DE19528305A1 - Substituted phenyluracile - Google Patents

Abstract

New substituted phenyluracils have the general formula (I), in which R<1> stands for hydrogen, cyano or halogen; R<2> stands for cyano, carbamoyl, thiocarbamoyl, halogen or optionally halogen-substituted alkyl or alkoxy; R<3> stands for the group A<1>-A<2>-A<3>, in which A<1>, A<2> and A<3> have the meanings given in the description; R<4> stands for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, halogen, alkoxycarbonyl, alkylamino, dialkylamino, or for alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio or alkinylthio optionally substituted by hydroxy, nitro, cyano, halogen or alkoxy; R<5> stands for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, halogen, alkoxycarbonyl, alkylamino, dialkylamino, or for alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio or alkinylthio optionally substituted by hydroxy, nitro, cyano, halogen or alkoxy; and R<6> stands for hydrogen, hydroxy, amino, cyano, or for alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl optionally substituted by cyano, nitro, halogen or alkoxy, or for cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or alkyl, with the exception of compounds 1-(4-chloro-2-fluoro-phenyl)-1,2,3,4-tetrahydro-2,4-dioxo-pyrimidin-5- carbonitril, 1-(3-chloro-4-fluoro-phenyl)-1,2,3,4-tetrahydro-2,4-dioxo-pyrimidin-5- carbonitril, 1-(4-chloro-3-trifluoromethylphenyl)-1,2,3,4-tetrahydro-2,4-dioxo-pyri midin-5-carbonitril, 1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-2,4-dioxo-pyrimidin-5-carbon itril, 1-[4-chloro-2-fluoro-5-(2-propinyloxy)-phenyl]-3-methyl-2,4-(1H,3H)-py ridindione. Also disclosed is a process for preparing these compounds and their use as herbicides.

Description

The invention relates to new substituted phenyluracils, processes for their manufacture position and their use as herbicides.

Substituted uraciles, such as. B. the compounds 1- (4-chloro-2-fluorophenyl) - 1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, 1- (3-chloro-4-fluorophenyl) - 1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, 1- (4-chloro-3-trifluoromethyl phenyl) -1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile and 1- (3,4-dichloro phenyl) -1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile (cf. US 4266056) so such as 1- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -3-methyl-2,4- (1H, 3H) -pyridine dion (cf. US 5298502) are already known from the patent literature. About one ago However, nothing is known about the bicidal activity of these compounds been.

The new substituted phenyluracils of the general formula (I) found

in which
R¹ represents hydrogen, cyano or halogen,
R² stands for cyano, carbamoyl, thiocarbamoyl, halogen or for alkyl or alkoxy which is optionally substituted by halogen,
R³ represents the group A¹-A²-A³, wherein
A¹ is a single bond, oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ is hydrogen, hydroxy, alkyl, alkenyl, alkynyl, alkoxy, aryl, alkylsulfonyl or Arylsulfonyl,
A¹ furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
A² represents a single bond, represents oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ represents hydrogen, hydroxy, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl,
A² furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
A³ represents hydrogen with the proviso that in this case A¹ and / or A² do not represent a single bond,
A³ furthermore for hydroxy, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbon, each optionally substituted by halogen or alkoxy or dialkoxy (thio) phosphoryl, for alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxy carbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxy carbonyl, each optionally substituted by halo, cyano, carboxy, alkyl and / or alkoxy carbonyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidene amino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, or for each aryl, aryloxy, aralkyl, arylalkoxy, optionally substituted by nitro, cyano, carboxy, halogen, alkyl, haloalkyl, alkyloxy, haloalkyloxy and / or alkoxy , Aryloxy carbonyl or arylalkoxycarbon yl stands,
A³ furthermore for each optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, tridylyl, furidyl, pyridinyl, pyriminyl, pyriminyl, pyriminyl, pyriminyl Thienylalkyl, oxazolylalkyl, isoxazolealkyl, thiazolealkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy, furylalkoxy, represents perhydropyranylalkoxy or pyridylalkoxy,
R⁴ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, halo gene, alkoxycarbonyl, alkylamino, dialkylamino, or for alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, optionally substituted by hydroxy, nitro, cyano, halogen or alkoxy, Alkynyloxy, alkylthio, alkenylthio or alkynylthio,
R⁵ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, halo gene, alkoxycarbonyl, alkylamino, dialkylamino, or for alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, optionally substituted by hydroxy, nitro, cyano, halogen or alkoxy , Alkylthio, alkenylthio or alkynylthio, and
R⁶ for hydrogen, hydroxy, amino, cyano, for each optionally substituted by cyano, nitro, halogen or alkoxy-substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, or for each optionally substituted by cyano, halogen or alkyl Cycloalkyl or cycloalkylalkyl,
where the previously known compounds 1- (4-chloro-2-fluorophenyl) -1,2,3,4-tetra hydro-2,4-dioxopyrimidine-5-carbonitrile, 1- (3-chloro-4- fluorophenyl) -1,2,3,4-tetra hydro-2,4-dioxopyrimidine-5-carbonitrile, 1- (4-chloro-3-trifluoromethyl-phenyl) -1,2,3,4- tetrahydro-2,4-dioxopyrimidine-5-carbonitrile and 1- (3,4-dichlorophenyl) - 1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile (cf. US 4266056) and 1- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -3-methyl-2,4- (1H, 3H) -pyridine-dione (see US 5298502) Disclaimers are excluded.

The new substituted phenyluracils of the general formula (I) are obtained if

(a) Halogenarenes of the general formula (II)

in which
R¹, R² and R³ have the meaning given above and
X¹ represents halogen,
with uracenes of the general formula (III)

in which
R⁴, R⁵ and R⁶ have the meaning given above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or if you
(b) aminoarenes of the general formula (IV)

in which
R¹, R² and R³ have the meaning given above,
with 3-alkoxy-1-oxo-2-alkenyl-carbamic acid esters of the general formula (V)

in which
R⁴, R⁵ and R⁶ have the meaning given above, and
R represents alkyl,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.

The compounds of the general formula (I) can also be prepared according to other conventional methods Methods in other compounds of general formula (I) according to the above Definition can be converted, for example by nucleophilic substitution (e.g. R³: F → OH, SH, NH₂, OCH₃, NHSO₂CH₃; by alkylation (e.g. R⁶: H → CH₃); or by further conversions of functional groups (e.g. R²:  CONH₂ → CN, CN → CSNH₂; R³: NO₂ → NH₂, NH₂ → F, Cl, Br, CN, NHSO₂CH 3, SO₂Cl) - cf. also the manufacturing examples.

The new substituted phenyluracils of the general formula (I) stand out from strong herbicidal activity.

In the definitions are the saturated or unsaturated hydrocarbon chains such as alkyl, alkenyl or alkynyl each straight or branched.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably Fluorine, chlorine or bromine, especially for fluorine or chlorine.

The invention preferably relates to compounds of formula (I), in which cher
R¹ represents hydrogen, cyano, fluorine, chlorine or bromine,
R² stands for cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for alkyl or alkoxy, each optionally substituted by fluorine and / or chlorine, each having 1 or 2 carbon atoms,
R³ represents the group -A¹-A²-A³,
in which
A¹ is a single bond, oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ is hydrogen, hydroxy, C₁-C₄-alkyl, C₃-C₄-alkenyl, C₃-C₄-alkynyl, C₁-C₄-alk oxy, phenyl, C₁-C₄-alkylsulfonyl or phenylsulfonyl,
A¹ further for each optionally substituted by fluorine, chlorine or bromine, C₁-C Alk-alkanediyl, C₂-C₆-alkenediyl, C₂-C₆-azaalkenedyl, C₂-C₆-alkynediyl, C₃-C₆-cycloalkanediyl, C₃-C₆-cycloalkenediyl or phenylene stands,
A² represents a single bond, represents oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, in which A⁴ represents hydrogen, hydroxy, C₁-C₄-alkyl, C₁-C₄-alkoxy, Phenyl, C₁-C₄ alkylsulfonyl or phenylsulfonyl,
A² further for each optionally substituted by fluorine, chlorine or bromine, C₁-C₆alkanediyl, C₂-C₆alkenediyl, C₂-C₆alkaalkenediyl, C₂-C₆alkanediyl, C₃-C₆cycloalkanediyl, C₃-C₆cycloalkenediyl or phenylene stands,
A³ represents hydrogen, with the proviso that in this case A¹ and / or A² do not represent a single bond,
A³ furthermore for hydroxy, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, for each optionally substituted by fluorine, chlorine or C₁-C₄alkoxy alkyl, alkoxy, alkylthio , Alkyl sulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkynyl, alkynyloxy optionally substituted by fluorine or chlorine , Alkynylamino or alkynyloxycarbonyl, each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, each for optionally by fluorine, chlorine, cyano, carboxy, C₁-C₄-alkyl and / or C₁-C₄-alkoxy-carbonyl substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidene amino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl each having 3 to 6 carbons Substance atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkyloxy, C₁ -C₄-haloalkyloxy and / or C₁-C₄-alkoxy-carbonyl-substituted phenyl, phenyloxy, phenyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, phenyloxycarbonyl or phenyl-C₁-C₄-alkoxycarbonyl,
A³ furthermore for each optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, ox etanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, azimidinyl, pyriminyl, pyriminyl, pyriminyl C₁-C₄-alkyl, furyl-C₁-C₄-alkyl, thienyl-C₁-C₄-alkyl, oxazolyl-C₁-C₄-alkyl, isoxazole-C₁-C₄-alkyl, thiazole-C₁-C₄-alkyl, pyridinyl- C₁-C₄-alkyl, pyrimidinyl-C₁-C₄-alkyl, pyrazolylmeth oxy, furylmethoxy, represents perhydropyranylmethoxy or pyridyl methoxy, or
R⁴ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, fluorine, chlorine, bromine, C₁-C₄-alkoxy-carbonyl, C₁-C₄-alkylamino, di- (C₁-C₄-alkyl) - amino, or for each optionally alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio or alkynylthio, each with up to 6 carbon atoms, is substituted by hydroxy, nitro, cyano, fluorine, chlorine, bromine or C₁-C₄alkoxy,
R⁵ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, fluorine, chlorine, bromine, C₁-C₄-alkoxy-carbonyl, C₁-C₄-alkylamino, di- (C₁-C₄-alkyl) - amino, or for each optionally alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio or alkynylthio, each having up to 6 carbon atoms, is substituted by hydroxy, nitro, cyano, fluorine, chlorine, bromine or C₁-C₄alkoxy, and
R⁶ for hydrogen, hydroxy, amino, cyano, for each optionally substituted by cyano, nitro, fluorine, chlorine, bromine or C₁-C₄alkoxy-substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkyl sulfonyl, each with up to 6 carbon atoms, or for cycloalkyl or cycloalkylalkyl which is optionally substituted by cyano, fluorine, chlorine, bromine or C₁-C₄alkyl and has 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups,
where the previously known compounds 1- (4-chloro-2-fluorophenyl) -1,2,3,4-tetra hydro-2,4-dioxopyrimidine-5-carbonitrile, 1- (3-chloro-4- fluorophenyl) -1,2,3,4-tetrahy dro-2,4-dioxopyrimidine-5-carbonitrile, 1- (4-chloro-3-trifluoromethylphenyl) -1,2,3,4- tetrahydro-2,4-dioxopyrimidine-5-carbonitrile and 1- (3,4-dichlorophenyl) -1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile (cf. US 4266056) and 1- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -3-methyl-2,4- (1H, 3H) -pyridinedione (cf. US 5298502) excepted by disclaimers are.

The invention relates in particular to compounds of the formula (I) in which
R¹ represents hydrogen, fluorine or chlorine,
R² represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, methyl or trifluoromethyl,
R³ represents the group -A¹-A²-A³,
in which
A¹ is a single bond, oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, where A⁴ is hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy , Ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl,
A¹ further for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2 -diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl or propyne-1,3-diyl,
A² represents a single bond, represents oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ represents hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy , Ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
A² furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2 -diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl or propyne-1,3-diyl,
A³ represents hydrogen, with the proviso that in this case A¹ and / or A² do not represent a single bond,
A³ furthermore for hydroxyl, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, n-, i-, each optionally substituted by fluorine, chlorine, methoxy or ethoxy -, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i -, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methyl amino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butyl amino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, di ethoxyphosphoryl or dipropoxyphosphoryl, diisopropoxyphosphoryl, for propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycar bonyl, each optionally substituted by fluorine or chlorine, Butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, for each cyclopropyl, cyclobutyl, optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl , Cyclo pentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyl oxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclo pentylmethyl, cyclohexylmethyl, cyclo-propyl methoxy, cyclobutyl methoxy, cyclopentyl methoxy, cyclohexyl methoxy cyclyl cyclyl carbonyl, cyclo cyclo methoxy cyclo cyclo methoxy cyclo cyclo methoxy cyclo cyclo methoxy cyclo cyclo methoxy cyclo cyclo methoxy or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, di fluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or Ethoxy carbonyl substituted phenyl, phenyloxy, benzyl, pheny methyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl,
A³ further for (in each case fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethylmylylylylylmethyl, furylmethylmylylylmethyl, furlmethylmethyl , Isoxazolmethyl, Thiazolmethyl, Pyridinyl methyl, Pyrimidinylmethyl, Pyrazolylmethoxy, Furylmethoxy or Pyridylmethoxy,
R⁴ represents hydrogen, cyano, fluorine, chlorine or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine,
R⁵ represents hydrogen, cyano, fluorine, chlorine or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine, and
R⁶ represents hydrogen, amino, cyano or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, Propynyl or butynyl,
where the previously known compounds 1- (4-chloro-2-fluorophenyl) -1,2,3,4-tetrahy dro-2,4-dioxopyrimidine-5-carbonitrile, 1- (3-chloro-4- fluorophenyl) -1,2,3,4-tetrahy dro-2,4-dioxopyrimidine-5-carbonitrile, 1- (4-chloro-3-trifluoromethylphenyl) -1,2,3,4- tetrahydro-2,4-dioxopyrimidine-5-carbonitrile and 1- (3,4-dichlorophenyl) -1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile (cf. US 4266056) and 1- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -3-methyl-2,4- (1H, 3H) -pyridinedione (cf. US 5298502) excepted by disclaimers are.

The radicals listed above or listed in preferred areas definitions apply to both the end products of the formula (I) and ent speaking for the respective starting materials or intermediate required for the production products. These residual definitions can be among themselves, that is, between the specified preferred ranges can be combined as desired.

Examples of the compounds of formula (I) according to the invention are in the groups listed below.  

Group 1

Ar has, for example, the meanings listed below:
2,4,5-trichlorophenyl, 2,4-dichloro-5-fluorophenyl, 2-chloro-4,5-difluorophenyl, 4-chloro-2, 5-difluorophenyl, 5-chloro 2,4-difluorophenyl, 2-fluoro-5-chloro-4-cyanophenyl, 2,4,5-trifluorophenyl, 2,5-dichloro-4-cyano-phenyl, 2-chloro-5-fluoro -4-cyanophenyl, 2-chloro-4,5-dicyano-phenyl, 2-chloro-4-fluoro-5-cyano-phenyl, 2,5-difluoro-4-cyano-phenyl, 2-chloro-4-cyano -5-methylphenyl, 2,4-dichloro-5-methoxyphenyl, 2,4-dichloro-5-ethoxyphenyl, 2,4-dichloro-5-n-propoxyphenyl, 2,4-dichloro- 5-i-propoxy-phenyl, 4-chloro-2-fluoro-5-methoxy-phenyl, 4-chloro-2-fluoro-5-ethoxy-phenyl, 4-chloro-2-fluoro-5-n-propoxy-phenyl , 4-chloro-2-fluoro-5-i-propoxy-phenyl, 2-fluoro-4-cyano-5-methylphenyl, 2,4-dichloro-5-methylphenyl, 2-chloro-4-cyano -5-trifluoromethyl-phenyl, 4-fluoro-3-trifluoromethyl-phenyl, 2-fluoro-4-cyano-5-trifluoromethyl-phenyl, 2-chloro-4-methyl-5-trifluoromethyl-phenyl, 2-chloro 5-fluoro-4-methoxy-phenyl, 2-fluoro-4-methoxy-5-methyl-phenyl, 2,5-difluoro-4-thiocarbamoyl phenyl, 2-chloro-4-fluoro-5-i-propoxy-phenyl , 2-fluoro-4-cyano-5-methoxy-phenyl, 2-fluoro-4-cyano-5-i-propoxy-phenyl, 2-chloro-4-cyano-5- (2-propynyloxy) phenyl, 2 - Fluoro-4-cyano-5- (1-methyl-2-propynyloxy) phenyl, 2-chloro-4-thiocarbamoyl-5-i-pro poxy-phenyl, 2-fluoro-4-cyano-5- (2nd propenyloxy) phenyl, 2-fluoro-4-chloro-5- (2-propenyloxy) phenyl, 2-chloro-4-cyano-5-methylsulfonylamino-phenyl, 2-fluoro-4-cyano-5-ethylsulfonylamino- phenyl, 2-fluoro-4-thiocarbamoyl-5-methylsulfonylamino-phenyl, 2-chloro-4-cyano-5-ethylsulfonylamino-phenyl, 2-fluoro-4-cyano-5-cyclopropylsulfonylamino-phenyl, 2-fluoro-4 -cyano-5-i-propylsulfonylamino-phenyl, 2-chloro-4-thiocarbamoyl-5-ethylsulfonylaminophenyl, 2-chloro-4-cyano-5-cyanamino-phenyl, 2-fluoro-4-cyano-5-trifluoromethylsulfonylamino- phenyl, 2-fluoro-4-cyano-5- (2,2-difluoroethylsulfonylamino) phenyl, 2-fluoro-4-cyano-5-phenylsulfonylamino-phenyl, 2-fluoro-4-cyano-5-t-butylsulfonylamino -phenyl, 2-chloro-4-cyano-5-methoxycarbonyl-phenyl, 2-fluoro-4-cyano-5ethoxycarbonyl-phenyl, 2-fluoro-4-thio carbamoyl-5-metho xycarbonyl-phenyl, 2-chloro-4-cyano-5- (N-cyclopropyl-ethy sulfonylamino) phenyl, 2-fluoro-4-cyano-5- (1-methyl-2-propynylthio) phenyl, 2-fluoro -4-cyano-5-methylamino-phenyl, 2-chloro-4-thiocarbamoyl-5-methoxy carbonylmethyl-phenyl, 2-chloro-4-cyano-5- (N-methyl-ethylsulfonylamino) -phenyl, 2-chloro 4-cyano-5-i-propoxycarbonylphenyl, 2-fluoro-4-cyano-5- (bis-ethylsulfonylamino) phenyl, 2-fluoro-4-cyano-5- (N-methylsulfonylylsulfonylamino) phenyl, 2 - fluoro-4-cyano-5- (1-methoxycarbonyl-ethoxy) phenyl, 2-fluoro-4-cyano-5-cyclopropyloxy-phenyl, 2-chloro-4-cyano-5-dimethylamino-phenyl, 2- Fluoro-4-cyano-5-tetrahydrofurylmethoxy-phenyl, 2-fluoro-4-cyano-5-aminophenyl, 2-fluoro-4-cyano-5-methylaminocarbonyl-phenyl, 2-fluoro-4-cyano-5- methylsulfonyloxy-phenyl, 2-chloro-4-cyano-5-difluoromethoxy-phenyl, 2-fluoro-4-cyano-5-ethoxycarbonyl methoxy-phenyl, 2-fluoro-4-cyano-5-dimethylaminocarbonyl-phenyl, 2-fluoro -4-cyano-5-cyanomethoxy-phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-propenyloxy) phenyl, 2-fluoro-4-cyano-5-h ydroxy-phenyl, 2-fluoro-4-cyano-5-nitro-phenyl, 2-fluoro-4-cyano-5-diethoxyphosphorylamino-phenyl, 2-fluoro-4-cyano-5-chlorosulfonyl-phenyl, 2-fluoro 4-cyano-5-formylamino-phenyl, 2-chloro-4-cyano-5-ethoxycarbonyloxy phenyl, 2-fluoro-4-cyano-5-diethoxyphosphorylmethoxy-phenyl, 2-chloro-4-cyano-5-hydroxyphenyl , 2-fluoro-4-cyano-5- (N, N-diacetylamino) phenyl, 2-fluoro-4-cyano-5-acetylamino-phenyl, 2-chloro-4-cyano-5-thiocyanato-phenyl , 2-fluoro-4-cyano-5-diethylaminooxy-phenyl, 2-fluoro-4-cyano-5-tetrahydrofuryloxy-phenyl, 2-fluoro-4-cyano-5-ureido-phenyl, 2-fluoro-4-cyano -5-dimethoxymethyleneaminophenyl, 2-chloro-4-cyano-5-ethoxymethyleneaminophenyl, 2-fluoro-4-cyano-5- (2-chloroethoxycarbonyloxy) phenyl, 2-chloro-4-cyano-5 -dimethylaminomethyleneaminophenyl, 2-chloro-4-cyano-5- (perhydropyran-4-yloxy) -phenyl, 2-fluoro-4-cyano-5- (2-methoxy carbonyl-ethyl) -phenyl, 2-chloro 4-cyano-5- (2-carboxy-2-chloroethyl) phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-methoxycarbonylethyl) phenyl, 2-fluoro-4- cyano-5- (2-chlorine -2-s-butoxycarbonyl) phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-carbamoyl-ethyl) phenyl, 2-fluoro-4-cyano-5- (2-chloro-2 -methoxycarbonyl-1-methyl-ethyl) -phenyl, - 2-fluoro-4-cyano-5- (1,2-dibromo-2-methoxycarbonyl-ethyl) -phenyl, 2-chloro-4-cyano-5- ( 2-chloro-2-i-propoxycarbonyl-ethyl) phenyl, 2,4-dichloro-5- (2-methoxycarbonyl ethyl) phenyl, 2-fluoro-4-cyano-5- (2-carboxy-2-chloro -ethyl) -phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-ethylaminocarbonyl-ethyl) -phenyl, 2-fluoro-4-cyano-5- (2-allyl aminocarbonyl-2-chloro ethyl) phenyl, 2-fluoro-4-cyano-5- (2-ethoxycarbonyl ethenyl) phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-cyclopropylaminocarbonyl-ethyl) phenyl, 2- Fluoro-4-cyano-5- (2-chloro-2-dimethylaminocarbonyl-ethyl) -phenyl, 2-chloro-4-cyano-5- (2-chloro-2-ethylsulfonylaminocarbonyl-ethyl) -phenyl, - 2-fluoro -4-chloro-5- (2-carboxy-ethenyl) phenyl, 2-fluoro-4-thiocarbamoyl-5- (2-ethylamino carbonyl-ethenyl) phenyl, 2-fluoro-4-cyano-5- (1 -ethoxycarbonyl-ethyl) -phenyl, 2-chloro-4-cyano-5- (1-ethoxycarbonylethyl) -phenyl, 2-chloro-4-cyan o-5-carboxyphenyl, 2-fluoro-4-chloro-5- (1-ethoxycarbonyl-ethyl) -phenyl, 2-fluoro-4-chloro-5- (1-i-propoxycarbonyl-ethyl) -phenyl, 2 -Fluoro-4-cyano-5-i-butoxy-phenyl, 2-chloro-4-cyano-5-i-butoxy-phenyl, 2-chloro-4-cyano-5- (2-methoxy-ethoxy) phenyl , 2-fluoro-4-chloro-5- (2-methoxyethoxy) phenyl, 2-fluoro-4-chloro-5-i-butoxyphenyl, 2-fluoro-4-hydroxy-5-i-propoxycarbonyl-phenyl , 2-fluoro-4-cyano-5- (2-oxetanyloxy) phenyl, 2-fluoro-4-cyano-5- (2-oxetanyloxycarbonylmethoxy) phenyl.

Group 2

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 3

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 4

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.  

Group 5

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 6

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 7

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.  

Group 8

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 9

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 10

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.  

Group 11

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 12

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 13

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.  

Group 14

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 15

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 16

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.  

Group 17

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 18

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 19

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.  

Group 20

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 21

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 22

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.  

Group 23

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 24

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 25

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.  

Group 26

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 27

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 28

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.  

Group 29

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 30

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 31

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.  

Group 32

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 33

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

Group 34

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.  

Group 35

Ar, R⁴ and R⁶ have, for example, those given above in Group 1 Meanings.

For example, 2-chloro-4,5-difluoro-benzonitrile and 1,2,3,4-tetra are used hydro-2,4-dioxopyrimidine-5-carbonitrile as starting materials, so the reaction sequence in process (a) according to the invention using the following formula are outlined:

For example, 2,4-dichloro-5-methoxy-aniline and 2-cyano-3-meth are used oxy-1-oxo-2-propenyl-carbamic acid methyl ester as starting materials, so the Reaction flow in the method (b) according to the invention by the following Formula scheme are outlined:

The process (a) according to the invention for the preparation of the compounds of Formula (I) to be used as starting materials are arenas by Formula (II) generally defined. In formula (II), R¹, R² and R³ have preference wise or in particular the meaning already mentioned above in Be prescription of the compounds of formula (I) to be prepared according to the invention preferably or as particularly preferred for R¹, R² and R³; X¹ preferably represents fluorine, chlorine or bromine, especially fluorine or Chlorine.

The starting materials of formula (II) are known and / or can be known Processes are produced (cf. EP 191181, EP 370332, EP 431373, EP 441064.

The process (a) according to the invention for the preparation of the compounds of Formula (I) Uracile to be used as starting materials are by the Formula (III) generally defined. In the formula (III), R⁴, R⁵ and R⁶ have preference wise or in particular the meaning already mentioned above in the description Exercise of the compounds of formula (I) to be prepared according to the invention preferred was indicated as or particularly preferred for R⁴, R⁵ and R⁶.

The starting materials of the formula (III) are known and / or can be known Processes are prepared (see. DE 34 02 193, Chem. Pharm. Bull. 20 (1972), 1380-1388).

The process (b) according to the invention for the preparation of the compounds of Aminoarenes to be used as starting materials are represented by the formula (I) Formula (IV) generally defined. In formula (IV), R¹, R² and R³ have preference wise or in particular the meaning already mentioned above in the description Exercise of the compounds of formula (I) to be prepared according to the invention preferred as indicated or as particularly preferred for R¹, R² and R³.

The starting materials of formula (IV) are known and / or can be known Processes are produced (cf. EP 224001).

The process (b) according to the invention for the preparation of the compounds of Formula (I) 3-alkoxy-1-oxo-2-alkenyl to be used as starting materials Carbamic acid esters are generally defined by the formula (V). In the formula  (V) R⁴, R⁵ and R⁶ preferably or in particular have the meaning the Ver already in the description of the Ver to be produced according to the invention bonds of the formula (I) preferably or as particularly preferred for R⁴, R⁵ and R⁶ was specified.

The starting materials of the formula (V) are known and / or can be known Processes are prepared (see. US 4266056, Chem. Pharm. Bull. 20 (1972), 1380-1388).

Processes (a) and (b) according to the invention for the preparation of the compounds of the formula (I) are preferably in the presence of a suitable reaction auxiliary carried out by means. The reaction aids generally come from usual inorganic or organic bases or acid acceptors into consideration. These preferably include alkali metal or alkaline earth metal acetate, amide, -carbonates, -hydrogencarbonate, -hydride, -hydroxide or -alkanolate, as in for example sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or Calcium hydrogen carbonate, lithium, sodium, potassium or calcium hy drid, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methanolate, ethanolate, n- or i-propanolate, n-, i-, s- or t-butanolate; Farther also basic organic nitrogen compounds, such as trimethyl amine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N- Dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dime thyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2- methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo- [2,2,2] octane (DABCO), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), and 1.8 diaza bicyclo [5,4,0] -undec-7-ene (DBU).

Processes (a) and (b) according to the invention for the preparation of the compounds of formula (I) are preferably carried out in the presence of a diluent guided. The usual organic diluents are generally used Solvent. These preferably include aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons, such as white pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, xylene, Chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane (Methylene chloride), trichloromethane (chloroform) or carbon tetrachloride, dialkyl  ethers, such as, for example, diethyl ether, diisopropyl ether, methyl t-butyl ether (MTBE), ethyl t-butyl ether, methyl t-pentyl ether (TAME), ethyl t-pentyl ether, Tetrahydrofuran (THF), 1,4-dioxane, ethylene glycol dimethyl ether or diethyl ether, diethylene glycol dimethyl ether or diethyl ether; Dialkyl ketones, as with for example acetone, butanone (methyl ethyl ketone), methyl i-propyl ketone or Methyl i-butyl ketone, nitriles, such as, for example, acetonitrile, propionitrile, butyro nitrile or benzonitrile; Amides, such as, for example, N, N-dimethylformamide (DMF), N, N-dimethyl-acetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexa methyl phosphoric acid triamide; Esters, such as, for example, methyl acetate, -ethyl ester, -n- or -i-propyl ester, -n-, -i- or -s-butyl ester; Sulfoxides, as in for example dimethyl sulfoxide; Alkanols, such as methanol, ethanol, n- or i-propanol, n-, i-, s- or t-butanol, ethylene glycol monomethyl ether or monoethyl ether, diethylene glycol monomethyl ether or monoethyl ether; their Mix with water or pure water.

The reaction temperatures can be carried out when carrying out the inventive Processes (a) and (b) can be varied over a wide range. In general one works at temperatures between 0 ° C and 200 ° C, preferably between 10 ° C and 150 ° C, especially between 20 ° C and 120 ° C.

Processes (a) and (b) according to the invention are generally described under Normal pressure carried out. However, it is also possible to use the inventive Processes under increased or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out processes (a) and (b) according to the invention, the off Common materials generally used in approximately equimolar amounts. It is however, it is also possible to use one of the components in a large excess to use. The implementation is generally in a suitable Ver diluent carried out in the presence of a reaction auxiliary and the Re action mixture is generally several hours at the required tem temperature stirred. The processing is carried out according to customary methods (cf. the manufacturing examples).

The active compounds according to the invention can be used as defoliants, desiccants, kraut tabs killers and especially used as a weed killer. Weeds in the broadest sense are understood to mean all plants that are in places  grow up where they are undesirable. Whether the substances according to the invention as total or selective herbicides act essentially depends on the applied Amount off.

The active compounds according to the invention can, for. B. ver in the following plants be applied:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matrica ria, anthemis, galinsoga, chenopodium, urtica, senecio, amaranthus, portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranun culus, Taraxacum.

Dicot cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, lactuca, cucumis, cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecu rus, apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, sorghum, panicum, saccharum, pineapple, asparagus, allium.

However, the use of the active compounds according to the invention is by no means limited to limited to these genera, but also extends in the same way other plants.

Depending on the concentration, the compounds are suitable for the total weed control z. B. on industrial and track systems and on paths and Places with and without tree cover. Likewise, the connections to the Un herb control in permanent crops, e.g. B. forest, ornamental wood, fruit, wine, citrus, Nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and  Hop plants, on ornamental and sports turf and pastures and for selective Weed control can be used in annual crops.

The compounds of formula (I) according to the invention are particularly suitable for selective control of monocot and dicot weeds in mono cotyledon cultures both pre-emergence and post-emergence.

To some extent, the compounds of formula (I) also show insecticidal and acaricidal effectiveness.

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated nated natural and synthetic substances as well as very fine encapsulation in polymers Fabrics.

These formulations are prepared in a known manner, e.g. B. by Ver mixing the active ingredients with extenders, i.e. liquid solvents and / or solid carriers, optionally using surface-active agents Agents, that is emulsifiers and / or dispersants and / or foam generators resources.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylene or methylene chloride, aliphatic coal water serstoffe, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and their ethers and esters, Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and Water.

As solid carriers come into question: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, as solid carriers for granules  come into question: z. B. broken and fractionated natural rocks like Calcite, marble, pumice, sepiolite, dolomite and synthetic granules inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or Foaming agents are possible: B. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fat alcohol ether, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersants come into question: z. B. Lignin sulfite liquor and methyl cellulose.

In the formulations, adhesives such as carboxymethyl cellulose, ver natural and synthetic polymers in powder, granular or latex form be used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well natural phospholipids such as cephalins and lecithins and synthetic phospho lipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalalo cyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, Cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 weight percent active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their form in mixtures with known herbicides for weed control Ver find application, whereby finished formulations or tank mixes are possible.

Known herbicides are suitable for the mixtures, for example anilides, such as B. Diflufenican and Propanil; Arylcarboxylic acids, such as. B. dichloropicolin acid, dicamba and picloram; Aryloxyalkanoic acids, such as. B. 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as B. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones, such as B. Chloridazon and Norflurazon; Carbamates, such as B. Chlorpropham, Desmedipham, Phenmedipham and Propham; Chloroacet anilides, such as B. alachlor, acetochlor, butachlor, metazachlor, metolachlor, Pretilachlor and propachlor; Dinitroanilines such as e.g. B. Oryzalin, Pendimethalin and  Trifluralin; Diphenyl ether, such as. B. acifluorfen, bifenox, fluoroglycofen, Fomesafen, halosafen, lactofen and oxyfluorfen; Ureas, such as B. chlorine toluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; Hydroxylamines, such as. B. Alloxydim, Clethodim, Cycloxydim, Sethoxydim and Tralkoxydim; Imidazolinones, e.g. B. Imazethapyr, Imazamethabenz, Imazapyr and imazaquin; Nitriles such as B. bromoxynil, dichlobenil and ioxynil; Oxy acetamides such as B. Mefenacet; Sulfonylureas, such as. B. Amidosulfuron, Ben sulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, Triasulfuron and tribenuron-methyl; Thiol carbamates such as e.g. B. butylates, cycloates, Dialallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; Triazines, e.g. B. Atrazin, Cyanazin, Simazin, Simetryne, Terbutryne and Terbutylazin; Triazinones such as e.g. B. hexazinone, metamitron and metribuzin; Others, such as B. aminotriazole, benfuresate, bentazone, cinmethylin, Clom azone, clopyralide, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and tridiphanes.

Also a mixture with other known active ingredients, such as fungicides, insects ticides, acaricides, nematicides, bird repellants, plant nutrients substances and soil structure improvers are possible.

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as use figs Solutions, suspensions, emulsions, powders, pastes and granules are used will. The application is done in the usual way, e.g. B. by pouring, spraying, Spray, sprinkle.

The active compounds according to the invention can be used both before and after the up run of the plants can be applied. You can also sow in the soil before sowing be incorporated.

The amount of active ingredient used can vary over a wide range. she depends essentially on the type of effect desired. In general the application rates are between 1 g and 10 kg of active ingredient per hectare of soil area, preferably between 5 g and 5 kg per ha.  

The manufacture and use of the active compounds according to the invention start out the following examples.

Manufacturing examples example 1 (Method (a))

6.5 g (0.05 mol) of 5-fluoro-uracil are mixed with 7.6 g (0.055 mol) of potassium carbonate 100 ml of dimethyl sulfoxide are initially charged with 7.9 g (0.05 mol) of 2,4,5-trifluorobenzonitrile added and stirred at 80 ° C for 12 hours. After cooling to room temperature is stirred with water, with conc. Hydrochloric acid adjusted to pH 4 and the precipitated product is isolated by filtration.

12 g (90% of theory) of 1- (2,5-difluoro-4-cyanophenyl) -5-fluorine are obtained uracil with a melting point <250 ° C.  

Example 2

1.1 g (0.015 mol) of butyn-1-ol- (3) in 80 ml of acetonitrile at 25 ° C. 0.45 g (0.015 mol) of sodium hydride (80% in paraffin) was added in portions. After stirring for 15 minutes at 25 ° C, 2.7 g (0.01 mol) of 1- (2,5-difluoro-4-cyano-phenyl) -5-fluoro-uracil added and the reaction mixture is stirred at 70 ° C for 12 hours. The mixture cooled to 25 ° C is under concentrated under reduced pressure, the residue stirred with water, with conc. Hydrochloric acid adjusted to pH 4 and the precipitated product by filtration isolated.

2.0 g (63% of theory) of 1- (2-fluoro-4-cyano-5-but-1-yn-3-yl-oxy) are obtained phenyl) -5-fluoro-uracil with a melting point of 175 ° C.  

Example 3

3.2 g (0.01 mol) of 1- (2-fluoro-4-cyano-5-but-1-yn-3-yl-oxy-phenyl) -5-fluoro-uracil are in 100 ml of acetonitrile with 0.36 g (0.012 mol) of 80% sodium hydride Stirred at 60 ° C for hours, then mixed with 1.6 g (0.011 mol) of methyl iodide and stirred at reflux temperature for 12 hours. The cooled reaction mi is concentrated under reduced pressure in a vacuum, mixed with water stirs, with conc. Acidified hydrochloric acid and filtered off the precipitated product. The Crude product is by means of column chromatography (mobile phase: cyclohexane / vinegar acid ethyl ester 1: 1) cleaned.

0.5 g (15% of theory) of 1- (2-fluoro-4-cyano-5-but-1-yn-3-yl-oxy) is obtained phenyl) -3-methyl-5-fluoro-uracil with a melting point of 141 ° C.

Analogous to Example 1, 2 and 3 and in accordance with the general description of Manufacturing methods according to the invention can, for example, also in the Compounds of formula (I) listed in Table 1 below will.

Table 1

Examples of the compounds of the formula (I)

Examples of use

In the application examples, the following compound is used as a comparison sub punch used:

1- (4-chloro-2-fluorophenyl) -1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5 - carbonitrile (be known from US 4266056).  

Example A Pre-emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether.

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, specifies the added amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours the soil is poured with the active ingredient preparation. You keep the The amount of water per unit area expediently constant. The active ingredient con Concentration in the preparation does not matter, only the effort is decisive amount of active ingredient per unit area.

After three weeks, the degree of damage to the plants is rated in% pest compared to the development of the untreated control.

It means:

0% no effect (like untreated control)
100% total annihilation.

For example, the compounds according to Her show in various tests position example 3, 15, 26, 30 and 32 with largely good tolerance to crops, such as. B. corn (0-50%) and an application rate of 125 g / ha strong effects against weeds such as Setaria (95-100%), Abutilon (100%), Amaranthus (100%), Gallium (70-100%), Sinapis (70-100%), Alopecurus (90%), Cyperus (95%).  

Example B Post emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether.

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, specifies the added amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

Test plants with a height of 5-15 cm are sprayed with the active substance preparation have so that the desired amounts of active ingredient per unit area be applied.

After three weeks, the degree of damage to the plants is rated in% Damage compared to the development of the untreated control.

It means:

0% no effect (like untreated control)
100% total annihilation.

For example, the compounds according to Her show in various tests position examples 3 and 30 with good tolerance to culture plants, such as B. corn (up to 25%) and an application rate of 125 g / ha strong Effective against weeds such as Setaria (95%), Abutilon (90-100%), Amaranthus (80-100%) and Sinapis (90%).

Claims (8)

1. Substituted phenyluracils of the general formula (I) in which
R¹ represents hydrogen, cyano or halogen,
R² stands for cyano, carbamoyl, thiocarbamoyl, halogen or for alkyl or alkoxy optionally substituted by halogen,
R³ represents the group A¹-A²-A³, wherein
A¹ is a single bond, oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ is hydrogen, hydroxy, alkyl, alkenyl, alkynyl, alkoxy, aryl, alkylsulfonyl or Arylsulfonyl,
A¹ furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
A² represents a single bond, represents oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ represents hydrogen, hydroxy, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl,
A² furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
A³ represents hydrogen with the proviso that in this case A¹ and / or A² do not represent a single bond,
A³ furthermore for hydroxy, amino, cyano, isocyano, thio cyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, each optionally substituted by halogen or alkoxy, Alk oxycarbonyl or dialkoxy (thio) phosphoryl, for alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl, each optionally optionally substituted by halogen, for each optionally by halogen, cyano, carboxy, alkyl and / or Alkoxycarbonyl substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidene amino, cycloalkyloxycarbonyl or cycloalkylalkoxy carbonyl, or for aryl, aryl, substituted in each case optionally by nitro, cyano, carboxy, halogen, alkyl, haloalkyl, alkyloxy, haloalkyloxy and / or alkoxycarbonyl oxy, aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxy approx rbonyl stands,
A³ further for each optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridinyl, pyriminyl, pyriminyl , Thienylalkyl, oxazolylalkyl, isoxazolealkyl, thiazolealkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy, furylalkoxy, represents perhydropyranylalkoxy or pyridylalkoxy,
R⁴ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, halogen, alkoxycarbonyl, alkylamino, dialkylamino, or for alkyl, alkenyl, alkynyl, alkoxy, alkoxy, alkenyloxy, alkynyloxy, each optionally substituted by hydroxy, nitro, cyano, halogen or alkoxy, Alkylthio, alkenylthio or alkynylthio,
R⁵ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, halogen, alkoxycarbonyl, alkylamino, dialkylamino, or for alkyl, alkenyl, alkynyl, alkoxy, alkoxy, alkenyloxy, alkynyloxy, each optionally substituted by hydroxy, nitro, cyano, halogen or alkoxy, Alkylthio, alkenylthio or alkynylthio, and
R⁶ for hydrogen, hydroxy, amino, cyano, for each optionally substituted by cyano, nitro, halogen or alkoxy substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, or for each optionally substituted by cyano, halogen or alkyl Cycloalkyl or cycloalkylalkyl,
except for the compounds 1- (4-chloro-2-fluoro-phenyl) -1,2,3,4-tetrahy dro-2,4-dioxopyrimidine-5-carbonitrile, 1- (3-chloro-4-fluoro -phenyl) -1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, 1- (4-chloro-3-trifluoromethylphenyl) -1,2,3,4-tetrahydro-2 , 4-dioxopyrimidine-5-carbonitrile, 1- (3,4-dichlorophenyl) -1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, 1- [4-chloro -2-fluoro-5- (2-propynyloxy) phenyl] -3-methyl-2,4- (1H, 3H) pyridinedione. 2. Substituted phenyluracils of the general formula (I) according to claim 1, characterized in that
R¹ represents hydrogen, cyano, fluorine, chlorine or bromine,
R² stands for cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for alkyl or alkoxy, each optionally substituted by fluorine and / or chlorine, each having 1 or 2 carbon atoms,
R³ represents the group -A¹-A²-A³,
in which
A¹ is a single bond, oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ is hydrogen, hydroxy, C₁-C₄-alkyl, C₃-C₄-alkenyl, C₃-C₄- alkynyl, C₁-C₄-alkoxy, phenyl, C₁-C₄-alkylsulfonyl or phenylsulfonyl,
A¹ further represents C₁-C₆-alkanediyl, C₂-C₆-alkanediyl, C₂-C₆-azaalkenediyl, C₂-C₆-alkynediyl, C₂-C₆-alkynediyl, C₃-C₆-cycloalkanediyl, C₃-C₆-cycloalkenediyl or phenylene, each optionally substituted by fluorine, chlorine or bromine ,
A² represents a single bond, represents oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, in which A⁴ represents hydrogen, hydroxy, C₁-C₄-alkyl, C₁-C₄-alkoxy, Phenyl, C₁-C₄ alkylsulfonyl or phenylsulfonyl,
A² further represents C₁-C₆-alkanediyl, C₂-C₆-alkanediyl, C₂-Cza-azaalkenediyl, C₂-C₆-alkynediyl, C₃-C₆-cycloalkanediyl, C₃-C₆-cycloalkanediyl, C₃-C₆-cycloalkenediyl or phenylene, each optionally substituted by fluorine, chlorine or bromine ,
A³ represents hydrogen, with the proviso that in this case A¹ and / or A² do not represent a single bond,
A³ furthermore for hydroxyl, amino, cyano, isocyano, thio cyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, for alkyl, alkoxy optionally substituted by fluorine, chlorine or C₁-C₄alkoxy, Alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phospho ryl each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino, alkylidene amino, alkenyloxycarbonyl, alkynyl which are optionally substituted by fluorine or chlorine, Alkynyloxy, alkynylamino or alkynyloxycarbonyl, each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, each for optionally by fluorine, chlorine, cyano, carboxy, C₁-C₄-alkyl and / or C₁-C₄-alkoxycarbo nyl substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, each with 3 to 6 carbon atoms nstoffatomen in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-Al kyloxy, C₁-C₄-haloalkyloxy and / or C₁-C₄-alkoxy-car bonyl-substituted phenyl, phenyloxy, phenyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, phenyloxycarbonyl or phenyl-C₁-C₄-alkoxycarbonyl,
A³ further for pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinylolinyl, pyridinyl, pyridine C₁-C₄-alkyl, furyl-C₁-C₄-alkyl, thienyl-C₁-C₄-alkyl, oxazolyl-C₁-C₄-alkyl, isoxazole-C₁-C₄-alkyl, thiazole-C₁-C₄-alkyl, pyridinyl-C₁- C₄-alkyl, pyrimidinyl-C₁-C₄-alkyl, pyrazolylmethoxy, furyl methoxy, represents perhydropyranylmethoxy or pyridylmethoxy, or
R⁴ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, fluorine, chlorine, bromine, C₁-C₄-alkoxy-carbonyl, C₁-C₄-alkylamino, di- (C₁-C₄-alkyl) -amino, or for each optionally alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio or alkynylthio, each with up to 6 carbon atoms, is substituted by hydroxy, nitro, cyano, fluorine, chlorine, bromine or C₁-C₁alkoxy.
R⁵ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, fluorine, chlorine, bromine, C₁-C₄-alkoxy-carbonyl, C₁-C₄-alkylamino, di- (C₁-C₄-alkyl) -amino, or for each optionally by Hy droxy, nitro, cyano, fluorine, chlorine, bromine or C₁-C₄-alkoxy sub-substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio or alkynylthio, each with up to 6 carbon atoms, and
R⁶ for hydrogen, hydroxy, amino, cyano, for each optionally substituted by cyano, nitro, fluorine, chlorine, bromine or C₁-C₄alkoxy substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, each with up to 6 carbon atoms, or for cycloalkyl or cycloalkylalkyl which is optionally substituted by cyano, fluorine, chlorine, bromine or C₁-C₄alkyl and has 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups,
except for the compounds 1- (4-chloro-2-fluoro-phenyl) -1,2,3,4-tetrahy dro-2,4-dioxopyrimidine-5-carbonitrile, 1- (3-chloro-4-fluoro -phenyl) -1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, 1- (4-chloro-3-trifluoromethylphenyl) -1,2,3,4-tetrahydro-2 , 4-dioxopyrimidine-5-carbonitrile, 1- (3,4-dichlorophenyl) -1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, 1- [4-chloro -2-fluoro-5- (2-propynyloxy) phenyl] -3-methyl-2,4- (1H, 3H) pyridinedione. 3. Substituted phenyluracils of general formula (I) according to claim 1, characterized in that
R¹ represents hydrogen, fluorine or chlorine,
R² represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, methyl or trifluoromethyl,
R³ represents the group -A¹-A²-A³,
in which
A¹ is a single bond, oxygen, sulfur, -SO-, -CO₂-, -CO- or the grouping -N-A⁴-, where A⁴ is hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, meth oxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethyl sulfonyl,
A¹ furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl or propyne-1,3-diyl,
A² represents a single bond, oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, where A⁴ represents hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, meth oxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
A² furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl or propyne-1,3-diyl,
A³ represents hydrogen, with the proviso that in this case A¹ and / or A² do not represent a single bond,
A³ furthermore for hydroxyl, amino, cyano, nitro, carboxy, carb amoyl, sulfo, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, n- which are optionally substituted by fluorine, chlorine, methoxy or ethoxy, n- , i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n- , i-, s- or t-pentyloxy, methylthio, ethyl thio, n- or i-propylthio, n-, i-, s- or t-butylthio, methyl sulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl , Ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butyl amino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, Dimethoxyphosphoryl, diethoxyphosphoryl or dipropoxyphosphoryl, diisopropoxyphosphoryl, for propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylidenamino, butylideneamino, propenyloxycarbonyl, which are optionally substituted by fluorine or chlorine, Butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, each for cyclopropyl, cyclobutyl, cyclopentyl, optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl , Cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclo butylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclo propylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidenamoxy, cyclohexylmethoxycarbonyl, cyclohexylmethoxycarbonyl, cyclohexylmethoxycarbonyl, cyclohexyl methoxycarbonyl, cyclohexylmethoxycarbonyl Cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted phenyl, phenyloxy, Benzyl, phenylethyl, Benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl,
A³ further for (in each case wholly or partially hydrated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, oxylolylmethyl, oxylolylmethyl thyl, isoxazolmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy,
R⁴ represents hydrogen, cyano, fluorine, chlorine or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine,
R⁵ represents hydrogen, cyano, fluorine, chlorine or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine, and
R⁶ represents hydrogen, amino, cyano or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, Propynyl or butynyl,
except for the compounds 1- (4-chloro-2-fluoro-phenyl) -1,2,3,4-tetrahy dro-2,4-dioxopyrimidine-5-carbonitrile, 1- (3-chloro-4-fluoro -phenyl) -1,2,3,4-trahydro-2,4-dioxopyrimidine-5-carbonitrile, 1- (4-chloro-3-trifluoromethylphenyl) -1,2,3,4- tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, 1- (3,4-dichlorophenyl) -1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, 1- [ 4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -3-methyl-2,4- (1H, 3H) pyridinedione. 4. Process for the preparation of substituted phenyluracils of the general formula (I) in which R¹, R², R³, R⁴, R⁵ and R⁶ have the meanings given in Claim 1,
characterized in that one
(a) Halogenarenes of the general formula (II) in which
R¹, R² and R³ have the meaning given above and
X¹ represents halogen,
with uracenes of the general formula (III) in which
R⁴, R⁵ and R⁶ have the meaning given above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or that one
(b) aminoarenes of the general formula (IV) in which
R¹, R² and R³ have the meaning given above,
with 3-alkoxy-1-oxo-2-alkenyl-carbamic acid esters of the general formula (V) in which
R⁴, R⁵ and R⁶ have the meaning given above, and
R represents alkyl,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent. 5. Herbicidal agents, characterized by a content of at least one substituted phenyluracil of the general formula (I) according to the claims Chen 1 to 4. 6. Process for combating undesirable plants, thereby ge indicates that substituted phenyluracils of the general formula (I) according to claims 1 to 4 on undesirable plants and / or lets their living space take effect. 7. Use of substituted phenyluracils of the general formula (I) according to claims 1 to 4 for combating undesirable plants Zen. 8. A process for the preparation of herbicidal compositions, characterized in that that substituted phenyluracils of the general formula (I) according to the Claims 1 to 4 with extenders and / or surface-active substances zen mixed.