EP1021441A1

EP1021441A1 - Substituted 2,4-diamino-1,3,5-triazine and their use as herbicides

Info

Publication number: EP1021441A1
Application number: EP98950080A
Authority: EP
Inventors: Hans-Jochem Riebel; Stefan Lehr; Uwe Stelzer; Markus Dollinger; Mark Wilhelm Drewes; Randy Allen Myers
Original assignee: Bayer AG
Current assignee: Bayer CropScience AG
Priority date: 1997-10-07
Filing date: 1998-09-24
Publication date: 2000-07-26
Also published as: CN1281450A; US6348435B1; KR20010024389A; WO1999018100A1; DE19744232A1; JP2001519348A; BR9812892A; AU9628098A; AU742963B2; CA2305806A1

Abstract

The invention relates to new substituted 2,4-diamino-1,3,5-triazines of formula (I) in which R1 is, for example, H or C¿1?-C6-alkyl, R?2¿ is, for example, H, C¿1?-C6-alkyl or -CO-R?6, R3¿ is, for example, C¿1?-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl or C3-C6-cycloalkyl, R?4¿ is, for example, H, C¿1?-C6-alkyl, or C3-C6-cycloalkyl, R?5¿ stands for one of the groups (a) or (b), in which R6 is C1-C6-alkyl, C1-C6-alkoxy or C2-C6-alkenyl, R?7 to R12¿ are, for example, H or certain organic radicals and Q stands for O or S. The invention also relates to a method and new intermediaries for the production of these compounds, and their use as herbicides.

Description

SUBSTITUTED 2, 4-DIAMINE0-1, 3, 5-TRIAZINE AND THEIR USE AS HERBICIDES

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

A number of substituted 2,4-diamino-triazines are already known from the (patent literature (cf. JP 63222166 - cited in Chem. Abstracts III: 97288w; cf. also US 3816419, US 3932167, EP 191496, EP 273328, EP 411153 / WO 90/09378) However, these compounds have so far not attained any particular importance.

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

R ^J

R "N ^' N (l)

.FT

R ^~ NNN 'IH

in which

R ^{1 represents} hydrogen or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C1-C4alkoxy,

R ^{2 represents} hydrogen, alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen or C1-C4alkoxy, or the group -CO-R ⁶ ,

R ³ for hydrogen, optionally substituted by cyano, hydroxy, halogen, C 1 -C4-alkoxy, -C-C4-alkylthio, C 1 -C4-alkylsulfinyl or C _] -C4-alkylsulfonyl-substituted alkyl having 1 to 6 carbon atoms, for each alkenyl or alkynyl optionally substituted by halogen or C 1 -C 4 -alkoxy each represents 2 to 6 carbon atoms, or represents cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or C 1 -C 4 -alkyl,

R ^{4 represents} hydrogen, alkyl having 1 to 6 carbon atoms optionally substituted by cyano, halogen or C _] -C4-alkoxy, or cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or C1-C4-alkyl,

R ^{5 represents} one of the groups below,

R ^{6 represents} hydrogen or alkyl, alkoxy, alkylamino or dialkylamino, each of which is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups or is optionally substituted by halogen, alkenyl having 2 to 6 carbon atoms,

R ⁷ for hydrogen, nitro, cyano, carbamoyl. Thiocarbamoyl, sulfamoyl,

Halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulfonyl or dialkylaminosulfonyl, each optionally substituted by cyano, halogen or C1-C4alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, for optionally by cyano, halogen or Cj-C ^ alkyl substituted cycloalkyl, or for each optionally substituted by nitro, cyano, carbamoyl, thiocarbamoyl, halogen, C1-C4-alkyl, C _j -C4-haloalkyl, C _] -C4-alkoxy or C1-C4-haloalkoxy Phenyl, phenoxy or phenylthio, R ⁸ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, bromine, for methyl substituted by cyano, halogen or C1-C4-alkoxy, for alkyl optionally substituted by cyano, halogen or C1-C4-alkoxy with 2 to 6 carbon atoms, for alkoxy, alkylthio, alkylsulfinyl, each optionally substituted by cyano, halogen or C1-C4alkoxy,

Alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulfonyl or dialkylaminosulfonyl each having 1 to 6 carbon atoms in the alkyl groups, for cycloalkyl optionally substituted by cyano, halogen or C1-C4alkyl, or for each optionally substituted by nitro, cyano, carbamoyl, thiocarbamoyl, halogen , -C-C4-alkyl, C] -C4-haloalkyl, -C-C4-alkoxy or Cj-C4-haloalkoxy substituted phenyl, phenoxy or phenylthio, and - in the event that R ⁹ is different from chlorine or methyl - also represents chlorine or methyl,

R ⁹ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine,

Bromine, for methyl substituted by cyano, halogen or C1-C4-alkoxy, for alkyl optionally substituted by cyano, halogen or Cj- - alkoxy having 2 to 6 carbon atoms, for alkoxy optionally substituted by cyano, halogen or C1-C4-alkoxy , Alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulfonyl or dialkylaminosulfonyl each having 1 to 6 carbon atoms in the alkyl groups, for cycloalkyl optionally substituted by cyano, halogen or C1-C4-alkyl, or -for each optionally by nitro, cyano , Carbamoyl, thiocarbamoyl, halogen, -CC4-alkyl, C] -C4-haloalkyl, C1-C4-alkoxy or -CC4-haloalkoxy substituted phenyl, phenoxy or phenylthio, and - in the event that R ^{8 is} chlorine or methyl is different - also represents chlorine or methyl,

R ¹⁰ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, for each optionally by cyano, halogen or C1-C4-

Alkoxy substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl,

Alkylcarbonyl, alkoxycarbonyl, alkylaminosulfonyl or dialkylaminosulfonyl each with 1 to 6 carbon atoms in the alkyl groups, for cycloalkyl optionally substituted by cyano, halogen or C1-C4-alkyl, or for each optionally nitro, cyano, carbamoyl, thiocarbamoyl, halogen, C1-C4-alkyl, C 1 -C 4- Haloalkyl, C] -C4-alkoxy or C1-C4-haloalkoxy-substituted phenyl, phenoxy or phenylthio,

R ¹¹ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulfonyl or dialkylaminosulfonyl, each optionally substituted by cyano, halogen or C1-C4alkoxy 1 to 6 carbon atoms in the alkyl groups, for cycloalkyl optionally substituted by cyano, halogen or Cj-G-alkyl, or for in each case optionally by nitro, cyano, carbamoyl, thiocarbamoyl, halogen, C1-C4-alkyl, Cι-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy-substituted phenyl, phenoxy or phenylthio,

R ¹² for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulfonyl or dialkylaminosulfonyl, each optionally substituted by cyano, halogen or C1-C4alkoxy 1 to 6 carbon atoms in the alkyl groups, for cycloalkyl optionally substituted by cyano, halogen or C1-C4-alkyl, or for in each case optionally by nitro, cyano, carbamoyl, thiocarbamoyl, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, Cj-C4-alkoxy or C1-C4-haloalkoxy substituted phenyl, phenoxy or phenylthio, and

Q represents oxygen or sulfur.

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

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

in which

R ¹ , R ² , R ⁴ and R ^{5 have} the meaning given above,

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

with alkoxycarbonyl compounds of the general formula (III)

R ³

.7 (HO

OR

in which

R ^{3 has} the meaning given above and

R represents alkyl,

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

or if you

(b) for the preparation of compounds of the formula (I) in which R ^{2 is} from

Hydrogen is different

2,4-diamino-l, 3,5-triazines of the general formula (Ia) R ^J

R ^{^} N ^ N

(la)

H

R ^J NNN

MR

in which

R ¹ , R ³ , R ⁴ and R ^{5 have} the meaning given above,

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

XR ² (IV)

in which

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

X represents halogen, alkoxy, -O-CO-R ⁶ or -O-SO ₂ -OR ² ,

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

The new substituted 2,4-diamino-1,3,5-triazines of the general formula (I) are notable for their strong and selective herbicidal activity. To a certain extent, the compounds of the general formula (I) also show fungicidal and insecticidal activity.

The compounds of the general formula (I) according to the invention optionally contain an asymmetrically substituted carbon atom and can then be in various enantiomeric (R- and S -configured forms) or diastereoisomers

Shapes are available. The invention relates both to the various 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 - in each case in connection with heteroatoms, such as in alkoxy or alkylthio - are each straight-chain or branched.

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

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

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

R ² for hydrogen, - for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or for the grouping -CO- R ⁶ stands,

R ³ for hydrogen, each optionally by cyano, hydroxyl, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i- Propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted methyl,

Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for each optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy, propenyl, Butenyl, ethynyl, propynyl or butynyl, or represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which are each optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl,

R ⁴ for hydrogen, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or for in each case optionally by cyano, Fluorine, chlorine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,

R ^{5 represents} one of the groups below,

R ⁶ for hydrogen or for each optionally by cyano, fluorine, chlorine,

Bromine, methoxy, ethoxy, n- or i-propoxy 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, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, or if necessary by fluorine, chlorine and / or bromine-substituted ethenyl,

Propenyl or butenyl,

R ⁷ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, n-, i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy -, s- or t-

Butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t- Butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl or diethylaminosulfonyl, each for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, or for each optionally by nitro, cyano, carbamoyl, thiocarbamoyl, 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 , Phenoxy or phenylthio,

R ⁸ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, bromine, for methyl substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, for each ethyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , n- or i-propyl, n-, i-, s- or t-butyl, for methoxy, ethoxy, n- or i-propoxy, n-, i, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy -, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,

Methylsulfinyl, ethylsulfmyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl or diethylaminosulfonyl, each optionally substituted by cyano, fluorine, ethyl, chlorobutyl, cyclyl, methyl, cyclobutyl , Cyclopentyl or cyclohexyl, or for each optionally by nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoro- methyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy or phenylthio, and - in the event that R ^{9 is} chlorine or methyl is different - also represents chlorine or methyl.

Bromine, for methyl substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for in each case optionally by cyano, fluorine, chlorine, methoxy or

Ethoxy substituted ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for each optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methyl - sulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl or diethylaminosulfonyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl or methyl Cyclobutyl, cyclopentyl or cyclohexyl, or for each optionally by nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluor - Methyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy or phenylthio, and - in the event that R ⁸ of Chlorine or methyl is different - also stands for chlorine or methyl.

R ¹⁰ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine,

Chlorine, bromine, each for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i, optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy -Propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-. s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-

Butyroyl, methoxycarbonyl, ethoxycarbonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl or diethylaminosulfonyl, for each cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, or for each optionally by nitro, cyloyl carbam 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, phenoxy or phenylthio,

R ¹¹ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, chlorine, bromine, for each optionally by cyano, fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy , Methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, Methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl or diethylaminosulfonyl, for each cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, or for each optionally by nitro, cyano, carbamoyl, thiocarbamoyl, 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, phenoxy or phenylthio,

R ¹² for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine,

Chlorine, bromine, each for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i, optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy Propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, Acetyl, propionyl, n- or i-

Butyroyl, methoxycarbonyl, ethoxycarbonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl or diethylaminosulfonyl, for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, or for each optionally by nitro, cyano, carbano , Thiocarbamoyl, 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, phenoxy or phenylthio, and

Q represents oxygen or sulfur. The invention relates in particular to compounds of the formula (I) in which

R ^{1 represents} hydrogen,

R ^{2 represents} hydrogen or the grouping -CO-R ⁶ ,

R ³ for hydrogen, for each methyl, ethyl, n- or i-propyl optionally substituted by cyano, hydroxy, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, for each optionally substituted by fluorine, Chlorine or methoxy substituted ethenyl or propenyl, or represents cyclopropyl optionally substituted by cyano, fluorine, chlorine or methyl,

R ⁴ for each methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or for optionally by

Cyano, fluorine, chlorine or methyl substituted cyclopropyl,

R ^{5 represents} one of the groups below,

R ^{6 represents} hydrogen or methyl, ethyl, n- or i-propyl, methoxy or ethoxy which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or ethenyl or propenyl which is optionally substituted by fluorine and / or chlorine stands,

R ⁷ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine,

Chlorine, bromine, for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , Methylsulfinyl, Ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for cyclopropyl optionally substituted by cyano, fluorine, chlorine or methyl, or for each optionally substituted by nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, tri fluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy substituted

Phenyl, phenoxy or phenylthio,

R ⁸ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, bromine, for ethyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, n- or i-propyl, each optionally using

Cyano, fluorine, chlorine, methoxy or ethoxy substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for optionally cyclopropyl substituted by cyano, fluorine, chlorine or methyl, or for each optionally by

Nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy or phenylthio, and - in the event that R ⁹ is different from chlorine or methyl - also represents chlorine or methyl,

R ⁹ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, bromine, for ethyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, n- or i-propyl, for each optionally substituted by cyano, fluorine, Chlorine, bromine, methoxy or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,

Methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for cyclopropyl optionally substituted by cyano, fluorine, chlorine or methyl, or for each optionally substituted by nitro, cyano, carbamoyl, thiocarbamoyl, 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, phenoxy or phenylthio, and - stands for the case that R ⁸ is different from chlorine or methyl - also represents chlorine or methyl,

R ¹⁰ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, methoxy or ethoxy substituted by cyano, fluorine, chlorine, methoxy or ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for cyclopropyl optionally substituted by cyano, fluorine, chlorine or methyl, or for each if necessary by

Nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy or phenylthio,

R ¹ * for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine,

Chlorine, bromine, for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , Methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for optionally by cyano, fluorine, chlorine or

Methyl-substituted cyclopropyl, or represents in each case optionally substituted by nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy, phenyl, phenoxy or phenylthio,

R ¹² for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, methoxy or ethoxy substituted by cyano, fluorine, chlorine, methoxy or ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for cyclopropyl optionally substituted by cyano, fluorine, chlorine or methyl, or for each if necessary by Nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy or phenylthio, and

Q represents oxygen or sulfur.

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

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

Group 1

R ³ has, for example, the meanings given below:

Hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyanomethyl, 1-cyano-ethyl, 2-cyano-ethyl, 1-cyano-1-methyl-ethyl, Hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, chlorofluoromethyl, chlorobromomethyl, chlorodifluoromethyl, fluorodichloromethyl, bromodifluoromethyl, trichloromethyl, 1-fluoro-ethyl, 2-fluoro- ethyl, 1-chloro-ethyl, 2-chloro-ethyl, 1-chloro-1-fluoro-ethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1 -Fluor- 1-methyl- ethyl, 2-fluoro-1-methyl-ethyl, 1-chloro-1-methyl-ethyl, 1- Fluoro-1-methyl-propyl, 1-chloro-1-ethyl-propyl, 1-fluoro-1-ethyl-propyl, 1-chloro-1-ethyl-propyl, 1-fluoro-2-methyl-propyl, l- Chloro-2-methyl-propyl, 1-chloro-propyl, 2-chloro-propyl, 3-chloro-propyl, 1-chloro-1-methyl-ethyl, 2-chloro-1-methyl-ethyl, 1, 1- Difluoro-ethyl, 1,2-difluoro-ethyl, 1,1-dichloro-ethyl, 2,2,2-trifluro-ethyl, 1,2,2,2-tetra-fluoro-ethyl, perfluoroethyl, 1, 1- Difluoropropyl, 1, 1-dichloropropyl, perfluoropropyl, 1-

Fluorobutyl, 1-chlorobutyl, perfluoropentyl, perfluorohexyl, methoxymethyl, 1, 1-dimethoxy-methyl, 1-methoxyethyl, 2-methoxy-ethyl, 1,1-dimethoxy-ethyl, ethoxymethyl, 1- Ethoxyethyl, 2-ethoxy-ethyl, 2-methoxy-1-methyl-ethyl, 2-methoxy-1-ethyl-ethyl, 2-ethoxy-1-methyl-ethyl, 2-ethoxy-1-ethyl-ethyl, methylthiomethyl, Ethylthiomethyl, 1-methylthio-ethyl, 2-methylthioethyl, 1-ethylthio-ethyl, 2-ethylthioethyl, methylsulfinylmethyl, ethylsulfinylmethyl, methylsulfonylmethyl, ethylsulfonylmethyl, vinyl, 1-chloro-vinyl, 2-chloro-vinyl, 1 - Fluorovinyl, 2-fluorovinyl, 1-bromovinyl, 2-bromovinyl, 1,2-dichlorovinyl, 1,2-dibromovinyl, 1,2-difluorovinyl, 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, l-chloro-2-propenyl, l-fluoro-2-propenyl, l-bromo-2-propenyl, 1,2-dichloro-l-propenyl, 1,2-dibromo-l-propenyl, 1,2-difluoro-l-propenyl, 1, 1-dichloro-2-propenyl, l, l-dibromo-2-propenyl, 1, 1-difluoro-2-propenyl, 1, 1,3,3,3- Pentafluoro-2-propenyl, 2-buten-1-yl, 2-buten-2-yl, 3-chloro-2-butenyl, 3-bromo-2-butenyl, 3,3,3-trifluoro-2-butenyl, Ethynyl, 2-chloro-ethynyl, 2-bromo-ethynyl, 1-

Propynyl, 2-propynyl, 3,3,3-trifluoro-l-propynyl, cyclopropyl, 2-fluoro-cyclopropyl, 2-chloro-cyclopropyl, 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl.

Group 2

R ³ has, for example, the meanings given above in Group 1. Group 3

R ³ has, for example, the meanings given above in Group 1.

Group 4

R ³ has, for example, the meanings given above in Group 1.

Group 5

R ³ has, for example, the meanings given above in Group 1. - left

Group 6

R ³ has, for example, the meanings given above in Group 1.

Group 7

R ³ has, for example, the meanings given above in Group 1.

Group 8

R ³ has, for example, the meanings given above in Group 1. Group 9

R ³ has, for example, the meanings given above in Group 1.

Group 10

R ³ has, for example, the meanings given above in Group 1.

Group 11

R ³ has, for example, the meanings given above in Group 1. Group 12

R ³ has, for example, the meanings given above in Group 1.

Group 13

R ³ has, for example, the meanings given above in Group 1.

Group 14

R ³ has, for example, the meanings given above in Group 1. Group 15

R ³ has, for example, the meanings given above in Group 1.

Group 16

R ³ has, for example, the meanings given above in Group 1.

Group 17

R ³ has, for example, the meanings given above in Group 1. Group 18

R ³ has, for example, the meanings given above in Group 1.

Group 19

R ³ has, for example, the meanings given above in Group 1.

Group 20

R ³ has, for example, the meanings given above in Group 1. Group 21

R ³ has, for example, the meanings given above in Group 1.

Group 22

R ³ has, for example, the meanings given above in Group 1.

Group 23

R ³ has, for example, the meanings given above in Group 1. Group 24

R ³ has, for example, the meanings given above in Group 1.

Group 25

R ³ has, for example, the meanings given above in Group 1.

Group 26

R ³ has, for example, the meanings given above in Group 1. Group 27

R ³ has, for example, the meanings given above in Group 1.

Group 28

R ³ has, for example, the meanings given above in Group 1.

Group 29

R ³ has, for example, the meanings given above in Group 1. Group 30

R ³ has, for example, the meanings given above in Group 1.

Group 31

R ³ has, for example, the meanings given above in Group 1.

Group 32

R ³ has, for example, the meanings given above in Group 1. Group 33

R ³ has, for example, the meanings given above in Group 1.

Group 34

R ³ has, for example, the meanings given above in Group 1.

Group 35

R ³ has, for example, the meanings given above in Group 1. Group 36

R ³ has, for example, the meanings given above in Group 1.

Group 37

R ³ has, for example, the meanings given above in Group 1.

Group 38

R ³ has, for example, the meanings given above in Group 1. Group 39

R ³ has, for example, the meanings given above in Group 1.

Group 40

R ³ has, for example, the meanings given above in Group 1.

Group 41

R ³ has, for example, the meanings given above in Group 1. Group 42

R ³ has, for example, the meanings given above in Group 1.

Group 43

R ³ has, for example, the meanings given above in Group 1.

Group 44

R ³ has, for example, the meanings given above in Group 1. Group 45

R ³ has, for example, the meanings given above in Group 1.

Group 46

R ³ has, for example, the meanings given above in Group 1.

Group 47

R ³ has, for example, the meanings given above in Group 1. Group 48

R ³ has, for example, the meanings given above in Group 1.

Group 49

R ³ has, for example, the meanings given above in Group 1.

Group 50

R ³ has, for example, the meanings given above in Group 1 Group 51

R ³ has, for example, the meanings given above in Group 1

Group 52

R ³ has, for example, the meanings given above in Group 1

Group 53

R ³ has, for example, the meanings given above in Group 1 Group 54

R ³ has, for example, the meanings given above in Group 1.

Group 55

R ³ has, for example, the meanings given above in Group 1.

Group 56

R ³ has, for example, the meanings given above in Group 1. Group 57

R ³ has, for example, the meanings given above in Group 1.

Group 58

R ³ has, for example, the meanings given above in Group 1.

Group 59

R ³ has, for example, the meanings given above in Group 1. Group 60

R ³ has, for example, the meanings given above in Group 1.

Group 61

R ³ has, for example, the meanings given above in Group 1.

Group 62

R ³ has, for example, the meanings given above in Group 1. Group 63

R ³ has, for example, the meanings given above in Group 1.

Group 64

R ³ has, for example, the meanings given above in Group 1.

Group 65

R ³ has, for example, the meanings given above in Group 1.

Group 66

R ³ has, for example, the meanings given above in Group 1.

Group 67

R ³ has, for example, the meanings given above in Group 1.

Group 68

R ³ has, for example, the meanings given above in Group 1. Group 69

R ³ has, for example, the meanings given above in Group 1.

Group 70

R ³ has, for example, the meanings given above in Group 1.

Group 71

R ³ has, for example, the meanings given above in Group 1. Group 72

R ³ has, for example, the meanings given above in Group 1.

Group 73

R ³ has, for example, the meanings given above in Group 1.

Group 74

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

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

Group 76

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

Group 77

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

Group 78

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

Group 79

R3 has, for example, the meanings given above in Group 1.

Group 80

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

Group 81

R- has, for example, the meanings given above in Group 1. Group 82

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

Group 83

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

Group 84

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

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

Group 86

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

Group 87

R ^ has, for example, the meanings given above in Group 1. Group 88

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

Group 89

R3 has, for example, the meanings given above in Group 1.

Group 90

R ^ has, for example, the meanings given above in Group 1. Group 91

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

Group 92

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

Group 93

R- has, for example, the meanings given above in Group 1. Group 94

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

Group 95

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

Group 96

R ^ has, for example, the meanings given above in Group 1. Group 97

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

Group 98

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

Group 99

R ^ has, for example, the meanings given above in Group 1. Group 100

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

Group 101

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

Group 102

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

Group 103

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

Group 104

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

Group 105

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

Group 106

R- has, for example, the meanings given above in Group 1. Group 107

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

Group 108

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

Group 109

R ^ has, for example, the meanings given above in Group 1. Group 110

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

Group 111

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

Group 112

R ^ has, for example, the meanings given above in Group 1. Group 113

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

Group 114

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

Group 115

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

Group 116

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

Group 117

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

Group 118

R has, for example, the meanings given above in Group 1. Group 119

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

Group 120

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

Group 121

R ^ has, for example, the meanings given above in Group 1. Group 122

R3 has, for example, the meanings given above in Group 1.

Group 123

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

Group 124

R- ^> has, for example, the meanings given above in Group 1. Group 125

R3 has, for example, the meanings given above in Group 1.

Group 126

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

Group 127

R has, for example, the meanings given above in Group 1. Group 128

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

Group 129

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

Group 130

R ^ has, for example, the meanings given above in Group 1. Group 131

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

Group 132

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

Group 133

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

Group 134

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

If, for example, l- (l-thien-3-yl-propyl) biguanide and methyl trifluoroacetate are used as starting materials, the course of the reaction in process (a) according to the invention can be outlined using the following formula:

If, for example, 2-amino-4- (l-methyl-2,2,2-trifluoro-ethyl) -6- (l-thien-

2-yl-ethylamino) -l, 3,5-triazine and acetyl chloride as starting materials, the course of the reaction in process (b) according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the substituted biguanides to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I). In the formula (II), R ¹ , R ² , R ⁴ and R ⁵ preferably or in particular have those meanings which are preferred or particularly preferred for R ¹ already in connection with the description of the compounds of the formula (I) according to the invention , R ² , R ⁴ and R ^{5 were} given. Suitable acid adducts of compounds of the formula (II) are their addition products with protonic acids, such as, for example, with hydrogen chloride (hydrogen chloride), hydrogen bromide (hydrogen bromide), sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.

The starting materials of the general formula (II) are, with the exception of 1- (2-furyl-methyl) -biguanide (-hydrochloride) and 1-- (2-thienyl-methyl) -biguanide (-hydrochloride) - cf. J. Am. Chem. Soc. 81 (1959), 3728-3736 and US 2961377 - not yet known from the literature; with the exception of l- (2-furyl-methyl) -biguanide (-hydrochloride) and l- (2-thienyl-methyl) -biguanide (-hydrochloride) as new substances

Subject of the present application.

The substituted biguanides of the general formula (II) are obtained if amines of the general formula (V)

RT ^ ⁵ (V)

H

in which

R ⁴ and R ^{5 have} the meaning given above,

- and / or acid adducts of compounds of the general formula (V), such as, for example, the hydrochlorides - with cyanoguanidines of the general formula (VI)

H .

N

FT II <N

(VI)

N N

R ¹ H

in which

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

optionally in the presence of a reaction auxiliary, e.g. Hydrogen chloride, and optionally in the presence of a diluent, e.g. n-Decane, toluene or 1,2-dichlorobenzene, at temperatures between 100 ° C and 200 ° C (see. The preparation examples).

The compounds of the formulas (V) and (VI) are known and / or can be prepared by processes known per se.

Formula (III) provides a general definition of the alkoxycarbonyl compounds to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I). In the formula (III), R ³ preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R ³ ; R preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl.

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

Formula (Ia) provides a general definition of the 2,4-diamino-1,3,5-triazines to be used as starting materials in process (b) according to the invention for the preparation of compounds of the formula (I). In formula (Ia), R ¹ , R ³ , R ⁴ and R ^{5 have} preferably or in particular those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R ¹ , R ³ , R ⁴ and R ⁵ .

The starting materials of the general formula (Ia) are also new compounds

Subject of the present application; they can be prepared according to process (a).

Formula (IV) provides a general definition of the alkylating or acylating agents which are further to be used as starting materials in process (b) according to the invention for the preparation of compounds of the formula (I). In formula (IV), R ² preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R ² ; X preferably represents fluorine, chlorine, bromine, iodine, methoxy, ethoxy, acetyl, methoxysulfonyloxy or ethoxysulfonyloxy.

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

The processes according to the invention for the preparation of the compounds of the formula (I) are optionally carried out using a reaction auxiliary. The usual inorganic or organic bases or acid acceptors are suitable as reaction aids for processes (a) and (b). These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as, for example

Sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium - or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methanolate, ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclo- hexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, l, 4-diazabicyclo [2,2,2] octane (DABCO), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), or 1,8-diazabicyclo [5,4,0 ] -undec-7-en

(DBU).

Possible diluents for carrying out processes (a) and (b) according to the invention are inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as methyl isopropyl ketone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile or butyrotitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; Alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The reaction temperatures can be varied within a substantial range when carrying out processes (a) and (b) according to the invention. In general, temperatures between 0 ° C and 180 ° C, preferably between

10 ° C and 150 ° C.

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

0, 1 bar and 10 bar - to be carried out. To carry out the processes according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).

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

The active compounds according to the invention can e.g. can be used in the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca,

Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datüra, Viola, Galeopsis, Papaver, Centaurea, Trifolaxac, Ranif.

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

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

Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Sci us, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Phalaris, Aegilops

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

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

The compounds are suitable, depending on the concentration, for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on decorative and sports turf and pasture land and for selective purposes Weed control can be used in annual crops

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

Cultures both pre-emergence and post-emergence

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, loose powders, granules, suspension-emulsion concentrates, impregnated with active ingredients

Natural and synthetic substances as well as very fine encapsulation in polymeric substances

These formulations are prepared in a known manner, e.g. B by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents

Emulsifiers and / or dispersants and / or foaming agents If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. Liquid solvents are essentially aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or Methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, as well as water

Solid carrier materials that come into question are, for example, ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillomite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, and solid carrier materials for granules Question e.g. broken and fractionated natural rocks such as calcite, marble,

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

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalms and lecithins and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils

Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizine, azo and metal phthalocyanine dyes substances and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.

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

The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amidochlor, amidosulfüron, asulam, atrazine, azimsulfüron, benazolin, benfuresate, bensulfon (-methyl) , Bentazon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butylate,

Cafenstrole, Carbetamide, Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (- ethyl), Chlornitrofen, Chlor sulfüron, Chlortoluron, Cinmethylin, Cinosulfüron, Clethodim, Clodinafop (-propargyl), Clomazone, Clopyralid, Clopyrasethyluronamonamylamyluronamuron , Cyanazines, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Difenzoquat, Diflufenican , Dimefüron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, EPTC, Esprocarb, Ethalfluralin, Ethametsulfüron (-methyl), Ethofümesate, Ethoxyfen, Flobropanidethyl, Fenox (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulfüron, Fluazifop (-butyl), Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), flupoxam, flupropacil, flurenol, fluridone, fluroxypyr, flurprimidol, flurtamone, F omesafen, glufosinate (-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop (-ethoxyethyl), hexazinones, imazamethabenz (- methyl), imazamethapyr, imazamox, imazapyr, imazaquin, imazethapyr, imazosulfuron, isalinoxin Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfüron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfüron, Norflurazon Orbencarb, Oriparfluid, Oxyzalin, Oxyzalin, Oxyzalin, Oxyzalin , Pretilachlor, Primisulfüron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propyz- amide, Prosulfocarb, Prosulfüron, Pyrazolate, Pyrazosulfüron (-ethyl), Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobacin, Quinofacin, Quoxacin, Quacin, (Quacin), Quinacin, (- ethyl), Quizalofop (-p-tefüryl), Rimsulfüron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazafluoramide , Thidiazimin, Thifen-sulf ron (-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfüron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifluralin and Triflusulfüron.

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

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.

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

The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha. The preparation and use of the active compounds according to the invention can be seen from the examples below.

MANUFACTURING EXAMPLES:

example 1

(Method (a))

2.4 g (44 mmol) of sodium methylate are stirred with a mixture of 10.0 g (40 mmol) of l- (l-thien-2-yl-ethyl) -biguanide hydrochloride, 4.5 g (40 mmol) Methyl propionate and 80 ml of methanol are added and the reaction mixture is stirred at room temperature (about 20.degree. C.) for 15 hours. The mixture is then diluted to about twice the volume with diethyl ether, the organic phase is washed twice with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.

3.2 g (32% of theory) of 2-amino-4-ethyl-6- (l-thien-2-yl-ethylamino) - 1,3,5-triazine are obtained as an amorphous mass.

Example 2

(Method (b)) A mixture of 4.0 g (16 mmol) of 2-amino-4-ethyl-6- (l-thio-2-yl-ethylamino) - 1,3,5-triazine and 35 ml of acetic anhydride is at 120 ° for 2 hours C to 130 ° C stirred After cooling to room temperature, the mixture is diluted with 100 ml of water and the mixture is stirred for one hour. The product which has crystallized is then isolated by suction

2.1 g (45% of theory) of 2-acetylamino-4-ethyl-6- (l-thien-2-yl-ethylamino) -l, 3,5-triazine of melting point 153 ° C. are obtained

Analogous to preparation examples 1 and 2 and in accordance with the general

Description of the production processes according to the invention can also be used, for example, to prepare the compounds of the formula (I) listed in Table 1 below

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

Table 1: (continued)

O 99/18100

77

Table 1: (continued)

Starting materials of the formula (Dp:

Example (11-11

60 g of 33% aqueous hydrochloric acid are added to 63.5 g (0.50 mol) of l- (thien-2-yl) ethylamine and 100 ml of methanol and the mixture is concentrated in a water jet vacuum. After adding toluene to the residue, the mixture is concentrated again. 42 g (0.50 mol) of cyanoguanidine are added to the remaining residue and the mixture is held (as a melt) at 150 ° C. to 160 ° C. for 3 hours. When it cools down, the product solidifies like a glass.

122.5 g (99% of theory) of l- (l-thien-2-yl-ethyl) -biguanide hydrochloride are obtained.

Analogously to Example (II-1), 1- (l-thien-2-yl-propyl) -biguanide hydrochloride (II-2) is also obtained, likewise as a glass-like mass; further also

l- (l-thien-3-yl-ethyl) biguanide hydrochloride (II-3) and

1 - [1 - (3-methylthien-2-yl) ethyl] biguanide hydrochloride (II-4),

each as a glassy mass. Preproducts of formula (V):

Example (V-l)

step 1

150 ml of formic acid are added dropwise at 140 ° C. to 160 ° C. while stirring to a mixture of 100 g (0.79 mol) of 2-acetylthiophene and 300 ml of formamide, and the reaction mixture is stirred at 160 ° C. for 2 hours. After cooling to room temperature, the mixture is diluted to about twice the volume with toluene, washed twice with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.

78 g (64% of theory) of N- (l-thien-2-yl-ethyl) -formamide are obtained as an amorphous residue.

Level 2

A mixture of 75 g (0.48 mol) of N- (l-thien-2-yl-ethyl) -formamide, 120 ml of conc. Hydrochloric acid and 50 ml of water are heated under reflux for 3 hours and then concentrated in a water jet vacuum. The residue is shaken with water / methylene chloride, the aqueous phase is made alkaline with 2N sodium hydroxide solution and shaken with toluene. The toluene phase is dried with sodium sulfate and filtered. The filtrate is worked up by distillation under reduced pressure.

24.8 g (41% of theory) of 1 - (thien-2-yl) ethylamine with a boiling point of 40 ° C. at 0.8 mbar are obtained.

Analogously to example (VI), 1 - (thien-2-yl) propylamine (V-2) with a boiling point of 52 ° C. at 0.7 mbar is also obtained.

Examples of use:

Example A

Pre-emergence test

Solvent 5 parts by weight of acetone

Emulsifier 1 part by weight of alkylaryl polyglycol ether

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

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active compound preparation, so that the desired amounts of active compound are applied per unit area. The concentration of the spray broth is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha become

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

Mean it

0% = no effect (like untreated control)

100% = total annihilation

In this test, for example, the compounds according to Preparation Examples 15 and 22 show strong tolerance to crop plants, such as maize, with very good tolerability

Effect against weeds

"A ι" material ("active ingredient") Table A: Pre-emergence test / greenhouse

Active ingredient according to expenditure Corn Setaria Amaran- Galium Sinapis

Manufacturing example no. quantity (g ai./ha) thus

(15) 1000 90 100 100

(22) 1000 100 95 100 100

Example B

Post emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

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

Concentration.

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

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

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

It means:

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

In this test, for example, the compounds according to Preparation Example 1, 2, 5, 6, 11, 13, 14, 15, 16, 18, 20, 21, 22 and 24 show strong activity against crop plants such as maize, some of which are well tolerated Weeds. Table B: Post emergence test / greenhouse

Active ingredient according to expenditure Corn Setaria Abutilon Amaran- Sinapis Manufacturing example no. quantity (g ai./ha) thus

0) 1000 30 100 100 100

(2) 1000 90 100 100 100

Table B (continued)

(11) 1000 30 100 100 100 100

(14) 1000 30 100 100 100 100

Table B (continued)

Active ingredient according to expenditure - Corn Setaria Abutilon Amaran- Sinapis Manufacturing example no. quantity (g ai./ha) ^thus

(15) 1000 100 100 100 100

(16) 1000 10 100 100 100 100

Table B (continued)

(18) 1000 20 100 100 100 100

(20) 1000 100 100 100 100

Table B (continued)

(21) 1000 100 100 100 100

Table B (continued)

Active ingredient according to expenditureSetaria Abutilon Amaran- Sinapis Manufacturing example no. quantity (g ai./ha) thus

(22) 1000 100 100 100 100

Table B (continued)

Active ingredient according to expenditure - Corn Setaria Abu- Amaran- Sinapis Xan- Produktionsb sp. -No. quantity (g ai./ha) ^{tilon thus thium}

(6) 1000 100 100 100

(13) 1000 10 100 100 100 80

Table B (continued)

Active ingredient according to expenditureSetaria Amaran- Sinapis Xan- Manufacturing example no. quantity (g ai./ha) thus thium

(24) 1000 100 100 100 100

Claims

claims

1. Substituted 2,4-diamino-1, 3, 5-triazines of the general formula (I),

in which

R ^{1 represents} hydrogen or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C 4 -C 4 -alkoxy,

R ³ for hydrogen, for optionally substituted by cyano, hydroxy, halogen, C1-C4-alkoxy, C1-C4-alkylthio, -C -C ₄ -alkylsulfinyl or C1-C4- alkylsulfonyl-substituted alkyl having 1 to 6 carbon atoms, each optionally by Halogen or C1-C4-alkoxy-substituted alkenyl or alkynyl each having 2 to 6 carbon atoms, or cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or C 1 -C 4 -alkyl,

R ⁴ for hydrogen, for optionally by cyano, halogen or Ci -C4-

Alkoxy substituted alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or C 1 -C 4 -alkyl, R ^{5 represents} one of the groups below,

R ^{6 represents} hydrogen or alkyl, alkoxy, alkylamino or dialkylamino, each of which is optionally substituted by cyano, halogen or C1-C4-alkoxy, each having 1 to 6 carbon atoms in the alkyl groups or is optionally substituted by halogen-substituted alkenyl having 2 to 6 carbon atoms ,

R ⁷ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulfonyl or dialkylaminosulfonyl, each optionally substituted by cyano, halogen or Cj-C4-alkoxy 1 to 6 carbon atoms in the

Alkyl groups, for cycloalkyl optionally substituted by cyano, halogen or C ₁ -C 4 alkyl, or for each optionally substituted by nitro, cyano, carbamoyl, thiocarbamoyl, halogen, C ₁ -C 4 alkyl, C ₁ -C 4 haloalkyl, C ₁ -C 4 Alkoxy or Cj-C4 -haloalkoxy-substituted phenyl, phenoxy or phenylthio,

R ⁸ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, bromine, for methyl substituted by cyano, halogen or Cj-C4-alkoxy, for alkyl optionally substituted by cyano, halogen or Ci - C4-alkoxy with 2 to 6 carbon atoms, each for alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulfonyl or dialkylaminosulfonyl, each optionally substituted by cyano, halogen or C 1 -C 6 -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, for optionally substituted by cyano, halogen or C1 -C4 alkyl substituted Cycloalkyl, or represents in each case optionally substituted by nitro, cyano, carbamoyl, thiocarbamoyl, halogen, C1-C4-alkyl, C] -C4-haloalkyl, C1-C4-alkoxy or Cj-C4-haloalkoxy substituted phenyl, phenoxy or phenylthio , and - in the event that R ⁹ is different from chlorine or methyl - also represents chlorine or methyl,

R ⁹ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, bromine, for methyl substituted by cyano, halogen or C ₁ -C 4 alkoxy, for alkyl optionally substituted by cyano, halogen or C ₁ -C 4 alkoxy 2 to 6 carbon atoms, for alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulfonyl or dialkylaminosulfonyl each having 1 to 6 carbon atoms in the alkyl groups, optionally substituted by cyano, halogen or C 4 -C alkoxy, for optionally by cyano, halogen or C] -C4 alkyl substituted

Cycloalkyl, or for phenyl, phenoxy or phenylthio which is in each case optionally substituted by nitro, cyano, carbamoyl, thiocarbamoyl, halogen, C1-C4-alkyl, C 1 -C 4 -haloalkyl, C1-C4-alkoxy or C _] -C4-haloalkoxy , and - in the event that R ⁸ is different from chlorine or methyl - also represents chlorine or methyl,

R ¹⁰ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulfonyl or dialkylaminosulfonyl, optionally substituted by cyano, halogen or C 4 -C 4 -alkoxy in each case 1 to 6 carbon atoms in the alkyl groups, for cycloalkyl optionally substituted by cyano, halogen or C1-C4-alkyl, or for in each case optionally by nitro, cyano, carbamoyl, thiocarbamoyl, halogen, C1-C4-alkyl, Ci - C4-haloalkyl , -C-C4-alkoxy or Cj-C4-haloalkoxy substituted phenyl, phenoxy or phenylthio, R ¹¹ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulfonyl or dialkylaminosulfonyl or optionally substituted by cyano, halogen or C 4 -C 4 -alkoxy 1 to 6 carbon atoms in each

Alkyl groups, for cycloalkyl optionally substituted by cyano, halogen or C1-C4-alkyl, or for in each case optionally by nitro, cyano, carbamoyl, thiocarbamoyl, halogen, C 1 -C 4 -alkyl, Cj-C4-haloalkyl, Cj-C4-alkoxy or -C -C-haloalkoxy-substituted phenyl, phenoxy or phenylthio,

R ¹² for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulfonyl or dialkylaminosulfonyl each optionally substituted by cyano, halogen or Cj-C4-alkoxy 1 to 6 carbon atoms in the alkyl groups, for cycloalkyl optionally substituted by cyano, halogen or C1-C4-alkyl, or for each in each case optionally by nitro, cyano, carbamoyl, thiocarbamoyl, halogen, C1-C4-alkyl, C 1 -C 4 -haloalkyl , C1 -C4 alkoxy or C] -C4 haloalkoxy substituted phenyl, phenoxy or phenylthio, and

Q represents oxygen or sulfur.

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

R ^{1 represents} hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, R ² for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy or for the grouping -CO-R ⁶ stands,

R ^{3 represents} hydrogen, each optionally by cyano, hydroxy,

Fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally by fluorine, chlorine, bromine, methoxy or

Ethoxy-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, or represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl,

R ^{5 represents} one of the groups below,

R ^{6 represents} hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t- which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy. Butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, Di- methylamino or diethylamino, or represents ethenyl, propenyl or butenyl optionally substituted by fluorine, chlorine and / or bromine,

R ⁷ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl,

Fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl,

Ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl or diethylaminosulfonyl, for cyclopropyl, cyclobyl or cyclyl, or cyclyl, butyl, or cyclyl, butyl, or hexyl, respectively, optionally substituted by cyano, fluorine, chlorine, bromine or methyl for each optionally by nitro, cyano, carbamoyl, thiocarbamoyl, 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, phenoxy or phenylthio,

R ⁸ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, bromine, for methyl substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, for each ethyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , n- or i-

Propyl, n-, i-, s- or t-butyl, for methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy -Butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl,

Methoxycarbonyl, ethoxycarbonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl or diethylaminosulfonyl, each optionally with cyano, fluorine, chlorine, bromine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or for each optionally by nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, 1-, s- or t- Butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy or phenylthio, and - in the event that R ^{9 is} chlorine or methyl is different - also represents chlorine or methyl,

R ⁹ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl,

Fluorine, bromine, for methyl substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for ethyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, n- or i-propyl, n-, i-, s- or t-butyl, for methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- each substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, methylaminosulfonyl, ethylaminosulfonyl or dimethylethylaminosulfonyl or dimethylaminosulfonyl , for in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or for in each case optionally by nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n - or i-propyl, n-, 1-, s- or t-butyl, trifluorom ethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy or phenylthio, and - in the event that R ^{8 is} chlorine or methoxy is different - also represents chlorine or methyl,

R ¹⁰ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, chlorine, bromine, for each methyl, ethyl, n- or l- substituted by cyano, fluorine, chlorine, methoxy or ethoxy Propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl, optionally for cyano, diethylaminosulfonyl Fluorine, chlorine, bromine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or for each optionally by nitro, cyano, carbamoyl, thiocarbamoyl, 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, phenoxy or phenylthio,

R ¹¹ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl,

R ¹² for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, chlorine, bromine, for each optionally by cyano, fluorine, Chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl,

Ethoxycarbonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl or diethylaminosulfonyl, for each cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted with cyano, fluorine, chlorine, bromine, methyl or ethyl, or for each optionally with nitro, cyano, carbamoyl, thiocarbamoyl

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, phenoxy or phenylthio, and

Q represents oxygen or sulfur.

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

R ^{1 represents} hydrogen,

R ^{2 represents} hydrogen or the grouping -CO-R ⁶ ,

R ^{3 represents} hydrogen, each optionally by cyano, hydroxy,

Fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, for each optionally substituted by fluorine, chlorine or methoxy or ethenyl or propenyl, or for each optionally by Cyano, fluorine, chlorine or methyl substituted

Cyclopropyl stands, R ^{4 represents} in each case methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or represents cyclopropyl optionally substituted by cyano, fluorine, chlorine or methyl,

R ^{5 represents} one of the groups below,

R ⁶ for hydrogen or for each optionally by cyano, fluorine,

Chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, methoxy or ethoxy, or represents in each case optionally substituted by fluorine and / or chlorine ethenyl or propenyl,

R ⁷ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl,

Fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy -Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for cyclopropyl optionally substituted by cyano, fluorine, chlorine or methyl, or for each optionally substituted by nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine , Bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy or phenylthio,

R ⁸ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl,

Fluorine, bromine, for each optionally by cyano, fluorine, chlorine,

Methoxy or ethoxy substituted ethyl, n- or i-propyl, for each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for optionally by cyano, fluorine, chlorine or methyl sub substituted cyclopropyl, or for each optionally by nitro,

Cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy is substituted phenyl, phenoxy or phenylthio, and - in the event that R ⁹ is different from chlorine or methyl - also for chlorine or methyl stands,

R ⁹ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, bromine, for ethyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, n- or i-propyl, for each optionally substituted by cyano, fluorine, Chlorine, bromine, methoxy or

Ethoxy substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, optionally by cyano, fluorine, chlorine or methyl substituted cyclopropyl, or for each optionally by nitro,

Cyano, carbamoyl, thiocarbamoyl, 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, phenoxy or phenylthio, and - in the event that R ⁸ is different from chlorine or methyl

- also represents chlorine or methyl,

R ¹⁰ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl,

Fluorine, chlorine, bromine, for each methyl, ethyl, n- or i- substituted by cyano, fluorine, chlorine, methoxy or ethoxy

Propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for cyclopropyl optionally substituted by cyano, fluorine, chlorine or methyl, or phenyl, phenoxy or phenylthio which is optionally substituted by nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy,

R ¹ ! for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for cyclopropyl optionally substituted by cyano, fluorine, chlorine or methyl, or for each optionally substituted by Nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy or phenylthio,

R ¹² for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, chlorine, bromine, for each optionally by cyano, fluorine,

Chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl , Methoxycarbonyl, ethoxycarbonyl, for optionally substituted by cyano, fluorine, chlorine or methyl

Cyclopropyl, or for phenyl, phenoxy or phenylthio which is optionally substituted by nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy, and

Q represents oxygen or sulfur. Process for the preparation of substituted 2,4-diamino-l, 3,5-triazines of the formula (I) according to Claim 1, characterized in that

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

(il)

NNN "^ R ⁵ i

R H H

in which

R ¹ , R ² , R ⁴ and R ^{5 have} the meaning given in claim 1,

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

with alkoxycarbonyl compounds of the general formula (III)

R ³

O ^ OR

in which

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

R represents alkyl,

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

2,4-diamino-l, 3,5-triazines of the general formula (Ia)

R °

R ^{^} NN

(Ia)

5 / \ y ^ C s ^ \ ^ H

R N N N

H k

in which

R ¹ , R ³ , R ⁴ and R ^{5 have} the meaning given above,

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

XR ² (IV)

in which

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

X represents halogen, alkoxy, -O-CO-R ⁶ or -O-SO ₂ -OR ² ,

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

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

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

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

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

9. Substituted biguanides of the general formula (II)

H . H .

NNR ^{^}

R (II)

NNR ^J i

H H

in which

R ¹ , R ² , R ⁴ and R ^{5 have} the meaning given in claim 1,

- And acid adducts of compounds of the general formula (II) - with the exception of the compounds 1- (2-furyl-methyl) -biguanide (-hydrochloride) and 1 - (2-thienyl-methyl) -biguanide (-hydrochloride).