Substituted thienyl(amino)sulfonylureas and herbicide agent based on the same

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to new substituted thienyl(amino)sulfonylureas of formula I ,

wherein A represents nitrogen or methane; Q represents direct bond or imino; R1 represents fluorine, chlorine, bromine, unsubstituted C1-C4-alkyl, C1-C4-alkoxyl optionally substituted with halogen, unsubstituted C1-C4-alkylthio, or di(C1-C4-alkyl)amino; R2 represents hydrogen or C1-C4-alkyl. Compounds of present invention are useful as herbicide agents.

EFFECT: new compounds with herbicide activity.

5 cl, 11 tbl, 5 ex

 

The invention relates to new substituted thienyl(amino)sulfonylureas, methods for their preparation and their use as herbicides.

It is already known that certain substituted teilzunehmen have a weed-killing properties (see the application for the European patent 30142, application for U.S. patent 4481029, application for U.S. patent 4599103, application for U.S. patent 4701535, the application for the European patent 97122, application for U.S. patent 4549898, the application for the European patent 207609, application for U.S. patent 4668281). Herbicide activity of these known compounds, however, not in all cases is satisfactory. Currently received new substituted thienyl(amino)sulfonylureas of the General formula (I):

in which

A represents nitrogen atom or methine group;

Q means a simple link or aminogroup;

R1means a hydrogen atom, a halogen atom or, respectively, possibly substituted (substituted) alkyl, alkoxyl, allylthiourea, alkylamino, dialkylamino, alloctype or geterotsiklicheskikh;

R2means a hydrogen atom, a halogen atom or, respectively, possibly substituted (substituted) alkyl, alkoxyl, allylthiourea, alkylamino, dialkylamino, alloctype or geterotsiklicheskikh;

R3means a hydrogen atom or in which can be substituted by alkyl;

R4means a halogen atom or a possibly substituted alkyl and, in the case when Q means aminogroup, also a hydrogen atom; and

R5means a hydrogen atom or, respectively, possibly substituted alkyl, alkenyl, quinil, cycloalkyl, cycloalkenyl or heterocyclyl;

and salts of compounds of formula (I).

Saturated or unsaturated hydrocarbon groups as alkyl, alkenyl or quinil, also in combination with heteroatoms, as in alkoxide, if possible, respectively, are lineinymi or branched.

Possibly substituted residues may be substituted one or more times, and when multiple substitution, the substituents may be the same or different.

Preferred substituents, respectively, the field values available in above - and below formulas residues are highlighted below:

And preferably means a nitrogen atom or methine group;

Q preferably means a simple link or aminogroup;

R1preferably means hydrogen atom, halogen atom, respectively, possibly replaced (substituted) by cyano, halogen or alkoxyl with 1-4 carbon atoms alkyl, alkoxyl, allylthiourea, alkylamino or dialkylamino respectively with 1-4 carbon atoms in the alkyl groups, or may zameshano what cyano, halogen, alkyl with 1-4 carbon atoms or alkoxyl with 1-4 carbon atoms fenoxaprop, acetamidoxime, ferrochrome or tetrahydropyranyloxy;

R2preferably means hydrogen atom, halogen atom, respectively, possibly replaced (substituted) by cyano, halogen or alkoxyl with 1-4 carbon atoms alkyl, alkoxyl, allylthiourea, alkylamino or dialkylamino respectively with 1-4 carbon atoms in the alkyl groups or, respectively, possibly substituted by cyano, halogen, alkyl with 1-4 carbon atoms or alkoxyl with 1-4 carbon atoms fenoxaprop, acetamidoxime, ferrochrome or tetrahydropyranyloxy;

R3preferably means hydrogen atom or a possibly substituted by alkoxyl with 1-4 carbon atoms, alkylcarboxylic with 1-4 carbon atoms in the alkyl part or alkoxycarbonyl with 1-4 carbon atoms in the CNS part of alkyl with 1-4 carbon atoms;

R4preferably means maybe substituted by cyano, halogen or alkoxyl with 1-4 carbon atoms, alkyl with 1-6 carbon atoms, and when Q means aminogroup, also a hydrogen atom;

R5preferably means hydrogen atom, possibly substituted by cyano, halogen or alkoxyl with 1-4 carbon atoms, alkyl with 1-6 and what Ohm carbon; accordingly, possibly substituted with halogen of alkenyl or quinil respectively with 2-6 carbon atoms; accordingly, possibly substituted by cyano, halogen or alkyl with 1-4 carbon atoms, cycloalkyl or cycloalkenyl respectively with 3-6 carbon atoms in cycloalkyl groups and perhaps with 1-4 carbon atoms in the alkyl part, or possibly substituted by cyano, halogen, alkyl with 1-4 carbon atoms or alkoxyl with 1-4 carbon atoms oxetanyl, furyl or tetrahydrofuryl;

And particularly preferably denotes a nitrogen atom or methine group;

Q particularly preferably by means of a simple link or aminogroup;

R1particularly preferably denotes a hydrogen atom, fluorine atom, chlorine, bromine, iodine or possibly replaced (substituted) by cyano, fluorine, chlorine, methoxy group or ethoxypropane methyl, ethyl, n - or isopropyl, methoxy group, ethoxypropan, n - or isopropoxy, methylthiourea, ethylthiourea, n - or isopropylthio, methylaminopropyl, ethylamino, n - or isopropylamino, dimethylaminopropyl or diethylaminopropyl;

R2particularly preferably denotes fluorine atom, chlorine, bromine or possibly replaced (substituted) by cyano, fluorine, chlorine, methoxy group or ethoxypropan is methyl, ethyl, n - or isopropyl, methoxy group, ethoxypropan, n - or isopropoxy, methylthiourea, ethylthiourea, n - or isopropylthio, methylaminopropyl, ethylamino, n - or isopropylamino, dimethylaminopropyl or diethylaminopropyl;

R3particularly preferably denotes a hydrogen atom or, respectively, possibly substituted by a methoxy group, ethoxypropane, n - or isopropoxy, acetyl, propionyl, n - or isobutyryl, methoxycarbonyl, etoxycarbonyl, n - or isopropoxycarbonyl methyl or ethyl;

R4especially preferably means, respectively, possibly substituted by cyano, fluorine, chlorine, methoxy group or ethoxypropane methyl, ethyl, n - or isopropyl, n-, ISO-, sec - or tert-butyl;

R5particularly preferably denotes a hydrogen atom; consequently possibly substituted by cyano, fluorine, chlorine, methoxy group, ethoxypropane, n - or isopropoxy methyl, ethyl, n - or isopropyl, n-, ISO-, sec - or tert-butyl; accordingly, possibly substituted by fluorine, chlorine or bromine propenyl, butenyl, PROPYNYL or butynyl or possibly substituted by cyano, fluorine, chlorine, bromine, stands, ethyl, n - or isopropyl cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or CEC shall heximer;

And in the highest degree preferably means a nitrogen atom or methine group;

Q in the highest degree preferably means a simple link or aminogroup;

R1highly preferably denotes a hydrogen atom, fluorine atom, chlorine, bromine; consequently possibly replaced (substituted) by fluorine, chlorine, methoxy group or ethoxypropane methyl, ethyl, methoxy group, ethoxypropan, methylthiourea, ethylthiourea, methylaminopropyl, ethylamino; or dimethylaminopropyl;

R2highly preferably means a fluorine atom, chlorine, bromine; consequently possibly replaced (substituted) by fluorine, chlorine, methoxy group or ethoxypropane methyl, ethyl, methoxy group, ethoxypropan, methylthiourea, ethylthiourea, methylaminopropyl, ethylamino; or dimethylaminopropyl;

R3highly preferably means hydrogen atom or methyl;

R4highly preferably means, respectively, possibly substituted by fluorine or chlorine, methyl, ethyl, n - or isopropyl;

R5highly preferably means, respectively, possibly substituted by fluorine, chlorine, methoxy group or ethoxypropane methyl, ethyl, n - or isopropyl or possibly substituted by fluorine or chlorine propenyl or PROPYNYL;

And often preferably who appoints methine group;

R1and R2often preferably means a methoxy group;

R3often means preferably a hydrogen atom.

The object of the invention preferably also are sodium, potassium, magnesium, calcium, ammonium, alkylammonium with 1-4 carbon atoms in the alkyl part, dialkylammonium with 1-4 carbon atoms in each alkyl part, trialkylamines with 1-4 carbon atoms in each alkyl part, tetraalkylammonium with 1-4 carbon atoms in each alkyl part, trialkylsilanes with 1-4 carbon atoms in each alkyl part, cycloalkylcarbonyl with five or six carbon atoms in cycloalkyl parts and diallylmethylamine with 1-2 carbon atoms in each alkyl part of the salts of the compounds of formula (I)in which A, Q, R1, R2, R3, R4and R5are preferably the above value.

The above General or specified in the preferred areas of residue values apply both to the end products of the formula (I), and accordingly it is necessary in each case to obtain the original substances, respectively, of the intermediate products. These residue values can be combined in any way with each other, hence also between these areas of preferred compounds.

According from what briteney preferred those compounds of formula (I), in which there is a combination of the above as preferred values of residues.

According to the invention particularly preferred those compounds of formula (I), in which a combination of the above as particularly preferred values of residues.

According to the invention in a highly preferred those compounds of formula (I), in which a combination of the above as highly preferred residue values.

According to the invention often preferred compounds in which R1, R2, R3or Rather have one of these as is often the preferred values.

Examples according to the invention compounds of formula (I) are listed below in groups.

Group 1

A, Q, R1, R2and R3have in this group of compounds, for example, the following value:

H
AndQRlR2R3
SN-Och3Och3H
SNNHOch3Och3H
SN-CH3Och3
SNNHCH3Och3H
SN-CH3CH3H
SNNHCH3CH3H
SN-CLOch3H
SN-HCH3H
N-CH3Och3CH3
N-Och3Och3CH3
N-CH3Och3H

AndQRlR2R3
NNHCH3Och3H
N-Och3Och3H
NNHOch3Och3H
N-With the 3CH3H
N-OCHF2N(CH3)2H
N-CH3S3H
N-With2H5Och3H
N-CH3OS2H5H
N-HOch3H
N-Och3H
N-CH3N(CH3)2H
SN-Och3H
CH-CH3H
SN-CLH

AndQRlR2R3
N -NN
N-N(CH3)2Och2CF3N

Group 2

A, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 3

And, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 4

A, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 5

And, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 6

A, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 7

A, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 8

And, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 9

And, Q, R1, R2and R3 thus, for example, have specified above in group 1 value.

A group of 10

A, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 11

A, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 12

And, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 13

A, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 14

And, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 15

And, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 16

A, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 17

And, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 18

A, Q, R1, R2and R3p and this, for example, have specified above in group 1 value.

Group 19

A, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

The group of 20

And, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 21

A, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 22

A, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 23

And, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

24

A, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

Group 25

And, Q, R1, R2and R3thus, for example, have specified above in group 1 value.

New substituted thienyl(amino)sulfonylureas of the General formula (I) have strong herbicide action.

New substituted thienyl(amino)sulfonylureas of the General formula (I) receive, if

(a) aminoethane General formula (II):

in which

A, R1and R2have the above meaning,

enter into interaction with thienyl(amino)sulfosalicylate General formula (III):

in which

Q, R4and R5have the above meaning,

if necessary in the presence of an auxiliary for the reaction means and

if necessary in the presence of a diluent;

or, if

(b) substituted aminoethane General formula (IV):

in which

A, R1and R2have the above meaning,

Z means a halogen atom, alkoxyl or alloctype; and

R has the above for R3value or means the group-C(O)-Z; enter into interaction with derivatives of thiophene of the General formula (V):

in which

Q, R4and R have the above significance,

if necessary in the presence of an auxiliary for the reaction means and

if necessary in the presence of a diluent;

or, if

(C) aminoethane General formula (II):

in which

A, R1and R2have the above meaning,

enter into interaction with derivatives of thiophene of the General formula (VI):

in which

Q, R4and R5they who have the above significance and

Z means a halogen atom, alkoxyl or alloctype,

if necessary in the presence of an auxiliary for the reaction means and

if necessary in the presence of a diluent;

or, if

(g) aminoethane General formula (II):

in which

A, R1and R2have the above meaning,

enter into interaction with chlorosulfonylisocyanate, if necessary in the presence of a diluent and the resulting chlorosulfonylisocyanate General formula (VII):

in which

A, R1and R2have the above meaning,

after an interim allocation or "in situ",

enter into interaction with substituted aminothiophene General formula (VIII):

in which

R4and R5have the above meaning,

if necessary in the presence of an auxiliary for the reaction means and

if necessary in the presence of a diluent;

and, if necessary, obtained by the methods (a), (b), (C) or (d) the compounds of formula (I) by conventional methods transferred to salt.

If the starting compounds are used, for example, 2-amino-4-methoxy-6-methylpyrimidine and 4-etoxycarbonyl-2-triptorelin-3-inculturalization, protein the e reaction in the case of proposed according to the invention method (a) can be represented the following formula scheme:

If the starting compounds are used, for example, 2-methoxycarbonylamino-4-methoxy-6-trifluoromethyl-1,3,5-triazine and 2-ethyl-4-isopropoxycarbonyl-3-sulfonamide, the reaction in the case of proposed according to the invention method (b) can be represented the following formula scheme:

If the starting compounds are used, for example, 2-amino-4-chloro-6-methoxypyridazine and N-(4-etoxycarbonyl-2-metallian-3-ylsulphonyl)-O-phenylurethane, the reaction in the case of proposed according to the invention method (C) can be represented the following formula scheme:

If the starting compounds are used, for example, 2-amino-4-methoxy-6-cryptomaterial, chlorosulfonylisocyanate and ethyl ester of 3-amino-2-ethylthiophen-4-carboxylic acid, the reaction in the case of proposed according to the invention method (g) can be represented the following formula scheme:

Used as source materials for the production of compounds of General formula (1) in the case of proposed according to the invention methods (a), (b) and (d) aminoethane all fall under the formula (II). In the formula (II) A, R1and R2preferably respectively in particular have the EIT is to be placed, which have already been mentioned above in connection with the description of compounds of formula (I) as preferred, respectively, as particularly preferred for A, R1and R2.

Aminazine formula (I) are known, partly commercially available synthetic chemicals.

Used later as a source of substances in the case of proposed according to the invention method (a) thienyl(amino)sulfonylation all fall under the formula (III). In the formula (III) Q, R4and R5preferably respectively in particular have those meanings which have already been mentioned above in connection with the description of compounds of formula (I) as preferred, respectively, as particularly preferred for Q, R4and R5.

Educt of the formula (III) are known and/or can be obtained in itself known (see European patent 30142, application for U.S. patent 4481029, application for U.S. patent 4599103 and application for U.S. patent 4701535).

Thienyl(amino)sulfonylation formula (III) receive, if the derivatives of thiophene above General formula (V) enter into interaction with phosgene, respectively thiophosgene, if necessary, in the presence of alkylsulfonate, as, for example, utilitzant, if necessary in the presence of an auxiliary reaction means, as, for example, diazabicyclo[2,2,2]OK the Academy of Sciences, and in the presence of a diluent, such as toluene, xylene or chlorobenzene, at temperatures in the range from 80 to 150°and at the end of the interaction of volatile components distilled off under reduced pressure.

Used as starting materials in the case of proposed according to the invention of the means (b) to obtain compounds of formula (I) substituted aminoethane all fall under the formula (IV). In the formula (IV), A, R1and R2preferably respectively in particular have those meanings which have already been mentioned above in connection with the description of compounds of formula (I) as preferred, respectively, as particularly preferred for A, R1and R2; Z preferably denotes fluorine atom, chlorine, bromine, alkoxy with 1-4 carbon atoms or fenoxaprop, in particular a chlorine atom, a methoxy group, ethoxypropan or fenoxaprop.

Educt of the formula (IV) are known and/or can be obtained in itself known methods (see U.S. patent 4690707, patent Germany 19501174).

Used later as a source of substances in the case of proposed according to the invention method (b) derivatives of thiophene all fall under the formula (V). In the formula (V) Q, R4and R5preferably respectively in particular have those meanings which have already been mentioned above in connection with the description of compounds of formula (I) as PR is doctitle respectively, as particularly preferred for Q, R4and R5.

Educt of the formula (V) are known and/or can be obtained in itself known (see European patent 30142, application for U.S. patent 4481029, application for U.S. patent 4599103 and application for U.S. patent 4701535, sample receipt).

Used as starting materials in the case of proposed according to the invention method () to obtain the compounds of formula (I) substituted derivatives of thiophene all fall under the formula (VI). In the formula (VI) Q, R4and R5preferably respectively in particular have those meanings which have already been mentioned above in connection with the description of compounds of formula (I) as preferred, respectively, as particularly preferred for Q, R4and R5; Z preferably denotes fluorine atom, chlorine, bromine, alkoxy with 1-4 carbon atoms or fenoxaprop, in particular a chlorine atom, a methoxy group, ethoxypropan or fenoxaprop.

Educt of the formula (VI) are known and/or can be obtained in itself known methods.

Used as starting materials in the case of proposed according to the invention of the means (g) to obtain compounds of General formula (I) substituted aminothiophene all fall under the formula (VIII). In the General formula (VIII) R4and R5preferably respectively in particular have those meanings which have already would what and described above in connection with the description of compounds of formula (I) as preferred, accordingly, as particularly preferred for R4and R5.

The original substance of General formula (VIII) are known and/or can be obtained in itself, izvestnimi ways (see Aust. J. Chem.,1907-1916 (1995)).

As diluents for carrying out the invention methods (a), (b), (C) and (d) use first of all inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, if necessary, halogenated hydrocarbons, such as benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers like diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or etilenglikolevye or diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; NITRILES like acetonitrile, propionitrile or benzonitrile; amides like N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformamide, N is an organic or triamide hexamethylphosphoric acid; esters as methyl acetate or ethyl acetate, and the sulfoxidov as dimethyl sulfoxide.

Proposed according to the invention, the method (a), (b), (C) and (d) is preferably carried out in the presence of a suitable helper for the reactions the funds. As such, use all customary inorganic or organic bases. These include, for example, hydrides, hydroxides, amides, alcoholate, acetates, carbonates or bicarbonates of alkali or alkaline earth metals, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, tert-butyl potassium, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, and also tertiary amines, as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, pyridine N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclo, Diisobutylene or databaseconnect.

In the implementation proposed according to the invention methods (a), (b), (C) and (d) the reaction temperature can vary in a wide range of values. In General, operate in temperatures from -20 to +150°C, preferably from -10 to +120°C.

Proposed according to the invention, the method (a), (b), (C) and (d) perform, in General, under normal pressure. However, proposed according to the invention methods can also be carried out at elevated or reduced pressure, in General, in the range from 0.1 to 10 bar.

To carry out the proposed according to the invention methods (a), (b), (C) and (is) parent substance use, in General, in approximately equimolar amounts. However, you can also use one component in a larger excess. The transformation carried out in a suitable diluent in the presence of an auxiliary for the reaction means and the reaction mixture is stirred, in General, for several hours at the required temperature. Treatment is carried out in the usual ways (see receipt).

Of proposed according to the invention compounds of General formula (I) in case of necessity you can get salt. Such salts are simply a way according to the usual methods of salt formation, for example by dissolving or dispersing the compounds of formula (I) in a suitable solvent, such as dichloromethane, acetone, tert-butyl methyl ether or toluene, and adding a suitable base. Then salt if necessary after prolonged stirring, can be distinguished by concentration or filtration under vacuum.

Proposed according to the invention the biologically active substances can be used as defoliants, desicants, means for pre-harvest destruction of tops and in particular as a means for destroying weeds. Under the weed in its broadest sense must be understood all plants which grow in locations where they are undesired. Act opredelyaemye according to the invention substances as herbicides common actions or selective herbicides, depends essentially on the quantities used.

Proposed according to the invention the biologically active substances can be applied, for example, in the case of the following plants:

Dicotyledonous families: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Ccntaurea, Chenopodium. Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphoroia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoca, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis. Papaver, Phaibilis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida. Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Species, Such As Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

Two culture collections: Arachis, Beta, Brassica, Cucumis. Cucurbita, Hclianthus, Daucus, Glycine. Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds families: Aegilops, Agropyron, Agrostis, Alopceurus, Apera, Avena, Brachiaria, Bromus, Cenchms, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Monocots culture collections: Album, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.

The use of biologically active substances according to the invention, however, is in no way limited to these families, but equally applies also to other plants.

Depending on the concentration of biologically active substances according to the invention is suitable for a public fight with what makami, for example, industrial buildings, railway tracks, roads and squares, overgrown and not overgrown with trees. Biologically active substances according to the invention can also be used for combating weeds in perennial crops, for example forests, decorative plantings of tree species, fruit plantations, vineyards, plantations of citrus, nuts, bananas, coffee plantations, tea plantations, plantations of rubber trees, oil palm trees, cocoa, fruit plantings and hop fields, on ornamental lawns and sports fields, hay-pasture, and for the selective combating of weeds in annual crops.

Proposed according to the invention the compounds of formula (I) have a strong herbicide activity and a broad spectrum of action in case of application in soil and aboveground parts of plants. To a certain extent they are also suitable for the selective combating of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops as pre-emergence method, and post-harvest method.

Biologically active substances can be converted to conventional preparative form as solutions, emulsions, wettable powders, suspensions, dusty, powdered drugs, pastes, soluble powders, granules, suspension the but-emulsion concentrates, impregnated with biologically active substances of natural and synthetic substances, as well as the hyperfine encapsulation in polymeric substances.

These preparative form get in a known manner, for example by mixing the biologically active substances with a neutral fillers, therefore, liquid solvents and/or solid carriers, if necessary, by using surface-active substances, therefore, emulsifiers and/or dispersants and/or foam-forming agents.

In the case of using water as a neutral filler can be applied, for example, organic solvents as auxiliary solvents. As liquid solvents are essentially used aromatic hydrocarbons like xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, as chlorobenzene, chloroethylene and dichloromethane, aliphatic hydrocarbons like cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols like butanol or glycol and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethylsulfoxide, and water.

As per rdih media use, for example, ammonium salts and natural stone flour as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic stone flour as highly dispersed silicic acid, alumina and silicates; as solid carriers for granules are used, for example, crushed and fractionated rocks as calcite, marble, pumice, thick, dolomite, and also synthetic granules of inorganic and organic flour, granules of organic material such as sawdust, coconut shell, corn cobs and stalks of tobacco plants; emulsifiers and/or foaming agents are used, for example, nonionic and anionic emulsifiers, as polyoxyethylene esters of fatty acids, simple polyoxyethylene ethers of fatty alcohols, for example alkylarylsulphonate ethers, alkyl sulphonates, alkyl sulphates, arylsulfonate, and also protein hydrolysates; as dispersing agents are used, for example, ligninsulfonate liquors and methylcellulose.

In the formulation can be used to improve the adhesion means, as carboxymethylcellulose, natural and synthetic powdered, granular, or Latecoere polymers such as gum Arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, as capalini the lecithins, and synthetic phospholipids. Other additives can be mineral and vegetable oils.

You can use dyes, inorganic pigments, for example iron oxide, titanium dioxide, ferrocyanide blue, and organic dyes, as alizarin, azo and metallophthalocyanine dyes, and trace elements such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Preparative forms contain, in General, 0.1 to 95 wt.%, preferably 0.5 to 90 wt.% biologically active substances.

Proposed according to the invention the biologically active substances can be used as such or in their formulation also in a mixture with known herbicides for weed control, with the finished formulation or tank mix.

To use mixtures are known herbicides, for example, the following:

acetochlor, acifluorfen(-sodium), klonipin, alachlor, aloxide(-sodium), ametrine is high, amithlon, amidosulfuron, anilofos, Azul, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl), beforethat, encultured(-methyl), bentazon, benzamycin, benzefoam, benzoylperoxy(-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromobutyl, bromophenoxy, bromoxynil, butachlor, butoxide, butyl, cafestol, galaxidi, carbetamide, carfentrazone(-ethyl), chlorethoxyfos, chloramben, x is oredson, chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlortoluron, cinidon(-ethyl), cinmetacin, chinaculture, clefoxydim, clethodim, clodinafop-(-propargyl), clomazone, clomipram, clopyralid, cloperastine(-methyl), karasulu(-methyl), cumyluron, cyanazine, cybotron, cycloate, cycloaliphatic, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), dicloflam, diacetyl(-ethyl)difenzoquat, diflufenican, diflubenzuron, dimefuron, timepart, dimethachlor, deltamethrin, dimethenamid, Dimexidum, dinitramine, diphenamid, Diquat, dithiopyr, Diuron, damron, aprobada, ARTS, asbroker, ethalfluralin, atomiculture(-methyl), ethofumesate, idoxifene, ethoxysulfuron, etamesonic, fenoxaprop(-P-ethyl), phentramin, planrep-(-isopropyl), planrep(isopropyl-L), planrep(-methyl), flazasulfuron, florasulam, fluazifop(-P-butyl), flatlet, flucarbazone, flufenacet, flumetsulam, flumiclorac(pencil), flumioxazin, flubiprofen, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam, flourophenyl, flupyrsulfuron-(-methyl-sodium), flurenol(-butyl), fluridone, fluroxypyr(-methyl), flurried, flurtamone, fluthiacet(-methyl), flutamide, fomesafen, glufosinate(-ammonium), glyphosate(-isopropylammonium), galasoft, haloxyfop(-ethoxyethyl), haloxyfop(P-methyl), hexazinone, imazamethabenz(-meth is l), imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron(-methyl-sodium), ioxynil, isopropylene, Isoproturon, Sauron, isoxaben, isoxaflutole, isoxaflutole, isocaporate, lactofen, lenacil, linuron, MSRA, MSR, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metaventure, metobromuron, (alpha)metolachlor, metosulam, metoxuron, metribuzin, metsulfuron(-methyl), molinet, monolinuron, nitroanilide, napropamide, neburon, nicosulfuron, norflurazon, arrancars, oryzalin, oxadiargyl oxadiazon, oxasulfuron, oxacyclobutane, oxyfluorfen, paraquat, pelargonia acid, pendimethalin, pentalyn, phenoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron-(-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate, pyrazosulfuron(-ethyl), paradoxien, perbenzoic, perimutter, peridot, Perminova(-methyl), pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-tefuryl), rimsulfuron, sethoxydim, Simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tabulam, tebuthiuron, tepraloxydim, terbutylazine, terbutryn, tanishlar, tefloned, thiazopyr, thidiazuron, thifensulfuron(-methyl), tio is ncarb, thiocarbonyl, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.

It is also possible mixture with other known biologically active substances, such as fungicides, insecticides, acaricides, nematicides, substances for protection against vyklevyvanija birds, substances for plant nutrition and means to improve soil structure.

Biologically active substances can be applied individually, in the form of their formulations or forms prepared from them by further dilution of applications as ready-to-use solutions, suspensions, emulsions, powders, pastes and granulates. Application carried out in the usual manner, for example by watering, spraying, atomized spraying, spreading.

Proposed according to the invention the biologically active substances can be applied both before and after emergence of the plants. They can also be make before sowing in the soil.

The amount of biologically active substance may vary within wide limits. It depends essentially on the kind of desired effect. In General, application rates range from 1 g to 10 kg, preferably from 5 g to 5 kg, biologically active substances per hectare of soil surface.

Receipt and application of the proposed according to the invention the biological the key active substances follows from the following examples.

Examples retrieve

Example 1

(method (b))

0.75 g (2.9 mmol) of 2-Phenoxycarbonylamino-4-methoxy-6-methyl-1,3,5-triazine are dissolved in 40 ml of acetonitrile and mixed successively with 0.75 g (3.2 mmol) of the methyl ester of 2-methyl-3-allfamilies-4-carboxylic acid and 0.49 g (3.2 mmol) of diazabicyclo. The reaction mixture is stirred for 12 hours at room temperature (about 20°) and then concentrated in vacuo water-jet pump. The residue is treated with dichloromethane, washed with 2 N. hydrochloric acid and water, dried over magnesium sulfate and filtered. The filtrate was concentrated in a water jet vacuum pump, the residue insist with diethyl ether and precipitated precipitated crystalline product produce by filtration under vacuum.

Get 0,60 g (52% of theoretical amount) of N-(4-methoxy-6-methyl-1,3,5-triazine-2-yl)-N'-(4-methoxycarbonyl-2-metallian-3-ylsulphonyl)urea with a melting point (so square) 195°C.

Example 2

(method (g))

1,05 g (7.5 mmol) Chlorosulfonylisocyanate bring in 75 ml of dichloromethane. After cooling to a temperature of -10°to this mixture with stirring is added dropwise a solution of 1.16 g (7.5 mmol) of 2-amino-4,6-dimethoxypyrimidine in 30 ml of dichloromethane and the mixture is stirred t is within 30 minutes at a temperature of -10° C. and Then at a temperature of 0°to this mixture is added dropwise a solution of 1.28 g (7.5 mmol) of methyl ester of 3-amino-2-methylthiophene-4-carboxylic acid and 0.75 g (7.5 mmol) of triethylamine in 50 ml dichloromethane and the reaction mixture is stirred for 12 hours at room temperature (about 20°). Then to this mixture was added 100 ml of water and 100 ml of 2 N. hydrochloric acid, the organic phase is separated, washed with 50 ml of water, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo water pump and the residue crystallized from ethanol.

Obtain 2.1 g (66% of theoretical amount) of N-(4,6-dimethoxy-pyrimidine-2-yl)-N'-(4-methoxycarbonyl-2-metallian-3-enaminocarbonyl)urea with a melting point of 174°C.

Similarly, according to the methods of examples 1 and 2, and accordingly the General description of the proposed according to the invention, a method of obtaining can also be obtained, for example, listed below in table 1 compounds of General formula (I).

Table 1
Examples of compounds of formula (1)
Example No.AndQR1R2R3R 4R5So square (°)
3SNNHOch3Och3NN-C3H7With2H5140
4SNNHOch3Och3HISO-C3H7With2H5154
5SNNHOch3Och3NWith2H5CH3195
6SN-Och3Och3HCH3CH3194

Educt of the formula (V)

Example (V-1)

Stage 1

A solution of 19.9 g (0.29 mol) of sodium nitrite in 60 ml of water at a temperature of from 0 to 5°with stirring, added dropwise to a solution of 42.7 g (0.25 mol) of methyl ester of 3-amino-2-methylthiophene-4-carboxylic acid in 75 ml of 10%hydrochloric acid. The reaction mixture is stirred for 60 minutes at a temperature of from 0 to 5°C. Then the excess nitrite is removed is by using amidosulfonic. The mixture is then at a temperature of from 0 to 5°under stirring is added dropwise to a solution of 35 g (0.55 mol) of sulfur dioxide in 300 ml of dichloromethane. After adding 1.5 g of the chloride of monovalent copper and 1.5 g of dodecyltrimethylammonium the reaction mixture is stirred for 60 minutes at a temperature of 40°With a further 12 hours at a temperature of 20°C. Then the reaction mixture is added 18 ml of 35%hydrochloric acid, the mixture is stirred for four hours at a temperature of 20°and then the phases are separated. The aqueous phase is additionally extracted with dichloromethane, the combined organic phases are washed with water, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo water pump and the residue crystallized from hexane.

Get of 51.7 g (81% of theoretically calculated amount) of acid chloride of 4-methoxycarbonyl-2-methylthiophene-3-sulfonic acids.

Stage 2

A mixture of 45 g (177 mmol) of acid chloride of 4-methoxycarbonyl-2-methylthiophene-3-sulfonic acids, 34 g (354 mmol) of ammonium carbonate and 400 ml of dichloromethane is stirred for 12 hours at room temperature (about 20°). After filtration from the filtrate the solvent is distilled off in a water jet vacuum pump, the residue insist with diethyl ether and the crystalline product produce by tfilter is byvania under vacuum.

Get a 21.5 g (52% of theoretical amount) of 4-methoxycarbonyl-2-methylthiophene-3-sulfonamida.

Examples of the application

Example

Predsjedava test

Solvent: 5 mass. parts of acetone

Emulsifier: 1 mass. part of a simple alkylarylsulphonates ether

For obtaining the target composition with a biologically active substance, 1 mass. part of the biologically active substance is mixed with the specified amount of solvent, add the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. Approximately 24 hours later, the soil is sprayed with the composition with a biologically active substance in such a way that cause, respectively, the desired amount of biologically active substances per unit area. The concentration of the working solution is chosen so that in 1000 l of water per hectare applied, respectively, the desired amount of biologically active substances.

Three weeks later assess the degree of damage to the plants in% damage in comparison with the development of the untreated control plants.

When you do this:

0% means that there is no action (as untreated control plants);

100% means total destruction.

In this test, for example, link is according to the example of obtaining 1, 2, 3, 4, 5 and 6, when partly good compatibility with respect to cultivated plants, such as cotton, corn and soybeans, have a strong action against weeds.

Example B

Post-harvest test

Solvent: 5 mass. parts of acetone

Emulsifier: 1 mass. part of a simple alkylarylsulphonates ether

For obtaining the target composition with a biologically active substance, 1 mass. part of the biologically active substance is mixed with the specified amount of solvent, add the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Using the composition of biologically active substances are sprayed with the test plants which have a height of 5-15 cm, so that cause, respectively, the desired amount of biologically active substances per unit area. The concentration of the working solution is chosen so that in 1000 l of water per hectare applied, respectively, the desired amount of biologically active substances.

Three weeks later assess the degree of damage to the plants in% damage in comparison with Razvitie untreated control plants.

When you do this:

0% means that there is no action (as untreated control plants);

100% means total destruction.

In this test, for example, the compounds according to the example of getting 1, 2, 5 and 6, when partly good compatibility with respect to cultivated plants, such as barley and wheat, have a strong action against weeds.

1. Compounds of General formula (I)

in which

A represents nitrogen atom or methine group;

Q means a simple link or aminogroup;

R1means fluorine atom, chlorine, bromine, unsubstituted alkyl with 1-4 carbon atoms, unsubstituted or substituted with halogen alkoxy with 1-4 carbon atoms, an unsubstituted alkylthiols with 1-4 carbon atoms or dialkylamino with 1-4 carbon atoms in the alkyl groups;

R2means fluorine atom, chlorine, bromine, unsubstituted alkyl with 1-4 carbon atoms, unsubstituted or substituted with halogen alkoxy with 1-4 carbon atoms, an unsubstituted alkylthiols with 1-4 carbon atoms, dialkylamino with 1-4 carbon atoms in the alkyl groups;

R3means a hydrogen atom or n is substituted by alkyl with 1-4 carbon atoms;

R4means unsubstituted alkyl with 1-6 carbon atoms; R5means maybe substituted with halogen or alkoxyl with 1-4 carbon atoms, alkyl with 1-6 carbon atoms or an unsubstituted cycloalkyl with 3-6 carbon atoms, and salts of compounds of formula (I).

2. Compounds according to claim 1, characterized in that

R1means fluorine atom, chlorine, bromine, methyl, ethyl, n - or isopropyl, possibly substituted by fluorine, chlorine, methoxy, ethoxy, n - or isopropoxy, the unsubstituted metalcorp, ethylthiourea, n - or isopropylthio, dimethylaminopropyl or diethylaminopropyl;

R2means fluorine atom, chlorine, bromine, methyl, ethyl, n - or isopropyl, possibly substituted by fluorine, chlorine, methoxy, ethoxy, n - or isopropoxy, the unsubstituted metalcorp, ethylthiourea, n - or isopropylthio, dimethylaminopropyl or diethylaminopropyl;

R3means a hydrogen atom, methyl or ethyl;

R4means methyl, ethyl, n - or isopropyl, n-, ISO-, sec - or tert-butyl;

R5means maybe substituted by fluorine, chlorine, methoxy group, ethoxypropane, n - or isopropoxy methyl, ethyl, n - or isopropyl, n-, ISO-, sec - or tert-butyl, unsubstituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl the L.

3. Compounds according to claim 1, characterized in that

R1means fluorine atom, chlorine, bromine, methyl, ethyl, possibly substituted by fluorine, chlorine, methoxy, ethoxy, the unsubstituted metalcorp, ethylthiourea or dimethylaminopropyl;

R2means fluorine atom, chlorine, bromine, methyl, ethyl, possibly substituted by fluorine, chlorine, methoxy, ethoxy, the unsubstituted metalcorp, ethylthiourea or dimethylaminopropyl;

R3means a hydrogen atom or methyl;

R4means methyl, ethyl, n - or isopropyl;

R5means maybe substituted by fluorine, chlorine, methoxy group or ethoxypropane methyl, ethyl, n - or isopropyl.

4. Compounds of General formula (I) according to one of paragraphs. 1-3, represents sodium, potassium, magnesium, calcium, ammonium, alkylammonium with 1-4 carbon atoms in the alkyl part, dialkylammonium with 1-4 carbon atoms in each alkyl part, trialkylamines with 1-4 carbon atoms in each alkyl part, tetraalkylammonium with 1-4 carbon atoms in each alkyl part, trialkylsilanes with 1-4 carbon atoms in each alkyl part, cycloalkylcarbonyl with five or six carbon atoms in cycloalkyl parts and diallylmethylamine with 1-2 carbon atoms in each alkyl part of the salts of these compounds.

5. Herbicide environments the creation, characterized in that it contains a compound according to any one of paragraphs. 1-4 and the usual neutral extenders and/or surfactants.



 

Same patents:

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to new substituted thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)ons of general formula I

(wherein Q represents oxygen or sulfur; R1 represents unsubstituted alkyl; R2 represents hydrogen, halogen, unsubstituted alkyl; R3 represents hydrogen, halogen, alkyl optionally substituted with alkoxy, alkoxy or arylthio, optionally substituted with alkoxy or halogen, unsubstituted cycloalkyl or cycloalkyloxy, or unsubstituted arylalkoxy or aryloxy; R4 represents unsubstituted alkyl, alkoxy, dialkylamino, cycloalkyl) and their salts. Compounds of present invention are useful as herbicide agents. Also disclosed is herbicide composition and new synthetic intermediates for compounds of formula I.

EFFECT: new compounds and intermediates thereof with herbicide activity.

16 cl, 13 tbl, 67 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to derivatives of benzodiazepine. Invention describes a derivative of benzodiazepine of the formula (I): wherein dotted lines show the possible presence of a double bond; R1, R2, R3, R4 and R5 are given in the invention claim; n represents 0, 1, 2, 3 or 4; X represents sulfur atom (S) or -NT wherein T is give in the invention claim; A represents hydrogen atom, (C6-C18)-aryl group substituted optionally with one or more substitutes Su (as given in the invention claim) or (C1-C12)-alkyl; or in alternative variant R4 and R5 form in common the group -CR6=CR7 wherein CR6 is bound with X and wherein R6 and R7 are given in the invention claim, and their pharmaceutically acceptable salts with acids or bases. It is implied that compounds corresponding to one of points (a)-(e) enumerated in the invention claim are excluded from the invention text. Also, invention describes methods for preparing compounds of the formula (I) and a pharmaceutical composition eliciting the hypolipidemic activity. Invention provides preparing new compounds eliciting the useful biological properties.

EFFECT: improved preparing method, valuable medicinal properties of compounds.

20 cl, 6 tbl, 192 ex

FIELD: organic chemistry, pharmacy.

SUBSTANCE: invention relates to new derivatives of benzimidazole represented by the following formula (I) or its salt:

wherein R1 represents (lower)-alkyl group; R2 represents aromatic (lower)-alkyl group that can be substituted with one or more groups taken among halogen atom, alkyl group, halogen-(lower)-alkyl group, nitro-group, aromatic group, aromatic (lower)-alkoxy-group, (lower)-cycloalkyloxy-(lower)-alkyl group, aromatic (lower)-alkyl group, aromatic (lower)-alkenyl group, aromatic (lower)-alkynyl group, aromatic oxy-(lower)-alkyl group, (lower)-cycloalkyl-(lower)-alkoxy-group, alkenyl group, (lower)-alkoxy-group, (lower)-alkylthio-group and (lower)-alkanesulfonylcarbamoyl group; R3 represents alkyl group, hydroxy-(lower)-alkyl group, alkenyl group, aromatic group, halogenated aromatic group, (lower)-alkyl aromatic group, (lower)-alkenyl aromatic group or aromatic (lower)-alkenyl group; -X- represents cross-linking group represented by one of the following formulas: (II) , (III) , (IV) , (V) . Also, invention relates to pharmaceutical compositions eliciting activity that reduces blood glucose level based on this compound. Invention provides preparing new compounds and pharmaceutical compositions based on thereof used for prophylaxis and treatment of damaged tolerance to glucose, diabetes mellitus, insulin-resistance syndrome, vascular failures syndrome, hyperlipidemia and cardiovascular disorders.

EFFECT: valuable medicinal properties of compounds and compositions.

16 cl, 1 tbl, 86 ex

The invention relates to organic chemistry and can find application in medicine

The invention relates to organic chemistry and can find application in medicine

The invention relates to sulfhemoglobinemia heterocyclic compound represented by formula (I), its pharmaceutically acceptable salts and their hydrates

where the values of A, B, K, T, W, X, Y, U, V, Z, R1specified in paragraph 1 of the claims

The invention relates to new derivatives of amidine General formula (I’)

where it is:

in which R1, R2and R3HE or1-C6alkyl, C1-C6alkoxy, R4- H1-C6alkyl, R5- H1-C6alkyl or the radical:

where R10, R11and R12- OH or H, R13- H1-C6alkyl; or the radical:

where R18, R19and R20- H, HE, C1-C6alkyl, R21and R22- H, C1-C6alkyl, or R21-alkylsulfonyl, alkylsulfonyl, alkylaryl, and R22- H or the radical:

where T is -(CH2)k-, k = 1, 2, R27- H, C1-C6alkyl

The invention relates to new imidazole derivative of the formula (I):where R1represents phenyl or pyridinyl, substituted by substituents selected from the group comprising (1) phenyl, (2) furyl, thienyl, (3) halogen, (4) halogen(lower)alkyl, (5) lower alkylthio, (6) nitro, (7) lower alkenyl, optionally substituted phenyl, (8) lower quinil, optionally substituted phenyl, (9) lower alkoxy, optionally substituted cyclo(lower)alkyl or phenyl, (10) lower alkyl, optionally substituted, phenyloxy or (11) amino, optionally substituted protected carboxyla; R2represents lower alkyl; R3represents halogen or lower alkyl; R4represents (1) lower alkenyl, optionally substituted phenyl, (2) phenyl, optionally substituted lower alkyl or lower alkenyl, (3) lower alkyl or (4) thienyl, optionally substituted with halogen; a represents a lower alkylene and L represents a simple bond, a lower albaniles or lower alkylene, optionally substituted phenyl or pyridinyl, or-X-CH2- where X represents O or NR5where R5represents hydrogen or n is

FIELD: agriculture, in particular method for controlling of weeds.

SUBSTANCE: claimed method for controlling of weeds in tolerant maize cultures includes application of composition comprising (A) road spectrum herbicide from group (A1) glufosinate (salt) and analogs, (A2) glyfosate (salt) and analogs; (B) one or more herbicides from group (B1) cyanazin, alachlor, nicosulfurone, rimsulfurone, sulkotrion, mesotrion, and penthoxamid; (B2) pendimethalyne, methosulam, isoxaflutol, metribuzin, chloransulam, flumetsulam, linuron, florasulam, and isoxachlorotol; and (B3) bromoxinyl, chlorpyralid, tifensulfuron, MCPA (2-methyl-4-chlorophenoxyacetic acid), halosulfuron, and sulfosulfuron, wherein (A) and (B) components are in synergic effective ration. Also disclosed are herbicidal compositions including compound from group (A1) or )F2) and herbicide from group (B).

EFFECT: effective controlling of weeds in tolerant maize cultures.

6 cl, 55 tbl, 3 ex

FIELD: organic chemistry, agriculture, herbicide composition.

SUBSTANCE: invention relates to herbicide composition, containing conventional inert additives and mixture of a) herbicidically effective amount of substance satisfying the formula I [in formula R1 and R3 are the same or different C1-C4-alkyl; R4 and R5 together form groups of formulae: -C-R6(R7)-O-C-R8(R9)-C-R10(R11)-C-R12(R13)-(Z1), -C-R14(R15)-C-R16(R17)-O-C-R18(R19)-C-R20(R21)-(Z2), or -C-R22(R23)-C-R24(R25)-C-R26(R27)-O-C-R28(R29)-(Z3), wherein each R6-R29 is hydrogen; G is hydrogen or -C(X2)-X3-R31; X2 and X3 independently are oxygen; R31 is C1-C10-alkyl]; b) herbicidic synergic amount of at least one herbicide selected from group containing sulfonylureas, phenoxyacetic acids, as well as florsulam, tralcoxidim, klodinafol-propargil, phenoxaprop-P-ethyl, trifluramine, pendimethaline, picolinafen, etc. Composition also may contain safety effective amount of protective agent, such as chloquintocet-mexyl and additive (e.g., mineral oil or C8-C22-fat acid alkyl esters) in amount of 0-2 mass %. Also disclosed is method for selective controlling of weeds and grassy plants in cultural plants by treatment of cultural plants, seeds or seedlings thereof, or vegetation area thereof with claimed composition.

EFFECT: effective composition and method for weed controlling.

5 cl, 11 tbl, 7 ex

FIELD: agriculture, in particular herbicide compositions.

SUBSTANCE: invention relates to weed controlling method for tolerant grain crops using (A) road spectrum herbicides selected from group (A1) glufosinate (salt) and related compounds; (A2) glyphosate (salt) and related compounds; and (B) one or more herbicides selected from group containing (B1) herbicides selectively effecting in grain crops especially against monocotyledonous weeds effecting on folia and/or soil (residual benefit); or (B2) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting especially on folia; or (B3) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting on folia or soil; or (B4) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting on folia; wherein components (A) and (B) are used in synergic ration. Also are described herbicide compositions containing (A1) ) glufosinate (salt) and related compounds and herbicide from group (B); as well as herbicide compositions containing(A2) glyphosate (salt) and related compounds and herbicide from group (B); wherein components (A) and (B) are used in synergically effective ration.

EFFECT: effective controlling of weeds in grain crops.

6 cl, 70 tbl, 3 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: claimed mixture from herbicides and antidotes contains (A) herbicidically active substance based on phenylsulfonylureas of formula I and salts thereof (in formula R1 is hydrogen or C1-C6-alkyl; R2 is C1-C3-alkyl; R3 is C1-C3-alkoxy; R4 is hydrogen or C1-C4-alkyl; Hal is fluorine, chlorine, bromine, or iodine); and (B) antidote of formulae II or III , wherein X is hydrogen, halogen, C1-C4-alkyl; C1-C4-alkoxy, nitro or C1-C4-haloalkyl; Z is hydroxyl, C1-C8-alkoxy, C3-C6-cycloalkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy; R5 is C1-C2-alkandiyl chain optionally substituted with one or two C1-C4 alkyl residues or (C1-C3-alcoxy)carbonyl; W is bivalent heterocyclic residue; n = 1-5; in weight ratio herbicide/antidote of 100:1-1:100. Also disclosed is method for protection of cultural plants against phytotoxic side effect of herbicidically active substance of formula I. Claimed method includes antidote application of formulae II or III on plant, plant parts, plant seeds or seeding areas before or together with herbicidically active substance in amount of 0.005-0.5 kg/hectare in weight ratio of 100:1-1:100.

EFFECT: mixture for effective selective weed controlling in cultural plant, particularly in maize and grain cultures.

8 cl, 2 ex, 7 tbl

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes a synergistic composition of herbicides comprising components (A) and (B) wherein (A) represents herbicide taken among the group of the formula (I):

wherein R1 means (C1-C4)-alkyl; R2 means (C1-C4)-alkyl; R3 means hydrogen atom; X and Y mean (C1-C4)-alkoxy-group; (B) represents one or two herbicides taken among the group of compounds or their acceptable forms: alachlor, metolachlor, acetochlor, dimetenamide, atrazine, cyanasin, metribusin, fluthiamide, nicosulfuron, rimsulfuron, primisulfuron, pendimetalin, sulcotrion, dicamba, mesotrion, isoxachlortol, metosulam, anilofos, fenoxaprop-ethyl, setoxydim, diclofop-methyl, MCPA, bromoxynil, pyridat, clopyralid, iodosulfuron-methyl, ethoxysulfuron, amidosulfuron, gluphosinat-amminium, isopropylammonium-glyphosate, imasetapir wherein components (A) and (B) are taken in the effective doses. Also, invention describes a method for control of weeds by using above indicated herbicide composition. Invention provides the development of the synergistic herbicide composition eliciting high activity.

EFFECT: improved method for control, valuable properties of composition.

6 cl, 26 tbl, 3 ex

The invention relates to the field of plant protection products that can be used against weeds in tolerant or resistant crops sugar beet and which as a herbicide biologically active substances contain a combination of two or more herbicides

The invention relates to chemical means of protection of grain crops from weeds, and in particular to compositions comprising chlorsulfuron and dicamba

The invention relates to organic chemistry and agriculture, in particular to the derived SIM-triazine as a compound that protects against fetotoksicheskoe actions of herbicides in the cultivation of sunflower (antidote)
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