Substituted benzoylpyrazoles and herbicide agent based on thereof

FIELD: organic chemistry, herbicides.

SUBSTANCE: invention describes substituted benzoylpyrazoles of the general formula (I): wherein Q means oxygen atom (O); R1 means alkyl with 1-6 carbon atoms; R2 means hydrogen atom; R3 and R4 mean independently of one another hydrogen atom, halogen atom, alkyl with 1-4 carbon atoms substituted with halogen atom; R5 means hydrogen atom, alkyl with 1-6 carbon atoms; Y means hydrogen atom; Z means alkoxyamino-group with 1-6 carbon atoms, alkylamino-group with 1-6 carbon atoms, substituted alkoxy-group with 1-4 carbon atoms, N-alkylalkoxyamino-group with 1-4 carbon atoms, phenyl substituted with halogen atom, monocyclic heterocyclyl, heterocyclylamino-group, group -N=(heterocyclyl) chosen from the group: furyl, tetrahydrofurylmethylamino-group, isoxazolyl, dihydroisoxazolyl (isoxazolinyl), tetrahydroisoxazolyl (isoxazolidinyl), tetrahydro-(2H)-1,2-oxazine-2-yl, dihydrothiazolyl (thiazolinyl), oxadiazolylamino-, thiadiazolylamino-group, piperidinyl, piperidinylamino-group, 2-oxo-1,3-diazacyclohexyl, morpholinyl, morpholinylamino-group, respectively, and substituted if necessary with alkyl with 1-4 carbon atoms, halogenalkyl with 1-4 carbon atoms, cycloalkyl with 3-6 carbon atoms involving their all possible tautomeric forms and possible salts. Also, invention describes a herbicide agent based in proposed compounds. Proposed compounds possess herbicide activity.

EFFECT: valuable properties of compounds and agent.

4 cl, 5 tbl, 77 ex

 

The invention relates to new nitrogen-containing heterocyclic compounds possessing biological activity, and more particularly to substituted benzoylpyrazoles and herbicide tool based on them.

It is already known that certain substituted benzoylpyrazoles, such as the compounds N-[2,6-dichloro-3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-phenyl]-acetamide", she methyl ester [2,6-dichloro-3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-phenyl]-carbamino acid, N′-[2,6-dichloro-3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-phenyl]-N,N-diethyl-urea, methyl ester [2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-6-methyl-sulfonyl-phenyl]-carbamino acid, N′-[2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-N,N-diethyl-urea, N-[3-[(1-ethyl-5-hydroxy-1H-pyrazole-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-ndimethylacetamide, N-[3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-propanamide, N-[3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-acetamide", she N′-[2-chloro-3-[(1-ethyl-5-hydroxy-1H-pyrazole-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-N,N-diethyl-urea, N-[3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-formamide, methyl ester [3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-2-methyl-6-methylsulfone is-phenyl]-carbamino acid, N-[2-chloro-3-[(1-ethyl-5-hydroxy-1H-pyrazole-4-yl)-carbonyl]-6-methylsulphonyl - phenyl]-ndimethylacetamide, N-[2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-ndimethylacetamide, N-[3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-2,2,2-tri-peracetate, N-[3-[(1-ethyl-5-hydroxy-1H-pyrazole-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-2,2,2-Cryptor-ndimethylacetamide, N-[3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-N-methyl-formamide, methyl ester N-[2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-N-methyl-carbamino acid, N-[2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-N,N′-diethyl-N-methyl-urea and methyl ester of N-[2,6-dichloro-3-[(5-hydroxy-1-methyl-1H-pyrazole-4-yl)-carbonyl]-phenyl]-N-methyl-carbamino acid (see Japanese patent application JP-A-11292849 in Chem. Abstracts 131:286507), have a weed-killing properties (see also European patent application EP-A-352543, U.S. patent US-A-5846907, international patent application WO-A-96/26206, WO-A-97/41105, WO-A-97/41116, WO-A-97/41117, WO-A-97/41118, WO-A-97/46530, WO-A-98/28981, W0-A-98/31681, WO-A-98/31682, WO-A-99/07697, WO-A-99/10328, W0-A-00/58306).

Object of the invention is the expansion of the range of the substituted benzoylpyrazoles with high herbicide activity without symptoms of phytotoxicity.

The problem is solved offer Emami substituted benzoyl-pyrazoles of General formula (I),

which.

Q - O (oxygen),

R1is alkyl with 1-6 carbon atoms,

R2- hydrogen

R3, R4independently of one another denote hydrogen, halogen, alkyl with 1-4 carbon atoms, substituted with halogen,

R5is hydrogen, alkyl with 1-6 carbon atoms,

Y is hydrogen,

Z means alkoxyamino with 1-6 carbon atoms,

substituted alkoxy with 1-4 carbon atoms, alkylamino with 1-6 carbon atoms; N-alkyl-alkoxyamino with 1-4 carbon atoms, cycloalkenyl with 3-6 carbon atoms, phenyl, substituted by halogen, monocyclic heterocyclyl, heterocyclisation, -N=(heterocyclyl) from a number of furil, tetrahydrofurfurylamine, pyrrolidinyl, pyrrolidinyl, 2-oxo-1,3-diazocyclopentadiene, isoxazolyl, dihydroisoxazole (isoxazoline), tetrahydroisoquinoline (isoxazolidine), tetrahydro-(2H)-1,2-oxazin-2-yl, dihydrothiazolo (thiazoline), oxadiazolidine, thiadiazolidine, piperidinyl, piperidylamine, 2-oxo-1,3-disallowance, morpholinyl, Mor-vainillina, respectively, optionally substituted by alkyl with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, cycloalkyl with 3-6 carbon atoms,

including all possible tautomeric forms and possible salt.

Preferred substituted benzoylpyrazoles formula (I) are the two who are compounds have

R1is methyl, ethyl, n - or ISO-propyl,

R2- hydrogen

R3, R4independently of one another denote hydrogen, fluorine, chlorine, bromine, deformity, trifluoromethyl, dichloromethyl, trichloromethyl,

R5is hydrogen, methyl, ethyl, n - or ISO-propyl, n - or ISO-butyl,

Y is hydrogen,

Z - methoxyamino, amoxilina, n - or ISO-propoxyimino, N-methylmethanamine, phenyl, substituted by fluorine, chlorine, bromine, monocyclic heterocyclyl, heterocyclisation, group-N=(heterocyclyl) from a number of furil, tetrahydrofurfurylamine, pyrrolidinium, 2-oxo-1,3-diaza-cyclopentyl, isoxazolyl, dihydroisoxazole (isoxazoline), tetrahydroisoquinoline (isoxazolidine), dihydrothiazolo (thiazoline), oxadiazolidine,thiadiazolidine, piperidinyl, piperidylamine, 2-oxo-1,3-diaza-cyclohexyl, morpholinyl, morpholinyl-amino, respectively, when necessary, replaced by stands, ethyl, n - or ISO-propylene, n-, ISO-, sec - or tert-bootrom.

Preferred substituted benzoylpyrazoles formula (I) are compounds in which

Q - O (oxygen),

R1is methyl, ethyl, n - or ISO-propyl,

R2- hydrogen

R3, R4independently of one another denote hydrogen, fluorine, chlorine, bromine, methyl, ethyl, deformity, trifluoromethyl, dichloromethyl, trichloromethyl,

R5in the location, methyl, ethyl, n - or ISO-propyl,

Y is hydrogen,

Z - methoxyamino, amoxilina, n - or ISO-propoxyimino, N-methylmethanamine, phenyl, substituted by fluorine, chlorine, bromine, monocyclic heterocyclyl, heterocyclisation, group-N=(heterocyclyl) from a number of furil, tetrahydropyrimidine, 2-oxo-1,3-diaza-cyclopentyl, isoxazolyl, dihydroisoxazole (isoxazoline), tetrahydroisoquinoline (isoxazolidine), dihydrothiazolo (thiazoline), piperidinyl, piperidylamine, 2-oxo-1,3-diaza-cyclohexyl, morpholinyl, morpholinium, respectively, if necessary, replaced by stands, ethyl, n- or ISO-propylene, n-, ISO-, sec - or tert-bootrom.

Substituted benzoylpyrazoles formula (I) belong to the category of low-toxic substances.

New substituted benzoylpyrazoles General formula (I) can be obtained due to the fact that

(a) pyrazoles of General formula (II)

in which

R1, R2and Y have indicated above values

subjected to interaction with substituted benzoic acids of General formula (III),

in which

Q, R3, R4, R5and Z are indicated above values

or their reactive derivatives, such as, for example, the corresponding acid halides, anhydrides, acids, cyanides acids or other attributes of the data ethers,

if necessary, in the presence of a dehydrating agent, if necessary, in the presence of one or more auxiliary additives and, if necessary, in the presence of one or more diluents, or

(b) substituted benzoylpyrazoles General formula (Ia)

in which

Q, R1, R2, R3, R4, R5and Z are indicated above values

subjected to interaction with compounds of General formula (IV)

in which

Y is indicated above values, excluding hydrogen, and

X represents halogen,

- or, if necessary, with the corresponding acid anhydrides, isocyanates or isothioscyanates,

if necessary, in the presence of one or more auxiliary additives and, if necessary, in the presence of one or more diluents,

and, if necessary, obtained according to a) or b) the compounds of formula (I) under the definitions of the substituents is subjected to electrophilic or nucleophilic reactions of substitution or oxidation reactions or known recovery methods or compounds of formula (I) in the usual way transferred to salt.

New substituted benzoylpyrazoles General formula (I) can be principally obtained as shown in the following diagram:

(C) interaction is of aminobenzotriazole General formula (V) with a halogen compounds(thio)carbonyl General formula (VI) or if necessary, with the corresponding ISO(thio)cyanate (Q, R1, R2, R3, R4, R5, Y and Z are indicated above values, X represents halogen):

(d) interaction from(thio)cyanobenzoate General formula (VII) with nucleophilic compounds of General formula (VIII) (Q, R1, R2, R3, R4, Y and Z have the indicated higher values):

If you use, for example, 3-chloro-5-hydroxy-1-methyl-pyrazole and 3-[(qi-apropriation)-(methylamino)]-5-fluoro-benzoic acid as starting compounds, the reaction according to method (a) can be described with the following formula scheme:

If you use, for example, 2-methoxy-ethyl ester N-[3-chloro-4-[(1-ethyl-5-hydroxy-1H-pyrazole-4-yl)-carbonyl]-phenyl]-N-ethyl-carbamino acid and benzoyl chloride as starting compounds, the reaction according to method (b) can be described with the following formula scheme:

The initial compounds of General formula (II) are known and/or can be obtained by known methods (see European patent application EP-A-240 001).

The initial compounds of General formula (III) are known and/or can be obtained by known methods (see patent application JP-A-112 92 849 and sample receipt).

Substituted benzoic acid of General formula (III) receive, if esters of benzoic acids of General formula (IIIa),

in which

Q, R3, R4, R5and Z are indicated above values and

R means alkyl, in particular methyl or ethyl,

subjected to contact with water, if necessary, in the presence of an auxiliary agent such as, for example, sodium hydroxide, and, if necessary, in the presence of a diluent, such as, for example, Tetra-hydrofuran, at temperatures between 0°and 100°With (see examples receipt).

Necessary as preproduction esters of benzoic acids of General formula (IIIa) are known and/or can be obtained by known methods (see patent application of Japan JP-A-112 92 849 and sample receipt).

Esters of benzoic acids of General formula (IIIa) is obtained if

(α) esters of benzoic acids of General formula (IX)

in which

Q, R3, R4, R5and Z have the above values and

R means alkyl, in particular methyl or ethyl, is subjected to the interaction with the halogen compounds(thio)carbonyl General formula (VI)

in which

Q and Z have the above values and

X represents halogen, in particular fluorine, chlorine or brough is,

- or, if necessary, with the corresponding ISO(thio)cyanate,

if necessary, in the presence of an acid acceptor, such as, for example, potassium carbonate or triethylamine, and optionally in the presence of a diluent, such as, for example, methyl isobutyl ketone or acetonitrile, at temperatures between 0°and 100°With (see examples),

or if (β) esters of ISO(thio)cyanobenzoic acids of General formula (X)

in which

Q, R3and R4have the above values and

R means alkyl, in particular methyl or ethyl,

subjected to interaction with nucleophilic compounds of General formula (VIII)

in which

Z has the above values

if necessary, in the presence of excipients, such as, for example, triethylamine, and optionally in the presence of a diluent, such as, for example, acetonitrile or toluene, at temperatures between 10°120°With (see examples receipt).

The initial compounds of General formula (IV) are known chemicals for synthesis.

The initial compounds of General formula (VI) are known organic compounds. The initial compounds of General formula (V) can be obtained in a known manner.

The initial compounds of General form is s (VIII) are known chemicals for synthesis. The initial compounds of General formula (VII) can be obtained in a known manner.

The initial compounds of General formula (X) can be obtained in a known manner.

Method (a) for new substituted benzoylpyrazoles General formula (I), if necessary, preferably carried out using a dehydrating agent. Moreover, it is possible to use conventional chemicals, suitable for transformation with water.

Suitable dehydrating agents are, for example, dicyclohexylcarbodiimide, anhydride papapostolou acid and carbonyl-bis-imidazole.

Particularly suitable dehydrating agent is dicyclohexylcarbodiimide and anhydride papapostolou acid.

Method (a) obtaining new substituted benzoylpyrazoles General formula (I), if necessary, is carried out with the use of adjuvants.

Suitable auxiliary additives are, for example, sodium cyanide, potassium cyanide, acetonecyanohydrin, 2-cyano-2-(trimethylsilyloxy)-propane and trimethylsilylacetamide.

Particularly suitable auxiliary additive is trimethylsilane.

Methods (a) and (b) is conducted preferably by using one or more reaction auxiliary additives. As reaction auxiliary additives for proposed according to the invention the method is in (a) and (b) in General, use the usual inorganic or organic bases or acid acceptors. These include preferably the acetates of the alkali or alkaline earth metal amides alkali or alkaline earth metals, carbonates of alkaline or alkaline earth metals, carbonates of alkaline or alkaline earth metals, hydrides of alkali or alkaline earth metals, hydroxides of alkaline or alkaline earth metals or alkanoate alkaline or alkaline earth metals, such as, for example, sodium acetate, potassium or calcium, lithium amide, sodium, potassium or calcium, sodium carbonate, potassium or calcium, bicarbonate of sodium, potassium or calcium, lithium hydride, sodium, potassium or calcium hydroxide of lithium, sodium, potassium or calcium, methanolic sodium or potassium, ethanolic sodium or potassium, n-or ISO-propanol sodium or calcium, n-, -ISO-, sec - or tert-butanolate sodium or calcium; in addition, basic organic nitrogen compounds, such as trimethylamine, triethylamine, tri-Propylamine, tributylamine, ethyl-Diisopropylamine, N,N-dimethyl-cyclo-hexylamine, dicyclohexylamine, ethyl dicyclohexylamine, N,N-dimethyl-aniline, N,N-dimethyl-benzylamine, pyridine, 2-methyl-pyridine, 3-methyl-pyridine, 4-methyl-pyridine, 2,4-dimethyl-pyridine, 2,6-dimethyl-pyridine, 3,4-dimethyl-pyridine and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, N-ethyl-piperidine, N-methyl-morpholine, N-ethyl-morpholine,1,4-diazabicyclo[2,2,2]-octane (DABCO), 1,5-diazabicyclo[4,3,0]-non-5-ene (DBN)or 1,8-diazabicyclo[5,4,0]-undec-7-ene (DBU).

As auxiliary additives for methods (a) and (b) also use interphase catalysts. Such catalysts are, for example, are:

the tetrabutylammonium bromide, tetrabutylammonium chloride, chloride, Tetra-octylamine, tetrabutylammonium hydrosulfate, chloride methyl-trioctyl-ammonium chloride hexadecyl-trimethylammonium, bromide, hexadecyl three-methylamine, chloride, benzyl-trimethylammonium chloride benzyl-triethyl-ammonium hydroxide benzyl-trimethylammonium, hydroxide benzyl-triethyl-ammonium chloride benzyl-tributylamine, bromide benzyl-tributylamine, bromide tetrabutylphosphonium, chloride tetrabutylphosphonium, bromide, tributyl-hexadecylamine, chloride butyl-triphenylphosphane, bromide, ethyl-trioctylphosphine, bromide tetraphenylporphine.

Methods for obtaining compounds of General formula (I) is preferably carried out in an environment of one or more diluents. In addition to water as diluents used first of all inert organic solvents. These include, in particular, aliphatic, acyclic or aromatic, optionally halogenated hydrocarbons, such as benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, tetrachloro the'étang; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or etilenglikolevye ether or etilenglikolevye ether; ketones, such as acetone, butanone or methyl-isobutyl-ketone; NITRILES, such as acetonitrile, propionitrile or butyronitrile; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or triamide hexamethylphosphoric acid; esters such as methyl ester of acetic acid or ethyl ester of acetic acid; sulfoxidov, such as dimethyl sulfoxide; alcohols such as methanol, ethanol, n - or ISO-propanol, simple etilenglikolevye ether, simple etilenglikolevye ether, simple diethylethylenediamine ether, simple diethylethylenediamine ether, mixtures thereof with water or pure water.

When carrying out processes (a) and (b) the reaction temperature may vary within wide limits. Generally operate at temperatures between 0°150°C, preferably between 10°120°C.

Methods (a) and (b) is conducted usually under normal pressure. However, it is also possible ways at elevated or reduced pressure (typically between 0.1 bar and 10 bar).

When carrying out processes (a) and (b) the initial substance is usually used in approximately equimolar quantities. One is also possible to use one component in a larger excess. The transformation is usually carried out in a suitable diluent in the presence of adjuvants and the reaction mixture is stirred generally for several hours at the required temperature. The transformation carried out by conventional methods (see examples receipt).

Substituted benzoylpyrazoles formula (I) can be used as defoliants, desicants, agents inhibit the growth of grasses and, in particular, as agents for the destruction of weeds. Under the weeds understood all plants which grow in places where they are unwanted. Total or selective herbicide action substituted benzoylpyrazoles formula (I) usually depends on their consumption rates. They can be used, for example, to fight with these plants.

Dicotyledonous weed species: Abutilon (abutilon), Amaranthus (amaranth), Ambrosia (ragweed), Anoda, Anthemis (Popovka), Aphanes, Atriplex (quinoa), Bellis (Daisy), Bidens (series), Capsella (shepherd's purse), Carduus (Thistle), Cassia (Cassia), Centaurea (cornflower), Chenopodium (pigweed), Cirsium (Thistle), Convolvulus (bindweed), Datura (Datura), Desmodium, Emex, Erysimum (wallflower), Euphorbia (spurge), Galeopsis, Galinsoga (galinsoga), Galium (bedstraw), Hibiscus (hibiscus), Ipomoea (morning glory), Kochia (Kochia), Lamium (dead-nettle), Lepidium (cress), Lindernia, Matricaria (Matricaria), Mentha (mint), Mercurialis (prelesnik), Mullugo, Myosolis (forget-me-not), Paraver (IAC), Pharbilis, Plantago (plantain)Polygonum (knotweed), Portulaca (portal is) Ranunculus (Buttercup), Raphanus (radish), Rorippa, Rotala, Rumex (sorrel), Salsola (Salsola), Senecio (Senecio), Sesbania (sesbania), Sida (SIDA), Sinapis (mustard), Solanum (nightshade), Sonchus (oten), Spenoclea, Stellaria (starwort), Taraxacum (dandelion), species, such as thlaspi, Trifolium (clover), Urtica (nettle), Veronica (Veronica), Viola (violet), Xanthium (cocklebur).

Dicotyledonous cultivated plants species: Arachis (peanut), Beta (beet), Brassica (cabbage), Cucumis (cucumber), Cucurbita (pumpkin), Helianyhus (sunflower), Daucus (carrot), Glycine (soybean), Gossypium (cotton), Ipomoea (morning glory), Lactuca (lettuce), Linum (flax), Lycopersicon (tomato), Nicotiana (tobacco), Phaseolus (bean), Pisum (pea), Solanum (nightshade), Vicia (vetch).

Monocotyledonous weeds species: Aegilops (Aegilops), Agropyron (Wheatgrass), Agrostis (bentgrass), Alopecurus (Alopecurus), Apera, Avena (oats), Brachiaria, Bromus (brome), Cenchrus, Commelina (commelina), Cynodon (cynodon), Cyperus (Cyperus), Dactyloctenium, Digitaria (weed), Echinochloa (barnyard grass), Eleocharis (bolotnitsa), Eleusine (Eleusis), Eragrostis (polovicka), Eriochloa, Festuca (fescue), Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium (the chaff), Monochoria, Panicum (millet), Paspalum (buckwheat), Phalaris (Canary grass), Phleum (Timothy grass), PoA (bluegrass), Rottboellia, Sagittaria (arrowhead), Scirpus (bulrush), Setaria (spickle), Sorghum (sorghum).

Monocotyledonous plants species: Allium (onion), Ananas (pineapple), Asparagus (asparagus), Avena (oats), Hordeum (barley), Oryza (rice), Panicum (millet), Saccharum (sugar cane), Secale (rye), Sorghum (sorghum), Triticale (triticale), Triticum (wheat), Zea (maize).

The use of substituted benzoylpyrazoles fomula (I), proposed the e according to the invention the active substance is in no way limited to these types, and also equally apply to other plants.

Proposed according to the invention the active substance depending on concentration are suitable for the complete destruction of weeds, for example, industrial equipment and railway tracks and on the roads and squares with or without growth the growth of trees. It is also possible application of the proposed according to the invention the active substances for combating weeds in perennial cultures, for example, when planting the tree, ornamental, fruit, wine, citrus, walnut, banana, coffee, tea, rubber, oil-palm, cocoa, fruit and hop crops, ornamental lawns and sports fields and pastures, and for the selective combating of weeds in annual crops.

Proposed according to the invention the active substance demonstrate a strong herbicide activity and a wide range of soil and green parts of plants above the ground surface. They are also particularly suitable for the selective combating of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, processing as before the shoot and after the shoot of the plants.

Proposed according to the invention the active substance in a certain concentration or rate of application can also be used for oribi of noxious animals and fungal or bacterial diseases of plants. The data of the active substance, if necessary, can also be used as an intermediate or intermediates for the synthesis of other active substances.

According to the invention can be processed by all plants and plant parts. Moreover, under plants understand all plants and plant populations such as desired and not desired wild or cultivated plants (including cultivated plants of natural origin). Cultivated plants can be plants that may be received conventional methods of breeding and optimization or biotechnological and geotechnologies methods or by combinations of such methods, including the transgenic plants and plant varieties are protected or not protected by the security documents. Under parts of plants understand all surface and ground parts and organs of plants, such as shoots, leaves, flowers and roots, and as examples of lead leaves, needles, stems, trunks, flowers, fruit bodies, fruits and seeds and also roots, tubers and rhizomes. Parts of plants is also of crop products and vegetative and generative materials reproduction, for example cuttings, tubers, rhizomes, horizontal cuttings and seeds.

Proposed according to the invention the treatment of the plants and plant parts with the active compounds of PR is lead directly or impacts on the environment, habitat or closed repository conventional processing methods, such as dipping, spraying, evaporation, spraying, spreading, smearing, and when processing materials reproduction, in particular in the treatment of seeds, also a single-layer or multilayer wrapping.

The active substance can be translated in the usual preparative forms such as solutions, emulsions, wettable powders, suspensions, powders, pollinating agents, pastes, soluble powders, granules, concentrates, emulsions and suspensions, natural and synthetic substances impregnated with active substance, and microencapsulated in a polymer capsule form.

Such preparative form get in a known manner, for example by mixing the active substances with diluents, such as liquid solvents and/or solid carriers, optionally using surfactants, such as emulsifiers and/or dispersants and/or foam.

If the diluent water use, as auxiliary solvents can also be used, for example, organic solvents. As liquid solvents are used aromatic compounds such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatics is their hydrocarbons, such as chlorobenzene, chlorethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol and also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethylsulfoxide, and water.

As solid carriers used, for example, ammonium salts and natural powdered silicates, such as kaolin, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic powdered silicas, such as highly dispersed silicic acid, alumina and silicates; as carriers for granules are used, for example, crushed and fractionated natural rocks such as calcite, marble, pumice, thick, dolomite, and also synthetic granules of inorganic and organic powder, and granules of organic material such as sawdust, coconut shell, corn cobs and stalks of tobacco; as emulsifiers and/or foaming agent is used, for example, nonionic and anionic emulsifiers, such as esters polyoxyethylene fatty KIS is on, ethers polyoxyethylenated fatty alcohols, for example a simple alkylarylsulphonates ether, alkylsulfonate, alkylsulfate, arylsulfonate, and also protein hydrolysates; as dispersing agents are used, for example, exhaust lignin sulphate liquor and methyl cellulose.

Preparative form may contain binding agents, as carboxymethyl cellulose, powdered, granular and Latecoere natural and synthetic polymers such as gum Arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalin and lecithins, and synthetic phospholipids. Other additives can be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue, and organic dyestuffs, such as alizarin dyes, azo dyes and metallophthalocyanine dyes, and trace elements as nutrients, as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Preparative forms contain in General between 0.1 and 95 wt.%, preferably between 0.5 and 90 wt.%, the active substance.

Proposed according to the invention the active substance can be used for weed control as such or in their formulation also in a mixture with known what herbicide and/or substances, to improve compatibility with cultivated plants (protective agent), and you can use ready preparative forms or mixtures in the tank. It is also possible mixture with agents for weed control, which contain one or more known herbicides and protective substances.

For mixing use a known herbicides, such as acetochlor, alfthan(-sodium), klonipin, alachlor, aloxide(-sodium), ametrine is high, nicarbazin, amithlon, amidosulfuron, anilofos, Azul, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin(-ethyl), beforethat, encultured(-methyl), bentazon, bestindian, benzamycin, benzefoam, benzoylperoxy(-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromobutyl, bromophenoxy, bromoxynil, butachlor, butoverall (-allyl), butoxide, butyl cafestol, galaxidi, carbetamide, carfentrazone (-ethyl), chlorethoxyfos, chloramben, ozone chloride, chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlortoluron, cinidon(-ethyl), cinmetacin, kinokultura, clefoxydim, clethodim, clodinafop(-propargyl), clomazone, clomipram, clopyralid, cloperastine(-methyl), karasulu(-methyl), cumyluron, cyanazine, cybotron, cycloate, cycloaliphatic, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, desmedipham, diallate, dicamba, diclofop (-R), diclofop(-methyl), dicloflam, diacetyl(-ethyl), the WPPT is soquet, diflufenican, diflubenzuron, dimefuron, timepart, dimethachlor, deltamethrin, dimethenamid, Dimexidum, dinitramine, diphenamid, Diquat, dithiopyr, Diuron, damron, apoprotein, ARTS, asbroker, ethalfluralin, atomiculture(-methyl), ethofumesate, idoxifene, ethoxysulfuron, etamesonic, fenoxaprop(-P-ethyl), phentramin, planrep(-isopropyl-isopropyl-L-methyl), flazasulfuron, florasulam, fluazifop(-P-butyl), flatlet, flucarbazone (-sodium), flufenacet, flumetsulam, flumiclorac(pencil), flumioxazin, flubiprofen, flumetsulam, fluometuron, perchloride, verglichen(-ethyl), flupoxam, flypaper, flupyrsulfuron(-methyl-sodium), flurenol(-butyl), fluridone, fluroxypyr(-butoxypropyl, -meptyl), flurried, flurtamone, fluthiacet(-methyl), flutamide, fomesafen, foramsulfuron, glufosinate(-ammonium), glyphosate(-isopropylammonium), galasoft, haloxyfop(-ethoxyethyl, -R-methyl), hexazinone, imazamethabenz(-methyl), imazamethabenz imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron(-methyl-sodium), ioxynil, isopropylene, Isoproturon, Sauron, isoxaben, isoxaflutole, isoxaflutole, isocaporate, lactofen, lenacil, linuron, MSRA, mecoprop, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metaventure, metobromuron, (alpha)metolachlor, metosulam, metoxuron, metribuzin, m is sulfuron(-methyl), molinet, monolinuron, nitroanilide, napropamide, neburon, nicosulfuron, norflurazon, arrancars, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxacyclobutane, oxilorphan, paraquat, pelargonia acid, pendimethalin, pentalyn, phenoxazone, phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron(-methyl), proplusr, prometryn, propachlor, propanil, propaquizafop, propisochlor, propoxycarbazone(-sodium), propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolyl, pyrazolate, pyrazosulfuron(-ethyl), paradoxien, perbenzoic, perimutter, peridot perinatal, piritramid, Perminova(-methyl), pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(-P-ethyl, P-tefuryl), rimsulfuron, sethoxydim, Simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-(methyl), sulfosate, sulfosulfuron, tabulam, tebuthiuron, tepraloxydim, terbutylazine, terbutryn, tanishlar, tefloned, thiazopyr, thidiazuron, thifensulfuron(-methyl), thiobencarb, thiocarbonyl, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridian, trifluralin, trifloxysulfuron, triflusulfuron(-methyl), tritosulfuron.

In addition, mixing also apply protective substances, such as

AD-67, BAS-145138 bookshaker, cloquintocet (-mexyl), simerini, 2,4-D, DKA-24, dichlormid, damron, felorin, thoracal (-ethyl), Florasol, fluxotine, furilazole, isoxadifen (-ethyl), MSRA, mecoprop (-R), mefenpyr (-diethyl), MG-191, oxybutinin, PPG-1292, R-29148.

Can also be mixed with other active ingredients, such as fungicides, insecticides, acaricides, nematicides, protective substances from biting birds, nutrients and agents for improving soil structure.

The active substance can be applied as such, in the form of their formulations or forms prepared from them using the following dilution forms, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granulates. The introduction of active substances is carried out in the usual way, for example by watering, spraying, atomizing, spilling.

Proposed according to the invention the active substance can be entered before the shoot and after the shoot of the plants. Active substances can be introduced into the soil before sowing.

Used the consumption rate of the active substance may vary within wide limits. It mainly depends on the desired effect. Consumption rate, in General, is between 1 g and 10 kg of active substance per hectare of land, preferably between 5 g and 5 kg per hectare

As was already indicated above, according to the invention it is possible to treat all plants or parts thereof. In a preferred embodiment, about abayat species and varieties of plants, and parts thereof, grown or received conventional biological methods of cultivation, such as crossing or merging protoplasts. In the following preferred embodiment, handle transgenic plants and plant varieties obtained geotechnologies methods, optionally in combination with conventional methods (genetically modified organisms), and parts thereof. The notion of "part" or "parts of plants" or "plant organs" explained above.

Particularly preferred process according to the invention of the plants, respectively, received in trade or used varieties. Under the plant varieties understand plants with specific properties (characteristics), which are conventional breeding, by mutagenesis or by recombinant DNA techniques. This can be varieties, biotypes and genotypes.

Thanks proposed according to the invention the processing depending on the species and varieties of plants, their location and growth conditions (soils, climate, vegetation period, diet) are also possible unexpected (synergistic) effects. Thus, it is possible to reduce consumption norms, and/or expansion of the spectrum, and/or amplification steps used according to the invention substances and agents (also in combination with other agrochemical active substances and to improve the growth of the cultural plants, the increased tolerance of cultivated plants is relatively high or low temperatures, increased tolerance of cultivated plants are relatively drought or salt content in the water or soil, the increase in the intensity of flowering, easier harvesting, accelerated maturation, higher actual yield of high quality and/or higher nutritional value of the crop, high storage stability and/or processibility of the harvested crop, which is greater than originally expected effect.

It is preferable according to the invention the treated transgenic (received genotoksicskimi methods) plants or plant varieties are all plants received geotechnological modification of genetic material, which contributes to a particularly preferred securities properties (characteristics) of such plants. Such properties are, for example, improved plant growth, increased tolerance to relatively high or low temperatures, increased tolerance relative to drought or salt content in the water or soil, the increased intensity of flowering, easier harvesting, accelerated maturation, higher actual yield of high quality and/or higher nutritional value of the crop, high storage stability and/or processibility of the harvested crop. The trail is concerned, and particularly preferred examples of such properties are high protection against animal and microbial pests, such as insects, mites, phytopathogenic fungi, bacteria and/or viruses, as well as a high tolerance of plants relative to certain herbicide active substances. Transgenic plants are, for example, important cultivated plants such as cereals (wheat, rice), maize, soybeans, potatoes, cotton, canola, and vegetable crops (along with fruits, apples, pears, citrus crops and grapes), and particularly preferably produce corn, soybeans, potatoes, cotton and oilseed rape. As properties (attributes) are particularly preferred are the high protection of plants from insects due emerged in the plant toxins, in particular those that are formed in plants (hereinafter "Bt plants") using the genetic material from Bacillus thuringiensis (for example, genes CryIA(a), CryIA(b)CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, 3b and CryIF and also combinations thereof). As properties (attributes) are particularly characterized by high protection of plants against fungi, bacteria and viruses due to systemic acquired resistance (SAR), systemio, phytoalexin, elicitors, as well as resistance genes and corresponding experimental proteins and toxins. In addition, as properties (attributes) are particularly characterized by high tolerance of plants relative to certain herbicide active substances, e.g. the measures imidazoline, of the sulfonylureas, glyphosate or phosphinotricin (for example, "PAT-gene"). Genes with, respectively, the required properties (attributes), and can also exist in transgenic plants in combinations with each other. "Bt plants" are, for example, maize, cotton, soybeans and potatoes, which are sold under the trade names YIELD GARD®(for example, corn, cotton, soybeans), KnockOut®(for example maize), StarLink®(for example maize), Bollgard®(cotton), Nucotn®(cotton) and NewLeaf®(potatoes). Plants are tolerant to the herbicides are, for example, maize, cotton and soybean, which are sold under the trade names Roundup Ready®(tolerant glyphosate, for example corn, cotton, soybeans), Liberty Link®(tolerance to phosphinotricin, for example rape), IMI®(tolerant imidazoline) and STS®(tolerance to sulfonylureas, for example maize). Plants resistant to herbicides (conventionally grown on the basis of tolerance to herbicides)are, for example, the varieties sold under the trade name Clearfield®(for example, corn). Naturally, this also has implications for varieties of plants with such or in the future developed genetic properties (features)that will be in the future virusheat the camping or to do in the future on the market.

According to the invention these plants particularly preferably can be treated with compounds of General formula (I) or proposed according to the invention mixtures of the active substance, and in addition to good weed control is a synergistic effect in transgenic plants or plant varieties. The above field preferred values of active substances or mixtures are also used for processing of such plants. Especially notable is the treatment of plants specifically mentioned in this text, compounds or mixtures.

The collection and use of proposed according to the invention the active substances are explained by the following examples.

Obtaining compounds of Formula (I)

Example 1

A mixture of 2,80 g (8,43 mmol) of 2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl)-carbonyl]-amino]-benzoic acid, 0,945 g (8,43 mmol) 1-ethyl-5-hydroxy-pyrazole, 2,10 g (10.1 mmol) of dicyclohexylcarbodiimide and 30 ml of acetonitrile is stirred for 18 hours at room temperature (about 20° (C) and then filtered. The filtrate is mixed with 0,335 g (3,37 mmol) trimethylsilylacetamide and 1.70 g (to 16.9 mmol) of triethylamine, the mixture is stirred for 18 hours at room temperature and then concentrated under reduced pressure. The residue is stirred with 10%aqueous solution of CA is bonate sodium and then shaken with a simple diethyl ether. After the separation (and removal) of the organic phase the aqueous solution is acidified with concentrated hydrochloric acid and precipitated when this crystalline product is isolated by extraction.

Get 1,60 g (32.5% of theoretical) 1N-[2,6-dichloro-3-[(1-ethyl-5-hydroxy-1H-pyrazole-4-yl)-carbonyl]-phenyl]-3-methyl-2-oxo-1-imidazolidinecarboxamide.

logP (pH 2.3): 1,58.

Analogously to example 1, and in accordance with the above General description of the method and also you may receive, for example, are shown in the following table 1 compounds of General formula (I-1), (I-2) or (I-3).

The determination of the logP values given in table 1, carried out according to EEC-Directive 78/831 Annex V.A8 using HPLC (high performance liquid chromatography) on a column with treatment phases (18). Temperature: 43°C. Solvents: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% to 90% acetonitrile.

Calibration is carried out using unbranched Alkan-2-ones (with 3 to 16 carbon atoms), in which the logP values are known (op is adelene logP values is performed using retention time by linear interpolation between two successive alkanoate).

Getting the source compounds of the formula (III):

Example (III-1)

The mixture of 11.3 g (32,9 mmol) of a compound methyl ester 2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl)-carbonyl]-amino]-benzoic acid, 50 ml water, 50 ml of tetrahydrofuran and 1.3 g of sodium hydroxide is stirred for 18 hours at room temperature (about 20°) and then concentrated under reduced pressure to about half volume. The mixture is then shaken with a simple diethyl ether, the organic phase is separated (and removed) and the aqueous phase is acidified with concentrated hydrochloric acid. Fallen in this crystalline product is isolated by extraction.

Get 9,1 g (81.5 per cent of theoretical) of 2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl)-carbonyl]-amino]-benzoic acid.

logP (pH 2.3): 1,35.

Analogously to example (III-1) is also possible to obtain, for example, are shown in the following table 2 compounds of General formula (III)

Getting the source compounds of the formula (IIIa):

Example (IIIa-1)

A mixture of 12.3 g (50 mmol) of a compound methyl ester 2,4-dichloro-3-isocyanato-benzoic acid, 5.0 g (50 mmol) of 1-methyl-2-oxo-imidazolidine, a few drops of triethylamine and 100 ml of acetonitrile AC who're asked for 18 hours at room temperature (about 20° C) and then concentrated under reduced pressure. Then the rest degenerous simple diethyl ether and the crystalline product isolated by extraction.

Obtain 11.4 g (60% of theoretical) of a compound methyl ester 2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl)-carbonyl]-amino]-benzoic acid.

logP (pH 2.3): 1,94.

Analogously to example (IIIa-1) also may receive, for example, are shown in the following table 3 compounds of General formula (IIIa).

Biological examples

Example

Research before you shoot plants

Solvent: 5 wt.% acetone

Emulsifier: 1 wt.% simple alkylarylsulphonates ether

To obtain the necessary form of the active substance 1 wt.% active substances specified in table 4, is mixed with the specified amount of solvent, add the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration.

The seeds of the studied plants are sown in normal soil. After 24 hours, the soil is sprayed in the finished form of the active substance so that the desired amount of active substance was in the unit square. The concentration of the active substance in the working solution is determined so that the desired quantity is the proportion of the active substance was in 1000 litres of water per hectare.

Three weeks later analyze the degree of plant damage in % damage in comparison with the development of the untreated control plants. Mean:

0% = result not available (untreated control samples)

100% = total destruction of weeds

The results of the studies summarized in table 4.

Table 4
Herbicide action in % relative
The analyzed compound of example No.The rate of application of the compounds, g/hectareABUTH1)AMARE2)CHEAL3)DATST4)GALAP9)SOLNI6)STEME7)VIOAR8)Damage to wheat in %
1125100-100100--1001000
2125100-100--100--0
3250100100--100100 100-0
4500100100------0
5125100-100100----0
6250100100100100-100100-0
1)ABUTH Abutilon theophrasti
2)CHEAL Chenopodium album
3)SOLNI Solanum nigrum
4)VIOAR Viola arvensis
5)AMARE Amaranthus retroflexus
6)DATST Datura stramonium
7)GALAP Galium aparine
8)STEME Stellaria media

Example B

The study of post-emergent plants:

solvent: 5 wt.% acetone

emulsifier: 1 wt.% simple alkylarylsulphonates ether

To obtain the necessary form of the active substance 1 wt.% active substances specified in table 5, is mixed with the specified amount of solvent, add the specified amount of EMU is igator and the concentrate is diluted with water to the desired concentration.

The investigated plants with a height of 5-15 cm are sprayed with the finished form of the active substance so that the desired amount of active substance was in the unit square. The concentration of the working solution is determined so that a desired amount of the active substance was in 1000 litres of water per hectare.

Three weeks later analyze the degree of plant damage in % damage in comparison with the development of the untreated control plants. Mean:

0% = result not available (untreated control samples)

100% = total destruction of weeds

The results of the studies summarized in table 5.

Table 5
Herbicide action in % relative
The analyzed compound of example No.The rate of application of the compounds, g/hectareABUTH1)AMARE2)CHEAL3)DATST4)ECHCG9)SOLNI6)STEME7)VIOAR8)Damage to wheat in %
125095-9595-- 95950
2125--100100-100-1000
3250---95959595-0
4125-959595-9595-0
1)-8)see notes to table 4
9)Echinochloa grus galli

If pre-emergence or post-harvest processing plants to use the herbicide agent containing as an active substance of the compound of examples 6-62, achieved similar results with the results given in tables 4, 5.

Examples of specific herbicide funds

The fine powder (dust-like tool)

The fine powder is obtained by mixing 10 weight. parts of the compounds of General formula (I) with 90 weight. parts of talc as inert substance and then crushed in a hammer mill.

Dispersible powder

Easily dispersible in water, humidified powder is such that the cm who're asked 25 parts by weight of compounds of General formula (I), 64 weight parts of kaolin-containing quartz as inert substance, 10 parts by weight of potassium salt of a lignin-sulfonic acids and 1 weight. part of the sodium salt oleoylethanolamide acid as wetting and dispersing means and ground in a rod mill.

Dispersible concentrate

Easily dispersible in water concentrate get so that mixing 20 parts by weight of compounds of General formula (I), 6 weight. parts of alkylphenol ether (®Triton X 207), 3 weight. part isotridekanolethoxylate ether (8 EO) and 71 weight. part of paraffinic mineral oil (boiling, for example, from about 255 to 277° (C) and milled in a ball mill to a fineness of less than 5 microns.

Emulsifiable concentrate

Emulsifiable concentrate is obtained by mixing 15 weight. parts of the compounds of General formula (I) with 75 weight. parts of cyclohexanone as solvent and 10 weight. parts of oxyethylated Nonylphenol as emulsifier.

Dispersible in water, the granules

Dispersible in water granulate get so that mixed

75 weight. parts of the compounds of General formula (I),

10 weight. parts of the calcium salt of ligninsulfonate,

5 weight. parts sodium lauryl sulphate,

3 weight. parts polyvinyl alcohol and

7 weight. parts of kaolin

<> on the rod mill and the resulting powder granularit in the vortex layer by spraying with water as the granulating liquid.

1. Substituted benzoylpyrazoles General formula (I)

in which Q means O (oxygen),

R1means alkyl with 1-6 carbon atoms,

R2means hydrogen,

R3, R4independently of one another denote hydrogen, halogen; alkyl with 1-4 carbon atoms, substituted with halogen,

R5means hydrogen; alkyl with 1-6 carbon atoms,

Y represents hydrogen;

Z means alkoxyamino with 1-6 carbon atoms; substituted alkoxy with 1-4 carbon atoms, alkylamino with 1-6 carbon atoms; N-alkyl-alkoxyamino with 1-4 carbon atoms; cyclooctylamino with 3-6 carbon atoms; phenyl, substituted with halogen; monocyclic heterocyclyl, heterocyclisation, -N=(heterocyclyl) from a number of furil, tetrahydrofurfurylamine, pyrrolidinyl, pyrrolidinyl, 2-oxo-1,3-diazocyclopentadiene, isoxazolyl, dihydroisoxazole (isoxazoline), tetrahydroisoquinoline (isoxazolidine), tetrahydro-(2H)-1,2-oxazin-2-yl, dihydrothiazolo (thiazoline), oxadiazolidine, thiadiazolidine, piperidinyl, piperidylamine, 2-oxo-1,3-disallowance, morpholinyl, morpholinium, respectively, the ri having substituted by alkyl with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, cycloalkyl with 3-6 carbon atoms, including all possible tautomeric forms and possible salt.

2. Substituted benzoylpyrazoles formula (I) according to claim 1, in which

R1is methyl, ethyl, n - or ISO-propyl,

R2- hydrogen

R3, R4independently of one another denote hydrogen, fluorine, chlorine, bromine, deformity, trifluoromethyl, dichloromethyl, trichloromethyl,

R5is hydrogen, methyl, ethyl, n - or isopropyl, n - or isobutyl,

Y is hydrogen,

Z - methoxyamino, amoxilina, n - or isopropylamino, N-methylmethanamine, phenyl, substituted by fluorine, chlorine, bromine, monocyclics heterocyclyl, heterocyclisation, group-N=(heterocyclyl) from a number of furil, tetrahydrofurfurylamine, pyrrolidinium, 2-oxo-1,3-diazocyclopentadiene, isoxazolyl, dihydroisoxazole (isoxazoline), tetrahydroisoquinoline (isoxazolidine), dihydrothiazolo (thiazoline), oxadiazolidine, thiadiazolidine, piperidinyl, piperidylamine, 2-oxo-1,3-disallowance, morpholinyl, morpholinium, respectively optionally substituted stands, ethyl, n - or the isopropyl, n-, ISO-, sec - or tert-bootrom.

3. Substituted benzoylpyrazoles formula (I) according to claim 1, in which

Q - O (oxygen),

R1is methyl, ethyl, n - or isopropyl,

R2- hydrogen

R3, R4independently of one another denote hydrogen, fluorine, chlorine, bromine, methyl, ethyl, deformity, trifluoromethyl, dichloromethyl, trichloromethyl,

R5is hydrogen, methyl, ethyl, n - or isopropyl,

Y is hydrogen,

Z - methoxyamino, amoxilina, n - or isopropylamino, N-methylmethanamine, phenyl, substituted by fluorine, chlorine, bromine, monocyclic heterocyclyl, heterocyclisation, group-N=(heterocyclyl) from a number of furil, tetrahydropyrimidine, 2-oxo-1,3-diazocyclopentadiene, isoxazolyl, dihydroisoxazole (isoxazoline), tetrahydroisoquinoline (isoxazolidine), dihydrothiazolo (thiazoline), piperidinyl, piperidylamine, 2-oxo-1,3-diaza-cyclohexyl, morpholinyl, morpholinium, respectively optionally substituted stands, ethyl, n - or isopropyl, n-, ISO-, sec - or tert-bootrom.

4. Herbicide agent, characterized in that it contains a compound according to one of claims 1 to 3, and conventional additives.



 

Same patents:

FIELD: chemistry of heterocyclic compounds, medicine, pharmacy.

SUBSTANCE: invention relates to novel heterocyclic compounds of the general formula (I): wherein R1 represents hydrogen atom or (C1-C6)-alkyl; R2 represents hydrogen atom, -CO-R3 wherein R3 represents (C2-C6)-alkyl substituted optionally with halogen atom, -CO-C(R4)=C(R4)-R5 wherein R4 represents hydrogen atom or (C1-C4)-alkyl; R5 represents (C1-C8)-alkyl, (C2-C8)-alkenyl and others; Y represents compound of the formula: wherein R7 represents hydrogen atom or (C1-C4)-alkyl; R8 represents (C5-C8)-alkyl, (C4-C8)-cycloalkyl and others; X represents oxygen atom or sulfur atom and others. Also, invention relates to pharmaceutically acceptable salts of these compounds. Compounds of the formula (I) possess hypoglycemic and/or hypolipidemic activity and can be used in medicine in treatment of diabetes mellitus, hyperlipidemia, hyperglycemia, diseases caused by resistance to insulin and other diseases.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.

28 cl, 3 tbl, 131 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to novel substituted derivatives of 4-phenyltetrahydroisoquinoline of the general formula (I): wherein R1, R2, R3 and R4 mean independently of one another hydrogen (H), fluorine (F), chloride (Cl), bromine (Br) atoms, CaH2a+1 wherein one or more atoms H are substituted with F, -NR11R12 or -SOj-R15 wherein a = 1-8; R11 and R12 mean independently of one another H, CeH2e+1 or CrrH2rr-1 wherein e = 1-4; rr = 3, 4, or in common with nitrogen atom to which they are bound form a cycle chosen from group consisting of pyrrolidinyl, piperidinyl, N-methylpiperazinyl, piperazinyl or morpholine; j = 1 or 2; R15 means CkH2k+1 wherein k = 1-8; R5 means CpH2p+1 or CssH2ss-1; p = 1-8; ss = 3-8; R6 means H; R7, R8 and R9 mean independently of one another mean -SOwR23, -NR32COR30, NR32CSR30, -NR32SObbR30, H, F, Cl, Br, -OH, -NH2, CeeH2ee+1, -NR40R41, -CONR40R41 or -COOR42 wherein w = 0, 1 or 2; bb = 2 or 3; R23 means NR25R26 wherein R25 and R26 mean independently of one another H or CzH2z+1, CzzH2zz-1 wherein z = 1-8; zz = 3-8 wherein in CzH2z+1 and CzzH2zz-1 one or more H atoms are substituted with fluorine atom and one or more CH2-groups are substituted with -C(=O) or NR27 wherein R27 means H or CaaH2aa+1 wherein aa = 1-4; or R25 and R26 in common with nitrogen atom to which they are bound form 5-, 6- or 7-membered cycle; R30 means H, CccH2cc+1, CyyH2yy-1, pyrrolydinyl, piperidinyl wherein in their cycles CH2-group can be substituted with oxygen atom (O) or -NR33; R32 and R33 mean independently of one another H or ChH2h+1 wherein cc = 1-8; yy = 3-8; h = 1-8 wherein in the group ChH2h+1 one or more hydrogen atoms are substituted with fluorine atom, and in the groups CccH2cc+1 and CyyH2yy-1 one or more hydrogen atoms can be substituted with fluorine atom, and CH2-group can be substituted with O or -NR31 wherein NR31 means H, methyl, ethyl, acetyl or -SO2CH3; or R30 means 6-membered heteroaryl with 1-4 nitrogen atoms, 0 or 1, S-atoms or 0, or 1 O-atom that represents unsubstituted or substituted with up to three substitutes chosen from group consisting of F, Cl, Br, J, CooH2oo+1 wherein one or more hydrogen atoms can be substituted with fluorine atom, -NO2 or -NR70R71 wherein oo = 1-8; R70 and R71 mean independently of one another H, CuuH2uu+1 or -COR72 wherein uu = 1-8; R72 means H, CvvH2vv+1 wherein vv = 1-8; ee = 1-8; R40 and R41 mean independently of one another H, CttH2tt+1 or -C(NH)NH2 wherein tt = 1-8 and wherein in the group CttH2tt+1 one or more CH2-groups can be substituted with NR44 wherein R44 means CggH2gg+1 wherein gg = 1-8; R42 means H or ChhH2hh+1 wherein hh = 1-8 being, however, two substitutes from group R7, R8 and R9 can't mean -OH simultaneously, and at least one residue from R7, R8 and R9 must be chosen from group consisting of -CONR40R41, -OvSOwR23, -NR32COR30, -NR32CSR30 and -NR32SObbR30. Also, invention relates to using above given compounds for preparing a medicinal agent. Also, invention considers a medicinal agent representing inhibitor of sodium-proton exchange of subtype III (NHE3) based on proposed compounds. Invention provides synthesis of novel compounds, a medicinal agent based on thereof for aims of treatment of such diseases as nervous system ischemia, insult and brain edema, in treatment of snore, shock, impaired respiratory impulse, as purgative agents, as agents against extoparasites, for prophylaxis of gall stones formation, as anti-atherosclerotic agents, agents against diabetes mellitus later complications, cancer diseases, fibrous diseases, endothelial dysfunction, hypertrophies and hyperplasia of organs and others.

EFFECT: valuable medicinal properties of compounds and medicinal agents.

21 cl, 15 tbl, 221 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention proposes novel derivatives of thiazole that able for effective binding and activating PPARα and/or PPARγ simultaneously and, respectively, combine antiglycemic effect caused by activation of PPARγ with anti-dyslipidemic effect caused by activation of PPARα. Also, the claim describes compounds of the formula (I): wherein substitutes from R1 to R10 as well as X and Y are determined in the description and invention claim, and their pharmaceutically acceptable salts and esters also. Also, the proposed invention describes pharmaceutical compositions possessing antagonistic activity with respect to PPARα and/or PPARγ comprising compound of the formula (I) as an active component and pharmaceutically acceptable carrier and/or additive. Except for, the invention proposes claimed compounds as therapeutically active substances for treatment and/or prophylaxis of diseases mediated by agonists of PPARα and/or PPARγ, such as diabetes mellitus, non-insulin dependent diabetes mellitus, elevated blood pressure, increased level of lipids and cholesterol, atherosclerotic diseases, metabolic syndrome, endothelial dysfunction, procoagulant state, dyslipidemia, ovary polycystic syndrome, inflammatory or proliferative diseases.

EFFECT: valuable medicinal properties of compounds.

27 cl, 140 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to derivatives of benzothiazole of the general formula (I): and their pharmaceutically acceptable acid-additive salts used as ligands of adenosine receptors and to a medicinal agent based on thereof. In compound of the general formula (I) R means phenyl, pyridine-2-yl, -C(O)-O-(lower)-alkyl, -C(O)-(lower)-alkyl, -C(O)-morpholinyl, -C(O)-NR'2, -(CH2)n-NR'2 or -(CH2)n-O-(lower)-alkyl; R' means hydrogen atom or (lower)-alkyl. Compounds can be used in treatment and prophylaxis of diseases mediated by adenosine receptors A2A and A1, for example, in Alzheimer's disease, some depressive states, toxicomania, Parkinson's disease.

EFFECT: valuable medicinal properties of compounds.

15 cl, 3 sch, 6 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to derivatives of nicotine- or isonicotine-benzothiazole of general formulas (IA) and (IB) their pharmaceutically acceptable acid-additive salts and a medicinal agent based on thereof. In compounds of general formula (IA) and (IB) R1 means phenyl, piperidine-1-yl or morpholine; A means -O-; R means -(CH2)n-N(R'')-C(O)-lower alkyl, -(CH2)n-O-lower alkyl, -(CH2)n-O-(CH2)n-O-lower alkyl, lower alkyl, -(CH2)n-morpholinyl, -(CH2)n-phenyl, -(CH2)n-N(R''), -(CH2)n-pyridinyl, -(CH2)n-CF3, -(CH2)n-2-oxopyrrolidinyl or (C4-C6)-cycloalkyl; R'' mean(s) independently of one another hydrogen atom or lower alkyl; n= 1 or 2; A means -N(R')-; R means lower alkyl, (C4-C6)-cycloalkyl, -(CH2)n-O-lower alkyl, -(CH2)n-pyridinyl, -(CH2)n-piperidinyl, -(CH2)n-phenyl, -(CH2)n-N(R'')-C(O)-lower alkyl, -(CH2)n-morpholinyl or -(CH2)n-N(R'')2; R' and R'' mean independently of one another hydrogen atom or lower alkyl; n = 1 or 2; or A means -CH2-; R means -N(R'')-(CH2)m-O-lower alkyl, -N(R'')2, S-lower alkyl, or R means azethidinyl, pyrrolidinyl or piperidinyl that are substituted optionally with hydroxy-group or lower alkoxy-group; or R means morpholinyl, -N(R'')-(CH2)m-(C4-C6)-cycloalkyl, -N(R'')-(CH2)m-C(O)-O-lower alkyl, -O-(CH2)m-O-lower alkyl or alkoxy-group; R'' mean(s) independently of one another hydrogen atom or lower alkyl; m = 1, 2 or 3; or A means -S-; R means lower alkyl, or A-R mean in common piperazinyl substituted with alkyl, -C(O)-lower alkyl or oxo-group, or group A-R means piperidinyl substituted with lower alkoxy-group or hydroxy-group, or group A-R means morpholinyl substituted with lower alkyl, or group A-R means (C4-C6)-cycloalkyl, azethidine-1-yl optionally substituted with hydroxy-group or lower alkoxy-group, or group A-R means thiomorpholinyl-1,1-dioxo-group, tetrahydropyrane or 2-oxa-5-azabicyclo[2.2.1]hept-5-yl. Proposed compounds can be used in treatment of diseases mediated by adenosine A2A-receptors, for example, Alzheimer disease, some depressive states, toxicomania and Parkinson's disease.

EFFECT: valuable medicinal properties of compounds and agent.

37 cl, 10 sch, 109 ex

FIELD: organic chemistry, biochemistry.

SUBSTANCE: invention relates to using compounds represented by the general formula (II): wherein Ra and Rb are chosen independently from hydrogen atom, alkyl, cycloalkyl, aryl (optionally substituted with a group chosen from alkyl, halogen atom and alkoxy-group), -(Z)n-aryl (optionally substituted with a group chosen from alkyl, halogen atom and alkoxy-group), -(Z)nC(O)OR3; Z is chosen independently from -C(R3)(R4)-; R3 and R4 are chosen independently from hydrogen atom, alkyl and 6-membered cycle with nitrogen atom as a heteroatom; n has values 0, 1 or 2; X and Y are chosen independently from =O, =S and =N(R3). These compounds are active component in preparing a pharmaceutical composition designated in treatment of diseases wherein glycogen synthase-kinase 3-beta (GSK-3) is involved. Also, invention relates to compounds represented by the general formula (II) wherein Ra is chosen from -CH2Ph, -CH2CO2Et, 4-OMePh, 4-MePh and 4-BrPh; Rb is chosen from Me and -CH2CO2Et; X and Y represent =O. Also, invention relates to a pharmaceutical composition possessing GSK-3-inhibitory activity and containing compound of the general formula (II) as an active component. Invention provides using heterocyclic inhibitors of glycogen synthase-kinase-3β.

EFFECT: valuable biochemical and medicinal properties of inhibitors.

17 cl, 5 tbl, 5 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to derivatives of piperidine of the general formula (I): or their pharmaceutically acceptable salts wherein rings A and B represent optionally substituted benzene rings; R1 represents alkyl, hydroxyl, thiol, carbonyl, sulfinyl, unsubstituted or substituted sulfonyl group and others; R2 represents hydrogen atom, hydroxyl, amino-group, alkyl, unsubstituted or substituted carbonyl group or halogen atom; Z represents oxygen atom or group -N(R3)- wherein R3 and R4 represent hydrogen atom or alkyl group under condition that N-acetyl-1-benzyloxycarbonyl-2-phenyl-4-piperidineamine is excluded. Compounds of the formula (I) or their salts possess antagonistic activity with respect to tachykinin NK1-receptors and can be used in medicine in treatment and prophylaxis of inflammatory, allergic diseases, pain, migraine, diseases of central nervous system, digestive organs and others.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition, improved method of treatment.

18 cl, 138 tbl, 527 ex

FIELD: medicine.

SUBSTANCE: compound is represented by structural formula

or its pharmaceutically permissible salts, where R1 is the hydrogen atom (1), C1-8acyl(2), hydroxyl (3), halogen atom (5), C2-8acyl (3), C1-8-alcocsy (4), substituted with phenyl or C2-8acyl, substituted with NR2R3; R2R3 independently represent hydrogen atom (1) or C1-8acyl(2), X and Y each independently representing C (1), CH (2) or N (3). is (1) single or (2) double bond. is 5-7-member carbocyclic group or 5-7-member partially or fully saturated heterocyclic group defined in claim 1 of invention. A is one of A1 to A5 groups defined by claim 1 of the invention. The compounds show inhibiting properties relative to poly(ADP-ribose)polymerase are usable as prophylactic and/or curative drugs for treating ischemic diseases (in brain, spinal cord, heart, digestive tract, skeletal muscle, eye retina, e.t.c.), inflammatory diseases (intestinal inflammation, disseminated sclerosis, arthritis, e.t.c.), neurodegenerative disorders (extrapyramidal disorder, Alzheimer disease, muscle dystrophy, cerebrospinal canal stenosis in lumbar segment of the vertebral column, e.t.c.), diabetes, stroke, cerebral injury, hepatic insufficiency, hyperalgesia, e.t.c. The compounds are also of use in struggling against retroviruses (HIV and others), as sensitizing agents for treating cancer cases and immunodepressant agents.

EFFECT: enhanced effectiveness of treatment.

19 cl, 90 tbl

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to novel substituted indoles or its pharmaceutically acceptable salts of the formula (I): , wherein R1 means hydrogen (H) atom, halogen atom, -CN, nitro-group, -SO2R4, -OH, -OR4, -SO2NR5R6, -CONR5R6, -COOH, -COOCH3, -NR5R6, phenyl, naphthyl or (C1-C6)-alkyl wherein the latter group is possibly substituted with one or more substitutes chosen independently from halogen atom, -OR8 and -NR5R6 wherein x = 2; R2 means (C1-C7)-alkyl; R3 means phenyl, naphthyl or heteroaryl and each of them is possibly substituted with one or more substitutes chosen independently from H, halogen atom, -CN, -OH, -SO2R4, -OR4, -SO2NR5R6, -CONR5R6, phenyl, naphthyl, (C1-C6)-alkyl wherein the latter group is possibly substituted with one or more substitutes chosen independently from halogen atoms, -OR8 and -NR5R6, -S(O)xR7 wherein x = 2; R4 means (C1-C6)-alkyl; R5 and R6 mean independently H, (C1-C6)-alkyl, or R5 and R6 in common with nitrogen atom to which they are bound can form 6-membered saturated heterocyclic ring comprising one atom chosen from -NR16; R7 means (C1-C6)-alkyl; R8 means H, (C1-C6)-alkyl; R16 means H, -COY-(C1-C4)-alkyl wherein Y means oxygen atom (O) and wherein alkyl group in the substitute group can be direct, branched or cyclic, and wherein heteroaryl means 5-6-membered heteroaromatic ring comprising from 1 to 3 heteroatoms chosen from nitrogen (N), oxygen (O) and sulfur (S) atoms, or means 6,6-condensed bicyclic aromatic ring system comprising one nitrogen atom. Compounds of the formula (I) can be used in production of a medicinal agent used in treatment of asthma and chronic obstructive disease.

EFFECT: valuable medicinal properties of compounds.

7 cl, 2 tbl, 59 ex

FIELD: organic chemistry, herbicides.

SUBSTANCE: invention relates to a compound of the general formula [I]: wherein R1 and R2 can be similar or different and each represents (C1-C10)-alkyl group; each among R3 and R4 represents hydrogen atom; R5 and R6 can be similar or different and each represents hydrogen atom or (C1-C10)-alkyl group; Y represents 5-6-membered aromatic heterocyclic group or condensed aromatic heterocyclic group comprising one or some heteroatoms chosen from nitrogen atom, oxygen atom and sulfur atom wherein heterocyclic group can be substituted with 0-6 of similar or different groups chosen from the following group of substitutes α, and so on; n means whole values from 0 to 2; [Group of substitutes α]: hydroxyl group, halogen atoms, (C1-C10)-alkyl groups, (C1-C10)-alkyl groups wherein each group is monosubstituted with group chosen from the following group of substitutes β, (C1-C4)-halogenalkyl groups, (C3-C8)-cycloalkyl groups, (C1-C10)-alkoxy-groups, (C1-C10)-alkoxy-groups wherein each group is monosubstituted with group chosen from the following group of substitutes and so on; [Group of substitutes β]: hydroxyl group, (C3-C8)-cycloalkyl groups that can be substituted with halogen atom or alkyl group, (C1-C10)-alkoxy-group, (C1-C10)-alkylthio-groups, (C1-C10)-alkylsulfonyl groups, (C1-C10)-alkoxycarbonyl groups, amino-group, carbamoyl group (wherein its nitrogen atom can be substituted with similar or different (C1-C10)-alkyl groups), (C1-C6)-acyl groups, (C1-C10)-alkoxyimino-groups, cyano-group, optionally substituted phenyl group; [Group of substitutes γ]: optionally substituted phenyl group, optionally substituted aromatic heterocyclic groups, cyano-group. Also, invention relates to herbicide comprising derivative of isoxazoline of the formula [I] as an active component or its pharmaceutically acceptable salt. Invention provides the development of isoxazoline derivative possessing the herbicide activity with respect to resistant weeds, selectivity for cultural crop and weed.

EFFECT: valuable herbicide properties of substances.

18 cl, 24 tbl, 106 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention describes novel compounds of the general formula (I) wherein p, R1, R2, R3 and A are determined in the invention description, their individual isomers and their pharmaceutically acceptable salts. Proposed compounds possess antagonistic effect with respect to muscarinic receptors that allows their using in treatment and prophylaxis of diseases yielding to treatment with muscarinic receptor antagonist. Also, invention describes a pharmaceutical composition containing these compounds.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.

23 cl, 22 ex

FIELD: chemistry of heterocyclic compounds, medicine, pharmacy.

SUBSTANCE: invention relates to novel heterocyclic compounds of the general formula (I): wherein R1 represents hydrogen atom or (C1-C6)-alkyl; R2 represents hydrogen atom, -CO-R3 wherein R3 represents (C2-C6)-alkyl substituted optionally with halogen atom, -CO-C(R4)=C(R4)-R5 wherein R4 represents hydrogen atom or (C1-C4)-alkyl; R5 represents (C1-C8)-alkyl, (C2-C8)-alkenyl and others; Y represents compound of the formula: wherein R7 represents hydrogen atom or (C1-C4)-alkyl; R8 represents (C5-C8)-alkyl, (C4-C8)-cycloalkyl and others; X represents oxygen atom or sulfur atom and others. Also, invention relates to pharmaceutically acceptable salts of these compounds. Compounds of the formula (I) possess hypoglycemic and/or hypolipidemic activity and can be used in medicine in treatment of diabetes mellitus, hyperlipidemia, hyperglycemia, diseases caused by resistance to insulin and other diseases.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.

28 cl, 3 tbl, 131 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention describes novel aromatic compounds that can be used in treatment of diseases or pathological states accompanying by inflammation, for example, chronic inflammation diseases. Invention describes compound of the formula (II): wherein G means phenyl, pyridinyl, pyrazolyl and wherein G is substituted with one or some groups R1, R2 or R3; Ar means naphthyl; X means (C5-C8)-cycloalkyl or cycloalkenyl optionally substituted with 1-2 oxo-groups, phenyl, furanyl, pyridinyl or pyrazolyl; Y means a bond or saturated either unsaturated branched or unbranched (C1-C4)-carbon chain wherein one or some methylene groups are optionally and independently substituted with oxygen (O) or nitrogen (N) atoms; Y is optionally substituted with oxo-group; Z means phenyl, tetrahydropyranyl, tetrahydrofuranyl, 1,3-dioxolanonyl, morpholinyl, thiomorpholinyl, piperidinyl, piperidinonyl, piperazinyl, pentamethylenesulfoxidyl wherein each of them is optionally substituted with 1-3 (C1-C6)-alkyls or group -CONH2, (C1-C6)-alkyl, nitrile, hydroxy-group, (C1-C6)-alkoxy-group, secondary or tertiary amine wherein amine nitrogen is bound covalently with (C1-C3)-alkyl or (C1-C5)-alkoxyalkyl, tetrahydrofuranyl-(C1-C3)-alkyl, nitrile-(C1-C3)-alkyl, carboxamide-(C1-C3)-alkyl; R1 means independently in each case (C1-C10)-alkyl which is optionally partially or completely halogenated and optionally substituted with 1-3 hydroxy-groups, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyl, cycloheptanyl wherein each of them is optionally substituted with 1-3 groups -CN, halogen atom, (C3-C6)-alkynyl branched or unbranched carbon chain and one or some methylene groups is optionally replaced for atom O and indicated alkynyl group is optionally substituted with one or some (C1-C4)-alkyl groups; R2 means branched or unbranched (C1-C6)-alkyl that is optionally partially or completely halogenated, branched or unbranched (C1-C4)-alkoxy-group that in each case is optionally partially or completely halogenated, halogen atom, (C1-C6)-alkoxy-group, hydroxy-group, mono- or di-(C1-C4)-alkyl-amino-group, group -OR6, nitro-group or group mono- or di-(C1-C4)-alkyl-amino-S(O)2 that is optionally partially or completely halogenated, or group -H2NSO2; R3 in each case means independently phenyl, pyridinyl, pyrimidyl, pyrrolidinyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyl, cycloheptanyl, (C1-C4)-alkynyl group or branched or unbranched (C1-C6)-alkoxy-group wherein each of them is optionally partially halogenated, -OR18 or (C1-C6)-alkyl optionally substituted with group -OR18, amino-group or mono- either di-(C1-C5)-alkyl-amino-group, (C2-C6)-alkynyl branched or unbranched carbon chain wherein one or some methylene groups are optionally replaced for atom O, and indicated alkynyl group is optionally substituted with one or some (C1-C4)-alkyl groups; R6 means (C1-C4)-alkyl that is optionally partially or completely halogenated; in each case R18 means independently hydrogen atom, (C1-C4)-alkyl; W means atom O, and its pharmaceutically acceptable derivatives. Also, invention describes a pharmaceutical composition containing these compounds and a method for treatment of disease mediated by cytokines and based on indicated compounds. Invention provides synthesis of novel compounds possessing valuable biological properties.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition, improved method of treatment.

12 cl, 1 tbl, 38 ex

FIELD: organic chemistry, chemical technology, medicine, pharmacy.

SUBSTANCE: invention relates to novel oxazolidinones of the general formula (I): , their pharmaceutically acceptable salts, hydrates and salt hydrates that inhibit factor Xa selectively and possess anti-thrombosis effect. Also, invention relates to a method for synthesis of these compounds (variants) and using the known substituted oxazolidinones of the general formula (A): as agent inhibiting factor Xa selectively and possessing anti-thrombosis effect, and to a medicinal agent based on at least one compound of the formula (I) or at least one compound of the general formula (A). Values of substitutes R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are given in the invention claim.

EFFECT: improved method of synthesis, valuable medicinal properties of compounds and agent.

10 cl, 2 tbl, 252 ex

FIELD: organic chemistry, chemical technology, insecticides.

SUBSTANCE: invention relates to derivatives of N-heteroaryl-4-(halogenalkyl)nicotinamide represented by the general formula (I): wherein R represents (C1-C6)-alkyl group that can be substituted with one or some halogen atoms; R1 represents hydrogen atom, (C1-C6)-alkyl group that can be substituted with one or some substituted chosen from group of substitutes A, (C2-C6)-alkenyl group or acyl group; X represents group of the formula -C-R2 or nitrogen atom; each among R2 and R3 represents independently hydrogen atom, halogen atom, (C1-C6)-alkyl group that can be substituted with one or some substitutes chosen from group of substitutes A, (C3-C7)-cycloalkyl group, (C2-C6)-alkenyl group, (C3-C7)-cycloalkenyl group, formyl group, group of the formula: -CH=NOR4 (wherein R4 represents hydrogen atom or (C1-C6)-alkyl group, cyano-group, phenyl group that can be substituted with one or some substitutes chosen from group of substitutes B, 5- or 6-membered heterocyclic group (heterocycle comprising 1-2 heteroatoms that are similar and chosen from nitrogen atom), (C1-C6)-alkoxy-group, (C1-C6)-alkylthio-group or phenoxy-group. The group of substitutes A represents group consisting of halogen atom, (C1-C6)-alkoxy-group, (C1-C6)-alkylthio-group, cyano-group and phenyl group. The group of substitutes B represents group consisting of halogen atom, (C1-C6)-alkyl group that can be substituted with one or some substitutes chosen from above given group of substitutes A, (C1-C6)-alkoxy-group that can be substituted with one or some substitutes chosen from above given group of substitutes A, or its salt. Also, invention relates to insecticide comprising a derivative of N-heteroaryl-4-(halogenalkyl)nicotinamide or its salt as an active component and a carrier optionally. Also, invention relates to a method for synthesis of derivative of N-heteroaryl-4-(halogenalkyl)nicotinamide. Invention provides synthesis of derivatives of N-heteroaryl-4-(halogenalkyl)nicotinamide possessing the high insecticide activity.

EFFECT: improved method of synthesis, valuable properties of derivatives.

18 cl, 3 tbl, 91 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to novel derivatives of benzimidazole of the general formula (I): wherein A represents -CH2- or -C(O)-; Y represents -S- or -NH-; R1 and R2 represent independently hydrogen atom, (C1-C8)-alkyl, (C5-C9)-bicycloalkyl optionally substituted with one or some similar or different (C1-C6)-alkyl radicals, or radical of the formula -(CH2)n-X wherein X represents amino-group, (C3-C7)-cycloalkyl and other values of radicals also given in the invention claim; R3 represents -(CH2)p-W-(CH2)p'-Z3 wherein W3 represents a covalent bond, -CH(O)- or -C(O)-; Z3 represents (C1-C6)-alkyl, aryl radical, heteroaryl and other values of radical also; V3 represents -O-, -S-, -C(O)-, -C(O)-O-, -SO2- or a covalent bond; Y3 represents (C1-C6)-alkyl radical optionally substituted with one or some halogen-radicals, amino-group, di-((C1-C6)-alkyl)-amino-group, phenylcarbonylmethyl, heterocycloalkyl or aryl radicals; p, p' and p'' represent independently a whole number from 0 to 4; R4 represents radical of the formula: -(CH2)s-R''4 wherein R''4 represents heterocycle comprising at least one nitrogen atom and optionally substituted with (C1-C6)-alkyl or aralkyl, and other values of radicals given in the invention claim also. Also, invention relates to a pharmaceutical composition showing antagonistic property with respect to GnRH and based on these compounds. Also, using above proposed compounds for preparing a medicament is considered. Invention provides synthesis of novel compounds, preparing pharmaceutical composition and medicament based on thereof in aims for treatment of such diseases as endometriosis, fibroma, polycystic ovary, breast, ovary and endometrium cancer, gonadotropic hypophysis desensitization in medicinal stimulation of ovary in fertility treatment in females.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.

18 cl, 2 tbl, 538 ex

FIELD: organic chemistry, anti-microbial preparations.

SUBSTANCE: invention relates to compounds useful as anti-microbial agents. Claimed compounds are effective against to certain human and animal pathogens, including Gram-positive aerobic bacteria such as multi-resistant staphylococcus, streptococcus and enterococcus, as well as anaerobic organisms such as species Bacterioides spp. and Clostridia spp., and acid resistant organisms such as Mycobacterium tuberculosis, Mycobacterium avium, and Mycobacterium spp.

EFFECT: new anti-microbial agents.

2 ex, 5 tbl

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to novel substituted indoles or its pharmaceutically acceptable salts of the formula (I): , wherein R1 means hydrogen (H) atom, halogen atom, -CN, nitro-group, -SO2R4, -OH, -OR4, -SO2NR5R6, -CONR5R6, -COOH, -COOCH3, -NR5R6, phenyl, naphthyl or (C1-C6)-alkyl wherein the latter group is possibly substituted with one or more substitutes chosen independently from halogen atom, -OR8 and -NR5R6 wherein x = 2; R2 means (C1-C7)-alkyl; R3 means phenyl, naphthyl or heteroaryl and each of them is possibly substituted with one or more substitutes chosen independently from H, halogen atom, -CN, -OH, -SO2R4, -OR4, -SO2NR5R6, -CONR5R6, phenyl, naphthyl, (C1-C6)-alkyl wherein the latter group is possibly substituted with one or more substitutes chosen independently from halogen atoms, -OR8 and -NR5R6, -S(O)xR7 wherein x = 2; R4 means (C1-C6)-alkyl; R5 and R6 mean independently H, (C1-C6)-alkyl, or R5 and R6 in common with nitrogen atom to which they are bound can form 6-membered saturated heterocyclic ring comprising one atom chosen from -NR16; R7 means (C1-C6)-alkyl; R8 means H, (C1-C6)-alkyl; R16 means H, -COY-(C1-C4)-alkyl wherein Y means oxygen atom (O) and wherein alkyl group in the substitute group can be direct, branched or cyclic, and wherein heteroaryl means 5-6-membered heteroaromatic ring comprising from 1 to 3 heteroatoms chosen from nitrogen (N), oxygen (O) and sulfur (S) atoms, or means 6,6-condensed bicyclic aromatic ring system comprising one nitrogen atom. Compounds of the formula (I) can be used in production of a medicinal agent used in treatment of asthma and chronic obstructive disease.

EFFECT: valuable medicinal properties of compounds.

7 cl, 2 tbl, 59 ex

FIELD: chemistry of heterocyclic organic compounds, medicine.

SUBSTANCE: invention relates to a novel heterocyclic derivative of the formula (I'): , wherein R1 represents hydrogen atom or (C1-C6)-alkyl; R2 represents-CO-C(R4)=C(R4)-R5 wherein R4 represents hydrogen atom; R5 represents (C2-C8)-alkenyl; R3 represents hydrogen atom or (C1-C4)-alkyl; X represents oxygen atom or sulfur atom; R20 represents phenyl substituted with unsubstituted (C1-C6)-alkyl, (C1-C6)-alkyl substituted with fluorine atom, (C1-C4)-alkoxy-group, phenyl-(C1-C4)-alkoxy-group, hydroxyl group, halogen atom, nitro-group, unsubstituted amino-group or amino-group substituted with (C1-C4)-alkyl; n means a whole number from 1 to 4, or to its pharmaceutically acceptable salt. Also, invention relates to heterocyclic derivative of the formula (I): , wherein R1 represents hydrogen atom or (C1-C6)-alkyl; R2 represents -CO-C(R4)=C(R4)-R5 wherein R4 represents hydrogen atom; R represents (C4-C8)-alkyl or (C2-C8)-alkenyl or -CO-C≡C-R6 wherein R6 represents (C1-C8)-alkyl; R3 represents hydrogen atom or (C1-C4)-alkyl; X represents oxygen atom or sulfur atom; n means a whole number from 1 to 4, or its pharmaceutically acceptable salt. Compounds of the formulas (I') and (I) are effective as a hypoglycemic agent, hypolipidemic agent, agent improving resistance to insulin, therapeutic agent in treatment of diabetes mellitus, therapeutic agent in treatment of diabetes mellitus complications, agents enhancing tolerance to glucose, anti-arteriosclerotic agent, agents against obesity or agent for X syndrome.

EFFECT: valuable medicinal properties of derivatives.

14 cl, 2 tbl, 56 ex

FIELD: organic chemistry, herbicides.

SUBSTANCE: invention relates to a compound of the general formula [I]: wherein R1 and R2 can be similar or different and each represents (C1-C10)-alkyl group; each among R3 and R4 represents hydrogen atom; R5 and R6 can be similar or different and each represents hydrogen atom or (C1-C10)-alkyl group; Y represents 5-6-membered aromatic heterocyclic group or condensed aromatic heterocyclic group comprising one or some heteroatoms chosen from nitrogen atom, oxygen atom and sulfur atom wherein heterocyclic group can be substituted with 0-6 of similar or different groups chosen from the following group of substitutes α, and so on; n means whole values from 0 to 2; [Group of substitutes α]: hydroxyl group, halogen atoms, (C1-C10)-alkyl groups, (C1-C10)-alkyl groups wherein each group is monosubstituted with group chosen from the following group of substitutes β, (C1-C4)-halogenalkyl groups, (C3-C8)-cycloalkyl groups, (C1-C10)-alkoxy-groups, (C1-C10)-alkoxy-groups wherein each group is monosubstituted with group chosen from the following group of substitutes and so on; [Group of substitutes β]: hydroxyl group, (C3-C8)-cycloalkyl groups that can be substituted with halogen atom or alkyl group, (C1-C10)-alkoxy-group, (C1-C10)-alkylthio-groups, (C1-C10)-alkylsulfonyl groups, (C1-C10)-alkoxycarbonyl groups, amino-group, carbamoyl group (wherein its nitrogen atom can be substituted with similar or different (C1-C10)-alkyl groups), (C1-C6)-acyl groups, (C1-C10)-alkoxyimino-groups, cyano-group, optionally substituted phenyl group; [Group of substitutes γ]: optionally substituted phenyl group, optionally substituted aromatic heterocyclic groups, cyano-group. Also, invention relates to herbicide comprising derivative of isoxazoline of the formula [I] as an active component or its pharmaceutically acceptable salt. Invention provides the development of isoxazoline derivative possessing the herbicide activity with respect to resistant weeds, selectivity for cultural crop and weed.

EFFECT: valuable herbicide properties of substances.

18 cl, 24 tbl, 106 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to novel compounds of cyclic amine of the general formula (1): , their pharmaceutically acceptable salts or hydrates wherein each among R1, R2 and R3 represents independently hydrogen atom, halogen atom, hydroxy-group, (C1-C8)-alkoxy-group; each among W1 and W2 represents independently nitrogen atom (N) or -CH; X represents oxygen atom (O), -NR4, -COONR4 or -NR4CO; R4 represents hydrogen atom, (C1-C8)-alkyl, (C3-C6)-alkynyl, substituted or unsubstituted phenyl, unsubstituted benzyl, unsubstituted indanyl wherein substitute(s) of phenyl represent(s) 1-3 groups or atoms chosen from (C1-C8)-alkyl, (C1-C8)-alkoxy-group, (C1-C8)-alkoxy-group substituted with 1-3 halogen atoms, (C1-C8)-alkylthio-group, (C1-C8)-alkylsulfonyl, halogen atom, trifluoromethyl group and (C1-C3)-alkylenedioxy-group; each among l, m and n represents number 0 or 1. Proposed compounds possess inhibitory effect on cell adhesion and/or cell infiltration and can be used as a medicinal agent and pharmaceutical composition based on thereof.

EFFECT: valuable biological and medicinal properties of compounds and pharmaceutical composition.

6 cl, 1 tbl, 439 ex

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