Derivative amide

 

(57) Abstract:

Usage: as an agricultural fungicide for control of plant diseases. The inventive 2-(2,4-dimethylthiazol-5-carboxamido)-2-(2-furyl)acetonitrile, so pl. 108 - 109C, yield 74% 2-(2,4-dimethylthiazol-5-carboxamido)-2-(3-furyl) acetonitrile, so pl. 94 - 96C, yield 74% 2-(2,4-dimethylthiazol-5-carboxamido)-2-(2-thienyl)acetonitrile, so pl. of 127.5 - 128,5C, yield 65%. 1 C. p. F.-ly, 11 PL.

The invention relates to new derivatives of Amida, receiving and containing agricultural fungicides.

As prevailing agricultural fungicides for control of plant diseases caused by mold, such as Pythiaccae and peronosporaceae, genus peronospora known Captan, captafol, dithiocarbamate and so on. However, they all have a preventive effect and hardly have a curative effect. This fungicidal activity is insufficient for control of plant diseases at the stage of after-ripening of phytopathogenic fungi. This is a disadvantage, because depending on the circumstances sometimes require the use of fungicides after the initial development of phytopathogenic fungi. Therefore, there always exists a significant need to change the activity, such as healing effects. This is especially important for control of plant diseases, with a quick manifested by symptoms such as caused Peronosporales. Recently, for this purpose, metalaxyl, i.e., N-(2,6-dimetilfenil)-N-(methoxyacetyl)ELA - Nina methyl ester, with excellent systemic activity and showing good curative effect. However, since the resistance of organisms to metalaxyl decreased soon after its commercialization, its curative effect could not be appreciated. Under these circumstances there is a need for new fungicides with excellent systemic activity and showing a permanent healing effect, especially fungicide which is effective to mildew of grapes.

As a result of intensive studies, it was found that the amide compounds of the formula I

R (I) where R1and R2are the same or different and each denotes a hydrogen atom or a C1-3is an alkyl group, and R3denotes 2-follow group, 3-follow group, 2-thienyl group or a 3-thienyl group, exhibit strong fungicidal activity with excellent systemic activity and healing lastly I-1

(I-1) where R represents methyl group or ethyl group, and R 2-thienyl group or a 3-thienyl group.

Especially preferred are the compounds of formula I-2

H3C (I-2) where R takes the specified values.

Hitherto been known a large number of amide compounds, which are useful fungicides and/or herbicides. Among them, such amide compounds (I) according to the chemical structure of the compounds of formula (I), where the thiazole ring is substituted by a substituted benzene, furan, thiophene, benzofuranyl or pyridine ring, the compounds of formula (I), where the thiazole ring is substituted by a substituted benzene ring, furan or thiophene ring, the compounds of formula (I), where thiazoline ring substituted 4-substituted benzene ring, the compounds of formula (I), where the thiazole ring is substituted by an alkyl, alkenylphenol, alkoxyalkyl, cycloalkyl, haloalkyl or haloalkenes group. However, the known compounds are not effective enough to plant diseases, especially diseases caused by phytopathogenic fungi, such as Peronosparales (for example, mildew, late in the mold), and systematic activity. In addition, the operation of the amide compounds (I), especially compounds (I-2), on plant diseases caused by phytopathogenic fungi, without showing any phytotoxicity is completely unexpected and not resulting from these known patents and publications.

The amide compounds (I) can be obtained, for example, by linking halogen, carboxylic acid anhydride of the formula II

(II) where R1and R2each accept these values, and aminonitriles formula III

H2N--R3(III) where R3adopt these values in their reactive form. Some typical methods for the implementation of this process will be further explained in detail.

Methodology A.

According to this method of conducting the reaction of halogen and hydride acid of formula (IV)

R (IV) where R1and R2each accept certain values and X denotes a halogen atom (e.g. chlorine, bromine), aminonitriles formula (III) or its salt to obtain the compound (I).

Usually the reaction is carried out at a temperature from -30 to 50aboutC, preferably from 0aboutWith up to room temperature for from 30 minutes to 24 hours, preferably 1-8 hours, usually in the presence of a base. Examples of bases are tertiary amines (Aprile base (for example, sodium hydroxide, potassium hydroxide, calcium carbonate, sodium hydride) and so on. Aminonitriles (III) or its salt and the base can be used respectively in amounts of 1 to 2 EQ. and from 1 to 3 EQ. to 1 EQ. halogen and hydride acid (IV). In addition, aminonitriles (III) can also be used as a basis. Optionally the reaction may be used any solvent, and examples include aliphatic hydrocarbons (e.g. hexane, heptane, ligroin, petroleum ether), aromatic hydrocarbons (e.g. benzene, toluene, xylene), halogenated hydrocarbons (e.g. chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene), ethers (e.g. diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone), esters (e.g. ethyl formate, ethyl acetate, butyl acetate, diethylmalonate), nitro compounds (for example, nitromethane, nitrobenzene), NITRILES (e.g. acetonitrile, isobutyronitrile), acid amides (for example, formamide, N,N-dimethylformamide, N,N-dimethylacetamide), sulfur compounds (e.g. dimethyl sulfoxide, sulfolane) and so giving, such as sodium hydride. These solvents may be used alone or in combinations.

After completion of the reaction, the reaction mixture may be subjected to post-processing by itself in a standard way, for example, by washing it with water, separation and concentration of the organic layer and, optionally, purification of the resulting product. Cleaning can be applied chromatography or recrystallization.

Methodology Century

According to this method of conducting the reaction of the carboxylic acid (II) with N, N1-conidiomata formula (V)

(V) and receiving elliminate formula (VI)

R (VI) where R1and R2each take certain values, and then spend the reaction elimidate (VI) with aminonitriles (III) or its salt with producing amide compounds (I).

Response to initial and subsequent stages are usually carried out sequentially without allocation of elimidate (VI), because it is not sufficiently stable. These reactions can be carried out at temperatures from -30 to 50aboutC, preferably from 0aboutWith up to room temperature over 30 min to 24 h, preferably from 1 to 8 hours, the Ratio of carboxylic acid (II), N, N

After completion of the reaction, the reaction mixture may be subjected to post-processing by itself in a standard way, for example by washing it with water, separation and concentration of the organic layer and, optionally, purification of the resulting product. Cleaning can be applied chromatography or recrystallization.

In these methodologies, some of the carboxylic acid (II) and halides of the acids (IV) are known, others can be obtained by known methods, for example 2,4-disubstituted thiazole-5-carboxylic acid, 2,4-disubstituted thiazole-5-carbonylchloride, N,N1-conidiomata.

Aminonitriles (III) can be easily obtained by the reaction of the corresponding aldehyde with ammonia and cyanide of potassium or sodium according to the reaction of Striker.

The amide compounds (I) of the invention have one asymmetric carbon atom in their molecules, so for them there are two optical isomers. A practical embodiment of the methods of preparation of amide compounds (I) shown in the examples.

P R I m e R 1 (compound 1). It races the conditions cooling with ice with stirring. After that, the temperature of the mixture is brought to room temperature and to the mixture at a time add 2,4-dimethyl-5-diazocarbonyl acid (1,57 g, 10 mol) and stirring is continued for 30 min, resulting in 5-imidazolidinyl-2,4-dimethylthiazole. To the mixture is added dropwise a solution of 2-(2-furyl)aminoacetonitrile (1,46 g, 12 mmol) in dry tetrahydrofuran under conditions of cooling with ice, and the resulting mixture was stirred at room temperature for 1 h After completion of the reaction, the tetrahydrofuran is removed under reduced pressure to division remainder. To the residue is added water and extracted with ethyl acetate. The ethyl acetate layer washed twice with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain crude crystals. Recrystallization from ethanol yields a 2.0 g of 2-(2,4-dimethylthiazol-5-carboxamido)-2-(2-fu - RIS) of acetonitrile in the form of colorless crystals with a melting point of 108-109aboutC. the Yield 74%

P R I m m e R 2 (compound 2). To a solution of 2-(3-furyl)aminoacetonitrile (1,46 g, 12 mmol) and triethylamine (1.20 g, 12 mmol) in tetrahydrofuran (30 ml) is added slowly a solution of 2,4-dimethylthiazol-5-carbonylchloride (1.75 g, 10 mmol) in tetrahydrofuran (10 ml) in the tion continued for 3 hours The solvent is removed under reduced pressure to division remainder. To the residue is added water and extracted with ethyl acetate. The ethyl acetate layer washed with water and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to get crude oil. The oil is purified by chromatography on a column of silica gel (eluent: n-hexane-ethyl acetate 2 1 by volume) with the receipt of 1.93 g of 2-(2,4-dimethylthiazol-5-carboxamido)-2-(3-furyl)acetonitrile in the form of colorless crystals with a melting point of 94-96aboutC. the Yield 74%

P R I m e R 3 (compound 3). To a solution of imidazole (2,27 g, 40 mmol) in dry tetrahydrofuran (60 ml) is added dropwise thionyl chloride (1.20 g, 10 mmol) in cooling with ice with stirring. After the temperature of the mixture is brought to room temperature, to the mixture at once add, 2,4-dimethyl-5-diazocarbonyl acid (of 1.57 g, 10 mmol), and stirring is continued for 30 minutes To the mixture is added dropwise a solution of 2-(2-thienyl)aminoacetonitrile (1.65 g, 12 mmol) in dry tetrahydrofuran under conditions of cooling with ice, and the resulting mixture was stirred at room temperature for 1 h After completion of the reaction, the tetrahydrofuran is removed under reduced pressure to division ostad the m magnesium sulfate and concentrated under reduced pressure to get crude oil. The oil is purified by chromatography on a column of silica gel (eluent n-hexane-ethyl acetate 2 1 by volume) to obtain crude crystals. Recrystallization from a mixture of n-hexene-ethyl acetate leads to the production of 1.80 g of 2-(2,4-dimethylthiazol-5-carboxamide(2-(2-thienyl)of acetonitrile in the form of colorless crystals with a melting point of 127.5-128,5aboutC. Exit 65%

P R I m e R 4 (compound 4). To a solution of imidazole (2,72 g, 40 mmol) in dry tetrahydrofuran (60 ml) is added dropwise thionyl chloride (1.20 g, 10 mmol) in cooling with ice with stirring. After the temperature of the mixture is brought to room temperature, to the mixture at a time add 2,4-dimethyl-5-diazocarbonyl acid and stirring is continued for another 30 minutes To the mixture is added dropwise a solution of 2-(3-thienyl)aminoacetonitrile (1.65 g, 12 mmol) in dry tetrahydrofuran under conditions of cooling with ice, and the resulting mixture was stirred at room temperature for 1 h After completion of the reaction, the tetrahydrofuran is removed under reduced pressure to division remainder. To the residue is added water and extracted with ethyl acetate. The ethyl acetate layer is washed twice with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure, the-hexane-ethyl acetate 2 1 by volume) to obtain crude crystals. Recrystallization from a mixture of n-hexane-ethyl acetate leads to the production of 1.95 g of 2(2,4-dimethylthiazol-5-carboxamido)-2-(3-tional) of acetonitrile in the form of colorless crystals with a melting point 94-95aboutC. the Yield 70%

P R I m e R 5 (compound 5). To a solution of imidazole (2,72 g, 40 mmol) in dry tetrahydrofuran (60 ml) is added dropwise thionyl chloride (1.20 g, 10 mmol) in cooling with ice with stirring. After the temperature of the mixture is brought to room temperature, to the mixture at a time add 2-methyl-4-ethyl-5-diazocarbonyl acid (1,71 g, 10 mmol) and stirring is continued for another 30 minutes To the mixture is added dropwise a solution of 2-(2-furyl)aminoacetonitrile (1,46 g, 12 mmol) in dry tetrahydrofuran under conditions of cooling with ice and the resulting mixture was stirred at room temperature for 1 h After completion of the reaction, the tetrahydrofuran is removed under reduced pressure until a precipitate. To the residue is added water and extracted with ethyl acetate. The ethyl acetate layer is washed twice with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to get crude oil. The oil is purified by chromatography on a column (eluent n-hexane-ethyl acetate 2 1 plucene of 1.59 g of 2-(2-methyl-n-utiltity-5-carboxamido)-2-(2-furyl)acetonitrile, in the form of colorless crystals with a melting point 125-126aboutC. Exit 57%

P R I m e R 6 (compound 6). To a solution of imidazole (2,72 g, 40 mmol) in dry tetrahydrofuran (60 ml) is added dropwise thionyl chloride (1.20 g, 10 mmol) in cooling with ice with stirring. After the temperature of the mixture is brought to room temperature, to the mixture at a time add 2-methyl-4-ethyl-5-diazocarbonyl acid (1.65 g, 10 mmol) and stirring continued for 30 minutes To the mixture are added dropwise a solution of 2-(2-thienyl)aminoacetonitrile (1.65 g, 12 mmol) in dry tetrahydrofuran under conditions of cooling with ice, and the resulting mixture was stirred at room temperature for 1 h After completion of the reaction, the tetrahydrofuran is removed under reduced pressure to division remainder. To the residue is added water and extracted with ethyl acetate. The ethyl acetate layer was washed with water twice, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain crude oil. The oil is purified by chromatography on a column of silica gel (eluent n-hexane ethyl acetate 2 1 by volume) to obtain crude crystals. Recrystallization from a mixture of n-hexane in ethyl acetate yields a 2-(2-methyl-4-utilizou-5-carboxamido)-2-(2-thienyl)of acetonitrile in which Astaro imidazole (2,72 g, 40 mmol) in dry tetrahydrofuran (60 ml) was added dropwise thionyl chloride (1.20 g, 10 mmol) in cooling with ice with stirring. After the mixture is brought to room temperature, to the mixture at a time add 2-methyl-4-n-propyl-5-thiocarbamoyl acid (1.85 g, 10 mmol), and stirring is continued for another 1 hour To the mixture is added dropwise a solution of 2-(2-thienyl)aminoacetonitrile (1.65 g, 12 mmol) in dry tetrahydrofuran under conditions of cooling with ice, and the resulting mixture was stirred at room temperature for 3 hours After completion of the reaction, the tetrahydrofuran is removed under reduced pressure to division remainder. The ethyl acetate layer is washed twice with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to get crude oil. The oil is purified by chromatography on a column of silica gel (eluent n-hexane ethylacetate 1 by volume) to obtain crude crystals. Recrystallization from n-hexane-ethyl acetate leads to the production of 1.61 g of 2-(2-methyl-4-n-propitiatory-5-carboxamido)-2-(2-thienyl)of acetonitrile in the form of colorless crystals with a melting point 125-126aboutC. Exit 53%

P R I m e R 8 (compound 9). To a solution of imidazole (2,72 g, 4 is Edom under stirring. After the temperature of the mixture is brought to room temperature, to the mixture at a time add 2-methyl-4-isopropyl-5-diazocarbonyl acid (1.85 g, 10 mmol) and stirring is continued for 1 hour To the mixture are added dropwise a solution of 2-(2-thienyl)aminoacetonitrile (1.65 g, 12 mmol) in dry tetrahydrofuran under conditions of cooling with ice, and the resulting mixture was stirred at room temperature for 3 hours After completion of the reaction, the tetrahydrofuran is removed under reduced pressure to division remainder. To the residue is added water and extracted with ethyl acetate. The ethyl acetate layer washed twice with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to get crude oil. The oil is purified by chromatography on a column of silica gel (eluent n-hexane ethyl acetate 2 1 by volume) to obtain 1,49 g 2-(2-methyl-4-isopropylthiazole-5-carboxamide(2-(2-t - enyl)of acetonitrile in the form of a viscous oil. NMR (CDCl3) 1,26/6H, doublet, J 6 Hz), 2,62/3H, singlet), 3,70/1H, septet, J 6 Hz), 6,35/1H, doublet, J 8 Hz), 6,8-7,1 (4H, multiplet). Exit 49%

According to the method specified receive amide compounds (I), are presented in table. 1.

For practical use of amide compounds (I) as the applied powders, suspensions, powders or granules. Such composite shapes can be formed essentially by standard methods, for example by mixing at least one of the amide compounds (I) with an appropriate solid or liquid carrier (s) or diluent (solvent) and, if necessary, with the appropriate additives (additives) (e.g., surfactants, binders, dispersants, stabilizers) to improve the dispersive ability of the pigment and other properties of the active ingredient.

Examples of the solid carriers or diluents are powders or granules of kaolin, attapulgite, bentonite, acid mica, pyrophyllite, talc, hard-shelled land, calcite powder from a stalk of corn, nut powders, urea, ammonium sulfate, synthetic hydrated silicon dioxide and so on. As the liquid carrier or diluent can be represented as aromatic hydrocarbons (e.g. xylene, methylnaphthalene), alcohols (e.g. isopropanol, ethylene glycol cellulose), ketone (e.g. acetone, cyclohexanone, isophorone), soybean oil, hapkoman oil, dimethylsulfoxide, acetonitrile, water and so on.

Surface-active agent used. the reamers surface-active agent include anionic surfactants and nonionic surfactants, such as alkyl sulphates, alkylarylsulfonate, diallylmalonate, phosphates polyoxyethyleneglycol ethers, condensates of naphthalenesulfonate and formaldehyde, polyoxyethylene alkilany ether, polyoxyethylene-polyoxypropylene the first block copolymers, esters sorbitan and fatty acid esters of polyoxyethylene sorbitan and fatty acids. Examples of the auxiliary agents include ligninsulfonate, sodium alginate, polyvinyl alcohol, gum Arabic of Arabicas, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate), and so on.

With the aim of obtaining the fungicidal effect of the amide compounds (I) can be used at doses from 0.01 to 50 g, preferably from 0.05 to 10 g per ar (0.01 ha). Typically, the concentration of active ingredient in the fungicidal compositions of the invention can vary from 0.01 to 99.9 wt. preferably from 1 to 90 wt. For practical use of the composition obtained in the above form, usually diluted with water to a concentration of from 0.0001 to 0.5 wt. preferably from 0.0005 to 0.2 wt. the active ingredient and then it is used after Tacho any dilution.

It should also be noted that the amide compounds (I) can be used in a mixture with other fungicides to enhance their fungicidal activity. In addition, they can be applied with insecticides, miticides, nematicides, herbicides, plant growth regulators, fertilizers and so on.

As indicated, the amide compounds (I) show a reading fungicidal activity. For example, they are preventive, curative and systemic activity against a broad spectrum of plant diseases caused by phytopathogenic fungi, typical examples of which are mildew of vegetables or radish (Peronospora. brassicae), spinato (Peronospora. spinaciae), tobacco (Peronospora. tabacina), cucumber (Pseudoperonospora), grape (Plasmopara viticola) or parsley (Plasmopara nivea), the rotten Apple, strawberry or panaca (Phytophthora cactorum), tomato or cucumber (Phytophthora copsici), pineapple (Phytophthora cinnamomi), potato, tomato, or eggplant (Phytophthora infestans) or tobacco Fava beans or onions (Phytophthora nicotranae var. nicotianae), blackleg spinach (Phythium sp.) or cucumber (Phythium aphanidermatum), rot root Browning wheat (Phytium sp.) black leg sprouts tobacco (Pythium debaryanum), Phythium rot of soybean (Phythium aphanidermatum), P. debaryanum, P./irregulari, P. myiotylum, P. ultimam and so on.

Some of the practical implementation of f is 2">

Example composition 1. 50 wt. h each of compounds 1-14, 3 wt.h. ligninsulfonate calcium, 2 wt.h. arylsulfonate sodium and 45 wt.h. synthetic hydrated silica are mixed and thoroughly milled to obtain wettable powder.

Example composition 2. 25 wt.h. each of compounds 1-14, 3 wt.h. polyoxyethylene sorbent of monooleate, 3 wt.h. SMS and 69 wt.with. water was mixed thoroughly and grind to obtain particles smaller than 4 microns to obtain a suspension.

Example of composition 3. 2 wt.h. each of compounds 1-14, 88 wt.h. kaolin and 10 wt.h. talc was mixed thoroughly and grind until you get a powder.

Example of composition 4. 20 wt.h. each of compounds 1-14, 14 wt.h. polyoxyethylenesorbitan ether, 6 wt.h. dodecylbenzenesulfonate calcium and 60 wt. hours of xylene were mixed together to obtain an emulsion concentrate.

Example of composition 5. 2 wt.h. each of compounds 1-14, 1 wt.h. synthetic hydrated silicon dioxide, 2 wt.h. ligninsulfonate calcium, 30 wt.h. bentonite and 65 wt.h. kaolin were mixed and thoroughly sprayed with the addition of water to obtain pellets.

Typical test data showing significant fungicidal asset is I: 100% means no infection; 0% means that the plant is fully infected in comparison with a control plant.

Were used for comparisons of the compounds are presented in table. 2.

Test example 1. Preventive action on the rot of potato (Phytophthora infestans).

A plastic pot filled sandy soil and plant potatoes (Danshaku), followed by cultivation in a greenhouse for 40 days. On the shoots of the tested plants carefully sprinkle the test compound, is formed in the form of a wettable powder according to example compositions 1 and diluted with water to a certain concentration, and on the tested plants inoculant by spraying a suspension of spores of Phytophthora infestans, after which the plants stand over night in wet conditions. Then the plants germinate within 5 days under illumination and observation. The results are presented in table. 3.

Test example 2.

Healing effects on the rot of potato (Phytophthora infestans). A plastic pot filled sandy soil and plant potatoes (Danshaku), followed by cultivation in a greenhouse for 40 days. A spore suspension of Phytophthora infestans inoculant spray over the sprouts subjects R the TES in the form of a wettable powder according to example compositions 1 and diluted with water to a certain concentration, carefully sprinkle over the test plants, which are then further grown for 5 days under illumination and observation. The results are presented in table. 3.

Test example 3. Preventive action against rot of tomato (Phytophthora infestans).

A plastic pot filled sandy soil and sow the seeds of tomato (Ponte Rosa), followed by cultivation in a greenhouse for 20 days. Test the connection formed in the form of a wettable powder according to example compositions 1 and diluted with water to a certain concentration, carefully sprinkle over the sprouts at the stage of 2-3 leaves of the test plants and the spore suspension of Phytophthora infestans inoculant splash over examinees plants, then leave the plants in conditions of high humidity at 20aboutWith during the night. Further subjects of the plants grown for 5 days under illumination and under supervision. The results are presented in table. 3.

Test example 4. Curative effect against rot of tomato Phytophthora infestans.

A plastic pot filled sandy soil and sow the seeds of tomato (Ponte Rosa), followed by cultivation in a greenhouse for protected plants, then leave the plants in conditions of high humidity at 20aboutWith during the night. Compound formed in the form of a wettable powder according to example compositions 1 and diluted with water to a certain concentration, carefully sprinkle over examinees plants, and then allow them to grow for 5 days at the lighting and under supervision. The results are presented in table. 3.

Test example 5. Preventive action against mildew of grapes Plasmopara viticola.

A plastic pot filled sandy soil, and seeds of grapes (Berry-A) sow in it, followed by cultivation in a greenhouse for a period of 50 days. The test connection is formed in the form of a wettable powder according to example compositions 1 and diluted with water to a certain concentration, carefully sprinkle over the sprouts on stage 6-7 leaves of test plants, and the spore suspension Plasmopara viticola inoculant by spraying over the subjects for the plants, and then leave them in conditions of high humidity at 20aboutWith during the night. Further subjects to allow plants to grow for 8 days under illumination and under supervision. The results present the LASS="ptx2">

A plastic pot filled sandy soil and sow the seeds of grapes (Barry-A), followed by cultivation in a greenhouse for a period of 50 days. The spore suspension Plasmopara viticola inoculant spray over the sprouts on stage 6-7 leaves of test plants, and then leave them in conditions of high humidity at 20aboutWith during the night. The test connection is formed in the form of a wettable powder according to example compositions 1 and diluted with water to a certain concentration, carefully sprinkle over examinees plants, and then allow them to grow for 8 days under illumination and under supervision. The results are presented in table. 3.

Test example 7. Preventive action against mildew of cucumber Pseudoperonospora cubensis.

A plastic pot filled sandy soil and sow in it the seeds of cucumber (Sagamihanjiro), followed by cultivation in a greenhouse for 14 days. Test the connection formed in the form of a wettable powder according to example compositions 1 and diluted with water to a certain concentration, carefully sprinkle over the sprouts of the test plants, and the spore suspension Pseudoperonospora cubensis inoculant by rasbridge is H. Further subjects of the plants grown for 5 days under illumination and under supervision. The results are presented in table. 3.

Test example 8. Curative activity against downy mildew of cucumber Pseudoperonospora cubensis.

A plastic pot filled sandy soil and sow the seeds of cucumber (Sagamihanjiro), followed by cultivation in a greenhouse for 14 days. The spore suspension Pseudoperonospora cubensis inoculant by spraying over the sprouts of the test plants, which are then left overnight at 20aboutWith and in wet conditions. The test connection is formed in the form of a wettable powder according to example compositions 1 and diluted with water to a certain concentration, carefully sprinkle over the test plants are then grown for 8 days under illumination and under supervision. The results are presented in table. 3.

Test example 9. Test impregnation of the soil against rot of tomato Phytophthora infestans.

Plastic pots filled sandy soil and sow in them the seeds of tomato (Ponte Rosa), and then cultivated in a greenhouse for 20 days. When the sprouts have reached the stage of 2-3 leaves, compound, formed as emulsionable and the subjects of the plants remain in a greenhouse during the night. A spore suspension of Phytophthora infestans inoculant by spraying over the subjects for the plants then remain at 20aboutWith during the night in conditions of high humidity. Further subjects of the plants grown for 5 days under illumination and under observation for preventive action. The results are presented in table. 4.

Test example 10.

Phytotoxicity.

Over the sprouts grapes (Berry-A), tomato (Ponte Rosa) and cucumber (Sagamihanjiro) spray test compound formed in the form of a wettable powder according to example compositions 1 and diluted with water to a certain concentration, and allow the test plants to grow in the greenhouse for 2 weeks under the supervision of the phytotoxicity to test plants. Phytotoxicity is assessed visually on a scale of 0, 1, 2, 3, 4 or 5 depending on the extent of the damage, where 5 indicates the absence of plant growth due to phytotoxicity, and 0 indicates the absence of phytotoxicity. The results are presented in table. 5.

Test example 11. Preventive action against vyprevaniya cucumbers from (Phythium aphanidermatum).

The test compound in the composition of the formulation in the form of granules, prigoda soil fill a plastic tray, sowed seeds of cucumber (variety Sagamihanjiro). Experimental plants were cultured for 11 days at the 27aboutWith under lighting and subjected to monitoring in relation to preventive actions. The results are shown in table. 6.

Test example 12. Preventive effect against the damage of potato plants, characterized by zalaganjem them and abscission of leaves without decay (caused by the fungus Phytophthora infestans.

Plastic pan filled sandy soil and its plant potatoes (variety Danashaku), followed by cultivation in a greenhouse for 40 days. The test compound used in the composition mulgirigala concentrate, corresponding to the formulation of example 4 and diluted with water to the desired concentration. The resulting solution thoroughly spray the seedlings on their outer surface of the test plants, then inoculant a spore suspension of Phytophthora infestans by distribution over the test plants, which are left to stand at 20aboutWith all night in the condition of humidity. Next, subjects plants additionally grown for 5 days under illumination and observation. The results are shown in table. 7.

Test example 13. Curative effect against damage plants cartop"ptx2">

Plastic pan filled sandy soil and its plant potatoes (variety Danashaku), and then cultivated in a greenhouse for 40 days. Spores suspension of Phytophthora infestans inoculant through distribution over a germination test plants, which subsequently allowed to stand at 20aboutWith all night in the condition of humidity. The test compound in the composition of the formulation in the form of mulgirigala concentrate according to formulation example 4 was diluted with water to a prescribed concentration. The resulting solution is carefully sprayed the subjects of the plants on the surface and additionally grow their 5 days at the illumination and observation. The results are shown in table. 7.

Test example 14. Preventive effect against late damage to tomato plants, characterized by zalaganjem them and abscission of leaves without decay (caused by the fungus Phytophthora infestans.

Plastic pan filled sandy soil and plant its seedlings of tomato (variety Ponte Rosa), then cultivated in a greenhouse for 20 days. The test compound is administered in a composition mulgirigala concentrate according to formulation example 4 and diluted with water to a prescribed concentration. The resulting solution is carefully sprayed on the nfestans by the distribution of the experimental plants, leave to stand at 20aboutOn the night in wet conditions. Further experimental plants additionally grown for 5 days under illumination and observation. The results are shown in table. 7.

Test example 15. The healing effect against late damage to tomato plants, characterized by zalaganjem them and abscission of leaves without decay (caused by the fungus Phytophthora infestans.

Plastic pan filled sandy soil and plant its seedlings of tomato (variety Ponte Rosa), followed by cultivation in a greenhouse for 20 days. Inoculant a spore suspension of Phytophthora infestans by distributing the seedlings experienced plants under development with 2-3 leaves. Then the plants are left to stand at 20aboutOn the night in wet conditions. The test compound is administered in a composition mulgirigala concentrate, corresponding to the formulation of example 4 and diluted with water to a prescribed concentration. The solution thoroughly sprayed over the test plants. They additionally grow to 5 days at the illumination and observation. The results are shown in table. 7.

Test example 16. Warning against false-powdery mildew (mildew) plants of grapes, called Pl(grade Barry-A), which are then cultivated in a greenhouse 50 days. The test compound in the composition mulgirigala concentrate according to formulation example 4 was diluted with water to a prescribed concentration. The solution is carefully sprayed the outside of the seedlings at the stage of development 6-7 leaves. Test plants inoculant spore suspension Plasmopara viticola through distribution on the test plants. They are left to stand at 20aboutOn the night in wet conditions. Subjects plants grown for 8 days under the light and see. The results are shown in table. 7.

Test example 17. Healing action against false-powdery mildew (mildew) plants of grape, caused by Plasmopara viticola.

Plastic pan filled sandy soil and plant plants grapes (variety Barry-A), followed by cultivation in a greenhouse 50 days. The spore suspension Plasmopara viticola inoculant by distributing the seedlings at the stage of development from 6 to 7 leaves of the test plants. They then leave to stand at 20aboutOn the night in wet conditions. The test compound in the composition mulgirigala concentrate according to formulation example 4 was diluted with water to a prescribed concentration. The resulting solution thoroughly opiskelijat shown in the table. 7.

Test example 18. Warning against false-powdery mildew (mildew) cucumber caused by Pseudoperonospora cubensis.

Plastic pan filled sandy soil and plant seeds of cucumber (variety Sagamihanjiro), then cultivated in a greenhouse for 14 days. The test compound in the composition mulgirigala concentrate according to formulation example 4 was diluted with water to a prescribed concentration and the resulting solution is carefully sprayed the outside of the seedlings tested plants. The spore suspension Pseudoperonospora cubensis inoculant by distributing on the test plants, which are left to stand at 20aboutOn the night in wet conditions. Subjects plants additionally grown for 5 days under illumination and observation. The results are shown in table. 7.

Test example 19. Healing action against false-powdery mildew (mildew) cucumber caused by Pseudoperonospora cubensis.

Plastic pan filled sandy soil and sow seeds of cucumber (variety: Sagamihanjiro), followed by cultivation in a greenhouse for 14 days. The spore suspension Pseudoperonospora cubensis inoculant by the distribution of test plants, which are then left to stand at 20aboutOn the night in terms of the 4 and diluted with water to a prescribed concentration, use to thoroughly spraying the seedlings of the tested plants. They additionally grown for 8 days under illumination and observation. The results are shown in table. 7.

Test example 20. Preventive effect against the damage of potato plants, characterized by zalaganjem them and abscission of leaves without decay (caused by fungi Phytophthora infestans). Plastic pan filled sandy soil and planted there potatoes (variety Danshaku), followed by cultivation in a greenhouse for 40 days.

The test compound in the composition of the powder corresponding to the formula of example 3, is dissolved in water and diluted to a prescribed concentration and used for a thorough spraying on top of the seedlings tested plants. Spores suspension of Phytophthora infestans inoculant the distribution of the test plants, which are then left to stand at 20aboutOn the night in wet conditions. These plants are additionally grown for 9 days at illumination and observation. The results are shown in table. 8.

Test example 21. Curative effect against the damage of potato plants, characterized by zalaganjem them and abscission of leaves without decay (caused by fungi Phytophthora infes Then cultivated in a greenhouse for 40 days. A spore suspension of Phytophthora infestans inoculant by distributing the seedlings tested plants, which are left to stand at 20aboutOn the night in wet conditions. The test compound in the composition of the powder corresponding to the formula of example 3 is diluted with water to a specified concentration and the resulting solution is thoroughly sprayed over the test plants, which subsequently additionally grown for 5 days under illumination and observation. The results are shown in table. 8.

Test example 22. Preventive effect against late damage to tomato plants, characterized by zalaganjem them and abscission of leaves without rot, caused by Phytophthora infestans.

Plastic pan filled sandy soil and sow the seedlings of tomato (variety Ponte Rosa), followed by cultivation in a greenhouse for 20 days. The test compound in the composition of the powder corresponding to the formula of example 3, is dissolved in water and diluted to the prescribed concentration. The resulting solution is carefully sprayed the surface of the seedlings at the stage of development of 2-3 leaves of test plants. Spores in suspension of Phytophthora infestans inoculant distribution for tested plants that leave tsumani and observation. The results are shown in table. 8.

Test example 23. The healing effect against late damage to tomato plants, characterized by zalaganjem them and abscission of leaves without decay (caused by the fungus Phytophthora infestans.

Plastic pan filled sandy soil and plant the seedlings of tomato (variety Ponte Rosa), followed by cultivation in a greenhouse for 20 days. Inoculant spore suspension of Phytophthora infestans by distributing the seedlings at the stage of development of 2-3 leaves of test plants. Then the plants are left to stand at 20aboutWith all night in wet conditions. The test compound in the composition of the powders, whose formula is shown in example 3, is dissolved in water, dilute with water to a specified concentration and the resulting solution is thoroughly sprayed with subjects outside plants, which further grown for 5 days under illumination and observation. The results are shown in table. 8.

Test example 24. Prevent action against false-powdery mildew (mildew) plants of grape (Plasmopara viticola).

Plastic pan filled sandy soil and plant vines (Berry-A) and cultivated in a greenhouse 50 days. Powders, soderi. The resulting solution thoroughly spray the seedlings of test plants at the stage of development 6-7 leaves. Spores of Plasmopara viticola in suspension inoculant through the distribution of the experimental plants. They are left to stand at 20aboutOn the night in wet conditions. Subjects plants additionally grown for 8 days under illumination and observation. The results are shown in table. 8.

Test example 25. Healing action against false-powdery mildew (mildew) in grapevines, caused by Plasmopara viticola.

Plastic pan filled sandy soil and planted there the seedlings vines (Berry-A), followed by cultivation in a greenhouse 50 days. Inoculant the spore suspension Plasmopara viticola by distributing the seedlings of test plants at the stage of development from 6 to 7 leaves. Then these plants are left to stand at 20aboutOn the night in wet conditions. The test compound in the composition of the powder corresponding to the formula of example 3, is dissolved in water and diluted to the prescribed concentration. The resulting solution is thoroughly sprayed with subjects outside plants and additionally grow their 8 days when the illumination and observation. The results are shown in table. 8.

Plastic pan filled sandy soil and planted there the seedlings of cucumber (variety Sagamihanjiro), and then cultivated in a greenhouse for 14 days. The test compound in the composition of the powders according to the recipe of example 3 is dissolved in water and diluted to the prescribed concentration. The resulting solution is carefully sprayed the outside of the seedlings tested plants. Disputes Pseudoperonospora cubensis, which is in suspension, inoculant by distributing them on the test plants, which are left to stand at 20aboutOn the night in wet conditions. Subjects plants additionally grown for 5 days under illumination and observation. The results are shown in table. 8.

Test example 27. Healing effect on false-powdery mildew (mildew cucumbers), caused by Pseudoperonospora cubensis.

Plastic pan filled sandy soil and plant out the seedlings of cucumber (variety Sagamihanjiro), and then cultivated in a greenhouse for 14 days. Disputes Pseudoperonospora cubensis in suspension inoculant distribution outside of seedlings tested plants, which are then left to stand overnight at 20aboutWith moisture. The test compound in the composition of the powders according to the recipe of example 3 is dissolved in water, dilute to produciendo grown for 8 days under illumination and observation. The results are shown in table. 8.

Test example 28. Preventing effect against the damage of potato plants, characterized by zalaganjem them and falling leaves without decay (caused by fungi Phytophthora infestans).

Plastic pan filled sandy soil and plant there, the tubers (variety: Danshaku) and cultivated in a greenhouse for 40 days. The test compound in the composition of the suspension formulation of example 2 is dissolved in water and the resulting solution diluted to a prescribed concentration, thoroughly sprayed over the seedlings of the tested plants. Then the spores of Phytophthora infestans in the composition of the suspension inoculant the distribution of the test plants, which are left to stand at 20aboutOn the night in wet conditions. Subjects plants additionally grown for 5 days under illumination and observation. The results are shown in table. 9.

Test example 29. A curative effect against the damage of potato plants characterized by their withering and falling leaves without decay (caused by fungi Phytophthora infestans).

Plastic pan filled sandy soil and plant there, the tubers (variety Danshaku) and cultivated in a greenhouse is to stand at 20aboutOn the night in wet conditions. The suspension containing the test compound corresponding to the formula of example 2, diluted with water to a specified concentration and the resulting solution is thoroughly sprayed over the test plants. They additionally grow to 5 days at the illumination and observation. The results are shown in table. 9.

Test example 30. Preventing effect against damage to tomato plants, characterized by zalaganjem them and abscission of leaves without decay (caused by fungi Phitophthora infestans).

Plastic pan filled sandy soil and plant seedlings of tomato (variety Ponte Rosa) and cultivated in a greenhouse for 20 days. The suspension containing the test compound corresponding to the formula of example 2, diluted with water to a specified concentration and the resulting solution is thoroughly sprayed over the seedlings in the development stage of 2-3 leaves of test plants. Spores of Phytophthora infestans in suspension inoculant the distribution of the test plants, which are left to stand at 20aboutOn the night in wet conditions. Subjects plants additionally grown for 5 days under illumination and observation. The results are shown in table. 9.

ICP them and abscission of leaves without decay (caused by fungi Phytophthora infestans).

Plastic pan filled sandy soil and plant seedlings of tomato (variety Ponte Rosa) and cultivated in a greenhouse for 20 days. Spores of Phytophthora infestans in suspension inoculant distribution of seedlings at the stage of development of 2-3 leaves of test plants, which then leave to stand at 20aboutOn the night in wet conditions. The suspension containing the test compound corresponding to the formula of example 2, diluted with water to a specified concentration and the resulting solution is thoroughly sprayed over the test plants. They additionally grow to 5 days at the illumination and observation. The results are shown in table. 9.

Test example 32. Prevent action against false-mealy (mildew) of grapevine, caused by Plasmopara viticola.

Plastic pan filled sandy soil and plant the seeds of the vine (grape Berry-A), followed by cultivation in a greenhouse 50 days.

The suspension containing the test compound corresponding to the formula of example 2, diluted with water to a specified concentration and the resulting solution is carefully sprayed on the seedlings at the stage of development 6-7 leaves of test plants. Spores of Plasmopara viticola in>TheOn the night in wet conditions. Subjects plants additionally grown for 8 days under illumination and observation. The results are shown in table. 9.

Test example 33. Healing effect on false-powdery mildew (mildew) grapes, caused by Plasmopara viticola.

Plastic pan filled sandy soil and planted there the seedlings vines (Berry-A), followed by cultivation in a greenhouse 50 days. Inoculant the spore suspension Plasmopara viticola by distributing the seedlings of test plants at the stage of development from 6 to 7 leaves. Then these plants are left to stand at 20aboutOn the night in wet conditions. The test compound in the composition of the powder corresponding to the formula of example 3, is dissolved in water and diluted to the prescribed concentration. The resulting solution is thoroughly sprayed with subjects outside plants and additionally grow their 8 days when the illumination and observation. The results are shown in table. 8.

Test example 34. Preventing effect on false-powdery mildew (mildew) cucumber caused by Pseudoperonospora cubensis.

Plastic pan filled sandy soil and planted there the seedlings of cucumber (variety Sagamihanjiro)astonaut in water and diluted to the prescribed concentration. The resulting solution is carefully sprayed the outside of the seedlings tested plants. Then spores Pseudoperonospora cubensis, which is in suspension, inoculant by distributing them on the test plants, which are left to stand at 20aboutOn the night in wet conditions. Subjects plants additionally grown for 5 days under illumination and observation. The results are shown in table. 9.

Test example 35. Curative activity against downy mildew of cucumber caused by Pseudoperonospora cubensis.

Plastic pan filled sandy soil and sow seeds of cucumber (variety Sagamihanjiro), followed by cultivation in a greenhouse for 14 days. Disputes Pseudoperonospora cubensis in suspension inoculant by distributing the seedlings tested plants, which are then left to stand at 20aboutOn the night in wet conditions. The suspension containing the test compound corresponding to the formula of example 2, diluted with water to a specified concentration and the resulting solution is thoroughly sprayed with subjects outside of the plant. These plants are additionally grown for 8 days under illumination and observation. The results are shown in table. 9.

However, to further confirm the advantage is For comparison we used the following connections:

Compound G: CH

The specified connection in General is described in the ed. St. USSR N 270632.

Compound H: H2N

The specified connection specifically described in the ed. St. USSR N 270632.

Test method and results.

Curative effect on cucumbers affected downy mildew (Pseudoperonospora cubensis).

The tests were carried out by the method described in test example 8. The test results are presented in table. 10.

Soil analysis mitospores of tomato (Phytophthora infestans).

The tests were carried out by the method described in example 9. The test results are presented in table. 11.

Thus, from all the above data it is clear that all proposed connections are far superior in the properties of known compounds. Only connection is at the level proposed for antifungal activity. However, from the data table. 5 shows that at the dose of 500 hours /million connection has a significant phytotoxicity, whereas the compounds of the invention do not possess phytotoxic even at the dose of 1000 hours/million and so it is superior to the well-known compound for safety for crops.

1. DERIVATIVE AMIDE of the formula I

the pas;

R32-furilla group, 3-furilla group, 2-Taanilinna group or 3-thienyl group.

2. Derivative amide under item 1, in which R1and R2each a methyl group.

Priority signs:

23.03.88 under item 1;

26.05.87 on p. 2.

 

Same patents:

The invention relates to new derivatives substituted benzoylbenzene-, biphenyl - 2-oxazolidinone acid, which has inhibitory activity against lipoxygenase, phospholipase A2and which are leukotriene antagonists; derivatives, which are suitable for use as anti-inflammatory, antiallergic agents, but also as protectors

The invention relates to new chemical compounds derived benzothiazine responsible of General formula I

where R1lower alkyl WITH1-C4

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

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: 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.

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: 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, 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

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to biologically active compounds, in particular, to substituted 5R1,6R2-thiadiazine-2-amines and pharmaceutical compositions comprising thereof that can be used in medicine as potential pharmacologically active substances eliciting the unique combination of properties: expressed anticoagulant activity in combination with capacity to inhibit aggregation of platelets. Effect of these substances differ from preparations used in medicinal practice and they can be used therefore in treatment of such diseases as myocardium infarction, disturbance in cerebral circulation, rejection of transplanted organs and tissues and so on. Indicated compounds correspond to the formula (I):

wherein values of radicals R1, R2 and R3 are given in the invention claim.

EFFECT: valuable medicinal properties of compounds.

4 cl, 2 tbl, 7 dwg, 33 ex

FIELD: organic chemistry, chemical technology, medicine.

SUBSTANCE: invention relates to a method for preparing derivatives of indole of the general formula (I):

wherein R1 represents hydroxy-group; R2 represents hydrogen atom, (C1-C6)-alkyl, (C1-C6)-alkoxy-group, (C2-C6)-alkoxyalkyl or 4-methoxybenzyl; R3 represents hydrogen atom or (C1-C6)-alkyl; each among R4 and R represents independently hydrogen atom, (C1-C6)-alkyl or (C1-C6)-alkoxy-group; D represents an ordinary bond, (C1-C6)-alkylene, (C2-C6)-alkenylene or (C1-C6)-oxyalkylene; in the group-G-R6 wherein G represents an ordinary bond, (C1-C6)-alkylene; R represents saturated or unsaturated carbocyclic ring (C3-C15) or 4-15-membered heterocyclic ring comprising 1-5 atoms of nitrogen, sulfur and/or oxygen wherein this ring can be substituted. Also, invention describes a method for preparing derivatives of indole and DP-receptor antagonist comprising derivative of the formula (I) as an active component. As far as compounds of the formula (I) bind with DP-receptors and they are antagonists of DP-receptors then they can be useful for prophylaxis and/or treatment of diseases, for example, allergic diseases.

EFFECT: improved preparing method, valuable medicinal properties of compounds.

11 cl, 7 tbl, 353 ex

FIELD: pharmaceutical chemistry, medicine.

SUBSTANCE: invention relates to substituted pyridines and pyridazines with angiogenesis inhibition activity of general formula I

(I)1, wherein ring containing A, B, D, E, and L represents phenyl or nitrogen-containing heterocycle; X and Y are various linkage groups; R1 and R2 are identical or different and represent specific substituents or together form linkage ring; ring J represents aryl, pyridyl or cycloalkyl; and G's represent various specific substituents. Also disclosed are pharmaceutical composition containing claimed compounds, as well as method for treating of mammalian with abnormal angiogenesis or treating of increased penetrability using the same.

EFFECT: new pyridine and pyridazine derivatives with angiogenesis inhibition activity.

26 cl, 6 tbl, 114 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention elates to novel derivatives of uracil of the formula [I] possessing herbicide activity, a herbicide composition based on thereof and to a method for control of weeds. In derivatives of uracil of the formula [I] the group Q-R3 represents a substituted group taken among:

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

EFFECT: improved preparing method, valuable properties of compounds.

40 cl, 16 sch, 12 tbl, 65 ex

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