WO1999020600A1

WO1999020600A1 - Substituted n-aryl-o-aryloxyalkyl carbamates and their use as herbicides

Info

Publication number: WO1999020600A1
Application number: PCT/EP1998/006374
Authority: WO
Inventors: Hans-Jochem Riebel; Johannes Rudolf Jansen; Peter Heitkämper; Markus Dollinger; Mark-Wilhelm Drewes; Ingo Wetcholowsky; Ernst Rudolf Gesing; Joachim Kluth; Stefan Lehr; Randy Allen Myers
Original assignee: Bayer Aktiengesellschaft
Priority date: 1997-10-20
Filing date: 1998-10-07
Publication date: 1999-04-29
Also published as: CA2307344A1; AU1151499A; CN1276787A; JP2001520216A; BR9812956A; DE19746267A1; EP1025078A1

Abstract

The invention relates to novel substituted n-aryl-o-aryloxyalkyl carbamates of general formula (I), wherein m represents the numbers 0, 1 or 2, n represents the numbers 0, 1, 2, 3 or 4, R1 represents cyano, halogen or alkyl or alkoxy, said alkyl or alkoxy being optionally substituted by cyano, halogen or C¿1?-C4 alkoxy and each having 1 to 4 carbon atoms; R?2¿ represents alkyl optionally substituted by cyano, halogen or C¿1?-C4 alkoxy and each having 1 to 4 carbon atoms, R?3¿ represents cyano, fluorine, bromine, iodine or alkyl, alkoxy or alkoxy carbonyl optionally substituted by cyano, halogen or C¿1?-C4 alkoxy, each having up to 4 carbon atoms; and R?4¿ represents cyano, bromine, iodine or alkyl, alkoxy or alkoxy carbonyl optionally substituted by cyano, halogen or C¿1?-C4 alkoxy, each having up to 4 carbon atoms, excluding the compound N-(2-methoxy-5-methyl-phenyl)-O-[1-(3-trifluoromethyl-phenoxymethyl)-propyl]-carbamate. The invention also relates to methods for producing the inventive substituted n-aryl-o-aryloxyalkyl carbamates and to their use as herbicides.

Description

SUBSTITUTED N-ARYL-O-ARYLOXYALKYL CARBAMATES AND THEIR USE AS HERBICIDES

The invention relates to new substituted N-. Aryl-O-aryloxyalkyl carbamates, processes for their preparation and their use as herbicides.

It is known that certain substituted N-ryl-O-aryloxyallcyl carbamates such as e.g. the compounds N- (2-chlorophenyl) -O- [l- (3-trifluoromethylphenoxymethyl) propyl] carbamate, N- (2-trifluoromethylphenyl) -O- [1 - (3-trifluoromethyl- phenoxy-methyl) -propyl] -carbamate and N- (3-trifluoromethyl-phenyl) -O- [l- (3-trifluoromethyl-phen-oxymethyl) -propyl] -carbamate, have herbicidal properties (cf. US-A-

5,099,059 and US-A-5,152,827). However, the herbicidal activity of these known compounds is not satisfactory in all respects.

The new substituted N-aryl-O-aryloxyalkyl-carbamates of the general formula (I) have now been found

in which

m represents the numbers 0, 1 or 2,

n stands for the numbers 0, 1, 2, 3 or 4, with the proviso that the sum of m and n is at least 1 in each individual case,

R ^{1 represents} cyano, halogen or, in each case, alkyl or alkoxy, each of which is substituted by cyano, halogen or C1-C4-alkoxy, each having 1 to 4 carbon atoms, R ^{2 represents} alkyl which has 1 to 4 carbon atoms and is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy,

R ^{3 represents} cyano, fluorine, bromine, iodine or alkyl, alkoxy or alkoxycarbonyl, each optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, each having up to 4 carbon atoms, and - in the event that m represents 1 or 2 stands - also stands for chlorine, as well

R ^{4 represents} cyano, bromine, iodine or in each case optionally substituted by cyano, halogen or C1-C4-alkoxy .Allcyl, alkoxy or alkoxycarbonyl each having up to 4 carbon atoms, and - in the event that m represents 1 or 2 - also stands for fluorine or chlorine,

however, the previously known compound N- (2-methoxy-5-methylphenyl) -O- [1- (3-trifluoromethylphenoxymethyl) propyl] carbamate - see US-A-5099059 and US-A-

5152827 each Table I, Compound No 40 - is excluded by disclaimer

The compounds of the general formula (I) according to the invention contain an asymmetrically substituted carbon atom and can therefore exist in different enantiomeric (R- and S-configured forms) or diasteromeric forms. The invention relates to both the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) as well as the mixtures of these stereoisomeric compounds

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

m represents the numbers 0, 1 or 2, n stands for the numbers 0, 1, 2 or 3, with the proviso that the sum of m and n is at least 1 in each individual case,

R ¹ for cyano, fluorine, chlorine, bromine or in each case methyl, ethyl, n- or l- which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy

Propyl, n-, I-, s- or t-butyl, methoxy, ethoxy, n- or l-propoxy,

R ² represents methyl, ethyl, n- or l-propyl, n-, I-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

R ^{3 represents} cyano, fluorine, bromine, iodine or in each case optionally by cyano, fluorine,

Chlorine, methoxv or ethoxy substituted methyl, ethyl, n- or l-propyl, n-, l-, s- or t-butyl, methoxy, ethoxy, n- or l-propoxy, methoxycarbonyl,

Ethoxycarbonyl, n- or l-propoxycarbonyl stands, and - if m stands for 1 or 2 - also stands for chlorine, and

R ^{4 is} cyano, bromine, iodine or in each case optionally by cyano, fluorine, chloro,

Methoxy or ethoxy substituted methyl, ethyl, n- or l-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or l-propoxy, n-, I-, s- or t- Butoxy, methoxycarbonyl, ethoxycarbonyl, n- or l-propoxycarbonyl, and - if m stands for 1 or 2 - also stands for fluorine or chlorine,

however, the previously known compound N- (2-methoxy-5-methylphenyl) -O- [l- (3-tiformomethylphenoxymethyl) propyl] carbamate - see US-A-5099059 and US-A-5152827, respectively Table I, Compound No 40 - is excluded by disclaimer

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

m represents the numbers 0 or 1,

n stands for the numbers 0, 1 or 2, with the proviso that in each individual case the

Sum of m and n is at least 1, R ^{1 represents} cyano, fluorine, chlorine, bromine or in each case methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine or chlorine,

R ² represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy,

R ^{3 is} cyano, fluorine, bromine or in each case optionally by fluorine, chlorine,

Methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, methoxy,

Ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and - in the event that m stands for 1 - also stands for chlorine, and

R ⁴ for cyano, bromine. Iodine or in each case optionally by fluorine, chlorine,

Methoxy or ethoxv substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-

Propoxycarbonyl, and - if m stands for 1 - also stands for fluorine or chlorine,

5152827 each Table I, Compound No 40 - is excluded by disclaimer

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 thereof

Residual definitions can be combined with one another, that is, also between the specified preferred ranges

The new substituted N-aryl-O-aryloxyalkyl carbamates of the general formula (I) are notable for their strong and selective herbicidal activity

Surprisingly, the new substituted N-aryl-O-aryloxyall yl-carbamates of the general formula (I) show considerably greater herbicidal activity than that previously known compounds N- (2-chlorophenyl) -O- [1 - (3-trifluoromethylphenoxymethyl) propyl] carbamate, N- (2-trifluoromethylphenyl) -O- [l- (3- trifluoromethyl-phenoxymethyl) propyl] carbamate and N- (3-trifluoromethyl-phenyl) -O- [l- (3-trifluoromethyl-phenoxymethyl) propyl] carbamate

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

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

Group 1

n, R ³ and R ⁴ have, for example, the meanings given in the list below:

Group 2

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1. Giuppe 3

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 4

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 5

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1. Group 6

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 7

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

group

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1. Group 9

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 10

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 11

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 12

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 13

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 14

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 15

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1

Group 16

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 17

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 18

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 19

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 20

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 21

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 22

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 23

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 24

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 25

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 26

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 27

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 28

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 29

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

Group 30

n, R ³ and R ⁴ have, for example, the meanings given above in Group 1.

The new substituted N-aryl-O-aryloxyalkyl-carbamates of the general formula (I) are obtained if

(a) Aryloxyalkyl chloroformate of the general formula (II)

in which

m, R ¹ and R ^{2 have} the meaning given above,

with arylamines of the general formula (III)

in which

n, R ³ and R ^{4 have} the meaning given above,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or if you

(b) aryloxyalkanols of the general formula (IV)

in which

m, R ¹ and R ^{2 have} the meaning given above,

with aryl isocyanates of the general formula (V)

in which

n, R ³ and R ^{4 have} the meaning given above,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent

If, for example, chloroformic acid [1- (2-fluoro-5-trifluoromethyl-phen-oxymethyl) propyl] ester and methyl 2-amino-4-ethylbenzoate are used as starting materials, the course of the reaction in the process according to the invention (a ) are outlined by the following formula scheme

If, for example, 2- (3,5-Bιs-tπfluormethyl-phenoxy) -l-methyl-ethanol and 2-bromo-6-methyl-phenyhsocyanate are used as starting materials, the course of the reaction in process (b) according to the invention can be outlined by the following formula become

The aryloxyaryl chloroformate to be used as starting materials in the process (a) according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (II). In the formula (II), m, R ¹ and R ² preferably or in particular those meanings which have already been mentioned above in connection with the description of the compounds of the formula according to the invention (I) preferably or as particularly preferred for m, R ¹ and R ²

The starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. US-A-5099059, US-A-5152827,

US-A-5399545)

The arylamines to be used further as starting materials in process (a) according to the invention are generally defined by the formula (III). In formula (III), n, R ³ and R ⁴ 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 have been indicated preferably or as particularly preferred for n, R ³ and R ⁴

The starting materials of the general formula (III) are known synthetic chemicals

The aryloxyalkanols to be used as starting materials in the process (b) according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (IV). In the formula (IV), m, 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 m, R ¹ and R ²

The starting materials of the general formula (IV) are known and / or can be prepared by processes known per se (cf. US-A-5099059, US-A-5152827,

US-A-5399545)

The ary socyanates to be used further as starting materials in process (b) according to the invention are generally defined by the formula (V). In formula (V), n, R ³ and R ⁴ 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 n, R ³ and R ⁴ The starting materials of the general formula (V) are known synthetic chemicals.

The usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries for processes (a) and (b).

These preferably include .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 methoxide, ethanolate, n or i propanolate, n, i, i or t butanolate; basic organic nitrogen compounds such as 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 [4J,0] non-5-ene (DBN), or 1,8-diazabicyclo [5,4,0] undec-7-ene (DBU).

Inert organic solvents are particularly suitable as diluents for carrying out processes (a) and (b) according to the invention. 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-

Methyl pyrrolidone or hexamethyl phosphoric acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol colmonoethyl 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 processes (a) and (b) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C

Processes (a) and (b) according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0J bar and 10 bar

To carry out processes (a) and (b) according to the invention, the starting materials are generally used in approximately aquimolar amounts. However, it is also possible to use one of the components in a large excess. The reaction is generally carried out in a suitable diluent, if appropriate 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 (see the production examples)

The active compounds according to the invention can be used as defo ants, desiccants, herbicides and, in particular, as herb weed killers. Weeds in the broadest sense are to be understood as all plants which grow up 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.

Dicotyledon weeds of the genera ^* Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, .Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Car- duus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurunc, Trifolium Taraxacum

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

Monocot weeds of the genera Echinochloa, Setaria, Panicum, Digitaria,

Phleum, Poa, Festuca, Eleusine, Brachiaπa, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbπsty s, Sagittaπa, Eleochaπs, Scirpus, Paspalum, Ischaemum, Sphenoclea, Agactyloctena, Dactyloctena

Monocot cultures of the genera Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, .Pananas, 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, e.g. on industrial and track systems and on paths and squares with and without tree cover. The connections can also be used 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 decorative and sports turf and pasture land and for selective purposes Weed control can be used in annual crops

The compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process The active 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 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 alkylnaphthalamine, 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 silica, aluminum oxide and silicates, are suitable as solid carriers for granules Question: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersing agents are, for example, lignin sulfite waste 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 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example

Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Am tryne, Amidochlor, .Amidosulfüron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benfüresate - Bensulfüron ( methyl), bentazone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxime, bromoxynil, butachlor, butroxydim, butylates, cafenstrole, caloxydim,

Carbetamides, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfüron, Chlortoluron, Cinmethylin, Cinosulfüron, Clethodim, Clodinafop (-propargyl), Clomazone, Clomepyronopyronopyridopyromopyromopyromopyron, Clomepyromopyron, Clomepyromopyromopyron, ), Cloransulam (-methyl), cumyluron, cyanazines, cycloates, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, dialates, dicamba, Diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefüron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamide, diquat, dithiopyr uron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalflura n, Ethametsulfüron (- methyl), Ethofümesate, Ethoxyfen, Ethoxysulfüron, Etobenzanid, Fenoxaprop (-P-ethyl), Flamprop (-ιsopropyl), Flamprop (-ιsopropyl-L), Flamprop (-methyl), Flazasulf- uron, Fluazιfop (-P-butyl), Flumetsulam, Flumιclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsulam, Fluometuron, Fluorochloπdone, Fluoroglycofen (-ethyl), Fluoropoxam, Flupropsulfur, Flupropacil (-methyl, -sodium), flurenol (-butyl), fluπdone, fluroxypyr (-meptyl), flurpπmidol, flurtamone, fluthιacet (-methyl), fluthiamide, fomesafen, glufosιnate (-ammonιum), glyphosate (-ιsopropylammonumι Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz- (-methyl), Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalm, Isoproturon, Isourox, Isoxopaben , Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobe nzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron, metπbuzin, metsulfüron (-methyl), Mo nate, Mono nuron, Naproani de, Napropamide, Neburon, Nicosulfüron, Norflurazon, Orbencarb, Oryza- n, Oxadiazongyl, Oxadiazongyl , Oxasulfüron, Oxaziclomefone, Oxyfluorfen, Paraquat, Pelargonsaure, Pendimetha n, Pentoxazone, Phenmedipham, Piperophos, Pretilachlor, Pπmιsulfüron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propisethyl, Sulfur (Prosulfon), Prosulfon () , Pyrazolate, Pyra- zosulfüron (-ethyl), Pyrazoxyfen, Pyπbenzoxim Pyπbuticarb, Pyπdate, Pyπmιnobac (- methyl), Pyπthιobac (-sodιum), Quinchlorac, Quinmerac, Quinoclamine, Quιzalofop (- P-ethylefür) ), Rimsulfüron, Sethoxydim, Simazine, Simetryn, Sulcotπone, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfüron, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thia-zopyr, -thiobenzuron-thiomethiazurium rb, tiocarbazil, tralkoxydim,

Tπallate, Tnasulfüron, Tπbenuron (-methyl), Tnclopyr, Tndiphane, Tnfluralin and Tnflusulfüron

A mixture with other known active compounds, such as fungicides, insecticides, acacids, nematicides, bird repellants, plant nutrients, and soil structure improvers 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. Scatter

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

The amount of active ingredient used can vary over a wide range. It 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, 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

Preparation Examples:

example 1

(Method (a))

3.0 g (25 mmol) chloroformic acid [1- (3-trifluoromethylphenoxymethyl) propyl] ester (racemic) are stirred at room temperature (approx. 20 ° C.) with a solution of 2.5 g (10 mmol) of 2J-dimethyl-aniline in 80 ml of toluene and the reaction mixture is stirred for 15 hours at room temperature. It is then washed with water and 1N hydrochloric acid, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.

3.5 g (92% of theory) of N- (2,3-dimethylphenyl) -O- [l- (3-trifluoromethylphenoxymethyl) propyl] carbamate (racemate) are obtained as a crystalline residue of melting point 76 ° C.

Analogously to preparation example 1 and in accordance with the general description of the preparation processes according to the invention, for example the compounds of the formula (I) shown in Table 1 below can also be prepared.

In all cases, these are racemates. The position of R ¹ is - where necessary - stated so that the CF ₃ group is always in the 3 position. The

Structures were confirmed by ^Ϊ H NMR spectra. Table 1: Examples of the compounds of the formula (I)

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of allcylaryl 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 level

Concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amounts of active ingredient 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, 2, 3 and 4, with good tolerance to crop plants, such as, for example, maize, barley and soybeans, show strong activity against weeds. 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 with a height of 5-15 cm are sprayed with the preparation of active compound in such a way that the desired amounts of active compound are applied per unit area. The concentration of the spray broth is chosen so that in

1000 1 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

Mean it

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

In this test, for example, the compounds according to Preparation Examples 1, 2 and 4, with good tolerance to crop plants, such as, for example, maize, show a strong action against weeds

Claims

claims

1. Substituted N-.Aryl-O-aryloxyalkyl-carbamates of the general formula (I)

in which

m stands for the numbers 0, 1 or 2.

n stands for the numbers 0, 1, 2, 3 or 4, with the proviso that in each

In individual cases the sum of m and n is at least 1,

R ^{1 represents} cyano, halogen or in each case optionally substituted by cyano, halogen or C _] -C4-alkoxy alkyl or alkoxy each having 1 to 4 carbon atoms,

R ^{2 represents} alkyl which has 1 to 4 carbon atoms and is optionally substituted by cyano, halogen or C 4 -C 4 -alkoxy,

R ^{3 represents} cyano, fluorine, bromine, iodine or in each case optionally substituted by cyano, halogen or C 4 -C 4 -alkoxy-substituted alkyl, alkoxy or alkoxycarbonyl each having up to 4 carbon atoms, and - in the event that m represents 1 or 2 - also stands for chlorine, as well

R ^{4 represents} cyano, bromine, iodine or in each case optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy. Alkyl, alkoxy or alkoxycarbonyl each having up to 4 carbon atoms, and - in the event that m represents 1 or 2 - also stands for fluorine or chlorine, except the compound N- (2-methoxy-5-methylphenyl) -O- [l- (3-trifluoromethylphenoxymethyl) propyl] carbamate.

Substituted N-.Aryl-O-aryloxyalkyl-carbamates of the general formula (I) according to Claim 1, characterized in that

m represents the numbers 0, 1 or 2,

n for the numbers 0, 1,

2 or 3, with the proviso that in each

In individual cases the sum of m and n is at least 1,

R ¹ for cyano, fluorine, chlorine, bromine or in each case, if appropriate

Cyano, fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,

R ² 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 is} cyano, fluorine, bromine, iodine or in each case optionally by cyano,

Fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and - in the event that m represents 1 or 2 - also represents chlorine, and

R ^{4 is} cyano, bromine, iodine or in each case methyl, ethyl, n- or i- which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy

Propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i- Propoxycarbonyl, and - in the event that m represents 1 or 2 - also represents fluorine or chlorine,

except for the compound N- (2-methoxy-5-methyl-phenyl) -O- [l- (3-trifluoromethyl-phenoxymethyl) propyl] carbamate.

3. Substituted N-aryl-O-aryloxyalkyl carbamates of the general formula (I) according to Claim 1, characterized in that

m represents the numbers 0 or 1,

n stands for the numbers 0, 1 or 2, with the proviso that in each

In individual cases the sum of m and n is at least 1,

R ^{1 represents} cyano, fluorine, chlorine, bromine or in each case methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine or chlorine,

R ^{3 is} cyano, fluorine, bromine or in each case optionally by fluorine,

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

Propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl,

Ethoxycarbonyl, n- or i-propoxycarbonyl stands, and - in the event that m stands for 1 - also stands for chlorine, and

R ^{4 is} cyano, bromine, iodine or in each case optionally by fluorine, chlorine,

Methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl,

Methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and - in the event that m is

1 stands for - also stands for fluorine or chlorine, except for the compound N- (2-methoxy-5-methyl-phenyl) -O- [l- (3-trifluoromethyl-phenoxymethyl) propyl] carbamate.

4. Process for the production of substituted N-aryl-O-aryloxyalkyl-carbamates of the general formula (I) according to one of Claims 1 to 3, characterized by reacting

(a) Aryloxyalkyl chloroformate of the general formula (II)

in which

m, R ¹ and R ^{2 have} the meaning given in one of claims 1 to 3,

with arylamines of the general formula (III)

in which

n, R ³ and R ^{4 have} the meaning given in one of claims 1 to 3, optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,

or

(B)

of the general formula (IV)

in which

m, R ¹ and R ^{2 have} the meaning given in one of claims 1 to 3,

with aryl isocyanates of the general formula (V)

in which

n, R ³ and R ^{4 have} the meaning given in one of Claims 1 to 3,

optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent.

5. Use of at least one substituted N-aryl-O-aryloxyalkyl carbamate according to one of claims 1 to 3 for combating undesirable plants.

6. Herbicidal agent, characterized by the content of at least one substituted N-.Aryl-0-aryloxyalkyl-carbamate according to one of claims 1 to 3.