Derivative benzothiophen-2-carboxamide-s,s-dioxide, the retrieval method, fungicidal and microbicide tool

 

(57) Abstract:

Usage: in order to protect plants from pathogenic microorganisms and fungal diseases. The inventive derivative benzothiophen-2-carboxamide S, S-dioxide of the formula I

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where R1is unsubstituted or substituted alkyl, alkenyl or quinil, unsubstituted or substituted cycloalkyl or cycloalkenyl or unsubstituted or substituted arakyl, aralkyl, aralkyl or aryl; R2is a hydrogen atom or unsubstituted or substituted alkyl, or R1and R2together with the nitrogen atom to which they relate, signify unsubstituted or substituted heterocycle, and R3, R4, R5and R6independently from each other mean a hydrogen atom, a halogen atom, a cyano, a nitro-group, alkyl, alkoxygroup, allylthiourea, halogenated, halogenlampe or halogenation, fungicidal, and the composition of microbicide based on them. 3 S. and 1 C.p. f-crystals, 7 PL.

The invention relates to new benzothiophen-2-carboxamide-S,S-dioxides having valuable properties, in particular to derive benzothiophen-2-carboxamide - S,S-dioxide of the General formula I

< / BR>
where

R1unbranched or branched ALK is or alkoxycarbonyl with 1 to 8 carbon atoms in each alkyl part, unbranched or branched alkenyl with 2 to 12 carbon atoms, unbranched or branched quinil with 2 to 12 carbon atoms or unsubstituted or once to six times substituted by alkyl cyclohexyl or cyclohexylmethyl, unsubstituted or once to fivefold substituted in the phenyl part of the same or different substituents phenyl, phenylalkyl or phenylalkyl with 1 to 12 carbon atoms in each unbranched or branched alkyl or alkenylphenol parts, and as the substituents of the phenyl can be called a halogen atom, hydroxyl, cyano, formylamino, unbranched or branched alkyl, alkoxygroup with 1 to 4 carbon atoms, unbranched or branched halogenated, halogenlampe with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, unbranched or branched, dialkylamino, alkylsulphonyl, alkylcarboxylic, alkoxycarbonyl, aminocarbonyl, N-alkylaminocarbonyl, N,N-dialkylaminoalkyl, formylamino, alifornian;

R2a hydrogen atom or an unbranched or branched alkyl with 1 to 18 carbon atoms, unsubstituted or singly or multiply substituted by the same or different for the together with the nitrogen atom, to which they relate, signify unsubstituted or singly or multiply substituted, saturated five - to semicolony a heterocycle, which may contain in addition to the nitrogen atom, an oxygen atom and a Deputy may be alkoxycarbonyl with 1 to 4 carbon atoms;

R3, R4, R5and R6independently from each other mean a hydrogen atom, halogen atom, alkoxygroup with 1 to 6 carbon atoms.

New derivatives of benzothiophene-2-carboxamide-S,S-dioxide above General formula (I) receive due to the fact that the compound of General formula II

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where

R1, R2, R3, R4, R5and R6have the above meanings, is subjected to the interaction with the oxidizing agent, if necessary, in the environment of a diluent.

Suddenly the proposed benzothiophen-2-carboxamide-S, S-dioxides of the General formula (I) have a better fungicidal action than the known benzothiophen-2-carboxamide-S, S-dioxide according to the application DE N 3832848, for example, 3-chloro-N-(1-phenylethyl)-benzothiophen-2-carboxamide-S, S-dioxide. Furthermore, they are clearly the best of microbicide action than the known compound 3-(1-imidazolyl)-N-(1-phenylethyl)-benzothiophen-2 - carboxamide-S,S-dioxide and 3-methylthio-N-(1-is derived benzothiophen-2-carboxamide-S,S - dioxide above General formula (I) p. 1, in which R1branched or unbranched alkyl with 1 to 6 carbon atoms, cyclohexyl, phenyl, phenylalkyl substituted once or twice by halogen, alkoxyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, R2a hydrogen atom, lower alkyl; R3, R4, R5, R6independently from each other hydrogen atom, halogen atom.

In the case of using as the starting compound, for example, anilide benzothiophen-2-carboxylic acid, and the oxidizing agent hydrogen peroxide, the reaction of the proposed method can be described using the following schema:

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Used for the implementation of the proposed method benzothiophen-2-carboxamide or known, or they can get similar known methods.

As the oxidant for the implementation of the proposed method can be used with all commonly used for oxidation of sulfur oxidizers. It is preferable to use hydrogen peroxide or organic nagkalat, for example, peracetic acid, 4-nitromidazole acid or 3-chlormadinone acid, or inorganic oxidizing agents such as, for example, nationality acid, potassium permanganate or chromic acid.

If necessary, the proposed method can be carried out in the presence of an auxiliary agent. As an auxiliary agent can be used with all commonly used organic and inorganic agents, binding acid. Preferably use hydroxides, acetates or carbonates of alkaline or alkaline-earth metals such as calcium hydroxide or sodium, sodium acetate or sodium carbonate.

If necessary, the proposed method can be carried out in the presence of a suitable catalyst. As a catalyst can be used with all commonly used for such okislenii sulfur catalysts. Preferably used to implement in a large range of temperature.

Usually the interaction is carried out at a temperature from -30oC to +100oC, preferably from 0oC to +80oC.

To implement the proposed method on the mole benzothiophen-2-carboxamide of General formula (II) typically use 2.0 to 10.0 mol, preferably 2.0 to 5.0 mol oxidant, if appropriate, 1.0 to 1.3 mol of the base used as an auxiliary agent, and, if appropriate, 0.001 to 1.0 mol, preferably from 0.005 to 0.05 mole of catalyst.

Interaction, processing and selection of target products is carried out using known methods.

Offer active substances have a strong action against pests and can in practice be used for controlling undesirable harmful organisms. Thus, these active substances are suitable, e.g. for applications in plant protection, in particular as a fungicide funds.

In the field of plant protection fungicidal agent used to combat plasmodiophoromycota, oamietta, chytridiomycetes, zygomaticum, Ascomycetes, basidiomycetes and deuteromycetes.

In addition to the described actions against pathogens in plants predlagamom, known in the protection of materials. Therefore, the proposed substances are perfectly suited for the protection of technical materials.

Under the technical material in this context refers to materials produced for use in the technique. As technical materials, using the proposed substances to be protected from alteration or destruction by microbes can be called adhesives, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants fluids and other materials, smitten and destroyed by microorganisms. Among the protected materials should also be called part of the production plants, for example, the cooling circuits that can be damaged by the multiplication of microorganisms. In the framework of the present invention as technical materials first considers adhesives, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and liquid paths of the cooling medium.

As microorganisms that can cause destruction or modification of technical materials, can be called, naprimer activity directed against fungi, in particular moulds, causing discoloration of the wood mushrooms and destructive tree mushrooms (basidiomycetes), as well as against the mucous membranes of organisms and algae.

Depending on their physical and/or chemical properties of the proposed connection can be translated in the usual form of application, for example, solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, small conclusion in polymeric materials, or shell for the treatment of seed, as well as in preparations intended for finest distribution and used for production of cold or warm mist.

These drugs get known techniques, for example, by mixing the active substances with solvents, i.e. liquid solvents, pressurized liquefied gases and/or solid carriers, if appropriate using surface-active agents, i.e. agents, emulsification and/or dispersion and/or forming foam funds. In the case of using water as a diluent it is also possible to use organic solvents such as alcohols, as an auxiliary solvent. As a liquid the bathrooms aromatic compounds or chlorinated aliphatic hydrocarbons as, e.g. the chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons, e.g. cyclohexane or paraffins, e.g. gasoline or other petroleum fractions, alcohols, e.g. ethanol, isopropanol, butanol, benzyl alcohol or glycol and their ethers and esters, ketones, e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as, e.g. dimethylformamide or dimethylsulfoxide, and water. By liquefied gaseous diluents or carriers are meant such liquids at room temperature and under atmospheric pressure are in the gas state, e.g. working gases for spray aerosols as, for example, halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. As a solid carrier can be used, e.g. natural mine flour as, e.g. kaolin, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic mine flour as, e.g. highly dispersed silicic acid, alumina and silicates. As a solid carrier for granules can be used, e.g. broken and fractionated natural rocks such as, for example, ka is and granules of organic material, for example, sawdust, Solopov coconut, corn cobs and stalks of tobacco. As agent for emulsifying and/or foam can be used, for example, nonionic and anionic emulsifiers, e.g. complex polyoxyethylenic a fatty acid ester, a simple polyoxyethylene ether of fatty alcohol series as, e.g. simple alkylarylsulphonates ether, alkyl sulphonates, arylsulfonate and the products of hydrolysis of proteins, and as a means of dispersion can be used, for example, exhaust lignin-sulphite lye or methylcellulose.

The preparations can contain adhesion agents such as carboxymethylcellulose, natural and synthetic polymers in the form of a powder, granular or latex as, for example, gum Arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as Catalina and lecithins, and synthetic phospholipids. In addition, the additives can be mineral and vegetable oils.

The preparations may contain colouring agents, e.g. inorganic pigments such as, e.g. iron oxide or titanium or ferocity blue, and organic dyes such as, for example, alizarin dyes, azo dyes and metallic is it, molybdenum or zinc.

In General, the preparations contain 0.1 to 95 wt. the active substance, preferably 0.5 to 90%

Offer active substances may be present in the preparations in the form of a mixture with other known active substances, for example, fungicides, insecticides, acaricides and herbicides, and also as mixtures with fertilizers or growth regulators.

The active substance can be used as such, in the form of drugs or derived from these preparations, for example, in the form of ready to use solutions, suspensions, powders, and means for spraying, pastes, soluble powders and granules. The application is carried out in a known manner, for example by casting, raspryskivanii, atomization, dispersion, foaming, smears, etc. in Addition, the active substance can be applied by finest distribution, or by injection contains the active drug substance or the active substances in the soil. The active substance is also suitable for processing seed.

When processing parts of plants, the concentration of the active substance can vary in drugs in a wide range. Usually it is between 1 and 0.0001 wt. predpochtitelnei, lying between 0.001 and 50 g per kg of seed, preferably between 0.01 and 10 g

For soil required concentration of active substance in the range of 0.0001 to 0.1 wt. preferably of 0.001 to 0.02 wt.

Microbicide funds usually contain the active substance in quantities of 1

95%, preferably 10 75%

The concentration of the active substance in a particular application depends on the type and population of microorganisms, as well as on the composition of the protected material. The optimal applied amount can be determined by test series. In General, the concentration of use is in the range from 0.001 to 5%, preferably from 0.05 to 1.0% by weight of the protected material.

When used as a means to protect the materials proposed active substances can also be in the form of a mixture with other known active substances.

In addition, the compounds of formula (I) have good activity against microbes, in particular antifungal activity. They are especially active against wide range of fungi, in particular against dermatophytes and sprout mushrooms, and biphasic fungi.

The present invention also includes Asia one or several active substances, or consisting of one or several active substances.

In addition, the present invention encompasses pharmaceutical products in ready to use form. This means that the preparations are in the form of separate units, for example, tablets, pills, capsules, pills, suppositories and ampoules, the content of active substances which may correspond to a certain percentage or multiple of an individual dose. Finished unit may contain, for example, 1, 2, 3 or 4 individual doses or half, third or quarter individual doses. Preferably one individual dose contains the active substance corresponding to a daily dose or half, third or quarter of the daily dose.

Under non-toxic, inert pharmaceutically portable media refers to solid, semi-solid or liquid diluents, fillers and excipients of any kind.

As the preferred pharmaceutical preparations include, for example, tablets, pills, capsules, pills, granules, suppositories, solutions, suspensions and emulsions, pastes, ointments, gels, creams, lotions, powders or sprays.

Tablets, pills, capsules is APR. (a) fillers or diluents such as, for example, starches, lactose, sucrose, glucose, mannitol and silicic acid, (b) binders, e.g. carboxymethylcellulose, alginates, gelatine and polyvinylpyrrolidone, (C) stabilizers humidity as, e.g. glycerol (g) softeners as, for example, talc, calcium stearate and magnesium and solid polyethylene glycols, (d) the dissolution retarders, as for example, paraffin, (f) resorption accelerators such as, for example, Quaternary ammonium compounds, (g) wetting as, for example, cetyl alcohol and glycerol monostearate, (h) promote the absorption of substances such as, for example, kaolin and bentonite, and other excipients as, for example, agar-agar, calcium carbonate and sodium bicarbonate, or mixtures mentioned under (a) to (I) substances.

Tablets, coated tablets, capsules, pills and granules can be provided with customary coatings and shells, if necessary, containing pigments, and their composition can be chosen so that the active substance or active substances completely or preferably released only in a certain part of the intestinal tract, in case of necessity slow and the quality of the mass use, for example, polymeric substances and wonam the form of one or more of the foregoing carriers.

Suppositories can contain, along with one or more active substances conventional soluble and water-insoluble carriers, such as polyethylene glycols and fats such as, for example, cocoa oil and high esters as, for example, ester of the alcohol with 14 carbon atoms and a fatty acid with 16 carbon atoms or mixtures of these substances.

Ointments, pastes, creams and gels along with one or more active substances may contain conventional carriers, for example, animal and vegetable oils, waxes, paraffins, starch, tragant, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicic acid, talc and zinc oxide, or mixtures of these substances.

Powders and aerosols along with one or more active substances may contain conventional carriers, for example, lactose, talc, silicic acid, aluminium hydroxide, calcium silicate and polyamide powder or mixtures of these substances, and sprays can additionally contain customary working environment, for example, chlorinated and fluorinated hydrocarbons.

Solutions and emulsions along with one or more active substances may contain conventional carriers, for example, solvents, zamedlitel Silovye alcohol, the benzyl benzoate, propylene glycol, 1,3-butyleneglycol, dimethylformamide, oils, in particular cottonseed oil, peanut oil, corn oil, olive oil, castor oil and sesame oil, glycerol, clearinterval, tetrahydrofurfuryl alcohol, polyethylene glycol and an ester of a fatty acid sorbitan or mixtures of these substances.

For parenteral giving the solutions and emulsions can be sterile and gemotologicakim.

Suspension along with one or more active substances may contain conventional carriers, such as liquid diluents such as, for example, water, ethyl alcohol, propyl alcohol, suspendresume means as, for example, ethoxylated isostearyl alcohols, esters of polyoxyethylenesorbitan and polyoxyethylenesorbitan, microcrystalline cellulose, metaservices aluminum, bentonite, agar-agar and tragant or a mixture of these substances.

These preparations may also contain dyes, preservatives and improve the smell and taste of funds, for example peppermint oil and eucalyptus oil, and sweet substances such as saccharin.

therapeutically active compounds should contain Easy the whole mixture.

In addition, the above-mentioned means, along with the proposed active substances may contain further pharmaceutically active substances.

The above pharmaceutical medications get known by according to known methods, for example, by mixing one or more active substances with one or more carriers.

The present invention also relates to the use of active substances and containing one or more of these substances, pharmaceutical preparations for the prevention, alleviation and/or treatment of the above diseases in medicine and veterinary.

The active substance or pharmaceutical preparations suitable for local, oral, parenteral, intraperitoneal and/or rectal villas, preferably parenteral villas, in particular intravenous villas.

In General and in medicine and in veterinary medicine to achieve the desired effect, it is expedient to give the proposed active substance in a total quantity of about 1 to 200 mg, preferably from about 5.0 to 150 mg per kg of body weight per day, if necessary, in the form of several individual doses.

In the case of oral villas offer active in the day, and in the case of parenteral villas in total amount of about 1 to 50 mg, preferably from 2.5 to 25 mg per kg of body weight per day.

However, depending on the species and body weight treat human or animal, the type and severity of the disease, type of drug, and giving medicines, as well as period or period of villas may be necessary to deviate from the indicated doses. Thus, in some cases it may be sufficient cottage is less than the specified amounts of the active substance, while in other cases, you must give more than the specified number. On the basis of their expert knowledge will be able to determine the required and optimal in a particular case, the dose and type of villas active substances.

Obtaining new compounds of General formula (I) is illustrated in the following example.

Example 1.

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6 g (0,0237 mol) anilide benzothiophen-2-carboxylic acid and 9.3 g (0,0947 mol) of 35% aqueous hydrogen peroxide solution dissolved in 47 ml of glacial acetic acid, and stirred at a temperature of 50oC for 20 hours For processing water is added, the precipitation is sucked off, washed twice with water and then dried.

Obtain 5.5 g (82% of theory) of S,S-dioxide is soedineniya

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To 8 g (0,0407 mol) of acid chloride of benzothiophen-2-carboxylic acid in 150 ml of toluene at room temperature with stirring 7.6 g (0,0814 mol) of aniline. After the addition, continue to stir at a temperature of 50oC for 5 h, then the reaction mixture was poured into water, the precipitated precipitate is sucked off, washed twice with water and dried.

Obtain 7.9 g (77% of theory) of anilide benzothiophen-2-carboxylic acid with a melting point of 188oC.

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To 57,5 g (0,324 mol) benzothiophen-2-carboxylic acid in 600 ml of chlorobenzene at a temperature of phlegmy with stirring, add drops of 57.8 g (0,468 mol) of thionyl chloride. After the addition, continue to stir at a temperature of phlegmy until the generation of gas. For processing the reaction mixture is allowed to cool to room temperature, then concentrated in vacuo, the residue is stirred with n-hexane, the precipitated precipitate is sucked off and dried.

Get 57.4 g (90% of theory) of acid chloride of benzothiophen-2-carboxylic acid, which can be used for further reactions without additional purification.

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84 g (0,438 mol) of a compound methyl ether benzothiophen-2-carboxylic acid in 218 ml of ethanol is mixed with 36,8 the promotional mix is allowed to cool, the ethanol is then removed in vacuo, the aqueous residue was washed with simple diethyl ether, acidified by adding diluted hydrochloric acid, the precipitated precipitate is sucked off, washed with water and dried.

Get 60.1 g (77% of theory) benzothiophen-2-carboxylic acid with a melting point above 220oC.

Analogously to example 1 and according to the information gain is given in table. 1 benzothiophen-2-carboxamide-S,S-dioxides of the General formula I.

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In table. 1 the following abbreviations: n, normal structure; i izotropnye; t, tertiary; s secondary.

The following examples illustrate how the properties of the new compounds of the formula (I).

Example 147. Experience with Venturia (Apple) / protective effect.

For obtaining appropriate for the drug 1 wt.h. the active substance is mixed with 4.7 wt.h. acetone and 0.3 wt.h. simple alkylarylsulphonates ether, and the resulting concentrate is diluted with water to the desired concentration of the active substance.

To determine the protective activity, young plants are sprayed with containing the active drug substance to the formation of droplets. After drying, the layer of herb inoculant with an aqueous suspension of theC and a relative humidity of 100% in one day.

Then the plants transferred to the greenhouse, where they are stored at a temperature of 20oC and a relative humidity of approximately 70%

After 12 days after inoculation evaluate the results of experience.

Active substances, their concentration in the preparations and the experimental results are summarized in the following table. 2.

Example 148. Experience with Leptosphaeria nodorum (wheat) / protective effect.

For obtaining appropriate for the drug 1 wt.h. the active substance is mixed with 100 wt.h. of dimethylformamide and 0.25 wt.h. simple alkylarylsulphonates ether, and the resulting concentrate is diluted with water to the desired concentration of the active substance.

To determine the protective activity, young plants are sprayed with containing the active drug substance to humidity. After drying of the layer of deposited drug plants are sprayed with a spore suspension Leptospaeria nodorum. Plants left to stand in an incubation chamber at a temperature of 20oC and a relative humidity of 100% for two days.

Then the plants transferred to the greenhouse, where they are stored at a temperature of approximately 15oC and relative plaintive substances, their concentration in the preparations and the experimental results are summarized in the following table. 3.

Example 149. Experience in antifungal activity in vitro.

Experiments on activity in vitro was carried out by inoculation of spores using average 5103up to 104spores per ml of substrate. As the nutrient medium used for dermatophytes and moulds, environment milieu epreuve d" Sabourad; for yeast broth with glucose.

The incubation temperature was 28 37oC, and the incubation period of 24 to 96 h for yeasts and 96 h for dermatophytes and moulds.

Active substances, their concentration in the preparations and the experimental results are summarized in the following table. 4.

Example 150. For explanation of activity against fungi and bacteria below the image defined minimum concentration of inhibition proposed benzothiophen-2-carboxamide-S,S-dioxides.

From beer wort and peptone (fungi) or meat extract and peptone (bacteria) receive agar, to which is added offer of the active substance in a concentration from 0.1 mg/l to 5000 mg/L. After solidification of agar add pure cultures are shown in the following table. 5 test organisms. Store at temperature is the minimum concentration of inhibition. The minimum concentration of inhibition is the concentration at which there is no propagation of the microorganisms.

Active substances, their concentration in the preparations and the experimental results are summarized in the following table. 5.

Example 151. Experience with Cochliobolus sativus (barley)/protective effect.

For obtaining appropriate for the drug 1 wt.h. the active substance is mixed with 100 wt.h. of dimethylformamide and 0.25 wt.h. simple alkylarylsulphonates ether, and the resulting concentrate is diluted with water to a concentration of the active substances listed in table. 6.

To determine the protective effect of young plants are sprayed with containing the active drug substance to the formation of droplets. After drying, the layer of herb inoculant water suspension of conidia of Cochliobolus sativus and leave to stand in the incubation chamber at a temperature of 20oC and a relative humidity of 100% within 48 hours

Then the plants transferred to the greenhouse, where they are stored at a temperature of 20oC and a relative humidity of approximately 80%

Upon expiration of 7 days after inoculation evaluate the results of experience.

The asset is ytophtora (tomatoes)/protective effect.

For obtaining appropriate for the drug 1 wt.h. the active substance is mixed with 4.7 wt.with. acetone and 0.3 wt.h. simple alkylarylsulphonates ether, and the resulting concentrate is diluted with water to a concentration of the active substances listed in table. 7.

To determine the protective effect of young plants are sprayed with containing the active drug substance to the formation of droplets. After drying, the layer of herb inoculant water suspension of conidia Phytophtora infestans and leave to stand in the incubation chamber at a temperature of 20oC and a relative humidity of 100% for 3 days, after which evaluate the results of experience.

Active substances, their concentration in the preparations and the experimental results are summarized in table. 7.

Given the above data on the activity of the new derivatives benzothiophen-2-carboxamide-S, S-dioxide of the formula (V) is a further object of the invention is a fungicidal and microbicide agent, containing in addition to the standard target additives as active substance a compound of General formula (I)

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where

R1unbranched or branched alkyl with 1 to 6 carbon atoms, haloalkyl, alkoxyalkyl is once or twice substituted by halogen and/or alkyl with 1 to 4 carbon atoms, phenyl, substituted alkoxyl with 1 to 4 carbon atoms, phenylalkyl with 1 to 4 carbon atoms in the alkyl part, unsubstituted or substituted once or twice by halogen, alkoxyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms;

R2a hydrogen atom, lower alkyl;

R3, R4, R5, R6independently from each other hydrogen atom, halogen atom, or alkoxy with 1 to 6 carbon atoms, in an effective amount.

The proposed tool is illustrated by the following examples.

Example 153. 5 wt.h. the active substance according to example 6 are mixed with 95 wt. including flour, natural rocks and the resulting mixture is finely pulverized. The obtained pulverized product can be applied to plants or their habitat.

Example 154. 50 wt.h. the active substance of example 1 is mixed with 1 wt. including dibutyldithiocarbamate, 4 wt.h. ligninsulfonate, 8 mass.h. highly dispersed silicic acid and 37 wt.h. flour natural rocks and the resulting mixture is pulverized to obtain a powder. The resulting wettable powder before use, mix with water, taken in sufficient quantity to establish the desired concentration of the active substance.

Patem as an emulsifier to add a 10 weight. parts of the mixture dodecylbenzenesulfonate calcium and nonylphenolethoxylates ether. The resulting emulsion concentrate before use, dilute with water to the desired concentration of the active substance.

Example 156. To 91 wt.h. sand particle size of 0.5 to 1.0 mm successively added 2 wt.h. spun oil and 7 wt.h. a powder mixture consisting of 75 weight. parts of the active substance according to example 16 and 25 wt.h. flour natural rocks. The resulting mixture is treated in the mixer until a homogeneous free flowing and non-dusting granulate, which in sufficient quantity can be scattered on the plants or their habitat.

1. Derivative benzothiophen-2-carboxamide-S,S-dioxide of the General formula I

< / BR>
where R1unbranched or branched alkyl with 1 to 20 carbon atoms, unbranched or branched halogenated, cianelli, oxyalkyl, alkoxyalkyl or alkoxycarbonyl with 1 to 8 carbon atoms in each alkyl part, unbranched or branched alkenyl with 2 to 12 carbon atoms, unbranched or branched quinil with 2 to 12 carbon atoms, unsubstituted or once to six times substituted by alkyl cyclohexyl or College and substituents phenyl, phenylalkyl or phenylalkyl with 1 to 12 carbon atoms in each unbranched or branched alkyl or alkenylphenol parts, and as the substituents of the phenyl can be called a halogen atom, hydroxyl, cyano, hormonetherapy, unbranched or branched alkyl, alkoxygroup with 1 to 4 carbon atoms, unbranched or branched halogenated, halogenlampe with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, unbranched or branched, dialkylamino, alkylsulphonyl, alkylcarboxylic, alkoxycarbonyl, aminocarbonyl, N-alkylaminocarbonyl, N,N-dialkylamino carbonyl, formylamino, alifornian;

R2a hydrogen atom or an unbranched or branched alkyl with 1 to 18 carbon atoms, unsubstituted or singly or multiply substituted by identical or different substituents from the group comprising hydroxyl group, a halogen atom, a cyano;

R1and R2together with the nitrogen atom to which they relate, signify unsubstituted or singly or multiply substituted, saturated five - to semicolony a heterocycle, which may contain in addition to the nitrogen atom, an oxygen atom and a Deputy may bitesnich a hydrogen atom, halogen atom, alkoxygroup with 1 to 6 carbon atoms.

2. The method of obtaining derivatives benzothiophen-2-carboxamide-S,S-dioxide of the General formula I on p. 1, characterized in that the compound of General formula II

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where R1, R2, R3, R4, R5and R6have the above values,

subjected to interaction with the oxidizing agent, if necessary, in the environment of a diluent.

3. Derivative benzothiophen-2-carboxamide-S,S-dioxide of the General formula I under item 1, in which R1branched or unbranched alkyl with 1 to 6 carbon atoms, cyclohexyl, phenyl, phenylalkyl substituted once or twice by halogen, alkoxyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, R2a hydrogen atom, a lower alkyl, R3, R4, R5, R6independently from each other hydrogen atom, halogen atom, possessing fungicidal and microbicide activity.

4. Fungicidal and microbicide remedy containing the active substance, derived benzothiophen-2-carboxamide-S,S-dioxide and the target additives, characterized in that as the derived benzothiophen-2-carboxamide-S,S-dioxide it contains a compound of General formula I

< / BR>
where R1nerazvit the th 1 to 6 carbon atoms in the alkyl part, cyclohexyl, phenyl, unsubstituted or once or twice substituted by halogen and/or alkyl with 1 to 4 carbon atoms, phenyl, substituted alkoxyl with 1 to 4 carbon atoms, phenylalkyl with 1 to 4 carbon atoms in the alkyl part, unsubstituted or substituted once or twice by halogen, alkoxyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms;

R2a hydrogen atom, lower alkyl;

R3, R4, R5, R6independently from each other hydrogen atom, halogen atom or alkoxy with 1 to 6 carbon atoms,

in an effective amount.

 

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< / BR>
in particular 1,3-bis(2'-hydroxy-3'-morpholinopropan)-6-methyluracil(a); 1,3-bis(2'-hydroxy-3'-piperidinoethyl)-6-stands-rallu (b); 3-bis(2'-hydroxy-3'-morpholinopropan)-5-hydroxy-6-methyluracil (); 1,3-bis(2'-hydroxy-3'-piperidinoethyl)- 5-hydroxy-6-methyluracil (g); 1,3-bis(2'-hydroxy-3'-morpholinopropan)-5-(2'-hydro - XI-3'-morpholinoethoxy)-6 - methyluracil (d) and 1,3-bis(2'-hydroxy-3'-piperidinoethyl)-5-(2'-hydroxy-3'-piperidino - poxy)- 6-methyluracil (E), showing immunotropic and anti-inflammatory activity

- aminoacyl)-5,10-dihydro-11h-dibenzo[b, e] [1,4]- diazepin-11-ons or their salts, possess antiarrhythmic activity" target="_blank">

The invention relates to the field of chemistry, particularly to the new series of compounds - 5-(-aminoacyl)-5,10-dihydro-11N - dibenzo [b,e]-[1,4]-diazepin-11-Onam General formula

where R1is a hydrogen atom or chlorine;

R2is a hydrogen atom or a C1-C2-alkyl;

R3- C1-C2-alkyl or cyclohexyl, or R2and R3together with the nitrogen atom can be morpholinyl or N-methylpiperazine balance; provided that, if R2is a hydrogen atom, R3can be1-C3-alkyl or cyclohexyl,

n=3-6;

m = 0-1; X=Cl or Br

The invention relates to new biologically active chemical compounds, namely, to derive a cyclic amide of the formula I

R1-(CH2)n-Z,

where R1group cyclic amide, such as 2H-3,4-dihydro-1,3-benzoxazin-2-she, 2H-3,4-dihydro-1,3-benzoxazin-2,4-dione, and 1,2,3,4-tetrahydroquinazoline-2,4-dione, and 1,2,3,4-tetrahydroquinazolin-2-it, 1,2,3,4-tetrahydropyrido(3,2-d)-pyrimidine-2,4 - dione, and 1,2,3,4-tetrahydropyrido(3,2-d)pyrimidine-2-it, 1,2,3,4-tetrahydropyrimidine-2,4-dione, pyrrolidin-2-it, 1,2,3,4 - tetrahydropyridine-2-it, 5H-6,7,8,9-tetrahydropyrido(3,2-b)azepin-6-she N-5,6,7,8-tetrahydropyrido(2,3-b)azepin - 8-she, 2H-3,4-dihydropyrido(2,3-e)-1, 3-oxazin-2-thione or 2-she pyrrolidine (3,4-b)-pyrazin-5-she 1H-2,3,4,5-tetrahydrothieno(2,3-b)indol-2-it, 8H-4,5,6,7-tetrahydrothieno(2,3-b)thiophene-7-she 4H-pyrazolo(5,4-f)benzazepin-9-it, isoindoline-1,3-dione, benzoxazolyl-2-it, unsubstituted or substituted lower alkyl, lower alkoxy, halogen, the nitro-group, carboxy, benzoyl or benzyl, n is zero or an integer from 1 to 6, Z is a group of formula (A) or (B):

N-(CH2)mR2(A) or -(CH2)p, dioxolane, furan, tetrahydrofuran, methylfuran or thiophene, m is an integer from 1 to 3; R3is lower alkyl; R4is phenyl or a radical of dioxolane, furan or thiophene, p = 1, provided that when R1radical 1,2,3,4-tetrahydrobenzo-2-or 1,2,3,4-tetrahydroquinazoline-2,4-dione, R2and R4are not phenyl or substituted by a halogen phenyl, or their pharmacologically acceptable salts with antiacetylcholinesterase activity

The invention relates to new derivatives of arylsulfonamides having, in particular, valuable pharmacological properties, more particularly to a derivative of arylsulfonamides General formula (I)

< / BR>
where R1benzyl, thienyl, chloranil, tetramethylene pentamethylbenzyl, phenyl, unsubstituted or monosubstituted by a halogen atom, a nitro-group, stands, metaxylem or trifluoromethyl, phenyl, disubstituted by chlorine atoms or methoxypropane,

R2a hydrogen atom, methyl,

R3pyridyl,

R4and R5hydrogen atoms or together denote a carbon-uglerodnoi communication,

R6hydroxyl, methoxyl,

A group of the formula

< / BR>
where R7and R8a hydrogen atom or together denote a methylene or ethylene group

X N-methyl-aminogroup or sulfur atom, and the group-CHR7associated with the group-NR2-,

B a carbon-carbon bond or unbranched Allenova group with 2-4 carbon atoms,

their mixtures, isomers or individual isomers and physiologically tolerated additive salts with bases, if R6means hydroxyl, which

The invention relates to the field of chemistry of biologically active substances, which may have application in medicine
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