DE19709703A1 - Substituted arylalkyl uracils - Google Patents

Abstract

The invention relates to novel substituted arylalkylruracils of general formula (I), wherein A stands for straight-chained or branched alkanediyl with two or more carbon atoms, Ar means in each case optionally substituted phenyl or naphthyl, R<1> is hydrogen, amino or optionally substituted alkyl, R<2> stands for halogen-substituted alkyl, and R<3> means hydrogen, halogen or alkyl. The invention also relates to a method for the production and use thereof as herbicides.

Description

The invention relates to new substituted arylalkyluracils, processes for their manufacture position and their use as herbicides.

A large number of substituted benzyluracils are already from the (patent) Literature known (cf. US 5391541, WO 9504461, WO 9701543). This ver however, bonds have not gained any special significance.

New substituted arylalkyluracils of the general formula (I) have now been found

in which
A represents straight-chain or branched alkanediyl having two or more carbon atoms,
Ar represents in each case optionally substituted phenyl or naphthyl,
R ^{1 represents} hydrogen, amino or optionally substituted alkyl,
R ^{2 represents} halogen substituted alkyl and
R ^{3 represents} hydrogen, halogen or alkyl.

The new substituted arylalkyluracils of the general formula (I) are obtained if

• (a) aminoalkenates of the general formula (II)
  in which
  R ² and R ^{3 have} the meanings given above and
  A ^{1 represents} alkyl, aryl or arylalkyl,
  with arylalkyl urethanes (arylalkyl carbamates) of the general formula (III)
  in which
  A and Ar have the meanings given above and
  A ^{2 represents} alkyl, aryl or arylalkyl,
  if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
  or if you
• (b) substituted arylalkyluracils of the general formula (Ia),
  in which
  A, Ar, R ² and R ^{3 have} the meanings given above,
  with 1-aminooxy-2,4-dinitro-benzene or with alkylating agents of the general formula (IV)
  XA ³ (IV)
  in which
  A ^{3 represents} optionally substituted alkyl and
  X represents halogen or the grouping -O-SO ₂ -OA ³ ,
  if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.

The new substituted arylalkyluracils of the general formula (I) stand out from strong herbicidal activity. They also show good tolerability against important crops, such as. B. corn.

The invention preferably relates to compounds of the formula (I) in which
A represents straight-chain or branched alkanediyl having two to four carbon atoms,
Ar for each optionally by amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, C ₁ -C ₄ alkyl (which is optionally substituted by fluorine and / or chlorine) and / or C ₁ -C ₄ Alkoxy (which is optionally substituted by fluorine and / or chlorine) is substituted phenyl or naphthyl,
R ^{1 represents} hydrogen, amino or alkyl having 1 to 4 carbon atoms which is optionally substituted by cyano, fluorine or chlorine,
R ^{2 represents} fluorine and / or chlorine-substituted alkyl having 1 to 4 carbon atoms and
R ^{3 represents} hydrogen, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms.

The invention relates in particular to compounds of the formula (I) in which
A for ethane-1,1-diyl ("ethylidene"), ethane-1,2-diyl ("dimethylene"), propane-1,1-diyl ("propylidene"), propane-1,2-diyl or propane 1,3-diyl ("trimethylene"),
Ar represents phenyl optionally substituted by amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and / or trifluoromethoxy,
R ^{1 represents} hydrogen, amino, methyl or ethyl,
R ² represents methyl or ethyl substituted by fluorine and / or chlorine and
R ^{3 represents} hydrogen, chlorine, bromine or methyl.

The radicals listed above or listed in preferred areas definitions apply both to the end products of the formula (I) and correspondingly for the starting or intermediate products required for the production. This Residual definitions can be between themselves, that is, between the specified ones areas can be combined as required.

If, for example, 3-amino-2,4,4,4-tetrafluoro-crotonic acid methyl ester and N- [1- (4-chlorophenyl) ethyl] -O-methyl-carbamate are used as starting materials, the course of the reaction can be as follows Process (a) according to the invention are outlined by the following formula:

For example, 1- [2- (2-fluoro-4-trifluoromethyl-phenyl) -ethyl] -5-chloro-4-chlorodifluoromethyl-3,6-dihydro-2,6-dioxo-1 (2H) -pyrimidine and Ethyl bromide as starting materials, the course of the reaction in process (b) according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the aminoalkenic acid esters to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I). In the formula (II), R ² and R ³ preferably or in particular have those meanings which have been given above or in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R ² and R ³ ; A ¹ is preferably C ₁ -C ₄ alkyl, phenyl or benzyl, especially methyl or ethyl.

The starting materials of the general formula (II) are known and / or can be according to known processes can be prepared (cf. J. Heterocycl. Chem. 9 (1972), 513-522).

Formula (III) provides a general definition of the arylalkyl urethanes (arylalkyl carbamates) to be used further as starting materials in process (a) according to the invention. In formula (III), A and Ar preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for A and Ar; A ² preferably represents C ₁ -C ₄ alkyl, phenyl or benzyl, in particular methyl or ethyl.

The starting materials of the general formula (III) are known and / or can be according to known methods can be prepared (cf. J. Org. Chem. 45 (1980), 4519-4522; loc. cit. 48: 2520-2527 (1983); Synthesis 1980, 385-387; Tetrahedron: Asymmetry 1992, 281-286; loc. cit. 1994, 363-370).

The arylalkyl urethanes (arylalkyl carbamates) of the general formula (III) are obtained, for example, if arylalkyl amines of the general formula (V)

H ₂ NA-Ar (V)

in which
A and Ar have the meanings given above,
with chloroformic acid esters of the general formula (VI)

A ² -O-CO-Cl (VI)

in which
A ^{2 has} the meaning given above,
optionally in the presence of an acid acceptor, such as. B. pyridine, and if appropriate in the presence of a diluent, such as. B. methylene chloride, at temperatures between 0 ° C and 100 ° C (see. The manufacturing examples).

Formula (Ia) provides a general definition of the substituted arylalkyluracils to be used as starting materials in process (b) according to the invention for the preparation of compounds of formula (I). In the formula (Ia), A, Ar, R ² and R ³ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention, preferably or as particularly preferred for A, Ar , R ² and R ^{3 were} given.

The starting materials of the general formula (Ia) for process (b) are new substances also the subject of the present application; you can according to the invention according to method (a).

Formula (IV) provides a general definition of the alkylating agents which are further to be used as starting materials in process (b) according to the invention. In the formula (IV), R ¹ and R ² preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R ¹ and R ² were.

Stand in the formula (IV)
A ³ preferably for alkyl with 1 to 4 carbon atoms optionally substituted by cyano, fluorine or chlorine, in particular for methyl or ethyl, and
X preferably for fluorine, chlorine, bromine or iodine, or for the grouping -O-SO ₂ -OA ³ , in particular for chlorine or bromine.

The starting materials of formula (IV) are known organic synthetic chemicals.

The reaction auxiliaries for processes (a) and (b) are generally the usual ones Lichen inorganic or organic bases or acid acceptors into consideration. Here preferably include alkali metal or alkaline earth metal acetates, amides, carbo nates, 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 metha nolate, ethanolate, n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; continue too basic organic nitrogen compounds, such as trimethylamine, tri ethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclo hexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-Di methyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-di methyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-di methylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2,2,2] octane (DABCO), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), or 1,8-diazabicyclo [5,4,0] -undec-7-ene (DBU).

As a diluent for carrying out processes (a) and (b) Inert organic solvents are particularly suitable. This includes in particular aliphatic, alicyclic or aromatic, optionally halogenated Hydrocarbons, such as gasoline, benzene, toluene, xylene, chlorobenzene, Dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, tetra  chlorinated carbon, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or Methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N- Methyl pyrrolidone or hexamethyl phosphoric acid triamide; Esters such as acetic acid methyl ester or ethyl acetate, and sulfoxides or sulfones, such as dimethyl sulfoxide or tetramethylene sulfone ("sulfolane").

The reaction temperatures can be carried out when carrying out the inventive Processes (a) and (b) can be varied over a wide range. In general one works at temperatures between 0 ° C and 200 ° C, preferably between 10 ° C and 150 ° C.

Processes (a) and (b) according to the invention are generally described under Nor painting done. However, it is also possible to use the ver drive under increased 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 carried out in the presence of a reaction auxiliary and the reaction mixture is generally stirred for several hours at the required temperature. The Refurbishment is carried out according to customary methods (see Her position examples).

The active compounds according to the invention can be used as defoliants, desiccants, kraut tabs killers and especially used as a weed killer. Weeds in the broadest sense are understood to mean all plants that are found in places  grow where they are undesirable. Whether the substances according to the invention as total or Selective herbicides act essentially depends on the amount used.

The active compounds according to the invention can, for. B. used in the following plants will:

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, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicot 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, Alopecums, Apera.

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

However, the use of the active compounds according to the invention is by no means limited to these Limited genres, but extends in the same way to others Plants.

Depending on the concentration, the compounds are suitable for the total weed control z. B. on industrial and track systems and on paths and squares  with and without tree cover. Likewise, the connections to weed beds fighting in permanent crops, e.g. B. forest, ornamental wood, fruit, wine, citrus, nut, Banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hops plants, on ornamental and sports turf and pastures and for selective weeds fighting in annual crops.

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

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, sol Liche powder, granules, suspension emulsion concentrates, impregnated with active ingredient Natural and synthetic substances as well as very fine encapsulation in polymeric substances.

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients with extenders, i.e. liquid solvents and / or solid Carriers, if necessary using surface-active agents, that is Emulsifiers and / or dispersants and / or foaming agents.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkylnaph thalines, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. 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.

As solid carriers come into question: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont  morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, come as solid carriers for granules in question: e.g. B. broken and fractionated natural rocks such as calcite, marble, Pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules made of organic material such as sawdust, Coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam Generating funds are possible: z. B. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; as dispersants come into question: z. B. lignin sulfite and Methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho lipids such as cephalins and lecithins and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan and organic dyes such as alizarin, azo and metal phthalocyanine substances 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 Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also used in a mixture with known herbicides for weed control find, where ready formulations or tank mixes are possible.

Known herbicides are suitable for the mixtures, for example  Acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Asulam, Atrazine, Azimsulfuron, Ben azoline, benfuresate, bensulfuron (-methyl), bentazone, benzofenap, benzoylprop (- ethyl), bialaphos, bifenox, bromobutide, bromofenoxim, bromoxynil, butachlor, Butylates, cafenstroles, carbetamides, chloromethoxyfen, chloramben, chloridazon, Chlorimuron (-ethyl), chloronitrofen, chlorosulfuron, chlorotoluron, cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl), Clomazone, Clopyralid, Clo pyrasulfuron, chlorosulam (methyl), cumyluron, cyanazines, cycloates, cyclo sulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedi pham, dialallate, dicamba, diclofop (methyl), difenzoquat, diflufenican, di mefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, di nitramine, diphenamide, diquat, dithiopyr, diuron, dymron, EPTC, Esprocarb, Ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen, etobenzanide, Fenoxaprop (-ethyl), Flamprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (- methyl), flazasulfuron, fluazifop (-butyl), flumetsulam, flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone, Fluoroglyco fen (-ethyl), flupoxam, flupropacil, flurenol, fluridone, fluroxypyr, hallway primidol, flurtamone, fomesafen, glufosinate (-ammonium), glyphosate (-iso propylammonium), halosafen, haloxyfop (-ethoxyethyl), hexazinones, imazametha benz (-methyl), imazamethapyr, imazamox, imazapyr, imazaquin, imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxa pyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Met azachlor, methabenzthiazuron, metobenzuron, metobromuron, metolachlor, meto sulam, metoxuron, metribuzin, metsulfuron (-methyl), molinate, monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon Orbencarb, Oryzalin, Oxadiazon, Oxyfluorfen, Paraquat, Pendimethalin, Phenmedipham, Piperophos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazo sulfuron (-ethyl), pyrazoxyfen, pyributicarb, pyridate, pyrithiobac (-sodium), quin chlorac, quinmerac, quizalofop (-ethyl), quizalofop (-p-tefuryl), rimsulfuron,  Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometu ron (-methyl), sulfosate, tebutam, tebuthiuron, terbuthylazine, terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfurnn (-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenu ron (-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.

Also a mixture with other known active ingredients, such as fungicides secticides, acaricides, nematicides, bird repellants, plant nutrients fabrics and soil structure improvers are possible.

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use Solutions, suspensions, emulsions, powders, pastes and granules are used will. The application is done in the usual way, e.g. B. by pouring, spraying, Spray, sprinkle.

The active compounds according to the invention can be used both before and after emergence of the plants are applied. They can also be planted in the soil before sowing be working.

The amount of active ingredient used can vary over a wide range. she depends essentially 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 area, preferably between 5 g and 5 kg per ha.

The manufacture and use of the active compounds according to the invention are based on following examples.

Manufacturing examples

example 1

(Method (a))

A mixture of 12 g (40 mmol) of 3-amino-4,4,4-crotonic acid ethyl ester, 11 g Potassium carbonate and 100 ml of N-methyl-pyrrolidone is kept at 100 ° C for one hour touched. Then 9.4 g (40 mmol) of N- [2- (4-chlorophenyl) ethyl] -O-ethyl-car bamat added and the reaction mixture is 8 hours at 140 ° C and on finally stirred for a further 18 hours at room temperature (approx. 20 ° C). After stirring with water is shaken with ethyl acetate, the organic phase is separated off and the aqueous phase after acidification with 2N hydrochloric acid again with ethyl acetate ester shaken. The combined organic phases are washed with water, dried with sodium sulfate and filtered. The solvent is removed from the filtrate Water jet vacuum carefully distilled off.

3.0 g (24% of theory) of 1- [2- (4-chlorophenyl) ethyl] -4-trifluoromethyl-3,6-dihydro-2,6-dioxo-1 (2H) pyrimidine are obtained as an amorphous residue.
¹ H NMR (DMSO-D6, δ): 6.23 ppm.

Example 2

(Method (b))

A mixture of 1.0 g (3.1 mmol) of 1- [2- (4-chlorophenyl) ethyl] -4-trifluoromethyl- 3,6-dihydro-2,6-dioxo-1 (2H) pyrimidine, 0.4 g (3.1 mmol) of dimethyl sulfate, 0.8 g Potassium carbonate and 100 ml acetone is refluxed for 7 hours and then stirred for a further 48 hours at room temperature (approx. 20 ° C.). Then in the water jet concentrated in vacuo, the residue is stirred with water and the crystalline product Product isolated by suction.

0.8 g (78% of theory) of 1- [2- (4-chlorophenyl) ethyl] -3-methyl-4-trifluoro are obtained methyl-3,6-dihydro-2,6-dioxo-1 (2H) -pyrimidine, melting point 127 ° C.

Example 3

(Method (b))

A mixture of 1.0 g (3.1 mmol) of 1- [2- (4-chlorophenyl) ethyl] -4-trifluoromethyl- 3,6-dihydro-2,6-dioxo-1 (2H) pyrimidine, 0.27 g sodium hydrogen carbonate and 100 ml N, N-dimethylformamide is stirred for 30 minutes at room temperature (approx. 30 ° C). After adding 0.4 g (3.1 mmol) of 1-aminooxy-2,4-dinitro-benzene, the Re  action mixture for 5 hours and after adding a further 0.4 g of 1-aminooxy-2,4- Dinitro-benzene stirred for a further 48 hours at room temperature. After stirring with Water is shaken with ethyl acetate, the organic phase separated and the aqueous phase after acidification with 2N hydrochloric acid again with ethyl acetate ester shaken. The combined organic phases are washed with water, dried with sodium sulfate and filtered. The filtrate is in a water jet vacuum concentrated, the residue digested with diisopropyl ether and the crystalline Product isolated by suction.

0.75 g (73% of theory) of 3-amino-1- [2- (4-chlorophenyl) ethyl] -4-trifluoro are obtained methyl-3,6-dihydro-2,6-dioxo-1 (2H) -pyrimidine, melting point 146 ° C.

Analog to the preparation examples 1 to 3 and in accordance with the general Be The production processes according to the invention can also be written, for example the compounds of formula (I) listed in Table 1 below be put.  

Examples of the compounds of the formula (I)

Examples of the compounds of the formula (I)

Starting materials of formula (III)

Example (III-1)

A mixture of 7.8 g (50 mmol) of 2- (4-chlorophenyl) ethylamine, 6.0 g (55 mmol) Chloroformic acid ethyl ester, 7.9 g pyridine and 100 ml methylene chloride turns 18 Stirred for hours at room temperature (approx. 20 ° C). Then it is made with 2N hydrochloric acid acidifies, the organic phase separated and the aqueous phase with methylene chloride re-extracted. The combined organic phases are ge with sodium sulfate dries and filtered. The solvent is removed from the filtrate in a water jet vacuum carefully distilled off.

11.0 g (96% of theory) of N- [2- (4-chlorophenyl) ethyl] -O-ethyl-carbamate are obtained as an amorphous residue.

Analogously to Example (III-1), for example, the compounds of the general formula (III) listed in Table 2 below can also be prepared.

Examples of the compounds of the formula (III)

Examples of the compounds of the formula (III)

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 prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours the soil is poured with the active ingredient preparation. You keep the water quantity per unit area expediently constant. The drug concentration in the preparation does not matter, only the application rate of the Active ingredient 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 annihilation.

In this test, for example, the compound according to Production Example 12 shows an application rate of 1000 g / ha is well tolerated by culture plants, such as B. maize and strong action against weeds such as Setaria (100%), Amaranthus (100%) and Xanthium (90%).  

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, mix 1 Part by weight of active ingredient with the specified amount of solvent, specifies the added amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

With the active ingredient preparation, test plants are sprayed, which have a height of 5-15 cm have so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 1000 l water / ha the desired amounts of active ingredient are applied.

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 Example 3 show 12 and 13 with a rate of application of 1000 g / ha a good tolerance against about crops, such as. B. corn and strong action against weeds such as Setaria (80%), Abutilon (100%), Amaranthus (100%) and Galium (100%).

Claims (9)

1. Substituted arylalkyl uracils of the general formula (I)
in which
A represents straight-chain or branched alkanediyl having two or more carbon atoms,
Ar represents in each case optionally substituted phenyl or naphthyl,
R ^{1 represents} hydrogen, amino or optionally substituted alkyl,
R ^{2 represents} halogen substituted alkyl and
R ^{3 represents} hydrogen, halogen or alkyl. 2. Substituted arylalkyluracils of general formula (I) according to claim 1, characterized in that
A represents straight-chain or branched alkanediyl having two to four carbon atoms,
Ar for in each case optionally by amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, C ₁ -C ₄ -alkyl (which is optionally substituted by fluorine and / or chlorine) and / or C ₁ - C ₄ alkoxy (which is optionally substituted by fluorine and / or chlorine) is substituted phenyl or naphthyl,
R ^{1 represents} hydrogen, amino or alkyl having 1 to 4 carbon atoms which is optionally substituted by cyano, fluorine or chlorine,
R ^{2 represents} fluorine and / or chlorine-substituted alkyl having 1 to 4 carbon atoms and
R ^{3 represents} hydrogen, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms. 3. Substituted arylalkyluracils of the general formula (I) according to claim 1, characterized in that
A for ethane-1,1-diyl ("ethylidene"), ethane-1,2-diyl ("dimethylene"), propane-1,1-diyl ("propylidene"), propane-1,2-diyl or propane 1,3-diyl ("trimethylene"),
Ar represents phenyl optionally substituted by amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and / or trifluoromethoxy,
R ^{1 represents} hydrogen, amino, methyl or ethyl,
R ² represents methyl or ethyl substituted by fluorine and / or chlorine and
R ^{3 represents} hydrogen, chlorine, bromine or methyl. 4. Process for the preparation of the substituted arylalkyluracils of the general formula (I),
in which
A represents straight-chain or branched alkanediyl having two or more carbon atoms,
Ar represents in each case optionally substituted phenyl or naphthyl,
R ^{1 represents} hydrogen, amino or optionally substituted alkyl,
R ^{2 represents} halogen substituted alkyl and
R ^{3 represents} hydrogen, halogen or alkyl,
characterized in that one

• (a) aminoalkenates of the general formula (II)
  in which
  R ² and R ^{3 have} the meanings given above and
  A ^{1 represents} alkyl, aryl or arylalkyl,
  with arylalkyl urethanes (arylalkyl carbamates) of the general formula (III)
  in which
  A and Ar have the meanings given above and
  A ^{2 represents} alkyl, aryl or arylalkyl,
  or that one
• (b) substituted arylalkyluracils of the general formula (Ia),
  in which
  A, Ar, R ² and R ^{3 have} the meanings given above,
  with 1-aminooxy-2,4-dinitro-benzene or with alkylating agents of the general formula (IV)
  XA ³ (IV)
  in which
  A ^{3 represents} optionally substituted alkyl and
  X represents halogen or the grouping -O-SO ₂ -OA ³ .

5. Herbicidal agents, characterized by a content of at least one substituted arylalkyluracil of formula (I) according to claim 1. 6. Process for combating undesirable plants, thereby characterized in that substituted arylalkyluracils of the formula (I) according to claim 1 to undesirable plants and / or their habitat can act. 7. Use of substituted arylalkyluracils of the formula (I) according to the Claim 1, for controlling unwanted plants. 8. A process for the preparation of herbicidal compositions, characterized in that that substituted arylalkyl uracils of the formula (I) according to Claim 1 mixed with extenders and / or surface-active substances. 9. Substituted arylalkyluracils of the general formula (Ia),
in which
A represents straight-chain or branched alkanediyl having two or more carbon atoms,
Ar represents in each case optionally substituted phenyl or naphthyl,
R ^{2 represents} halogen substituted alkyl and
R ^{3 represents} hydrogen, halogen or alkyl.