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

1999-04-01

2002-08-27

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S233000, C504S234000, C544S206000, C544S208000

Reexamination Certificate

active

06440903

ABSTRACT:

This is a 371 of PCT EP 97/05317, filed Sep. 29, 1997.
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. Pat. No. 3,932,167, EP 191496, EP 273328, EP 411153/WO 90/09378, JP 62294669—cited in Chem. Abstracts 109: 129062v). 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 hydroxyl-, cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 6 carbon atoms,
R
2
represents hydrogen, represents formyl, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, 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 napththylsulphonyl,
R
3
represents optionally cyano-, halogen- or C
1
-
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,
X represents a substituent from the following group:
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
Z represents hydrogen, hydroxyl, 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, represents in each case optionally halogen-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,
but excluding the compounds
2-amino- 4-methoxy-6-[1-(3-chlorophenyl)-ethylamino]-1,3,5-triazine, 2-amino-4-methoxy-6-[1-(3-methyl-phenyl)-ethylamino]-1,3,5-triazine, 2-amino-4-chloro-6-[1-(3-trifluoromethyl-phenyl)-ethylamino]-1,3,5-triazine, 2-amino-4-chloro-6-[1-(3-nitrophenyl)-ethylamino-1,3,5-triazine, 2-amino-4-chloro-6-[1-(3-chloro-phenyl)-ethylamino]-1,3,5-triazine and 2-amino-4-chloro-6-[1-(3-methyl-phenyl)-ethylamino]-1,3,5-triazine
(which are already known from JP 62294669).
The novel 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
, R
3
and X 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 aminotriazines of the general formula (IV)
 in which
R
3
, X and Z are each as defined above and
X
1
represents halogen or alkoxy
are reacted with nitrogen compounds of the general formula (V)
 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,
or when
(c) substituted aminotriazines of the general formula (VI),
 in which
R
1
, R
2
and Z are each as defined above and
X
2
represents halogen or alkoxy
are reacted with amino compounds of the general formula (VII),
 in which
R
3
and X are each as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(d) to prepare compounds of the formula (I), except for those where R
2
=H, 2,4-diamino-1,3,5-triazines of the general formula (Ia)
 in which
R
1
, R
3
, X and Z are each as defined above
are reacted with alkylating, acylating or sulphonylating agents of the general formula (VIII)
Y—R
2
  (VIII)
 in which
R
2
is as defined above—except for hydrogen—and
Y represents halogen, alkoxy, alkoxysulphonyloxy or acyloxy,
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), (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) 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 hydroxyl-, cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted alkyl having 1 to 4 carbon atoms,
R
2
represents hydrogen, represents formyl, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally cyano-, fluorine-, chlorine-, 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-, trifluoromethoxy-, methoxycarbonyl- or ethoxycarbonyl-substituted phenylcarbonyl or phenylsulphonyl,
R
3
represents optionally hydroxyl-, cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted alkyl having 1 to 4 carbon atoms or represents optionally cyano-, fluorine-, chlorine-, methyl- or ethyl-substituted cycloalkyl having 3 to 6 carbon atoms,
x represents a substituent from the group below:
hydroxyl, cyano, nitro, fluorine, chlorine, bromine, iodine, in each case optionally hydroxyl-, cyano-, fluorine- or chlorine-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms, in each case optionally fluorine- or chlorine-substituted alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 4 carbon atoms in the alkyl groups, in each case optionally hydroxyl-, cyano-, nitro-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or

Affiliated with

Also associated with

Rating

Substituted 2,4-diamino-1,3,5-triazines as herbicides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Substituted 2,4-diamino-1,3,5-triazines as herbicides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted 2,4-diamino-1,3,5-triazines as herbicides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2973335