Substituted phenyluracils

Details Substituted phenyluracils Substituted phenyluracils

2001-04-24

2002-08-20

Shah, Mukund J. (Department: 1624)

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

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C544S311000, C544S312000, C544S313000

Reexamination Certificate

active

06437126

ABSTRACT:

The invention relates to novel substituted phenyluracils, to processes for their preparation and to their use as herbicides.
It is known that certain substituted uracils have herbicidal properties (cf. DE 4131038, DE 4237920, DE 4329537, EP 408382/U.S. Pat. Nos. 5,084,084/5,127,935/5,154,755, EP 542685, EP 563384, EP 648749, U.S. Pat. Nos. 4,979,982, 5,169,430, WO 91/00278, WO 95/25725). However, these compounds have hitherto not obtained any importance worth mentioning.
This invention, accordingly, provides the novel substituted phenyluracils of the general formula (I)
in which
R
1
represents hydrogen, halogen or optionally substituted alkyl,
R
2
represents optionally substituted alkyl,
R
3
represents hydrogen, amino or represents alkyl, alkenyl or alkinyl, each of which is optionally substituted,
R
4
represents hydrogen, cyano or halogen,
R
5
represents cyano or thiocarbamoyl, and
R
6
represents one of the groups below
 in which
Q
1
and Q
2
each represent oxygen or sulphur,
R
7
in each case represents hydrogen or optionally substituted alkyl,
R
8
represents hydrogen, hydroxyl, amino or represents alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkinyl, cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylcarbonylamino, cycloalkylsulphonylamino, aryl, aryloxy, arylamino, arylcarbonylamino, arylsulphonylamino, arylalkyl, arylalkoxy, arylalkylamino, each of which is optionally substituted, and
R
9
and R
10
each represent alkyl.
The novel substituted phenyluracils of the general formula (I) are obtained when
(a) alkenylphenyluracils of the general formula (II)
 in which
R
1
, R
2
, R
3
, R
4
, R
5
and R
7
are each as defined above and
R
11
and R
12
each represent hydrogen, cyano, carboxyl or represent alkyl or alkoxycarbonyl, each of which is optionally substituted, are reacted with ozone, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or when
(b) carbonylphenyluracils of the general formula (Ia)
 in which
R
1
, R
2
, R
3
, R
4
, R
5
and R
7
are each as defined above are reacted with amino compounds of the general formula (III)
H
2
N—R
8
  (III)
 in which
R
8
is as defined above
or with acid adducts of compounds of the formula (II)
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or when
(c) carbonylphenyluracils of the general formula (Ia)
 in which
R
1
, R
2
, R
3
, R
4
, R
5
and R
7
are each as defined above, are reacted with alcohols and/or mercaptans of the general formulae (IVa) or (IVb)
 in which
Q
1
, Q
2
, R
9
and R
10
are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary.
The compounds of the general formula (I) can also be converted into other compounds of the general formula (I) in accordance with the above definition using other customary methods, for example by amination and/or alkylation (for example R
3
: H→NH
2
, H→CH
3
), reaction with hydrogen sulphide (for example R
5
: CN→CSNH
2
).
The novel substituted phenyluracils of the general formula (I) have strong herbicidal activity.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, 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, fluorine, chlorine, bromine or optionally fluorine- and/or chlorine-substituted C
1
-C
4
-alkyl,
R
2
represents optionally fluorine- and/or chlorine-substituted C
1
-C
4
-alkyl,
R
3
represents hydrogen, amino, represents optionally cyano-, fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted C
1
-C
6
-alkyl or represents optionally fluorine- and/or chlorine-substituted C
2
-C
6
-alkenyl or C
2
-C
6
-alkinyl,
R
4
represents hydrogen, cyano, fluorine or chlorine,
R
5
represents cyano or thiocarbamoyl, and
R
6
represents one of the groups below
 in which
Q
1
and Q
2
each represent oxygen or sulphur,
R
7
in each case represents hydrogen or represents optionally halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl,
R
8
represents hydrogen, hydroxyl, amino, represents C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylamino, di-(C
1
-C
4
-alkyl)-amino, C
1
-C
4
-alkylcarbonylamino or C
1
-C
4
-alkyl-sulphonylamino, each of which is optionally substituted by halogen, C
1
-C
4
-alkoxy or C
1
-C
4
-alkoxy-carbonyl, represents C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy or C
2
-C
6
-alkinyl, each of which is optionally substituted by halogen, represents C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkyloxy, C
3
-C
6
-cycloalkylamino, C
3
-C
6
-cycloalkyl-carbonylamino or C
3
-C
6
-cycloalkylsulphonylamino, each of which is optionally substituted by halogen or C
1
-C
4
-alkyl, or represents phenyl, phenoxy, phenylamino, phenylcarbonylamino, phenylsulphonylamino, phenyl-C
1
-C
4
-alkyl, phenyl-C
1
-C
4
-alkoxy, phenyl-C
1
-C
4
-alkylamino, each of which is optionally substituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-halogenoalkoxy, and
R
9
and R
10
each represent C
1
-C
4
-alkyl.
The invention in particular relates to compounds of the formula (I) in which
R
1
represents hydrogen, fluorine, chlorine, bromine or optionally fluorine- and/or chlorine-substituted methyl or ethyl,
R
2
represents optionally fluorine- and/or chlorine-substituted methyl or ethyl,
R
3
represents hydrogen, amino, represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or represents optionally fluorine- and/or chlorine-substituted propenyl, butenyl, propinyl or butinyl,
R
4
represents hydrogen, fluorine or chlorine,
R
5
represents cyano or thiocarbamoyl, and
R
6
represents one of the groups below
 in which
Q
1
and Q
2
each represent oxygen or sulphur,
R
7
in each case represents hydrogen or represents methyl or ethyl, each of which is optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R
8
represents hydrogen, hydroxyl, amino, represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, acetylamino, propionylamino, n- or i-butyroylamino, methylsulphonylamino or ethylsulphonylamino, each of which is optionally substituted by fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, represents propenyl, butenyl, propenyloxy, butenyloxy, propinyl or butinyl, each of which is optionally substituted by fluorine, chlorine or bromine, represents cyclopentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy, cyclopentylaamino, cyclohexylamino, cyclopropylcarbonylamino, cyclobutylcarbonylamino, cyclopentylcarbonylamino, cyclohexylcarbonylamino, cyclopropylsulphonylamino, cyclobutylsulphonylamino, cyclopentylsulphonylamino or cyclohexylsulphonylamino, each of which is optionally substituted by fluorine, chlorine, bromine, methyl or ethyl, or represents phenyl, phenylamino, phenylcarbonylamino, phenylsulphonylamino, benzyl, benzyloxy or benzylamino, each of which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, and
R
9
and R
10
each represent methyl or ethyl.
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 tile preferred ranges stated.
Examples of the compounds of the formula (I) according to the invention are l

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