Substituted phenyl uracils

Details Substituted phenyl uracils Substituted phenyl uracils

2000-05-23

2002-08-13

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S240000, C504S236000, C544S310000, C544S311000, C544S312000, C544S295000, C544S296000, C544S284000

Reexamination Certificate

active

06432879

ABSTRACT:

The invention relates to novel substituted phenyluracils, to processes for their preparation and to their use as herbicides.
A large number of substituted aryluracils have already been disclosed in the (patent) literature (cf. JP-A-05 202 031, JP-A-05 039 272, U.S. Pat. Nos. 5,344,812, 5,399,543, WO-A-95/17096). However, these compounds have as yet not attained any particular importance.
This invention, accordingly, provides novel substituted phenyluracils of the general formula (I)
in which
n represents the number 0, 1, 2 or 3,
Q represents O, S. SO, SO
2
, NH or N(alkyl),
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 or represents one of the groupings below —NH—CO—R
7
or —N(CO—R
7
)
2
,
R
5
represents nitro, amino, hydroxyl, mercapto, carboxyl, cyano, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, aminosulfonyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino or bis-alkylsulfonyl-amino,
R
6
represents optionally substituted aryl or represents optionally substituted heterocyclyl from the group consisting of furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, dioxolanyl, dioxanyl, benzodioxanyl, pyrrolyl, pyrazolyl, imidazolyl, benzimidazolyl, triazolyl, oxazolyl, isoxazolyl, benzoxazolyl, thiazolyl, isothiazolyl, benzothiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, and
R
7
represents hydrogen or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl.
In the definitions, the hydrocarbon chains, such as alkyl—also in combination with heteroatoms, such as in alkoxy—are in each case straight-chain or branched.
The invention preferably provides substituted phenyluracils of the formula (I), in which
n represents the number 0, 1, 2 or 3,
Q represents O, S, SO, SO
2
, NH or N(C
1
-C
4
-alkyl),
R
1
represents hydrogen, amino or optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 4 carbon atoms,
R
2
represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl or alkoxycarbonyl having in each case 1 to 4 carbon atoms,
R
3
represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 4 carbon atoms,
R
4
represents nitro, amino or represents one of the groupings below —NH—CO—R
7
or —N(CO—R
7
)
2
,
R
5
represents nitro, amino, hydroxyl, mercapto, carboxyl, cyano, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, aminosulfonyl, halogen, or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino or bis-alkylsulfonyl-amino having in each case 1 to 6 carbon atoms in the alkyl groups,
R
6
represents in each case optionally nitro-, cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, sulfo-, chlorosulfonyl-, aminosulfonyl-, 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
-alkylsulfinyl-, C
1
-C
4
-halogenoalkylsulfinyl-, C
1
-C
4
-alkylsulfonyl-, C
1
-C
4
-halogenoalkylsulfonyl- or C
1-C
4
-alkoxy-carbonyl-substituted phenyl, naphthyl or heterocyclyl from the group consisting of furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, dioxolanyl, dioxanyl, benzodioxanyl, pyrrolyl, pyrazolyl, imidazolyl, benzimidazolyl, triazolyl, oxazolyl, isoxazolyl, benzoxazolyl, thiazolyl, isothiazolyl, benzothiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, and
R
7
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 6 carbon atoms in the alkyl groups, represents in each case optionally cyano- or halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally nitro-, cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, sulfo-, chlorosulfonyl-, aminosulfonyl-, 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
-alkylsulfinyl-, C
1
-C
4
-halogenoalkylsulfinyl-, C
1
-C
4
-alkylsulfonyl-, C
1
-C
4
-halogenoalkyl sulfonyl- or C
1
-C
4
-alkoxycarbonyl-substituted phenyl, naphthyl or heterocyclyl from the group consisting of furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, benzodioxanyl, pyrrolyl, pyrazolyl, imidazolyl, benzimidazolyl, oxazolyl, isoxazolyl, benzoxazolyl, benzothiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl.
The invention relates in particular to compounds of the formula (I) in which
n represents the number 0, 1 or 2,
Q represents O, S, SO, SO
2
, NH or N(CH
3
),
R
1
represents hydrogen, amino or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,
R
2
represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, fluorine-, chlorinc-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,
R
3
represents hydrogen, fluorine, chlorine, bromine or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl,
R
4
represents nitro, amino or represents one of the groupings below —NH—CO—R
7
or —N(CO—R
7
)
2
,
R
5
represents nitro, amino, hydroxyl, mercapto, carboxyl, cyano, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, aminosulfonyl, fluorine, chlorine, bromine, or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, bis-methylsulfonyl-amino or bis-ethylsulfonyl-amino,
R
6
represents in each case optionally nitro-, cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, sulfo-, chlorosulfonyl-, aminosulfonyl-, 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
-alkylsulfinyl-, C
1
-C
4
-halogenoalkylsulfinyl-, C
1
-C
4
-alkylsulfonyl-, C
1
-C
4
-halogenoalkylsulfonyl- or C
1
-C
4
-alkoxy-carbonyl-substituted phenyl, naphthyl or heterocyclyl from the group consisting of furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, dioxolanyl, dioxanyl, benzodioxanyl, pyrrolyl, pyrazolyl, imidazolyl, benzimidazolyl, triazolyl, oxazolyl, isoxazolyl, benzoxazolyl, thiazolyl, isothiazolyl, benzothiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, and
R
7
represents hydrogen, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl,

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