2,6-disubstituted pyridine or 2,4-disubstituted pyrimidines, processes for their preparation, herbicide composition and method of controlling undesirable vegetation

 

(57) Abstract:

Describes the new 2,6-disubstituted pyridine or 2,4-disubstituted pyrimidines of General formula I, where X is an oxygen atom; Z is NH, CH; A is phenyl, substituted by a fluorine atom or triptorelin group, pyridyl substituted by a chlorine atom, pyrazolyl, substituted triptoreline and methyl group or methyl and tert-butilkoi group, differentialis, each of R1independently is a group selected from hydrogen atom, halogen atom, lower alkyl, lower alkylthio, lower alkoxyl; R2each, independently, is a group selected from a hydrogen atom, trifloromethyl, lower alkyl, trifloromethyl, halogen atom; m = 1 - 2, n = 0 to 2, provided that when A represents 1-methyl-3-cryptomaterial-5-ilen group, n = 0, X is an oxygen atom, Z is a group CH, then R2is not hydrogen, 3-trifluoromethyl, or 2,4-dichloro or 2,4-Dimethylol. The compounds exhibit herbicide activity. Describes how to obtain the compounds of formula I, herbicide activity on the basis of the above compounds and a method of controlling undesirable vegetation. 8 C. and 1 C.p. f-crystals, 13 tables.

The invention relates to some 2,6-disubstituted prideby with the growth of unwanted vegetation.

Pyridine, pyrimidines and their derivatives are widely used in the pharmaceutical field, as well as in agriculture (herbicides, fungicides, acaricides, sedative, repellents to deter birds), as reagents, intermediates and chemicals for the plastics and textile industries.

For example, 2-arylpyrimidine and 2-pyrimidinyl-6-arylpyrimidine described as fungicides (DE 4029654 and JO 2131-480 respectively). EP 263958 concerns with herbicide properties 2,6-diphenylpyridine and structurally related 2,4-diphenylpyridine, which, allegedly, are also herbicides are disclosed in EP 354766 and 425547 respectively. Another example is 2,6-diphenoxybenzene, which are presented in EP 572093 as herbicides. In DE 2935578 described that 4-phenoxy-2-pyrazole-1-yl-pyrimidine exhibit fungicidal activity. In the work Huelsen (Diplomarbeit, Konstanz, 1993) described four different 2-(1-methyl-3-trifluoromethyl-pyrazole-5 - yloxy)-6-phenylpyridine, however, their biological activity is not disclosed.

Now unexpectedly discovered that a good herbicide activity are similar in structure to new derivatives of pyridine and pyrimidine, having as aryl group, and ar is alnost crops at pre - and post-harvest application as compared to deciduous, and grassy weeds.

Thus, the present invention relates to 2,6-substituted pyridinium and 2,4-substituted the pyrimidines of General formula I

< / BR>
where X is an oxygen atom,

Z - NH, CH,

A is phenyl, substituted by a fluorine atom or triptorelin group, pyridyl substituted by a chlorine atom, pyrazolyl, substituted triptoreline and methyl group or methyl and tert-butilkoi group, differentialis.

each of R1independently is a group selected from hydrogen atom, halogen atom, lower alkyl, lower alkylthio, lower alkoxyl,

R2each, independently, is a group selected from a hydrogen atom, trifloromethyl, lower alkyl, trifloromethyl, halogen atom,

m = 1-2,

n = 0-2,

provided that, if a represents 1-methyl-3 - cryptomaterial-5-ilen group, n = 0, X is an oxygen atom,

Z is a group CH, then R2is not hydrogen, 3-trifluoromethyl, or 2,4-dichloro or 2,4-Dimethylol.

The preferred compounds are substituted 2-phenyl-6-oxopyrimidine formula IA

(IA)

where a represents a 3-triptoreline, 2-chloropyrid-4-yl or 1-methyl-3-cryptomaterial-5-Il,

R12"in addition, may be C1-C4-alkyl group, in particular tert-butilkoi, with the exception of compounds where a - 1-methyl-3-cryptomaterial-5-yl, R1is hydrogen, R2, R2"is hydrogen, R2'- trifluoromethyl; R2is hydrogen, R2'= R2"is chlorine or methyl; R2, R2', R2"- hydrogen.

Representative compounds are the following:

2-(1'-methyl-3'-cryptomaterial-5'-yloxy)-6-(4"- triptoreline)pyridine,

2-(2', 4'-differenl)-6-methyl-4-(1"-methyl-3"- cryptomaterial-5"-yloxy)pyrimidine,

2-(2',4'-differenl)-6-methyl-4-(3"-triptoreline)pyrimidine,

2-(2'-chloropyrid-4'-yloxy)-(4"-triptoreline)pyridine,

2-(2'-chloropyrid-4'-yloxy)-6-(3"-triptoreline)pyridine,

2-(3'-chlorophenyl)-5-methyl-4-(1"-methyl-3"-cryptomaterial-5"- yloxy)pyrimidine,

2-(3'-chlorophenyl)-5-methyl-4-(3"-triptoreline)pyrimidine,

2-(4'-forfinal)-6-methyl-4-(3"-triptoreline)pyrimidine,

2-(4'-forfinal)-4-(1"-methyl-3"-cryptomaterial-5"-yloxy)- 5-methylpyrimidin,

2-(4'-forfinal)-(1"-methyl-3"-cryptomaterial-5"-yloxy)-6 - IU)-5,6-dimethyl-2-(4'-trifloromethyl)pyrimidine,

4-(2"-chloropyrid-4"-yloxy)-5,6-dimethyl-2-(4'-triptoreline)pyrimidine,

4-(2"-chloropyrid-4"-yloxy)-5-methyl-2-(4'-trifloromethyl)pyrimidine,

4-(2"-chloropyrid-4"-yloxy)-5-methyl-2-(4'-triptoreline)pyrimidine,

4-(2"-chloropyrid-4"-yloxy)-6-methyl-2-(4'-trifloromethyl)pyrimidine,

4-(2"-chloropyrid-4"-yloxy)-6-methyl-2-(4'-triptoreline)pyrimidine,

5-ethyl-6-(4"-triptoreline)-2-(3'-triptoreline)pyridine,

4-methyl-6-(4"-trifloromethyl)-2-(1'-methyl-3'- cryptomaterial-5'-yloxy)pyridine,

4-methyl-6-(4"-trifloromethyl)-2-(2'-chloropyrid-4'-yloxy)pyridine,

4-methyl-6-(4"-triptoreline)-2-(1'-methyl-3'- cryptomaterial-5'-yloxy)pyridine,

4-methyl-6-(4"-triptoreline)-2-(2'-chloropyrid-4'-yloxy)pyridine,

4-methyl-6-(4"-triptoreline)-2-(2"-chloropyrid-4'-yloxy)pyridine,

4-methyl-6-(4"-forfinal)-2-(1'-methyl-3'-cryptomaterial - 5'-yloxy)pyridine,

5,6-dimethyl-2-(4'-trifloromethyl)-4-(1"-methyl-3"- cryptomaterial-5"-yloxy)pyrimidine,

5,6-dimethyl-2-(4'-trifloromethyl)-4-(3"-triptoreline)pyrimidine,

5,6-dimethyl-2-(4'-triptoreline)-4-(3"-triptoreline)pyrimidine,

5,6-dimethyl-4-(1"-methyl-3"-cryptomaterial-5"-yloxy)-2- (4'-thrift
5-methyl-2-(3'-were)-4-(3"-triptoreline)pyrimidine,

5-methyl-2-(4'-trifloromethyl)-4-(1"-methyl-3"- cryptomaterial-5"-yloxy)pyrimidine,

5-methyl-2-(4'-trifloromethyl)-4-(3"-triptoreline)pyrimidine,

5-methyl-2-(4'-triptoreline)-4-(1"-methyl-3"- cryptomaterial-5"-yloxy)pyrimidine,

5-methyl-4-(3"-triptoreline)-2-(4'-triptoreline)pyrimidine,

6-(4"-forfinal)-2-(1'-methyl-3'-cryptomaterial-5'- yloxy)pyridine,

6-methyl-2-(4'-trifloromethyl)-4-(1"-methyl-3"- cryptomaterial-5"-yloxy)pyrimidine,

6-methyl-2-(4'-trifloromethyl)-4-(3"-triptoreline)pyrimidine,

6-methyl-4-(3"-triptoreline)-2-(4'-triptoreline)pyrimidine,

6-ethyl-2-(4'-triptoreline)-4-(1"-methyl-3"- cryptomaterial-5"-yloxy)pyrimidine,

6-ethyl-2-(4'-triptoreline)-4-(3-triptoreline)pyrimidine,

6-ethyl-2-(4'-triptoreline)-4-(2'-chloropyrid-4'-yloxy)pyrimidine,

6-methoxymethyl-2-(4'-chlorophenyl)-4-(1"-methyl-3"- cryptomaterial-5"-yloxy)pyrimidine,

4-(3"-triptoreline)-2-(4'-triptoreline)pyrimidine,

4-(1"-methyl-3"-cryptomaterial-5"-yloxy)-2-(4'- triptoreline)pyrimidine,

6-chloro-2-(4'-triptoreline)-4-(1"-m is pyrazole-5-yloxy)pyrimidine,

6-fluoro-2-(4'-triptoreline)-4-(1"-methyl-3"- cryptomaterial-5"-yloxy)pyrimidine,

6-methoxy-2-(4'-triptoreline)-4-(3"-triptoreline)pyrimidine,

6-methoxy-2-(4'-triptoreline)-4-(1"-methyl-3"- cryptomaterial-5"-yloxy)pyrimidine,

6-methoxy-2-(4'-triptoreline)-4-(2'-chloropyrid-4'- yloxy)pyrimidine,

5-methoxy-2-(4'-triptoreline)-4-(3"-triptoreline)pyrimidine,

5-methoxy-2-(4'-triptoreline)-4-(1"-methyl-3"- cryptomaterial-5"-yloxy)pyrimidine,

5-methoxy-2-(4'-triptoreline)-4-(2'-chloropyrid-4'- yloxy)pyrimidine.

Compounds according to the invention can be obtained in the usual way.

Acceptable is the way to obtain 2,6-disubstituted pyridines or 2,4-disubstituted pyrimidines of General formula I on p. 1 consists in the fact that the compound of General formula III

< / BR>
subjected to interaction with the compound of General formula IV

A-XM

where Z, A, R1, R2, m, n and X are defined in paragraph 1;

Hal represents a halogen atom;

M represents a metal atom.

The method of obtaining compounds of General formula I, where R1is the lowest alkoxyl or lower alkylthio, lies in the interaction of the compounds of General formulas is .1 and R1above.

Alternatively, the method of obtaining substituted 2-phenyl-4,6 - dioxopyrimidine formula XV

< / BR>
where A, R2and m specified in paragraph 1, is that the connection formulas

< / BR>
where R2and m above, Hal is a halogen atom,

subjected to interaction with the compound of the formula

A-OM,

where a has the values listed above, and M is a metal atom.

Also proposed substituted 2-phenyl-4,6-dioxopyrimidine General formula XV

< / BR>
where A, R2and m are defined above,

as intermediate compounds for the synthesis of compounds of General formula I.

The compound of General formula I, if desired, may be isolated and purified using conventional methods.

The proposed connection in the field of applied non-toxic doses.

Compound XV can be obtained from III, where R1is Hal, Z is nitrogen, Hal, R2and m are defined above, by reacting with IV, described above, X denotes oxygen, with about 2 equivalents IV.

In practice, the interaction can be performed in the absence or in the presence of a solvent, which contributes to the interaction, or at least not Massa N,N-dimethylformamide or dimethylsulfoxide, or sulfolan, or ether, such as tetrahydrofuran or dioxane, or alcohols, or water, or mixtures thereof. The interaction is carried out at a temperature between room temperature and the boiling temperature of the reaction mixture, preferably at elevated temperature, especially at temperatures of distillation.

The compounds of formula III in which Z represents C-H group and n is 0, can be obtained by reacting compounds with the General formula V

< / BR>
where R2and m are defined above,

with aldehyde, suitable is usually formaldehyde, and dialkylamino, is appropriate dimethylamine, according to Org. Synthesis Col. Vol. III. 305f, in a solvent, usually alcohol, preferably ethanol, to obtain the compounds of General formula VI

< / BR>
which, according to DBP 2147288 (1971), consistently interact with the ammonium salt, is suitable ammonium acetate, and a compound of General formula VII

< / BR>
where Y is alkoxygroup or NH2group, preferably ethoxypropane, in a solvent, is appropriate alcohol, preferably ethanol, to obtain the compounds of General formula VIII

< / BR>
which then transform by reacting VIII with phosphoryl-halides (Muller. That Is, Cm, at elevated temperatures, ideally at the boiling point, to obtain the compounds of General formula III.

An alternative and preferred method of obtaining compounds of General formula III in which Z represents C-H - a group that includes the interaction of 2,6-dihalogenide General formula IX

< / BR>
where R1and n are defined above, and each of Hal1and Hal2independently represents a halogen atom,

with ORGANOMETALLIC derivatives of benzene of General formula (X), when approximately equimolar ratio,

< / BR>
where R2and m are defined above and M represents an alkali metal atom, or boron, or tin, or magnesium, or zinc, or copper, optionally in the presence of a catalyst based on transition metals.

The alkali metal may be any alkali metal, preferably lithium, and the reaction can be carried out in an aprotic polar solvent, preferably ether, to obtain the compounds of General formula III, especially as shown in Cook and Wakcfield, J. Chem.Soc., 1969, 2376, or in non-polar solvents, or water, for example as described in Ali, N. M. et al.. Tetrahedron, 1992, 8117.

The compounds of formula III where Z denotes CH, Hal represents fluorine, R1is the denotes CH, Hal represents fluorine, R2and m are defined above and R1is in position 3 and is methylthioribose (or another group of the above together, which is introduced in the form of an electrophilic reagent) is similar to the method described in Gingor, T., Marsais. F. and Queguiner, G.,J. Organometallic Chem., 1981, 139-150.

The method of obtaining compounds of formula III in which Z represents a nitrogen atom, includes the interaction of the hydrochloride of benzamidine General formula XI

< / BR>
where R2and m above,

with compounds of the formula XII or salt

< / BR>
where R11and R12regardless, defined above;

O-alkyl group typically represents a methoxy or ethoxy,

getting pyrimidinone General formula XIII, in which R1can also be a hydroxyl

< / BR>
Compounds of General formula XI are known or can be obtained in accordance with known literature methods, for example in Tetrahedron, 33, 1675f (1979) and J. Org.Chem., 26, 412f (1960).

The interaction of compounds of formulas XI and XII can be carried out in accordance with Liebigs Ann. 1980, 1392F in organic solvents, typically alcohols, preferably ethanol, in the presence of a base, usually of alkoxides of metals, suppose the organisations of the formula III, basically as described in Davies and Pigott, J. Chem. Soc. 1945, 347, by interacting with phosphorylchloride, or thionylchloride, or with phosgene, preferably with phosphorylchloride, phosphorylation, preferably in the absence of solvent, at elevated temperatures, to obtain the compounds of formula III.

The compounds of formula III with the values specified above for R1=F, can be obtained from compound III when R1is chlorine or amino, in accordance with known literature methods such as those described in C. W. Tullock et al., J. Am.Chem.Soc. 1960, 5197 or Kiburis J., Klister J., J. Chem.Soc.Chem.Com. 1969, 381.

Compounds of General formula IV are known or can be obtained by known methods. They can be obtained and allocated separately or can be prepared in situ. Typically, the compound of General formula XIV

A-XH (XIV)

where A and X are defined above,

subjected to interaction with a suitable metal-containing base, for example a carbonate, and a metal hydride. The preferred metal salt is a salt of sodium or potassium.

The present invention also provides the use of compounds of General formula I as a herbicide. Further, in accordance with the invention, provided is izia according to the invention, or a compound of formula I. as useful effect is achieved by applying a spray of leaves, the locus most preferably represents plants that are on the area of crop growth, typical crops are cereals, maize, soybean, sunflower or cotton. However, for these compounds with pre-emergence herbicide action, can also be applied to the soil. The dose of the active ingredient may, for example, be in the range of from 0.01 to 10 kg/ha, preferably from 0.05 to 1 kg/ha

The present invention also includes a method of obtaining a herbicide composition according to the invention, which involves mixing the compounds of formula I with at least one carrier.

Preferably the composition should be at least two carriers, at least one of which is a surface-active agent.

The carrier in the compositions according to the invention may be any substance which combines the active ingredient to facilitate application to the locus, which must be processed, which can be plants, seeds or soil, or in order to facilitate their storage, tracedata in a gaseous state, but can be compressed so as to form a liquid, and can be used any media commonly used in the preparation of herbicide formulations. Preferably the composition according to the invention contain from 0.5 to 95% by weight of the active ingredient.

Suitable solid carriers include natural and synthetic clays and silicates, for example natural silicates such as diatomaceous earth; magnesium silicates, for example, only; silicates of aluminum-magnesium, for example, attapulgite and vermiculite; aluminum silicates, for example kaolinites, montmorillonite and micas; calcium carbonate; calcium sulphate; ammonium sulphate; synthetic hydrated silicon oxides and synthetic calcium silicates or aluminum; elements, for example carbon and sulphur; natural and synthetic resins, such as coumarone resins, polyvinyl chloride and styrene polymers and copolymers; solid polihlorvinila; bitumen; 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, color tetrachlorophenol, perchloroethylene and trichloroethane. Are often suitable mixtures of different liquids.

Agricultural compositions often receive and transported in a concentrated form, which is subsequently diluted by the user before use. The presence of small amounts of media, which is a surface-active agent, facilitates this process of dilution. Thus, it is preferable that at least one carrier in a composition according to the invention was 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 can be an emulsifier, dispersant or wetting agent; it may be nonionic or ionic. Examples of suitable surface-active agents include the sodium or calcium salts of polyacrylic acids and ligninsulfonate acids; the condensation products of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitol, sucrose or pentaerythrol; their condensates with atilia or p-ochiltree, with ethylene oxide and/or propylene oxide; sulfates or sulfonates of these condensation products, salts of alkaline or alkaline earth metals, preferably sodium salt, and esters of sulfuric or sulfonic acids containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulfate, secondary alkyl sulphates of sodium, sodium salt from sulphonated castor oil, and alkylarylsulfonate sodium, such as dodecylbenzenesulfonate; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.

Herbicide compositions according to the invention can also contain other active ingredients, for example compounds with insecticidal or fungicidal properties, or other herbicides.

Ready-to-use composition containing the compounds according to the invention can contain 100 g of the active ingredient (compound of formula (I), 30 g of the dispersant, 3 g of antifoam, 2 g structural agent, 50 g of antifreeze additives that lower the freezing temperature, 0.5 g biocidal agent, and water to make 1000 ml Before use, the composition is diluted with water to obtain the desired concentration of the active ingredient.

The following examples illustrate isobars spectrometry.

Examples

Example 1:

Hydrochloride - dimethylaminopropiophenone

The acetophenone (29,1 ml, 0.25 mol), paraformaldehyde (12.0 g, 0.40 mol) and dimethylamine hydrochloride (28.5 g, 0.35 mol) is suspended in ethanol (50 ml). Added concentrated hydrochloric acid (0.5 ml) and the mixture was heated under reflux for 4 hours Then added acetone (200 ml) and the resulting clear solution was allowed to cool to room temperature. The precipitate was collected by filtration and was led from ethanol to obtain specified in the connection header (40,7 g, 76,0% of theoretical yield) in the form of colorless crystals with so pl. 158oC.

Examples 2-4:

Additional examples of compounds of General formula VI obtained as described in example 1. Details are given in table 1.

Example 5:

6-Phenyl-2-pyridone

Ethyl-2-CHLOROACETATE (10,6 ml, 0.1 mol) was slowly added to a hot (105oC) pyridine (8,9 ml, 0.11 mol), the temperature was maintained in the range of 100oC to 110oC. the Obtained brown oil was dissolved in ethanol (60 ml) were added hydrochloride - dimethylaminopropiophenone (17,7 g, 0.1 mol; obtained in accordance with example 1) and ammonium acetate (60 g) and boiled mixture with reverse Kholodilov of water, collected by means of filtration and purified by recrystallization from toluene. Specified in the title compound was obtained as colorless crystals (4.71 g, yield 28%) with T. pl. 200oC.

Examples 6-8:

Additional examples of compounds are obtained analogously to example 5.

Details are given in table II.

Example 9:

2-Bromo-6-phenylpyridine

A mixture of 6-phenylpyridine (3 g, 17.5 mmol, obtained according to example 5) and phosphorylated (7.2 g, 25,0 mmol) was heated to 100oC for 5 hours, the Cooled mixture was poured into water (40 ml) and brought the pH to 9 by adding a saturated solution of sodium carbonate. Then the layers were separated and the aqueous layer was extracted with ethyl acetate (50 ml). The combined organic layers were dried over anhydrous magnesium sulfate and the solvent evaporated in vacuum. Raw (untreated) product has led from aqueous ethanol. Subsequent purification via thin-layer chromatography (silica gel, hexane/ethyl acetate 9/1 about. /about. ) gave 2-bromo-6-phenylpyridine (3.1 g, yield 76%) as light brown crystals with so pl. 50oC.

Examples 10-12:

Additional compounds of General formula III obtained according to procedures similar to that shown in example 9. Adolescents>/BR>A mixture of 2-bromo-6-phenylpyridine (0.5 g, 2.1 mmol; obtained according to example 9), 1-methyl-3-trifluoromethyl-5-hydroxypyrazol (0.65 g, 3.9 mmol), potassium carbonate (0.6 g, 4.3 mmol) and N,N-dimethylformamide (2 ml) was heated under reflux for 12 hours Then the reaction mixture was placed directly into a column for thin-layer chromatography (silica gel). Elution with a mixture of hexane/ethyl acetate (9/1 vol/about.) gave specified in the title compound (0.35 g, yield 52%) as a pale yellow oil.

Examples 14-16:

The compounds described in table IV, obtained by methods similar to that shown in example 13.

Example 17:

2-Fluoro-6-(4'-forfinal)pyridine

Utility (105,0 ml, 0.26 mol, 2.5 M solution in hexane) was added to a solution of 1-bromo-4-fervently (34,3 ml, 0.31 mol) in anhydrous diethyl ether (200 ml) at -20oC. the Mixture was stirred for 60 min and then was cooled to -40oC. was Added 2,6-diporphyrin (22.7 ml, 0.25 mol) and gave the reaction mixture to warm to room temperature. Subsequently the mixture was washed with a saturated aqueous solution of ammonium chloride (300 ml). The layers were separated and the aqueous layer washed with diethyl ether 3 times (100 ml). After drying the combined organic layers over anhydrous shrevei (silica gel, hexane/AcOEt 8/2) to give colorless crystals of 2-fluoro-6-(4'-forfinal)pyridine (19,8 g, yield of 41.0%) with T. pl. 34oC.

Example 18:

2-Fluoro-6-(4'-forfinal)-4-methylpyridin

A mixture of 2-bromo-6-fluoro-4-methylpyridine (9.5 g, 50 mmol), 4-ferbinteanu acid (7.8 g, 56 mmol), sodium bicarbonate (of 12.6 g, 150 mmol), water (200 ml) and catalytic amounts of tetrakis(triphenylphosphine)palladium(0) in dimethyl ether in a nitrogen atmosphere was heated under reflux for a whole night. After filtering the reaction mixture, the solvents were removed under reduced pressure. The residue was distributed between water and ethyl acetate. The layers were separated and the aqueous layer washed with ethyl acetate. After drying the combined organic layers over anhydrous magnesium sulfate the solvent was removed in vacuum. The crude product was purified using thin-layer column chromatography (silica gel, pentane/ethyl acetate 9/1) to give colorless crystals of 2-fluoro-6-(4'-forfinal)-4-methylpyridine (3.7 g, yield 36,1%) with T. pl. 49oC.

Example 19:

2-Fluoro-6-(4'-tryptophanyl)-3-methylthiopyridine

To a solution of 2-fluoro-6-(4'-tryptophanyl)pyridine (2.4 g, 10 mmol, obtained according to the method of example 17), using 1-bromo-4-cryptomaterial in cachestore) at -70oC. After 2 h of incubation at -70oC was added dimethyl disulfide (1,41 g, 15 mmol) and gave the reaction mixture to warm to -20oC. the Mixture was hydrolyzed and extracted with diethyl ether. After separation the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed and the crude product was purified using thin-layer column chromatography (silica gel). Elution with a mixture of hexane/ethyl acetate (20/1.about.) resulted in the receipt specified in the title compound (1.2 g, yield 42%) with T. pl. 70-73oC.

Examples 20-23:

Analogously to example 17 were obtained samples of the compounds described in table V.

Example 24:

2-(3'-Chloropyrid-5'-yloxy)-6-(4"-torpedolike)pyridine

A mixture of 2-fluoro-6-(4'-forfinal)pyridine (1.9 g, 10 mmol, obtained in accordance with example 17), 3-chloro-5-hydroxypyridine (1.4 g, 11.0 mmol) and potassium carbonate (1.5 g, 11.0 mmol) in sulfolane was heated under reflux for 8 hours the Mixture was allowed to cool to room temperature and then filtered through a layer of silica gel, which was further washed with ethyl acetate. The resulting layers of the organic solution were combined and the solvent evaporated in vacuum. The remaining substance was placed in the upper part of the column gave 2-(3'-chloropyrid-5'-yloxy)-6-(4"-torpedolike)pyridine (1.4 g, yield 46%) as light brown crystals with so pl. 139oC.

Examples 25-39:

Additional compounds are obtained analogously to example 24.

Details are presented in table VI.

Example 40:

Hydrochloride 4-ferbenstein

4-Perbenzoate (10 g, 83 mmol) was dissolved in a mixture of anhydrous ethanol (5 ml) and diethyl ether (70 ml). The reaction mixture was cooled to the temperature of the ice bath and saturated with gaseous hydrogen chloride for 90 minutes the Mixture was allowed to warm to room temperature and stirred her during the night.

The colorless precipitate was filtered off, washed with diethyl ether and dissolved in anhydrous ethanol (20 ml). Added diethyl ether (100 ml), saturated with gaseous ammonia, and the solution was stirred for 3 hours

The resulting suspension was filtered and the solvent from the filtrate was removed under vacuum. The residue is washed with diisopropyl ether. After drying was obtained colorless crystals (5,15 g, 35.5 per cent) with so pl. 210oC.

Examples 41-50:

The following compounds of General formula XI obtained using methods similar to that shown in example 40. Details are given in table VII.

Example 51:

2-(4'-F. ivali for 30 min at room temperature. Next there was added the hydrochloride of 4-ferbenstein (1.47 g, 8.5 mmol) (from example 40) and the mixture was stirred for another 30 minutes was Added dropwise methyl-2-formylpyridine (1 g, 10.6 mmol) and the reaction mixture was allowed to mix at room temperature for 4 days.

After cooling, the solvent was removed in vacuum and the residue was dissolved in aqueous sodium hydroxide (10 ml, 1 M). Then pH of the mixture was brought to 5 with 2 M hydrochloric acid. The precipitate was filtered and washed with diisopropyl ether. After drying was obtained colorless crystals (0,44 g, 10.3 per cent) with so pl. > 250oC.

Example 52:

6-Hydroxy-2-(4'-triptoreline)-4-pyrimidinone

Hydrochloride 4-triptorelin (of 22.4 g, 0.1 mol, from example 41) was added to a solution of potassium methylate (0.22 mol) in anhydrous methyl alcohol (65 ml) and was stirred for 15 min at room temperature. Added diethylmalonate (of 12.6 ml, 0.11 mol) and the mixture was heated under reflux for 4 hours After cooling, the resulting suspension was diluted with methyl alcohol (50 ml). The solvent was removed in vacuum and the residue was dissolved in water (50 ml). Then pH of the mixture was brought to 1 using concentrated hydrochloric acid. The precipitate was filtered and primer 53:

5-Methoxy-2-(4'-triptoreline)-4-pyrimidinone

To a suspension of sodium hydride (60%, 6 g, 0.15 mol) in anhydrous THF (225 ml) was added over 30 min a solution of methylmetacrylate (14.9 ml, 0.15 mol) in methylformate (11,1 ml, 0.18 mol). The mixture was stirred for 2 h at room temperature. After adding diethyl ether (300 ml) of the resulting sodium salt of monoallelic of methylmethanesulfonate can be selected by means of suction. Further, this sodium salt (0,075 mol) was added to the hydrochloride 4-triftorperasin (16,8 g of 0.075 mmol, from example 41) in anhydrous ethanol (150 ml) and the mixture was stirred for 48 h at room temperature. After heating under reflux for 1 h, to the mixture was added water (100 ml) and the solution was filtered.

the pH of the filtrate is brought to 5 with acetic acid and removing the ethanol under vacuum. The precipitate was filtered and washed with ethyl alcohol. After drying the obtained crystals (13,7 g, 68%) with T. pl. > 200oC.

Examples 54-78

The method demonstrated in example 51, the following compounds of General formula III. Details are given in table VIII.

Example 79:

2-(4'-Forfinal)-4-chloro-5-methylpyrimidin

A mixture of 2-(4'-holodilnik within 1 h

The main part of the excess phosphorus oxychloride was removed in vacuo and extinguished the remainder water (10 ml) to hydrolyze the remaining reagent. The mixture was neutralized and then extracted with ethyl acetate (50 ml). After drying the organic layer with anhydrous magnesium sulfate, the solvent was removed in vacuum. Specified in the header connection (0,63 g, 72.6 per cent) was obtained as colorless crystals with so pl. 133oC.

Example 80:

2-(4'-Chlorophenyl)-4,5-dichloro-6-methoxypyridazine

To a solution of 2-(4'-chlorophenyl)-4,5,6-trichloropyridine (1.85 g, 6.3 mmol) in methyl alcohol (30 ml), THF (60 ml) was added a solution of sodium (0,145 g, 6.3 mmol) in methyl alcohol (10 ml) and the mixture was stirred at room temperature overnight. After removal of the solvent in vacuo the residue was added dichloromethane and the resulting mixture was washed with water. After drying the organic layer with anhydrous magnesium sulfate, the solvent was removed. Treatment of the residue with pentane gave specified in the title compound (1.75 g, 96%) as colorless crystals with so pl. 157-159oC.

Examples 81-108:

Compounds of General formula XIII, listed in table IX are obtained analogously to the method described in example 79.

Example 109:

2-(4'-Ftais example 81), ,,- 3-hydroxybenzonitrile (0,49 g, 3 mmol) and potassium carbonate (0,41 g, 3 mmol) in N,N-dimethylformamide (3 ml) was heated under reflux for 2 h

After cooling, was added ethyl acetate (10 ml) and the suspension was filtered through a layer of silica gel, using ethyl acetate. The solvent of the filtrate was removed under vacuum and the residue was purified via thin-layer chromatography on a column of silica gel using a mixture of hexane/ethyl acetate 7/2. Removal of solvent gave colorless crystals (0,53 g, 56.4 per cent) with so pl. 58oC.

Examples 110-183:

The following compounds of General formula I obtained according to the method of example 109. Details are given in table X.

Example 184:

4,6-Bis(2"-chloropyrid-4"-yloxy)-2-(4'-triptoreline)pyrimidine

A mixture of 4,6-dichloro-2-(4'-triptoreline)pyrimidine (with 2.93 g, 10 mmol) (from example 107), 2-chloro-4-hydroxypyridine (2.85 g, 22 mmol) and potassium carbonate (3.04 from g, 22 mmol) in anhydrous N,N-dimethylformamide (20 ml) was heated at 80oC for 1 h

After cooling, the solvent was removed under vacuum, was added ethyl acetate and the suspension was filtered through a layer of silica gel. The resulting solution is washed three times with water. After drying organicauthority on silica gel using mixtures of hexane/ethyl acetate 8/2. Removal of solvent gave colorless crystals (4.1 g, 86%) with T. pl. 141oC.

Examples 185-187:

Compounds of General formula XVa, listed in the table. XI, prepared similarly to the method of example 184. Details are given in table XI.

Example 188:

6-Methoxy-4-(2"-chloropyrid-4"-yloxy)-2- (4'-triptoreline)pyrimidine

4,6-Bis(2"-chloropyrid-4"-yloxy)-2-(4'- triptoreline)pyrimidine (2.0 g, 4.2 mmol) (from example 184) was dissolved in anhydrous methyl alcohol (5 ml), to this solution was added dropwise a solution of potassium methylate (4.2 mmol) in methyl alcohol (1.2 ml) and the mixture was heated under reflux for 30 minutes

The solvent was removed in vacuum and the residue was purified via thin-layer chromatography on silica gel using mixtures of hexane/ethyl acetate 9/1. Removal of solvent gave colorless crystals (1.0 g, 62%) with T. pl. 128oC.

Example 189:

4,6-Dibromo-2-(4'-triptoreline)pyrimidine

A mixture of 4,6-dihydroxy-2-(4'-triptoreline)pyrimidine (5,12 g, 20 mmol) and oxybromide phosphorus (10 ml) was heated for 3 h at 100oC. To the resulting hot suspension was added ice, and then the product can be highlighted by suction. After drying parmely I obtained using the methods of examples 188 or 189. Details are given in table XII.

Example 204:

6-Vinyl-4-(1"-methyl-3"-cryptomaterial-5"-yl)-2- (4'-triptoreline)pyrimidine

A mixture of 6-bromo-4-(1"-methyl-3"-cryptomaterial-5"-yl)-2-(4'- triptoreline)pyrimidine (2 g, 4.3 mmol, from example 201), vinyltrimethylsilane (1,4 ml, 4.7 mmol), tetrakis(triphenylphosphine)-palladium(0) (0.1 g, 0.09 mmol), toluene (20 ml) and three crystals of di-(tert-butyl)-4-METHYLPHENOL was heated under reflux for 90 minutes, After cooling, was added 1,2-called solution of fluoride pyridinium in THF/pyridine (4 ml) and pyridine (2 ml). The solution was stirred for 17 h at room temperature. To the resulting mixture were added ethyl acetate (100 ml) and the solution was twice washed with water and saturated sodium bicarbonate solution. After drying the organic layer with anhydrous magnesium sulfate, the solvent was removed and the residue was purified via thin-layer chromatography on silica gel using mixtures of hexane/ethyl acetate 7/3. Removal of solvent gave a nearly colorless crystals (1.45 g, 82%) with T. pl. 112oC.

Example 205:

Herbicide activity:

To assess their herbicide activity of the compounds according to the invention was tested using YSA Oryza sativa

GLXMA Glycine max

BEAVA Beta vulgaris

ZEAMX Zea mays

ALOMY Alopecurus myosuroides

AVEFA Avena fatua

ECHCG Echinocloa crus-galli

SETVI Setaria viridis

GALAP Galium aparine

STEME Stellaria media

CHEAL Chenopodium album

VERPE Veronica persica

LAMPU Lamium purpureum

VIOAR Viola arvensis

SIDSP Sida spinosa

AMBAR Ambrosia artemisifolia

ABUTH Abutilon theophrasti

IPOPU Ipomoea purpurea

SINAL Sinapis alba

AMARE Amaranthus retroflexus

The tests were divided into two categories - pre-emergence and post-harvest. Pre-emergence testing included the spraying liquid compositions based on compounds in the soil, in which the newly sown seeds of the above-mentioned plant species. Post-harvest trials were included spraying rising seedlings of the above kinds of such compounds.

The soil used in the tests was a prepared garden soil. Used in the tests finished compositions were obtained from solutions of test compounds in acetone containing 0.4% (wt.) surfactants of the type condensate of alkylphenol with ethylene oxide, available under the trademark TRITON X 55. Solution in acetone was diluted with water, and the resulting composition contained 1000 g or 300 g of active substance per hectare in a volume equivalent to 400 l/ha as a control s - samples of raw seedling plants, rising on untilled soil.

Herbicide effects of the tested compounds was determined visually in twenty days after spraying the foliage and soil (in the case of examples 13-16 thirteen days after treatment) and recorded on a ten-point scale (0-9). A score of 0 indicates the same growth as untreated control object, a score of 9 indicates a total loss. An increase of 1 unit linear scale corresponds to an increase in the degree of exposure by approximately 10%. Asterisks indicate that these species were not processed in this test.

The test results presented in the following table XIII, in which the compounds are determined by reference to the preceding examples. Asterisks indicate that these species were not processed in this test. The designation "pre-" and "post-" in the column "Method of use" match pre-emergence and post-harvest application of this connection.

1. 2,6-Disubstituted pyridine or 2,4-disubstituted pyrimidines of General formula I

< / BR>
where X is an oxygen atom;

Z - NH, CH,

A is phenyl, substituted by a fluorine atom or triptorelin group, pyridyl, replacing the Oh group, differentialis;

R1each, independently, is a group selected from hydrogen atom, halogen atom, lower alkyl, lower alkylthio, lower alkoxyl,

R2each, independently, is a group selected from a hydrogen atom, trifloromethyl, lower alkyl, trifloromethyl, halogen atom,

m = 1 to 2;

n = 0 - 2,

provided that, if A is 1-methyl-3-cryptomaterial-5-ilen group, n = 0, X is an oxygen atom, Z is a group CH, then R2is not hydrogen, 3-trifluoromethyl, or 2,4-dichloro or 2,4-Dimethylol.

2. Connection on p. 1, selected from the group consisting of compounds:

2-(1'-methyl-3'-cryptomaterial-5'-yloxy)-6-(4"-triptoreline)pyridine,

2-(2', 4'-differenl)-6-methyl-4-(1"-methyl-3"-cryptomaterial-5"-yloxy)pyrimidine,

2-(2', 4'-differenl)-6-methyl-4-(3"-triptoreline)pyrimidine,

2-(2'-chloropyrid-4'-yloxy)-(4"-triptoreline)pyridine,

2-(2'-chloropyrid-4'-yloxy)-6-(3"-triptoreline)pyridine,

2-(3'-chlorophenyl)-5-methyl-4-(1"-methyl-3"-cryptomaterial-5"-yloxy)pyrimidine,

2-(3'-chlorophenyl)-5-methyl-4-(3"-triptoreline)pyrimidine,

2-(4'-forfinal)-6-methyl-4-(3"-triptoreline)pyrimidine,

2-(4'-hotelportal-5"-yloxy)-6-methylpyrimidin,

4-(2"-chloropyrid-4"-yloxy)-2-(2',4'-differenl)-5-methylpyrimidin,

4-(2"-chloropyrid-4"-yloxy)-5,6-dimethyl-2-(4'-trifloromethyl)pyrimidine,

4-(2"-chloropyrid-4"-yloxy)-5,6-dimethyl-2-(4'-triptoreline)pyrimidine,

4-(2"-chloropyrid-4"-yloxy)-5-methyl-2-(4'-trifloromethyl)pyrimidine,

4-(2"-chloropyrid-4"-yloxy)-5-methyl-2-(4'-triptoreline)pyrimidine,

4-(2"-chloropyrid-4"-yloxy)-6-methyl-2-(4'-trifloromethyl)pyrimidine,

4-(2"-chloropyrid-4"-yloxy)-6-methyl-2-(4'-triptoreline)pyrimidine,

5-ethyl-6-(4"-triptoreline)-2-(3'-triptoreline)pyridine,

4-methyl-6-(4"-trifloromethyl)-2-(1'-methyl-3'-cryptomaterial-5'-yloxy)pyridine,

4-methyl-6-(4"-trifloromethyl)-2-(2'-chloropyrid-4'-yloxy)pyridine,

4-methyl-6-(4"-triptoreline)-2-(1'-methyl-3'-cryptomaterial-5'-yloxy)pyridine,

4-methyl-6-(4"-triptoreline)-2-(2'-chloropyrid-4'-yloxy)pyridine,

4-methyl-6-(4"-forfinal)-2-(1'-methyl-3'-cryptomaterial-5'-yloxy)pyridine,

5,6-dimethyl-2-(4'-trifloromethyl)-4-(1"-methyl-3"-cryptomaterial-5"-yloxy)pyridine,

5,6-dimethyl-2-(4'-trifloromethyl)-4-(3"-triptoreline)pyrimidine,

5,6-dimethyl-2-(4'-triptoreline)-4-(3"-triptoreline)pyrimidine,
5-methyl-2-(3'-were)-4-(3"-triptoreline)pyrimidine,

5-methyl-2-(4'-trifloromethyl)-4-(1"-methyl-3"-cryptomaterial-5"-yloxy)pyrimidine,

5-methyl-2-(4'-trifloromethyl)-4-(3"-triptoreline)pyrimidine,

5-methyl-2-(4'-triptoreline)-4-(1"-methyl-3"-cryptomaterial-5"-yloxy)pyrimidine,

5-methyl-4-(3"-triptoreline)-2-(4'-triptoreline)pyrimidine,

6-(4"-forfinal)-2-(1'-methyl-3'-cryptomaterial-5'-yloxy)pyridine,

6-methyl-2-(4'-trifloromethyl)-4-(1"-methyl-3"-cryptomaterial-5"-yloxy)pyrimidine,

6-methyl-2-(4'-trifloromethyl)-4-(3"-triptoreline)pyrimidine,

6-methyl-4-(3"-triptoreline)-2-(4'-triptoreline)pyrimidine,

6-ethyl-2-(4'-triptoreline)-4-(1"-methyl-3"-cryptomaterial-5"-yloxy)pyrimidine,

6-ethyl-2-(4'-triptoreline)-4-(3"-triptoreline)pyrimidine,

6-ethyl-2-(4'-triptoreline)-4-(2'-chloropyrid-4'-yloxy)pyrimidine,

6-methoxymethyl-2-(4'-chlorophenyl)-4-(1"-methyl-3"-cryptomaterial-5"-yloxy)pyrimidine,

4-(3"-triptoreline)-2-(4'-triptoreline)pyrimidine,

4-(1"-methyl-3"-cryptomaterial-5"-yloxy)-2-(4'-triptoreline)pyrimidine,

6-chloro-2-(4'-triptoreline)-4-(1"-the pyrazole-5-yloxy)pyrimidine,

6-fluoro-2-(4'-triptoreline)-4-(1"-methyl-3"-cryptomaterial-5"-yloxy)pyrimidine,

6-methoxy-2-(4'-triptoreline)-4-(3"-triptoreline)pyrimidine,

6-methoxy-2-(4'-triptoreline)-4-(1"-methyl-3"-cryptomaterial-5"-yloxy)pyrimidine,

6-methoxy-2-(4'-triptoreline)-4-(2'-chloropyrid-4'-yloxy)pyrimidine,

5-methoxy-2-(4'-triptoreline)-4-(3"-triptoreline)pyrimidine,

5-methoxy-2-(4'-triptoreline)-4-(1"-methyl-3"-cryptomaterial-5"-yloxy)pyrimidine,

5-methoxy-2-(4'-triptoreline)-4-(2'-chloropyrid-4'-yloxy)pyrimidine.

3. Substituted 2-phenyl-6-oxopyrimidine formula IA

< / BR>
where A represents A 3-triptoreline, 2-chloropyrid-4-yl or 1-methyl-3-cryptomaterial-5-Il,

R1matter specified in paragraph 1;

R2, R2'and R2"independently represent a hydrogen atom, fluorine atom, chlorine or bromine, one or two of them also represent trifluoromethyl, triptoreline, R2"in addition, may be C1- C4- alkyl group, in particular tert-butilkoi, with the exception of compounds where A is 1-methyl-3-cryptomaterial-5-yl, R1is hydrogen, R2, R2"is hydrogen, R2'- trifluoromethyl; R2is hydrogen,6-dioxopyrimidine General formula XY

< / BR>
where A, R2and m is defined in paragraph 1.

5. The method of obtaining 2,6-disubstituted pyridines or 2,4-disubstituted pyrimidines of General formula I on p. 1, characterized in that the compound of General formula III

< / BR>
interacts with the compound of General formula IY

A - XM,

where Z, A, R1, R2, m, n and X are defined in paragraph 1;

Hal represents a halogen atom;

M represents a metal atom.

6. Method of production of 2,4-disubstituted pyrimidines of General formula I

< / BR>
where R1means the lowest alkoxyl, lower alkylthio;

A, R2m have the meanings specified in paragraph 1 of the formula

characterized in that the compound of the General formula XY

< / BR>
where A, R2m mentioned above,

subjected to interaction with the compound of General formula R1- H or its salt with a metal, where R1above.

7. The method of obtaining substituted 2-phenyl-4,6-dioxopyrimidine formula XY

< / BR>
where A, R2and m specified in paragraph 1,

characterized in that the compound of the formula

< / BR>
where R2and m above,

Hal is a halogen atom,

subjected to interaction with the compound of the formula

A - OM,

where A has the values listed above, and M is a metal atom.

8. Herbicidetolerant-active agent.

9. A way of combating the growth of unwanted vegetation on the locus, characterized in that it includes processing of this locus an effective amount of compound on the PP.1 to 3.

 

Same patents:

The invention relates to new triazolylmethyl tertiary amine of the formula I, where A is a simple bond or lower Allenova group; B is a lower alkyl, a group (a), naphthyl, pyridyl, thienyl, thiazolyl, benzothiazolyl, hinely, benzofurazanyl or benzothiazolyl, possibly substituted with halogen or alkyl; D - ring group, (b) or benzofurazanyl; E - ring - 4H-1,2,4-triazole or 1H-1,2,4-triazolyl; R1- H, halogen, cyano-, nitro-group, CF3, lower alkyl or alkoxy; R2is hydrogen or halogen; R3- halogen, cyano-, nitro-, CF3or amino group, provided that when both R1and R2are chlorine atoms, And a methylene

The invention relates to new Amida 4 - oxoazetidin-2-sulphonic acids and their salts, to a process of obtaining

The invention relates to pyrazole derivative of the General formula I, where g2, g3and g6hydrogen; g4- chlorine atom or bromine, WITH1-C3-alkyl, trifluoromethyl, or phenyl; g5is hydrogen or chlorine atom; w2, w3, w5and w6is hydrogen or chlorine atom; w4is hydrogen, a chlorine atom, a C1-C3-alkyl, C1-C3-alkoxy or nitro; X is a direct bond or the group -(CH2)nN(R3)-, where R3is hydrogen or C1-C3-alkyl; n is 0 or 1; R4is hydrogen or C1-C3-alkyl and, when X is a direct bond, R is a group-NR1R2where R1is hydrogen, C1-C6-alkyl or cyclohexyl, and R2- C1-C6-alkyl, non-aromatic carbocyclic radical WITH3-C15possibly substituted by a hydroxyl group, one or more1-C5-alkilani,1-C5alkoxygroup or halogen; amino group WITH1-C4-alkyl in which the amino may dazamide1-C3-alkyl, cyclohexyl1-C3-alkyl; phenyl, unsubstituted or substituted with halogen, or WITH1-C5-alkyl; phenyl WITH1-C3-alkyl, diphenyl1-C3-Olinala, hinokitiol and oxybutylene, unsubstituted or substituted C1-C3-alkyl or benzyl; 1-adamantaneacetic; C1-C3-alkyl, substituted aromatic heterocycle selected from pyrrolyl, pyridyl or indolyl, unsubstituted or substituted C1-C5-alkyl, or R1and R2form together with the nitrogen atom to which they relate, pyrrolidinyl, piperidyl or morpholinyl; or the group R5that represents phenyl WITH1-C3-alkyl, unsubstituted or substituted C1-C5-alkyl; cyclohexyl1-C3-alkyl, or 2-norbornylene; when X represents a group -(CH2)nN(R3)-, R represents a group R2Athat represents a non-aromatic carbocyclic radical WITH3-C15; phenyl substituted by halogen; phenyl WITH1-C3-alkyl, possibly substituted with halogen; indolyl, possibly substituted C1-C5alkoxygroup; anthracene, or group with other2bin which R2b- cyclohexyl, substituted, phenyl, unsubstituted or substituted by one or two halogen atoms, WITH1-C5-alkyl or C1-C5alkoxygroup or their acid additive salts

The invention relates to 1,4-disubstituted the piperazines of General formula (I), which means the group-CO - or-CH2-OCO; D - heteroaryl selected from a range including 1, 3, 5-triazinyl, pyrimidinyl and pyridinyl, possibly substituted by one or two substituents selected from a range, including mono-(C1-C6)-alkylamino, mono-(C3-C7)- alkynylamino-, di-(C1-C6)-alkylamino-,

(C1-C6)-alkyl-(C3-C7)-alkylamino and pyrrolidin-I-yl group; Raand Rbis a hydrogen atom or (C1-C3)-alkyl; n is an integer from 1 to 4; their enantiomers, racemic mixtures and their salts with pharmaceutically acceptable acids and bases

The invention relates to a new method of obtaining 2-substituted 4,6-dialkoxybenzene General formula I

< / BR>
in which

R1and R2may be the same or different and mean (C1-C4)-alkyl, and R3means R4-O-, R4-S - or R4R5N-, where R4equal to C1-C4-alkyl, R5means a hydrogen atom, a C1-C4-alkyl or phenyl; 2-N-alkylamino-4,6-dimethoxypyrimidine and method for producing a halogen-substituted pyrimidine

Ammonium salts // 2106346

The invention relates to an improved process for the preparation of substituted N-(1,3,5-triazine-2-yl)aminocarbonyl-arylsulfonamides General formula

< / BR>
where R1= Cl, COOCH3;

R2= OCH3N(CH3)2;

R3= CH3, ON=C(CH3)2, ON=C(CH3)C2H5;

R4= H, CH3,

used in agriculture as herbicides and plant growth regulators

The invention relates to new derivatives of catechol and their pharmaceutically acceptable salts and esters which are useful as medicaments, antioxidants

The invention relates to new derivatives of sulfamethoxypyrazine and herbicides containing them as active ingredients

The invention relates to a derivative of propionic acid, useful as fungicides, to fungicidal compositions containing them and to methods used to combat fungi, especially fungal infections of plants

The invention relates to organic synthesis and concerns a method for obtaining substituted falicov and heterocyclic falicov General formula

(I) where ring a is selected from the group comprising residues:

a) phenyl,

b) pyridyl,

b) five-membered heteroaromatic ring containing oxygen, sulfur or nitrogen as a heteroatom;

R cyano, formyl, ketonuria group, carboxyl group, which may be in the form of the free acid, ester or salt, carnemolla group or mono - or disubstituted carnemolla group or ring

Z

Y1, Y2and Y3attached to carbon atoms and are independently hydrogen, halogen, hydroxyl, C1-8-alkyl, C2-8-alkenyl,2-8-quinil,1-8-alkoxy, C2-8-alkenylamine,2-8-alkyloxy,1-8-alkylsulfonate, each of which may be substituted by 1 to 6 halogen atoms and conjugated WITH1-8-alkoxyl,2-8-acyl, phenyl WITH1-8-alkoxyl, phenylthio, each of which can be substituted one or three halogen atoms;

Y1and Y2>W3, W4and W5independently is CH, CR3or N;

Z is a bridge consisting of elements selected from the group of methylene, substituted methylene, -C(O)-;

R1and R2each independently hydrogen, halogen, C1-8-alkyl, C1-8-alkoxy, C2-8-alkenylamine,2-8-alkyloxy, each of which may be substituted by 1 to 6 halogen atoms, 5 - or 6-membered heterocycle-C1-8-alkoxy, phenyloxy or phenyl-C1-8-alkoxy, each of which may be substituted by 1-3 substituents selected from halogen or1-8-alkyl; R2WITH1-8-alkyl, phenyl-C1-8-alkoxy or phenyl;

X and Y each independently hydrogen, hydroxyl, halogen, cyano, C1-8-alkyl, C1-8-alkoxy, C1-8-alkoxycarbonyl,2-8-acyloxy, carbamoylated,1-8-alkylthio, phenyloxy, phenyl S, each of which may be substituted by 1-3 halogen atoms, or together they predstavljaet,S,NH,NOR12илиCR13R14;

or X and R together may form a bridge having the formula-C(O)-O - or-C(O)-NR2where the carbonyl is attached to A; with the proviso that when R carboxyl in free ether or salt and X and Y together javlautsa, one of the rings a and b contains a heteroatom
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