EP1060170A1 - Optically active substituted 2,4-diamino-1,3,5-triazines as herbicides - Google Patents

Abstract

The invention relates to novel optically active substituted 2,4-diamino-1,3,5-triazines of formula (I), wherein Ar represents optionally substituted aryl, aryl being a carbocyclical or heterocyclical, monocyclical or bicyclical aromatic grouping from the following series: phenyl, naphthyl, pyridinyl, pyrimidinyl, furyl, benzofuryl, thienyl and benzothienyl and the possible substituents being selected from the following series: cyano, nitro, carbamoyl, thiocarbamoyl, halogen, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C1-C4-alkylthio, C1-C4-halogenalkylthio, C1-C4-alkylsulfinyl, C1-C4-halogenalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-halogenalkylsulfonyl, C1-C4-alkylamino and C1-C4-alkoxy-carbonyl; R1 represents alkyl with 1 to 4 carbon atoms, R2 represents alkyl optionally substituted with hydroxy, cyano, halogen or C¿1?-C4-alkoxy, with 1 to 4 carbon atoms, and R?3¿ represents alkyl optionally substituted with cyano, halogen or C¿1?-C4-alkoxy, with 2 to 4 carbon atoms, the substituents on the carbon atom to which R?1¿ is bonded being arranged in R-configuration. The invention also relates to methods and novel intermediate products for producing the inventive substituted 2,4-diamino-1,3,5-triazines and to their use as herbicides.

Description

 - 1 -

OPTICALLY ACTIVE SUBSTITUTED 2,4-DIAMINO-l, 3,5-TRIAZINE AS HERBICIDES

The invention relates to new optically active substituted 2,4-diamino-l, 3,5-triazines, processes and new intermediates for their preparation and their use as

Herbicides.

A number of substituted 2,4-diamino-triazines are already known from the (patent literature) (cf. US 3 816 419, US 3 932 167, EP 273 328, EP 411 153 / WO 90/09378, WO 97/00254 , WO 97/08156) However, these compounds have so far not attained any particular importance.

The new optically active substituted 2,4-diamino-1,3,5-triazines of the general formula (I) have now been found

R ²

R ³ N ^ NR ¹

J II

O ^ N ^ N ^ N (I) II

H H in which

Ar stands for optionally substituted aryl, where aryl stands for a carbocyclic or heterocyclic, monocyclic or bicyclic, aromatic

Grouping is from the series phenyl, naphthyl, pyridinyl, pyrimidinyl, furyl, benzofuryl, thienyl and benzothienyl and the possible substituents from the series cyano, nitro, carbamoyl, thiocarbamoyl, halogen, C1 -C4 alkyl, C 1 -C 4 haloalkyl, C ] -C4-alkoxy, -C-C4-haloalkoxy, C1 -C4-alkylthio, Cι-C ₄ -haloalkylthio, Cι-C4-alkylsulfinyl, C 1 -C ₄ -halo-alkylsulfinyl, Cj-C4-alkylsulfonyl, C} - C4-haloalkylsulfonyl, C1-C4-alkylamino and C \ -C4-alkoxy-carbonyl are selected, R ^{1 represents} alkyl with 1 to 4 carbon atoms,

R ² represents alkyl with 1 to 4 carbon atoms optionally substituted by hydroxy, cyano, halogen or C 1 -C 4 -alkoxy, and

R ^{3 represents} alkyl which has 2 to 4 carbon atoms and is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy,

where the substituents on the carbon atom to which R ^{1 is} attached in R-

Configuration.

The new optically active substituted 2,4-diamino-1,3,5-triazines of the general formula (I) are obtained if optically active substituted 2,4-diamino-1,3,5-triazines of the general formula (II )

R ^{1 '} N ^' N ^' N ^N Ar (II) I i HH in which

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

with acylating agents of the general formula (III)

R ³ y ⁽ in ⁾

in which - 3 -

R ^{3 has} the meaning given above and

X represents halogen or the grouping -O-CO-R ³ ,

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

The new optically active substituted 2,4-diamino-1,3,5-triazines of the general formula (I) are notable for strong and selective herbicidal activity.

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

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

Ar stands for optionally substituted aryl, aryl stands for a carbocyclic or heterocyclic, monocyclic or bicyclic, aromatic group from the series phenyl, naphthyl, pyridinyl, pyrimidinyl, furyl, benzofuryl, thienyl and benzothienyl and the possible substituents from the series cyano , Nitro, carbamoyl, thiocarbamoyl, halogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, Chlorodifluromethoxy, fluorodichloromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methyl - 4 -

sulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, dimethylamino, diethylamino, methoxycarbonyl and ethoxycarbonyl are selected,

R ^! represents methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,

R ^{2 stands} for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, each optionally substituted by hydroxy, cyano, fluorine, chlorine, bromine, methoxy or ethoxy, and

R ³ for each optionally by cyano, fluorine, chlorine, bromine, methoxy or

Ethoxy substituted ethyl, n- or i-propyl, n-, i-, s- or t-butyl,

wherein the substituents on the carbon atom to which R ^{1 is} attached are arranged in the R configuration.

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

Ar represents optionally substituted aryl, where aryl represents a carbocyclic or heterocyclic, monocyclic or bicyclic, aromatic group from the series phenyl, naphthyl, pyridinyl, pyrimidinyl, furyl,

Benzofuryl, thienyl and benzothienyl and the possible substituents from the series cyano, nitro, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, trifluoromethylthio, , Methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, dimethylamino, diethylamino, methoxycarbonyl and ethoxycarbonyl are selected,

R ^{1 represents} methyl, ethyl, n- or i-propyl, - 5 -

R ^{2 represents} in each case methyl, ethyl, n- or i-propyl which is optionally substituted by hydroxyl, cyano, fluorine, chlorine, bromine, methoxy or ethoxy, and

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

wherein the substituents on the carbon atom to which R ^{1 is} attached are arranged in the R configuration.

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 radical definitions can be combined with one another, that is to say also between the specified preferred ranges.

Examples of the compounds of formula (I) according to the invention are listed in the groups below.

Group 1

C ₂ H ₅ NX ^. N CH,, - ^ N ^ N ^ K NΓ ^' I i HH

R ^ has, for example, the meanings given below:

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-hydroxyethyl, cyano-methyl, 1-cyano-ethyl, 2-cyano-ethyl, 1-cyano- 1-methyl-ethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, chlorofluoromethyl. Chlorobromomethyl, chlorodifluoromethyl, fluorodichloromethyl, bromodifluoromethyl, trichloro- 6 -

methyl, 1-fluoro-ethyl, 2-fluoro-ethyl, 1-chloro-ethyl, 2-chloro-ethyl, 1-chloro-1-fluoro-ethyl, 1-fluoropropyl, 2-fluoropropyl, 3- Fluoropropyl, 1-fluoro- 1-methyl-ethyl, 2-fluoro-1-methyl-ethyl, 1-chloro-1-methyl-ethyl, 1-fluoro-1-methyl-propyl, 1-chloro-1- ethyl-propyl, 1-fluor-1-ethyl-propyl, 1-chloro-1-ethyl-propyl, 1-fluoro-2-methyl-propyl, 1-chloro-2-methyl-propyl, 1-chloro-propyl, 2-chloropropyl, 3-chloropropyl, 1-chloro-1-methyl-ethyl, 2-chloro-1-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-dichloropropyl, perfluoropropyl, 1- Fluorobutyl, 1-chlorobutyl, methoxymethyl, 1,1-dimethoxy-methyl, 1-methoxy ethyl, 2-methoxy-ethyl, 1,1-dimethoxy-ethyl, ethoxymethyl, 1-ethoxyethyl, 2-ethoxy -ethyl, 2-methoxy-1-methyl-ethyl, 2-methoxy-l-ethyl-ethyl, 2-ethoxy-1-methyl-ethyl or 2-ethoxy-l-ethyl-ethyl.

Group 2

R ^

C ₃ H ₇ N ^ N CH,

I H

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

Group 3

R

H ₃ C CH,

N N CH,

O ^'NNN i

H H

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

R ²

C ₂ H ₅ NX ^' . N? ₂ H ₅

O ^ ^ N ^ N- i

H H

R2 has, for example, the meanings given above in Group 1.

Group 5

R '

C ₃ H ₇ NN? ₂ ^H s

O ^ N ^ N ^ N ^'

H H

R2 has, for example, the meanings given above in Group 1.

Group 6

R '

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

Group 7

R ²

C ₂ H ₅ N ^ N CH ₃

O ^ N N N I ι

H H

^{^} CH, R- has, for example, the meanings given above in Group 1. - 8th -

Group 8

R ^

C, H ₇ H ^ "N CH,

, A NA ^'

I H

^{^} CH,

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

Group 9

R ^

H ₃ C CH ³ VM

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

Group 10

R ^

C ₂ H ₅ N ^ ϊsl C ₂ H ₅

O ^ N ^ N ^ N ^' II

H H H,

R ^ has, for example, the meanings given above in Group 1. - 9

Group 1 1

R ^<*

C ₃ H ₇ N ^ ^ C ₂ H ₅

O ^ N ^ N ^ N I I

H H

^* CH,

R2 has, for example, the meanings given above in Group 1.

Group 12

R '

H ₃ C CH,

N N

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

Group 13

R ²

C 2H "'5 _B HN CH,

O ^ N ^ N ^ ^' i

H H CI

R2 has, for example, the meanings given above in Group 1.

Group 14

C ₃ H ₇ N ^ N CH, O ^ N ^ N ^ N ^'

H H

^* CI R2 has, for example, the meanings given above in Group 1. 10

Group 15

R "

H ₃ C CH _{3 |} -

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

Group 16

R ^

C ₂ H ₅ NT N? ₂ H ₅

O ^ N IM ^

I I H H

^H CI

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

Group 17

R '

C ₃ H ₇ N ^ "NC ₂ H ₅

O ^ N ^ N ^ N 'I I

H H CI

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

Group 18

R ^

^{HC CH3} ^

^{N N}

R ^ has, for example, the meanings given above in Group 1. 11 -

Group 19

R ^

92 5 N ^' NC rH "" 3

O X ^ N X N. - N

H

R2 has, for example, the meanings given above in Group 1.

Group 20

R ^

C ₃ H ₇ N ^ ^ N CH, i, N ^ N ^'

I H H

R2 has, for example, the meanings given above in Group 1.

Group 21

R

H ₃ C CH _{3 |}

N ^ ^ N CH ₃

IH

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

Group 22

R ^z

C 2- 5 N i ^ N C _, 2H 5,

O "" N

I.

H

R2 has, for example, the meanings given above in Group 1. 12

Group 23

R

C ₃ H ₇ N ^ ^ NC 2H "" 5

O ^" 'Ϊ \ ΛT ^' NΛ ^'

I.

HH

R2 has, for example, the meanings given above in Group 1.

Group 24

H.C PH

N ^{^} N? ₂ H ₅ er ^{^} N '^ N' ^ N

H H

R2 has, for example, the meanings given above in Group 1.

Group 25

R ²

C ₂ H ₅ NX ^' . N CH,

XN ^' Nλ ^' N

I i

HH OCH,

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

Group 26

R ^

C N ^ ^ C

OCH,

R has, for example, the meanings given above in Group 1. - 13th

Group 27

R '

H ₃ C CH ₃ I ³ VN ^ l CH,

O ^ N ^ N ^ N '

H H OCH

R2 has, for example, the meanings given above in Group 1.

Group 28

R ^

C ₂ H ₅ "H? ₂ H ₅

O'

I I H H OCH,

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

Group 29

R '

C ₃ H ₇ H ^ "C ₂ H _{5 0 NNN} ,

I I

H H) CH,

R2 has, for example, the meanings given above in Group 1. - 14-

Group 30

R "

H ₃ C CH _{3 |}

Nx ^ N 9 ₂ H ₅

O ^ N Λ ^' ϊsλr ^* N ^' i

H H

OCH,

R2 has, for example, the meanings given above in Group 1.

Group 31

R ^

C ₂ H ₅ N ^' N CH,

O ^' X NX ^' ^ N

I i

H H

R2 has, for example, the meanings given above in Group 1.

Group 32

R ^

C ₃ H ₇ NT N CH ₃

R2 has, for example, the meanings given above in Group 1.

Group 31

R

^{Hc c} MN ^ J

R has, for example, the meanings given above in Group 1. - 15 -

Group 34

R '

C ₂ H ₅ ^ "NC ₂ H _{5 0 NN} Λ _N

I I

HH

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

Group 35

R ^

C ₃ H ₇ N ^ NC ₂ H ₅

O Λ ^' NΛ ^' Ϊ \ ΛT

R2 has, for example, the meanings given above in Group 1.

Group 36

R ^

HC CH ³ VN ^{' ^} N

O ^ N II

H H

R2 has, for example, the meanings given above in Group 1.

Group 37

R ²

C ₂ H ₅ N ^ N CH _{3 o N} OCH,

I -SA _N ι

HH

R has, for example, the meanings given above in Group 1. - 16 -

Group 38

C ₃ H ₇ NT N CH,

_{0 N} A _N λ OCH,

I H

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

Group 39

R ^

H ₃ C CH ₃

^ ^

OCH,

R2 has, for example, the meanings given above in Group 1.

Group 40

R ^

C ₂ H ₅ N ^{^} N? ₂ H ₅

OCH,

R2 has, for example, the meanings given above in Group 1.

Group 41

^C ₃ H ₇ ^? ₂ H ₅

"OCH"

I I

H H x ^ x

R has, for example, the meanings given above in Group 1. 17-

Group 42

R ^

H ₃ C CH ³ \ / NT ^{^} N? ₂ H ₅

OCH,

O ^ N ^ N ^{' ^} N

IHH

R2 has, for example, the meanings given above in Group 1.

Group 43

R ^

C ₂ H ₅ NT J CH,

_{0 N N N}

II

H H

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

Group 44

C ₃ H ₇ N ^* N CH, c IA N ^ N

I HH

R2 has, for example, the meanings given above in Group 1.

Group 45

R ^

^H 3 ^{C CH3} ^

R2 has, for example, the meanings given above in Group 1. - 18th

Group 46

R "

₂ H ₅ N ^' N? ₂ H ₅

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

Group 47

C ₃ H ₇ NT N 9 ₂ H ₅

O ^ N ^ N ^ NII

H H

R2 has, for example, the meanings given above in Group 1.

Group 48

"X ^C AN

O ^ N 'NI XX H

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

Group 49

R " ^*

C ₂ H ₅ NT CH ₃

I I

H H

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

Group 50

R '

C ₃ H ₇ ψ ^ N CH ₃

-W ΗΛ ^' N

HH

R2 has, for example, the meanings given above in Group 1.

Group 51

R CH

R2 has, for example, the meanings given above in Group 1.

Group 52

R

C ₂ H ₅ N ^ ^ NC ₂ H _{5 0 NN} Λ _N

II

H H

R2 has, for example, the meanings given above in Group 1.

Group 53

R

C ₃ H ₇ NT NC ₂ H ₅ X o XX

HH

R has, for example, the meanings given above in Group 1. 20 -

Group 54

H ₃ C CH ₃

IS

O ^ N ^ N

H

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

Group 55

R ^

C ₂ H ₅ ^ N

_{0 NN} Λ _N

H H

R2 has, for example, the meanings given above in Group 1.

Group 56

R ^

C ₃ H ₇ N ^

I H

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

Group 57

R "

H ₃ C CH ³ V

I XX H

R has, for example, the meanings given above in Group 1. 21 -

Group 58

C ₂ H ₅ N x ^{^} N ΛN

HH

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

Group 59

R ^

C ₃ H ₇ N ^ N

Ö x I * x IHH

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

Group 60

R ^

H ₃ C CH ³ V NT N

I XX I

H H

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

Group 61

R '

C ₂ H ₅ N ^ NX o IXX I

H H

R2 has, for example, the meanings given above in Group 1. 22-

Group 62

R '

C ₃ H ₇ WN

_{0 NN} Λ _N

H H

R2 has, for example, the meanings given above in Group 1.

Group 63

H ₃ C CH ₃ ϊ

Y N ^^ N CH

_{0 NN} Λ _N

II

H H

R2 has, for example, the meanings given above in Group 1.

Group 64

R

C ₂ H ₅ NN

X IX I HH

R2 has, for example, the meanings given above in Group 1.

Group 65

R ^

^C 3 7 ff

_{0 NN} Λ _N

II

H H

R has, for example, the meanings given above in Group 1. 23

Group 66

H ₃ C CH,

N 'N

R2 has, for example, the meanings given above in Group 1.

Group 67

R ^z H- N ^ J

Ö XΛ ^* NΛ ^'

I. I HH

R2 has, for example, the meanings given above in Group 1.

Group 68

C ₃ H ₇ NT "NO ^ N ^ NN

H H

R2 has, for example, the meanings given above in Group 1.

Group 69

R ^

^{H3C CH3} ^ ι \ r -j

C ^{^} UXNIXH

R2 has, for example, the meanings given above in Group 1. 24 -

Group 70

R ^

C ₂ H ₅ NN

_{0 N} A _N λ

IH

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

Group 71

R ^

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

Group 72

R ^

H ₃ C CH ³ \ / N / ^ - N

O ^' "" N ^ TJ ^^ N

H H

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

Group 73

R ^

C ₂ H ₅ | NJT NX o IXX I

H H

R2 has, for example, the meanings given above in Group 1. - 25 -

Group 74

R '^'

R2 has, for example, the meanings given above in Group 1.

Group 75

^H3C x V / ^C \ NX ^{' ^} N

X Ϊ \ T

IH

R2 has, for example, the meanings given above in Group 1.

Group 76

^C ₂ H ₅ N ^ N

O ^ N ^ N ^ NII

H H

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

Group 77

R ^

C ₃ H ₇ ι \ r "N _{c NN} A _N

I I

HH

R2 has, for example, the meanings given above in Group 1. - 26

Group 78

R '

H ₃ C CH ³ <x ^

R2 has, for example, the meanings given above in Group 1.

Group 79

R ^

C ₂ H ₅ N ^ ^ N CH,

_{0 NN} Λ _N

I I

H H

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

Group 80

R

C ₂ H ₅ N ^ ^? ₂ H ₅

R2 has, for example, the meanings given above in Group 1.

For example, if (R) -2-amino-4- (l-methyl-3-phenyl-propylamino) -6- (l-fluoro-ethyl) -l, 3,5-triazine and propionic acid chloride are used as starting materials, then the

The course of the reaction in the process according to the invention can be outlined by the following formula: - 27 -

"CH," CH,

+ CI-CO-C ₂ H ₅

CH, a 5 N N CH 3

Λ Λ. HCI

H ₂ N ^" .IST θX \ N- ^{' '} N

H _^ J ^» HH

The optically active substituted 2,4- to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I)

Diamino-1,3,5-triazines are generally defined by the formula (II). In the formula (II), Ar, R ¹ and R ² preferably or in particular have those meanings which are preferred or particularly preferred for Ar, R ¹ and R above in connection with the description of the compounds of the formula (I) according to the invention ^{2 were} specified.

The starting materials of the general formula (II) are not yet known from the literature; As new substances, they are the subject of previous patent applications (cf. DE 19641693 / LeA 31975; DE 19641694 / LeA 31994).

The optically active substituted 2,4-diamino-1,3,5-triazines of the general formula (II) are obtained if

(a) optically active substituted biguanides of the general formula (IV)

H . H _N ,

NNR ¹

NNN (IV) iii

H H H in which

Ar and R 'have the meaning given above, - 28 -

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

with alkoxycarbonyl compounds of the general formula (V)

R ² -CO-OR (V) in which

R ^{2 has} the meaning given above and

R represents alkyl,

optionally in the presence of a reaction auxiliary, e.g. Sodium methylate, and optionally in the presence of a diluent, e.g. Methanol, at

Converts temperatures between 0 ° C and 100 ° C (see. DE 19641693 / LeA 31975; DE 19641694 / LeA 31994; see also WO 97/08156; manufacturing examples).

The optically active substituted biguanides of the general formula (IV) required as precursors are not yet known from the literature; they are as new

Substances the subject of previous patent applications (cf. DE 19641693 / LeA 31975; DE 19641694 / LeA 31994).

The optically active substituted biguanides of the general formula (IV) are obtained if optically active substituted alkylamino compounds of the general

Formula (VI)

(VI) - 29 -

in which

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

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

with cyanoguanidine of the formula (VII)

X. N

H .. NΛ ^' N ^" HH ^ _jj rj

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 492 615, production examples).

The optically active substituted alkylamino compounds of the general formula (VI) required as precursors are known and / or can be prepared by processes known per se (cf. DE 3 426 919; DE 4 000 610; DE 4 332 738, EP 320 898; EP 443 606; Tetrahedron: Asymmetry 5 (1994), 817-820;

Tetrahedron Lett. 29: 223-224 (1988); loc. cit. 36: 3917-3920 (1995)).

Formula (III) provides a general definition of the acylating agents which are further to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I). In formula (III), R ³ 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 ³ ; X preferably represents fluorine, - 30 -

Chlorine, bromine, acetyloxy, propionyloxy, n- or i-butyroyloxy, especially for chlorine, acetyloxy or propionyloxy.

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

The process according to the invention for the preparation of compounds of the general formula (I) is optionally carried out using a reaction auxiliary. The usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries. 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 methoxide, 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-dimethyl-cyclohexylamine, 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).

The process according to the invention for the preparation of compounds of the general formula (I) is optionally carried out using a diluent. Inert organic solvents are particularly suitable as diluents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as - 31 -

as petrol, 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-methylpyrrolidone 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 the process according to the invention. In general, temperatures between 0 ° C and 200 ° C, preferably between 10 ° C and

150 ° C.

The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under increased or reduced pressure - generally between 0.1 bar and 10 bar.

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

The reaction is optionally 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. The processing is carried out according to customary methods (cf. the manufacturing examples). - 32 -

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, Dutilon, Emo 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.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Iochasumirumum, Scalumumum, Scalumumum , Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium. - 33 -

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 compounds for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pastures 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 monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers

Substances.

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents

Agents, ie 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 alkyl - 34 -

naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes 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.

Possible solid carriers are: e.g. 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

Silicic acid, aluminum oxide and silicates, as solid carriers for granules are possible: e.g. 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 stems; 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. Further

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. - 35 -

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, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl), Bentazon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-ethyl) Bromobutides, bromofenoxim, bromoxynil, butachlor, butroxydim, butylates, cafenstrole, caloxydim, carbetamides, carfentrazone (-ethyl), chloromethoxyfen, chloramben,

Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cin- methylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulyl- azine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, diclofop (-methyl), diclosulam, diethyl ( -ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphen- a id, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Espuraluron, Ethrocam, Esprocuron methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, fenoxaprop (-P-ethyl), flamprop (-isopropyl), flamprop (-isopropyl-L),

Flamprop (-methyl), flazasulfuron, fluazifop (-P-butyl), flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacuron, flu (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-meptyl), Flurprimidol, Flur- tamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium),

Glyphosate (-isopropylammonium), halosafen, haloxyfop (-ethoxyethyl), haloxy- - 36 -

fop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxaflutole, Isactapyrifonil, Lactopyrofenop, Mox MCPP, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfonon (-methyl), Molinate, Monolinuron, Naproanilide, Nicroposulfuron, Neburon, Carburetone Oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron (-methyl), prometryn, propa chloros, propylchloride, propafloril Prosulfocarb,

Prosulfuron, pyraflufen (-ethyl), pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxime, pyributicarb, pyridate, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop, -P Quizalofop (-P-te-furyl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Terbuthyl-azine, Terbutryn, Thenylchloride, Thiazopyramide, Thiafiazole Thifensulfuron (-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribbenuron (-methyl), Triclopyr, Tridiphane, Trifluralin and Triflusulfuron.

A mixture with other known active ingredients, such as fungicides,

Insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil structure improvers are 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 customary manner, for example by watering, spraying, spraying or scattering. - 37 -

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.

- 38

Manufacturing examples;

example 1

CH 3

CH,

CV, 2H '', 5 N 7 - NI CH, N ^'

A mixture of 3.4 g (11 mmol) of (R) -2-amino-4- (l-methyl-3-phenyl-propyl-amino) -6- (l-fluoro-l-methyl-ethyl) -l, 3 , 5-triazine and 10 g (77 mmol) of propionic anhydride are stirred at 120 ° C. for two hours. After cooling to room temperature (approx. 20 ° C.), the mixture is diluted with 200 ml of water and stirred at room temperature for 15 hours. After decanting off the aqueous phase, the residue is taken up in methylene chloride, washed with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.

3.0 g (76% of theory) of (R) -2-propionylamino-4- (l-methyl-3-phenyl-propylamino) -6- (l-fluoro-l-methyl-ethyl) -l are obtained, 3,5-triazine as an amorphous residue. 20th

[α]

D -5.0 °.

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

R ²

R ° N

O ^ XN (I)

H - 39 -

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

Ex. Ar P ^" R2 ^~ R ^ ^" Physical.

No data

CH ₃ CHFCH-, C ₂ H ₅

CH ₃ CHC1CH, C ₂ H ₅

CH ₃ CF (CH ₃ ) ₂ C ₃ H ₇ -n

CH ₃ CF (CH ₃ ) ₂ C ₃ H ₇ -i

^

C ₂ H ₅ CF (CH ₃ ) ₂ C ₂ H ₅

C ₂ H ₅ CHFCH ₃ C ₂ H ₅

C ₂ H ₅ CHCICH ₃ C ₂ H ₅

"CH, C ₂ H ₅ CHFCH, C ₂ H ₅

"CH, C ₂ H ₅ CF (CH ₃ ) ₂ CH ₅ ^■ 40 -

Starting materials of formula (II): Example (II- 1)

CH,

-CH,

N ^' N

A mixture of 18 g (66 mmol) (R) -l- (l-methyl-3-phenyl-propyl) -biguanide hydrochloride, 3.6 g (66 mmol) sodium methylate and 50 ml methanol is stirred for 30 minutes at room temperature ( approx. 20 ° C) and then 8.2 g (61 mmol) of 2-fluoro-isobutyric acid ethyl ester were added. The reaction mixture is then stirred at room temperature for 18 hours, diluted to about three times the volume with methylene chloride, washed with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.

6.5 g (34% of theory) of (R) -2-amino-4- (l-methyl-3-phenyl-propyl-amino) -6- (l-fluoro-1-methyl-ethyl) - 1,3,5-triazine as an amorphous residue.

Starting materials of formula (IV):

Example (IV- 1)

N N CH x HCl

HHH - 41 -

A mixture of 17.9 g (96 mmol) of (R) -l-methyl-3-phenyl-propylamine hydrochloride and 8.1 g (96 mmol) of cyanoguanidine is heated to 160 ° C. (internal temperature) for three hours. The melt formed in this way is then diluted with approximately 100 ml of 1,2-dichlorobenzene at the temperature indicated above and - after cooling to room temperature - with approximately the same amount of diethyl ether. The product obtained in crystalline form is isolated by suction.

18.0 g (70% of theory) of (R) -l- (l-methyl-3-phenyl-propyl) -biguanide hydrochloride are obtained.

- 42 -

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 specified amount is given

Amount of emulsifier and dilute the concentrate 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, so that the desired amounts of active ingredient are applied per unit area. The concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.

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 destruction

In this test, for example, the compound according to Preparation Example 1, with good tolerance to crop plants, such as sunflowers, shows a strong action against weeds. Table A1: Pre-emergence test / greenhouse v ©

SO

Active ingredient according to effort- Alope- Setaria Abu- Ama- Sinapis Preparation example no. quantity (g ai./ha) curus tilon ranthus

C ₂ H ₅ N CH ₃

O

(1) 1000 100 100 95 100 100

O

H

O

Table A-2: Pre-emergence test / greenhouse

Active ingredient according to expenditure- Sun- Echino- Cheno- Solanum Preparation example no. quantity (g ai./ha) flower chloa podium

CH 3

CH,

C N

-! ^* *.

(1) 250 10 100 100 100

n

H

O

- 45 -

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 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 the desired amounts of active compound are applied in 1000 l of water / ha.

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 destruction

In this test, for example, the compound according to Preparation Example 1 shows a strong action against weeds. Table B: Post emergence test / greenhouse see above

\O

Active ingredient according to effort- Alope- Avena Setaria Abu- Ama- Sinapis Xan-

Production example no. quantity (g ai./ha) curus fatua tilon ranthus thium

CH 3

CH,

C ₂ H ₅ N - N CH ₃

H

(1) 1000 90 90 90 95 100 100 90

O

H

O

Claims

- 47 -patent claims

1. Optically active substituted 2,4-diamino-l, 3,5-triazines of the general formula (I),

R ^

R ³ N ^ R ¹

_{0 NN} Λ _N (I) i

H H in which

Ar stands for optionally substituted aryl, aryl stands for a carbocyclic or heterocyclic, monocyclic or bicyclic, aromatic group from the series phenyl, naphthyl, pyridinyl, pyrimidinyl, furyl, benzofuryl, thienyl and benzothienyl and the possible substituents from the series cyano , Nitro, carbamoyl, thiocarbamoyl, halogen, -C4-C4-alkyl, Cj-C4-haloalkyl, C-C4-alkoxy, C-C4-haloalkoxy, C-C4-alkylthio, Cι-C4-haloalkylthio, Cι-C4 -Alkylsulfinyl, -C -C-haloalkylsulfinyl, C-C4- alkylsulfonyl, Cι -C4-haloalkylsulfonyl, Cι-C4-alkylamino and Cι -C4 alkoxycarbonyl are selected,

R ^{1 represents} alkyl with 1 to 4 carbon atoms,

R ^{2 represents} alkyl which has 1 to 4 carbon atoms and is optionally substituted by hydroxy, cyano, halogen or C1-C4-alkoxy, and

R ^{3 represents} alkyl which has 2 to 4 carbon atoms and is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, - 48 -

wherein the substituents on the carbon atom to which R ^{1 is} attached are arranged in the R configuration.

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

Ar stands for optionally substituted aryl, where aryl stands for a carbocyclic or heterocyclic, monocyclic or bicyclic, aromatic group from the series phenyl, naphthyl, pyridinyl, pyrimidinyl, furyl, benzofuryl, thienyl and benzothienyl and the possible substituents from Cyano, nitro, carbamoyl, thiocarbamoyl, halogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, di- fluoromethoxy, trifluoromethoxy, chlorodifluromethoxy, fluorodichloromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylmethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, methyl trifluoromethyl, trifluoromethyl, ethylamino, methoxycarbonyl and ethoxycarbonyl are selected,

R ^{1 represents} methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,

R ^{2 represents} in each case methyl, ethyl, n- or i-propyl, n-, i- or s-butyl which is optionally substituted by hydroxyl, cyano, fluorine, chlorine, bromine, methoxy or ethoxy, and

R ³ represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, - 49 -

wherein the substituents on the carbon atom to which R ^{1 is} attached are arranged in the R configuration.

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

Ar stands for optionally substituted aryl, aryl stands for a carbocyclic or heterocyclic, monocyclic or bicyclic, aromatic group from the series phenyl, naphthyl, pyridinyl, pyrimidinyl, furyl, benzofuryl, thienyl and benzothienyl and the possible substituents from the series cyano , Nitro, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfmyl, trifluoromethylsulfonyl, trifluoromethylsulfonyl

Trifluoromethylsulfonyl, dimethylamino, diethylamino, methoxycarbonyl and ethoxycarbonyl are selected,

R ^{1 represents} methyl, ethyl, n- or i-propyl,

R ² represents methyl, ethyl, n- or i-propyl optionally substituted by hydroxy, cyano, fluorine, chlorine, bromine, methoxy or ethoxy, and

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

wherein the substituents on the carbon atom to which R ^{1 is} attached are arranged in the R configuration. - 50

4. (R) -2-propionylamino-4- (l-methyl-3-phenyl-propylamino) -6- (l-fluoromethyl-ethyl) -l, 3,5-triazine of the formula (1)

fH ₃ -CH ₃

CH ₅ N ^ N CH, (1)

CAN AN AH

according to claim 1.

A process for the preparation of compounds of formula (I) according to claim 1, characterized in that optically active substituted 2,4-diamino 1,3,

5-triazines of the general formula (II)

R 'N ^ NR ¹ NNN Ar (II)

I H H in which

Ar, R ¹ and R ^{2 have} the meaning given in claim 1,

with acylating agents of the general formula (III)

R ^J

O 'X in which - 51 -

R ^{3 has} the meaning given in claim 1 and

X represents halogen or the grouping -O-CO-R ³ ,

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

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

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

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

9. 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.