Substituted aminophenyluracils

Details Substituted aminophenyluracils Substituted aminophenyluracils

1998-01-14

2001-10-09

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S310000, C544S311000, C544S312000

Reexamination Certificate

active

06300280

ABSTRACT:

The invention relates to novel substituted aminophenyluracils, to a process for their preparation and to their use as herbicides and insecticides.
It is known that certain substituted aminophenyluracils have herbicidal properties (cf. EP-408 382/U.S. Pat. No. 5 084 084/U.S. Pat. No. 5 127 935/U.S. Pat. No. 5 154 755, EP-563 384, DE-44 12 079), but they have hitherto not attained any major importance either as herbicides or as insecticides.
This invention, accordingly, provides the novel substituted aminophenyluracils of the general formula (I)
in which
Q represents oxygen or sulphur,
R
1
represents hydrogen, cyano or halogen,
R
2
represents cyano, thiocarbamoyl, halogen or represents optionally substituted alkyl,
R
3
represents respectively optionally substituted alkyl, cycloalkyl, aryl, arylalkyl or heteroaryl,
R
4
represents respectively optionally substituted cycloalkyl, aryl or heteroaryl,
R
5
represents hydrogen, halogen or represents respectively optionally substituted alkyl or alkoxy,
R
6
represents optionally substituted alkyl and
R
7
represents hydrogen, hydroxyl, amino or represents respectively optionally substituted alkyl, alkoxy, alkenyl or alkinyl.
The novel substituted aminophenyluracils of the general formula (I) are obtained when appropriate sulphonylaminophenyluracils of the general formula (II)
in which
Q, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
are each as defined above, are reacted with acid derivatives of the general formula (III)
R
4
—CO—X  (III)
in which
R
4
is as definied above and
X represents halogen or the grouping —CO—R
4
,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
The novel substituted aminophenyluracils of the general formula (I) have strong herbicidal and insecticidal 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 fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably provides compounds of the formula (I) in which
Q represents oxygen or sulphur,
R
1
represents hydrogen, cyano, fluorine or chlorine,
R
2
represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, or represents optionally fluorine- and/or chlorine-substituted alkyl having 1 to 4 carbon atoms,
R
3
represents optionally cyano-, fluorine-, chlorine-, bromine-, C
1
-C
4
-alkoxy- or C
1
-C
4
-alkylthio-substituted alkyl having 1 to 6 carbon atoms,
R
3
furthermore represents optionally cyano-, fluorine-, chlorine-, bromine- or C
1
-C
4
-alkyl-substituted cycloalkyl having 3 to 8 carbon atoms,
R
3
furthermore represents phenyl, naphthyl, benzyl, phenylethyl, thienyl, pyrazolyl, pyridinyl or quinolinyl, possible substituents in each case being:
fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, dimethylaminosulphonyl, diethylaminosulphonyl, respectively optionally fluorine- and/or chlorine-substituted C
1
-C
4
-alkylsulphinyl or C
1
-C
4
-alkylsulphonyl, respectively optionally, fluorine-, chlorine-, bromine-, cyano-, methoxy- or ethoxy-substituted C
1
-C
4
-alkoxycarbonyl or respectively optionally fluorine-, chlorine-, bromine-, cyano-, methyl-, methoxy-, trifluoromethyl- and/or trifluoromethoxy-substituted phenyl, phenyloxy or phenylthio;
R
4
represents optionally cyano-, fluorine-, chlorine-, bromine- or C
1
-C
4
-alkyl-substituted cycloalkyl having 3 to 8 carbon atoms,
R
4
furthermore represents respectively optionally substituted phenyl, naphthyl, furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridinyl, pyrimidinyl or quinolinyl, possible substituents in each case being: fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, dimethylamino, dimethylaminosulphonyl, diethylaminosulphonyl, respectively optionally fluorine- and/or chlorine-substituted C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl or C
1
-C
4
-alkylsulphonyl or optionally fluorine-, chlorine-, bromine-, cyano-, methoxy- or ethoxy-substituted C
1
-C
4
-alkoxycarbonyl;
R
5
represents hydrogen, fluorine, chlorine, bromine or represents respectively optionally fluorine- and/or chlorine-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms,
R
6
represents optionally fluorine- and/or chlorine-substituted alkyl having 1 to 4 carbon atoms and
R
7
represents hydrogen, hydroxyl, amino or represents respectively optionally fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkenyl or alkinyl having in each case up to 6 carbon atoms.
The invention in particular provides compounds of the formula (I) in which
Q represents oxygen or sulphur,
R
1
represents hydrogen, cyano, fluorine or chlorine,
R
2
represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl or trifluoromethyl,
R
3
represents respectively optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
R
3
furthermore represents respectively optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
R
3
furthermore represents respectively optionally substituted phenyl, naphthyl, benzyl, phenylethyl, thienyl, pyrazolyl, pyridinyl or quinolinyl, possible substituents being: fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, methoxycarbonyl, ethoxycarbonyl, n-or i-propoxycarbonyl,
R
4
represents optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
R
4
furthermore represents respectively optionally substituted phenyl, naphthyl, furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridinyl or pyrimidinyl, possible substituents in each case being: fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, dimethylamino, dimethylaminosulphonyl or diethylaminosulphonyl, respectively optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, respectively optionally fluorine-, chlorine-, bromine-, cyano-, methoxy- or ethoxy-substituted methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, respectively optionally fluorine-, chlorine-, bromine-, cyano-, methyl-, methoxy-, trifluormethyl- and/or trifluoromethoxy-substituted phenyl, phenyloxy or phenylthio,
R
5
represents hydrogen, fluorine, chlorine, bromine or represents respectively optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl,
R
6
represents optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl and
R
7
represents hydrogen, amino or represents respectively optionally fluorine-and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyl, butenyl, propinyl or butinyl.
The general of preferred radical definitions listed above are valid radicals for the end products of formula (I) and also, in a corresponding manner, for the starting materials or intermediates which are required in each case for the preparation. These radical definitions can be combined with each other at will, i.e. combinations between the given preferred ranges are also possible.
Using, for example, 1-(4-chloro-2-fluoro-5-methylsulphonylamino-phenyl)-3,6-dihydro-2,6-

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