Substituted benzoylcyclohexenones

FIELD: organic chemistry.

SUBSTANCE: invention describes novel substituted benzoylcyclohexenones of the general formula (I): wherein values Q, Y, Z, R1-R5 and their possible tautomeric forms and their possible salts given in the invention claim. Invention proposes substituted benzoylcyclohexenones of the general formula (I) that possess the herbicide activity.

EFFECT: valuable property of compounds.

2 cl, 10 tbl, 6 ex

 

The invention relates to new substituted benzoylacetone possessing biological activity, in particular herbicide activity.

To date, it is known that certain substituted benzoylacetone or benzoylecgonine, such as the compounds N-[2,6-dichloro-3-[(3,3-dimethyl-2,6-dioxo-cyclohexyl)carbonyl]-phenyl]ndimethylacetamide, N-[2-chloro-3-[(2,6-dioxo-cyclohexyl)-carbonyl]-4-nitro-phenyl]ndimethylacetamide, N-[2-chloro-3-[(2,6-dioxo-cyclohexyl)-carbonyl]phenyl]-acetamide", she N-[2,6-dichloro-3-[(2,6-dioxo-cyclohexyl)carbonyl]-phenyl]ndimethylacetamide (see U.S. patent US-A-4780127), show herbicide properties (see also European patent application EP-A-090262, EP-A-135191, EP-A-137963, EP-A-186118, EP-A-186119, EP-A-186 120, EP-A-319075, international patent application WO-A-96/26200, WO-A-97/46530, WO-A-99/07688, WO-A-99/10327, WO-A-00/05221, WO-A-00/21924). However, these compounds do not meet all the necessary requirements.

The objective of the invention is the expansion of the Arsenal substituted benzoylacetone with high biological activity, in particular herbicide activity.

The problem is solved proposed substituted benzoylacetonate General formula (I)

in which Q represents O (oxygen) or S (sulfur),

R1represents hydrogen, alkyl with 1-6 atoms in which laroda,

R2represents hydrogen, alkyl with 1-6 carbon atoms, or together with R1is alcander with 2-5 carbon atoms,

R3represents halogen, halogen substituted alkyl containing up to 4 carbon atoms, alkoxy containing up to 4 carbon atoms,

R4represents hydrogen, halogen,

R5represents hydrogen, alkyl with 1-6 tomamae carbon

Z represents amino, alkylamino, optionally substituted alkoxy with 1-4 carbon atoms, alkoxyimino respectively with 1-6 carbon atoms in the alkyl groups; dialkylamino, N-alkylalkoxysilane or diacylhydrazine respectively with 1-4 carbon atoms in the alkyl groups; cyclooctylamino with 3-6 carbon atoms in cycloalkyl group; substituted with halogen phenyl; arylalkylamine to 6 carbon atoms in the aryl group and from 1 to 4 carbon atoms in the alkyl part; accordingly, if necessary, alkyl with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, cycloalkyl with 3-6 carbon atoms substituted heterocyclyl, heterocyclisation, -N=(heterocyclyl) from a number of furyl, tetrahydrofurfurylamine, thienyl, pyrrolidinyl, pyrrolidinone, Oxymetazoline, isoxazolyl, di-hydroisoquinoline (isoxazoline), tetrahydroisoquinoline (isoxazolidine), tetrahydro-(2H)-1,2-oxazin-2-yl, dihydrate is alil (thiazoline), thiadiazolidine, piperidinyl, piperidylamine, morpholinyl, piperazinil, 2-oxo-1,3-disallowances, exterritoriality,

including all possible tautomeric forms and the possible salts.

New substituted benzoylacetone General formula (I), which are classified as toxic substances obtained if cyclohexandione ("hydroxycyclohexanone") of General formula (II)

in which R1and R2have the above meanings, is subjected to the interaction with the substituted benzoic acids of General formula (III),

in which Q, R3, R4, R5and Z have the above values,

or their reactive derivatives, such as the corresponding acid chlorides of the acids, anhydrides, acids, cyanides acids or esters,

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

and, if necessary, immediately after that with the thus obtained compounds of General formula (I) in the definition of the substituents usual conduct of electrophilic or nucleophilic substitution reactions or reactions of oxidized is I or restore or compounds of General formula (I) in the usual way transferred to salt.

New substituted benzoylacetone General formula (I) essentially can be obtained, as schematically presented below.

Interact of aminobenzoylamino General formula (IV) with halogen(thio)carbonyl compounds of General formula (V) or, if necessary, with the relevant ISI(thio)cyanate (Q, R1, R2, R3, R4, R5, Y and Z are values above, X represents halogen):

The compounds used in the claimed methods (α) and (β) as educt, generally defined by the formula (IV) and (V). In formulas (IV) and (V) Q, R1, R2, R3, R4, R5, Y and Z have the meanings which have already been mentioned above in connection with the description of the inventive compounds of the formula (I).

Educt of the formula (V) are known compounds.

Educt of the formula (IV) can be obtained by known methods.

Interact ISO(thio)cyanobenzylidene General formula (VI) with nucleophilic compounds of General formula (VII); (Q, R1, R2, R3, R4, Y and Z are values above):

If, for example, as the outcome of the s substance use cyclohexane-1,3-dione and 2-chloro-4-[(dimethylaminoethyl-methylamino)]-benzoic acid, the course of reaction when the claimed method can be represented by the following scheme:

The original substance of General formula (II) are known and/or can be obtained by known methods.

The original substance of General formula (III) are known and/or can be obtained by known methods (see Japanese patent application JP-A-11292849, sample receipt).

Substituted benzoic acid of General formula (III) are obtained when the ester of benzoic acid of General formula (IIIa)

in which Q, R3, R4, R5and Z have the above meanings and R represents alkyl, in particular methyl or ethyl, is subjected to contact with water, if necessary, in the presence of gidrolizuemye auxiliary agent, such as caustic soda, and, if necessary, in the presence of a diluent, such as tetrahydrofuran, at temperatures between 0°and 100°With (see examples receipt).

Esters of benzoic acid of General formula (IIIa)required as starting materials, are known and/or can be obtained by known methods (see Japanese patent application JP-A-11292849, sample receipt).

Esters of benzoic acid of General formula (IIIa) is obtained if (α) ester of aminobenzoic acid of General formula (IX)

the where Q, R3, R4, R5and Z have the above meanings and R represents alkyl, in particular methyl or ethyl, is subjected to the interaction with halogen(thio)carbonyl compounds of General formula (VI)

in which Q and Z have the above meanings and

X represents halogen, in particular fluorine, chlorine or bromine,

- or, if necessary, with the corresponding ISO(thio)cyanate - if necessary, in the presence of an acid acceptor, such as potassium carbonate or triethylamine, or, if necessary, in the presence of a diluent, such as methyl isobutyl ketone or acetonitrile, at temperatures between 0°and 100°With (see examples), or if

(β) ether ISO(thio)cyanobenzoic acid of General formula (X)

in which Q, R3and R4have the above values and

R represents alkyl, in particular methyl or ethyl,

subjected to interaction with nucleophilic compounds total

formula (VIII)

in which Z has the above meaning,

if necessary, in the presence of a reaction auxiliary agent, such as triethylamine, and optionally in the presence of a diluent, such as acetonitrile or toluene, the ri temperatures between 10° With 120°With (see examples receipt).

Educt of formula (VI) and (VIII) are known compounds.

Educt of formula (IX) and (X) can be obtained by known methods.

Way to generate new substituted benzoylacetone General formula (I) is carried out preferably using a dehydrating agent. You get the usual chemical reagents suitable for binding water.

As examples for this include dicyclohexylcarbodiimide, anhydride papapostolou acid and carbonyl-bis-imidazole.

As is particularly well suitable dehydrating agents include dicyclohexylcarbodiimide and anhydride papapostolou acid.

Way to generate new substituted benzoylacetone General formula (I) is carried out, if necessary, with the use of an auxiliary agent.

As examples for this include sodium cyanide, potassium cyanide, acetocyanohydrin, 2-cyano-2-(trimethylsilyloxy)-propane and trimethylsilylacetamide.

As particularly well suited AIDS should be called trimethylsilylacetamide.

As an auxiliary agent is also suitable conventional inorganic or organic bases or acid acceptors. To them preferably include acetates, amides, carbonates, the bicarbonates, hydrides, hydroxides or alcoholate alkaline or alkaline earth metals, such as 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, methanolate, ethanolate, n - or ISO-propanolol, n - or ISO-, sec - or tert-butanolate sodium or potassium; in addition, basic organic nitrogen compounds, such as trimethylamine, triethylamine, Tripropylamine, tributylamine, ethyl-Diisopropylamine, N,N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl dicyclohexylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl - and 3,5-dimethylpyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylaminopyridine, 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 a further auxiliary means of suitable catalysts phase transfer. As examples of such catalysts include:

tetrabutylammonium-bromide, tetrabutylammonium chloride, tetraoctylammonium-chloride, tetrabutylammonium-hydrosulphate, methyl-trioctyl-ammonium-x is arid, hexadecyl-ammonium-chloride, hexadecyltrimethylammonium-bromide, benzyl-ammonium-chloride, benzyl-triethylammonium-chloride, benzyl-ammonium-hydroxide, benzyl-triethylammonium-hydroxide, benzyl-tributylammonium-chloride, benzyl-tributylammonium-bromide, tetrabutylphosphonium-bromide, tetrabutylphosphonium-chloride, tributyl-hexadecylamine-bromide, butyl triphenylphosphonium-chloride, ethyl-trioctylphosphine-bromide, tetraphenylphosphonium-bromide.

The method of obtaining compounds of General formula (I) in each case is carried out preferably using one or more diluents. As diluents are considered, first of all inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or dimethyl or diethyl ether of ethylene glycol; 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-m is formanilide, N-methyl-pyrrolidone or hexamethylene phosphoric 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, onomatology ether of ethylene glycol, monotropy ether of ethylene glycol, onomatology ether of diethylene glycol, monotropy ether of diethylene glycol.

The reaction temperature can vary in a wide area. In General operate at temperatures between 0°150°C, preferably between 10°120°C.

In General the reaction is carried out at normal pressure. It is still possible to conduct the reaction at elevated or reduced pressure -- in General between 0.1 bar and 10 bar.

Source materials used in the General case, approximately equimolecular quantities. But it is also possible to use components in a larger excess. In the General case, the interaction is carried out in a suitable diluent in the presence of a reaction auxiliary agent, and the reaction mixture is in General stirred for several hours at the required temperature. The processing is carried out by conventional methods (see examples receipt).

Substituted benzoylecognine (hereinafter referred to as "active compounds") can be used as esfoliante, desicant, means for haulm destruction and, especially, as a means to eradicate weeds. Under the weeds in the broadest sense should be understood all plants which grow in locations where they are undesired. Are there active substances such as herbicides solid or as herbicides are selective, dependent quantities. The active substance can be used in the following plants:

Dicotyledonous weed species: Abultion, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Species, Such As Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

Two culture types: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanium, Vicia.

Monocotyledonous weeds species: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Monocots culture species: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.

However, the use of active substances in any case is not limited to the criminal code of the related species, and applies equally well to other plants.

The active substance in a concentration suitable for the total combating of weeds, for example, industrial enterprises and railway tracks and on the roads and places with greenery and without them. The active substance may also be used for combating weeds in perennial cultures, for example, in forest plantations, ornamental plantings, fruit plantations, vineyards, citrus crops, nuts, bananas, coffee, tea, rubber, olive trees, cocoa, berry crops and hops, for decorative and sports lawns and pastures, and for the selective combating of weeds in annual crops.

The active substance of the formula (I) show a strong herbicide activity and a broad spectrum of action when applied to the soil and above-ground parts of plants. In a known environment, it is also suitable for the selective combating of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, as if making up shoots, and post-harvest method.

Active substances in certain concentrations or application rates can also be used for combating animal pests and fungal or bacterial plant diseases. If necessary, they can also be used as an intermediate or the similar products for the synthesis of other active substances.

According to the invention can be processed by all plants or plant parts. Under the plant refers to all plants and plant populations such as desired or undesired wild plants or crop plants (including naturally occurring crop plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization or using biotechnology and gentechnologie methods, or a combination of these methods, including the transgenic plants and including the plant varieties protected or not protected with the protection of varieties. Under the plant parts must be understood all above-ground or below-ground parts and organs of plants, such as shoot, leaf, flower and root, in the form of examples of leaves, needles, stems, trunks, flowers, fruit bodies, fruits and seeds and also roots, tubers and rhizomes. The parts of plants are also the fruits of the harvest, as well as vegetative and generative breeding material, for example cuttings, tubers, rhizomes, horizontal cuttings and seeds.

Treatment of plants and plant parts with the active compounds is carried out directly or through effects on their environment, living space or storage space by the customary treatment methods, for example, by dipping, spreading the, treatment pairs, fog, scattering, smearing and in the case of breeding material, in particular seeds, furthermore, using a single-layer or multi-layer shells.

The active substance can be converted into customary formulations, such as solutions, emulsions, powders for spraying, suspensions, powders, funds in the form of dusts, pastes, soluble powders, granules, concentrated suspensions and emulsions, impregnated with active natural substances and synthetic substances, as well as microencapsulation in polymeric substances.

These compounds may be obtained in a known manner, for example by mixing the active substances with extenders, as well as liquid solvents and/or solid carriers, optionally with the use of surface-active agents, and emulsifiers and/or dispersing funds and/or foaming agents.

In the case of using water as a filler can also be used, for example, organic solvents as auxiliary solvents. As liquid solvents are discussed in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromaticheskie compounds and chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons is childbirth, 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 are considered: for example ammonium salts and natural crushed rock, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or hard-shelled land, and synthetic powdered solids, such as highly dispersed silicic acid, alumina and silicates, as solid carriers for granules are considered: for example, crushed and fractionated natural rocks such as calcite, marble, pumice, thick, dolomite, and also synthetic granules of inorganic and organic powdered solid rock, and granules of organic materials such as sawdust, coconut shell, corn cobs and stalks of tobacco; as emulsifiers and/or foaming agents are considered: for example nonionic and anionic emulsifiers, such as esters polyoxyethylene fatty acids, ethers polyoxyethylene LM is different alcohols, for example, alkyldiphenylamine esiri, alkyl sulphonates, alkyl sulphates, arylsulfonate, and also protein hydrolysates; as dispersing funds are considered: for example lignin-sulphite liquor and methylcellulose.

The compositions can be used adhesive means, such as carboxymethylcellulose, natural and synthetic powdered, granular or latex 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.

Can be used colorants such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyanide blue, and organic dyestuffs, such as alizarin, azo dyes and phthalocyanine metals, and small amounts of nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

In General, the compositions contain between 0.1 and 95 mass% of the active substance, preferably between 0.5 and 90%.

The active substance can be used as such or in their formulations, also in a mixture with known herbicides and/or substances that improve tolerance to herbicides cultivated plants in weed control ("Safener"), while the possible finished formulations or tank mixes. It is also possible mixture with the means of weed control, which contain one or more known herbicides and a substance that improves the tolerance of herbicides cultural lastenemy (Safener).

For mixtures can be considered known herbicides, for example, Acetochlor, Acifluorfen (-sodium), Klonipin, Alachlor, Aloxide (-sodium), ametrine is high, Nicarbazin, Amithlon, Amidosulfuron, Anilofos, Azul, Atrazine, Azafenidin, Azimsulfuron, Beflubutamid, Benazolin (-ethyl), Belforest, 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), Gametocytes, Chloramben, ozone chloride, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Zinedin (-ethyl), Cinmetacin, Chinaculture, Clefoxydim, Clethodim, Clodinafop (propargyl), Clomazone, Clomipram, Kopirali, Cloperastine (-methyl), Karasulu (-methyl), Cumyluron, Cyanazine, Cybotron, Cycloate, Cycloaliphatic, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, Desmedipham, Diallate, Dicamba, Dichlorprop (-R), Diclofop (-methyl), Dicloflam, Diacetyl (-ethyl), Difenzoquat, Diflufenican, Diflubenzuron, Dimefuron, Timepart, Dimethachlor, Dimetane is Rin, Dimethenamid, Dimexidum, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Damron, Aprobada, 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, Flumeturon, Flurochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flourophenyl, Fluspirilene (-methyl-sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-butoxypropyl, -meptyl), Flurried, Flurtamone, Fluthiacet (-methyl), Flutamide, Fomesafen, Foramsulfuron, Glufosinate (-ammonium), Glyphosate (Isopropylamine), 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, Metsulfuron (-methyl), Molinet, Monolinuron, Nitroanilide, Napropamide, Nebur is h, Nicosulfuron, Norflurazon, Arrancars, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxacyclobutane, Oxyfluorfen, Paraquat, Pelargonia acid, Pendimethalin, Pentalyn, Phenoxazone, Phenmedipham, Picolinafen, Piperophos, Pretilachlor, Primisulfuron (-methyl), Proporsal, 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, Arbutin, Tanishlar, Tefloned, Thiazopyr, Thidiazuron, Thifensulfuron (-methyl), Thiobencarb, Thiocarbonyl, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifluralin, Trifloxysulfuron, Triflusulfuron (-methyl), Tritosulfuron.

For mixtures, it also covers the known substance, tolerance to herbicides cultural lastenemy (Safener), for example, AD-67, BA3-145138, Enoxacin, Cloquintocet (-mexyl), Simerini, 2,4-D, DKA-24, Dichlormid, Damron, Fencl the Rome, Fenchlorphos (-ethyl), Florasol, Fluxotine, Furilazole, Isoxadifen (-ethyl), MSRA, Mecoprop (-R), Mefenpyr (-diethyl), MG-191, Oxybutinin, PPG-1292, R-29148.

A mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, protective substances from birds, nutrients for plants and tools that improve soil structure, are also possible.

The active substance may be introduced as such, in the form of their formulations or finished forms obtained from them by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granulates. Introduction in the normal way, for example, by irrigation, spraying, spreading, spilling.

The active substance can be applied both before and after germination of the plants. They can be incorporated into the soil before sowing.

Make the number of active substances can vary over a wide area. They depend largely on the type of desired effect. In the General case, make a number lying between 1 g and 10 kg of active substance per hectare of soil surface, preferably between 5 g and 5 kg per hectare.

As already mentioned, according to the invention can be processed by all plants and their parts. In one preferred form of execution are handled naturally occurring wild sludge is obtained using conventional biological methods of removing, such as crossing or merging protoplasm, the plant species or plant varieties, and their parts. In another preferred form of execution are processed transgenic plants and plant varieties, which were obtained using gentechnologie methods, optionally in combination with conventional methods (genetically modified organisms), and parts thereof. The notion of "part" or "parts of plants" was explained above.

Particularly preferably, according to the invention are processed, respectively, plants sales cultivars or varieties in use. Under the plant varieties understand plants with specific properties ("characteristics"), which is obtained as a normal excretion, and by mutagenesis or by using recombinant DNA technology. This can be varieties, bio - and genotypes.

Depending on the plant species or varieties of plants, their cultivation and growing conditions (soil, climate, vegetation period, feeding), due to the inventive processing can also occur suradditions ("synergistic") effects. So, for example, possible reduced consumption rates and/or widening the range of actions, and/or increased activity used according to the invention substances and tools - also in combination with other agrochemical active substances, the best growth of the seedlings to the cultural plants, increased tolerance of cultivated plants against high and low temperatures, increased tolerance of cultivated plants in relation to drought or in relation to the content in the ground water or salts, increased intensity of flowering and easier harvesting, accelerated ripening, higher yields, higher quality and/or higher nutritional value of food crops, the best capacity for storage and/or processing food crops that exceed the originally expected effects.

To the preferred transgenic (received hentainiches) plants or plant varieties subject to processing according to the invention, belong to all the plants, which are obtained using gentechnologie modification of the genetic material that makes these plants are especially preferred securities properties (characteristic features). Examples of such properties are better plant growth, increased tolerance to high and low temperatures, increased tolerance to drought or in relation to the content in the ground water or salts, increased power and intensity of flowering and easier harvesting, accelerated ripening, higher yields, higher quality and/or higher nutritional value of food is mswb harvest, the best capacity for storage and/or processing food crops. Other and especially celebrated examples of such properties are enhanced resistance of plants to damage by animal and microbial pests, such as against insects, acaridae, plant pathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants in relation to certain herbicide active substances. As examples of transgenic plants mentioned are the important crop plants, such as cereals (wheat, rice), maize, soybeans, potatoes, cotton, rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes, cotton and canola are noted. As properties (characteristics) are especially marked increased resistance of plants against insects, due to plant toxins, such as those formed by the genetic material from Bacillus Thuringiensis (for example, through gene CrylA(a), CrylA(b), CrylA(c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, r3b and CrylF, as well as their combinations] in plants (hereafter Bt-plants). As properties (characteristics) also emphasised the increased resistance of plants against fungi, bacteria and viruses due to systemic acquired the resist is tion (SAR), Sistemine, Phytoalexin, Elicitin and resistance genes and correspondingly eksponirovannykh proteins and toxins. As properties (characteristics) are especially marked increased tolerance of plants in relation to certain herbicide active substances, such as imidazolinones, sulfonylureas, Glyphosate or Phosphinotricin (for example the "PAT" gene). Genes accompanying accordingly, the desired properties (characteristic features), can occur in combination with each other in transgenic plants. As examples of "Bt plants" should be called varieties of corn, cotton varieties, soybean varieties and potato varieties 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). As examples tolerant to herbicides plant should be called varieties of corn, cotton varieties and soybean varieties which are sold under the trade names Roundup Ready®(tolerance to Glyphosate, for example maize, khlopchatnik, soybean), Liberty Link®(tolerance to Phosphinotricin, for example rape), IMI®(tolerance to imidazolinones) and STS® (tol runtest in relation to the sulfonylureas, for example maize). As herbicide-resistant plants (usually bred for herbicide tolerance) should be mentioned cultivars (e.g., corn), sold under the name Clearfield®. It is clear that these provisions also apply to plant varieties that will be displayed in the future or will do in the future on the market, with the specified or derived in future genetic properties (characteristics).

See plants, according to the invention can be particularly preferably treated with compounds of formula (I) or mixtures of active substances, in addition to the effective control of weeds appear above the synergistic effects of transgenic plants or plant varieties. Preferred areas specified above for the active substances or mixtures, are also applicable to the treatment of these plants. Especially it is necessary to emphasize the treatment of the plants with the compounds or mixtures described specifically in this text.

The preparation and use of the inventive active substance can be seen from the following examples.

Examples:

Example 1-1

The mixture 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) of cyclohexane-1,3-dione, 2,10 g (10.1 mm is l) dicyclohexylcarbodiimide and 30 ml of acetonitrile is stirred for 18 hours at room temperature (about 20° C) and then filtered. To the filtrate add 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 evaporated under reduced pressure. The residue is stirred with 10%aqueous sodium carbonate solution and then shaken with diethyl ether. After the separation (and drop) the organic phase the aqueous solution is acidified with concentrated hydrochloric acid and was isolated by suction drawn when this crystalline product.

Obtain 2.20 g (49% of theory) of N-[2,6-dichloro-3-[(2,6-dioxo-cyclohexyl)-carbonyl]-phenyl]-3-methyl-2-oxo-1-imidazolidinecarboxamide.

logP(pH 2.3):2,07

Analogously to example 1 and, accordingly, a General description of the retrieval method can be obtained, for example, shown in the following tables I-1 through I-5 compounds of General formula (I-1) or (I-2).

In these tables use the following abbreviations:

i=ISO-structure

n=normal structure.

Table I-1: Examples of compounds of formula (I), and consequently R1and R2are hydrogen and Y is hydroxy.

# exampleQ(Position) R3(The situation is s) R 4R5ZFormula Physical. data
1-2O(2)

Cl
(4)

Cl
H(l-2) logP=2,33
1-3O(2)

Cl
(4)

Cl
H(l-2) logP=1,97
1-4O(2)

Cl
(4)

Cl
H(l-2) logP=2,33
1-5O(2)

Cl
(4)

Cl
H(l-2) logP=1,60
1-6O(2)

Cl
(4)

Cl
H(l-2) logP=1,81
1-7O(2)

Cl
(4)

Cl
HN(C2H5)2(l-2) logP=2,21
1-8O(2)

Cl
(4)

Cl
HNHCH3(l-2) logP=1,46
1-9O(2)

Cl
(4)

Cl
H NHC2H5(l-2) logP=1,70
1-10O(2)

Cl
(4)

Cl
HN(CH3)2(l-2) logP=1,64
1-11O(2)

Cl
(4)

Cl
H(l-2)
1-12O(2)

Cl
(4)

Cl
HNHC3H7-i(l-2) logP=1,99
1-13O(2)

Cl
(4)

Cl
H(l-2) logP=1,77
1-14O(2)

Cl
(4)

Cl
H(l-2) logP=1,90
1-15O(2)

Cl
(4)

Cl
H(l-2) logP=2,65
1-16O(2)

Cl
(4)

Cl
H(l-2) logP=2,98

# exampleQ(Position) R3(ulozhenie) R 4R5ZFormula Physical. data
1-17O(2)

Cl
(4)

Cl
H(l-2) logP=1,81
1-18O(2)

Cl
(4)

Cl
H(l-2) logP=1,72
1-19O(2)

Cl
(4)

Cl
H(l-2)

logP=2,78
1-20O(4)

CF3
-H(l-1) logP=2.57 m
1-21O(2)

Cl
(4)

Cl
H(l-2) logP=1,94
1-22O(2)

Cl
(4)

Cl
H(l-2) logP=3,86
1-23O(4)

CF3
-CH3(l-1) logP=2,04
1-24O(2)

Cl
(4)

Cl
H(l-2) logP=of 2.26
1-25O(2)

Cl
(4)

Cl
HNH2(l-2) logP=1,29
1-26O(2)

Cl
(4)

Cl
HNHC3H7-n(l-2) logP=1,98
1-27O(2)

Cl
(4)

Cl
H(l-2) logP=1,58
1-28O(2)

Cl
(4)

Cl
HN(C3H7-n)2(l-2) logP=2,95
1-29O(2)

Och3
-H(l-3) logP=1,93

O
# exampleQ(Position) R3(Position) R4R5ZFormula Physical. data
1-30O(2)

Cl
(4)

Cl
H(l-2) logP=2,34
1-31 O(2)

Cl
(4)

Cl
H(l-2) logP=2,36
1-32O(2)

Cl
(4)

Cl
H(l-2)

logP=2,04
1-33O(2)

Cl
(4)

Cl
H(l-2) logP=2,40
1-34O(2)

Cl
(4)

Cl
H(l-2) logP=1,88
1-35O(2)

Cl
(4)

Cl
H(l-2) logP=2,37
1-36O(2)

Cl
(4)

Cl
H(l-2) logP=2,02
1-37O(2)

Cl
(4)

Cl
H(l-2) logP=2,08
1-38O(2)

Cl
(4)

Cl
H(l-2) logP=2,96
1-39(2)

Cl
(4)

Cl
H(l-2) logP=1,93
1-40S(2)

Cl
(4)

Cl
H(l-2) logP=2,28

# exampleQ(Position) R3(Position) R4R5ZFormula Physical. data
1-41O(2)

Cl
(4)

Cl
H(l-2) logP=2,52
1-42O(2)

Cl
(4)

Cl
H(l-2)

Y=SC6H5logP=2,98
1-43O(2)

Cl
(4)

Cl
H(l-2) logP=1,96
1-44O(2)

Cl
(4)

Cl
H(l-2) logP=2,22
1-45O(2)

Cl
(4)

Cl
H/td> (l-2)

TPL: 195°

Table I-2: Examples of compounds of formula (I), and consequently R1represents methyl in the 4-position, R2represents methyl in the 4-position and Y represents hydroxy.

# exampleQ(Position) R3(Position) R4R5ZFormula Physical. data
2-1O(2)

Cl
(4)

Cl
H(1-2) logP=2,61
2-2O(2)

Cl
(4)

Cl
H(1-2) logP=2.57 m
2-3O(2)

Cl
(4)

Cl
H(1-2) logP=2,83

Table I-3: Examples of compounds of formula (I), and consequently R1represents methyl in the 5-position, R2represents hydrogen and Y is hydroxy.

# exampleQ(The situation is s) R 3(Position) R4R5ZFormula Physical. data
3-1O(2)

Cl
(4)

Cl
H(1-2) logP=2,33
3-2O(2)

Cl
(4)

Cl
H(1-2) logP=2,25
3-3O(2)

Cl
(4)

Cl
H(1-2) logP=2,52

Table I-4: Examples of compounds of formula (I), and consequently R1represents methyl in the 5-position, R2represents methyl in the 5-position and Y represents hydroxy.

# exampleQ(Position) R3(Position) R4R5ZFormula Physical. data
4-1O(2)

Cl
(4)

Cl
H(1-2) logP=2,54
4-2O(2)

Cl
(4)

Cl
H (1-2) logP=2,59
4-3O(2)

Cl
(4)

Cl
H(1-2) logP=of 2.51
4-4O(2)

Cl
(4)

Cl
H(1-2) logP=was 2.76

Table I-5: Examples of compounds of formula (I), and consequently R1and R2are dimethylene group between positions 4 and 6 - "(4)-CH2CH2-(6) - and Y represents hydroxy.

# exampleQ(Position) R3(Position) R4R5ZFormula Physical. data
5-1O(2)

Cl
(4)

Cl
H(1-2) logP=2,23

The determination of the logP values specified in example I-1 table I-1, I-2, I-3, I-4, I-5 and in the following tables 2, 3 carried out according to EEC-order 79/831 Annex V.A8 by HPLC (high performance liquid chromatography) on a column with a reversible phase (18) in the acidic region (a 0.1%aqueous phosphoric acid) and a temperature of 43° C. as eluent using acetonitrile with a linear gradient from 10% acetonitrile to 90% acetonitrile.

The calibration is carried out with unbranched Alkan-2-areas (3-16 carbon atoms), the logP values are known (determination of the logP values on the basis of retention times using linear interpolation between the two following each other by alkenone).

Educt of the formula (III):

Example (III-1)

A mixture of 11.3 g (32,9 mmol) of the methyl ester of 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 evaporated under reduced pressure to approximately half volume. Then shaken with diethyl ether, the organic phase is separated (and drop) and the aqueous phase is acidified with concentrated hydrochloric acid. Fallen in this crystalline product produce by using suction.

Get 9,1 g (81.5% of theory) 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) can be obtained, for example, compounds of General formula (III), are shown in table 2.

Table 2: Examples of compounds of the form is s (III)

# example(Position) R3(Position)R4(Regulations)

Physical. data
III-2(2)

Cl
(4)

Cl
logP=1,17
III-3(2)

Cl
(4)

Cl
logP=1,58
III-4(2)

Cl
(4)

Cl
logP=0,78
III-5(2)

Cl
(4)

Cl
logP=1,05
III-6(2)

Cl
(4)

Cl
logP=1,50
III-7(4)

CF3
-logP=2,43

# example(Position) R3(Position) R4(Regulations)

Physical. data
III-8(4)

CF3
-logP=2,13
III-9(4)

CF3
-logP=2,70
III-10(2)

Cl
(4)

Cl
logP=1,16
III-11(2)

Cl
(4)

Cl
logP=1,03

Educt of the formula (IIIa):

Example (IIIa-1)

A mixture of 12.3 g (50 mmol) of methyl ester of 2,4-dichloro-3-isocyanatobenzene acid, 5.0 g (50 mmol) of 1-methyl-2-oxo-imidazolidine, a few drops of triethylamine and 100 ml of acetonitrile is stirred for 18 hours at room temperature (about 20°) and then evaporated under reduced pressure. After that, the residue triturated with diethyl ether, and the crystalline product produce by using suction.

Obtain 11.4 g (60% of theory) of methyl ether of 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) can be obtained, for example, compounds of General formula (IIIa), are shown in table 3.

Table3:Examples of compounds of the formula (III)

# exampleR(Position) R3(Position) R4(Regulations)

Physical. data
IIIa-2CH3(2)

Cl
(4)

Cl
logP=1,34
IIIa-3CH3(2)

Cl
(4)

Cl
logP=1,64
IIIa-4CH3(2)

Cl
(4)

Cl
logP=0,50
IIIa-5CH3(2)

Cl
(4)

Cl
logP=2,02
IIIa-6CH3(4)

CF3
-logP=3,35
IIIa-7CH3(4)

CF3
-logP=was 2.76

# exampleR(Position) R3 (Position) R4(Regulations)

Physical. data
IIIa-8CH3(4)

CF3
-logP=3,10
IIIa-9CH3(2)

Cl
(4)

Cl
logP=3,45
IIIa-10CH3(2)

Cl
(4)

Cl
logP=3,43
IIIa-11CH3(2)

Cl
(4)

Cl
logP=1,55
IIIa-12CH3(2)

Cl
(4)

Cl
logP=1,80
IIIa-13CH3(2)

Cl
(4)

Cl
logP=0,93

Examples of the application

Example

Test before germination on the surface

Solvent: 5 mass parts of acetone

Emulsifier: 1 mass part Alki allprivileges ether

For obtaining the target composition with the active substance is mixed 1 mass part of the active substance with the specified amount of solvent, add the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are planted in normal soil. After 24 hours, the soil is sprayed with the composition with the active substance so that per unit area applied, respectively, a desired amount of the active substance. The concentration of active substance in the broth for spraying is selected so that in 1000 l of water per hectare were applied, respectively, a desired amount of the active substance.

After three weeks, assess the degree of damage to the plants in % damage in comparison with the development of the untreated control. Thus take:

0% = no action (as untreated control)

100% = total destruction.

The active substance, the rate of flow of treated plants and the results of the experiment are summarized in table 4.

Table 4
The degree of damage to plants in %
The active substance of example No.The consumption rate of the active. substance g/haAMAREABUH CHEALDATSTMATINPOAANSOLNISTEMEVIOAR
1-3250-9999----99-
1-5125--9999999999-99
1-6250-100-100-----
1-152509090909090-9090-
AMARE = Amaranthus retroflexus
ABUTH = Abutilon theophrasti
CHEAL = Chenopodium album
DATST = Datura stramonium
MATIN = Matricaria inodora
POAAN = Poa annua
SOLNI = Solanum nigrum
STEME = Stellaria media
VIOAR = Viola arvensis

The example In

Test after germination on the surface

Dissolve the l: 5 mass parts of acetone

Emulsifier: 1 mass part alkylarylsulphonates ether

For obtaining the target composition with the active substance is mixed 1 mass part of the active substance with the specified amount of solvent, add the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Test plants which have a height of from 5 to 15 cm are sprayed with the composition with the active substance so that was applied, respectively, the desired quantity of active substance per unit area. The concentration of the broth for spraying is selected so that in 1000 l of water/ha was applied, respectively, the desired amount of the active substance.

After three weeks, assess the degree of damage to the plants in % damage in comparison with the development of the untreated control. Thus take:

0% = no action (as untreated control)

100% = total destruction.

The active substance, the rate of flow of treated plants and the results of the experiment are summarized in table 5.

Table 5
The degree of damage to plants in %
The active substance of example No.The consumption rate of the active. substance g/haCHEAL DATSTDIGSAMATINSINALSOLNISTEMEXANST
1-1320----80-80-
1-32509595---95--
1-525090----9090-
1-6125-1009095-10095-
1-23250-90-90-909090
CHEAL = Chenopodium album
DATST = Datura stramonium
DIGSA = Digitaria sanguinalis
MATIN = Matricaria inodora
SINAL = Sinapis arvensis
STEME = Stellaria media
XANST = Xanthium strumarium

The example

Experience in sown rice (greenhouse)

Solvent: 5 mass is t, acetone,

Emulsifier: 1 mass part alkylarylsulphonates ether.

For obtaining the target composition with the active substance is mixed 1 mass part of the active substance with the specified amount of solvent and emulsifier, and by mixing with water to dilute to the desired concentration.

Vessels for plants (dimensions: 20 cm × 20cm × 9 cm; surface 1/200 ar) filled with soil from the rice field. Seeds of rice and weeds are planted in a moist breeding ground. At the stage 1.5-2 leaf rice make a diluted composition of the active substance in the form of spraying (process leaves).

One day after treatment of test vessels are immersed in water, to the height of water above them was 3 see Then tested the samples incubated under flooded conditions (water depth 3 cm).

4 weeks after application of the active substance assess the degree of damage to the plants in % damage (or impact on weeds) in comparison with untreated control. Thus take:

0% = no action (as untreated control)

100% = total destruction.

The active substance, the rate of flow of treated plants and the results of the experiment are summarized in table 6. The rest of the claimed compounds possess similar activity.

Table 6
The degree of damage to plants in %
The active substance of example No.The consumption rate of the active. substance g/haABUTHCHEALDATSTDIGSAECHCGMATINSOLNIXANSTRice
1 -3125-9090---900
1 -5125-----95--0
1 -6250---9090---0
1 -231259090-----900
ABUTH=Abutilon theophrasti
CHEAL=Chenopodium album
DATST=Datura stramonium
DIGSA=Digitaria sanguinalis
ECHCG=Echinochloa crus gali
MATIN=Matricaria inodora
SOLNI=Solanum nigrum
XANST=Xanthium strumarium

1. Substituted benzoylacetone General formula (I)

in which Q represents O (oxygen) or S (sulfur),

R1represents hydrogen, alkyl with 1-6 carbon atoms,

R2represents hydrogen, alkyl with 1-6 carbon atoms, or together with R1is alcander with 2-5 carbon atoms,

R3represents halogen, halogen substituted alkyl containing up to 4 carbon atoms, alkoxy containing up to 4 carbon atoms,

R4represents hydrogen, halogen,

R5represents hydrogen, alkyl with 1-6 carbon atoms,

Y represents hydroxy,

Z represents amino, alkylamino, optionally substituted alkoxy with 1-4 carbon atoms, alkoxyimino, respectively, with 1-6 carbon atoms in the alkyl groups; dialkylamino, N-alkylalkoxysilane or diacylhydrazine, respectively, with 1-4 carbon atoms in the alkyl groups; cyclooctylamino with 3-6 carbon atoms in cycloalkyl group; substituted with halogen phenyl; arylalkylamine to 6 carbon atoms in the aryl group and from 1 to 4 carbon atoms in the alkyl part; accordingly, when the mu is the necessity of an alkyl with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, cycloalkyl with 3-6 carbon atoms substituted heterocyclyl, heterocyclisation, -N=(heterocyclyl) from a number of furyl, tetrahydrofurfurylamine, thienyl, pyrrolidinyl, pyrrolidinone, Oxymetazoline, isoxazolyl, dihydroisoxazole (isoxazoline), tetrahydroisoquinoline (isoxazolidine), tetrahydro-(2H)-1,2-oxazin-2-yl, dihydrothiazolo (thiazoline), thiadiazolidine, piperidinyl, piperidylamine, morpholinyl, piperazinil, 2-oxo-1,3-diaza-cyclohexyl, exterritoriality, including all possible tautomeric forms and possible salt.

2. Substituted benzoylacetone according to claim 1, having the formula

in which Q, R1, R2, R3, R4, R5, Y and Z are specified in claim 1 value.

Priority signs:

16.05.2001 - all values of the radicals R1-R5, Y, Z and Q, except for the radical Z, concerning substituted cycloalkyl with 3-6 carbon atoms heterocyclyl, heterocyclisation, -N=(heterocyclyl) from a number of furyl, tetrahydrofurfurylamine, thienyl, pyrrolidinyl, pyrrolidinone, Oxymetazoline, isoxazolyl, tetrahydrooxazolo (isoxazolidine), dihydroisoxazole (isoxazoline), tetrahydroisoquinoline (isoxazolidine), tetrahydro-(2H)-1,2-oxazin-2-yl, dihydrothiazolo (tiasa inil), thiadiazolidine, piperidinyl, piperidylamine, morpholinyl, piperazinil, 2-oxo-1,3-diaza-cyclohexyl, exterritoriality, unsubstituted tetrahydro-(2H)-1,2-oxazin-2-yl, which have priority from 03.05.2002.



 

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FIELD: organic chemistry, pharmaceuticals.

SUBSTANCE: invention relates to compounds of general formula I and salt thereof, wherein F is non-aromatic ring system containing five carbon atoms and at least one double bond wherein one ring carbon atom is optionally substituted with X group, such as S, O, or SO2, and one or more ring carbon atoms are optionally substituted with R1; D represents S, O, SO2, NR4, or CH2; Z1 and Z2 are independently O; Y is steryl, mono- or polycyclic non-substituted ring system, containing one or more X group such as S, O, SO2, N; m, n, p, r and q = 0 or 1; meanings of the rest substituents are as defined in specification. Also invention relates to compounds of general formula I , wherein m, n, and q = 0; r = 1. Disclosed is pharmaceutical composition having inhibitory activity in relates to dihydroorotate dehydrogenase (DHODH) containing effective amount of said compound in free form or in form of pharmaceutically acceptable salts together with pharmaceutically acceptable diluents or carriers. Compounds of formula I are useful as drug inhibiting DHODH for treatment of disease or therapeutic condition in which inhibition of DHODH is beneficial.

EFFECT: new compounds as anti-inflammatory, immunomodulating, and anti-proliferative agents.

13 cl, 1 tbl, 1 dwg, 76 ex

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EFFECT: valuable medicinal and biochemical properties of derivatives.

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11 cl, 29 ex

FIELD: organic chemistry, agriculture, insecticides.

SUBSTANCE: invention relates to a substituted anilide derivative of the formula (I): wherein R1 represents hydrogen atom, (C1-C6)-alkyl group; R2 represents hydrogen atom, halogen atom or halogen-(C1-C6)-alkyl group; R3 represents hydrogen atom, halogen atom, (C1-C6)-alkyl group, hydroxyl group or (C1-C6)-alkoxy-group; t = 1; m = 0; each among X that can be similar or different represents (C2-C8)-alkyl group, hydroxy-(C1-C6)-alkyl group or (C3-C6)-cycloalkyl-(C1-C6)-alkyl group; n = 1 or 2; Z represents oxygen atom; Q means a substitute represented by any of the following formulae: Q1-Q3, Q6, Q8-Q12, Q14-Q19, Q21 and Q23 (wherein each among Y1 that can be similar or different represents halogen atom, (C1-C6)-alkyl group, and so on); Y2 represents (C1-C6)-alkyl group or halogen-(C1-C6)-alkyl group; Y3 represents (C1-C6)-alkyl group, halogen-(C1-C6)-alkyl group or substituted phenyl group; p represents a whole number from 1 to 2; q represents a whole number from 0 or 2; r represents a whole number from 0 to 2. Also, invention proposes a chemical for control of pests of agricultural and fruit crops. The chemical comprises substituted anilide derivative of the formula (I) as an active component and represents insecticide, fungicide or acaricide. Also, invention proposes a method for addition of the chemical for control of pests of agricultural and fruits crops. Also, invention proposes aniline derivative represented by the general formula (II): wherein R1 represents hydrogen atom, (C1-C6)-alkyl group; R2 represents hydrogen atom, halogen atom or halogen-(C1-C6)-alkyl group; R3 represents hydrogen atom, halogen atom, (C1-C6)-alkyl group, hydroxyl group or (C1-C6)-alkoxy-group; t = 1; m = 0; each among X that can be similar or different represents (C2-C8)-alkyl group, hydroxy-(C1-C6)-alkyl group or (C3-C6)-cycloalkyl-(C1-C6)-alkyl group; n = 1 or 2. Invention provides the development of anilide derivative as insecticide, fungicide and acaricide against pests of agricultural and fruit crops.

EFFECT: valuable properties of compound.

5 cl, 6 tbl, 27 ex

The invention relates to new derivatives of amidine General formula (I’)

where it is:

in which R1, R2and R3HE or1-C6alkyl, C1-C6alkoxy, R4- H1-C6alkyl, R5- H1-C6alkyl or the radical:

where R10, R11and R12- OH or H, R13- H1-C6alkyl; or the radical:

where R18, R19and R20- H, HE, C1-C6alkyl, R21and R22- H, C1-C6alkyl, or R21-alkylsulfonyl, alkylsulfonyl, alkylaryl, and R22- H or the radical:

where T is -(CH2)k-, k = 1, 2, R27- H, C1-C6alkyl

The invention relates to compounds of formula (I)

in which f represents phenylenebis radical, a represents the radical

in which Rl, R2, R3, R4, R5represent independently a hydrogen atom, IT is a group or an unbranched or branched alkyl or alkoxyalkyl having from 1 to 6 carbon atoms; R11represents a hydrogen atom, an unbranched or branched alkyl radical having from 1 to 6 carbon atoms, or the radical

in which Rl, R2, R3, R4, R5represent independently a hydrogen atom, IT is a group or an unbranched or branched alkyl or alkoxyalkyl having from 1 to 6 carbon atoms; b is a thiophene; W is absent or represents an Association or S; X represents a bond or a radical -(CH2)k-NR16-, -O-, -CO-, -NR16-CO-, and so forth, and k is 0 or 1; Y represents a bond or a radical selected from the radicals -(CH2)m-, -(CH2)m-O-(CH2)n, -(CH-Q-(CH2)n; and Q represents pieperazinove radical, m and n are equal to integers from 0 to 6; R16, R17, R18represent independently a hydrogen atom, or a salt of the compounds

The invention relates to amide derivative of the formula I

< / BR>
where R3represents (1-6C)alkyl or halogen; m is 0, 1, 2 or 3; R1represents hydroxy, halogen, trifluoromethyl, nitro, amino, (1-6C)alkyl, (2-6C)alkenyl, (2-6C)quinil, (1-6C)alkoxy, (1-6C)alkylamino, di-[(1-6C)alkyl] amino, amino-(2-6C)alkylamino, (1-6C)alkylamino-(2-6C)alkylamino etc

-ol)amine in racemic or enantiomeric form, or their pharmaceutically acceptable salt, method of production thereof and pharmaceutical composition" target="_blank">

The invention relates to a derivative of N-(2,4 - or 2,5-disubstituted tetrahydrofuranyl)-N-(phenylethyl--ol) amine in racemic or enantiomeric form of General formula I

H2)n-NH-CH2-C(I) where R represents a linear or branched alkyl group containing from 1 to 10 carbon atoms; pyridyl or thienyl, phenyl radical or substituted phenyl radical of the formula II

(II) where the radicals R1, R2, R3, R4and R5independently represent a hydrogen atom, halogen atom, alkoxy radical containing from 1 to 5 carbon atoms, or alkylsulfonyl radical containing from 1 to 5 carbon atoms;

n is from 1 to 10; and its pharmaceutically acceptable salts

FIELD: medicine, pharmacy.

SUBSTANCE: invention relates to new acid-additive nitrate salts of compounds taken among salbutamol, cetirizine, loratidine, terfenadine, emedastine, ketotifen, nedocromil, ambroxol, dextrometorphan, dextrorphan, isoniazide, erythromycin and pyrazinamide. Indicated salts can be used for treatment of pathology of respiratory system and elicit an anti-allergic, anti-asthmatic effect and can be used in ophthalmology also. Indicated salts have less adverse effect on cardiovascular and/or gastroenteric systems as compared with their non-salt analogues. Also, invention proposes pharmaceutical compositions for preparing medicinal agents for treatment of pathology of respiratory system and comprising above indicated salts or nitrate salts of metronidazol or aciclovir.

EFFECT: improved and valuable properties of compounds.

6 cl, 5 tbl, 19 ex

The invention relates to compounds of the formula I

< / BR>
in which R1denotes-C(=NH)-NH2which may be substituted once by a group-COA, -CO-[C(R6)2]n-Ar, -COOA, -HE or normal aminosidine group

< / BR>
R2denotes H, A, OR6N(R6)2, NO2CN, Hal, NHCOA, NHCOAr, NHSO2A, NHSО2Ar, COOR6, SOPS(R6)2, CONHAr, COR6, COAr, S(O)nA or S(O)nAr,

R3means And, cycloalkyl, - [C(R6)2]nAr, - [C(R6)2]n-O-Ar, -[C(R6)2]nHet or-C(R6)2=C(R6)2-Ar,

R6denotes H, a or benzyl,

X is absent or represents-CO-, -C(R6)2-, -C(R6)2-C(R6)2-, -C(R6)2-CO-, -C(R6)2-C(R6)2-CO-, -C(R6)= C(R6)-CO-, NR6CO-, -N{[CR6)2]n-COOR6} -CO - or-C(COOR6R6-C(R6)2-CO-,

Y represents-C(R6)2-, -SO2-, -CO-, -COO - or-CONR6-,

And denotes alkyl with 1-20 C-atoms, where one or two CH2-groups can be replaced by O - or S-atom or single, two - or three-fold substituted by the group And, Ah', OR6N(R6)2, NO2CN, Hal, NHCOA, NHCOAr', NHSO2A, NHSО2Ar', COOR6, CON(R6)2, CONHAr', COR6, COAr', S(O)nA or S(O)nAr is phenyl or naphthyl,

AG' refers to unsubstituted or one-, two - or three-fold substituted by a group A, OR6N(R6)2, NO2CN, Hal, NHCOA, COOR6, SOPS(R6)2, COR6or S(0)nA phenyl or naphthyl,

Het denotes a single or dual core unsubstituted or one - or multi-substituted by a group of Hal, A, Ar', COOR6, CN, N(R6)2, NO2, Ar-CONH-CH2and/or carbonyl oxygen saturated or unsaturated heterocyclic ring system containing one, two, three or four identical or different heteroatoms, such as nitrogen, oxygen or sulphur,

Hal denotes F, C1, Br or J,

n denotes 0, 1 or 2,

and their salts

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

The invention relates to cavemosum derivative of formula (1) with a broad spectrum of antibacterial activity against different species of pathogenic bacteria, including MRSA

< / BR>
where X Is N or CY and Y denotes H or halogen; R1is amino or a protected amino group; R2is hydrogen or optionally substituted (ness.)alkyl; R3denotes hydrogen or lower alkyl; R4indicates Bogoroditse optionally substituted (NISS

The invention relates to aryl - and getelemen carboalkoxylation acids of formula 1

< / BR>
where R1selected from the group of arrow or getarrow, R2selected from the group of Akilov

The invention relates to new heterocyclic substituted phenoxyacetamide, methods for their preparation and use as a means protivodiareynogo

The invention relates to a new above-mentioned compounds, method of their production and the means of containing this compound, useful for combating fungi and insect pests
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