Derivatives triazolyl, the way they are received and fungicidal agent

 

(57) Abstract:

Describes the new derivatives triazolyl General formula I, where R1means a linear alkyl with 1-6 carbon atoms, substituted gaelicforum or halohydrocarbons, phenyl, substituted by halogen or haloalkoxy; R2means cycloalkyl with 3-7 carbon atoms, substituted by halogen or cyano, linear or branched alkyl with 1-6 carbon atoms which may be substituted by halogen, alkoxygroup with 1-4 carbon atoms or halohydrocarbons, or phenyl, substituted by halogen; x is the group-SH, -SR3, -SO3N or-SO3H, where R3means a linear alkyl with 1-6 carbon atoms or terratial, and their acid additive salts or complexes with metal salts. The compounds exhibit fungicidal activity. Describes the method of obtaining them, as well as fungicidal agent based on the compounds of General formula I. 3 S. and 1 C.p. f-crystals, 2 PL.

The invention relates to new nitrogen-containing heterocyclic compounds possessing biological activity, in particular fungicidal activity, and more particularly to a derivative triazolyl, the way they are received and fungicidal gildroy activity (see application EP N 086 251, C 07 D 249/08, 07.01.1988 year).

The objective of the invention is the expansion of derivatives triazolyl possessing biological activity, in particular fungicidal activity.

The problem is solved proposed derivative of the formula (I)

< / BR>
where R1means a linear alkyl with 1-6 carbon atoms, substituted gaelicforum or halohydrocarbons, phenyl, substituted by halogen or haloalkoxy,

R2means cycloalkyl with 3-7 carbon atoms, substituted by halogen or cyano, linear or branched alkyl with 1-6 carbon atoms which may be substituted by halogen, alkoxygroup with 1 to 4 carbon atoms or halohydrocarbons, or phenyl substituted by halogen,

X represents the group-SH, -SR3, -SO2R3or-SO3H, where R3means a linear alkyl with 1-6 carbon atoms or terratial.

Preferred derivatives triazolyl formula (I) is 2-(1-chlorocyclopropane)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4 - triazole-1-yl)-propan-2-ol.

For the formation of acid additive salts preferably used halogen acids, such as hydrochloric acid and bromisovalbromisoval carboxylic acid and hydroxycarbonate acid, for example acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid, and sulfonic acids, for example p-toluensulfonate and 1.5-naphthalenedisulfonate, as well as saccharin and tishrin.

Preferred complexes with metal salts are addition products of salts of metals of the II-IV main group and I and II and also IV to VIII of the side groups of the periodic system of the elements and those derived triazolyl formula I, in which R1, R2and X have the above values.

Especially preferred are salts of copper, zinc, manganese, magnesium, tin, iron and Nickel. The anions of these salts can be those that are formed from acids, which give physiologically tolerated the addition products. Particularly preferred acids of this type are halogen acids, for example hydrochloric acid and Hydrobromic acid, then phosphoric acid, nitric acid and sulphuric acid.

Derivatives triazolyl formula (I) in which X represents-SH-group can be in the "mercapto"form

< / BR>
or in the tautomeric "Tino"-Fe triazolyl formula (I) belong to the category of metal-toxic substances.

Derivatives triazolyl formula (I) in which X represents the group-SR3where R3means terratial, and their acid additive salts or complexes with metal salts get due to the fact that the compound of formula (II)

< / BR>
where R1and R3have the above values,

subjected to sequential interaction with a strong base and diphenyl-disulfide of formula (III)

R4S-S-R4(III)

where R4means phenyl,

in the presence of a diluent, followed by separation of the target product in free form or in the form of an acid additive salt or complex salt of the metal.

This method is an additional object of this application.

Derivatives triazolyl formula (I), where R1, R2and X have the above meanings, can be obtained as follows.

(a) Hydroxyethyl-triazole of the formula (II)

< / BR>
where R1and R2have the above values,

or

sequentially subjected to transformation with a strong base and sulfur in the presence of a diluent and then hydrolyzing with water, optionally in the presence of acid,

or

) is subjected to interaction with sulfur in the presence of published received options ( ) and ( ) the compounds of formula (Ia)

< / BR>
in which R1and R2have the above values,

subjected to interaction with halogen compounds of the formula (IV)

R5-Hal (IV)

in which R5means a linear alkyl with 1 to 6 carbon atoms or phenyl,

Hal means chlorine, bromine or iodine,

in the presence of acid binding means, and in the presence of a diluent, and the resulting compounds of the formula (IB)

< / BR>
in which R1, R2and R5have the above values, if necessary, subjected to interaction with oxidizing means in the presence of a diluent,

b) Derivatives triazolyl formula (Ia)

< / BR>
in which R1and R2have the above values,

subjected to interaction with potassium permanganate in the presence of a diluent,

and finally, if necessary, to the obtained compounds of formula (I) attach an acid or metal salt.

The proposed method for obtaining derivatives triazolyl formula (I) in which X represents the group SR3that is explained in the following.

If used as a starting compound 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(1,2,4-triazole-1-yl)-propan-2-ol, n-utility as seemai:

< / BR>
Hydroxyethyl-triazole of the formula (II) and diphenyl disulfides of the formula (III) are known or can be obtained by known methods.

As strong bases are all normal for this type of reactions a strong Foundation based on alkali metals. Preferably used n-utility, Li-aminobutiramida amide, sodium hydride, sodium amide and potassium-tert.-butyl mixed with tetramethylethylene-diamine.

As diluents are all normal for this type of reactions of organic solvents. Preferred are ethers, such as tetrahydrofuran, dioxane, diethyl ether and 1,2-dimethoxyethan, the liquid ammonia or strongly polar solvents, such as dimethylsulfoxide.

The reaction temperature can vary in a wide interval. Typically operate at temperatures between -70oC and +20oC, preferably between -70oC and 0oC.

When carrying out the proposed method are usually under normal pressure. But you can also work at elevated or reduced pressure.

The above-mentioned methods (a) and (b), which are not objects of the invention are explained in the following.

-ol, n-utility as a strong Foundation and powder sulfur as reactant, the course of the first stage of the method (a), version ( ), can be represented by the following scheme:

< / BR>
If used as a starting compound 2-(1-chloro - cyclopropyl)- 1-(2-chlorophenyl)-1-(1,2,4-triazole-1-yl)-propan-2-ol, sulfur powder as a reagent and N-methyl-pyrrolidone as a solvent, the flow of the first stage of the method (a), version (), can be represented by the following scheme:

< / BR>
If used as a starting compound 2-(1 - chloro-cyclopropyl)- 1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazole-1 - yl)-propan-2-ol and methyliodide as reactant, the course of the second stage of the method (a) can be represented by the following scheme:

< / BR>
If used as a starting compound 2-(1-chloro - cyclopropyl)-1-(2-chlorophenyl)-3-5-methylthio-1,2,4-triazole-1 - yl)propan-2-ol and an excess of hydrogen peroxide as oxidant, the course of the third stage of the method (a) can be represented by the following scheme:

< / BR>
If used as a starting compound 2-(1 - chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazole-1 - yl)-propan-2-ol as an oxidant, potassium permanganate, then the flow of method (b) can be represented by the following scheme:

When carrying out the first stage of the method (s) for option (a) is usually introduced in one mole of hydroxyethyl-triazole of the formula (II) two to three equivalents, preferably 2.0 to 2.5 equivalents, of a strong base, and then an equivalent amount or an excess of sulfur. The interaction can occur in the atmosphere of inert gas, such as argon or nitrogen. Operate at the same temperature and the same pressure as in the conduct of the proposed method. Processing occurs with conventional methods. Usually in such a way that the reaction mixture is extracted with poorly water-soluble organic solvent, dried the combined organic phases concentrated and the remaining residue is purified if necessary by recrystallization and/or chromatography.

When carrying out the first stage of the method (a), version (),, ispolzuyuschihsya are amides, such as dimethylformamide and dimethylacetamide, also heterocyclic compounds such as N-methyl-pyrrolidone, and also ethers, such as diphenyl ether.

When carrying out the first stage of the method (a), version (), sulfur is used usually in powder form. After the interaction can optionally be treated with water or acid. The processing carried out in the same way as hydrolysis when carrying out the first stage of the method (s) for option ().

The reaction temperature during the first stage of the method (s) for option (a) can vary in a wide interval. Typically operate at temperatures between 150oC and 300oC, preferably between 180oC and 250oC.

When carrying out the first stage of the method (s) for option (a) is usually introduced by one mole hydroxyethyl-triazole of the formula (II) from one to five moles, preferably 1.5 to 3 mol, of sulfur. Processing occurs with conventional methods. Usually in such a way that the reaction mixture is extracted with poorly water-soluble organic solvent, dried the combined organic phases concentrated and the remaining residue is purified if necessary by recrystallization and/or chromatography.

Halogen of Priya second stage of the method (a) all customary inorganic or organic bases. Preferably apply hydroxide of alkali or alkaline earth metals such as sodium hydroxide, potassium hydroxide, calcium hydroxide, or ammonium hydroxide, carbonates of alkali metals such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, acetates, alkali or alkaline earth metals such as sodium acetate, potassium acetate, calcium acetate, and also tertiary amines, such as trimethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, diazabicyclo, Diisobutylene or databaseconnect.

As the diluent used in the second stage of the method (a) all the usual reactions of inert organic solvents. Preferably used ethers, for example diethyl ether, methyl-tert.-butyl ether, dimethyl ether of ethylene glycol, tetrahydrofuran or dioxane, and the NITRILES, for example acetonitrile, and, in addition, highly polar solvents such as dimethylsulfoxide or dimethylformamide.

The reaction temperatures when carrying out the second stage of the method (a) can vary in a wide interval. Typically operate at temperatures between 0oC and 120oC, preferably between the underwater triazolyl formula (Ia) from one to two moles of a halogen compound of the formula (IV), and an equivalent amount or an excess of acid binding means. Processed by conventional methods. Usually in such a way that the reaction mixture is mixed with a water base and is poorly miscible with water, an organic solvent, the organic phase is separated, dried and concentrated. The resulting product is distilled from existing impurities, if necessary, by recrystallization.

As the oxidizing agent used in the third stage of the method (a) all applicable to the oxidation of sulfur substances. It is preferable to use hydrogen peroxide, nagkalat, for example peracetic acid and meta-chloro-nabintou acid, and, in addition, inorganic salts, such as potassium permanganate.

As the diluent used in the third stage of the method (a) all the usual reaction solvents. If using hydrogen peroxide or nagkalat as oxidant, the diluent used is preferably acetic acid or glacial acetic acid. If you are working with potassium permanganate as oxidant, use water or alcohols, such as tert.-butanol.

The reaction temperatures when carrying out the third with the 00oC, preferably between 10oC and 100oC.

When carrying out the third stage of the method (a) is usually introduced to one mol of the compounds of formula (IB) an equivalent amount or an excess of oxidant. If you want to obtain SO-connections, work with equimolar quantities. If you want to get SO2connection, then take the excess oxidant. Processed by conventional methods. Usually do so that is diluted with ice or water, if necessary, alkalinized by addition of base, extracted with poorly miscible with water, an organic solvent, dried the combined organic phases concentrated and the resulting product is optionally recrystallized. If you are working with potassium permanganate in aqueous solution, proceed in such a way that the solid is filtered off, washed and dried.

Obtained according to the above methods triazole derivatives of the formula (I) can be converted into salts accession acids or complexes with metal salts.

Salts of compounds of formula (I) with acids get a simple way by conventional methods, for example by dissolving the compounds of formula (I) in a suitable inert solvent and adding sour is on cleaned by rinsing with an inert organic solvent.

Complexes of compounds of the formula (I) with metal salts can be a simple way by the well-known methods, for example by dissolving the metal salt in alcohol, for example ethanol, and adding to the compounds of formula (I). Complexes in a known manner, for example by filtration, is isolated and optionally purified by recrystallization.

As mentioned above, derivatives of triazole of the formula (I) exhibit fungicidal activity.

Therefore, a further object of the invention is a fungicidal agent which contains derived triazolyl formula (I) or its acid additive salt or complex salt of the metal.

Derivatives triazolyl formula (I) hereinafter referred to as "active substances".

The active substance can be applied as such, in the form of concentrates or cooked of them working forms, such as ready-to-use solutions, emulsifiable concentrates, emulsions, foams, suspensions, powders for spraying, pastes, soluble powders, preparations for dusting and pellets. The application in the normal way, for example by watering, spraying, spreading, spraying, smearing, etc. Also enabled the substance incorporated into the soil. You can also process the seed.

When processing parts of plants the concentration of the active substance in a form ready for use, vary in a wide interval: usually, they range from 1 to 0.0001 wt.%, preferably from 0.5 to 0.001 wt.%.

When the seed treatment, the amount of active substance is usually from 0.001 to 50 g per kg of seed, preferably from 0.01 to 10 g

During cultivation, the concentration of active substance in the applications is from 0.00001 to 0.1 wt.%, preferably from 0.0001 to 0.02 wt.%.

Concentration when using active substances depends on the type and origin of fungi, as well as on the composition of the protected material. The optimal number is determined by a number of experiments. Usually the concentration of application range from 0.001 to 5 wt.%, preferably from 0.05 wt.% to 1.0 wt.%, counting on the protected material.

Deriving triazolyl formula (I) is illustrated by the following examples.

Example 1

< / BR>
Option

A mixture of 3.12 g (10 mmol) of 2-(1-chloro-cyclopropyl)- 1-(2-chlorophenyl)-3-(1,2,4-triazole-1-yl)-propan-2-ol and 45 ml of absolute tetrahydrofuran is mixed at 20oC with 8.4 ml (21 mmol) of n-utility in GE mmol) of sulfur powder and stirred for 30 minutes at -70oC. is Heated to -10oC, mixed with ice water and set to pH 5 by adding dilute sulfuric acid. Repeatedly extracted with ethyl acetate, dried the combined organic phases with sodium sulfate and concentrated under reduced pressure. Get so 3.2 g (93% of theory) of 2-(1-chloro-cyclopropyl)- 1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazole-1-yl)-propan-2-ol in the form of a solid, which after recrystallization melted at 138-139oC.

Option

A mixture of 3.12 g (10 mmol) of 2-(1-chloro-cyclopropyl)- 1-(2-chlorophenyl)-3-(1,2,4-triazole-1-yl)-propan-2-ol, 0.96 g (30 mmol) of sulfur powder and 20 ml of absolute N-methyl-pyrrolidone is heated with stirring for 44 hours at 200oC. Then the reaction mixture was concentrated under reduced pressure (0.2 mbar). The resulting crude product (3.1 g) is recrystallized from toluene. Obtain 0.7 g (20% of theory) of 2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(5 - mercapto-1,2,4-triazole-1-yl)-propan-2-ol in the form of solid, which melts at 138-139oC.

Example 2

< / BR>
The mixture of 3.43 g (10 mmol) of 2-(1-chloro-cyclopropyl)-1-(2 - chlorophenyl)-3-(5-mercapto-1,2,4-triazole-1-yl)-propan-2-ol, 20 ml of absolute acetonitrile and 1.38 g (10 mmol) of potassium carbonate mixed with with 0.93 ml (15 malestrom sodium carbonate and repeatedly extracted with ethyl acetate. The combined organic phases are dried and concentrated under reduced pressure. Get so 3.4 g (95% of theory) of 2-(1 - chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazole 1-yl)- propan-2-ol in the form of butter.1H-NMR spectrum (200 MHz; deuterochloroform, TMS) = 0,6-of 1.05 (m, 4 H); and 2.7 (s, 3 H); 3,35 (AB, 2 H); 4,4 (AB, 2H); 4.7 in (OH); 7,2-7,6 (m, 4H); and 7.9(s,1 H).

= from 0.6 to 1.05 (m, 4H); and 2.7 (s, 3H); 3,35 (AB, 2H); 4,4 (AB, 2H); 4.7 in (OH); 7,2-7,6 (m, 4H); and 7.9 (s, 1 H).

Example 3

< / BR>
A solution of 3.57 g (10 mmol) of 2-(1-chloro-cyclopropyl)-1-(2 - chlorophenyl)-3-(5-methylthio-1,2,4-triazole-1-yl)-propan-2-ol in 40 ml of glacial acetic acid are mixed dropwise at 90oC and when mixed with 4 ml of an aqueous solution of hydrogen peroxide (35%). The reaction mixture is stirred after the addition of a further 30 minutes at 90oC, then cooled to room temperature, mixed with ice and alkalinized by addition of an aqueous caustic soda. Extracted repeatedly with ethyl acetate, dried the combined organic phases with sodium sulfate and concentrated under reduced pressure. The remaining slowly crystallized product is filtered off. Obtain 2.0 g (51% of theory) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5 - methylsulphonyl-1,2,4-triazole-1-yl)-propan-2-ol in the form of a solid substance, which has so pl. 125 is then-1,2,4-triazole-1-yl)-propan-2-ol, 1,58 g (10 mmol) of potassium permanganate and 20 ml of water is stirred for 30 minutes at room temperature. After this solid is sucked off, washed with water and dried. Obtain 2.0 g (100% of theory) of 2-(1-chlorocyclopropane)-1-(2-chlorophenyl)-3-(5-sulfo-1,2,4-triazole - 1-yl)-propan-2-ol in the form of a solid substance with so pl. 68-70oC.

Example 5

< / BR>
A mixture of 3.12 g (10 mmol) of 2-(1-chlorocyclopropane)-1-(2 - chlorophenyl)-3-(1,2,4-triazole-1-yl)-propan-2-ol and 45 ml of absolute tetrahydrofuran is mixed at -20oC with 8.4 ml (21 mmol) of n-utility in hexane and stirred for 30 minutes at 0oC. Then the reaction mixture is cooled to -70oC, mix from 2.18 g (10 mmol) of diphenyl-disulfide and slowly brought to room temperature. Stirred for 19 hours at room temperature, diluted with ethyl acetate and shaken several times with saturated aqueous sodium carbonate. The organic phase is dried with sodium sulfate and concentrated under reduced pressure. The remainder of 4.2 g chromatographic through 500 g of silica gel with a mixture of solvents petroleum ether/ethyl acetate at a ratio of 2: 1. After evaporation of the eluate obtain 3.5 g (84% of theory) of 2-(1 - chlorocyclopropane)-1-(2-chlorophenyl)-3-(5-phenylthio-1,2,4-triazole-1 - yl)-propan-2-ol in the form of a Mac is sleduushie examples illustrate the fungicidal activity of derivatives triazolyl formula (I).

Example 19

Test the protective activity against Erysiphe barley.

1 weight. part of the active substance N I-1 is mixed with 10 weight. parts of N-methyl-pyrrolidone as solvent and 0.6 weight. parts alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the resulting medium at a flow rate of the active substance, equal to 250 g/ha After drying the engraved plaque plants they pollinate disputes Erysiphe graminis f. sp. hordei.

Plants are placed in a greenhouse at a temperature of about 20oC and a relative humidity of about 80% to foster the development of powdery mildew pustules.

After 7 days of inoculation produce a percentage mark. When set to 100% activity compared to untreated control plants.

Example 20

Test the protective activity against Erysiphe in wheat.

1 weight. part of the active substance N I-1 is mixed with 10 weight. parts of N-methyl-pyrrolidone as solvent and 10 weight. parts alkylarylsulphonates ether as an emulsifier, and the concentrate produced rasbase obtained by means of the flow-rate of the active substance, equal to 250 g/ha After drying the engraved plaque plants they pollinate disputes Erysiphe graminis f. sp. tritici.

Plants are placed in a greenhouse at a temperature of about 20oC and a relative humidity of about 80% to foster the development of powdery mildew pustules.

After 7 days of inoculation produce a percentage mark. When set to 100% activity compared to untreated control plants.

Example 21

Test the protective activity against Pseudocerosporella herpotrichoides in wheat.

1 weight. part of the active substance N I-1 is mixed with 10 weight. parts of N-methyl-pyrrolidone as solvent and 0.6 weight. parts alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the resulting medium at a flow rate of the active substance, equal to 250 g/ha After drying the engraved plaque plants they pollinate disputes Pseudocerosporella herpotrichoides.

Plants are placed in a greenhouse at a temperature of about 20oC and a relative humidity of about 80% to foster the development of powdery mildew pustules.

compared with untreated control plants.

Example 22

Test the protective activity against Fusarium nivale (var. nivale) in wheat.

1 weight. part of the active substance N I-1 is mixed with 10 weight. parts of N-methyl-pyrrolidone as solvent and 0.6 weight. parts alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the resulting medium at a flow rate of the active substance, equal to 250 g/ha After drying the engraved plaque plants are pollinated with spores of Fusarium nivale (var. nivale).

Plants are placed in a greenhouse under translucent incubation mesh at a temperature of approximately 15oC and a relative humidity of about 100%.

After 21 days after inoculation produce a percentage mark. When set to 100% activity compared to untreated control plants.

Example 23

Test the protective activity against Fusarium culmorum in wheat.

1 weight. part of the active substance N I-1 N I-15, respectively, is mixed with 10 weight. parts of N-methyl-pyrrolidone as solvent and 0.6 weight. parts alkylarylsulphonates ether as an emulsifier and polycrystals young plants obtained by means of the flow-rate of the active substance, equal to 250 g/ha After drying the engraved plaque plants are pollinated with spores of Fusarium culmorum.

Plants are placed in a greenhouse under translucent incubation mesh at a temperature of about 20oC and a relative humidity of about 100%.

Later, 4 days after inoculation produce a percentage mark.

Establish that the active substance N I-1 is 100% fungicidal activity compared with untreated control plants, while the active substance N I-15 - 75% fungicidal activity.

Example 24

Repeat example 23 with the difference that the applied active substance N I-16 at a flow rate of 125 g/ha When set to 100% activity compared to untreated control plants.

Example 25

Test the protective activity against Pellicularia in rice.

1 weight. part of the active substance N I-1 mixed with 12.5 weight. parts of acetone as a solvent and 0.3 weight. parts alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to the desired concentration of the active substance, equal to 0.025 wt.%.

To test for protective activity, young plants are sprayed with the resulting environment is oxytelinae humidity of 100%.

8 days after inoculation produce a percentage mark. When set to 100% activity compared to untreated control plants.

Example 26

Test the protective activity against Sphaerotheca in cucumbers.

1 weight. part of the active substance N I-1 mixed with 4.7 weight. parts of acetone as a solvent and 0.3 weight. parts alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to the desired concentration of the active substance 1 h/ml

To test for protective activity, young plants are sprayed with up to the formation of droplets. After drying the engraved plaque plants are pollinated with conidia of the fungus Sphaerotheca fulidinea.

Plants are placed in a greenhouse at a temperature of about 23 - 24oC and a relative humidity of about 75% to foster the development of powdery mildew pustules.

10 days after inoculation produce a percentage mark. When set to 100% activity compared to untreated control plants.

Example 27

Test the protective activity against Botrytis in legumes.

1 weight. some of the listed in table 2 aktivnogo ether as an emulsifier, and the resulting concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the received vehicle at a flow rate of the active substance, equal to 500 g/ha After drying of the applied coating on each sheet put two agar piece with grown on them by the fungus Botrytis cinerea.

Inoculated plants are placed in the dark greenhouse at a temperature of about 23 - 24oC and a relative humidity of 100.

Later, 2 days after inoculation produce interest assessment by fungi on leaves. 0% means the degree of action, appropriate to the degree of action on untreated control plants, and 100% means that the lesion is not observed.

The active substance and the results of the experiment are shown in table 2.

1. Derivatives triazolyl formula I

< / BR>
where R1means a linear alkyl with 1 to 6 carbon atoms, substituted gaelicforum or halohydrocarbons, phenyl, substituted by halogen or haloalkoxy;

R2means cycloalkyl with 3 to 7 carbon atoms, substituted by halogen or cyano, linear or branched alkyl with 1 to 6 carbon atoms which may be substituted by halogen, alkoxygroup with 1 to 4 carbon atoms or halohydrocarbons, the R3means a linear alkyl with 1 to 6 carbon atoms or terratial,

and their acid additive salts or complexes with metal salts.

2. Derived triazolyl formula I under item 1, which represents a 2-(1-chlorocyclopropane)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazole-1-yl)-propan-2-ol.

3. A method of obtaining a triazole derivative of the formula I

< / BR>
where R1means a linear alkyl with 1 to 6 carbon atoms, substituted gaelicforum or halohydrocarbons, phenyl, substituted by halogen or haloalkoxy;

R2means cycloalkyl with 3 to 7 carbon atoms, substituted by halogen or cyano, linear or branched alkyl with 1 to 6 carbon atoms which may be substituted by halogen, alkoxygroup with 1 to 4 carbon atoms or halohydrocarbons, or phenyl, substituted by halogen;

X group-SR3where R3means terratial,

or their acid additive salts or complexes with metal salts, characterized in that the compound of formula II

< / BR>
where R1and R2have the above values,

subjected to sequential interaction with a strong base and diphenyl-disulfide of formula III

R4-S-SR4,

4. Fungicidal agent which contains derived triazolyl formula I under item 1 or an acid additive salt or complex salt of the metal.

 

Same patents:

The invention relates to the derivatives of pyrazole and herbicides containing them

The invention relates to a new vysokomernoa tritium compound -(2-propylene-4,6-dimethyl-8-oxymethyl)octyl-(3-hydroxy-4,5,6-trimethyl-6-ene)heptylene General formula I

< / BR>
which finds application in biochemical and biomedical studies, and to a method thereof, which lies in the interaction of the parent substance of General formula I with tritium water, by introducing into the reactor the initial substance, РdO or a mixture РdО with 5% РdО/Al2O3, the evacuation of the reactor filled with gaseous tritium and heated at local cold by freezing its upper part, then the reactor re-vacuum, heated to 65 - 85oC, then give him dioxane or a mixture of dioxane with triethylamine

The invention relates to new biologically active compound from a number of heterocyclic compounds of the formula I, showing the property activator germination of wheat seeds

The invention relates to a new benzodiazepine derivative of the formula I given in the text of the description, which are useful as medicines, which have an antagonistic effect against gastrin and/or CCK receptor-and their reception, where R1refers to a group-CH2CH(OH)(CH2)aR4or ketone group,- CH2CO(CH2)aR5where a = 0 or 1; R4- C1-C7-alkyl straight or branched chain or C3-C8-cycloalkyl; R5- C1-C8-alkyl, C3-C8-cycloalkyl,3-C8-cycloalkyl-C1-C8-alkyl, C1-C8-alkyl-C3-C8-cycloalkyl, pyrrolidyl, possibly substituted C1-C8-acyl, carbamoyl,1-C8-alkylamino-C1-C8-alkyl, or adamantylidene; R2is phenyl, substituted C1-C8-alkyl, C1-C8-alkoxyl, nitro, cyano, amino, halogen, C1-C8-alkylaminocarbonyl, di-(C1-C8-alkylaminocarbonyl, carboxy, C1-C8-allmineral, carboxyhemoglobin, carboxy(C1-C8)alkyl, or pyridylethyl, possibly substituted C1-C8-alkyl; R3- peloid in the 7-position of the benzodiazepine ring; W is hydrogen or C1-C8the alkyl in the 8-position of the benzodiazepine ring, or its pharmaceutically acceptable salt

The invention relates to compounds which inhibit the protease encoded by human immunodeficiency virus, or their pharmaceutically acceptable salts, and such compounds are used for the prevention of infection by HIV, treating infection by HIV and the treatment of acquired as a result immunodeficiency syndrome (AIDS)

The invention relates to therapeutic tools, specifically setidentityproviderid N-substituted nitrogenous heterocyclic compounds and methods of producing such compounds, intermediate products used in obtaining, compositions containing such compounds and the use of such heterocycles

The invention relates to new substituted heterocyclic compounds, process for the preparation of these compounds and pharmaceutical compositions containing them as active substances

The invention relates to new derivatives of phenyl-oxo-alkyl-(4-piperidinyl)benzoate of formula I, their N-oxide forms, salts and steric isomer forms, where R1- halogen, R2is hydrogen, R3- C1-6-alkyl, or R2and R3form together a bivalent radical of the formula -(CH2)2- or -(CH2)3-, Alk-C1-6-alcander, R4is hydrogen or C1-6-alkoxy, R5, R6and R7is hydrogen, halogen, C1-6-alkyl, C1-6-alkyloxy or R5and R6taken together , form a bivalent radical of the formula-NR8-C(O)-NR9- or-NH-C(NH-R10)=N-, where R8and R9is hydrogen, C1-6-alkyl, R10is hydrogen, C1-6-alkylsulphonyl, C1-6-allyloxycarbonyl

The invention relates to pharmaceutical compositions for inhibiting gonadotropinreleasing hormone, which contains condensed-bicyclic compound consisting of a Homo - or heterocyclic 5-7-membered ring groups, Homo - or heterocyclic 5-7-membered ring group

The invention relates to a piperidine derivative of General formula (I) where Z represents the group -(CH2)m-CH(OR3) or a carbonyl group, R1is hydrogen or (C1- C3)alkyl, R2- (C1- C3)alkyl, or R1and R2together form a chain -(CH2)n, where n is the number of 3 - 5, or -(CH2)2-O-(CH2)2-, m = 0 - 1, n = 1 - 2, R3- hydrogen or-COCH3and R4- hydrogen, -CH3, -OH or-OCH3provided that when Z represents a carbonyl group, h = 2, or their pharmaceutically acceptable salts

The invention relates to new aryl-substituted derivatives of piperidine, which has antagonistic activity to the receptor NK3person, to a method for their production and to their use in pharmaceutical compositions

-methoxykynuramine acids" target="_blank">

The invention relates to a method of producing methylamino- methoxykynuramine acids of the formula I, where Y represents a C-organic radical through reaction of Pinner interaction achilleid formula II with an alcohol and subsequent interaction of the formed in the Pinner reaction of ester of the formula (IV) with hydroxylamine to obtain the oxime of the formula V by methylation of the oxime of the formula V to oximoula ether of the formula VI or b) somethingitaliano obtaining oximoula ester of formula VI, followed by interaction oximoula ester of formula VI with methylamine, characterized in that in the reaction of Pinner used alcohol of the formula III R-OH, boiling point above 75°C
Up!