Aminoheterocyclamide derivatives eliciting pesticide activity

FIELD: organic chemistry, pesticides, agriculture.

SUBSTANCE: invention relates to compounds that elicit high pesticide activity and can be used in control of pests of domestic and agricultural animals. Indicated compounds show the formula (I):

wherein R1 means halogen atom, (C1-C6)-halogenalkyl; R2 means hydrogen atom (H), (C1-C6)-alkyl, (C1-C6)-alkylene-phenyl; X1 means nitrogen atom (N); X2 means group C(CN); X3 means oxygen atom (O); Q means CH; R3 and R4 mean independently of one another hydrogen atom (H) or in common with carbon atom with which they are bound form (C3-C7)-cycloalkyl ring; R5 means a substitute taken among group including (C1-C6)-halogenalkyl, halogen atom being if m above 1 then substitutes R5 can be similar or different; m = 1, 2 or 3; n = 0 or 1. Also, invention describes a method for their preparing and method for control of pests.

EFFECT: valuable pesticide properties of compounds.

7 cl, 3 tbl, 14 ex

 

The present invention relates to new substituted aminoheterocycles formula

where

R1denotes hydrogen, halogen, C1-C6alkyl, C1-C6alkoxy, C1-C6haloalkyl or unsubstituted or substituted by 1-5 substituents phenyl, where the substituents are selected from the group including C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, aryloxy, halogen, cyano and nitro, and if the number of substituents exceeds 1, the substituents may be the same or different;

R2denotes hydrogen, C1-C6alkyl, (C1-C6alkylene)phenyl, pyridyl, COOR6, CONR7R8, COR6, allyl or CH2-O-R6;

X1denotes N;

X2denotes C(CN). C(COOR6), (COR6), With(SOR6), C(CONR7R8) or C(NO2);

X3denotes O or S;

Q represents CH or N;

R3and R4independently of one another denote hydrogen, C1-C6alkyl or together with the carbon atom to which they are attached, form a C3-C7cycloalkyl ring;

R5denotes a Deputy selected from the group comprising C1-C6alkyl, C2-C6alkenyl,2-C6quinil, C1-C6haloalkyl, C1-C 6alkoxy, aryloxy, halogen, cyano, hydroxy, amino, nitro, and substituted by 1-5 substituents phenyl, where the substituents are selected from the group including C1-C6alkyl, C2-C6alkenyl, C2-C6quinil, C1-C6haloalkyl, C1-C6alkoxy, aryloxy, halogen, cyano, hydroxy, amino and nitro, and if the number of phenyl substituents exceeds 1, then they may be the same or different, and when m is greater than 1, the substituents R5may be the same or different;

R6represents C1-C6alkyl, phenyl or benzyl;

R7and R8independently of one another denote hydrogen or C1-C6alkyl;

m denotes 1, 2 or 3; and

n denotes 0 or 1; to receive them and their use for combating pests, and pesticides containing at least one of these compounds.

Substituted aminoheterocycles having pesticidal activity, as described, for example, in DE 19727162. However, presented in this document active ingredients are not always fully satisfy the requirements from the point of view of efficiency and spectrum of activity. In this regard, there is a need for the development of active substances that have a higher pesticide activity. In the claimed invention found that aminoheterocycles form the s I have a very high pesticidal activity, first of all in respect of endoparasites.

The alkyl group present in the definition of the substituents may be straight or branched chain and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl and hexyl, as well as their branched isomers.

Typically, halogen denotes fluorine, chlorine, bromine or iodine. This definition applies to halogen in combination with other concepts, such as haloalkyl or halophenol.

Haloalkyl groups preferably have a chain consisting of 1 to 6 carbon atoms. Haloalkyl represents, for example, vermeil, deformity, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-triptorelin, 2-foretel, 2-chloroethyl, pentafluoroethyl, 1,1-debtor-2,2,2-trichloroethyl, 2,2,3,3-tetraborate and 2,2,2-trichloroethyl; preferably trichloromethyl, diperchlorate, deformity, trifluoromethyl and dichlorofluoromethyl.

Alkoxygroup preferably have a chain consisting of 1 to 6 carbon atoms. Alkoxy denotes, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy, as well as all isomers pentyloxy, hexyloxy; preferably methoxy and ethoxy.

Preferred are the compounds of formula I, in which

R1denotes halogen, C1-C6alkyl, C1-C6alcox is, C1-C6haloalkyl or unsubstituted or substituted by 1-5 substituents phenyl, where the substituents are selected from the group including C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, aryloxy, halogen, cyano and nitro, and if the number of amestitelj exceeds 1, then they may be the same or different;

R2denotes hydrogen, C1-C6alkyl, (C1-C6alkylene)phenyl or pyridyl;

X1denotes N;

X2denotes C(CN);

X3denotes O or S;

Q represents CH or N;

R3and R4independently of one another denote hydrogen, C1-C6alkyl or together with the carbon atom to which they are bound, form a3-C7cycloalkyl ring;

R5denotes a Deputy selected from the group comprising C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, aryloxy, halogen, cyano, hydroxy, amino, Jethro, and, if m is greater than 1, the substituents may be the same or different;

m denotes 1, 2 or 3; and

n denotes 0 or 1.

Especially preferred compounds of formula I include compounds of formula Ia

where the substituents have the meanings specified for formula I.

Preferred compounds of formulas I and Ia are:

(1) compound of formula I, in which X3means Of;

(2) the compound of the formula I, in which R1denotes halogen or1-C6haloalkyl; preferably fluorine, chlorine or1-C4haloalkyl; more preferably chlorine or C1-C2haloalkyl; most preferably chlorine or trifluoromethyl;

(3) the compound of the formula I, in which R2denotes hydrogen or C1-C6alkyl; preferably hydrogen or C1-C2alkyl; most preferably hydrogen;

(4) the compound of the formula I, in which R3and R4independently of one another denote hydrogen, C1-C2alkyl, or together with the carbon atom to which they are attached, form a C3-C6cycloalkyl ring; preferably hydrogen, or together with the carbon atom to which they are bound, form a3-C5cycloalkyl ring; most preferably hydrogen, or together with the carbon atom to which they are bound, form cyclopropyl ring;

(5) the compound of the formula I, in which m denotes 1 or 2, preferably 2;

(6) the compound of the formula I in which n denotes 0;

(7) the compound of the formula I, in which R1denotes halogen or C1-C6haloalkyl; R2denotes hydrogen or C1-C6alkyl; R3and R4independently from each other is oznachaet hydrogen, C1-C2alkyl or together with the carbon atom to which they are attached, form a C3-C6cycloalkyl ring; m represents 1 or 2; and n denotes 0;

(8) the compound of the formula I, in which R1denotes a fluorine, chlorine or1-C4haloalkyl; R2denotes hydrogen or C1-C2alkyl; R3and R4denote hydrogen or together with the carbon atom to which they are bound, form a3-C5cycloalkyl ring; m is 2; and n denotes 0;

(9) the compound of the formula I, in which R1denotes chlorine or C1-C2haloalkyl; R2denotes hydrogen; R3and R4denote hydrogen or together with the carbon atom to which they are bound, form cyclopropyl ring; m is 2; and n denotes 0.

Another object of the invention is a method of obtaining compounds of formula I and optionally their enantiomers, for example, characterized in that the compound of the formula

which is known or may be produced analogously to corresponding known compounds and in which R1, R2X1and X2have the meanings specified for formula I, is subjected to the interaction with the compound of the formula

which is known or can be obtained is nelogicno corresponding known compounds and in which X 3, R3, R4, R5, m, n and Q have the meanings specified for formula I and Z represents a leaving group, optionally in the presence of a basic catalyst, and if necessary, the compound of formula I obtained by this process or any other method, or its enantiomer can be converted into another compound of formula I or its enantiomer, the mixture of enantiomers, which can be obtained with this process, share and produce the desired enantiomer.

Acceptable leaving groups are halogen, C1-C6alkoxy or hydroxy, preferably chlorine.

Acceptable grounds, which facilitate the reaction are, for example, trialkylamine, basic heterocycles or phosphines. As the preferred examples, it should be noted, for example, triethylamine, diisopropylethylamine, pyridine, 4-(N,N-dimethylamino)pyridine, chinaclonidine, 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU) and triphenylphosphine. It is preferable to diisopropylethylamine.

The reagents can be subjected to interact with each other in native form, i.e. without addition of a solvent or diluent, for example in the molten state. However, it is more preferable to add an inert solvent or diluent or a mixture thereof. Examples of such solvents or diluents, which is worth mentioning, include aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, tetralin, chlorobenzene, dichlorobenzene, Brabanthal, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, carbon tetrachloride, dichloroethane, trichloride or tetrachloride; ethers, such as diethyl ether, DIPROPYLENE ether, diisopropyl ether, disutility ether, methyl tert-butyl ether, onomatology ether of ethylene glycol, monotropy ether of ethylene glycol, dimethyl ether of ethylene glycol, dimethoxyethane ether, tetrahydrofuran or dioxane; ketones, such as acetone, methyl ethyl ketone or methyl isobutyl ketone; amides such as N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N is an organic or triamide hexamethylphosphoric acid; NITRILES, such as acetonitrile or propionitrile; and sulfoxidov, such as dimethylsulfoxide. If we consider the reaction is carried out in the presence of a base, then used in excess of base, such as triethylamine, pyridine, N-methylmorpholine or N,N-diethylamine, can also serve as a solvent or diluent. Preferred are halogenated hydrocarbons, especially dichloromethane.

The reaction is expediently carried out at temperatures from about -20°C to about +150°who, preferably from about -10°C to about +80°S, most preferably from about 0°C to about +40°C.

According to a preferred variant, the compound of formula II is subjected to interaction with the compound of the formula III at a temperature of from 0° to 120°C, preferably 20°With, in a halogenated hydrocarbon, preferably dichloromethane.

The compound of formula I, for example, depending on the number, absolute and relative configuration of the asymmetric carbon atoms may be present in the form of one of the possible isomers or mixtures thereof, such as pure isomers, such as antipodes and/or diastereoisomer, or a mixture of isomers, such as enantiomeric mixtures, such as racemates, mixtures of diastereoisomers or racemic mixtures, the invention relates both to the pure isomers and to all possible mixtures of isomers, it means both above and below in the context of describing, even if not specifically described details stereochemical structure.

Depending on the source of the products and processes of a mixture of diastereoisomers and racemic mixtures of compounds of the formula I obtained by the method according to the invention or any other method, can be divided by a known method on the net diastereoisomers or racemates, based on the physico-chemical differences of the constituents, for example, using fractionated crystallization, distillation and/or chromatography.

The mixture of enantiomers, such as racemates, can be divided into the optical antipodes by known methods, for example by recrystallisation from an optically active solvent, chromatography on chiral adsorbents, for example, liquid chromatography high pressure (ghvd) on the cellulose acetate, with the use of appropriate microorganisms, by cleavage of a specific immobilized enzymes, via the formation of the included compounds, for example using chiral crown ethers, in complex with which may be included on only one enantiomer.

According to the invention in addition to highlight the corresponding mixtures of isomers to obtain pure diastereoisomers or enantiomers, you can use well-known methods diastereoselective or enantioselective synthesis, for example, carrying out the method according to the invention using doctow who have the appropriate acceptable stereochemical structure.

If the individual components differ in biological activity, then in any case it is advisable to select or synthesize biologically more active isomer, for example, a mixture of enantiomers or isomers, for example, a mixture of enantiomers.

The agreement is but the method according to the invention, it is preferable to apply the initial and intermediate products, which allow to obtain the compounds of formula I, described above as preferred.

The invention also relates to a method for which is described in the example.

The source and intermediate products, which are new and which are used according to the invention for preparing compounds of formula I, and their use and method of production thereof are also an object of the invention.

The compounds of formula I according to the invention not only possess a wide spectrum of activity and can be used as an effective active substances for pest control, including, in particular combating endo - and ectoparasites of animals, but they also are well tolerated by warm-blooded animals, fish and plants.

In the context of the present description under ectoparasites see, in particular, insects, mites and insects Parasitiformes mites. They include insects of the orders: Lepidoptera, Coleoplera, Homoptera, Heteroptera, Diptera, Thysanopteru, Orthoptera, Anoplura, Siphonaptera, Mallophaga, Thysanura, Isoptera, Psocoptera u Hymenoptera. In particular, mention should be made of ectoparasites that annoy people or animals and carry pathogens, for example flies such as Musca domestica, Musca vetustissima, Musca autumnalis, Fannia canicularis, Sarcophaga carnaria, Lucilia cuprina, Hypoderma bovis, Hypoderma lineatum, Chrysomyia chloroppyga, Dermatobia hominis, Cochliomyia hominivorax, Gasterophilus intestinalis, Oestrus ovis, Stomoxys calcitrans, Haematobia irritans, and mosquitoes (Nematocera), such as Culiciae, Simuliidae, Psychodidae, as well as blood-sucking parasites, for example fleas, such as Ctenocephalides felis and Ctenocephalides canis (cat and dog fleas), Xenopsylla cheopis, Pulex irritans, Dermatophilus penetrans, lice, such as Damalina ovis, Pediculus humanis, biting flies and horseflies (Tabanidae), Haematopota spp., such as Haematopota pluvialis, Tabanidea spp., such as Tahanus nigrovittatus, Chrysopsinae spp.,such as Chrysops caeculiens, flies CE-CE, such as the species R. Glossinia, biting insects, particularly cockroaches, such as Blalella germanica, Blatta orientalis, Periplaneta americana, mites, such as Dermanyssus gallinae, Sarcoptes scabiei, Psoroptes ovis and Psorergates spp., and finally, but not least, Parasitiformes mites. The latter belong to the order Acarina.

Known characteristic representatives of Parasitiformes mites are, for example, Boophilus, Amblyomma, Anocentor, Dermacentor, Haemaphysalis, Hyalomma, Ixodes, Rhipicentor, Margaropus, Rhipicephalus, Argas, Otobius and Ornithodoros and the like, which preferably are attacking warm-blooded animals, including farm animals, such as cattle, pigs, sheep and goats, poultry such as chickens, turkeys and geese, fur-bearing animals such as mink, foxes, chinchillas, rabbits and the like, as well as domestic animals such as cats and dogs, and even people can't avoid their attacks.

The compounds of formula I can also be used to kill insects with sanitary-hygienic value, primarily representatives of the order Diptera, families Sarcophagidae, Anophilidae Culicidae; units Orthoptera, Dictyoptera (e.g., family Blattidae) and Hymenoplera (for example, family Formicidae).

The compounds of formula I also have a fairly high activity against mites and insects that are pests of plants. When used to combat spider mites of the order Acarina they are effective against eggs, nymphs and adults Tetranychidae (Tetranychus spp. and Panonychus spp.).

They have a pronounced activity against sucking insects of the order Homoptera, especially against pests of the families Aphididae, Delphacidae, Cicadellidae, Psyllidae, Loccidae, Diaspididae and Eriophydidae (for example, mite grape Volochkova on citrus fruits); units Hemiptera, Heteroptera and Thysanoptera, and eating plants insects of the orders Lepidoptera, Coleoptera, Diptera and Orthoptera.

They can also be used as soil insecticides to control soil pests.

Thus, the compounds of formula I are effective against all stages of the development of sucking insects and insect pests of crops such as cereals, cotton, rice, corn, soy, potatoes, vegetable crops, fruit crops, tobacco, hops, citrus, avocado and other cultivated plants.

The compounds of formula also have efficacy against living on plant nematodes of the genera Meloidogyne, Heterodera, Pratylenchus, Ditylenchus, Radopholus, Rizoglyphus etc.

In particular, the compounds are effective against helminths, in which endoparasitic nematodes can cause serious diseases of mammals and poultry, for example, sheep, pigs, goats, cows, horses, donkeys, dogs, cats, Guinea pigs and exotic birds. Typical and this plan nematodes are: At, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostonum, the recommended dose rate, Charbertia, Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris and Parascaris.

A particularly important feature of the compounds of the formula I is their effectiveness against parasites resistant to the active substances from the class of benzimidazole.

Some pests belonging to the species Nematodirus, Cooperia and Oesophagostomim, infect the gastrointestinal tract of an animal host, while other representatives of the species At and Ostertagia parasites in the stomach, and representatives of the species Dictyocaulns Lodge in the lung tissue. Parasites of the families Filariidae and Setariidae can be found in the cells of the inner tissues and organs, e.g. heart, blood vessels, lymph nodes and subcutaneous tissue. Especially important parasite is a worm that dwells in the heart of dogs, Dirofilaria immitis. The compounds of formula I are highly effective against these parasites.

In addition, the compounds of formula I can preferably be applied on the I control pathogenic parasites of man. From these typical representatives of which are found in the gastrointestinal tract, are the representatives of the genera Ancylostoma, Necator, Ascaris, Strongyloides, Trichinella, Capillaria, Trichuris and Enterobius. Compounds of the present invention are also effective against parasites of the genera Wuchereria, Brugia, Onchocerca and Loa from the family Filariidae that live in the blood, tissues and various organs, as well as against Dracunculus and parasites of the genera Strongyloides and Trichinella, which, in particular, affect the gastrointestinal tract.

Under high pesticidal activity of the compounds of formulas I understand the activity that is causing the mortality of the above pests at least 50-60%. In particular, the compounds of formula I are characterized by a very long residual action.

The active compounds according to the invention and compositions containing them against pests of the animal Kingdom can be substantially broadened and adapted to prevailing circumstances by addition of other insecticides and/or acaricides. Interest additives can, for example, to include representatives of the following classes of active ingredients: organophosphorus compounds, NITROPHENOL and their derivatives, formamidine, urea, carbamates, pyrethroids, chlorinated hydrocarbons, neonicotinoids and preparations based on Bacillus thuringiensis.

The connection forms of the crystals of I are preferably used in unmodified form or preferably in combination with auxiliary substances, usually used in cooking techniques preparative forms, and they are subjected to conventional processing, receiving mulgirigala concentrates, ready-to-use solutions for spraying or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusty, granules or microencapsulated in a polymer preparations. Also like the composition, processing methods, such as spraying, spraying in the form of a mist, dusting, scattering or watering, selected depending on the objectives and the prevailing circumstances.

Preparative form, i.e. the agents, preparations or compositions containing the active substance of the formula I or combinations of these active ingredients with other used in the agrochemical active substances and optionally a solid or liquid auxiliary substance well-known method, for example, thorough mixing and/or grinding the active substances with extenders for compositions, e.g. solvents, solid carriers and optionally a surface-active substances (surfactants).

As solvents can be used: aromatic hydrocarbons, preferably alkylbenzene fraction having 8-12 carbon atoms, such as xiaowei mixtures or alkylated naphthalenes, aliphatic or llolita the practical hydrocarbons, such as cyclohexane, paraffins or tetrahydronaphthalene, alcohols, such as ethanol, propanol or butanol, glycols and their ethers and esters, such as propylene glycol, a simple broadcast dipropyleneglycol, ethylene glycol or a simple onomatology or - ethyl ether of ethylene glycol, ketones such as cyclohexanone, isophorone or datetoday alcohol, highly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, or water, vegetable oils, such as rapeseed, castor, coconut or soya oil, and optionally a silicone oil.

The solid carriers used, for example Farrukh Dustov and dispergiruyushchie powders usually are crushed natural mineral fillers such as calcite, talc, kaolin, montmorillonite or attapulgite. To improve the physical properties it is also possible to add highly dispersed silicon dioxide or fine absorptive polymers. Acceptable consisting of small particles adsorptive carriers for granules are the carriers are porous types, for example pumice, broken brick, thick or bentonite, and suitable nearbyrumi carriers are materials such as calcite or sand. Moreover, it is possible to apply a large number of pre-granulated materials reorgan the ical or organic origin, such as, in particular, dolomite or comminuted into powder residues.

Suitable surface-active substances depending on the nature of the active substance of the formula I to be included in the preparative form, or combinations of these active ingredients with other insecticides or acaricides, are nonionic, cationogenic and/or anionic surfactants having good emulsifying, dispersing and wetting properties. Under surfactants also need to understand the mixture of surface-active substances.

Acceptable anionic surfactants may be either the so-called water-soluble Soaps or water-soluble synthetic surface-active substances.

Acceptable Soaps are salts of alkali metals, salts of alkaline-earth metal or unsubstituted or substituted ammonium salts of higher fatty acids (C10-C22), for example sodium salts or potassium salts of oleic or stearic acid, or mixtures of natural fatty acids, which can be obtained e.g. from coconut oil or tall oil. As surface-active substances can be applied methyltaurine fatty acids.

But more often use the so-called Sint the static surface-active substances, in particular, the sulfonates of fatty alcohols, sulfates of fatty alcohols, sulfonated benzimidazole derivatives or alkylarylsulfonates.

As a rule, sulfonates or sulfates, fatty alcohol used in the form of salts of alkali metals, salts of alkaline earth metal or unsubstituted or substituted ammonium salts, and they usually have an alkyl radical bearing from 8 to 22 carbon atoms, and alkyl includes alkyl fragment of acyl radicals, e.g. the sodium or calcium salt of lignosulfonic acid, ester modellserie acid or a mixture of sulfates of fatty alcohols obtained from natural fatty acids. These compounds also include salts of esters of sulfuric acid, and adducts sulfonic acids of fatty alcohol/ethylene oxide. Sulfonated benzimidazole derivatives preferably contain 2 sulfonic group and one radical of a fatty acid containing from 8 to 22 carbon atoms. Examples of alkylarylsulfonates are sodium, calcium or triethanolamine salt dodecylbenzenesulfonic acid, dibutylaminoethanol acids or condensation products of naphtalenesulfonic acid/formaldehyde. Also acceptable are corresponding phosphates, e.g. salts of ether phosphoric acid and adduct para-Nonylphenol with 4 to 14 by moles ethyleneoxide links, or phospholipids.

p> Nonionic surfactants are preferably derived polyglycolic ether and aliphatic or cycloaliphatic alcohols, of saturated or unsaturated fatty acids and ALKYLPHENOLS, these derivatives contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon fragment and 6-18 carbon atoms in the alkyl fragment of alkyl phenols. Also acceptable nonionic surfactants are the water-soluble adducts of polyethylene oxide and polypropylenglycol, ethylenediaminetetra and alkylpolyoxyethylene containing 1-10 carbon atoms in the alkyl chain, these adducts have 20-250 groups etilenglikolevykh ether and 10-100 groups of propylene glycol ether. The above compounds typically contain 1-5 etilenglikolevykh links to the movie propylene glycol.

Examples of nonionic surfactants are nonylphenolethoxylates, ethers, castor oil and polyglycol, adducts of polypropylene/polyethylene oxide, tributyltinoxide, polyethylene glycol and octylphenoxypolyethoxyethanol. Also acceptable are esters of fatty acids and polyoxyethylenesorbitan, such as triolein of polyoxyethylenesorbitan.

Cationogenic surfactants preferably before the represent Quaternary ammonium salt, which have as a substituent at least one8-C22alkyl radical and, as additional substituents (ness.)alkyl, optionally halogenated (ness.)alkyl, benzyl or hydroxy(ness.)alkyl radicals. The salts are preferably in the form of halides, methylsulfate or ethylsulfate. Examples are chloride of stearylamine or bromide, benilde(2-chloroethyl)ethylamine.

Surfactants, which are usually used in cooking techniques preparative forms are described, for example, in the following publications:

″Mc Cutcheon''s Detergents and Emulsifiers Annual″, McPublishing Corp., Glen Rock, NJ, USA, 1988";

.Stache, "Tensid-Taschenbuch" (Surfactants Handbook, 2nd ed., C. Hanser Publishing, Munich, Vienna, 1981;

M. and J. Ash. "Encyclopedia of Surfactants", vol I-III, Chemical Publishing Co., New York, 1980-1981.

The preferred preparative forms for warm-blooded animals with the aim of combating helminths alauda solutions, emulsions, suspensions (for infusion), food additives, powders, tablets including effervescent tablets, boluses, capsules, microcapsules and compositions for irrigation, and as excipients for these compositions should be used physiologically acceptable excipients.

As binders for tablets and boluses is possible to apply the modified polymer of natural substances that dissolve the s in water or alcohol, such as starch, cellulose derivatives, or proteins (e.g., methylcellulose, carboxymethylcellulose, metilgidroxiatilzelllozu, proteins such as Zein, gelatin and the like), as well as synthetic polymers such as polyvinyl alcohol, polyvinylpyrrolidone, etc. Tablets also contain fillers (e.g. starch, microcrystalline cellulose, sugar, lactose, etc.), substances that improve slip, and baking powder.

If deworming drugs are in the form of concentrated feed for them as carriers used, for example, preferred foods, pellets or protein concentrates. Such concentrates or compositions can contain in addition to the active substances, additives, vitamins, antibiotics, chemotherapeutic agents or other pesticides, primarily bactericides, fungicides, coccidial or even hormone preparations, substances having anabolic effect, or substances that accelerate growth, which affect the quality of meat destined for the slaughter of animals, or which in some other way have a positive effect on the body. If a song or part of them active substances of formula I directly added to feed or drinking bowls, cooked food or drink contain loads the existing substances preferably in a concentration of about of 0.0005 to 0.02 wt.% (5-200 ppm million).

The processing composition according to the invention of animals to be processed, can be done topically, orally, parenterally or subcutaneously, and the composition may be in the form of solutions, emulsions, suspensions (for infusion), powders, tablets, boluses, capsules or intended for irrigation forms.

The compounds of formula I according to the invention can be applied individually or in combination with other biocides. For example, for efficiency, you can combine them with pesticides with the same mode of action or to broaden the spectrum of action, they can be combined with compounds with different mechanism of action. Also, it may be appropriate to add ingredients that have repellent properties, so-called repellents. If you want to widen the spectrum of action against endoparasites, such as a worm, the compounds of formula I preferably combine with substances possessing endoparasiticides properties. Of course, they can also be used in combination with antibacterial agents. Since the compounds of formula I are imagetitle", this means that they are efficiency, primarily in the adult stages of the parasite target, it may be advisable to add pesticides that are effective just in relation to juvenile stages. In this way the can is about to fight with most parasites, causing great economic damage. In addition, efforts to avoid development of resistance. Many combinations may also have a synergistic effect, i.e. in this case the total amount of applied active substance can be reduced, which is desirable from an environmental point of view. A preferred group of component combinations and the most preferred components of the combinations below, this combination in addition to the compound of the formula I can contain one or more components.

Suitable components for blending include biocides, for example, the following insecticides and acaricides that have different mechanisms of action and are well known to the person skilled in the art, such as chitin synthesis inhibitors, growth regulators; active substances that have the same mechanism of action, and juvenile hormones (analogues of juvenile hormone); active substances with emagazines activity; insecticide with a broad spectrum of action; acaricides and nematicides with a wide range of actions; and a well-known deworming drugs and substances deterring insects and/or mites, the aforementioned repellents or detergents.

Examples of suitable insecticides and acaricide is, which do not limit the scope of the invention, are:

(I) aldicarb;

(II) azinphos-methyl;

(III) benfuracarb;

(IV) bifenthrin;

(V) buprofezin;

(VI) carbofuran;

(VII) dibutylamino;

(VIII) cartap,

(IX) chlorfluazuron;

(X) chlorpyrifos;

(XI) cyfluthrin;

(XII) lambda cigalotrin;

(XIII) alpha-cypermethrin;

(XIV) Zeta-cypermethrin;

(XV) deltamethrin;

(XVI) diflubenzuron;

(XVII) endosulfan;

(XVIII) ethiofencarb;

(XIX) fenitrothion;

(XX) fenobucarb;

(XXI) fenvalerate;

(XXII) formation;

(XXIII) methiocarb;

(XXIV) heptenophos;

(XXV) Imidacloprid;

(XXVI) isoprocarb;

(XXVII) methamidophos;

(XXVIII) methomyl;

(XXIX) mevinphos;

(XXX) parathion;

(XXXI) parathion-methyl;

(XXXII) fozalon;

(XXXIII) pirimicarb;

(XXXIV) propoxur;

(XXXV) teflubenzuron;

(XXXVI) terbufos;

(XXXVII) triazamate;

(XXXVIII) abamectin;

(XXXIX) fenobucarb;

(XL) tebufenozide;

(XLI) fipronil;

(XLII) beta-cyfluthrin;

(XLIII) selfloader;

(XLIV) fenpyroximate;

(XLV) pyridaben;

(XLVI) fenazaquin;

(XLVII) of pyriproxyfen;

(XLVIII) of pyrimidifen;

(XLIX) nitenpyram;

(L) NI-25, acetamiprid;

(LI) avermectin B1;

(LII) plant extract having activity against insects;

(LIIIII) composition containing nematodes, with activity against insects;

(LIVIV) the composition p is obtainable from Bacillus subtilis;

(LV) composition containing mushrooms with activity against insects;

(LVI) composition containing viruses with activity against insects;

(LVIIVII) SA 303 630;

(LVIIIVII) acetat;

(LIXIX) acrinathrin;

(LX) alankar;

(LXI) alphamethrin;

(LXII) amitraz;

(LXIII) AZ 60541;

(LXIV) azinphos;

(LXV) azinphos M;

(LXVI) azocyclotin;

(LXVII) bendiocarb;

(LXVIII) bensultap;

(LXIX) beta-cyfluthrin;

(LXX) VRMS;

(LXXI) papenbrock;

(LXXII) bromophos;

(LXXIII) bofenkamp;

(LXXIV) butocarboxim;

(LXXV) butylparaben;

(LXXVI) cadusafos;

(LXXVII) carbaryl;

(LXXVIII) carbophenothion;

(LXXIX) cloethocarb;

(LXXX) chlorethoxyfos;

(LXXXI) chlormephos;

(LXXXII) CIS-resmethrin;

(LXXXIII) clozaril;

(LXXXIV) clofentezine;

(LXXXV) canapos;

(LXXXVI) cicloprofen;

(LXXXVII) cyhexatin;

(LXXXVIII) demeton M;

(LXXXIX) demeton S;

(XC) demeton-S-methyl;

(XCI) dichlofenthion;

(XCII) diclofe;

(XCIII) diation;

(XCIV) dimethoate;

(XCV) dimethylene;

(XCVI) dioxathion;

(XCVII) edifenphos;

(XCVIII) emamectin;

(XCIX) esfenvalerate;

(C) ation;

(CI) etofenprox;

(S) ethoprophos;

(III) etrimfos;

(CIV) fenamiphos;

(CV) fenbutatin;

(CVI) fanatical;

(CVII) fenpropathrin;

(VIII) feneral;

(CIX) fenthion;

(AU) fluazinam;

(XI) flucycloxuron;

(CXII) flucythrinate;

(CXII) flufenoxuron;

(CXIV) plutopress;

(CXV) fonofos;

(CXVI) fosthiazate;

(CXVII) tupfenrock;

(CXVIII) HCH;

(CXIX) hexaflumuron;

(SHH) hexythiazox;

(CXXI) iprobenfos;

(CXXII) isofenphos;

(CXXIII) isoxathion;

(CXXIV) ivermectin;

(CXXV) lambda cigalotrin;

(CXXVI) Malathion;

(CXXVII) mecarbam;

(CXXVIII) resolvents;

(CXXIX) metaldehyde;

(SHHH) metolcarb;

(CXXXI) milbemectin;

(CXXXII) moxidectin;

(CXXXIII) naled;

(CXXXIV) NC 184;

(CXXXV) omethoate;

(CXXXVI) oxamyl;

(CXXXVII) oxydemeton M;

(CXXXVIII) oxidation;

(CXXXIX) permethrin;

(CXL) pintout;

(CXLI) Fort;

(CXLII) phosmet;

(CXLIII) facsim;

(CXLIV) pirimiphos M;

(CXLV) pirimiphos;

(CXLVI) promecarb;

(CXLVII) propafol;

(CXLVIII) prothiofos;

(CXLIX) procoat;

(CL) pyraclofos;

(CLI) peralatan-tion;

(CLII) prismatron;

(CLIII) feverfew;

(CLIV) RH 5992;

(CLV) coalition;

(CLVI) sabots;

(CLVII) sulfotep;

(CLVIII) sulprofos;

(CLIX) tebufenpyrad;

(CLX) tebupirimfos;

(CLXI) tefluthrin;

(CLXII) temephos;

(CLXIII) terram;

(CLXIV) tetrachlorvinphos;

(CLXV) titanox;

(CLXVI) thiodicarb;

(CLXVII) thiofanox;

(CLXVIII) thionazin;

(CLXIX) thuringiensis;

(CLXX) tralomethrin;

(CLXXI) threaten;

(CLXXII) triazophos;

(CLXXIII) treasure;

(CLXXIV) trichlorfon;

(CLXXV) triflumuron;

(CLXXVI) timetaken;

(CLXXVII) validation;

(CLXXVIII) xiller;

(CLXXIX YI 5301/5302;

(CLXXX) decamethrin;

(CLXXXI) DPX-MP062;

(CLXXXII) RH-2485;

(CLXXXIII) D2341;

(CLXXXIV) XMC (3,5-climatecarbon);

(CLXXXV) lufenuron;

(CLXXXVI) fluazuron;

(CLXXXVII) methoprene;

(CLXXXVIII) hydroprene;

(CLXXXIX) fenoxycarb;

(CXC) chlorfenapyr or

(CXCI) spinosad.

Examples of acceptable deworming drugs, which do not limit the scope of the invention below, some of these as examples of compounds in addition to the anthelminthic activity also possess insecticidal and acaricidal properties and in some cases have already been included in the above list:

(A1) praziquantel =2-cyclohexylcarbonyl-4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-α]isoquinoline

(A2) closantel =3,5-did-N-[5-chloro-2-methyl-4-(a-cyano-4-chlorbenzyl)-phenyl]salicylamide

(A3) triclabendazole =5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole

(A4) levamisole =L-(-)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1b]thiazole

(A5) mebendazole = methyl ester (5-benzoyl-1H-benzimidazole-2-yl)carbamino acid

(A6) omphalitis = macrocyclic product of the fermentation of the fungus Omphalotus learins described in WO 97/20857

(A7) abamectin = avermectin B1

(A8) ivermectin =22,23-dihydroavermectin B1

(A9) moxidectin =5-O-demethyl-28-deoxy-25-(1,3-dimethyl-1-butenyl)-6,28-epoxy-23-(methoxyimino)milbemycin

(A10) doramectin =25-cyclohexyl-5-O-demethyl-25-de(1-meth is propyl)avermectin Ala

(A11) milbemectin = mixture milbemycin A3 and milbemycin A4

(A12) milbemycin =5-oxime milbemectin

Examples of suitable substances with repellent properties (repellents or detergents), which do not limit the scope of the invention, are:

(R1) D (N,N-dimethyl-m-toluamide)

(R2) KBR 3023 N-butyl-2-oxycarbonyl-(2-hydroxy)piperidine

(R3) Zemiata =N-2,3-dihydro-3-methyl-1,3-thiazol-2-ilidene-2,4-xylidene

These components for the mixtures are known to experts in this field. Most of them are described in various editions of the Handbook of pesticides (Pesticide Manual, The British Crop Protection Council, London), a described in various editions of The Merck Index, Merck & Co., Inc., Rahway, New Jersey, USA or in patents. So in the list below are some examples of literary sources, with references to these active substances.

(I) 2-methyl-2-(methylthio)Propionaldehyde-O-methylcarbamate (aldicarb), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, p.26;

(II) S-(3,4-dihydro-4-oksobenzo[d|-[1,2,3]triazine-3-ylmethyl)-O,O-dimethylphosphorodithioate (azinphos-methyl), see The Pesticide Manual, 11th ed., (1997), The British Crop Protection Council, London, p.67;

(III) methyl-N-[2,3-dihydro-2,2-dimethylbenzofuran-7-jocstarbunny(methyl)aminothio]-N-isopropyl-β-alaninate (benfuracarb), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London p.96;

(IV) 2-methylbiphenyl-3-ylmethyl-(Z)-(1RS)-cis-3-(2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate (bifenthrin), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, page 118;

(V) 2-tert-Butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazin-4-one (buprofezin), see The Pesticide Manual, 11thed., (1997), The British Crop Protection Council, London, p.157;

(VI) 2,3-dihydro-2,2-dimethylbenzofuran-7-yl-methylcarbamate (carbofuran), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(VII) 2,3-dihydro-2,2-dimethylbenzofuran-7-yl-(dibutylamino)methylcarbamate (carbosulfan), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(VIII) S,S'-(2-dimethylaminomethylene)-bis(THIOCARBAMATE) (cartap), see The Pesticide Manual, 11eed., (1997), The British Crop Protection Council, London, str;

(IX) 1-[3,5-dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-differentail)urea (chlorfluazuron), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(X) O,O-diethyl-O-3,5,6-trichloro-2-pyridylacetate (chlorpyrifos), see The Pesticide Manual, 11eed., (1997), The British Crop Protection Council, London, str;

(XI) (RS)-α-cyano-4-fluoro-3-phenoxybenzyl-(1RS,3RS;1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (cyfluthrin), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XII) mixture of (S)-α-cyano-3-phenoxybenzyl-(Z)-(1R,3R)-3-(2-chloro-3,3,3-tryptophanyl)-2,2-dimethyl who eloprofessional and (R)-α -cyano-3-phenoxybenzyl-(Z)-(1R,3R)-3-(2-chloro-3,3,3-tryptophanyl)-2,2-dimethylcyclopropanecarboxylate (lambda cigalotrin), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XIII) the racemate comprising (S)-α-cyano-3-phenoxybenzyl-(1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and (R)-α-cyano-3-phenoxybenzyl-(1S,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (alpha-cypermethrin), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XIV) a mixture of the stereoisomers of (S)-α-cyano-3-phenoxybenzyl (1RS,3RS,1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate(Zeta-cypermethrin), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XV) (S)-α-cyano-3-phenoxybenzyl-(1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate (deltamethrin). see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XVI) (4-chlorophenyl)-3-(2,6-differentail)urea (diflubenzuron), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XVII) (1,4,5,6,7,7-hexachloro-8,9,10-trinorborn-5-ene-2,3-rebismart)sulfite (endosulfan), see The Pesticide Manual, 11th ed., (1997), The British Crop Protection Council, London, str;

(XVIII) α-ethylthio-ortho-trimethylarsine (ethiofencarb), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XIX) O,O-dimethyl-O-4-nitro-m-tolylphosphino (fenitrothion), see The Pesticid Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XX) 2-second-butylphenylmethyl (fenobucarb), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XXI) (RS)-α-cyan-3-phenoxybenzyl-(RS)-2-(4-chlorophenyl)-3-methylbutyrate (fenvalerate), see The Pesticide Manual, 11thed., (1997), The British Crop Protection Council, London, str;

(XXII) S-[formyl(methyl)carbamoylmethyl]-O,O-dimethyl-phosphorodithioate (formation). see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XIII) 4-methylthio-3,5-xylylenediisocyanate (methiocarb), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XXIV) 7-chlorobicyclo[3.2.0]hepta-2,6-Dien-6-endimetriosis (heptenophos), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XXV) 1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamino (Imidacloprid, see The Pesticide Manual, 11eed., (1997), The British Crop Protection Council, London, str;

(XXVI) 2-isopropylaminocarbonyl (isoprocarb), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XXVII) O,S-dimethylphosphorodithioate (methamidophos), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XXVIII) of S-methyl-N-(methylcarbamoyl)thioacetimidate (methomyl), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XXIX) methyl-3-(diethoxyphosphoryloxy)but-2-ENOAT (mevinphos), see The Pesticide Manual, 11-eed., (197), The British Crop Protection Council, London, str;

(XXX) O,O-dimethyl-O-4-nitrophenylphosphate (parathion), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XXXI) O,O-dimethyl-O-4-nitrophenyl-fosfertil (parathion-methyl), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XXXII) S-6-chloro-2,3-dihydro-2-oxo-1,3-benzoxazol-3-ylmethyl-O,O-dimethylphosphorodithioate (fozalon), see The Pesticide Manual, 11th ed., (1997), The British Crop Protection Council, London, str;

(XXXIII) 2-dimethylamino-5,6-dimethylpyrimidin-4-yl-dimethylcarbamate (pirimicarb), see The Pesticide Manual, 11thed., (1997), The British Crop Protection Council, London, str;

(XXXIV) 2-isopropoxybenzonitrile (propoxur), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XXXV) 1-(3,5-dichloro-2,4-differenl)-3-(2,6-differentail)urea (teflubenzuron), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XXXVI) S-tert-butylthioethyl-O,O-dimethyl-phosphorodithioate (terbufos), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XXXVII) ethyl-(3-tert-butyl-1-dimethylcarbamoyl-1H-1,2,4-triazole-5-ylthio)acetate, (triazamate), see The Pesticide Manual, 11thed., (1997), The British Crop Protection Council, London, str;

(XXXIII) abamectin, see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, page 3;

(XXXIX) 2-second-butylphenylmethyl (fenobucarb), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Coucil, London, str;

(XL) N-tert-butyl-N'-(4-methylbenzoyl)for 3,5-dimethylbenzophenone (tebufenozide), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XLI) (±)-5-amino-1-(2,6-dichloro-α,α,α-Cryptor-para-tolyl)-4-triftormetilfullerenov-3-carbonitrile (fipronil), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XLII)(RS)-α-NATO-4-fluoro-3-phenoxybenzyl(1RS,3RS; 1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate(beta-cyfluthrin), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XLIII) (4-ethoxyphenyl)-[3-(4-fluoro-3-phenoxyphenyl)propyl](dimethyl)silane(selfloader), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XLIV) of tert-butyl (E)-α-(1,3-dimethyl-5-Phenoxyethanol-4-ylmethylamino)-para-toluate (fenpyroximate), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XLV) 2-tert-butyl-5-(4-tert-butylbenzyl)-4-chloropyridin-3(2H)-he(pyridaben), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XLVI) 4-[[4-(1,1-dimetilfenil)phenyl]ethoxy]hinzelin (fenazaquin), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str.507;

(XLVII) 4-phenoxyphenyl-(RS)-2-(pyridyloxy)propyl ether (pyriproxifen), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(XLVIII) 5-chloro-N-{2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy}-6-ethylpyrimidine-4-amine(pyrimidifen), see The Pesticide Manual, 11thed., (1997), The British Crop Protection Council, London, str;

(XLIX) (E)-N-(6-chloro-3-pyridylmethyl)-N-methyl-N'-methyl-2-nitropyridinium (nitenpyram), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(L) (E)-N1-[(6-chloro-3-pyridyl)methyl]-N2-cyano-N1-methylacetamide (NI-25, acetamiprid), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, page 9;

(LI) avermectin B1see The Pesticide Manual, 11thed., (1997), The British Crop Protection Council, London, page 3;

(LII) plant extract having activity against insects, especially (2R,6aS,12aS)-1,2,6,6a,12,12A-hexahydro-2-Isopropenyl-8,9-dimethoxypropane[3,4-b]furo[2,3-h]chromen-6-he(rotenone), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, CTR; and the extract of Azadirachta indica, primarily azadirachtin, see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, p.59; and

(LIII) a composition comprising possessing activity against insects, nematodes, preferably Heterorhabditis bacteriophora and Heterorhabditis megidis, see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str; Steinernema feltiae, see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str, and Steinernema scapterisci, see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(LIV) the composition obtained from Bacillus subtilis, cm. The Pesticide Manual, 11eed. (1997), The British Crop Protection Council, London, p.72; or the as the basis of a strain of Bacillus thuringiensis with the exception of the compounds selected from GC91 or NCTC11821; The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, p.73;

(LV) a composition comprising possessing activity against insects, fungi, preferably Verticillium lecanii, see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str; Beauveria brogniartii, cm. The Pesticide Manual, 11thed., (1997), The British Crop Protection Council, London, p.85; and Beauveria bassiana, see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, p.83;

(LVI) a composition comprising possessing activity against insect viruses, preferably Neodipridon Sertifer NPV, see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str; Mamestra brassicae NPV, cm. The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, CTR; and the virus of Cydia pomonella granulosis, see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str.291;

(CLXXXI) 7-chloro-2,3,4α,5-tetrahydro-2-[methoxycarbonyl(4-trifloromethyl)carbarnoyl]indole[1,2e]oxazoline-4-carboxylate (DPX-MP062, indoxacarb), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, str;

(CLXXXII) N'-tert-butyl-N'-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzoate (RH-2485, methoxyfenozide), see The Pesticide Manual, 11-eed., (1997), The British Crop Protection Council, London, CTR; and

(CLXXXIII) isopropyl ether (N'-[4-methoxybiphenyl-3-yl]-hydrazinecarboxamide acid (D 2341), see Brighton Crop Protection Conference, 1996, 487-493;

(R2) Book of Abstracts. 212th ACS National Meeting, Orlando, FL, August 2529 (1996), AGRO-020. Publisher: American Chemical Society, Washington, D.C. CONEN: 63BFAF.

In accordance with the foregoing, another important object of the present invention are combined composition of drugs designed to combat parasites on warm-blooded animals, characterized in that they contain in addition to the compounds of formula I at least one active ingredient having the same or different mechanism of action, and at least one physiologically acceptable carrier. The present invention is not limited dvukhkomponentnye combinations.

As a rule, anthelmintic compositions according to the invention contain from 0.1 to 99 wt.%, preferably from 0.1 to 95 wt.% the active substance of the formula I, Ia or mixtures thereof, from about 99.9 to 1 wt.%, preferably from 99,8 to 5 wt.%, solid or liquid excipients, including from 0 to 25 wt.%, first of all, from 0.1 to 25 wt.% surface-active substances.

Method of irrigation or point of application involves the application of the compounds of formula I on the limited area of the skin or hair, preferably on the back of the neck or along the spine of the animal. This is implemented by, for example, by applying a composition for irrigation or point of application with a brush or by spraying on a relatively small area wool, with which the active substance is distributed on bernuy area wool almost automatically as a result of the presence in the composition of the components, conducive to the spread that occurs as a result of the movement of the animal.

Compositions for irrigation or spot coating preferably contain media that contribute to the rapid spread over the surface of the skin and fur of an animal host, which is usually referred to as contributing to the spread of oils. For this purpose, suitable, for example, oil solutions; alcohol and isopropanolamine solutions, for example solutions in 2-octyldodecanol or oleilove alcohol; solutions in esters of monocarboxylic acids, such as isopropylmyristate, isopropyl, oxalic ether of laurinovoj acid, alerby ester of oleic acid, decroly ester of oleic acid, exellent, aerolef, decillia, esters of capric acid and saturated fatty alcohols with a chain length of C12-C18; solutions of esters of dicarboxylic acids, such as dibutyl phthalate, diisopropylnaphthalene, diisopropyl ether, adipic acid, di-n-adipat or solutions of esters of aliphatic acids, such as glycols. It may be appropriate to also include dispersing agent used in the pharmaceutical or cosmetic industry. Their examples are 2-pyrrolidone, 2-(N-alkyl)pyrrolidone, acetone, polyethylene glycol and its ethers and esters, propylene glycol or synthetic triglycerides.

Oil solutions include, for example, vegetable oils such as olive oil, peanut oil, sesame oil, pine oil, linseed oil or castor oil. Vegetable oil can also be in epoxydecane form. You can also apply waxes and silicone oils.

Typically, compositions for irrigation or point of application contain from 1 to 20 wt.% the compounds of formula I, from 0.1 to 50 wt.% dispersing agent and from 45 to the 98.9 wt.% the solvent.

Methods of irrigation and point of application is most preferable can be used to herd animals such as cattle, horses, sheep and pigs, in cases when it is difficult or long to process all the animals by oral or by injection. Due to its simplicity this method, of course, can also be used for all other animals, including some domestic animals or Pets, and it is convenient for pet owners, because often it can be applied without special care veterinarian.

Despite the fact that as provided in the sale of preferred compositions concentrated compositions, the end user typically uses dilute compositions.

Such compositions may also contain other ingredients such as stabilizers, defoamers, viscosity regulators, binders of veshestva adhesives, as well as other active ingredients for achieving specific effects.

Anthelmintic compositions of this type, which uses the end user, are also the object of the present invention.

According to the invention in all methods of pest control or in each of the compositions for combating animal active substances of formula I can be used in all of their steric configurations or mixtures thereof.

The invention also includes a method of preventive protection of warm-blooded animals, especially productive livestock, poultry and pet animals from parasitic helminths, which is that active substances of the formula I or compositions containing active substances administered to animals or as additives to food or in drink, or in solid or liquid form, orally or by injection, or parenteral. The invention also includes the use of compounds of the formula I according to the invention according to one of the above ways.

Below the invention is explained using examples that do not limit its scope; the term "active substance" includes compounds shown in table 1.

Below shows the compositions of the preferred compositions (% means wt.%).

Examples of compositions

1. Mulgirigala concentrates
ingredientsa)b)in)
the active ingredient25%40%50%
dodecylbenzenesulfonate calcium5%8%6%
polietilenglikolya ether of castor oil (36 moles ethyleneoxide links)5%--
polietilenglikolya ether tributyltin (30 moles ethyleneoxide links)-12%4%
cyclohexanone-15%20%
Kiselyova mixture65%25%20%

From these concentrates after dilution with water it is possible to prepare emulsions of any desired concentration.

2. Mulgirigala concentrates
ingredientsa)b)in)
the active ingredient10%8%60%
polietilenglikolya ether op (4-5 moles ethyleneoxide links)3%3%2%
dodecylbenzenesulfonate calcium3% 4%4%
polietilenglikolya ether of castor oil (35 moles ethyleneoxide links)4%5%4%
cyclohexanone30%40%15%
Kiselyova mixture50%40%15%

From these concentrates after dilution with water it is possible to prepare emulsions of any desired concentration.

3. Suspension concentrate
the active ingredient40%
ethylene glycol10%
polietilenglikolya ether of Nonylphenol (15 moles ethyleneoxide links)6%
sodium lignosulphonate10%
carboxymethylcellulose1%
37%aqueous formaldehyde solution0,2%
silicone oil in the form of a 75%aqueous emulsion0,8%
water32%

Finely ground active ingredient is thoroughly mixed with auxiliary substances. In this way receive a suspension concentrate from which after dilution with water it is possible to prepare suspensions of any desired concentration.

4. The powder mixture, dispersible in water
ingredientsa)b)in)
the active ingredient25%50%75%
sodium lignosulphonate5%5%-
oleic acid3%-5%
diisobutyldimethoxysilane sodium-6%10%
polietilenglikolya ether op (7-8 moles ethyleneoxide links)-2%-
highly dispersed silicon dioxide5%10%10%
kaolin62%27%-

The active ingredient is thoroughly mixed with auxiliary substances and crushed in an appropriate mill. Get wettable powders which can be diluted with water to obtain suspensions of the desired concentration.

5. Dusty
ingredientsa)b)
the active ingredient2%5%
highly dispersed silicon dioxide 1%5%
talc97%-
kaolin-90%

By carefully mixing the carriers with the active ingredient and grinding in the mill get ready-to-use dusty.

6. Granules
a)b)
the active ingredient5%10%
kaolin94%-
highly dispersed silicon dioxide1%-
attapulgite-90%

The active ingredient is dissolved in methylene chloride, sprayed on the carrier and the solvent is then concentrated by evaporation in a vacuum. Granules of this type can be mixed with food.

7. Granules
the active ingredient10%
sodium lignosulphonate2%
carboxymethylcellulose1%
kaolin87%

Mix the active ingredient with excipients crushed and moistened with water. This mixture ekstragiruyut and then vysushivaet air stream.

8. Granules
the active ingredient3%
polyethylene glycol (molecular weight 200)3%
kaolin94%

Finely ground active ingredient is uniformly fed into the mixer, to the kaolin moistened with polyethylene glycol. In this way receive a dust free granules coated.

9. Tablets or boluses
I active ingredient33,00%
the methylcellulose0,80%
silicic acid, vysokodispersnye0,80%
corn starch8,40%
II lactose crystal22,50%
corn starch17,00%
microcrystal, cellulose16,50%
magnesium stearate1,00%

I Methylcellulose mixed in water. After swelling of the product are added during the mixing of silicic acid and the mixture is suspended until a homogeneous state. Mix the active ingredient and the corn starch. To this mixture was added aqueous suspension and mix until pasty state. Received the th mass granularit through a sieve type 12 M and dried.

II All 4 excipient thoroughly mixed.

III Obtained at stages I and II pre-mixed and pressed, receiving tablets or boluses.

10. Injectable forms

A. Oil carrier (slow release)
1. the active ingredient0.1 to 1.0 g
peanut butterto 100 ml
2. the active ingredient0.1 to 1.0 g
sesame oilto 100 ml

Receiving: the Active substance is dissolved with stirring and optionally at low heat in oil, and after cooling, the solution is brought to the desired volume and sterile-filtered through a suitable membrane filter with openings 0,22 mm

B. mixing with the water solvent (average speed release)
the active ingredient0.1 to 1.0 g
4-hydroxymethyl-1,3-dioxolane (clearinterval)40 g
1,2-propandiolto 100 ml
the active ingredient0.1 to 1.0 g
glyceryltrinitrate40 g
1,2-propandiol100 the l

Receiving: the Active substance is dissolved with stirring in part of the solvent is brought to the desired volume and sterile-filtered through a suitable membrane filter with openings 0,22 mm

Century Water solubilized (quick release)
1. the active ingredient0.1 to 1.0 g
polyethoxysiloxane castor oil
(40 ethylenoxide links)10 g
1,2-propandiol20 g
benzyl alcohol : 1 g
water for injectionto 100 ml
2. the active ingredient0.1 to 1.0 g
polyethoxysiloxane servicemanual
(20 ethylenoxide links)8 g
4-hydroxymethyl-1,3-dioxolane (clearinterval)20 g
benzyl alcohol : 1 g
water for injectionto 100 ml

Receiving: the Active substance is dissolved in the solvents and surface-active substance and bring water to the desired volume. Sterilize by filtration through a suitable membrane filter with openings 0,22 is m

11. The solution for irrigation
A.
the active ingredient5 g
isopropylmyristate10 g
isopropanolto 100 ml
B.
the active ingredient2 g
exellent5 g
the triglyceride with an average chain length15 g
ethanolto 100 ml
Century
the active ingredient2 g
aerolef5 g
N-organic40 g
isopropanolto 100 ml

The water system also are preferred for oral administration and/or chewing.

The composition can also include additional excipients, such as stabilizers, for example, optionally epoxydecane vegetable oil (epoxydecane coconut oil, rapeseed oil or soybean oil); defoamers, typically silicone oil; preservatives; viscosity regulators; binders; and adhesives, as well as fertilizers or other chemical agents is La achieve certain effects.

In the described compositions can also add other biologically active substances or additives which are neutral with respect to compounds of formula I and have no harmful effects on the animal host, which can be processed, as well as mineral salts or vitamins.

Below the invention is explained using examples that do not limit its scope. The letter "h" refers to hours.

Examples retrieve

Example 1: [N-(5-cyano-4-cryptomaterial-2-yl)]-1-[3,5-dichlorine-2-yl]-cyclopropyl-1-carbonamide

278 mg of 1-[3,5-dichlorine-2-yl]cyclopropyl-1-carboxylic acid are dissolved at room temperature in a nitrogen atmosphere in 3.3 ml of oxalicacid add a drop of dimethylformamide and the mixture is refluxed for 2 hours After concentration by evaporation under vacuum, the residue is dissolved in 5 ml of anhydrous dichloromethane, then add 193 mg of 2-amino-5-cyano-4-cryptomaterial, then 0,46 ml diisopropylethylamine and 23.6 mg of 4-dimethylaminopyridine. The mixture is stirred for 20 h at room temperature in a nitrogen atmosphere, and then washed with a small amount of water, 25 ml of a saturated aqueous solution of sodium bicarbonate and, finally, 25 ml of saturated solution of sodium chloride. After drying the organic phase over magnesium sulfate, filtration and concentration by evaporation, the residue is cidaut on jhud-column, getting listed in the title compound with a melting point 195-197°C.

Using the above method, it is possible to obtain the compounds shown below in tables 1-3. The melting temperature is given in °C.

td align="left"> 1.54
Table 1

No.R1R3,R4N(R5)mPhys. data
1.1ClH,H03-Cl
1.2ClH,H05-Cl
1.3ClH,H05-CF3
1.4ClH,H03,5-Cl2
1.5ClH,H03-Br, 5-Cl
1.6ClH,H03-F, 5-Cl
1.7ClH,H03-Cl, 5-CF3
1.8ClH,H13-Cl
1.9C H,H15-Cl
1.10ClH,H15-CF3
1.11ClH,H13,5-Cl2
1.12ClH,H13-Br, 5-Cl
1.13ClH,H13-F, 5-Cl
1.14ClH,H13-Cl, 5-CF3
1.15Cl-CH2CH2-03-Cl
1.16Cl-CH2CH2-05-Cl
1.17Cl-CH2CH2-05-CF3
1.18Cl-CH2CH2-03,5-Cl2
1.19Cl-CH2CH2-03-Br, 5-Cl
1.20Cl-CH2CH2-03-F, 5-Cl
1.21Cl-CH2CH2-03-Cl, 5-CF3
1.22Cl-CH2CH2-13-Cl
1.23Cl-CH2CH2-15-Cl
1.24Cl-CH2CH2-15-CF3
1.25Cl-CH2CH2-13,5-Cl2
1.26Cl-CH2CH2-13-Br, 5-Cl
1.27Cl-CH2CH2-13-F, 5-Cl
1.28Cl-CH2CH2-13-Cl, 5-CF3
1.29CF3H,H03-Cl
1.30CF3H,H05-Cl
1.31CF3H,H05-CF3
1.32 CF3H,H03,5-Cl2
1.33CF3H,H03-Br, 5-Cl
1.34CF3H,H03-F, 5-Cl
1.35CF3H,H03-Cl, 5-CF3
1.36CF3H,H13-Cl
1.37CF3H,H15-Cl
1.38CF3H,H15-CF3
1.39CF3H,H13,5-Cl2
1.40CF3H,H13-Br, 5-Cl
1.41CF3H,H13-F, 5-Cl
1.42CF3H,H13-Cl, 5-CF3
1.43CF3-CH2CH2-03-Cl
1.44CF3-CH2CH2-05-Cl
1.45CF3-CH2CH2-05-CF3
1.46CF3-CH2CH2-03,5-Cl2tPL: 195-197°C
1.47CF3-CH2CH2-03-Br, 5-CltPL: 157-159°
1.48CF3-CH2CH2-03-F, 5-Cl
1.49CF3-CH2CH2-03-Cl, 5-CF3
1.50CF3-CH2CH2-13-Cl
1.51CF3-CH2CH2-15-Cl
1.52CF3-CH2CH2-15-CF3
1.53CF3-CH2CH2-13,5-Cl2
CF3-CH2CH2-13-Br, 5-Cl
1.55CF3-CH2CH2-13-F, 5-Cl
1.56CF3-CH2CH2-13-Cl, 5-CF3

Table 2

No.R1R3,R4(R5)mFistance
2.1ClN,N3-Cl
2.2ClN,N5-Cl
2.3ClN,N5-CF3tPL: 177-178°C
2.4ClN,N3,5-Cl2
2.5ClN,N3-Br, 5-Cl
2.6ClN,N3-F, 5-Cl
2.7ClN,N3-Cl, 5-CF3
2.8Cl 2CH2-3-Cl
2.9Cl-CH2CH2-5-Cl
2.10Cl-CH2CH2-5-CF3
2.11Cl-CH2CH2-3,5-Cl2
2.12Cl-CH2CH2-3-Br, 5-Cl
2.13Cl-CH2CH2-3-F, 5-Cl
2.14Cl-CH2CH2-3-Cl, 5-CF3
2.15CF3H,H3-Cl
2.16CF3H,H5-Cl
2.17CF3H,H5-CF3
2.18CF3H,H3,5-Cl2
2.19CF3H,H3-Br, 5-Cl
2.20CF3H,H3-F, 5-Cl
2.21CF3 H,H3-CL, 5-CF3
2.22CF3-CH2CH2-3-Cl
2.23CF3-CH2CH2-5-Cl
2.24CF3-CH2CH2-5-CF3
2.25CF3-CH2CH2-3,5-Cl2
2.26CF3-CH2CH2-3-Br, 5-Cl
2.27CF3-CH2CH2-3-F, 5-Cl
2.28CF3-CH2CH2-3-Cl, 5-CF3
2.29ClH,H3-Cl
2.30ClH,H5-Cl
2.31ClH,H5-CF3tPL: 192-193°C
2.32ClH,H3,5-Cl2
2.33ClH,H3-Br, 5-ClÈA;
2.34ClH,H3-F, 5-Cl
2.35ClN,N3-Cl, 5-CF3
2.36Cl-CH2CH2-3-Cl
2.37Cl-CH2CH2-5-Cl
2.38Cl-CH2CH2-5-CF3
2.39Cl-CH2CH2-3,5-Cl2
2.40C1-CH2CH2-3-Br, 5-Cl
2.41C1-CH2CH2-3-F, 5-Cl
2.42C1-CH2CH2-3-Cl, 5-CF3
2.43CF3H,H3-Cl
2.44CF3H,H5-Cl
2.45CF3H,H5-CF3
2.46CF3H,H3,5-Cl2
2.47CF3H,H3-Br, 5-Cl
2.48CF3H,H3-F, 5-Cl
2.49CF3H,H3-Cl, 5-CF3
2.50CF3-CH2CH2-3-Cl
2.51CF3-CH2CH2-5-Cl
2.52CF3-CH2CH2-5-CF3
2.53CF3-CH2CH2-3,5-Cl2
2.54CF3-CH2CH2-3-Br, 5-Cl
2.55CF3-CH2CH2-3-F, 5-Cl
2.56CF3-CH2CH2-3-Cl, 5-CF3

Table 3

No.R1R2R3, R4(R5)mPhys. data
3.1ClCH3H,H5-CF3
3.2ClCH3H,H3,5-Cl2
3.3ClCH3H,H3-Cl, 5-CF3
3.4ClCH3-CH2CH2-5-CF3
3.5ClCH3-CH2CH2-3,5-Cl2
3.6ClCH3-CH2CH2-3-Cl, 5-CF3
3.7ClWith2H5H,H5-CF3
3.8ClWith2H5H,H3,5-Cl2
3.9ClWith2H5H,H3-Cl, 5-CF3ÈA;
3.10ClWith2H5-CH2CH2-5-CF3
3.11ClWith2H5-CH2CH2-3,5-Cl2
3.12ClWith2H5-CH2CH2-3-Cl, 5-CF3
3.13ClPINES3H,H5-CF3
3.14ClPINES3H,H3,5-Cl2
3.15ClPINES3H,H3-Cl, 5-CF3
3.16ClPINES3-CH2CH2-5-CF3
3.17ClPINES3-CH2CH2-3,5-Cl2
3.18ClPINES3-CH2CH2-3-Cl, 5-CF3
3.19ClCH2With6H5H,H5-CF3
3.20ClCH2With6H5H,H3,5-Cl2
3.21ClCH2With6H5H,H3-Cl, 5-CF3
3.22ClCH2With6H5-CH2CH2-5-CF3
3.23ClCH2With6H5-CH2CH2-3,5-Cl2
3.24ClCH2With6H5-CH2CH2-3-Cl, 5-CF3
3.25ClCH2OC2H5H,H5-CF3
3.26ClCH2OC2H5H,H3,5-Cl2
3.27ClCH2OC2H5 H,H3-Cl, 5-CF3
3.28ClCH2OC2H5-CH2CH2-5-CF3
3.29ClCH2OC2H5-CH2CH2-3,5-Cl2
3.30ClCH2OC2H5-CH2CH2-3-Cl, 5-CF3
3.31ClSOOS2H5H,H5-CF3
3.32ClSOOS2H5H,H3,5-Cl2
3.33ClSOOS2H5H,H3-Cl, 5-CF3
3.34ClSOOS2H5-CH2CH2-5-CF3
3.35ClSOOS2H5-CH2CH2-3,5-Cl2
3.36ClSOOS2H5-CH2CH2-3-Cl, 5-CF3
3.37ClSOOS6H5H,H5-CF3
3.38ClSOOS6H5H,H3,5-Cl2
3.39ClSOOS6H5H,H3-Cl, 5-CF3
3.40ClSOOS6H5-CH2CH2-5-CF3
3.41ClSOOS6H5-CH2CH2-3,5-Cl2
3.42ClSOOS6H5-CH2CH2-3-Cl, 5-CF3
3.43ClSOON2With6H5H,H5-CF3
3.44ClSOON2With6H5H,H3,-Cl 2
3.45ClSOON2With6H5H,H3-Cl, 5-CF3
3.46ClSOON2With6H5-CH2CH2-5-CF3
3.47ClSOON2With6H5-CH2CH2-3,5-Cl2
3.48ClSOON2With6H5-CH2CH2-3-Cl, 5-CF3
3.49ClSOS6H5H,H-5-CF3
3.50ClSOS6H5H,H3,5-Cl2
3.51ClSOS6H5H,H3-Cl, 5-CF3
3.52ClSOS6H5-CH2CH2-5-CF3
3.53ClSOS6 H5-CH2CH2-3,5-Cl2
3.54ClSOS6H5-CH2CH2-3-CL, 5-CF3
3.55ClCONHC2H5H,H5-CF3
3.56ClCONHC2H5H,H3,5-Cl2
3.57ClCONHC2H5H,H3-Cl, 5-CF3
3.58ClCONHC2H5-CH2CH2-5-CF3
3.59ClCONHC2H5-CH2CH2-3,5-Cl2
3.60ClCONHC2H5-CH2CH2-3-Cl, 5-CF3
3.61CF3CH3H,H5-CF3
3.62 CF3CH3H,H3,5-Cl2
3.63CF3CH3H,H3-Cl, 5-CF3
3.64CF3CH3-CH2CH2-5-CF3
3.65CF3CH3-CH2CH2-3,5-Cl2
3.66CF3CH3-CH2CH2-3-Cl, 5-CF3tPL: 133-135°
3.67CF3With2H5H,H5-CF3
3.68CF3With2H5H,H3,5-CF3
3.69CF3With2H5H,H3-Cl, 5-CF3
3.70CF3With2H5-CH2CH2-5-CF3
3.71CF3With2H5-CH2CH2-3,5-Cl2
3.72CF3With2H5-CH2CH2-3-Cl, 5-CF3tPL: 127-130°
3.73CF3PINES3H,H5-CF3
3.74CF3PINES3H,H3,5-Cl2
3.75CF3PINES3H,H3-Cl, 5-CF3
3.76CF3PINES3-CH2CH2-5-CF3
3.77CF3PINES3-CH2CH2-3,5-Cl2
3.78CF3PINES3-CH2CH2-3-Cl, 5-CF3
3.79CF3CH2With H5N,N5-CF3
3.80CF3CH2With6H5N,N3,5-Cl2
3.81CF3CH2With6H5N,N3-Cl, 5-CF3
3.82CF3CH2With6H5-CH2CH2-5-CF3
3.83CF3CH2With6H5-CH2CH2-3,5-Cl2
3.84CF3CH2With6H5-CH2CH2-3-Cl, 5-CF3tPL: 149-151°
3.85CF3CH2OS2H5N,N5-CF3
3.86CF3CH2OS2H5N,N3,5-Cl2
3.87CF3CH2OS2 H5N,N3-Cl, 5-CF3
3.88CF3CH2OS2H5-CH2CH2-5-CF3
3.89CF3CH2OS2H5-CH2CH2-3,5-Cl2
3.90CF3CH2OS2H5-CH2CH2-3-Cl, 5-CF3
3.91CF3SOOS2H5N,N5-CF3
3.92CF3SOOS2H5N,N3,5-Cl2
3.93CF3SOOS2H5N,N3-Cl, 5-CF3
3.94CF3SOOS2H5-CH2CH2-5-CF3
3.95CF3SOOS2H5-With the 2CH2-3,5-Cl2
3.96CF3SOOS2H5-CH2CH2-3-Cl, 5-CF3
3.97CF3SOOS6H5N,N5-CF3
3.98CF3SOOS6H5N,N3,5-Cl2
3.99CF3SOOS6H5N,N3-Cl, 5-CF3
3.100CF3SOOS6H5-CH2CH2-5-CF3
3.101CF3SOOS6H5-CH2CH2-3,5-Cl2
3.102CF3SOOS6H5-CH2CH2-3-Cl, 5-CF3
3.103CF3SOON2With6H5N,N 5-CF3
3.104CF3PINES2With6H5N,N3,5-Cl2
3.105CF3COOCl2With6H5N,N3-Cl, 5-CF3
3.106CF3SOON2With6H5-CH2CH2-5-CF3
3.107CF3SOON2With6H5-CH2CH2-3,5-Cl2
3.108CF3SOON2With6H5-CH2CH2-3-Cl, 5-CF3
3.109CF3SOS6H5N,N5-CF3
3.110CF3SOS6H5N,N3,5-Cl2
3.111CF3SOS6H5N,N3-Cl, 5-CF3
3.112CF3SOS6H5-CH2CH2-5-CF3
3.113CF3SOS6H5-CH2CH2-3,5-Cl2
3.114CF3SOS6H5-CH2CH2-3-Cl, 5-CF3
3.115CF3CONHC2H5N,N5-CF3
3.116CF3CONHC2H5N,N3,5-Cl2
3.117CF3CONHC2H5N,N3-Cl, 5 - CF3
3.118CF3CONHC2H5-CH2CH2-5-CF3
3.119CF3CONHC2H5-CH2CH2-3,5-Cl2
3.120C 3CONHC2H5-CH2CH2-3-Cl, 5-CF3
3.121ClCH3N,N5-CF3
3.122ClCH3N,N3,5-Cl2
3. 123ClCH3N,N3-Cl, 5-CF3
3.124ClCH3-CH2CH2-5-CF3
3.125ClCH3-CH2CH2-3,5-Cl2
3.126ClCH3-CH2CH2-3-Cl, 5-CF3
3.127ClWith2H5N,N5-CF3
3.128ClWith2H5N,N3,5-Cl2
3.129ClWith2H5 N,N3-Cl, 5-CF3
3.130ClWith2H5-CH2CH2-5-CF3
3. 131ClWith2H5-CH2CH2-3.5-Cl2
3.132ClWith2H5-CH2CH2-3-Cl, 5-CF3
3.133ClPINES3N,N5-CF3
3.134ClPINES3N,N3,5-Cl2
3.135ClPINES3N,N3-Cl, 5-CF3
3.136ClPINES3-CH2CH2-5-CF3
3.137ClPINES3-CH2CH2-3,5-Cl2
3.138ClPINES3 -CH2CH2-3-Cl, 5-CF3
3.139ClCH2With6H5N,N5-CF3
3.140ClCH2With6H5N,N3,5-Cl2
3.141ClCH2With6H5N,N3-Cl, 5-CF3
3.142ClCH2With6H5-CH2CH2-5-CF3
3.143ClCH2With6H5-CH2CH2-3,5-Cl2
3.144ClCH2With6H5-CH2CH2-3-Cl, 5-CF3
3.145ClCH2OC2H5N,N5-CF3
3.146ClCH2OC2H5N,N3,5-Cl2ÈA;
3.147ClCH2OC2H5N,N3-Cl, 5-CF3
3.148ClCH2OC2H5-CH2CH2-5-CF3
3.149ClCH2OC2H5-CH2CH2-3,5-Cl2
3.150ClCH2OC2H5-CH2CH2-3-Cl, 5-CF3
3.151ClSOOS2H5N,N5-CF3
3.152ClSOOS2H5N,N3.5-Cl2
3.153ClSOOS2H5N,N3-Cl, 5-CF3
3.154ClSOOS2H5-CH2CH2-5-CF3
3.155ClSOOS2H5-The n 2CH2-3,5-Cl2
3.156ClSOOS2H5-CH2CH2-3-Cl, 5-CF3
3,157ClSOOS6H5N,N5-CF3
3.158ClSOOS6H5N,N3,5-Cl2
3.159ClSOOS6H5N,N3-Cl, 5-CF3
3.160ClSOOS6H5-CH2CH2-5-CF3
3.161ClSOOS6H5-CH2CH2-3,5-Cl2
3.162ClSOOS6H5-CH2CH2-3-Cl, 5-CF3
3.163ClSOON2With6H5N,N5-CF3
3.164 ClSOON2With6H5N,N3,5-Cl2
3.165ClSOON2With6H5N,N3-Cl, 5-CF3
3.166ClSOON2With6H5-CH2CH2-5-CF3
3.167ClSOON2With6H5-CH2CH2-3,5-Cl2
3.168ClSOON2With6H5-CH2CH2-3-Cl, 5-CF3
3.169ClSOS6H5N,N5-CF3
3.170ClSOS6H5N,N3,5-Cl2
3.171ClSOS6H5N,N3-Cl, 5-CF3
3.172ClSOS6H5-CH2CH2 -5-CF3
3.173ClSOS6H5-CH2CH2-3,5-Cl2
3.174ClSOS6H5-CH2CH2-3-Cl, 5-CF3
3.175ClCONHC2H5N,N5-CF3
3.176ClCONHC2H5N,N3,5-Cl2
3.177ClCONHC2H5N,N3-Cl, 5-CF3
3.178ClCONHC2H5-CH2CH2-5-CF3
3.179ClCONHC2H5-CH2CH2-3,5-Cl2
3.180ClCONHC2H5-CH2CH2-3-Cl, 5-CF3
3.181CF3 CH3N,N5-CF3
3.182CF3CH3N,N3,5-Cl2
3.183CF3CH3N,N3-Cl, 5-CF3
3.184CF3CH3-CH2CH2-5-CF3
3.185CF3CH3-CH2CH2-3,5-Cl2
3.186CF3CH3-CH2CH2-3-Cl, 5-CF3
3.187CF3With2H5N,N5-CF3
3.188CF3With2H5N,N3,5-Cl2
3.189CF3With2H5N,N3-Cl, 5-CF3
3.190 3With2H5-CH2CH2-5-CF3
3.191CF3With2H5-CH2CH2-3,5-Cl2
3.192CF3With2H5-CH2CH2-3-Cl, 5-CF3
3.193CF3PINES3N,N5-CF3
3.194CF3PINES3N,N3,5-Cl2
3.195CF3PINES3N,N3-Cl, 5-CF3
3.196CF3PINES3-CH2CH2-5-CF3
3.197CF3PINES3-CH2CH2-3,5-Cl2
3.198CF3PINES3-CH2CH2- 3-Cl, 5-CF3
3.199CF3CH2With6H5N,N5-CF3
3.200CF3CH2With6H5N,N3,5-Cl2
3.201CF3CH2With6H5N,N3-CL, 5-CF3
3.202CF3CH2With6H5-CH2CH2-5-CF3
3.203CF3CH2With6H5-CH2CH2-3,5-Cl2
3.204SRHCH2With6H5-CH2CH2-3-Cl, 5-CF3
3.205CF3CH2OC2H5N,N5-CF3
3.206CF3CH2OC2H5N,N3,5-Cl2
3.207CF3CH2OC2H5N,N3-Cl, 5-CF3
3.208CF3CH2OC2H5-CH2CH2-5-CF3
3.209CF3CH2OC2H5-CH2CH2-3,5-Cl2
3.210CF3CH2OC2H5-CH2CH2-3-Cl, 5-CF3
3.211CF3SOOS2H5N,N5-CF3
3.212CF3SOOS2H5N,N3,5-Cl2
3.213CF3SOOS2H5N,N3-Cl, 5-CF3
3.214CF3SOOS2H5-CH2CH2-5-CF3
3.215CF3SOOS2H5-CH2CH2-3,5-Cl2
3.216CF3SOOS2H5-CH2CH2-3-Cl, 5-CF3
3.217CF3SOOS6H5N,N5-CF3
3.218CF3SOOS6H5N,N3,5-Cl2
3.219CF3SOOS6H5N,N3-Cl, 5-CF3
3.220CF3SOOS6H5-CH2CH2-5-CF3
3.221CF3SOOS6H5-CH2CH2-3,5-Cl2
3.222CF3SOOS6H5-CH2CH2-3-Cl, 5-CF3
3.223CF3 SOON2With6H5N,N5-CF3
3.224CF3SOON2With6H5N,N3,5-Cl2
3.225CF3SOON2With6H5N,N3-Cl, 5-CF3
3.226CF3SOON2With6H5-CH2CH2-5-CF3
3.227CF3SOON2With6H5-CH2CH2-3,5-Cl2
3.228CF3SOON2With6H5-CH2CH2-3-Cl, 5-CF3
3.229CF3SOS6H5N,N5-CF3
3.230CF3SOS6H5N,N3,5-Cl2
3.231CF3 SOS6H5N,N3-Cl, 5-CF3
3.232CF3SOS6H5-CH2CH2-5-CF3
3.233CF3SOS6H5-CH2CH2-3,5-Cl2
3.234CF3SOS6H5-CH2CH2-3-Cl, 5-CF3
3.235CF3CONHC2H5N,N5-CF3
3.236CF3CONHC2H5N,N3,5-Cl2
3.237CF3CONHC2H5N,N3-Cl, 5-CF3
3.238CF3CONHC2H5-CH2CH2-5-CF3
3.239 is available for downloadCF3CONHC2H5-CH2CH2- 3,5-Cl2
3.240CF3CONHC2H5-CH2CH2-3-Cl, 5-CF3

Biological examples.

1. Activity in vivo against Trichostrongylvs colubriformis and At contortus on clawed Mongolian gerbils (Meriones unguiculatus) using subcutaneous injection

6-8-week-old Mongolian gerbis infect simultaneously by artificial feeding approximately 2000 larvae of the third age as T. colubriformis and H. contortus. After 6 days after infection of gerbils subjected to light anaesthesia with N2O and treated by subcutaneous injection in the neck region of the test compound, dissolved in a mixture consisting of 2 parts DMSO and 1 part of polyethylene glycol 400, 100, 32, and 10 - 0.1 mg/kg On the ninth day (3 days after treatment), when a large part of the N. contortus is still on the 4th larval stage, and a large part of T. colubriformis is immature imaginal stage, gerbils kill in order to count the number of worms. Efficiency in % reduction in the number of worms in each gerbil, comparing with the geometric mean number of worms found 8 infected and untreated gerbils.

In this experiment established that by means of compounds of the formula I achieved a noticeable reduction of infection by nematodes.

Almost similar result was obtained by oral administration of the active substance.

2. Insecticidal intestinal activity against Spodoptera littoralis

All experienced grown in pot culture of the cotton plant at the stage 5 leaves sprayed with a solution of acetone/water containing 1, 3, 12.5 or 50 part./million test the connection.

Then after obtained when the spray coating has dried, the plants infect approximately 30 larvae (first instar (L1)) Spodoptera littoralis. For each test compound and each option are used for 2 plants. The experience is carried out at a temperature of about 24°C and relative humidity of 60%. Interim and final evaluation of the mortality of adult insects, larvae and caused by pogrizli damage carried out after 24, 48 and 72 hours

It is established that the compounds of formula I cause a total loss after 24 h at the concentrations applicable only 3 part./million

3. Activity against phyto-toxic ticks

Sensitive to organophosphorus insecticides Tetranychus urticae

On the primary leaves of bean (Phaseolus vulgaris) for 16 h before the experiment placed a piece of leaf, which is used for mass cultivation of T. urticae. After removal of this piece of sheet plants infected all stages of development of cle is her sprayed until dripping a solution of the test compound containing 0.2, 0.4 or 1.6 to frequent./million test connection. The temperature in the greenhouse is about 25°C. After 7 days using a microscope to assess the percentage of loss of mobile stages (adults and nymphs) and eggs.

It is established that the compounds of formula I cause a total loss when using the current concentration of 0.4 ppm million

4. Activity against larvae of the first instar (L1) Lucilia sericata

1 l of the aqueous suspension of the test compound is mixed with 3 ml of medium for growth of larvae at a temperature of about 50°receiving the homogenate containing the active substance 250 or 125 ppm million In each tube for the experiment placed approximately 30 larvae Luculia (L1).

After 4 days, determine the level of mortality. It is established that the compounds of formula I cause 100%loss when using the current concentration of 250 ppm million

5. Acaricidal activity against Boophilus microplus (line Biarra)

The piece of tape is attached horizontally to the sheet of PVC so that it is in a number of backs side by side, you could host 10 sucked the blood of the female ticks Boophilus microplus (line Biarra). With a needle for injection each tick injected 1 µl of fluid. The liquid is a mixture 1:1 of ethylene glycol and ACET is on and in it dissolve a certain amount of active substance per 1, of 0.1 or 0.01 μg per tick. Control ticks injected by the injection of a solution without active substance. After processing mites survive under normal conditions in the insectary at a temperature of about 28°C and relative humidity 80% up to egg laying and hatching of eggs, nymphs of the first age of the control ticks. The activity of test compounds evaluated using IR90, i.e. determining the dose of the active substance, in which 9 out of 10 female ticks (=90%) lay eggs, from which even after 30 days are not hatched nymphs.

Value IR90the tested compounds of the formula I is 0.1 µg.

6. Efficacy in vitro against sucked the blood of the female ticks Boophilus microplus (line BIARRA):

Spend four series of experiments, each of which use 10 sucked the blood of adult female mites resistant to organophosphorus insecticides line BIARRA, which is glued to the sticky tape and closed for 1 h with a cotton swab impregnated with an aqueous suspension or emulsion of the test compound in a concentration of 500, 125, 31 and 8 ppm million assessment of the experience carried out after 28 days, determining the level of mortality, the number of laid eggs and the number of hatched larvae.

To evaluate the activity of test compounds using the following criteria:

- the number of females that quickly died to uklady the project for eggs;

- the number of females that did not die within a certain time, but not laid eggs;

- the number of cases when there was the deposition of eggs, but in which there was no formation of embryos;

- the number of cases when there was the deposition of eggs, and they were led embryos, of which no developed larvae;

the number of cases when the embryos were led, one has been developed larvae, which revealed no anomalies for 26-27 days.

In this experiment established that the compounds of formula I induce rapid death of more than 80% of female ticks.

7. Contact action against Aphis craccivora

The pea seedlings infested by all stages of aphids, spray with a solution of the active substance prepared from mulgirigala concentrate, using if necessary a solution with a concentration of active substance 50, 25 or 12.5 ppm million Through evaluation after 3 days, determine died or fell from plants more than 80% of aphids. Only this level of activity is classified as efficiency.

It is established that the compounds of formula I caused a total loss (=100%) at a concentration of 12.5 ppm million

8. Larvicide activity against Aedes aegypti

The amount of 0.1%aqueous acetone solution of the active substance sufficient to obtain the required concentrations of 10, 3.3-or 16 ppm million, add by pipette onto the surface of 150 ml of water in the container. After evaporation of the acetone in the container make about 30-40 3-day-old larvae of Aedes. Mortality determined after 1, 2 and 5 days.

In this experiment established that the compounds of formula I at a concentration of 1.6 ppm million cause the complete destruction of all the larvae just after 1 day.

9. Efficacy in vivo against adult fleas Clenocephalides felis in domestic cats after oral administration

Test compounds administered orally before or after a meal domestic cats in a gelatin capsule, dose is 0.5-20 mg/kg After 1, 3, 7 and 10 days after treatment for each cat put about 100 fleas (about 50 males and about 50 females), depending on the result of the previous infestation by fleas.

Effectiveness (% reduction in the number of fleas) is determined based on the number of live fleas found after combing of wool within 10 min after 1 day after each new infected fleas; however, the efficiency in % corresponds to the average value of the number of live fleas on control animals minus the number of live fleas on treated animals divided by the average number of live fleas on control animals and multiplied by 100.

Paralyzed fleas found in the cells of cats and combed out of the wool is, collected and placed into a thermostat with a temperature of 28°C and relative humidity 70% and after 24 h to determine the number of survivors/victims insects. If the majority of paralyzed fleas were killed, then the test compound is considered as imagie for fleas, and if the majority of fleas survived, it is considered that the connection has the ability to cause knockdown.

In this experiment established that the compounds of formula I called at 80%mortality of fleas.

10. Efficacy in vivo against adult fleas Ctenocephalides felis in domestic cats after point processing

The tested compounds by spot application of treated domestic cats, the dose is 0.5-10 mg/kg After 1, 3, 7 and 10 days after treatment for each cat put about 100 fleas (about 50 males and about 50 females), depending on the result of the previous infestation by fleas.

Effectiveness (% reduction in the number of fleas) is determined based on the number of live fleas found after combing of wool within 10 min after 1 day after each new infected fleas; however, the efficiency in % corresponds to the average value of the number of live fleas on control animals minus the number of live fleas on treated animals divided by the average number of live fleas on to ntalnyh animals and multiplied by 100.

Paralyzed fleas found in the cells of cats and combed wool, collected and placed into a thermostat with a temperature of 28°C and relative humidity 70% and after 24 h to determine the number of survivors/victims insects. If the majority of paralyzed fleas were killed, then the test compound is considered as imagie for fleas, and if the majority of fleas survived, it is considered that the connection has the ability to cause knockdown.

In this experiment established that the compounds of formula I cause the death of more than 90% of the fleas 35 days.

11. Efficacy in vitro against nymphs mblyomm hebraeum

About 5 hungry nymphs placed in polystyrene laboratory test tube containing 2 ml of solution, suspension or emulsion of the test compound.

After immersion for 10 min and shaking during 2x10 in vibration experienced mixer tubes closed with dense cotton swab and rotate. After all the liquid is absorbed with a cotton swab push it to the middle of the experimental tubes, which continue to rotate, resulting in most of the fluid is squeezed out of the cotton swab and flows down to below the Petri dish.

Experienced test tubes and then to assess incubated at room temperature in the room in daylight. After 14 days experienced tubes pogruzhaet a beaker with boiling water. If ticks are starting to react to the heat, believe that the test compound has no activity in the studied concentration, otherwise the mites are dead, and the test compound is considered active in the studied concentration. All compounds studied in concentrations from 0.1 to 100 ppm million

This experience revealed that the tested compounds of formula I cause the death of more than 80% of the ticks.

12. Activity against Dermanyssus gallinae

Into the open top of the container make 2-3 ml of a solution containing 10 ppm million active substance and about 200 mites (Dermanyssus gallinae)at different stages of development. Then the container is closed with a cotton swab, shaken for 10 min until complete wetting of ticks, then briefly turned to full absorption of the test solution with a cotton swab. After 3 days, determine the mortality of mites, counting the number of dead individuals and Express it in %.

It is established that the compounds of formula I possess high activity against Dermanyssus gallinae.

13. Activity against Musca domestica

A lump of sugar cube-shaped handle with a solution of the test compound so that the concentration of the test compound in the Sahara after drying over night was 250 ppm million This processed piece of sugar put in al minieval Cup with a damp piece of cotton wool which contribute 10 adults resistant to organophosphorus insecticides strain of Musca domestica, serves a laboratory beaker and incubated at 25°C. After 24 h to determine mortality.

In this experiment established that the compounds of formula I possess high activity against Musca domestica.

1. The compounds of formula

where R1denotes halogen or C1-C6haloalkyl;

R2denotes hydrogen, C1-C6alkyl or (C1-C6alkylene)phenyl;

X1denotes N;

X2denotes C(CN);

X3means Of;

Q represents CH;

R3and R4independently of one another denote hydrogen or together with the carbon atom to which they are bound, form a3-C7cycloalkyl ring;

R5denotes a Deputy selected from the group comprising C1-C6haloalkyl, halogen, and, if m is greater than 1, the substituents R5may be the same or different;

m denotes 1, 2 or 3; and

n denotes 0 or 1.

2. Method of producing compounds of the formula I according to claim 1, consisting in the fact that the compound of the formula

which is known or which can be obtained analogically known compounds, and in which R1, R2X1and X2have the meanings specified for formula I, is subjected to the interaction with the compound of the formula

which is known or which can be obtained analogously to corresponding known compounds and in which X3, R3, R4, R5, m, n and Q have the meanings indicated for formula I, Z represents a leaving group, optionally in the presence of a basic catalyst, the mixture of enantiomers, which can be obtained as a result of this process, share and produce the desired enantiomer of the compounds of formula I.

3. Composition for combating pests which comprises as active ingredient at least one compound of formula I according to claim 1 in combination with carriers and/or dispersing agents.

4. The compounds of formula I according to claim 1 for pest control.

5. Method of pest control, which consists in the fact that effective as a pesticide, the amount of at least one of the compounds of formula I according to claim 1 handle pests or their habitat.

6. The compounds of formula I according to claim 1 for combating parasites of warm-blooded animals.

7. The compounds of formula I according to claim 1 for the preparation of pharmaceutical compositions intended to combat parasites.



 

Same patents:

FIELD: organic chemistry, chemical technology, agriculture.

SUBSTANCE: invention describes substituted azadioxocycloalkenes of the general formula (I): wherein A means unsubstituted or methyl-substituted dimethylene; Ar means unsubstituted or fluorine-substituted ortho-phenylene, thiophendiyl or pyridindiyl; E means group of the formula: wherein G means oxygen atom, groups -O-CH2-, -CH2-O- or -C(CH3)=N-O-CH2-; Z means unsubstituted or substituted phenyl, pyrimidinyl or thiadiazolyl, or naphthyl. Invention describes 4 methods for preparing compounds of the formula (I), 5 species of intermediate compounds used for preparing compounds of the formula (I), fungicide agents comprising compound of the formula (I) as an active substance, a method for preparing fungicide agents, method for control of harmful fungi using compound of the formula (I). Compounds of the formula (I) show fungicide properties and therefore they can be used in agriculture.

EFFECT: improved preparing methods, valuable properties of compounds.

13 cl, 5 tbl, 18 ex

FIELD: organic chemistry.

SUBSTANCE: method relates to new method for production of 5-chloro-4-[(2-imidazoline-2-yl)amino]-2,1,3-benzothiadiazole hydrochloride of formula I . Claimed compound is high effective drug and is used in medicine as myorelaxant of central action. Claimed method includes condensation of N,N-dimethyldichloromethyleneammonium chloride with 5-chloro-4-amino-1,1,3-benzothiadiazole in organic solvent followed by treatment of formed alpha-chloroformamidine of formula R-N=C(Cl)N(CH3)2, wherein R is 5-chloro-2,1,3-benzothiazol-4-yl, with ethylenediamine. Formed intermediate of formula R-N=C(NH-CH2-CH2-NH2)N(CH3)2 is treated with hydrochloric acid, heated in organic solvent and 5-chloro-4-[(2-imidazoline-2-yl)amino]-2,1,3-benzothiadiazole hydrochloride of formula I is isolated.

EFFECT: simplified method for preparation of target compound directly in hydrochloride form.

FIELD: pharmaceutical industry, medicine.

SUBSTANCE: invention relates to 5-membered N-heterocyclic compounds and salts thereof having hypoglycemic and hypolipidemic activity of general formula I , wherein R1 is optionally substituted C1-C8-alkyl, optionally substituted C6-C14-aryl or optionally substituted 5-7-membered heterocyclic group, containing in ring 1-4 heteroatoms selected from oxygen, sulfur and nitrogen; or condensed heterocyclic group obtained by condensation of 5-7-membered monoheterocyclic group with 6-membered ring containing 1-2 nitrogen atoms, benzene ring, or 5-membered ring containing one sulfur atom; { is direct bond or -NR6-, wherein R6 is hydrogen atom or C1-C6-alkyl; m = 0-3, integer; Y is oxygen, -SO-, -SO2- or -NHCO-; A ring is benzene ring, condensed C9-C14-aromatic hydrocarbon ring or 5-6-membered aromatic heterocyclic ring containing 1-3 heteroatoms selected from oxygen and nitrogen, each is optionally substituted with 1-3 substituents selected from C7-C10-aralkyloxy; hydroxyl and C1-C4-alkoxy; n = 1-8, integer; B ring is nitrogen-containing 5-membered heterocycle optionally substituted with C1-C4-alkyl; X1 is bond, oxygen or -O-SO2-; R2 is hydrogen atom, C1-C8-alkyl, C7-C13-aralkyl or C6-C14-aryl or 5-6-membered heterocyclic group containing in ring 1-3 heteroatoms selected from oxygen, sulfur and nitrogen, optionally substituted with 1-3 substituents; W is bond, C1-C20-alkylene or C1-C20-alkenylene; R3 is -OR8 (R8 is hydrogen or C1-C4-alkyl) or -NR9R10 (R9 and R10 are independently hydrogen or C1-C4-alkyl). Compounds of present invention are useful in treatment of diabetes mellitus, hyperlipidemia, reduced glucose tolerance, and controlling of retinoid-associated receptor.

EFFECT: new medicines for treatment of diabetes mellitus, hyperlipidemia, etc.

26 cl, 518 ex, 3 tbl

FIELD: organic chemistry, pharmaceutical composition.

SUBSTANCE: new isoindoline-1-on-glucokinase activators of general formula I , as well as pharmaceutically acceptable salts or N-oxide thereof are disclosed. In formula A is phenyl optionally substituted with one or two halogen or one (law alkyl)sulfonyl group, or nitro group; R1 is C3-C9cycloalkyl; R2 is optionally monosubstituted five- or six-membered heterocyclic ring bonded via carbon atom in cycle to amino group, wherein five- or six-membered heteroaromatic ring contains one or two heteroatoms selected form sulfur, oxygen or nitrogen, one of which is nitrogen atom adjacent to carbon atom bonded to said amino group; said cycle is monocyclic or condensed with phenyl via two carbon atoms in cycle; said monosubstituted with halogen or law alkyl heteroaromatic ring has monosubstituted carbon atom in cycle which in not adjacent to carbon atom bonded to amino group; * is asymmetric carbon atom. Claimed compounds have glucokinase inhibitor activity and useful in pharmaceutical composition for treatment of type II diabetes.

EFFECT: new isoindoline-1-on-glucokinase activators useful in treatment of type II diabetes.

23 cl, 3 dwg, 43 ex

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

SUBSTANCE: invention relates to derivatives of heteroarylalkylpiperazine of the general formula (I):

wherein m = 1, 2 or 3; q means NH or oxygen atom (O); R1, R2, R3, R4 and R5 are taken independently among the group including hydrogen atom, (C1-C15)-alkyl, OR20 wherein R20 represents hydrogen atom; R6, R7 and R8 represent hydrogen atom; R9, R10, R11, R12, R13, R14, R15 and R16 are taken independently among the group including hydrogen atom, (C1-C4)-alkyl; or R9 and R10 in common with carbon atom to which they are joined form carbonyl group; R17 means heteroaryl that is taken among the group including indolyl, benzoxazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, pyridyl, benzopyrazinyl substituted optionally with 1-2 substitutes taken among the group including hydrogen atom, CF3 group, (C1-C8)-alkyl, phenyl, CON(R20)2. Compounds elicit property as a partial inhibitor of oxidation of fatty acids and can be used in therapy for protection of skeletal muscles against results of muscular or systemic diseases. Also, invention describes a pharmaceutical composition based on the claimed compounds.

EFFECT: valuable medicinal properties of compounds.

39 cl, 3 tbl, 25 ex

The invention relates to organic chemistry and can find application in medicine

The invention relates to new derivatives of nitrogen-containing heterocyclic compounds of the formula

or their pharmaceutically acceptable salts, where R1represents H, COCOR2, COOR3or SO2R3, R2is1-6alkyl, C1-6alkenyl,5-7cycloalkyl, 2-thienyl, 3-thienyl, phenyl or substituted phenyl, R3is phenylalkyl,represents a saturated five-membered nitrogen-containing heterocyclic ring with one nitrogen atom or benzododecinium saturated six-membered nitrogen-containing heterocyclic ring;is oxazol, oxadiazole or thiazole, And is associated with carbon atom of the five-membered heteroaromatic rings and represents COO(CH2)mAr,where R1has the values listed above or is CONR4(CH2)mAr or (CH2)mO(CH2)nAr and R1cannot be COCOR2or SO2R3, R4represents H or<

The invention relates to sulfhemoglobinemia heterocyclic compound represented by formula (I), its pharmaceutically acceptable salts and their hydrates

where the values of A, B, K, T, W, X, Y, U, V, Z, R1specified in paragraph 1 of the claims

The invention relates to new and nitrate salts of compounds of formulas (I) to(VI), which can be used in medicine for the treatment of bone disorders such as abnormalities in bone and joints
The invention relates to a method for producing 5-chloro-4-/(2-imidazolin-2-yl)amino/-2,1,3-benzothiadiazole the hydrochloride by hydrochlorination 5-chloro-4-/(2-imidazolin-2-yl)amino/-2,1,3-benzothiadiazole of concentrated hydrochloric acid in the environment of ethyl alcohol at 20-35With target product is separated from the reaction mixture by dilution with water, heating to 75-80With that clarification of the resulting solution activated carbon, cooling the clarified solution to 0-2With, then the selected product is filtered, washed with alcohol and dried at 70C in vacuum (120 mm RT.CT.) get 5-chloro-4-/(2-imidazolin-2-yl)amino/-2,1,3-benzothiadiazole hydrochloride with a melting point 292-294C (with decomposition) and mass fractions of the main substance of at least 99.8%, the product yield is 80% on the original basis

The invention relates to new compounds of the formula (I) or their salts, where X, Y independently is hydrogen, halogen; Z is oxygen; Q is chosen among the Q1-Q9described in the claims and containing heterocycles with nitrogen, and sulfur; Ar is pyridyl, pyrimidyl, pyridazinyl, triazolyl, thiazolyl, isothiazole or phenyl, or pyridyl, pyrimidyl, pyridazinyl, triazolyl, thiazolyl, isothiazole or phenyl substituted with up to five substituents, when Q - Q3or Q6substituted phenyl is excluded

The invention relates to benzylchloride formula I or its salts, where R1- (C1-C6)alkyl, (C1-C4)cianelli, (C1-C4)hydroxyalkyl, (C3-C6)cycloalkyl, (C1-C6)halogenated, benzyl which may be substituted with halogen, thiazolyl; R2and R3independently - H, (C1-C4)alkyl, or R1and R2together with the sulfur atom and the carbon form a 3-8-membered ring; R4- H, halogen; And - hydrazinoacetate or hydrosonography group of formula A1 or A2; R9- H, halogen, NO2, CN, (C1-C4)alkyl, (C1-C4)halogenated, (C1-C4)alkoxy, (C1-C4)halogenoalkane, (C1-C4)alkylthio, (C1-C4)allogenicity, (C2-C4)alkylsulfonyl, (C1-C4)halogenated.sulphonated, phenyl which may be substituted with halogen, phenoxy, which may be substituted with halogen; R10- H; R11, R12, R13independently - H, (C1-C6)alkyl, (C1-C4)halogenated, (C2-C10)alkoxyalkyl, (C3-C8)alkoxyalkyl, (C2-C6)alkylthiol, (C1-C4)cianelli, benzyl which may be substituted with halogen, (C1-C4)halogenation, (C1-C4)alkyl, -COR14, -COOR15THAT IS SOP(R16R17, -SO2R20-C(R21)= HR22; or R12and R13together can form a group of the formula = CR23R24; R14- (C1-C20)alkyl, (C1-C8)halogenated, (C2-C12)alkoxyalkyl,oxyalkyl, phenyl; R16- H, (C1-C4)alkyl; R17- H, (C1-C6)alkyl, phenyl which may be substituted; R20- (C1-C4)halogenated, (C2-C4)dialkylamino; R21- (C1-C6)alkyl; R22- acyl, (C2-C6)alkoxycarbonyl; R23, R24independently - H, halogen, (C1-C6)alkyl, -NR25R26; R25and R26independently - H, (C1-C4)alkoxy, (C2-C12)alkoxyalkyl; Q1and Q2is nitrogen or CR9m = 1 to 3, n = 0, 1, 2

The invention relates to a means to control weeds, in particular to the herbicide agent containing as an active ingredient (A) nitrile 1-(3-chloro-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyridine-2-yl)-5-(methylpropylamine)-4-pyrazolecarboxylate acid, and optionally, as an active ingredient (B) a substance selected from the group comprising bentazon, molinet, Diuron, thiobencarb, butachlor, pretilachlor, timepart, fenoxaprop-ethyl, clomipram, cinmetacin, bromobutyl, chinkara, mefenacet, pyrazosulfuron-ethyl, asbroker, chinaculture, tanishlar, cumyluron, MK 243, nitroanilide, anilofos, belforest, bifenox, SN-900, MSRA, nitrofen, oxadiazon, pendimethalin, simetryn, sulcotrione (SA), trifluralin, piperophos, perimutter, ethoxysulfuron, benzylbromide, pyrazolate, paradoxien, benzefoam, cycloaliphatic, cyhalofop, NBA-061 and azimsulfuron

The invention relates to new chemical substances, which can be a fungicidal active substance means, in particular to Amida alkoxybenzenes acid, fungicidal tool and method of controlling fungal diseases of plants

The invention relates to ether compounds and their use

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

FIELD: organic chemistry, pesticides, agriculture.

SUBSTANCE: invention relates to compounds that elicit high pesticide activity and can be used in control of pests of domestic and agricultural animals. Indicated compounds show the formula (I):

wherein R1 means halogen atom, (C1-C6)-halogenalkyl; R2 means hydrogen atom (H), (C1-C6)-alkyl, (C1-C6)-alkylene-phenyl; X1 means nitrogen atom (N); X2 means group C(CN); X3 means oxygen atom (O); Q means CH; R3 and R4 mean independently of one another hydrogen atom (H) or in common with carbon atom with which they are bound form (C3-C7)-cycloalkyl ring; R5 means a substitute taken among group including (C1-C6)-halogenalkyl, halogen atom being if m above 1 then substitutes R5 can be similar or different; m = 1, 2 or 3; n = 0 or 1. Also, invention describes a method for their preparing and method for control of pests.

EFFECT: valuable pesticide properties of compounds.

7 cl, 3 tbl, 14 ex

Up!