WO1999048886A1

WO1999048886A1 - Substituted aminooxyalkanecarboxamides

Info

Publication number: WO1999048886A1
Application number: PCT/EP1999/001688
Authority: WO
Inventors: Roland Andree; Markus Dollinger; Mark Wilhelm Drewes; Ingo Wetcholowsky; Randy Allen Myers
Original assignee: Bayer Aktiengesellschaft
Priority date: 1998-03-25
Filing date: 1999-03-15
Publication date: 1999-09-30
Also published as: AU2836899A; DE19813047A1

Abstract

The invention relates to novel substituted aminooxyalkanecarboxamides of general formula (I), wherein A represents an optionally substituted alkanediyl, R1 represents hydrogen or optionally substituted alkyl, R2 represents hydrogen or optionally substituted alkyl, R3 represents hydrogen, hydroxy, amino or optionally substituted alkyl, alkoxy, alkylamino, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl and R4 represents hydrogen or optionally substituted alkyl, alkoxy, alkylamino, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl or together with R3, alkanediyl which can be optionally substituted and/or optionally interrupted by a heteroatom from the series O (oxygen), S (sulphur), N (nitrogen) at the beginning or end of or inside the carbon chain. The invention also relates to a method for producing the inventive substituted aminooxyalkanecarboxamides and to their use as herbicides.

Description

- 1 -

Substituted aminooxyalkane carboxamides

The invention relates to new substituted aminooxyalkane carboxamides, a process for their preparation and their use as herbicides.

It is known that certain substituted aminooxyalkane carboxamides have herbicidal properties (cf. EP-A-427 445, US-A-5 002 605, US-A-5 314 865). However, these previously known compounds have no particular significance.

The new substituted aminooxyalkane carboxamides of the general formula (I) have now been found

Ν R ^

O

/ r R, 3rd

A

-Ν (I)

O in what

A represents optionally substituted alkanediyl,

Rl represents hydrogen or optionally substituted alkyl,

R.2 represents hydrogen or optionally substituted alkyl,

R.3 represents hydrogen, hydroxy, amino, or optionally substituted alkyl, alkoxy, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, and - 2 -

R ^ for hydrogen or for optionally substituted alkyl, alkoxy, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or together with R ^ for optionally substituted and / or optionally by a heteroatom from the O series (Oxygen), S (sulfur), N (nitrogen) at the beginning - or end - or interrupted alkanediyl in the carbon chain.

The compounds of the general formula (I) according to the invention optionally contain asymmetrically substituted carbon atoms and can then be present in various enantiomeric (R- and S-configured forms) or diastereomeric forms. The invention relates both to the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) and to the mixtures of these stereoisomeric compounds.

The general formula (I) summarizes the two general formulas (IA) and (IB)

(IA) dB)

In the definitions, the hydrocarbon chains, such as alkyl - also in connection with heteroatoms, such as in alkoxy - are each straight-chain or branched.

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

A represents alkanediyl with 1 to 4 carbon atoms optionally substituted by halogen, - 3 -

R 1 represents hydrogen or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C1-C4-alkoxy,

R2 represents hydrogen or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C1-C4alkoxy,

R ^ for hydrogen, hydroxy, amino, for each optionally substituted by hydroxy, cyano, halogen or C] -C4-alkoxy alkyl, alkoxy or alkylamino each having 1 to 6 carbon atoms, for each optionally substituted by cyano or halogen with alkenyl or alkynyl each having 2 to 6 carbon atoms, each for cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or C1-C4alkyl

3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to

4 carbon atoms in the alkyl part, each optionally with nitro, cyano, formyl, carbamoyl, thiocarbamoyl, 1J-dioxolan-2-yl, halogen, C

C4-Alkyl, Cι-C4-haloalkyl, C1-C4-alkoxy, Cι-C4-haloalkoxy, C \ - C4-alkylcarbonyl or Cι-C4-alkoxy-carbonyl substituted aryl or arylalkyl with 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by cyano, carbamoyl, thiocarbamoyl, halogen, C 1 -C 4 -alkyl, C 1 -

C4-haloalkyl, C | -C4-alkoxy or -CC-C4-haloalkoxy substituted heterocyclyl or heterocyclylalkyl from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidylmethylmylylyl, furyl , Pyrazolylmethyl, imidazolylmethyl, oxazolylmethyl, thiazolylmethyl, oxadiazolylmethyl, thiadiazolylmethyl, pyridinylmethyl, pyrimidinylmethyl, and

R4 for hydrogen, each for alkyl, alkoxy or alkylamino optionally substituted by hydroxy, cyano, halogen 'or C 1 -C 4 -alkoxy, each with

1 to 6 carbon atoms, for each optionally by cyano or Ha- logen-substituted alkenyl or alkynyl, each having 2 to 6 carbon atoms, for cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or C1-C4-alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by nitro, cyano, formyl,

Carbamoyl, thiocarbamoyl, halogen, 1,3-dioxolan-2-yl, C1-C4-alkyl, C \ - C4-haloalkyl, Cj-C4-alkoxy, Cj-C4-haloalkoxy, C _] -C4-alkylcarbonyl or -C4-Alkoxy-carbonyl-substituted aryl or arylalkyl having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by cyano, carbamoyl, thiocarbamoyl, halogen, C1 -C4 alkyl, Cι-C4 -Halogen- a kyl, -CC-C4-alkoxy or -CC-C4-haloalkoxy substituted heterocyclyl or heterocyclylalkyl from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridylmethylmethyl, pyriminyl, pyriminyl Thienylmethyl, pyrrolylmethyl,

Pyrazolylmethyl, imidazolylmethyl, oxazolylmethyl, thiazolylmethyl, oxadiazolylmethyl, thiadiazolylmethyl, pyridinylmethyl, pyrimidinylmethyl, or together with R ^ for optionally substituted by halogen and / or optionally by a heteroatom from the series O (oxygen), S (sulfur), N (sulfur Nitrogen) at the beginning - or end - or within the

Carbon chain interrupted alkanediyl having 2 to 6 carbon atoms.

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

A represents methylene (-CH ₂ -) or dimethylene (-CH ₂ CH ₂ -) optionally substituted by fluorine and / or chlorine,

R 1 represents hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, - 5 -

R ^ represents hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

R ^ for hydrogen, hydroxy, amino, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, which are each optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy or ethoxy , Ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, for each optionally propenyl, butenyl, propynyl or butynyl substituted by cyano, fluorine, chlorine or bromine, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylniethyl each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl , for each optionally by nitro, cyano, carbamoyl, thiocarbamoyl, formyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy , n- or i-propoxy, difluoromethoxy,

Trifluoromethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl-substituted phenyl or benzyl, or for each optionally substituted by cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl , n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted heterocyclyl or heterocyclylalkyl from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl , Thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, furylmethyl, thienylmethyl, pyrrolylmethyl, pyrazolylmethyl, imidazolylmethyl, oxazolylmethyl, thiazolylmethyl, oxadiazolylmethyl, thiadiazolylmethyl, pyrimidinylmethyl

R4 for hydrogen, for methyl, ethyl, n- or i-propyl, "n-, i-, s- or t-butyl, methoxy, ethoxy, n, each optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy or ethoxy - or i-propoxy, n-, i-, s- or t-

Butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t- - 6 -

Butylamino, for propenyl, butenyl, propynyl or butynyl, each optionally substituted by cyano, fluorine, chlorine or bromine, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclo- butylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally with nitro, cyano, carbamoyl, formyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted phenyl or benzyl, or for each optionally substituted by cyano, carbamoyl, thiocarbamoyl, Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted heterocyclyl or heterocyclylalk yl from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, oxadiazolyl,

Thiadiazolyl, pyridinyl, pyrimidinyl, morpholinyl, furylmethyl, thienylmethyl, pyrrolylmethyl, pyrazolylmethyl, imidazolylmethyl, oxazolylmethyl, thiazolylmethyl, oxadiazolylmethyl, thiadiazolylmethyl, pyridinylmethyl, propanidylmethyl (di or methylimyl), tri or methylimyl, CH ₂ CH ₂ CH ₂ -), butane-1,4-diyl (tetramethylene,

-CH ₂ CH ₂ CH ₂ CH ₂ -), pentane-1,5-diyl (pentamethylene,

-CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ -), hexane-1,6-diyl (hexamethylene,

-CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ -), 1-oxa-butane-1,4-diyl (-OCH ₂ CH ₂ CH ₂ -) l-oxapentane-l, 5-diyl (- OCH ₂ CH ₂ CH ₂ CH ₂ -), or 3-oxapentane-1,5-diyl (-CH ₂ CH ₂ OCH ₂ CH ₂ -).

A very particularly preferred group are the compounds of formula (I) in which

A for methylene (-CH ₂ -), difluoromethylene (-CF ₂ -), dimethylene (-CH ₂ CH ₂ -),

Trifluorodimethylene (-CF ₂ CHF-) or tetrafluorodimethylene (-CF CF ₂ -), - 7 -

Rl stands for hydrogen,

R ^ represents methyl, ethyl, n- or i-propyl,

R ^ stands for hydrogen, and

R4 represents phenyl or benzyl optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or morpholinyl.

The general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products 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.

The new substituted aminooxyalkane carboxamides of the general formula (I) are notable for strong and selective herbicidal activity.

To a certain extent, the compounds of formula (I) also show insecticidal activity.

The new substituted aminooxyalkane carboxamides of the general formula (I) are obtained if carbonyl compounds of the general formula (II)

(H)

in which A and Rl have the meaning given above,

with aminooxyalkane carboxamides of the general formula (III)

H "NR ² \

R ^J

(III)

-N

O R "in which

R2, R- ³ and R4 have the meaning given above,

if appropriate in the presence of a diluent.

If, for example, 1,4-benzodioxane-6-aldehyde and 1,4-aminooxy-propionic acid anilide are used as starting materials, the course of the reaction in the process according to the invention can be outlined using the following formula:

H

H ₂ NL N

O

The process according to the invention for the preparation of compounds of

Formula (I) carbonyl compounds to be used as starting materials are generally defined by formula (II). In formula (II), A and R preferably have ¹ or in particular those meanings which have already been given 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 R ¹ .

The starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. J. Org. Chem. 37 (1972), 673).

The aminooxyalkane carboxamides to be used further as starting materials in the process according to the invention are generally defined by the formula (III). In formula (III), R ² , R ³ and R ⁴ preferably or in particular have those

Meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R ² , R ³ and R ⁴ .

The starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf. J. Org. Chem. 32 (1967), 2417-2425; loc. Cit. 33 (1968), 2963- 2966; DE-A-3615473; EP-A-427445; EP-A-427549; US-A-5002605; US-A-5314865; manufacturing examples).

The process according to the invention for the preparation of the compounds of the formula (1) is preferably carried out using a diluent. Inert organic solvents are particularly suitable as diluents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; 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-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides, - 10 -

such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol 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 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 be used, for example, in the following plants: - 11 -

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Sonuum, Carduus , Rorippa, 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, Brasica, Lactuca, Cucumis, Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Iochasumirumum, Scalumumum, Scalumumum , 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 are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, for example forest, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants. genes, on ornamental and sports turf and pastures and for selective weed control in annual crops. - 12 -

The compounds of 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 can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie 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: for example 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, as solid carriers for granules come into question: eg broken and fractionated natural rocks such as calcite, marble, - 13 -

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 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 hydrolysates; 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, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0J 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 are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin,

Azimsulfuron, benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazone, - 14 -

Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramethoxyfen Chloridazon, Chlor imuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlorotoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl),

Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (- methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2, 4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufen- zopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid,

Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxy sulfuron, Etobenzanid, Fenoxaprop (-P-ethyl), Flamp isopropyl), flamprop (-isopropyl-L), flamprop (-methyl), flazasulfuron, fluazifop (-P-butyl), flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumet-sulam, fluometuron, fluorochloridone, fluoroglycofenofen (-ethyl), Flupoxam, Flu-propacil, Flurpyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fome- safen, glufosinate (-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop (-ethoxy ethyl), haloxyfop (-P-methyl), hexazinone, imazamethabenz (- methyl), imazamethapyr, imazamox, imazapyr, imazaquin, imazethapyr - Sulfuron, Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxaflutole, Isoxa- pyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenac et, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolechlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Norfluron, Nicosulfur Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, Pelargonic acid, Pendimethalin, Pentoxazone, Phenmedipham, Piperophos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propa-chloro, Propa-chloro, Propa-chloro, Propa-chloro Propyzamide, prosulfocarb, prosulfuron, pyra- - 15 -

flufen (-ethyl), pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop (-P-ethyl), quizalof -P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (- methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Terbuthylazine, Ter-butryn, Thenylchlor, Thiafluamide, Thiazonyryridium, Thiazonyryridone - methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.

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 compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. 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 emergence of the plants. 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. - 16 -

Manufacturing examples;

example 1

A mixture of 1.0 g (4.5 mmol) of N- (2,4-dimethyl-phenyl) -2-aminooxy-butyramide (racemic), 0.84 g (4.5 mmol) of 2J-difluoromethylene dioxy- Benzaldehyde and 100 ml of ethanol are heated under reflux for two hours and then concentrated in a water jet vacuum. The residue is shaken with a mixture of about 100 ml of ethyl acetate and about 100 ml of 1N hydrochloric acid, the organic phase is separated off, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.

1.6 g (91% of theory) of N- (2,4-dimethyl-phenyl) -2- (2J-difluoromethyl-phenylmethylene-aminooxy) -butyramide (racemate) are obtained as a crystalline residue with a melting point of 100 ° C. .

Analogously to Preparation Example 1 and in accordance with the general description of the preparation process according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) - or of the formulas (IA) or (IB) listed in Table 1 below. 17

:NO'

OA

(IA)

18th

Table 1: Examples of the compounds of the formulas (IA) and (IB)

E.g. no. general physical. Formula A Rl R ² R ³ R ⁴ data and stereochem.

Information

2 (IB) -CF ₂ CF ₂ - HC ₂ H ₅ H - CH, m.p .: 62 ° C

Ό (racemate)

(IA) -CF ₂ - HCH ₅ H mp: 86 ° C

AJ (Racemat)

4 (IA) -CF ₂ CF ₂ - HC ₂ H ₅ H (amorphous)

-CF ₂ - HC ₂ H ₅ H Jo (Racemate)

5 (IA) "0 m.p .: 1 ₂ 9 ° C (racemate)

6 (IA) -CF ₂ - HC ₂ H ₅ H CH ₃ Mp .: 1 14 ° C

J ^ό (racemate)

7 (IA) -CF ₂ - HC ₂ H ₅ H mp: 100 ° C

A? (Racemate)

CH ₃

8 (IA) -CF ₂ - HC ₂ H ₅ H (amorphous), (racemate)

9 (IB) -CF ₂ - HCH ₅ H Mp .: 90 ° C

O L, (racemate)

10 (IA) -CH ₂ - HCH ₅ H mp: 108 ° C

J (racemate)

1 1 (IB) -CH ₂ - HC ₂ H ₅ H y (amorphous) (racemate)

19

E.g. no. general physical. Formula R ¹ R ² R ³ R «data and stereochem.

Information

12 (IA) -CF ₂ - HC ₂ H ₅ H Mp .: 90 ° C (racemate)

13 (IA) -CF ₂ CF ₂ - HC ₂ H ₅ H (amo h) (racemate)

14 (IA) -CH ₂ - HC ₂ H ₅ H mp: 94 ° C (racemate)

15 (IB) -CF ₂ - HC ₂ H ₅ H (amorphous) (racemate)

16 (IA) -CF ₂ CF ₂ - HCH ₅ H Mp .: 98 ° C (racemate)

17 (IA) -CH ₂ - HCH ₅ H (racemate) m.p .: 89 ° C

18 (IB) -CF ₂ - HC ₂ H ₅ H (racemate)

// (amoφh)

19 (IB) -CH ₂ - HC ₂ H ₅ H (racemate)

// mp: 93 ° C

₂ 0 (IB) -CH ₂ - HC ₂ H ₅ H (racemate)

// Mp .: 77 ° C

Cl '

21 (IA) -CF ₂ - HCH ₅ H mp: 108 ° C

-Q (racemate)

Cl 20th

E.g. no. general physical.

Formula A Rl R ² R ³ R ⁴ data and stereochem.

Information

2 ₂ (IA) -CF ₂ CF ₂ - HC ₂ H ₅ H -o mp: 1 13 ° C

(Racemate)

\

Cl

23 (IA) -CH ₂ - HC ₂ H ₅ H -o mp: 96 ° C

(Racemate)

\

Cl

24 (IB) -CF ₂ - HC ₂ H ₅ H -o (racemate)

(amorphous)

\

Cl

25 (IB) -CH ₂ - HC ₂ H ₅ H -o mp: 81 ° C

(Racemate)

\

Cl

26 (IA) -CF ₂ - HC ₂ H ₅ H (racemate)

_ ^ - c. (amorphous)

27 (IA) -CF ₂ CF ₂ - HC ₂ H ₅ H

^~ ^ ^a mp: 9 ₂ ° C (racemate)

28 (IA) -CH ₂ - HC ₂ H ₅ H -o- m.p .: 1 18 ° C (racemate)

29 (IB) -CF ₂ - HC ₂ H ₅ H -Q (racemate) (amoφh)

30 (IB) -CH ₂ - HC ₂ H ₅ H Mp .: 105 ° C

_ ^ _ α (racemate)

31 (IA) -CF ₂ - HCH ₅ H (racemate)

32 (IA) -CF ₂ CF ₂ - HC ₂ H ₅ H ^y F

(Racemate)

F

- 21

E.g. no. general physical. Formula A Rl R ² R ³ R ⁴ data and stereochem.

Information

33 (IA) -CH ₂ - HC ₂ H ₅ H (racemate)

34 (IB) -CF ₂ - H ^y F

C ₂ H ₅ H (racemate)

35 (IB) -CH ₂ - H ^y F

CH ₅ H (racemate) ^y F

36 (IA) -CF ₂ - HC ₂ H ₅ H -o (racemate)

37 (IA) -CF ₂ CF ₂ - H CH ₃ H -o (racemate)

38 (IA) -CH ₂ - H CH ₃ H -o * (racemate)

39 (IB) -CF ₂ - H CH ₃ H

- ^ (racemate)

40 (IB) -CH ₂ - HC ₂ H ₅ H (racemate)

-O '

41 (IA) -CF ₂ - HC ₂ H ₅ H (racemate)

- <Fp.:95°C

F ^/

42 (IA) -CF ₂ CF ₂ - HC ₂ H ₅ H (racemate) (amoφh) r

43 (IA) -CH ₂ - HCH ₅ H (racemate) mp: 1 1 1 ° C

44 (IB) -CF ₂ - HC ₂ H ₅ H (racemate) - mp: 71 ° C

A

22

E.g. no. general physical. Formula A Rl R ² R ³ R ⁴ data and stereochem.

Information

45 (IB) -CH ₂ - HC ₂ H ₅ H (racemate)

-o ^→ mp: 84 ° C

46 (IA) -CF ₂ - HC ₂ H ₅ H mp: 85 ° C

-Q (racemate)

CF ₃

47 (IA) -CF ₂ CF ₂ - HCH ₅ H (racemate)

-Q mp: 10 ₂ ° C

CF ₃

48 (IA) -CH ₂ - HC ₂ H ₅ H (racemate)

A mp: 9 ₂ ° C

C ₃

49 (IB) -CF ₂ - HC ₂ H ₅ H (racemate)

-Q mp: 97 ° C

CF ₃

50 (IB) -CH ₂ - HC ₂ H ₅ H (racemate)

- ^Q (amoφh)

CF ₃

51 (IA) -CF ₂ - HC ₂ H ₅ H -.: 54 ° C (racemate) erp mp

ci

52 (IA) -CF ₂ CF ₂ - HC ₂ H ₅ H 01 (racemate) he ci

53 (IA) -CH ₂ - HCH ₅ H - acemat) (amoφh) erp (R

ci

- 23

E.g. no. general physical. Formula A Rl R ² R ³ R ⁴ data and stereochem.

Information

54 (IB) -CF ₂ - HC ₂ H ₅ H - (racemate) (amoφh) er ci

55 (IB) -CH ₂ - HC ₂ H ₅ H (racemate) m.p .: 78 ° C er ci

56 (IA) -CF ₂ - HC ₂ H ₅ H 01

(Racemat) he

57 (IA) -CF ₂ CF ₂ - HC ₂ H ₅ H (racemate)

he

58 (IA) -CH ₂ - HCH ₅ H (racemate) mp: 7 ₂ ° C c

59 (IB) -CF ₂ - HCH ₅ H - -c, (racemate) (amoφh) er

60 (IB) -CH ₂ - HCH ₅ H (racemate) m.p .: 119 ° C er

61 (IA) -CF ₂ - HC ₂ H ₅ H CL (racemate)

- e ^b r

62 (IA) -CF ₂ CF ₂ - HC ₂ H ₅ H (racemate)

he

- 24 -

E.g. no. general physical. Formula R ¹ R ² R ³ R ⁴ data and stereochem.

Information

63 (IA) -CH ₂ - HC ₂ H ₅ H CL (racemate)

//

Cl '

64 (IB) -CF ₂ - HC ₂ H ₅ H CL (racemate)

//

Cl '

65 (IB) -CH ₂ - HC ₂ H ₅ CL (racemate)

//

he

66 (IA) -CF, HCH ₅ H (amoφh)

(Racemate)

67 (IA) -CF ₂ CF ₂ - HC ₂ H ₅ H (amoφh)

(Racemate)

68 (IA) -CF, H CH, H mp: 134 ° C

CH. (Racemate)

69 (IA) -CF, CF, HC ₂ H ₅ H mp: 69 ° C

(Racemate)

70 (IA) -CF-CF, - HC ₂ Hi H Mp .: 74 ° C

(Racemate)

CH,

(IA) -CH, - C ₂ H _S H mp: 1 ₂ 5 ° C

(Racemate)

CH, - 25th

E.g. no. general physical.

Formula A Rl R ² R ³ R ⁴ data and stereochem.

Information

72 (IB) -CF ₂ - HC ₂ H ₅ H mp: 94 ° C

H ₃ C ^ 9 (racemate)

CH ₃

73 (IA) -CH ₂ - HC ₂ H ₅ H

H ₃ C ^ ^y Mp .: 108 ° C (racemate)

74 (IB) -CF ₂ - HC, H ₅ H

HsC ^ y Mp .: 97 ° C (racemate)

75 (IB) -CH ₂ - HC ₂ H ₅ H mp: 118 ° C

H ₃ C (racemate)

CH ₃

76 (IB) -CH ₂ - HC ₂ H ₅ H

H ₃ C "y Mp .: 144 ° C (racemate)

CH ₃

77 (IA) -CF ₂ CF ₂ - HC ₂ H ₅ H Mp .: 97 ° C (racemate)

H ₃ C

ό

26

Starting materials of formula (III):

Example (III-l)

step 1

A solution of 13.8 g (60 mmol) of 2-bromo-butyric acid bromide (racemic, 90%) in 50 ml of methylene chloride is stirred at 20 ° C. to 30 ° C. to a mixture of 6J g (60 mmol) 2, 4-Dimethyl-aniline, 6.0 g (60 mmol) of triethylamine and 100 ml of methylene chloride added dropwise. The reaction mixture is two more

Stirred at 20 ° C to 25 ° C for hours and then mixed with 100 ml of water. The organic phase is separated off and the aqueous phase is extracted twice with 50 ml of methylene chloride. The combined organic phases are dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with hexane and the crystalline product is isolated by suction.

12.6 g (93% of theory) of N- (2,4-dimethyl-phenyl) -2-bromobutyric acid amide (racemate) of melting point 133 ° C. are obtained. 27

Level 2

A mixture of 11.2 g (40 mmol) of N- (2,4-dimethyl-phenyl) -2-bromobutyric acid amide (racemic), 6.8 g (40 mmol) of N-hydroxy-phthalimide, 9 ml Triethylamine and 100 ml of N, N-dimethylformamide are stirred at room temperature (approx. 20 ° C.) for 18 hours and then concentrated under reduced pressure. The residue is shaken with a mixture of ethyl acetate and water, the organic phase is separated off, the aqueous phase is extracted three times with ethyl acetate, the combined organic phases are washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with diethyl ether and the crystalline product is isolated by suction.

8.9 g (63% of theory) of N- (2,4-dimethylphenyl) -2- (phthalimidooxy) butyric acid amide (racemate) of melting point 123 ° C. are obtained.

level 3

A mixture of 8.0 g (23 mmol) of N- (2,4-dimethyl-phenyl) -2- (phthalimidooxy) butyric acid amide (racemic), 2.3 g of hydrazine hydrate and 200 ml of ethanol becomes two 28 -

Stirred at 40 ° C for hours. After cooling with ice, the precipitated phthalohydrazide is then separated off by filtration and the solvent is carefully distilled off from the filtrate in a water jet vacuum.

4.5 g (88% of theory) of N- (2,4-dimethyl-phenyl) -2-aminooxy-butyramide (racemate) of melting point 108 ° C. are obtained.

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

H, N FT

² \

O- R ^J

R Table 2: Examples of the compounds of the formula (III)

Ex. Physical. Data and stereo¬

No.R2 R3 R4 chem. Information ιπ-2 C ₂ H ₅ H CH ₃ (amorphous)

J ^ό (racemate)

πι-3 C ₂ H ₅ H Jx Mp .: 80 ° C (racemate) ιπ-4 C ₂ H ₅ H _γ . (amorphous) (racemate) ιπ-5 C ₂ H ₅ H ^y (amorphous) (racemate) ιπ-6 C ₂ H ₅ H r C. Cr

AS 29

Ex. Physical. Data and stereo

No.R2 R3 R4 chem. Details ιπ-7 C ₂ H ₅ H

π-8 C ₂ H ₅ H - er ι ^P

-A Cl ιπ-9 C ₂ H ₅ H

J> °

III- 10 C ₂ H ₅ H

III-11 C ₂ H ₅ H 7

F

III-12 C ₂ H ₅ H

J,

III- 13 C ₂ H ₅ H

he

III- 14 C ₂ H ₅ H

III- 15 C ₂ H ₅ H - er

N 0

- 30 -

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 specified amount is given

Amount of emulsifier and dilute the concentrate with water to the desired concentration.

Seeds of the test plants are sown in normal soil, after about 24 hours the soil is sprayed with the active compound preparation in such a way that the desired amounts of active compound 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 compounds according to Preparation Examples 1, 3 and 7, with good tolerance to crop plants, such as, for example, maize, barley, cotton and soya, show a strong action against weeds. - 31 -

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 to 15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound 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.

It means:

0% - no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds according to Preparation Examples 1, 3 and 7 show with good tolerance to crop plants, such as e.g.

Corn and wheat, strong weed control.

Claims

- 32 patent claims

1. Substituted aminooxyalkane carboxamides of the general formula (I),

(i) σ in which

A represents optionally substituted alkanediyl,

Rl represents hydrogen or optionally substituted alkyl,

R ^ represents hydrogen or optionally substituted alkyl,

R ^{J stands} for hydrogen, hydroxyl, amino, or for optionally substituted alkyl, alkoxy, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, and

R4 represents hydrogen or alkyl which is optionally substituted,

Alkoxy, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or together with R ^ for optionally substituted and / or optionally by a heteroatom from the series O (oxygen), S (sulfur), N ( Nitrogen) at the beginning - or end - or interrupted alkanediyl within the carbon chain.

2. Substituted aminooxyalkane carboxamides according to claim 1, characterized in that - 33 -

A represents alkanediyl with 1 to 4 carbon atoms optionally substituted by halogen,

Rl for hydrogen or for optionally by cyano, halogen or

C1 -C4 alkoxy substituted alkyl having 1 to 6 carbon atoms,

R3 for hydrogen, hydroxy, amino, for alkyl, alkoxy or alkylamino, each of which is optionally substituted by hydroxy, cyano, halogen or C 1 -C 4 -alkoxy, each having 1 to 6 carbon atoms, for alkenyl or alkynyl, each optionally substituted by cyano or halogen, each having 2 up to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or C1-C4-alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by nitro, cyano, formyl , Carbamoyl, thiocarbamoyl, l, 3-dioxolan-2-yl, halogen, C1 - C4-alkyl, Cι-C4-haloalkyl, Cτ -C4-alkoxy y, Cι-C4-haloalkoxy, Cι-C4-alkyl- carbonyl or Cj-C4-alkoxy-carbonyl-substituted aryl or arylalkyl with 6 or 10 carbon atoms in the

Aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for heterocyclyl which is optionally substituted by cyano, carbamoyl, thiocarbamoyl, halogen, C1-C4-alkyl, Cj-C4-haloalkyl, C1-C4-alkoxy or C1-C4-halooxy Heterocyclylalkyl from the series furyl, thienyl, pyrrolyl, pyrazolyl,

Imidazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, - 34 -

Pyrimidinyl, furylmethyl, thienylmethyl, pyrrolylmethyl, pyrazolylmethyl, imidazolylmethyl, oxazolylmethyl, thiazolylmethyl, oxadiazolylmethyl, thiadiazolylmethyl, pyridinylmethyl, pyrimidinylmethyl, and

for hydrogen, for in each case optionally substituted by hydroxy, cyano, halogen or C 1 -C 4 -alkoxy alkyl, alkoxy or alkylamino each having 1 to 6 carbon atoms, for in each case optionally substituted by cyano or halogen alkenyl or alkynyl each having 2 to 6 carbon atoms, for in each case optionally substituted by cyano, halogen or C 1 -C 4 -alkyl cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by nitro, cyano, formyl, carbamoyl, thiocarbamoyl, halogen, lJ-dioxolan-2-yl, C1-C4-

Alkyl, Cj-C4Halogenalkyl, C1-C4-alkoxy, Cι-C4-haloalkoxy, Cι-C4-alkylcarbonyl or C] -C4-alkoxy-carbonyl substituted aryl or arylalkyl with 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each heterocyclyl or heterocyclylalkyl from the which is optionally substituted by cyano, carbamoyl, thiocarbamoyl, halogen, Cj-G ^ -alkyl, C 1 -C 4 -haloalkyl, C1-C4-alkoxy or C 1 -C 4 -alkalkoxy Range furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, morpholinyl, furylmethyl, thienylmethyl, pyrrolylmethyl, pyrazolylmethyl, thidylolylmethyl, oxazolylmethylmethyl, oxazolylmethylmethyl, oxazolylmethylmethyl, oxazolylmethylmethyl, oxazolylmethylmethyl, oxazolylmethylmethyl, oxazolylmethylmethyl, oxazolylmethylmethyl, oxazolethylmethyl together with R ^J for optionally substituted by halogen and / or optionally by a hetero atom from the series O (oxygen), S (sulfur), N (nitrogen) - 35 -

at the beginning - or end - or interrupted alkanediyl having 2 to 6 carbon atoms in the carbon chain.

3. Substituted aminooxyalkane carboxamides according to claim 1, characterized in that

A for each optionally substituted by fluorine and / or chlorine

Methylene (-CH ₂ -) or dimethylene (-CH ₂ CH ₂ -),

Rl for hydrogen or for each optionally by cyano, fluorine,

Chlorine, methoxy or ethoxy is substituted methyl, ethyl, n- or i-propyl,

R2 for hydrogen or for methyl, ethyl, n- or i- which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy

Propyl stands,

R ^ for hydrogen, hydroxy, amino, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, each optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy or ethoxy ,

Ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, each for optionally by Cyano, fluorine, chlorine or bromine-substituted propenyl, butenyl, propynyl or butynyl, each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl

Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylniethyl, each optionally with nitro, cyano, carbamoyl, thiocarbamoyl, formyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i- propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, acetyl, propionyl, - 36 -

Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl-substituted phenyl or benzyl, or for each optionally substituted by cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted heterocyclyl or heterocyclylalkyl from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, oxadiazolyl, oxadiazolyl, oxadiazolyl, oxadiazolyl, , Pyridinyl, pyrimidinyl, furylmethyl, thienylmethyl, pyrrolylmethyl, pyrazolylmethyl, imidazolylmethyl, oxazolylmethyl, thiazolylmethyl, oxadiazolylmethyl, thiadiazolylmethyl, pyridinylmethyl, pyrimidinylmethyl, and

for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or, in each case optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy or ethoxy i-

Propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, each optionally with cyano, fluorine, chlorine or bromine substituted propenyl, butenyl, propynyl or butynyl, for each cyclopropyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl,

Cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally with nitro, cyano, carbamoyl, formyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl substituted phenyl or benzyl, or for in each case optionally by cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, Difluoromethoxy or trifluoromethoxy substituted - 37 -

Heterocyclyl or heterocyclylalkyl from the range furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, morpholinyl, furylmethyl, thienylmethyl, pyrrolylmethyl, pyethylolylylylylethyl, pyrazolylylylethyl Pyrimidinylmethyl, or together with R ³ for propane-1J-diyl (trimethylene, -CH ₂ CH ₂ CH ₂ -), butane-1,4-diyl (tetramethylene, -CH ₂ CH ₂ CH ₂ CH ₂ -), pentane -l, 5-diyl (pentamethylene, -CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ -), hexane-1,6-diyl (hexamethylene, -CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ -) , 1-oxa-butane-1,4-diyl

(-OCH ₂ CH ₂ CH ₂ -) l-oxapentane-l, 5-diyl (-OCH ₂ CH ₂ CH ₂ CH ₂ -), or 3-oxapentane-l, 5-diyl (-CH ₂ CH ₂ OCH ₂ CH ₂ -) is.

4. A process for the preparation of substituted aminooxyalkane carboxamides according to claim 1, characterized in that carbonyl compounds of the general formula (II)

R.

(H)

in which

A and Rl have the meaning given in claim 1,

with aminooxyalkane carboxamides of the general formula (III) H, NR ² ² O- - R °

(III)

-N

OR ^« in which - 38 -

R ^, R ³ and R ^ have the meaning given in claim 1,

if appropriate in the presence of a diluent.

5. Use of at least one substituted Aminooxyalkancarboxamid according to any one of claims 1 to 3 for controlling unwanted plants.

6. Herbicidal agent, characterized by the content of at least one substituted aminooxyalkane carboxamide according to one of claims 1 to

3 and usual extenders.