WO1999021841A1

WO1999021841A1 - Substituted aryloxy alkyl amino triazines

Info

Publication number: WO1999021841A1
Application number: PCT/EP1998/006511
Authority: WO
Inventors: Stefan Lehr; Hans-Jochem Riebel; Uwe Stelzer; Rolf Kirsten; Andreas Lender; Katharina Voigt; Markus Dollinger; Mark Wilhelm Drewes; Ingo Wetcholowsky; Yukiyoshi Watanabe; Randy Allen Myers
Original assignee: Bayer Aktiengesellschaft; Nihon Bayer Agrochem K.K.
Priority date: 1997-10-24
Filing date: 1998-10-14
Publication date: 1999-05-06
Also published as: EP1034168A1; CA2307093A1; KR20010024451A; AU2047399A; CN1277606A; BR9812769A; DE19746994A1; JP2001521028A

Abstract

The invention relates to novel substituted aryloxy alkyl amino triazines of formula (I) wherein R1 stands, for example, for H or C¿1?-C6 alkyl; R?2¿ stands, for example, for H, C¿1?-C6-alkyl or C1-C6 alkyl carbonyl; R?3¿ stands, for example, for C¿2?-C6 alkyl, R?4¿ stands for example for H or C¿1?-C4 alkyl; AR stands, for example, for substituted or unsubstituted phenyl and Z stands, for example, halogen, C1-C6 alkyl, C1-C6 hydroxy alkyl, C1-C6 halogen alkyl or C3-C6 cyclo alkyl. The invention also relates to a method for the production and use thereof as herbicides.

Description

Substituted aryloxyalkyl aminotriazines

The invention relates to new substituted aryloxyalkylaminotriazines, processes for their preparation and their use as herbicides.

A number of substituted aryloxyalkylaminotriazines are already known from the (patent literature) (cf. EP 273328, EP 411153 / WO 90/09378). However, these compounds have not hitherto gained any particular importance.

There have now been the new substituted aryloxyalkylaminotriazines of the general

Formula (I)

R, FT

N ^'

in which

R ^{1 represents} hydrogen or alkyl having 1 to 6 carbon atoms optionally substituted by hydroxy, cyano, halogen or Cj-Cj-alkoxy,

R ^{2 represents} hydrogen, formyl or, in each case optionally by cyano,

Halogen or C j -C -] - alkoxy substituted alkyl, alkylcarbonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups,

R ³ for alkyl optionally substituted by hydroxy, cyano, halogen or Cj-Czj-alkoxy having 2 to 6 carbon atoms or for optionally by

Cyano, halogen or Ci-Cj-alkyl substituted cycloalkyl having 3 to 6 carbon atoms, R ^{4 represents} hydrogen or alkyl having 1 to 4 carbon atoms,

Ar represents optionally substituted phenyl, naphthyl, tetralinyl or heterocyclyl,

the possible heterocyclyl groupings are preferably selected from the following group:

Furyl, benzofuryl, thienyl, benzothienyl, thiazolyl, benzthiazolyl, oxazolyl, benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, pyridinyl and

Pyrimidinyl,

and the possible substituents are each preferably selected from the following group:

Hydroxy, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, in each case optionally substituted by hydroxy, cyano or halogen, alkyl or alkoxy each having 1 to 6 carbon atoms, in each case optionally substituted by halogen, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylamino, Alkylcarbonylamino, alkylsulfonylamino, bis-alkylcarbonylamino, bis-alkylsulfonylamino, N-alkyl-N-alkylcarbonylamino or N-alkyl-N-alkylsulfonylamino each having 1 to 6 carbon atoms in the alkyl groups, respectively phenyl or phenoxy optionally substituted by hydroxy, cyano, nitro, halogen, Cj-Cj-alkyl, Ci-Cj-haloalkyl, CJ-C4-alkoxy or C \ -C4-haloalkoxy, and in each case optionally substituted by halogen methylenedioxy or ethylenedioxy,

and

for halogen, for each optionally by hydroxy, cyano, halogen, C} - C4-alkoxy, -C -C4-alkylcarbonyl, -C -C4-alkoxy-carbonyl, C1-C4- alkyl thio, C 1 -C 4 alkylsulfonyl or C 4 -C 4 alkylsulfonyl substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, or for optionally by cyano, halogen or C1-C4 Alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,

found.

The new substituted aryloxyalkylaminotriazines of the general formula (I) are obtained if

(a) aryloxyalkyl biguanides of the general formula (II)

in which

R ¹ , R ² , R ³ , R ⁴ and Ar have the meaning given above,

and / or acid adducts of compounds of the general formula (II)

with alkoxy carbonyl compounds of the general formula (III)

Z-CO-OR '(III)

in which

Z has the meaning given above and R 'represents alkyl,

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

or if you

(b) substituted halotriazines of the general formula (IV)

in which

R ³ , R ⁴ , Ar and Z have the meaning given above and

X represents halogen,

with nitrogen compounds of the general formula (V)

in which

R ¹ and R ^{2 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 you

(c) substituted aminotriazines of the general formula (VI)

^R V ^R2

in which

R ¹ , R ² and Z have the meaning given above and

Y ^{1 represents} halogen or alkoxy,

with aryloxyalkylamines of the general formula (VII)

in which

Ar, R ³ and R ^{4 have} the meaning given above,

or if you (d) for the preparation of compounds of the formula (I) in which R ^{2 is} different from hydrogen,

Aryloxyalkylaminotriazines of the general formula (Ia)

in which

R ¹ , R ³ , R ⁴ , Ar and Z have the meaning given above,

with alkylating or acylating agents of the general formula (VIII)

Y ² -R ² (VIII)

in which

R ² has the meaning given above with the exception of hydrogen and

Y ^{2 represents} halogen, -OR ² or -O-CO-R ² ,

and optionally on the compounds of the general formula (I) obtained according to the processes described under (a), (b), (c) or (d), as part of the above definition of substituents, by further conversions by customary methods. The new substituted aryloxyalkylaminotriazines of the general formula (I) are notable for strong and selective herbicidal activity

The compounds of the general formula (I) according to the invention contain at least one asymmetrically substituted carbon atom and can therefore exist in different enantiomeric (R and S-configured forms) or diastereomeric forms. The invention relates to the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) as well as the mixtures of these isomeric compounds

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

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine

The invention preferably relates to compounds of the formula (I) in which

R ¹ for hydrogen or for each optionally by hydroxy, cyano, fluorine,

Chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl. is n-, i-, s- or t-butyl,

R ^{2 represents} hydrogen, formyl, or methyl, ethyl substituted in each case by cyano, fluorine, chlorine, bromine, methoxy or ethoxy,

Acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl or ethoxycarbonyl,

R ³ each represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy or ethoxy or each which is optionally substituted by cyano, fluorine, chlorine, Methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, R ^{4 represents} hydrogen or methyl,

Furyl, benzofüryl, thienyl, benzothienyl, thiazolyl, benzthiazo'yl, oxazolyl,

Benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, pyridinyl and pyrimidinyl,

Hydroxy, cyano, carbamoyl, thiocarbamoyl, nitro, fluorine, chlorine, bromine, each optionally substituted by hydroxy, cyano, fluorine 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, each optionally substituted by fluorine or chlorine, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n - or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, dimethylamino, diethylamino, acetylamino, methylsulfononamino , Ethylsulfonylamino, bis-acetylamino, bis-methylsulfonylamino, N-methyl-N-acetylamino or N-methyl-N-methylsulfonylamino, each optionally by hydroxy, cyano, nitro, fluorine, chlorine, bromine, Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-Bu toxy, difluoromethoxy or trifluoromethoxy substituted phenyl or phenoxy, and also methylene dioxy or ethylenedioxy optionally substituted by fluorine or chlorine, and

Z for fluorine, chlorine, bromine, for each optionally by hydroxy, cyano, nitro, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-

Butoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl 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, methylsulfinyl, Ethylsulfinyl, n- or i-

Propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, or for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl which is optionally substituted by cyano, fluorine, chlorine, methyl or ethyl.

From the compounds of the compounds previously defined as preferred (“preferably”)

The following groups are particularly noteworthy for formula (I):

(A) the compounds of the formula (I) in which R ¹ , R ² , R ³ , R ⁴ and Z have the meaning indicated above and Ar represents in each case optionally substituted phenyl or naphthyl, the possible substituents having the meaning indicated above to have;

(B) the compounds of the formula (I) in which R ¹ , R ² , R ³ , R ⁴ and Z have the meaning given above and Ar represents optionally substituted heterocyclicl, the possible heterocyclyl groups and the possible substituents being the have previously given meaning.

The invention relates in particular to compounds of the formula (I) in which

R ^{1 represents} hydrogen or methyl or ethyl which is optionally substituted by cyano, fluorine, methoxy or ethoxy, R ^{2 represents} hydrogen or methyl, ethyl, acetyl or propionyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

R ³ represents ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy,

R ^{4 represents} hydrogen,

Ar represents in each case optionally substituted phenyl or naphthyl,

where the possible substituents are in particular selected from the following group:

Hydroxy, cyano, nitro, fluorine, chlorine, bromine, each optionally through

Hydroxy, cyano, fluorine 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, each optionally substituted by fluorine or chlorine, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, each optionally by hydroxy, cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy-substituted phenyl or phenoxy, and also methylene dioxy optionally substituted by fluorine or chlorine or ethylenedioxy,

and

for each optionally by hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, Methylsulfinyl, ethylsulfinyl, n- or l-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or l-propylsulfonyl substituted methyl, ethyl, n- or l-propyl, n-, l-, s- or t-butyl, or for each optionally cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted by cyano, fluorine, chlorine, methyl or ethyl

The following groups should be particularly emphasized from the compounds of the formula (I) defined above as being particularly preferred

(A) the compounds of the formula (I) in which R ¹ , R ² , R ³ , R ⁴ and Z have the meaning indicated above and Ar represents in each case optionally substituted phenyl or naphthyl, the possible substituents having the meaning indicated above with the proviso that the substituents of the carbon atom to which R ^{3 is} attached are arranged in the R configuration,

(B) the compounds of the formula (I) in which R ¹ , R ² , R ³ , R ⁴ and Z have the meaning indicated above and Ar represents in each case optionally substituted phenyl or naphthyl, the possible substituents having the meaning indicated above have, with the proviso that the substituents of the carbon atom to which R ^{3 is} bound, are arranged in the S configuration

The general or preferred range definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for production. These radical definitions can be combined with one another, that is to say also between the preferred ranges indicated

Examples of the compounds of the formula (I) according to the invention are listed in the groups below. The general formulas here each stand for the R-enantiomers, the S-enantiomers and the racemates Group 1

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given in the list below.

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, chlorofluoromethyl, chlorobromomethyl,

Chlorodifluoromethyl, fluorodichloromethyl, bromodifluoromethyl, trichloromethyl, 1-fluoro-ethyl, 2-fluoro-ethyl, 1-chloro-ethyl, 2-chloro-ethyl, 1-bromo-ethyl, 1-chloro-1-fluoro-ethyl, 1 - Fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 1-bromopropyl, 1-fluor-1-methyl-ethyl, 2-fluoro-l-methyl-ethyl, 1-chloro-1-methyl-ethyl, 1-fluoro-1-methyl-propyl, 1-chloro-1-ethyl-propyl, 1 -

Fluoro-1-ethyl-propyl, l-fluoro-2-methyl-propyl, l-chloro-2-methyl-propyl, 2-chloro-l-methyl-ethyl, 1, 1-difluoro-ethyl, 1,2- Difluoro-ethyl, 1, 1-dichloro-ethyl, 2,2,2-trifluoro-ethyl, 1,2,2,2-tetrafluoro-ethyl, perfluoroethyl, 1, 1-difluoropropyl, 1,1-dichloro- propyl, perfluoropropyl, 1-fluorobutyl, 1-chlorobutyl, perfluorobutyl, perfluoropentyl, perfluoro-hexyl, 1-hydroxyethyl, 1-hydroxy-1-methyl-ethyl, 1-hydroxypropyl, methoxy-methyl, Ethoxymethyl, dimethoxy-methyl, 1-methoxyethyl, 2-methoxy-ethyl, 1, 1-dimethoxy-ethyl, 1-ethoxyethyl, 2-ethoxy-ethyl, 2,2-dimethoxy-ethyl, 2,2-diethoxy- ethyl, 2-methoxy-l-methyl-ethyl, 2-methoxy-1-ethyl-ethyl, 2-ethoxy-l-methyl-ethyl, 2-ethoxy-l-ethyl-ethyl, 2,2-bis-methoxy- methyl, methylthiomethyl, ethylthiomethyl, 1-methylthio-ethyl, 2-methylthioethyl, 1-ethylthio-ethyl, 2-ethylthioethyl, methylsulfinylmethyl, ethylsulfinylmethyl, methylsulfonylmethyl, ethylsulfonylmethyl, cyclopropyl, 1-cyano-cyclopropyl, 1-fluorine 1-chloro-cyc lopropyl, 2-cyano-cyclopropyl, 2-fluorocyclopropyl, 2-chloro-cyclopropyl, 2,2-difluoro-cyclo- propyl, 2,2-dichlorocyclopropyl, cyclobutyl, 2,2-difluorocyclobutyl, 2,2,3-trifluorocyclobutyl, 2,2-difluoro-3-chlorocyclobutyl, cyclopentyl, cyclohexyl.

Group 2

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 3

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 4

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 5

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 6

(a racemate, b R enantiomers, c. S enantiomers)

Z has, for example, the meanings given above in Group 1

Group 7

(a racemate, b R enantiomers, c S enantiomers)

Z has, for example, the meanings given above in Group 1

Group 8

(a racemate, b R enantiomers, c S enantiomers)

Z has, for example, the meanings given above in Group 1 Group 9

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 10

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 1

(a racemate, b R enantiomers, c S enantiomers)

Z has, for example, the meanings given above in Group 1

Group 12

(a racemate, b R enantiomers, c S enantiomers)

Z has, for example, the meanings given above in Group 1

Group 13

(a racemate, b R enantiomers, c S enantiomers)

Z has, for example, the meanings given above in Group 1 Group 14

(a racemate, b R enantiomers, c S enantiomers)

Z has, for example, the meanings given above in Group 1

Group 15

(a racemate, b R enantiomers, c S enantiomers)

Z has, for example, the meanings given above in Group 1

Group 16

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 17

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 18

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 19

(a racemate, b R enantiomers, c S enantiomers)

Z has, for example, the meanings given above in Group 1

Group 20

(a racemate, b R enantiomers, c S enantiomers)

Z has, for example, the meanings given above in Group 1

Group 21

(a racemate, b R enantiomers, c S enantiomers)

Z has, for example, the meanings given above in Group 1

Group 22

(a racemate, b R enantiomers, c S enantiomers)

Z has, for example, the meanings given above in Group 1

Group 23

(a racemate, b R enantiomers, c S enantiomers)

Z has, for example, the meanings given above in Group 1 Group 24

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 25

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 26

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 27

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 28

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 29

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 30

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 31

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 32

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 33

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 34

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 35

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 36

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 37

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1

Group 38

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 39

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 40

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 41

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 42

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 43

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 44

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 45

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 46

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 47

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 48

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 49

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 50

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 51

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 52

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 53

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 54

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 55

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 56

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 57

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 58

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 59

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 60

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 61

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 62

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 63

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 64

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 65

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 66

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 67

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 68

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 69

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 70

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 71

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 72

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 73

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 74

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 75

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 76

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 77

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 78

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 79

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 80

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 81

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 82

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 83

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 84

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 85

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 86

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 87

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 88

(a: racemates, b: R enantiomers, c: S enantiomers)

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

Group 89

(a: racemates, b: R enantiomers, c: S enantiomers)

Z has, for example, the meanings given above in Group 1. Group 90

(a racemate, b R enantiomers, c S enantiomers)

Z has, for example, the meanings given above in Group 1

Group 91

(a Racemate b R enantiomers, c S enantiomers)

Z has, for example, the meanings given above in Group 1

Group 92

(a: racemates, b: R enantiomers, c: S enantiomers)

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

If, for example, 1- (1-phenoxymethyl-propyl) -biguanide and methyl trifluoroacetate are used as starting materials, the course of the reaction in process (a) according to the invention can be outlined using the following formula:

If, for example, 2-chloro-4- (l-phenoxymethyl-propylamino) -6-trifluoromethyl-l, 3,5-triazine and ethylamine are used as starting materials, the course of the reaction in process (b) according to the invention can be outlined by the following formula become:

If, for example, 2-amino-4-methoxy-6-trifluoromethyl-l, 3,5-triazine and 1-phenoxymethyl-propylamine are used as starting materials, the course of the reaction in process (c) according to the invention can be outlined using the following formula:

If, for example, 2-amino-4- (l-phenoxymethyl-propylamino) -6-trifluoromethyl-l, 3,5-triazine and acetyl chloride are used as starting materials, the course of the reaction in process (d) according to the invention can be carried out by the following Formula scheme are outlined:

The process (a) according to the invention for the preparation of compounds of

Formula (I) to be used as starting materials aryloxyalkyl biguanides are generally defined by formula (II). In the formula (II), R ¹ , R ² , R ³ , R ⁴ and Ar preferably or in particular have those meanings which have already been described above in connection with the description of the compounds of the formula (I), preferably or as in particular were preferably given for R ¹ , R ² , R ³ , R ⁴ and Ar.

The starting materials of the general formula (II) are not yet known from the literature; as new substances, they are the subject of a previous, not previously published patent application (cf. DE-A-19641691 of 10.10.1996 - LeA31995).

Suitable acid adducts of compounds of the formula (II) are their addition products with protonic acids, such as, for example, with hydrogen chloride (hydrogen chloride), Hydrogen bromide (hydrogen bromide), sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.

The aryloxyalkyl biguanides of the general formula (II) are obtained if substituted aryloxyalkylamines of the general formula (VII)

in which

R ³ , R ⁴ and Ar have the meaning given above,

and / or acid adducts of compounds of the general formula (VII), such as e.g. the hydrochloride -

with cyanoguanidine ("dicyandiamide") of the formula (IX)

N

II ^ ^N

I I

H H

optionally in the presence of a reaction auxiliary, e.g. Hydrogen chloride, and optionally in the presence of a diluent, e.g. n-Decane or 1,2-dichlorobenzene, reacted at temperatures between 100 ° C and 200 ° C (cf. EP 492615, production examples).

The aryloxyalkylamines of the general required as precursors

Formula (VII) are known and / or can be prepared by processes known per se (cf. Acta Pol. Pharm. 53 (1996), 47-52 - cited in Chem. Abstracts 126 46897, Angew Chem 106 (1994), 1041-1043, Bull Soc Chim Belg 85 (1976), 421-425, loc cit 86 (1977), 1003-1007, J Med Chem 10 (1967), 717-724, J Am Chem Soc 97 (1975), 6900-6901, Tetrahedron Lett 35 (1994), 3745-3746, DE 3222152, DE 3221540, EP 355351, EP 601486, ZA6903772, production examples)

The alkoxycarbonyl compounds to be used further as starting materials in the process (a) according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (III). In formula (III) Z preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as being particularly preferred for Z, R 'preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl

The starting materials of the formula (III) are known synthetic chemicals

The substituted halogentazines which are used as starting materials in the process (b) according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (IV). In the formula (IV), R ³ , R ⁴ , Ar and Z preferably or in particular those meanings which have already been mentioned above in connection with the description of the compounds of the formula according to the invention

(I) preferably or as particularly preferred for R ³ , R ⁴ , Ar and Z, X preferably represents fluorine or chlorine, in particular chlorine

The starting materials of the general formula (IV) are not yet known from the literature, as new substances they are the subject of a preliminary, unpublished patent application (cf. DE-A-19641691 dated 10 10 1996 - LeA31995)

You get the substituted Halogenentπazine of the general formula (IV), if you corresponding Dihalogentπazine of the general formula (X) X

N ^' N (X)

^? N ^ X ¹

in which

X and Z have the meaning given above and

X ^{1 represents} halogen,

with substituted aryloxyalkylamines of the general formula (VII)

in which

R ³ , R ⁴ and Ar have the meaning given above,

optionally in the presence of an acid acceptor, e.g. Ethyldiisopropylamine and optionally in the presence of a diluent, e.g. Tetrahydrofuran or dioxane, at temperatures between -50 ° C and + 50 ° C (see. The manufacturing examples).

Formula (VI) provides a general definition of the substituted aminotriazines to be used as starting materials in process (c) according to the invention for the preparation of compounds of the formula (I). In the formula (VI), R ¹ , R ² and Z preferably or in particular have those meanings which have already been described above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R ¹ , R ² and Z specified were; Y ¹ preferably represents fluorine, chlorine, methoxy or ethoxy, in particular chlorine or methoxy.

The starting materials of the general formula (VI) are known and / or can be prepared by processes known per se (cf. WO 95/11237).

Formula (VII) provides a general definition of the substituted aryloxyalkylamines to be used further as starting materials in process (c) according to the invention. In formula (VII), R ³ , R ⁴ and Ar preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R ³ , R ⁴ and Ar were specified.

The starting materials of the general formula (VII) are known and / or can be prepared by processes known per se (cf. DE 3426919; DE 4000610; DE

4332738, EP 320898; EP 443606; Tetrahedron: Asymmetry 5 (1994), 817-820; Tetrahedron Lett. 29: 223-224 (1988); loc. cit. 36: 3917-3920 (1995); Manufacturing examples).

The process (d) according to the invention for the preparation of compounds of

Formula (I) to be used as starting materials aryloxyalkylaminotriazines are generally defined by the formula (Ia). In the formula (Ia), R ¹ , R ³ , R ⁴ Ar and Z preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) preferably or as particularly preferred for R ¹ , R ³ , R ⁴ Ar and Z were given.

The starting materials of the general formula (Ia) as new substances are the subject of the present application, but in some cases also the subject of a previous, not previously published patent application (cf. DE-A-19641691 of 10.10.1996 -

LeA31995); they can be prepared by processes (a), (b) or (c) according to the invention (cf. the preparation examples). Formula (VIII) provides a general definition of the alkylating or acylating agents to be used further as starting materials in process (d) according to the invention. In the formula (VTII), R ^2, with the exception of hydrogen, preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R ² ; Y ² preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, acetyloxy or propionyloxy, in particular chlorine, methoxy or acetyloxy.

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

The processes according to the invention for the preparation of the compounds of the formula (I) are optionally carried out using a reaction auxiliary.

Suitable reaction auxiliaries for processes (a), (b), (c) and (d) are generally the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as 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 - -methanolat, -ethanolat, -n- or -i-propanolat, -n-, -i-, -s- or -t-butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimethyl benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2,2,2] octane

(DABCO), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), or 1,8-diazabicyclo [5,4,0] undec-7-ene (DBU). Suitable diluents for carrying out processes (a), (b), (c) and (d) in addition to water are, in particular, inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, 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 methyl or isopropyl Methyl isobutyl ketone, nitriles, such as acetonitrile, propionitrile or butyronitrile, amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrohdon or hexamethlylphosphoric acid 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), (b), (c) and (d) according to the invention. In general, temperatures between -20 ° C. and + 300 ° C., preferably between -10 ° C and + 250 ° C

The processes (a), (b), (c) and (d) 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 increased or reduced pressure - generally between 0.1 bar and 10 bar - to be carried out

To carry out the processes according to the invention, the starting materials are generally used in approximately aquimolar amounts. However, it is also possible to use one of the components in a larger excess

The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally agitated several hours at the required temperature. 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 e.g. can be used in the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium,

Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicot 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, Agrostis, Alopecurus, Apera.

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 other plants.

Depending on the concentration, the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover. Likewise, the connections for weed control in permanent crops, e.g. forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea -, gum, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective weed control in annual crops

The compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledons

Cultures both pre-emergence and post-emergence

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, impregnated with active compounds

Natural and synthetic substances as well as very fine encapsulation 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

Emulsifiers and / or dispersants and / or foaming agents

If water is used as an extender, it is also possible, for example, to use organic solvents as auxiliary solvents. Aromatic solvents, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes, are essentially suitable as liquid solvents or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. 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

Solid carrier materials that come into question are, 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, and solid carrier materials for granules Question e.g. broken and fractionated natural rocks such as calcite, marble,

Pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust. Coconut shells, corn cobs and tobacco stalks, as emulsifying and / or foam-generating agents are suitable, for example, nonionic and anionic emulsifiers. such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates, and dispersants are, for example, lignin sulfite liquor and methyl cellulose

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, 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, for example 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 0.1 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), Ametryne, Amidochlor, Amidosulfüron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfüron, Benazolin (-ethyl), Benfüresate, Bensulfüron (-methyl)

Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyidaz, Chloronben, Chloramben, Chloramben, Chlorimuron (-ethyl), chloronitrofen, chlorosulfuron, chlorotoluron, cin- methylin, cinosulfuron, clethodim, clodinafop (-propargyl), clomazone, clomeprop,

Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (-methyl), Cumyluron, Cyanazines, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefüron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Dihenamidon, Diquxurflam Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop (- P-ethyl), Flamprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl ), Flaza-sulfurone, fluazifop (-P-butyl), flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), fluopoxam, flupropacil, flurpyrsulfuron ( , -sodium), flurenol (-butyl), fluridone, fluroxypyr (-meptyl), flurprimidol, flurtamone, fluthiacet (-methyl), fluthiamide, fomesafen, glufosi nate (-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop (-ethoxyethyl), haloxyfop (-P-methyl), hexazinones, imazamethabenz (- methyl), imazamethapyr, imazamox, imazapyr, imazaquin, imazethapyr, imazosulf- Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfüron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfüron, Norflurazon, Oxbenulfadonzon, Orbencarbadiazon, Orbencarbadiazon, Orbencarbadiazon Oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfüron (-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulfuronethyl, prosulfuron-carbons, pro Pyrazolate, Pyrazosulfüron (-ethyl), Pyrazoxyfen, Pyribenzoxim, Pyributicarb, Pyridate, Pyriminobac (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P -tefüryl), Rimsulfüron, Sethoxydim, Simazine, Simetryn,

Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfüron, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfüron (-methyl), Thiobencarb, Trioxycarbonuron, Sulfur -methyl), triclopyr, tridiphane, trifluralin and triflusulfüron.

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 compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. 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.

Production examples: Example 1

(Method (a))

A mixture of 3.2 g (10 mmol) (R / S) -l- [l-ethyl-2- (3,5-dimethyl-phenoxy) -ethyl] -biguanide hydrochloride (racemic) prepared at -10 ° C ), 1.3 g (10.6 mmol) trifluoroacetic acid methyl ester, 1.0 g (20 mmol) sodium methylate, 2.75 g zeolite molecular sieve and 20 ml methanol is approx. 15 hours at approx. 0 ° C stirred. It is then suctioned off, the filtrate is diluted to about three times the volume with water, shaken with ethyl acetate, the organic phase is separated off, washed with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.

2.0 g (92% by HPLC, ie 52% of theory) (R / S) -2-amino-4-trifluoromethyl-6- [1 - (3,5-dimethylphenoxymethyl) propylamino] are obtained. - 1,3,5-triazine (Racemat) as an amorphous residue; logP: 3.77 ^b) .

Analogously to Example 1 and in accordance with the general description of the production processes according to the invention, for example, the ones in

Compounds of formula (I) listed in Table 1 are prepared.

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

Ex - R ⁱ R ² R ³ R ⁴ Ar Physical.

No data and stereochemical information

HHC ₂ H ₅ H HO-, CH, (amo h) (racemate)

C ₂ H ₅

10 HHC ₂ H ₅ H CHFCHq (amorphous) (racemate)

^C ₂ H ₅

11 HHC ₂ H ₅ HC ₂ H ₅ (amorphous) (racemate)

C ₂ H ₅

12 HHC ₂ H ₅ H Br C ₂ H ₅ (amorphous) (racemate)

C ₂ H ₅

13 HHC ₂ H ₅ H Bι H, (amorphous) (racemate)

C ₂ H ₅

14 HHC ₂ H ₅ H CFq (amorphous) (racemate)

Cl

15 HHC ₂ H ₅ H cι- .CH, (amorphous) (racemate)

Cl

Ex. R ^l R ² R ³ R ⁴ Ar Physical.

No data and stereochemical information

23 HHC ₇ ₂ H ⁿ 5 HC ₂ H ⁿ 5 (amorphous) (racemate) logP: 2.64 ^b)

24 HHC ₂ H ₅ H CH ₃ (amorphous) (racemate) logP: 2.25 ^b)

CH,

25 HHC ₇ ₂ H ⁿ 5 H CF ₃ (amorphous) (racemate) logP: 3.36 ^b)

CH,

26 HHC ₇ ₂ H "5 H CF (CH ₃ ) ₂ (amorphous) (racemate) logP: 2.87 ⁾

27 HHC ₂ H ⁿ 5 H CF, (amorphous)

(Racemate) logP: 3, 18 ^b)

28 HHC ₂ H ₅ H CHFCH, (amorphous) (racemate) logP: 2.56 ^b)

29 HH G> H ⁿ 5 HC ₂ H ₅ (amorphous) (racemate) logP: 2.52 ^b)

Ex, Rl R ² R ³ R ⁴ Ar Physical.

No data and stereochemical information

90 HHCH ₅ H CHFCH ₃ (amorphous) (racemate)

91 HHC ₂ H ₅ H CF (CH ₃ ) ₂ logP: 2.74 ^b) (racemate)

92 HHC ₂ H ₅ H CF _q m.p .: 110 ° C (racemate)

93 HHC ₂ H ₅ H (amorphous) (racemate)

94 HHC ₂ H ₅ H (amorphous)

(Racemate)

95 H H B

C ₂ H ₅ H c-, CH, (amorphous) (racemate)

96 HHC ₂ H ₅ HC ₂ H ₅ (amorphous) (racemate)

Ex. - R ^l R ² R ³ R ⁴ Ar Physical.

No data and stereochemical information

184 HHC ₂ H ₅ H CH ₂ OCH ₃ logP: 2.61 ⁾ (racemate)

185 HHC ₂ H ₅ H CF (CH ₃ ) ₂ logP: 2.41 ^b) (racemate)

186 HHC ₂ H ₅ H CHFCH, logP: 2.44 ^a) (racemate)

187 HHC ₂ H ₅ H CF, logP: 3.74 ^a) (racemate)

HHCH ₅ H CH ₂ OCH ₃ logP: 1.90 a ⁾ (racemate)

The logP values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V A8 by HPLC (High Performance Liquid Chromatography) on a phase inversion column (C 18) temperature 43 ° C

(a) Eluents for determination in the acidic range 0.1% aqueous phosphoric acid, acetonitrile, linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^a )

(b) Eluents for the determination in the neutral range 0.01 molar aqueous phosphate buffer solution, acetonitrile, linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with " ⁾

The calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones)

The lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals Starting materials of formula (II) Example (11-1

A mixture of 12 g (52 mmol) (R, S) -l-ethyl-2- (3,5-dimethyl-phenoxy) -ethylamine hydrochloride (racemic) and 4.3 g (52 mmol) of cyano triturated in the Morser - Guanidine (dicyandiamide) is heated to 160 ° C. in a round bottom flask (“in bulk”, ie without the addition of a diluent). The resulting melt is kept at this temperature for about 30 minutes and is magnetically stirred. After it has cooled slightly, the still warm melt becomes brought into solution with 70 ml of methanol and the solvent is then carefully distilled off in a water jet vacuum

16.2 g (100% of theory) of l- [l- (3,5-dimethylphenoxymethyl) propyl] biguanide hydrochloride (racemate) are obtained as a solid product

Analogously to Example (II-1), the compounds of the formula (II) or their hydrochlorides listed in Table 2 below can also be prepared, for example

Table 2: Examples of the compounds of the formula (II) - (hydrochloride)

Starting materials of the formula (VII): Example (VII-1)

step 1

A mixture of 21.6 g (0.20 mol) of m-cresol, 20.0 g (0.26 mol) of 1,2-epoxy-butane and 0.5 g (0.02 mol) of lithium hydroxide is added for 20 hours Stirred 180 ° C. Then the mixture is taken up in about twice the amount of toluene, washed with 1N sodium hydroxide solution and then with water, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum and the residue is distilled under more reduced pressure at a bath temperature of at most about 160 ° C., the product crystallizing out in the cooler.

28 g (78% of theory) of 1- (3-methylphenoxymethyl) propanol with a boiling point of 84 ° C. (at 0.4 mbar) are obtained.

Level 2

177 g (0.98 mol) of l- (3-methyl-phenoxymethyl) propanol are placed in 980 ml of pyridine and 112 g (0.98 mol) of methanesulfonic acid chloride are slowly metered in at room temperature with stirring. The reaction mixture is stirred for 15 hours Stirred at 20 ° C and then concentrated in a water jet vacuum. The residue is taken up in water, with conc. Acidified with hydrochloric acid, shaken with methylene chloride, the organic phase is washed with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum

227 g (90% of theory) of methanesulfonic acid [1- (3-methylphenoxymethyl) propyl] ester are obtained as an oily residue

1H-NMR (CDC1 ₃ , δ) 3.08 ppm (s, S0 ₂ CH ₃ )

level 3

210 g (0.81 mol) of methanesulfonic acid [1- (3-methylphenoxymethyl) propyl] ester are dissolved in 500 ml of methanol and ammonia is dissolved in an autoclave at approx

100 ° C and a maximum of about 2 bar is metered in until the end of the ammonia uptake can be recognized on the basis of the measured internal pressure. After opening the autoclave, the contents are transferred to a round bottom flask and concentrated in a water jet vacuum, the residue is mixed with 400 ml of 2N sodium hydroxide solution and mixed with Methylene chloride shaken The organic phase is dried with sodium sulfate and filtered

The filtrate is concentrated in a water jet vacuum and the residue is distilled at a greatly reduced pressure (bath temperature maximum approx. 150 ° C.) 102 g (72% of theory) of 1- (3-methylphenoxymethyl) propylamine (boiling point: 80 ° C.-82 ° C. at 0.7 mbar) are obtained. Level 4

101 g (0.57 mol) of l- (3-methylphenoxymethyl) propylamine are placed in 1500 ml of tetrahydrofuran and at 0 ° C. to 20 ° C. hydrogen chloride (gas) is introduced with stirring until the solution is saturated. The crystalline product is isolated by suction.

83 g (67% of theory) of 1- (3-methylphenoxymethyl) propylamine hydrochloride are obtained.

Enantiomer separation of the compounds of the formula (VII):

74.2 g (0.45 mol) of 1-phenoxymethyl propylamine and 51.5 g (0.50 mol) of methyl methoxyacetate are placed in 450 ml of methyl t-butyl ether. At 40 ° C., 3.7 g of ^® Novozym 435 (Novo Nordisk) are added and the mixture is stirred at this temperature for 150 minutes. After suction, the filtrate is concentrated with 250 ml of ice water and with 39 ml. Hydrochloric acid added and stirred for 20 minutes. The organic solvent is then distilled off in a water jet vacuum and, after addition of 200 ml of water, extracted three times with dichloromethane (“extraction solution A”). The aqueous phase is adjusted to pH = 13 with 2N sodium hydroxide solution and extracted with dichloromethane. After drying with sodium sulfate, filtering and concentrating the filtrate in a water jet vacuum, 35.1 g (S) -l-phenoxymethyl-propylamine (94.5% of the Theory, ee 88.3%)

The extraction solution A is dried with sodium sulfate and filtered, the filtrate is concentrated in a water jet vacuum. The (R) -N-methoxyacetyl-1-phenoxymethyl-propylamine obtained as the crude product is concentrated in 300 ml of water and 60 ml. Hydrochloric acid was taken up and heated to boiling under reflux for 20 hours. After extraction with dichloromethane, drying with sodium sulfate, filtration and concentration of the filtrate in a water jet vacuum, 30.7 g of (R) -l-phenoxymethyl-propylamine (79.5% of theory) are obtained , 93.2% ee)

As described above using individual examples, the compounds of the formula (VII) listed in Table 3 below can also be prepared analogously

Table 3 Examples of the compounds of the formula (VII)

Supplement to Table 1: Examples 26a and 26 b

The two optical isomers (enantiomers) contained in the racemate described in Table 1 above under Example 26 were also prepared individually as such:

a) R enantiomer - logP: 2.86 (at pH 7.5); b) S-enantiomer - logP: 2.86 (at pH 7.5).

Examples of use:

In the application examples described below, the known compound of the formula (A) was used as the reference substance:

N- [2- (3,5-Dimethyl-phenoxy) -l-methyl-ethyl] -6- (l-fluoro-l-methyl-ethyl) -l, 3,5-triazine-2,4-diamine - known from EP 411153.

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 level

concentration

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active compound preparation, so that the desired amounts of active compound are applied per unit area. The concentration of the spray mixture is chosen so that in 1 000 l of water / ha the respective desired amounts of active ingredient are applied

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

Mean it

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

In this test, for example, the compounds according to Preparation Examples 1, 2, 3, 4, 5, 6, 37 and 38, with good tolerance to crop plants, such as maize, in some cases show strong activity against weeds (cf. Table A) "ai" = active ingredient ("active ingredient") Table A: Pre emergence test / greenhouse

Active ingredient according to the application rate of maize Setaria amaran-galium, manufacturing example no. (g ai./ha) thus

(2) 1000 95 80

(38) 1000 20 70 90 100

Table A (continued)

Active ingredient according to the amount of corn Setaria Abutilon Amaran Sinapis manufacturing example -No. (g ai./ha) thus

(3) 1000 100 60 70 80

(6) 1000 20 80 70 80 100

Table A (continued)

Active ingredient according to the application rate Alope-Setaria Abu- Amaran- Galium Sinapis Manufacturing example no. (g ai./ha) curus tilon thus

(5) 1000 80 90 70 90 80 100

Table A (continued)

Active ingredient according to the application rate of maize Alope- Setaria AbuAma- Sinapis Manufacturing example no. (g ai./ha) curus tilon ranthus

(1) 1000 20 80 95 80 80 70

(4) 1000 80 100 90 70

Table A (continued)

Active ingredient according to the application rate Digitaria Echino-Cassia Datura Solanum Veronica Manufacturing example no. (g ai./ha) chloa

(37) 500 95 95 100 95 100 100

Example B

Post emergence test

Solvent 5 parts by weight of acetone

Emulsifier 1 part by weight of alkylaryl polyglycol ether

concentration

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

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

Mean it

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

In this test, for example, the compounds according to Preparation Examples 1, 2, 3, 4, 5, 6, 37 and 38, with good tolerance to crop plants such as, for example, maize and wheat, show strong activity against weeds (cf. Table B) Table B: Post emergence test / greenhouse

Active ingredient according to the application rate of Abu- Matri- Stellaria Viola Xanthium

Manufacturing example no. (g ai./ha) tilon caria

(A) 250 80 50 70 70 70

(37) 250 100 95 90 100 90

Table B (continued)

Active ingredient according to application rate Setaria Abu- Matri- Stellaria Viola Her stellungsb sp. -No. (g ai./ha) tilon caria

co

(A) 250 70 80 50 70 70 I.

(38) 250 80 95 70 80 100

Table B (continued)

Active ingredient according to the application rate of maize Alo- Setaria Abu- Ama- Sinapis Manufacturing example no. (g ai./ha) pecurus tilon ranthus

(1) 1000 20 70 95 100 100 100

Table B (continued)

Active ingredient according to the application rate Alosetaria Abutilon Ama- Galium Sinapis Manufacturing example no. (g ai./ha) pecurus ranthus

(2) 1000 90 95 80 95 100 95 r

(3) 1000 80 100 95 100 90 100

Table B (continued)

(4) 1000 70 80 80 90 100

(5) 1000 80 100 95 100 95 100

Table B (continued)

Active ingredient according to the application rate of Alosetaria Abutilon Ama- Galium Sinapis. -No. (g ai./ha) pecurus ranthus

(6) 1000 90 100 100 100 95 100

Table B (continued)

Active ingredient according to the application rate of wheat Ama- Datura Ipomoea Solanum Manufacturing example no. (g ai./ha) ranthus

(37) 125 95 95 100 95

Table B (continued)

Active ingredient according to the application rate of wheat maize Setaria Cassia Cheno - manufacturing example no. (g ai./ha) podium

(38) 125 70 95 100 95 95

Claims

claims

1. Substituted aryloxyalkylaminotriazines of the general formula (I)

^R X- ^R

in which

R ² for hydrogen, for formyl or for each optionally by

Cyano, halogen or Cj-C-j-alkoxy substituted alkyl, alkylcarbonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups,

R ³ for optionally by hydroxy, cyano, halogen or C1 -C4-

Alkoxy substituted alkyl having 2 to 6 carbon atoms or substituted by cyano, halogen or Cj-C-i-alkyl

Cycloalkyl having 3 to 6 carbon atoms,

R ^{4 represents} hydrogen or alkyl having 1 to 4 carbon atoms,

Ar represents optionally substituted phenyl, naphthyl, tetralinyl or heterocyclyl, the possible heterocyclyl groupings are preferably selected from the following group:

Furyl, benzofuryl, thienyl, benzothienyl, thiazolyl, benzthiazolyl, oxazolyl, benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, pyridinyl and pyrimidinyl,

Hydroxy, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, each of which is optionally substituted by hydroxy, cyano or halogen-substituted alkyl or alkoxy each having 1 to 6 carbon atoms, each optionally substituted by halogen, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylamino, Alkylcarbonylamino, alkylsulfonylamino, bis-alkylcarbonylamino, bis-alkylsulfonylamino, N-alkyl-N-alkylcarbonylamino or N-alkyl-N-alkylsulfonylamino each having 1 to 6 carbon atoms in the alkyl groups, each optionally by Hydroxy, cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or Cj-

C4-haloalkoxy-substituted phenyl or phenoxy, and in each case halogen-substituted methylenedioxy or ethylenedioxy,

and

for halogen, for each optionally by hydroxy, cyano,

Halogen, C ₁ -C ₄ -alkoxy, C ₁ -C 4 -alkylcarbonyl, C ₄ -C ₄ -alkoxycarbonyl, C ₁ -C -alkylthio, C ₁ -C ₄ -alkylsulfinyl or C ₁ -C 4 -alkylsulfonyl-substituted alkyl, alkoxy, Alkylcarbonyl, alkoxycarbonyl,

Alkylthio, alkylsulfinyl or alkylsulfonyl, each with 1 to 6 carbons Stofifatomen in the alkyl groups, or for optionally substituted by cyano, halogen or Cj-C4-alkyl cycloalkyl having 3 to 6 carbon atoms

Compounds of formula (I) according to claim 1, characterized in that therein

R ^{1 stands} for hydrogen or for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy or ethoxy,

R ^{2 stands} for hydrogen, for formyl, or for methyl, ethyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl or ethoxycarbonyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy,

R ³ for each optionally by hydroxy, cyano, fluorine, chlorine,

Methoxy or ethoxy substituted ethyl, n- or i-propyl, n-, i-, s- or t-butyl or represents in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,

R ^{4 represents} hydrogen or methyl,

the possible heterocyclyl groupings are preferably selected from the following group Furyl, benzofuryl, thienyl, benzothienyl, thiazolyl, benzthiazolyl, oxazolyl, benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, pyridinyl and pyrimidinyl,

and the possible substituents are each preferably selected from the following group '

Hydroxy, cyano, carbamoyl, thiocarbamoyl, nitro, fluorine, chlorine, bromine, each optionally substituted by hydroxy, cyano, fluorine 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, each optionally substituted by fluorine or chlorine, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i Propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, dimethylamino, diethylamino, acetylamino, propionylsulfonyl, methylsulfonyl amino, bis-acetyl-amino, bis-methylsulfonyl-amino, N-methyl-N-acetyl-amino or N-methyl-N-methylsulfonylamino, each optionally by hydroxy, cyano, nitro, fluorine, chlorine, bromine,

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, Difluoromethoxy or trifluoromethoxy-substituted phenyl or phenoxy, and also methylene dioxy or ethylenedioxy optionally substituted by fluorine or chlorine,

and

for fluorine, chlorine, bromine, for each optionally by hydroxy, cyano, nitro, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, n-, i-

, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, methyl sulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl 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, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl,

Ethylsulfonyl, n- or i-propylsulfonyl, or for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl.

Compounds of formula (I) according to claim 1, characterized in that therein

R ^{1 represents} hydrogen or methyl or ethyl which is optionally substituted by cyano, fluorine, methoxy or ethoxy,

R ^{2 stands} for hydrogen, or for methyl, ethyl, acetyl or propionyl which is in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

R ^{4 represents} hydrogen,

Ar represents in each case optionally substituted phenyl or naphthyl,

the possible substituents are each preferably selected from the following group:

Hydroxy, cyano, nitro, fluorine, chlorine, bromine, each methyl, ethyl optionally substituted by hydroxy, cyano, fluorine or chlorine, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, each optionally by fluorine or chlorine substituted acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n - or i-Propylsulfonyl, each optionally by hydroxy, cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy , n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy substituted

Phenyl or phenoxy, and also methylene dioxy or ethylenedioxy optionally substituted by fluorine or chlorine,

and

Z for each optionally by hydroxy, cyano, fluorine, chlorine,

Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-

Propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl,

Methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or for each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

4. A process for the preparation of compounds of formula (I) according to claim 1, characterized in that

(a) aryloxyalkyl biguanides of the general formula (II)

in which

R ¹ , R ² , R ³ , R ⁴ and Ar have the meaning given in claim 1,

and / or acid adducts of compounds of the general formula (II)

with alkoxycarbonyl compounds of the general formula (III)

Z-CO-OR '(III)

in which

Z has the meaning given in claim 1 and

R 'represents alkyl,

or that one

(b) substituted halotriazines of the general formula (IV) X

in which

R ³ , R ⁴ , Ar and Z have the meaning given above and

X represents halogen,

with nitrogen compounds of the general formula (V)

R ¹ A. R ²

N ( _V )

H

in which

R ¹ and R ^{2 have} the meaning given above,

or that one

(c) substituted aminotriazines of the general formula (VI)

N N (VI)

Z ^' ^ NY

in which

R ¹ , R ² and Z have the meaning given above and

Y ^{1 represents} halogen or alkoxy,

with aryloxyalkylamines of the general formula (VII)

in which

Ar, R ³ and R ^{4 have} the meaning given above,

or that one

(d) for the preparation of compounds of the formula (I) in which R ^{2 is} different from hydrogen,

Aryloxyalkylaminotriazines of the general formula (Ia)

in which

R ¹ , R ³ , R ⁴ , Ar and Z have the meaning given above,

with alkylating or acylating agents of the general formula (VIII)

Y ² -R ² (VIII)

in which

R ² has the meaning given above with the exception of hydrogen and

Y ^{2 represents} halogen, -OR ² or -O-CO-R ² ,

and optionally on the compounds of the general formula (I) obtained according to the processes described under (a), (b), (c) or (d), as part of the above definition of substituents, by further conversions by customary methods.

5. Herbicidal agents, characterized in that they contain at least one compound of the formula (I) according to Claim 1.

6. Use of compounds of formula (I) according to claim 1 for combating undesirable plant growth.

7. A method of combating weeds, characterized in that compounds of the formula (I) according to Claim 1 are allowed to act on the weeds or their habitat.

8. A process for the preparation of herbicidal compositions, characterized in that compounds of the formula (I) according to Claim 1 are mixed with extenders and / or surface-active agents.