WO1996036614A1

WO1996036614A1 - Aminouracil derivates

Info

Publication number: WO1996036614A1
Application number: PCT/EP1996/001819
Authority: WO
Inventors: Roland Andree; Mark Wilhelm Drewes; Markus Dollinger; Hans-Joachim Santel
Original assignee: Bayer Aktiengesellschaft
Priority date: 1995-05-15
Filing date: 1996-05-02
Publication date: 1996-11-21
Also published as: DE19517732A1; AU5812296A

Abstract

The invention relates to novel aminouracil derivatives of general formula (I) in which R?1, R2, R3, R4 and R5¿ have the meanings given in the description, a process for their production and their use as herbicides.

Description

Aminouracil derivatives

The invention relates to new aminouracil derivatives, a process for their preparation and their use as herbicides.

It is known that certain substituted uracils have herbicidal properties (cf. EP 408382 / US 5084084 / US 5127935 / US5154755, EP 563384, DE 4412079). However, these compounds have so far had no significant significance.

The new aminouracil derivatives of the general formula (I) have now been found

in which

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

R ^{2 represents} cyano, thiocarbamoyl, halogen or optionally substituted alkyl,

R ³ represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heterocyclyl,

R ^{4 represents} hydrogen, halogen or in each case optionally substituted alkyl or alkoxy and

R ^{5 represents} optionally substituted alkyl. The new aminouracil derivatives of the general formula (I) are obtained if uracil derivatives of the general formula (II)

in which

R ¹ , R ² , R ³ , R ⁴ and R ^{5 have} the meanings given above,

with an electrophilic aminating agent, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.

The new aminouracil derivatives of the general formula (I) are notable for strong herbicidal activity.

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, chlorine, bromine or iodine,

R ^{2 represents} cyano, thiocarbamoyl, fluorine, chlorine, bromine, or alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and / or chlorine, R ³ is optionally substituted by cyano, fluorine, chlorine, bromine, C _r C ₄ alkoxy or _C] -C ₄ -alkylthio-substituted alkyl having 1 to 6 carbon atoms,

R ³ furthermore represents alkenyl or alkynyl, each with 2 to 6 carbon atoms, optionally substituted by fluorine, chlorine and / or bromine,

R ³ furthermore represents cycloalkyl or cycloalkylalkyl with 3 to 8 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the alkyl part, optionally substituted by cyano, fluorine, chlorine, bromine or C ₁ -C ₄ alkyl,

R ³ furthermore for each optionally by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, by C _r C ₄ alkyl, C _r C ₄ alkoxy, C _r C ₄ alkylthio, C _r C ₄ - Alkylsulfιnyl or C _r C ₄ -alkylsulfonyl (which are each optionally substituted by fluorine and / or chlorine), by dimethylaminosulfonyl or diethylaminosulfonyl, by C - C ₄ -alkoxy-carbohyl (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 , Thienyl, pyrazolyl, pyridinyl or quinolinyl,

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

R ^{5 represents} alkyl with 1 to 4 carbon atoms optionally substituted by fluorine and / or chlorine.

The invention relates in particular to compounds of the formula (I) in which

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

R ^{2 represents} cyano, thiocarbamoyl, fluorine, chlorine, bromine, methyl, difluoromethyl or trifluoromethyl, R ³ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

R ³ furthermore represents cyclopropyl, cyclobutyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl,

Cyclopentyl or cyclohexyl,

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, n- or i-propylthio,

Methylsulfinyl, ethylsulfinyl, n- or i-propyl sulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted phenyl, naphthyl, benzyl, benzyl, Pyrazolyl or pyridinyl,

R ^{4 represents} hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine, and

R ^{5 represents} methyl, ethyl, n- or i-propyl optionally substituted by fluorine and / or chlorine.

The general or preferred radical definitions 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 residual definitions can be combined with one another, that is to say also between the specified preferred ranges.

For example, if 1- (4-chloro-2-fluoro-5-methylsulfonylamino-phenyl) -3,6-dihydro-2,6-dioxo-4-methyl-1 (2H) -pyrimidine is used as the starting material and 1-amino- oxy-2,4-dinitro-benzene as an electrophilic aminating agent, the course of the reaction in the process according to the invention can be outlined using the following formula:

The uracil derivatives to be used 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 (II). In the formula (II), R ¹ , R ² , R ³ , R ⁴ and R ⁵ preferably or in particular have those meanings which have already been mentioned above for

Description of the compounds of the formula (I) to be prepared according to the invention have been given preferably or as particularly preferred for R ¹ , R ² , R ³ , R ⁴ and R ⁵ .

The starting materials of the formula (II) are known and / or can be prepared by processes known per se (cf. EP 408382 / US 5084084 / US

5127935 / US5154755, EP 563384, DE 4412079).

The process according to the invention is carried out using an electrophilic aminating agent. The usual electrophilic amination agents can be used here. Examples include l-aminooxy-2,4-dinitro-benzene (2,4-dinitro-phenyl-hydroxylamine) and hydroxylamine-O-sulfonic acid.

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 or organic bases or acid acceptors are generally suitable as reaction auxiliaries. This preferably includes alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as 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 methanolate, ethanolate, n- or i-propanolate, n-, i-, s- or t-butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimethyl benzylamine, 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 diethyl ether, diisopropyl ether, methyl t-butyl ether, ethyl t-butyl ether, methyl t-pentyl ether (MTBE), 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 i-propyl ketone or methyl i-butyl ketone, nitriles, such as, for example, acetonitrile, propionitrile, butyronitrile or benzonitrile; Amides, such as, for example, 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 i-propyl ester, n-, i- 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 -20 ° C and + 100 ° C, preferably between 0 ° C and 80 ° C, in particular between 20 ° C and 60 ° 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, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronicaex, Abutil 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 compounds of the formula (I) are suitable for total weed control, 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 weed control in annual crops.

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

The active ingredients 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 and very fine encapsulations in polymers Fabrics.

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

Possible solid carriers are: e.g. Ammonium salts and natural rock flours, such as kaolins, clays,

Talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, 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 and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; 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; suitable 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 phthalo- 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 weed control 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, metolochlor, 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, metsulfuron-methyl, nicosulfuron, primi sulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates, e.g. Butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates; Triazines, e.g. Atrazin, cyanazin, simazin, simetryne, terbutryne and terbutylazin; Triazinones, e.g. 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 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 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.

MANUFACTURING EXAMPLES:

example 1

2.1 g (5 mmol) of l- (4-cyano-2-fluoro-5-ethylsulfonylaminophenyl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidine are in 20 ml of N, N-dimethylformamide and 0.5 g (20 mmol) of sodium hydride are added. The mixture is stirred for 15 minutes at room temperature (approx. 20 ° C). Then 1 g (5 mmol) of l-aminooxy-2,4-dinitro-benzene (2,4-dinitro-phenyl-hydroxylamine) is added and the mixture is stirred at about 20 ° C. for about 30 minutes. Then another 1 g and, after stirring for a further 30 minutes, another 0.5 g of l-aminooxy-2,4-dinitro-benzene are added to the mixture, after which the mixture is stirred for a further 4 hours at approx. For working up, the mixture is diluted to about three times the volume with ethyl acetate. The mixture is then added to approximately the same volume of a saturated aqueous sodium chloride solution, the organic phase is separated off and the aqueous phase is subsequently extracted with ethyl acetate. The combined organic solutions are washed with water, dried with sodium sulfate and filtered. After concentrating the filtrate, the crude product obtained as a residue is purified by column chromatography (silica gel, cyclohexane / ethyl acetate, vol .: 1/1).

0.25 g (11% of theory) of 3-amino-l- [4-cyano-2-fluoro-5- (l-ethylsulfonylhydrazino) phenyl] -3,6-dihydro-2 are obtained, 6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidine with melting point 267 ° C.

Analogously to Example 1 and in accordance with the general description of the production process according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) listed in Table 1 below.

Table 1: Examples of the compounds of the formula (I)

Example R ¹ RR ³ R ⁴ R ⁵ Schmelz¬

No. point (° C)

2 F CN nC ₃ H ₇ H CF ₃ 200

3 F CN iC ₃ H ₇ H CF ₃ 275

4 F CN CH ₃ H CF ₃

5 F CN CH ₃ CH ₃ CF ₃

6 F CN C ₂ H ₅ Cl CF ₃

7 F CN CH ₃ H CHF ₂

8 F CN nC ₄ H ₉ H CHF ₂

9 F CN nC ₃ H ₇ H CHF ₂

10 F s CH, H CF,

NH "

11 H CN nC ₃ H ₇ Cl CF ₃

12 H CN C ₂ H ₅ H CF ₂ C1 (Continued in Table 1)

Example R ¹ R ^ R ^ά R ⁴ R ⁵ melting

No. point (° C)

13 F CN C ₂ H ₅ H CF ₂ CF ₃ 14 FS CH, H CHF-,

NH,

16 F CN CH ₃ H CF ₂ C1

17 F s CH ₃ H CF ₂ C1

^ NH ₂

18 F CN C ₂ H ₅ H CHF ₂

19 F s C ₂ H ₅ H CF ₂ CF _;

^ NH ₂

20 F CN C ₂ H ₅ CH ₃ CF ₂ CF-

21 F s CH ₃ CH ₃ CF ₃

^ NH ₂

22 F CN C ₂ H ₅ Cl CF ₂ C1

23 FS CH ₃ H CF ₂ C1 - ^ NH ₂

24 F CN C ₂ H ₅ Cl CF ₃

25 F CN nC ₅ H _π H CF ₃

26 F Cl C ₂ H ₅ H CF ₃

27 Cl Cl C ₂ H ₅ H CF ₃

28 F Br C ₂ H ₅ H CF ₃

29 F Cl C ₂ H ₅ CH ₃ CF ₃

30 F Cl CH ₃ H CF ₃

31 F CN -CH ₂ CH CH ₂ C1 H CF ₃ Examples of use:

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 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 1, 2 and 3 show very strong activity against weeds such as abutilone (80-100%) with very good tolerance to crop plants, such as maize, (0%) and an application rate of 125 g / ha. ), Amaranthus (80-100%), Galium (90%) and Sinapis (80%). Example B

Post 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.

Test plants which have 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 1000 l of water / 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 destruction

In this test, for example, the compound according to Preparation Example 1 shows good compatibility with crop plants, such as Corn (5%) and one

Application rate of only 30g / ha very strong action against weeds such as Abutilon (100%), Amaranthus (100%), Galium (100%) and Sinapis (100%).

Claims

claims

1. Aminouracil derivatives of the general formula (I)

in which

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

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

R ^{5 represents} optionally substituted alkyl.

2. Aminouracil derivatives of the general formula (I) according to claim 1, characterized in that

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

R ^{2 stands} for cyano, thiocarbamoyl, fluorine, chlorine, bromine, or for alkyl with 1 to 4 carbon atoms optionally substituted by fluorine and / or chlorine, R ^{3 represents} alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, fluorine, chlorine, bromine, 0, -0 ₄ -alkoxy or C _] -C ₄ -alkylthio,

R ³ furthermore each represents alkenyl or alkynyl, each substituted by fluorine, chlorine and / or bromine, each having 2 to 6

Carbon atoms,

R ³ furthermore represents cycloalkyl or cycloalkylalkyl with 3 to 8 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the alkyl part, optionally substituted by cyano, fluorine, chlorine, bromine or C 1 -C ₄ -alkyl,

R ³ for each optionally by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, by CC ₄ alkyl, C _r C ₄ alkoxy, C _r C ₄ alkylthio, C, -C ₄ alkylsulfonyl or C _] -C ₄ alkylsulfonyl (which are each optionally substituted by fluorine and / or chlorine), by dimethylaminosulfonyl or

Diethylaminosulfonyl, by C _r C ₄ -alkoxy-carbonyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy), by phenyl, phenyloxy or phenylthio (which in each case optionally by fluorine, chlorine, bromine, cyano , Methyl, methoxy, trifluoromethyl and / or trifluoromethoxy are substituted) substituted phenyl, naphthyl, benzyl, phenylethyl, thienyl, pyrazolyl, pyridinyl or quinolinyl,

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

R ^{1 represents} hydrogen, cyano, fluorine or chlorine, R ^{2 represents} cyano, thiocarbamoyl, fluorine, chlorine, bromine, methyl, difluoromethyl or trifluoromethyl,

R ³ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

R ³ furthermore represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl which is 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, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, methoxycarbonyl,

Ethoxycarbonyl, n- or i-propoxycarbonyl substituted phenyl, naphthyl, benzyl, thienyl, pyrazolyl or pyridinyl,

4. Process for the preparation of aminouracil derivatives of the general

Formula (I)

in which

R, 1 ¹ , t R ^" , τ K3 ^ό , t R> 4 ^μ and R ^{3 have} the meanings given in claim 1,

characterized in that one

Uracil derivatives of the general formula (II)

in which

R, ι, R »2 ~, R τ, 3, r R4 and R have the meanings given above,

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

6. A method for controlling unwanted plants, characterized gekenn¬ characterized in that aminouracil derivatives of the general formula (I) according to claims 1 to 4 are allowed to act on undesirable plants and / or their habitat.

7. Use of aminouracil derivatives 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 aminouracil derivatives of the general formula (I) according to Claims 1 to 4 are mixed with extenders and / or surface-active substances.