylic acid 15 90 ± 0.2b 63.64 4-Methyl-2-(piperidin-1-yl)pyrimidine-5-yl-carboxylic acid 15 87 ± 0.3b 58.18 2-((4-Methoxyphenyl)amino)- 15 89 ± 0.3b 61.82 Petition 870250091259, dated 06 / 10 / 2025, page 30 / 45 26 / 31 4-Methylpyrimidine-5-yl-carboxylic acid 4-Methyl 1-2-(4-methylpiperazin-1-yl)pyrimidine-5-yl-carboxylic acid 15 83 ± 0.2c 50.91 Sodium salt of 2-benzylamino-4-methylpyrimidine-5-yl-carboxylic acid 15 111 ± 0.1c 101.82 Ethanolamine salt of 2-benzylamino-4-methylpyrimidine-5-yl-carboxylic acid 15 104 ± 0.2a 89.09 Potassium salt of 4-methyl-2-(piperidin-1-yl)pyrimidine-5-yl-carboxylic acid 15 98 ± 0.1c 78.18 Propanolamine salt of 2-((4-methoxyphenyl)amino)-4-methylpyrimidine-5-yl-carboxylic acid 15 105 ± 0.3b 90.91 Lithium salt of 4-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-yl-carboxylic acid 15 103 ± 0.2 87.27

[075] Yield and average fruit weight of the zucchini variety Tintoretto (Cucurbita pepo subsp. pepo) after treatment with known 2-amino-4-methylpyrimidine-5-yl-carboxylic acids, compared with the corresponding novel salts, according to the invention. Table 9 Product Name Fruit Weight, kg Increase in fetal weight compared to control, % Yield, kg / m2 Increase in yield compared to control, % Water (control) 1.65 ± 0.03 7.50 ± 0.03 2-Benzylamino-4-methylpyrimidine-5-ylcarboxylic acid 1.78 ± 0.04a 7.88 8.34 ± 0.04a 11.21 2-((4-Methoxyphenyl)amino)-4-methylpyrimidine-5-ylcarboxylic acid 1.84 ± 0.02b 11.52 8.55 ± 0.04a 14.00 4-Methyl 1-2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 1.81 ± 0.02b 9.70 8.46 ± 0.03b 12.80 Sodium salt of acid 2.18 ± 0.02c 32.12 10.23 ± 0.02b 36.40 Petition 870250091259, dated 06 / 10 / 2025, page 31 / 45 27 / 31 2-benzylamino-4-methylpyrimidine-5-ylcarboxylic acid Triethanolamine salt of 2-benzylamino-4-methylpyrimidine-5-ylcarboxylic acid 2.15 ± 0.03b 30.3 9.87 ± 0.03b 31.6 Propanolamine salt of 2-((4-methoxyphenyl)amino)-4-methylpyrimidine-5-ylcarboxylic acid 2.08 ± 0.03b 26.06 9.73 ± 0.03a 29.73 Lithium salt of 4-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 2.12 ± 0.04a 28.48 9.82 ± 0.04a 30.93

[076] Germination and shoot length of the pea variety «Orlus» (Pisum L.) after treatment with known 2-amino-4-methylpyrimidine-5-yl-carboxylic acids, in comparison with the corresponding new salts, according to the invention. Table 10 Product Name Seed Germination, % Increase in germination compared to control, % Sprout length on day 10, cm Increase in sprout length compared to control, % Water (control) 89.0 - 8.25 ± 0.04 - 2-((4-Methoxyphenyl)amino)4-methylpyrimidine-5-ylcarboxylic acid 93.3 4.8 11.26 ± 0.03b 36.48 4-Methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 93.4 4.9 11.54 ± 0.04a 39.87 4-Methyl-2-(morpholin-4-yl)pyrimidine-5-ylcarboxylic acid 93.0 4.5 11.31 ± 0.02b 37.1 4-Methyl-2 Acid- 92.9 4.4 11.22 ± 0.03c 36.0 Petition 870250091259, dated 06 / 10 / 2025, page 32 / 45 28 / 31 (piperidin-1-yl)pyrimidine-5-ylcarboxylic acid Ethanolamine salt of 4-methyl-2-(morpholin-4-yl)pyrimidine-5-ylcarboxylic acid 94.9 6.6 12.55 ± 0.03b 52.1 Propanolamine salt of 2-((4-methoxyphenyl)amino)4-methylpyrimidine-5-ylcarboxylic acid 94.8 6.5 12.42 ± 0.02c 50.55 Lithium salt of 4-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 95.2 7.0 12.94 ± 0.03c 56.85 Phenethylamine salt of 4-methyl-2-(piperidin-1-yl)pyrimidine-5-ylcarboxylic acid 94.5 6.2 12.88 ± 0.03c 56.1

[077] Yield and weight of a head of white cabbage of the variety “Podarok” (“Gift”) (Brassica oleracea L.) after treatment with known 2-amino-4-methylpyrimidine-5-yl-carboxylic acids, compared with the corresponding new salts, according to the invention. Table 11 Product Name Yield, q / ha Yield increase compared to control, % Marketable yield, q / ha Increase in marketable yield compared to control, % Average weight of a cabbage head, kg Water (control) 48.3 ± 0.04 - 46.1 ± 0.02 - 2.11 ± 0.01 Acid 2- 54.8 ± 0.02b 13.5 52.4 ± 0.02b 13.7 2.25 ± 0.01b Petition 870250091259, dated 06 / 10 / 2025, page 33 / 45 29 / 31 Benzylamino-4-methylpyrimidine-5-ylcarboxylic acid 4-Methyl 1-2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 55.0 ± 0.02b 13.9 54.3 ± 0.01c 17.8 2.30 ± 0.01b 4-Methyl-2-(piperidin-1-yl)pyrimidine-5-ylcarboxylic acid 56.7 ± 0.02b 17.4 54.2 ± 0.02b 17.6 2.34 ± 0.01b Ethanolamine salt of 2-benzylamino-4-methylpyrimidine-5-ylcarboxylic acid 61.6 ± 0.02b 27.5 58.9 ± 0.02b 27.8 2.47 Lithium salt of 4-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-ylcarboxylic acid 69.5 ± 0.02c 43.9 66.4 ± 0.02c 44.0 2.54 Potassium salt of 4-methyl-2-(piperidin-1-yl)pyrimidine-5-ylcarboxylic acid 64.9 ± 0.02b 34.4 62.2 ± 0.02c 34.9 2.51 ± 0.01b

[078] Yield and fruit weight of Flamingo variety sweet pepper (Capsicum annuum L.) after treatment with known 2-amino-4-methylpyrimidine-5-ylcarboxylic acids, compared with the corresponding new salts, according to the invention. Table 12 Product Name Fruit Weight, g Increase in fetal weight compared to control, % Yield, kg / m2 Increase in yield compared to control, % Water (control) 89.76 ± 0.02 - 4.38 ± 0.03 - 2-Benzylamino-4-methylpyrimidine-5-ylcarboxylic acid 99.58 ± 0.03b 10.94 5.62 ± 0.01c 28.31 2-((4-Methoxyphenyl)amino)-4-methylpyrimidine-5- 103.72 ± 0.02c 15.55 6.04 ± 0.02b 37.90 Petition 870250091259, dated 06 / 10 / 2025, pages 34 / 45 30 / 31 2-(3,4-Dihydroisoquinoline-2(1H)-yl)-4-methylpyrimidine-5-ylcarboxylic acid 98.93 ± 0.03c 10.2 5.93 ± 0.01c 35.4 Sodium salt of 2-benzylamino-4-methylpyrimidine-5-ylcarboxylic acid 128.14 ± 0.02b 42.76 7.93 ± 0.02b 81.05 Sodium salt of 2-(3,4-dihydroisoquinoline-2(1H)-yl)-4-methylpyrimidine-5-ylcarboxylic acid 127.89 ± 0.02b 42.5 7.80 ± 0.02c 78.1 Propanolamine acid salt 2-((4-methoxyphenyl)amino)4-methylpyrimidine-5-yl-carboxylic acid 126.53 ± 0.03b 40.96 7.85 ± 0.01b 79.22

[079] Yield of mushrooms (Bisporus white) after treatment with known 2-amino-4-methylpyrimidin-5-yl-carboxylic acids, compared with the corresponding new salts, according to the invention. Table 13 Product Name S, m2 Yield, kg / m2 Yield increase compared to control, % Water (control) 2 4.8 ± 0.2a - 2-Benzylamino-4-methylpyrimidine-5-ylcarboxylic acid 2 5.4 ± 0.2a 12.5 4-Methyl-2-((3-methylphenyl)amino)pyrimidine-5-ylcarboxylic acid 2 5.2 ± 0.3c 8.0 Sodium salt of 2-benzylamino-4-methylpyrimidine-5-ylcarboxylic acid 2 6.1 ± 0.2a 27.0 Triethanolamine salt of 4-methyl-2-((3-methylphenyl)amino)pyrimidine-5-ylcarboxylic acid 2 5.9 ± 0.3c 22.9 Petition 870250091259, dated 06 / 10 / 2025, pages 35 / 45 31 / 31 a - the differences with the control are significant (P < 0.05); b - the differences with the control are significant (P < 0.01); c - the differences with the control are significant (P < 0.001) Petition 870250091259, dated 06 / 10 / 2025, pp. 36 / 45

Claims

1 / 4 CLAIMS 1. Compound being a salt of N-substituted 2-amino-4-methylpyrimidine-5-ylcarboxylic acids, corresponding to general formula (I) CHARACTERIZED in that X+ is selected from the cations Na+, K+, Li-, 1 / 2 Mg2+, 1 / 2 Ca2+, NH4+, H3N+CH2CH2OH, H3N+CH2CH2CH2OH, HN+(CH2CH2OH)3, H3N+CH2CH2C6H5, or anh3+, A2NH2+, A3NH+, A represents C1-C12 alkyl, C1-C12 aryl, C5-C12 heterocyclyl, C5-C12 heteroaryl, wherein heterocyclyl and heteroaryl contain 1 to 3 heteroatoms selected from N, O and S, wherein each A is optionally substituted by one or plus groups independently selected from halogen, amino-, thio-, hydroxy, R = hydrogen, Ri represents C1-C1 alkyl; a phenyl optionally substituted with one or more substituents selected from -(C1-C4), alkyl, methoxy, ethoxy, halogen; phenyl-(C1-C4)alkyl;or R+R1, together with a nitrogen atom, represent pyrrolidine, hydroquinoline, hydroisoquinoline, piperidine, morpholine, piperazine, optionally substituted by one or more substituents selected from halogen, -(C1C4)alkyl and Ce-C1C2 aryl.; 2. Compound according to claim 1, CHARACTERIZED by the fact Petition 870250091259, dated 06 / 10 / 2025, page 37 / 45 2 / 4 that Ri represents methyl, ethyl, propyl; phenyl, optionally substituted by one or two substituents selected from methyl, ethyl; methoxy, halogen; and phenyl-(C1-C2)alkyl-.

3. Compound according to claim 1, CHARACTERIZED in that R+Ri together with a nitrogen atom represent pyrrolidine, hydroquinoline, hydroisoquinoline, piperidine, morpholine, piperazine, optionally substituted by one or two substituents selected from methyl, ethyl, halogen and phenyl.

4. Compound according to claim 1, CHARACTERIZED in that the cation is Na+, K+, Li+, 1Λ Mg2+, 1Λ Ca2+, NH4+, H3N+CH2CH2OH, H3NXH2CH2CH2OH, H3N+ CH2CH2C6H5, HN+(CH2CH2OH)3.

5. Compound according to claim 1, CHARACTERIZED in that the compound is selected from the group consisting of salts of 2-(2-phenylethyl)amino-4-methylpyrimidin-5-yl-carboxylic acid, 4-methyl-2-(pyrrolidin-1-yl)pyrimidin-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(1H)yl)-4-methylpyrimidine-5-yl-carboxylic acid, 4-methyl-2-((2,4-difluorophenyl)amino)pyrimidine-5-yl-carboxylic acid 4-methyl-2-((4methylphenyl)amino)pyrimidine-5-yl-carboxylic acid, 4-methyl-2-(morpholin-4-yl)pyrimidin-5-ylcarboxylic acid, 4-methyl-2-(piperidin-1-yl)pyrimidin-5-yl-carboxylic acid, 4-methyl-2-((3methylphenyl)amino)pyrimidin-5-yl-carboxylic acid.

6. Compound according to claim 5, CHARACTERIZED in that the salt is a potassium salt, an ethanolamine salt, a sodium salt, a propanolamine salt, a lithium salt, a phenethylamine salt, or a triethanolamine salt.

7. Compound, according to claim 1, CHARACTERIZED by being selected from a sodium salt of 2-benzylamino-4-methylpyrimidin-5-ylcarboxylic acid, a potassium salt of 4-methyl-2-(piperidin-1-yl)pyrimidin-5-yl acid. Petition 870250091259, dated 06 / 10 / 2025, page 1. 38 / 45 3 / 4 carboxylic acid, an ethanolamine salt of 4-methyl-2-(morpholine-4-yl)pyrimidin-5-ylcarboxylic acid, a sodium salt of 2-benzylamino-4-methylpyrimidin-5-ylcarboxylic acid, an ethanolamine salt of 2-benzylamino-4-methylpyrimidin-5-ylcarboxylic acid, a potassium salt of 4-methyl-2-(piperidin-1-yl)pyrimidin-5-ylcarboxylic acid, a propanolamine salt of 2-((4-methoxyphenyl)amino)-4-methylpyrimidin-5-ylcarboxylic acid, a lithium salt of 4-methyl-2-(4-methylpiperazin-1-yl)pyrimidin-5-ylcarboxylic acid, a potassium salt of 4-methyl-2-((2,4-difluorophenyl)amino)pyrimidin-5-ylcarboxylic acid, a salt sodium 4-methyl-2-((4-methylphenyl)amino)pyrimidin-5-yl-carboxylic acid,a lithium salt of 4-methyl-2-(phenethylamino)pyrimidin-5-yl-carboxylic acid, an ethanolamine salt of 4-methyl-2-(morpholin-4-yl)pyrimidin-5-yl-carboxylic acid, a phenethylamine salt of 4-methyl-2-(piperidin-1-yl)pyrimidine-5-yl-carboxylic acid, a sodium salt of 2(3,4-dihydroisoquinoline-2(1H)-yl)-4-methylpyrimidine-5-yl-carboxylic acid, a triethanolamine salt of 4-methyl-2-((3-methylphenyl)amino)pyrimidin-5-yl-carboxylic acid, and a triethanolamine salt of 2-benzylamino-4-methylpyrimidin-5-yl-carboxylic acid.

8. Method for producing a salt, according to any one of claims 1 to 7, CHARACTERIZED in that it comprises contacting water and / or an organic solvent, an N-substituted 2-amino-4-methylpyrimidin-5-ylcarboxylic acid or its corresponding ester with a solution of a corresponding hydroxide of Na, K, Li, Mg, Ca, NH3; and isolating the resulting salt.

9. Method according to claim 8, CHARACTERIZED in that the contact is made in water and / or an organic solvent selected from ethanol, methanol, or a combination thereof.

10. Method according to claim 8, CHARACTERIZED in that contact is made during heating.

11. Method for producing a salt, according to any one of claims 1 to 7, CHARACTERIZED in that it comprises contacting in water N-substituted 2-amino-4-methylpyrimidin-5-yl-carboxylic acid or its corresponding ester with carbonate or hydrocarbonate of Na, K, Li, Mg, Ca, NH3; and isolating the resulting salt.

12. Method for producing a salt, according to any one of claims 1 to 7, CHARACTERIZED in that it comprises contacting water and / or an organic solvent, an N-substituted 2-amino-4-methylpyrimidin-5-ylcarboxylic acid or its corresponding ester with aliphatic and aromatic amines, and isolating the resulting salt.

13. Method according to claim 12, CHARACTERIZED in that the contact is made in water and / or an organic solvent selected from ethanol, methanol, or a combination thereof.

14. Method according to claim 13, CHARACTERIZED in that contact is made during heating.

15. Use of a compound, according to any one of claims 1 to 7, CHARACTERIZED in that it is for stimulating the growth of plants or fungi.

16. Use, according to claim 15, CHARACTERIZED in that the stimulation of plant or fungal growth is selected from stimulation of germination energy, stimulation of seed germination, stimulation of seedling biometrics, stimulation of root formation, and stimulation of yield in a wide range of crops.

17. Use, according to claim 15, CHARACTERIZED in that the stimulation of plant growth is carried out in 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, rhododendron, velvet bean, wheat, potato, sunflower, corn, zucchini, pea, cabbage, bell pepper and mushroom. Petition 870250091259, dated 06 / 10 / 2025, pp. 40 / 45