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

Details Substituted 2,4-diamino-1,3,5-triazine and their use as... Substituted 2,4-diamino-1,3,5-triazine and their use as...

2000-05-01

2002-02-19

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S207000

Reexamination Certificate

active

06348435

ABSTRACT:

TECHNICAL FIELD OF THE INVENTION
The invention relates to novel substituted 2,4-diamino-1,3,5-triazines, to processes and novel intermediates for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
A number of substituted 2,4-diamino-triazines are already known from the (patent) literature (cf. JP 63222166—cited in Chem. Abstracts 111:97288w; cf. also U.S. Pat. Nos. 3,816,419, 3,932,167, EP 191496, EP 273328, EP 411153/WO 90/09378). However, these compounds have hitherto not attained any particular importance.
DETAILED DESCRIPTION OF THE INVENTION
This invention now provides the novel substituted 2,4-diamino-1,3,5-triazines of the general formula (I)
in which
R
1
represents hydrogen or represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 6 carbon atoms,
R
2
represents hydrogen, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 6 carbon atoms or represents the grouping —CO—R
6
,
R
3
represents hydrogen, represents optionally cyano-, hydroxyl-, halogen-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-alkylsulphinyl- or C
1
-C
4
-alkyl-sulphonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally halogen- or C
1
-C
4
-alkoxy-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,
R
4
represents hydrogen, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 6 carbon atoms, or represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,
R
5
represents one of the groupings below,
R
6
represents hydrogen or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups or represents optionally halogen-substituted alkenyl having 2 to 6 carbon atoms,
R
7
represents hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulphonyl or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl, or represents in each case optionally nitro-, cyano-, carbamoyl-, thiocarbamoyl-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted phenyl, phenoxy or phenylthio,
R
8
represents hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, bromine, represents cyano-, halogen- or C
1
-C
4
-alkoxy-substituted methyl, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 2 to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulphonyl or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl, or represents in each case optionally nitro-, cyano-, carbamoyl-, thiocarbamoyl-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted phenyl, phenoxy or phenylthio, and—if R
9
is different from chlorine or methyl—also represents chlorine or methyl,
R
9
represents hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, bromine, represents cyano-, halogen- or C
1
-C
4
-alkoxy-substituted methyl, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 2 to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulphonyl or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl, or represents in each case optionally nitro-, cyano-, carbamoyl-, thiocarbamoyl-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted phenyl, phenoxy or phenylthio, and—if R
8
is different from chlorine or methyl—also represents chlorine or methyl,
R
10
represents hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulphonyl or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl, or represents in each case optionally nitro-, cyano-, carbamoyl-, thiocarbamoyl-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted phenyl, phenoxy or phenylthio,
R
11
represents hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulphonyl or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl, or represents in each case optionally nitro-, cyano-, carbamoyl-, thiocarbamoyl-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted phenyl, phenoxy or phenylthio,
R
12
represents hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminosulphonyl or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl, or represents in each case optionally nitro-, cyano-, carbamoyl-, thiocarbamoyl-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted phenyl, phenoxy or phenylthio, and
Q represents oxygen or sulphur.
The novel substituted 2,4-diamino-1,3,5-triazines of the general formula (I) are obtained when
(a) substituted biguanides of the general formula (I)
 in which
R
1
, R
2
, R
4
and R
5
are as defined above,—and/or acid adducts of compounds of the general formula (II)—are reacted with alkoxycarbonyl compounds of the general formula (III)
 in which
R
3
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, or when
(b) to prepare compounds of the formula (I) in which R
2
is different from hydrogen, 2,4-diamino-1,3,5-triazines of the general formula (Ia)
 in which
R
1
, R
3
, R
4
and R
5
are as defined above are reacted with alkylating or acylating agents of the general formula (IV)
X—R
2
  (IV)
 in which
R
2
is as defined above, except for hydrogen, and
X represents halogen, alkoxy, —O—CO—R
6
or —O—SO
2
—O—R
2
, 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) or (b).
The novel substituted 2,4-diamino-1,3,5-triazines of the general formula (I) have strong and selective herbicidal activity.
To a certain extent, the compounds of the general formula (I) also have fungicid

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