WO2000017157A1

WO2000017157A1 - Optically active substituted n-aryl-o-aryloxyalkyl-carbamates

Info

Publication number: WO2000017157A1
Application number: PCT/EP1999/006754
Authority: WO
Inventors: Hans-Jochem Riebel; Ernst Rudolf F. Gesing; Johannes Rudolf Jansen; Joachim Kluth; Rolf Grosser; Mark Wilhelm Drewes; Dieter Feucht; Rolf Pontzen; Ingo Wetcholowsky
Original assignee: Bayer Aktiengesellschaft
Priority date: 1998-09-24
Filing date: 1999-09-13
Publication date: 2000-03-30
Also published as: DE19843763A1; CN1316989A; BR9914049A; CA2345073A1; AU5977899A; PL346858A1; JP2002526471A; EP1115700A1; AR020416A1; KR20010074841A

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, C¿1?-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; R?1¿ represents alkyl which has 1 to 4 carbon atoms and which is optionally substituted by cyano, halogen or C¿1?-C4-alkoxy and R?2¿ represents hydrogen or alkyl which has 1 to 4 carbon atoms and which is optionally substituted by cyano, halogen or C¿1?-C4-alkoxy, whereby the substituents on the carbon atom, on which R?1¿ 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

Optically active substituted N-aryl-O-aryloxyalkyl carbamates

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

It is known that certain substituted N-aryl-O-aryloxyalkyl carbamates have herbicidal properties (cf. US Pat. No. 5,099,059, US Pat. No. 5,152,827, US Pat. No. 5,194,661). However, the herbicidal activity of these known compounds is not satisfactory in all respects.

The new optically active substituted N-aryl-O-aryloxyalkylcarbamates of the general formula (I) have now been found

in which

Arl for an optionally substituted, monocyclic or bicyclic, carbocyclic or heterocyclic grouping from the series phenyl, naphthyl, tetralinyl, furyl, benzofuryl, thienyl, benzothienyl, pyridinyl,

Quinolinyl, isoquinolinyl or the - also optionally substituted below grouping

where A is optionally substituted by halogen alkanediyl having 1 to 3 carbon atoms, and where the possible substituents are preferably selected from the following list: cyano, nitro, halogen, each optionally substituted by halogen alkyl, alkoxy, alkylthio, alkylsulfinyl , Alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl each having up to 5 carbon atoms,

Ar2 for optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or by (in each case optionally by cyano, halogen, C, -C ₄ alkoxy, C, -C ₄ alkylthio, C, -C ₄ - alkylsulfinyl or C _r C ₄ -alkylsulfonyl-substituted) alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl each having up to 4 carbon atoms in the alkyl groups, substituted aryl having 6 or 10 carbon atoms,

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

R ^{2 represents} hydrogen or alkyl having 1 to 4 carbon atoms which is optionally substituted by cyano, halogen or C _r C ₄ alkoxy,

with the proviso that in the compounds of the general formula (I) the substituents on the carbon atom to which R ^{1 is} bonded are arranged such that the plane of oscillation of polarized light is rotated to the left, ie that the compounds of the formula (I) exist as (-) - enantiomers.

In the definitions, the hydrocarbon chains, such as alkyl, are also straight-chain or branched, in each case in conjunction with heteroatoms, such as in alkoxy.

Arl preferably represents one of the abovementioned groups, where A represents methyl which is optionally substituted by fluorine and / or chlorine. len or dimethylene (ethane-l, 2-diyl), and where the possible substituents are preferably selected from the following list: cyano, nitro, fluorine, chlorine, bromine, each optionally substituted by fluorine and / or chlorine, 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.

AJ2 preferably represents in each case optionally through nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or through (in each case optionally through 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, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, acetyl, Propionyl, n- or s-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl or diethylaminocarbonyl substituted phenyl or naphthyl.

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

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

Ar * particularly preferably represents phenyl, which in the 3-position is a substituent from the series cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or Contains i-propyl, chloromethyl, fluoromethyl, dichloromethyl, difluoromethyl, trichloromethyl, trifluoromethyl, methoxy, ethoxy, fluoromethoxy, difluoromethoxy, chlorofluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy and optionally contains a further substituent in a different position according to the preceding list.

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

R ¹ particularly preferably represents methyl or ethyl.

R ² particularly preferably represents hydrogen, methyl or ethyl.

According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred.

According to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

The general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These residual definitions can be combined with one another, that is, also between the specified preferred ranges. Examples of the compounds of the general formula (I) according to the invention are listed in the groups below.

Group 1

Ar ² has, for example, the meanings given below: 2-chloro-3-fluorophenyl, 2,3-dichlorophenyl, 2-chloro-3-bromophenyl, 2-chloro-3-methylphenyl, 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-fluorophenyl, 2,4-dichlorophenyl, 2-chloro-4-bromophenyl, 2-chloro-4-methylphenyl, 2-chloro-4-ethylphenyl, 2 -Chlor-4-trifluoromethyl-phenyl, 2-chloro-4-cyano-phenyl, 2-chloro-4-methoxy-phenyl, 2-chloro-4-ethoxy-phenyl, 2-chloro-5-fluorophenyl , 2,5-dichlorophenyl, 2-chloro-5-bromophenyl, 2-chloro-5-methylphenyl, 2-chloro-5-ethylphenyl, 2-chloro-5-trifluoromethylphenyl, 2 -Chlor-5-cyano-phenyl, 2-chloro-5-methoxy-phenyl, 2-chloro-5-ethoxy-phenyl, 2-chloro-6-fluorophenyl, 2,6-dichlorophenyl, 2-chlorine -6-bromophenyl, 2-chloro-6-methylphenyl, 2-chloro-6-ethylphenyl, 2-chloro-6-trifluoromethylphenyl, 2-chloro-6-cyano-phenyl, 2-chlorine -6-methoxyphenyl, 2-chloro-6-ethoxyphenyl; 2,3-difluorophenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-3-bromophenyl, 2-fluoro-3-methylphenyl, 2-fluoro-3-ethylphenyl, 2- Fluoro-3-trifluoromethyl-phenyl, 2-fluoro-3-cyano-phenyl, 2-fluoro-3-methoxy-phenyl, 2-fluoro-3-ethoxy-phenyl, 2,4-difluorophenyl, 2-fluoro- 4-chlorophenyl, 2-fluoro-4-bromophenyl, 2-fluoro-4-methylphenyl, 2-fluoro-4-ethylphenyl, 2-fluoro-4-trifluoromethylphenyl, 2-fluoro 4-cyano-phenyl, 2-fluoro-4-methoxy-phenyl, 2-fluoro-4-ethoxy-phenyl, 2,5-difluorophenyl, 2-fluoro-5-chlorophenyl, 2-fluoro-5- bromophenyl, 2-fluoro-5-methylphenyl, 2-fluoro-5-ethylphenyl, 2-fluoro-5-trifluoromethylphenyl, 2-fluoro-5-cyano-phenyl, 2-fluoro 5-methoxyphenyl, 2-fluoro-5-ethoxyphenyl, 2,6-difluorophenyl, 2-fluoro-6-chlorophenyl, 2- - o -

Fluoro-6-bromophenyl, 2-fluoro-6-methylphenyl, 2-fluoro-6-ethylphenyl, 2-fluoro-6-trifluoromethylphenyl, 2-fluoro-6-cyano-phenyl, 2- Fluoro-6-methoxy-phenyl, 2-fluoro-6-ethoxy-phenyl;

2-bromo-3-fluorophenyl, 2-bromo-3-chlorophenyl, 2,3-dibromophenyl, 2-bromo-3-methylphenyl, 2-bromo-3-ethylphenyl, 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-chlorophenyl, 2,4-dibromophenyl, 2-bromo-4-methylphenyl,

2-bromo-4-ethylphenyl, 2-bromo-4-trifluoromethylphenyl, 2-bromo-4-cyano-phenyl,

2-bromo-4-methoxyphenyl, 2-bromo-4-ethoxyphenyl, 2-bromo-5-fluorophenyl, 2-bromo-5-chlorophenyl, 2,5-dibromo-phenyl, 2- Bromo-5-methyl-phenyl, 2-bromo-5-ethylphenyl, 2-bromo-5-trifluoromethyl-phenyl, 2-bromo-5-cyano-phenyl, 2-bromo-5-methoxy-phenyl, 2- Bromo-5-ethoxyphenyl, 2-bromo-6-fluorophenyl, 2-bromo-6-chlorophenyl, 2-bromo-6-bromophenyl, 2-bromo-6-methylphenyl, 2- Bromo-6-ethylphenyl,

2-bromo-6-trifluoromethylphenyl, 2-bromo-6-cyano-phenyl, 2-bromo-6-methoxyphenyl, 2-bromo-6-efhoxyphenyl;

2-methyl-3-fluorophenyl, 2-methyl-3-chlorophenyl, 2-methyl-3-bromophenyl, 2,3-dimethylphenyl, 2-methyl-3-ethylphenyl, 2- Methyl-3-trifluoromethyl-phenyl, 2-methyl-3-cyano-phenyl, 2-methyl-3-methoxy-phenyl, 2-methyl-3-ethoxy-phenyl, 2-methyl-4-fluorophenyl, 2- Methyl-4-chlorophenyl, 2-methyl-4-bromophenyl, 2,4-dimethylphenyl, 2-methyl-4-ethylphenyl, 2-methyl-4-trifluoromethylphenyl, 2 -

Methyl-4-cyano-phenyl, 2-methyl-4-methoxy-phenyl, 2-methyl-4-ethoxy-phenyl, 2-methyl-5-fluorophenyl, 2-methyl-5-chlorophenyl, 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-fluorophenyl, 2-methyl-6-chlorophenyl, 2-methyl-6-bromophenyl, 2,6-

Dimethylphenyl, 2-methyl-6-ethylphenyl, 2-methyl-6-trifluoromethylphenyl, 2-methyl-6-cyano-phenyl, 2-methyl-6-methoxyphenyl, 2-methyl-6- ethoxy-phenyl; 2-ethyl-3-fluorophenyl, 2-ethyl-3-chlorophenyl, 2-ethyl-3-bromophenyl, 2-ethyl-3-methylphenyl, 2,3-diethylphenyl, 2- Ethyl-3-trifluoromethyl-phenyl, 2-ethyl-3-cyano-phenyl, 2-ethyl-3-methoxy-phenyl, 2-ethyl-3-ethoxy-phenyl, 2-ethyl-4-fluorophenyl, 2- Ethyl-4-chlorophenyl, 2-ethyl-4-bromophenyl, 2-ethyl-4-methylphenyl, 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-fluorophenyl, 2-ethyl-5-chlorophenyl, 2-ethyl-5-bromophenyl, 2-ethyl-5-methylphenyl, 2,5-diethylphenyl, 2- Ethyl-5-trifluoromethyl-phenyl, 2-ethyl-5-cyano-phenyl, 2-ethyl-5-methoxy-phenyl, 2-ethyl-5-ethoxy-phenyl, 2-ethyl-6-fluorophenyl, 2- Ethyl 6-chlorophenyl, 2-

Ethyl-6-bromophenyl, 2-ethyl-6-methylphenyl, 2,6-diethylphenyl, 2-ethyl-6-trifluoromethylphenyl, 2-ethyl-6-cyano-phenyl, 2- Ethyl 6-methoxyphenyl, 2-ethyl-6-ethoxyphenyl;

2-trifluoromethyl-3-fluorophenyl, 2-trifluoromethyl-3-chlorophenyl, 2-trifluoromethyl-3-bromophenyl, 2-trifluoromethyl-3-methylphenyl, 2-trifluoromethyl-3-ethylphenyl,

2,3-bis-trifluoromethyl-phenyl, 2-trifluoromethyl-3-cyano-phenyl, 2-trifluoromethyl-3-methoxy-phenyl, 2-trifluoromethyl-3-ethoxy-phenyl, 2-trifluoromethyl-4-fluorophenyl nyl, 2-trifluoromethyl-4-chlorophenyl, 2-trifluoromethyl-4-bromophenyl, 2-trifluoromethyl-4-methylphenyl, 2-trifluoromethyl-4-ethylphenyl, 2,4-bis -trifluoromethyl-phenyl, 2-trifluoromethyl-4-cyano-phenyl, 2-trifluoromethyl-4-methoxy-phenyl, 2-

Trifluoromethyl-4-ethoxyphenyl, 2-trifluoromethyl-5-fluorophenyl, 2-trifluoromethyl-5-chlorophenyl, 2-trifluoromethyl-5-bromophenyl, 2-trifluoromethyl-5-methylphenyl, 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-fluorophenyl, 2-trifluoromethyl-6-chlorophenyl, 2-trifluoromethyl-6-bromophenyl, 2-trifluoromethyl-6-methylphenyl, 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-fluorophenyl, 2-cyano-3-chlorophenyl, 2-cyano-3-bromophenyl, 2-cyano-3-methylphenyl, 2-cyano-3-ethylphenyl, 2-cyano-3-trifluoromethyl-phenyl,

2,3-dicyano-phenyl, 2-cyano-3-methoxy-phenyl, 2-cyano-3-ethoxy-phenyl, 2-cyano-4-fluorophenyl, 2-cyano-4-chlorophenyl, 2- Cyano-4-bromophenyl, 2-cyano-4-methylphenyl, 2-cyano-4-ethylphenyl, 2-cyano-4-trifluoromethylphenyl, 2,4-dicyano-phenyl, 2-cyano- 4-methoxy-phenyl, 2-cyano-4-ethoxy-phenyl, 2-cyano-5-fluorophenyl, 2-cyano-5-chlorophenyl, 2-cyano-5-bromophenyl, 2-cyano- 5-methylphenyl, 2-cyano-5-ethylphenyl, 2-cyano-5-trifluoromethylphenyl, 2,5-dicyano- phenyl, 2-cyano-5-methoxyphenyl, 2-cyano-5-ethoxyphenyl, 2-cyano-6-fluorophenyl, 2-cyano-6-chlorophenyl, 2-cyano-6-bromo -phenyl, 2-cyano-6-methylphenyl, 2-cyano-6-ethylphenyl, 2-cyano-6-trifluoromethylphenyl, 2-cyano-6-cyanophenyl, 2-cyano-6 -methoxy-phenyl, 2-cyano-6-ethoxy-phenyl; 2-methoxy-3-fluorophenyl, 2-methoxy-3-chlorophenyl, 2-methoxy-3-bromophenyl,

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-fluorophenyl, 2-methoxy-4-chlorophenyl, 2-methoxy-4-bromophenyl, 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-ethoxyphenyl, 2-methoxy-5-fluorophenyl, 2-methoxy-5-chlorophenyl, 2-methoxy-5-bromophenyl, 2-methoxy-5-methylphenyl, 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-fluorophenyl, 2-methoxy-6-chlorophenyl, 2-methoxy-6-bromophenyl, 2-methoxy-6-methylphenyl, 2-methoxy-6-ethylphenyl, 2-methoxy- 6-trifluoromethyl-phenyl, 2-methoxy-6-cyano-phenyl, 2,6-dimethoxy-phenyl, 2-methoxy-6-ethoxy-phenyl;

2-ethoxy-3-fluorophenyl, 2-ethoxy-3-chlorophenyl, 2-ethoxy-3-bromophenyl, 2-ethoxy-3-methylphenyl, 2-ethoxy-3-ethylphenyl, 2-ethoxy-3-trifluoromethylphenyl, 2-ethoxy-3-cyano-phenyl, 2-ethoxy-3-methoxyphenyl, 2,3-diethoxyphenyl, 2-

Ethoxy-4-fluorophenyl, 2-ethoxy-4-chlorophenyl, 2-ethoxy-4-bromophenyl, 2-ethoxy-4-methylphenyl, 2-ethoxy-4-ethylphenyl , 2-ethoxy-4-trifluoromethyl-phenyl, 2-ethoxy-4-cyano-phenyl, 2-ethoxy-4-methoxy-phenyl, 2,4-diethoxy-phenyl, 2-ethoxy-5-fluorophenyl , 2-ethoxy-5-chlorophenyl, 2-ethoxy-5-bromophenyl, 2-ethoxy-5-methylphenyl, 2-ethoxy-5-ethylphenyl, 2-ethoxy-5-trifluoromethylphenyl , 2-ethoxy-5-cyano-phenyl, 2-ethoxy-5-methoxy-phenyl, 2,5-diethoxy-phenyl, 2-ethoxy-6-fluoro-phenyl, 2-ethoxy-6-chlorophenyl , 2-ethoxy-6-bromophenyl, 2-ethoxy-6-methylphenyl, 2-ethoxy-6-ethylphenyl, 2-ethoxy-6-trifluoromethylphenyl, 2-ethoxy-6-cyano-phenyl , 2-ethoxy-6-methoxy-phenyl, 2,6-diethoxy-phenyl. Group 2

Ar ² has, for example, the meanings given above in Group 1.

Group 3

Ar ² has, for example, the meanings given above in Group 1.

Group 4

Ar ² has, for example, the meanings given above in Group 1.

Group 5

Ar ² has, for example, the meanings given above in Group 1. Group 6

Ar ² has, for example, the meanings given above in Group 1.

Group 7

Ar ² has, for example, the meanings given above in Group 1.

Group 8

Ar ² has, for example, the meanings given above in Group 1. Group 9

Ar ² has, for example, the meanings given above in Group 1.

Group 10

Ar ² has, for example, the meanings given above in Group 1.

Group 11

Ar ² has, for example, the meanings given above in Group 1.

Group 12

Ar ² has, for example, the meanings given above in Group 1. Group 13

Ar ² has, for example, the meanings given above in Group 1.

Group 14

Ar ² has, for example, the meanings given above in Group 1.

Group 15

Ar ² has, for example, the meanings given above in Group 1.

Group 16

Ar ² has, for example, the meanings given above in Group 1.

Group 17

Ar ² has, for example, the meanings given above in Group 1.

Group 18

Ar ² has, for example, the meanings given above in Group 1.

Group 19

Ar ² has, for example, the meanings given above in Group 1. Group 20

Ar ² has, for example, the meanings given above in Group 1.

Group 21

Ar ² has, for example, the meanings given above in Group 1.

Compounds according to groups 1 to 3 with the above requirement are particularly preferred.

Most preferred are compounds according to group 2 with the above proviso.

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

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

(a) arylamines of the general formula (II)

H _N ^ Ar ² N (ll)

R ² in which

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

with chloroformic acid esters of the general formula (III)

in which

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

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

or if - in the event that R ^{2 is} hydrogen -

(b) aryl isocyanates of the general formula (IV)

Ar ² 0 = C = NT (IV) in which

Ar ^{2 has} the meaning given above,

with substituted alkanols of the general formula (V)

Ar ¹ R ¹

(V)

O. ^ .H

O ^'

in which

Ar and R have the meaning given above, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.

If, for example, (-) - chloroformic acid [1- (3-methylphenoxymethyl) propyl] ester and 2-fluoro-6-methyl-aniline are used as starting materials, the course of the reaction in process (a) according to the invention can be carried out by the following Formula scheme are outlined:

If, for example, (-) - 1- (3-trifluoromethyl-phenoxymethyl) butanol and 2-chloro-5-methoxy-phenyl isocyanate are used as starting materials, the course of the reaction in process (b) according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the arylamines to be used as starting materials in process (a) according to the invention for the preparation of compounds of the general formula (I). In the general formula (II), Ar and R ² preferably have those meanings which have already been given above in connection with the description of the compounds of the general formula (I) according to the invention as preferred or particularly preferred for Ar ² and R ² . The starting materials of the general formula (II) are known organic synthetic chemicals.

Formula (III) provides a general definition of the chloroformate esters to be used further as starting materials in process (a) according to the invention. In the general formula (III), Ar ¹ and R ¹ preferably have those meanings which have already been given as preferred or particularly preferred for Ar ¹ and R ¹ in connection with the description of the compounds of the general formula (I) according to the invention.

The starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf. US Pat. No. 5,099,059, US Pat. No. 5,152,827, US Pat. No. 5,399,545).

Formula (IV) provides a general definition of the aryl isocyanates to be used as starting materials in process (b) according to the invention for the preparation of compounds of the general formula (I). In the general formula (IV), Ar ² preferably has the meaning which has already been given as preferred or particularly preferred for Ar ² in connection with the description of the compounds of the general formula (I) according to the invention.

The starting materials of the general formula (IV) are known organic synthetic chemicals.

Formula (V) provides a general definition of the substituted alkanols to be used further as starting materials in process (b) according to the invention. In the general formula (V), Ar ¹ and R ¹ preferably have those meanings which have already been given above as preferred or particularly preferred for Ar ¹ and R ¹ in connection with the description of the compounds of the general formula (I) according to the invention. - lo -

The starting materials of the general formula (V) are known and / or can be prepared by processes known per se (cf. US Pat. No. 5,099,059, US Pat. No. 5,152,827, US Pat. No. 5,399,545).

The usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries for processes (a) and (b). These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or

Calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methanolate, ethanolate, -n- or -i-propanolate, - n-, -i-, -s- or -t-butanolate; basic organic nitrogen compounds such as 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).

Inert organic solvents are particularly suitable as diluents for carrying out processes (a) and (b) according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated

Hydrocarbons such as gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile;

Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methyl-pyrrolidone or 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, their mixtures with water or pure water.

The reaction temperatures can be varied within a substantial range when carrying out processes (a) and (b) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

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

To carry out processes (a) and (b) according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a large excess. The reaction is generally carried out in a suitable diluent, if appropriate in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The active compounds according to the invention can be used, for example, in the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

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

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria,

Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Arostegilopus, Arostegilop, Arostopsilium, Aecropis Phalaris.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to others

Plants.

Depending on the concentration, the active compounds according to the invention are suitable for combating total weeds, for example on industrial and rail tracks and on paths and squares with and without tree growth. The active compounds according to the invention for combating weeds in permanent crops, for example forest, ornamental wood, Fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, used on ornamental and sports turf and pasture land and for selective weed control in annual crops become.

The compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and decotyledon crops, both in the pre-emergence and in the post-emergence process.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances. These formulations are prepared in a known manner, e.g. B. by

Mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils , Alcohols, such as butanol or glycol, and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. The following are suitable as solid carriers: for example ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules Question: eg broken and fractionated natural rocks such as calcite,

Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.

Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0J and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible. Known herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), am tryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azim-sulfurone, benazoline (- ethyl), benfuresate, bensulfuron (-methyl), bentazone, benzopenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxime, bromoxynil, butachlor, butroxydim, butylate, cafenstrole, caloxydim , Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinidone (-ethyl), Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl)

Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam- (-methyl), Cumyluron, Cyanazines, 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, Difluefenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid,

Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop (-P-ethyl) - propyl), flamprop (-isopropyl-L), flamprop (-methyl), flazasulfuron, fluazifop (-P-butyl), fluazolate, flucarbazone, flufenacet, flumetsulam, flumiclorac (-pentyl),

Flumioxazin, Flumipropyn, Flumetsulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurpyrsulfuron (-methyl, -sodium), Fluronol (-butyl), Fluridone, Fluroxypyr (-mprimidol, Fluroxypyr (-meptidol), Fluroxypyr (-meptylol) , Fluthiacet- (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl),

Hexazinone, imazamethabenz (-methyl), imazamethapyr propalin, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, ioxynil, iso-, isoproturon, isouron, isoxaben, Isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolochlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Mono- linuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orben-carb, oryzalin, oxadiargyl, oxadiazon, oxasulftiron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone, phenmediphamisulfonuronophone, promoterpylsulfonone (prom), piperoxynilurone, pore Propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen (-ethyl),

Pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxime, 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, Ter-butryn, Thenylchlor, Thiafluamide, Thiazopyridium, Thiazopyron, Thiazopyrid, Thiazopyrid, , Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifluralin and Triflusulfuron.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

The active ingredients as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use

Solutions, suspensions, emulsions, powders, pastes and granules are used. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.

The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.

The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.

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

Manufacturing examples

example 1

(Method (b)

A mixture of 1.20 g (5 mmol) (-) - l-ethyl-2- (3-trifluoromethyl-phenoxy) - ethanol, 0.70 g (5 mmol) 2,3-dimethyl-phenyl isocyanate, 0J g ( 10 mmol) of triethylamine and 20 ml of acetonitrile is stirred for 15 hours at room temperature (approx. 20 ° C.) and then carefully concentrated in a water jet vacuum. The residue is digested with petroleum ether and the crystalline product is isolated by suction.

1.3 g (68% of theory) (-) - N- (2,3-dimethylphenyl) -O- [l-ethyl-2- (3-

20 trifluoromethylphenoxy) ethyl] carbamate with a melting point of 68 ° C .; [αj. = + 24.8 °.

Analogously to Example 1 and in accordance with the general description of the production processes according to the invention, it is also possible, for example, to prepare the compounds of the general formula (I) listed in Table 1 below.

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

Starting materials of the general formula (V):

Example (V-l)

Separation of the racemate into the individual enantiomers:

The racemate was separated at room temperature (approx. 20 ° C) by HPLC (High Performance Liquid Chromatography) on the chiral stationary silica gel phase Chiracel OD ^® using a mixture of n-heptane and isopropanol as eluent and photometric detection.

Column: Chiracel OD ^® 20μm (manufacturer: Daicel, Japan) 500 * 40 mm

Eluens: n-heptane / isopropanol (vol. 10: 1)

Flow: 30 ml / min

Detection: UV 254 nra

Sample application: 100 mg racemate (= 2.5 ml of a solution of 1 g racemate in

25 ml eluent)

After analytical testing for enantiomeric purity, the eluate fractions were combined accordingly, evaporated under reduced pressure and used as a crude product for further reactions.

The left-turning enantiomer elutes under the above conditions

20 first. Specific rotation value of the left-turning enantiomer: [α] „= -15.9 (measured in chloroform) at a concentration of 20 mg / ml solution.

The total amount was separated in this way by repeated application of 100 mg of racemate each. Examples of use:

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area. The concentration of the spray liquor is chosen so that the desired amount of active compound is applied in 1000 liters of water per hectare.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means: 0% = no effect (like untreated control)

100% = total annihilation

In this test, for example, the compounds according to Preparation Examples 1 and 2, with good tolerance to crop plants, such as, for example, wheat, barley, cotton and soybeans, show a strong action against weeds. Example B

Post emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired level

Concentration.

Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that in

1000 1 water / ha the desired amounts of active ingredient are applied.

It means:

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

In this test, for example, the compounds according to Preparation Examples 1 and 2 show a strong action against weeds.

Claims

claims

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

in which

Ar * for an optionally substituted, monocyclic or bicyclic, carbocyclic or heterocyclic group from the series phenyl, naphthyl, tetralinyl, furyl, benzofuryl, thienyl,

Benzothienyl, pyridinyl, quinolinyl, isoquinolinyl or the - also optionally substituted below grouping

where A is halogen-substituted alkanediyl having 1 to 3 carbon atoms, and the possible substituents are preferably selected from the following list:

Cyano, nitro, halogen, each optionally substituted by halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl each having up to 5 carbon atoms,

Ar-2 for optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or by (in each case optionally by cyano, halogen, C, -C ₄ - alkoxy, C _r C ₄ - alkylthio, C, -C ₄ Alkylsulfinyl or C, -C ₄ -alkylsulfonyl substituted) alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, Alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl each having up to 4 carbon atoms in the alkyl groups substituted aryl having 6 or 10 carbon atoms,

with the proviso that in the compounds of the general formula (I) the substituents on the carbon atom to which R ^{1 is} bonded are arranged such that the plane of oscillation of polarized light is rotated to the left, ie that the compounds of the formula (I) are present as (-) - enantiomers.

2. Substituted N-aryl-O-aryloxyalkyl carbamates according to claim 1, characterized in that

Arl for an optionally substituted, monocyclic or bicyclic, carbocyclic or heterocyclic group from the series phenyl, naphthyl, tetralinyl, furyl, benzofuryl, thienyl, benzothienyl, pyridinyl, quinolinyl, isoquinolinyl or the - also optionally substituted below groups

A stands for methylene or dimethylene (ethane-1J-diyl) which is optionally substituted by fluorine and / or chlorine, and where the possible substituents are preferably selected from the following list:

Cyano, nitro, fluorine, chlorine, bromine, each optionally substituted by fluorine and / or chlorine, 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 ^ for each optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or by (in each case optionally by 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 , Ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, acetyl, propionyl, n- or s-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i -Propoxycarbonyl, methyl aminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl or diethylaminocarbonyl substituted

Phenyl or naphthyl,

R 'represents methyl, ethyl, n- or i-propyl, and

R ^{2 represents} hydrogen, methyl, ethyl, n- or i-propyl. Substituted N-aryl-O-aryloxyalkyl-carbamates according to claim 1, characterized in that

Arl represents phenyl, which in the 3-position is a substituent from the series cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-

Contains propyl, chloromethyl, fluoromethyl, dichloromethyl, difluoromethyl, trichloromethyl, trifluoromethyl, methoxy, ethoxy, fluoromethoxy, difluoromethoxy, chlorofluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy and optionally contains another substituent in a different position according to the preceding list,

Ar-2 for optionally by nitro, cyano, fluorine, chlorine, bromine or by (in each case optionally substituted by fluorine or chlorine) methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,

Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, dimethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl or dimethylaminocarbonyl, substituted

R ^{1 represents} methyl or ethyl, and

R ^{2 represents} hydrogen, methyl or ethyl.

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) H, .Ar '

^* N ^' (II)

R 'in which

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

with chloroformic acid esters of the general formula (III)

in which

Ar and R have the meaning given in one of claims 1 to 3,

or that - if R ^{2 is} hydrogen -

(b) aryl isocyanates of the general formula (IV)

Ar ² 0 = C = N ^ (IV) in which

Ar ^{2 has} the meaning given in one of claims 1 to 3,

with substituted alkanols of the general formula (V)

in which Ar and R have the meaning given in one of claims 1 to 3,

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

Process for controlling unwanted plants, characterized in that at least one substituted N-aryl-O-aryloxyalkyl carbamate according to one of Claims 1 to 3 is allowed to act on undesired plants and / or their habitat.

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

Herbicidal agent, characterized by the content of at least one substituted N-aryl-O-aryloxyalkyl carbamate according to one of Claims 1 to 3 and conventional extenders.