MXPA97004047A - Carbam herbicides - Google Patents

Abstract

The present invention relates to a compound of the formula I: wherein Q represents a group, R represents halogen, trifluoromethyl, cyano, nitrohaloalkoxy of 1 to 3 carbon atoms, Z represents hydrogen or halogen, or Z and R together form a group - OCF2O in the 2 and 3 position of the phenyl ring, R1 represents alkyl of 1 to 5 carbon atoms, R2, R3, R4 and R5 independently of each other represent hydrogen, methyl or ethyl, X represents oxygen, sulfur, -SO- or -SO2-; Y represents hydrogen, halogen, alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, ociano, n represents 0, 1, 2, n1 represents 0, 1 and m represents 0, 1 with the condition that m represents 1 when Q represents group (1) or (2), as well as its diastereomers and enantiomer

Description

CARBAMATE HERBICIDES The present invention relates to novel N-phenyl and N-heteroarylalkylcarbamates substituted with herbicidal action, with processes for their preparation, with compositions containing these N-phenyl and N-heteroarylalkylcarbamates as active ingredients, as well as their use to combat weeds , above all in crops of useful plants such as cereals, rice, corn, soybeans and cotton. Alkyls and phenylcarbamates substituted with herbicidal action are already known and are described for example in U.S. Patent Applications published for opposition US-A-5,078,783; US-A-5, 099, 059; US-A-5, 152, 827; US-A-5,194,661, and US-A-5, 399, 545. New N-phenyl and N-heteroarylalkylcarbates substituted with herbicidal qualities have already been found, which are characterized by good activity. The compounds according to the invention are equivalent to formula I: where: Q represents a group ~ _) (') • -P'U (2) or "'" '(R represents halogen, trifluoromethyl, cyano, nitro or haloalkoxy of 1 to 3 carbon atoms; Z represents hydrogen or halogen; Z and R together form a group -OCF20 at the 2 and 3 position of the phenyl ring, W represents alkyl of 1 to 5 carbon atoms, R2, R3, R4, and R5 independently represent hydrogen, methyl or ethyl; X represents oxygen, sulfur, -SO- or -S02-; Y represents hydrogen, halogen, alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 3 carbon atoms, or cyano; n represents 0 , 1, or 2, n represents 0, or 1, and m represents 0 or 1, with the proviso that m represents 1 when Q represents group (1) or (2), as well as its diastereomers and enantiomers.

In the above definitions it is to be understood under halogen, iodine, and preferably fluorine, chlorine, and bromine. Suitable alkyl groups are straight-chain or branched alkyl groups, for example methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, n-pentyl , and its isomers; preferably methyl and ethyl. As the haloalkyl groups, alkyl groups substituted one or more times, especially substituted 1 to 3 times with halogen, where halogen represents bromine or iodine and especially fluorine or chlorine, for example fluoromethyl, difluoromethyl, chloromethyl, dichloromethyl, trichloromethyl and especially trifluoromethyl. Suitable alkoxy groups are, for example, methoxy, ethoxy, n-propyloxy, and iso-propyloxy. Suitable haloalkoxy groups are, for example, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,2,2-tetrafluoroethoxy; preferably difluoromethoxy and trifluoromethoxy. The N-phenyl and N-heteroarylalkylcarbamates according to the invention of the formula I possess good selectivity in crops of useful plants such as cereals, rice, soybean and cotton in the application in the post-emergence procedure, but especially in the application in the pre-emergency procedure. The possible presence of at least one asymmetric carbon atom in the compounds of the formula I, in the position β with respect to the phenyl-X group and in the carbon atom? and / or β-benzyl, when R 4 and R are different from R 5 or R 3, it is associated with the fact that the compounds can be present both as optically active isomers and also in the form of racemic mixtures. The optically active compounds of the formula I can be obtained according to known separation methods, such as for example the fractional crystallization, of the racemic mixtures or by means of an enantioselective synthesis. In the present invention, all optically pure antipodes, as well as racemates, are to be understood under active ingredients of formula I. Insofar as reference is not made especially to the different optical antipodes, those racemic mixtures are to be understood under the indicated formula, which are formed in the indicated preparation procedure. Preferred are compounds of formula I in which the radical R represents chloro, bromo, trifluoromethyl or trifluoromethoxy. Also preferred are compounds of the formula I in which Z represents hydrogen or fluorine. Preferred compounds of the formula I are also those compounds in which represents methyl or ethyl. In addition, the compounds of the formula I in which R 2, R 3, R 4 and R 5 independently of each other represent hydrogen or methyl are preferred. Of these compounds, those in which R2, R3, and R4 represent hydrogen are particularly preferred, and R5 represents methyl.

Also preferred are compounds of formula I in which R.sup.2, R.sup.3, and R. represent hydrogen, R.sup.5 represents methyl or ethyl and Q represents group (1), (2) or (3).

Especially preferred are those compounds in which R 5 represents methyl and Q represents group (1) or (2). Also preferred are compounds of formula I, in which X represents oxygen or sulfur. Also preferred are compounds of formula I, in which Q represents group (1) or (2); n represents 1; and Y is attached in ortho or meta position with respect to the binding site. Of these compounds, those in which Y is attached in the ortho position to the binding site are especially preferred. Further preferred are compounds of the formula I in which Y represents hydrogen, fluorine, chlorine, methyl, trifluoromethyl, methoxy or cyano. Important compounds of formula I are those in which Q represents group (1); R represents chloro, cyano, nitro, trifluoromethyl, trifluoromethoxy or difluoromethoxy; Z represents hydrogen or Z and R together form a group 0CF20-in position 2 and 3 of the phenyl ring; X represents oxygen or sulfur; Y represents hydrogen, 2-fluoro, 2- or 3-chloro, 2-methyl, or 2-trifluoromethyl; n represents 0 or 1; R? represents methyl or ethyl; R2 represents hydrogen; and R3, R4, and R5 independently represent hydrogen or methyl.

Other important compounds of the formula I are those in which Q represents the group 'R represents trifluoromethyl or trifluoromethoxy; Z represents hydrogen; or Z and R together form a group -OCF20- in position 2 and 3 of the phenyl ring; X represents oxygen or sulfur; Y represents hydrogen, 3- or 5-chloro or 3-methyl; R? represents ethyl; R 2 represents hydrogen or methyl; R3 represents hydrogen; and m represents 0. Also important are compounds of formula I, in which Q represents the group R represents trifluoromethyl or trifluoromethoxy; Z represents hydrogen; or Z and R together form a -OCF20 group in position 2 and 3 of the phenyl ring; X represents oxygen or sulfur; Y represents hydrogen, 3-chloro or 3-methyl; W? represents ethyl; R2 and R3 represent hydrogen; R4 and R5 independently of each other represent hydrogen or methyl; and m represents 1. Important compounds of formula I are those in which Q represents the group R represents trifluoromethyl or trifluoromethoxy; Z represents hydrogen; or Z and R together form a group -OCF20- in position 2 and 3 of the phenyl ring; X represents oxygen; Y represents hydrogen; R? represents ethyl; R 2 represents hydrogen or methyl; R3 represents hydrogen; and m represents 0. Also important are compounds of formula I, in which Q represents the group R represents trifluoromethyl or trifluoromethoxy; Z represents hydrogen; or Z and R together form a group -OCF20- in position 2 and 3 of the phenyl ring; X represents oxygen; Y represents hydrogen; R x represents ethyl, R 2 and R 3 represent hydrogen; R4 and R5 independently of each other represent hydrogen or methyl; and m represents 1. Also important are the compounds of the formula I, in which Q represents the group R represents trifluoromethyl or trifluoromethoxy; Z represents hydrogen; or Z and R together form a group -OCF20- in position 2 and 3 of the phenyl ring; X represents oxygen; Y represents hydrogen or 3-methyl; Rx represents ethyl; R2, R3, and R5 represent hydrogen; R 4 represents hydrogen or methyl; and m represents 1. As especially preferred compounds those of the formulas la and Ib are to be mentioned. where Q has the meaning indicated in formula I. Especially important among these compounds are those compounds of the formulas la and Ib, where Q represents the group Y represents hydrogen, fluorine, chlorine, methyl, trifluoromethyl, methoxy or cyano; n represents 0, 1, or 2; and n? represents 0 or l. Also preferred are compounds of the formula I in which the β-carbon atom is present in an optically pure form as the (-) enantiomer. The process according to the invention for the preparation of the compounds of the formula I is carried out analogously to known processes and is characterized in that a) for the preparation of the compounds of the formula I, a compound of the formula II where R, Z, X and X have the meaning indicated in formula I, optionally in the presence of a catalyst in an inert organic solvent, with a benzyl isocyanate of formula III where R 2, R 3, R 4 R 5, Q and i have the meanings indicated in formula I in the presence or absence of a catalyst in an organic solvent b) is chloroformil a compound of formula II firstly under usual conditions, preferably with phosgene or diphosgene, to obtain a compound of the formula IV where in the formulas II and IV the radicals R, Z, Rx and X have the meaning indicated in formula I, and then this product is allowed to react with an amine of the formula V where R2, R3, R4, R5, Q and have the meaning indicated under formula I, in an inert organic solvent in the presence of a proton scavenger, for example tertiary amine or pyridine. The variants of procedure a) and b) respond to Reaction Scheme 1. of Reaction l; The addition reaction according to the variant of the a) can be conveniently carried out if the alcohol of the formula II and the isocyanate of the III are added in an inert aprotic organic solvent such as an athiphatic or cyclic, for example, diethylether, 1,2-ethane, tetrahydrofuran or dioxane, or a hydrocarbon or chlorinated, such as for example methylene chloride, or an aromatic, for example toluene or xylene or an ester, for example an ethyl acetate in the presence of a dor, for example 4-N, N-dimethylaminopyridine, mine, dibutyltin dilaurate and / or dibutyltin diacetate, preferably at temperatures ranging from 20 ° C to the reflux temperature of the reaction mixture. In the process variant b) the chloroformate of formula IV is allowed to react with the amine of formula V conveniently in an inert aprotic organic solvent in the presence of organic, in a manner analogous to that indicated in the variant of process a), at temperatures between -20 ° C and + 40 ° C, preferably between + 5 ° C and + 20 ° C. The reaction mixture obtained is washed during the preparation, preferably with water and dilute acid, in order to be able to separate the secondary products of amine as salts. The alcohols of the formula II (lia, Xx = -0- or -S-, Ilb, and lie) can be prepared according to known conventional procedures (for example, U.S. Patent Application published for opposition US-A-5,099,059 and Patent WO 94/10132), such as, for example, according to Reaction Scheme 2, which is presented below. ITTGT? I ^ rt? * 1?, N? • H The preparation of the intermediate product of the formula Ilia can also be carried out in the presence of lithium hydroxide onhydrate and in the absence of solvents under pressure, as is described in World Patent WO 94/10132. The alcohols of the formula II can be separated into the enantiomers for example, by means of liquid chromatography in chiral carrier materials, for example by HPLC in Chiracel-OD-H (Daicel) and 2 percent isopropanol in normal hexane as eluent . Another possibility for obtaining enantiomerically pure alcohols of the formula II is the enantioselective hydrogenation of α-phenoxyketones with BINAP-Ru (II) catalyst complexes. The enantiomer (-) of the compounds of the formula II is to be understood as the optical antipode of the formula lie, which is eluted first, ie before the (+) enantiomer, by means of an HPLC on a Chiracel-OD- column. H of Daicel with the mixture of normal hexane and 2 percent isopropanol as eluent, or that are formed in the enantioselective hydrogenation of a-phenoxyketone, catalyst complex Ru2Cl4 [(R) -BINAP] 2 [N (C2H5) 3] in excessive amounts (enantiomer excess up to> 96 percent (Reaction Scheme 2a) The process according to the invention for the preparation of optically active compounds of the formula ° =). where R, Rlf X and Z have the meaning indicated in claim 1 and the β-carbon atom is presented in optically pure form as the (-) enantiomer, characterized in that a compound of the formula VIII is subjected where R, Rx, X and Z have the indicated meaning, to a hydrogenation reaction catalyzed by (R) -BINAP-Ru (II) in an alcohol solvent, such as for example methanol or ethanol, optionally in the presence of a catalytic amount of a protonic acid such as for example hydrochloric acid or nitric acid. The process for the enantioselective hydrogenation of α-phenoxyketones of the formula VIII with catalysts (R) -BINAP-Ru (II) is carried out according to the Scheme of Reaction 2a. Reaction Scheme 2a: VIII .. _ llcrt anticr.erc (-) Enantioselectively homogeneous hydrogenations of α-functionalized ketones with complexes of BINAP-Ru (II) catalysts are known and are described for example in J. Am. Chem. Soc. 110, 629 (1988). The enantioselective hydrogenation reaction according to the invention starts from the ketones of the formula VIII and is new. Ketones of formula VIII are known or can be prepared according to known methods such as for example those described in J. Am. Chem. Soc. 68, 38 (1946). The enantioselective hydrogenation reaction is advantageously carried out in alcohols, such as for example R6-OH, where R6 represents alkyl of 1 to 4 carbon atoms, especially in methanol or ethanol. As a catalyst, BINAP-Ru (II) complexes are applied, such as those described in U.S. Patent Application published for opposition ÜS-A-4,691,037, but especially Ru2Cl4 [(R) -2, 2'-bis (diphenylphosphino ) -l, l'-dynaphthyl] 2 [N (C2H5) 3] = Ru2Cl4 [(R) -BINAP] 2 [N (C2H5) 3]. In this, the concentration of the catalyst complex for the development of enantioselective hydrogenation is not very critical. As co-catalyst, a protonic acid, such as, for example, hydrochloric acid or nitric acid, may also be added. The hydrogenation is preferably carried out at pressures ranging from atmospheric pressure to 100 bar, especially under weakly increased pressure, up to 80 bar and at temperatures ranging from 10 ° C to the boiling point of the solvent used, preferably at temperatures between 20 and 20 bar. ° C and 40 ° C. Under conventional hydrogenation conditions in dilute alcoholic solutions R6-OH, where R6 represents alkyl of 1 to 4 carbon atoms for example a concentration of 1.0 to 1.2 molar of the ketone of the formula VIII, it is formed as a stable undesired by-product, up to 30 percent in varying amounts, the acetal of formula IX. This acetal is also formed in hydrogenations without the addition of acid. The aforementioned formation of acetals in certain metal complexes, especially in Ru (II) complexes, is analyzed, for example, in J. Organomet. Chem. 415, 127 (1991) and Synlett 1993, 751. According to J. Am. Chem. Soc. 117, 4423 (1995) the formation of acetal in the course of the enantioselective hydrogenation of β-ketoesters in the presence of i-Pr-BPE-Ru (II) as a catalyst can be suppressed by the addition of water (10 percent water-methanol mre). It has now surprisingly been found that with an increase in the concentration of ketone of formula VIII in the hydrogenation solution, the formation of acetal can be suppressed to a large extent or completely; for example in an approximately 30 percent hydrogenation solution (concentration of about 1.3 molar of ketone of formula VIII), for example only a maximum of 20 percent of acetal of formula IX and in a hydrogenation solution are formed. Approximately 65 percent (concentration of about 2.8 molar of the ketone of formula VIII) does not form any acetal of formula IX. The crude alcohol yield of formula II generally amounts to > 90 percent, where under the indicated reaction conditions the excess of enantiomers of the desired enantiomer (-) lie goes up to > 96 percent depending on the substituents R, R ^ X and Z. In this, the absolute configuration (not known in the present case) of the alcohol formed is determined by means of the configuration of the catalyst complex employed. In the enantioselective hydrogenation process according to the invention, the use of the RuCl [(R) -BINAP] 2 [N (C2H5) 3] complex leads mainly to the desired enantiomeric (-) alcohol of the formula lie. The optically pure alcohols of the formula lie (enantiomers (-)) are new and therefore also constitute a purpose of the present invention. The enantioselective synthesis of the optically active compounds of the formula I in position β with respect to the phenyl-X group (enantiomers (-)) of the corresponding optically active alcohols of the formula lie (enantiomers (-)) can be carried out by example analogously to the process variants described in a) and b) (Reaction Scheme 1). The isocyanates of the formula III can be purchased or can be prepared analogously to known processes, such as those described for example in Houben-Weyl, "Methoden der Organischen Chemie", Vol. VIII, Seiten 119 ff, Thieme-Verlag Stuttgart, 1952. Amines of formula V can be purchased or can be prepared analogously to known processes, such as those described for example in Houben-Weyl, "Methoden der Organischen Chemie", Vol. XI (1), Thieme-Verlag Stuttgart, 1957. The preparation of the chloroformate derivatives of the formula IV is carried out according to methods known per se, such as those described, for example, in US Patent Applications Published for Opposition US-A-5,099,059; US-A-5, 078,783, and in World Patent 94/10132. The compounds of the formulas I, lía, Ilb, líe, and IV can be isolated and purified by methods known per se. It is also usual for the person skilled in the art in which sequence certain reactions are suitably carried out under the variants of processes a) and b), in order to prevent possible secondary reactions. Insofar as selective synthesis is not carried out to isolate pure isomers, the product can be presented as a mixture of two or more isomers. The isomers can be prepared according to methods known per se. The intermediary products of the formula Ilb where R x and X have the meaning indicated under formula I, are known from World Patent WO 94/10132. For the intermediate products of formulas II and IV the same preferences apply as for the compounds of formula I. The starting compounds of formulas VI and VII necessary for the preparation process are known or can be prepared according to different procedures known from the literature, for example for compounds of the formula Via according to the following Reaction Scheme 3.

Reaction Scheme 3: X Via The preparation of the required initial compound of the formula X is described in the published European patent application for opposition EP-A-0, 198, 797. The formulations, ie the compositions, preparations or products containing the substance of the formula I and optionally one or more solid or liquid auxiliary substances are prepared in the known manner, for example by intimately mixing and / or grinding the active ingredients with diluents, such as, for example, solvents, solid carrier substances or optionally surface activity (surfactants). Suitable solvents are: aromatic hydrocarbons, especially the fractions of 8 to 12 carbon atoms such as mixtures of alkylbenzene, for example mixtures of xylenes, or alkylated naphthalenes; aliphatic and cycloaliphatic hydrocarbons, such as paraffin, cyclohexane or tetrahydronaphthalene; alcohols, such as ethanol, propanol, or butanol. Glycols, as well as ethers and esters, such as propylene glycol or dipropylene glycol ether, ketones, such as cyclohexanone, isophorone or diacetone alcohol, highly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or water. Vegetable oils, as well as their esters, such as rapeseed, castor oil or soybean oil. Eventually also silicone oils. As solid carrier substances, for example for dusts and dispersible powders, natural rock powders, such as calcite, talc, kaolin, montmorillonite or attapulgite, are generally used. To improve the physical qualities, highly dispersed silicic acids or highly dispersed absorbent polymers can also be added. As carriers in adsorbent particles for granulates, porous types, such as, for example, pumice, brick powder, sepiolite or bentonite, are suitable. As nonabsorbent carrier materials, for example calcite or sand. In addition, a large number of pregranulated materials of inorganic or organic nature, such as dolomite or pulverized plant residues, can also be used. As surfactant compounds, they come into consideration according to the type of active ingredient to be formulated of the formula I, nonionic, cationic, and / or anionic surfactants, with good emulsifying, dispersing and wetting qualities. Surfactant mixtures are also to be understood as surfactants. Suitable anionic surfactants can be both so-called water-soluble soaps and also water-soluble synthetic surface-active compounds. As soaps, mention may be made of alkali metal salts, alkaline earth metal salts or substituted or unsubstituted ammonium salts of higher fatty acids of 10 to 22 carbon atoms, such as, for example, the sodium or potassium salts of oleic or stearic acid. , or mixtures of natural fatty acids, which can be obtained, for example, from coconut or tallow oil. In addition, methyl taurine salts of fatty acids should also be mentioned. However, the so-called synthetic surfactants, especially fatty alcohol sulfonates, fatty alcohol sulfates, sulfonated benzimidazole derivatives or alkylaryl sulphonates are more frequently used. Sulfonates or sulfates of fatty alcohols are generally present in the form of alkali metal salts, alkaline earth metal salts, or substituted or unsubstituted ammonium salts, they have an alkyl radical having 8 to 22 carbon atoms, where alkyl also includes the alkyl portion of the acyl radicals, for example the sodium or calcium salt of lignosulfonic acid, of the dodecylsulfuric ester or of a mixture of fatty alcohol sulfates prepared from natural fatty acids. This group also includes the sulfuric ester and sulfonic acid salts of fatty alcohol-ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain two sulfonyl groups and a fatty acid radical of 8 to 22 carbon atoms. Alkylaryl sulphonates are, for example, the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or a condensation product of naphthalenesulfonic acid formaldehyde. In addition, the corresponding phosphates, such as, for example, the salts of the phosphoric ester of an adduct of p-nonylphenol- (4-14) ethylene oxide or phospholipids, are also suitable. Suitable as nonionic surfactants are polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which may contain from 3 to 30 glycol ether groups and from 8 to 20 carbon atoms. in the hydrocarbon radical (aliphatic) and from 6 to 18 carbon atoms in the alkyl radical of the alkylphenols. Other suitable nonionic surfactants are the adducts of polyethylene oxide and of the solubles, which contain from 20 to 250 ethylene glycol ether groups and from 10 to 100 propylene glycol ether groups, with polypropylene glycol, ethylene diamine propylene glycol and alkyl polypropylene glycol with 1 to 10 carbon atoms. in the chain of alkyl. The compounds mentioned generally contain from 1 to 5 ethylene glycol units per unit of propylene glycol. Examples of nonionic surfactants include nonylphenol polyethoxyethanols, castor oil polyglycol ether, polypropylene-polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and oxylphenoxypolyethoxyethanol.The corresponding fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate, are also considered. In the case of cationic surfactants, it is above all quaternary ammonium salts, which have as substituents N, at least one alkyl radical of 8 to 22 carbon atoms; and as other substituents contain lower alkyl, optionally halogenated radicals, benzyl or hydroxyalkyl lower radicals. The salts are preferably present as halides, methyl sulfates or ethyl sulfates, for example stearyltrimethylammonium chloride or benzyl-di- (2-chloroethyl) -ethylammonium bromide. The surfactants customary in the formulation technique are described, among others, in the following publications. "Me Cutcheon's Detergents and Emulsifiers Annual," Me Publishing Corp., Glen Rock, New Jersey, 1988. M. and J. Ash, "Encyclopedia of Surfactants," Vol. I-III, Chemical Publishing Co., New York, 1980 -1981. Dr. Helmut Stache "Tensid-Taschenbuch", Cari Hanser Verlag, Munich / Vienna 1981. Herbicidal preparations generally contain between 0.1 and 99 percent especially between 0.1 and 95 percent of the active ingredient of formula I, between 1 and 99 percent of an auxiliary substance solid or liquid and between 0 and 25 percent, especially between 0.1 and 25 percent of a surfactant. While the concentrated compositions are preferred as commercial merchandise, the final consumer generally employs diluted compositions. The compositions may also contain other aggregates such as stabilizers, for example, optionally epoxidized vegetable oils (coconut oil, epoxidized rapeseed or soybean oil), defoamers, for example silicone oil, preservatives, viscosity regulators, adherent binders, as fertilizers or other active ingredients to obtain special effects. Preferred formulations have especially the following composition: (% = weight percentage) Emulsifiable concentrates Active ingredient 1 to 90%, preferably 5 to 50% Surfactant 5 to 30%, preferably 10 to 20% Liquid carrier agent 15 to 94%, preferably 70 to 85% Dusting agents Active ingredient 0.1 to 10%, preferably 0.1 to 1% Solid carrier agent 99.9 to 90%, preferably 99.9 to 99% Concentrates for suspensions: Active ingredient 5 to 75%, preferably 10 to 50% Water 94 to 24%, preferably 88 to 30% Surfactant 1 to 40%, preferably 2 to 30% Wettable powder Active ingredient 0.5 to 90%, preferably 1 to 80% Surfactant 0.5 to 20%, preferably 1 to 15% Solid carrier material 5 to 95%, preferably 15 to 90% Granules Active ingredient 0.5 to 30%, preferably 3 to 15% Solid carrier material 99.5 to 70%, preferably 9785% A. Examples of formulations for the active ingredients of formula I (% »Percentage by weight) 1. Wettable powders a) b) Or active ingredient according to Tables 1-6 20% 50% 0.5% Lignosulfone or sodium 5% 5% 5% Sodium lauryl sulphonate 3% - Sodium diisobutyl naphthalenesulfonate - 6% 6% Octyl phenol polyethylene glycol ether 2% 2 % (7-8 moles of ethylene acid) Highly dispersed silica 5% 27% 27% Kaolin 67 Sodium chloride - - 59.5% The active ingredient mixes well with the auxiliary substances and is milled well in a suitable mill. Wettable powders are obtained which can be diluted with water to obtain suspensions of any desired concentration. 2. Concentrates for emulsions a) b) Active ingredient according to Tables 1-6 10% 1% Calcium dodecylbenzenesulfonate 3% 3% Octylphenolpolyethyleneglycol ether 3% 3% (4-5 moles of ethylene oxide) Polyethylene glycol ether of castor oil 4% 4 % (36 moles of ethylene oxide) Cyclohexanone 30% 10% Mixture of xylenes 50% 79% Emulsions of any desired concentration can be prepared from the concentrates by dilution with water. 3. Dusting agents a) b) Active ingredient according to Tables 1-6 0.1% 1% Talcum 99.9% Kaolin - 99% Intimate mixing of the carrier substance with the active ingredient provides ready-to-use dusts. 4_. Granulate for extruder a) b) Active ingredient according to Tables 1-6 10% 1% Sodium lignosulfonate 2% 2% Carboxymethylcellulose 1% 1% Kaolin 87% 96% The active ingredient is mixed with the auxiliary substances, milled and moistened with water. This mixture is extruded and then dried in the air stream.

. Coated granules Active ingredient according to Tables 1-6 3% Polyethylene glycol (PM200) 3% Kaolin 94% The finely ground active ingredient is applied evenly on the kaolin moistened with polyethylene glycol in a mixer. In this way, powder-free coated granules are obtained. 6. Concentrate for suspensions a) b) Active ingredient according to Tables 1-6 5% 40% Ethylene glycol 10% 10% Nonylphenyl polyethylene glycol ether 1% 6% (15 moles of ethylene oxide) Sodium lignosulfonate 5% 10% Carboxymethylcellulose 1% 1% Aqueous solution of formaldehyde at 37% 0.2% 0.2% Silicone oil in the form of an emulsion 00..88 %% 0.8% aqueous at 75% Water 77% 32% The finely ground active ingredient is intimately mixed with the auxiliary substances. In this way, a concentrate for suspensions is obtained, from which suspensions of any desired concentration can be prepared by means of dilution with water. 7. Saline solution Active ingredient according to Tables 1-6 5% Isopropylamine 1% Octylphenolpolyethyleneglycol ether 91% (78 moles of ethylene oxide) The compounds of the formula I are applied in unaltered form, as they are obtained from the synthesis, or preferably as compositions together with the conventional auxiliary agents in the formulation technique and are therefore prepared in the manner known per se as, for example, concentrates. for emulsions, solutions for direct spraying or for diluting, diluted emulsions, wettable powders, soluble powders, dusts, granules and also encapsulated in polymeric substances for example. The application procedures such as spraying, spraying, dusting, dispersing or watering are selected, as well as the type of composition, according to the desired objectives and the given conditions. The application quantities range generally between 0.005 and 2 kilograms per hectare, preferably between 0.01 and 1 kilograms per hectare.

B. Preparation examples Example Hl; l- (3-trifluoromethylphenoxy) -2-butanol (p r or d u c t or intermediate.

C 40.5 grams of 3-hydroxybenzotrifluoride, 18.0 grams of a-butylene oxide, and 1.0 grams of lithium hydroxide monohydrate are heated in a pump tube (pressure vessel) for 16 hours at 140 ° C. After cooling the reaction vessel, the reaction mixture is dissolved in 200 milliliters of ethyl acetate, the organic phase is washed with water, and then dried over sodium sulfate. After concentrating, the desired product, l- (3-trifluoromethylphenoxy) -2-butanol, is obtained in a yield of 54.0 grams and with a high purity. The product is still applied without further purification in the next reaction.

Example H2: 1-f3-chlorophenoxy) -2-butanol (intermediate) Obtained analogously to Example Hl using 51.4 grams of 3-chlorophenol, 28.8 grams of a-butylene oxide, and 1.0 grams of lithium hydroxide monohydrate , oil, in a yield of 71.4 grams; boiling point 83-84 ° C / 0.04 Torr.

Example H3: l- (3-cyanophenoxy) -2-butanol (intermediate product) Obtained analogously to that described in Example Hl using 20.7 grams of 3-cyanophenol, 13.8 grams of a-butylene oxide and 0.5 grams of lithium hydroxide monohydrate, oil in a yield of 25.9 grams; boiling point 116-118 ° C / 0.04 Torr.

Example H4: 0- (3-trifluoromethylphenoxy) -2-butyl chloroformate (intermediate) 46.8 grams of 1- (3-trifluoromethylphenoxy) -butan-2-ol are mixed in 200 milliliters of toluene with 125 milliliters of a toluene solution of 1.93 molar phosgene, and 0.5 milliliters of N, N-dimethylformamide. After the slightly exothermic reaction is heated for 8 hours at 60 ° C. After concentrating the reaction mixture, the desired product, the chloroformate of 0- (3-trifluoromethylphenoxy) -2-butyl, which is applied in the next reaction without further purification, is obtained quantitatively.

Example H5: 0-f l-f3-trifluoromethylphenoxy) -2-butyl-N- (2-phenylethyl) carbamate Et O OCH2CHO-C-NH-CH2-CH2- (? __ fC (? R, -01 -) To 2.9 grams (0.01 moles of O- (3-trifluoromethylphenoxy) -2-butyl chloroformate in 20 milliliters of methylene chloride is added dropwise to a solution of 1.2 grams (0.01 moles) of 2-phenylethylamine and 1.1 grams (0.011 moles). ) of triethylamine in 20 milliliters of methylene chloride, After 14 hours the solution is poured into cold dilute hydrochloric acid, the organic phase is separated, washed with water, dried with sodium sulfate and concentrated in a rotary evaporator. The pure product is obtained by means of column chromatography on silica gel with ethyl acetate / hexane, 1/3, as an eluent and allows obtaining 3.4 grams (theoretical 80.5 percent) of a colorless oil with an index of refraction nD25 1.5015 The biologically active (-) isomer (the chromatographic separation in the two isomers (+) and (-) takes place in the alcohol stage of formula II) has a boiling point of 49-50 ° C .

Example H6: (-) - Enantiomer of 1- (3-trifluoromethylphenoxy) -butan-2-ol (intermediate) Transfer successively with a steel capillary to a steel autoclave under argon, 87.9 grams of l- (3-trifluoromethylphenoxy) butan-2-one dissolved in 130 milliliters of methanol and 0.641 grams of Ru2Cl4 [(R) -2, 2 '-bis (diphenylphosphino) -l, 1-dinaphthyl] 2 [N (C2H5] - Ru2Cl4 [(R) -BINAP] 2 [N (C2H5) 3] and 1.2 milliliters of 1N hydrochloric acid in three cycles (20 bar, atmospheric pressure) the inert gas of argon is displaced by hydrogen and then hydrogenated under 80 bar of hydrogen pressure at 20 ° C. After 69 hours the absorption of hydrogen has finished The reaction mixture is extracted from the autoclave The residue obtained is dissolved in ethyl acetate / hexane, 1/4, and to remove the catalyst, it is filtered through a short silica gel column after evaporation. The collected fractions obtained the desired product with a yield of 87.9 grams (99 percent of the theoretical co), refractive index nD221.4611; [a] 20365-18.7 ± 0.2 ° (c = 1.0 in methanol). The purity of the (-) enantiomer is measured by HPLC on a Chiracel-OD-H column (4.6 x 250 millimeters) of Daicel with the mixture of normal hexane and 2 percent isopropanol as eluent. The excess of the enantiomer (ee) is 94.2 percent (enantiomer (-)). Under the indicated HPLC chromatographic conditions, the (-) enantiomer is eluted first, ie before the enantiomer (+) In an analogous manner, the compounds of the formula I are prepared, which are indicated below in Tables 1 to 6.

The enantiomers (-) indicated in the following Tables 1 and 2 refer to the asymmetric carbon atom in the β position with respect to the phenyl-X group in the compounds of the formula I and are prepared from the corresponding enantiomeric alcohols (-) of the formula lie.

Table 1: Compounds of the formula le Csrnp. R X n Y Rj R2 R3 R4 R5 Physical dates 1. 1 CF3 H 0 H Et H H H H? Q 1-5015 1. 2 CF3 H 0 1 2-C1 Et H H H H? Q 1.5084 1. 3 CF3 H 0 H Me H H H H 1.4 CF3 H 0 1 2-Me Et H H H H? Q 1.5067 1. 5 CF3 H 0 H Et H H Me H? Q 1.5025 1. 6 CF3 H 0 H Et H Me H H P. f. 4S-58 ° C 1. 7 CF3 Hs H Et HHHH 1.8 CF3 H 0 1 2-CF3 Et HHHH '1.9 CF3 H 0 1 3-C1 Et HHHH 1.10 CF3 H 0 1 4-F Et HHHH 1.11 CF3 H 0 H Et HH Et H 1.12 CF3 H 0 H Et H Me Me H 1.13 CF3 H 0 H Et HH Me Me 1.14 OCF3 H 0 H Et HHHH 1.15 OCF3 H 0 1 2-F Et HHHH 1.16 OCF3 H 0. 1 2-Me Et HHHH 1.17 OCF3 H 0 1 2 -Me Et HH Me H 1.18 CN H 0 H Et HHHH 1.19 N02 H 0 H Et HHHH 1.20 Cl H 0 H Et HHHH 1.21 -O-CF O- 0 H Et HHHH 1.22 -O-CF • 2-0- 0 1 2-Me Et HHHH 1.23 F3 H 0 1 2-C1 Et HH Me H n Q I.51 13 1. 24 CF3 H 0 1 2-C1 Et H H Me Me n n l.5135 R X n Y Ri R: 3 ^ 5 ^^ s physical i 25 OCHF? -I 0 H Et H H H H 1 26 CF3 H 0 H Et H H H H P. f. 49-50 ° C: (Enantiomer (-) 27 CF3 H O H Et H H Me H Oil: Enantiomer (-) Table 2: Compounds of the formula Id Corp. R Z X nt Y Ri R2 R3 Physical data 2. 1 CF3 H 0 H Et HH no 1,4892 2.2 CF3 H 0 H Et Me H 2.3 F3 HSH Et HH 2.4 OCF3 H 0 H Et HH 2.5 CF3 H 0 1 5-C1 Et HH 45-48 ° C 2.6 CF3 H 0 1 3 -Mc Et HH 60-62 ° C 2.7 CF3 H 0 l 3-C1 Et HH 68-70 ° C 2.8 -0-CF2-0- 0 H Et HH 2.9 OCF3 H 0 1 3-Me Et HH 68 ° C; Enantianero (-) 2. 10 OCF3 H 0 1 3-C1 Et H H 2.11 CF3 H 0 H Et H H 65-66 ° C; Enantißmero (. 2. 12 CF3 H 0 1 3-Me The H H 77-78 ° C; Enantidome (-Table 3: Compounds of the formula le r- -. R Z X n l Y? R2 R3 R4 R5 Physical data 3. 1 CF3 H 0 H Et H H H H Oil 3. 2 CF3 H 0 1 3-Me Et H H H H Oil CF3 H 0 1 3-Cl Et H H H H 3.4 CF3 H 0 H Et H H Me H Oil 3. 5 CF3 H 0 1 3-Me Et H H Me H 3.6 CF3 H 0 1 3-Cl Et H H Me H 3.7 CF3 H 0 H Et H H Me Me 3.8 -OCF 20- 0 H Et H H H H 3.9 CF 3 HSH Et H H H H 3.10 OCF 3 H 0 H Et HHHH 3.11 OCF3 H 0 H Et H H Me H 3.12 OCF 3 H 0 1 3-Me Et H H H H 3.13 OCF 3 H 0 1 3-Me Et H H Me H Table 4: Compounds of the formula If Coa ?. R Z X nj Y l R2 3 Physical data 4. 1 CF3 H O H Et H H 63-65 ° C 4.2 CF3 H 0 H Et Me H 4.3 OCF3 H 0 H Et H H Table 5: Compounds of the formula Ig R2 R4? • V-X-CH2-C iH-0- Yn, C-N-C-C (Ig) H I | R3 R5 Comp. R Z X nj Y Rl R2 3 R4 R5 Physical data N ° . 1 CF3 H 0 H Et HHHH 62-64 ° C 5.2 CF3 H 0 H Et HH Me H 52-53 ° C 5.3 CF3 H 0 H Et HH Me Me 5.4 OCF3 H 0 H Et HHHH 5.5 -OCF20- 0 H Et HHHH Table 6; Compounds of the formula Ih I run. R X n Rj R R3 R4 5 Physical data N ° 6. 1 CF3 H O H Et H H H H Oil 6.2 OCF3 H 0 1 3-Me Et H H H H 6.3 CF3 H 0 H Et H H Me H Oil 6.4 OCF, H 0 H Et H H Me H Table 7: Compounds of the formula lie (enaptimers (-)) Physical baths 7. 1 CF3 H 0 CH3 7.2 F3 H 0 C2H5 n ^ 1.4611 7. 3 F3 H 0 n-C3H7 7.4 F3 H 0 i-C3H7 7.5 OCF3 H 0 CH3 7.6 OCF3 H 0 C2H5 n ^ 1.4515 7. 7 OCF3 H 0 n-C3H7 7.8 OCF3 H 0 i-C3H7 7.9 -OCF20- 0 CH3 7.10 -OCF20- 0 C2H5 C. Biological examples Example Bl: Description of the test to determine the herbicidal action in pre-emergence The monocotyledonous and dicotyledonous test plants are planted in plastic pots with standard soil. Immediately after sowing, the test substances in aqueous suspension, prepared from a 25 percent wettable powder (Formulation Example 1), are sprayed in accordance with the dosage of 2 kilograms of active ingredient per hectare (500 liters of water per hectare). Next, the test plants are grown in the greenhouse under optimal conditions. The test is evaluated after three weeks with a scale of values of 9 levels (1 = complete damage, 9 = no damage). Valuation levels from 1 to 4 (especially from 1 to 3) mean that a good to very good herbicidal action occurs. The same result is obtained with a concentrated wettable powder (Formulation Example 3), with a dispersible granulate (Formulation Example 4), with an emulsifiable concentrate (Formulation Example 2) or with a concentrate for suspensions (Formulation Example 6) . The test plants were: Setaria, Sinapis, Stellaria. In this test the compounds of the formula I according to the examples in Table 1 show a strong herbicidal action. Examples to demonstrate the good herbicidal action of the compounds of the formula I are presented in Table Bl: Table Bl: Action in pre-emergency -O:! 1-- Dosage Se? Ap :? Sinapis St laria 1. 1 2 1 1 1.2 2 1 1 1.4 2 2 1 1.5 2 2 1 1.23 2 j 1 1.26 2 1 1 1.27 2 1 1 2.1 2 2 .5 2.6 2 1 (r-acema o) 2.7 2 2 (racemate) 2.11 2 1 3.1 2 2 2 3.2 2 2 3.4 2 2 5.2 2 2 2 6.1 2 1 1 6.3 9 1 1 Example B2: Description of the test to determine the post-emergence herbicidal action (contact herbicide) The monocotyledonous test plants are grown and dicotyledonous in the greenhouse in plastic pots with standard soil and in the stadium from 4 to 6 leaves are sprayed with an aqueous suspension, prepared from a 25 percent wettable powder (Formulation Example 1), of the test substances, corresponding to a dosage of 2 kilograms of active ingredient per hectare (500 liters of water per hectare). Then, the test plants continue to be cultivated in the greenhouse under optimal conditions. After about 18 days the test is evaluated with a scale of values of 9 levels (1 = complete damage, 9 = no damage). Valuation levels from 1 to 4 (especially from 1 to 3) mean that a good to very good herbicidal action occurs. The same result is obtained with a concentrated wettable powder (Formulation Example 3), a dispersible granulate (Formulation Example 4), an emulsifiable concentrate (Formulation Example 2), or a concentrate for suspensions (Formulation Example 6). The test plants were: Setaria, Sinapis, Stellaria. Also in this test the compounds of the formula I according to the examples in Table 1 show a good herbicidal action.

Examples to demonstrate the good herbicidal action of the compounds of the formula I are presented in Table B2.

Table B2: Post-emergency action. op.p.No Dosage Setaria Sinapis Stellai (gSA./ha] 1. 4 2 4 1 4 1.5 2 4 1 4 1.26 2 3 1 3 2.1 2 4 2 4 2.11 2 3 1 4 6.1 2 2 1 2 6.3 2 4 2 3

Claims (33)

1. A compound of the formula I where: Q represents a group -, R represents halogen, trifluoromethyl, cyano, nitro or haloalkoxy of 1 to 3 carbon atoms; Z represents hydrogen or halogen; or Z and R together form a group -? CF0 at position 2 and 3 of the phenyl ring; i represents alkyl of 1 to 5 carbon atoms; R2, R3, R, and R5 independently of each other represent hydrogen, methyl or ethyl; X represents oxygen, sulfur, -SO- or -S02-; Y represents hydrogen, halogen, alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, or cyano; n represents 0, 1, or 2; n¿ represents 0, or l; and m represents 0 or 1, with the proviso that m represents 1 when Q represents group (1) or (2); as well as its diastereomers and enantiomers.
2. 2. A compound according to claim 1, wherein R represents chloro, bromo, trifluoromethyl or trifluoromethoxy.
3. 3. A compound according to claim 1, wherein Z represents hydrogen or fluorine.
4. 4. A compound according to claim 1, wherein R2 represents methyl or ethyl.
5. 5. A compound according to claim 1, wherein R2, R3, R4, and R5 independently of each other represent hydrogen or methyl.
6. 6. A compound according to claim 5, wherein R2, R3, and R4 represent hydrogen and R5 represents methyl.
7. 7. A compound according to claim 1, wherein R2, R3, and R4 represent hydrogen, R5 represents methyl or ethyl and Q represents group (1), (2), or (3).
8. 8. A compound according to claim 7, wherein R5 represents methyl and Q represents group (1) or (2).
9. 9. A compound according to claim 1, wherein X represents oxygen or sulfur.
10. 10. A compound according to claim 1, wherein Q represents group (1) or (2); n represents 1; and Y is attached in ortho or meta position with respect to the binding site.
11. 11. A compound according to claim 10, wherein Y is attached ortho to the binding site.
12. 12. A compound according to claim 1, wherein Y represents hydrogen, fluorine, chlorine, methyl, trifluoromethyl, methoxy or cyano.
13. 13. A compound according to claim 1, wherein Q represents group (1); R represents chloro, cyano, nitro, trifluoromethyl, trifluoromethoxy or difluoromethoxy; Z represents hydrogen or Z and R together form a group 0CF20-in position 2 and 3 of the phenyl ring; X represents oxygen or sulfur; Y represents hydrogen, 2-fluoro, 2- or 3-chloro, 2-methyl, or 2-trifluoromethyl; n represents 0 or 1; Rx represents methyl or ethyl; R2 represents hydrogen; and R3, R4, and R5 independently represent hydrogen or methyl.
14. 14. A compound according to claim 1, wherein Q represents the group R represents trifluoromethyl or trifluoromethoxy; Z represents hydrogen; or Z and R together form a group -0CF20- in position 2 and 3 of the phenyl ring; X represents oxygen or sulfur; Y represents hydrogen, 3- or 5-chloro or 3-methyl; R? represents ethyl; R 2 represents hydrogen or methyl; R3 represents hydrogen; and m represents 0.
15. 15. A compound according to claim 1, wherein Q represents the group R represents trifluoromethyl or trifluoromethoxy; Z represents hydrogen; or Z and R together form a -0CF20 group in positions 2 and 3 of the phenyl ring; X represents oxygen or sulfur; Y represents hydrogen, 3-chloro or 3-methyl; R? represents ethyl; R2 and R3 represent hydrogen; R4 and R5 independently of each other represent hydrogen or methyl; and m represents 1.
16. 16. A compound according to claim 1, wherein Q represents the group R represents trifluoromethyl or trifluoromethoxy; Z represents hydrogen; or Z and R together form a group -0CF20- in position 2 and 3 of the phenyl ring; X represents oxygen; Y represents hydrogen; R? represents ethyl; R 2 represents hydrogen or methyl; R3 represents hydrogen; and m represents 0.
17. 17. A compound according to claim 1, wherein Q represents the group
18. R represents trifluoromethyl or trifluoromethoxy; Z represents hydrogen; or Z and R together form a group -OCF20- in position 2 and 3 of the phenyl ring; X represents oxygen; Y represents hydrogen; R x represents ethyl, R, and R 3 represent hydrogen; R4 and R5 independently of each other represent hydrogen or methyl; and m represents 1. 18. A compound according to claim 1, wherein Q represents the group
19. R represents trifluoromethyl or trifluoromethoxy; Z represents hydrogen; or Z and R together form a group -0CFa0- in position 2 and 3 of the phenyl ring; X represents oxygen; Y represents hydrogen or 3-methyl; Rx represents ethyl; R2, R3, and R5 represent hydrogen; R 4 represents hydrogen or methyl; and m represents 1. 19. A compound according to claim 1 of the formula la or Ib where Q has the meaning indicated in claim 1. 20. A compound according to claim 19, wherein Q represents the group
20. Y represents hydrogen, fluorine, chlorine, methyl, trifluoromethyl, methoxy or cyano; n represents 0, 1, or 2; and n represents o or l.
21. 21. A compound according to claim 1, wherein the β-carbon atom is presented in optically pure form as the (-) enantiomer.
22. 22. A process for the preparation of the compounds of the formula I according to claim 1, characterized in that a compound of the formula II is reacted where R, Z, Rj ^ and X have the meaning indicated in claim 1, with a compound of the formula III where R2, R3, R4, R5, Q and m have the meaning indicated in claim 1, optionally in the presence of a catalyst in an inert organic solvent.
23. 23. A process for the preparation of the compounds of the formula I according to claim 1, characterized in that first a compound of the formula II is chloroformilized under usual conditions, preferably with phosgene or diphosgene, to obtain a compound of the formula IV wherein in the formulas II and IV, the radicals R, Z, RL and X have the meaning indicated in claim 1, and then this product is reacted with a compound of the formula V where R2, R3, R4, R5, Q and m have the meaning indicated in claim 1, in an inert organic solvent in the presence of a proton scavenger, such as for example a tertiary amine or pyridine.
24. 24. A herbicidal composition containing a compound of the formula I according to claim 1.
25. 25. A composition according to claim 24, which contains between 0.1 and 95 percent of a compound of the formula I, between 1 and 99 percent of a solid or liquid auxiliary substance and between 0 and 25 percent, especially between 0.1 and 25 percent of a surfactant.
26. 26. A method for combating unwanted plant growth characterized in that a compound of the formula I according to claim 1 or a composition containing this compound in an effective amount is applied on the plants or their place of growth.
27. 27. A method according to claim 26 characterized in that a compound of the formula I is applied in an amount ranging between 0.005 and 2 kilograms per hectare.
28. 28. A method according to claim 26 for selectively controlling pre- or post-emergence weeds in crops of useful plants, especially cereal crops, rice, corn, soybeans, and cotton.
29. 29. The use of a compound of the formula I according to claim 1, to selectively combat in pre- or post-emergence, weeds in crops of useful plants, especially in crops of cereals, rice, corn, soybean and cotton.
30. 30. The use of a composition according to claim 24, to selectively combat in pre- or postemergence, weeds in crops of useful plants, especially in crops of cereals, rice, corn, soybeans, and cotton.
31. 31. A compound of the formula lie where R, Rx, X and Z have the definition indicated in claim 1 and the β-carbon atom is presented in optically pure form as the (-) enantiomer.
32. 32. A compound according to claim 31, wherein R represents chloro, bromo, trifluoromethyl, or trifluoromethoxy; R 'represents methyl or ethyl; X represents oxygen; and Z represents hydrogen or fluorine.
33. 33. A process for the preparation of optically active compounds of the formula lie where R, Rl t X, and Z have the meaning indicated in claim 1, and the β-carbon atom is presented in optically pure form as the (-) enantiomer, characterized in that it is subjected to a compound of the formula VIII where R, Rlf X and Z have the indicated meaning, to a hydrogenation reaction catalyzed with (R) -BINAP-Ru (II) in an alcohol solvent. SUMMARY N-phenyl and substituted N-heteroarylalkylcarbamates of the formula I where: Q represents a group R represents halogen, trifluoromethyl, cyano, nitro or haloalkoxy of 1 to 3 carbon atoms; Z represents hydrogen or halogen; or Z and R together form a -0CF20 group in the 2 and 3 position of the phenyl ring; R represents alkyl of 1 to 5 carbon atoms; R2, 3, R4, and R5 independently of each other represent hydrogen, methyl or ethyl; X represents oxygen, sulfur, -SO- or -S02-; Y represents hydrogen, halogen, alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, or cyano; n represents 0, 1, or 2; represents O, or 1; and m represents 0 or 1, with the proviso that m represents 1 when Q represents group (1) or (2); as well as its diastereomers and enantiomers, present herbicidal qualities in pre- and postemergence. The preparation of these compounds and their use as herbicidal active ingredients are described. * * * * *