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

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

2000-07-10

2002-06-18

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S206000, C544S207000, C544S208000, C544S209000, C504S232000, C504S233000, C504S234000

Reexamination Certificate

active

06407041

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 aryloxyalkylaminotriazines is already known from the (patent) literature (cf. EP-273 328, EP-411 153/WO 90/09378). However, these compounds have hitherto not obtained any particular significance.
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
Q represents O (oxygen), S (sulphur), SO, SO
2
, NH or N(alkyl),
R
1
represents hydrogen or represents optionally substituted alkyl,
R
2
represents hydrogen, represents formyl or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl,
R
3
represents in each case optionally substituted alkyl or cycloalkyl,
R
4
represents hydrogen or alkyl,
R
5
represents hydrogen or alkyl,
Ar represents in each case optionally substituted aryl or heteroaryl, and
Z represents hydrogen, cyano, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenyl, alkinyl or cycloalkyl.
The novel substituted 2,4-diaminotriazines of the general formula (I) are obtained when
(a) biguanides of the general formula (II)
 in which
Q, R
1
, R
2
, R
3
, R
4
, R
5
and Ar 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)
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 halogenotriazines of the general formula (TV)
 in which
Q, R
3
, R
4
, R
5
, Ar and Z are as defined above and
X represents halogen,
are reacted with nitrogen compounds of the general formula (V)
in which
R
1
and R
2
are as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(c) substituted aminotriazines of the general formula (VI)
 in which
R
1
, R
2
and Z are as defined above and
Y
1
represents halogen or alkoxy,
are reacted with substituted alkyl amines of the general formula (VII)
in which
Q, Ar, R
3
, R
4
and R
5
are as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(d) substituted 2,4-diamino-1,3,5-triazines of the general formula (Ia)
 in which
Q, R
1
, R
3
, R
4
, R
5
, Ar and Z are as defined above
are reacted with alkylating or acylating agents of the general formula (VIII)
in which
R
2
is as defined above, except for hydrogen, and
Y
2
represents halogen, —O—R
2
or —O—CO—R
2
,
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 on the compounds of the general formula (I) obtained by the processes described under (a), (b), (c) or (d).
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) and/or diasteromeric 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—including 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 fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably provides compounds of the formula (I) in which
Q represents O (oxygen), S (sulphur), SO, SO
2
, NH or N(C
1
-C
4
-alkyl),
R
1
represents hydrogen or represents optionally hydroxyl-, cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 6 carbon atoms,
R
2
represents hydrogen, represents formyl or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl having in each case 1 to 6 carbon atoms in the alkyl groups,
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,
R
5
represents hydrogen or alkyl having 1 to 4 carbon atoms,
Ar represents in each case optionally substituted phenyl, naphthyl, tetralinyl or heteroaryl,
where the possible heteroaryl groupings are preferably selected from the following group:
furyl, benzofuryl, thienyl, benzothienyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, imidazolyl, pyrrolyl, pyridinyl, pyrimidinyl,
and where the possible substituents are in each case selected from the following group:
hydroxyl, cyano, carbamoyl, thiocarbamoyl, 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, alkylsulphonyl, dialkylamino, alkylcarbonylamino, alkylsulphonylamino, bis-alkylcarbonyl-amino, bis-alkylsulphonyl-amino, N-alkyl-N-alkylcarbonyl-amino or N-alkyl-N-alkylsulphonyl-amino 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 in each case optionally halogen-substituted methylenedioxy or ethylenedioxy, and
Z represents hydrogen, cyano, halogen, represents in each case optionally hydroxyl-, cyano-, 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, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkenyl or alkinyl having in each case 2 to 4 carbon atoms in the alkenyl or alkinyl groups, or represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms.
From among the compounds of the general formula (I) defined above as being preferred (“preferably”), particular emphasis is given to the following groups:
(A) the compounds of the formula (I) in which Q, R
1
, R
2
, R
3
, R
4
, R
5
and Z are as defined above and Ar represents in each case optionally substituted phenyl or naphthyl, where the possible substituents are as defined above;
(B) the compounds of the formula (I) in which Q, R
1
, R
2
, R
3
, R
4
, R
5
and Z are as defined above and Ar represents optionally substituted heterocyclyl, where the possible heterocyclyl groupings and the possible substituents are as defined above.
The invention relates in particular to compounds of the formula (I) in which
Q represents O (oxygen), S (sulphur) or NH,
R
1
represents hydrogen or represents in each case optionally hydroxyl-, cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
R
2
represents hydrogen, represents formyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy- or ethoxy-substitu

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