Substituted derivatives of pyrazole and a means of having a weed-killing activity

 

(57) Abstract:

Describes the new substituted pyrazole derivatives of General formula (I), where R1is alkyl with 1-4 carbon atoms, R2- allylthiourea with 1-4 carbon atoms or alkyloxy with 1-4 carbon atoms, unsubstituted or substituted by one or more halogen atoms; R1and R2form together a group -(CH2)m-; R3is hydrogen or halogen; R4is hydrogen, nitro, cyano or the group-C(O)NH2; R5group-C(=Y)-R6, -CH2-CH(R3)-COOR7where R6denotes hydrogen, alkyl with 1-6 carbon atoms, unsubstituted or substituted by one or more identical or different substituents from the group comprising halogen, hydroxyl, or a group OR16where R16denotes hydrogen, alkyl with 1-6 carbon atoms, substituted by one or more identical or different substituents from the group comprising halogen and alkoxy with 1-4 carbon atoms; Y is oxygen, a group-N OR17and-C(R18)-R19where R17denotes hydrogen, alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, quinil with 3-6 carbon atoms, alkoxycarbonyl-alkyl with 1-4 carbon atoms in alkoxycarbonyl part and 1-4 at each independently from each other hydrogen, halogen, cyano, alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, alkoxycarbonyl-alkyl with 1-4 carbon atoms in alkoxycarbonyl part and 1 to 4 carbon atoms in the alkyl part, which may optionally be substituted by halogen atoms; R7is alkyl with 1-4 carbon atoms, and R3have the above significance, or group (a), (b), (C), (d), where R8means hydrogen or alkyl with 1-4 carbon atoms; R9, R10, R11, R12, R13and R14each independently from each other hydrogen, halogen, alkyl with 1-4 carbon atoms, unsubstituted or substituted by halogen, alkyl with 1-4 carbon atoms and alkoxycarbonyl with 1-4 carbon atoms, substituted by one or more identical or different substituents from the group comprising hydroxyl and alkoxy with 1-4 carbon atoms; R15is alkyl with 1-4 carbon atoms; m = 3 or 4; n = 0, 1, 2 or 3; p = 0 or 1; X is oxygen or sulfur; Z is oxygen or sulfur; W is oxygen or carbon; compounds possess herbicide activity. Also described herbicide agent based on the compounds of formulas. 2 S. and 3 C.p. f-crystals, 2 PL.

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The invention relates to a new isododecane and means have a weed-killing activity.

Known derivatives of pyrazole with herbicide activity (see application WO 94/08999, MKI: 07 D 471/04, A 01 N 43/56, 28.04.1994,).

Object of the invention is the expansion of the range of the derivatives of pyrazole, which can be an active substance means having a weed-killing activity.

The problem is solved proposed substituted derivatives of pyrazole of the General formula (I)

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in which R1is alkyl with 1-4 carbon atoms,

R2-alkylthio group with 1-4 carbon atoms or alkyloxy with 1-4 carbon atoms, unsubstituted or substituted by one or more atoms of halogen,

R1and R2form together a group -(CH2)m-,

R3is hydrogen or halogen,

R4is hydrogen, nitro, cyano or the group-C(O)NH2,

R5group

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where R6denotes hydrogen, alkyl with 1-6 carbon atoms, unsubstituted or substituted by one or more identical or different substituents from the group comprising halogen, hydroxyl, or a group OR16where R16denotes hydrogen, alkyl with 1-6 carbon atoms, substituted by one or more of the Y is oxygen, group-N OR17or

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where R17denotes hydrogen, alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, quinil with 3-6 carbon atoms, alkoxycarbonyl-alkyl with 1-4 carbon atoms in alkoxycarbonyl part and 1 to 4 carbon atoms in the alkyl part, which may optionally be substituted by halogen atoms, R18and R19each independently from each other hydrogen, halogen, cyano group, alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, alkoxycarbonyl-alkyl with 1-4 carbon atoms in alkoxycarbonyl part and 1 to 4 carbon atoms in the alkyl part, which may optionally be substituted by halogen atoms, R7alkyl with 1 to 4 carbon atoms, a R3has the above value,

or group

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where R8means hydrogen or alkyl with 1-4 carbon atoms, R9, R10, R11, R12, R13and R14each independently from each other hydrogen, halogen, alkyl with 1-4 carbon atoms, unsubstituted or substituted by halogen, alkyl with 1-4 carbon atoms and alkoxycarbonyl with 1 to 4 carbon atoms, substituted by one or more identical or different substituents from the group comprising hydroxyl and alkoxyl from 1-4 at the
X is oxygen or sulfur,

Z is oxygen or sulfur,

W is oxygen or carbon.

In the first preferred group of substituted derivatives of pyrazole of the General formula (I) include compounds in which

R1is methyl,

R2- methylthio or diformitatii,

R1and R2together denote a group -(CH2)4-,

R3is hydrogen, chlorine or bromine,

R4is hydrogen, nitro, cyano or the group-C(O)NH2,

R5group

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where R6denotes hydrogen, alkyl with 1-6 carbon atoms or a group-OR16where R16denotes hydrogen, alkyl with 1-6 carbon atoms, unsubstituted or substituted by one or more identical or different substituents from the group comprising halogen and alkoxy with 1-4 carbon atoms,

Y is oxygen, a group-N OR17or

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R17denotes hydrogen, alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, quinil with 3-6 carbon atoms, alkoxycarbonyl-alkyl with 1-4 carbon atoms in alkoxycarbonyl part and 1 to 4 carbon atoms in the alkyl part, which can be substituted by halogen atoms, R18and R19each independently from each other hydrogen, halogen, cyano, alkyl with 1-6 atoms oglers 1-4 carbon atoms in the alkyl part, which may be substituted by halogen atoms: alkoxy with 1-4 carbon atoms, R7is hydrogen or alkyl with 1-4 carbon atoms, a R3has the above value,

or group

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where R8means hydrogen or alkyl with 1-4 carbon atoms, R9, R10, R11, R12, R13and R14each independently from each other hydrogen, alkyl with 1-4 carbon atoms or alkoxycarbonyl with 1-4 carbon atoms, substituted by one or more identical or different substituents from the group comprising hydroxyl and alkoxy with 1-4 carbon atoms, R15is alkyl with 1-4 carbon atoms,

m = 3 or 4,

n = 0, 1, 2 or 3,

p = 0 or 1,

X is oxygen or sulfur,

Z is oxygen or sulfur,

W is oxygen or carbon.

The second group of preferred substituted derivatives of pyrazole of the General formula (I) include compounds in which

R1is methyl,

R2- deformedarse,

R1and R2together form a group -(CH2)4-,

R3- chlorine,

R4- nitro or cyano,

R5group

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where R6means hydrogen or a group-OR16where R16means alkyl with 1-6 carbon atoms,

Y >9each independently from each other hydrogen, halogen,

or group

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where R8means hydrogen, R9, R10, R11, R12, R13and R14each independently from each other hydrogen, alkyl with 1-4 carbon atoms, alkoxycarbonyl-alkyl with 1-4 carbon atoms in alkoxycarbonyl part and 1 to 4 carbon atoms in the alkyl part or haloalkyl with 1-4 carbon atoms,

n = 0,

p = 0 or 1,

X is oxygen.

Compounds of the above General formula (I) can be obtained in the following way:

A) Compound of General formula (II)

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in which R1, R2and R3have the above meanings, is subjected to the interaction with the compound of General formula (III)

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in which R4means a group-COOR7where R7have the above significance, or a group-C(O)NH2,

R5have the above values except formyl group, and b means a group OR16or

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where R16, R17and R18each independently of one another denotes alkyl with 1-4 carbon atoms, or

B) in the case when R5denotes a formyl group, a compound of General formula (Ia)

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in which R1, R2, R
In the case when R5refers to a group-CYR6where R6have the above values, Y represents oxygen,

in the compound of General formula (IB)

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in which R1, R2, R3and R4have the above values, enter the metal ion by reaction with the appropriate reason and then interact with the acyl compound of General formula (IV) or (V)

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in which R6has the above value, a D means chlorine, bromine, group OR20or

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where R20, R21and R22have the above values, while if R6means hydrogen, D is a group-OR20or

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or

G) in the case when R5mean group

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in which R6has the above value, a Y means a group of-N OR17in which R17have the above values

the compound of General formula (IB)

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in which R1, R2, R3, R4and R6have the above meanings, is subjected to the interaction with the compound of General formula (VI)

H2N - OR17, (VI)

in which R17have the above values

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where R18and R19have the above values, the compound of General formula (IB)

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in which R1, R2, R3, R4and R6have the above meanings, is subjected to the interaction with the compound of General formula (VII) or (VIII)

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in which R18and R19have the above significance, and R23means alkyl with 1 to 4 carbon atoms,

or

E) in the case when R5means one of the groups

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in which R8, R9, R10, R11, R12, R13, R14, R15n, p and W have the above values?

the compound of General formula (Iك)

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in which R1, R2, R3, R4, R8and n have the above meanings, is subjected to the interaction with the compound of General formula (IX), (X) or (XI)

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in which R9, R10, R11, R12, R13, R14, R15, p, and W have the above values,

or

G. in the case when R5mean group

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in which R8, R9, R10, R11, R12, R13, R14, n and p have the above values,

the compound of General formula (Ia)

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in which R
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in which R9, R10, R11, R12, R13, R14, Z and p have the above values,

or

C) the compound of General formula (Ie)

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in which R1, R2, R3and R4have the above values,

first diasterous obtaining compounds of General formula (If)

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in which R1, R2, R3and R4have the above values,

and then subjected to the interaction with the Michael acceptor of General formula (XIII)

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in which R24and R25each independently of one another denote hydrogen, alkyl with 1-4 carbon atoms or halogen, and R26means alkyl with 1-4 carbon atoms,

or

And the connection of the above formula (Ia) etherification with alcohol of General formula (XIV)

R16- OH, (XIV)

in which R16have the above meaning.

Compounds of General formula (I) in which R4means the group-C(O)NH2can be obtained according to the method described in the journal "Tetrahedron", T. 29, 435 (1973).

The oxidation in accordance with the method according to variant B) can be performed as described, for example, in the book Houben-Weyl, T. VII, 1, pp. 135 and beyond (1954) or so E 3, page 231 and forth (1983). Connection LASS="ptx2">

The method according to option b) is effectively carried out by reaction of the educt of the formula (IB) in an appropriate solvent at a temperature of from -100 to +40oC with the appropriate base to obtain the compounds of General formula (Z)

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in which R1, R2, R3and R5have the above values and the metalmeans a metal cation, such as lithium, sodium or potassium. The intermediate compound of formula (Z) directly, i.e. without any additional processing, reacts with the compound according to formula (IV) or (V) at a temperature of from -100 to +100 C.

Suitable solvents can be ethers, such as diethyl ether, tetrahydrofuran or 1,4-dioxane.

As a basis you can specify utility, diisopropylamide, sodium hydride or a tertiary butyl potassium.

Known compounds of General formula (IB), which is used as educt. Obtaining them are described in the aforementioned application WO 94/08 999.

Compounds used in variant D) of the method can be obtained by the method described in the book Advanced Organic Chemistry, 1985, page 864 and forth and in the literature, to which it made reference.

The, described in the article by A. I. Meyers in the journal "J. Am. Chem. Soc.", so 92 p. 6644, (1970).

Substances corresponding to variant C) of the method can be obtained in accordance with methods described in U.S. patent 5 250 504.

Etherification version) method is widely known and can be performed in accordance with conventional ways, such as, for example, the methods described in the book Houben-Weyl, so E5, page 659 and forth (1985).

The above reaction can be carried out in the presence of solvents or without them, for which, if necessary, can be used such solvents or diluents which are inert to the reagents. Examples of such solvents or diluents, respectively, are aliphatic and aromatic hydrocarbons, each of which may be optionally florinian, such as, for example, hexane, cyclohexane, petroleum ether, white spirit, benzene, toluene, xylan, methylene chloride, chloroform, carbon tetrachloride, telengard, trichloroethylene and chlorobenzol; ethers, such as diethyl ether, methyl ether, methyl-tert.butyl ether, diisopropyl ether, disutility ether, dioxane and tetrahydrofuran; ketonitriles, acetonitrile and propionitrile; alcohols, such as methanol, ethanol, isopropanol, butanol, tert.butanol, tert.amyl alcohol and ethylene glycol; esters, such as, for example, ethyl acetate and amylacetate, acid amides, such as dimethylformamide and dimethylacetamide, sulfoxidov, such as, for example, dimethyl sulfoxide, sulfones, such as, for example, sulfolan, bases such as pyridine and triethylamine, carboxylic acids, such as acetic acid; mineral acids, such as sulfuric acid and hydrochloric acid.

Resulting from the above reactions, the compounds are purified by conventional methods, for example by crystallization or chromatography.

Compounds in accordance with the present invention in General are colorless or with light yellow color crystalline or viscous substances, which are mainly readily soluble in chlorinated hydrocarbons, such as methylene chloride or chloroform, ethers, such as diethyl ether or tetrahydrofuran, alcohols, such as methanol or ethanol, ketones such as acetone or butanone, Amidah such kalaemia substituted pyrazole derivatives of the above General formula (I) can represent an active substance means, have a weed-killing activity, which is an additional object of the present invention. The proposed tool may be mixed with carriers and/or auxiliary additives.

The proposed tool can be any standard medication in the form of a concentrate which can be diluted with water to the desired concentration.

As examples of drugs can be called powders, spray preparations, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid carriers or diluents, and, if necessary, with addition of binders, wetting agents, emulsifiers and/or dispersants.

Suitable liquid carriers are, for example aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide, as well as fractions, mineral and vegetable oils.

Suitable solid carriers are minerals, such as bentonite, silica gel, talc, kaolin, attapulgite, chalk, and vegetable products, such as flour.

Examples of surfactants are lignin-sulphonate formaldehyde, sulfates of fatty alcohols, and substituted benzenesulfonate and their salts.

The number of the corresponding active substance (s) in a variety of compositions may vary over a wide range. For example, the composition may contain from about 10 to 90 wt.% the active substance, from about 90 to 10 wt.% liquid or solid carrier and optionally can include up to 20 wt.% surface-active substances.

The application can be done by conventional methods, for example, by spraying, using water as the carrier, in an amount from about 100 to 1000 liters/hectare

The following drugs a-D illustrate the proposed remedy.

Drug AND

10 weight. parts of the compounds of formula (I), for example, the compounds of example 2, is mixed with 90 weight. parts of talc and the resulting mixture is milled. Get sprayed the drug.

Drug B

25 weight. parts of the compounds of formula (I), for example, the compounds of example 8, is mixed with 64 weight. parts kalisoderjasimi quartz, 10 weight. parts ligninsulfonate potassium and 1 weight. part alarmlistener sodium as wetting agent and dispersant, and the resulting mixture is milled. Get despergiruemaya 14, mixed with 6 weight. parts alkylpolyglycoside ether (trade name: Triton X 207), 3 weight. parts isotridekanolethoxylate ether containing 8 ethylenoxide links, and 71 weight. part of paraffinic mineral oil boiling within 255-277oC and the resulting mixture is ground to a fineness of below 5 microns. Get dispersible in water concentrate.

Drug

15 weight. parts of the compounds of formula (I), for example, the compounds of example 1, is mixed with 75 weight. parts of cyclohexanone as solvent and 10 weight. parts atsetilirovanie of Nonylphenol as emulsifier. Get emulsifiable in water concentrate.

The drug D

75 weight. parts of the compounds of formula (I), for example, the compounds of example 3 is mixed with 10 weight. parts ligninsulfonate calcium, 5 weight. parts of lauryl sodium, 3 weight. parts of polyvinyl alcohol and 7 weight. parts of kaolin, the resulting mixture is pulverized and the resulting powder granularit fluidized bed by sprayed water. Get dispersible granules in water.

Obtaining compounds of formula (I) is illustrated by the following examples.

Example 1

1-(4-chloro-5-deformedarse-1-methyl-3-pyrazolyl)-5-formyl-4 - pyrazole-carbon is Tyl-4-pyrazole - carbonitrile, then add 15.2 g Harrogate pyridinium oxide of aluminum. Stirring is continued for 1 hour at room temperature, then the reaction mixture is filtered under vacuum through Celite (Celite) and purified through column chromatography using mixtures of hexane/ethyl acetate. Yield: 1.8 g, which corresponds to 62% of theory

nD20= 1,54066

Example 2

(E/Z) 1-(4-chloro-5-deformedarse-1-methyl-3-pyrazolyl)-5 - methoxyaminomethyl-4-carbonitril

To 4 ml of pyridine added and 0.46 g (1.5 mmol) 1-(4-chloro-5 - deformedarse-1-methyl-3-pyrazolyl)-5-formyl-4-pyrazole - carbonitrile at room temperature, then add 0.25 g (3.0 mmol) of the hydrochloride of O-methyl-hydroxylamine. This mixture is stirred for 2 hours at room temperature, poured into water and shaken with ethyl acetate. The mixture is dried over magnesium sulfate and concentrated. Cleaning is carried out on a chromatographic column using a mixture of hexane/ethyl acetate.

Yield: 0.3 g, which corresponds to 60% of theory

So pl. 95-98oC

Example 3

1-(4-chloro-5-deformedarse-1-methyl-3-pyrazolyl)-5-(2 - methoxyphenyl)-4-pyrazole-carbonitrile

To 10 ml of tetrahydrofuran added 2.9 g (8.4 mmol) methoxymethyl-triphenylphosphonium chloride and 5.6 C. The orange solution is stirred for a further 30 minutes and then slowly added dropwise 1.0 g (3.3 mmol) of 1-(4-chloro-5-deformedarse-1-methyl-3 - pyrazolyl)-5-formyl-4-pyrazole-carbonitrile. Stirring is continued for 2 hours at room temperature. The reaction mixture was then added to the water, shaken out with ethyl acetate, dried over magnesium sulfate and concentrated. Cleaning is done with the help of a chromatographic column using a mixture of hexane/ethyl acetate.

Example 4

1 -(4-chloro-5-deformedarse-1-methyl-3-pyrazolyl)-5-(1,3 - dioxolane-2 - yl)-4-pyrazole-carbonitrile

In 30 ml of toluene was dissolved 0.6 g (2.0 mmol) 1-(4-chloro-5 - deformedarse-1-methyl-3-pyrazolyl)-5-formyl-4-pyrazole-carbonitrile and added 0.14 g (2.2 mmol) of ethylene glycol and a catalytic amount of paratoluenesulfonyl. This mixture is heated for 2 hours on a water separator, the cooled solution is washed with sodium chloride solution, then dried and concentrated.

Yield: 0.68 g, which corresponds to 98% of theory

So pl. 70-72oC

Example 5

1 -(4-chloro-5-deformedarse-1-methyl-3-pyrazolyl)-5-(1,1 - diacetoacetate)-pyrazole-4-carbonitrile

5 ml of acetic anhydride is cooled to l) 1-(4-chloro-5-deformedarse-1-methyl-3 - pyrazolyl)-5-formyl-4-pyrazole-carbonitrile, and stirring is continued for the following 1.5 hours at room temperature. Add 9 ml of 10% sodium acetate solution, stirring is continued for 20 minutes at room temperature and then the mixture is shaken out with ethyl acetate. United an ethyl acetate phase is washed with sodium hydrogen carbonate solution and sodium chloride, dried and concentrated. Cleaning produce through column chromatography using a mixture of hexane and ethyl acetate.

Yield: 2.5 g, which corresponds to 80 % of theory

So pl. 84-85oC

Example 6

complex ethyl ester of 2-chloro-3-[1-(3-chloro-4,5,6,7 - tetrahydropyrazolo-[1,5-a]-pyridine-2-yl)-4-cyan-5-pyrazolyl]-2 - methyl-propionic acid

To 20 ml of acetonitrile is added 1.6 g (of 15.5 mmol) of tert.butylnitrite, 20 ml of ethyl methacrylate and 1.52 g of copper chloride (II) and 2,62 g (10 mmol) 5-amino-1-(3-chloro-4,5,6,7 - tetrahydropyrazolo-[1,5-a] -pyridine-2-yl)-4-pyrazole-carbonitrile three portions. This mixture was stirred at room temperature for 20 hours, add to 50 ml of 2-normal hydrochloric acid, extracted 3 times with dichloromethane, dried over magnesium sulfate and concentrated. Cleaning is carried out on a chromatographic column using a mixture of hexane/ethyl acetate.

Yield: 570 mg, which corresponds to 62% of theory

nD20= 1,53942

Similarly receive the compounds of formula (I), summarized in table 1.

The following example explains herbicide activity proposed tools.

Example 62

Listed in table 2 plants after germination in the greenhouse processed are listed in table 2 compounds, taken in an amount of 0.1 kg/ha When this connection is used in the form of an emulsion with a flow rate of 500 litres of water per ha, and sprayed evenly over the plants. 2 weeks after treatment to determine the degree of damage to the plants on a scale of 0-4. 0 means no damage; 1 - 1-24% damage, 2 - 25-74% damage, 3 - 75-89% damage, a 4 - 90-100% damage.

The results of the experience is given:

ALOMY - Lisovolik field (Alopecurus myosuroides)

AGRRE - wild Rye (Elymus repens)

AVEFA - wild Oats (Avena fatua)

BROTE - Fire roofing (Bromus tectorum)

SETVI - Mice green (Setaria viridis)

PANSS - Millet (Panicum sp.)

SORHA - Sorghum Aleppo (Sorghum halepense)

CYPES - Syt edible (Cyperus esculentus)

ABUTH - Gradnika Theophrastus (Abutilon theophrasti)

IPOSS - Bindweed purple (lpomoea purpurea)

GALAP - cleaver (Galium aparine)

MATCH - Camomile (Matricaria chamomilla)

POLSS - Knotweed (Polygonum sp.)

SEBEX - Sesbania (Sesbania exaltata)

SOLSS - Nightshade (Solanum sp.)

VERP5 - Veronica Persian (Veronica persica)

V/OSS - Violet (Viola sp.)1

1. Substituted pyrazole derivatives of General formula I

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in which R1is alkyl with 1 to 4 carbon atoms;

R2- allylthiourea with 1 to 4 carbon atoms or alkyloxy with 1 to 4 carbon atoms, unsubstituted or substituted by one or more halogen atoms;

R1and R2form together a group -(CH2)m-;

R3is hydrogen or halogen,

R4is hydrogen, nitro, cyano or the group-C(O)NH2,

R5group

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where

R6means hydrogen, alkyl with 1 to 6 carbon atoms, unsubstituted or substituted by one or more SUP> denotes hydrogen, alkyl with 1 to 6 carbon atoms substituted by one or more identical or different substituents from the group comprising halogen and alkoxy with 1 to 4 carbon atoms; Y is oxygen, a group-N or SIG17and

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where R17denotes hydrogen, alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, quinil with 3 to 6 carbon atoms, alkoxycarbonyl-alkyl with 1 to 4 carbon atoms in alkoxycarbonyl part and 1 to 4 carbon atoms in the alkyl part, which may optionally be substituted by halogen atoms;

R18and R19each independently from each other hydrogen, halogen, cyano, alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxycarbonyl-alkyl with 1 to 4 carbon atoms in alkoxycarbonyl part and 1 to 4 carbon atoms in the alkyl part, which may optionally be substituted by halogen atoms;

R7is hydrogen, alkyl with 1 to 4 carbon atoms;

R3has the above value,

or group

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where R8means hydrogen or alkyl with 1 to 4 carbon atoms;

R9, R10, R11, R12, R13and R14each independently from each other hydrogen, halogen, alkyl with 1 to 4 atoms in the of Lerida, substituted by one or more identical or different substituents from the group comprising hydroxyl and alkoxy with 1 to 4 carbon atoms;

R15is alkyl with 1 to 4 carbon atoms;

m = 3 or 4;

n = 0, 1, 2 or 3;

p = 0 or 1;

X is oxygen or sulfur;

Z is oxygen or sulfur;

W is oxygen or carbon.

2. Substituted pyrazole derivatives of General formula I under item 1, in which R1is methyl; R2- methylthio or diformitatii; R1and R2together denote a group -(CH2)4; R3is hydrogen, chlorine or bromine; R4is hydrogen, nitro, cyano or the group-C(O)NH2; R5group

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where R6denotes hydrogen, alkyl with 1 to 6 carbon atoms or a group-or SIG16where R16denotes hydrogen, alkyl with 1 to 6 carbon atoms, unsubstituted or substituted by one or more identical or different substituents from the group comprising halogen and alkoxy with 1 to 4 carbon atoms; Y is oxygen, a group-N or SIG17and

< / BR>
where R17denotes hydrogen, alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, quinil with 3 to 6 carbon atoms, alkoxycarbonyl-alkyl with 1 to 4 carbon atoms in alkoxycarbonyl part and 1 to 4 atoms of carbon is about from each other hydrogen, halogen, cyano, alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxycarbonyl-alkyl with 1 to 4 carbon atoms in alkoxycarbonyl part and 1 to 4 carbon atoms in the alkyl part, which can be substituted by halogen atoms, alkoxy with 1 to 4 carbon atoms;

R7is hydrogen or alkyl with 1 to 4 carbon atoms;

R3has the above value,

or group

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where R8means hydrogen or alkyl with 1 to 4 carbon atoms;

R9, R10, R11, R12, R13and R14each independently from each other hydrogen, alkyl with 1 to 4 carbon atoms or alkoxycarbonyl with 1 to 4 carbon atoms, substituted by one or more identical or different substituents from the group comprising hydroxyl and alkoxy with 1 to 4 carbon atoms;

R15is alkyl with 1 to 4 carbon atoms;

m = 3 or 4;

n = 0, 1, 2 or 3;

P = 0 or 1;

X is oxygen or sulfur;

Z is oxygen or sulfur;

W is oxygen or carbon.

3. Substituted pyrazole derivatives of General formula I under item 1, in which R1is methyl; R2- deformedarse; R1and R2together form a group -(CH2)4-; R3- chlorine; R4- nitro or cyanol 1 6 carbon atoms; Y is oxygen, a group-N or SIG17and

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where R17means alkyl with 1 to 6 carbon atoms; R18and R19each independently from each other hydrogen, halogen, or a group

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where R8means hydrogen;

R9, R10, R11, R12, R13and R14each independently from each other hydrogen, alkyl with 1 to 4 carbon atoms, alkoxycarbonyl-alkyl with 1 to 4 carbon atoms in alkoxycarbonyl part and 1 to 4 carbon atoms in the alkyl part or haloalkyl with 1 to 4 carbon atoms;

n = 0;

p = 0 or 1;

X is oxygen.

4. A means of having a weed-killing activity, characterized in that it comprises at least one of the compounds according to paragraphs.1 - 3.

5. A means of having a weed-killing activity on p. 4, mixed with carriers and/or auxiliary additives.

 

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The invention relates to new derivatives pyridonecarboxylic acid, antitumor means containing them as effective ingredients, and to methods of producing new derivatives pyridonecarboxylic acid and t

The invention relates to new methods and intermediate products to obtain pharmaceutically acceptable salts of the acids of formula afterinvoke of the antibiotic 7- (1,5,6)- (6-amino-3-azabicyclo[3,1,0]Gex - 3-yl)-1-(2,4-differenl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthiridine-3-carboxylic acid

The invention relates to a derivative (azetidin-1-illlil)lactams of the formula (I) and their pharmaceutically acceptable salts, where R - (C1-C6)-alkyl, optionally substituted by-COOH, -COO((C1-C4)-alkyl), (C3-C7-cycloalkyl, aryl or het1and (C3-C7-cycloalkyl, optionally substituted with 1-2 substituents selected from (C1-C4)-alkyl and fluorine; R1is phenyl, optionally substituted by 1-2 halosubstituted; R2- -CONR3R4, -CONR5((C3-C7-cycloalkyl), -NR3R4that gets3or a group of formula (a), (b), (C); X - (C1-C4-alkylene; X1- directional communication, X2- directional communication or CO; m = 1; used in the treatment of diseases by producing antagonistic action on tachykinin, working in human NK1-, NK2- and NK3the receptor or in their combinations

The invention relates to a new derived tetrazole having effect in reducing blood sugar and lipid in the blood, and it contains the tool for use in the treatment of diabetes and hyperlipemia

The invention relates to a new derivative of bisexuality and its pharmaceutically acceptable salts, are useful as pharmaceuticals, in particular as a hypoglycemic drugs (drugs that increase insulin sensitivity), and containing pharmaceutical compositions

The invention relates to the field of organic chemistry and more particularly to the synthesis of biologically active compounds that may be useful in therapy
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