Derivative sulfamethoxypyrazine and selective herbicida composition

 

(57) Abstract:

Usage: agriculture, chemical plant protection products. The inventive product of the formula Q-SO2NHC(= 0)N(L)G, where Q is-N[SO2N(CH3)2] Or", or-N[SO2N(CH3)2]R"', R" - C1-C4-alkyl, C2-C4alkenyl, C1-C4-alkyl, substituted C1-C4-alkoxy, phenyl, R"' - C1-C4-alkyl, L is hydrogen, C1-C4-alkyl, B is methyl, methoxy, C - methyl, methoxy, deformedarse. Selective herbicide composition containing 2-40% of the product and the rest of the target additives. 2 S. p. f-crystals, 10 ill., 33 table.

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

To protect important agricultural crops such as rice, wheat, corn, soy, cotton and sugar beet, weed and, thereby, to increase the yield it is absolutely necessary to use herbicides. Especially in recent time required selective herbicides that can selectively kill weeds without showing phytotoxicity in relation to cultural plants when applied to the leaves of cultural R is ing plants and weeds. In addition, to avoid environmental pollution and reduce transportation costs and use in for many years conducted research and development in respect of compounds with high herbicide activity at low doses. Some of the compounds having such properties, currently used as selective herbicides. However, there is still a need for better compounds having such properties.

As an example, the source of the known prior art, showing a chemical structure similar to the structure of the compounds of the present invention, Japanese patent publication, which is not examined, NN 103371/1983, 48973/1985 and 151577/1989 disclose compounds having a sulfonylurea, related to the nitrogen atom.

Do not pass the examination Japanese patent publication NN 48973/1985 and 151577/1989 disclose compounds having the sulfonylurea attached to the nitrogen atom sulfonamidnuyu patterns. However, the compounds of the present invention, in which the sulfonylurea attached to the nitrogen atom of the special sulfa structures were not known, and they are new compounds.

Infusion for important crop plants and studied herbicide properties of many compounds with the aim of finding compounds with higher herbicide activity and selectivity. In the result, it was found that the derivative sulfamethoxypyrazine the following formula /1/ and their agricultural suitable salt (referred to hereafter compounds of the present invention) exhibit unusually strong herbicide activity against many weeds with tillage or during the processing of the leaves, and at the same time they have a high level of security for important crops such as wheat, corn, cotton, soybean, sugar beet and rice. The present invention was achieved on the basis of this findings. On the other hand, since the compounds of the present invention show herbicide activity at a very low dose compared to conventional herbicides, they are also useful as herbicides for orchards, or for non-agricultural lands.

Namely, the present invention is derived sulfamethoxypyrazine formula /1/ or their salts:

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where Q represents a (see Fig.1).

where R11is a /1-6/C alkyl group, /3-7/C cycloalkyl group /3-7/C cycloalkenyl group /1-6/C alkyl group, substituted /3--6/C alkenylphenol group, /2-6/C alkylamino group /1-6/C alkyl group, substituted /1-6/C alkoxy group, a /1-6/C alkyl group, substituted /1-6/C alkylthio group /1-6/C alkyl group, substituted /1-6/C mono - or di alkylamino group /1-6/C mono - or polyalkylene group /2-6/C mono - or poly-haloalkyl group /1-6/C alkyl group, substituted cyano group /1-6/C alkyl group, substituted /1-6/C alkoxycarbonyl group /2-6/C alkenylphenol group, substituted /1-6/C alkoxycarbonyl group /1-6/C mono - or poly-haloalkyl group, substituted /1-6/C alkoxycarbonyl group /1-6/C alkyl group, substituted /1-6/C mono - or di-alkylaminocarbonyl group /1-6/C alkoxycarbonyl group /1-6/C mono - or di-alkylaminocarbonyl group, cyano group /1-6/C alkyl group, substituted /1-6/C alkylcarboxylic group, /1-6/C alkylcarboxylic group /1-6/C mono - or poly-haloalkylthio group, phenyl or benzyl group (provided that such a phenyl or benzyl group may be mono - or poly-substituted by a halogen atom, triptorelin group, nitro group /1-6/C alkyl group, /1-6/C alkoxy group or /1-6/C alkoxycarbonyl group), 3-6-membered heterocyclic group (provided, of chlorodi and sulfur, in the ring and may be mono - or poly-substituted by a halogen atom, triptorelin group, a nitro group, a /1-6/C alkyl group, /1-6/C alkoxy group or /1-6/C alkoxycarbonyl group /1-6/C alkyl group, substituted 3-6-membered heterocyclic group (provided that such heterocyclic group contains from 1 to 3 hetero-atoms selected from the group consisting of nitrogen atoms, oxygen and sulphur, the ring may be mono - or poly-substituted by halogen atom, triptorelin group, nitro group /1-6/C alkyl group, /1-6/C alkoxy group or /1-6/C alkoxycarbonyl group)

R12represents a hydrogen atom, a /1-6/C alkyl group, /2-6/C alkenylphenol group /2-6/C alkylamino group, phenyl or benzyl group (provided that such a phenyl group or benzyl group may be substituted by a halogen atom, triptorelin group /1-6/C alkyl, /1-6/C alkoxy group or /1-6/C alkoxycarbonyl group)

R13is /1-6/C alkyl group, phenyl or benzyl group (provided that such a phenyl or benzyl group may be substituted by a halogen atom, triptorelin group /1-6/C alkyl group, /1-6/C alkoxy group, a /1-6/C of arcoxia what have they are attached, saturated 5-7 membered heterocyclic group, or R12and R13form together with the oxygen atom and the nitrogen atom to which they are attached, a 5-7 membered heterocyclic group,

R21is /1-6/C alkyl group, /3-7/C cycloalkyl group /1-6/C alkyl group, substituted /3-7/C cycloalkyl group /1-6/C alkyl group, substituted /3-7/C mono-or poly-geluidsisolering group /2-6/C alkenylphenol group /2-6/C alkylamino group /1-6/C alkyl group, substituted /1-6/C alkoxy group, a /1-6/C alkyl group, substituted /1-6/C alkylthio group, /1-6/C alkyl group, substituted /1-6/C mono - or di alkylamino group /1-6/C mono - or poly-haloalkyl group /2-6/C mono - or poly-haloalkyl group /1-6/C alkyl group, substituted cyano group /1-6/C alkyl group, substituted /1-6/C alkoxycarbonyl group /2-6/C alkenylphenol group, substituted /1-6/C alkoxycarbonyl group /1-6/C alkyl group, substituted /1-6/C mono - or di-alkylaminocarbonyl group /1-6/C alkoxycarbonyl group /1-6/C mono - or di-alkylaminocarbonyl group, cyano group /1-6/C alkyl group, substituted /1-6/C alkylcarboxylic group /1-6/C alkylcarboxylic group /1-6/C mono - or poly-ha is th group can be mono - or poly-substituted by halogen atom, triptorelin group, nitro group /1-6/C alkyl group, /1-6/C alkoxy or /1-6/C alkoxycarbonyl group), 5-6-membered heterocyclic group (provided that such heterocyclic group contains from 1 to 3 heteroatoms selected from the group consisting of nitrogen atoms, oxygen and sulfur, in the ring, and this heterocyclic group may be mono-or poly-substituted by a halogen atom, triptorelin group, nitro group /1-6/C alkyl, /1-6/C alkoxy or /1-6/C alkoxycarbonyl group)

R22represents a hydrogen atom or /1-6/C alkyl group,

R23represents a hydrogen atom or /1-6/C alkyl group,

R24represents a hydrogen atom, a /1-6/C alkyl group, a halogen atom, a /1-6/C mono - or poly-haloalkyl group /1-6/C alkyl group, substituted /1-5/C alkoxy group, a /1-6/C alkyl group, substituted /2-6/C alkenylamine group /1-6/C alkyl group, substituted /2-6/C alkyloxy group /1-6/C alkyl group, substituted /1-6/C mono - or poly-haloalkoxy group /1-6/C alkyl group, substituted /1-6/C-alkylthio group /1-6/C alkyl group, substituted /1-6/C alkylsulfonyl group /1-6/C alkyl group, substituted cyano group /1-6/C alkoxycarbonyl g is /1-6/C alkyl group, substituted /1-6/C alkylcarboxylic group

R25represents a hydrogen atom or /1-6/C alkyl group,

R26represents a hydrogen atom or /1-6/C alkyl group,

R27represents a hydrogen atom or /1-6/C alkyl group,

R28represents a hydrogen atom, a /1-6/C alkyl group, /1-6/C mono - or poly-haloalkyl group /1-6/C alkyl group, substituted /1-6/C alkoxy group, a /1-6/C alkyl group, substituted /2-6/C alkenylamine group /1-6/C alkyl group, substituted /2-6/C alkyloxy group /1-6/C alkyl group, substituted /1-6/C alkylthio group /1-6/C alkyl group, substituted /1-6/C alkylsulfonyl group, /1-6/C alkyl group, substituted cyano group /1-6/C alkoxycarbonyl group /1-6/C alkylcarboxylic group /1-6/C alkyl group, substituted /1-6/C alkoxycarbonyl group, or /1-6/C alkyl group, substituted /1-6/C alkylcarboxylic group;

L represents a hydrogen atom, a /1-6/C alkyl group, /2-6/C alkenylphenol group or /2-6/C alkylamino group;

X represents an oxygen atom or sulfur;

G represents a group

,

where A represents A CH group or a nitrogen atom, and each of B and C independently represents /1-4/C alkyl group, /1-4/C the present invention is also selective herbicide, containing one or more compounds of the present invention as active ingredients.

Further, the present invention represents a herbicide composition comprising one or more compounds of the present invention and one representative selected from the group consisting of alachlor, acetochlor, metahara, primisulfuron and nicolsufuron as active ingredients.

Now the present invention will be described in detail with reference to the preferred embodiment of the invention.

The compounds of formula I of the present invention can easily be obtained using any of the following reaction schemes 1 to 6.

Reaction scheme 1

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In the above formulas, Q, G, L and X have the meanings defined above.

In particular, sulfimidosulfides(thio)cyanate derivative (II) is dissolved in a sufficiently dried inert solvent such as dioxane, acetonitrile or acetone, then adds a pyrimidine or triazine derivative of formula (III), the mixture is stirred, whereby the reaction usually proceeds smoothly, and it turns out the connection /I/ of the present invention. When the reaction proceeds with difficulty, can be added very nabatat sodium or potassium carbonate, whereby the reaction proceeds freely.

Reaction scheme 2

< / BR>
In the above formulas, Q, G, L and X have the meanings defined above, and Y represents /1-6/C alkyl group or phenyl group.

Namely, sulfimidosulfides derived /IV/ subject interaction with chlorine ether/tio/formic acid or di-ether/tio/carboxylic acid in a solvent such as acetone, methyl ethyl ketone or acetonitrile, in the presence of a base such as potassium carbonate, to obtain the compounds of /X/. Then it is heated together with the connection /III/ in a solvent such as toluene, to obtain the compounds (I) of the present invention.

Reaction scheme 3

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In the above formulas, Q, G, L and Y have the meanings defined above.

The reaction of sulphonamide /VI/ with phenyl N-chlorosulfonylisocyanate (VII; Y is phenyl group) or alkyl N-chlorosulfonylisocyanate (VII; Y /1-6/C alkyl group) is usually performed with the use of from 0.5 to 3.0 mol, preferably from 0.9 to 1.2 mol urethane derivative /VII/ mol sulphonamide /VI/.

The reaction temperature may be optionally selected in the range from -50oC to 100oC, preferably from -20oC to the amount of from 0.5 to 4.0 mol per mol of sulphonamide /VI/.

Suitable bases include metal hydrides such as sodium hydride, a metal alcoholate such as sodium ethylate, altimetry, such as n-utility, organic bases such as triethylamine, pyridine and 1,8-diazabicyclo/5,4,0/-7-undecene (DWI), and inorganic bases such as potassium hydroxide and sodium hydroxide. Especially preferred to use a metal hydride.

A suitable solvent for this reaction is a solvent inert to the reaction, which includes aromatic hydrocarbons such as benzene, toluene or xylene, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as ethyl ether, isopropyl ether, dioxane or tetrahydrofuran, a nitrile such as acetonitrile or propionitrile, hydrocarbons such as petroleum ether, petroleum benzene or hexane, a ketone, such as acetone or methyl ethyl ketone, esters such as ethyl acetate, amides such as N,N-dimethylformamide, N, N-dimethylacetamide or triamide, N,N,N',N'-hexamethylphosphoric acid. These solvents can be used alone or in combination as a mixture. Especially preferable to apply a simple ester or AMI is ylcarbamate (Y; X=0, Y represents a lower alkyl group) and connection /III/ heated in a solvent such as benzene or toluene, to obtain the compounds of the present invention (1; X=0).

Reaction scheme 4

< / BR>
In the above formulas, Q, G, L and Y have the meanings defined above.

Namely, the derived sultaniasultania /IV/ subject interaction with urethane derivative /VIII/ in a solvent such as acetone, acetonitrile or dioxane, in the presence of inorganic bases such as potassium carbonate, or organic bases such as triethylamine, or DWI, to obtain the compounds of the present invention (1; X=0).

Reaction scheme 5

< / BR>
In the above formulas, Q, G and L have the meanings given above.

Namely Amin /III/ undergoes reaction with chlorosulfonylisocyanate in a solvent such as tetrahydrofuran, dimethoxyethane, acetonitrile, propionitrile, N,N-dimethylformamide, dichloromethane, dichloroethane, benzene or toluene, and then subjected to interaction with sulphonamide /VI/ in the presence of a base, such as triethylamine, pyridine, sodium hydride, sodium methylate, sodium ethylate, sodium hydroxide, potassium hydroxide or potassium carbonate, who's above formulas, Q and G have the meanings defined above.

In particular, sulfimidosulfides derived /IV/ subject interaction with isothiocyanates derived /IX/ in a solvent such as acetone, acetonitrile or dioxane, in the presence of inorganic bases such as potassium carbonate, or organic bases such as triethylamine or DWI, to obtain the compounds of the present invention (1; X=S, L=H).

Sulfimidosulfides/tio/ zinatova derivative (II) used as starting material in reaction scheme 1, can be synthesized from a derivative of sultaniasultania /IV/ in accordance with the methods described, for example, in examined Japanese patent publications NN 148879/1983, 31775/1984 and 13266/1980.

Next, sulfamethoxypyridazine (II; X=0) can also be synthesized according to the method of reaction scheme 7 in accordance with the method described, for example, not in the examined Japanese patent publication N 81320/1974.

Reaction scheme 7

< / BR>
In the above formulas, Q has the values defined above.

Derived sulfimidosulfides/tio/cyanate /II/, sulfimidosulfides derived /IV/, phenyl N-sulfamethazole/tio/to the as intermediates in the present invention, are also new compounds. Sulfimidosulfides derived /IV/ may be synthesized from a derivative of sulphonamide /VI/ methods of reaction schemes 8 and 9.

Reaction scheme 8

< / BR>
In the above formulas, Q has the values defined above.

In reaction scheme 8, the removal of the tert-butilkoi group is carried out using triperoxonane acid. The number triperoxonane acid may optionally be selected in the range of from an equimolar amount to an excessive amount. Triperoxonane acid can also be used as solvent without any problems.

The reaction temperature may be optionally selected in the range from -50oC to 80oC, preferably from -20oC to 30oC.

When this reaction is applied, the solvent is inert to the reaction, the solvent includes aromatic hydrocarbons such as benzene, toluene or xylene, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as ethyl ether, isopropyl ether, dioxane or tetrahydrofuran, NITRILES, such as acetonitrile Il the tone or methyl, esters, such as ethyl acetate, amides such as N,N-dimethylformamide, N,N-dimethylacetamide or triamide, N,H,N',N'-hexamethylphosphoric acid. These solvents can be used alone or in combination as mixtures.

Reaction scheme 9

< / BR>
In the above formulas, Q has the values defined above.

In reaction scheme 9 reaction of tert-butanol with chlorosulfonylisocyanate can be carried out in the manner known in itself, for example, in accordance with not the examined Japanese patent publication N 101323/1975.

The reaction of sulphonamide /VI/ with tert-butylchloride is carried out using from 0.5 to 3.0 mol, preferably from 0.9 to 1.2 mol of tributyltinchloride per mole of sulphonamide /VI/.

The reaction temperature can be selected optionally in the range from -50oC to 100oC, preferably from -20oC to 30oC.

The reaction may be carried out using different bases. The base is used in amounts of from 0.5 to 4.0 mol, preferably from 0.8 to 2.2 mol, per mole of sulphonamide /VI/. Passing the base include metal hydrides such as sodium hydride, a metal alcoholate such as sodium ethylate,5,4,0/-7-undecene (DBU) and inorganic bases, such as potassium hydroxide or sodium hydroxide. Especially preferred to use a metal hydride.

A suitable solvent for the reaction is a solvent inert to the reaction, which includes aromatic hydrocarbons such as benzene, toluene or xylene, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as ethyl ether, isopropyl ether, dioxane or tetrahydrofuran, NITRILES, such as acetonitrile or propionitrile, hydrocarbons such as petroleum ether, petroleum benzene or hexane, ketones, such as acetone or methyl ethyl ketone, esters such as ethyl acetate, amides such as N,N-dimethylformamide, N, N-dimethylacetamide or triamide, N,N,N',N'-hexamethylphosphoric acid. These solvents can be used alone or in combination as mixtures. Especially preferable to apply a simple ester or amide.

In reaction scheme 3 phenyl N-chlorosulfonylisocyanate (VII; Y is a lower alkyl group) can be prepared by methods known per se, in accordance for example with the publication of Chemische Berichte, T. 96, S. 56 /1963/. The sulphonamide /VI/, used as starting material in 42 /1944/, in U.S. patent 2 826 594, in Journal of Synthetic Organic Chemistry, Japan, T. 27 (N 10), S. 980 /1969/, U.S. patent 2 624 729, Chemische Berichti, I. 111, C. 1915 /1978/, not examined Japanese patent publications N 79894/1978 and N 208289/1983, Jndian Journal of Chemistry, Section B. T. 21B, S. 941 /1982/. As typical examples will be given of the synthesis of N,N-dimethyl-N'-methoxytyramine, N-methyl-N-methoxy-N'-ethylsulfonyl, N-methyl-N-methoxy-N'-methoxytyramine, N,N-dimethyl-N'-triftormetilfosfinov, N-methyl-N-methoxy-N'-trichlorotriethylamine and 2-methoxy-1,2,5-thiadiazolidine-1,1-dioxide as the reaction schemes 10-15.

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Currently, the syntheses of the compounds of the present invention will be described as examples. However, it should be understood that the present invention is in no way limited to such specific examples.

Example 1

Obtaining 1-[(N-dimethylsulphamoyl-N-methoxyamino)sulfonyl] -3-/4,6-dimethoxypyrimidine-2-yl/urea

< / BR>
To 100 ml of dry tetrahydrofuran (THF) containing 1,87 g (42,9 mmol) of 55% sodium hydride was added 3.0 g (of 19.5 mmol) of N,N-dimethyl-N'-methoxytyramine dissolved in 20 ml of dry THF under ice cooling, and the mixture was continuously Persepolis at the same temperature for 10 minutes

Then to the mixture dropwise dependo was heated to room temperature and continuously stirred at room temperature for one hour.

The reaction mixture was poured into 500 ml of ice water containing 5 g of 35% hydrochloric acid, and was extracted with diethyl ether. Diethyleneamine layer was sequentially washed with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. Then the solvent was distilled under reduced pressure, giving of 5.4 g of phenyl N-[(N-dimethylsulphamoyl-N-methoxyamino)sulfonyl] carbamate in the form of an orange oil.

Then a mixture containing 3 g (8.5 mmol) of the above compounds of 0.93 g (6 mmol) of 2-amino-4,6-dimethoxypyrimidine and 20 ml of dry benzene was heated under reflux for 10 minutes After cooling, the solvent was distilled under reduced pressure. The residue was washed with diethyl ether and collected by filtration, giving 1.0 g of the desired product 1-[(N-dimethylsulphamoyl-N-methoxyamino] sulfonyl-3-/4,6-dimethoxypyrimidine-2-yl/urea. The melting point of 166-167oC.

Example 2

Obtaining 1-[(N-(N-methyl-N - methoxyaminomethyl)-N-ethylamino)-sulfonyl]-3-/4,6-dimethoxypyrimidine-2-yl/urea

< / BR>
To 50 ml of dry tetrahydrofuran (THF) containing 1.60 g (to 36.7 mmol) of 55% sodium hydride was added 2.8 g (of 16.7 mmol) N-methyl-N-tags at the same temperature for 10 minutes

Then dropwise added 30 ml of dry THF containing 4,13 g (17.5 mmol) of phenyl-N-chlorosulfonylisocyanate, and the mixture was gradually warmed to room temperature and continuously stirred at room temperature for one hour.

The reaction mixture was poured into 500 ml of ice water containing 4 g of 35% hydrochloric acid, and was extracted with diethyl ether. Diethyleneamine layer was sequentially washed with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. Then the solvent was distilled under reduced pressure, giving 5.0 g of phenyl N-[(N-(N-methyl-N-methoxyaminomethyl)-N-ethylamino)sulfonyl] carbamate in the form of an orange oil.

Then a mixture containing 2.5 g (6.8 mmol) of the above compounds, 0.74 g (4.8 mmol) of 2-amino-4,6-dimethoxypyrimidine and 50 ml of dry benzene, was heated under reflux for 10 minutes After cooling the mixture, the solvent was distilled under reduced pressure. The residue was washed with diethyl ether and collected by filtration, giving 1.2 g of the desired 1-[(N-(N-methyl-N-methoxyaminomethyl)-N-ethylamino)sulfonyl] -3-/4,6-dimethoxypyrimidine-2-yl/urea. Melting point: 157-158oC.


< / BR>
To 15 ml of dry tetrahydrofuran (THF) containing 0.25 g (of 6.25 mmol) of 60% sodium hydride was added 0,43 g and 2.83 mmol) 2-methoxy-1,2,5-thiadiazolidine-1,1-dioxide dissolved in 5 ml dry THF under ice cooling, and the mixture was Persepolis in a stream of nitrogen at room temperature for 14 h

Then the system was cooled to 0oC, and to it was added 10 ml of dry THF containing 0.7 g (3 mmol) phenyl-N - chlorosulfonylisocyanate dropwise. The mixture was gradually warmed to room temperature and continuously stirred at room temperature for one hour.

The reaction mixture was poured into 100 ml of ice water containing 0.6 g of 35% hydrochloric acid, and was extracted with diethyl ether. Diethyleneamine layer was sequentially washed with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. Then the solvent was distilled under reduced pressure, giving 0.7 g of the desired phenyl N-/2-methoxy-1,2,5-thiadiazolidine-1,1-dioxide-5-sulfonyl/carbamate as a yellow viscous oil.

Then a mixture comprising 0.7 g (2 mmol) of the above compound, 0.31 g (2 mmol) 2-amino-4,6-dimethoxypyrimidine and 10 ml of dry benzene, was heated with skim milk is the STATCOM, obtained were washed with diethyl ether and was obtained 0.5 g of the desired 1-(2-methoxy-1,2,5-thiadiazolidine-1,1-dioxide-5-sulfonyl)-3-(4,6-dimethoxypyrimidine-2-yl)urea. Melting point: 162-163oC.

Structure and physical properties of the compounds obtained by the same method as described in the previous examples shown in Fig.2-10.

Now table. 1-26 are examples of specific compounds of the present invention, including the compounds obtained in the previous examples. However, it should be understood that the compounds of the present invention is not limited to such specific examples.

The symbols used in the tables have the following meanings: Me: methyl group, Et: ethyl group, Pr n: sawn group, Pr i: ISO-propyl group, Pr c: cyclopropyl group, Bu n: n-bucilina group, Bu s: Deut. -bucilina group, Bu i: isobutylene group, Bu t: tert-bucilina group, Pen-n; n-pencilina group, Ph: phenyl group, and Gn has the same meaning as the above-mentioned symbol G, and includes Ga, Gb, Gc, defined below.

Ga G1 G13 (i.e., it represents all of the G1 G13).

Go G1 G6 (i.e., it represents all of the G1 G6).

Gc G1 G3 (i.e., it represents all of the G1 G3).

Quaeda with a suitable carrier, for example, a solid carrier such as clay, talc, bentonite or diatomaceous earth, or a liquid carrier such as water, alcohol (such as methanol or ethanol), aromatic hydrocarbons (such as benzene, toluene or xylene), chlorinated hydrocarbons, simple, ether, ketone, ester (such as ethyl acetate), or acid amide (such as dimethylformamide). If desired, can be added emulsifier, dispersing agent, suspendisse the agent, the agent that promotes penetration, distribution, or stabilizer to obtain if necessary forms, such as liquid ready form of the drug, emulsifiable concentrate, wettable powder, dust, granules or liquid drug.

Now will be given examples of formulations of herbicides containing the invention as an active ingredient. However, it should be understood that the present invention is in no way limited to such specific examples. In the following examples, preparative forms "part" means "part by weight".

Example 1 formulation of the present invention:

Wettable powder

Compound No. 1 of the present invention 20 parts

Gilit And (trademark of kaolin clay type, producing the active agent and anionic surface-active agent, manufactured by Toho chemical industry Co. Ltd.) 2 parts

Corplex (trade mark agent that prevents coagulation, consisting of a mixture of surfactants and finely ground powder of silicon dioxide produced by the firm Shionogi pharmaceutical Co. Ltd.) 2 parts

The above ingredients homogeneous pulverized and mixed with the formation of a wettable powder.

Example 2 preparative form:

Wettable powder

Compound No. 2 of the present invention 40 parts

Zicklin A (trade name kaolin clay type, manufactured Gilit industries, Co. Ltd.) 54 part

Sobol 5039 (trade name of a mixture of nonionic and anionic surfactants, produced by Toho chemical industry Co. Ltd.) - part 2

Corplex (trade name of an agent that prevents coagulation, consisting of a mixture of surface-active agent and a fine powder of silicon dioxide produced Shionogi pharmaceutical Co. Ltd.) 4 pieces

The above ingredients homogeneous pulverized and mixed with the formation of a wettable powder.

Example 3 preparative form:

Emulsifiable concentrate

Link is argovie name of a mixture of nonionic and anionic surfactants, produced by Toho chemical industry Co. Ltd.) - 5 parts

The above ingredients homogeneous blend with the formation of the emulsifiable concentrate. When using the above emulsifiable concentrate is diluted with water in 10-10000 times and used so that the amount of active ingredient 0.005 to 10 kg per hectare.

Example 4 formulation:

Fluid drug

Compound No. 4 of the present invention 25 parts

Agrisol S-710 (trade name of a surfactant manufactured by Kao Corporation), 10 parts

Rooks 1000C (trade name, anionic surfactant manufactured by Toho chemical industry Co. Ltd.) 0.5 parts

1% Rhodopol water (trade name thickener manufactured by Rhone-Poulenc) 20 parts

Water 44,5 parts

The above ingredients homogeneous mixed with obtaining a fluid drug.

Example 5 formulation:

Fluid drug

Compound No. 20 of the present invention 40 parts

Agrisol S-710 10 parts

Rooks 1000C 0.5 parts

1% Rhodopol water 20 parts

Water 29.5 parts

These ingredients homogeneous mixed with obtaining current is the shadow part 1

Bentonite and 55 parts

Talc 44 parts

The above ingredients are mixed and homogeneous pulverized, and after adding a small amount of water and the mixture was mixed and granulated with a granulating mechanism extrusion type, followed by drying to obtain granules.

In addition, the compound of the present invention can be combined with other herbicides, various insecticides, fungicides and agents synergies during preparation preparative forms or during the application, depending on the need.

As such other herbicides may be, for example, the compound described in Farm Chemicals Handbook (1989).

For example, the compound of the present invention can be mixed with herbicides such as alachlor, acetochlor, metalochlor, primisulfuron, nicosulfuron, atrazine, cyanazine, EPTC, 2,4-D, butyl, dicamba, bromoxynil, tridiphane, metsulfuron-methyl, thifensulfuron-methyl, triasulfuron, Isoproturon, chlorotoluron, diflufenican, methabenzthiazuron, diclofop-methyl, difenzoquat, fenoxaprop-ethyl, bentazon, trifluralin, pendimethalin and N-[(4,6 - dimethoxypyrimidine-2-yl)aminocarbonyl]-3-chloro-4-methoxycarbonyl-1-IU what woadie or antidote), such as 1,8-naphthoic anhydride or N,N-diallyl-2,2-dichloroacetamide.

The compound of the present invention can be used to combat a variety of weeds not only in the field of agriculture and horticulture in fields such as upland fields, flooded paddy fields or in gardens, but also on non-agricultural land, such as playgrounds, unused vacant land or areas along railroads.

The dose varies depending on location, season, method of application, type of weeds to be destroyed, type of cultivated plants and so on. However, the usual dose is in the range of 0.005 to 10 kg per hectare in the form of the amount of the active ingredient.

Now weed-killing activity of the compounds of the present invention will be described in detail with reference to the following examples of tests. Rooms compounds referred to in the examples of the tests correspond to the numbers of the compounds given above.

Example 1 tests:

Test for herbicide action soil

A plastic box having a length of 15 cm, a width of 22 cm and a depth of 6 cm, filled with sterilized diluvial soil, and sown the seeds Echinochlo they cover thickness of about 1.5 cm, and then on the soil surface was applied a solution of the herbicide evenly so that the active ingredient is distributed in a given concentration. Herbicide solution was prepared by diluting the wettable powder described in the preceding examples preparative forms water and deposited on the whole surface of the soil using a hand sprayer. Four weeks after the herbicide solution was determined herbicide effects against each weed and indicators of phytotoxicity against cultivated plants on the basis of the following standard estimates. The results are shown in table.27. (Norm compounds correspond to the numbers of the compounds in the examples). Some of the compounds of the present invention show selectivity for certain cultivated plants.

Standard evaluation:

5: the Degree of inhibition of growth of more than 90% (almost completely faded)

4: degree of suppression of the growth from 70 to 90%

3: degree of suppression of the growth from 40% to 70%

2: the Degree of suppression of the growth from 20 to 40%

1: degree of suppression of the growth from 5% to 20%

0: the Degree of inhibition of growth of less than 5% (almost ineffective)

Above, the degree of inhibition of growth was calculated with the poverhnosti soil in the treated area;

N weight of terrestrial weeds in the untreated area.

The test example 2:

Test for herbicide action in the processing of leaves

Plastic box with a length of 15 cm, a width of 22 cm and a depth of 6 cm was filled with sterilized diluvial soil and spots were sown the seeds of Echinochloa crus-galli, Digitaria adscendens, Cyperus microiria, Solanum nigrum, Galinsoga ciliata, Rorippa indica, Oryza sativa, Zea mays, Triticum aestivum, Glycine max, gossypium herbaceum and Beta vulgaris, and the top seeds were covered with soil of a thickness of about 1.5 cm When various weeds and cultivated plants were grown to stage 2 or 3 sheets, the sheets were uniformly sprayed with a solution of the herbicide so that the active ingredient was applied at a given concentration.

The herbicide solution was prepared by dilution with water wettable powder described in the above examples, preparative forms and deposited on the entire surface of the foliage of weeds and cultivated plants using a small sprayer. Four weeks after the herbicide solution was determined, and herbicide effects on weeds and phytotoxicity in respect of each of cultivated plants on the basis of the standard ratings described in test example 1. The results are shown in tab is blowing abbreviations

Dose: the Dose of active ingredient /kg/ha/

EC: Echinochloa crus-golli (barnyardgrass) barnyard grass

DI: Digitaria adscendens (large crabgrass) weed

CY: Cyperus microiria (annual sedge) sedge annual

SO: Solanum nigrum (black hightshade) nightshade black

GA: Galinsoga ciliata (hairy galinsoga) galinsoga hairy

RO: Rorippa indica (fieldcress) gershnik Indian

OR: Oryza sativa (rice) rice

ZE: Zea mays (corn) corn

TR: Triticum aestivum (wheat) wheat

GL: Glycine max (soybean) soybean

GO: Gossypium herbaceum (cotton) cotton

BE: Beta vulgaris (sugar beet) sugar beet

Next, the present inventors have conducted studies with the aim of increasing herbicide effects of the compounds of the present invention. In the result it was found that when the compound of the present invention is added to one of alachlor, acetochlor, metolachlor, primisulfuron and nicosulfuron, herbicide effect not only reaches the sum of the effects of the corresponding compounds, but it turns Energeticheskiy effect, without showing any phytotoxicity against crops.

To prove the advantages of the claimed compounds was conducted the experiment in accordance with the foregoing method of test example 1. Thus obtained results are shown in table.

The main weeds found in a corn field, designated as A, B, C, D.

The results are presented in table.A.

From table.And it is seen that the compounds of this application has surpassed known in 2-8 times herbicide effect and 8 times the level of security in relation to corn.

A: Xanthium strumarium

B: Ipomoea purpurea

C: Chenopodium album

D: Datura stramonium

ZE: Zea mays (corn)

Energeticheskiy herbicide effect of a mixture of herbicides will be explained below as follows.

Namely, the individual active compounds may find some of their own shortcomings in terms herbicide activity in many cases. In this case, when there are two active connections, if this herbicide activity is more than the simple sum of the relevant activities of the two compounds (i.e., the expected activity), it is sinergeticheskim effect. The expected activity for a given combination of two herbicides can be calculated as follows (Colby, S. R. Calculation of the synergistic and antagonistic activities of combinations of herbicides. Weed, so 15, S. 20-22, 1967.

< / BR>
where the degree of suppression, when the herbicide And note the e suppression, when you apply a kg/ha of herbicide A and b kg/ha of herbicide B.

Namely, if the actual degree of suppression is greater than the degree of suppression, calculated by the above formula, the activity in combination is considered as exhibiting herbicide action.

Now it will be explained specifically with reference to examples. However, these compounds, the proportions in their formulation and types preparative forms according to the present invention should not be construed as limited to such specific examples. In these examples, "parts" means "parts by weight".

Example 7 formulation:

Wettable powder

Connection N3 of the present invention 10 parts

Primisulfuron 10 parts

Gilit PFP (trade mark clay Malinovskogo type, produced Zicklin industries Co. Ltd.) 72 part

Sobol 5039 (trade mark sulfate Olkiluoto ether, produced by Toho chemical industry Co. Co., Ltd.) 2 parts

Soybean oil 2 parts

Corplex # 80 (trademark fine powder of silicon dioxide produced Shionogi pharmaceutical Co. Ltd.) 4 pieces

The above ingredients homogeneity was pulverizadores and mingled with the formation of zmajeva is his invention 10 parts

Nicosulfuron 10 parts

Gilit PFP (trade mark clay kaolin type, manufactured Gilit industries, Co., Ltd.) 72 part

Sobol 5039 (trade mark sulfate Olkiluoto ether, produced by Toho chemical industry Co. Ltd.) 2 parts

Soybean oil 2 parts

Corplex # 80 (trademark fine powder of silicon dioxide produced Shionogi pharmaceutical Co. Ltd.) 4 pieces

The above ingredients homogeneity was pulverizadores and mingled with the formation of a wettable powder.

Example 9 formulation:

Suspension concentrate

Compound No. 3 of the present invention 2 parts

Alachlor 38 parts

Sorbon T-80 (trade mark of polyoxyethylene sorbitan monooleate, produced by Toho chemical industry Co. Ltd.) 5 parts

Wigum (brand magnesium-aluminum-silicate, manufactured by Vanderbyl To.) 5 parts

Water 50 parts

The above ingredients were uniformly mixed and pulverizadores using a sand mill to obtain a suspension concentrate having a particle size of at most 5 μm.

Example 10 formulation:

Suspension concentrate

Compound No. 3 of the present izobretatelnye above ingredients were uniformly mixed and pulverizadores using a sand mill to obtain a suspension concentrate, having a particle size of at most 5 μm.

Example 11 formulation:

Granules

Compound No. 3 of the present invention 5 parts

Metalochlor 75 parts

Aron A (trade mark of polycarboxylate manufactured by Toagosei chemical industry Co. Ltd.) 7 parts

Senecio C (trade mark ligninsulfonate, manufactured by San-Kokusaku pulp Co. Ltd.) 10 parts

Powder Nylex (brand ET-PA produced by Nippon oil & Feto To. Ltd.) 2 parts

Gilit PFP (trade mark clay kaolin type, manufactured Gilit industries, Co. Ltd.) part 1

To the above ingredients was added a suitable amount of water, and the mixture was pulverizadores and mixed to obtain a suspension, which was granulated to obtain granules, and the moisture was removed using a spray dryer:

Example 12 formulation:

Granules

Compound No. 3 of the present invention 5 parts

Alachlor 75 parts

Aron A, 7 parts

Senecio C 10 parts

Powder Nulex 2 parts

Gilit PFP (trade mark clay kaolin type) 1 piece

To the above ingredients was added a suitable amount of water, and the mixture of pulv is using spray dryers.

Example 3 tests:

Test for herbicide action soil

Plastic box with a length of 30 cm, a width of 30 cm and a depth of 10 cm was filled with sterilized Nagorno soil and spots were inoculated maize seeds (Zia mays), spickle green (Sitaria viridis), limnocharis (Abutilon theophrasti) and cocklebur (Xanthium strumarium), and the seeds were covered with soil layer thickness of about 0.5 cm on the day of sowing was applied herbicide solution in water for spraying at a rate of 5 l/ha Herbicide solution, which was used, were prepared by dilution of the formulation described in the previous examples, preparative forms, water, and was applied using a small sprayer. The weight of the surface part of each weed was measured after three weeks after application, and the degree of regulation of growth (%) was calculated using the following equation.

The degree of regulation of growth (%) (1 T/N) x 100

where T is the weight of terrestrial weeds in the treated area;

N weight of terrestrial weeds in the untreated plot.

The results of the test for herbicide action provided by individual herbicides, shown in the table.29. The results of the test for herbicide action mixture Hesperia:

Test for herbicide action in the processing of growth stage

Plastic box with a length of 30 cm, a width of 30 cm and a depth of 10 cm was filled with sterilized Nagorno soil and spots were sown the seeds of maize (Zea mays), spickle green (Setaria viridis), limnocharis (Abutilon theophrasti) and cocklebur (Xanthium strumarium/, and the seeds were covered with soil of a thickness of 0.5 cm On the tenth day after inoculation growth stage were sprayed herbicide solution with a quantity of sprayed water 5 l/ha Herbicide solution for spraying was prepared by dilution preparative forms obtained in accordance with the previous examples preparative forms water was sprayed using a small sprayer. The weight of the surface part of each weed was measured after two weeks after application, and the degree of regulation or inhibition of growth (%) was obtained in the same manner as in test example 3.

Test results of the individual herbicide herbicides are shown in table.31.

Test results of herbicide action of a mixture of herbicides shown in the table. 32. (The numbers of the compounds correspond to the numbers of the compounds given in the examples).

In table.29-32 use the>/BR>AB: Abutilon theophrasti (limnocharis)

XA: Xanthium strumarium (cocklebur)

ZE: Zea mays (corn)

mV: Measured value

W: the Expected value.

1. Derivative sulfamethoxypyrazine General formula I

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where Q is

< / BR>
< / BR>
where R" C1C4is an alkyl group, a C2- C4-Alchemilla group2WITH4-Alchemilla group or1WITH4is an alkyl group, substituted C1- C4-alkoxygroup, phenyl;

R"' C1C4is an alkyl group;

L is hydrogen or C1WITH4is an alkyl group;

G -

< / BR>
where methyl or methoxy;

With methyl, methoxy or deformedarse.

2. Selective herbicide composition comprising the active ingredient is a derivative of the sulfonylureas and the target additives, characterized in that as a function of sulfonylureas it contains a compound of formula I under item 1 in the following ratio of ingredients, wt.

Active ingredient 2 40

The target additive and the Rest

Priority signs:

04.12.89 when

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or

< / BR>
2R" C1C4is an alkyl group, R"' C1- C4is an alkyl group, L is hydrogen, G methoxy, methoxy, methyl;

04.12.89 p

 

Same patents:

The invention relates to new chemical substances, which have valuable pharmacological properties, more particularly to a nitrogen-containing heterocyclic compounds of General formula I

< / BR>
where X is oxygen or sulfur;

Y is carbon or nitrogen;

Z is carbon or nitrogen, and Y and Z are not simultaneously mean nitrogen;

R1and R2independent from each other and denote hydrogen, alkyl with 1 to 6 carbon atoms, halogen, trifluoromethyl, nitrile, alkoxy with 1 to 6 carbon atoms, a group of CO2R7where R7means hydrogen or alkyl with 1 to 6 carbon atoms, group-C(O)NR8R9where R8and R9not dependent from each other and denote hydrogen, alkyl with 1 to 3 carbon atoms, methoxy or together with the nitrogen form a morpholine, pyrrolidine or piperidine-NR10R11where R10and R11denote hydrogen or alkyl with 1 to 6 carbon atoms, group-C(O)R12where R12means alkyl with 1 to 6 carbon atoms, group-SO2R12where R12has the specified value, -NHC(O)R12where R12has the specified value, -NHSO2R12where R12has a specified value, and-SO2NR13R14where R13and R142R12where R12has the specified value, -NHC(O)R12where R12has the specified value, -NHSO2R12where R12has the specified value, -SO2NR13R14where R13and R14have a specified value, a nitrogroup, 1-piperidinyl, 2-, 3 - or 4-pyridine, morpholine, thiomorpholine, pyrrolidine, imidazole, unsubstituted or substituted at the nitrogen by alkyl with 1 to 4 carbon atoms, 2-thiazole, 2-methyl-4-thiazole, dialkylamino with 1 to 4 carbon atoms in each alkyl group, or alkilany ether with 1 to 4 carbon atoms;

R4an ester of formula-CO2R16where R16means alkyl with 1 to 4 carbon atoms, the amide of formula C(O)NR17R18where R17and R18independent from each other and denote hydrogen, alkyl with 1 to 2 carbon atoms, methoxy or together with the nitrogen form a morpholine, piperidine or pyrrolidine, phenyl, unsubstituted or substituted by residues from the group comprising halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, 3-methyl-1,2,4-oxadiazol-5-yl, 2 - or 3-thienyl, 2-, 3 - or 4-pyridyl, 4-pyrazolylborate 4 stands, the ketone of the formula C(O)R19'where R19means alkyl with 1 to 3 carbon atoms, phenyl or 1-Mei-2-yl, a simple ester of the formula-CH2OR20where R20means alkyl with 1 to 3 carbon atoms, thioether formula-CH2SR20where R20has the specified value, the group CH2SO2CH3amines of the formula-CH2N(R20)2where R20has the specified value, the remainder of the formula-CH2NHC(O)R21where R21means methyl, amino or methylamino - group-CH2NHSO2Me2where Me denotes methyl carbamate of the formula CH2OC(O)NHCH3;

R5and R6independent from each other and denote hydrogen or methyl;

n is 0,1 or 2,

Provided that the substituents are not simultaneously have the following meanings: Y and Z is carbon, R1or R2hydrogen, halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, cyano, nitro, trifluoromethyl, R3unsubstituted phenyl and R4group-C(O)OR16'where R16'means hydrogen, alkyl, alkenyl or quinil, group-C(O)N(R18')(R19'), where R18'and R19'denote hydrogen, alkyl with 1 to 6 carbon atoms, phenyl, alkoxy or together with the nitrogen form pyrrolidine, piperidine or morpholine, cyanotic, unsubstituted phenyl and 4-imidazole,

in the form of a racemate or an individual enantiomers and their salts, are inhibitors of leukotriene biosynthesis

The invention relates to new 2-sharonlee heterocyclic carboxylates, inhibiting the enzymatic activity of proteolytic enzymes, containing compositions, to a method of their use for the treatment of diseases associated with degeneration of the tissues, and to a method of production thereof

The invention relates to new benzanilide derivatives, processes for their preparation and the pharmaceutical compositions

The invention relates to organic chemistry, and more specifically to new connections - hydrochloridum 2-aminoimidazole and 2-aminothiazole General formula (1),

< / BR>
aryl, the substituent in position 4 and a disulfide bridge in the position 5, where X is alkylamino, for example, methylamino, and R1-R2is hydrogen; X-methylaminopropyl, and R1-alkyl, for example methyl and R2is hydrogen; X-methylaminopropyl, and R1-alkoxygroup, for example, methoxy and R2is hydrogen; X-methylaminopropyl, and R1-ethoxypropan and R2is hydrogen; X-methylaminopropyl, and R1halogen, for example chlorine and RF2is hydrogen; X-methylaminopropyl, and R1-R2-alkoxygroup, for example, methoxy; X-atramentaria, and R1-alkoxygroup, for example, methoxy and R2is hydrogen; X is sulfur, and R1-alkoxygroup, for example, methoxy and R2is hydrogen; X is sulfur, and R1-R2-alkoxygroup, for example, methoxy; X is sulfur, and R1halogen, for example fluorine and R2-hydrogen

The invention relates to new heterocyclic derivatives of substituted 2-acylamino-5-thiazolo exhibiting affinity to the receptor cholecystokinin and gastrin to a method for producing such compounds and to pharmaceutical compositions based on

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

The invention relates to a method for obtaining new pyrimidine derivatives possessing valuable fungicidal properties, which can find application in agriculture

The invention relates to pyrimidine derivative of the General formula I:

where R1- alkyl-(C1-C4), O-alkyl-(C1-C4), halogen;

R2- alkyl-(C1-C4), O-alkyl-(C1-C4);

n = 3-5;

Z = COOH, COO-alkyl-(C1-C4), CONHSO2C6H5with herbicide activity, and to a method of controlling undesirable vegetation by processing them in the locus, namely, that the treatment is carried out pyrimidine derivatives of General formula I:

where R1- alkyl-(C1-C4), O-alkyl-(C1-C4), halogen;

R2- alkyl-(C1-C4), O-alkyl(C1-C4);

n = 3-5;

Z = COOH, COO-alkyl-(C1-C4), CONHSO2C6H5in the amount of 1-10 kg/ha

The invention relates to methods of producing derivatives of 2-anilinopyrimidines or acid additive salts of novel biologically active compounds, which can find application in agriculture

The invention relates to allpresan replacement pyrimidines, in particular 2-amino - and 2-substituted amino-4-substituted-5-hydroxypyrene-dyn, which may be substituted in the 6 position, pharmaceutical compositions containing these compounds as active ingredients and methods of treatment using these compounds

The invention relates to a method of obtaining a new connection group 6-(4)-dipyrimidine, specifically dipyrimidine containing zenatello group with a cyclic nitrogen atom, and in the 4th and 5th position of the molecule OCH3and NH2groups, respectively, formula 1

(I)

Known the proposed synthesis of 4-carbomethoxy-5-(N-formyl-N-(2-cyanoethyl-amino)-1,2,3-thiadiazole of the formula (A)

(A)A study of biological activity of compounds (A)

The invention relates to new biologically active compounds derived pyrimidine-4-or their pharmaceutically acceptable salts with serotoninergicheskoi, dopaminergically, antihistaminic activity, and compositions on their basis
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