RU2109011C1 - Derivatives of iminosulfonylurea, method of weed abolishing or suppressing - Google Patents

Abstract

FIELD: organic chemistry. SUBSTANCE: invention relates to derivatives of iminosulfonylurea of the formula (I) or its salt $$$ where Q is: Q1 - $$$; Q2 - $$$; Q3 - $$$; Q4 - $$$; Q5 - $$$; Q6 - $$$; Q7 - $$$; Q8 - $$$ or Q9 - $$$ where Q1, Q2 and Q5 - sulfur, oxygen or nitrogen atom monosubstituted with any substituent except for hydrogen atom; in Q6, Q7 and Q8 J means sulfur or oxygen atom; in Q1-Q8 nitrogen atom in Q-ring is substituted with any substituent except for hydrogen atom; carbon atom in Q-ring can be substituted with any substituent; in Q9 sulfur atom and nitrogen atom at carbon atom to which Q-imino-group is bound are substituted with any substituents except for hydrogen atom; X means oxygen or sulfur atom; L means hydrogen atom, $$$-alkyl group, $$$-alkenyl group or $$$-alkynyl group; A means CH-group or nitrogen atom; each of B and D means independently $$$-alkyl group, $$$-alkoxyl group, mono-, di- or polyhalogen-$$$-alkyl group, mono-, di- or polyhalogen-$$$-alkyl group, mono-, di- or polyhalogen-$$$-alkoxyl group, halogen atom, $$$-alkylamino-group or di-$$$-alkylamino group. Herbicide containing this derivative and herbicide method of control over weed that involves the use of this derivative. EFFECT: improved method of synthesis. 9 cl, 30 tbl

Description

 The invention relates to new derivatives of iminosulfonylurea, useful as active ingredients in weed control compositions.

 The use of herbicides is necessary to protect the crops of plants important for agricultural production, such as rice, wheat, corn, soybeans, cotton and sugar beets, from weeds and, thereby, to increase the yield. In recent years, the use of selective herbicides that are capable of selectively controlling weeds without showing any phytotoxicity towards the planted plants while treating the leaves of cultivated plants and weeds in the area where useful plantings and weeds coexist is especially desirable. In order to avoid environmental pollution and reduce the cost of transportation and processing for many years, searches and development of compounds having high herbicidal activity at low doses have been carried out. Some of the compounds having such properties are currently used as selective herbicides. However, there remains a need for new improved compounds having the above properties.

 A chemical structure similar to that of the compounds of the present invention is disclosed in Japanese Patent Publication No. 15962/1983, No. 103371/1983, No. 126859/1983, No. 48973/1985, No. 214785/1985, No. 134377/1986, No. 151577 / 1989, N 45473/1990, N 91060/1990, N 7284/1991 and N 68561/1991 and US patents 4,559,081, 4,592,776, 4,602,939, 4,622,065, 4,666,508, 4,696,695 and 4,741,762. However, compounds like the compounds of the present invention are not known at all and are new compounds.

где Q представляет:

где R₁ - C₁-C₆-алкил, CH₂-CO-A, CH₂-O-A,
где A - C₁-C₆алкил, C₂-C₆алкенил, который может быть замещен группой фенила или атомами галогена, C₂-C₆алкинил, CH₂-CO-A группа, где A имеет вышеуказанные значения, C₁-C₂алкил-O-алкил, который может быть замещен фенильной группой, -CH₂S-A группа, где A определено выше, -CH₂-CN группа, C₁-C₂алкилфенильная группа, где фенил может быть замещен алкоксигруппой или атомами галогена;
R₂ - атом галогена, C₁-C₆алкил или фенил;
R₃ - водород, C₁-C₆алкил или атом галогена;
R₄ - C₁-C₆алкил, C₂-C₆алкенил, который может быть замещен атомами галогена, C₂-C₆алкинил, -CH₂-O-A, где A - C₁-C₆алкил (соединение 64-a) или фенил;
R₅ - водород или C₁-C₆алкил;
R₆ - C₁-C₆алкил;
R₇ - C₁-C₆алкил;
R₈ - C₁-C₆алкил, C₂-C₆алкенил, C₂-C₆алкинил или -CH₂-CO-A группа, где A - C₁-C₆алкил;
R₉ - водород или C₁-C₆алкил;
R₁₀ - C₁-C₆алкил, C₂-C₆алкинил (соединение 17-c), C₂-C₆алкенил, который может быть замещен группой бензила или атомами галогена;
R₁₁ - метил или водород;
R₁₂ - C₁-C₆алкил, C₂-C₆алкенил, C₂-C₆алкинил, -CH₂-CO-A группа, -CH₂-COO-A группа, CH₂O-A группа или CH₂-S-A группа, где A имеет указанные значения;
R₁₃ - C₁-C₆алкил или -CH₂-O-A группа, где A имеет указанные значения;
R₁₄ - C₁-C₆алкил или C₂-C₆алкенил;
R₁₅ - C₁-C₆-алкил, C₂-C₆-алкенил или C₂-C₆-алкинил;
R₁₆ - C₁-C₆-алкил;
R₁₇ - C₁-C₆-алкил, C₁-C₆-алкокси, -CO-A группа, где A имеет указанные значения, фенил или C₂-C₆-алкенил, при условии, что R₁₆ и R₁₇ могут вместе образовывать четырехчленное алкильное кольцо;
L - водород, C₁-C₆-алкил;
группа A в кольце - CH-группа или атом азота;
B и D независимо C₁-C₆-алкил, C₁-C₆-алкокси, C₁-C₆-галоалкокси или атом галогена.The inventors of the present invention have carried out extensive research over the years to develop selective herbicides for important agricultural plants and studied the herbicidal properties of many compounds in order to find compounds having high herbicidal activity as well as selectivity. As a result, it was found that a derivative of iminosulfonylurea with the formula / I / or its salt suitable for agriculture:

where Q represents:

where R ₁ is C ₁ -C ₆ alkyl, CH ₂ -CO-A, CH ₂ -OA,
where A is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl which may be substituted by a phenyl group or halogen atoms, C ₂ -C ₆ alkynyl, CH ₂ -CO-A group, where A has the above meanings, C ₁ -C ₂ alkyl-O-alkyl which may be substituted by a phenyl group, -CH ₂ SA group, where A is defined above, -CH ₂ -CN group, C ₁ -C ₂ alkylphenyl group, where phenyl may be substituted by alkoxy group or atoms halogen;
R ₂ is a halogen atom, C ₁ -C ₆ alkyl or phenyl;
R ₃ is hydrogen, C ₁ -C ₆ alkyl or a halogen atom;
R ₄ is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl which may be substituted by halogen atoms, C ₂ -C ₆ alkynyl, -CH ₂ -OA, where A is C ₁ -C ₆ alkyl (compound 64- a) or phenyl;
R ₅ is hydrogen or C ₁ -C ₆ alkyl;
R ₆ is C ₁ -C ₆ alkyl;
R ₇ is C ₁ -C ₆ alkyl;
R ₈ is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or a-CH ₂ -CO-A group, where A is C ₁ -C ₆ alkyl;
R ₉ is hydrogen or C ₁ -C ₆ alkyl;
R ₁₀ is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkynyl (compound 17-c), C ₂ -C ₆ alkenyl, which may be substituted with a benzyl group or halogen atoms;
R ₁₁ is methyl or hydrogen;
R ₁₂ is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, -CH ₂ -CO-A group, -CH ₂ -COO-A group, CH ₂ OA group or CH ₂ - SA group, where A has the indicated meanings;
R ₁₃ is a C ₁ -C ₆ alkyl or -CH ₂ -OA group, where A has the indicated meanings;
R ₁₄ is C ₁ -C ₆ alkyl or C ₂ -C ₆ alkenyl;
R ₁₅ is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl;
R ₁₆ is C ₁ -C ₆ alkyl;
R ₁₇ is C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, -CO-A group, where A has the indicated meanings, phenyl or C ₂ -C ₆ -alkenyl, provided that R ₁₆ and R ₁₇ may together form a four-membered alkyl ring;
L is hydrogen, C ₁ -C ₆ alkyl;
group A in the ring — CH group or nitrogen atom;
B and D are independently C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy or a halogen atom.

 The proposed compound can be used as a herbicide for upland fields, which can be applied in any way, for example, in the process of soil cultivation, in the form of additives introduced into the soil during processing or during spraying of leaves.

 The dosage of the compound according to the invention varies depending on the place of application, season, method of application, type of weeds that are being controlled, type of crops, etc. However, usually the dose is from 0.0001 to 10 kg, preferably from 0.005 to 5 kg per hectare (ha) of active ingredient.

 The compound of the invention can be combined with other herbicides, various insecticides, fungicides, plant growth regulators, synergism agents or preservatives, the compound of the invention being combined with other herbicides either during the preparation of the formulation or at the time of application, as the case may be.

 In particular, the addition of a compound of the invention to other herbicides when they are applied to the soil or during the spraying process helps to reduce costs by lowering the dose or expanding the spectrum of the herbicidal action, or this method of application can achieve a stronger herbicidal effect due to the synergistic effect of the combined herbicides. In this case, many known herbicides can be combined at the same time. In combination with the compound of the invention, for example, the compounds described in the Agricultural Chemicals Handbook (1990) can be used.

 If the compounds of the invention are intended to be used as a herbicide, it is usually mixed with a suitable carrier, for example, a solid carrier, such as clay, talc, bentonite, diamite earth or fine silica powder, or with a liquid carrier, such as water, alcohol (such like isopropanol, butanol, benzyl alcohol or furyl alcohol), aromatic hydrocarbons (such as toluene or xylene), ether (such as anisole), ketone (such as cyclohexanone or isophorone), an ester (such as butyl acetate), an acid amide (such ka to N-methylpyrrolidone) or a halogenated hydrocarbon (such as chlorobenzene). If desired, a surfactant, emulsifier, dispersant, penetrating agent, wetting agent, thickener, antifreeze, coagulation preventing agent, aphid stabilizer are added; these substances are added during the manufacture of liquid compositions, emulsifiable concentrates, wettable powders, dry fluid mixtures, fine powders or granules.

 Among the weeds against which the compound of the invention is directed, for example, weeds of the genus Solanaceae, such as Solanum nigrum and Datura stramonium, weeds of the genus Malvaceae, such as Abutilor theophrosti and Side spinosa, weeds of the genus Convolvulaceae, such as Ipomoea spps., For example, Ipomoea purpurea and Calystegia spps., Weeds of the genus Amaranthus lividus and Amaranthus viridis, weeds of the genus Compositae, such as Xanthium strumarium, Amborosia artemisaefolia, Helianthus annuu, Galinsoga ciliat, Girsium arvense, Senecio vulgaris goryufera and Erigeru , Sinapis arvensis and Gapsella Bursapastris, weeds of the genus Polygonaceae, such as Polygonum Blumei and Polygonum convolvlus, weeds of the genus Portu lacaceae, such as Portulaca oleracea, weeds of the genus Chenopodiaceae, such as Chenopodium album, Chenopodium ficifolium and Kochia scoparis, weeds of the genus Caryophyllaceae, such as Stellaria media, weeds of the genus Scrophulariaceae, such as Veronica persica, weeds of the genus Commelinaceae, such as Commeeina labisis like Lamium amplexicaule and Lamium purpureum, weeds of the genus Euphorbiaceae, such as Euphorbia supina and Euphorbia maculata, weeds of the genus Rubiaceae, such as Galium spurium, Galium aparine and Rubia akane, weeds of the genus Violaceae, such as Viola arvensis, weeds of the genus Leg exaltata and Gassia obtusifolia, Graminaceous weeds such as Sorgham bicolor, Panicum dichotomiflorum, Sorghum halepense, Echinochloa crus-galli, Digitaria adscendens, Avena fat ua, Eleusine indica, Setaria viridis and Alopecurus aequalis, and weeds of the genus Cyperaceous, such as Cyperus rotundas and Cyperus esculentus.

 Further, the compound according to the invention can be used as a herbicide for flooded fields, and the introduction of this compound is carried out in any way, for example, during tillage or by spraying. Flooded weeds include, for example, weeds of the genus Alismataceae, such as Alisma canaliculatum, Saqittaria trifolia and Saqittaria pygmaea, weeds of the genus Cyperaceae, such as Cyperus difformis, Cyperus serotinus, Scirpus juncoides, and Eleocharis kurocerema pyuridaemaeraaria daemata Potenderiaceae weeds, such as Monochoria vaginalis, Potamogetonaceae weeds, such as Potamogeton distinetus, Lythraceae weeds, such as Rotala indica, and Gramineae weeds, such as Echinochloa crus galli.

 The proposed compound can be used not only to control various weeds on agricultural fields and in orchards, such as fields on highlands, flooded fields or orchards, but also on non-agricultural fields, such as sports fields, wastelands or roadsides.

 The compound of the invention is readily prepared by reactions according to schemes 1 to 5.

 Reaction scheme N 1.

(2)
Q - H (3)

В вышеприведенных формулах Q, G и L имеют вышеуказанные значения, а Z представляет собой атом галогена.

(2)
Q - H (3)

In the above formulas, Q, G and L have the above meanings, and Z represents a halogen atom.

 Namely, amine (2) is reacted with chlorosulfonyl isocyanate in a solvent such as tetrahydrofuran, dimethoxyethane, acetonitrile, propionitrile, dimethylformamide, dichloromethane, dichloroethane, benzene or toluene, and then react with imine (3) or (4) in the presence of a base such as triethylamine, pyridine, sodium hydride, sodium methoxide, sodium ethoxide, sodium hydroxide, potassium hydroxide or potassium carbonyl, to obtain the compound of the invention (1: X = 0).

 Reaction scheme N 2.

В вышеприведенных формулах Q, G, L и Z имеют вышеуказанные значения, а Y представляет собой C_1-6 алкильную группу или фенильную группу.

In the above formulas, Q, G, L and Z have the above meanings, and Y represents a C _1-6 alkyl group or a phenyl group.

 Namely: the interaction of the imine (3) or (4) with phenyl-N-chlorosulfonylcarbamate (5: Y = phenyl group) or with alkyl-N-chlorosulfonylcarbamate (5: Y = lower alkyl) is carried out using the carbamate derivative (5) in the amount of from 0.5 to 3.0 mol per mol of imine (3) or (4). It is preferable to use imine in an amount of from 0.9 to 1.2 mol.

The reaction temperature is chosen arbitrarily, the reaction can take place at temperatures ranging from -50 ^o C to 100 ^o C, but it is desirable to carry out the reaction at temperatures from -20 ^o C to 30 ^o C.

 This reaction can be carried out using various bases. The amount of base may be from 0.5 to 4.0 mol per mol of imine (3) or (4).

 A suitable base may be, for example, an organic base such as triethylamine or pyridine, a metal hydride such as sodium hydride, an inorganic base such as sodium hydroxide, potassium hydroxide or potassium carbonate, or a metal alkoxide such as sodium methoxide or sodium ethoxide.

 A solvent suitable for this reaction is a solvent inert to the reaction, for example, an aromatic hydrocarbon such as benzene, toluene or xylene, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as ethyl ether, isopropyl ether, dioxane or tetrahydrofuran, a nitrile such as acetonitrile or propionitrile, a hydrocarbon such as petroleum ether, pyrobenzene or n-hexane, a ketone such as acetone or methyl ethyl ketone, an ester such as ethyl acetate or an amide, such as dimethylformamide, dimethylacetamide or hexamethylphosphoric triamide.

 These solvents can be used individually or in combination or in mixtures.

 Most preferred is an ether or amide.

 Then, phenyl-N-substituted-iminosulfonylcarbamate (6: X = 0, Y = phenyl group) or alkyl-N-substituted-iminosulfonylcarbamate (6: X = 0, Y = lower alkyl) and compound (2) are heated in a solvent such like benzene, toluene or dioxane, to obtain the compounds of the invention (1: X = 0).

 Reaction scheme N 3.

В вышеприведенных формулах Q. G, L и Y имеют вышеуказанные значения.

In the above formulas, Q. G, L, and Y have the above meanings.

 The substituted iminsulfonamide derivative (7) is reacted with the carbamate derivative (8) in a solvent such as acetone, acetonitrile or dioxane in the presence of an inorganic base such as potassium carbonate or an organic base such as triethylamine or 1,8-diazabicyclo [5.4.0 ] -7-ugadecene (DBU) to obtain the compounds of the present invention (1: X = 0).

 Reaction scheme N 4.

В вышеприведенных формулах Q, G, L, X и Y имеют вышеуказанные значения.

In the above formulas, Q, G, L, X, and Y have the above meanings.

 The substituted iminosulfonamide derivative (7) is reacted with a (thio) chloroformate or with a (thio) carbonic ester in a solvent such as acetone, methyl ethyl ketone, acetonitrile, dioxane or tetrahydrofuran in the presence of a base such as potassium carbonate, triethylamine or pyridine, to obtain the compound (6), which is then heated together with the compound (2) in a solvent such as toluene, benzene or dioxane, to obtain the compound according to the invention (1).

 Reaction scheme N 5.

В вышеприведенных формулах Q и G имеют вышеуказанные значения.

In the above formulas, Q and G have the above meanings.

 The substituted iminosulfonamide derivative (7) is reacted with the isothiocyanate derivative (9) in a solvent such as acetone, acetonitrile, dioxane or tetrahydrofuran in the presence of an inorganic base such as potassium carbonate or an organic base such as triethylamine or DBU to give the compound according to the present invention (1: X = S, L = H).

The intermediate compounds used in the present invention, i.e. a substituted iminosulfonamide derivative (7), phenyl-N-substituted-iminosulfonyl (thio) carbamate (6: Y = phenyl group) and alkyl-N-substituted-iminosulfonyl (thio) carbamate (6: Y = C _1-6 alkyl), are also new compounds.

 The substituted iminosulfonamide derivative (7) can be synthesized from imine (3) or (4) by the methods indicated in reaction schemes NN 6 and 7.

 Reaction scheme N 6.

В вышеприведенных формулах Q и Z имеют вышеуказанные значения.

In the above formulas, Q and Z have the above meanings.

 According to reaction scheme N 6, the interaction of tert-butanol with chlorosulfonyl isocyanate can be carried out by a method that is known per se, for example, by the method described in Japanese Patent Publication No. 101323/1975.

 The interaction of imine (3) or (4) with tert-butyl sulfamoyl chloride is carried out using tert-butyl sulfamoyl chloride in an amount of from 0.5 to 3.0 mol per mol of imine (3) or (4). It is preferable to use from 0.9 to 1.2 mol.

The reaction temperature is chosen arbitrarily, it should be in the range from -50 ^o C to 100 ^o C. Preferably the temperature should be from -20 ^o C to 30 ^o C.

 This reaction can be carried out using various bases. The amount of base is from 0.5 to 4.0 mol per mol of imine (3) or (4). Preferably, the amount of base should be in the range of 0.8 to 2.5 mol. A suitable base can be, for example, a metal hydride, such as sodium hydride, an organic base, such as triethylamine or pyridine, an inorganic base, such as sodium hydroxide, potassium hydroxide or potassium carbonate, or a metal alkoxide, such as sodium methoxide or sodium ethoxide.

 A solvent suitable for the reaction is a solvent inert to the reaction, for example, an aromatic hydrocarbon such as benzene, toluene or xylene, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as ethyl ether, isopropyl ether, dioxane or tetrahydrofuran, a nitrile such as acetonitrile or propionitrile, a hydrocarbon such as petroleum ether, pyrobenzene or n-hexane, a ketone such as acetone or methyl ethyl ketone, an ester such as ethyl acetate, or an amide such as dimethylformamide, dimethylacetamide or hexamethylphosphoric triamide.

 These solvents can be used individually and in a mixture. Most preferred are ether or amide.

 Reaction scheme N 7.

В вышеприведенных формулах Q имеет вышеуказанное значение.

In the above formulas, Q has the above meaning.

 According to reaction scheme N 7, the removal of the tert-butyl group is carried out using trifluoroacetic acid.

 The amount of trifluoroacetic acid is chosen arbitrarily from an equimolar amount to an excess. Trifluoroacetic acid can be used as a solvent.

The reaction temperature is arbitrarily selected from temperatures ranging from -50 ^° C to 80 ^° C. Preferably, from temperatures ranging from -20 ^° C to 30 ^° C.

 If a solvent is used for this reaction, then the solvent must be inert for the reaction, for example, such a solvent may be an aromatic hydrocarbon such as benzene, toluene or xylene, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such such as ethyl ether, isopropyl ether, dioxane or tetrahydrofuran, nitrile such as acetonitrile or propionitrile, a hydrocarbon such as petroleum ether, pyrobenzene or n-hexane, a ketone such as acetone or methyl ethyl ketone, an ester such as ethyl acetate, or an amide such as dimethylformamide, dimethylacetamide or hexamethylphosphoric triamide. These solvents can be used individually or in a mixture.

 According to the reaction scheme, N 2 phenyl-N-chlorosulfonylcarbamate (5: Y = phenyl group) and alkyl-N-chlorosulfonylcarbamate (5: Y = lower alkyl) can be synthesized in a known manner, for example, by the method described in Chemiche Berichte, no. 96, p. 56 (1963).

 For the above reaction, imines (3) and (4) can be used as starting materials; these imines can be synthesized by the method described in US patent N 4237302, in publications published in the Chemical Society, p.307 (1956), Chemical and Pharmaceutical Bulletin, no. 26, p. 3658 (1978), Journal of organie chemistry, issue 30, p. 4298 (1965), in East German patent N 291 757, in Journal of American Chemical Society, issue 93, p. 552 (1971 ), in US patent N 4 054 652, in UK patent N 752 003, in Chemische Berichte, issue 92, p. 1928 (1959), in Journal of Medicinal Chemistry, issue. 6, p. 266 (1963), Chemical Abstracts, no. 64, 14171e (1996 and Belgian Patent No. 654,416.

 Examples of synthesis schemes for 2-imino-3-ethoxythiazolidine hydrobromide, 2-imino-3-n-propoxythiazolidine hydrobromide and 2-imino-3-methoxy-4,5-dimethylthiazoline hydrochloride are shown (see reaction schemes NN 8 , 9 and 10).

Optimum Embodiment
Now we turn to a detailed description of the synthesis of compounds of the invention in the form of reference and working examples. The present invention is not limited to the following specific examples.

 Reference example a-1.

 Obtaining 2-imino-3-methylthiazole-4-in-hydroiodide.

В 125 мл диметилформамида растворили 50 г (0,5 моль) 2-аминотиазола и добавили при комнатной температуре 90 г (0,63 моль) метилиодида. Смесь перемешивали при комнатной температуре в течение 48 ч. Затем в реакционную смесь добавили 1000 мл этилацетата. Образовавшиеся кристаллы собрали фильтрацией, промыли этилацетатом и высушили до получения 105 г 2-имино-3-метилтиазол-4-ин-гидроиодида.

50 g (0.5 mol) of 2-aminothiazole were dissolved in 125 ml of dimethylformamide and 90 g (0.63 mol) of methyl iodide was added at room temperature. The mixture was stirred at room temperature for 48 hours. Then, 1000 ml of ethyl acetate was added to the reaction mixture. The resulting crystals were collected by filtration, washed with ethyl acetate and dried to obtain 105 g of 2-imino-3-methylthiazole-4-in-hydroiodide.

Melting point: 181-183 ^o C.

 2-imino-3-methylthiazol-4-in-hydroiodide was neutralized with potassium carbonate to obtain 2-imino-3-methylthiazol-4-in.

Boiling point: 55-60 ^o C at a pressure of 1 mm Hg

 Reference example a-2.

 Obtaining 2-imino-3-n-butylthiazolidine.

В 25 мл диметилформамида растворили 8,2 г (80 ммоль) 2-амино-2-тиазолидина и при комнатной температуре добавили 18,4 г (100 ммоль) n-бутил-иодида. Реакционную смесь нагревали и перемешивали при 60^oC в течение 10 ч, затем оставляли охлаждаться до комнатной температуры. В реакционную смесь добавили 300 мл этилацетата и перемешивали при комнатной температуре в течение 10 мин. Образовавшееся маслянистое вещество отделяли декантацией от раствора этилацетата; эту операцию проводили дважды. Затем этилацетат, содержащий маслянистое вещество, отгоняли при пониженном давлении до получения 2-имино-3-n-бутилтиазолидин-гидроиодида в виде неочищенного продукта реакции.

8.2 g (80 mmol) of 2-amino-2-thiazolidine was dissolved in 25 ml of dimethylformamide, and 18.4 g (100 mmol) of n-butyl iodide was added at room temperature. The reaction mixture was heated and stirred at 60 ^° C. for 10 hours, then allowed to cool to room temperature. 300 ml of ethyl acetate was added to the reaction mixture and stirred at room temperature for 10 minutes. The resulting oily substance was separated by decantation from a solution of ethyl acetate; this operation was performed twice. Then, ethyl acetate containing an oily substance was distilled off under reduced pressure to obtain 2-imino-3-n-butylthiazolidine hydroiodide as a crude reaction product.

Thereafter, 2-imino-3-n-butylthiazolidine hydroiodide was stirred with 5.28 g (80 mmol) of 85% potassium hydroxide in 300 ml of methanol at room temperature for 1 hour. Methanol was distilled off under reduced pressure. Then 200 ml of chloroform was added to the residue, insoluble matter precipitated was removed by filtration. Chloroform was distilled off under reduced pressure to obtain 6.9 g of 2-imino-3-n-butylthiazolidine, which was obtained by distillation under reduced pressure. Boiling point: 85-89 ^o C / 0.26 torr.

 Reference example a-3.

 Obtaining 2-imino-1,3-dimethylamidazole-4-in-hydrochloride.

16,9 г (150 ммоль) креатинина растворили в 100 мл N, N = диметилформамида. Затем добавили 27,6 г (194 ммоль) метилиодида, нагрели смесь до 50^oC и перемешивали при этой температуре в течение 2 ч, а после этого - при комнатной температуре перемешивали смесь в течение ночи. В реакционную смесь добавили 500 мл этилацетата и выпавшие кристаллы собрали фильтрацией. Полученные кристаллы промыли этилацетатом и высушили до получения 26,2 г 2-имино-1,3-диметилимидазолидин-4-он-гидроиодида в виде белого кристаллического вещества.

16.9 g (150 mmol) of creatinine was dissolved in 100 ml of N, N = dimethylformamide. Then, 27.6 g (194 mmol) of methyl iodide were added, the mixture was heated to 50 ^° C and stirred at this temperature for 2 hours, and then the mixture was stirred at room temperature overnight. 500 ml of ethyl acetate was added to the reaction mixture, and the precipitated crystals were collected by filtration. The resulting crystals were washed with ethyl acetate and dried to obtain 26.2 g of 2-imino-1,3-dimethylimidazolidin-4-one hydroiodide as a white crystalline solid.

 Then 150 ml of a methanol solution containing 5.17 g (78.4 mmol) of 85% potassium hydroxide, 20 g (78.4 mmol) of 2-imino-1,3-dimethylimidazolidin-4-one-hydroiodide was added and the mixture was stirred at room temperature for 20 minutes The solvent was distilled off under reduced pressure. Then, 200 ml of chloroform was added to the residue, insoluble matters were filtered off. The filtrate was dried with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 9.0 g of 2-imino-1,3-dimethylimidazolidin-4-one.

 800 mg (21.0 mmol) of lithium aluminum hydride was suspended in 20 ml of dry tetrahydrofuran and 200 ml of a solution of dry tetrahydrofuran containing 1.5 g (11.8 mmol) of 2-imino-1,3-dimethyl-imidazolidin-4-one was added , the additive was produced at room temperature. The mixture was stirred at this temperature overnight. Then, 10 ml of ethyl acetate was carefully added to the reaction mixture, and after that, 5 ml of water, insoluble matters were filtered off. The pH of the filtrate was adjusted to 3 with concentrated hydrochloric acid, then the solvent was distilled off under reduced pressure. The resulting crystals were washed with a mixture of solvents: ethyl ether and ethanol, to obtain 1.2 g of 2-imino-1,3-dimethylimidazole-4-in-hydrochloride.

Melting point: 168-171 ^o C
The structure and physical properties of the compounds obtained by the methods of reference examples a-1 to a-3 are presented in table. 13a-1, 13a-2 and 13a-3.

 Reference example b-1.

 Obtaining 2-imino-3-n-propylthiadiazole-4-in-hydroid.

В 40 мл диметилформамида растворили 8,1 г (80 ммоль) 2-аминотиадиазола и при комнатной температуре добавили 17,0 г (100 ммоль) n-пропил-иодида. Смесь нагревали до 60^oC в течение 30 мин, затем оставили охлаждаться, после чего перемешивали при комнатной температуре в течение 24 ч. Затем в реакционную смесь добавили 500 мл этилацетата. Образовавшиеся кристаллы собрали фильтрацией, промыли этилацетатом и высушили до получения 13,1 г искомого 2-имино-3-n-пропилтиадиазол-4-ин-гидроиодида.

8.1 g (80 mmol) of 2-aminothiadiazole was dissolved in 40 ml of dimethylformamide, and 17.0 g (100 mmol) of n-propyl iodide was added at room temperature. The mixture was heated to 60 ^° C. for 30 minutes, then left to cool, and then stirred at room temperature for 24 hours. Then, 500 ml of ethyl acetate was added to the reaction mixture. The resulting crystals were collected by filtration, washed with ethyl acetate and dried to obtain 13.1 g of the desired 2-imino-3-n-propylthiadiazole-4-in-hydroiodide.

Melting point: 121-124 ^o C.

 The structure and physical properties of the compounds obtained by this method in example b-1 are presented in table. 13b.

 Reference example c-1.

 Obtaining 2-imino-3-n-propoxythiazolidine hydrobromide.

22 г (197 ммоль) n-пропоксиамин-гидрохлорида растворили в 100 мл воды и добавили 200 мл этилендихлорида. Затем в несколько порций при охлаждении добавили 27,2 г (197 ммоль) карбоната калия и после этого по капле добавили 21,3 г (196 ммоль) этилхлорформиата, добавку производили при температуре не выше 10^oC. После повышения температуры до комнатной смесь перемешивали в течение 4 ч. Слой этилендихлорида отделяли, затем водный слой дважды экстрагировали 100 мл хлороформа. Слой этилендихлорида и слой хлороформа соединяли и промыли насыщенным водным раствором хлорида натрия, затем высушили безводным сульфатом натрия. После этого растворитель отгоняли при пониженном давлении. В результате перегонки под пониженным давлением получали 27 г этил-N-n-пропоксикарбамата.

22 g (197 mmol) of n-propoxyamine hydrochloride were dissolved in 100 ml of water and 200 ml of ethylene dichloride was added. Then, in several portions, while cooling, 27.2 g (197 mmol) of potassium carbonate was added, and then dropwise added 21.3 g (196 mmol) of ethyl chloroformate, the addition was carried out at a temperature not exceeding 10 ^o C. After increasing the temperature to room temperature, the mixture was stirred for 4 hours. The ethylene dichloride layer was separated, then the aqueous layer was extracted twice with 100 ml of chloroform. The ethylene dichloride layer and the chloroform layer were combined and washed with a saturated aqueous solution of sodium chloride, then dried with anhydrous sodium sulfate. After that, the solvent was distilled off under reduced pressure. Distillation under reduced pressure yielded 27 g of ethyl Nn-propoxycarbamate.

Boiling point 88 ^o C at a pressure of 2.5 mm RT. Art.

8.73 g (218 mmol) of 60% sodium hydride was suspended in 200 ml of dry tetrahydrofuran, then 50 ml of a solution of dry tetrahydrofuran containing 26.7 g (182 mmol) of ethyl Nn-propoxycarbamate was added, the dropwise addition was made under cooling on ice bath (at a temperature not exceeding 10 ^o C). After warming to room temperature, the mixture was stirred for 20 minutes and again cooled in an ice bath. Then 121.4 g (646 mmol) of 1,2-dibromoethane were added, the additive was made in one portion. The temperature was gradually raised and then the mixture was heated under reflux for 2 hours. The mixture was allowed to cool to room temperature, then the solvent was partially distilled off under reduced pressure. The residue was poured into 100 ml of ice water and extracted with 100 ml of chloroform three times. The chloroform layer was washed with a saturated aqueous solution of sodium chloride, then dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and 42.0 g of ethyl N- (2-bromoethyl) -Nn-propoxycarbamate were obtained by distillation under reduced pressure.

Boiling point 97 ^o C at a pressure of 0.4 mm RT. Art.

 A mixture containing 41.7 g (164 mmol) of ethyl N-2 (bromoethyl) -Nn-propoxycarbamate, 16.2 g (213 mmol) of thiourea and 200 ml of ethanol was distilled under reflux for 5 hours. Then the mixture was left cooled and the solvent was distilled off under reduced pressure. After that, 300 ml of chloroform was added to the residue, and the mixture was stirred at room temperature for 10 minutes. After removal of insoluble matter by filtration, chloroform was distilled off under reduced pressure. Ethyl ether and a small amount of water were added to the residue to cause crystallization. The resulting crystals were collected by filtration to obtain 50 g of S- [2- (N-ethoxycarbonyl-N-n-propoxy) aminoethyl] isothiourea hydrobromide.

Melting point 74-76 ^o C.

5.0 g (15.2 mmol) of S- [2- (N-ethoxycarbonyl-Nn-propoxy) aminoethyl] isothiourea hydrobromide and 0.27 g (15.0 mmol) of water were added to 30 ml of a 30% solution hydrogen bromide in acetic acid and the mixture was heated to 55 ^° C and stirred for 4 hours. After that, the mixture was allowed to cool, acetic acid was distilled off under reduced pressure. Ethyl ether and a small amount of ethanol were added to the residue to cause crystallization. The crystals were collected by filtration to obtain 3.8 g of S- [2- (Nn-propoxy) aminoethyl] isothiourea hydrobromide.

Melting point 112-113 ^o C.

 3.8 g (14.7 mmol) of S- [2- (Nn-propoxy) aminoethyl] isothiourea hydrobromide was added to 60 ml of ethanol and the mixture was heated under reflux for 3 hours. The mixture was allowed to cool, then ethanol was distilled off under reduced pressure. pressure. Ethyl ether and a small amount of ethanol were added to the residue to cause crystallization. The crystals were collected by filtration to obtain 3.2 g of 2-imino-3-n-propoxythiazolidine hydrobromide.

Melting point 117-119 ^o C.

 Reference example c-2.

 Preparation of 2-imino-3-methoxy-4-methylthiazole-4-in hydrochloride.

5,67 г (70 ммоль) тиоцианата натрия растворяли в 12 мл воды, раствор нагревали до 80^oC. Затем в раствор в течение часа по капле добавили 5,55 г (60 ммоль) хлорацетона, после чего смесь перемешивали при этой же температуре в течение 3 ч. Смесь охлаждали до комнатной температуры, затем добавляли 60 мл этилового эфира. Водный слой отделяли и удаляли. Слой этилового эфира дважды промывали 10 мл воды, затем растворитель отгоняли под пониженным давлением до получения 6,0 г тиоцианоацетона.

5.67 g (70 mmol) of sodium thiocyanate was dissolved in 12 ml of water, the solution was heated to 80 ^o C. Then, 5.55 g (60 mmol) of chloroacetone was added dropwise to the solution over an hour, after which the mixture was stirred at the same temperature for 3 hours. The mixture was cooled to room temperature, then 60 ml of ethyl ether was added. The aqueous layer was separated and removed. The ethyl ether layer was washed twice with 10 ml of water, then the solvent was distilled off under reduced pressure to obtain 6.0 g of thiocyanoacetone.

 2.30 g (20 mmol) of thiocyanoacetone and 1.67 g (20 mmol) of methoxyamine hydrochloride were dissolved in 10 ml of ethanol, the solution was heated under reflux for 5 hours. Ethanol was distilled off under reduced pressure. Then, 50 ml of ethyl acetate was added to the resulting residue. The precipitated crystals were collected by crystallization to obtain 3.34 g of 2-imino-3-methoxy-4-methylthiazole-4-in hydrochloride.

Melting point 145-155 ^o C (decomposes).

 The structure and physical properties of the compounds obtained by the above methods, according to examples from s-1 to s-2, are presented in table. 13s-1, 13s-2 and 13s-3.

 Reference example d-1.

 Obtaining 3-methyl-2-iminothiazolidin-4-one hydroiodide.

11,6 г (0,1 моль) псевдогидантоина суспендировали в 150 мл диметилформамида и добавили 17 г (0,12 моль) метилиодида. Затем смесь перемешивали при 60^oC в течение часа. После охлаждения смесь вылили в 1000 мл этилацетата, выпавшие кристаллы собрали фильтрацией, получив 15 г 3-метил-2-иминотиазолидин-4-он-гидроиодида в виде бледно-желтых кристаллов.

11.6 g (0.1 mol) of pseudohydantoin was suspended in 150 ml of dimethylformamide and 17 g (0.12 mol) of methyl iodide was added. The mixture was then stirred at 60 ^° C. for one hour. After cooling, the mixture was poured into 1000 ml of ethyl acetate, and the precipitated crystals were collected by filtration to obtain 15 g of 3-methyl-2-iminothiazolidin-4-one hydroiodide as pale yellow crystals.

Melting point 237-238 ^o C.

 Reference example d-2.

 Obtaining 1-methyl-3-n-propyl-2-iminoimidazolidin-4-one hydroiodide.

9,04 г (80 ммоль) креатинина суспендировали в 50 мл диметилформамида, затем добавили 17,0 г (100 моль) n-пропилиодида. Затем смесь нагревали до 70-80^oC при перемешивании до тех пор, пока креатинин полностью не растворился. Смесь оставили охлаждаться, затем добавили 500 мл этилацетата. Выпавшие кристаллы собрали фильтрацией, получив 10,6 г 1-метил-3-n-пропил-2-иминоимидазолидин-4-он-гидроиодида.

9.04 g (80 mmol) of creatinine was suspended in 50 ml of dimethylformamide, then 17.0 g (100 mol) of n-propyl iodide was added. Then the mixture was heated to 70-80 ^o C with stirring until creatinine was completely dissolved. The mixture was allowed to cool, then 500 ml of ethyl acetate was added. Precipitated crystals were collected by filtration to obtain 10.6 g of 1-methyl-3-n-propyl-2-iminoimidazolidin-4-one hydroiodide.

Melting point 159-161 ^o C.

 1-methyl-3-n-propyl-2-iminoimidazolidin-4-one hydroiodide was neutralized as described below to obtain 1-methyl-3-n-propyl-2-iminoimidazolidin-4-one. 2.83 g (10 mmol) of 1-methyl-3-n-propyl-2-iminoimidazolidin-4-one hydroiodide was added in 25 ml of methanol containing 0.66 g (10 mmol) of an 85% potassium hydroxide solution, the mixture was stirred at room temperature for one hour. Methanol was distilled off under reduced pressure, chloroform was added to the residue. Precipitated crystals were removed by filtration. Chloroform was distilled off under reduced pressure to obtain 1.16 g of 1-methyl-3-n-propyl-2-iminoimidazolidin-4-one as an oily substance.

 The structures and physical properties of the compounds obtained by the methods described in reference examples d-1 and d-2 are presented in table. 13d.

 Reference example e-1.

 Preparation of 3,6-dihydro-3-n-propyl-2H-1,3-thiazin-2-imine.

1,3 г (11,4 ммоль) 2-амино-6H-1,3-тиазина растворяли в 4 мл диметилформамида, затем добавили 2,4 г (14,1 ммоль) n-пропилиодида. Смесь нагревали до 50^oC в течение часа, затем перемешивали при комнатной температуре в течение ночи. В реакционный раствор добавили 100 мл этилацетата, смесь перемешали и оставили отстаиваться. Затем слой этилацетата отделили и удалили декантацией. После этого оставшееся маслянистое вещество растворили в 50 мл метанола и при комнатной температуре добавили 30 мл раствора метанола, содержащего 0,75 г (11,4 ммоль) 85% гидроксида калия. Затем смесь перемешивали при той же температуре в течение часа, после чего метанол отогнали под пониженным давлением. В остаток добавили 60 мл хлороформа, нерастворимые вещества удалили фильтрацией. Фильтрат концентрировали под пониженным давлением. Оставшееся маслянистое вещество очищали колоночной хроматографией на кремнеземе (элюент: хлороформ) до получения 0,4 г 3,6-дигидро-3-n-пропил-2H-1,3-тиазин-2-имина в виде маслянистого вещества.

1.3 g (11.4 mmol) of 2-amino-6H-1,3-thiazine was dissolved in 4 ml of dimethylformamide, then 2.4 g (14.1 mmol) of n-propyl iodide was added. The mixture was heated to 50 ^° C. for one hour, then stirred at room temperature overnight. 100 ml of ethyl acetate was added to the reaction solution, the mixture was stirred and left to settle. Then the ethyl acetate layer was separated and removed by decantation. After that, the remaining oily substance was dissolved in 50 ml of methanol and 30 ml of a methanol solution containing 0.75 g (11.4 mmol) of 85% potassium hydroxide was added at room temperature. The mixture was then stirred at the same temperature for one hour, after which methanol was distilled off under reduced pressure. 60 ml of chloroform was added to the residue, insoluble matters were removed by filtration. The filtrate was concentrated under reduced pressure. The remaining oily substance was purified by silica column chromatography (eluent: chloroform) to obtain 0.4 g of 3,6-dihydro-3-n-propyl-2H-1,3-thiazin-2-imine as an oily substance.

 Reference example 2-e.

 Preparation of 3,4,5,6-tetrahydro-3-methyl-2H-1,3-thiazin-2-imine.

3,13 г (27 ммоль) 2-амино-4,5-дигидро-6H-1,3-тиазина растворяли в 20 мл изопропилового спирта и добавили 4,26 г (30 ммоль) метилиодида. Смесь нагревали с обратным холодильником в течение часа, затем оставляли охлаждаться. Растворитель отгоняли под пониженным давлением. Затем растворяли оставшееся маслянистое вещество в 200 мл метанола и добавили 70 мл раствора метанола, содержащего 1,68 г (25,5 ммоль) 85% гидроксида калия, добавку производили при комнатной температуре. Смесь перемешивали при той же температуре в течение 5 мин, затем метанол отгоняли под пониженным давлением. В остаток добавили 300 мл хлороформа, затем высушили безводным сульфатом натрия. Неорганические вещества удаляли фильтрацией, хлороформ отгоняли под пониженным давлением до получения 3 г 3,4,5,6-тетрагидро-3-метил-2H-1,3-тиазин-2-имина в виде бледно-красного маслянистого вещества.

3.13 g (27 mmol) of 2-amino-4,5-dihydro-6H-1,3-thiazine was dissolved in 20 ml of isopropyl alcohol and 4.26 g (30 mmol) of methyl iodide was added. The mixture was refluxed for one hour, then allowed to cool. The solvent was distilled off under reduced pressure. Then the remaining oily substance was dissolved in 200 ml of methanol and 70 ml of a methanol solution containing 1.68 g (25.5 mmol) of 85% potassium hydroxide was added, the addition was carried out at room temperature. The mixture was stirred at the same temperature for 5 minutes, then methanol was distilled off under reduced pressure. 300 ml of chloroform was added to the residue, then dried with anhydrous sodium sulfate. Inorganic substances were removed by filtration, chloroform was distilled off under reduced pressure to obtain 3 g of 3,4,5,6-tetrahydro-3-methyl-2H-1,3-thiazin-2-imine as a pale red oily substance.

 The structure and characteristics of the compounds obtained by the methods described in reference examples e-1 and e-2 are presented in table. 13e-1 and 13e-2.

 Reference example f-1.

 Obtaining 2-imino-3-methyloxazolidine hydroiodide.

15 г (122 ммоль) 2-амино-2-оксазолин-гидрохлорида перемешивали с 8,4 г (128 ммоль) 85% гидроксида калия в 400 мл метанола при комнатной температуре в течение часа. Метанол отгоняли под пониженным давлением, затем добавляли 500 мл хлороформа. Выпавшие в осадок нерастворимые вещества удаляли фильтрацией. Хлороформ отгоняли под пониженным давлением до получения 10,5 г 2-амино-2-оксазолина.

15 g (122 mmol) of 2-amino-2-oxazoline hydrochloride was stirred with 8.4 g (128 mmol) of 85% potassium hydroxide in 400 ml of methanol at room temperature for one hour. Methanol was distilled off under reduced pressure, then 500 ml of chloroform was added. Insoluble matter precipitated was removed by filtration. Chloroform was distilled off under reduced pressure to obtain 10.5 g of 2-amino-2-oxazoline.

 Then 10.5 g of 2-amino-2-oxazoline was dissolved in 40 ml of dimethylformamide and 22 g (155 mmol) of methyl iodide were added, the addition was carried out at room temperature. The mixture was stirred at room temperature for 48 hours. Then, 1000 ml of ethyl acetate was added. The resulting crystals were collected by filtration, washed with ethyl acetate and dried, yielding 23 g of 2-imino-3-methyloxazolidine hydroiodide.

Melting point 165-169 ^o C.

 The structure and characteristics of the compounds obtained by the method described in example f-1 are presented in table. 13f.

 Reference example g-1.

 Obtaining N, N-dimethyl-S-methylisothiourea hydroiodide.

35 г (0,5 моль) N,N-диметилцианамида растворяли в смешанном растворе 70 мл пиридина и 70 мл триэтиламина, затем нагревали раствор до 60^oC. Через смесь в течение 30 мин пропускали газообразный сероводород. Затем реакционную смесь оставляли охлаждаться до комнатной температуры и добавляли 300 мл этилового эфира. Выпавшие в осадок кристаллы собирали фильтрацией и промывали этиловым эфиром до получения 48 г N,N-диметилтиомочевины в виде бледно-коричневых кристаллов.

35 g (0.5 mol) of N, N-dimethylcyanamide were dissolved in a mixed solution of 70 ml of pyridine and 70 ml of triethylamine, then the solution was heated to 60 ^° C. Gaseous hydrogen sulfide was passed through the mixture for 30 minutes. Then the reaction mixture was allowed to cool to room temperature and 300 ml of ethyl ether was added. The precipitated crystals were collected by filtration and washed with ethyl ether to obtain 48 g of N, N-dimethylthiourea in the form of pale brown crystals.

Melting point 163 - 164 ^o C.

 10.4 g (0.1 mol) of N, N-dimethylthiourea was suspended in 80 ml of ethanol and 17 g (0.12 mol) of methyl iodide was added.

 The mixture was refluxed for 30 minutes. Then the reaction mixture was allowed to cool to room temperature, after which the solvent was distilled off under reduced pressure. The resulting crystals were collected by filtration and dried to obtain 20 g of N, N-dimethyl-S-methylisothiourea hydroiodide as yellow crystals.

Melting point 84 - 85 ^o C.

 Reference example g-2.

 Obtaining N-ethyl-N-methyl-S-methylisothiourea hydroiodide.

7,08 г (120 ммоль) N-этил-N-метиламина растворяли в 80 мл сухого ацетона, затем охлаждали раствор до 0^oC. В раствор по капле добавляли 13,1 г (100 ммоль) этоксикарбонилизотиоцианата. Затем температуру реакционной смеси повышали до комнатной и смесь перемешивали в течение 2 ч. Растворитель отгоняли под пониженным давлением. В полученный остаток добавили 80 мл концентрированной соляной кислоты. Температуру реакционной смеси повысили до 80^oC и перемешивали смесь при этой температуре в течение 5 ч. Затем смесь охладили до 0^oC и постепенно добавили карбонат аммония для того, чтобы нейтрализовать реакционную смесь (pH от 6 до 7). После добавки небольшого количества воды смесь трижды экстрагировали 100 мл этилацетата. Слой этилацетата промывали водой и высушивали безводным сульфатом натрия. Затем растворитель отгоняли под пониженным давлением. Полученный кристалл промывали смесью растворителей (этанол/n-гексан) до получения 5,8 г N-этил-N-метилтиомочевины в виде белых кристаллов.

7.08 g (120 mmol) of N-ethyl-N-methylamine was dissolved in 80 ml of dry acetone, then the solution was cooled to 0 ^° C. 13.1 g (100 mmol) of ethoxycarbonyl isothiocyanate was added dropwise. Then the temperature of the reaction mixture was raised to room temperature and the mixture was stirred for 2 hours. The solvent was distilled off under reduced pressure. 80 ml of concentrated hydrochloric acid was added to the resulting residue. The temperature of the reaction mixture was raised to 80 ^° C. and the mixture was stirred at this temperature for 5 hours. Then the mixture was cooled to 0 ^° C. and ammonium carbonate was gradually added in order to neutralize the reaction mixture (pH 6 to 7). After adding a small amount of water, the mixture was extracted three times with 100 ml of ethyl acetate. The ethyl acetate layer was washed with water and dried with anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The resulting crystal was washed with a solvent mixture (ethanol / n-hexane) to obtain 5.8 g of N-ethyl-N-methylthiourea as white crystals.

Melting point 124 - 125 ^o C.

 5.8 g (49 mmol) of N-ethyl-N-methylthiourea was dissolved in 10 ml of N, N-dimethylformamide. At room temperature, 8.8 g (62 mmol) of methyl iodide was added, then the mixture was stirred for 15 hours. 500 ml of ethyl acetate was added to the mixture, and the precipitated crystals were collected by filtration, and then washed with ethyl acetate to obtain 3.1 g of N-ethyl- N-methyl-S-methylisothiourea hydroiodide as pale yellow crystals.

Melting point 94 - 97 ^o C.

 Reference example g-3.

 Obtaining N-methoxy-N-methyl-S-methylisothiourea hydroiodide.

1,83 г (30 ммоль) N-метокси-N-метиламина растворяли в 20 мл дихлорметана, раствор охлаждали до 0^oC. Затем по капле добавляли 3,93 г (30 ммоль) этоксикарбонил-изотиоцианата. После этого температуру смеси повышали до комнатной и смесь перемешивали в течение 15 ч. Растворитель отгоняли под пониженным давлением и в полученный остаток добавляли 20 мл концентрированной соляной кислоты. Температуру реакционной смеси повышали до 80^oC, и смесь перемешивали при этой температуре в течение 5 ч. После этого смесь охлаждали до 0^oC и постепенно добавляли карбонат аммония, чтобы нейтрализовать реакционную смесь (pH от 6 до 7). После добавки 10 мл воды смесь трижды экстрагировали 50 мл этилацетата. Слой этилацетата промывали водой и высушивали безводным сульфатом магния. Затем растворитель отгоняли под пониженным давлением до получения 2,0 г N-метокси-N-метилтиомочевины в виде бледно-желтых кристаллов.

1.83 g (30 mmol) of N-methoxy-N-methylamine was dissolved in 20 ml of dichloromethane, the solution was cooled to 0 ^° C. Then, 3.93 g (30 mmol) of ethoxycarbonyl-isothiocyanate was added dropwise. After that, the temperature of the mixture was raised to room temperature and the mixture was stirred for 15 hours. The solvent was distilled off under reduced pressure, and 20 ml of concentrated hydrochloric acid was added to the obtained residue. The temperature of the reaction mixture was raised to 80 ^° C., and the mixture was stirred at this temperature for 5 hours. After this, the mixture was cooled to 0 ^° C. and ammonium carbonate was gradually added to neutralize the reaction mixture (pH 6 to 7). After adding 10 ml of water, the mixture was extracted three times with 50 ml of ethyl acetate. The ethyl acetate layer was washed with water and dried with anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain 2.0 g of N-methoxy-N-methylthiourea as pale yellow crystals.

Melting point 30 - 32 ^o C.

 1.76 g (14.7 mmol) of N-methoxy-N-methylthiourea were dissolved in 5 ml of N, N-dimethylformamide. At room temperature, 2.09 g (14.7 mmol) of methyloidide was added and the mixture was stirred at the same temperature for 15 hours. Then, 500 ml of ethyl acetate was added and the precipitated crystals were collected by filtration and washed with ethyl acetate to obtain 2.7 g of N- methoxy-N-methyl-S-methylisothiourea hydroiodide as pale yellow crystals.

Melting point 122 - 124 ^o C.

 The structure and physical properties of the compounds obtained by the method described in the reference examples from g-1 to g-3 are presented in table. 13g.

 Example a-1.

 Preparation of 1- (3-methyl-4-thiazolin-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

1,55 г (10 ммоль) 2-амино-4,6-диметоксипиримидина растворяли в 20 мл сухого тетрагидрофурана и по капле добавляли 1,42 г (10 ммоль) хлорсульфонил-изоцианата, добавку производили при температурах от -10 до -5^oC. Температуру реакционной смеси повысили до 0^oC и перемешивали смесь в течение 5 мин. Затем реакционную смесь опять охладили до -30^oC и по капле добавили 1,14 г (10 ммоль) 2-имино-3-метилтиазол-4-ина и 1,11 г (11 ммоль) триэтиламина, растворенного в 10 мл сухого тетрагидрофурана. Температуру реакционной смеси повысили до комнатной и перемешивали смесь в течение часа. Затем растворитель отогнали при пониженном давлении. После этого добавили воду, чтобы получить осадок. Выпавшие в осадок кристаллы собрали фильтрацией и промыли ацетонитрилом до получения 1,5 г искомой 1-(3-метил-4-тиазолин-2-сульфонилимино)-3-(4,6- диметоксипиримидин-2-ил)-мочевины.

1.55 g (10 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 20 ml of dry tetrahydrofuran and 1.42 g (10 mmol) of chlorosulfonyl isocyanate was added dropwise, the addition was carried out at temperatures from -10 to -5 ^o C. The temperature of the reaction mixture was raised to 0 ^° C. and the mixture was stirred for 5 minutes. Then the reaction mixture was again cooled to -30 ^° C. and 1.14 g (10 mmol) of 2-imino-3-methylthiazol-4-in and 1.11 g (11 mmol) of triethylamine dissolved in 10 ml of dry tetrahydrofuran were added dropwise . The temperature of the reaction mixture was raised to room temperature and the mixture was stirred for one hour. Then, the solvent was distilled off under reduced pressure. After that, water was added to obtain a precipitate. The precipitated crystals were collected by filtration and washed with acetonitrile to obtain 1.5 g of the desired 1- (3-methyl-4-thiazolin-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

Melting point 214 - 215 ^o C.

 Example a-2.

 Preparation of 1- (3-n-propyl-4-thiazolin-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

1,55 г (10 ммоль) 2-амино-4,6-диметоксипиримидина растворряли в 30 мл сухого тетрагидрофурана и по капле добавили 1,42 г (10 ммоль) хлорсульфонил-изоцианата, добавку производили при температуре не выше -20^oC. Температуру смеси повысили до 0^oC, затем смесь снова охладили до температуры не выше -20^oC. После этого по капле добавили 2,70 г (10 ммоль) 2-имино-3-n-пропилтиазол-4-ин-гидроиодида и 2,22 г (22 ммоль) триэтиламина, растворенного в 30 мл сухого тетрагирофурана. Температуру реакционной смеси повысили до комнатной, затем смесь перемешивали в течение часа. После этого растворитель отгоняли под пониженным давлением. В остаток добавили воду, смесь трижды экстрагировали хлороформом. Слой хлороформа промыли последовательно водой и насыщенным водным раствором хлорида натрия, затем высушили безводным сульфатом натрия. Растворитель отогнали под пониженным давлением. Полученные кристаллы промыли этиловым эфиром до получения 3 г искомой 1-(3-n-пропил-4-тиазолин-2-сульфонилимино)-3- (4,6-диметоксипиримидин-2-ил)мочевины.

1.55 g (10 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 30 ml of dry tetrahydrofuran and 1.42 g (10 mmol) of chlorosulfonyl isocyanate was added dropwise, the addition was carried out at a temperature not exceeding -20 ^o C. The temperature of the mixture was raised to 0 ^° C., then the mixture was again cooled to a temperature not higher than -20 ^° C. After this, 2.70 g (10 mmol) of 2-imino-3-n-propylthiazole-4-in-hydroiodide was added dropwise and 2.22 g (22 mmol) of triethylamine dissolved in 30 ml of dry tetrahydrofuran. The temperature of the reaction mixture was raised to room temperature, then the mixture was stirred for one hour. After that, the solvent was distilled off under reduced pressure. Water was added to the residue, the mixture was extracted three times with chloroform. The chloroform layer was washed successively with water and a saturated aqueous solution of sodium chloride, then dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting crystals were washed with ethyl ether to obtain 3 g of the desired 1- (3-n-propyl-4-thiazolin-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

Melting point 166 - 167 ^o C.

 Example a-3.

 Preparation of 1- (3-n-butylthiazolidin-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

1,55 г (10 ммоль) 2-амино-4,6-диметоксипиримидина растворяли в 40 мл сухого тетрагидрофурана и по капле при -40^oC добавили 1,42 г (10 ммоль) хлорсульфонил-изоцианата. Температуру реакционной смеси повысили до 0^oC, затем смесь снова охладили до -60^oC. Затем добавили 1,90 г (12 ммоль) 2-имино-3-n-бутилтиазолидина, суспендированного в 40 мл сухого тетрагидрофурана, содержащего 1,33 г (13 ммоль) триэтиламина. Температуру реакционной смеси повысили до комнатной и перемешивали смесь в течение часа. Затем растворитель отогнали под пониженным давлением. В остаток добавили воду и трижды экстрагировали смесь хлороформом. Слой хлороформа промывали последовательно водой и насыщенным водным раствором хлорида натрия, затем высушивали безводным сульфатом натрия. После этого растворитель отогнали под пониженным давлением. Полученные кристаллы промывали этиловым эфиром до получения 2,8 г искомой 1-(3-n-бутилтиазолидин-2-сульфониламино)-3-(4,6-диметоксипиримидин- 3-ил)мочевины.

1.55 g (10 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 40 ml of dry tetrahydrofuran and 1.42 g (10 mmol) of chlorosulfonyl isocyanate was added dropwise at -40 ^° C. The temperature of the reaction mixture was raised to 0 ^° C., then the mixture was again cooled to -60 ^° C. Then, 1.90 g (12 mmol) of 2-imino-3-n-butylthiazolidine suspended in 40 ml of dry tetrahydrofuran containing 1.33 was added. g (13 mmol) of triethylamine. The temperature of the reaction mixture was raised to room temperature and the mixture was stirred for one hour. Then, the solvent was distilled off under reduced pressure. Water was added to the residue, and the mixture was extracted three times with chloroform. The chloroform layer was washed successively with water and a saturated aqueous solution of sodium chloride, then dried with anhydrous sodium sulfate. After that, the solvent was distilled off under reduced pressure. The resulting crystals were washed with ethyl ether to obtain 2.8 g of the desired 1- (3-n-butylthiazolidin-2-sulfonylamino) -3- (4,6-dimethoxypyrimidin-3-yl) urea.

Melting point 139 - 140 ^o C.

 Example a-4.

 Preparation of 1- (1,3-dimethyl-4-imidazolin-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

540 мг (3,46 ммоль) 2-амино-4,6-диметоксипиримидина растворяли в 30 мл сухого тетрагидрофурана и по капле добавили 490 мг (3,46 ммоль) хлорсульфонил-изоцианата, добавку производили при температуре от -20 до -15^oC. Затем температуру реакционной смеси повысили до 0^oC и после этого смесь снова охладили до -20^oC. Затем добавили смесь, состоящую из 600 мг (4,07 ммоль) 2-имино-1,3-диметилимидазол-4-ин-гидрохлорида, 820 мг (8,13 ммоль) триэтиламина и 30 мл сухого тетрагидрофурана. Температуру реакционной смеси повысили до комнатной, и перемешивали смесь при это температуре в течение 3 ч. Затем растворитель отогнали под пониженным давлением. В полученный остаток добавили 60 мл воды, кристаллы собрали фильтрацией. Полученные кристаллы промыли смесью растворителей (этиловый эфир, ацетонитрил и ацетон) до получения 200 мг искомой 1-(1,3-диметил-4-имидазолин-2-сульфонил-имино)-3- (4,6-диметоксипиримидин-2-ил)мочевины.

540 mg (3.46 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 30 ml of dry tetrahydrofuran and 490 mg (3.46 mmol) of chlorosulfonyl isocyanate was added dropwise, the addition was carried out at a temperature of from -20 to -15 ^o C. Then, the temperature of the reaction mixture was raised to 0 ^° C. and then the mixture was again cooled to -20 ^° C. Then a mixture of 600 mg (4.07 mmol) of 2-imino-1,3-dimethylimidazole-4-in was added. -hydrochloride, 820 mg (8.13 mmol) of triethylamine and 30 ml of dry tetrahydrofuran. The temperature of the reaction mixture was raised to room temperature, and the mixture was stirred at this temperature for 3 hours. Then, the solvent was distilled off under reduced pressure. 60 ml of water was added to the obtained residue, and crystals were collected by filtration. The resulting crystals were washed with a mixture of solvents (ethyl ether, acetonitrile and acetone) to obtain 200 mg of the desired 1- (1,3-dimethyl-4-imidazolin-2-sulfonyl-imino) -3- (4,6-dimethoxypyrimidin-2-yl ) urea.

Melting point 201 - 203 ^o C.

 The structure and physical properties of the compounds obtained by the methods described in examples a-1 to a-4 are presented in table. 14a-1, 14a-2, and 14a-3.

 Example b-1

 Preparation of 1- (3-n-propyl-4-thiadiazolin-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

1,55 г (10 ммоль) 2-амино-4,6-диметоксипиримидина растворяли в 40 мл сухого тетрагидрофурана и по капле при температуре -40^oC добавили 1,42 г (10 ммоль) хлорсульфонилизоцианата. Температуру реакционной смеси повысили до 0^oC, после чего смесь опять охладили до -40^oC. Затем добавили 2,58 г (9,5 ммоль) 2-имино-3-n-пропил-тиадиазол-4-ин-гидроиодида, суспендированного в 40 мл сухого тетрагидрофурана, содержащего 2,22 г (22 ммоль) триэтиламина. Температуру реакционной смеси повысили до комнатной, смесь перемешивали в течение часа. Затем растворитель отогнали при пониженном давлении, в полученный остаток добавили воду. Смесь трижды экстрагировали хлороформом. Слой хлороформа последовательно промывали насыщенным водным раствором хлорида натрия и водой, затем высушивали безводным сульфатом натрия. После этого растворитель отогнали под пониженным давлением. Полученные кристаллы промывали ацетонитрилом, получив 2,25 г искомой 1-(3-n-пропил-4-тиадиазолин-2-сульфонилимино) -3-(4,6-диметоксипиримидин-2-ил)мочевины.

1.55 g (10 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 40 ml of dry tetrahydrofuran, and 1.42 g (10 mmol) of chlorosulfonyl isocyanate was added dropwise at a temperature of -40 ^° C. The temperature of the reaction mixture was raised to 0 ^o C, after which the mixture was again cooled to -40 ^o C. Then, 2.58 g (9.5 mmol) of 2-imino-3-n-propyl-thiadiazole-4-in-hydroiodide was added, suspended in 40 ml of dry tetrahydrofuran containing 2.22 g (22 mmol) of triethylamine. The temperature of the reaction mixture was raised to room temperature, the mixture was stirred for one hour. Then, the solvent was distilled off under reduced pressure, and water was added to the obtained residue. The mixture was extracted three times with chloroform. The chloroform layer was washed successively with a saturated aqueous solution of sodium chloride and water, then dried with anhydrous sodium sulfate. After that, the solvent was distilled off under reduced pressure. The resulting crystals were washed with acetonitrile to obtain 2.25 g of the desired 1- (3-n-propyl-4-thiadiazolin-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

Melting point: 189-190 ^o C.

 The structure and physical properties of the compounds obtained by the method described in example b-1 are presented in table. 14b.

 Example c-1

 Preparation of 1- (3-ethoxythiazolidin-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

1,55 г (10 ммоль) 2-амино-4.6-диметоксипиримидина растворяли в 20 мл сухого тетрагидрофурана и по капле при температуре от -10 до -5^oC добавили 1,42 г (10 ммоль) хлорсульфонилизоцианата. Температуру реакционной смеси повысили до 0^oC и перемешивали смесь в течение 5 мин. Реакционную смесь снова охлаждали до -30^oC и постепенно добавили 2,72 г (12 ммоль) 2-имино-3- этокситиазолидингидробромида в 2,43 г (24 ммоль) триэтиламина, суспендированного в 10 мл сухого тетрагидрофурана. Температуру смеси повысили до комнатной, и далее перемешивали смесь в течение 20 мин. Затем растворитель отогнали при пониженном давлении, добавили в полученный остаток воду. Выпавшие в осадок кристаллы трижды экстрагировали 100 мл хлороформа, экстракт промывали один раз 100 мл воды и высушивали безводным сульфатом натрия. Растворитель отогнали при пониженном давлении. Полученные кристаллы промывали этиловым эфиром и ацетонитрилом, получив 2,1 г искомой 1-(3-этокситиазолидин-2- сульфонилимино)-3-(4,6-диметоксипиримидин-2-ил)мочевины.

1.55 g (10 mmol) of 2-amino-4.6-dimethoxypyrimidine was dissolved in 20 ml of dry tetrahydrofuran and 1.42 g (10 mmol) of chlorosulfonyl isocyanate was added dropwise at a temperature of -10 to -5 ^° C. The temperature of the reaction mixture was raised to 0 ^° C. and the mixture was stirred for 5 minutes. The reaction mixture was again cooled to -30 ^° C and 2.72 g (12 mmol) of 2-imino-3-ethoxythiazolidine hydrobromide in 2.43 g (24 mmol) of triethylamine suspended in 10 ml of dry tetrahydrofuran were gradually added. The temperature of the mixture was raised to room temperature, and then the mixture was stirred for 20 minutes. Then, the solvent was distilled off under reduced pressure, water was added to the obtained residue. The precipitated crystals were extracted three times with 100 ml of chloroform, the extract was washed once with 100 ml of water and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting crystals were washed with ethyl ether and acetonitrile to obtain 2.1 g of the desired 1- (3-ethoxythiazolidin-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

Melting point 175-176 ^o C.

 Example c-2.

0,62 г (4,0 ммоль) 2-амино-4,6-диметоксипиримидина растворили в 30 мл сухого тетрагидрофурана и по капле при -50^oC добавили 0,57 г (4,0 ммоль) хлорсульфонил-изоцианата. Температуру реакционной смеси повысили до комнатной и потом опять охладили смесь до -50^oC. После этого добавили 1,2 г (5,0 ммоль) 2-имино-3-n-пропокси-тиазолидин-гидробромида, суспендированного в 20 мл сухого тетрагидрофурана, содержащего 1,01 г (10,0 ммоль) триэтиламина. Температуру реакционной смеси постепенно повысили до комнатной, смесь перемешивали в течение 10 мин. Затем растворитель отгоняли при пониженном давлении, в полученный остаток добавили воду. Смесь трижды экстрагировали 50 мл хлороформа. Слой хлороформа промывали насыщенным водным раствором хлорида натрия и высушили безводным сульфатом натрия. Затем растворитель отгоняли при пониженном давлении. В полученный остаток добавили этиловый эфир и небольшое количество ацетонитрила, чтобы вызвать кристаллизацию. Кристаллы собрали фильтрацией, получив 0,65 г искомой 1-(3-n- пропокситиазолидин-2-сульфонилимино)-3-(4,6-диметоксипиримидин-2- ил)мочевины.Preparation of 2- (3-n-propoxythiazolidin-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea

0.62 g (4.0 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 30 ml of dry tetrahydrofuran, and 0.57 g (4.0 mmol) of chlorosulfonyl isocyanate was added dropwise at -50 ^° C. The temperature of the reaction mixture was raised to room temperature and then the mixture was again cooled to -50 ^° C. After this, 1.2 g (5.0 mmol) of 2-imino-3-n-propoxy-thiazolidine-hydrobromide suspended in 20 ml of dry tetrahydrofuran were added. containing 1.01 g (10.0 mmol) of triethylamine. The temperature of the reaction mixture was gradually raised to room temperature, the mixture was stirred for 10 minutes. Then, the solvent was distilled off under reduced pressure, and water was added to the obtained residue. The mixture was extracted three times with 50 ml of chloroform. The chloroform layer was washed with a saturated aqueous solution of sodium chloride and dried with anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. Ethyl ether and a small amount of acetonitrile were added to the resulting residue to cause crystallization. The crystals were collected by filtration to obtain 0.65 g of the desired 1- (3-n-propoxythiazolidin-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

Melting point 173 - 175 ^o C.

 Example c-3

 Preparation of 1- (3-n-propoxythiazolidin-2-sulfonylimino) -3- (4,6-dimethoxytriazin-2-yl) urea.

3,76 г (40,0 ммоль) фенола растворяли в 40 мл сухого тетрагидрофурана и по капле при -50^oC добавили 5,66 г (40,0 ммоль) хлорсульфонил-изоцианата. Температуру реакционной смеси повысили до комнатной, затем снова охладили смесь до -50^oC. После этого добавили 10,6 г (44 ммоль) 2-имино-3-пропокситиазолидин- гидробромида, суспендированного в 20 мл сухого ацетонитрила, содержащего 8,08 г (80 ммоль) триэтиламина. Температуру реакционной смеси постепенно повысили до комнатной и перемешивали смесь в течение 10 мин. Затем растворитель отогнали при пониженном давлении и в полученный остаток добавили воду. Смесь трижды экстрагировали 70 мл хлороформа. Слой хлороформа промыли насыщенным водным раствором хлорида натрия и высушили безводным сульфатом натрия. Растворитель отгоняли при пониженном давлении. В полученный остаток добавили для кристаллизации этиловый эфир и небольшое количество воды. Образовавшиеся кристаллы собрали фильтрацией, получив 14 г фенил-N-(3-n-пропокситиазолидин-2- сульфонилимино)карбамата. Затем 0,72 г (2,0 ммоль) полученного карбамата растворили в 30 мл сухого диоксана и добавили 0,23 г (1,5 ммоль) 2-амино-4,6-диметокситриазина. Смесь нагревали с обратным холодильником в течение 4 ч. Растворитель отогнали при пониженном давлении, добавили этиловый эфир и небольшое количество воды, чтобы вызвать кристаллизацию. Образовавшиеся кристаллы собрали фильтрацией, получив 0,3 г искомой 1-(3-n-пропокситиазолидин-2-сульфонилимино)-3-(4,6-диметокситриазин-2- ил)мочевины.

3.76 g (40.0 mmol) of phenol were dissolved in 40 ml of dry tetrahydrofuran and 5.66 g (40.0 mmol) of chlorosulfonyl isocyanate was added dropwise at -50 ^° C. The temperature of the reaction mixture was raised to room temperature, then the mixture was again cooled to -50 ^° C. Then, 10.6 g (44 mmol) of 2-imino-3-propoxythiazolidine hydrobromide suspended in 20 ml of dry acetonitrile containing 8.08 g were added. (80 mmol) of triethylamine. The temperature of the reaction mixture was gradually raised to room temperature and the mixture was stirred for 10 minutes. Then, the solvent was distilled off under reduced pressure, and water was added to the obtained residue. The mixture was extracted three times with 70 ml of chloroform. The chloroform layer was washed with a saturated aqueous solution of sodium chloride and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Ethyl ether and a small amount of water were added to the resulting residue to crystallize. The resulting crystals were collected by filtration to obtain 14 g of phenyl-N- (3-n-propoxythiazolidine-2-sulfonylimino) carbamate. Then 0.72 g (2.0 mmol) of the obtained carbamate was dissolved in 30 ml of dry dioxane and 0.23 g (1.5 mmol) of 2-amino-4,6-dimethoxytriazine was added. The mixture was refluxed for 4 hours. The solvent was distilled off under reduced pressure, ethyl ether and a small amount of water were added to cause crystallization. The resulting crystals were collected by filtration to obtain 0.3 g of the desired 1- (3-n-propoxythiazolidin-2-sulfonylimino) -3- (4,6-dimethoxytriazin-2-yl) urea.

Melting point 166 - 167 ^o C.

 Example c-4.

 Preparation of 1- [3- (3-chloroallyloxy) thiazolidin-2-sulfonylimino] - 3- (4-methyl-6-methoxytriazin-2-yl) urea.

0,84 г (6 ммоль) 2-амино-4-метил-6-метокситриазина суспендировали в 20 мл сухого тетрагидрофурана и по капле при комнатной температуре добавили 0,85 г (6 ммоль) хлорсульфонил-изоцианата. Реакция проходила со слабым выделением тепла, и постепенно реакционная смесь превратилась в бледно-желтый раствор. После этого постепенно добавили 1,64 г (6 ммоль) 2-имино-3-(3-хлораллилокси)тиазолидин-гидробромида и 1,43 г (14 ммоль) триэтиламина, суспендированного в 15 мл сухого тетрагидрофурана, смесь перемешивали при комнатной температуре в течение 30 мин. Растворитель отгоняли при пониженном давлении, в полученный остаток добавили воду. Полученное маслянистое вещество трижды экстрагировали 80 мл хлороформа. Экстракт промыли одной порцией воды в 100 мл и высушили безводным сульфатом натрия. Растворитель отогнали при пониженном давлении. Полученные кристаллы промыли этиловым эфиром и ацетонитрилом, получив 1,2 г искомой 1[3-(3-хлораллилокси)-тиазолидин-2-сульфонилимино]-3-(4-метил-6- метокситриазин-2-ил)мочевины.

0.84 g (6 mmol) of 2-amino-4-methyl-6-methoxytriazine was suspended in 20 ml of dry tetrahydrofuran, and 0.85 g (6 mmol) of chlorosulfonyl isocyanate was added dropwise at room temperature. The reaction was carried out with little heat, and gradually the reaction mixture turned into a pale yellow solution. After this, 1.64 g (6 mmol) of 2-imino-3- (3-chloroallyloxy) thiazolidine hydrobromide and 1.43 g (14 mmol) of triethylamine suspended in 15 ml of dry tetrahydrofuran were gradually added, the mixture was stirred at room temperature in within 30 minutes The solvent was distilled off under reduced pressure, and water was added to the obtained residue. The resulting oily substance was extracted three times with 80 ml of chloroform. The extract was washed with one portion of water in 100 ml and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting crystals were washed with ethyl ether and acetonitrile, yielding 1.2 g of the desired 1 [3- (3-chloroallyloxy) thiazolidin-2-sulfonylimino] -3- (4-methyl-6-methoxytriazin-2-yl) urea.

Melting point 145-147 ^o C.

 Example c-5.

 Preparation of 1- (3-methoxy-4-methyl-4-thiazolin-2-sulfonylimino) - -3- (4,6-dimethoxypyrimidin-2-yl) urea.

1,78 г ( 5 ммоль) 2 -амино-4,6-диметоксипиримидина растворили в 10 мл сухого тетрагидрофурана и по капле при температуре от -20 до -15^oC добавили 0,71 г (5 ммоль) хлорсульфонилизоцианата. Температуру смеси повысили до 0^oC, смесь перемешивали в течение 5 мин. Затем смесь снова охладили до -20^oC и добавили 0,90 г (5 ммоль) 2-имино-3-метокси-4-метилтиазол-4-ин-гидрохлорида и 1,11 г (11 ммоль) триэтиламина, суспендированного в 10 мл сухого тетрагидрофурана, добавку производили постепенно. Температуру реакционной смеси повысили до комнатной, смесь перемешивали 20 мин. Растворитель отгоняли при пониженном давлении, в полученный остаток добавили воду. Выпавшие в осадок кристаллы трижды экстрагировали 50 мл хлороформа. Экстракт промыли 50 мл воды и высушили безводным сульфатом натрия. Растворитель отогнали при пониженном давлении. Полученные кристаллы промыли этиловым эфиром и ацетонитрилом, получив 1,02 г искомой 1-(3-метокси-4-метил-4-тиазолидин-2-сульфонилимино)-3- (4,6-диметоксипиримидин-2-ил)-мочевины.

1.78 g (5 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 10 ml of dry tetrahydrofuran and 0.71 g (5 mmol) of chlorosulfonyl isocyanate was added dropwise at a temperature of from -20 to -15 ^° C. The temperature of the mixture was raised to 0 ^° C., the mixture was stirred for 5 minutes. The mixture was then cooled again to −20 ^° C. and 0.90 g (5 mmol) of 2-imino-3-methoxy-4-methylthiazole-4-in-hydrochloride and 1.11 g (11 mmol) of triethylamine suspended in 10 were added. ml of dry tetrahydrofuran, the addition was made gradually. The temperature of the reaction mixture was raised to room temperature, the mixture was stirred for 20 minutes. The solvent was distilled off under reduced pressure, and water was added to the obtained residue. The precipitated crystals were extracted three times with 50 ml of chloroform. The extract was washed with 50 ml of water and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting crystals were washed with ethyl ether and acetonitrile to obtain 1.02 g of the desired 1- (3-methoxy-4-methyl-4-thiazolidin-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

Melting point 183 - 185 ^o C.

 The structure and physical properties of the compounds obtained by the methods described in examples c-1 to c-5 are presented in table. 14c-1, 14c-2 and 14c-3.

 Example d-1

 Preparation of 1- (3-methylthiazolidin-2-one-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

1,55 г (10 ммоль) 2-амино-4,6-диметоксипиримидина растворяли в 30 мл сухого тетрагидрофурана и по капле при температуре от -20^oC до -15^oC добавляли 1,42 г (10 ммоль) хлорсульфонилизоцианата. Температуру реакционной смеси повысили до 0^oC, смесь перемешивали в течение 10 мин. Затем реакционную смесь опять охладили до -30^oC и добавили смесь, содержащую 2,84 г (11 ммоль) 3-метил-2-имино-тиазолидин-4-он-гидроидида, 2,22 г (22 ммоль) триэтиламина и 30 мл сухого тетрагидрофурана. Температуру реакционной смеси повысили до комнатной и перемешивали смесь при этой температуре в течение 20 мин. Затем растворитель отогнали при пониженном давлении и в полученный остаток добавили 100 мл воды. Выпавшие в осадок кристаллы трижды экстрагировали 100 мл хлороформа. Слой хлороформа промыли водой и высушили безводным сульфатом натрия. Затем растворитель отогнали при пониженном давлении. Полученные кристаллы промыли смесью растворителей (этиловый эфир/ацетонитрил) и собрали фильтрацией, получив 1,5 г искомой 1-(3-метиотиазолидин-4-он-2- сульфонилимино)-3-(4,6-диметоксипиримидин-2-ил)мочевины в виде бесцветных кристаллов.

1.55 g (10 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 30 ml of dry tetrahydrofuran, and 1.42 g (10 mmol) of chlorosulfonyl isocyanate was added dropwise at a temperature of from -20 ^° C to -15 ^° C. The temperature of the reaction mixture was raised to 0 ^° C., the mixture was stirred for 10 minutes. Then the reaction mixture was again cooled to -30 ^° C and a mixture was added containing 2.84 g (11 mmol) of 3-methyl-2-imino-thiazolidin-4-one-hydride, 2.22 g (22 mmol) of triethylamine and 30 ml dry tetrahydrofuran. The temperature of the reaction mixture was raised to room temperature and the mixture was stirred at this temperature for 20 minutes. Then, the solvent was distilled off under reduced pressure, and 100 ml of water was added to the obtained residue. The precipitated crystals were extracted three times with 100 ml of chloroform. The chloroform layer was washed with water and dried with anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The resulting crystals were washed with a solvent mixture (ethyl ether / acetonitrile) and collected by filtration to obtain 1.5 g of the desired 1- (3-methiotiazolidin-4-one-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea in the form of colorless crystals.

Melting point 200-201 ^o C.

 Example d-2

 Preparation of 1- (1-methyl-3-n-propylimidazolidin-4-one-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

1,16 г (7,5 ммоль) 2-амино-4,6-диметоксипиримидина растворили в 20 мл сухого тетрагидрофурана и по капле при температуре -40^oC добавили 1,07 г (7,5 ммоль) хлорсульфонил-изоцианата. Температуру реакционной смеси повысили до 0^oC, затем смесь опять охладили до -40^oC. После этого добавили смесь, включающую 1,16 г (7,5 ммоль) 1-метил-3-n-пропил-2-иминоимидазолидин-4-она, 0,83 г (8,2 ммоль) триэтиламина и 20 мл сухого тетрагидрофурана. Температуру реакционной смеси повысили до комнатной и перемешивали смесь в течение 2 ч. Затем растворитель отогнали при пониженном давлении и в полученный остаток добавили 100 мл воды. Смесь трижды экстрагировали 100 мл хлороформа. Затем слой хлороформа промыли водой и высушивали безводным сульфатом натрия. Растворитель отогнали при пониженном давлении и выпавшие в осадок кристаллы промыли смесью растворителей (этиловый эфир-ацетонитил) и собрали фильтрацией, получив 0,16 г искомой 1-(1-метил-3-n-пропилимидазолидин-4-он-2-сульфонилимино)-3- (4,6-диметоксипиримидин-2-ил)мочевины.

1.16 g (7.5 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 20 ml of dry tetrahydrofuran, and 1.07 g (7.5 mmol) of chlorosulfonyl isocyanate was added dropwise at a temperature of -40 ^° C. The temperature of the reaction mixture was raised to 0 ^o C, then the mixture was again cooled to -40 ^o C. After this was added a mixture comprising 1.16 g (7.5 mmol) of 1-methyl-3-n-propyl-2-iminoimidazolidin-4 -one, 0.83 g (8.2 mmol) of triethylamine and 20 ml of dry tetrahydrofuran. The temperature of the reaction mixture was raised to room temperature and the mixture was stirred for 2 hours. Then, the solvent was distilled off under reduced pressure, and 100 ml of water was added to the obtained residue. The mixture was extracted three times with 100 ml of chloroform. Then, the chloroform layer was washed with water and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the precipitated crystals were washed with a mixture of solvents (ethyl ether-acetonityl) and collected by filtration to obtain 0.16 g of the desired 1- (1-methyl-3-n-propylimidazolidin-4-one-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

Melting point 96-98 ^o C. The structure and physical properties of the compounds obtained by the method described in examples d-1 and d-2 are shown in table. 14d.

 Example d-1

 Preparation of 1- (3-methylthiazolidin-2-one-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

1,55 г (10 ммоль) 2-амино-4,6-диметоксипиримидина растворяли в 30 мл сухого тетрагидрофурана и по капле при температуре от -20^oC до -15^oC добавили 1,42 г (10 ммоль) хлорсульфонилизоцианата. Температуру реакционной смеси повысили до 0^oC, смесь перемешивали в течение 10 мин. Затем реакционную смесь опять охладили до -30^oC и добавили смесь, содержащую 2,84 г (11 ммоль) 3-метил-2-имино-тиазолидин-4-он-гидроиодида, 2,22 г (22 ммоль) триэтиламина и 30 мл сухого тетрагидрофурана. Температуру реакционной смеси повысили до комнатной и перемешивали смесь при этой температуре в течение 20 мин. Затем растворитель отогнали при пониженном давлении и в полученный остаток добавили 100 мл воды. Выпавшие в осадок кристаллы трижды экстрагировали 100 мл хлороформа. Слой хлороформа промыли водой и высушили безводным сульфатом натрия. Затем растворитель отогнали при пониженном давлении. Полученные кристаллы промыли смесью растворителей (этиловый эфир/ацетонитрил) и собрали фильтрацией, получив 1,5 г искомой 1-(3-метилтиазолидин-4-он- 2-сульфонилимино)3-(4,6-диметоксипиримидин-2-ил)мочевины в виде бесцветных кристаллов.

1.55 g (10 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 30 ml of dry tetrahydrofuran, and 1.42 g (10 mmol) of chlorosulfonyl isocyanate was added dropwise at a temperature of from -20 ^° C to -15 ^° C. The temperature of the reaction mixture was raised to 0 ^° C., the mixture was stirred for 10 minutes. Then the reaction mixture was again cooled to -30 ^° C. and a mixture was added containing 2.84 g (11 mmol) of 3-methyl-2-imino-thiazolidin-4-one-hydroiodide, 2.22 g (22 mmol) of triethylamine and 30 ml dry tetrahydrofuran. The temperature of the reaction mixture was raised to room temperature and the mixture was stirred at this temperature for 20 minutes. Then, the solvent was distilled off under reduced pressure, and 100 ml of water was added to the obtained residue. The precipitated crystals were extracted three times with 100 ml of chloroform. The chloroform layer was washed with water and dried with anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The resulting crystals were washed with a solvent mixture (ethyl ether / acetonitrile) and collected by filtration to obtain 1.5 g of the desired 1- (3-methylthiazolidin-4-one-2-sulfonylimino) 3- (4,6-dimethoxypyrimidin-2-yl) urea in the form of colorless crystals.

Melting point 200-201 ^o C.

 Example d-2

 Preparation of 1- (1-methyl-3-n-propylimidazolidin-4-one-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

 Example e-1.

 Preparation of 1- (3,6-dihydro-3-n-propyl-2H-1,3-thiazin-2-sulfonyl-imino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

0,32 г (2,06 ммоль) 2-амино-4,6-диметоксипиримидина растворили в 40 мл сухого тетрагидрофурана и раствор охладили до -40^oC. При этой же температуре по капле добавили 0,29 г (2,05 ммоль) хлорсульфонил-изоцианата. Затем температуру повысили до 0^oC. Смесь снова охладили до -40^oC и затем по капле добавили смешанный раствор, включающий 0,4 г (2,56 ммоль) 3,6-дигидро-3-n-пропил-2H-1,3-тиазин-2-имина, 0,26 г (2,57 ммоль) триэтиламина и 40 мл сухого тетрагидрофурана. Смесь постепенно прогрели до комнатной температуры при перемешивании, затем растворитель отогнали при пониженном давлении. В остаток добавили 100 мл воды и после этого смесь дважды экстрагировали 50 мл хлороформа. Слой хлороформа промыли водой и высушили безводным сульфатом натрия. Затем хлороформ отогнали при пониженном давлении. Полученные кристаллы промыли ацетонитрилом, затем этиловым эфиром до получения 0,3 г искомой 1-(3,6-дигидро-3-n-пропил-2H-1,3-тиазин-2- сульфонилимино)-3-(4,6-диметоксипиримидин-2-ил)мочевины.

0.32 g (2.06 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 40 ml of dry tetrahydrofuran and the solution was cooled to -40 ^° C. At the same temperature, 0.29 g (2.05 mmol) was added dropwise. ) chlorosulfonyl isocyanate. The temperature was then raised to 0 ^° C. The mixture was again cooled to -40 ^° C. and then a mixed solution of 0.4 g (2.56 mmol) of 3,6-dihydro-3-n-propyl-2H-1 was added dropwise. , 3-thiazin-2-imine, 0.26 g (2.57 mmol) of triethylamine and 40 ml of dry tetrahydrofuran. The mixture was gradually warmed to room temperature with stirring, then the solvent was distilled off under reduced pressure. 100 ml of water was added to the residue, and then the mixture was extracted twice with 50 ml of chloroform. The chloroform layer was washed with water and dried with anhydrous sodium sulfate. Then, chloroform was distilled off under reduced pressure. The obtained crystals were washed with acetonitrile, then with ethyl ether to obtain 0.3 g of the desired 1- (3,6-dihydro-3-n-propyl-2H-1,3-thiazin-2-sulfonylimino) -3- (4,6- dimethoxypyrimidin-2-yl) urea.

Melting point 161-163 ^o C.

 Example e-2.

 Preparation of 1- (3,4,5,6-tetrahydro-3-methyl-2H-1,3-thiazin-3-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

1,55 г (10 ммоль) 2-амино-4,6-диметоксипиримидина растворили в 30 мл сухого тетрагидрофурана и по капле при температуре от -15^oC до -5^oC добавили 1,42 г (10 ммоль) хлорсульфонилизоцианата. Реакционный раствор нагрели до 0^oC и перемешивали в течение 15 мин. Затем раствор снова охладили до -30^oC и по капле добавили смешанный раствор, состоящий из 1,56 г (12 ммоль) 3,4,5,6-тетрагидро-3-метил-2H-1,3-тиазин-2-имина, 1,21 г (12 ммоль) треэтиламина и 10 мл сухого тетрагидрофурана. Реакционный раствор постепенно прогрели до комнатной температуры при перемешивании, затем растворитель отогнали при пониженном давлении. В остаток добавили 80 мл воды и выпавшие в осадок кристаллы трижды экстрагировали 60 мл хлороформа. Слой хлороформа промыли водой и высушили безводным сульфатом натрия. Затем хлороформ отогнали под пониженным давлением.

1.55 g (10 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 30 ml of dry tetrahydrofuran, and 1.42 g (10 mmol) of chlorosulfonyl isocyanate was added dropwise at a temperature of from -15 ^° C to -5 ^° C. The reaction solution was heated to 0 ^° C and stirred for 15 minutes. Then the solution was again cooled to -30 ^° C and a mixed solution of 1.56 g (12 mmol) of 3,4,5,6-tetrahydro-3-methyl-2H-1,3-thiazin-2- was added dropwise. imine, 1.21 g (12 mmol) of triethylamine and 10 ml of dry tetrahydrofuran. The reaction solution was gradually warmed to room temperature with stirring, then the solvent was distilled off under reduced pressure. 80 ml of water was added to the residue, and the precipitated crystals were extracted three times with 60 ml of chloroform. The chloroform layer was washed with water and dried with anhydrous sodium sulfate. Then chloroform was distilled off under reduced pressure.

 The resulting crystals were washed with a solvent mixture (ethyl ether / acetonitrile) to obtain 1.2 g of the desired 1- (3,4,5,6-tetrahydro-3-methyl-2H-1,3-thiazine-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

Melting point 188-190 ^o C.

 The structure and physical properties of the compounds obtained by the method described in examples e-1 and e-2 are presented in table. 14e-1 and 14e-2.

 Example f-1.

 Preparation of 1- (3-methyloxazolidin-2-sulfonylimino) -3- (4,6-dimethoxypyrimidin-2-yl) urea.

1,55 г (10 ммоль) 2-амино-4,6-диметоксипиримидина растворили в 30 мл сухого тетрагидрофурана и по капле при -20^oC добавили 1,42 г (10 ммоль) хлорсульфонил-изоцианата. Температуру реакционной смеси повысили до -5^oC и перемешивали смесь в течение 5 мин. Затем реакционную смесь снова охладили до -20^oC и добавили смесь, содержащую 2,28 г (10 ммоль) 2-имино-3-метилоксазолидин-гидроиодида, 2,22 г (22 ммоль) триэтиламина и 30 мл сухого тетрагидрофурана. Температуру реакционной смеси повысили до комнатной и перемешивали смесь при этой температуре в течение часа. Затем растворитель отогнали при пониженном давлении и в полученный остаток добавили 100 мл воды. Выпавшие в осадок кристаллы собрали фильтрацией, промыли водой, а затем смесь растворителей (этиловый эфир/ацетонитрил) и высушили, получив 0,8 г искомой 1-(3-метилоксазолидин-2-сульфонилимино)-3-(4,6-диметоксипиридимидин-2-ил) мочевины.

1.55 g (10 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 30 ml of dry tetrahydrofuran, and 1.42 g (10 mmol) of chlorosulfonyl isocyanate was added dropwise at -20 ^° C. The temperature of the reaction mixture was raised to -5 ^° C and the mixture was stirred for 5 minutes. Then the reaction mixture was again cooled to −20 ^° C. and a mixture was added containing 2.28 g (10 mmol) of 2-imino-3-methyloxazolidine hydroiodide, 2.22 g (22 mmol) of triethylamine and 30 ml of dry tetrahydrofuran. The temperature of the reaction mixture was raised to room temperature and the mixture was stirred at this temperature for one hour. Then, the solvent was distilled off under reduced pressure, and 100 ml of water was added to the obtained residue. The precipitated crystals were collected by filtration, washed with water, and then a solvent mixture (ethyl ether / acetonitrile) and dried, yielding 0.8 g of the desired 1- (3-methyloxazolidin-2-sulfonylimino) -3- (4,6-dimethoxypyridimidine- 2-yl) urea.

Melting point 174-175 ^o C.

 The structure and physical properties of the compounds obtained by the method described in example f-1 are presented in table.14f.

 Example g-1.

 Preparation of 1- [N- (methylthio-N, N-dimethylamino) methylene) aminosulfonyl] -3- (4,6-dimethoxypyrimidin-2-yl) urea.

1,55 г (10 ммоль) 2-амино-4,6-диметоксипиримидина растворили в 40 мл сухого тетрагидрофурана и по капле при температуре от -20^oC до -15^oC добавили 1,42 г (10 ммоль) хлорсульфонил-изоцианата. Температуру реакционной смеси повысили до 0^oC и затем смесь опять охладили до -20^oC. После этого добавили 2,5 г (10,2 ммоль) N,N-диметил-S-метилизотиомочевины гидроиодида, 2,22 г (22 ммоль) триэтиламина и 30 мл сухого тетрагидрофурана. Температуру реакционной смеси повысили до комнатной и перемешивали смесь в течение 10 мин. Затем растворитель отогнали при пониженном давлении, в полученный остаток добавили 80 мл воды. Смесь трижды экстрагировали 30 мл хлороформа. Слой хлороформа промыли водой и высушили безводным сульфатом натрия. Затем растворитель отогнали при пониженном давлении. Полученные кристаллы промыли смесью растворителей (этиловый эфир/ацетонитрил), получив 2 г искомой 1-[N-((метилтио-N, N-диметиламино)метилен)аминосульфонил] -3- (4,6-диметоксипиримидин-2-ил)мочевины.

1.55 g (10 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 40 ml of dry tetrahydrofuran, and 1.42 g (10 mmol) of chlorosulfonyl isocyanate was added dropwise at a temperature of from -20 ^° C to -15 ^° C. . The temperature of the reaction mixture was raised to 0 ^° C. and then the mixture was again cooled to -20 ^° C. After this, 2.5 g (10.2 mmol) of N, N-dimethyl-S-methylisothiourea hydroiodide, 2.22 g (22 mmol) were added. ) triethylamine and 30 ml of dry tetrahydrofuran. The temperature of the reaction mixture was raised to room temperature and the mixture was stirred for 10 minutes. Then, the solvent was distilled off under reduced pressure, and 80 ml of water was added to the obtained residue. The mixture was extracted three times with 30 ml of chloroform. The chloroform layer was washed with water and dried with anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The resulting crystals were washed with a solvent mixture (ethyl ether / acetonitrile) to obtain 2 g of the desired 1- [N - ((methylthio-N, N-dimethylamino) methylene) aminosulfonyl] -3- (4,6-dimethoxypyrimidin-2-yl) urea .

Melting point 167-168 ^o C.

 Example g-2.

 Preparation of 2- [N - ((methylthio-N-ethyl-N-methylamino) methylene) amino-sulfonyl] -3- (4,6-dimethoxypyrimidin-2-yl) urea.

1,55 г (10 ммоль) 2-амино-4,6-диметоксипиримидина растворили в 40 мл сухого тетрагидрофурана и по капле при температуре от -20^oC до -15^oC добавили 1,42 г (10 ммоль) хлорсульфонил-изоцианата. Температуру смеси повысили до 0^oC, и смесь снова охладили до -20^oC. Затем добавили смесь, содержащую 2,60 г (10 ммоль) N-этил-N-метил-S-метилизотиомочевины гидрохлорида, 2,22 г (22 моль) триэтиламина и 30 мл сухого тетрагидрофурана. Температуру реакционной смеси повысили до комнатной и перемешивали смесь в течение час. Затем растворитель отогнали при пониженном давлении и в полученный остаток добавили 80 мл воды. Смесь трижды экстрагировали 50 мл хлороформа. Слой хлороформа промыли водой, затем высушили безводным сульфатом натрия. После этого растворитель отогнали при пониженном давлении. Полученные кристаллы промыли ацетонитрилом, получив 1,32 г искомой 1-[N-((метилтио-N-этил-N-метиламино)-метилен)амино-сульфонил]-3- (4,6-диметоксипиримидин-2-ил)мочевины.

1.55 g (10 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 40 ml of dry tetrahydrofuran, and 1.42 g (10 mmol) of chlorosulfonyl isocyanate was added dropwise at a temperature of from -20 ^° C to -15 ^° C. . The temperature of the mixture was raised to 0 ^° C. and the mixture was again cooled to −20 ^° C. Then a mixture was added containing 2.60 g (10 mmol) of N-ethyl-N-methyl-S-methylisothiourea hydrochloride, 2.22 g (22 mol) of triethylamine and 30 ml of dry tetrahydrofuran. The temperature of the reaction mixture was raised to room temperature and the mixture was stirred for one hour. Then, the solvent was distilled off under reduced pressure, and 80 ml of water was added to the obtained residue. The mixture was extracted three times with 50 ml of chloroform. The chloroform layer was washed with water, then dried with anhydrous sodium sulfate. After that, the solvent was distilled off under reduced pressure. The resulting crystals were washed with acetonitrile to obtain 1.32 g of the desired 1- [N - ((methylthio-N-ethyl-N-methylamino) methylene) amino-sulfonyl] -3- (4,6-dimethoxypyrimidin-2-yl) urea .

Melting point 143-144 ^o C.

 Example g-3.

 Preparation of 1- [N - ((methylthio-N-methoxy-N-methylamino) methylene) amino-sulfonyl] -3- (4,6-dimethoxypyrimidin-2-yl) urea.

0,78 г (5 ммоль) 2-амино-4,6-диметоксипиримидина растворили в 20 мл сухого тетрагидрофурана и по капле при температуре от -20^oC до -15^oC добавили 0,71 г (5 ммоль) хлорсульфонил-изоцианата. Температуру реакционной смеси повысили до 0^oC, затем смесь снова охладили до -20^oC. После этого добавили смесь, содержащую 1,31 г (5 ммоль) N-метокси-N-метил-S-метилизотиомочевины гидроиодида, 1,11 г (11 ммоль) триэтиламина и 15 мл сухого тетрагидрофурана. Температуру реакционной смеси повысили до комнатной, смесь перемешивали в течение часа. После этого растворитель отогнали при пониженном давлении, в полученный остаток добавили 40 мл воды. Смесь трижды экстрагировали 25 мл хлороформа. Слой хлороформа промыли водой, высушили безводным сульфатом натрия. Затем растворитель отогнали при пониженном давлении. Полученный кристалл промыли ацетонитрилом, получив 1,51 г искомой 1-[N-((метилтио-N-метокси-N-метиламино)метилен)аминосульфонил]-3- (4,6-диметоксипиримидин-2-ил)мочевины.

0.78 g (5 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 20 ml of dry tetrahydrofuran and 0.71 g (5 mmol) of chlorosulfonyl isocyanate was added dropwise at a temperature of from -20 ^° C to -15 ^° C. . The temperature of the reaction mixture was raised to 0 ^° C., then the mixture was again cooled to -20 ^° C. After this, a mixture containing 1.31 g (5 mmol) of N-methoxy-N-methyl-S-methylisothiourea hydroiodide, 1.11 g was added. (11 mmol) of triethylamine and 15 ml of dry tetrahydrofuran. The temperature of the reaction mixture was raised to room temperature, the mixture was stirred for one hour. After this, the solvent was distilled off under reduced pressure, 40 ml of water was added to the obtained residue. The mixture was extracted three times with 25 ml of chloroform. The chloroform layer was washed with water, dried with anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The resulting crystal was washed with acetonitrile to obtain 1.51 g of the desired 1- [N - ((methylthio-N-methoxy-N-methylamino) methylene) aminosulfonyl] -3- (4,6-dimethoxypyrimidin-2-yl) urea.

Melting point 165-167 ^o C.

 The structure and physical properties of the compounds obtained by the method described in examples g-1 to g-3 are presented in table. 14g.

The following are specific examples of herbicides containing the compounds of the present invention. The scope of the present invention is not limited to these specific examples. In the following examples, the word parts means mass parts
Wettable powder, parts by weight:
The compound according to the invention - 5-80
Solid Carrier - 10-85
Surfactant - 1-10
Others - 1-5
Among other substances, for example, an agent that prevents coagulation may be present.

Emulsifiable concentrate, parts by weight:
The compound according to the invention - 1-30
Liquid carrier - 30-95
SAW - 5-15
Flowable herbicide, parts by weight:
The compound according to the invention - 5-70
Liquid carrier - 15-65
SAW - 5-12
Other - 5-30
Among other substances, for example, a thickening agent may be present.

Granular wettable powder (loose in dry form), parts by weight:
The compound according to the invention - 20-90
Solid Carrier - 10-60
Surfactant - 1-20
Granular herbicide, parts by weight:
The compound according to the invention is 0.1-10
Solid media - 90-99.9
Others - 1-5
An example of the formulation of a-1: wettable powder, parts by weight:
Compound N 1-a according to the invention - 20
Ziklit A (trade name for kaolin clay manufactured by Ziklit Industries Co. Ltd.) - 76
"Soprol 5039" (the trade name for a mixture of nonionic surfactant and anionic surfactant, manufactured by Toho Chemical Industry Co. Ltd.). - 2
"Karpleks" (the trade name for an agent that prevents coagulation and includes white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 2
The above ingredients are crushed to a homogeneous state and mixed until a wettable powder is formed.

Example formulation a-2: wettable powder, parts by weight:
Compound N 2-a according to the invention - 40
Ziklit A (trade name for kaolin clay produced by Ziklit Industries Co. Ltd.) - 54
"Sorpol 5039" (trade name for a mixture of nonionic surfactants and anionic surfactants, manufactured by Toho Chemical Industry Co. Ltd.) - 2
"Karpleks" (trade name for an agent that prevents coagulation and includes white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 4
The above ingredients are crushed to a homogeneous state and mixed until a wettable powder is obtained.

An example of the formulation a-3: emulsifiable concentrate, parts by weight:
Compound N 3-a according to the invention - 5
N, N - dimethylformamide - 15
Xylene - 75
Sorpol 2680 (trade name for a mixture of non-ionic surfactants and anionic surfactants, manufactured by Toho Chemical Industry Co. Ltd.) - 5
The above ingredients are mixed to form an emulsifiable concentrate.

An example of the formulation of a-4: a flowable herbicide, parts by weight:
Compound N 7-a according to the invention - 25
"Argizol S-710" (trade name for a nonionic surfactant manufactured by Kao Corp.) - 10
"Runox 1000C" (trade name of anionic surfactant produced by the company "Toho Chemical Industry Co. Ltd.") - 0.5
1% Rodopol water (trade name of the thickener produced by Ron-Pulenk) - 20
Water - 44.5
The above ingredients are mixed until a flowable herbicide is obtained.

An example of the formulation of a-5: a flowable herbicide, parts by weight:
Compound N 8-a according to the invention - 40
"Agrizol S-710" (trade name of nonionic surfactant manufactured by Kao Corp.) - 10
"Runox 1000C" (trade name of anionic surfactant produced by the company "Toho Chemical Industries Co. Ltd.") - 0.5
1% Rhodopol water (trade name of the thickener produced by Ron-Polens) - 20
The above ingredients are mixed until a flowable herbicide is obtained.

Formulation example a-6: granular wettable powder (free-flowing in dry form), parts by weight:
Compound N 10-a according to the invention - 75
"Isobane N 1" (trade name of anionic surfactant produced by the company "Kurarai Isoprene Chemical Co. Ltd.") - 10
"Varinex N" (trade name for anionic surfactant manufactured by Sanio Kokusaku Pulp Co. Ltd.) - 5
"Karpleks # 80" (trade name for white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 10
The above ingredients are mixed and crushed to obtain a dry bulk powder.

Example formulation a-7: granular herbicide, parts by weight:
Compound N 69-a according to the invention - 1
Bentonite - 55
Talc - 44
The above ingredients are mixed and ground, after adding a small amount of water, the mixture is mixed and granulated using an extruder-type granulator, and then dried to obtain granules.

Formulation example b-1: wettable powder, parts by weight:
Compound N 1-b according to the invention - 20
Ziklit A (trade name for kaolin clay manufactured by Ziklit Industries Co. Ltd.) - 76
"Sorpol 5039" (trade name for a mixture of nonionic surfactants and anionic surfactants, manufactured by Toho Chemical Industry Co. Ltd.) - 2
"Karpleks" (the trade name for an agent that prevents coagulation and includes white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 2
The above ingredients are crushed and mixed until a wettable powder is obtained.

Formulation example b-2: wettable powder, parts by weight:
Compound N 2-b according to the invention - 40
Ziklit A (trade name for kaolin clay manufactured by Ziklit Industries Co. Ltd.) - 54
"Sorpol 5039" (trade name for a mixture of nonionic surfactants and anionic surfactants, manufactured by Toho Chemical Industry Co. Ltd.) - 2
"Karpleks" (trade name for an agent that prevents coagulation and includes white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 4
The above ingredients are crushed and mixed until a wettable powder is obtained.

Formulation example b-3: emulsifiable concentrate, parts by weight:
Compound N 3-b according to the invention - 5
Xylene - 75
N, N-dimethylformamide - 15
"Sorpol 26800" (trade name for a mixture of nonionic surfactants and anionic surfactants, manufactured by Toho Chemical Industry Co. Ltd.) - 5
The above ingredients are mixed to obtain an emulsifiable concentrate.

Formulation Example b-4: Flowable Herbicide, parts by weight:
Compound N 1-b according to the invention - 25
"Agrizol S-710" (trade name of nonionic surfactant, manufactured by Kao Corp.) - 10
"Runox 1000C" (trade name of anionic surfactant manufactured by "Toho Chemical Industry Co. Ltd.") - 0.5
1% Rodopol water (trade name for thickener manufactured by Ron-Paulenk) - 20
Water - 44.5
The above ingredients are mixed until a flowable herbicide is obtained.

Formulation Example b-5: Fluid Herbicide, parts by weight:
Compound N 4-b according to the invention - 40
"Agrizol S-710" (trade name of nonionic surfactant, manufactured by Kao Corp.) - 10
"Runox 1000C" (trade name of anionic surfactant manufactured by "Toho Chemical Industry Co., Ltd.") - 0.5
1% Rodopol water (trade name of the thickener manufactured by Ron-Polenk) - 20
Water - 29.5
The above ingredients are mixed until a flowable herbicide is obtained.

Formulation example b-6: granular wettable powder (free-flowing in dry form), parts by weight:
Compound N 5-b according to the invention - 75
"Isobane N 1" (trade name of anionic surfactant manufactured by "Kurari Isoprene Chemical Co. Ltd.") - 10
"Vanirex N" (trade name for anionic surfactant manufactured by Sanio Kokusaku Pal Co. Ltd.) - 5
"Karpleks # 80" (trade name for white soot produced by Shionogi Pharmacyutical Co. Ltd.) - 10
The above ingredients are mixed and crushed to obtain a dry bulk powder.

Formulation example b-7: granular herbicide, parts by weight:
Compound N 6-b according to the invention - 1
Bentonite - 55
Talc - 44
the above ingredients are mixed and ground, after adding a small amount of water, the mixture is mixed and granulated using an extruder-type granulator, and then dried to obtain granules.

Formulation example c-1: wettable powder, parts by weight:
Compound N 1-c according to the invention - 20
Ziklit A (the trade name for kaolin clay manufactured by Ziklit Industries Co. Ltd.) - 76
"Sorpol 5039" (trade name for a mixture of nonionic surfactants and anionic surfactants, manufactured by Toho Chemical Industry Co. Ltd.) - 2
"Karpleks" (the trade name for an agent that prevents coagulation and includes white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 2
The above ingredients are crushed and mixed until a wettable powder is obtained.

An example of the formulation of c-2: wettable powder, parts by weight:
Compound N 2-c according to the invention - 40
Ziklit A (trade name for kaolin clay manufactured by Ziklit Industries Co. Ltd.) - 54
"Sorpol 5039" (trade name for a mixture of nonionic surfactant and anionic surfactant manufactured by Toho Chemical Industry Co. Ltd.) - 2
"Karpleks" (trade name for an agent that prevents coagulation and includes white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 4
The above ingredients are ground to a homogeneous state and mixed until a wettable powder is obtained.

Formulation Example c-3: Emulsifiable Concentrate, parts by weight:
Compound N 12c according to the invention - 5
Xylene - 75
N, N-dimethylformamide - 15
Sorpol 2680 (trade name for a mixture of non-ionic surfactants and anionic surfactants, manufactured by Toho Chemical Industry Co. Ltd.) - 5
The above ingredients are mixed to obtain an emulsifiable concentrate.

Formulation Example c-4: Fluid Herbicide, parts by weight:
Compound N 24-c according to the invention - 25
"Agrizol S-710" (trade name of nonionic surfactant manufactured by Kao Corp.) - 10
"Runox 1000C" (trade name of anionic surfactant manufactured by "Toho Chemical Industry Co. Ltd.") - 0.5
1% Rodopol water (trade name of Ron-Paulenk thickener manufactured by the company) - 20
Water - 44.5
The above ingredients are mixed until a uniform flowing herbicide is obtained.

An example of the formulation of c-5: a flowable herbicide, parts by weight:
Compound N 37-c according to the invention - 40
"Agrizol S-710" (trade name of nonionic surfactant manufactured by Kao Corp.) - 10
"Runox 1000C" (trade name of anionic surfactant manufactured by "Toho Chemical Industry Co. Ltd.") - 0.5
1% Rodopol water (trade name of the thickener manufactured by Ron-Polenk) - 20
Water - 29.5
The above ingredients are mixed until a uniform flowing herbicide is obtained.

Formulation example c-6: granular wettable powder (loose in dry form), parts by weight:
Compound N 45-c according to the invention - 75
"Isobane N 1; (trade name of anionic surfactant manufactured by Kurarai Isoprene Chemical Co. Ltd.") - 10
"Vanirex N" (trade name for anionic surfactant manufactured by Sanio Kokusaku Pulp Co. Ltd.) - 5
"Karpleks # 80" (trade name for white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 10
The above ingredients are mixed and crushed to obtain a dry bulk powder.

Formulation Example c-7: Granular Herbicide, parts by weight:
Compound N 48-c according to the invention - 1
Bentonite - 55
Talc - 44
The above ingredients are mixed and crushed, after the addition of a small amount of water, the mixture is mixed and granulated using an extruder type granulator, and then dried to obtain granules.

An example of the formulation of d-1: wettable powder, parts by weight:
Compound N 1-d according to the invention - 20
Ziklit A (trade name for kaolin clay manufactured by Ziklit Industries Co. Ltd.) - 76
"Sorpol 5039" (trade name for a mixture of nonionic surfactant and anionic surfactant manufactured by Toho Chemical Industry Co. Ltd.) - 2
"Karpleks" (the trade name for an agent that prevents coagulation and includes white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 2
The above ingredients are crushed and mixed until a wettable powder is obtained.

An example of the formulation of d-2: wettable powder, parts by weight:
Compound N 2-d according to the invention - 40
Ziklit A (trade name for kaolin clay manufactured by Ziklit Industries Co. Ltd.) - 54
"Sorpol 5039" (trade name for a mixture of nonionic surfactant and anionic surfactant manufactured by Toho Chemical Industry Co. Ltd.) - 2
"Karpleks" (trade name for an agent that prevents coagulation and includes white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 4
The above ingredients are crushed and mixed until a wettable powder is obtained.

An example of the formulation of d-3: emulsifiable concentrate, parts by weight:
Compound N 3-d according to the invention - 5
Xylene - 75
N, N-dimethylformamide - 15
"Sorpol 2680" (trade name for a mixture of nonionic surfactant and anionic surfactant manufactured by Toho Chemical Industry Co. Ltd.) - 5
The above ingredients are mixed until a homogeneous emulsifiable concentrate is obtained.

An example of the formulation of d-4: a flowable herbicide, parts by weight:
Compound N 4-d according to the invention - 25
"Agrizol S-710" (trade name of nonionic surfactant manufactured by Kao Corp.) - 10
"Runox 1000C" (trade name of anionic surfactant manufactured by "Toho Chemical Industry Corp. Ltd.") - 0.5
1% Rodopol water (trade name of Ron-Paulenk thickener manufactured by the company) - 20
Water - 44.5
The above ingredients are mixed until a uniform flowing herbicide is obtained.

An example of the formulation of d-5: a flowable herbicide, parts by weight:
Compound N 5-d according to the invention - 40
"Agrizol S-710" (trade name of nonionic surfactant manufactured by Kao Corp.) - 10
"Runox 10000C" (trade name of anionic surfactant manufactured by Toho Chemical Industry Corp. Ltd.) - 0.5
1% Rodopol water (trade name of Ron-Paulenk thickener manufactured by the company) - 20
Water - 29.5
The above ingredients were mixed to obtain a uniform flowable herbicidal composition.

An example of the formulation of d-6: granular wettable powder (loose in dry form), parts by weight:
Compound N 6-d according to the invention - 75
"Isobane N 1" (trade name of anionic surfactant manufactured by "Kurarai Isopren Chemical Co. Ltd.") - 10
"Vanirex N" (trade name for anionic surfactant manufactured by Sanio Kokusaku Pulp Co. Ltd.) - 5
"Karpleks # 80" (trade name for soot produced by the company "Shionogi Pharmacyutical Co. Ltd.") - 10
The above ingredients are mixed and crushed to obtain a dry bulk powder.

An example of the formulation of d-6: granular composition, parts by weight:
Compound N 9-d according to the invention - 1
Bentonite - 55
Talc - 44
The above ingredients are mixed and crushed, after adding a small amount of water, the mixture is mixed and granulated using an extruder-type granulator, and then dried to obtain granules.

An example of the formulation of e-1: wettable powder, parts by weight:
Compound N 1 according to the invention - 20
Ziklit A (trade name for kaolin clay manufactured by Ziklit Industries Co. Ltd.) - 76
"Sorpol 5039" (trade name for a mixture of nonionic surfactant and anionic surfactant manufactured by Toho Chemical Industry Co. Ltd.) - 2
"Karpleks" (the trade name for an agent that prevents coagulation and includes white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 2
The above ingredients are crushed to a homogeneous mass and mixed to obtain a wettable powder.

An example of the formulation of e-2: wettable powder, parts by weight:
Compound N 2 according to the invention - 40
Ziklit A (trade name for kaolin clay manufactured by Ziklit Industries Co. Ltd.) - 54
"Sorpol 5039" (trade name for a mixture of nonionic surfactant and anionic surfactant manufactured by Toho Chemical Industry Co. Ltd.) - 2
"Karpleks" (trade name of an agent that prevents coagulation and includes white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 4
The above ingredients are crushed and mixed until a wettable powder is obtained.

An example of the formulation of e-3: emulsifiable concentrate, parts by weight:
Compound N 3rd according to the invention - 5
Xylene - 75
N, N-dimethylformamide - 15
Sorpol 2680 (trade name for a mixture of nonionic surfactant and anionic surfactant manufactured by Toho Chemical Industry Co. Lead.) - 5
The above ingredients are mixed to obtain an emulsifiable concentrate.

An example of the formulation of e-4: a flowable herbicidal composition, parts by weight:
Compound N 4 according to the invention - 25
Agrizol S-710 "(trade name of nonionic surfactant manufactured by Kao Corp.) - 10
"Runox 1000C" (trade name of anionic surfactant manufactured by "Toho Chemical Idastri Co. Ltd.") - 0.5
1% Rodopol water (trade name of Ron-Paulenk thickener manufactured by the company) - 20
Water - 44.5
The above ingredients are mixed to obtain a flowable herbicidal composition.

An example of the formulation of e-5: a flowable herbicidal composition, parts by weight:
Compound N 5th according to the invention - 40
"Agrizol S-710" (trade name of nonionic surfactant manufactured by Kao Corp.) - 10
"Runox 1000C" (trade name of anionic surfactant manufactured by "Toho Chemical Industry Co. Ltd.") - 0.5
1% Rodopol water (trade name of Ron-Paulenk thickener manufactured by the company) - 20
Water - 29.5
The above ingredients are mixed to obtain a flowable herbicidal composition.

An example of the formulation of e-6: granular wettable powder (loose in dry form), parts by weight:
Compound N 1 according to the invention - 75
"Isobane N 1" (trade name of anionic surfactant manufactured by "Kurarai Isopren Chemical Co. Ltd.") - 10
"Vanirex N" (trade name for anionic surfactant manufactured by Sanio Kokusaku Pulp Co. Ltd.) - 5
"Karpleks # 80" (trade name for white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 10
The above ingredients are mixed and crushed to obtain a dry bulk powder.

An example of the formulation of e-7: granular composition, parts by weight:
Compound N 5th according to the invention - 1
Bentonite - 55
Talc - 44
The above ingredients are mixed and ground, after adding a small amount of water, the mixture is mixed and granulated using an extruder-type granulator, and then dried to obtain granules.

Example formulations f-1: wettable powder, parts by weight:
Compound N 1-f according to the invention - 20
Ziklit A (trade name for kaolin clay manufactured by Ziklit Idustries Co. Ltd.) - 76
"Sorpol 5039" (trade name for a mixture of nonionic surfactants and anionic surfactants, manufactured by Toho Chemical Industry Co. Ltd.) - 2
"Karpleks" (the trade name for an agent that prevents coagulation and includes white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 2
The above ingredients are ground to a homogeneous state and mixed until a wettable powder is obtained.

Formulation example f-2: wettable powder, parts by weight:
Compound N 2-f according to the invention - 40
Ziklit A (trade name for kaolin clay manufactured by Ziklit Idustries Co. Ltd.) - 54
"Sorpol 5039" (trade name for a mixture of nonionic surfactants and anionic surfactants, manufactured by Toho Chemical Industry Co. Ltd.) - 2
"Karpleks" (trade name for coagulation preventing agent, manufactured by Shionogi Pharmacyutical Co.) - 4
The above ingredients are crushed and mixed until a wettable powder is obtained.

Formulation example f-3: emulsifiable concentrate, parts by weight:
Compound N 1-f according to the invention - 5
Xylene - 75
N, N-dimethylformamide - 15
"Sorpol 2680" (trade name for a mixture of nonionic surfactant and anionic surfactant manufactured by Toho Chemical Industry Co. Ltd.) - 5
The above ingredients are mixed to obtain an emulsifiable concentrate.

Formulation example f-4: flowable herbicidal composition, parts by weight:
Compound N 2 according to the invention - 25
"Agrizol S-710" (trade name of nonionic surfactant manufactured by Kao Corp.) - 10
"Runox 1000C" (trade name of anionic surfactant manufactured by "Toho Chemical Industry Co. Ltd.") - 0.5
1% Rodopol water (trade name of Ron-Paulenk thickener manufactured by the company) - 20
Water - 44.5
The above ingredients are mixed to obtain a flowable herbicidal composition.

Formulation example f-5: flowable herbicidal composition, parts by weight:
Compound N 2 according to the invention - 40
"Agrizol S-710" (trade name of nonionic surfactant manufactured by Kao Corp.) - 10
"Runox 1000C" (trade name of anionic surfactant manufactured by "Toho Chemical Industry Co. Ltd.") - 0.5
1% Rodopol water (trade name of Ron-Paulenk thickener manufactured by the company) - 20
Water - 29.5
The above ingredients are mixed to form a flowable combicidal composition.

"Vanirex N" (trade name for anionic surfactant manufactured by Sanio Kokusaku Palp. Co. Ltd.) - 5
"Karpleks # 80" (trade name for soot produced by the company "Shionogi Pharmacyutical Co. Ltd.") - 10
The above ingredients are mixed and crushed to obtain a dry bulk powder.

Formulation example f-7: granular herbicidal composition, parts by weight:
The compound according to the invention N 2-f - 1
Bentonite - 55
Talc - 44
The above ingredients are mixed and ground, after adding a small amount of water, the mixture is mixed and granulated using an extruder-type granulator, and then dried to obtain granules.

Example formulations g-1: wettable powder, parts by weight:
The compound according to the invention N1-g - 20
Ziklit A (trade name for kaolin clay manufactured by Ziklit Industries Co. Ltd.) - 76
"Sorpol 5039" (trade name for a mixture of nonionic surfactant and anionic surfactant manufactured by Toho Chemical Industry Co. Ltd.) - 2
"Karpleks" (trade name for coagulation-preventing agent, including white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 2
The above ingredients are crushed and mixed until a wettable powder is obtained.

An example of the formulation of g-2: wettable powder, parts by weight:
Compound N 2-g according to the invention - 40
Ziklit A (trade name for kaolin clay manufactured by Ziklit Industries Co. Ltd.) - 54
"Sorpol 5039" (trade name for a mixture of nonionic surfactant and anionic surfactant manufactured by Toho Chemical Industry Co. Ltd.) - 2
"Karpleks" (trade name for an agent that prevents coagulation and includes white soot, manufactured by Shionogi Pharmacyutical Co. Ltd.) - 4
The above ingredients are crushed and mixed until a wettable powder is obtained.

Formulation example g-3: emulsifiable concentrate, parts by weight:
Compound N 3-g according to the invention - 5
Xylene - 75
N, N-dimethylformamide - 15
"Sorpol 2680" (trade name for a mixture of nonionic surfactant and anionic surfactant manufactured by Toho Chemical Industry Co. Ltd.) - 5
The above ingredients are mixed to obtain an emulsifiable concentrate.

Formulation example g-4: flowable herbicidal composition, parts by weight:
Compound N 4-g according to the invention - 25
"Agrizol S-710" (trade name of nonionic surfactant produced by the company "Co. Corp.") - 10
"Runox 10000C" (trade name of anionic surfactant manufactured by Toho Chemical Industries Co. Ltd.) - 0.5
1% of Rodopol water (trade name of Ron-Paulenk thickener) - 20
Water - 44.5
The above ingredients are mixed to obtain a flowable herbicidal composition.

Formulation example g-5: flowable herbicidal composition, parts by weight:
Compound N 5-g according to the invention - 40
"Agrizol S-710" (trade name of non-inogenic surfactant manufactured by Kao Corp.) - 10
"Runox 10000C" (trade name of anionic surfactant manufactured by Toho Chemical Industries Co. Ltd.) - 0.5
1% Rodopol water (trade name of Ron-Paulenk thickener manufactured by the company) - 20
Water - 29.5
The above ingredients are mixed to obtain a flowable herbicidal composition.

Formulation example g-6: granular wettable powder (free-flowing in dry form), parts by weight:
Compound N 12-g according to the invention - 75
"Isobane N 1 (trade name of anionic surfactant manufactured by Kurarai Isoprene Chemical Co. Ltd.") - 10
"Vanirex N" (trade name for anionic surfactant manufactured by Sanio Kokusaku Pulp Co. Ltd.) - 5
"Karpleks # 80" (trade name for soot produced by the company "Shionogi Pharmacyutical Co. Ltd.") - 10
The above ingredients are mixed and crushed to obtain a dry bulk powder.

Formulation example g-7: granular herbicidal composition, parts by weight:
Compound N 19-g according to the invention - 1
Bentonite - 55
Talc - 44
The above ingredients are mixed and crushed, after adding a small amount of water, the mixture is mixed and granulated using an extruder-type granulator, and then dried to obtain granules.

 In use, the above wettable powders, emulsifiable concentrates, flowable compositions or granular wettable powders are diluted 50-100 times with water and used so that the amount of active ingredient is from 0.0001 to 10 kg per hectare.

 The following is a detailed description of the herbicidal action of the compounds of the invention exhibited by these compounds during the tests.

 Test example 1: Test-1 on the herbicidal effect in the process of tillage.

 A plastic box 15 cm long, 22 cm wide and 6 cm deep was filled with sterilized diluvial soil and the seeds of Echinochloa crus-galli, Digitaria adcendens, Cyperus microiria, Solanum nigrum, Galinsoga ciliata, Rorippa indica, Oryza sativa, Zea mesticum, Tritum max, Gossypium spp., after which it was covered with a layer of soil with a thickness of 1.5 cm and the surface was treated with a solution of the herbicide so that the active ingredient was evenly distributed in a given concentration. The herbicide solution was prepared as follows: a wettable powder obtained according to the above recipe examples was diluted with water and the resulting solution was sprayed over the entire surface of the soil. Four weeks after the application of the herbicidal solution, the herbicidal effect for each type of weed and phytotoxicity for each type of crop were determined on the basis of a standard growth rate estimation procedure. The results are presented in table. fifteen.

Standard growth estimates:
5: Suppression (reduction) of growth by more than 90% (almost complete destruction).

 4: Decrease in growth by 70-90%.

 3: Reduced growth by 40-70%.

 2: Decrease in growth by 20-40%.

 1: Decrease in growth by 5-20%.

 0: Decrease in growth by less than 5% (almost no effectiveness).

,
где T - масса сорняков выше уровня поверхности почвы обработанного участка;
N - масса сорняков выше уровня поверхности почвы необработанного участка.The above indicators of growth reduction were calculated using the following equation:

,
where T is the mass of weeds above the soil surface of the treated area;
N is the mass of weeds above the soil surface of the untreated area.

 Test example 2: Test-1 on the herbicidal effect when processing leaves.

 A plastic box 15 cm long, 22 cm wide and 6 cm deep was filled with sterilized diluvial soil and the seeds of Echinochloa crus-galli, Digitaria adscendens, Avena fatua, Cyperus microiria, Solanum nigrum, Galinsoga ciliata, Rorippa indica, Oryzaaysiva were sown individually , Triticum aestivum, Glycinemax, Gossypium spp., Beta vulgaris, after which the seeds were covered with a layer of soil about 1.5 cm thick. When various types of weeds and crops reached a growth stage of 2-3 leaves, the surface of the leaves was uniformly sprayed with a herbicidal solution in this way so that the active ingredient is applied at a predetermined ontsentratsii. A herbicidal solution was prepared by diluting with water a wettable powder obtained in accordance with the above examples of formulations, and thoroughly spraying the entire surface of the leaves of weeds and crops with this solution. Four weeks after spraying, the herbicidal effect for each type of weed and phytotoxicity for each type of crop were determined using the standard growth rate estimation procedure (described in Test Example 1).

 The results are shown in table. sixteen.

 Test Example 3: Test-1 on the herbicidal effect of a herbicide applied during an irrigation process.

Alluvial soil was placed on a 1/5000 acre Wagner growing vessel, then water was poured and the soil was mixed with water until the soil was irrigated by flooding at a water depth of 4 cm. Seeds of Echinochloa crus-galli, Sciprus juncoides, Monochoria vaginalis, Rotala were sown in this vessel indica and planted tubers of Sagittaria pygmeae, Cyperus serotinus. Then, rice shoots were transplanted there at the 2.5-leaf growth stage. The vessel was placed in a greenhouse, where the temperature was maintained at 25-30 ^o C, and plants were grown. On the third day after sowing and planting the plants, a diluted solution of the herbicide was added dropwise through a measuring pipette to the water surface, the herbicide was applied so that the dose was at a predetermined level. Three weeks after the application of the herbicide, the herbicidal effect on different types of weeds and rice was determined on the basis of the standard growth rate estimation procedure (described in test example 1). The results are shown in table. 17.

In the table. 15, 16 and 17, the connection numbers correspond to the connection numbers in the examples, and the letter characters have the following meanings:
A: Echinochloa crus-galli (chicken millet);
B: Digitaria Adscendens (dewdrop);
C: Avena fatua (empty oats);
D: Cyperus Microiria (sedge);
E: Solanum nigrum (black nightshade);
F: Galinsoga ciliata (Galinsoga);
G: Rorippa indica (field cress);
H: Scirpus juncoides (reeds);
I: Monochoria vaginalis;
J: Rotala indica (rotala);
K: Sagittaria pygmaea (arrowhead);
L: Cyperus serotinus (sedge);
a: Oryza sativa (rice);
b: Zea mays (maize);
c: Triticum aestivum (wheat);
d: Glycine max (soybean cultured);
e: Gossypium spp. (cotton);
f: Beta vulgaris (sugar beet).

 Test example 4: Test-2 on herbicidal activity when applying the herbicide in the process of tillage.

 A plastic box 21 cm long, 13 cm wide and 7 cm deep was filled with sterilized diliuvial soil and individually sown with seeds of Echinochloa crus-galli, Setaria virids, Avena fatua, Alopecurus myosuroides, Abutilon theophrasti, Xanthium, Strumarium, Amarantpius viromidius, Veromarium, Amaranthus virids persica, Stellaria media, Zea mays, Oryza sativa, Oryza sativa, Glycine max, Gossypium spp, Triticum aestivum, Beta vulgaris and covered the seeds with a layer of soil about 1.5 cm thick, after which a solution of the herbicide was applied to the soil surface so that the active the ingredient was distributed over the surface in a given concentration. The herbicide solution was obtained by diluting with water a wettable powder obtained in accordance with the above formulation examples; the solution was sprayed onto the soil. Three weeks after the application of the herbicidal solution, on the basis of the standard growth rate estimation procedure (below), the herbicidal action was evaluated for each type of crop. The results are shown in table. 18.

 Some of the compounds of the invention have shown selective effect on certain crops.

Standard growth estimates:
5: Suppression (reduction) of growth by more than 90% (almost complete destruction).

 4: Decrease in growth by 70-90%.

 3: Reduced growth by 40-70%.

 2: Decrease in growth by 20-40%.

 1: Decrease in growth by 5-20%.

 0: Decrease in growth by less than 5% (practical lack of effectiveness).

 Test example 5: Test-2 on the herbicidal effect when processing leaves.

 A plastic box 21 cm long, 13 cm wide and 7 cm deep was filled with sterilized diluvial soil and sowed (separately) with seeds of Echinochloa crus-galli, Setaria viridis, Avena fatua, Alopecurus myosuroides, Abutilon theophrasti, Xanthium strumaridis, Amhus, Amaranth Veronica persica, Stellaria media, Zea mays, Oryza sativa, Glycine max, Gossypium spp, Triticum aestivum, Beta vulgaris and covered the seeds with a layer of soil about 1.5 cm thick. When various weeds and crops sprouted to a 2-3-leaf stage, leafing uniformly sprayed with the herbicidal solution so that the active ingredient is applied at a predetermined concentration. The herbicidal solution was obtained by diluting the wettable powder obtained in accordance with the above examples of formulations, the entire surface of the leaves of weeds and crops was sprayed with water, the resulting solution. Three weeks after spraying, the herbicidal effect for each type of weed and phytotoxicity for each type of crop were determined on the basis of the standard growth rate estimation procedure (described in Example 4). The results are shown in table. 19.

 Test example 6: Test-2 on the herbicidal effect when applying the herbicide at the growth stage during flooding irrigation.

Alluvial soil was placed on a 1/5000 acre Wagner growing vessel, then the water was poured and the soil was mixed with water until the soil was irrigated by flooding at a water depth of 4 cm. Seeds of Echinochloa crus-galli, Scirpus juncoides, Monochoria vaginalis were sown in the above vessel. Rotala indica. The vessel was placed in a greenhouse, where the temperature was maintained at 25-30 ^o C. When Echinochloa crus-galli, Scirpus juncoides, Monochoria vaginalis, rotala indica reached a 1-2-stage growth stage, a diluted herbicide solution was added dropwise to the water surface through a measuring pipette, the herbicide was applied in such a way that its dose was at a predetermined level. Three weeks after the application of the herbicide based on a standard estimate of the growth rate described in Test Example 4, the herbicidal effect of various weed species was visually determined. The results are shown in table. 20.

In the table. 18, 19 and 20, the numbers of the compounds correspond to the numbers of these compounds in the examples, and the letter characters have the following meanings:
A: Echinochloa crus-galli (chicken millet);
B: Setaria viridis (green bristle);
C: Avena fatua (empty oats);
D: Alopecurus myosuroides;
E: Abutilon theopharasti (Theophrastes cable car);
F: Xanthium strumarium (common gimmick);
G: Amaranthus viridis (Amaranth);
H: ipomola spp. (morning glory);
I: Veronica persica (Persian Veronica);
J: Stellaria media (middle stellate);
a: Zea mays (maize);
b: Oryza sativa (rice);
c: Glycine max (soybean cultured);
d: Gossypium spp. (cotton);
e: Triticum aestivum (wheat);
f: Beta vulgaris (sugar beet).

Claims (10)

1. Derivatives of iminosulfonylurea of the formula I or their salts

where Q is

where R ₁ - C ₁ - C ₆ -alkyl, -C ₁ - C ₂ -alkyl-CO ₂ -A group, where A - C ₁ - C ₆ -alkyl, C ₂ - C ₆ -alkenyl, which may be substituted a phenyl group or halogen atoms, a C ₂ - C ₆ alkynyl, CH ₂ - CO - A group, where A has the indicated meanings, C ₁ - C ₂ alkyl-O-alkyl, which may be substituted with a phenyl group, -CH ₂ SA group, where A is defined above, —CH ₂ —CN group, C ₁ - C ₂ -alkylphenyl group, where phenyl may be substituted with alkoxy or halogen atoms;
R ₂ is a hydrogen atom, C ₁ is C ₆ alkyl or phenyl;
R ₃ is hydrogen, C ₁ -C ₆ alkyl or a halogen atom;
R ₄ is C ₁ -C ₆ alkyl, C ₂ is C ₆ alkenyl which may be substituted with halogen atoms, C ₂ is C ₆ alkynyl or CH ₂ OA, where A is as defined, phenyl;
R ₅ is hydrogen or C ₁ -C ₆ alkyl;
R ₆ is C ₁ -C ₆ alkyl;
R ₇ is C ₁ -C ₆ alkyl;
R ₈ is C ₁ -C ₆ alkyl, C ₂ is C ₆ alkenyl, C ₂ is C ₆ alkynyl or —CH ₂ —CO — A is a group wherein A is C ₁ is C ₆ alkyl;
R ₉ is hydrogen or C ₁ -C ₆ alkyl;
R _{1 0} - C ₁ - C ₆ -alkyl, C ₂ - C ₆ -alkynyl, C ₂ - C ₆ -alkenyl, which may be substituted by a benzyl group or halogen atoms;
R _{1 1} is methyl or hydrogen;
R _{1 2} - C ₁ - C ₆ -alkyl, C ₂ - C ₆ -alkenyl, C ₂ - C ₆ -alkynyl, -CH ₂ - CO - A group, -CH ₂ - COO - A group, CH ₂ O - A group or CH ₂ - S - A group, where A has the indicated meanings;
R _{1 3} - C ₁ - C ₆ -alkyl or -CH ₂ - O - A group, where A has the indicated meanings;
R _{1 4} is C ₁ -C ₆ alkyl or C ₂ -C ₆ alkenyl;
R _{1 5} is C ₁ -C ₅ alkyl, C ₂ is C ₆ alkenyl or C ₂ is C ₆ alkynyl;
R _{1 6} - C ₁ - C ₆ -alkyl;
R _{1 7} - C ₁ - C ₆ -alkyl, C ₁ - C ₆ -alkoxy, -CO - A group, where A has the indicated meanings, phenyl or C ₂ - C ₆ -alkenyl, provided that R _{1 6} and R _{1 7} may together form a four-membered alkyl ring;
L is hydrogen or C ₁ -C ₆ alkyl;
group A in the ring — CH — group or nitrogen atom;
B and D are independently C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy or a halogen atom.  2. The compound according to claim 1, where Q is Qa1, qa2 or Qc1.  3. The compound according to claim 1, where Q is Qa1.  4. The compound according to claim 1, where Q is Qa2.  5. The compound according to claim 1, where Q is Qc1. 6. A method of killing or controlling weeds by treating soil or plants with a sulfonylurea derivative, characterized in that a compound of the general formula is used as a sulfonylurea derivative

where q

where R ₁ is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl which may be substituted by a halogen atom, C ₂ -C ₆ alkynyl, -CH ₂ -O-A, -CH ₂ -CO-A , -CH ₂ -S-A, where A is C ₁ -C ₆ alkyl;
R ₂ is hydrogen;
R ₃ is hydrogen, C ₁ -C ₆ alkyl or a halogen atom;
R ₄ is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl which may be substituted by a halogen atom, C ₂ -C ₆ alkynyl or —CH ₂ —O-A, where A has the indicated meanings;
R ₅ is hydrogen or C ₁ -C ₆ alkyl;
R ₆ is C ₁ -C ₆ alkyl;
R ₈ is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl;
R ₉ is hydrogen;
R _{1 0} is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, which may be substituted by a halogen atom or C ₂ -C ₆ alkynyl;
R _{1 2} is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, -CH ₂ -O-A, where A has the indicated meanings;
R _{1 3} - C ₁ -C ₆ -alkyl, -CH ₂ -O-A, where A has the indicated meanings;
R _{1 4} is C ₂ -C ₆ alkenyl;
R _{1 5} is C ₁ -C ₆ alkyl;
R _{1 6} is C ₁ -C ₆ alkyl;
R _{1 7} is C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₂ -C ₆ alkenyl;
L is hydrogen;
group A in the ring — CH group or nitrogen atom;
B and D independently are C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy,
in the amount of 0.04 - 10.0 kg / ha.  7. The method according to claim 6, characterized in that use compound I according to claim 3.  8. The method according to claim 6, characterized in that use compound I according to claim 4.  9. The method according to claim 6, characterized in that use compound I according to claim 5. Priority by signs:
06/28/91 - compounds of formula I, where Q is

where R ₁ is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl substituted with phenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₂ alkyl -CO ₂ - A, where A is C ₁ - C ₆ alkyl;
R ₂ is C ₁ -C ₆ alkyl, phenyl;
R ₃ is hydrogen, C ₁ -C ₆ alkyl, halogen,
or Q-

where R ₄ is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl;
R ₅ is hydrogen;
08/14/91 - a compound of formula I, where Q is

where R ₁ is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, which is substituted by a halogen atom, C ₁ -C ₂ -alkyl-O-alkyl, which may be substituted by phenyl; -CH ₂ SA group, where A is C ₁ -C ₆ alkyl; -CH ₂ CN group,
or Q -

where R ₄ is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, CH ₂ CO-A, where A is C ₁ -C ₆ alkyl;
09/25/91 - compounds of the formula I, where Q is

where R _{1 0} is C ₁ -C ₇ alkyl;
D is C ₁ -C ₆ alkyl. 12/03/91 - compounds of formula I, where Q is

where R _{1 0} is C ₁ -C ₆ -, C ₂ -C ₆ alkenyl;
D is C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy,
or Q -

where R ₆ is C ₁ -C ₆ alkyl;
01/20/92 - compounds of the formula I, where Q is

where R ₁ is C ₁ -C ₂ alkylphenyl, where phenyl may be substituted by alkoxy or halogen atoms, C ₂ -C ₆ alkenyl which may be substituted by halogen atoms, C ₂ -C ₆ alkynyl, C ₁ -C ₂ -alkyl-O-alkyl;
R ₂ and R ₃ are hydrogen,
or Q -

where R ₄ is C ₂ -C ₆ alkenyl which may be substituted by halogen atoms;
R ₅ is hydrogen;
03.24.92 - compounds of the formula I, where Q is

where R _{1 0} is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, which may be substituted with halogen atoms.

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