CA2267928C - Substituted 2-amino-4-alkylamino-1,3,5-triazines as herbicides - Google Patents

Substituted 2-amino-4-alkylamino-1,3,5-triazines as herbicides Download PDF

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CA2267928C
CA2267928C CA002267928A CA2267928A CA2267928C CA 2267928 C CA2267928 C CA 2267928C CA 002267928 A CA002267928 A CA 002267928A CA 2267928 A CA2267928 A CA 2267928A CA 2267928 C CA2267928 C CA 2267928C
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ethyl
phenyl
propylamino
substituted
unsubstituted
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CA2267928A1 (en
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Hans-Jochem Riebel
Stefan Lehr
Uwe Stelzer
Yukiyoshi Watanabe
Markus Dollinger
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

The invention relates to novel substituted 2-amino-4-alkylamino-1,3,5- triazines of the formula (I) <IMG> in which R1 represents in each case optionally substituted alkyl having 2 to 6 carbo n atoms or cycloalkyl having 3 to 6 carbon atoms, R2 represents hydrogen or represents alkyl having 1 to 4 carbon atoms, A represents oxygen or methylene, Ar represents in each case optionally substituted phenyl, naphthyl or heterocyclyl, and Z represents hydrogen, represents halogen or represents in each case optionally substituted alkyl, alkoxy, alkylcarboxyl, alkoxycarbonyl, alkylthio, alkyl- sulphinyl, alkylsulphonyl, alkenyl or alkinyl, to processes and to novel intermediates for their preparation and to their u se as herbicides.

Description

Le A 31 995-Foreign Countries Lu/klu/ngb/NT
j Substituted 2-amino-4-alkylamino-1,3,5-triazines The invention relates to novel substituted 2-amino-4-alkylamino-1,3,5-triazines, to processes and to novel intermediates for their preparation and to their use as herbicides.

A number of substituted 2,4-diamino-triazines is already known from the (patent) literature (c~ US 3816419, US 3932167, EP 191496, EP 273328, EP 411153 / WO
90/09378, WO 97/00254, WO 97/08156). However, these compounds have hitherto not attained any particular importance.

This invention, accordingly, provides the novel substituted 2-amino-4-alkylamino-1,3,5-triazines of the general formula (I) N -N R' (I) Z ~N N Ar H R2 A, in which R1 represents in each case optionally substituted alkyl having 2 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms, R2 represents hydrogen or represents alkyl having 1 to 4 carbon atoms, A represents oxygen or methylene Ar represents in each case optionally substituted phenyl, naphthyl or hetero-cyclyl, and Le A 31 995-Foreign Countries Z represents hydrogen, represents halogen or represents in each case optionally substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkyl-sulphinyl, alkylsulphonyl, alkenyl or alkinyl.

The novel 2-amino-4-alkylamino-1,3,5-triazines of the general formula (I) are ob-tained when (a) substituted biguanides of the general formula (II), H, N H, N R' (II) H~N'U" N'U" N A~Ar in which R1, R2, A and Ar are each as defined above - and/or acid adducts of compounds of the general formula (II) -are reacted with alkoxycarbonyl compounds of the general formula (III) Z-CO-OR' (III) in which Z is as defined above and R' represents alkyl, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, Le A 31 995-Foreign Countries or when (b) substituted triazines of the general formula (IV) X' N' -N R' (IV) R
Z \N N A~Ar i R-z H
in which Rl, R2, A, Ar and Z are each as defined above and X I represents halogen or alkoxy are reacted with ammonia, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or when (c) substituted triazines of the general formula (V), NN (V) ~

in which Z is as defined above and X2 represents halogen or alkoxy Le A 31 995-Foreign Countries are reacted with substituted alkylamines of the general formula (VI), R' H2N A~Ar (VI) in which R1, R2, A and Ar are each as defined above, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and, if appropriate, further conversions within the scope of the above definition of substituents are carried out by customary methods on the compounds of the general formula (I) obtained by the processes described under (a), (b) or (c).

The novel substituted 2-amino-4-alkylamino-1,3,5-triazines of the general formula (I) have 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 be present in different enantiomeric (R- and S-configured forms) or diastereomeric forms. The invention relates both to the different possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I), and to the mixtures of these isomeric compounds.

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

Le A 31 995-Foreign Countries Halogen generally represents fluorine, chlorine, bromine or iodine, preferably represents fluorine, chlorine or bromine, and in particular represents fluorine or chlorine.

The invention preferably provides compounds of the formula (I) in which R 1 represents optionally hydroxyl-, cyano-, halogen- or C 1-C4-alkoxy-substituted alkyl having 2 to 4 carbon atoms or represents optionally cyano-, halogen- or C,-C4-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, R2 represents hydrogen, methyl or ethyl, A represents oxygen or methylene, Ar represents in each case optionally substituted phenyl, naphthyl or heterocyclyl, where the possible heterocyclyl groupings are preferably selected from the group below:

furyl, benzofuryl, dihydrobenzofuryl, tetrahydrofuryl, thienyl, benzothienyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, quinolinyl, isoquinolinyl, pyridinyl and pyrimidinyl, and where the possible substituents are in each case preferably selected from the group below:

hydroxyl, cyano, nitro, halogen, in each case optionally hydroxyl-, cyano- or halogen-substituted alkyl or alkoxy having in each case 1 to 6 carbon atoms, in each case optionally halogen-substituted alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case I to 6 carbon Le A 31 995-Foreign Countries atoms in the alkyl groups, in each case optionally hydroxyl-, cyano-, nitro-, halogen-, C I-C4-alkyl, C 1-C4-halogenoalkyl-, C I-Cq.-alkoxy- or C 1-C4-halogenoalkoxy-substituted phenyl or phenoxy, and also in each case optionally halogen-substituted methylenedioxy or ethylenedioxy, and Z represents hydrogen, represents halogen, represents in each case optionally hydroxyl-, cyano-, nitro-, halogen-, C 1-C4-alkoxy-, C 1-C4-alkyl-carbonyl-, C 1-C4-alkoxy-carbonyl-, C 1-C4-alkylthio-, C 1-C4-alkylsulphinyl- or C 1-C4-alkylsulphonyl-substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, or represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms.

From among the compounds of the formula (I) defined above as preferred ("preferably"), particular emphasis is given to the following groups:

(A) the compounds of the formula (I) in which A, RI, R2 and Z are each as defined above and Ar represents in each case optionally substituted phenyl or naphthyl, the possible substituents being as defined above;

(B) the compounds of the formula (I) in which A, R1, R2 and Z are each as defined above and Ar represents in each case optionally substituted heterocyclyl, the possible heterocyclyl groupings and the possible substituents being as defined above.

The invention in particular relates to compounds of the formula (I) in which RI represents in each case optionally hydroxyl-, cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted ethyl, n- or i-propyl, n-, i-, s- or t-butyl or Le A 31 995-Foreign Countries represents in each case optionally cyano-, fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, R2 represents hydrogen or methyl, A represents oxygen or methylene, Ar represents in each case optionally substituted phenyl, naphthyl or heterocyclyl, where the possible heterocyclyl groups are preferably selected from the group below:

furyl, benzofuryl, dihydrobenzofuryl, tetrahydrofuryl, thienyl, benzothienyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, quinolinyl, isoquinolinyl, pyridinyl and pyrimidinyl, and where the possible substituents are in each case preferably selected from the group below:

hydroxyl, cyano, nitro, fluorine, chlorine, bromine, in each case optionally hydroxyl- 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, in each case optionally fluorine- or chlorine-substituted acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n-or i-propylsulphonyl, in each case optionally hydroxyl-, 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 Le A 31 995-Foreign Countries phenoxy, and also in each case optionally fluorine- or chlorine-substituted methylenedioxy or ethylenedioxy, and Z represents hydrogen, fluorine, chlorine, bromine, represents in each case optionally hydroxyl-, cyano-. nitro-. fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, methylthio-ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-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, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or represents in each case optionally fluorine-, chlorine- or bromine-substituted ethenyl, propenyl, butenyl, ethinyl, propinyl or butinyl.

From among the compounds of the formula (I) defined above as being particularly preferred, particular emphasis is given to the following groups:

(AA) the compounds of the formula (I) in which A, R1, R2 and Z are each as defined above and Ar represents in each case optionally substituted phenyl or naphthyl, the possible substituents being as defined above, with the proviso that the substituents of the carbon atom to which R' is attached are arranged in the R configuration;

(BB) the compounds of the formula (I) in which A, R1, R2 and Z are each as defined above and Ar represents in each case optionally substituted phenyl or naphthyl, the possible substituents being as defined above, with the proviso that the substituents of the carbon atom to which Ri is attached are arranged in the S configuration;

Le A 31 995-Foreign Countries (CC) the compounds of the formula (I) in which A, R1, R2 and Z are each as defined above and Ar represents in each case optionally substituted furyl, thienyl, pyridinyl or pyrimidinyl, the possible substituents being as defined above, with the proviso that these compounds are present as racemic mixtures;

(DD) the compounds of the formula (I) in which A, R1, R2 and Z are each as defined above and Ar represents in each case optionally substituted furyl, thienyl, pyridinyl or pyrimidinyl, the possible substituents being as defined above, with the proviso that the substituents of the carbon atom to which R1 is attached are arranged in the R
configuration;

(EE) the compounds of the formula (I), in which A, Rl, R2 and Z are each as defined above and Ar represents in each case optionally substituted furyl, thienyl, pyridinyl or pyrimidinyl, the possible substituents being as defined above, with the proviso that the substituents of the carbon atom to which R1 is attached are arranged in the S
configuration;

The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and also, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with each other at will, i.e. including combinations between the abovementioned preferred ranges.

Examples of the compounds of the formula (I) according to the invention are listed in the groups below. The general formulae here represent in each case the R
enantiomers, the S enantiomers and the racemates.

Le A 31 995-Foreign Countries Group 1 J~ J, Z N N
H
Here, Z has, for example, the meanings given below:

Hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, chlorofluoromethyl, chlorobromomethyl, chlorodifluoromethyl, fluorodichloromethyl, bromodifluoro-methyl, trichloromethyl, 1-fluoro-ethyl, 2-fluoro-ethyl, 1-chloro-ethyl, 2-chloro-ethyl, 1-chloro-l-fluoro-ethyl, 1-fluoro-propyl, 2-fluoro-propyl, 3-fluoro-propyl, 1-fluoro-l-methyl-ethyl, 2-fluoro-l-methyl-ethyl, 1-chloro-l-methyl-ethyl, 1-fluoro-l-methyl-propyl, 1-chloro-l-ethyl-propyl, 1-fluoro-l-ethyl-propyl, 1-chloro-l-ethyl-propyl, 1-fluoro-2-methyl-propyl, 1-chloro-2-methyl-propyl, 1-chloro-propyl, 2-chloro-propyl, 3-chloro-propyl, 1-chloro-l-methyl-ethyl, 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-difluoro-propyl, 1,1-dichloro-propyl, perfluoropropyl, 1-fluoro-butyl, 1-chloro-butyl, perfluoropentyl, perfluorohexyl, 1-hydroxyl-ethyl, acetyl, 1,1-bis-acetyl-methyl, 1-acetyl-l-methoxycarbonyl-methyl, 1-acetyl-l-ethoxycarbonyl-methyl, methoxymethyl, 1, 1 -dimethoxy-methyl, 1-methoxyethyl, 2-methoxy-ethyl, 1,1-dimethoxy-ethyl, ethoxymethyl, 1-ethoxyethyl, 2-ethoxy-ethyl, 2-methoxy-l-methyl-ethyl, 2-methoxy-l-ethyl-ethyl, 2-ethoxy-l-methyl-ethyl, 2-ethoxy-l-ethyl-ethyl, methylthiomethyl, ethylthiomethyl, 1-methylthio-ethyl, 2-methylthioethyl, 1-ethylthio-ethyl, 2-ethylthioethyl, methyl-sulphinylmethyl, ethylsulphinylmethyl, methylsulphonylmethyl, ethylsulphonyl-methyl, methoxy, ethoxy, n- or i- propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, fluoromethoxy, Le A 31 995-Foreign Countries difluoromethoxy, trifluoromethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, vinyl, 1-chloro-vinyl, 2-chloro-vinyl, 1-fluoro-vinyl, 2-fluoro-vinyl, 1-bromo-vinyl, 2-bromo-vinyl, 1,2-dichloro-vinyl, 1,2-dibromo-vinyl, 1,2-difluoro-vinyl, 2,2-dichloro-vinyl, 2,2-difluoro-vinyl, 2,2-dibromo-vinyl, 1-chloro-2-fluoro-vinyl, 2-bromo-2-chloro-vinyl, trichlorovinyl, allyl, 2-chloro-allyl, 3-chloro-allyl, 3,3-dichloro-allyl, 1-propenyl, isopropenyl, 1-chloro-2-propenyl, 1-fluoro-2-propenyl, 1-bromo-2-propenyl, 1,2-dichloro-l-propenyl, 1,2-dibromo-l-propenyl, 1,2-difluoro-l-propenyl, 1,1-dichloro-2-propenyl, 1,1-dibromo-2-propenyl, 1,1-difluoro-2-propenyl, 1,1,3,3,3-pentafluoro-2-propenyl, 2-buten-l-yl, 2-buten-2-yl, 3-chloro-2-butenyl, 3-bromo-2-butenyl, 3,3,3-trifluoro-2-butenyl, ethinyl, 2-chloro-ethinyl, 2-bromo-ethinyl, 1-propinyl, 2-propinyl, 3,3,3-trifluoro-l-propinyl.

Group 2 J~ (1-2) Z N N
H

Here, Z has, for example, the meanings given above in group 1.
Group 3 ~ (I-3) Z \N N
H

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

Le A 31 995-Foreign Countries Group 4 NHz N N C2H5 Br ~ (I-4) Z \N N
H
Here, Z has, for example, the meanings given above in group 1.

Group 5 N N CzH5 NO2 Z N A, N
H
Here, Z has, for example, the meanings given above in group 1.

Group 6 NHz ~ cl-s) Z \N N
H
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 7 N N CzH5 CF3 J~ (1-7) Z N N
H
Here, Z has, for example, the meanings given above in group 1.

Group 8 NHZ

J~ c1-$>
Z N N
H
Here, Z has, for example, the meanings given above in group 1.

Group 9 J~ (1-9) Z N N
i H
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 10 N J-' N C2H5 OCF3 I II (I-10) Z/'\N~N
H
Here, Z has, for example, the meanings given above in group 1.

Group 11 I I (I-11) Z NJ, N
H
Here, Z has, for example, the meanings given above in group 1.

Group 12 N / N CzH5 COOC2H5 ~ 1 (I-12) Z Ni1~N

H
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 13 (1-13) Z 'N N
H
Here, Z has, for example, the meanings given above in group 1.

Group 14 N N CzH5 SOCH3 (I-14) Z N N
i H
Here, Z has, for example, the meanings given above in group 1.

Group 15 (I-15) Z \N N
H
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 16 N / _ N CZH5 J~ J, F (1-16) Z N N
H
Here, Z has, for example, the meanings given above in group 1.

Group 17 NHz N_/ _N C2H5 ~ ~ CI (1-17) Z N N I
H
Here, Z has, for example, the meanings given above in group 1.

Group 18 N N C H
(1-18) " _N~N Br i I
H

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

Le A 31 995-Foreign Countries Group 19 J~ J~ N~ (1-19) I
H

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

Group 20 (1-20) CH

I
H

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

Group 21 NHZ
NNCH CF (I-21) I
H

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

Le A 31 995-Foreign Countries Group 22 N J,' N C2H5 Z" _" _N OCH (1-22) H
Here, Z has, for example, the meanings given above in group 1.

Group 23 ~ (1-23) Z \N N
I
H
F
Here, Z has, for example, the meanings given above in group 1.

Group 24 I I~ (1-24) Z~\N~N CI
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 25 N J-, N C 2 H 5 ~ (1-25) Z N N
H
Br Here, Z has, for example, the meanings given above in group 1.

Group 26 NHz ~ (1-26) Z \N N
H

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

Group 27 N N C H
K C 2 H 5 ~ (1-27) Z N N

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

Le A 31 995-Foreign Countries Group 28 N N CzHs I\ ~ (1-28) ZJN N
H

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

Group 29 NHz N_/ _N CzHS
~ (1-29) Z \N N
H

Here, Z has, for example, the meanings given above in group 1.
Group 30 ~ (1-30) Z N N
H

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

Le A 31 995-Foreign Countries Group 31 NHz (1-31) ~
Z \N N
H

Here, Z has, for example, the meanings given above in group 1.
Group 32 N N CZHS
(1-32) Z'J~ N J~ N
I
H

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

Group 33 C2 5 ~ (1-33) Z" NN
i H
COOCzH5 Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 34 N "/ N C2 5 (1-34) Z N N
H

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

Group 35 N / N C2 5 ~ ~ (1-35) Z N N
H

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

Group 36 NHz C2 5 ~ (1-36) Z N N
H
so2CH3 Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 37 CI (I-37) Z N N

CI
Here, Z has, for example, the meanings given above in group 1.

Group 38 NHz N N CzHS
CI (1-38) Z N N
H

CI
Here, Z has, for example, the meanings given above in group 1.

Group 39 N / _ N CZHS CI
~ (I-39) Z \N N

CI
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 40 NHZ
N N CZHS CI
(I-40) Z 'It\N N H

Ct Here, Z has, for example, the meanings given above in group 1.

Group 41 N ./ _ N C2H5 CI
~ (1-41) ZNN H CI

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

Group 42 ~ (1-42) Z~NN H F

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

Le A 31 995-Foreign Countries Group 43 N -/ _ N C2H5 F
~ (I-43) Z \N N
H

F
Here, Z has, for example, the meanings given above in group 1.
Group 44 N_/ _N C2H5 F
Z 'It\ jI (1-44) NJ~N
H
F
Here, Z has, for example, the meanings given above in group 1.

Group 45 J~ J~ F (1-45) Z N N
H
F
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 46 N -/_ N C 2 H 5 J~ J~ F (1-46) Z N N
H

F
Here, Z has, for example, the meanings given above in group 1.
Group 47 (1-47) ~
Z \N N
H
CI

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

Group 48 NHz N / _ N C 2 H 5 CI
~ (1-48) Z \N N
H Z__1 F
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 49 ~ (I-49) Z \N N
H

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

Group 50 N_/ _N C 2 H 5 ~ CH (1-50) Here, Z has, for example, the meanings given above in group 1.
Group 51 NJ-1 N CzHs ~ (1-51) Z~NN CH3 i I
H

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

Le A 31 995-Foreign Countries Group 52 ~ (1-52) Z \N N
H

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

Group 53 NHZ

~ ~ (1-53) Z N N

H CI

Here, Z has, for example, the meanings given above in group 1.
Group 54 ~ (1-54) Z~NN
H
F
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 55 ~ (I-55) Z \N N

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

Group 56 ~ (1-56) Z N N
i H

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

Group 57 Z'11~ NN
i H
F

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

Le A 31 995-Foreign Countries Group 58 N / _ N C 2 H 5 ~ (1-58) Z \N N S
I
H
Here, Z has, for example, the meanings given above in group 1.

Group 59 N / _ N C2H5 ~ (1-59) Z \N N S
H
Here, Z has, for example, the meanings given above in group 1.

Group 60 N J-, N C 2 H 5 ~ (1-60) Z~NN N

i I
H

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

Le A 31 995-Foreign Countries Group 61 N -/ _ N C 2 H 5 ~ (1-61) Z N N N
H

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

Group 62 NHZ
N -/ _ N CZHS
(1-62) Z \N N N

CI
Here, Z has, for example, the meanings given above in group 1.

Group 63 N N C H
(1-63) Z N N
H N
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 64 N ./ _ N C 3 H 7 -n ~ (1-64) Z N N
H
Here, Z has, for example, the meanings given above in group 1.

Group 65 NHZ
N -/ _ N C3H7-i ~ (1-65) Z N N
H
Here, Z has, for example, the meanings given above in group 1.

Group 66 J~ J' '~~ O (1-66) Z N N
H
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 67 N N C3H~ n ~ (I-67) Z~NN_ vG
H
Here, Z has, for example, the meanings given above in group 1.
Group 68 NHz N J-1, N C3H~ i y (1-68) Z" NN -vC H

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

Group 69 ~ (1-69) Z~NN

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

------ -------- - ---Le A 31 995-Foreign Countries Group 70 N J_ N CzHS
~ ~ (1-70) Z N N I O
H
' O
Here, Z has, for example, the meanings given above in group 1.

Group 71 ~ ~ (1-71) Z N N N

N A C''(C'H3)3 Here, Z has, for example, the meanings given above in group 1.

Group 72 NHz Z \ (1-72) N N
H
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 73 ~ '., O (1-73) Z N N_ v I
H

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

Group 74 CF3 (i-74) Z" _N_ _N" 0 I

H cHere, Z has, for example, the meanings given above in group 1.

Group 75 N N C H
(1-75) Z NN vG
I
H

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

Le A 31 995-Foreign Countries Group 76 N N CZHS
~ ~ (1-76) Z N N ~ I

F
Here, Z has, for example, the meanings given above in group 1.
Group 77 F (1-77) J~ J, 0 Z N N~
i H

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

Group 78 fl (1-78) Z" _NN 0 i I
H
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 79 ~ ~ O (1-79) Z N N v H

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

Group 80 NHZ
N -/_ N CZHS
ZN~NO CH (I-80) Here, Z has, for example, the meanings given above in group 1.

Group 81 NJ~11 N CZHS
j (1-81) Z NN_ vG

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

Le A 31 995-Foreign Countries Group 82 ~ J~ O (1-82) Z N
H a Here, Z has, for example, the meanings given above in group 1.

Group 83 C25 (1-83) ZN" N~O
I
H

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

Group 84 ~ (1-84) Z~NN -v0 I
H

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

Le A 31 995-Foreign Countries Group 85 N_/ -N CZHS
Z'J~NN" 0 / CH3 I
H ~

Here, Z has, for example, the meanings given above in group 1.
Group 86 Z~ N N O CH3 Here, Z has, for example, the meanings given above in group 1.
Group 87 NHz Z" _N_ _N~O CH3 I
H

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

Le A 31 995-Foreign Countries Group 88 N_/ -N CzHS
Z~N~N~G (1-88) N
~
H \N CH3 Here, Z has, for example, the meanings given above in group 1.
Group 89 N N CZHS
( (1-89) Z'~ NN~0 ~
rN N

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

Group 90 N -:~kN C2H5 (1-90) Z \N ~N 't~~ 0 S
H
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 91 N J-1, N CZHS
~ O (1-91) Z N N N
H ~
Here, Z has, for example, the meanings given above in group 1.
Group 92 N_/ _N C2H
~
Z'Jz~' N~N- v O (1-92) H
' Here, Z has, for example, the meanings given above in group 1.
Group 93 N N C H
I ~ (1-93) Z ~NJ~N O

H
Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 94 N / N C 2 H 5 Z ~ N ~ N N CH3 (1-94) I
H

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

Group 95 N J-1 N CzHs Z~ N~ N O ~N (1-95) J.CF3 H

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

Group 96 N N CzHS
~ 'y_' O (1-96) Z N N_ v ~S

H Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Group 97 J~ l~ ~O (1-97) ~
Z N N rN N
H C(CH3)3 Here, Z has, for example, the meanings given above in group 1.

Group 98 N"/ _N C2H5 J~ J~ ~ O (1-98) ~
Z N N C--N N
H CH(CH3)2 Here, Z has, for example, the meanings given above in group 1.

Le A 31 995-Foreign Countries Using, for example, 1-(1-ethyl-3-phenyl-propyl)-biguanide and methyl trifluoro-acetate as starting materials, the course of the reaction in the process (a) according to the invention can be illustrated by the following equation:

0 OCH3 H, N H, N C H NHs II
y + H, N\ N C2H5 CF3 N N N 2 -CH30H )ll, ~
H H H -H20 F N N ( H

Using, for example, 2-chloro-4-(1-ethyl-3-phenyl-propylamino)-6-trifluoromethyl-1,3,5-triazine and ammonia as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following equation:

N N CzHS + NH3 ~

~ A, HCI
F3C N N F3C N N ~
H H
Using, for example, 2-amino-4-methoxy-6-trifluoromethyl-1,3,5-triazine and 3-phenyl- l-ethyl-propylamine as starting materials, the course of the reaction in the process (c) according to the invention can be illustrated by the following equation:
NH

~ ~
N" \ N + HzN HOCH3 i~ N CZHS
~
i F3C N N I~
F3C~ N OCH3 H
/
The formula (II) provides a general definition of the substituted biguanides to be used as starting materials in the process (a) according to the invention for preparing compounds of the formula (I). In the formula (11), Rl, R2, A and Ar each preferably or in particular have those meanings which have already been mentioned above, in Le A 31 995-Foreign Countries connection with the description of the compounds of the formula (I) according to the invention, as being preferred or as being particularly preferred for R1, R2, A
and Ar.
Examples of the substituted biguanides of the formula (II) which may be mentioned are:

1-(1-ethyl-3-phenyl-propyl)-, 1-(1-n-propyl-3-phenyl-propyl)-, 1-(1-i-propyl-3 -phen-yl-propyl)-, 1-(1-cyclopropyl-3 -phenyl-propyl)-, 1-(1-ethyl-3 -(2-fluoro-phenyl)-prop-yl)-, 1-(1-ethyl-3-(3-fluoro-phenyl)-propyl)-, 1-(1-ethyl-3-(4-fluoro-phenyl)-propyl)-, 1-(1-ethyl-3-(2-chloro-phenyl)-propyl)-, 1-(1-ethyl-3-(3-chloro-phenyl)-propyl)-, 1-1 0 (1-ethyl-3-(4-chloro-phenyl)-propyl)-, 1-(1-ethyl-3-(2-bromo-phenyl)-propyl)-, 1-(1-ethyl-3-(3-bromo-phenyl)-propyl)-, 1-(1-ethyl-3-(4-bromo-phenyl)-propyl)-, 1-(1-ethyl-3-(2-nitro-phenyl)-propyl)-, 1-(1-ethyl-3-(3-nitro-phenyl)-propyl)-, 1-(1-ethyl-3-(4-nitro-phenyl)-propyl)-, 1-(1-ethyl-3-(2-methyl-phenyl)-propyl)-, 1-(1-ethyl-3-(3-methyl-phenyl)-propyl)-, 1-(1-ethyl-3-(4-methyl-phenyl)-propyl)-, 1-(1-ethyl-3-(2-trifluoromethyl-phenyl)-propyl)-, 1-(1-ethyl-3-(3-trifluoromethyl-phenyl)-propyl)-, 1-(1-ethyl-3-(4-trifluoromethyl-phenyl)-propyl)-, 1-(1-ethyl-3-(2-methoxy-phenyl)-propyl)-, 1-(1-ethyl-3-(3-methoxy-phenyl)-propyl)-, 1-(1-ethyl-3-(4-methoxy-phen-yl)-propyl)-, 1-(1-ethyl-3 -(2-difluoromethoxy-phenyl)-propyl)-, 1-(1-ethyl-3 -(2-di-fluoromethoxy-phenyl)-propyl)-, 1-(1-ethyl-3 -(2-difluoromethoxy-phenyl)-propyl)-, 1-(1-ethyl-3-(2-trifluoromethoxy-phenyl)-propyl)-, 1-(1-ethyl-3-(3-trifluoromethoxy-phenyl)-propyl), 1-(1-ethyl-3-(4-trifluoromethoxy-phenyl)-propyl)-, 1-(1-ethyl-3-(2-methoxycarbonyl-phenyl)-propyl)-, 1-(1-ethyl-3-(2-ethoxycarbonyl-phenyl)-propyl)-, 1-(1-ethyl-3-(4-methoxycarbonyl-phenyl)-propyl)-, 1-(1-ethyl-3-(4-ethoxycarbonyl-phenyl)-propyl)-, 1-(1-ethyl-3-(2-methylthio-phenyl)-propyl)-, 1-(1-ethyl-3-(4-meth-ylthio-phenyl)-propyl)-, 1-(1-ethyl-3-(2-methylsulphinyl-phenyl)-propyl)-, 1-(1-eth-yl-3-(4-methylsulphinyl-phenyl)-propyl)-, 1-(1-ethyl-3-(2-methylsulphonyl-phenyl)-propyl)-, 1-(1-ethyl-3-(4-methylsulphonyl-phenyl)-propyl)-, 1-(1-ethyl-3-(3,4-di-chloro-phenyl)-propyl)-, 1-(1-ethyl-3-(2,4-dichloro-phenyl)-propyl)-, 1-(1-ethyl-3-(2,5-dichloro-phenyl)-propyl)-, 1-(1-ethyl-3-(2,6-dichloro-phenyl)-propyl)-, 1-(1-ethyl-3-(2,6-difluoro-phenyl)-propyl)-, 1-(1-ethyl-3-(2,5-difluoro-phenyl)-propyl)-, 1-(1-ethyl-3-(2,4-difluoro-phenyl)-propyl)-, 1-(1-ethyl-3-(3,4-difluoro-phenyl)-prop-Le A 31 995-Foreign Countries yl)-, 1-(1-ethyl-3-(3,5-difluoro-phenyl)-propyl)-, 1-(1-ethyl-3-(2-fluoro-4-chloro-phenyl)-propyl)-, 1-(1-ethyl-3-(4-fluoro-2-chloro-phenyl)-propyl)-, 1-(1-ethyl-3-(2,4-dimethyl-phenyl)-propyl)-, 1-(1-ethyl-3-(3,4-dimethyl-phenyl)-propyl)-, 1-(1-ethyl-3-(3,5-dimethyl-phenyl)-propyl)-, 1-(1-ethyl-3-(2,5-dimethyl-phenyl)-propyl)-, 1-(1-ethyl-3-(2-chloro-6-methyl-phenyl)-propyl)-, 1-(1-ethyl-3-(4-fluoro-2-methyl-phen-yl)-propyl)-, 1-(1-ethyl-3-(2-fluoro-4-methyl-phenyl)-propyl)-, 1-(1-ethyl-3-(2-fluoro-5-methyl-phenyl)-propyl)-, 1-(1-ethyl-3-(5-fluoro-2-methyl-phenyl)-propyl)-, 1-(1-ethyl-3-thien-2-yl-propyl)-, 1-(1-ethyl-3-thien-3-yl-propyl)-, 1-(1-ethyl-pyridin-2-yl-propyl)-, 1-(1-ethyl-3-pyridin-3-yl-propyl)- and 1-(1-ethyl-3-pyridin-4-yl-propyl)-biguanide.

Suitable acid adducts of compounds of the formula (II) are their addition products with protic acids, such as, for example with hydrogen chloride, hydrogen bromide, sulphuric acid, methanesulphonic acid, benzenesulphonic acid and p-toluene-sulphonic acid.

The starting materials of the general formula (II) have hitherto not been disclosed in the literature; as novel substances, they also form part of the subject matter of the present application.

The novel substituted biguanides of the general formula (II) are obtained when substituted alkylamines of the general formula (VI), R' H2N Ar (VI) in which R1, R2, A and Ar are each as defined above Le A 31 995-Foreign Countries - and/or acid adducts of compounds of the general formula (VI), such as, for example, the hydrochlorides -are reacted with cyanoguanidine ("dicyanodiamide") of the formula (VII) H, N

H.NA, NN (VII) i i H H

if appropriate in the presence of a reaction auxiliary, such as, for example, hydrogen chloride, and if appropriate in the presence of a diluent, such as, for example, n-decane or 1,2-dichloro-benzene, at temperatures between 100 C and 200 C (cf.
EP
492615, Preparation Examples).

The substituted alkylamino compounds of the general formula (VI) required as precursors for this purpose are known and/or can be prepared by processes known per se (cf. J. Med. Chem. 10 (1967); 717-724; J. Am. Chem. Soc. 97 (1975), 6901; Tetrahedron Lett. 35 (1994), 3745-3746; DE 3222152; DE 3221540; EP
355351; EP 601486; Preparation Examples).

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

The starting materials of the formula (III) are known chemicals for synthesis.

Le A 31 995-Foreign Countries The formula (IV) provides a general definition of the substituted triazines to be used as starting materials in the process (b) according to the invention for preparing compounds of the formula (I). In the formula (IV), R1, R2, A, Ar and Z each 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, as being preferred or as being particularly preferred for R1, R2, A, Ar and Z; X1 preferably represents fluorine, chlorine, bromine, methoxy or ethoxy, and in particular represents chlorine or methoxy.

Examples of the substituted triazines of the formula (IV) which may be mentioned are:

2-(1-ethyl-3-phenyl-propylamino)-, 2-(1-ethyl-3-(2-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-fluoro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-chloro-phen-yl)-propylamino)-, 2-(1-ethyl-3 -(4-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3 -(3 -bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-nitro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(3-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methoxy-phenyl)-pro-pylamino)-, 2-(1 -ethyl-3 -(4-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-di-fluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-trifluoromethoxy-phenyl)-propylamino)-, 1-(1-ethyl-3-(3-trifluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethoxy-phenyl)-propylamino)-, (1 -ethyl-3-(2-methoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-ethoxy-carbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxycarbonyl-phenyl)-propyl-Le A 31 995-Foreign Countries amino)-, 2-(1-ethyl-3-(4-ethoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylthio-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-methylthio-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(3,4-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2,4-dichloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2,5-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-di-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-chloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3 -(4-fluoro-2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-chloro-6-methyl-phenyl)-propylamino)-, (1-ethyl-3-(4-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-5-methyl-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(5-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-thien-2-yl-propylamino)-, 2-(1-ethyl-3-thien-3-yl-propylamino)-, 2-(1-ethyl-3-pyridin-2-yl-propylamino)-, 2-(1-ethyl-3-pyridin-3-yl-propylamino)- and 2-(1-ethyl-3-pyridin-4-yl-propylamino)- -4,6-dichloro-1,3,5-triazine;

2-(1-ethyl-3-phenyl-propylamino)-, 2-(1-ethyl-3-(2-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-fluoro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-nitro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(3-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methyl-phenyl)-propylarnino)-, 2-(1-ethyl-3-(4-methyl-phenyl)-propylamino)-, 2-(1-Le A 31 995-Foreign Countries ethyl-3-(2-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-di-fluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-trifluoromethoxy-phenyl)-propylamino)-, 1-(1-ethyl-3 -(3 -trifluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethoxy-phenyl)-propylamino)-, (1-ethyl-3-(2-methoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-ethoxy-carbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxycarbonyl-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-ethoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylthio-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-methylthio-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(3,4-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2,4-dichloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2,5-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-di-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-chloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-fluoro-2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-chloro-6-methyl-phenyl)-propylamino)-, (1-ethyl-3-(4-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-5-methyl-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(5-fluoro-2-methyl-phenyl)-propylamino)-, 2 -(1 -ethyl -3 -thien-2-yl-propylamino)-, 2-(1-ethyl-3-thien-3-yl-propylamino)-, 2-(1-ethyl-3-pyridin-2-yl-propylamino)-, 2-(1-ethyl-3-pyridin-3-yl-propylamino)- and 2-(1-ethyl-3-pyridin-4-yl-propylamino)- -4-chloro-6-methyl-1,3,5-triazine;

Le A 31 995-Foreign Countries 2-(1-ethyl-3-phenyl-propylamino)-, 2-(1-ethyl-3-(2-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-fluoro-phenyl)-propyl-amino)-, 2-(1 -ethyl-3 -(2-chloro-phenyl)-propylamino)-, 2-(1 -ethyl-3 -(3 -chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-nitro-phenyl)-propyl-amino)-, 2-(1-ethyl-3 -(3 -nitro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-di-fluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-trifluoromethoxy-phenyl)-propylamino)-, 1-(1-ethyl-3-(3-trifluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-trifluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-ethoxy-carbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxycarbonyl-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-ethoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethy? 3-(2-methylthio-phenyl)-propylamino)-, 2-(1 -ethyl-3 -(4-methylthio-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-dichloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2,5-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-di-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-fluoro-4-chloro-phenyl)-propyl-Le A 31 995-Foreign Countries amino)-, 2-(1-ethyl-3-(4-fluoro-2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(3,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-chloro-6-methylphenyl)-propylamino)-, 2-(1-ethyl-3-(4-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-5-methyl-phenyl)-propylamino)-, (1-ethyl-3-(5-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-thien-2-yl-propyl-amino)-, 2-(1-ethyl-3-thien-3-yl-propylamino)-, 2-(1-ethyl-3-pyridin-2-yl-propyl-amino)-, 2-(1-ethyl-3-pyridin-3-yl-propylamino)- and 2-(1-ethyl-3-pyridin-4-yl-propylamino)- -4-chloro-6-trifluoromethyl-1,3,5-triazine;

2-(1-ethyl-3 -phenyl-propylamino)-, 2-(1-ethyl-3 -(2-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-fluoro-phenyl)-propylamino)-, 2-(1 -ethyl-3-(4-fluoro-phenyl)-propyl-amino)-, 2-(1-ethyl-3 -(2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(3 -chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3 -(3 -bromo-phenyl)-propylamino)-, (1-ethyl-3-(4-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-nitro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(3-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-di-fluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-trifluoromethoxy-phenyl)-propylamino)-, 1-(1-ethyl-3-(3-trifluoromethoxy-phenyl)-propylamino)-, 2 -(1 -ethyl -3 -(4 -trifluoromethoxy-phenyl)-propylamino) -, 2-(1-ethyl-3-(2-methoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-ethoxy-carbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxycarbonyl-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-ethoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-Le A 31 995-Foreign Countries methylthio-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylthio-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-dichloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2,5-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-di-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-chloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-fluoro-2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-chloro-6-methylphenyl)-propylamino)-, 2-(1-ethyl-3-(4-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-5-methyl-phenyl)-propylamino)-, (1-ethyl-3-(5-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-thien-2-yl-propyl-amino)-, 2-(1-ethyl-3 -thien-3 -yl-propylamino)-, 2-(1-ethyl-3 -pyridin-2-yl-propyl-amino)-, 2-(1-ethyl-3-pyridin-3-yl-propylamino)- and 2-(1-ethyl-3-pyridin-4-yl-propylamino)- -4-chloro-6-(1-fluoro-ethyl)-1,3,5-triazine;

2-(1-ethyl-3-phenyl-propylamino)-, 2-(1-ethyl-3-(2-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-fluoro-phenyl)-propylamino)-, 2-(l -ethyl-3 -(4-fluoro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-nitro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(3-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-trifluoromethyl-Le A 31 995-Foreign Countries phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-di-fluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-trifluoromethoxy-phenyl)-propylamino)-, 1-(1-ethyl-3-(3-trifluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethoxy-phenyl)-propylamino)-, (1-ethyl-3-(2-methoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-ethoxy-carbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxycarbonyl-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-ethoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylthio-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylthio-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-dichloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2,5-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-di-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2,6-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-chloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-fluoro-2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(3,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-chloro-6-methyl-phenyl)-propylamino)-, (1 -ethyl-3-(4-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-5-methyl-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(5-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-thien-2-yl-propylamino)-, 2-(1-ethyl-3-thien-3-yl-propylamino)-, 2-(1-ethyl-3-pyridin-2-yl-propylamino)-, 2-(1-ethyl-3-pyridin-3-yl-propylamino)- and 2-(1-ethyl-3-pyridin-4-yl-propylamino)- -4-chloro-6-(1-fluoro-l-methyl-ethyl)-1,3,5-triazine;

Le A 31 995-Foreign Countries 2-(1-ethyl-3-phenyl-propylamino)-, 2-(1-ethyl-3-(2-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-fluoro-phenyl)-propyl-amino)-, 2-(1 -ethyl-3 -(2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-bromo-phenyl)-propylamino)-, 2-(1 -ethyl-3 -(2-nitro-phenyl)-propyl-amino)-, 2-(1-ethyl-3 -(3 -nitro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-di-fluoromethoxy-phenyl)-propylamino)-, 2-(1 -ethyl-3 -(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-trifluoromethoxy-phenyl)-propylamino)-, 1-(1-ethyl-3-(3-trifluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethoxy-phenyl)-propylamino)-, (1-ethyl-3 -(2-methoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-ethoxy-carbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxycarbonyl-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-ethoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylthio-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylthio-phenyl)-propyl-amino)-, 2-(1-ethyl-3 -(2-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-dichloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2,5-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-di-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-difluoro-phenyl)-propylamino)-, 2-(1 -ethyl -3 -(2,4 -difluoro-phenyl)-propylamino)-, 2-(1 -ethyl- 3 -(3,4-di fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-chloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-fluoro-2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-Le A 31 995-Foreign Countries dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-chloro-6-methyl-phenyl)-propylamino)-, (1-ethyl-3-(4-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1 -ethyl-3 -(2-fluoro-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-5-methyl-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(5-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-thien-2-yl-propylamino)-, 2-(1-ethyl-3 -thien-3 -yl-propylamino)-, 2-(1-ethyl-3 -pyridin-2-yl-propylamino)-, 2-(1-ethyl-3-pyridin-3-yl-propylamino)- and 2-(1-ethyl-3-pyridin-4-yl-propylamino)- -4-chloro-6-methoxy-1,3,5-triazine;

2-(1-ethyl-3-phenyl-propylamino)-, 2-(1-ethyl-3-(2-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-fluoro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-chloro-phenyl)-propylaznino) -, 2-(1-ethyl-3 -(2-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-nitro-phenyl)-propyl-amino)-, 2-(1-ethyl-3 -(3 -nitro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(3 -methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-di-fluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-trifluoromethoxy-phenyl)-propylamino)-, 1-(1-ethyl-3-(3-trifluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethoxy-phenyl)-propylamino)-, (1-ethyl-3-(2-methoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-ethoxy-carbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxycarbonyl-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-ethoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylthio-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylthio-phenyl)-propyl-Le A 31 995-Foreign Countries amino)-, 2-(1-ethyl-3-(2-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-dichloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2,5-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-di-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2,6-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-chloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-fluoro-2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-chloro-6-methylphenyl)-propylamino)-, 2-(1-ethyl-3-(4-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-5-methyl-phenyl)-propylamino)-, (1-ethyl-3-(5-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-thien-2-yl-propyl-amino)-, 2-(1-ethyl-3 -thien-3 -yl-propylamino)-, 2-(1-ethyl-3 -pyridin-2-yl-propyl-amino)-, 2-(1-ethyl-3-pyridin-3-yl-propylamino)- and 2-(1-ethyl-3-pyridin-4-yl-propylamino)- -4-chloro-6-(2,2,2-trifluoro-ethoxy)-1,3,5-triazine;

2-(1-ethyl-3-phenyl-propylamino)-, 2-(1-ethyl-3-(2-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-fluoro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-nitro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(3-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-nitro-phenyl)-propylamino)-, 2 -(1 -ethyl -3 -(2 -methyl -phenyl)-propyl amino)-, 2-(1-ethyl-3-(3-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methyl-phenyl)-propylamino)-, 2-(1-ethyl -3 -(2-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethyl-phenyl)-propylamino)-, 2-(1-Le A 31 995-Foreign Countries ethyl-3-(2-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-di-fluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-trifluoromethoxy-phenyl)-propylamino)-, 1-(1-ethyl-3 -(3 -trifluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethoxy-phenyl)-propylamino)-, (1-ethyl-3-(2-methoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-ethoxy-carbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxycarbonyl-phenyl)-propyl-amino)-, 2-(1-ethyl-3 -(4-ethoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-methylthio-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylthio-phenyl)-propyl-amino)-, 2-(1-ethyl-3 -(2-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(3,4-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2,4-dichloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2,5-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-di-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-chloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-fluoro-2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(3,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-dimethyl-phenyl)-propylamino)-, 2-(1 -ethyl-3 -(2,5 -dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-chloro-6-methylphenyl)-propylamino)-, 2-(1-ethyl-3-(4-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-5-methyl-phenyl)-propylamino)-, (1-ethyl-3-(5-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-thien-2-yl-propyl-amino)-, 2-(1-ethyl-3-thien-3-yl-propylamino)-, 2-(1-ethyl-3-pyridin-2-yl-propyl-amino)-, 2 -(1 -ethyl -3 -pyridin-3 -yl -propyl amino)- and 2-(1-ethyl-3-pyridin-4-yl-propylamino)- -4-chloro-6-methylthio-1,3,5-triazine;

Le A 31 995-Foreign Countries 2-(1-ethyl-3-phenyl-propylamino)-, 2-(1-ethyl-3-(2-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-fluoro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-nitro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(3-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(3 -trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-di-fluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-trifluoromethoxy-phenyl)-propylamino)-, 1 -(1-ethyl-3 -(3 -trifluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethoxy-phenyl)-propylamino)-, (1 -ethyl-3 -(2-methoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-ethoxy-carbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxycarbonyl-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-ethoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylthio-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylthio-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-dichloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2,5-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-di-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-chloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-fluoro-2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-Le A 31 995-Foreign Countries dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-chloro-6-methylphenyl)-propylamino)-, 2-(1-ethyl-3-(4-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-5-methyl-phenyl)-propylamino)-, (1-ethyl-3-(5-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-thien-2-yl-propyl-amino)-, 2-(1-ethyl-3-thien-3-yl-propylamino)-, 2-(1-ethyl-3-pyridin-2-yl-propyl-amino)-, 2-(1-ethyl-3-pyridin-3-yl-propylamino)- and 2-(1-ethyl-3-pyridin-4-yl-propylamino)- -4-chloro-6-methylsulphinyl-1,3,5-triazine;

2-(1-ethyl-3-phenyl-propylamino)-, 2-(1-ethyl-3-(2-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-fluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-fluoro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-bromo-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-nitro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(3-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-nitro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(3-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-di-fluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-difluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-trifluoromethoxy-phenyl)-propylamino)-, 1-(1-ethyl-3-(3-trifluoromethoxy-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-trifluoromethoxy-phenyl)-propylamino)-, (1-ethyl-3-(2-methoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-ethoxy-carbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methoxycarbonyl-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-ethoxycarbonyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylthio-phenyl)-propylamino)-, 2-(1-ethyl-3-(4-methylthio-phenyl)-propyl-Le A 31 995-Foreign Countries amino)-, 2-(1-ethyl-3 -(2-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-methylsulphinyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(4-methylsulphonyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(3,4-dichloro-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2,4-dichloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(2,5-dichloro-phenyl)-propylamino)-, 2-(1 -ethyl-3 -(2,6-di-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,6-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-difluoro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-4-chloro-phenyl)-propyl-amino)-, 2-(1-ethyl-3-(4-fluoro-2-chloro-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,4-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(3,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2,5-dimethyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-chloro-6-methylphenyl)-propylamino)-, 2-(1-ethyl-3 -(4-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3 -(2-fluoro-4-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-(2-fluoro-5-methyl-phenyl)-propylamino)-, (1-ethyl-3-(5-fluoro-2-methyl-phenyl)-propylamino)-, 2-(1-ethyl-3-thien-2-yl-propyl-amino)-, 2-(1-ethyl-3-thien-3-yl-propylamino)-, 2-(1-ethyl-3-pyridin-2-yl-propyl-amino)-, 2-(1-ethyl-3-pyridin-3-yl-propylamino)- and 2-(1-ethyl-3-pyridin-4-yl-propylamino)- -4-chloro-6-methylsulphonyl-1,3,5-triazine.

The starting materials of the general formula (IV) have hitherto not been disclosed in the literature; as novel substances, they also form part of the subject-matter of the present application.

The novel substituted triazines of the general formula (IV) are obtained when triazines of the general formula (VIII) X' N N (VIII) Le A 31 995-Foreign Countries in which X1 and Z are each as defined above and X3 represents halogen are reacted with substituted alkylamines of the general formula (VI) R' H 2 N Ar (VI) in which RI, R2, A and Ar are each as defined above, if appropriate in the presence of an acid acceptor, such as, for example, ethyldiisopropylamine, and if appropriate in the presence of a diluent, such as, for example, tetrahydrofuran or dioxane, at temperatures between -50 C and +50 C
(cf.
the Preparation Examples).

The formula (V) provides a general definition of the substituted triazines to be used as starting materials in the process (c) according to the invention for preparing compounds of the formula (I). In the formula (V), Z preferably or in particular has that meaning which has already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred or as being particularly preferred for that; X2 preferably represents fluorine, chlorine, bromine, methoxy or ethoxy, and in particular represents chlorine or methoxy.

Le A 31 995-Foreign Countries The starting materials of the general formula (V) are known and/or can be prepared by processes known per se (cf. WO 95/11237).

The formula (VI) provides a general definition of the substituted alkylamines further to be used as starting materials in the process (c) according to the invention. In the formula (VI), R1, R2, A and Ar each preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (IV) according to the invention, as being preferred or as being particularly preferred for RI, R2, A and Ar.

The starting materials of the general formula (VI) 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 (1988), 223-224; loc. cit. 36 (1995), 3917-3920; Preparation Examples).

If appropriate, the processes according to the invention for preparing the compounds of the formula (I) are carried out using a reaction auxiliary. Suitable reaction auxiliaries for the processes (a), (b) and (c) are, in general, 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 alkoxides, such as, for example, sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide or potassium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylmine, N,N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-ethyl-Le A 31 995-Foreign Countries 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-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-diaza-bicyclo[5,4,0]-undec-7-ene (DBU).

Suitable diluents for carrying out the processes (a), (b) and (c) according to the invention are especially inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride;
ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; ketones, such as methyl isopropyl ketone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate, sulphoxides, such as dimethyl sulphoxide; 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, mixtures thereof with water or pure water.

In the practice of the processes (a), (b) and (c) according to the invention, the reaction temperatures can be varied over a relatively wide range. Generally, the reaction is carried out at temperatures between 0 C and 300 C, preferably between 10 C and 250 C.

The processes (a), (b) and (c) according to the invention are generally carried out at atmospheric pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

Le A 31 995-Foreign Countries In the practice of the processes according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess of one of the components. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred for several hours at the temperature required.
Work-up is carried out by conventional methods (cf. the Preparation Examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed-killers. By weeds in the broadest sense, there are to be understood all plants which grow in locations where they are undesirable.

Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in connection with the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.
Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and 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 and Phalaris.

Le A 31 995-Foreign Countries Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.

The compounds are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and railway tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for controlling weeds in perennial cultures, for example forests, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, on lawns, turf and pasture land, and for the selective control of weeds in annual cultures.

The compounds of the formula (I) according to the invention are suitable in particular for selectively controlling monocotyledonous and dicotyledonous weeds in monocotyledonous and dikotyledonous crops, 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, suspo-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersing agents and/or foam-forming agents.

Le A 31 995-Foreign Countries If the extender used is water, it is also possible to employ for example organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chioroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water.

Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fmely divided silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam-forming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and also protein hydrolysates; suitable dispersing agents are: for example lignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Other possible additives are mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes, such as alizarin dyes, azo dyes and Le A 31 995-Foreign Countries metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.

Possible components for the mixtures are known herbicides, for example acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, asulam, atrazine, azimsulfuron, benazolin, benfuresate, bensulfuron(-methyl), bentazon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bromobutide, bromofenoxim, bromoxynil, butachlor, butylate, cafenstrole, carbetamide, chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl), chlomitrofen, chlorsulfuron, chlortoluron, cinmethylin, cinosulfuron, clethodim, clodinafop(-propargyl), clomazone, clopyralid, clopyrasulfuron, cloransulam(-methyl), cumyluron, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), difenzoquat, diflufenican, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl), ethofumesate, ethoxyfen, etobenzanid, fenoxaprop-ethyl, flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl), flazasulfuron, fluazifop(-butyl), flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam, flupropacil, flurenol, fluridone, fluroxypyr, flurprimidol, flurtamone, fomesafen, glufosinate(-ammonium), glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl), hexazinone, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapyr, imazaquin, imazethapyr, imazosulfuron, ioxynil, isopropalin, isoproturon, isoxaben, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, metamitron, Le A 31 995-Foreign Countries metazachlor, methabenzthiazuron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon orbencarb, oryzalin, oxadiazon, oxyfluorfen, paraquat, pendimethalin, phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl), prometryn, propachlor, propanil, propaquizafop, propyzamide, prosulfocarb, prosulfuron, pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyributicarb, pyridate, pyrithiobac(-sodium) quinchlorac, quinmerac, quizalofop(-ethyl), quizalofop(-p-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, tebutam, tebuthiuron, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.
Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, are 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 customary manner, for example by watering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.

Le A 31 995-Foreign Countries The preparation and use of the active compounds according to the invention can be seen from the Examples below.

Preparation Examples:
Example 1 F I
'N N

(Process (a)) At approximately 22 C, a mixture of 2.0 g (7 mmol) of (R/S)-1-(1-ethyl-3-phenyl-propyl)-biguanide hydrochloride (racemic), 1.89 g (14 mmol) of ethyl 2-fluoro-isobutyrate, 0.76 g (14 mmol) of sodium methoxide and 12 ml of methanol is stirred for about 15 hours. The mixture is then diluted to about 3 times its original volume using water and shaken with ethyl acetate, and the organic phase is separated off washed with water, dried with sodium sulphate and filtered. The solvent is carefully distilled off from the filtrate under water pump vacuum. The residue is purified by column chromatography (silica gel, ethyl acetate).

This gives 1.44 g (64% of theory) of (R/S)-2-amino-4-(1-fluoro-1-methyl-ethyl)-6-(1-ethyl-3-phenyl-propylamino)-1,3,5-triazine (racemate).

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

Le A 31 995-Foreign Countries Ni N R
Z" K N N
, Ar (1) H

Table 1: Examples of compounds of the formula (I) Ex. No. R R A Ar Z Physical data and stereochemical specification 2 C2H5 H 0 CF3 m.p.:100 C
(racemate) 3 C2H5 H 0 CF3 (amorphous) (R enantiomer) 4 C2H5 H 0 CF3 (amorphous) (S enantiomer) ocH, (racemate) ocH, (R enantiomer) ocH, (S enantiomer) 8 C2H5 H CH2 CF(CH3)2 (amorphous) SCH 3 (racemate) Le A 31 995-Foreign Countries Table 1 (continued) Ex. R R A Ar Z Physical data No. and stereochemical specifications 9 C2H5 H CH2 I CF(CH3)2 (R enantiomer) C2H5 H CHz CF(CH3)2 (S enantiomer) 11 C2H5 H CH2 S CF3 (amorphous) 0\/ (racemate) 12 C2H5 H CH2 CF3 (amorphous) ~ ~ (racemate) S

13 C2H5 H CH2 N CF3 m.p.:74 C
CI (racemate) 14 C2H5 H CH2 ~N CF3 (amorphous) ~ ~ (racemate) C2H5 H CH2 CF3 (amorphous) (racemate) 16 C2H5 H CH2 / CF3 (amorphous) ~ (racemate) ~ N

17 C2H5 H 0 CF3 (amorphous) ri 11 N C(CH3)3 (racemate) 18 C2H5 H CH2 CHFCH3 (amorphous) CI (racemate) Le A 31 995-Foreign Countries Table 1 (continued) Ex. R R A Ar Z Physical data No. and stereochemical specifications 19 C2H5 H CH2 CHFCH3 (amorphous) (racemate) S

20 C2H5 H CH2 CHFCH3 (amorphous) (racemate) 21 C2H5 H CH2 N CHFCH3 (amorphous) (racemate) 22 C2H5 H CH2 N CF(CH3)2 (amorphous) ( (racemate) 23 C2H5 H CH2 S CHFCH3 (amorphous) Q/ (racemate) 24 C2H5 H CH2 S CF(CH3)2 (amorphous) 0\/ (racemate) 25 C2H5 H CH2 / N CF(CH3)2 (amorphous) CI (racemate) 26 C2H5 H CH2 CF(CH3)2 (amorphous) (racemate) 27 C3H7-i H CH2 CF3 (amorphous) I / CI (racemate) 28 C3H7-i H CH2 CHFCH3 (amorphous) I / CI (racemate) Le A 31 995-Foreign Countries Table 1 (continued) Ex. R R2 A Ar Z Physical data No. and stereochemical specifications 29 C3H7-i H CH2 CF(CH3)2 (amorphous) (racemate) 30 C3H7-n H CH2 I~ CF(CH3)2 (amorphous) / cl (racemate) 31 C3H7-n H CH2 ~ CHFCH3 (amorphous) I / ci (racemate) 32 C3H7-n H CH2 CF3 (amorphous) I / Cl (racemate) 33 C2H5 H CH2 CF(CH3)2 (amorphous) (racemate) S

34 C2H5 H CH2 CF3 (amorphous) SCH3 (racemate) 35 C2H5 H CH2 CHFCH3 (amorphous) SCH3 (racemate) 36 C2H5 H 0 CHFCH3 (amorphous) N c(cH,), (racemate) 37 C2H5 H 0 CF(CH3)2 (amorphous) \N c(cH), (racemate) 38 C2H5 H 0 C2H5 (amorphous) ~
\N c(cH,), (racemate) 39 C2H5 H 0 CHFCH3 (amorphous) (racemate) Le A 31 995-Foreign Countries Table 1 (continued) Ex. R R A Ar Z Physical data No. and stereochemical specifications 40 C2H5 H 0 C2H5 (amorphous) (racemate) 41 C2H5 H CH2 CF3 (amorphous) (racemate) 42 C2H5 H 0 CF3 (amorphous) (racemate) 43 C2H5 H CH2 CF3 (amorphous) (S enantiomer) 44 C2H5 H 0 CF3 (amorphous) (S enantiomer) 45 C2H5 H CH2 CF3 (amorphous) (R enantiomer) 46 C2H5 H 0 CF3 (amorphous) I / ci (R enantiomer) 47 C2H5 H CH2 CF(CH3)2 (amorphous) ~ IN (racemate) 48 C2H5 H CH2 C2H5 (amorphous) / \ (racemate) S

49 C2H5 H CH2 CH2OCH3 (amorphous) / \ (racemate) S

Le A 31 995-Foreign Countries Table 1 (continued) Ex. R R A Ar Z Physical data No. and stereochemical specifications 50 C2H5 H CH2 CH2SCH3 (amorphous) b~\ (racemate) S
51 C2H5 H CH2 CHCICH3 (amorphous) b/\ (racemate) S

52 C2H5 H CH2 CHC12 (amorphous) / \ (racemate) S
53 C2H5 H CH2 C2H4OCH3 (amorphous) b/\ (racemate) S
54 C2H5 H CH2 CH2CH(OCH3)2 (amorphous) b/\ (racemate) S
55 C2H5 H CH2 C2H4OCH3 (amorphous) S
\ DI (racemate) 56 C2H5 H CH2 CH2CH(OCH3)2 (amorphous) (racemate) O\S

57 C2H5 H CH2 C2H5 (amorphous) (racemate) OS

58 C2H5 H CH2 CH2OCH3 (amorphous) (racemate) O\S

59 C2H5 H CH2 CH2SCH3 (amorphous) (racemate) OS

Le A 31 995-Foreign Countries Table 1 (continued) Ex. R R A Ar Z Physical data No. and stereochemical specifications 60 C2H5 H CH2 S CHCICH3 (amorphous) (racemate) 61 C21-15 H CH2 S CHC12 (amorphous) (racemate) Le A 31 995-Foreign Countries Starting materials of the formula (II):

Example (11-1) H\N H\i CzHs H x HCI
~N N N /
I I I ~
H H H

A mixture of 2.9 g (14.5 mmol) of 1-ethyl-3-phenyl-propylamine hydrochloride (racemic), 1.22 g (14.5 mmol) of cyanoguanidine (dicyandiamide) and 30 ml of 1,2-dichloro-benzene is heated at 140 C to 150 C for 8 hours. The crystalline product which is obtained after cooling is isolated by filtration with suction.

This gives 3.6 g (87% of theory) of 1-(1-ethyl-3-phenyl-propyl)-biguanide hydrochloride (racemate).

The reaction can be carried out at the same temperature even without solvent -i.e. in the melt.

By the method of Example (11-1), it is also possible to prepare, for example, the compounds of the formula (II) and their hydrochlorides listed in Table 2 below.

IN R, (I') H,IN H1 H~N~N~N A~Ar Le A 31 995-Foreign Countries Table 2: Examples of compounds of the formula (II) -(hydrochlorides) Ex. No. R R2 A Ar Physical data and stereochemical specifications (11-2) C2H5 H 0 (racemate) (11-3) C2H5 H CH2 \ I OCH (racemate) (11-4) C2H5 H CH2 aSCH (racemate) (11-5) C2H5 H CH2 asocH3 (racemate) (11-6) C2H5 H CH2 "-aso2CH3 (racemate) (11-7) C2H5 H CH2 S

0/\ (racemate) (11-8) C2H5 H CH2 (racemate) S

(11-9) C2H5 H CH2 N

ci (racemate) Le A 31 995-Foreign Countries Table 2 (continued) Ex. No. R R A Ar Physical data and stereochemical specifications (11-10) C2H5 H CH2 (racemate) (II-11) C2H5 H CH2 N

(racemate) (II-12) C2H5 H CH2 (racemate) (11-13) C2H5 H 0 r-N'k(CH (amorph ous) 3)3 (hydrochloride) (racemate) Le A 31 995-Foreign Countries Starting materials of the formula (V):

Example (V-1) CZHS
H, N
I I
H

Step 1 CZHS
O /
I
\

A mixture of 19.3 g(0.134 mol) of ethyl propionyl acetate, 7.5 g(0.11 mol) of sodium methoxide, 60 ml of ethanol and 50 ml of 10% strength aqueous sodium hydroxide solution is initially charged at room temperature (approximately 20 C) and the reaction mixture is, after dropwise addition of 12.6 g(0.10 mol) of benzyl chloride, stirred at approximately 60 C for about 5 hours. The mixture is subsequently concentrated under water pump vacuum and the residue is stirred with 50 ml of 10% strength sodium hydroxide solution at approximately 60 C for 3 hours.

The pH is then adjusted to 4 using 10% strength aqueous hydrochloric acid, and the mixture is shaken with diethyl ether. The organic phase is dried with sodium sulphate and filtered. The filtrate is concentrated under water pump vacuum and the residue is purified by column chromatography (silica gel/ethyl acetate).

This gives 13.9 g (85% of theory) of 1-phenyl-pentan-3-one.
Step 2 HO N /
~

Le A 31 995-Foreign Countries A mixture of 13.9 g (86 mmol) of 1-phenyl-pentan-3-one, 8.9 g (128 mmol) of hydroxylamine hydrochloride and 10.1 g (128 mmol) of pyridine is stirred at approximately 75 C for 2 hours. After cooling, the mixture is shaken with water/ethyl acetate and the organic phase is separated off, dried with sodium sulphate and filtered. The solvent is carefully distilled off from the filtrate under water pump vacuum. The residue, which essentially contains the compound 1-phenyl-pentan-3-one oxime of the above formula, is employed for the next step without any further purification.

Step 3 H, N /
H ~

With stirring, 6.5 g(0.17 mol) of lithium aluminium hydride in 130 ml of tetrahydrofuran are added to a mixture of the product obtained in accordance with the description of step 2 and 130 ml of tetrahydrofuran, and the reaction mixture is stirred at approximately 60 C for 30 minutes. After cooling, the mixture is admixed with a solution of 1 g of sodium hydroxide in 30 ml of water, and the mixture is stirred at approximately 60 C for 30 minutes. After cooling, the mixture is filtered and the filtrate is concentrated under water pump vacuum. The residue is purified by column chromatography (silica gel, ethyl acetate).

This gives 6.3 g (45% of theory) of (R/S)-1-ethyl-3-phenyl-propylamine (racemate).

Le A 31 995-Foreign Countries Use Examples:

Example A
Pre-emergence-test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is watered with the preparation of active compound. The amount of water per unit area is advantageously kept constant. The concentration of active compound in the preparation is immaterial, only the application rate of active compound per unit area matters.

After three weeks, the degree of damage to the plants is scored visually in %
damage in comparison to the development of the untreated control.

The figures denote:

0% = no effect (like untreated control) 100 % = total destruction In this test, the compounds of Preparation Examples 1, 2, 12, 19, 21, 22, 29, 33, 41 and 45, for example, show strong activity against weeds, and some of them are Le A 31 995-Foreign Countries tolerated well by crop plants, such as, for example, maize, wheat and cotton (cf.
Table A).

In the tables below, "ai" means "active ingredient".

f } = .
CZ

Table A (continued) Active compound of Application rate Wheat Cotton Cheno- Solanum Veronica Viola Preparation Ex. No. (g of ai./ha) podium ~-' CH
F ~Ha HC N N ~
I I I ~.
N~NH2 N

(22) 500 0 0 100 100 100 100 Uh Table A: Pre-emergence test/greenhouse Active compound of Application rate Maize Cotton Alope- Digi- Abu- Galium Matri-Ex. No. (g of ai./ha) curus taria tilon caria ~
Preparation I o N N CZHS

co (1) 500 0 0 100 100 100 100 100 ~ ! = =
Table A (continued) CD
Active compound of Application rate Wheat Digi- Echi- Abu- Amaran- Da- Poly-Vero-Ex. No. (g of ai./ha) taria nochloa tilon thus tura gonum nica Preparation cD
.

)-II, ~N
HNN NH

0JH3 (12) 500 0 80 100 100 100 100 100 100 ~ $ . .
Table A (continued) OJ

Active compound of Application rate Wheat Digi- Echi- Abu- Amaran- Da- Poly-Vero- CD
Preparation Ex. No. (g of ai./ha) taria nochloa tilon thus tura gonum nica ...
HC

(X(LNLNH
s (19) 500 0 100 100 100 100 100 100 100 ~ j . .
Table A (continued) Active compound of Application rate Maize Abutilon Amaranthus Sinapis Preparation Ex. No. (g of ai./ha) CD
~o w ~ CF3 Y

~N CD
NN NH
2 ~
~
~
., ~.
cv ~

(2) 1000 20 80 100 100 {

'~ , . .
Table A (continued) Active compound of Application rate Alopecu Setaria Abutilon Amaranthus Galium Preparation Ex. No. (g of ai./ha) rus N ~N
H3c ~
N~N NH2 H 9t N

(21) 1000 100 90 90 95 80 N ~N
%\
N~N NH2 H
N

(22) 1000 90 70 100 95 100 y j . .
Table A (continued) Active compound of Application rate Alopecurus Setaria Abutilon Amaranthus Galium Preparation Ex. No. (g of ai./ha) CI / F w N N CH

N N H3C CH3 YI ~-' ~=

(29) 1000 70 - 80 80 80 cD

N"/ -N

/\ /~
H "I
N N NHZ

I

(41) 1000 90 100 100 100 95 Table A (continued) OJ
N r Active compound of Application rate Alope- Setaria Abuti- Ama- Galium Preparation Ex. No. (g of ai./ha) curus lon ranthus N N

N N N H 2 ~ H 3 I N

(45) 1000 80 95 100 100 100 Table A (continued) OJ

CD
Active compound of Application rate Alo- Setaria Abu- Ama- Sinapis Xan- w Preparation Ex. No. (g of ai./ha) pecurus tilon ranthus thium ~

H3c cH3 I

I CA
H N)"N:/~NH 2 s (33) 1000 100 100 90 100 100 90 Le A 31 995-Foreign Countries 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 which have a height of 5-15 cm are sprayed with the preparation of active compound such that the particular amounts of active compounds desired are applied per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 1000 1 of water/ha.

After three weeks, the degree of damage to the plants is scored visually in %
damage in comparison to the untreated control.

The figures denote:

0 % = no effect (like untreated control) 100 % = total destruction In this test, the compounds of Preparation Examples 1, 2, 4, 11, 12, 19, 22, 23, 24, 33, 41, 43, 44, 45 and 46, for example, show strong activity against weeds, and some of them are tolerated well by crop plants, such as, for example, maize and wheat (cf.
Table B).

Table B: Post-emergence test/greenhouse a Active compound of Application rate Wheat Echino- Abutilon Datura Ipomoea Veronica Y, Preparation Ex. No. (g of ai./ha) chloa ...
NH2 ~

F A
NN

(1) 250 0 80 100 100 100 100 i i . .
Table B (continued) OJ
Active compound of Application rate Maize Setaria Ama- Xanthium CD
Preparation Ex. No. (g of ai./ha) ranthus Yl CD
N ~N
H /\ %\

=~
...
cD

CI

(46) 1000 0 100 100 70 Table B (continued) OJ

>
Active compound of Application rate Wheat Echino- Setaria Ama- Ipo- Poly- Sola-Preparation Ex. No. (g of ai./ha) chloa ranthus moea gonum num ~
CFs CD
N ~N

/\ %\
HN N NHZ
CD
OX"H3 (12) 500 10 90 95 100 100 100 100 Table B (continued) CD
a Active compound of Application rate Wheat Echino- Setaria Ama- Ipo- Poly- Sola-Ex. No. (g of ai./ha) chloa ranthus moea gonum num Preparation :x3 H3C N

yLNNH2 s (19) 500 - 100 100 100 100 100 100 N IN

N" 'NNH

es (11) 500 10 80 95 100 100 100 100 4 n ' ON Table B (continued) Active compound of Application rate Wheat Echino- Setaria Ama- Ipo- Poly- Sola-o ~p Ex. No. (g of ai./ha) chloa ranthus moea gonum num Y, Preparation HC N ~ N
F
S
H N CH3 ti H

(24) 500 - 100 80 100 100 95 95 N::~ N
N'N NH

Hs (43) 500 10 - 90 100 100 100 100 Table B (continued) OJ

Active compound of Application rate Alope- Seta- Abu- Ama- Galium Xan- cv Preparation Ex. No. (g of ai./ha) curus ria tilon ranthus thium F CH~Hs HC N \ N
N'J"N NH

(22) 1000 - 80 70 95 80 70 ~ , .
Table B (continued) CD
Active compound of Application rate Alope- Seta- Abu- Ama- Galium Xan-Preparation Ex. No. (g of ai./ha) curus ria tilon ranthus thium cD
...

NJ N

H /\ /\ I

(41) 1000 80 100 100 100 100 100 Table B (continued) N r CD
t a ~O ~
Active compound of Application rate Alope- Seta- Abu- Ama- Galium Xan- Y, -4 Preparation Ex. No. (g of ai./ha) curus ria tilon ranthus thium ITI
....

NI kN

N N ~ NH
H
g (2) 1000 70 100 100 100 100 100 ~ F .
Table B (continued) CD
4 >
f W
Active compound of Application rate Alope- Seta- Abu- Ama- Galium Xan-Ex. No. (g of ai./ha) curus ria tilon ranthus thium , Preparation NH

\ I w (43) f , .
Table B (continued) Active compound of Application rate Alope- Seta- Abu- Ama- Galium Xan- a ~o w Preparation Ex. No. (g of ai./ha) curus ria tilon ranthus thium CFs N ~N
/\ ~

/ Hs ~ ~
CI ~ ~
(44) }

Table B (continued) Active compound of Application rate Alope- Seta- Abu- Ama- Galium Xan-Ex. No. (g of ai./ha) curus ria tilon ranthus thium Preparation CF3 v, N ~N

N) 'N NH

(45) Table B (continued) Active compound of Application rate Alope- Seta- Abu- Ama- Galium Xan-Ex. No. (g of ai./ha) curus ria tilon ranthus thium Preparation ~
N ~N (D.
HNI
N)"'N NH

(4) {

i F .
Table B (continued) OJ
N r CD

Active compound of Application rate Alope- Avena Cy- Se- Abu- Ama- Sina- Xan-Ex. No. (g of ai./ha) curus fatua perus taria tilon ranthus pis thium Preparation ~
NHz o ~
H3C N/\N
S F
H N H

(23) 1000 90 100 100 100 100 100 100 100 ~

F

N tN

N NH
I

s (33) 1000 80 100 90 100 100 100 100 -

Claims (10)

CLAIMS:
1. A substituted 2-amino-4-alkylamino-1,3,5-triazine of the general formula (I):

wherein:

R1 represents:
(i) unsubstituted or hydroxy-, cyano-, halogeno-or C1-C4-alkoxy-substituted alkyl having 2 to 4 carbon atoms, or (ii) unsubstituted or cyano-, halogeno- or C1-C4-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms;

R2 represents hydrogen, methyl or ethyl;
A represents oxygen or methylene;

Ar represents unsubstituted or substituted phenyl, unsubstituted or substituted naphthyl, or unsubstituted or substituted heterocyclyl, wherein the heterocyclyl is selected from the group consisting of:

furyl, benzofuryl, dihydrobenzofuryl, tetrahydrofuryl, thienyl, benzothienyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, quinolinyl, isoquinolinyl, pyridinyl and pyrimidinyl, and wherein the substituents are selected from the group consisting of:

(i) hydroxy, cyano, nitro or halogen, (ii) unsubstituted or hydroxy-, cyano-, halogeno-or C1-C4-alkoxy-substituted alkyl having 1 to 6 carbon atoms, (iii) unsubstituted or hydroxy-, cyano-, halogeno-or C1-C4-alkoxy-substituted alkoxy having 1 to 6 carbon atoms, (iv) unsubstituted or halogeno-substituted alkylcarbonyl having 1 to 6 carbon atoms in the alkyl group, (v) unsubstituted or halogeno-substituted alkoxycarbonyl having 1 to 6 carbon atoms in the alkyl group, (vi) unsubstituted or halogeno-substituted alkylthio having 1 to 6 carbon atoms in the alkyl group, (vii) unsubstituted or halogeno-substituted alkylsulfinyl having 1 to 6 carbon atoms in the alkyl group, (viii) unsubstituted or halogeno-substituted alkylsulfonyl having 1 to 6 carbon atoms in the alkyl group, (ix) unsubstituted or hydroxy-, cyano-, nitro-, halogeno-, C1-C4-alkyl-, C1-C4-halogenoalkyl-, C1-C4-alkoxy-or C1-C4-halogenoalkoxy-substituted phenyl, (x) unsubstituted or hydroxy-, cyano-, nitro-, halogeno-, C1-C4-alkyl-, C1-C4-halogenoalkyl-, C1-C4-alkoxy-or C1-C4-halogenoalkoxy-substituted phenoxy, (xi) unsubstituted or halogeno-substituted methylenedioxy, and (xii) unsubstituted or halogeno-substituted ethylenedioxy; and Z represents:
(i) hydrogen, or (ii) unsubstituted or hydroxy-, cyano-, nitro-, halogeno-, C1-C4-alkoxy-, C1-C4-alkylcarbonyl-, C1-C4-alkoxycarbonyl-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-or C1-C4-alkylsulphonyl-substituted alkyl having 1 to 6 carbon atoms, or (iii) unsubstituted or hydroxy-, cyano-, nitro-, halogeno-, C1-C4-alkoxy-, C1-C4-alkylcarbonyl-, C1-C4-alkoxycarbonyl-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-or C1-C4-alkylsulphonyl-substituted alkylcarbonyl having 1 to 6 carbon atoms in the alkyl group, or (iv) unsubstituted or hydroxy-, cyano-, nitro-, halogeno-, C1-C4-alkoxy-, C1-C4-alkylcarbonyl-, C1-C4-alkoxycarbonyl-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-or C1-C4-alkylsulphonyl-substituted alkoxycarbonyl having 1 to 6 carbon atoms in the alkyl group, or (v) unsubstituted or hydroxy-, cyano-, nitro-, halogeno-, C1-C4-alkoxy-, C1-C4-alkylcarbonyl-, C1-C4-alkoxycarbonyl-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-or C1-C4-alkylsulphonyl-substituted alkylsulphinyl having 1 to 6 carbon atoms in the alkyl group, or (vi) unsubstituted or hydroxy-, cyano-, nitro-, halogeno-, C1-C4-alkoxy-, C1-C4-alkylcarbonyl-, C1-C4-alkoxycarbonyl-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-or C1-C4-alkylsulphonyl-substituted alkylsulphonyl having 1 to 6 carbon atoms in the alkyl group, or (vii) unsubstituted or halogeno-substituted alkenyl having 2 to 6 carbon atoms, or (viii) unsubstituted or halogeno-substituted alkinyl having 2 to 6 carbon atoms.
2. A compound of the general formula (I) as claimed in claim 1, wherein:

R1 represents:

(i) unsubstituted or hydroxy-, cyano-, fluoro-, chloro-, methoxy- or ethoxy-substituted ethyl, n- or i-propyl, or n-, i-, s- or t-butyl, or (ii) unsubstituted or cyano-, fluoro-, chloro-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;

R2 represents hydrogen or methyl;
A represents oxygen or methylene;

Ar represents unsubstituted or substituted phenyl, unsubstituted or substituted naphthyl, or unsubstituted or substituted heterocyclyl, wherein the heterocyclyl is selected from the group consisting of:

furyl, benzofuryl, dihydrobenzofuryl, tetrahydrofuryl, thienyl, benzothienyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, quinolinyl, isoquinolinyl, pyridinyl and pyrimidinyl, and wherein the substituents are selected from the group consisting of:

(i) hydroxy, cyano, nitro, fluoro, chloro or bromo, (ii) unsubstituted or hydroxyl-, cyano-, fluoro-or chloro-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, or n-, i-, s- or t-butoxy, (iii) unsubstituted or fluoro- or chloro-substituted acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, or n- or i-propylsulphonyl, (iv) unsubstituted or hydroxy-, cyano-, nitro-, fluoro-, chloro-, bromo-, 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 (v) unsubstituted or fluoro- or chloro-substituted methylenedioxy or ethylenedioxy; and Z represents:
(i) hydrogen, or (ii) unsubstituted or hydroxy-, cyano-, nitro-, fluoro-, chloro-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, or n- or i-propylsulphonyl, or (iii) unsubstituted or fluoro-, chloro- or bromo-substituted ethenyl, propenyl, butenyl, ethinyl, propinyl, or butinyl.
3. A compound of the general formula (I) as claimed in claim 2, wherein R1 represents ethyl, n- or i-propyl, cyclopropyl or cyclobutyl;

R2 represents hydrogen or methyl;
A represents oxygen or methylene;

Ar represents unsubstituted or substituted phenyl, unsubstituted or substituted naphthyl, or unsubstituted or substituted heterocyclyl, wherein the heterocyclyl is selected from the group consisting of:

furyl, benzofuryl, dihydrobenzofuryl, tetrahydrofuryl, thienyl, benzothienyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, quinolinyl, isoquinolinyl, pyridinyl and pyrimidinyl, and wherein the substituents are selected from the group consisting of:

(i) fluoro or chloro, and (ii) unsubstituted or fluoro- or chloro-substituted methyl, ethyl, or n- or i-propyl; and Z represents unsubstituted or fluoro- or chloro-substituted methyl, ethyl, or n- or i-propyl.
4. A process for preparing a compound of the general formula (I) according to any one of claims 1 to 3, comprising:

(a) reacting, optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent, a substituted biguanide of the general formula (II) or an acid adduct thereof:

wherein R1, R2, A and Ar are as defined in any one of claims 1 to 3, with an alkoxycarbonyl compound of the general formula (III) :

wherein:

Z is as defined in any one of claims 1 to 3, and R' represents alkyl; or (b) reacting, optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent, a substituted triazine of the general formula (IV):

wherein:

R1, R2, A, Ar and Z are as defined in any one of claims 1 to 3, and X1 represents halogen or alkoxy, with ammonia; or (c) reacting, optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent, a substituted triazine of the general formula (V):

wherein:

Z is as defined in any one of claims 1 to 3, and X2 represents halogen or alkoxy, with a substituted alkylamine of the general formula (VI):

wherein R1, R2, A and Ar are as defined in any one of claims 1 to 3.
5. A herbicidal composition comprising at least one compound of the general formula (I) according to any one of claims 1 to 3, and an extender, a surfactant or a mixture thereof.
6. Use of a compound of the general formula (I) according to any one of claims 1 to 3, or a composition according to claim 5, for controlling undesirable vegetation.
7. A method for controlling weeds, wherein a compound of the general formula (I) according to any one of claims 1 to 3, or a composition according to claim 5, is allowed to act on weeds or their habitat.
8. A process for preparing a herbicidal composition comprising mixing a compound of the general formula (I) according to any one of claims 1 to 3, with an extender, a surfactant or a mixture thereof.
9. A substituted triazine of the general formula (IV) as defined in claim 4.
10. A substituted biguanide of the general formula (II) as defined in claim 4, or an acid adduct thereof.
CA002267928A 1996-10-10 1997-09-29 Substituted 2-amino-4-alkylamino-1,3,5-triazines as herbicides Expired - Fee Related CA2267928C (en)

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