WO1997001542A1

WO1997001542A1 - Substituted carbonylaminophenyluracils

Info

Publication number: WO1997001542A1
Application number: PCT/EP1996/002612
Authority: WO
Inventors: Roland Andree; Mark Wilhelm Drewes; Markus Dollinger; Hans-Joachim Santel
Original assignee: Bayer Aktiengesellschaft
Priority date: 1995-06-29
Filing date: 1996-06-17
Publication date: 1997-01-16
Also published as: CN1193319A; CA2225828A1; AR006084A1; AR002596A1; AU6304396A; JPH11508545A; EP0835247A1; BR9609319A; KR19990028225A; DE19523640A1

Abstract

The invention concerns novel substituted carbonylaminophenyluracils of general formula (I) in which R?1, R2, R3, R4, R5, R6 and R7¿ have the meanings given in the description. The invention further concerns a method of preparing these compounds and their use as herbicides.

Description

Substituted carbonylaminophenyluracile

The invention relates to new substituted carbonylaminophenyluracils, processes for their preparation and their use as herbicides.

It is known that certain substituted aminophenyluracils have herbicidal properties (cf. EP 408382 / US 5084084 / US 5127935 / US 5154755, EP 563384 / US 5356863, EP 648749). However, these connections have so far had no significant significance. The new substituted carbonylaminophenyluracils of the general formula (I) have now been found

in which

R ^{1 represents} hydrogen, cyano or halogen,

R ^{2 represents} cyano or halogen,

R ^{3 represents} in each case optionally substituted cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,

R ^{4 stands} for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl or for the grouping -CO-R ³ , in which R ^{3 has} the meaning given above, R ^{5 represents} hydrogen, halogen or optionally substituted alkyl or alkoxy,

R ^{6 represents} optionally substituted alkyl and

R ^{7 stands} for hydrogen or for optionally substituted alkyl, alkoxy, alkenyl or alkynyl.

The new substituted aminophenyluracils of the general formula (I) are obtained if corresponding aminophenyluracils of the general formula (II)

in which R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ and R ^{7 have} the meanings given above, and

R ^{8 represents} hydrogen, trifluoroacetyl or alkylsulfonyl, with acid derivatives of the general formula (III)

R ³ -CO-X (III) in which

R ^{3 has} the meaning given above and

X represents halogen or the grouping -O-CO-R ³ , if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.

The new substituted carbonylaminophenyluracils of the general formula (I) are notable for strong herbicidal activity. The starting materials of the formula (II) are also herbicidally active to a certain extent.

In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkynyl, are each straight-chain or branched.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine. The invention preferably relates to compounds of the formula (I) in which

R ^{1 represents} hydrogen, cyano, fluorine or chlorine,

R ^{2 represents} cyano, fluorine, chlorine or bromine,

R ^{3 represents} in each case cycloalkyl or cycloalkylalkyl which is optionally substituted by cyano, fluorine, chlorine, bromine or C ₁ -C ₄ -alkyl and has 3 to 8 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the alkyl part,

R ³ furthermore for each optionally by fluorine, chlorine, bromine, cyano, roitro, carboxy, carbamoyl, thiocarbamoyl, by C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfionyl or C ₁ -C ₄ alkylsulfonyl

(which are each optionally substituted by fluorine and / or chlorine), by dimethylaminosulfonyl or diethylaminosulfonyl, by C ₁ -C ₄ -alkoxycarbonyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy), by phenyl , Phenyloxy or phenylthio (which are each optionally substituted by fluorine, chlorine, bromine,

Cyano, methyl, methoxy, trifluoromethyl and / or trifluoromethoxy are substituted) substituted phenyl, Νaphthyl, benzyl, phenylethyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridinyl or quinolinyl, R ^{4 represents} hydrogen, in each case optionally substituted by cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxycarbonyl alkyl, alkenyl or alkynyl each having up to 10 carbon atoms, R ⁴ furthermore represents cycloalkyl or cycloalkylalkyl which is optionally substituted by cyano, fluorine, chlorine, bromine or C ₁ -C ₄ -alkyl and has 3 to 8 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the alkyl part,

R ⁴ furthermore for each optionally by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, by C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl (which are each optionally substituted by fluorine and / or chlorine), by dimethylaminosulfonyl or diethylaminosulfonyl, by C ₁ - C ₄ alkoxycarbonyl (which is optionally substituted by fluorine, chlorine, Bromine, cyano, methoxy or ethoxy is substituted) by phenyl, phenyloxy or phenylthio (which are each optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and / or trifluoromethoxy) substituted phenyl, naphthyl, benzyl, phenylethyl , Fuiyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridinyl or quinolinyl, or represents the group -CO-R ³ , in which R ^{3 has} the meaning preferably given above,

R ^{5 represents} hydrogen, fluorine, chlorine, bromine or alkyl or alkoxy each optionally substituted by fluorine and / or chlorine, each having 1 to 4 carbon atoms, R ^{6 represents} alkyl optionally substituted by fluorine and / or chlorine having 1 to 4 carbon atoms and

R ^{7 stands} for hydrogen or for alkyl, alkoxy, alkenyl or alkynyl, each optionally substituted by cyano, fluorine, chlorine or C ₁ -C ₄ -alkoxy, each having up to 6 carbon atoms. The invention relates in particular to compounds of the formula (I) in which

R ^{1 represents} hydrogen, fluorine or chlorine, R ^{2 represents} cyano, fluorine, chlorine or bromine,

R ³ represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl,

R ³ for each optionally by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, by dimethylaminosulfonyl or diethylaminosulfonyl, by methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, by phenyl, phenyloxy or phenylthio substituted phenyl, naphthyl, furyl, benzyl, benzyl , Tetrahydrothienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridinyl or quinolinyl,

R ⁴ for hydrogen, for each methyl, ethyl, n- or i-propyl, n- substituted by cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy-carbonyl , i-, s- or t-butyl, n-, i-, s- or t-pentyl, propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl,

R ⁴ also represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, R ⁴ also represents in each case optionally by Fluorine, chlorine, bromine, cyano,

Nitro, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, by dimethylaminosulfonyl or diethylaminosulfonyl Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, by phenyl,

Phenyloxy or phenylthio substituted phenyl, naphthyl, benzyl, phenylethyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridinyl or quinolinyl, or for which Grouping -CO-R ³ , in which R ^{3 has} the meaning given above as being particularly preferred,

R ^{3 represents} hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy, R ^{6 represents} methyl, ethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, chlorofluoroethyl, trifluoroethyl , Trichloroethyl, chlorodifluoroethyl, fluorodichloroethyl, tetrafiuorethyl, chlorotrifluoroethyl or pentafluoroethyl and R ^{7 represents} hydrogen or methyl, ethyl, n- or i-propyl, n-, i- or optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy s-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyl, butenyl, propynyl or butynyl.

The general or preferred definitions of radicals listed above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.

If, for example, 1- (4-chloro-2-fluoro-5-methylsulfonylamino-phenyl) -3,6-dihydro-2,6-dioxo-3,5-dimethyl-4-difluoromethyl-1 (2H) -pyrimidine and 2-fluorobenzoyl chloride as starting materials, the course of the reaction in the process according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the aminophenyluracils to be used as starting materials in the process according to the invention for the preparation of the compounds of the formula (I). In the formula (II), R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ and R ⁷ preferably or in particular have the meaning which, as described above, in the description of the compounds of the formula (I) to be prepared according to the invention are preferred or was particularly preferably indicated for R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ and R ⁷ ; R ⁸ preferably represents hydrogen, trifluoroacetyl or C ₁ -C ₄ alkylsulfonyl. The starting materials of the formula (II) are known and / or can be prepared by processes known per se (cf. EP 408382, EP 648749, production examples).

The acid derivatives to be used further as starting materials in the process according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (III). In the formula (III), R ³ preferably or in particular has the meaning which has already been mentioned above in the description of the compounds of the formula (I) to be prepared according to the invention preferably or as particularly preferred for R ³ ; X preferably represents fluorine, chlorine or bromine, in particular fluorine. The starting materials of the formula (III) are known synthetic chemicals.

The process according to the invention for the preparation of the compounds of the formula (I) is preferably carried out in the presence of a suitable reaction auxiliary. The usual inorganic auxiliaries generally come see or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or

Calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n- or i-propanolate, n-, i- , s- or t-butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5-ethyl-2- methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2,2,2] octane (DABCO), 1,5-diazabicyclo [4,3,0] -non- 5-ene (DBN), and 1.8 diazabicyclo [5,4,0] -undec-7-ene (DBU).

The process according to the invention for the preparation of the compounds of the formula (I) is preferably carried out in the presence of a diluent. The usual organic solvents are generally suitable as diluents. These preferably include aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons, such as, for example, pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane (methylene chloride), trichloromethane (chloroform or carbon tetrachloride, dialkyl ethers, such as, for example, diethyl ether, diisopropyl ether, methyl t-butyl ether (MTBE), ethyl t-butyl ether, methyl t-pentyl ether (TAME), ethyl t-pentyl ether, tetrahydrofuran (THF), 1, 4-dioxane, ethylene glycol dimethyl ether or diethyl ether, diethylene glycol dimethyl ether or diethyl ether; Dialkyl ketones, such as, for example, acetone, butanone (methyl ethyl ketone), methyl 1-propyl ketone or methyl 1-butyl ketone, nitriles, such as, for example, acetonitrile, propionitrile, butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide (DMF), N, N-dimethyl-acetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethyl-phosphoric acid triamide; Esters, such as, for example, methyl acetate, ethyl ester, n- or -1-propyl ester, -n-, -1- or -s-butyl ester; Sulfoxides such as dimethyl sulfoxide; Alkanols, such as, for example, methanol, ethanol, n- or i-propanol, n-, i-, s- or t-butanol, ethylene glycol monomethyl ether or monoethyl ether, diethyl glycol monomethyl ether or monoethyl ether; their mixtures with water or pure water.

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and

120 ° C.

The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers.

Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The active compounds according to the invention can e.g. can be used in the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea,

Trifolium, Ranunculus, Taraxacum. Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus,

Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.

Depending on the concentration, the active compounds according to the invention are suitable for combating total weeds e.g. on industrial and track systems and on

Because of and places with and without tree cover. Likewise, the compounds for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective purposes Weed control can be used in annual crops.

The active compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.

The active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders,

Dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as fine encapsulation in polymeric substances.

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

The following are suitable as solid carriers:

e.g. Ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silicic acid, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well

Granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.

Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalates can be used cyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%. The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.

Known herbicides, for example anilides, such as e.g. Diflufenican and Propanil; Aryl carboxylic acids, e.g. Dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, e.g. 2.4 D, 2.4 DB, 2.4

DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, e.g. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones, e.g. Chloridazon and norflurazon; Carbamates, e.g. Chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides, e.g. Alachlor, acetochlor, butachlor, metazachlor, metolachlor,

Pretilachlor and propachlor; Dinitroanilines, e.g. Oryzalin, pendimethalin and trifluralin; Diphenyl ethers, e.g. Acifluorfen, Bifenox, Fluoroglycofen, Fomesafen, Halosafen, Lactofen and Oxyfluorfen; Ureas, e.g. Chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; Hydroxylamines, e.g. Alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; Imidazolinones, e.g. Imazethapyr, imazamethabenz, imazapyr and imazaquin; Nitriles, e.g. Bromoxynil, dichlobenil and ioxynil; Oxyacetamides, e.g. Mefenacet; Sulfonylureas, e.g. Amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuronmethyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl,

Triasulfuron and tribenuron-methyl; Thiol carbamates such as butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates; Triazines such as atrazine, cyanazine, simazin, simetryne, terbutryne and terbutylazine; Triazinones such as hexazinone, metamitron and metribuzin; Others such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane. A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

The active ingredients as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use

Solutions, suspensions, emulsions, powders, pastes and granules are used. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.

The active compounds according to the invention can be applied both before and after the plants emerge. They can also be worked into the soil before sowing.

The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 10 g and 10 kg of active ingredient per hectare of soil, preferably between 50 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the examples below.

Preparation Examples:

example 1

1.3 g (6 mmol) of 3,5-dichlorobenzoyl chloride are stirred with a mixture of 2.1 g (5 mmol) of 1- (4-cyano-2-fluoro-5-ethylsulfonylamino-phenyl) -3, 6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine, 1 ml of triethylamine and 50 ml of acetonitrile are added and the reaction mixture is stirred at 20 ° C. for 24 hours. It is then concentrated in a water jet vacuum, the residue is shaken with 1N hydrochloric acid / ethyl acetate, the organic phase is separated off, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with diethyl ether / petroleum ether and the crystalline product is isolated by suction.

0.90 g (30% of theory) of 1- [4-cyano-2-fluoro-5- (3,5-dichlorobenzoylamino) phenyl] -3,6-dihydro-2,6-dioxo- 3-methyl-4-trifluoromethyl-1 (2H) -ρyrimidine, melting point 212 ° C. Analogously to Example 1 and in accordance with the general description of the production process according to the invention, the compounds of the formula (I) listed in Table 1 below can also be prepared, for example.

Starting materials of formula (II): Example (II-1)

A mixture of 1.67 g (4 mmol) of 1- (4-cyano-2-fluoro-5-methylsulfonylaminophenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H ) -pyrimidine, 1.05 g

(5 mmol) trifluoroacetic anhydride, 1.5 g triethylamine and 20 ml acetonitrile is stirred at 20 ° C. for 30 minutes and then concentrated in a water jet vacuum. The residue is shaken with 1N hydrochloric acid / ethyl acetate, the organic phase is separated off, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum and the residue is column chromatographed (silica gel,

Hexane / ethyl acetate, vol .: 4: 1) worked up.

1.0 g (59% of theory) of 1- (4-cyano-2-fluoro-5-trifluoroacetylaminophenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 ( 2H) -pyrimidine with a melting point of 105 ° C.

Example (II-2)

A mixture of 2.19 g (5 mmol) of 1- (4-cyano-2-fluoro-5-trifluoroacetylaminophenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H ) -pyrimidine, 0.76 g (6 mmol) of dimethyl sulfate, 0.83 g of potassium carbonate and 50 ml of acetone is heated under reflux for 3 hours and then concentrated in a water jet vacuum. The residue is stirred with 1N hydrochloric acid / diethyl ether; then the crystalline product is isolated by suction.

1.4 g (64% of theory) of 1- [4-cyano-2-fluoro-5- (N-methyl-N-trifluoroacetylamino) phenyl] -3,6-dihydro-2,6-dioxo- 3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine with a melting point of 202 ° C.

Example (II-3)

0.17 g (1.2 mmol) of pivalic acid chloride are stirred with a mixture of 0.50 g (1.2 mmol) of 1- (4-cyano-2-fluoro-5-trifluoroacetylamino-phenyl) -3,6- dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine, 1 ml of triethylamine and 50 ml of acetonitrile are added and the reaction mixture is stirred at 20 ° C. for 18 hours and at 60 ° C. for a further 15 hours . It is then concentrated in a water jet vacuum, the residue is shaken with 1N hydrochloric acid / ethyl acetate, the organic phase is separated off, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum and the residue is worked up by column chromatography (silica gel, chloroform / ethyl acetate, vol .: 1: 1).

In addition to unreacted 1- (4-cyano-2-fluoro-5-trifluoroacetylaminophenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine (first fraction : 0.30 g) 0.2 g (50% of theory) 1- (4-cyano-2-fluoro-5-aminophenyl) -3,6-dihydro-2,6-dioxo-3-methyl- 4-trifluoromethyl-1 (2H) pyrimidine as the second fraction. Melting point: 195 ° C.

The compound to be prepared according to Example (II-3) is not yet known from the literature; it is the subject of the present application as a new compound. Application examples: Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is watered or sprayed with the active ingredient preparation. The amount of water per unit area is expediently kept constant. The concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area. After three weeks, the degree of damage to the plants is rated in%

Damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control)

100% = total destruction In this test, for example, the compounds according to Preparation Examples 1, 2, 3 and 4 and (II-1) and (II-2) show strong activity against weeds such as Alopecurus (70 -95%), Avena (80-100%), Setaria (100%), Abutilon (100%), Amaranthus (95-100%) and Sinapis (100%). Example B

Post emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, mix 1 part by weight of active compound with the stated amount of solvent, add the stated amount of emulsifier and dilute the concentrate with water to the desired concentration.

Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in about 1000 l / ha.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:

0% = no effect (like untreated control)

100% = total annihilation

In this test, for example, the compounds according to Preparation Examples 1, 2, 3 and 4 and (II-1) and (II-2) show a strong action against weeds such as abutilone (100%), amaranthus ( 90-100%) and Sinapis (80-100%).

Claims

claims

Carbonylaminophenyluracile of the general formula (I)

in which

R ^{1 represents} hydrogen, cyano or halogen,

R ^{2 represents} cyano or halogen,

R ^{4 stands} for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl or for the group -CO- R ³ , in which R ^{3 has} the meaning given above,

R ^{5 represents} hydrogen, halogen or optionally substituted alkyl or alkoxy,

R ^{6 represents} optionally substituted alkyl and

2. Process for the preparation of aminophenyluracils of the general

Formula (I),

in which

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ^{7 have} the meanings given in Claim 1, characterized in that corresponding aminophenyl-uracils of the general formula (II)

in which

R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ and R ^{7 have} the meanings given above, and R ^{8 represents} hydrogen, trifluoroacetyl or alkyl sulfonyl, with acid derivatives of the general formula (III) R ³ -CO-X (III) in which

R ^{3 has} the meaning given above and

3. Carbonylaminophenyluracile of the general formula (I) according to claim 1, characterized in that

R ^{1 represents} hydrogen, cyano, fluorine or chlorine, R ^{2 represents} cyano, fluorine, chlorine or bromine,

R ^{3 represents} in each case optionally substituted by cyano, fluorine, chlorine, bromine or C ₁ -C ₄ alkyl cycloalkyl or cycloalkylalkyl having 3 to 8 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the alkyl part, R ³ furthermore in each case optionally by fluorine , Chlorine, bromine,

Cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, through C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ - C ₄ alkylsulfonyl (which are each optionally substituted by fluorine and / or chlorine), by dimethylaminosulfonyl or diethylaminosulfonyl, by C ₁ -C ₄ alkoxycarbonyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy), by phenyl , Phenyloxy or phenylthio (which are each optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and / or trifluoromethoxy) substituted phenyl, naphthyl, benzyl, phenylethyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl , Pyrazolyl, pyridinyl or quinolinyl, R ^{4 represents} hydrogen, each optionally substituted by cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy-carbonyl-substituted alkyl, alkenyl or alkynyl each having up to 10 carbon atoms, R ⁴ for each optionally by cyano, fluorine, chlorine,

Bromine or C ₁ -C ₄ alkyl-substituted cycloalkyl or cycloalkylalkyl having 3 to 8 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the alkyl part,

R ⁴ furthermore for each optionally by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, by C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ - C ₄ alkyl (which are each optionally substituted by fluorine and / or chlorine) sulfonyl, by dimethylaminosulphonyl or diethylaminosulphonyl, by C ₁ -C ,, - alkoxy-carbonyl (which is optionally substituted by fluorine Chlorine, bromine, cyano, methoxy or ethoxy is substituted) by phenyl, phenyloxy or phenylthio (which are each optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and / or trifluoromethoxy) substituted phenyl, naphthyl, benzyl , Phenylethyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl,

Is pyrazolyl, pyridinyl or quinolinyl, or represents the group -CO-R ³ , in which R ^{3 has} the meaning preferably given above,

R ^{5 represents} hydrogen, fluorine, chlorine, bromine or alkyl or alkoxy, each optionally substituted by fluorine and / or chlorine, each having 1 to 4 carbon atoms,

R ^{6 represents} optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms and

R ^{7 represents} hydrogen or alkyl, alkoxy, alkenyl or optionally substituted by cyano, fluorine, chlorine or C ₁ -C ₄ alkoxy

Alkynyl each having up to 6 carbon atoms.

4. Carbonylaminophenyluracile of the general formula (I) according to claim 1, characterized in that

R ^{1 represents} hydrogen, fluorine or chlorine,

R ^{2 represents} cyano, fluorine, chlorine or bromine, R ³ each optionally represents cyano, fluorine, chlorine, bromine,

Methyl, ethyl, n- or i-propyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,

R ³ for each optionally by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, by dimethylaminosulfonyl or diethylaminosulfonyl, by methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl

Phenyl, phenyloxy or phenylthio substituted phenyl, naphthyl, benzyl, phenylethyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridinyl or quinolinyl, R ^{4 represents} hydrogen, each optionally substituted by cyano, carboxy,

Carbamoyl, thiocarbamoyl, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy carbonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- , i-, s- or t-pentyl, propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl, R ⁴ furthermore in each case optionally by cyano, fluorine, chlorine,

Bromine, methyl, ethyl, n- or i-propyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,

R ⁴ furthermore each for optionally by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, by dimethylaminosulfonyl or diethylaminosulfonyl, by methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbon Phenyl, phenyloxy or

Phenylthio substituted phenyl, naphthyl, benzyl, phenylethyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridinyl or quinolinyl, or for which

Grouping -CO-R is where R ^{3 has} the meaning given above as being particularly preferred,

R ^{5 represents} hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy,

R ⁶ for methyl, ethyl, difluoromethyl, dichloromethyl, trifluoromethyl,

Trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, chlorofluoroethyl, trifluoroethyl,

Trichlorethyl, chlorodifluoroethyl, fluorodi chloroethyl, tetrafluoroethyl, chlorotrifluoroethyl or pentafluoroethyl and

R ⁷ for hydrogen or for each optionally by cyano, fluorine,

Chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyl, Butenyl, propynyl or butynyl.

5. Herbicidal agents, characterized in that they contain at least one carbonylaminophenyluracil of the general formula (I) according to Claims 1 to 4.

6. A method for controlling unwanted plants, characterized in that carbonylaminophenyluracils of the general formula (I) according to Claims 1 to 4 are allowed to act on undesired plants and / or their habitat.

7. Use of carbonylaminophenyluracils of the general formula (I) according to Claims 1 to 4 for combating undesirable

Plants.

8. A process for the preparation of herbicidal compositions, characterized in that carbonylaminophenyluracils of the general formula (I) according to Claims 1 to 4 are mixed with extenders and / or surface-active substances.

9. aminophenyluracil of the general formula (II)

in which

R ^{1 represents} fluorine,

R ^{2 represents} cyano,

R ⁴ , R ⁵ and R ⁸ each represent hydrogen,

R ^{6 represents} trifluoromethyl and

R ^{7 represents} methyl.

10. Use of aminophenyluracils of the general formula (II)

in which

R ^{1 represents} hydrogen, cyano or halogen,

R ^{2 represents} cyano or halogen,

R ⁴ for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl or for the grouping -CO-

R ³ stands in which R ^{3 has} the meaning given above, R ^{5 stands} for hydrogen, halogen or for optionally substituted alkyl or alkoxy,

R ^{6 represents} optionally substituted alkyl and

R ^{7 stands} for hydrogen or for optionally substituted alkyl, alkoxy, alkenyl or alkynyl, and R ^{8 stands} for hydrogen, trifluoroacetyl or alkylsulfonyl, for combating undesired plants.