Substituted phenyluracils with herbicidal effect

Details Substituted phenyluracils with herbicidal effect Substituted phenyluracils with herbicidal effect

2000-09-05

2003-04-15

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S309000, C544S310000, C544S311000, C544S312000, C544S313000, C544S314000

Reexamination Certificate

active

06548449

ABSTRACT:

The invention relates to novel substituted phenyluraciles, to processes for their preparation and to their use as herbicides.
A large number of substituted aryluraciles is already known from the (patent) literature (cf. U.S. Pat. No. 5,399,543, WO-A-95 17 096). However, these compounds have hitherto not attained any particular significance.
This invention, accordingly, provides novel substituted phenyluraciles of the general formula (I)
in which
m represents the numbers 0,1 or 2,
n represents the numbers 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 hydrogen, cyano or halogen,
R
5
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 or alkylsulphonylamino, and
R
6
represents nitro, amino or represents one of the groupings below —NH—R
8
, —N(R
8
)
2
, —NH—SO
2
—R
8
, —N(R
8
)(SO2—R
8
), —N(SO
2
—R
8
)
2
, —NH—CO—R
9
, —N(R
8
)(CO—R
9
), —N(CO—R
9
)
2
, —N(SO
2
—R
8
)(CO—R
9
),
R
7
represents nitro, amino, hydroxyl, mercapto, 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, alkylsulphonyl-amino or bis-alkylsulphonyl-amino,
R
8
represents in each case optionally substituted alkyl, alkenyl, cycloalkyl, aryl, arylalkyl or heterocyclyl, and
R
9
represents hydrogen or represents in each case optionally substituted alkyl, alkoxy, alkylamino, dialkylamino, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
except for the prior-art compounds 1-[4-(4-nitro-phenylmethoxy-phenyl)]-3-methyl-4-trifluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine and 1-[2-fluoro-4-(4-nitro-phenylmethoxy-phenyl)]-3-methyl-4-trifluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine (cf. U.S. Pat. No. 5,399,543 and WO-A-95 17 096).
In the definitions, the hydrocarbon chains, such as alkyl—including in combination with heteroatoms, such as an alkoxy—are in each case straight-chain or branched.
The invention preferably provides substituted phenyluraciles of the formula (I) in which
m represents the numbers 0, 1 or 2,
n represents the numbers 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 6 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 up to 6 carbon atoms,
R
3
represents hydrogen, halogen or optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 6 carbon atoms,
R
4
represents hydrogen, cyano or halogen,
R
5
represents nitro, amino, hydroxyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, sulpho, 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 or alkylsulphonylamino having in each case up to 6 carbon atoms, and
R
6
represents nitro, amino or one of the groupings below —NH—R
8
, —N(R
8
)
2
, —NH—SO
2
—R
8
, —N(R
8
)(SO2—R
8
), —N(SO
2
—R
8
)
2
, —NH—CO—R
9
, —N(R
8
)(CO—R
9
), —N(CO—R
9
)
2
, —N(SO
2
—R
8
)(CO—R
9
),
R
7
represents nitro, amino, hydroxyl, mercapto, carboxyl, cyano, carbamoyl, thiocarbamoyl, sulpho, 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 or bis-alkylsulphonyl-amino having in each case up to 6 carbon atoms,
R
8
represents optionally halogen-substituted alkyl having 1 to 6 carbon atoms, represents optionally halogen-substituted alkenyl having 2 to 6 carbon atoms, represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, represents in each case optionally nitro-, cyano-, thiocarbamoyl-, 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 C
1
-C
4
-alkoxy-carbonyl-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, or represents optionally 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- or C
1
-C4-halogenoalkylsulphonyl-substituted heterocyclyl from the series consisting of furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridyl, pyrimidyl, and
R
9
represents hydrogen, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms, 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 group and optionally 1 to 4 carbon atoms in the alkyl moiety, represents in each case optionally nitro-, cyano-, thiocarbamoyl-, 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 C
1
-C
4
-alkoxy-carbonyl-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, or represents optionally cyano-, halogen-, C1-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- or C
1
-C
4
-halogenoalkylsulphonyl-substituted heterocyclyl from the series consisting of furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridyl, pyrimidyl,
except for the prior-art compounds 1-[4-(4-nitro-phenylmethoxy-phenyl)]-3-methyl-4-tri fluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine and 1-[2-fluoro-4-(4-nitro-phenylmethoxy-phenyl)]-3-methyl-4-trifluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine (cf. U.S. Pat. No. 5,399,543 and WO-A-95 17 096).
The invention relates in particular to compounds of the formula (I) in which
m represents the numbers 0, 1 or 2,
n represents the numbers 0, 1 or 2,
Q represents O, S, SO, SO
2
, NH or N(CH
3
),
R
1
represents hydrogen, amino or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
R
2
represents carboxyl, cyano, carbamoyl, thiocarbamoyl, or represents in each case optionally cyano-, fluorine-, chlorine-, methox

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