Derivatives triazolopyrimidine, the retrieval method, the fungicidal composition

 

(57) Abstract:

Usage: in agriculture as fungicides. The inventive product derivatives triazolopyrimidine formula 1, where R1- C1-12-alkyl, C2-6alkenyl etc., R2is hydrogen, C1-4-alkylhalides etc. Reagent 1: compound of formula II. Reagent 2: compound of formula III: HN R1R2. Fungicidal composition containing the compounds of formula I. 3 C. and 4 h.p. f-crystals, 14 PL.

(I)

(II)

The invention relates to certain derivatives of triazolopyrimidine, to methods for their preparation, to compositions containing such compounds and to their use as fungicides.

In EP-A-0071792 described compounds of General formula

< / BR>
in which R1is alkyl, halogen, alkoxy, cyano, cycloalkyl, aryl, aryloxy, aaltio, arylalkyl, arylalkyl or arylalkyl, each may be substituted by halogen or alkoxy, or R1nis benzene, indinavir or tetrahydronaphthalene ring condensed with a phenyl ring, and the aromatic fragments of the above-mentioned groups optionally substituted by alkyl, alkoxy, halogen or cyano, n is 1 or 2, R2P> is the same as R2but can also be halogen, cyano or alkoxycarbonyl, or together with R3can form alkylenes chain containing up to 2 double bonds. Indicated that the compounds are active against various phytopathogenic fungi, especially class phykomycets. However, the proof of fungicidal activity is provided only for 17 of 80 described compounds against Plasmopara viticola, a class representative filmicity mushrooms.

Now found a new class derived triazolopyrimidine, which shows a different spectrum fungicidal activity, the new compounds are particularly active against fungi, which are representatives of the class of records of Ascomycetes, such as Venturia inaequalis, Botrytis cinerea and alternotia soloni.

According to the invention features a compound of General formula

< / BR>
in which R1is optionally substituted by alkyl, alkenyl, quinil, alkadienes, cycloalkyl, bicycloalkyl or heterocyclic group, R2is a hydrogen atom or alkyl group, or R1and R2together with the neighboring nitrogen atom are optionally substituted heterocyclic ring, R3is optional salmenkaita hydrogen atom or amino group, the alkyl, cycloalkyl or bicycloalkyl, and R6is a hydrogen atom or alkyl.

When the compound contains an alkyl, alkenyl, quinil or akadeemiline replacement group, they can be linear or branched and may contain up to 12, preferably up to 6, and especially up to 4 carbon atoms. Bicycloalkyl group may contain from 4 to 12, preferably 4 to 8 carbon atoms. The aryl group may be any aromatic hydrocarbon group, especially phenyl or naftilos group. Heterocyclic ring may be saturated or unsaturated ring containing at least one heteroatom, 3-6-ticleni ring is preferable, and particularly preferably 5-6-ticleni ring. Especially preferred are nitrogen-containing heterocycles, such as aziridinyl, pyrrolidinyl, morfini and thiazolyl.

When any of the above substituents are indicated as optionally substituted, the substitute groups, which optionally may be present, can be any of those usually used in the development of pesticide compounds and/or their modifications to influence their structure/activity, stability, permeability, and other properties.hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, formyl, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulfonyl, alkylsulfonyl, carbarnoyl, alkylamino, phenyl, phenoxy, benzyl, benzyloxy, heterocyclyl, especially furyl, and cycloalkyl, especially cyclopropyl. Usually can be 0-3 substituent. When any of the above substituents is or contains substitutional alkyl group, it may be linear or branched and may contain up to 12, preferably up to 6, and especially up to 4 carbon atoms. When any of the above substituents is or contains an aryl or cycloalkyl fragment, by itself, aryl or cycloalkyl fragment can be substituted by one or more halogen atoms, nitro, cyano, alkyl, haloalkyl, alkoxy or haloalkoxy. If cycloalkyl and heterocyclic groups optional substituents include groups which together with two adjacent carbon atoms cycloalkyl or heterocyclic group to form a saturated or unsaturated hydrocarbon ring. In other words, a saturated or unsaturated hydrocarbon ring may be optionally condenser is B>1-12-alkyl, C2-6-alkenyl, C2-6-quinil, C4-12-alkadienes, more preferably C4-8-alkadienes, C3-8-cycloalkyl or C4-8-bicycloalkyl or 3-6 ticleni a heterocycle, each group or ring are optionally substituted by one or more substituents selected among halogen atoms, preferably chlorine, nitro, cyano, hydroxyl, C1-4-alkyl, especially methyl, C1-4-haloalkyl, especially CF3C1-4-alkoxy, especially Me-O-, C1-4-haloalkoxy, especially CF3-O, amino, C1-4-alkylamino, di-C1-4-alkylamino, formyl, C1-4-haloalkylthio, di-C1-4-alkoxyphenyl, purile and diploid-C3-6-cycloalkyl, or in the case when R1is C3-8-cycloalkyl or 3-6-ticleni a heterocycle, optionally ortho-fused with the benzene ring.

Preferably R2is a hydrogen or C1-4-alkyl.

Also preferably, R3was the phenyl or naphthyl, each group optionally substituted by one or more substituents selected among halogen, nitro, cyano, hydroxyl, C1-12-alkyl, C1-12-haloalkyl, C1-12-al is carbonyl, carboxyl, phenyl, phenoxy and benzyloxy.

More preferably R3is phenyl, optionally substituted with up to three substituents selected among halogen atoms,C1-4-alkyl, C1-4-haloalkyl, C1-4-alkoxy, C1-4-haloalkoxy, phenoxy and benzyloxy, or naphthyl.

Preferably R4is hydrogen or halogen or the group-NR5R6where R5is a hydrogen atom or an amino group, a C1-4-alkyl, especially stands, C3-6-cycloalkyl or C4-8-bicycloalkyl, and R6is a hydrogen or C1-4-alkyl, especially stands.

Especially preferred subgroup of compounds of formula I is one in which R1is stands, ethyl, propylene, heptyl, dodecyl, benzyl, dichlorocyclopentane, furylmethyl, triftormetilfosfinov, dimethoxyphenethyl, Pentium, PROPYNYL, dimethyloctadecyl, cyclopropyl, cyclopentyl, oxacyclopentane, trimethylcyclopentanone, cyclohexyl, trimethylcyclohexyl, cyclooctyl, indenolol, bicycloheptene, dichloropyridine, pyrrolidinium, morpholinium, or benzothiazolium, R2is an atom of water is>is phenyl, florfenicol, chloro-phenyl, bromperidol, chloroform, were, propylphenyl, cryptomaterial, methoxyphenyl, ethoxyphenyl, acid, trimethoxyphenyl, cryptomaterial, biphenylyl, phenoxyphenyl, benzyloxyphenyl or naphthyl, and R4is hydrogen, fluorine, chlorine, bromine or iodine, or amino, methylamino, dimethylamino, hydrazino, cyclopentylamine or bicycloheptadiene.

The invention also provides a method for obtaining compounds of formula I, as defined above, which is that

a) introducing the reaction of compound of General formula

< / BR>
in which R3has the previously indicated meanings, and Hal is chlorine or bromine, with a compound of General formula

HNR1R2(III)

in which R1and R2are these values to obtain the compounds of formula I in which R4is a chlorine atom or bromine;

C) if desired, is introduced into the reaction of the compound of formula 1 obtained in stage (a) with a fluorinating agent to obtain compounds of formula I in which R4is a fluorine atom;

C) if desired, enter a compound of formula 1 obtained in stageii (a), to restore and desired, is introduced into the reaction of the compound of formula 1, obtained in stage (a) with the compound of the formula

HNR5R6(IV)

in which R5and R6have these values, to obtain the compounds of formula 1 in which R4is a group-NR5R6;

e) if desired, is introduced into the reaction of the compound of formula 1 obtained in stage (d), in which both R5and R6are hydrogen atoms, with diiodomethane in the presence diastereomer agent to obtain compounds of formula 1 in which R4is an atom of iodine.

Process stage (a) is usually carried out in the presence of a solvent. Suitable solvents are ethers, such as dioxane, diethyl ether, especially tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and toluene. The reaction is usually carried out at a temperature in the range of 0oC to 70oC, the preferred temperature interval is 10-35oC. it is Also preferred that the reaction was carried out in the presence of a base. Suitable bases include tertiary amines, such as triethylamine, and inorganic bases such as potassium carbonate and sodium carbonate. Alternatively the base can serve as an excess of the compounds of formula III.

oC) to the boiling temperature of the reaction mixture under reflux, the preferred temperature interval is the interval from the 40oC to the boiling temperature of the reaction mixture under reflux. Suitable fluorinating agents are the alkali metal fluorides, especially fluoride and potassium fluoride antimony.

Regenerating agent used in stage (C), is typically a catalytic hydrogenating agent, i.e., hydrogen gas is used at high pressure in the presence of a catalyst. Preferably the catalyst is palladium on coal. Also preferably, this stage was carried out in the presence of a base. Suitable bases are tertiary amines, such as triethylamine, and inorganic bases such as sodium carbonate or especially sodium hydroxide. This stage also usually carried out in the presence the temperature in the interval 0oC 70oC, the preferred temperature interval is the interval 10oC - 35oC.

Process stage (d) is usually carried out in the presence of a solvent. Suitable solvents are ethers, such as dioxane, diethyl ether and tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and especially toluene. The reaction is conveniently carried out at a temperature in the range of 20oC to the boiling temperature of the reaction mixture under reflux, the preferred temperature range of from 40oC to the boiling temperature of the reaction mixture under reflux. It is also preferred that the reaction was carried out in the presence of a base. Suitable bases are tertiary amines, such as triethylamine, and inorganic bases, such as potassium carbonate or sodium carbonate. Alternatively the base can serve as an excess of the compounds of formula IV.

When R1is the same Deputy, as R5and R2is the same Deputy, and R6in the resulting compound of formula 1, a compound of formula III will be the same as the compound of the formula IV, and, therefore, stage (a) and (d) can be carried out Coliseum on stage (e), can be any alkilany ester of nitrous acid. When using Olkiluoto ester of nitrous acid it can also serve as a co-solvent with diiodomethane. The reaction is usually carried out at a temperature of from 60oC to 120oC, the preferred reaction temperature is a temperature between 70oC to 110oC.

The compounds of formula II can be obtained by the reaction of compounds of General formula

< / BR>
in which R3matter mentioned previously, with glorieuses or brainwashin agent such as oxidoreductase or oxybromide phosphorus.

The compounds of formula V can be obtained by the reaction of 3-amino-1,2,4-triazole with the corresponding ester of malonic acid in alkaline conditions in accordance with the method of V. Makisumi, Chem. Pharm. Bull, 9, 801, /1961/.

The compounds of formula III and IV are known compounds or can be obtained by methods analogous to known methods.

It was found that compounds of General formula I possess fungicidal activity. Therefore, the invention also provides a fungicidal composition which contains a carrier and as active ingredient a compound of formula 1, described to enter the I formula 1, as described above, with at least one carrier. Such a composition may contain a single compound or a mixture of several compounds of the present invention. Also envisaged that different isomers or mixtures of isomers may have different levels or spectra of activity and, therefore, the composition can contain individual isomers or mixture of isomers.

The composition according to the invention preferably contains 0.5 to 95 wt. the active ingredient.

A carrier in a composition according to the invention is any material with which the active ingredient is formulated to facilitate application to be processed places, which may be, for example, plants, seeds or soil, or to facilitate storage, transport or processing. The carrier may be solid or liquid, including a material which is normally gaseous but which when compressed, forms a liquid, and can be used any of the media in the formulation of fungicidal compositions.

Suitable solid carriers include natural and synthetic clays and silicates, for example natural silicates such as hard-shelled land; magnesium silicates, such as talc; magnesium alumina and mica, calcium carbonate, calcium sulfate, ammonium sulfate, synthetic hydrated silicon oxides and synthetic aluminum silicate or calcium, elements such as carbon and sulfur, natural and synthetic resins, such as coumarone resins, polyvinyl chloride, polymers and copolymers of styrene, solid polihlorvinila, bitumen, waxes, such as beeswax, paraffin wax, and chlorinated mineral waxes; and solid fertilizers, for example superphosphates.

Suitable liquid carriers include water, alcohols, for example isopropanol and glycols, ketones, for example acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, ethers, aromatic or analiticheskie hydrocarbons such as benzene, toluene and xylene; petroleum fractions such as kerosene and light mineral oils; chlorinated hydrocarbons, for example carbon tetrachloride, perchloroethylene and trichloroethane. Often suitable are mixtures of different liquids.

Fungicidal compositions often form and transported in the form of concentrates, which are then diluted by the user before use. The presence of small amounts of media, which is a surface active agent, facilitates this process razvalivaetsya surface active agent. For example, the composition may contain at least two carriers, at least one of which is a surface-active agent.

Surface active agent may be an emulsifying agent, dispersing agent or wetting agent; it may be nonionic or ionic. Examples of suitable surface active agents include the sodium or calcium salts of polyacrylic acids, lignosulfonic acids; the condensation products of fatty acids or aromatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; esters of fatty acids and of glycerol, sorbitan, sucrose or pentaerythritol; condensates them with ethylene oxide and/or propylene oxide; condensation products of fatty alcohols or alkyl phenols, for example p-op or p-ochiltree, with ethylene oxide and/or propylene oxide; sulfates or sulfonates of these condensation products; alkali or alkaline earth salt, preferably the sodium salts of esters of sulfuric or sulfonic esters containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulphate, sodium secondary alkyl sulphates, sodium salts of sulforophane and copolymers of ethylene oxide and propylene oxide.

Compositions of the invention can be formed, for example, in the form of wettable concentrates, emulsions, suspension concentrates and aerosols. Wettable powders usually contain 25, 50 or 75 wt. the active ingredient and, in addition, they contain in addition to solid inert carrier 3-10 wt. dispersing agent and, if necessary, 0-10 wt. stabilizer(s) and/or other additives such as penetrants or thickeners. Dusty usually form in the form gustovich concentrate having a similar composition to that of a wettable powder but without a dispersant, and may be diluted in the field with other solid media to obtain a composition usually containing 0.5-10 wt. the active ingredient. Granules are usually prepared to have a size between 10 and 100 BS mesh /1,676 0,152 mm and can be manufactured by agglomeration or impregnation. Usually pellets containing 0.5-75 wt. the active ingredient and 0-10 wt. excipients, such as stabilizers, surfactants, slow release modifiers and binding agents. The so-called "dry flowable powders are composed of relatively small granules having a relatively high concentration of the active ingredient. Mulgirigala what about the ingredient, 2-20 wt. /the amount of emulsifiers and 0-20 wt./ the amount of excipients, such as stabilizers, penetrants and corrosion inhibitors. Suspension concentrates are usually thus to obtain stable nonsetting fluid product, they usually contain 10-75 wt. a suspending agent, such as protective colloids and thixotropic agents, 0-10 wt. other auxiliary substances, such as antifoams, corrosion inhibitors, stabilizers, penetrants and thickeners, and water or an organic liquid in which the active ingredient is practically insoluble; certain organic solids or inorganic salts may be dissolved in the formulation to prevent sedimentation or as antifreeze for the water.

Aqueous dispersions and emulsions, for example compositions obtained by dilution of a wettable powder with water, or concentrate according to the invention with water, also lie within the scope of the invention. These emulsions can be of the type water-in-oil or oil-in-water and to have mainetoday" texture.

Compositions of the invention can also contain other ingredients, for example other compounds with herbicide, insecticide or funghi present invention is the use of media, which will provide slow allocation fungicidal compounds in the environment surrounding the protected plant. Such formulations with delayed allocation can be made, for example, in the soil near the roots of plants of grapes or may include an adhesive component that allows to apply them directly on the stem of a plant grapes.

In addition, the invention provides the use as a fungicide compounds of General formula 1, as defined above, or a composition as defined above, and a method of combating fungi in their habitats, which is in the handling of habitats, which can be, for example, vegetable objects affected by fungi, seeds of such plants or the medium in which they grow such plants or in which they will be grown, such a compound or composition.

The invention is widely applied to protect crops against exposure to fungi. Typical crops which may be protected, are grapes, cereals such as wheat and barley, apples and tomatoes. The duration of protection is usually dependent on the selected connection, but also on many external factors, such to the e 5-chloro-6-/4-were/-7-cyclopentylamine-1,2,4-triazolo/1,5-a/pyrimidine

/R1cyclopentyl, R2H, R34-were, R4CI/

Dissolve 1.8 g /6 mmol/ 5.7-dichloro-6-/4-were/ -1,2,4-triazolo-/1,5-a/pyrimidine in tetrahydrofuran. Then add a solution of 0.51 g /6 mmol/ cyclopentylamine and 0.61 g /6 mmol/ cyclopentylamine under stirring and continue stirring for another 3 h at room temperature /20oC/. Then the reaction mixture is evaporated in vacuum and the residue extracted with dichloromethane and water /100 ml each/. The organic layer is dried over sodium sulfate and the solvent is evaporated in vacuum. The residue is crystallized from ethyl acetate, to obtain 1.7 g of 5-chloro-6-/4-were/ /-7-cyclopentylamine-1,2,4-triazolo/1,5-a/pyrimidine in the form of yellowish crystals, so pl. 158oC. the Output 87 of Teoret. H1NMR: 1,3-1,75 /2m, 8H/, 2,43 /c, IH/, to 3.73 /m, IH/, 5,97 /d, IH/, 7,25 /m, 4H/, 8,25 /s, IH/ ppm (ppm)

Example 2. Getting 5-bromo-6-phenyl-7-cyclopentylamine-1,2,4-triazolo/1,5-a/pyrimidine

/R1cyclopentyl, R2H, R3phenyl, R4bromine/

Dissolved in 40 ml of tetrahydrofuran and 2 g /5.7 mmole/ 5,7-dibromo-6-phenyl-1,2,4-triazolo-/1,5-a/-pyrimidine. Then add a solution of 0.61 g, 6 mmol/ creatinine and 0.51 g /6 mmol/ cyclopentylamine under stirring and continue stirring for another 2 h at counterrotation and water (100 ml each). The organic layer is dried over sodium sulfate and the solvent is evaporated in vacuum. After chromatography of the residue on a column of 3.5 to 15 cm silica gel, using as eluent ethyl acetate: petroleum ether in the ratio 3:7 obtain 0.6 g of 5-bromo-6-phenyl-7-cyclopentylamine-1,2,4-triazole/1,5-a/pyrimidine in the form of a yellowish oil. Exit 28% of theory.

1H-NMR: d 1,3-1,7 /2 m, 8H/, 3,64 /m, IH/, 6,05 /d, IH/, 7,34 /m, 2H/, 7,50 /m, 3H/, compared to 8.26 /s, IH/ ppm (ppm)

Example 3. Getting 6-/4-methoxyphenyl/-7-cyclopentylamine-1, 2, 4-triazolo-/1,5-a/-pyrimidine

/R1cyclopentyl, R2H, R34-methoxyphenyl, R4H/

Dissolve 5,1 g /14,8 mg/ DL 5-chloro-6-/4-methoxyphenyl/-7-cyclopentylamine-1, 2, 4-triazolo-/1,5-a/pyrimidine, obtained by the method of example 1, in a mixture of 100 ml of methanol and 15 ml of 1 H aqueous sodium hydroxide, was added 0.5 g of palladium on coal (5% E 10) and stirred the reaction mixture for 3 hours in hydrogen atmosphere (5 bar). The catalyst is filtered off and the filtrate is evaporated in vacuum. After chromatography of the precipitate on the column 3,5 C 15 cm silica gel, using as eluent ethyl acetate: petroleum ether 4:1, and evaporation of the solvent in vacuo obtain 2.6 g of 6-/4-methoxyphenyl/-7-cyclopentylamine-1, 2, 4-triazolo-/1,5-a/-pyrimidine in the form of bestv 2H/, 8,32 /s, IH/, 8.34 per /s, IH/ ppm (ppm)

Example 4. Getting 5-methylamino-6-phenyl-7-cyclopentylamine-1,2,4 - triazole/1,5-a/pyrimidine

/R1cyclopentyl/, R2H, R3- R5R6, R5CH3, R6H/.

Refluxed for 10 h in a mixture of 3.1 g /10 mmol/ 5-chloro-6-phenyl-7-cyclopentylamine-1,2,4-triazolo/1,5-a/ pyrimidine, obtained by the method of example 2, 5 ml of methylamine, 5 ml of diethylamine and 50 ml of toluene. After cooling, the reaction mixture is washed with 50 ml of water and separate the organic layer, dried over sodium sulfate and evaporated. Recrystallization of sediment from diisopropylamido ether gives 2.3 g of 5-methylamino-6-phenyl-7-cyclopentylamine-1,2,4-triazolo/1,5-a/pyrimidine as colorless crystals, so pl. 158-160oC. a Yield of 75% from Teoret.1H-NMR: d 1,25-1,7 /mm, 8H/ 2,95 /d, 3H/, 3,42 /m, IH/, 4,48 /m 5,55 /d, IH-/, 7,3-7,5 /m, 5H//, 8,03 /s, IH/.

Example 5. Getting 5-fluoro-6-/4-methoxyphenyl/-7-cyclopentylamine-1, 2, 4-triazolo/1,5-a/pyrimidine

/R1cyclopentyl, R2H, R34-methoxyphenyl, R4F/

Suspended 3.1 g /0.05 mol/ in a mixture of 60 ml of dry sulfolane and 20 ml of toluene, the mixture is then refluxed for 6 hours with water-separator. Add 8.5 g /0,025 mol/ 5-chlorate temperature and distilled azeotrope of sulfolane and toluene as long while the temperature of the reaction mixture does not rise to 200oC. Then the reaction mixture is left at this temperature for 3 days before cooling to room temperature, and then poured into 600 ml of water. The mixture is then filtered and the precipitate washed with water. Then the residue is dissolved in dichloromethane, extracted twice with water, dried over sodium sulfate and evaporated in vacuum solvent. Then the residue is washed twice with warm diethyl ether, the ether decanted fraction, then dried in vacuum. After flash-chromatography on silica gel using a mixture of petroleum ether and ethyl acetate as eluent, to obtain 4.5 g of 5-fluoro-6-/4-methoxyphenyl/-7-cyclopentylamine - 1,2,4-triazolo-/1,5-a/pyrimidine as a colourless solid crystals, so pl. 124oC. Yield 55% from Teoret.

Example 6. Getting 5-iodine-6-/2-chlorophenyl/-7-cyclopentylamine-1,2,4-triazolo-/1,5-a/pyrimidine

/R1cyclopentyl, R2H, R32-chlorophenyl, R41/

Mix together and 3.3 g /10 mmol/ 5-amino-6-/2-chlorophenyl/-7-cyclopentylamine-1,2,4-triazolo-/1,5-a/-pyrimidine, obtained by the method of example 4, and 50 ml diiodomethane. Add 20 ml of isopentylamine in nitrogen atmosphere and the reaction mixture is heated 3 hours at 90oC. Then reacciones-chromatography on a column of silica gel, using a mixture of petroleum ether and acetolactate 7:3 as eluent, get 1,33 g 5-iodine-6-/2-chlorophenyl/-7-cyclopentylamine-1,2,4-triazolo-/1,5-a/-pyrimidine as colorless crystals, so pl. 150oC. Yield: 30.3% from Teoret.

Examples 7-117. Work according to the procedures described in examples 1-6, get other compounds according to the invention, as more fully shown in the table. 1. In this table, the compounds are identified by reference to formula 1. Melting point, NMR spectrum, and C, H, N analysis for the compounds of examples 7-117 are given in table. 2.

Example 118. Getting 7-azepin-1-yl-5-chloro-6-(2-chloro-6-fluoro-phenyl)-2,2,4-triazolo/1,5-and/pyrimidine

R1, R2azepin-1-yl, R3-2-chloro-6-fluoro-phenyl, R4-chlorine

5,7-Dichloro-6-(2-chloro-6-fluoro-phenyl)-1,2,4-triazolo/1,5-a/-pyrimidine (16 g, 0.05 mol) is suspended in dichloromethane (100 ml). Add ASEAN (4.9 g, 0.05 mol) with stirring, and then triethylamine (5.5 g, by 0.055 mol). The reaction temperature (30-35oC) support with the aid of an ice bath. Then the reaction mixture was stirred for 3 h at ambient temperature, followed by washing two times with 1 N. hydrochloric acid and once with water. The organic layer is separated, dried with anhydrous sodium sulfate, and RA is utilmately ether (50 ml) are obtained as beige crystals (16,1 g, 85% of theoretical.), having a melting point of 152-154oC.

Examples 119-218. The following examples (patterns, PL. 3; the physical data table. 4 is synthesized analogously to the method of example 118.

< / BR>
Example 219. Fungicidal activity against Venturio inoequais on different types of Apple trees.

Cuttings of Apple varieties Morgenduft approximately 6 weeks of age treated with a solution of the test compound (400 ppm) in water /acetone/ Triton X or in water//methanol/Triton X. After 24 h infect plants with a suspension of conidia of Venturia inoqualis /about 50,000 conidia/ml, incubated in a dark climate chamber at 100% relative humidity for 48 h, and then maintained at a relative humidity of 95-99% and a temperature of 18-20oC during the day and 13oC during the night for about 14 days. The degree of contamination is evaluated according to the following scheme:

0 no intrusion

1 1-10% infection

2 11-40% infection

3 41-100% infection

The results of these tests are shown below.

Example N Activity

1 1

2 0

3 2,5

4 2,3

7 1,8

8 1

9 1

11 2,8

12 1,3

13 2,3

14 2

15 2,7

16 2,7

17 0

19 2,4

20 3

21 1,4

22 0

23 2,5

24 3
<>/BR>37 1,3

38 0

39 1,0

40 0

41 0

43 0

46 1,0

47 2,8

48 2,9

49 2,9

50 2,9

51 2,5

52 2,8

55 2,5x< / BR>
56 1,5x< / BR>
57 1,5x< / BR>
58 2,3x< / BR>
59 1,8x< / BR>
60 1,5x< / BR>
Example N Activity

61 0

62 0

63 0

64 0

70 0

71 1,3

73 2,8

80 0,8

81 2,3

82 2,3

83 1,6

86 1,3

87 0

88 0

91 2,0

105 0

106 0

107 0

xthe concentration of the test compound 200 ppm

Example 220. Determining values for MICK compounds against various phytopathogenic fungi.

The MIC /minimum inhibitory concentration was determined by tests with serial dilution using card microtitration with 48 cells. Dilutions of the tested compounds nutrient solution and the distribution of the cells is performed with the help of a robot processor TECAH P P 5000.

Compounds were diluted to the following concentrations: 100, 50, 25, 12,5, 6,25. 3613, 1,56, 0,73, 0,39, 0,20, 0,10 and 0.05 µg/ml.

To prepare the nutrient solution is neutralized juice V8 /trade name/ calcium carbonate and centrifuged. The supernatant was diluted with distilled water /1:5/ to the final concentration.

oC for 6-8 days. Determine the MIC value by visual evaluation boards. In the case of alternaria soloni, and Botrytis cinerca the lowest concentration in a series of diluted without mycelium growth is defined as the MIC value. For Septoria nodorum was not the MIC values, but only regularly observed a strong inhibition of growth.

The results of these tests are given in table. 5.

Example 221. The fungicidal activity of the compounds of the invention was tested using the following tests.

// Direct-protecting activity against late blight of tomato /Phytophtora infestars: PIP/

The test is directly protect test when using leaf spraying. Upper surface of leaves of tomato with two sprouted leaves (sort First in the field) are sprayed with a solution of active material in acetone/water 1:1, containing 0.04% tween-20 (trade name, a surface-active substance polyoxyethylene ether sorbitan). The plants are treated using automatic spraying line with atomizers nozzles. The concentration is equal to 1000 ppm, and the amount of spraying is 700 l/ha After 24 h in normal conditions of greenhouses upper surface of leaves inoculant by spraying water is agnosti and 5 days under the conditions of the growth chamber. The assessment is based on the percentage of diseased leaf area compared to control leaves.

/b/ a Direct protective effect against downy mildew /Plasmopara viticola: PVP/.

The test is a direct protect test using leaf spraying. The lower surface of leaves of whole plants of grapes (grape variety Cabernet Sauvignon) are sprayed with the test compound at a dose of 1000 ppm using an automated spray line, as described above in /a/ and after 24 h in normal conditions greenhouses lower surface of leaves inoculant by spraying with an aqueous suspension containing 2,5104zoosporangium inside host/ml Inoculated plants are incubated for 24 h in a room with high humidity, 5 days in normal conditions of the greenhouse, and then return for another 24 h in high humidity. The assessment is based on the determination of the percentage of leaf area covered with sporulation, compared to control leaves.

/c/ Activity against early rot of tomatoes /Alternoria solani-; AS/.

In this test measure the contact preventive activity of the tested compounds, applied by spraying on the leaves. Seedlings of tomato (variety Outdoor Girl) grow to the stage at which dissolved in the and/. Compound is applied in the form of solutions or suspensions in a mixture of acetone and water (50:50 volume/volume / containing 0.04% of surfactants /tween-20 trade name/. One day after treatment the seedlings inoculant spraying the upper surface of the leaves with a suspension of conidia of A. solani with 104spores/ml 4 days after inoculation the plants stand in a moist chamber at the 21oC. Disease assessed 4 days after inoculation, based on the percentage of leaf area covered by lesions.

/d/ Direct-protecting activity against gray mold of beans /Botrytis cinerea, BCB/.

The test is a direct protect test using leaf spraying. Upper surface of leaves of large beans (sort Sutton) are sprayed with the test compound at a dosage of 1000 ppm using an automated line for spraying, as described above in /a/. After 24 h after spraying the leaves inoculant with an aqueous suspension containing 105conidia/ml Within 4 days after inoculation the plants stand in a moist chamber at the 21oC. Disease assessed 4 days after inoculation, based on the percentage of leaf surface covered with lesions.

/e/ Asset is reattaching the leaf spraying. Leaves of wheat plants (variety Norman) at the stage of a single sheet inoculant by spraying with an aqueous suspension containing 1106spores/ml Inoculated plants are incubated for 24 h in a chamber with high humidity before processing. The plants are sprayed with a solution of the test compounds at a dose of 1000 ppm using an automated line for spraying, as described in /a/. After drying, the plants will last for 6-8 days at 22oC and moderate humidity, then evaluate. The assessment is based on the density of defects on the sheet in comparison with the leaves of the control plants.

/f/ Activity against brown rust of wheat /Puccinia recondita, PR/

The test is a direct protect test using leaf spraying. The winter wheat seedlings (cultivar avalon) has grown to the stage 1-1,5 leaves. Then the plants are sprayed with the test compound at a dose of 1000 ppm using an automated line for spraying, as described in /a/. Compound is applied in the form of a solution or suspension in a mixture of acetone-water / 50: 50 volume/volume / containing 0.04% of a surface-active agent tween-20 /trade name/. After 18-24 h after treatment sprouts inoculant spraying plants on all sides by water siah high humidity at 20-22oC. Then the plants can withstand under normal greenhouse conditions, i.e. at a moderate relative humidity and at 20oC. the Disease is assessed 10 days after inoculation, based on the percentage of leaf area covered sporelike pustules, compared with the control plants.

/g/ Activity against powdery mildew /Erysiphe graminis f.sp. hordei; EG/

The test is a direct therapeutic test using leaf spraying. Leaves of barley seedlings (cultivar Golden Promise) inoculant by dusting with conidia of powdery mildew on the day before the processing of the test compound. Inoculated plants stand all night in the greenhouse at room temperature and humidity before processing. The plants are sprayed with the test compound at a dose of 1000 ppm using an automated line for spraying, as described in /a/. After drying, the plants are returned to the chamber at 20-25oC and moderate humidity for 7 days, then evaluate. The evaluation is made based on the percentage of leaf area covered with sporulation, compared with the same control plants.

/h/ Activity against pyricularia rice /Pyricularia oryzae PO/

The test is a direct therapeutic test with ispolzovani suspension, contains 105spores/ml for 20-24 hours prior to processing the test connection. Inoculated plants are incubated overnight in high humidity and then allowed to dry before spraying the test compound at a dose of 1000 ppm using an automated line for spraying, as described in /a/. After treatment, the plants stand in rice camera at 25-30oC and high humidity. The evaluation is made after 4-5 days after treatment is based on the density of necrotic lesions on the leaf compared with the control plants.

/i/ Activity against Glazkova blotch of wheat in vitro /Pseudocercosporella herpotrichoides PHI/

In this test, measured in vitro activity of compounds against the fungus that causes ocellar spot of wheat. The test compound dissolved or suspended in acetone and added in aliquots of 4 ml of half the concentration of the potato-destrozado broth, distributed in Petri dishes with 25 compartments, to obtain a final concentration of 50 ppm connection and 2.5% acetone. Each compartment inoculant when the piston diameter 6 mm agar/mycelium taken from the 14-day culture of P. herpotrichoides. Plates are incubated at 20oC for 12 days until until high q is measured in vitro activity of compounds against Fusarium species, which cause rot of roots and stems. The test compound dissolved or suspended in acetone and added to the melt pologrebskogo potato-dextrose agar in order to obtain a final concentration of 50 ppm connection and 2.5% acetone. After placing an agar plate inoculant pistons 6 mm in diameter made of agar and mycelium taken from 7 day cultures of Fusarium p. Plates are incubated at 20oC for 5 days and measure radial growth of traffic.

// the Activity against Rhigoctonia in vitro /Rhigoctonia solani; RSI/

In this test measure the in vitro activity of compounds against Rhigoctonia solani, which causes root and stableboy rot. Compound dissolved or suspended in acetone and added in aliquots of 4 ml pologrebskogo potato-dextrose broth, placed in Petri dishes with 25 compartments, receive a final concentration of 50 ppm connection and 2.5% acetone.

Mushroom inoculat consists of mycelial fragments of R. solani grown in shaking culture, and add to the broth to ensure 2103fragments/ml of broth. Plates are incubated at 20oFrom 10 days before until it is time to assess the growth of mycelium.

The existence of control brisneyland more diluted control in accordance with the criteria:

0 less than 50% disease control

1 about 50-80% of the disease from control

2 more than 80% disease control

The results of these tests are shown in table.6.

Example 222. The fungicidal activity of the compounds of the invention was investigated using tests.

/a/ Anticorona activity downy mildew of grapes /Plasmopara viticola; PVA/

The test is a direct antispamovy test using leaf spraying. The lower surface of leaves of grapes /grape variety: Cabernet Sauvignon/ about 8 cm height inoculant water suspension containing 5104zoosporangium inside host/ml Inoculated plants are incubated for 24 h at 21oC in a chamber with high humidity, then 24 h in the greenhouse at 20oC and 40% relative humidity. Infected leaves sprayed with the bottom surface with a solution of the test compounds in water-acetone 1:1, containing 0.04% tween-20 /trade name, surface active agent polyoxyethylene ether sorbitan/. Plants sprayed using a track sprayer equipped with 2 air-atomizers nozzles. The concentration of 600 ppm, and spray volume of 750 l/ha After drying, the plants back into the greenhouse at 20

/b/ Direct-protecting activity against late blight of tomato / Phytophtora infestans PIP/

The test is a direct protect test using leaf spraying. Plant tomatoes with two true leaves /grade First field is/ are sprayed with the test compound at a dose of 600 ppm, as described in /a/. After drying, the plants are incubated for 24 h in the greenhouse at 20oC and 40% relative humidity. Upper surface of leaves then inoculant water suspension containing 2105zoosporangium inside host/ml Inoculated plants are incubated for 24 h at 18oC in a chamber with high humidity, and then 5 days in the growing chamber 15oC and 80% relative humidity under a 14 hour daylight. The assessment is based on the percent area diseased leaves compared with that in control leaves.

// Activity against early rot of tomatoes /Alternaria solani; AS/

The test is a direct preventive test using leaf spraying. The tomato seedlings /grade Outdoor Girl/ on a stage at which blossomed a second sheet, sprayed with the test compound at a dose of 600 RMP, as described in the coziness of the upper surface of the sheet with an aqueous suspension of A. Solqni conidia containing 1104conidia/ml After 4 days in a chamber with high humidity at 21oC evaluate the disease based on the percentage of surface area covered with lesions, compared with the control plants.

/d/ Direct-protecting activity against Botrytis beans /Botrytis cinerea BCB/

The test is a direct protect the test using leaf spraying. Legume plants /cultivar Sutton/ two pairs of leaves are sprayed with the test compound at a dose of 600 RMP, as described in /a/. After drying, the plants are incubated for 24 h in the greenhouse at 20oC and 40% relative humidity. Then the upper surface of leaves inoculant water suspension containing 1106conidia/ml Plants stand for 4 days at 22oC in a chamber with high humidity. The assessment is based on the percentage surface area of diseased leaves compared to control leaves

/e/ Activity against powdery mildew of barley / Erysiphe graminis f.sp. hordei; EG/

The test is a direct therapeutic test using leaf spraying. The leaves of the sprouts of barley /grade Golden Promise/ stage single sheet inoculant by dusting with conidia of powdery mildew, and incubated in talem at a dose of 600 ppm, as described in /a/. After drying, the plants back into the greenhouse at 18oC and 40% relative humidity for 7 days. The assessment is based on the percentage of leaf area covered with sporulation, as compared to that for the leaves of control plants.

/f/ Activity against pyricularia rice /Pyricularia oryzat PO/

The test is a direct therapeutic test using leaf spraying. The leaves of the sprouts of rice at the stage of the second sheet starts to bend (sort of Ichiishi), inoculant with an aqueous suspension containing 105spores/ml Inoculated plants are incubated for 24 h at 18oC in a chamber with high humidity, and then sprayed with the test compound at a dose of 600 ppm, as described in /a/. Treated plants stand 8-9 days in the greenhouse at 22oC and 90% relative humidity. The assessment is based on the density of necrotic lesions compared with the control plants.

/g/ Activity against Glazkova blotch of wheat in vitro /Pseudocercosporella herpotrichoides PHI/

This test measures the in vitro activity of compounds against fungi causing ocellar spot of wheat. The test compound dissolved or suspended in acetone and added in aliquots of 4 ml polyr the concentration of 10 ppm of the test compounds and 0,825% acetone. Mushroom AMF inoculum consists of mycelial fragments of P. herpotrichoides grown in polurakom potato-dextrose broth in flasks with shaking, add it to the broth in order to obtain 5104mycelial fragments/ml of broth. Petri dishes are incubated at 20oC for 10 days until, until it comes time to evaluate the growth of the mycelium.

/h/ Activity against Rhizoctoria in vitro /Rhizoctonia solani; RSI/.

In the test measured the activity in vitro of the compounds against Rhizoctoria solani, which causes stableboy and root rot. The test compound dissolved or suspended in acetone and added to 4 ml aliquots pologrebskogo potato-dextrose broth, distributed in a Petri dish with 25 compartments, to obtain a final concentration of 10 ppm connection and 0,825% acetone. Mushroom AMF inoculum consists of mycelial fragment of R. solani grown in polurakom potato-dextrose broth in flasks in shake culture was added to the broth in order to obtain 5104mycelial fragments/ml of broth. Petri dishes are incubated at 20oC for 10 days until, until the time of assessing the growth of the mycelium.

/i/ Activity against Apple scab in vitro /Ventbria inatqmalis; VII/
4propagules/ml of broth. Petri dishes are incubated at 20oC for 10 days until, until it comes time to evaluate the growth of the mycelium.

The degree of control of the disease in all the above tests are expressed as the evaluation compared or with untreated controls with controls, sprayed dilutions, in accordance with criteria:

0= less than 50% disease control

1= 50-80% disease control

2= more than 80% disease control

The results are given in table.7.

Example 223. The effective dose for > 90% inhibition of test compounds in the test with serial dilution against various phytopathogenic fungi.

The value of ED > 90 (effective dose > 90%) is determined by testing a series of dilutions using cards microtitration with 24 or 48 cells on charge. Dilution of the tested compounds in the nutrient solution and ancentral: 0,05, 0,10, 0,20, 0,39, 0,78, 1,56, 3,13, 6,25, 12,50, 25,00, 50,00 and 100,00 mg/ml To prepare the nutrient solution mixed vegetable juice V8 (333 ml) with calcium carbonate (4,95 g), centrifuged, the supernatant (200 ml) diluted with water (800 ml) and treated in an autoclave at 121oC for 30 minutes

In cell submit the appropriate inoculum (Alternaria solani, ALTESO; Botrytis cinerea, BOTRICI; Cercospora beticola, CERCBE; cladosporium herbarum, MYCOTA; Corticium rolfsii, SCLORO; Helminthosporium tritici repentis, PYRNTR; Leptosphaeria nodorum, LEPTNO; Micro nectriella nivalis, MICNI; Monilinia fructigenf, MONIFG; Mycosphaerella ligulicola, MYCOLG; Mycospharrella pinodes, MYCOPI; Rhizoctonia Solani, RHYZSO; Sclerotinia Sclerotiorum, SCLESC) in the form of a suspension of spores (50 ml; 5 x 105/ml) or sliced agar (6 mm) agar culture of the fungus.

After 6-12 days incubation at suitable temperatures (18-25oC) determine the magnitude of ED > 90 visual inspection of circuit boards. The lowest concentration in a series of dilutions with growth of mycelium less than 10% is taken as the value of ED > 90 (PL. 8-10).

Example 224. Determination of the activity of the tested compounds against powdery mildew of cereals.

This test measures the preventive activity of the tested compounds used in the form of a sprayed solution on the leaves.

Seedlings of cereals (barley, cultivar Golden pnomisc, wheat, grade Cormoran) expression is from 5000 ppm source solution for dilutions in acetone, containing 5000 ppm x 155 (non-ionic polyoxyethylenated SAS). Plants treated with automated spray line with the spray nozzle. The spray volume is 24 ml 24 h after treatment, the seedlings inoculant powdery mildew by shaking them over the plants of the original culture with sporliuk pathogen (barley Erysiphe framinis f.sp. hordei; wheat, Erysiphe framinis f.sp. tritici).

Then the plants are incubated for 3 h without air movement to give disputes to grow on the leaves. The plants are then kept in the greenhouse before symptoms appear. The assessment is based on the percentage of the affected area of the leaves compared with that in control leaves (table. 11).

Example 225. Determination of the activity of the tested compounds against piricularia rice (Pericularia oryzae)

This test measures protecting activity of the tested compounds after spraying the leaves. Rice seedlings (Oryza Sativa L. "M-9") grown in the greenhouse. Approximately two weeks after planting, plants, spray a solution of active material (200 ppm) in the solvent/surfactant containing 5% of acetone and 0.05% tweenTM20 (surfactant: polyoxyethylenesorbitan ether mo is awom to state runoff, plants and leave on 2-5 hours to air dry before inoculation. The inoculum is prepared from Pericularia oryzae Cavara (culture FD 7 FD 190) (PYRIOR) grown on plates with the medium of agar and oat flour, from which conidia are washed with a solution of 0.05% tween 20 in deionized water. Then the concentration of conidia was adjusted to 1000000 conidia on the ml Solution is used for inoculation of the leaves, including clamps, by means of spraying a suspension of conidia on plant. The plants are kept in a humid chamber (18-28oC, 100% relative humidity) within 24-48 hours Then the plants are placed in a greenhouse at 8-10 days. The assessment is based on the percentage of affected leaf surface compared to those on leaves of control plants. Activity is expressed as percent disease prevention using the rating scale shown below.

0 0

1 1-14

2 15 29

3 30 44

4 45 59

5 60 74

6 75 89

7 90 95

8 96 99

9 100

Example 226. Definition aktivnosti of the tested compounds in field trials against piricularia rice

This test measures therapeutic effect of the tested compounds. Rice (Oryza sativa var. Koshihikari) grown in field plots (1 m x 1 m; 1 m2). The plants are sprayed with test compounds th the Ki infected seedlings. The spray volume is 0.1 l/plot, which is equivalent to 1000 l/ha of Assessment results conducted on the 11th day after the first (11 DATI) and 15 days after the second application (15 DAT2). They are based on the percentage of affected leaf surface compared to those on leaves of control plants. Activity is expressed as a percentage of cure of illness (table.13).

Example 227. Activity against powdery mildew on grapevine (Uncinula necator)

This test measures the direct protect the activity of the tested compounds and test compounds used in the form of spraying foliage. Cuttings of the vine (grape variety müller-Thurgau) is grown to the stage of 6-8 leaves and then form again to 4 leaves of the same size. Plants are sprayed to the point of runoff with a spray box solution (20 ml, 200 ppm) of active material in water, composed of 5000 ppm initial solution in acetone containing 5000 ppm TRITONTMX 155. After 48 h after treatment, the cuttings inoculant conidia Uncinula necator (UNCINE) in special sporobolomyces tower. Disputes blow with Signorelli grape leaves (u. necator stock culture) in the top hole of the tower and give them for 5 min to settle the sheets. Then the plants are kept in a phytotron PI lamps with light 11200 Suite. The valuation is carried out after 21 days by visual inspection and is based on the percentage of the affected area three youngest leaves compared with that in the control plants.

The results of the tests are presented in table.14, in which the compounds are identified by reference to the previous number of examples and the foregoing. The absence of numerical values indicates that the above tests were not conducted. Rating O indicates the presence of the disease in untreated control plants, the top 100 in the absence of infection.

Fungicidal activity against Venturia inaegualis on Malus sp.

Seedlings of Apple varieties Morgenduft or Mac, aged about 6 weeks treated with a solution of the appropriate test compound (100 ppm) in water/acetone/TRITON X or in water/methanol/TRITON X. After 72 h infect plants with a suspension of conidia of Venturia Inaegualis (conc. 50,000 conidia/ml) (VENTIN), incubated in a dark climate chamber at 100% relative humidity for 48 h and then kept at a relative humidity of 95-99% and temperatures of about 18 to 20oC during the day and 13oC at night for about 14 days.

The results of the tests are presented in table.10, in which connection the IDA is pointed but what the above tests are not conducted. Rating O indicates the disease as untreated control plants, the top 100 in the absence of infection.

1. Derivatives triazolopyrimidine General formula I

< / BR>
where R1WITH1WITH12-alkyl, C2- C6alkenyl,2WITH6-quinil,4- C12-alkadienes,3WITH8-cycloalkyl or4- C8-bicycloalkyl or 3 to 6-membered heterocycle containing one heteroatom selected from oxygen, nitrogen or sulphur, each group or ring is optionally substituted by one or more substituents selected from the group comprising halogen, nitro or cyano, hydroxyl, C1WITH4-alkyl, C1WITH4-haloalkyl,1- C4-alkoxy, C1WITH4-haloalkoxy, amino or1- C4-alkylamino, di-C1WITH4-alkylamino, formyl, C1WITH4-alkoxycarbonyl, carboxyl group, phenyl, C1WITH4-haloalkylthio, di-C1WITH4-alkoxyphenyl, furyl, dihalo-C3WITH6-cycloalkyl or in the case when R1- C3WITH8-cycloalkyl or 3 to 6-membered heterocycle, it is not necessarily orthocone the2together with the neighboring nitrogen atom are optionally substituted heterocyclic ring;

R3phenyl or naphthyl, each group optionally substituted by one or more substituents selected from halogen atoms, nitro or ceanography, hydroxyl, C3WITH12-alkyl, C1- C12-haloalkyl,1WITH4-alkoxy, C1- C12-haloalkoxy, amino or1- C4-alkylamino, di-C1WITH4-alkylamino, formyl, C1WITH4-alkoxycarbonyl, carboxyl group, phenyl, phenoxy and benzyloxy;

R4hydrogen, halogen or a group NR5R6where R5hydrogen, the amino group, WITH1WITH4-alkyl, C3- C6-cycloalkyl or7WITH8-bicycloalkyl, and R6is hydrogen or C1WITH4-alkyl.

2. Connection on p. 1, where R3phenyl, forfinal, chlorophenyl, chlorophenyl or methoxyphenyl.

3. Connection on p. 1, where R4hydrogen, fluorine, chlorine, bromine or iodine, or amino, methylamino, dimethylaminopropyl, hydrazino, cyclopentylamine or bicycloheptadiene.

4. Connection on p. 1, where R4chlorine.

5. The way polucheniya General formula II

< / BR>
where R3has the specified values;

Hal is chlorine or bromine,

with a compound of General formula III

HNR1R2,

where R1and R2have the specified values,

obtaining the compounds of formula I, where R4chlorine or bromine,

C) if desired, is introduced into the reaction of the compound of formula I, obtained in stage a) with a fluorinating agent to obtain a compound of formula I, where R4fluorine, and (C) optionally, introducing the reaction of the compound of formula I, obtained in stage a) with a regenerating agent to obtain a compound of formula I, where R4hydrogen, d) if desired, is introduced into the reaction of the compound of formula I, obtained in stage a) with a compound of General formula IV

HNR5R6,

where R5and R6have the specified values,

to obtain the compound of formula I, where R4the group-NR5R6and (e) optionally, introducing the reaction of the compound of formula I, obtained in stage d) in which R5and R6both hydrogen, with diiodomethane in the presence diastereomer agent to obtain a compound of formula I, where R4the iodine.

6. Fungicidal composition comprising an active ingredient derived triazolopyrimidine and targeted supplements, UB>WITH1WITH12-alkyl, optionally substituted by fullam, phenyl, cryptomaterial,2WITH6alkenyl,1WITH12-alkadienes,3WITH8-cycloalkyl, optionally substituted by 1 to 3 substituents selected from the group of hydroxyl,1WITH4-alkyl, halogen, C4WITH8-bicycloalkyl, benzothiazolyl, morpholinyl, pyrrolidinyl, dichloropyridine, indanyl, R2hydrogen or C1WITH4-alkyl; R1and R2together with the adjacent nitrogen atom represent piperidine, optionally substituted phenyl, benzyl, formylamino, hydroxyl, one or two WITH1- C4-alkilani, diazinon, triazole, azepino, optionally substituted 2-hydroxyimino or one three1WITH4-alkilani; decahydroquinoline; 1,4-dioxa-8 azaspiro(4,5)decyl; 3,4-dihydro-2H-pyridine; R3naphthyl or phenyl, optionally substituted with one to three substituents selected from halogen atoms, nitro, C1WITH4-alkyl, trifloromethyl, triptoreline, phenyl, phenoxy, benzyloxy; R4hydrogen, halogen, the group-NR5R6where R5hydrogen, the amino group, WITH1- C4-alkyl, R6hydrogen or C1WITH4-getitnow activity.

 

Same patents:

The invention relates to the production of Riboflavin (vitamin B2)

The invention relates to 6-oxo-asiminoaei compounds, namely to new derivatives of 6-oxo-3,4,5,6-tetrahydro-1H-azepino [5,4,3-cd] indole with, if necessary, in the 3rd or 4th position of the skeleton of the ring substituted aminoalkyl balance, and their acid salts of accession, and to pharmaceutical preparations containing these compounds, process for the preparation of these compounds and intermediates for their production

The invention relates to the chemistry of the condensed nitrogen-containing heterocyclic systems and specifically relates to new compounds of the hydrobromide of 2-amino-4-acetylthiazole /5,4-in/indole of formula 1

< / BR>
The inventive compound is a derivative of the heterocyclic system thiazolo/5,4-in/indole type a:

< / BR>
Derivatives of this system, for example, 2,4-dimethylthiazole /5,4-in/indole (In), described as intermediate products for the synthesis of polymethine dyes used as photosensitizers [1 4] however, in the literature there is no information about the biological activity of the system (a) and its derivatives

The invention relates to a method for producing new derivatives triazolo-[4,3-a](1,4) benzodiazepines General formula I:

I,

where X is-CH=CH -, or S;

R1lower alkyl or trifluoromethyl;

R2chlorine or fluorine;

R3the radical of the formula R4-(CH2)nC or R5-O-CH2-C_C-, where n is the integer 0, 1 or 2;

R4phenyl or mono-, di-, or tricyclic 5-7-membered heterocyclic radical containing as heteroatoms 0 or S, and/or 1-3 nitrogen atom, unsubstituted or substituted lower alkoxy, oxo, actigraphy or chlorine,

R5phenyl or pyridylethyl provided that when n is 0, the radical R4must be attached through a carbon to carbon link, and that R5attached via a carbon to oxygen connection with RAG-antagonistic properties

The invention relates to a series of new derivatives of compounds known as "milbemycin", which are characterized by the presence of heterocyclic substituted mercaptoacetate group at the 13-position

The invention relates to certain 13-alkyl-23-imino - 13-halogen-23-imino-LL-F28249-compounds and to their use for combating endo - and ectoparasitic infections and infestations in warm-blooded animals

The invention relates to new 2-imidazolin-2-yl)thieno - foroperational compounds, to intermediates used to obtain these compounds, and the way of dealing with these compounds with unwanted annual and perennial plants, namely 6-(2-imidazolin-2-yl)thieno - and furo[2,3-b] and 5-(2-imidazolin-2-yl)thieno - and furo[3,2-b]the pyridine compounds and the corresponding 2,3-dihydrothieno and 2,3-dihydropyrimidine with structural formulas (Ia) and (Ib):

< / BR>
whererepresents a single or double bond; R1represents a C1-C4alkyl; R2represents a C1-C4alkyl or C3-C6cycloalkyl; R1and R2together with the carbon atom to which they are joined, can form WITH3-C6cycloalkyl, optionally substituted stands; And represents СООR3CHO, CH2OH, COCH2HE, CONHCH2CH2OH, CONHOH or

R3hydrogen, C1-C12alkyl, which can be broken od is alkoxy, halogen, hydroxyl, C3-C6cycloalkyl, benzyloxy, fullam, phenyl, furfuryl, galopera, lower alkylphenyl, lower alkoxyphenyl, nitrophenyl, carboxyla, lower alkoxycarbonyl, cyano, C1-C4alkylthio or three (lower) alkylammonium; C3-C6alkenyl, optionally substituted by one of the following groups:1-C3alkoxy, phenyl, halogen or two WITH1-C3alkoxygroup or two halogen groups; C3-C6cyclooctyl, optionally substituted by one or two1-C3alkyl groups; C3-C10quinil, optionally substituted by phenyl, halogen or CH2IT; or the cation of an alkali metal or alkaline-earth metal (CA, BA) manganese, copper, iron, ammonium, or organic ammonium; RWITHand RDrepresent N or CH3; Represents N; COR4or SO2R5provided that when a represents a COR4or SO2R5and is a СOOR3the radical R3cannot be hydrogen or a salt-forming cation; R4represents a C1-C11alkyl, chloromethyl or phenyl, optionally substituted A5 alkyl or phenyl, optionally substituted one metalno, chloro - or nitro-group; W represents 0 or S; X represents 0, S or whenis a single bond, the group S 0; Y and Y', Z and Z' represent hydrogen, halogen, C1-C6alkyl, C1-C4hydroxy (lower) alkyl, C1-C6alkoxy, C1-C6acyloxy, benzoyloxy, optionally substituted by one or two1-C4alkyl, C1-C4alkoxygroup or halogen; C1-C4alkylthio, phenoxy,1-C4haloalkyl,1-C4haloalkoxy, nitro, cyano, C1-C4alkylamino,1-C4dialkylamino,1-C4alkylsulfonyl or phenyl, optionally substituted by one or more1-C4the alkyl, C1-C4alkoxy, halogen, or any combination of these two groups, where Y and Z are the same provided that Y and Z represent hydrogen, halogen, alkyl or alkoxy, and when Y and Y' or Z and Z' are the same group they are hydrogen or alkyl; and taken together, Y and Z form a ring in which YZ has the structural formula -(CH2)n- where n являе/www.fips.ru/fullimg/rupat2/19962/004.dwl/2058313-8t.gif" ALIGN="ABSMIDDLE">-=where L, M, Q, and R7each represent hydrogen, halogen, nitro, C1-C4lower alkyl, C1-C4lower alkoxy, methoxy, phenyl, phenoxy, provided that only one of the radicals L, M, Q or R7may have a value different from hydrogen, halogen, C1-C4the alkyl or C1-C4alkoxy; or a pyridine-N-oxides, when W represents oxygen or sulfur and a is COOR3; and when R1and R2not the same, the optical isomers of these compounds, except for the case when R3represents a salt-forming cation, their salts kislotoustoichivam

The invention relates to a pesticide composition on the basis of new chemical compounds having pesticidal activity, and is used for pest control

The invention relates to new ways of combating nematodes

The invention relates to a new class of pesticides, which are 1,4-bis-substituted-2,6,7-dioxabicyclo(2.2.2)octane

The invention relates to new derivatives of benzo(b)naphthiridine General formula

R(I) where R1hydrogen, alkyl or hydroxyl radical;

R2hydrogen, linear or branched C1-C4-alkyl, foralkyl, cycloalkyl, alkyloxyalkyl or alkylamino radical;

R3WITH1-C4-alkyl, and R4and R5different and mean hydrogen or C1-C4-alkyl;

or R3hydrogen or alkyl, or cycloalkyl and R4and R5individually, each means hydrogen;

R6hydrogen or fluorine;

n is 1 or 2, or their salts, possess antibacterial property

The invention relates to the field of pest control, in particular fungicidal means on the basis pyrrol-carbonitrile and methods of combating fungi

FIELD: agriculture.

SUBSTANCE: invention describes a method for feeding potato and tomato with 6-benzylaminopurine an aqueous solution taken in the concentration 10-4 M and growing pants up to preparing harvest according to technology accepted for the culture crop. Invention proposes 3-fold treatment of plants for vegetation: at the lateral branching phase, at onset of forming economically value organs and immediately after the growth termination. Method provides the effective enhancing the productivity of the most important vegetable crops - tomato and potato.

EFFECT: improved enhancing method.

6 tbl, 4 ex

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