Substituted 2,4-diamino-1,3,5-triazines as herbicides

Details Substituted 2,4-diamino-1,3,5-triazines as herbicides Substituted 2,4-diamino-1,3,5-triazines as herbicides

1999-10-18

2002-06-04

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S206000, C504S232000, C504S233000

Reexamination Certificate

active

06399541

ABSTRACT:

This is a 371 National Application of PCT/EP98/01362, filed Mar. 9, 1998.
The invention relates to novel substituted 2,4-diamino-1,3,5-triazines, to processes for their preparation and to their use as herbicides.
A number of substituted 2,4-diamino-triazines, such as, for example, the compound 2-amino-4-(1-phenyl-ethylamino)-6-trifluoromethyl-1,3,5-triazine, are already known from the (patent) literature (cf. U.S. Pat. No. 3,816,419, cf. also U.S. Pat. No. 3,932,167, EP 191496, EP 273328, EP 411153/WO 90/09378). However, these compounds have hitherto not attained any particular importance.
This invention, accordingly, provides the novel substituted 2,4-diamino-1,3,5-triazines of the general formula (I),
in which
R
1
represents (in each case unsubstituted) phenyl or naphthyl,
R
2
represents alkyl,
R
3
represents hydrogen, represents halogen or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl,
R
4
represents hydrogen, represents halogen or represents optionally substituted alky,
R
5
represents hydrogen, represents halogen or represents optionally substituted alkyl, and
R
6
represents hydrogen or represents in each case optionally substituted alkyl, alkylcarbonyl or alkylsulphonyl,
but where the known compound 2-amino-4-(1-phenyl-ethylamino)-6-trifluoromethyl-1,3,5-triazine (cf. U.S. Pat. No. 3,816,419) is excluded by disclaimer.
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 (II)
in which
R
1
, R
2
and R
6
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)
in which
R
3
, R
4
and R
5
are each 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 that
(b) to prepare compounds of the formula (I) in which R
6
is different from hydrogen
2,4-diamino-1,3,5-triazines of the general formula (Ia)
in which
R
1
, R
2
, R
3
, R
4
and R
5
are each as defined above
are reacted with alkylating, acylating or sulphonylating agents of the general formula (IV)
X−R
6
  (IV)
in which
R
6
is as defined above, except for hydrogen, and
X represents halogen, alkoxy, acyloxy or alkoxysulphonyloxy,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and further conversions within the scope of the above definition of substituents are carried out by customary methods, if appropriate, on the compounds of the general formula (I) obtained according to 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.
Surprisingly, the 2,4-diamino-1,3,5-triazines of the general formula (I) according to the invention exhibit considerably stronger herbicidal activity than the prior-art compound 2-amino-4-(1-phenyl-ethylamino)-6-trifluoromethyl-1,3,5-triazine, and some of them are tolerated well by crop plants, such as, for example, barley and cotton.
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) and/or diastereomeric forms. 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, are in each case straight-chain or branched, including combination with heteroatoms, such as in alkoxy or alkylthio.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably provides compounds of the formula (I) in which
R
1
represents (in each case unsubstituted) phenyl or naphthyl,
R
2
represents alkyl having 1 to 6 carbon atoms,
R
3
represents hydrogen, represents halogen or represents in each case optionally halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms,
R
4
represents hydrogen, represents halogen or represents optionally halogen-substituted C
1
-C
6
-alkyl,
R
5
represents hydrogen, represents halogen or represents optionally halogen-substituted C
1
-C
6
-alkyl, and
R
6
represents hydrogen or represents in each case optionally halogen- or C
1
-C
4
-alkoxy substituted C
1
-C
6
-alkyl, C
2
-C
7
-alkylcarbonyl or C
1
-C
6
-alkyl-sulphonyl,
but where the known compound 2-amino-4-(1-phenyl-ethylamino)-6-trifluoromethyl-1,3,5-triazine (cf. U.S. Pat. No. 3,816,419) is excluded by disclaimer.
The invention relates in particular to compounds of the formula (I) in which
R
1
represents (in each case unsubstituted) phenyl or naphthyl,
R
2
represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
R
3
represents hydrogen, represents fluorine, chlorine, bromine, or represents in each case optionally 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, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,
R
4
represents hydrogen, represents fluorine, chlorine or bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
R
5
represents hydrogen, represents fluorine, chlorine or bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, and
R
6
represents hydrogen or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, n-, i-, s- or t-butylsulphonyl,
but where the known compound 2-amino-4-(1-phenyl-ethylamino)-6-trifluoromethyl-1,3,5-triazine (cf. U.S. Pat. No. 3,816,419) as excluded by disclaimer.
The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and, 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 given preferred ranges.
Using, for example, 1-(1-phenyl-propyl)-biguanide and methyl trifluoroacetate as starting materials, the course of the reaction of the process (a) according to the invention can be illustrated by the following equation:
Using, for example, 2-amino-4-(2,2,2-trifluoro-1-methyl-ethyl)-6-(1-phenyl-ethyl-amino)-1,3,5-triazine and acetyl chloride as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following equation:
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 the compounds of the formula (I). In the formula (II), R
1
, R
2
and R
6
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 R
1
, R
2
and R
6
.
Suitable acid adducts of compounds of the formula (I) are their addition products with protonic 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) are known and/or can be prepared by a process known per se (cf. U.S. Pat. No. 3,816,419; Ind

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