MXPA00003876A - Substituted n-aryl-o-aryloxyalkyl carbamates and their use as herbicides - Google Patents

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 C1-C4 alkoxy and each having 1 to 4 carbon atoms;R2 represents alkyl optionally substituted by cyano, halogen or C1-C4 alkoxy and each having 1 to 4 carbon atoms, R3 represents cyano, fluorine, bromine, iodine or alkyl, alkoxy or alkoxy carbonyl optionally substituted by cyano, halogen or C1-C4 alkoxy, each having up to 4 carbon atoms;and R4 represents cyano, bromine, iodine or alkyl, alkoxy or alkoxy carbonyl optionally substituted by cyano, halogen or C1-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

N-ARIL-O-ARYLOXIALQUIL-CARBAMATOS SUBSTITUIDOS AND ITS EMPLOYMENT AS HERBICIDES. Field of the invention. .__ The invention relates to novel substituted N-aryl-O-aryloxyalkyl carbamates, processes for their preparation and their use as herbicides. Description of the prior art. It is known that certain substituted N-aryl-O-aryloxyalkylcarbamates, such as for example the compounds N- (2-chloro-phenyl) -O- [l- (3-trifluoromethyl-phenoxymethyl) -propyl] -carbamates, N- ( 2-trifluoromethyl-phenyl) -O- [1- (3-trifluoromethyl-phenoxymethyl) -pro-pyl] -carbamate and N- (3-trifluoromethyl-phenyl) -O- [l- (3-trifluoromethyl-phenoxymethyl) - propyl] -carbamate, exhibit herbicidal properties (see US-A 5 099 059 and US-A-5 * - * 152 827). However, the herbicidal activity of these known compounds is not always satisfactory from all points of view. Detailed description of the invention. New substituted N-aryl-O-aryloxyalkyl carbamates of the general formula (I) have now been found, where m means the numbers 0, 1 or 2, n means the numbers 0, 1, 2, 3 or 4, with the proviso that in any case the sum of m and n is at least 1, R1 means cyano, halogen or means alkyl or alkoxy with respectively 1 to 4 REF. : 119053 carbon atoms substituted, where appropriate, by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, R2 means alkyl having 1 to 4 carbon atoms, optionally substituted by polycyanogen, by halogen or by alkoxy with 1 to 4 carbon atoms of carbon, R3 means cyano, fluorine, bromine, iodine or means alkyl, alkoxy or alkoxycarbonyl with respectively up to 4 carbon atoms, each optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, and - when m means 1 or 2, it also means chlorine, and also R 4 is cyano, bromo, iodo, or is alkyl, alkoxy or alkoxycarbonyl with up to 4 carbon atoms, respectively substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, and when m means 1 or 2, it also means fluorine or chlorine, but the previously known compound constituted by N- (2-met) is excluded from being claimed. oxy-5-methyl-phenyl) -O- [l- (3-trifluoromethyl-phenoxymethyl) -propyl] -carbamate -see US-A-5099059 and US-A-5152827 respectively table 1, compound no. 40-. The compounds according to the invention of the general formula (I) contain an asymmetrically substituted carbon atom and can therefore be present in various enantiomeric forms (forms with the R and S configuration) or diastereomeric forms. The invention relates both to the various possible individual enantiomeric or stereoisomeric forms of the compounds of the formula (I) as well as to the mixtures of these stereoisomeric compounds. In the definitions the hydrocarbon chains, such as alkyl - even in combination with heteroatoms, such as in alkoxy - are respectively straight chain or branched chain. The subject of the invention are preferably compounds of the formula (I), where m means the numbers 0, 1 or 2, n means the numbers 0, 1, 2 or 3, with the proviso that in each case the sum of m_ and n is almenes 1, R: means cyano, fluorine, chlorine, bromine or means methyl, ethyl, n- or i-propyl, n-, i- s- or t-butyl, methoxy, ethoxy, n- or i-propoxy substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, R2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted respectively by cyano, by fluorine, by chlorine, by methoxy or by ethoxy R3 means cyano, fluorine, bromine, iodine or means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl , n- or i-propoxycarbonyl substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, and - when m means 1 or 2- also means chlorine, as well as R4 means cyano, bromo, iodo or means methyl, ethyl, n- or i-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 respectively substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, and - when m means 1 or 2- also means fluorine or chlorine, but the previously known compound constituted by N- (2-methoxy-5-methyl-phenyl) -Q- [] is excluded from being claimed. 1- (3-trifluoromethyl-phenoxymethyl) -propyl] -carbamate -see US-A-5099059 and US-A-5152827 respectively table 1, compound no. 40-. The invention especially relates to the compounds of the formula (I), in which m means the numbers 0 or 1, n means the numbers 0, 1 or 2, with the proviso that in each case, in particular the sum of m and n is at least 1, - R1 means cyano, fluorine, chlorine, bromine or means methyl, ethyl, methoxy or ethoxy substituted, where appropriate, by fluorine or chlorine, R2 means methyl, ethyl, n- or i-propyl substituted respectively by fluorine, chlorine, methoxy or ethoxy, R3 means cyano, fluorine, bromine or means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted respectively, where appropriate, fluorine, chlorine, methoxy or ethoxy, and - when m means 1 - also chlorine, and also R 4 means cyano, bromo, iodo or means methyl, ethyl, n- or i-propyl, methoxy , ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl respectively substituted, if appropriate, by fluorine, by chlorine, by methoxy or by ethoxy, and - when m means 1 also means fluorine or chlorine, however, it is excluded if the previously known compound is claimed. consisting of N- (2-methoxy-5-methyl-phenyl) -O- [l- (3-trifluoromethyl-phenoxymethyl) -propyl] -carbamate -see US-A-5099059 and US-A-5152827 respectively table 1 , compound n ° 40-. The definitions of the residues given above in a general manner or indicated in the preferred ranges are valid both for the final products of the formula (I) and also, correspondingly, for the starting materials or the intermediate products necessary respectively for the preparation . These definitions of the remains can be combined arbitrarily with each other, that is to say even between the preferred ranges indicated. The new substituted N-aryl-O-aryloxyalkyl-carbamates of the formula - -general (I) are characterized by a powerful and selective herbicidal activity. Surprisingly, the new substituted N-aryl-O-aryloxyalkyl carbamates of the general formula (I) have a considerably higher herbicidal activity than the previously known compounds N- (2-chloro-phenyl) -O- [l- ( 3-trifluoromethyl-phenoxymethyl) -propyl] -carbamates, N- (2-trifluoromethyl-phenyl) -O- [l- (3-trifluoromethyl-phenoxymethyl) -propyl] -carbamate and N- (3-trifluoromethyl) phenyl) -O- [1- (3-trifluoromethyl-phenoxymethyl) -propyl] -carbamate. To some extent the compounds of the formula (I) also exhibit fungicidal and insecticidal activity. Examples of compounds according to the invention of the general formula (I) have been indicated in the following groups. Group 1.

In this case n, R3 and R4 have, by way of example, the meanings indicated in the following enumeration.

Group 2.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1.

Group 3.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 4.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 5.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1.

Group 6 In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 7.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 8.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1.

Group 9 In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 10.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 11.

In this case, n, R and R have, as exemplified, the meanings indicated in group 1.

Group 12 In this case n, R3 and R4 have, in an exemplary way, the meanings indicated in group 1. Group 13.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 14.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1.

Group 15 In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 16.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 17.

In this case n, R3 and R have, by way of example, the meanings indicated in group 1.

Group 18 In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 19.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 20.

In this case n, R and R have, by way of example, the meanings indicated in group 1.

Group 21 In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 22.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 23.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1.

- - Group 24.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 25.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 26.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1.

Group 27 In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 28.

In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. Group 29.

In this case n, R and R have, by way of example, the meanings indicated in group 1.

Group 30 In this case n, R3 and R4 have, by way of example, the meanings indicated in group 1. The new substituted N-aryl-O-aryloxyalkyl-carbamates of the general formula (I) are obtained, if (a) they are made reacting aryloxyalkyl chloroformates of the general formula (II) wherein m, R1 and R2 have the meaning indicated above, with arylamines of the general formula (III) wherein n, R3 and R4 have the meaning indicated above, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in presence of a diluent, or if (b) aryloxyalkanols of the general formula (IV) are reacted wherein m, R1 and R2 have the meaning indicated above, with aryl isocyanates of the general formula (V) wherein n, R3 and R4 have the meaning indicated above, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent. If, for example, chloroformate of [1- (2-fluoro-5-trifluoromethyl-phenoxymethyl) -propyl] and methyl 2-amino-4-ethyl-benzoate are used as starting materials, the development of the reaction may be schematized in the process (a) according to the invention by means of the following formula scheme: - - If, for example, 2- (3,5-bis-trifluoromethyl-phenoxy) -l-methyl-ethanol and 2-bromo-6-methyl-phenylisocyanate are used as starting materials, the development of the reaction in the procedure (b) according to the invention by means of the following formula scheme: The aryloxyalkyl chloroformates to be used as starting materials in the process (a) according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (II). In the formula (II) m, R1 and R2 preferably have or especially those meanings which have already been mentioned above, preferably or especially preferably for m, R1 and R2 in relation to the description of the compounds of the formula (I) according to the invention. The starting materials of the general formula (II) are known and / or can be prepared according to known processes (see US-A-5099059, US-A-152827, US-A-5399545). The arylamines to be further employed as starting materials in the process (a) according to the invention are generally defined by the formula (III). In the formula (III), n, R3 and R4 preferably have or especially those meanings that have already been mentioned above of preferably or very particularly preferably for n, R3 and R4 in relation to the description of the compounds of the formula (I) according to the invention.

The starting materials of the general formula (III) are chemical products-for known syntheses. The aryloxyalkanols to be used as starting materials in the process (b) according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (IV). In the formula (TV) m, R1 and R2 preferably have or especially those meanings which have already been mentioned above in a preferred manner or, more preferably, for m, R1 and R2 in relation to the description of the compounds of the formula (I) according to the invention. The starting materials of the general formula (IV) are known and / or can be prepared according to known processes (see US-A-5099059, US-A-5152827, US-A-5399545). The arylisocyanates to be further employed as starting materials in the process (b) according to the invention are generally defined by the formula (V). In the formula (V) n, R 3 and R 4 preferably have or especially those meanings which have already been mentioned above in a preferred manner or, more preferably, for n, R 3 and R 4 in connection with the description of the compounds of the formula (I) according to the invention. The starting materials of the general formula (V) are chemical products for known synthesis. As auxiliary agents for the reaction in processes (a) and (b), the usual inorganic or organic acid bases or acceptors are generally suitable. These preferably include acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates of alkali metals or - of alkaline earth metals, such as, for example, sodium, potassium or calcium acetate, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium bicarbonate; lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, methanolate, ethanolate, n- or i-propanolate, n-, i-, s- or t sodium or potassium butanolate; also basic organic nitrogenous compounds, such as for example trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N -dimethylbenzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl -pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino, pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2.2.2] -octane (DABCO), 1, 5-diazabicyclo [4] , 3.0] -non-5-ene (DBN), or 1,8-diazabicyclo- [5,4,0] -undec-7-ene (DBU). Suitable diluents for carrying out the processes (a) and (b) according to the invention are all inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic halogenated hydrocarbons, such as, for example, benzine, 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-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphorotriamide; 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 monoethyl ether, diethylene glycol mono- Methyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water. The reaction temperatures in carrying out the processes (a) and (b) according to the invention can vary within wide limits. In general it is "worked at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C. The 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 higher pressure or at a lower pressure, in general between 0.1 bar and 10 bar-. For carrying out the processes (a) and (b) 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 respectively. The reaction is generally carried out in a suitable diluent, if appropriate in the presence of an auxiliary agent of the reaction, and the reaction mixture is generally stirred for several hours at the required temperature. The preparation is carried out according to usual methods (see the preparation examples). The active compounds according to the invention can be used as defoliants, desiccants, herbicidal agents and especially as weed killers. By weeds, in the broadest sense, we must understand the plants that grow in places where they are unwanted. The fact that 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: . Bad dicotyledonous herbs of the following classes: 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. Dicotyledonous crops of the classes: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita. Bad monocotyledonous herbs of the following kinds: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum , Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera. Cultures of monocotyledonous classes: Oryza, Zea, Triticum, Hordeum, Avena, Sécale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. The use of the active compounds according to the invention, however, is not limited in any way to these classes, but they also extend equally over other plants. The compounds are suitable, depending on the concentration, to completely combat the weeds, for example, in industrial and road installations and in roads and squares, with and without tree growth. In the same way, the compounds can be used to control weeds in permanent crops, for example, in forest facilities, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee, of tea, rubber oil palms, cocoa, berries and hops, on paths ornamental and sporty and on surfaces of meadows and to fight weeds selectively in mono-annual crops. The compounds according to the invention of the formula (I) are especially suitable for the selective fight against monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both in the pre-emergence procedure and in the post-emergence process. The active ingredients can be converted into customary formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active compound , as well as micro-encapsulations in polymer materials. These formulations are prepared in known manner, for example, by mixing the active ingredients with extender materials, that is, with liquid solvents and / or solid excipients, where appropriate, using surfactants, that is, emulsifiers and / or dispersants and / o foam generating means. When using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. Particularly suitable liquid solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane. , or paraffins, for example, fractions of crude oil, mineral and vegetable oils, alcohols such as butanol, or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water.

- - As solid excipients come into consideration: for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earths and molten synthetic minerals, such as silicic acid, highly dispersed, aluminum oxide and silicates, as solid excipients for granulates are considered: for example, broken and fractionated natural minerals such as calcite, marble, stone pumice, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as granulates of organic materials, such as sawdust, coconut husk shells, corn ears and tobacco stems; suitable emulsifiers and / or foam generators are, for example, non-ionic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, polyoxyethylenated ethers of fatty alcohols, such as, for example, alkylaryl polyglycol ether, alkylsulfonates, alkyl sulfates, arylsulfonates, as well as the albumin hydrolysates; as dispersants they come into consideration: for example, sulfitic leaching of lignin and methylcellulose. Adhesives such as carboxymethylcellulose, natural and synthetic polymers powdery, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin, and synthetic phospholipids can be used in the formulations. -cos. Other additives can be mineral and vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, ferrocyanic blue and organic dyes, such as alizarin dyes, metallic azo and phthalocyanine dyes and trace nutrients, such as iron salts, can be employed. manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally contain between 0.1 to 95% by weight of active compound, preferably between 0.5 and 90%. The active compounds according to the invention can be used as such or in their formulations also in a mixture with known herbicides for controlling weeds, ready-to-use preparations or tank mixtures being possible. Suitable mixtures are known herbicides, for example: Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl) ), Benfiíresate, Bensulfuron (-methyl), Bentazon, Benzofenap, Benzoylprop- (ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxuydim, Carbetamide, Carfentrazone ( -ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, 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, Diflufenzopyr, Dimefur Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfi? ron (-methyl), Ethofumesate, Ethoxyfen, Ethoxy sulfuron, Etobenzanid, Fenoxaprop - (- P-ethyl), Framprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulfuron, Fluazifop (-P-butyl), Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsulam, Fluometuron, Fluor ochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flupyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-methyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Ruthia ide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium ), Halosafen ^ Haloxy fop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxaflutole , Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfi? Ron (-methyl), Molinate, Monolinuron, Naproanilide , Napropamide, Neburon, Nicosulftiron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulftiron, Oxaziclomefone, Oxyfluorfen, Paraquat, pelargonic acid, Pendimethalin, Pentoxazone, Phenmedipham, Piperophos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyribenzoxim, Pyributicarb, Pyridate, Pyriminobac (-methyl), Pyrithiobac (-sodium), Quinchlórac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P-teft? Ril), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulft? Ron (-methyl), Thiobencarb, Thiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifluralin and Tritosulfuron. A mixture with other known active substances is also possible, such as fungicides, insecticides, acaricides, nematicides, protective substances against ingestion by birds, nutrient substances of the plants and means for improving the structure of the ground.

The active compounds can be used as such, in the form of their formulations or in the forms of application prepared therefrom by further dilutions., such as ready-to-use solutions-suspensions, emulsions, powders, pastes and granulates. The use is carried out in the usual way, for example, by watering, spraying, spraying, spreading. The active products according to the invention can be applied both before and after the outbreak of the plants. They can also be incorporated into the soil before sowing. The quantities of active product used can vary within a wide range. These depend fundamentally on the type of the desired effect. In general, the amounts used are between 1 g and 10 kg of active product per hectare of land surface, preferably between 5 g and 5 kg per hectare. The preparation and use of the active substances according to the invention are deduced from the following examples: Preparation examples. Example 1.

(Procedure (a)). 3.0 g (25 mmol) of [1- (3-trifluoromethyl-phenoxymethyl) -propyl] (racemic) chloroformate are added at room temperature (approximately ° C), with stirring, to a solution of 2.5 g (10 mmol) of 2,3-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 with IN hydrochloric acid, Dry with sodium sulfate and filter. The solvent is carefully removed by distillation of the filtrate under vacuum from the water pump. 3.5 g (92% of theory) of N- (2,3-dimethyl-phenyl) -O- [1- (3-trifluoromethyl-phenoxymethyl) -propyl] -carbamate (racemate) are obtained in the form of crystalline residue with a melting point of 76 ° C. In a manner analogous to that of the preparation example 1 and correspondingly to the general description of the preparation processes according to the invention, for example, the compounds of the formula (I) indicated in table 1 below can also be prepared.

In all cases it is about racemates. The position of R1 is indicated - insofar as necessary - in such a way that the CF3 group is always in position 3. The structures were confirmed by the 'H-NMR spectra.

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

Example A. Pre-bud test. Solvent: 5 parts by weight of acetone. _ Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the preparation of active product in such a way that the desired amount of active product per unit area is applied. The concentration of the preparation is chosen in such a way that the quantity of active product desired in each case is applied in 1000 liters of water / hectare. After three weeks, the degree of damage of the plants is evaluated in% of damages compared to the development of the untreated control. They mean: 0% = no effect (same as untreated controls). 100% = total destruction. In this test they show, for example, the compounds according to the preparation examples 1, 2, 3 and 4, with a partially good compatibility with the crop plants, for example corn, barley and soybean, a potent effect against weeds . Example B. Post-emergence test. Solvent: 5 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether.

To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent, the amount of emulsifier indicated is added and the concentrate is diluted with water at the desired concentration. With the preparation of the active product, test plants having a height of 5 to 15 cm are sprayed in such a way that the desired quantities of active compound per unit area are respectively applied. The concentration of the sprayable broths is chosen in such a way that the desired quantity in each case of active product is applied in 1,000 liters of water / ha. After three weeks, the degree of damage of the plants is evaluated in% of damages compared to the development of the untreated controls. They mean: 0% = no effect (same as the untreated controls). 100% = total destruction. In this test, for example, the compounds according to Preparation Examples 1, 2 and 4 show a partially good compatibility with crop plants, for example corn, a potent effect against weeds. It is noted that in relation to this date, the best method known to the applicant for carrying out the aforementioned invention is that which is clear from the present description of the invention.

Claims (6)

1. Having described the invention as above, the content of the following claims is claimed as property: 1. Substituted N-aryl-O-aryloxyalkyl-carbamates of the general formula (I) characterized because; m means the numbers 0, 1 or 2, n means the numbers 0, 1, 2, 3 or 4, with the proviso that in any case the sum of m and n is at least 1, R 1 means cyano, halogen or means alkyl or alkoxy having respectively 1 to 4 carbon atoms substituted, where appropriate, by cyano, by halogen or by alkoxy having 1 to 4 carbon atoms, R2 means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, halogen or by alkoxy having 1 to 4 carbon atoms, R3 means cyano, fluorine, bromine, iodine or means alkyl, alkoxy or alkoxycarbonyl with respectively up to 4 carbon atoms, each substituted, where appropriate, by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, and when m means 1 or 2, it also means chlorine, and R 4 means cyano, bromo, iodo, or means alkyl, alkoxy or alkoxycarbonyl with up to 4 carbon atoms, respectively substituted, if appropriate, by cyano, halogen or alkoxy with 1 to 4 carbon atoms, and - when m means 1 or 2- also means fluorine or chlorine, with the exception of the compound N- (2-methoxy-5-methyl-phenyl) -O- [l- (3-trifluoromethyl phenoxymethyl) -propyl] -carbamate.
2. 2. - substituted N-aryl-O-aryloxyalkyl-carbamates of the general formula (I) according to claim 1, characterized in that m means the numbers 0, 1 or 2, - n means the numbers 0, 1, 2 or 3, with the condition that in each case the sum of m and n is at least 1, R 1 signifies cyano, fluorine, chlorine, bromine or means methyl, ethyl, n- or i-propyl, n-, i- s- or t-butyl, methoxy, ethoxy, n- or i-propoxy substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, R2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted respectively by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, R3 means cyano, fluorine, bromine, iodine or means methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl respectively substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, and -when m means 1 or 2-s also chlorine, as well as R 4 means cyano, bromo, iodo or means methyl, ethyl, n- or i-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 respectively substituted, if appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, and -when m means 1 or 2- also means fluorine or chlorine, with the exception of the compound N- (2-methoxy-5-methyl-phenyl) -O- [l- (3-trifluoromethyl-phenoxymethyl) -propyl] -carbamate.
3. 3. N-substituted aryl-O-aryloxyalkyl-carbamates of the general formula (I) according to claim 1, characterized in that m means the numbers 0 or 1, _ n means the numbers 0, 1 or 2, with the proviso that in each case, in particular the sum of m and n is at least 1, R 1 means cyano, fluorine, chlorine, bromine or means methyl, ethyl, methoxy or substituted etox respectively, where appropriate, fluorine or chlorine, R 2 is methyl, ethyl, n- or i-propyl, respectively substituted, if appropriate, by fluorine, chlorine, methoxy or ethoxy, R 3 is cyano, fluorine, bromine or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl respectively substituted, where appropriate, by fluorine, chlorine, methoxy or ethoxy, and - when m means -1 also means chlorine, and R4 means cyano, bromo, iodo or means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i- propoxycarbonyl respectively substituted, if appropriate, by fluorine, by chlorine, by methoxy or by ethoxy, and - when m means 1 - also means fluorine or chlorine, with the exception of the compound N- (2-methoxy-5-methyl-phenyl) -O- [l- (3-trifluoromethyl phenoxymethyl) -propyl] -carbamate.
4. 4. Process for obtaining the substituted N-aryl-O-aryloxyalkyl-carbamates of the general formula (I) according to one of claims 1 to 3, characterized in that (a) aryloxyalkyl chloroformates of the formula are reacted general (II) in which m, R1 and R2 have the meaning indicated in one of claims 1 to 3 with arylamines of the general formula (III) wherein n, R3 and R4 have the meaning indicated in one of claims 1 to 3, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, or (b) are made reacting aryloxyalkanols of the general formula (IV) wherein m, R1 and R2 have the meaning indicated in one of claims 1 to 3 with aryl isocyanates of the general formula (V) in which n, R3 and R4 have the meaning indicated in one of claims 1 to 3, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent. __
5. 5. Use of at least one substituted N-aryl-O-aryloxyalkyl carbamate according to one of claims 1 to 3, for the control of undesirable plants.
6. 6. Herbicidal agent, characterized in that it has a content of at least one substituted N-aryl-O-aryloxyalkyl carbamates according to one of claims 1 to 3.