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

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

2001-04-05

2002-06-11

Raymond, Richard L. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C544S298000, C546S069000, C546S074000, C546S290000, C546S290000, C558S391000, C560S034000, C564S234000

Reexamination Certificate

active

06403794

ABSTRACT:

TECHNICAL FIELD OF THE INVENTION
The invention relates to novel substituted 2-amino-4-alkylamino-1,3,5-triazines, to processes and to novel intermediates for their preparation and to their use as herbicides.
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. Pat. No. 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-amino-4-alkylamino-1,3,5-triazines of the general formula (I)
in which
R
1
represents in each case optionally substituted alkyl having 2 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms,
R
2
represents hydrogen or represents alkyl having 1 to 4 carbon atoms,
A represents oxygen or methylene
Ar represents in each case optionally substituted phenyl, napthyl or heterocyclyl, and
Z represents hydrogen, represents halogen or represents in each case optionally substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenyl or alkinyl.
The novel 2-amino-4-alkylamino-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
, A and Ar are each as defined above
and/or acid adducts of compounds of the general formula (II)
are reacted with alkoxycarbonyl compounds of the general formula (III)
Z—CO—OR′  (III)
in which
Z is as defined above and
R′ represents alkyl,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(b) substituted triazines of the general formula (IV)
 in which
R
1
, R
2
, A, Ar and Z are each as defined above and
X
1
represents halogen or alkoxy
are reacted with ammonia, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(c) substituted triazines of the general formula (V),
 in which
Z is as defined above and
X
2
represents halogen or alkoxy
are reacted with substituted alkylamines of the general formula (VI),
in which
R
1
, R
2
, A and Ar are each as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, further conversions within the scope of the above definition of substituents are carried out by customary methods on the compounds of the general formula (I) obtained by the processes described under (a), (b) or (c).
The novel substituted 2-amino-4-alkylamino-1,3,5-triazines of the general formula (I) have strong and selective herbicidal activity.
The compounds of the general formula (I) according to the invention contain at least one asymmetrically substituted carbon atom and can therefore be present in different enantiomeric (R- and S-configured forms) or diastereomeric forms. The invention relates both to the different possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I), and to the mixtures of these isomeric compounds.
In the definitions, the hydrocarbon chains, such as alkyl—also in combination with heteroatoms, such as in alkoxy or alkylthio—are in each case straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably represents fluorine, chlorine or bromine, and in particular represents fluorine or chlorine.
The invention preferably provides compounds of the formula (I) in which
R
1
represents optionally hydroxyl-, cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 2 to 4 carbon atoms or represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,
R
2
represents hydrogen, methyl or ethyl,
A represents oxygen or methylene,
Ar represents in each case optionally substituted phenyl, naphthyl or heterocyclyl,
where the possible heterocyclyl groupings are preferably selected from the group below:
furyl, benzofuryl, dihydrobenzofuryl, tetrahydrofuryl, thienyl, benzothienyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, quinolinyl, isoquinolinyl, pyridinyl and pyrimidinyl,
and where the possible substituents are in each case preferably selected from the group below:
hydroxyl, cyano, nitro, halogen, in each case optionally hydroxyl-, cyano- or halogen-substituted alkyl or alkoxy having in each case 1 to 6 carbon atoms, in each case optionally halogen-substituted alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 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-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms.
From among the compounds of the formula (I) defined above as preferred (“preferably”), particular emphasis is given to the following groups:
(A) the compounds of the formula (I) in which A, R
1
, R
2
and Z are each as defined above and Ar represents in each case optionally substituted phenyl or naphthyl, the possible substituents being as defined above;
(B) the compounds of the formula (I) in which A, R
1
, R
2
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 in each case optionally hydroxyl-, cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted ethyl, n- or i-propyl, n-, i-, s- or t-butyl or represents in each case optionally cyano-, fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
R
2
represents hydrogen or methyl,
A represents oxygen or methylene,
Ar represents in each case optionally substituted phenyl, naphthyl or heterocyclyl,
where the possible heterocyclyl groups are preferably selected from the group below:
furyl, benzofuryl, dihydrobenzofuryl, tetrahydrofuryl, thienyl, benzothienyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pyrrolyl, quinolinyl, isoquinolinyl, pyridinyl and pyrimidinyl,
and where the possible substituents are in each case preferably selected from the group below:
hydroxyl, cyano, nitro, fluorine, chlorine, bromine, in each case optionally hydroxyl- cyano-, fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, in each case optionally fluorine- or chlorine-substituted acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, in each case optionally hydroxyl-, cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl or phenoxy, and also in each case optionally fluorine- or chlorine-substituted methylenedioxy or ethylenedioxy,
and
Z represents hydro

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