Substituted p-trifluoromethylphenyluracils

Details Substituted p-trifluoromethylphenyluracils Substituted p-trifluoromethylphenyluracils

2000-08-01

2002-09-03

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S310000, C544S311000, C544S312000, C544S313000, C544S314000

Reexamination Certificate

active

06444616

ABSTRACT:

The invention relates to novel substituted p-trifluoromethylphenyluracils, to a process for their preparation and to their use as herbicides.
It is known that certain substituted p-trifluoromethylphenyluracils, such as, for example, the compound 3-(3-chloro-4-trifluoromethyl-phenyl)-6-(2,6-difluoro-phenyl)-[1H,3H]-pyrimidine-2,4-dione, have pesticidal properties, i.e. they are active against certain animal pests, in particular against insects and mites (cf. JP 05025142—cited in Chem. Abstracts 119:117269). However, nothing has yet been disclosed about a herbicidal activity of these compounds.
This invention, accordingly, provides the novel substituted p-trifluoromethylphenyluracils of the general formula (I)
in which
R
1
represents hydrogen, cyano or halogen,
R
2
represents the grouping A
1
—A
2
—A
3
in which
A
1
represents a single bond, represents O, S, —SO—, —SO
2
—, —CO— or the grouping —N—A
4
— in which A
4
represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl, alkoxy, aryl, alkylsulphonyl or arylsulphonyl,
A
1
furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene, each of which is optionally substituted by halogen,
A
2
represents a single bond, represents O, S, —SO—, —SO
2
—, —CO— or the grouping —N—A
4
13
in which A
4
represents hydrogen, hydroxyl, alkyl, alkoxy, aryl, alkylsulphonyl or arylsulphonyl,
A
2
furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene, each of which is optionally substituted by halogen,
A
3
represents hydrogen, hydroxyl, mercapto, amino, cyano, isocyanato, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chorosulphonyl, halogen, represents alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl, each of which is optionally substituted by halogen or alkoxy, represents alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl, each of which is optionally substituted by halogen, represents cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, each of which is optionally substituted by halogen, cyano, carboxyl, alkyl and/or alkoxy-carbonyl, or represents aryl, aryloxy, aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbonyl, each of which is optionally substituted by nitro, cyano, carboxyl, halogen, alkyl, halogenoalkyl, alkyloxy, halogenoalkyloxy and/or alkoxy-carbonyl,
A
3
furthermore represents in each case optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylalkyl, furylalkyl, thienylalkyl, oxazolylalkyl, isoxazolalkyl, thiazolalkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy, furylalkoxy, represents perhydropyranylalkoxy or pyridylalkoxy,
R
3
represents hydrogen, halogen or optionally halogen-substituted alkyl,
R
4
represents optionally halogen-substituted alkyl, and
R
5
represents hydrogen, amino or optionally hydroxyl-, cyano-, halogen- or alkoxy-substituted alkyl.
The novel substituted p-trifluoromethylphenyluracils of the general formula (I) are obtained when
aminoalkenoic esters of the general formula (II)
in which
R
3
and R
4
are each as defined above and
R represents alkyl, aryl or arylalkyl
are reacted with p-trifluoromethylphenyl isocyanates of the general formula (III)
in which
R
1
and R
2
are each as defined above
or with p-trifluoromethylphenylurathanes (p-trifluoromethylphenylcarbamates) of the general formula (IV)
in which
R
1
and R
2
are each as defined above and
R represents alkyl, aryl or arylalkyl,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, further conversions within the scope of the above definitions of substituents are carried out by customary methods on the resulting compounds of the formula (I).
The compounds of the general formula (I) can be converted by customary methods into other compounds of the general formula (I) according to the above definitions of substituents, for example by customary electrophilic or nucleophilic substitution reactions (for example R
2
: F→OH, SH, NH
2
, OCH
3
, SC
2
H
5
, NHC
3
H
7
, NHSO
2
CH
3
; R
5
: HNH
2
, CH
3
)—cf. also the preparation examples.
The novel substituted p-trifluoromethylphenyluracils of the general formula (I) have strong herbicidal activity. Additionally, they are well tolerated by important crop plants, such as, for example, wheat, barley and maize.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl—also in combination with heteroatom's, such as in alkoxy or alkylthio—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
R
1
represents hydrogen, cyano, fluorine, chlorine or bromine,
R
2
represents the grouping A
1
—A
2
—A
3
in which
A
1
represents a single bond, represents O, S, —SO—, —SO
2
—, —CO— or the grouping —N—A
4
— in which A
4
represents hydrogen, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, phenyl, C
1
-C
4
-alkylsulphonyl or phenylsulphonyl,
A
1
furthermore represents C
1
-C
6
-alkanediyl, C
2
-C
6
-alkenediyl, C
2
-C
6
-alkinediyl, C
3
-C
6
-cycloalkanediyl, C
3
-C
6
-cycloalkenediyl or phenylene, each of which is optionally substituted by fluorine or chlorine,
A
2
represents a single bond, represents O, S, —SO—, SO
2
—, —CO— or the grouping —N—A
4
— in which A
4
represents hydrogen, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, phenyl, C
1
-C
4
-alkylsulphonyl or phenylsulphonyl,
A
2
furthermore represents C
1
-C
6
-alkanediyl, C
2
-C
6
-alkenediyl, C
2
-C
6
-alkinediyl, C
3
-C
6
-cycloalkanediyl, C
3
-C
6
-cycloalkenediyl or phenylene, each of which is optionally substituted by fluorine or chlorine,
A
3
represents hydrogen, hydroxyl, mercapto, amino, cyano, isocyanato, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen, represents alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl having in each case 1 to 6 carbon atoms in the alkyl groups and being in each case optionally substituted by fluorine, chlorine, bromine or C
1
-C
4
-alkoxy, represents alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl having in each case 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups and being in each case optionally substituted by fluorine, chlorine or bromine, represents cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups and being in each case optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C
1
-C
4
-alkyl and/or C
1
-C
4
-alkoxy-carbonyl, or represents phenyl, phenyloxy, phenyl-C
1
-C
4
-alkyl, phenyl-C
1
-C
4
-alkoxy, phenyloxycarbonyl or phenyl-C
1
-C
4
-alkoxycarbonyl, each of which is optionally substituted by nitro, cyano, carboxyl, fluorine, chlorine, bromine, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkyloxy, C
1
-C
4
-halogenoalkyloxy and/or C
1
-C
4
-alkoxy-carbonyl, represents (in each case optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C
1
-C
4
-alkyl, furyl-C
1
-C
4
-alkyl, thienyl-C
1
-C
4
-al

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