KR20010074841A - Optically active substituted N-aryl-O-aryloxyalkyl-carbamates - Google Patents

Abstract

The present invention relates to optically active novel substituted N-aryl-O-aryloxyalkyl-carbamates of the general formula (I) below, their preparation and their use as herbicides.

Where

Ar ¹ is optionally substituted in each case and is selected from the group consisting of phenyl, naphthyl, tetralinyl, furyl, benzofuryl, thienyl, benzothienyl, pyridinyl, quinolinyl, isoquinolinyl A carbocyclic or heterocyclic group of a click or bicyclic, or an optionally substituted group of the following structural formulas:

Wherein A is optionally halogen-substituted and represents alkanediyl having 1 to 3 carbon atoms,

Possible substituents in each case are preferably cyano, nitro, halogen, in each case optionally halogen-substituted and in each case alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkyl with up to 5 carbon atoms Carbonyl, alkoxycarbonyl,

Ar ² is either nitro, cyano, carboxy, carbamoyl, thiocarbamoyl or halogen or (in each case optionally cyano-, halogen-, C ₁ -C ₄ -alkoxy-, C ₁ -C ₄ -alkyl Thio-, C ₁ -C ₄ -alkylsulfinyl- or C ₁ -C ₄ -alkylsulfonyl-substituted) in each case alkyl, alkoxy, alkylthio, alkylsulfinyl having up to 4 carbon atoms in the alkyl group Aryl having 6 to 10 carbon atoms optionally substituted by alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl,

R ¹ optionally represents cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted and alkyl having 1 to 4 carbon atoms,

R ² represents hydrogen or alkyl, optionally cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted and having from 1 to 4 carbon atoms,

However, the substituent on the carbon atom to which R ¹ is bonded is arranged so that the polarization vibration plane rotates to the left.

Description

Optically active substituted N-aryl-O-aryloxyalkyl-carbamates

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 compounds is not satisfactory in all respects.

The present invention relates to novel optically active N-aryl-O-aryloxyalkyl-carbamates, their preparation and their use as herbicides.

Accordingly, the present invention provides novel optically active N-aryl-O-aryloxyalkyl-carbamates of the general formula (I):

Where

Ar ¹ is optionally substituted in each case and is selected from the group consisting of phenyl, naphthyl, tetralinyl, furyl, benzofuryl, thienyl, benzothienyl, pyridinyl, quinolinyl, isoquinolinyl A carbocyclic or heterocyclic group of a click or bicyclic, or an optionally substituted group of the following structural formulas:

Wherein A is optionally halogen-substituted and represents alkanediyl having 1 to 3 carbon atoms,

Possible substituents in each case are preferably cyano, nitro, halogen, in each case optionally halogen-substituted and in each case alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkyl with up to 5 carbon atoms Carbonyl, alkoxycarbonyl,

Ar ² is either nitro, cyano, carboxy, carbamoyl, thiocarbamoyl or halogen or (in each case optionally cyano-, halogen-, C ₁ -C ₄ -alkoxy-, C ₁ -C ₄ -alkyl Thio-, C ₁ -C ₄ -alkylsulfinyl- or C ₁ -C ₄ -alkylsulfonyl-substituted) in each case alkyl, alkoxy, alkylthio, alkylsulfinyl having up to 4 carbon atoms in the alkyl group Aryl having 6 to 10 carbon atoms optionally substituted by alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl,

R ¹ optionally represents cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted and alkyl having 1 to 4 carbon atoms,

R ² represents hydrogen or alkyl, optionally cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted and having from 1 to 4 carbon atoms,

However, in the compound of general formula (I), the substituent on the carbon atom to which R ¹ is bonded is arranged such that the polarization oscillation plane is rotated to the left, that is, the compound of general formula (I) is present as a (-)-enantiomer. .

In the definition, hydrocarbon chains such as alkyl, including combinations with heteroatoms such as alkoxy, are each straight or branched chain.

Ar ¹ preferably represents one of the aforementioned groups, wherein A in each case optionally represents fluorine- and / or chlorine-substituted methylene or dimethylene (ethane-1,2-diyl), in which case Substituents are preferably cyano, nitro, fluorine, chlorine, bromine, in each case optionally fluorine- and / or chlorine-substituted 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-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, acetyl, propionyl, n- Or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl.

Ar ² is preferably respectively nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or iodine, or (in each case optionally cyano-, fluorine-, chlorine-, methoxy- , Ethoxy-, methylthio-, ethylthio-, methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- or ethylsulfonyl-substituted) 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-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methyl Amino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, acetyl, propionyl, n- or s-butyroyl, methoxy Carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, Amino-carbonyl, ethyl-amino-carbonyl, represents a n- or i- propylamino-carbonyl, dimethylamino-carbonyl or diethylamino carbonyl by a carbonyl, optionally substituted phenyl or naphthyl.

R ¹ preferably denotes methyl, ethyl, n- or i-propyl.

R ² preferably denotes hydrogen, methyl, ethyl, n- or i-propyl.

Ar ¹ is particularly preferably in the 3 position cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, chloromethyl, fluoromethyl, dichloromethyl, difluoromethyl, trichloromethyl , A substituent selected from the group consisting of trifluoromethyl, methoxy, ethoxy, fluoromethoxy, difluoromethoxy, chlorofluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy and optionally at other positions in the list above Phenyl comprising further substituents accordingly.

Ar ² is particularly preferably methyl, ethyl, n- or i-propyl, methoxy, ethoxy, preferably with nitro, cyano, fluorine, chlorine or bromine or (in each case optionally fluorine- or chlorine-substituted) , n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- Or phenyl optionally substituted by i-propylsulfonyl, dimethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl or dimethylaminocarbonyl.

R ¹ particularly preferably represents methyl or ethyl.

R ² particularly preferably represents hydrogen, methyl or ethyl.

Preferred compounds according to the invention are represented by compounds of the general formula (I) which comprise a combination of the meanings defined above as preferred.

Particularly preferred compounds according to the invention are represented by compounds of the general formula (I) which comprise a combination of meanings defined above as particularly preferred.

The general or preferred definitions of the abovementioned radicals also apply to the final product of the general formula (I) and similarly to the starting materials or intermediates required for each preparation. The definitions of these radicals can be combined with one another as desired, ie including combinations within defined preferred ranges.

Examples of compounds of formula (I) according to the invention are given in the following groups:

Group 1

Here, Ar ² has the meaning set forth below, for example:

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, 2-chloro- 4-trifluoromethyl-phenyl, 2-chloro-4-cyano-phenyl, 2-chloro-4-methoxy-phenyl, 2-chloro-4-ethoxy-phenyl, 2-chloro-5-fluoro -Phenyl, 2,5-dichloro-phenyl, 2-chloro-5-bromo-phenyl, 2-chloro-5-methyl-phenyl, 2-chloro-5-ethyl-phenyl, 2-chloro-5-trifluoro Chloromethyl-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-fluoro-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-phenyl, 2-fluoro-4-bromo-phenyl, 2-fluoro-4-methyl-phenyl, 2 -Fluoro-4-ethyl-phenyl, 2-fluoro-4-trifluoromethyl-phenyl, 2-fluoro-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-clock Rho-phenyl, 2-fluoro-6-bromo-phenyl, 2-fluoro-6-methyl-phenyl, 2-fluoro-6-ethyl-phenyl, 2-fluoro-6-trifluoromethyl- Phenyl, 2-fluoro-6-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- Nyl, 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-methyl- 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, 2-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-trifluor Romethyl-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-phenyl , 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-ethyl-6-methyl-phenyl, 2,6-diethyl-phenyl, 2-ethyl-6-trifluoro Romethyl-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-trifluoro Tyl-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-trifluoromethyl-6-methyl-phenyl, 2-trifluoromethyl-6-ethyl-phenyl, 2,6-bis-tri Fluoromethyl-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- Oxy-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-6-fluoro-phenyl, 2-cyano-6-chloro-phenyl, 2-cyano-6-bromo-phenyl, 2-cya No-6-methyl- Neyl, 2-cyano-6-ethyl-phenyl, 2-cyano-6-trifluoromethyl-phenyl, 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- Methoxy-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 Toxy-6-methyl- Neyl, 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-ethoxy-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-die Oxy-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-e Toxy-6-methyl- Neyl, 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

Here, Ar ² has the meaning given to group 1, for example.

Group 3

Here, Ar ² has the meaning given to group 1, for example.

Group 4

Here, Ar ² has the meaning given to group 1, for example.

Group 5

Here, Ar ² has the meaning given to group 1, for example.

Group 6

Here, Ar ² has the meaning given to group 1, for example.

Group 7

Here, Ar ² has the meaning given to group 1, for example.

Group 8

Here, Ar ² has the meaning given to group 1, for example.

Group 9

Here, Ar ² has the meaning given to group 1, for example.

Group 10

Here, Ar ² has the meaning given to group 1, for example.

Group 11

Here, Ar ² has the meaning given to group 1, for example.

Group 12

Here, Ar ² has the meaning given to group 1, for example.

Group 13

Here, Ar ² has the meaning given to group 1, for example.

Group 14

Here, Ar ² has the meaning given to group 1, for example.

Group 15

Here, Ar ² has the meaning given to group 1, for example.

Group 16

Here, Ar ² has the meaning given to group 1, for example.

Group 17

Here, Ar ² has the meaning given to group 1, for example.

Group 18

Here, Ar ² has the meaning given to group 1, for example.

Group 19

Here, Ar ² has the meaning given to group 1, for example.

Group 20

Here, Ar ² has the meaning given to group 1, for example.

Group 21

Here, Ar ² has the meaning given to group 1, for example.

Particularly preferred compounds according to the invention are given as compounds of groups 1 to 3 having the above conditions.

Most preferred compounds according to the invention are given as compounds of group 2 having the above conditions.

The novel substituted N-aryl-O-alkyl-carbamates of formula (I) according to the invention have potent and selective herbicidal activity.

The novel substituted N-aryl-O-alkyl-carbamate of formula (I) according to the invention,

(a) reacting the arylamine of the general formula (II) with the chloroformic acid ester of the general formula (III), if appropriate in the presence of a reaction aid and

When R ² is hydrogen,

(b) obtained by reacting aryl isocyanates of the general formula (IV) with substituted alkanols of the general formula (V), if appropriate in the presence of a reaction aid and, if appropriate, in the presence of a diluent:

Wherein Ar ¹ , Ar ² , R ¹ and R ² are each as defined above.

For example, (-)-[1- (3-methyl-phenoxymethyl) -propyl] chloroformate and 2-fluoro-6-methyl-aniline are used as starting materials and the process according to the invention ( The reaction process in a) can be represented by the following scheme:

For example, the process according to the invention (b) using (-)-1- (3-trifluoromethyl- methoxymethyl) -butanol and 2-chloro-5-methoxy-phenyl isocyanate as starting material, (b) The reaction process can be represented by the following scheme:

The general definition of arylamine used as starting material in the process (a) according to the invention for the preparation of compounds of general formula (I) is given by general formula (II). In the general formula (II), Ar ² and R ² preferably each refer to the meanings already mentioned as being preferred or particularly preferred for Ar ² and R ² in connection with the description of the compounds of general formula (I) according to the invention. Have

Starting materials of formula (II) are known synthetic organic chemicals.

In addition, the general definition of chloroformate used as starting material in process (a) according to the invention is given by the general formula (III). In formula (III), Ar ¹ and R ¹ are each preferably referring to the meanings already mentioned as being preferred or particularly preferred for Ar ¹ and R ¹ in connection with the description of the compounds of formula (I) according to the invention. Have

Starting materials of general formula (III) can be prepared by known and / or known methods per se (see US-A 5 099 059, US-A 5 152 827, US-A 5 399 545).

The general definition of aryl isocyanate used as starting material in the process (b) according to the invention for preparing the compound of general formula (I) is given by the general formula (IV). In the general formula (IV), Ar ² preferably has the meaning already mentioned as preferred or particularly preferred for Ar ² in connection with the description of the compound of general formula (I) according to the invention.

Starting materials of general formula (IV) are known synthetic organic chemicals.

In addition, the general definition of substituted alkanols used as starting materials in process (b) according to the invention is given by the general formula (V). In formula (V), Ar ¹ and R ¹ each preferably represent the meanings already mentioned as being preferred or particularly preferred for Ar ¹ and R ¹ in connection with the description of the compounds of formula (I) according to the invention. Have

Starting materials of formula (V) are known and / or may be prepared by methods known per se (see US-A 5 099 059, US-A 5 152 827, US-A 5 399 545).

Suitable reaction aids for carrying out the methods (a) and (b) according to the invention are generally customary inorganic or organic base or acid acceptors. Preferably, alkali or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrogenates, hydroxides or alkoxides, for example sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, Sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide or potassium methoxide, sodium Ethoxide or potassium ethoxide, sodium n- or i-propoxide or potassium n- or i-propoxide, sodium n-, i-, s- or t-butoxide or potassium n-, i-, s Or t-butoxide; Basic organic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclo Hexylamine, N, N-dimethyl-aniline, N, N-dimethylbenzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2, 2,2] -octane (DABCO), 1,5-diazabicyclo [4,3,0] -non-5-ene (DBN), or 1,8-diazabicyclo [5,4,0]- Undec-7-en (DBU).

Suitable diluents for carrying out the processes (a) and (b) according to the invention are especially inert organic solvents. In particular aliphatic, cycloaliphatic and aromatic, optionally halogenated hydrocarbons such as benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol 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 hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; Alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether; Water or purified water and mixtures thereof.

When carrying out the processes (a) and (b) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

Processes (a) and (b) according to the invention are generally carried out at atmospheric pressure. However, the process according to the invention can also be carried out under elevated or reduced pressure—generally between 0.1 bar and 10 bar.

To carry out the processes (a) and (b) according to the invention, the starting materials are generally used in almost equimolar amounts. However, one of the components may also use a relatively excess amount. The reaction is generally carried out in the presence of a suitable diluent and optionally in the presence of a reaction aid, and the reaction mixture is generally stirred for a long time at the required temperature. Post-treatment of the reaction is carried out by conventional methods (see Preparation Examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular weed killer. "Weeds" in the broad sense means all plants that grow in unwanted places. Whether the compounds 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 connection with the following plants:

Dicotyledonous weeds in the genus

Sinapis, Lepidium, Gallium,

Stellaria, Matricaria, Anthemis,

Galinsoga, Kenopodium, Urtica,

Senezio, 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 and

Taraxacum.

Dicotyledonous crops of the genus

Gossypium, Glycine, Beta, Doucus,

Phaeseolus, Pisum, Solanum, Linum,

Ipomoea, Vicia, Nicotiana,

Lycopersicon, Arachis, Brassica,

Lactuca, Cucumis and Cucurbita.

Monocot weeds in the genus

Echinochloa, Setaria, Panicum,

Digitaria, Phleum, Poa, Festus,

Eleusin, Brachiaria, Lolium,

Bromus, Avena, Cyperus, Sorghum,

Agropyron, Cynodon, Monochoria,

Fimbristylis, Sagittaria,

Eleocharis, Scirpus, Paspalum,

Ischaemum, Sphenoclea,

Dactyloctenium, Agrostis,

Allopecurus and Apera.

Monocotyledonous crops of the genus

Oryza, Zea, Triticum, Hordeum,

Avena, Secale, Sorghum, Panicum,

Saccharum, Ananas, Asparagus and

Allium.

However, the use of the active compounds according to the invention is not limited at all in the above, but extends to other plants in the same way.

The active compounds according to the invention are suitable for the overall control of weeds, depending on concentration, for example on industrial zones and railway lines, and on sidewalks and plazas with or without trees. Likewise, the active compounds according to the invention are for example forests, ornamental plantations, orchards, vineyards, citrus fields, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, palm plantations, cocoa plantations, soft fruit plantations and It can be used to control weeds from perennial crops growing on hop fields, lawns, sports fields and pastures, and to selectively control weeds from annual crops.

When applied to soil and the above-described plant cultivation, the compound of general formula (I) according to the present invention has a strong herbicidal activity and a broad spectrum of activity. To some extent these compounds are also suitable for the selective control of monocotyledonous or dicotyledonous weeds both before and after germination in monocotyledonous and dicotyledonous crops.

Active compounds can be prepared as solutions, emulsions, hydrating powders, suspensions, powders, powders, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active compounds, and microcapsules in polymeric materials. It may be converted to a conventional formulation. These formulations are prepared by known methods, for example by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, optionally using surfactants, ie emulsifiers and / or dispersants and / or foam-forming agents. .

When water is used as the extender, for example an organic solvent can also be used as an auxiliary solvent. As a liquid solvent, aromatic compounds, such as xylene, toluene, or alkyl naphthalene; Chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride; Aliphatic hydrocarbons such as cyclohexane or paraffins such as petroleum fractions, mineral oils and vegetable oils; Alcohols such as butanol or glycols and ethers and esters thereof; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; Water is suitable as well as strong polar solvents such as dimethylformamide and dimethyl sulfoxide.

Solid carriers include, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and highly dispersed silica, alumina and silicates Pulverized synthetic minerals such as are suitable. Solid carriers for granulation include, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calculi and dolomite; And synthetic granules of inorganic and organic powders; And granules of organic materials such as sawdust, coconut husks, corncobs and tobacco stems. Emulsifiers and / or foam-forming agents include, for example, nonionic and anionic emulsifiers, for example polyoxyethylene fatty alcohol ethers such as polyoxyethylene fatty acid esters, alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryls Sulfonates and proteolytic products are suitable. Suitable dispersants are, for example, lignin-sulfite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose; Natural and synthetic polymers in powder, granule or latex form, such as gum arabic, polyvinyl alcohol and polyvinyl acetate; And natural phospholipids such as cephalin and lecithin; And synthetic phospholipids can be used in the formulations. As other additives, mineral oil and vegetable oil may be used.

Inorganic pigments such as iron oxide, titanium oxide and prussian blue, and colorants such as alizarin dyes, azo dyes and organic dyes such as metal phthalocyanine dyes and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc You can also use

The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.

To control weeds, the active compounds according to the invention can be used on their own or as a mixture with known herbicides in the form of their preparations, and finished formulations or tank mixtures can be used.

The components of the mixture include known herbicides such as acetochloro, acifluorophene (-sodium), acloniphene, alachloro, alkoxydim (-sodium), amethrin, amidochloro, amidosulfuron, anil Lofos, asulam, atrazine, azaphenidine, azimsulfuron, bennazoline (-ethyl), benfurate, bensulfuron (-methyl), bentazone, benzophene, benzoylprop (-ethyl), viala Phos, bifenox, bispyribac (-sodium), bromobutide, bromophenoxime, bromocinyl, butachloro, butoxydim, butyrate, carfenstrol, caroxydim, carbetamid, carpent Lazone (-ethyl), clomethoxyphene, chloroambene, chloroidazone, chloroimron (-ethyl), chloronitrophene, chlorosulfuron, chlorotoluron, cinidon (-ethyl), cinmethylline, cynosul Furon, cletodim, clodinafop (-propazol), clomazone, clomeprop, clopyralide, clopyrasulfuron (-methyl ), Chloransullam (-methyl), cumyluron, cyanazine, cybutrin, cycloate, cyclosulfamuron, cyclooxydim, sihalofop (-butyl), 2,4-D, 2,4 -DB, 2,4-DP, desmedipham, diallate, dicamba, diclofo (-methyl), diclosullam, dietatyl (-ethyl), dipfencuart, diflufenican, diflufenzo Pyr, dimefuron, dimepiperate, dimethchloro, dimethamethrin, dimethenamide, dimexlam, dinitramine, diphenamide, diquat, dithiopyr, diuron, dimuron, epoph Rodan, EPTC, esprocarb, etaflularine, etamethsulfuron (-methyl), etofumesate, ethoxyphene, ethoxysulfuron, etobenzanide, phenoxaprop (-P-ethyl), flam Prop (-isopropyl), flamprop (-isopropyl-L), flamprop (-methyl), plazasulfuron, fluazifop (-P-butyl), fluazolate, flucarbazone, flu Penacet, flumetsulam , Flumichlorac (-pentyl), flumioxazine, flumipropine, flumetsulam, fluoromethuron, fluorochloridone, fluoroglycopene (-ethyl), flupoxam, flupropacyl, flu Pyrsulfuron (-methyl, -sodium), flurenol (-butyl), flulidone, fluoroxypyr (-methl), fluprimidol, flutamone, fluthiacet (-methyl), pullulti Amide, pomesapene, glufosinate (-ammonium), glyphosate (-isopropylammonium), halosafen, halooxyphosph (-ethoxyethyl), halooxyphosph (P-methyl), hexazinone, imaza Metabenz (-methyl), imazamethafil, imazamox, imazapic, imazaphyr, imazaquin, imazetapyr, imazosulfuron, iodosulfuron, oxynyl, isoprophalin, isoproturon, Isourone, isoxaben, isoxachlorotol, isoxaplutol, isoxapyrupif, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, mesotrione, Tamitron, metazachloro, metabenzthiazuron, methopenzuron, methopromouron, (alpha-) metolachloro, methotsalam, methoxuron, metribuzin, metsulfuron (-methyl), molinate , Monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzaline, oxadiargyl, oxadione, oxasulfuron, oxazilomethone, Oxyfluorophene, paraquat, ferragonic acid, pendimethalin, pentoxazone, phenmedifam, piperophosph, pretilachlor, primisulfuron (-methyl), promethrin, propachloro, propanyl, Propaquizapov, propisochloro, propizamide, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazolate, pyrazosulfuron (-ethyl), pyrazoxifen, pyribenzoxime , Pyributicab, pyridate, pyriminobac (-methyl), pyrithiobac (-sodium), quinclolac, quinmerak, quinoclamine, Zalofof (-P-ethyl), quizaloff (-P-tefuryl), rimsulfuron, cetoxydim, simazine, simethrin, sulforion, sulfentrazone, sulfomethuron (-methyl), Sulfosate, sulfosulfuron, tebutam, tebutiuurone, tephthaloxydim, tebutylazine, tebutrin, tenylchloro, triafluamide, thiazopyr, thidiazimine, thifensulfuron (-methyl), Thiobencarb, thiocarbazyl, tralcoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr, tridiphane, triluarine and triflusulfuron.

Mixtures with other known active compounds such as fungicides, insecticides, acaricides, nematicides, algae repellents, plant nutrients and soil structure improvers are also possible.

The active compounds can be used on their own, in the form of their formulations or in the forms of use prepared from them, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The active compound is used by conventional methods such as, for example, watering, spraying, atomizing or scattering.

The active compounds according to the invention can be used before and after germination of plants. They can also be incorporated into the soil before sowing.

The amount of active compound can vary within a significant range. This is essentially dependent on the nature of the desired effect. Generally, the amount used is from 1 g to 10 kg, preferably from 5 g to 5 kg of active compound per hectare of soil surface.

The preparation and use of the active compounds according to the invention can be seen from the following examples.

Manufacturing Example:

Example 1

[Method (b)]

(-)-1-ethyl-2- (3-trifluoromethyl-phenoxy) -ethanol 1.20 g (5 mmol), 2,3-dimethyl-phenyl isocyanate 0.70 g (5 mmol), triethylamine 0.1 g (10 mmol) ) And 20 ml of acetonitrile were stirred at room temperature (about 20 ° C.) for 15 minutes and then carefully concentrated under water pump vacuum. The residue was broken down into petroleum esters and the resulting crystalline product was separated by suction filtration.

1.3 g of (-)-N- (2,3-dimethylphenyl) -O- [1-ethyl-2- (3-trifluoromethyl-phenoxy) -ethyl] carbamate having a melting point of 68 캜 (68 of theory %) Was obtained; [a] _D ² ° = + 24.8 °.

By the method of Example 1 and according to the general description of the preparation process according to the invention, for example, compounds of the general formula (I) described in Table 1 below can also be prepared.

Table 1 : Examples of compounds of formula (I). These are each (-)-enantiomers.

Starting material of general formula (Ⅴ):

Example (V-1)

Separation of racemates into single enantiomers:

The racemate was subjected to Chilasel OD® on chiral stop silica gel using a mixture of n-heptane and isopropanol as mobile phase at room temperature (about 20 ° C) ^. (Chiracel OD ^? ) ^Was separated by HPLC (High Performance Liquid Chromatograph) and photometric detection.

Column: Chirasel OD ^? 20㎛ (Manufacturer: Daisel, Japan) 500 * 40㎜

Mobile phase: n-heptane / isopropanol (Vol. 10: 1)

Flow rate: 30 ml / min

Detection: UV 254nm

Sample charge: 100 mg racemate (= 2.5 ml of a solution of 1 g of racemate in 25 ml of mobile phase)

After analytical testing for enantiomer purity, the mobile phase fractions were collected, evaporated under reduced pressure and used as crude product for further reaction.

Under the conditions mentioned above, the left-handed enantiomer was eluted first. Intrinsic optical rotation of lecithin enantiomer: [α] _D ²⁰ = -15.9 in solution of concentration 20 mg / ml (measured in chloroform)

In each case the total amount was separated in this manner by repeated filling of 100 mg racemate.

Example of use:

Example A

Germination test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier is added, then the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Seeds of the test plants were sown in normal soil. After 24 hours, the preparation of the active compound was sprayed into the soil in such a way that a specific amount of the desired active compound per unit area was applied. The concentration of the spray solution was chosen in each case such that the desired amount of active compound was applied with 1000 liters of water per hectare.

After 3 weeks, the degree of damage to the plants was expressed as percent damage compared to the growth of the untreated control.

Numeric display:

0% = no effect (similar to untreated control)

100% = Destroy all

In this test, for example, Preparation Examples 1 and 2 compounds showed strong activity against weeds, with good suitability for crops such as barley, wheat, corn and soybeans.

Example B

Post Germination Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier is added, then the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Formulations of active compounds were sprayed by applying a desired concentration of the desired active compound per unit area to test plants with a height of 5-15 cm. The concentration of the spray solution was chosen in each case such that the desired amount of active compound was applied with 1000 liters of water per hectare.

After 3 weeks, the degree of damage to the plants was expressed as percent damage compared to the growth of the untreated control.

Numeric display:

0% = no effect (similar to untreated control)

100% = Destroy all

In this test, for example, the compounds of Preparation Examples 1 and 2 showed potent activity against weeds.

Claims (7)

Substituted N-aryl-O-aryloxyalkyl-carbamate of Formula (I): Where Ar ¹ is optionally substituted in each case and is selected from the group consisting of phenyl, naphthyl, tetralinyl, furyl, benzofuryl, thienyl, benzothienyl, pyridinyl, quinolinyl, isoquinolinyl A carbocyclic or heterocyclic group of a click or bicyclic, or an optionally substituted group of the following structural formulas: Wherein A is optionally halogen-substituted and represents alkanediyl having 1 to 3 carbon atoms, Possible substituents in each case are preferably cyano, nitro, halogen, in each case optionally halogen-substituted and in each case alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkyl with up to 5 carbon atoms Carbonyl, alkoxycarbonyl, Ar ² is either nitro, cyano, carboxy, carbamoyl, thiocarbamoyl or halogen or (in each case optionally cyano-, halogen-, C ₁ -C ₄ -alkoxy-, C ₁ -C ₄ -alkyl Thio-, C ₁ -C ₄ -alkylsulfinyl- or C ₁ -C ₄ -alkylsulfonyl-substituted) in each case alkyl, alkoxy, alkylthio, alkylsulfinyl having up to 4 carbon atoms in the alkyl group Aryl having 6 to 10 carbon atoms optionally substituted by alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl, R ¹ optionally represents cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted and alkyl having 1 to 4 carbon atoms, R ² represents hydrogen or alkyl, optionally cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted and having from 1 to 4 carbon atoms, In the compound of formula (I), the substituent on the carbon atom to which R ¹ is bonded is arranged such that the polarization oscillation plane is rotated to the left, that is, the compound of formula (I) is present as a (-)-enantiomer. do. The method of claim 1, Ar ¹ is optionally substituted in each case and is selected from the group consisting of phenyl, naphthyl, tetralinyl, furyl, benzofuryl, thienyl, benzothienyl, pyridinyl, quinolinyl, isoquinolinyl A carbocyclic or heterocyclic group of a click or bicyclic, or an optionally substituted group of the following structural formulas: Wherein A in each case optionally represents fluorine- and / or chlorine-substituted methylene or dimethylene (ethane-1,2-diyl), and in each case possible substituents are preferably cyano, nitro, fluorine, Chlorine, bromine, in each case optionally fluorine- and / or chlorine-substituted 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-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, Ethoxycarbonyl, n- or i-propoxycarbonyl, Ar ² is each nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or iodine, or (in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy -Methylthio-, ethylthio-, methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- or ethylsulfonyl-substituted) 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-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethyl Amino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, acetyl, propionyl, n- or s-butyroyl, methoxycarbonyl, Ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbon , Ethylamino-carbonyl, n- or i- propylamino-carbonyl, represents a dimethylamino-carbonyl group or a diethylamino-carbonyl phenyl or naphthyl optionally substituted by, R ¹ represents methyl, ethyl, n- or i-propyl, Substituted N-aryl-O-aryloxyalkyl-carbamate of formula (I), wherein R ² represents hydrogen, methyl, ethyl, n- or i-propyl. The method of claim 1, Ar ¹ is in position 3 cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, chloromethyl, fluoromethyl, dichloromethyl, difluoromethyl, trichloromethyl, trifluoro Substituents selected from the group consisting of methyl, methoxy, ethoxy, fluoromethoxy, difluoromethoxy, chlorofluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy and further substituents according to the above list optionally at other positions Represents phenyl containing Ar ² is nitro, cyano, fluorine, chlorine or bromine, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n-or (optionally fluorine- or chlorine-substituted in each case); i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propyl Phenyl optionally substituted by sulfonyl, dimethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl or dimethylaminocarbonyl, R ¹ represents methyl or ethyl, Substituted N-aryl-O-aryloxyalkyl-carbamate of formula (I), wherein R ² represents hydrogen, methyl or ethyl. (a) reacting the arylamine of the general formula (II) with the chloroformic acid ester of the general formula (III), if appropriate in the presence of a reaction aid and When R ² is hydrogen, (b) reacting aryl isocyanates of the general formula (IV) with the substituted alkanols of the general formula (V), if appropriate in the presence of a reaction aid and, if appropriate, in the presence of a diluent: Process for preparing a substituted N-aryl-O-aryloxyalkyl-carbamate according to any one of the preceding claims: Wherein Ar ¹ , Ar ² , R ¹ and R ² are each as defined in any one of claims 1 to 3. At least one substituted N-aryl-O-aryloxyalkyl-carbamate according to any one of claims 1 to 3 acts on unwanted plants and / or their habitats How to control plants. Use of at least one substituted N-aryl-O-aryloxyalkyl-carbamate according to any one of claims 1 to 3 for controlling unwanted plants. A herbicide comprising at least one substituted N-aryl-O-aryloxyalkyl-carbamate according to any one of claims 1 to 3 and a conventional extender.