Substituted 2,4-diamino-1,3,5-triazine as herbicide

Details Substituted 2,4-diamino-1,3,5-triazine as herbicide Substituted 2,4-diamino-1,3,5-triazine as herbicide

1999-04-07

2001-08-07

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S230000, C504S233000, C504S234000, C544S206000, C544S207000, C544S208000, C544S209000, C544S210000

Reexamination Certificate

active

06271178

ABSTRACT:

TECHNICAL FIELD OF THE INVENTION
The invention relates to novel substituted 2,4-diamino-1,3,5-triazines, to processes and to novel intermediates for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
A number of substituted 2,4-diamino-triazines is already known from the (patent) literature (cf. U.S. Pat. No. 3,816,419, U.S. 3,932,167, EP 191496, EP 273328, EP 411153/WO 90/09378, WO 97/00254, WO 97/08156). However, these compounds have hitherto not attained any particular importance.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides the novel substituted 2,4-diamino-1,3,5-triazines of the general formula (I)
in which
R
1
represents hydrogen or optionally substituted alkyl,
R
2
represents formyl or represents in each case optionally substituted alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, arylcarbonyl or arylsulphonyl,
R
3
represents in each case optionally substituted alkyl or cycloalkyl,
R
4
represents hydrogen or alkyl,
A represents oxygen or methylene,
Ar represents in each case optionally substituted aryl or heterocyclyl, and
Z represents hydrogen, hydroxyl, cyano, nitrogen, halogen or represents in each case optionally substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenyl or alinyl,
but excluding the compounds
2-formylamino-4-[1-methyl-3-(3ethoxy-phenyl)-propylamino]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine, 2-formylamino-4-[1-methyl-3-(2-cyano-phenyl)-propylamino]-6-(1,1,2,2-tetrafluoro-ethyl)-1,3,5-triazine and 2-formylamino-4-[1-methyl-3-(4-iodophenyl)-propylamino]-6(2-chloro-ethyl)-1,3,5-triazine.
(which have already been disclosed in WO 97/08156).
The novel 2,4-diamino-1,3,Striazines of the general formula (I) are obtained when
(a) 2,4-diamino-1,3,5-triazines of the general formula (11)
in which
R
1
, R
3
, R
4
, A, Ar and Z are each as defined above
are reacted with acylating or sulphonylating agents of the general formula (III)
Y—R
2
  (III)
in which
R
2
is as defined above and
Y represents halogen, alkoxy or —O—R
2
,
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), except for those where Z=NO
2
, substituted biguanidines of the general formula (IV)
in which
R
1
, R
2
, R
3
, R
4
, A and Ar are each as defined above
and/or acid adducts of compounds of the general formula (IV)
are reacted with alkoxycarbonyl compounds of the general formula (V)
Z—CO—OR′  (V)
in which
Z, with the exception of nitro, 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
(c) substituted triazines of the general formula (VI)
in which
R
3
, R
4
, A, Ar and Z are each as defined above and
x represents halogen or alkoxy
are reacted with nitrogen compounds of the general formula (VII)
in which
R
1
and R
2
are each as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, further conversions within the scope of the above definition of substituents are carried out by customary methods on the compounds of the general formula (I) obtained by the processes described under (a), (b) or (c).
The novel substituted 2,4-diamino-1,3,5-triazines of the general formula (I) have strong and selective herbicidal activity.
The compounds of the general formula (I) according to the invention contain at least one asymmetrically substituted carbon atom and can therefore be present in different enantiomeric (R- and S-configured forms) or diastereomeric forms. The invention relates both to the different possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I), and to the mixtures of these isomeric compounds.
In the definitions, the hydrocarbon chains, such as alkyl—also in combination with heteroatoms, such as in alkoxy or alkylthio—are in each case straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably represents fluorine, chlorine or bromine, and in particular represents fluorine or chlorine.
The invention preferably provides compounds of the formula (I) in which
R
1
represents hydrogen or represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 6 carbon atoms,
R
2
represents formyl, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, or represents in each case optionally cyano-, halogen-, C
1
-C
4
-alkyl-, halogeno-C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, halogeno-C
1
-C
4
-alkoxy- or C
1
-C
4
-alkoxy-carbonyl-substituted phenylcarbonyl, naphthylcarbonyl, phenylsulphonyl or naphthylsulphonyl,
R
3
represents optionally hydroxyl-, 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
4
represents hydrogen or alkyl having 1 to 4 carbon atoms,
A represents oxygen or methylene,
Ar represents in each case optionally substituted phenyl, naphthyl or heterocyclyl,
where the possible heterocyclyl radicals are preferably selected from the group below:
furyl, benzofuryl, dihydrobenzofuryl, tetrahydrofuryl, thienyl, benzothienyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, indolyl, pyridinyl, quinolinyl, isoquinolinyl and pyrimidinyl,
and where the possible substituents are in each case preferably selected from the group below:
hydroxyl, cyano, nitro, halogen, in each case optionally hydroxyl-, cyano- or halogen-substituted alkyl or alkoxy having in each case 1 to 6 carbon atoms, in each case optionally halogen-substituted alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, in each case optionally hydroxyl-, cyano-, nitro-, halogen-, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted phenyl or phenoxy, and also in each case optionally halogen-substituted methylenedioxy or ethylenedioxy, and
Z represents hydrogen, represents halogen, represents in each case optionally hydroxyl-, cyano-, nitro-, halogen-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkyl-carbonyl-, C
1
-C
4
-alkoxy-carbonyl-, C
1
-C
4
-alkylthio-, C
1
-C
4
-alkylsulphinyl- or C
1
-C
4
-alkylsulphonyl-substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, or represents in each case optionally halogen- or C
1
-C
4
-alkoxy-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms,
but excluding the compounds
2-formylamino-4-[1-methyl-3-(3-ethoxy-phenyl)-propylamino]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine, 2-formylamino-4-[1-methyl-3-(2-cyano-phenyl)-propylamino]-6-(1,1,2,2-tetrafluoro-ethyl)-1,3,5-triazine and 2-formylamino-4-[1-methyl-3-(4-iodo-phenyl)-propylamino]-6(2-chloro-ethyl)-1,3,5-triazine.
(which have already been disclosed in WO 97/08156).
From among the compounds of the formula (I) defined above as preferred (“preferably”), particular emphasis is given to the following groups:
(A) the compounds of the formula (I) in which A, R
1
, R
2
, R
3
, R
4
and Z are each as defined above and Ar represents in each case optionally substituted phenyl or naphthyl, the possible substituents being as defined above;
(B) the compounds of the formula (1) in which A, R
1
, R
2
, R
3
, R
4
and Z are each as defined above and Ar represents in each case optionally substituted heterocyclyl, the possible heterocyclyl groupings and the possible substituents being as defined above.
The invention in particular relates to compounds of the formula (I) in which
R
1
represents

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