Derivatives of pyrimidine with herbicide activity, the method of controlling undesirable vegetation

 

(57) Abstract:

Usage: in agriculture, in particular as a means of controlling undesirable vegetation. The inventive product - pyrimidine derivatives of f-crystals 1: , where R1- alkyl - C1-C4, O-alkyl - C1-C4halogen; R2-alkyl - C1-C4, O-alkyl, C1-C4; n = 3 - 5, Z = C(O))HE(O)O-alkyl - C1-C4C(O)=NH=S(O)2(O) -phenyl. Reagent 1: compound f-crystals II: , where L is tsepliaeva group. Reagent 2: compound f-crystals III . Reaction conditions in an inert organic solvent. The method of controlling undesirable vegetation are processing these pyrimidine derivatives, taken in an amount of 1 to 10 mg/ha 2 C. p. F.-ly, 2 tab.

The invention relates to new biologically active compounds - derivatives of pyrimidine, have a weed-killing activity, as well as to a method of controlling undesirable vegetation and may find application in agriculture.

A series of 2-substituted pyrimidine compounds known for its properties that contribute to the growth regulation of plants or weed-killing properties.

In a number of publications described herbicide properties rotlicht pyrimidine derivatives having replaced cycloalkanes in the 2-position, and these compounds are structurally and sterically different from the alkyl - and aryl-oxy/thio-pyrimidines described in these papers.

The invention relates to pyrimidine derivative of the General formula I:

where R1- alkyl-(C1-C4), O-alkyl-(C1-C4), halogen;

R2- alkyl-(C1-C4), O-alkyl-(C1-C4);

n = 3-5;

Z = COOH, COO-alkyl-(C1-C4), CONHSO2C6H5with herbicide activity, and to a method of controlling undesirable vegetation by processing them in the locus, namely, that the treatment is carried out pyrimidine derivatives of General formula I:

where R1- alkyl-(C1-C4), O-alkyl-(C1-C4), halogen;

R2- alkyl-(C1-C4), O-alkyl(C1-C4);

n = 3-5;

Z = COOH, COO-alkyl-(C1-C4), CONHSO2C6H5in the amount of 1-10 kg/ha.

Derivatives of pyrimidine obtained in a way that is the fact that the compound of General formula II:

where R1, R2and R3defined above, and L represents a leaving group, is subjected to a reaction between connection about the other compound of General formula I.

Leaving group is any group that is under the reaction conditions will be chipped off from the source material, thus stimulating a response in a specific area.

The leaving group L in the compound of General formula Alicino is a halogen atom such as bromine, chlorine or iodine, or preferably alkanesulfonyl group, for example methanesulfonyl.

Preferably, if the reaction proceeds in the presence of a base. This may serve, for example, alkali metal hydride such as potassium hydride or sodium hydride alkaline-earth metal such as calcium hydride; a carbonate or bicarbonate of alkali metal, for example potassium carbonate or sodium, or sodium bicarbonate; alkali metal alkoxide such as t-piperonyl potassium; or a tertiary amine such as triethylamine, pyridine or 1,8-diazabicyclo-5,4,0-undec-7-ene.

Usually, the reaction proceeds in the presence of an inert organic solvent such as a hydrocarbon solvent such as benzene or toluene; chlorinated hydrocarbons, such as dichloromethane or chloroform; alcohol, for example methanol or ethanol; an ether, for example diethyl ether, tetrahydrofuran, 1,4-dioxane; a ketone, such as acetone and formamide, dimethylacetamide or dimethyl sulfoxide; or a nitrile, for example acetonitrile; or in water with the appropriate selection agent, indicating the basic conditions for the reaction.

The proposed method can be implemented in a wide range of temperatures, for example from room temperature (20about(C) to a temperature of distillation of the reaction medium.

The number of reactants II and III may also vary within wide limits, for example from 0.1 to 10 mol of reagent II on 1 mol of reagent III. However, it is preferable to use equimolar amounts of II and III.

Needless to say that diastereoisomers and enantiomers of compounds of General formula I can be obtained using stereospecific source materials in the proposed method, with subsequent separation, if necessary, by chromatography, or in the case of enantiomers, these may be obtained using the technique of separation of a mixture of optical isomers.

The compound of General formula I obtained by the above method, can be easily converted into another compound of General formula I by standard methods. So, for example, the compound of General formula I, where R1 represents a halogen atom, for example ATO which is the group of ester may be hydrolyzed by standard methods to obtain the acid of formula I. Alternatively, hydrogenation, for example, benzyl ether complex of formula I, allows to obtain the corresponding acid.

The reaction for the conversion of acid and salt may be carried out using standard techniques.

Source pyrimidines of General formula II can be obtained using standard techniques (for example, see "Heterocyclic compounds", 16, "Pyrimidines". ed. D. J. Brown Interscience, 1962).

Compounds of General formula III are either known compounds or they can be obtained by standard methods. Compounds in which X is an oxygen atom, can be obtained, for example, through a reduction reaction of the corresponding cycloalkane-2-carboxylate in appropriate reducing conditions, for example using sodium borohydride in an inert solvent.

Compounds of General formula I showed a high level of activity when used as herbicides against undesirable plant species, and this activity took place in a wide range of application of the considered compounds, such as pre-emergence and post-harvest processing.

The invention also relates to gerbitz, the invention relates to the manufacture of specified herbicide composition by injecting media and compounds of the present invention.

Preferably, if the proposed composition includes at least two carriers, at least one of which is a surface-active substance.

The invention also relates to the use of the proposed connection offered as a herbicide. In addition, the invention relates to a method of controlling undesirable vegetation by processing the foci of its distribution proposed compound or composition. Such lesions can be, for example, soil or plants in the planting area. Treatment of these lesions may be pre-emergence or poslerodovoi. The dose of the active ingredient may comprise, for example, from 1 to 10 kg/ha and preferably from 1 to 4 kg/ha.

The media included in the proposed composition, can be any material Association with the active ingredient facilitates application of the specified composition on the treated lesions, such as plants, seeds or soil, or for easy storage or transportation. The specified media may be subjected to compression to a liquid state, and the specified media may be any standard medium customarily used in the preparation herbicide compositions. Preferred compositions contain from 0.5 to 95 wt.% the active ingredient.

Suitable solid carriers are natural and synthetic clays and silicates, for example natural silicas such as diatomites; magnesium silicates, for example, talc; magnesium silicates, for example attapulgite and vermiculite; aluminum silicates, for example kaolinites, montmorillonite and micas; calcium carbonate; calcium sulphate; ammonium sulphate; synthetic hydroxide silica and synthetic calcium silicates or aluminum; elements, for example, carbon and sulfur; natural and synthetic resins, such as coumarone resins, polyvinyl chloride, and styrene polymers and copolymers; solid polihlorvinila; bitumen; waxes; and solid fertilizers, for example, superphosphates.

Suitable liquid carriers are water; alcohols, for example isopropanol and glycols; ketones, for example acetone, metaliteracy ketone, methylisobutyl ketone and cyclohexane; ether; aromatic and aliphatic hydrocarbons, such as benzene, toluene and xylene; petroleum fractions such as kerosene and light mineral the representatives are also mixtures of different liquids, above.

Agronomic compositions often make up and transported in a concentrated form, and then, immediately before use, dilute. The presence of small amounts of surface-active substances (surfactants) can facilitate the process of dilution. Thus, it is preferable that at least one of those present in the composition of the media was surfactants. For example, the composition may contain at least two media, one of which is a surfactant.

Surface-active agent may be an emulsifying agent, dispersing agent or wetting agent, and the specified surfactant may be ionic or nonionic. Examples of suitable surfactants are the sodium and calcium salts of polyacrylic acids and lignosulfonic acids, condensates of fatty acids or aliphatic amino or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; esters of fatty acids of glycerol, sorbitan, sucrose or pentaerythritol; condensates with ethylene oxide and/or propylene oxide; condensation products of fatty alcohols or alkyl phenols, for example p-op or p-extertal, s or alkaline-earth metals, preferably sodium; esters of sulfuric or sulfonic acids containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulfate, secondary alkyl sulphates of sodium, sodium salts of sulfonated castor oil; and alkylarylsulfonate sodium such as dodecylbenzenesulfonate; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.

The proposed herbicide composition of the present invention may also contain other biologically active ingredients, such as compounds with herbicide, insecticide and fungicide properties.

The structure of the compounds obtained in accordance with the description of the examples was confirmed by mass spectrometry and NMR. Compounds were obtained then reduced to diastereoisomeric forms and terms of CIS - and TRANS refer to the spherical configuration of the resulting diastereoisomer.

P R I m e R 1. CIS-ethyl-2-(4,6-dimethoxypyrimidine-2-yl)oxocyclohexanecarboxylate.

Ethyl-cyclohexanol 2-carboxylate (85,0 g, 0.5 mol) was dissolved in ethanol (200 ml) and the resulting solution was cooled to 0aboutC. Then in small portions was added borohydride sodium (13,2 g, 0.35 mol), suspended platforms is UP>To the reaction mixture was slightly acidified by addition of 50% sulfuric acid and filtered. The filtrate was concentrated in vacuo, dissolved in ether and washed with sodium bicarbonate solution. The organic phase was dried with magnesium sulfate and evaporated in vacuum. The residue was chromatographically on silica gel, elwira first with a mixture of hexane and ethyl acetate (3:1), and then with a mixture of hexane and ethyl acetate at a ratio of 2:1, resulting received a 21.5 g of CIS - and 10.0 g of TRANS-ethyl-2-hydroxycyclohexanecarboxylate.

The resulting solution of CIS-hydroxyether (1,72 g, 0.01 mol) in dry dimethylformamide (10 ml) was added drop by drop to a stirred suspension of sodium hydride (0,48 g, when dispersion (60%) in dry dimethylformamide (20 ml). After stirring for 30 min, was added 4,6-dimethoxy-2-methanesulfonamide (2,18 g, 0.01 mol) and the resulting reaction mixture was hanging and was heated to 90aboutC for 16 hours the Mixture was concentrated in vacuum, diluted with water and was extracted with diethyl ether. A solution of diethyl ether was dried with sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel, elwira with a mixture of hexane and ethyl acetate (3:1). Yield 1.5 g (48%).

Elemental analysis:

Vicis the l)oxocyclohexanecarboxylate acid.

Sodium hydroxide (0.17 g) in water (20 ml) was added to a stirred solution of complex ethyl ester obtained in example 1 (1.3 g) in methanol (20 ml). The reaction mixture was stirred at room temperature overnight, concentrated in vacuo and diluted with water (100 ml). Then the aqueous solution was washed twice with diethyl ether, and then acidified with diluted hydrochloric acid. The acidified aqueous mixture was dried with magnesium sulfate and evaporated in vacuum. The residue was pereirae with hexane and was obtained as crude product in the form of a white solid, which was recrystallized from aqueous methanol and the result was obtained 0.6 g (51%) of the desired product having a melting point of 151-152aboutC.

Elemental analysis.

Calculated, %: From 55.3; H 6,4; N 9,9.

Found, %: From 55.3; H 6,5; N 10,1.

P R I m e R s 3-16. The compounds obtained in these examples using procedures similar to those described in examples 1 and 2, are presented in table.1, which shows also the results of chemical analyses and melting point. In table. 1 compounds identified by the indication of deputies in accordance with the formula (Fig. 2).

P R I m e R 19. TRANS-2-(4,6-dimethoxypyrimidine-2-yl)oxy-N - benzosulfimide in example 11, in dry tetrahydrofuran (10 ml) drop by drop) was added to a stirred solution of 1,1-carbonyldiimidazole (or 0.57 g) in dry tetrahydrofuran (10 ml) in the presence of nitrogen. The reaction mixture was stirred for 30 min at room temperature, was heated under reflux for 30 min and cooled to room temperature.

Then added benzosulfimide (0.56 g), and then one drop) was added 1,8-diazabicyclo-[5,4,0]-undec-7-ene (0,54) in dry tetrahydrofuran (5 ml). The reaction mixture is stirred for 24 h at room temperature, was heated under reflux for 6 h, and then poured into 1N hydrochloric acid (80 ml) and was extracted with diethyl ether (3 100 ml). The combined ether extracts were dried with magnesium sulfate and evaporated. The residue was chromatographically on silica gel, elwira mixture of dichloromethane and ethyl acetate 2:1, resulting in received 100 mg of target compound with a melting point 175aboutC.

Elemental analysis.

Calculated, %: C 54,1; H 5,5; N 10,0.

Found, %: C 53,8; H 6,0; N 10,3.

P R I m e R 20. Herbicide activity.

To evaluate herbicide activity of the compounds of the present invention were used trace O) flax seed (Linum usitatissimum, L.), white mustard (Sinapsis alba, M), sugar beet (Beta vulgaris, SB) and soybean (Glycine max, S).

The tests were carried out in two ways: by pre-emergence treatment and post-harvest processing. Pre-emergence treatment was performed by spraying the liquid composition containing the compound of the present invention, the soil in which the seeds were sown mentioned plant species. Post-harvest processing consisted of two types of tests: irrigation and spraying the leaves. When tested by irrigating the soil sprouted in 2 these plants were infiltrated with a liquid composition containing the compound of the present invention, a test of the second type, the leaves of germinated plants were sprayed with the specified composition.

As soil tests used loamy soil for cultivation of horticultural crops.

Compound for the treatment consisted of a solution of test compounds in acetone containing 0.4 wt. % condensate of alkylphenol and ethylene oxide (finished product trademark TRITON X = 155). Specified acetone solution was diluted with water and the resulting formulations were used when spraying the soil and foliage in doses, comprising 5 kg or 1 kg active the soup 10 kg of active ingredient per hectare in a volume, equivalent to approximately 3000 l/ha

When pre-emergence test and post-harvest testing in the quality control used raw sowed the ground with sprouted plants, respectively.

Herbicide activity of the tested compounds was evaluated visually after 12 days after spraying the foliage and soil, and 13 days after impregnation of the soil, by registering on the 0-9 scale. 0 corresponded to the untreated control variant, and figure 9 - total destruction. The increase by one unit on the scale meant a 10 per cent increase in the activity of the composition.

The results of the tests are presented in table.2, where connections are identified by the numbers of examples. Asterisks indicate that in this case the results were not obtained.

1. Derivatives of pyrimidine General formula

< / BR>
where R1- C1- C4-alkyl, O=C1- C4-alkyl, halogen;

R2= C1- C4-alkyl, O = C1- C4-alkyl;

n = 3 - 5;

Z IS COOH, COO = C1- C4-alkyl, NHSO2WITH6H5,

have a weed-killing activity.

2. The method of controlling undesirable vegetation by processing them in a locus different FROM4-alkyl, O - C1- C4-alkyl, halogen;

R2= C1- C4-alkyl, O = C1- C4-alkyl;

n = 3 - 5;

Z IS COOH, COO = C1- C4-alkyl, NHSO2C6H5,

in quantities of 1 to 10 kg/ha

 

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Fungicidal tool // 2002416

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes substituted benzoylcyclohexanediones of the general formula (I):

wherein m = 0 or 1; n = 0 or 1; A means a single bond or alkanediyl (alkylene) with 1-4 carbon atoms; R1 means hydrogen atom or unsubstituted alkyl with from 1 to 6 carbon atoms; R2 means methyl; R3 means hydrogen atom, nitro-, cyano-group, halogen atom, alkyl with from 1 to 4 carbon atoms substituted with halogen atom, alkoxy-group with from 1 to 4 carbon atoms or alkyl sulfonyl with from 1 to 4 carbon atoms; R4 means nitro-group, halogen atom, unsubstituted alkyl with from 1 to 4 carbon atoms of that substituted with halogen atom; Z means heterocycle, and herbicide agent based on thereof. Also, invention describes substituted derivatives of benzoic acid of the general formula (III):

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EFFECT: valuable properties of compounds.

7 cl, 8 tbl, 7 ex

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9 cl, 12 tbl, 3 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: method involves carrying out a seasonal single treatment of plant leaves with asymmetrical derivative of 4,6-bis-(aryloxy)pyrimidine of the formula: wherein X means chlorine atom (Cl), nitro- or cyano-group. Invention provides enhancing the long-term time of plants protection.

EFFECT: enhanced effectiveness and valuable properties of compounds.

6 cl, 6 tbl

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention relates to new derivatives of uracil of the formula [I] eliciting the herbicide effect, herbicide composition based on thereof and a method for suppression of weed growth. In the formula [I] W means oxygen (O), sulfur (S) atom or imino-group; Y means oxygen atom (O) or sulfur atom (S); R1 means (C1-C3)-alkyl or (C1-C3)-halogenalkyl; R2 means (C1-C3)-alkyl; R4 means hydrogen atom (H) or methyl; R5 means (C1-C6)-alkyl, (C1-C6)-halogenalkyl, (C3-C6)-alkenyl, (C3-C6)-halogenalkenyl, (C3-C6)-alkynyl or (C3-C6)-halogenalkynyl; X1 means halogen atom, cyano- or nitro-group; X2 means hydrogen atom (H) or halogen atom; each among X3 and X4 means independently hydrogen atom (H), halogen atom, (C1-C6)-alkyl, (C1-C6)-halogenalkyl, (C3-C6)-alkenyl, (C3-C6)-halogenalkenyl, (C3-C6)-alkynyl, (C3-C6)-halogenalkynyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-, (C1-C6)-halogenalkoxy-, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkoxy- or cyano-group. Also, invention relates to new intermediate substances used for preparing compounds of the formula [I] corresponding to formulae [VII] , [XXXIV] and [XXXIII] wherein in compound of the formula [VII] W means oxygen (O), sulfur (S) atom or imino-group; Y means oxygen (O) or sulfur atom (S); in compounds of formulae [XXXIV] and [XXXIII] W means oxygen atom (O); R17 means oxygen atom (O); R4 means hydrogen atom (H) or methyl. Also, invention relates to methyl- or ethyl-[2-(5-amino-2-chloro-4-fluorophenoxy)phenoxy]acetate not early described in the literature.

EFFECT: valuable herbicide properties of compounds.

23 cl, 17 sch, 9 tbl, 11 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to selective herbicidal compositions, containing customary auxiliary substances, as well as: a) herbicidal effective amount of compound of formula I or agriculture acceptable salt thereof wherein R are independently C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-alcoxy-C1-C4-alkyl, or C1-C4-alcoxy-C1-C4-alcoxy-C1-C4-alkyl; m = 2; Q is group of formula wherein R23 is hydroxyl and Y is C1-C4-alkylen bridge; and b) synergetically effective amount of one or more herbicides; and methods for controlling of undesired plants in tame cultures using the said composition. Also disclosed is composition containing customary auxiliary substances, as well as herbicidal and synergetically effective amount of 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one of formula 2.2 and herbicidal antagonistically effective amount of antidote of formula 3.1. Compositions based on 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one and herbicidal antagonistically effective amount of antidote, as well as methods for controlling of weeds and cereal grasses in tame cultures also are described.

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5 cl, 63 tbl, 12 ex

FIELD: organic chemistry, herbicides, agriculture.

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wherein a heterocyclic ring can be substituted with at least a substitute of a single species taken among the group involving halogen atom, (C1-C6)-alkyl-(C1-C6)-alkoxy; Y represents oxygen, sulfur atom, imino-group or (C1-C3)-alkylimino-group; R1 represents (C1-C3)-halogenalkyl; R2 represents (C1-C3)-alkyl; R3 represents OR7, SR8 or N(R9)R10; X1 represents halogen atom, cyano-group, thiocarbamoyl or nitro-group; X2 represents hydrogen or halogen atom wherein each among R7, R8 and R10 represents independently carboxy-(C1-C6)-alkyl and other substitutes given in the invention claim; R9 represents hydrogen atom or (C1-C6)-alkyl. Also, invention relates to intermediate compounds used in preparing uracil derivatives.

EFFECT: improved preparing method, valuable properties of compounds.

40 cl, 16 sch, 12 tbl, 65 ex

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EFFECT: improved preparing method, valuable properties of compounds.

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FIELD: agriculture, fungicides.

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8 cl, 12 ex

Herbicidal agent // 2271659

FIELD: organic chemistry, agriculture, herbicides.

SUBSTANCE: invention relates to herbicidal agent containing compound of general formula I wherein X represents residue X1 or X2 and Z, R1 and R2 are as defined in claim of invention, and additional active substance selected from group containing bromoxynil, dicamba, flufenacete, metolachlor, atrazine, pendimethaline, imazetapir, iodosulfuron, nicosulfuron, 2-amino-4-(1-fluoro-1-methyl)-6-(3-phenyl-1-cyclobuthyl-1-propylamino)-1,3,5-triazine and N-[(4,6-dimethoxy-pyrimidine-2-yl)-aminocarbonyl]-2-dimethylamino-carbonyl-5-formyl-benzenesulfonamide. Compound of formula I and additional active substance are taken in mass ratio of 1:20-10:1, respectively.

EFFECT: agent of high herbicidal activity.

6 cl, 15 ex

FIELD: organic chemistry, agriculture.

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EFFECT: enhanced effectiveness and valuable properties of compounds.

6 cl, 6 tbl

FIELD: organic chemistry, herbicides, agriculture.

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wherein a heterocyclic ring can be substituted with at least a substitute of a single species taken among the group involving halogen atom, (C1-C6)-alkyl-(C1-C6)-alkoxy; Y represents oxygen, sulfur atom, imino-group or (C1-C3)-alkylimino-group; R1 represents (C1-C3)-halogenalkyl; R2 represents (C1-C3)-alkyl; R3 represents OR7, SR8 or N(R9)R10; X1 represents halogen atom, cyano-group, thiocarbamoyl or nitro-group; X2 represents hydrogen or halogen atom wherein each among R7, R8 and R10 represents independently carboxy-(C1-C6)-alkyl and other substitutes given in the invention claim; R9 represents hydrogen atom or (C1-C6)-alkyl. Also, invention relates to intermediate compounds used in preparing uracil derivatives.

EFFECT: improved preparing method, valuable properties of compounds.

40 cl, 16 sch, 12 tbl, 65 ex

FIELD: organic chemistry of heterocyclic compounds, medicine, pharmacy.

SUBSTANCE: invention relates to derivatives of pyrimidine of the general formula (I) and their pharmaceutically acceptable acid-additive salts possessing properties of neurokinin-1 (NK) receptors antagonists. In the general formula (I): R1 means lower alkyl, lower alkoxyl, pyridinyl, pyrimidinyl, phenyl, -S-lower alkyl, -S(O2)-lower alkyl, -N(R)-(CH2)n-N(R)2, -O-(CH)n-N(R)2, -N(R)2 or cyclic tertiary amine as a group of the formula: R1 means lower alkyl, lower alkoxyl, pyridinyl, pyrimidinyl, phenyl, -S-lower alkyl, -S(O2)-lower alkyl, -N(R)-(CH2)n-N(R)2, -O-(CH)-N(R)2, -N(R)2 or cyclic tertiary amine of the formula: that can comprise additional heteroatom chosen from atoms N, O or S, and wherein this group can be bound with pyrimidine ring by bridge -O-(CH2)n-; R2 means hydrogen atom, lower alkyl, lower alkoxyl, halogen atom or trifluoromethyl group; R3/R3' mean independently of one another hydrogen atom or lower alkyl; R4 means independently of one another halogen atom, trifluoromethyl group or lower alkoxyl; R means hydrogen atom or lower alkyl; R means independently of one another hydrogen atom or lower alkyl; X means -C(OH)N(R)- or -N(R)C(O)-; Y means -O-; n = 1, 2, 3 or 4; m means 0, 1 or 2. Also, invention relates to a pharmaceutical composition comprising one or some compounds by any claim among claims 1-19 and pharmaceutically acceptable excipients. Proposed compounds can be used in treatment, for example, inflammatory diseases, rheumatic arthritis, asthma, benign prostate hyperplasia, Alzheimer's diseases and others.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.

21 cl, 1 tbl, 76 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a novel method that can be used in industry for synthesis of substituted aniline compound represented by the following general formula (6):

wherein in the general formula (6) each R1, R2 and R3 means independently alkyl group, alkoxy-group, alkoxyalkyl group, halogenalkyl group, carboxyl group, alkoxycarbonyl group, alkylcarboxamide group, nitro-group, aryl group, arylalkyl group, aryloxy-group, halogen atom or hydrogen atom; each X and Y means independently hydrogen atom, alkyl group, alkoxy-group, alkoxyalkyl group, halogenalkyl group, carboxyl group, alkoxycarbonyl group or halogen atom. Method involves oxidation of substituted indole compound represented by the following general formula (3):

(wherein values R1, R2, R, X and Y are given above) resulting to opening indole ring to yield acetanilide compound represented by the following general formula (4):

(wherein values R1, R2, R3, X and Y are given above) and Ac means acetyl group, and treatment of this compound by reduction and deacetylation. Also, invention relates to novel intermediate compounds. Proposed compound (6) can be used as intermediate substance for production of chemicals for agriculture and as medicinal agents.

EFFECT: improved method of synthesis.

20 cl, 1 sch, 3 tbl, 31 ex

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