WO1997005117A1

WO1997005117A1 - Substituted 1-phenyluracil derivatives, their preparation and their use as herbicides

Info

Publication number: WO1997005117A1
Application number: PCT/EP1996/003222
Authority: WO
Inventors: Karl-Heinz Linker; Kurt Findeisen; Roland Andree; Mark Wilhelm Drewes; Markus Dollinger; Hans-Joachim Santel
Original assignee: Bayer Aktiengesellschaft
Priority date: 1995-08-02
Filing date: 1996-07-22
Publication date: 1997-02-13
Also published as: AU6658596A; DE19528305A1

Abstract

New substituted phenyluracils have the general formula (I), in which R1 stands for hydrogen, cyano or halogen; R2 stands for cyano, carbamoyl, thiocarbamoyl, halogen or optionally halogen-substituted alkyl or alkoxy; R3 stands for the group A1-A2-A3, in which A?1, A2 and A3¿ have the meanings given in the description; R4 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; R5 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 R6 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-pyrimidin-5-carbonitril, 1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril, 1-[4-chloro-2-fluoro-5-(2-propinyloxy)-phenyl]-3-methyl-2,4-(1H,3H)-pyridindione. Also disclosed is a process for preparing these compounds and their use as herbicides.

Description

SUBSTITUTED 1-PHENYLURACIL DERIVATIVES, THEIR PRODUCTION AND THE USE THEREOF AS HERBICIDES

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

Substituted uraciles, e.g. the compounds l- (4-chloro-2-fluorophenyl) - l, 2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, l- (3-chloro-4-fluorophenyl ) - l, 2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, l- (4-chloro-3-trifluoromethylphenyl) -l, 2,3,4-tetrahydro-2, 4-dioxo-pyrirnidine-5-carbonitrile and l- (3,4-dichloro-10 phenyl) - !, 2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile (cf. US 4266056) as well as l- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -3-methyl-2,4- (1H, 3H) pyridinedione (cf. US 5298502) are already known from the patent literature. However, nothing has hitherto been disclosed about the herbicidal activity of these compounds.

15 The new substituted phenyluracils of the general formula (I) have now been found

R °

in which

R ^{1 represents} hydrogen, cyano or halogen,

20 R ^{~ stands} for cyano, carbamoyl, thiocarbamoyl, halogen or for alkyl or alkoxy which is optionally substituted by halogen,

K ^{Λ stands} for the grouping A -A "-A, in which A ^{1 stands} for a single bond, for oxygen, sulfur, -SO-, -SO -, -, - CO- or the grouping -NA ⁴ -, wherein A ^{4 stands} for hydrogen, hydroxy, alkyl, alkenyl, alkynyl, alkoxy, aryl , Alkylsulfonyl or arylsulfonyl,

A ¹ further for each optionally substituted by halogen

Alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkendiyl or phenylene,

Ar for a single bond, for oxygen, sulfur, -SO-, -SO -, -,

-CO- or the grouping -NA ⁴ - in which A ^{4 represents} hydrogen, hydroxy, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl,

A "furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,

A " ^{1 represents} hydrogen with the proviso that in this case A ¹ and / or A" do not represent a single bond

A * furthermore for hydroxy, amino, cyano, isocyano, thiocyanato,

Nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl,

Halogen, for in each case optionally substituted by halogen or alkoxy alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl,

Alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) - phosphoryl, for alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyloxy, alkynyloxy, alkynylamino or alkynyloxycarbonyl optionally substituted by halogen, each optionally substituted by halogen, cyano, Carboxy, alkyl and / or alkoxy-carbonyl substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, or for each optionally by nitro, cyano, carboxy, halogen, alkyl, haloalkyl, alkyloxy, halogene alkyl oxy and / or alkoxycarbonyl substituted aryl, aryloxy, aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbonyl, A ^" also for in each case fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinylolinyl, pyridinyl, pyriminyl, pyridinyl, pyriminyl Furylalkyl, thienylalkyl, oxazolylalkyl, isoxazolealkyl, thiazolealkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy, furylalkoxy, represents perhydropyranylalkoxy or pyridylalkoxy,

R is hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, halogen, alkoxycarbonyl, alkylamino, dialkylamino, or for alkyl, alkenyl, alkynyl, alkoxy which is optionally substituted by hydroxy, nitro, cyano, halogen or alkoxy , Alkenyloxy, alkynyloxy, alkylthio, alkenylthio or alkynylthio,

R ^{5 is} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, halogen, alkoxycarbonyl, alkylamino, dialkylamino, or for alkyl, alkenyl, alkynyl, alkoxy which is optionally substituted by hydroxy, nitro, cyano, halogen or alkoxy, Alkenyloxy, alkynyloxy, alkylthio, alkenylthio or alkynylthio, and

R ^{6 represents} hydrogen, hydroxyl, amino, cyano, each alkyl, alkenyl, alkynyl optionally substituted by cyano, nitro, halogen or alkoxy,

Alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, or for cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or alkyl,

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) -l, 2,3,4-tetra-hydro-2,4-dioxopyrimidine-5-carbonitrile, l- (4-chloro-3-trifluoromethyl-phenyl) - l, 2,3, 4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile and l- (3,4-dichlorophenyl) - l, 2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile ( see US 4266056) and 1 - [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -3-methyl-2,4- (1H, 3H) -pyridinedione (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

R ¹ , R ² and R ^{3 have} the meaning given above and

X represents halogen,

with uracenes of the general formula (III)

R ^D

in which

R, R and R have the meaning given above,

optionally in the presence of a reaction auxiliary and optionally in

In the presence of a diluent,

or if you

(b) aminoarenes of the general formula (IV)

in which

R ¹ , R ² and R ^{3 have} the meaning given above,

with 3-alkoxy-l-oxo-2-alkenyl-carbamic acid esters of the general formula (V)

in which

R ⁴ , R ⁵ and R ^{6 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 converted into other compounds of the general formula (I) according to the above definition by further conventional methods, for example by nucleophilic substitution (for example R ³ : F → OH, SH, NH ₂ , OCH ₃ , NHSO ₂ CH ₃ ; by alkylation (e.g. R ⁶ : H -> CH ₃ ); or by further conversions of functional groups (e.g. R ² : CONH-, → CN, CN → CSNH ₂ ; R ³ : NO ₂ → NH ₂ , NH-, → F, Cl, Br, CN, NHSO-, CH ₃ , SO-, Cl) - see also the manufacturing examples. The new substituted phenyluracils of the general formula (1) are notable for strong herbicidal activity

In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkynyl, are each straight-chain 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 the formula (I) in which

R ^{1 represents} hydrogen, cyano, fluorine, chlorine or bromine,

R "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,

R 'for grouping -A ^! -A ² -A ³ stands,

in which

A ¹ for a single bond, for oxygen, sulfur, -SO-, -SO -, -,

-CO- or the grouping -NA ⁴ -, wherein A ^{4 is} hydrogen, hydroxy, C _r C ₄ alkyl, C ₃ -C ₄ alkenyl, C ₃ -C ₄ alkynyl, C, -C ₄ alk - oxy, phenyl, C, -C ₄ alkylsulfonyl or phenylsulfonyl,

A ¹ furthermore for each optionally substituted by fluorine, chlorine or bromine, C _r C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, C ₂ -C ₆ -azaalkenediyl, C ₂ -C ₆ -alkynediyl, C ₃ -C _6- cycloalkanediyl, C ₃ -C ₆ -cycloalkenediyl or phenylene,

A "for a single bond, for oxygen, sulfur, -SO-, -SO -, -,

-CO- or the grouping -NA - where A ^{4 represents} hydrogen, hydroxy, C _r C ₄ alkyl, C _r C ₄ alkoxy, phenyl, C _r C ₄ alkylsulfonyl or phenylsulfonyl, A ^~ furthermore for C, -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, G, -C _f) -zazaalkenediyl, C ₂ -C ₆ -alkindiyl, C ₃ each optionally substituted by fluorine, chlorine or bromine -C ₆ -cycloalkanediyl, C ₃ -C ₆ -cycloalkenediyl or phenylene,

A ^{3 represents} hydrogen, with the proviso that in this case A ¹ and / or A do not represent a single bond,

A ³ furthermore for hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, for each optionally substituted by fluorine, chlorine or C _r C ₄ alkoxy, 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 optionally substituted by fluorine or chlorine, Alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, for each optionally by fluorine, chlorine, cyano, carboxy, C 1 -C ₄ -alkyl and / or C _] -C ₄ -alkoxy-carbonyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidene-amino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, each with 3 to 6 carbon 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, C _r C ₄ alkyl, C _r C ₄ haloalkyl, C _r C ₄ -alkyloxy,

C _j -C ₄ haloalkyloxy and / or C ₁ -C ₄ alkoxycarbonyl substituted phenyl, phenyloxy, phenyl-C _r C ₄ alkyl, phenyl-C _] -C ₄ alkoxy, phenyloxycarbonyl or phenyl-C _] -C ₄ -alkoxycarbonyl,

A ^J also for in each case fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl azinyl, pyrazolyl-C _] -C ₄ -alkyl, furyl-C _r C ₄ -alkyl, thienyl-C, -C ₄ -alkyl, oxazolyl-C _r C ₄ -alkyl, isoxazole-C _r C ₄ -alkyl , Thiazole-C, -C ₄ -al- kyl, pyridinyl-C, -C ₄ -alkyl, pyrimidιnyl-C, -C ₄ -alkyl, pyrazolylmethoxy, furylmethoxy, represents perhydropyranylmethoxy or pyridylmethoxy, or

R ⁴ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, fluorine, chlorine, bromine, C, -C ₄ -alkoxy-carbonyl, C, -C ₄ -alkylamino, di- (C, -C ₄ -alkyl) - amino, or for alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio or alkynylthio, each optionally substituted by hydroxy, nitro, cyano, fluorine, chlorine, bromine or C 1 -C ₄ -alkoxy, each with up to 6 Carbon atoms stands,

R ⁵ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, fluorine,

Chlorine, bromine, C, -C ₄ -alkoxy-carbonyl, C _r C ₄ -alkylamino, di- (C _r C ₄ -alkyl) - amino, or for each optionally by hydroxy, nitro, cyano, fluorine, chlorine, bromine or C ^ Q _j -alkoxy substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio or alkynylthio each having up to 6 carbon atoms, and

R ⁶ for hydrogen, hydroxy, amino, cyano, for alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, which are each optionally substituted by cyano, nitro, fluorine, chlorine, bromine or C 1 -C ₄ -alkoxy each having up to 6 carbon atoms, or represents in each case where appropriate by cyano, fluorine, chlorine, bromine or C _j -C ₄ alkyl-substituted

Cycloalkyl or cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups,

where the known compounds l- (4-chloro-2-fluorophenyl) -l, 2,3,4-tetra-hydro-2,4-dioxopyrimidine-5-carbonitrile, l- (3-chloro-4 -fluorophenyl) - 1,2,3, 4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, l- (4-chloro-3-trifluoromethyl-phenyl) -l, 2,3, 4- tetrahydro-2,4-dioxopyrirnidine-5-carbonitrile and l- (3,4-dichlorophenyl) -l, 2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile ( see US 4266056) and l- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -3-methyl-2,4- (1H, 3H) -pyridinedione (see US 5298502) excepted by disclaimer are

The invention relates in particular to compounds of the formula (I) in which R ^{1 represents} hydrogen, fluorine or chlorine,

R ^{2 represents} cyano, thiocarbamoyl, fluorine, chlorine, bromine, methyl or trifluoromethyl,

R ^{3 represents} the grouping -A'-A ² -A ³ ,

in which

A ^{1 represents} a single bond, represents oxygen, sulfur, -SO-, -SO, -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, methyl, ethyl, n- or i-propyl , Methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl,

A ¹ 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,

A 1 "stands for a single bond, for oxygen, sulfur, -SO-, -SO -, -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, methyl, ethyl, n- or i Propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,

A ² 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,

A ^J stands for hydrogen, with the proviso that in this case A ¹ and / or A ² do not represent a single bond,

A ³ furthermore for hydroxy, amino, cyano, nitro, carboxy, carbamoyl,

Sulfo, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i- substituted by fluorine, chlorine, methoxy or ethoxy

Propyl, 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, 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 -Butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxy- 5 carbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl or dipropoxyphosphoryl, diisopropoxyphosphoryl, each propylene, butenyl, propenyloxy optionally substituted by fluorine or chlorine , Butenyloxy, propenylamino, butenylamino, propylidene amino, butylidene amino, propenyl oxy car-10 bonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, for each optionally by fluorine, chlorine, cyano Carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl substituted cyclopropyl, cyclobutyl, cyclo-pentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyl¬ oxy, cycl ohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclo-propylmethoxy, cyclobutyl-methoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidenamino, cyclohexylidenamino, cyclopentyloxycarbonyl, cyclo-20 or hexyloxyhexylcarbonyl, cyclophenyloxyoxyyl, cyclohexyloxyoxy, 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-25 carbonyl substituted phenyl , Phenyloxy, benzyl, phenylethyl,

Benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl,

A ³ continues for (in some cases fully or partially hydrogenated)

Pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl,

Isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyri-

30 dinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolmethyl, thiazole methyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, R for hydrogen, cyano, fluorine, chlorine or for each optionally by

Fluorine and / or chlorine substituted methyl, ethyl, methoxy or ethoxy,

R ^{5 represents} hydrogen, cyano, fluorine, chlorine or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine, and

R ⁶ for hydrogen, amino, cyano or for 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 l- (4-chloro-2-fluorophenyl) -l, 2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, l- (3-chloro-4 -fluorophenyl) -l, 2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, l- (4-chloro-3-trifluoromethyl-phenyl) -l, 2,3, 4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile and 1 - (3,4-dichlorophenyl) - 1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile ( see US 4266056) and l- [4-chloro

2-fluoro-5- (2-propynyloxy) phenyl] -3-methyl-2,4- (1H, 3H) -pyridinedione (cf. US 5298502) are excluded by disclaimers

The general or preferred radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for production. These radical definitions can be as desired with one another, that is to say between the specified preferred ranges be combined

Examples of the compounds of formula (I) according to the invention are listed in the groups below Group 1

R ⁴ and R ⁶ have, for example, the meanings listed below:

R ^ϋ R ⁴ R ⁶ R ⁴ R ° R ⁴ R ^ö R ⁴

CH, Cl CHF ₂ NO,

> - ϊ> - \> - D> -

CHF ₂ CH ₃ CHF ₂ Cl CHF-, CHF, CHF, NO, SCH ₃ CH, SCH ₃ Cl S SCCHH ₃ , CHF ₂ SCH, NO, SCF, CH, SCF ₃ Cl S SCCFF ₃ , CHF ₂ SCF, NO ₂

SCF ₂ C1 CH ₃ SCF ₂ C1 Cl SCF ₂ C1 CHF ₂ SCF ₂ C1 NO, SCF ₂ CH ₃ CH ₃ SCF ₂ CH ₃ Cl SCF ₂ CH ₃ CHF ₂ SCF ₂ CH ₃ NO,

CN CH ₃ CN Cl CN CHF-, CN NO, CSNH, CH, CSNH ₂ Cl CSNH ₂ CHF ₂ CSNH, NO,

CH ₂ C≡CH CH ₃ CH, C≡CH Cl CH ₂ C≡CH CHF ₂ CH ₂ G≡CH NO,

HFHN (CH ₃ ) ₂ HC CHH ,, CCF ₃ H NH,

CH ₃ F CH ₃ N (CH ₃ ) ₂ CH, CH ₂ CF ₃ CH ₃ NH ₂

C ₂ H ₅ FC ₂ H ₅ N (CH ₃ ) ₂ C ₂ , HH ₅ r CH, CF C ₂ H ₅ NH, iC ₃ H ₇ F iC ₃ H ₇ N (CH ₃ ) ₂ iC ₃ H ₇ CH, CF ₃ iC ₃ H ₇ NH, nC ₃ H ₇ F nC ₃ H ₇ N (CH ₃ ) ₂ nC ₃ H ₇ CH ₂ CF ₃ nC ₃ H ₇ NH,

N (CH ₃ ) ₂ CH, CF ₃ NH, ϊ> - [> -

CHF ₂ F CHF ₂ N (CH ₃ ) ₂ CHF ₂ CH, CF ₃ C tH> F ₂ - - NH,

SCH ₃ F SCH ₃ N (CH ₃ ) ₂ SCH ₃ CH, CF ₃ SCH ₃ NH,

SCF ₃ F SCF ₃ N (CH ₃ ) ₂ SCF, CH ₂ CF ₃ SCF ₃ NH,

SCF ₂ C1 F SCF ₂ C1 N (CH ₃ ) ₂ SCF ₂ C1 CH, CF ₃ SCF ₂ C1 NH,

SCF ₂ CH ₃ F SCF, CH ₃ N (CH ₃ ) ₂ SCF, CH ₃ CH, CF ₃ SCF ₂ CH ₃ NH,

CN F CN N (CH ₃ ) ₂ CN CH, CF ₃ CN NH,

CSNH, F CSNH ₂ N (CH ₃ ) ₂ CSNH, CH, CF ₃ CSNH, NH,

CH, C≡CH F CH, C≡CH N (CH ₃ ) ₂ CH, C≡CH CH, CF ₃ CH, C≡CH NH,

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-cyano-phenyl, 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-propoxyphenyl, 4-chloro-2-fluoro-5-methoxyphenyl, 4-chloro-2-fluoro-5-ethoxyphenyl, 4-chloro-2-fluoro-5-n- propoxy-phenyl, 4-chloro-2-fluoro-5-i-propoxy-phenyl, 2-fluoro-4-cyano-5-methyl-phenyl, 2,4-dichloro-5-methyl-phenyl, 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-phen yl, 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- (l-methyl-2-propynyloxy) phenyl, 2-chloro-4-thiocarbamoyl-5-i-propoxyphenyl, 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-trifluoromethyl sulfonyl aminophenyl, 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-methoxycarbonyl-phenyl, 2-chloro-4-cyano-5- (N -cyclopropyl-ethysulfonylamino) -phenyl, 2-fluoro-4-cyano-5- (l-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-propoxycarbonyl-phenyl, 2- Fluoro-4-cyano-5- (bis-ethylsulfonylamino) phenyl, 2-fluoro-4-cyano-5- (N-methylsulfonylethylsulfonylamino) phenyl, 2-fluoro-4-cyano-5- (l-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-hydroxy-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-ethoxycarbonyloxyphenyl, 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-dimethoxymethyleneamino-phenyl, 2- Chloro-4-cyano5-ethoxymethyleneamino-phenyl, 2-fluoro-4-cyano-5- (2-chloro-ethoxycarbonyloxy) phenyl, 2-chloro-4-cyano-5-dimethylaminomethyleneamino-phenyl, 2-chloro-4 -cyano-5- (perhydropyran-4-yloxy) phenyl, 2-fluoro-4-cyano-5- (2-methoxycarbonylethyl) phenyl, 2-chloro-4-cyano-5- (2- carboxy-2-chloro-eth yl) phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-methoxycarbonyl-ethyl) phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-s-butoxycarbonyl) -phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-carbamoyl-ethyl) - phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-methoxycarbonyl-l-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-cy ano-5- (2-ethoxy carbonyl-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-c yano-5- (l-ethoxycarbonyl-ethyl) phenyl, 2-chloro-4-cyano-5- (l-ethoxycarbonylethyl) phenyl, 2-chloro-4-cyano-5-carboxyphenyl, 2-fluoro- 4-chloro-5- (l-ethoxycarbonyl-ethyl) -phenyl, 2-fluoro-4-chloro-5- (l-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- (2nd -methoxy-ethoxy) -phenyl, 2-fluoro-4-chloro-5-i-butoxyphenyl, 2-fluoro-4-hydroxy-5-i-propoxycarbonyl-phenyl, 2-fluoro-4-cyano-5- (2nd -oxetanyloxy) phenyl, 2-fluoro-4-cy an o-5- (2-oxetanyloxy carbonylmethoxy) phenyl. Group 2

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 3

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 4

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1. Group 5

R ^u

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 6

R ^ü ^v

Ar, R ⁴ and R ⁶ have, for example, those given above under Group 1

Meanings.

Group 7

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1. Group 8

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 9

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 10

^

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1. Group 11

R °

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 12

Ar, R ⁴ and R ⁶ have, for example, those given above under Group 1

Meanings.

Group 13

R ^D

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1. Group 14

Ar, R ⁴ and R ⁶ have, for example, those given above under Group 1

Meanings.

Group 15

Ar, R ⁴ and R ⁶ have, for example, those given above under Group 1

Meanings.

Group 16

Ar, R ⁴ and R ⁶ have, for example, those given above under Group 1

Meanings. Group 17

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 18

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 19

R ^ü

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1. Group 20

R "

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 21

Ar, R ⁴ and R ⁶ have, for example, those given above under Group 1

Meanings.

Group 22

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1. Group 23

R °

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 24

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 25

^{; J}

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1. Group 26

R ^u

Ar, R> 4 and R have, for example, those given above under Group 1

Meanings.

Group 27

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 28

R "

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1. Group 29

R °

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 30

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 31

Ar, R and R ⁶ have, for example, the meanings given above under Group 1. Group 32

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 33

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

Group 34

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1. Group 35

R ^u

Ar, R ⁴ and R ⁶ have, for example, the meanings given above under Group 1.

If, for example, 2-chloro-4,5-difluoro-benzonitrile and 1,2,3,4-tetra-hydro-2,4-dioxopyrimidine-5-carbonitrile are used as starting materials, the reaction can proceed in the process according to the invention (a) are sketched by the following formula scheme:

If, for example, 2,4-dichloro-5-methoxy-aniline and 2-cyano-3-methoxy-1-oxo-2-propenyl-carbamic acid methyl ester are used as starting materials, the course of the reaction in process (b) according to the invention can can be outlined by the following formula:

The haloarenes to be used as starting materials in the process (a) according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (II). In the formula (II), R ¹ , R ² and R ^J preferably or in particular the meaning that was already given above in the description of the compounds of the formula (I) to be prepared according to the invention, preferably or as being particularly preferred for R ¹ , R ² and R ³ , X ¹ preferably represents fluorine, chlorine or bromine, especially for fluorine or chlorine

The starting materials of the formula (II) are known and / or can be prepared by known processes (cf. EP 191 181, EP 370332, EP 431373, EP 441004

The uracils to be further used as starting materials in the process (a) according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (III). In the formula (III), R ⁴ , R ⁵ and R ⁶ preferably or in particular the meaning which has already been mentioned above in the description of the compounds of the formula (I) to be prepared according to the invention, preferably or as being particularly preferred for R ⁴ , R and R.

The starting materials of the formula (III) are known and / or can be prepared by known processes (cf. DE 3402193, 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 generally defined by the formula (IV). In the formula (IV), R ¹ , R ² and R ^J preferably or in particular have the meaning which have already been described above in connection with the Compounds of the formula (I) to be prepared according to the invention have been indicated preferably or as particularly preferred for R, R and R.

The starting materials of the formula (IV) are known and / or can be prepared by known processes (cf. EP 224001)

Formula (I) further 3-alkoxy-l-oxo-2-alkenyl carbamate esters to be used as starting materials are generally defined by the formula (V) in the formula

(V) R ⁴ , R ⁵ and R ⁶ preferably or in particular have the meaning which has already been mentioned above in the description of the compounds of the formula (I) to be prepared according to the invention preferably or as particularly preferred for R ⁴ , R ⁵ and R ⁶

The starting materials of the formula (V) are known and / or can be prepared by known processes (cf. 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 carried out in the presence of a suitable reaction auxiliary. The conventional inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries

These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium or potassium ¬ or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or Calcium hydroxide, sodium or potassium methanolate, ethanolate, n- or i-propanolate, n-, i-, s- or t-butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldi-cyclohexylamine, N, N-dimethyl-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 the formula (I) are preferably carried out in the presence of a diluent. Suitable diluents are generally the customary organic solvents. These preferably include aliphatic, ahcyclic and aromatic, optionally halogenated hydrocarbons, such as, for example, pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, Cyclohexane, methylcyclohexane, dichloromethane (methylene chloride), trichloromethane (chloroform) or carbon tetrachloride, dialkyl ether, 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 such as acetone, butanone (methyl ethyl ketone), methyl i-propyl ketone or methyl i-butyl ketone, nitriles such as acetonitrile, propionitrile, butyronitrile or benzonitrile; Amides, such as, for example, N, N-dimethylformamide (DMF), N, N-dimethyl-acetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethyl-phosphoric acid triamide; Esters, such as, for example, methyl acetate, ethyl ester, n- or i-propyl ester, n-, i- or s-butyl ester; Sulfoxides, such as dimethyl sulfoxide; Alkanols, such as, for example, 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 mixtures with water or pure water.

The reaction temperatures can be varied within a substantial range when carrying out processes (a) and (b) according to the invention. In general, temperatures between 0 ° C and 200 ° C, preferably between 10 ° C and 150 ° C, in particular between 20 ° C and 120 ° C.

Processes (a) and (b) according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between

0.1 bar and 10 bar.

To carry out processes (a) and (b) according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a large excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention as total or selective herbicides depend essentially on the amount used.

The active compounds according to the invention can e.g. can be used for the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduanus, Carduan , Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicotyledon 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, Alopecurus, Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

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

Depending on the concentration, the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and

Places with and without tree cover. Likewise, the compounds for weed control in permanent crops, for example forest, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and Hop plants, on ornamental and sports turf and pastures and for selective weed control in annual crops. The compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon crops both in the pre-emergence and in the post-emergence process

To a certain extent, the compounds of the formula (I) also have insecticidal and acaricidal activity

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers Fabrics

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents

»" Means

If water is used as an extender, organic solvents can also be used as auxiliary solvents. Liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes. Chlorethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example 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 lisobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl formamide and dimethyl sulfoxide, and water

Solid carrier materials that come into question are, for example, ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, as solid carrier materials for granules Question e.g. broken and fractionated natural rocks like

Calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as poly oxyethyl en fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: eg

Lignin sulfite liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine 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 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used as a weed control in a mixture with known herbicides, finished formulations or tank mixes being possible.

Known herbicides, for example anilides, such as e.g. Diflufenican and Propanil; Aryl carboxylic acids, e.g. Dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, e.g. 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, e.g. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones, e.g. Chloridazon and norflurazon; Carbamates, e.g. Chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides, e.g. Alachlor, acetochlor, butachior, metazachlor, metolachlor, pretilachlor and propachlor; Dinitroanilines, e.g. Oryzalin, pendimethalin and trifluralin; Diphenyl ethers, e.g. Acifluorfen, bifenox, fluoroglycofen,

Fomesafen, halosafen, lactofen and oxyfluorfen; Ureas, such as chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; Hydroxylamines such as alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; Imidazolinones such as imazethapyr, imazamethabenz, imazapyr and imazaquin; Nitriles such as bromoxynil, dichlobenil and ioxynil; Oxyacetamides, such as, for example, mefenacet; Sulfonylureas such as amidosulfuron, ben-sulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates such as butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates; Triazines such as atrazine, cyanazine, simazin, simetryne, terbutryne and terbutylazine; Triazinones such as hexazinone, metamitron and metribuzin;

Others, such as Aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.

The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.

The amount of active ingredient used can vary over a wide range. It essentially depends 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, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the examples below. Manufacturing examples:

example 1

H

(Method (a))

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

12 g (90% of theory) of l- (2,5-difluoro-4-cyanophenyl) -5-fluorouracil with a melting point> 250 ° C. are obtained.

Example 2

H

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

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

Example 3

3.2 g (0.01 mol) of l- (2-fluoro-4-cyano-5-but-l-in-3-yl-oxy-phenyl) -5-fluoro-uracil are dissolved in 100 ml of acetonitrile with 0 , 36 g (0.012 mol) of 80% sodium hydride stirred for one hour at 60 ° C, then mixed with 1.6 g (0.01 1 mol) of methyl iodide and stirred at reflux temperature for 12 hours. The cooled reaction mixture is concentrated under reduced pressure in vacuo, stirred with water, with conc. Acidified hydrochloric acid and filtered off the precipitated product. The crude product is purified by column chromatography (mobile phase: cyclohexane / ethyl acetate 1: 1).

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

Analogously to Examples 1, 2 and 3 and in accordance with the general description of the production processes according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) listed in Table 1 below.

Table 1: Examples of the compounds of the formula (I)

Example - R ¹ R ² R ³ R ⁴ R> R ⁶ Schmelz¬

No. point (° C)

4 F CN FH CF ₃ H> 250

5 F CN FH CF ₃ CH ₃ 172

6 F CN F H F H 219

7 F CN NHSO ₂ C ₂ H ₅ HF τ _ι H 96

8 F CN FH CH ₃ 102

9 F CN NHSO ₂ C ₃ H ₇ -i HFH 165

10 F CN FH CH ₃ H 212

1 1 F CN F H Cl H 132

14 CN H CH ₃ CH ₃ 1!

Example - R ¹ R ^ R- ¹ R ⁴ R ^s R ^ö Schmelz¬

No. point (° C)

17 F CN NHSO ₂ C ₂ H ₅ H Cl H 75 18 F CN OCH (CH ₃ ) ₂ H CH, H 229

22 F CN F CF ₃ FH 115

23 F CN OC ₂ H ₅ HFH 229

24 F CN OC ₃ H ₇ -i H CH ₃ CH ₃ 163

26 F CN OC ₃ H ₇ -i HF CH ₃ 162

27 F CN OC ₃ H _r i HFC ₂ H ₅ 159 Example - R ¹ R ² R ^J R ⁴ R ⁵ R ^ö Melting point (° C)

28 CN OC ₂ H ₅ H CH ₃ 178

31 CN OCH, HC ₂ H ₅ 158

32 CN H CH, 152

33 CN HFC ₂ H ₅ 154

34 F CN HF CH ₇ -i 138

37 F CN H CF C ₂ H ₅ 154 Example, R ¹ R ^ R ^j R ⁴ R ⁵ R ^ü Schmelz¬

No. point (° C)

40 F CN F H CN H 231

41 F CN F H Br H 230

42 F CN FH COOC ₂ H ₅ n 194

45 CN H Br C ₂ H ₅ 194

CH, Examples of use:

In the application examples, the following compound is used as a reference substance:

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

Example A

P re-em ergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours, the active ingredient preparation is poured onto the floor. You keep the

The amount of water per unit area expediently constant. The concentration of active substance in the preparation is irrelevant; the decisive factor is only the amount of active substance applied per unit area.

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

It means:

0% = no effect (like untreated control)

100% = total annihilation

In various tests, for example, the compounds according to preparation example 3, 15, 26, 30 and 32, with largely good tolerance to crop plants, such as maize (0-50%) and an application rate of 125 g / ha, show strong effects against weeds such as Setaria (95-100%), Abutilon (100%), Amaranthus (100%), Galium (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

Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray breaks is chosen so that the mixed amounts of active compound are applied in about 1000 l / ha.

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

In various tests, for example, the compounds according to Preparation Examples 3 and 30 show, in some cases, good tolerance to crop plants, such as Maize (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

claims

Substituted phenyluracils of the general formula (I)

in which

R ^{1 represents} hydrogen, cyano or halogen,

R ^{2 stands} for cyano, carbamoyl, thiocarbamoyl, halogen or for alkyl or alkoxy which is optionally substituted by halogen,

R represents the grouping A -A -A, wherein

A ^{1 represents} a single bond, represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, in which A ^{4 represents} hydrogen, hydroxy, alkyl, alkenyl, alkynyl, alkoxy, aryl, Alkylsulfonyl or arylsulfonyl,

furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,

represents a single bond, represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl, A ~ furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkynediyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,

A ^{3 represents} hydrogen with the proviso that in this case

5 A and / or A "do not stand for a single bond

A furthermore for hydroxy, amino, cyano, isocyano, thio cyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, for alkyl, alkoxy, alkylthio optionally substituted by halogen or alkoxy,

10 alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl, for alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbon, optionally substituted by halogen

15 each cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidene-amino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, optionally substituted by halogen, cyano, carboxy, alkyl and / or alkoxycarbonyl, or for each optionally by nitro, cyano,

20 carboxy, halogen, alkyl, haloalkyl, alkyloxy, haloalkyloxy and / or alkoxycarbonyl substituted aryl, aryloxy, aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbonyl,

A further for 25 fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyi, triazolyl, furyl,

Oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyrimidinyl, triazinyl, pyrazolylalkyl, furylalkyl, thienylalkyl, oxazolylalkyl, isoxazylyl, pyrid oxy represents perhydropyranylalkoxy or pyridylalkoxy,

R ⁴ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, halogen, alkoxycarbonyl, alkylamino, dialkylamino, or for each because alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio or alkynylthio is optionally substituted by hydroxy, nitro, cyano, halogen or alkoxy,

R ⁵ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, halogen, alkoxycarbonyl, alkylamino, dialkylamino, or for alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy optionally substituted by hydroxy, nitro, cyano, halogen or alkoxy, Alkynyloxy, alkylthio, alkenylthio or alkynylthio, and

R ⁶ for hydrogen, hydroxy, amino, cyano, for alkyl optionally substituted by cyano, nitro, halogen or alkoxy,

Alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, or for cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or alkyl,

except for the compounds l- (4-chloro-2-fluorophenyl) -l, 2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, l- (3-chloro-4- fluorophenyl) -l, 2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, l- (4-chloro-3-trifluoromethyl-phenyl) -l, 2,3,4-tetrahydro -2,4-dioxopyrimidine-5-carbonitrile, l- (3,4-dichlorophenyl) -l, 2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, l- [ 4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -3-methyl-2,4- (1H, 3H) pyridinedione

Substituted phenyluracils of the general formula (I) according to Claim 1, characterized in that

R ^{1 represents} hydrogen, cyano, fluorine, chlorine or bromine,

R ^{2 represents} cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or alkyl or alkoxy, each optionally substituted by fluorine and / or chlorine, each having 1 or 2 carbon atoms,

R ³ for the grouping -A ^! -A ² -A ³ stands,

in which A ¹ for a single bond, for oxygen, sulfur, -SO-,

-SO, -, -CO- or the grouping -NA ⁴ -, where A ^{4 is}

Hydrogen, hydroxy, C, -C ₄ alkyl, C ₃ -C ₄ alkenyl, C ₃ -C ₄ -

Alkynyl, C _r C ₄ alkoxy, phenyl, C ₁ -C ₄ alkylsulfonyl or

5 is phenylsulfonyl,

A ¹ also for C _] -C ₆ -alkanediyl, C -, - C ₆ -alkenediyl, G, - C ₆ -azaalkenediyl, C ₂ -C ₆ -alkindiyl, C ₃ -C _6- cycloalkanediyl, C ₃ -C ₆ -cycloalkenediyl or phenylene,

10 A ~ for a single bond, for oxygen, sulfur, -SO-,

-SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 is} hydrogen, hydroxy, C _r C ₄ alkyl, C _r C ₄ alkoxy, phenyl, C _j -C ₄ - alkylsulfonyl or phenylsulfonyl stands,

A further for C, -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, C ₂ -, each optionally substituted by fluorine, chlorine or 15 bromine,

C ₆ -Azaalkendiyl, C ₂ -C ₆ alkynediyl, C ₃ -C ₆ -cycloalkanediyl, C ₃ - C ₆ is cycloalkenediyl or phenylene,

A represents hydrogen, with the proviso that in this case A and / or A ^~ do not represent a single bond,

20 A also for hydroxy, amino, cyano, isocyano, thio cyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, each optionally substituted by fluorine, chlorine or C ₁ -C ₄ alkoxy Alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino,

25 dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl, each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino, alkylidene-amino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynyl, each optionally substituted by fluorine or chlorine.

30 amino or alkynyloxycarbonyl, each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, for each optionally by fluorine, chlorine, Cyano, carboxy, C, -C ₄ alkyl and / or C, -C ₄ alkoxy carbo¬ nyl substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkyl alkoxy, cycloalkylidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, each with 3 to 6 carbon 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, C _r C ₄ alkyl, C, -C ₄ haloalkyl, C _r C ₄ alkyl oxy, C _r C ₄ -haloalkyloxy and / or C, -C ₄ -alkoxy-carbonyl-substituted phenyl, phenyloxy, phenyl-C _r C ₄ -alkyl,

Phenyl-C, -C ₄ -alkoxy, phenyloxycarbonyl or phenyl-C, -C ₄ - alkoxycarbonyl,

3 further for each optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyylidinyl, pyridinyl, pyridine , pyrazolyl -C _r C ₄ -alkyl, furyl C _j -C ₄ -alkyl, thienyl-C, -C ₄ -alkyl, _oxazolyl-C] -C ₄ -alkyl, isoxazole-C _r C ₄ alkyl, Thiazole-C _] -C ₄ -alkyl, pyridinyl-C ₁ -C ₄ -alkyl, pyrimidinyl-C _] -C ₄ -alkyl, pyrazolylmethoxy, furyl methoxy, represents perhydropyranylmethoxy or pyridylmethoxy, or

R ⁴ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, fluorine, chlorine, bromine, C _] -C ₄ -alkoxy-carbonyl, C ₁ -C ₄ -alkylamino, di- (C, -C ₄ -alkyl) -amino, or for alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio or alkynylthio, optionally substituted by hydroxy, nitro, cyano, fluorine, chlorine, bromine or C 1 -C ₄ -alkoxy each has up to 6 carbon atoms,

R ⁵ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro,

Fluorine, chlorine, bromine, C _r C ₄ -alkoxy-carbonyl, C _r C ₄ alkylamino, di- (C, -C ₄ alkyl) amino, or represents optionally droxy respectively by Hy¬, nitro, cyano, fluorine , Chlorine, bromine or C, - ^ - alkoxy substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, Alkylthio, alkenylthio or alkynylthio each having up to 6 carbon atoms, and

R ^{6 represents} hydrogen, hydroxyl, amino, cyano, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, each optionally substituted by cyano, nitro, fluorine, chlorine, bromine or C _] -C ₄ -alkoxy,

Alkylsulphinyl, alkylsulphonyl each having up to 6 carbon atoms, or represents in each case optionally cyano-, fluorine, chlorine, bromine or C _r C ₄ -alkyl-substituted cycloalkyl or cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups,

except the compounds l- (4-chloro-2-fluorophenyl) - 1,2,3, 4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, l- (3-chloro-4- fluorophenyl) -l, 2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, l- (4-chloro-3-trifluoromethyl-phenyl) -l, 2,3,4-tetrahydro -2,4-dioxopyrimidine-5-carbonitrile, l- (3,4-dichlorophenyl) - l,

2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, l- [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

R ^{1 represents} hydrogen, fluorine or chlorine,

R ^{3 represents} the grouping -A ¹ -A ² -A ³ ,

in which

A ^{1 stands} for a single bond, for oxygen, sulfur, -SO-, -CO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 stands} for

Is hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl, A ¹ 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,

A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, methyl, ethyl, n- or i-propyl , Methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,

1

10 A ^~ 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,

A ^{3 represents} hydrogen, with the proviso that in this case 15 A ¹ and / or A ² do not represent a single bond,

A ³ furthermore for hydroxyl, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl which are optionally substituted by fluorine, chlorine, methoxy or ethoxy , n-, i-, s- or t-butyl, n-, i-, s- 20 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, methyl¬ sulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, 25 ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, Ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, di ethoxy phosphoryl or dipropoxyphosphoryl, diisopropoxyphosphoryl, for propenyl, butenyl, propenyloxy which are optionally substituted by fluorine or chlorine,

Butenyloxy, propenylamino, butenylamino, propylidene amino, butylidene amino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, Butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarb onyl,

Cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclo- butylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclo- propylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, Cyclopentylidenamino, cyclohexyl identical amino, cyclopentyloxycarbonyl, cyclohexyl oxycarbonyl, Cyc- lopentylmethoxycarbonyl or Cyclohexylmethoxycarbonyl, or in each case optionally nitro-, 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,

A ' ¹ furthermore for (in each case fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl,

Thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolmethyl, thiazolmethyl, pyridylmethylmethyl, pyridylmethylmethyl, pyridylmethylmethyl, pyridylmethylmethyl, pyridylmethylmethyl ,

R ^{4 represents} hydrogen, cyano, fluorine, chlorine or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine,

R ^{5 represents} hydrogen, cyano, fluorine, chlorine or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine, and R ⁶ for hydrogen, amino, cyano or for 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 the compounds l- (4-chloro-2-fluorophenyl) - 1,2,3, 4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, l- (3-chloro-4- fluorophenyl) -l, 2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, l- (4-chloro-3-trifluoromethyl-phenyl) -l, 2,3 , 4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile, 1 - (3, 4-di chlorophenyl) - 1,2,3, 4-tetrahydro-2,4-dioxopyrimidine-5- carbonitrile, l- [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)

^V

in which R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^{6 have} the meanings given in Claim 1,

characterized in that one

(a) Halogenarenes of the general formula (II)

in which R, R "and R ^{" have} the meaning given above and

X ^{1 represents} halogen,

with uracenes of the general formula (III)

R ^D

in which

R ⁴ , R ^ ¹ and R ^{6 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

R ¹ , R ² and R ^{3 have} the meaning given above,

with 3-alkoxy-l-oxo-2-alkenyl-carbamic acid esters of the general formula (V) R ^D

in which

R ⁴ , R ⁵ and R ^{6 have} the meaning given above, and

R represents alkyl,

5. Herbicidal agents, characterized by a content of at least one substituted phenyluracil of the general formula (I) according to claims 1 to 4.

6. A method for controlling undesirable plants, characterized in that substituted phenyluracils of the general formula (I) according to Claims 1 to 4 are allowed to act on undesired plants and / or their habitat.

7. Use of substituted phenyluracils of the general formula (I) according to Claims 1 to 4 for combating undesired plants.

8. A process for the preparation of herbicidal compositions, characterized in that substituted phenyluracils of the general formula (I) according to Claims 1 to 4 are mixed with extenders and / or surface-active substances.