Substituted phenyluracils

Details Substituted phenyluracils Substituted phenyluracils

2001-06-22

2002-03-26

Ford, John M. (Department: 1624)

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

Organic compounds

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

C544S309000, C544S310000, C544S311000, C544S312000, C544S313000, C544S314000

Reexamination Certificate

active

06362337

ABSTRACT:

TECHNICAL FIELD OF THE INVENTION
The invention relates to novel substituted phenyluracils, to processes for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
A large number of substituted aryluracils is already known from the (patent) literature (cf. JP-A-04178373—cited in Chem. Abstracts 118:59721; JP-A-05039272—cited in Chem. Abstracts 119:180805; JP-A-05202031—cited in Chem. Abstracts 120:107048; EP-A-545206; U.S. Pat. Nos. 5,169,430; 5,344,812; 5,399,543; WO-A-95/17096; WO-A-97/08953). However, these compounds have hitherto not attained any particular importance.
DETAILED DESCRIPTION OF THE INVENTION
Novel substituted phenyluracils of the general formula (I)
in which
n represents the numbers 0, 1, 2 or 3,
Q represents oxygen or sulphur,
R
1
represents hydrogen, amino or optionally substituted alkyl,
R
2
represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally substituted alkyl or alkoxycarbonyl,
R
3
represents hydrogen, halogen or optionally substituted alkyl,
R
4
represents nitro, amino, hydroxyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, aminosulphonyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, bis-alkylcarbonyl-amino, bis-alkylsulphonyl-amino or N-alkylcarbonyl-N-alkylsulphonyl-amino, and
R
5
represents hydrogen or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkenyloxy, alkenylamino, alkinyl, alkinyloxy, alkinylamino, cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylamino, aryl, aryloxy, arylthio, arylamino, arylalkyl, arylalkyoxy, arylalkylthio, arylalkylamino, heterocyclyl or heterocyclylalkyl
have now been found.
The invention preferably provides compounds of the formula (I) in which
n represents the numbers 0, 1, 2 or 3,
Q represents oxygen or sulphur,
R
1
represents hydrogen, represents amino or represents optionally cyano-, fluorine-, or chlorine-substituted alkyl having 1 to 4 carbon atoms,
R
2
represents cyano, carboxyl, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, fluorine- or chlorine-substituted alkyl or alkoxycarbonyl having in each case up to 4 carbon atoms,
R
3
represents hydrogen, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms,
R
4
represents nitro, amino, hydroxyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, sulfo, chlorosulphonyl, aminosulphonyl, halogen, or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, bis-alkylcarbonyl-amino, bis-alkylsulphonyl-amino or N-alkylcarbonyl-N-alkylsulphonyl-amino having in each case up to 5 carbon atoms in the alkyl groups, and
R
5
represents hydrogen, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 5 carbon atoms, represents in each case optionally cyano- or halogen-substituted alkenyl, alkenyloxy, alkenylamino, alkinyl, alkinyloxy or alkinylamino having in each case up to 5 carbon atoms, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 3 carbon atoms in the alkyl moieties, represents in each case optionally nitro-, cyano-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-halogenoalkylthio-, C
1
-C
4
-alkylsulphinyl-, C
1
-C
4
-halogenoalkylsulphinyl-, C
1
-C
4
-alkylsulphonyl-, C
1
-C
4
-halogenoalkylsulphonyl- or phenyl-substituted aryl, aryloxy, arylthio, arylamino, arylalkyl, arylalkoxy, arylalkylthio or arylalkylamino having in each case 6 or 10 carbon atoms in the aryl groups and optionally 1 to 3 carbon atoms in the alkyl moieties, or represents in each case optionally cyano-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted heterocyclyl or heterocyclylalkyl from the group consisting of furyl, tetrahydrofuryl, furyl-C
1
-C
4
-alkyl, benzofuryl, benzofuryl-C
1
-C
4
-alkyl, thienyl, thienyl-C
1
-C
4
-alkyl, benzothienyl, benzothienyl-C
1
-C
4
-alkyl, oxazolyl, oxazolyl-C
1
-C
4
-alkyl, benzoxazolyl, benzoxazolyl-C
1
-C
4
-alkyl, isoxazolyl, isoxazolyl-C
1
-C
4
-alkyl, benzisoxazolyl, benzisoxazolyl-C
1
-C
4
-alkyl, thiazolyl, thiazolyl-C
1
-C
4
-alkyl, benzothiazolyl, benzothiazolyl-C
1
-C
4
-alkyl, pyrazolyl, pyrazolyl-C
1
-C
4
-alkyl, oxadiazolyl, oxadiazolyl-C
1
-C
4
-alkyl, thiadiazolyl, thiadiazolyl-C
1
-C
4
-alkyl, pyridyl, pyridyl-C
1
-C
4
-alkyl, quinolyl, quinolyl-C
1
-C
4
-alkyl, pyrimiyl, pyrimidyl-C
1
-C
4
-alkyl.
The invention relates in particular to compounds of the formula (I) in which
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulphur,
R
1
represents hydrogen, amino, methyl or ethyl,
R
2
represents cyano, carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, chlorofluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoroethyl, fluorodichloroethyl, pentafluoroethyl, methoxycarbonyl or ethoxycarbonyl,
R
3
represents hydrogen, chlorine, bromine or methyl,
R
4
represents nitro, amino, hydroxyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, aminosulphonyl, fluorine, chlorine, bromine, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy- or ethoxy-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, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, n-, i-, s- or t-butylsulphonylamino, bis-methylsulphonyl-amino, bis-ethylsulphonyl-amino, N-acetyl-N-methylsulphonyl-amino or N-acetyl-N-ethylsulphonyl-amino, and
R
5
represents hydrogen, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-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, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, represents in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinylamino or butinylamino, represents in each case optionally cyano-, fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclo-pentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, represents in each

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