MXPA01003066A - Optically active substituted n-aryl-o-aryloxyalkyl-carbamates - Google Patents

Abstract

The invention relates to novel optically active substituted N-aryl-O-aryloxyalkyl-carbamates of general formula (I) in which Ar1 represents an optionally substituted, monocyclic or bicyclic, carbocyclic or heterocyclic grouping from the family of phenyl, naphthyl, tetralinyl, furyl, benzofuryl, thienyl, benzothienyl, pyridinyl, chinolinyl, isochinolinyl or the likewise optionally substituted following grouping (a), whereby A represents alkanediyl which has 1 to 3 carbon atoms and which is optionally substituted by halogen, and whereby the respective possible substituents are preferably selected from the following listing:cyano, nitro, halogen, and each being optionally substituted by halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl respectively having up to 5 carbon atoms;Ar2 represents alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl each having up to 4 carbon atoms and each being optionally substituted by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or (each being optionally substituted by cyano, halogen, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl or C1-C4-alkylsulfonyl) in the aryl which has 6 or 10 carbon atoms and which is substituted in the alkyl groups;R1 represents alkyl which has 1 to 4 carbon atoms and which is optionally substituted by cyano, halogen or C1-C4-alkoxy and R2 represents hydrogen or alkyl which has 1 to 4 carbon atoms and which is optionally substituted by cyano, halogen or C1-C4-alkoxy, whereby the substituents on the carbon atom, on which R1 is bound, are arranged in such a manner that the light polarized in the plane of polarization is turned to the left. The invention also relates to methods for producing the novel compounds and to their use as herbicides.

Description

N-ARIL-O-ARYLOXIALQUIL-CARBAMATES SUBSTITUTED OPTICALLY ACTIVE. Field of the invention. The invention relates to new optically active 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-aryloxyalkyl carbamates have herbicidal properties (see US-A 5 099 059, US-A 5 152 827, US-A 5 194 661). However, the herbicidal activity of these known compounds is not satisfactory from all points of view. Detailed description of the invention. New, optically active substituted N-aryl-O-aryloxyalkyl-carbamates of the general formula (I) have now been found, wherein Ar 1 means a carbocyclic or heterocyclic, monocyclic or bicyclic group, respectively substituted, if appropriate, of the series consisting of phenyl, naphthyl, tetralinyl, furyl, benzofuryl, thienyl, benzothienyl, / pyridinyl, quinolinyl, isoquinolinyl or the grouping, also substituted if necessary - following Ref: 127502 wherein A means alkanediyl having 1 to 3 carbon atoms, optionally substituted by halogen, and where the corresponding possible substituents are preferably chosen from the following enumeration: cyano, nitro, halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl , alkylcarbonyl, alkoxycarbonyl with, respectively, up to 5 carbon atoms, respectively substituted, if appropriate, by halogen, Ar 2 means aryl having 6 or 10 carbon atoms, optionally substituted by nitro, by cyano, by carboxy, by carbamoyl, by thiocarbamoyl , by halogen or by alkyl, by alkoxy, by alkylthio, by alkylsulfinyl, by alkylsulfonyl, by alkylamino, by dialkylamino, by alkylcarbonyl, by alkoxycarbonyl, by alkylaminocarbonyl or by dialkylaminocarbonyl with, respectively, up to 4 carbon atoms in the alkyl groups, (optionally substituted by cyano, by halogen, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms or by alkylsulfonyl with 1 to 4 carbon atoms carbon), R 1 means alkyl having 1 to 4 carbon atoms optionally substituted by cyano, halogen or alkoxy with 1 to 4 carbon atoms, and R 2 represents hydrogen or means alkyl with 1 to 4 carbon atoms substituted in case given by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, with the proviso that in the compounds of the general formula (I) the substituents are arranged on the carbon atom, to which R7 is attached so that the polarized light rotates to the left in the plane of oscillation, that is to say that the compounds of the formula (I) are presented as enantiomers (-). In the definitions the carbon chains, such as alkyl - even in combination with heteroatoms, as in alkoxy - are respectively straight-chain or branched chain. Preferably, Ar 1 denotes one of the groupings mentioned above, where A means methylene or dimethylene (1,2-diyl ethane) respectively substituted, if appropriate, by fluorine and / or by chlorine, and where the respective possible substituents are preferably chosen from the following enumeration: cyano, nitro, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n- , i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propyl-sulfinyl, methylsulfonyl, ethylsulphonyl, n- or i-propylsulphonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl respectively substituted, if appropriate, by fluorine and / or by chlorine. Preferably, Ar 2 means phenyl or naphthyl respectively substituted, if appropriate, by nitro, by cyano, by carboxy, by carbamoyl, by thiocarbamoyl, by fluorine, by chlorine, by bromine, by iodine or by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by n-, i-, s- or t-butoxy, by methylthio, by ethylthio, by n- or i-propylthio, by n-, i-, s- or t - butylthio, for methylsulfinyl, for ethylsulfinyl, for n- or i-propylsulfinyl, for methylsulphonyl, for ethylsulphonyl, for n- or i-propylsulphonyl, for methylamino, for ethylamino, for n- or i-propylamino, for n-, -, s- or t-butylamino, by dimethylamino, by diethylamino, by acetyl, by propionyl, by n- or s-butyroyl, by methoxycarbonyl, by ethoxycarbonyl, by n- or i- propoxycarbonyl, by methylaminocarbonyl, by ethylaminocarbonyl, by n- or i-propylaminocarbonyl, by dimethylaminocarbonyl or by diethylaminocarbonyl (optionally substituted by cyano, by fluorine, by chlorine, by methoxy, by ethoxy, by methylthio, by ethylthio, by methylsulfinyl, by ethylsulfinyl, by methylsulfonyl) or by ethylsulfonyl). Preferably, R1 means methyl, ethyl, n- or i-propyl. Preferably, R2 means hydrogen, methyl, ethyl, n- or i-propyl. Particularly preferably, Ar 1 means phenyl, which contains in the 3-position, a substituent of the series consisting of cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, chloromethyl, fluoro-methyl, dichloromethyl , difluoromethyl, trichloromethyl, trifluoromethyl, methoxy, ethoxy, fluoro-methoxy, difluoromethoxy, chlorofluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy and containing, if appropriate, in another position another substituent according to the preceding enumeration. Particularly preferably, Ar 2 denotes phenyl which is optionally substituted by nitro, cyano, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, by methylthio, by ethylthio, by n- or i-propylthio, by methylsulfinyl, by ethylsulfinyl, by n- or i-propylsulfinyl, by methylsulfonyl, by ethylsulphonyl, by n- or i-propylsulfonyl, by dimethylamino, by acetyl. by propionyl, by methoxycarbonyl, by ethoxycarbonyl or by dimethylaminocarbonyl (respectively substituted, where appropriate, by fluorine or by chlorine). Particularly preferably R1 means methyl or ethyl. Particularly preferably, R 2 is hydrogen, methyl or ethyl. According to the invention, the compounds of the formula (1) are preferred, in which a combination of the meanings indicated above is preferred. According to the invention, the compounds of the formula (I) in which a combination of the meanings indicated above are especially preferred are particularly preferred. The definitions of the residues indicated above in a general manner or in the preferred ranges are valid both for the final products of the formula (I) and also, correspondingly, for the starting materials or 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. Examples of compounds according to the invention of the general formula (I) are indicated in the following groups.

Group 1.

In this case Ar2 has, for example, the meanings indicated below: 2-chloro-3-fluoro-phenyl, 2,3-dichloro-phenyl, 2-chloro-3-bromo-phenyl, 2-chloro-3-methyl-phenyl , 2-chloro-3-ethyl-phenyl, 2-chloro-3-trifluoromethyl-phenyl, 2-chloro-3-cyano-phenyl, 2-chloro-3-methoxy-phenyl, 2-chloro-3-ethoxy-phenyl , 2-chloro-4-fluoro-phenyl, 2,4-dichloro-phenyl, 2-chloro-4-bromo-phenyl, 2-chloro-4-methyl-phenyl, 2-chloro-4-ethyl-phenyl, -chloro-4-trifluoromethyl-phenyl, 2-chloro-4-cyano-phenyl, 2-chloro-4-methoxy-phenyl, 2-chloro-4-ethoxy-phenyl, 2-chloro-5-fluoro-phenyl, , 5-dichloro-phenyl, 2-chloro-5-bromo-phenyl, 2-chloro-5-methyl-phenyl, 2-chloro-5-ethyl-phenyl, 2-chloro-5-trifluoromethyl-phenyl, 2-chloro -5-cyano-phenyl, 2-chloro-5-methoxy-phenyl, 2-chloro-5-ethoxy-phenyl, 2-chloro-6-fluoro-phenyl, 2,6-dichloro-phenyl, 2-chloro-6 -bromo-phenyl, 2-chloro-6-methyl-phenyl, 2-chloro-6-ethyl-phenyl, 2-chloro-6-trifluoromethyl-phenyl, 2-chloro-6-cyano-phenyl, 2-chloro-6 -methoxy-phenyl, 2-chloro-6-ethoxy-phenyl; 2,3-difluoro-phenyl, 2-fluoro-3-chloro-phenyl, 2-fluoro-3-bromo-phenyl, 2-fluoro-3-methyl-phenyl, 2-fluoro-3-ethyl-phenyl, 2- fluorine-3-trifluoromethyl-phenyl, 2-fluoro-3-cyano-phenyl, 2-fluoro-3-methoxy-phenyl, 2-fluoro-3-ethoxy-phenyl, 2,4-difluoro-phenyl, 2-fluoro- 4-chloro-phe nyl, 2-fluoro-4-bromo-phenyl, 2-fluoro-4-methyl-phenyl, 2-fluoro-4-ethyl-phenyl, 2-fluoro-4-trifluoromethyl-phenyl, 2- fluorine-4-cyano-phenyl, 2-fluoro-4-methoxy-phenyl, 2-fluoro-4-ethoxy-phenyl, 2,5-difluoro-phenyl, 2-fluoro-5-chloro-phenyl, 2-fluoro- 5-bromo-phenyl, 2-fluoro-5-methyl-phenyl, 2-fluoro-5-ethyl-phenyl, 2-fluoro-5-trifluoromethyl-phenyl, 2-fluoro-5-cyano-phenyl, 2-fluoro- 5-methoxy-phenyl, 2-fluoro-5-ethoxy-phenyl, 2,6-difluoro-phenyl, 2-fluoro-6-chloro-phenyl, 2-fluoro-6-bromo-phenyl, 2-fluoro-6- methyl-phenyl, 2-fluoro-6-ethyl-phenyl, 2-fluoro-6-trifluoromethyl-phenyl, 2-fluoro-o-cyano-phenyl, 2-fluoro-6-methoxy-phenyl, 2-fluoro-6- ethoxy phenyl; 2-bromo-3-fluoro-phenyl, 2-bromo-3-chloro-phenyl, 2,3-dibromo-phenyl, 2-bromo-3-methyl-phenyl, 2-bromo-3-ethyl-phenyl, 2- bromo-3-trifluoromethyl-phenyl, 2-bromo-3-cyano-phenyl, 2-bromo-3-methoxy-phenyl, 2-bromo-3-ethoxy-phenyl, 2-bromo-4-fluoro-phenyl, 2- bromo-4-chloro-phenyl, 2,4-dibromo-phenyl, 2-bromo-4-methyl-phenyl, 2-bromo-4-ethyl-phenyl, 2-bromo-4-trifluoromethyl-phenyl, 2-bromo- 4-cyano-phenyl, 2-bromo-4-methoxy-phenyl, 2-bromo-4-ethoxy-phenyl, 2-bromo-5-fluoro-phenyl, 2-bromo-5-chloro-phenyl, 2.5- dibromo-phenyl, 2-bromo-5-methyl-phenyl, 2-bromo-5-ethyl-phenyl, 2-bromo-5-trifluoromethyl-phenyl, 2-bromo-5-cyano-phenyl, 2-bromo-5- methoxy-phenyl, 2-bromo-5-ethoxy-phenyl, 2-bromo-6-fluoro-phenyl, 2-bromo-6-chloro-phenyl, 2-bromo-6-bromo-phenyl, 2-bromo-6- methyl-phenyl, 2-bromo-6-ethyl-phenyl, 2-bromo-6-trifluoromethyl-phenyl, 2-bromo-6-cyano-phenyl, 2-bromo-6-methoxy-phenyl, 2-bromo- 6-ethoxy phenyl; 2-methyl-3-fluoro-phenyl, 2-methyl-3-chloro-phenyl, 2-methyl-3-bromo-phenyl, 2,3-dimethyl-phenyl, 2-methyl-3-ethyl-phenyl, 2- methyl-3-trifluoromethyl-phenyl, 2-methyl-3-cyano-phenyl, 2-methyl-3-methoxy-phenyl, 2-methyl-3-ethoxy-phenyl, 2-p-ethyl-4-fluoro-phenyl, 2- methyl-4-chloro-phenyl, 2-methyl-4-bromo-phenyl, 2,4-dimethyl-phenyl, 2-methyl-4-ethyl-phenyl, 2-methyl-4-trifluoromethyl-phenyl, 3-methyl- 4-cyano-phenyl, 2-methyl-4-methoxy-phenyl, 2-methyl-4-ethoxy-phenyl, 2-methyl-5-fluoro-phenyl, 2-methyl-5-chloro-phenyl, 2-methyl- 5-bromo-phenyl, 2,5-dimethyl-phenyl, 2-methyl-5-ethyl-phenyl, 2-methyl-5-trifluoromethyl-phenyl, 2-methyl-5-cyano-phenyl, 2-methyl-5- methoxy-phenyl, 2-methyl-5-ethoxy-phenyl, 2-methyl-6-fluoro-phenyl, 2-methyl-6-chloro-phenyl, 2-methyl-6-bromo-phenyl, 2,6-dimethyl- phenyl, 2-methyl-6-ethyl-phenyl, 2-methyl-6-trifluoromethyl-phenyl, 2-methyl-6-cyano-phenyl, 2-methyl-6-methoxy-phenyl, 2-methyl-6-ethoxy- phenyl: 2-ethyl-3-fluoro-phenyl, 2-ethyl-3-chloro-phenyl, 2-ethyl-3-bromo-phenyl, 2-ethyl-3-methyl-phenyl, 2,3-diethyl-phen ilo, 2-ethyl-3-trifluoromethyl-phenyl, 2-ethyl-3-cyano-phenyl, 2-ethyl-3-methoxy-phenyl, 2-ethyl-3-ethoxy-phenyl, 2-ethyl-4-fluoro- phenyl, 2-ethyl-4-chloro-phenyl, 2-ethyl-4-bromo-phenyl, 2-ethyl-4-methyl-phenyl, 2,4-diethyl-phenyl, 2-ethyl-4-trifluoromethyl-phenyl, 2-ethyl-4-cyano-phenyl, 2-ethyl-4-methoxy-phenyl, 2-ethyl-4-ethoxy-phenyl, 2-ethyl-5-fluoro-phenyl, 2-ethyl-5-chloro-phenyl, 2-ethyl-5-bromo-phenyl, 2-ethyl-5-methyl-phenyl, 2,5-diethyl-phenyl, 2-ethyl-5-trifluoromethyl-phenyl, 2-ethyl-5-cyano-phenyl, 2- ethyl-5-methoxy-phenyl, 2-ethyl-5-ethoxy-phenyl, 2-ethyl-6-fluoro-phenyl, 2-ethyl-6-chloro-phenyl, 2-ethyl-6-bromo-phenyl, 2- elil-6-methyl-phenyl, 2,6-diethyl-phenyl, 2-ethyl-6-trifluoromethyl-phenyl, 2-ethyl-6-cyano-phenyl, 2-ethyl-6-methoxy-phenyl, 2-ethyl- 6-ethoxy-phenyl; 2-trifluoromethyl-3-fluoro-phenyl, 2-trifluoromethyl-3-chloro-phenyl, 2-trifluoromethyl-3-bromo-phenyl, 2-trifluoromethyl-3-methyl-phenyl, 2-trifluoromethyl-3-ethyl-phenyl, 2,3-bis-trifluoromethyl-phenyl, 2-trifluoromethyl-3-cyano-phenyl, 2-trifluoromethyl-3-methoxy-phenyl, 2-trifluoromethyl-3-ethoxy-phenyl, 2-trifluoromethyl-4-fluoro-phenyl, 2-trifluoromethyl-4-chloro-phenyl, 2-trifluoromethyl-4-bromo-phenyl, 2-trifluoromethyl-4-methyl-phenyl, 2-trifluoromethyl-4-ethyl-phenyl, 2,4-bis-trifluoromethyl- phenyl, 2-trifluoromethyl-4-cyano-phenyl, 2-trifluoromethyl-4-methoxy-phenyl, 2-trifluoromethyl-4-ethoxy-phenyl, 2-trifluoromethyl-5-fluoro-phenyl, 2-trifluoromethyl-5-chloro- phenyl, 2-trifluoromethyl-5-bromo-phenyl, 2-trifluoromethyl-5-methyl-phenyl, 2-trifluoromethyl-5-ethyl-phenyl, 2,5-bis-trifluoromethyl-phenyl, 2-trifluoromethyl-5 cyano-phenyl, 2-trifluoromethyl-5-methoxy-phenyl, 2-trifluoromethyl-5-ethoxy-phenyl, 2-trifluoromethyl-6-fluoro-phenyl, 2-trifluoromethyl-6-chloro-phenyl, 2-trifluoromethyl-6 bromo-phenyl, 2-trifluo Rmethyl-6-methyl-phenyl, 2-trifluoromethyl-6-ethyl-phenyl, 2,6-bis-trifluoromethyl-phenyl, 2-trifluoromethyl-6-cyano-phenyl, 2-trifluoromethyl-6-methoxy-phenyl, 2- trifluoromethyl-6-ethoxy-phenyl: 2-cyano-3-fluoro-phenyl, 2-cyano-3-chloro-phenyl, 2-cyano-3-bromo-phenyl, 2-cyano-3-methyl-phenyl, 2- cyano-3-ethyl-phenyl, 2-cyano-3-trifluoromethyl-phenyl, 2,3-dicyano-phenyl, 2-cyano-3-methoxy-phenyl, 2-cyano-3-ethoxy-phenyl, 2-cyano- 4-fluoro-phenyl, 2-cyano-4-chloro-phenyl, 2-cyano-4-bromo-phenyl, 2-cyano-4-methyl-phenyl, 2-cyano-4-ethyl-phenyl, 2-cyano- 4-trifluoromethyl-phenyl, 2,4-dicyano-phenyl, 2-cyano-4-methoxy-phenyl, 2-cyano-4-ethoxy-phenyl, 2-cyano-5-fluoro-phenyl, 2-cyano-5- chloro-phenyl, 2-cyano-5-bromo-phenyl, 2-cyano-5-methyl-phenyl, 2-cyano-5-ethyl-phenyl, 2-cyano-5-trifluoromethyl-phenyl, 2,5-dicyano- phenyl, 2-cyano-5-methoxy-phenyl, 2-cyano-5-ethoxy-phenyl, 2-cyano-o-phorophenyl, 2-cyano-6-chloro-phenyl, 2-cyano-6-bromo -phenyl, 2-cyano-6-methyl-phenyl, 2-cyano-6-ethyl-phenyl, 2-cyano-6-trifluoromethyl-f enyl, 2-cyano-6-cyano-phenyl, 2-cyano-6-methoxy-phenyl, 2-cyano-6-ethoxy-phenyl; 2-methoxy-3-fluoro-phenyl, 2-methoxy-3-chloro-phenyl, 2-methoxy-3-bromo-phenyl, 2-methoxy-3-methyl-phenyl, 2-methoxy-3-ethyl-phenyl, 2-methoxy-3-trifluoromethyl-phenyl, 2-methoxy-3-cyano-phenyl, 2,3-dimethoxy-phenyl, 2-methoxy-3-ethoxy-phenyl, 2-methoxy-4-fluoro-phenyl, 2- methoxy-4-chloro-phenyl, 2-methoxy-4-bromo-phenyl, 2-methoxy-4-methyl-phenyl, 2-methoxy-4-ethyl-phenyl, 2-methoxy-4-trifluoromethyl-phenyl, 2- methoxy-4-cyano-phenyl, 2,4-dimethoxy-phenyl, 2-methoxy-4-ethoxy-phenyl, 2-methoxy-5-fluoro-phenyl, 2-methoxy-5-chloro-phenyl, 2-methoxy- 5-bromo-phenyl, 2-methoxy-5-methyl-phenyl, 2-methoxy-5-ethyl-phenyl, 2-methoxy-5-trifluoromethyl-phenyl, 2-methoxy-5-cyano-phenyl, 2,5- dimethoxy-phenyl, 2-methoxy-5-ethoxy-phenyl, 2-methoxy-6-fluoro-phenyl, 2-methoxy-6-chloro-phenyl, 2-methoxy-6-bromo-phenyl, 2-methoxy-6 methyl-phenyl, 2-methoxy-6-ethyl-phenyl, 2-methoxy-6-trifluoromethyl-phenyl, 2-methoxy-6-cyano-phenyl, 2,6-dimethoxy-phenyl, 2-methoxy-6-ethoxy- phenyl; 2-e-oxo-3-fluoro-phenyl, 2-ethoxy-3-chloro-phenyl, 2-ethoxy-3-bromo-phenyl, 2-ethoxy-3-methyl-phenyl, 2-ethoxy-3-ethyl-phenyl, 2-ethoxy-3-trifluoromethyl-phenyl, 2-ethoxy-3-cyano-phenyl, 2-ethoxy-3-methoxy-phenyl, 2,3-diethoxy-phenyl, 2-ethoxy-4-fluoro-phenyl, 2- ethoxy-4-chloro-phenyl, 2-ethoxy-4-bromo-phenyl, 2-ethoxy-4-methyl-phenyl, 2-ethoxy-4-ethyl-phenyl, 2-ethoxy-4-trifluoromethyl-phenyl, 2- ethoxy-4-cyano-phenyl, 2-ethoxy-4-methoxy-phenyl, 2,4-diethoxy-phenyl, 2-ethoxy-5-fluoro-phenyl, 2-ethoxy-5-chloro-phenyl, 2-ethoxy- 5-bromo-phenyl, 2-ethoxy-5-methyl-phenyl, 2-ethoxy-5-ethyl-phenyl, 2-ethoxy-5-trifluoromethyl-phenyl, 2-ethoxy-5-cyano-phenyl, 2-ethoxy- 5-methoxy-phenyl, 2,5-diethoxy-phenyl, 2-ethoxy-6-fluoro-phenyl, 2-ethoxy-6-chloro-phenyl, 2-ethoxy-6-bromo-phenyl, 2-ethoxy-6- methyl-phenyl, 2-ethoxy-6-ethyl-phenyl, 2-ethoxy-6-trifluoromethyl-phenyl, 2-ethoxy-6-cyano-phenyl, 2-ethoxy-6-methoxy-phenyl, 2,6-diethoxy- phenyl. Group 2.

In this case Ar2 has, in an exemplary way, the meanings indicated above in group 1. Group 3.

In this case Ar2 has, by way of example, the meanings indicated above in group 1. Group 4.

In this case Ar2 has, by way of example, the meanings indicated above in group 1. Group 5.

In this case Ar2 has, by way of example, the meanings indicated above in group 1. Group 6.

In this case Ar2 has, by way of example, the meanings indicated above in group 1.

Group 7.

In this case Ar has, by way of example, the meanings indicated above in group 1. Group 8.

In this case Ar2 has, by way of example, the meanings indicated above in group 1. Group 9.

In this case Ar2 has, by way of example, the meanings indicated above in group 1.

Group 10 In this case Ar2 has, in an exemplary way, the meanings indicated above in group 1. Group 11.

In this case Ar2 has, by way of example, the meanings indicated above in group 1. Group 12.

In this case Ar2 has, by way of example, the meanings indicated above in group 1.

Gpfo 13.

In this case Ar2 has, in an exemplary way, the meanings indicated above in group 1. Group 14.

In this case Ar2 has, by way of example, the meanings indicated above in group 1. Group 15.

In this case Ar2 has, by way of example, the meanings indicated above in group 1.

Group 16 In this case Ar2 has, by way of example, the meanings indicated above in group 1. Group 17.

In this case Ar2 has, by way of example, the meanings indicated above in group 1. Group 18.

In this case Ar2 has, by way of example, the meanings indicated above in group 1.

Group 19 In this case Ar2 has, by way of example, the meanings indicated above in group 1. Group 20.

In this case Ar2 has, in an exemplary way, the meanings indicated above in group 1. Group 21.

In this case, Ar2 has, by way of example, the meanings indicated above in group 1. Particularly preferred are compounds according to groups 1 to 3 with the conditions indicated above.

The most preferred compounds are those corresponding to group 2 with the conditions indicated above. The new substituted N-aryl-O-alkyl-carbamates of the general formula (I) if (a) are reacted arylamines of the general formula (II) H \ Ar¿ N '(II) R2 wherein Ar2 and R2 have the meaning indicated above, with esters of the chloroformic acid of the general formula (III) wherein Ar1 and R1 have the meaning indicated above, optionally in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, or if-in the case where R2 means hydrogen- (b) ) arylisocyanates of the general formula (IV) are reacted .Ar 'Q = C = N' (IV) wherein Ar2 has the meaning indicated above, with substituted alkanols of the general formula (V) wherein Ar1 and R1 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, (-) - [1- (3-methyl-phenoxymethyl) -propyl] -chloroformate and 2-fluoro-6-methyl-aniline are used as starting materials, the development of the reaction in the case of the process (a) according to the invention by means of the following formula scheme: If, for example, (-) - l- (3-trifluoromethyl-phenoxymethyl) -butanol and 2-chloro-5-methoxy-phenylisocyanate are used as starting materials, the development of the reaction in the case of the process may be schematized. (b) according to the invention by means of the following formula scheme: The arylamines to be used as starting materials in the case of the process (a) according to the invention for the preparation of the compounds of the general formula (I) are generally defined by the formula (II). In the general formula (II), Ar2 and R2 preferably have those meanings which have already been mentioned above, preferably or more preferably for Ar2 and R2 in relation to the description of the compounds according to the invention of the general formula (I ). The starting materials of the general formula (II) are organic chemical products for known syntheses. The esters of chloroformic acid to be further employed as starting materials in the case of process (a) according to the invention are generally defined by means of formula (III). In the general formula (III), Ar1 and R1 preferably have those meanings which have already been mentioned above, preferably or particularly preferably for Ar1 and R1 in connection with the description of the compounds according to the invention of the general formula (I ). The starting materials of the general formula (III) are known and / or can be prepared according to processes known per se (see US-A-5 099 059, US-A-5 152 827, US-A-5 399 545). The arylisocyanates to be used as starting materials in the case of the process (b) according to the invention for the preparation of the compounds of the general formula (I) are generally defined by the formula (IV). In the general formula (IV), Ar 2 preferably has that meaning which has already been indicated above, preferably or particularly preferably for Ar 2 in connection with the description of the compounds according to the invention of the general formula (I).

The starting materials of the general formula (IV) are organic chemical products for known syntheses. The substituted alkanols to be used further as starting materials in the case of process (b) according to the invention are generally defined by means of formula (V). In the general formula (V), Ar1 and R1 preferably have those meanings which have already been mentioned above, preferably or particularly preferably for Ar1 and R1 in relation to the description of the compounds according to the invention of the general formula (I ).

The starting materials of the general formula (V) are known and / or can be prepared according to methods known per se (see US-A 099 059, US-A 5 152 827, US-A 5 399 545). Suitable reaction aids for processes (a) and (b) are generally the usual inorganic or organic acid bases or acceptors. These preferably include acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates of alkali metals or alkaline earth metals, such as, for example, sodium, potassium or calcium acetate, lithium amide, sodium, potassium amide. or of calcium, 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 sodium or potassium t-butanolate; also basic organic nitrogenous compounds such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, 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 [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, in particular, inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic halogenated hydrocarbons, such as, for example, benzene, 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, work is carried out 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 with a higher pressure or at a lower pressure, generally 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 a reaction auxiliary agent, 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: Dicotyledonous bad herbs of the classes: Sinapis Lepidium, Galium , Stellaria, atricaria, 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 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, Aegilops, Phalaris. 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 active compounds according to the invention are suitable, depending on the concentration, for totally combating weeds, for example, in industrial and road installations and on roads and squares, with and without tree growth. In the same way, 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, tea, rubber oil palms, cocoa, berries and hops, on ornamental and sports paths and on meadows and to selectively control weeds in mono-annual crops. The compounds according to the invention of the formula (I) show a potent herbicidal activity and a broad spectrum of activity on the ground and on the aerial parts of the plants. They are also suitable to some extent to selectively control monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both in the pre-emergence procedure and in the post-emergence procedure.

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 products with extender materials, that is, with liquid solvents and / or solid excipients, if appropriate, employing surfactants, that is, emulsifiers and / or dispersants and / or 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. Suitable solid excipients are, 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 come into consideration: for example, broken and fractionated natural minerals such as calcite, marble, pumice, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as granulates of organic materials, such as sawdust, coconut husks, corn ears and tobacco stems; Examples of suitable emulsifiers and / or foam generators are nonionic 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, and the like. albumin hydrolysates; Suitable dispersants are: for example, sulfuric 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. . 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 presented as such or in their formulations also in mixtures with known herbicides for the control of weeds, with formulations ready for use or tank mixtures being possible. Suitable mixtures include known herbicides, for example: Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron. Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl), Bentazon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Conidon (-ethyl) Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (- propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (-methyl). Cumyluron, Cyanazine, Cybutryne, 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, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (- ethyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop (-P-ethyl), Flamprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulfuron, Fluazifop (-P-butyl), Fluazolate, Flucarbazone, Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flupyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (- meptyl), Flu rimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Gly phosate (-isopropylammonium), Halosafen. Haloxyfop (-ethoxyethyl), Haloxyfop (-P-ethyl), Hexazinone, lmazamethabenz (-methyl). Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfuron, Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, etazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, etsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, 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), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P -tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thiobencarb, Thiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifluralin, and Triflusulfuron. 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 of the forms of application prepared therefrom by further dilutions, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. 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 amount of active product used can vary within a wide range. This depends fundamentally on the type of the desired effect.

They fundamentally depend 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 (b)). A mixture of 1.20 g (5 mol) of (-) - 1-ethyl-2- (3-trifluoromethyl-phenoxy) -ethanol is stirred for 15 hours at room temperature (approximately 20 ° C). , 70 g (5 mmol) of 2,3-dimethyl-phenylisocyanate, 0.1 g (10 mmol) of triethylamine and 20 ml of acetonitrile and then carefully concentrated by vacuum evaporation of the water tube. The residue is digested with petroleum ether and the crystalline product formed is isolated by suction filtration. 1.3 g (68% of theory) of (-) - N- (2,3-dimethyl-phenyl) -O- [l-ethyl-2- (3-trifluoromethyl-phenoxy) -ethyl] - are obtained carbamate with a melting point of 68 ° C; [CC] 20D = + 24.8 °. In a manner analogous to that of Example 1, and also according to the general description of the preparation processes according to the invention, compounds of the general formula (I) indicated in Table 1 below can be prepared, for example.

) Table 1: Examples of compounds of the general formula (I). In this case, they are respectively the (-) enantiomers. Starting products of the general formula (V): Example (V-1).

Separation of the racemate in the individual enantiomers: The separation of the racemate was carried out at room temperature (approximately 20 ° C) by HPLC (high performance liquid chromatography) in the chiral stationary silica gel phase Chiracel OD® using a mixture formed by n-heptane and by isopropanol as eluent and detection by photometry. Column: Chiracel OD® 20 μm (manufacturer: Daicel, Japan) 500 * 40 mm.

Eluent: n-heptane / isopropanol (volume 10: 1). Flow rate: 30 ml / minute. Detection: UV 254 nm. Sampling: 100 mg of racemate (= 2.5 ml of a solution of 1 g of racemate in 25 ml of eluent). The eluate fractions were combined correspondingly after the analytical test in relation to the purity of the enantiomers, concentrated by evaporation under reduced pressure and used as crude product for the subsequent reactions. Under the conditions indicated above, the levorotatory enantiomer was first eluted. Specific value of the rotation of the levorotatory enantiomer: [a] 20D = -15.9 (measured in chloroform) at a concentration of 20 mg / ml of solution. The total amount was thus separated by repeated runs of 100 mg each. Application examples: Example A. Pre-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 to the desired concentration. Seeds are sown from the test plants in normal soil. After about 24 hours, the soil is sprayed with the preparation of the active product in such a way that it is applied, respectively, the amount of active product desired per unit area. The concentration of the spray mixture will be chosen in such a way that it is applied in 1,000 liters of water per hectare, respectively, the amount of desired active product. After three weeks the degree of damage of the plants in% damage is evaluated in comparison with the development of control not treated. They mean: 0% = no effect (same as untreated controls). 100% = total destruction.

In this test, for example, the compounds according to the preparation examples 1 and 2 are shown, with a partially good compatibility with crop plants, such as, for example, wheat, barley, cotton and soya beans, 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 to the desired concentration. Test plants are sprayed, which have a height of 5 to 15 cm with the preparation of the active product, so that, respectively, the desired quantities of active compound per unit area are 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 the preparation examples 1 and 2 show a potent effect against weeds.

It is noted that, in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Claims (7)

1. CLAIMS Having described the invention as above, the content of the following is claimed as property: 1. Substituted N-aryl-O-aryloxyalkyl-carbamates of the general formula (I), characterized in that Ar1 means a carbocyclic or heterocyclic, monocyclic or bicyclic group, respectively substituted, if appropriate, of the series consisting of phenyl, naphthyl, tetralinyl, furyl, benzofuryl, thienyl, benzothienyl, pyridinyl, quinolinyl, isoquinol inyl or the grouping, replaced if necessary - next wherein A means alkanediyl having 1 to 3 carbon atoms, optionally substituted by halogen, and where the corresponding possible substituents are preferably chosen from the following enumeration: cyano, nitro, halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl , alkylcarbonyl, alkoxycarbonyl with, respectively, up to 5 carbon atoms, respectively substituted, if appropriate, by halogen, Ar 2 means aryl having 6 or 10 carbon atoms, optionally substituted by nitro, by cyano, by carboxy, by carbamoyl, by thiocarbamoyl , by halogen or by alkyl, by alkoxy, by alkylthio, by alkylsulfinyl, by alkylsulfonyl, by alkylamino, by dialkylamino, by alkylcarbonyl, by alkoxycarbonyl, by alkylaminocarbonyl or by dialkylaminocarbonyl with, respectively, up to 4 carbon atoms in the alkyl groups, (substituted, where appropriate, by cyano, by halogen, by alkoxy with 1 to 4 carbon atoms) or, for alkylthio having 1 to 4 carbon atoms, for alkylsulfinyl having 1 to 4 carbon atoms or for alkylsulfonyl with 1 to 4 carbon atoms), R 1 means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, and R2 means hydrogen or means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, with the proviso that in the compounds of the general formula (I) the substituents are arranged on the carbon atom, with which R is linked in such a way that the polarized light in the oscillation plane turns to the left, ie the compounds of the formula (I) are presented as enantiomers (-).
2. 2. Substituted N-aryl-O-aryloxyalkyl carbamates according to claim 1, characterized in that Ar1 means a carbocyclic or heterocyclic, monocyclic or bicyclic group, respectively substituted, if appropriate, of the series consisting of phenyl, naphthyl, tetralinyl, furyl, benzofuryl, thienyl, benzothienyl, pyridinyl, quinolinyl, isoquinolinyl, or the following groupings, also optionally substituted where A means methylene or dimethylene (ethane-1,2-diyl) respectively substituted, if appropriate, by fluorine and / or by chlorine, and wherein the respective possible substituents are preferably chosen from the following enumeration: cyano, nitro, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n-i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulphinyl, n- or i-propyl-sulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, acetyl, propyl onyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl. substituted respectively by fluorine and / or chlorine, respectively, means phenyl or naphthyl respectively substituted by nitro, by cyano, by carboxy, by carbamoyl, by thiocarbamoyl, by fluorine, by chlorine, by bromine, by iodine or by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by n-, i-, s- or t-butoxy, by methylthio, by ethylthio, by n- or i-propylthio, by n-, i-, s- or t-butylthio, by methylsulfinyl, by ethylsulfinyl, by n- or i-propylsulfinyl, by methylsulfonyl, by ethylsulfonyl, by n- or i-propylsulfonyl, by methylamino, by ethylamino, by n- or i-propylamino, by n-, i-, s- or t-butylamino, by dimethylamino, by diethylamino, by acetyl, by propionyl, by n- or s-butyroyl, by methoxycarbonyl, by ethoxycarbonyl, by n- or i-propoxycarbonyl, by methylaminocarbonyl, by ethylaminocarbonyl, by n- or i-propylaminocarbonyl, by dimethylaminocarbonyl or by diethylaminocarbonyl (each substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulphonyl or ethylsulphonyl), R 'means methyl, ethyl, n- or i-propyl and R3 means hydrogen, methyl, ethyl, n- or -propyl.
3. 3. Substituted N-aryl-O-aryloxyalkyl-carbamates according to claim 1, characterized in that Ar1 means phenyl, which contains in the 3-position a substituent of the series formed by cyano, by nitro, fluoro, chloro, bromo, methyl , ethyl, n- or i-propyl, chloromethyl, fluomomethyl, dichloromethyl, difluoromethyl, trichloromethyl, trifluoromethyl, methoxy, ethoxy, fluoro-methoxy, difluoromethoxy, chlorofluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy and containing, if appropriate, in another position another substituent according to previous enumeration, Ar 2 denotes phenyl optionally substituted by nitro, by cyano, by fluorine, by chlorine, by bromine or by methyl, by ethyl, by n- or i-propyl, by methoxy, by ethoxy, by n- or i-propoxy, by methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulphonyl, n- or i-propylsulphonyl, dimethylamino, acetyl, propionyl , by methoxycarbonyl, by ethoxycarbonyl or by dimethylaminocarbonyl (respectively substituted, where appropriate, by fluorine or by chlorine), R 1 signifies methyl or ethyl and R 2 signifies hydrogen, methyl or ethyl.
4. 4. Process for the preparation of substituted N-aryl-O-aryloxyalkyl-carbamates according to one of claims 1 to 3, characterized in that (a) arylamines of the general formula (II) are reacted H ^ Ar (II) R4 wherein Ar2 and R2 have the meaning indicated in one of claims 1 to 3, with esters of the chloroformic acid of the general formula (III) wherein Ar1 and R1 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 if - in the case of if R2 means hydrogen- ib), arylisocyanates of the general formula (IV) are reacted JV Q = C = N '(IV) wherein Ar2 has the meaning indicated in one of claims 1 to 3, with substituted alkanols of the general formula (V) wherein Ar1 and R1 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. Process for the control of undesirable plants, characterized in that a substituted N-aryl-O-aryloxyalkyl carbamate according to one of claims 1 to 3 is allowed to act on the undesirable plants and / or on its environment.
6. 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.
7. 7. Herbicidal agents, characterized in that they have a content of at least one substituted N-aryl-O-aryloxyalkyl carbamate according to one of claims 1 to 3 and customary extenders. N-ARIL-O-ARYLOXIALQUIL-CARBAMATES SUBSTITUTED OPTICALLY ACTIVE. SUMMARY OF THE INVENTION The invention relates to new optically active substituted N-aryl-O-aryloxyalkyl carbamates of the general formula (I) wherein Ar] means a carbocyclic or heterocyclic, monocyclic or bicyclic group, respectively substituted, if appropriate, of the series consisting of phenyl, naphthyl, tetralinyl, furyl, benzonyl, thienyl, benzothienyl, pyridinyl, quinolinyl, isoquinolinyl or the grouping , also replaced if necessary - next (a) wherein A means alkanediyl having 1 to 3 carbon atoms, optionally substituted by halogen, and where the corresponding possible substituents are preferably chosen from the following enumeration: cyano, nitro, halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl , alkylcarbonyl, alkoxycarbonyl with, respectively, up to 5 carbon atoms, each optionally substituted by halogen, Ar means aryl having 6 or 10 carbon atoms, optionally substituted by nitro, by cyano, by carboxy, by carbamoyl, by thiocarba oyl, by halogen or by alkyl, by alkoxy, by alkylthio, by alkylsulfinyl. by alkylsulfonyl, by alkylamino, by dialkylamino, by alkylcarbonyl, by alkoxycarbonyl, by alkylaminocarbonyl or by dialkylaminocarbonyl with. respectively, up to 4 carbon atoms in the alkyl groups, (substituted, where appropriate, by cyano, by halogen, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4) carbon atoms or by alkylsulfonyl with 1 to 4 carbon atoms). R1 means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, and R means hydrogen or means alkyl with 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, with the The proviso is that in the compounds of the general formula (I) the substituents are arranged on the carbon atom, with which R7 is linked in such a way that the polarized light in the oscillation plane turns to the left. The invention also relates to processes for obtaining the new compounds and their use as herbicides.