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

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

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Publication number
WO1997005117A1
WO1997005117A1 PCT/EP1996/003222 EP9603222W WO9705117A1 WO 1997005117 A1 WO1997005117 A1 WO 1997005117A1 EP 9603222 W EP9603222 W EP 9603222W WO 9705117 A1 WO9705117 A1 WO 9705117A1
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WIPO (PCT)
Prior art keywords
cyano
alkyl
alkoxy
chlorine
fluorine
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PCT/EP1996/003222
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German (de)
French (fr)
Inventor
Karl-Heinz Linker
Kurt Findeisen
Roland Andree
Mark Wilhelm Drewes
Markus Dollinger
Hans-Joachim Santel
Original Assignee
Bayer Aktiengesellschaft
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Priority to AU66585/96A priority Critical patent/AU6658596A/en
Publication of WO1997005117A1 publication Critical patent/WO1997005117A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil

Definitions

  • 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.
  • R 1 represents hydrogen, cyano or halogen
  • R ⁇ stands for cyano, carbamoyl, thiocarbamoyl, halogen or for alkyl or alkoxy which is optionally substituted by halogen,
  • K ⁇ 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 -, -,
  • 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
  • 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 al
  • 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,
  • R 1 , R 2 and R 3 have the meaning given above and
  • reaction auxiliary optionally in the presence of a reaction auxiliary and optionally in the presence of a reaction auxiliary
  • R 1 , R 2 and R 3 have the meaning given above,
  • R 4 , R 5 and R 6 have the meaning given above, and
  • R represents alkyl
  • 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
  • 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
  • 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,
  • 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 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
  • 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
  • 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,
  • 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,
  • 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 ,
  • 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,
  • a 3 continues for (in some cases fully or partially hydrogenated)
  • 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,
  • 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
  • R 4 and R 6 have, for example, the meanings listed below:
  • 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-dich
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, those given above under Group 1
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, those given above under Group 1
  • Ar, R 4 and R 6 have, for example, those given above under Group 1
  • Ar, R 4 and R 6 have, for example, those given above under Group 1
  • Ar, R 4 and R 6 have, for example, those given above under Group 1
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, those given above under Group 1
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R> 4 and R have, for example, those given above under Group 1
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
  • 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).
  • 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).
  • 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)
  • Aminoarenes to be used as starting materials are generally defined by 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.
  • 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
  • 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),
  • 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
  • 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,
  • 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
  • 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
  • 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:
  • Sorghum Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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 can also be used as a weed control in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • 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, pyrazosulfur
  • 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.
  • 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.
  • 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.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • 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.
  • the amount of water per unit area expediently constant.
  • concentration of active substance in the preparation is irrelevant; the decisive factor is only the amount of active substance applied per unit area.
  • 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%).
  • Setaria 95-100%
  • Abutilon 100%
  • Cyperus (95% Cyperus
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • 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.
  • 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.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • 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

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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

SUBSTITUIERTE 1-PHENYLURACIL DERIVATE, DEREN HERSTELLUNG UND DEREN VERWENDUNG ALS HERBIZIDESUBSTITUTED 1-PHENYLURACIL DERIVATIVES, THEIR PRODUCTION AND THE USE THEREOF AS HERBICIDES
Die Erfindung betrifft neue substituierte Phenyluracile, Verfahren zu ihrer Her- 5 Stellung und ihre Verwendung als Herbizide.The invention relates to new substituted phenyluracils, processes for their preparation and their use as herbicides.
Substituierte Uracile, wie z.B. die Verbindungen l-(4-Chlor-2-fluor-phenyl)- l,2,3,4-tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril, l-(3-Chlor-4-fluor-phenyl)- l,2,3,4-tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril, l-(4-Chlor-3-trifluormethyl- phenyl)-l,2,3,4-tetrahydro-2,4-dioxo-pyrirnidin-5-carbonitril und l-(3,4-Dichlor- 10 phenyl)-!, 2,3, 4-tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril (vgl. US 4266056) so¬ wie l-[4-Chlor-2-fluor-5-(2-propinyloxy)-phenyl]-3-methyl-2,4-(lH,3H)-pyridin- dion (vgl. US 5298502) sind bereits aus der Patentliteratur bekannt. Über eine her¬ bizide Wirksamkeit dieser Verbindungen ist jedoch bisher nichts bekannt ge¬ worden.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 Es wurden nun die neuen substituierten Phenyluracile der allgemeinen Formel (I) gefunden15 The new substituted phenyluracils of the general formula (I) have now been found
R°R °
Figure imgf000003_0001
Figure imgf000003_0001
in welcherin which
R1 für Wasserstoff, Cyano oder Halogen steht,R 1 represents hydrogen, cyano or halogen,
20 R~ für Cyano, Carbamoyl, Thiocarbamoyl, Halogen oder für jeweils gege¬ benenfalls durch Halogen substituiertes Alkyl oder Alkoxy steht,20 R ~ stands for cyano, carbamoyl, thiocarbamoyl, halogen or for alkyl or alkoxy which is optionally substituted by halogen,
KΛ für die Gruppierung A -A"-A steht, worin A1 fur eine Einfachbindung, fur Sauerstoff, Schwefel, -SO-, -SO-,-, - CO- oder die Gruppierung -N-A4- steht, worin A4 fur Wasserstoff, Hydroxy, Alkyl, Alkenyl, Alkinyl, Alkoxy, Aryl, Alkylsulfonyl oder Arylsulfonyl steht,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,
A1 weiterhin fur jeweils gegebenenfalls durch Halogen substituiertesA 1 further for each optionally substituted by halogen
Alkandiyl, Alkendiyl, Azaalkendiyl, Alkindiyl, Cycloalkandiyl, Cycloalkendiyl oder Phenylen steht,Alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkendiyl or phenylene,
Ar fur eine Einfachbindung, fur Sauerstoff, Schwefel, -SO-, -SO-,-,Ar for a single bond, for oxygen, sulfur, -SO-, -SO -, -,
-CO- oder die Gruppierung -N-A4- steht, worin A4 fur Wasserstoff, Hydroxy, Alkyl, Alkoxy, Aryl, Alkylsulfonyl oder Arylsulfonyl steht,-CO- or the grouping -NA 4 - in which A 4 represents hydrogen, hydroxy, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl,
A" weiterhin fur jeweils gegebenenfalls durch Halogen substituiertes Alkandiyl, Alkendiyl, Azaalkendiyl, Alkindiyl, Cycloalkandiyl, Cyc¬ loalkendiyl oder Phenylen steht,A "furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
A"1 fur Wasserstoff steht mit der Maßgabe, daß in diesem Fall A1 und/oder A" nicht fur eine Einfachbindung stehenA " 1 represents hydrogen with the proviso that in this case A 1 and / or A" do not represent a single bond
A* weiterhin fur Hydroxy, Amino, Cyano, Isocyano, Thiocyanato,A * furthermore for hydroxy, amino, cyano, isocyano, thiocyanato,
Nitro, Carboxy, Carbamoyl, Thiocarbamoyl, Sulfo, Chlorsulfonyl,Nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl,
Halogen, fur jeweils gegebenenfalls durch Halogen oder Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl,Halogen, for in each case optionally substituted by halogen or alkoxy alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl,
Alkylamino, Dialkylamino, Alkoxycarbonyl oder Dialkoxy(thio)- phosphoryl, fur jeweils gegebenenfalls durch Halogen substituiertes Alkenyl, Alkenyloxy, Alkenylamino, Alkylidenamino, Alkenyloxy- carbonyl, Alkinyl, Alkinyloxy, Alkinylamino oder Alkinyl oxy - carbonyl, fur jeweils gegebenenfalls durch Halogen, Cyano, Carb¬ oxy, Alkyl und/oder Alkoxy-carbonyl substituiertes Cycloalkyl, Cycloalkyloxy, Cycloalkylalkyl, Cycloalkylalkoxy, Cycloalkyliden- amino, Cycloalkyloxycarbonyl oder Cycloalkylalkoxycarbonyl, oder fur jeweils gegebenenfalls durch Nitro, Cyano, Carboxy, Halogen, Alkyl, Halogenalkyl, Alkyloxy, Hal ogenal kyl oxy und/oder Alkoxy¬ carbonyl substituiertes Aryl, Aryloxy, Aralkyl, Arylalkoxy, Aryloxy- carbonyl oder Arylalkoxycarbonyl steht, A" weiterhin für jeweils gegebenenfalls ganz oder teilweise hydriertes Pyrrolyl, Pyrazolyl, Imidazolyl, Triazolyl , Furyl, Oxiranyl, Oxetanyl, Dioxolanyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Iso¬ thiazolyl, Oxadiazolyl, Thiadiazolyl, Pyridinyl, Pyrimidinyl, Triazinyl, Pyrazolylalkyl, Furylalkyl, Thienylalkyl, Oxazolylalkyl, Isoxazolalkyl, Thiazolalkyl, Pyridinylalkyl, Pyrimidinylalkyl, Pyrazolylalkoxy, Furylalkoxy, für Perhydropyranylalkoxy oder Pyridylalkoxy steht,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 für Wasserstoff, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Nitro, Halo- gen, Alkoxycarbonyl, Alkylamino, Dialkylamino, oder für jeweils gege¬ benenfalls durch Hydroxy, Nitro, Cyano, Halogen oder Alkoxy substitu¬ iertes Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Alkylthio, Alkenylthio oder Alkinylthio steht,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,
R5 für Wasserstoff, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Nitro, Halo- gen, Alkoxycarbonyl, Alkylamino, Dialkylamino, oder für jeweils gegebe¬ nenfalls durch Hydroxy, Nitro, Cyano, Halogen oder Alkoxy substituiertes Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Alkylthio, Alkenylthio oder Alkinylthio steht, undR 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
R6 für Wasserstoff, Hydroxy, Amino, Cyano, für jeweils gegebenenfalls durch Cyano, Nitro, Halogen oder Alkoxy substituiertes Alkyl, Alkenyl, Alkinyl,R 6 represents hydrogen, hydroxyl, amino, cyano, each alkyl, alkenyl, alkynyl optionally substituted by cyano, nitro, halogen or alkoxy,
Alkoxy, Alkenyloxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, oder für je¬ weils gegebenenfalls durch Cyano, Halogen oder Alkyl substituiertes Cyclo¬ alkyl oder Cycloalkylalkyl steht,Alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, or for cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or alkyl,
wobei die vorbekannten Verbindungen l-(4-Chlor-2-fluor-phenyl)- 1,2,3, 4-tetra- hydro-2,4-dioxo-pyrimidin-5-carbonitril, l-(3-Chlor-4-fluor-phenyl)-l,2,3,4-tetra- hydro-2,4-dioxo-pyrimidin-5-carbonitril, l-(4-Chlor-3-trifluormethyl-phenyl)- l,2,3,4-tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril und l-(3,4-Dichlor-phenyl)- l,2,3,4-tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril (vgl. US 4266056) sowie l -[4- Chlor-2-fluor-5-(2-propinyloxy)-phenyl]-3-methyl-2,4-(lH,3H)-pyridindion (vgl. US 5298502) durch Disclaimer ausgenommen sind.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.
Man erhält die neuen substituierten Phenyluracile der allgemeinen Formel (I), wenn man (a) Halogenarene der allgemeinen Formel (II)The new substituted phenyluracils of the general formula (I) are obtained if (a) Halogenarenes of the general formula (II)
Figure imgf000006_0001
Figure imgf000006_0001
in welcherin which
R1, R2 und R3 die oben angegebene Bedeutung haben undR 1 , R 2 and R 3 have the meaning given above and
X für Halogen steht,X represents halogen,
mit Uracilen der allgemeinen Formel (III)with uracenes of the general formula (III)
RD R D
Figure imgf000006_0002
in welcher
Figure imgf000006_0002
in which
R , R und R die oben angegebene Bedeutung haben,R, R and R have the meaning given above,
gegebenenfalls in Gegenwart eines Reaktionshilfsmittels und gegebenenfalls inoptionally in the presence of a reaction auxiliary and optionally in
Gegenwart eines Verdünnungsmittels umsetzt,In the presence of a diluent,
oder wenn manor if you
(b) Aminoarene der allgemeinen Formel (IV)
Figure imgf000007_0001
(b) aminoarenes of the general formula (IV)
Figure imgf000007_0001
in welcherin which
R1, R2 und R3 die oben angegebene Bedeutung haben,R 1 , R 2 and R 3 have the meaning given above,
mit 3-Alkoxy-l-oxo-2-alkenyl-carbamidsäureestern der allgemeinen Formel (V)with 3-alkoxy-l-oxo-2-alkenyl-carbamic acid esters of the general formula (V)
Figure imgf000007_0002
Figure imgf000007_0002
in welcherin which
R4, R5 und R6 die oben angegebene Bedeutung haben, undR 4 , R 5 and R 6 have the meaning given above, and
R für Alkyl steht,R represents alkyl,
gegebenenfalls in Gegenwart eines Reaktionshilfsmittels und gegebenenfalls in Ge¬ genwart eines Verdünnungsmittels umsetzt.if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
Die Verbindungen der allgemeinen Formel (I) können auch nach weiteren üblichen Methoden in andere Verbindungen der allgemeinen Formel (I) gemäß obiger Definition umgewandelt werden, beispielsweise durch nucleophile Substitution (z.B. R3: F → OH, SH, NH2, OCH3, NHSO2CH3; durch Alkylierung (z.B. R6: H —> CH3); oder durch weitere Umwandlungen fünktioneller Gruppen (z.B. R2: CONH-, → CN, CN → CSNH2; R3: NO2 → NH2, NH-, → F, Cl, Br, CN, NHSO-,CH3, SO-,Cl) - vgl. auch die Herstellungsbeispiele. Die neuen substituierten Phenyluracile der allgemeinen Formel (1) zeichnen sich durch starke herbizide Wirksamkeit ausThe 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 den Definitionen sind die gesattigten oder ungesättigten Kohlenwasserstoff¬ ketten, wie Alkyl, Alkenyl oder Alkinyl jeweils geradkettig oder verzweigtIn the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkynyl, are each straight-chain or branched
Halogen steht im allgemeinen fur Fluor, Chlor, Brom oder lod, vorzugsweise furHalogen generally represents fluorine, chlorine, bromine or iodine, preferably
Fluor, Chlor oder Brom, insbesondere fur Fluor oder ChlorFluorine, chlorine or bromine, especially for fluorine or chlorine
Gegenstand der Erfindung sind vorzugsweise Verbindungen der Formel (I), in wel¬ cherThe invention preferably relates to compounds of the formula (I) in which
R1 fur Wasserstoff, Cyano, Fluor, Chlor oder Brom steht,R 1 represents hydrogen, cyano, fluorine, chlorine or bromine,
R" fur Cyano, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, oder fur je¬ weils gegebenenfalls durch Fluor und/oder Chlor substituiertes Alkyl oder Alkoxy mit jeweils 1 oder 2 Kohlenstoffatomen steht,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' fur die Gruppierung -A!-A2-A3 steht,R 'for grouping -A ! -A 2 -A 3 stands,
in welcherin which
A1 fur eine Einfachbindung, fur Sauerstoff, Schwefel, -SO-, -SO-,-,A 1 for a single bond, for oxygen, sulfur, -SO-, -SO -, -,
-CO- oder die Gruppierung -N-A4- steht, worin A4 fur Wasserstoff, Hydroxy, CrC4-Alkyl, C3-C4-Alkenyl, C3-C4-Alkinyl, C,-C4-Alk- oxy, Phenyl, C,-C4-Alkylsulfonyl oder Phenylsulfonyl steht,-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,
A1 weiterhin fur jeweils gegebenenfalls durch Fluor, Chlor oder Brom substituiertes CrC6- Alkandiyl, C2-C6-Alkendiyl, C2-C6-Azaalken- diyl, C2-C6- Alkindiyl, C3-C6-Cycloalkandiyl, C3-C6-Cycloalkendiyl oder Phenylen steht,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" fur eine Einfachbindung, fur Sauerstoff, Schwefel, -SO-, -SO-,-,A "for a single bond, for oxygen, sulfur, -SO-, -SO -, -,
-CO- oder die Gruppierung -N-A - steht, woπn A4 fur Wasserstoff, Hydroxy, CrC4-Alkyl, CrC4-Alkoxy, Phenyl, CrC4-Alkylsulfonyl oder Phenylsulfonyl steht, A~ weiterhin für jeweils gegebenenfalls durch Fluor, Chlor oder Brom substituiertes C,-C6-Alkandiyl, C2-C6-Alkendiyl, G,-Cf)-Azaalken- diyl, C2-C6-Alkindiyl, C3-C6-Cycloalkandiyl, C3-C6-Cycloalkendiyl oder Phenylen steht,-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,
A3 für Wasserstoff steht, mit der Maßgabe,daß in diesem Fall A1 und/oder A nicht für eine Einfachbindung stehen,A 3 represents hydrogen, with the proviso that in this case A 1 and / or A do not represent a single bond,
A3 weitwerhin für Hydroxy, Amino, Cyano, Isocyano, Thiocyanato, Nitro, Carboxy, Carbamoyl, Thiocarbamoyl, Sulfo, Chlorsulfonyl, Fluor, Chlor, Brom, für jeweils gegebenenfalls durch Fluor, Chlor oder CrC4-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkyl¬ sulfinyl, Alkylsulfonyl, Alkylamino, Dialkylamino, Alkoxycarbonyl oder Dialkoxy(thio)phosphoryl mit jeweils 1 bis 6 Kohlenstoff¬ atomen in den Alkylgruppen, für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes Alkenyl, Alkenyloxy, Alkenylamino, Al- kylidenamino, Alkenyloxycarbonyl, Alkinyl, Alkinyloxy, Alkinyl- amino oder Alkinyloxycarbonyl mit jeweils 2 bis 6 Kohlenstoff¬ atomen in den Alkenyl-, Alkyliden- oder Alkinylgruppen, für je¬ weils gegebenenfalls durch Fluor, Chlor, Cyano, Carboxy, C,-C4- Alkyl und/oder C]-C4-Alkoxy-carbonyl substituiertes Cycloalkyl, Cycloalkyloxy, Cycloalkylalkyl, Cycloalkylalkoxy, Cycloalkyliden- amino, Cycloalkyloxycarbonyl oder Cycloalkylalkoxycarbonyl mit jeweils 3 bis 6 Kohlenstoffatomen in den Cycloalkyl gruppen und gegebenenfalls 1 bis 4 Kohlenstoffatomen in den Alkylgruppen, oder für jeweils gegebenenfalls durch Nitro, Cyano, Carboxy, Fluor, Chlor, Brom, CrC4-Alkyl, CrC4-Halogenalkyl, CrC4-Alkyloxy,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,
Cj-C4-Halogenalkyloxy und/oder C1-C4-Alkoxy-carbonyl substitu¬ iertes Phenyl, Phenyloxy, Phenyl-CrC4-alkyl, Phenyl-C]-C4-alkoxy, Phenyloxycarbonyl oder Phenyl-C]-C4-alkoxycarbonyl steht,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,
AJ weiterhin für jeweils gegebenenfalls ganz oder teilweise hydriertes Pyrrolyl, Pyrazolyl, Imidazolyl, Triazolyl, Furyl, Oxiranyl, Ox- etanyl, Dioxolanyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Iso¬ thiazolyl, Oxadiazolyl, Thiadiazolyl, Pyridinyl, Pyrimidinyl, Tri¬ azinyl, Pyrazolyl-C]-C4-alkyl, Furyl-CrC4-alkyl, Thienyl-C,-C4-al- kyl, Oxazolyl-CrC4-alkyl, Isoxazol-CrC4-alkyl, Thiazol-C,-C4-al- kyl, Pyridinyl-C,-C4-alkyl, Pyrimidιnyl-C,-C4-alkyl, Pyrazolylmeth- oxy, Furylmethoxy, fur Perhydropyranylmethoxy oder Pyridyl- methoxy steht, oderA 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
R4 fur Wasserstoff, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Nitro, Fluor, Chlor, Brom, C,-C4-Alkoxy-carbonyl, C,-C4-Alkylamino, Di-(C,-C4-alkyl)- amino, oder fur jeweils gegebenenfalls durch Hydroxy, Nitro, Cyano, Fluor, Chlor, Brom oder C,-C4-Alkoxy substituiertes Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Alkylthio, Alkenylthio oder Alkinylthio mit jeweils bis zu 6 Kohlen stoff atomen steht,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,
R5 fur Wasserstoff, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Nitro, Fluor,R 5 for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro, fluorine,
Chlor, Brom, C,-C4-Alkoxy-carbonyl, CrC4-Alkylamino, Di-(CrC4-alkyl)- amino, oder fur jeweils gegebenenfalls durch Hydroxy, Nitro, Cyano, Fluor, Chlor, Brom oder C^Qj-Alkoxy substituiertes Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Alkylthio, Alkenylthio oder Alkinylthio mit jeweils bis zu 6 Kohlenstoffatomen steht, undChlorine, 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
R6 fur Wasserstoff, Hydroxy, Amino, Cyano, für jeweils gegebenenfalls durch Cyano, Nitro, Fluor, Chlor, Brom oder C,-C4-Alkoxy substituiertes Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkylthio, Alkylsulfinyl, Alkyl¬ sulfonyl mit jeweils bis zu 6 Kohlenstoffatomen, oder fur jeweils gege- benenfalls durch Cyano, Fluor, Chlor, Brom oder Cj-C4-Alkyl substituiertesR 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 oder Cycloalkylalkyl mit 3 bis 6 Kohlenstoffatomen in den Cycloalkylgruppen und gegebenenfalls 1 bis 4 Kohlenstoffatomen in den Alkylgruppen steht,Cycloalkyl or cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups,
wobei die vorbekannten Verbindungen l-(4-Chlor-2-fluor-phenyl)-l,2,3,4-tetra- hydro-2,4-dioxo-pyrimidin-5-carbonitril, l-(3-Chlor-4-fluor-phenyl)- 1,2,3, 4-tetrahy- dro-2,4-dioxo-pyrimidin-5-carbonitril, l-(4-Chlor-3-trifluormethyl-phenyl)-l,2,3,4- tetrahydro-2,4-dioxo-pyrirnidin-5-carbonitril und l-(3,4-Dichlor-phenyl)-l,2,3,4- tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril (vgl US 4266056) sowie l-[4-Chlor- 2-fluor-5-(2-propinyloxy)-phenyl]-3-methyl-2,4-(lH,3H)-pyridindion (vgl US 5298502) durch Disclaimer ausgenommen sindwhere 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
Die Erfindung betrifft insbesondere Verbindungen der Formel (I), in welcher R1 für Wasserstoff, Fluor oder Chlor steht,The invention relates in particular to compounds of the formula (I) in which R 1 represents hydrogen, fluorine or chlorine,
R2 für Cyano, Thiocarbamoyl, Fluor, Chlor, Brom, Methyl oder Trifluormethyl steht,R 2 represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, methyl or trifluoromethyl,
R3 für die Gruppierung -A'-A2-A3 steht,R 3 represents the grouping -A'-A 2 -A 3 ,
in welcherin which
A1 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO,-, -CO- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff, Hydroxy, Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylsulfonyl oder Ethylsulfonyl steht,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,
A1 weiterhin für Methylen, Ethan- 1,1 -diyl, Ethan- 1, 2-diyl, Propan- 1,1- diyl, Propan- 1, 2-diyl, Propan- 1,3-diyl, Ethen- 1, 2-diyl, Propen-1,2- diyl, Propen- 1,3-diyl, Ethin-1, 2-diyl oder Propin- 1,3-diyl steht,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" für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO-,-, -CO- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff, Hydroxy, Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl oder Phenylsulfonyl steht,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,
A2 weiterhin für Methylen, Ethan- 1,1 -diyl, Ethan- 1, 2-diyl, Propan- 1,1- diyl, Propan- 1, 2-diyl, Propan- 1,3-diyl, Ethen- 1, 2-diyl, Propen- 1,2- diyl, Propen-l,3-diyl, Ethin-1, 2-diyl oder Propin- 1,3 -diyl steht,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,
AJ für Wasserstoff steht, mit der Maßgabe, daß in diesem Fall A1 und/oder A2 nicht für eine Einfachbindung stehen,A J stands for hydrogen, with the proviso that in this case A 1 and / or A 2 do not represent a single bond,
A3 weiterhin für Hydroxy, Amino, Cyano, Nitro, Carboxy, Carbamoyl,A 3 furthermore for hydroxy, amino, cyano, nitro, carboxy, carbamoyl,
Sulfo, Fluor, Chlor, Brom, für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Sulfo, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i- substituted by fluorine, chlorine, methoxy or ethoxy
Propyl, n-, i-, s- oder t-Butyl, n-, i-, s- oder t-Pentyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, n-, i-, s- oder t- Pentyloxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propyl sulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl, Methyl¬ amino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butyl- amino, Dimethylamino, Diethylamino, Methoxycarbonyl, Ethoxy- 5 carbonyl, n- oder i-Propoxycarbonyl, Dimethoxyphosphoryl, Di- ethoxyphosphoryl oder Dipropoxyphosphoryl, Diisopropoxyphos- phoryl, für jeweils gegebenenfalls durch Fluor oder Chlor substitu¬ iertes Propenyl, Butenyl, Propenyloxy, Butenyloxy, Propenylamino, Butenylamino, Propylidenamino, Butylidenamino, Propenyl oxy car- 10 bonyl, Butenyloxycarbonyl, Propinyl, Butinyl, Propinyloxy, Butinyl- oxy, Propinylamino, Butinylamino, Propinyloxycarbonyl oder Bu- tinyloxycarbonyl, für jeweils gegebenenfalls durch Fluor, Chlor, Cyano, Carboxy, Methyl, Ethyl, n- oder i-Propyl, Methoxycarbonyl oder Ethoxycarbonyl substituiertes Cyclopropyl, Cyclobutyl, Cyclo- 15 pentyl, Cyclohexyl, Cyclopropyloxy, Cyclobutyloxy, Cyclopentyl¬ oxy, Cyclohexyloxy, Cyclopropylmethyl, Cyclobutylmethyl, Cyclo- pentylmethyl, Cyclohexylmethyl, Cyclo-propylmethoxy, Cyclobutyl- methoxy, Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclopen- tylidenamino, Cyclohexylidenamino, Cyclopentyloxycarbonyl, Cyc- 20 lohexyloxycarbonyl, Cyclopentylmethoxycarbonyl oder Cyclohexyl- methoxycarbonyl, oder für jeweils gegebenenfalls durch Nitro, Cyano, Carboxy, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i- Propyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Di¬ fluormethoxy, Trifluormethoxy, Methoxycarbonyl und/oder Ethoxy- 25 carbonyl substituiertes Phenyl, Phenyloxy, Benzyl, Phenylethyl,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 steht,Benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl,
A3 weiterhin für (jeweils gegebenenfalls ganz oder teilweise hydriertes)A 3 continues for (in some cases fully or partially hydrogenated)
Pyrrolyl, Pyrazolyl, Imidazolyl, Triazolyl, Furyl, Thienyl, Oxazolyl,Pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl,
Isoxazolyl, Thiazolyl, Isothiazolyl, Oxadiazolyl, Thiadiazolyl, Pyri-Isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyri-
30 dinyl, Pyrimidinyl, Triazinyl, Pyrazolylmethyl, Furylmethyl, Thie- nylmethyl, Oxazolylmethyl, Isoxazolmethyl, Thiazol methyl, Pyri- dinylmethyl, Pyrimidinylmethyl, Pyrazolylmethoxy, Furylmethoxy oder Pyridylmethoxy steht, R fur Wasserstoff, Cyano, Fluor, Chlor oder fur jeweils gegebenenfalls durch30 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
Fluor und/oder Chlor substituiertes Methyl, Ethyl, Methoxy oder Ethoxy steht,Fluorine and / or chlorine substituted methyl, ethyl, methoxy or ethoxy,
R5 fur Wasserstoff, Cyano, Fluor, Chlor oder fur jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, Methoxy oder Ethoxy steht, undR 5 represents hydrogen, cyano, fluorine, chlorine or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine, and
R6 fur Wasserstoff, Amino, Cyano oder fur jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Propenyl, Butenyl, Propinyl oder Butinyl steht,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,
wobei die vorbekannten Verbindungen l-(4-Chlor-2-fluor-phenyl)-l,2,3,4-tetrahy- dro-2,4-dioxo-pyrimidin-5-carbonitril, l-(3-Chlor-4-fluor-phenyl)-l,2,3,4-tetrahy- dro-2,4-dioxo-pyrimidin-5-carbonitril, l-(4-Chlor-3-trifluormethyl-phenyl)-l, 2,3,4- tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril und 1 -(3 ,4-Dichlor-phenyl)- 1,2,3,4- tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril (vgl US 4266056) sowie l-[4-Chlor-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-fluor-5-(2-propinyloxy)-phenyl]-3-methyl-2,4-(lH,3H)-pyridindion (vgl US 5298502) durch Disclaimer ausgenommen sind2-fluoro-5- (2-propynyloxy) phenyl] -3-methyl-2,4- (1H, 3H) -pyridinedione (cf. US 5298502) are excluded by disclaimers
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Reste¬ definitionen gelten sowohl fur die Endprodukte der Formel (I) als auch ent- sprechend fur die jeweils zur Herstellung benotigten Ausgangsstoffe bzw Zwi¬ schenprodukte Diese Restedefinitionen können untereinander, also auch zwischen den angegebenen bevorzugten Bereichen beliebig kombiniert werdenThe 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
Beispiele fur die erfindungsgemaßen Verbindungen der Formel (I) sind in den nachstehenden Gruppen aufgeführt Gruppe 1Examples of the compounds of formula (I) according to the invention are listed in the groups below Group 1
Figure imgf000014_0001
Figure imgf000014_0001
R4 und R6 haben hierbei beispielhaft die im Folgenden aufgeführten Bedeutungen:R 4 and R 6 have, for example, the meanings listed below:
Figure imgf000014_0002
Rϋ R4 R6 R4 R° R4 Rö R4
Figure imgf000014_0002
R ϋ R 4 R 6 R 4 R ° R 4 R ö R 4
CH, Cl CHF2 NO,CH, Cl CHF 2 NO,
>- ϊ>- \>- D>-> - ϊ> - \> - D> -
CHF2 CH3 CHF2 Cl CHF-, CHF, CHF, NO, SCH3 CH, SCH3 Cl S SCCHH3, CHF2 SCH, NO, SCF, CH, SCF3 Cl S SCCFF3, CHF2 SCF, NO2 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
SCF2C1 CH3 SCF2C1 Cl SCF2C1 CHF2 SCF2C1 NO, SCF2CH3 CH3 SCF2CH3 Cl SCF2CH3 CHF2 SCF2CH3 NO,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 CH3 CN Cl CN CHF-, CN NO, CSNH, CH, CSNH2 Cl CSNH2 CHF2 CSNH, NO,CN CH 3 CN Cl CN CHF-, CN NO, CSNH, CH, CSNH 2 Cl CSNH 2 CHF 2 CSNH, NO,
CH2C≡CH CH3 CH,C≡CH Cl CH2C≡CH CHF2 CH2G≡CH NO,CH 2 C≡CH CH 3 CH, C≡CH Cl CH 2 C≡CH CHF 2 CH 2 G≡CH NO,
H F H N(CH3)2 H C CHH,,CCF3 H NH,HFHN (CH 3 ) 2 HC CHH ,, CCF 3 H NH,
CH3 F CH3 N(CH3)2 CH, CH2CF3 CH3 NH2 CH 3 F CH 3 N (CH 3 ) 2 CH, CH 2 CF 3 CH 3 NH 2
C2H5 F C2H5 N(CH3)2 C 2,HH5r CH,CF C2H5 NH, i-C3H7 F i-C3H7 N(CH3)2 i-C3H7 CH,CF3 i-C3H7 NH, n-C3H7 F n-C3H7 N(CH3)2 n-C3H7 CH2CF3 n-C3H7 NH,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(CH3)2 CH,CF3 NH, ϊ>- [>-N (CH 3 ) 2 CH, CF 3 NH, ϊ> - [> -
CHF2 F CHF2 N(CH3)2 CHF2 CH,CF3 C tH>F2- - NH,CHF 2 F CHF 2 N (CH 3 ) 2 CHF 2 CH, CF 3 C tH> F 2 - - NH,
SCH3 F SCH3 N(CH3)2 SCH3 CH,CF3 SCH3 NH,SCH 3 F SCH 3 N (CH 3 ) 2 SCH 3 CH, CF 3 SCH 3 NH,
SCF3 F SCF3 N(CH3)2 SCF, CH2CF3 SCF3 NH,SCF 3 F SCF 3 N (CH 3 ) 2 SCF, CH 2 CF 3 SCF 3 NH,
SCF2C1 F SCF2C1 N(CH3)2 SCF2C1 CH,CF3 SCF2C1 NH,SCF 2 C1 F SCF 2 C1 N (CH 3 ) 2 SCF 2 C1 CH, CF 3 SCF 2 C1 NH,
SCF2CH3 F SCF,CH3 N(CH3)2 SCF,CH3 CH,CF3 SCF2CH3 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(CH3)2 CN CH,CF3 CN NH,CN F CN N (CH 3 ) 2 CN CH, CF 3 CN NH,
CSNH, F CSNH2 N(CH3)2 CSNH, CH,CF3 CSNH, NH,CSNH, F CSNH 2 N (CH 3 ) 2 CSNH, CH, CF 3 CSNH, NH,
CH,C≡CH F CH,C≡CH N(CH3)2 CH,C≡CH CH,CF3 CH,C≡CH NH,CH, C≡CH F CH, C≡CH N (CH 3 ) 2 CH, C≡CH CH, CF 3 CH, C≡CH NH,
Ar hat hierbei beispielhaft die im Folgenden aufgeführten Bedeutungen: 2,4,5-Trichlor-phenyl, 2,4-Dichlor-5-fluor-phenyl, 2-Chlor-4,5-difluor-phenyl, 4- Chlor-2,5-difluor-phenyl, 5-Chlor-2,4-difluor-phenyl, 2-Fluor-5-chlor-4-cyano- phenyl, 2,4,5-Trifluor-phenyl, 2,5-Dichlor-4-cyano-phenyl, 2-Chlor-5-fluor-4- cyanophenyl, 2-Chlor-4,5-dicyano-phenyl, 2-ChIor-4-fluor-5-cyano-phenyl, 2,5- Difluor-4-cyano-phenyl, 2-Chlor-4-cyano-5-methyl-phenyl, 2,4-Dichlor-5-methoxy- phenyl, 2,4-Dichlor-5-ethoxy-phenyl, 2,4-Dichlor-5-n-propoxy-phenyl, 2,4-Dichlor- 5-i-propoxy-phenyl, 4-Chlor-2-fluor-5-methoxy-phenyl, 4-Chlor-2-fluor-5-ethoxy- phenyl, 4-Chlor-2-fluor-5-n-propoxy-phenyl, 4-Chlor-2-fluor-5-i-propoxy-phenyl, 2-Fluor-4-cyano-5-methyl-phenyl, 2,4-Dichlor-5-methyl-phenyl, 2-Chlor-4-cyano-5- trifluormethyl-phenyl, 4-Fluor-3-trifluormethyl-phenyl, 2-Fluor-4-cyano-5-trifluor- methyl-phenyl, 2-Chlor-4-methyl-5-trifluormethyl-phenyl, 2-Chlor-5-fluor-4- methoxy-phenyl, 2-Fluor-4-methoxy-5-methyl-phenyl, 2,5-Difluor-4-thiocarbamoyl- phenyl, 2-Chlor-4-fluor-5-i-propoxy-phenyl, 2-Fluor-4-cyano-5-methoxy-phenyl, 2- Fluor-4-cyano-5-i-propoxy-phenyl, 2-Chlor-4-cyano-5-(2-propinyloxy)-phenyl, 2- Fluor-4-cyano-5-(l-methyl-2-propinyloxy)-phenyl, 2-Chlor-4-thiocarbamoyl-5-i- propoxy-phenyl, 2-Fluor-4-cyano-5-(2-propenyloxy)-phenyl, 2-Fluor-4-chlor-5-(2- propenyloxy)-phenyl, 2-Chlor-4-cyano-5-methylsulfonylamino-phenyl, 2-Fluor-4- cyano-5-ethylsulfonylamino-phenyl, 2-Fluor-4-thiocarbamoyl-5-methylsulfonyl- amino-phenyl, 2-Chlor-4-cyano-5-ethylsulfonylamino-phenyl, 2-Fluor-4-cyano-5- cyclopropylsulfonylamino-phenyl, 2-Fluor-4-cyano-5-i-propylsulfonylamino-phenyl,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-Chlor-4-thiocarbamoyl-5-ethylsulfonylaminophenyl, 2-Chlor-4-cyano-5-cyan- amino-phenyl, 2-Fluor-4-cyano-5-trifluormethyl sulfonyl amino-phenyl, 2-Fluor-4- cyano-5-(2,2-difluorethylsulfonylamino)-phenyl, 2-Fluor-4-cyano-5-phenylsulfonyl- amino-phenyl, 2-Fluor-4-cyano-5-t-butylsulfonylamino-phenyl, 2-Chlor-4-cyano-5- methoxycarbonyl-phenyl, 2-Fluor-4-cyano-5ethoxycarbonyl-phenyl, 2-Fluor-4-thio- carbamoyl-5-methoxycarbonyl-phenyl, 2-Chlor-4-cyano-5-(N-cyclopropyl-ethy- sulfonylamino)-phenyl, 2-Fluor-4-cyano-5-(l-methyl-2-propinylthio)-phenyl, 2- Fluor-4-cyano-5-methylamino-phenyl, 2-Chlor-4-thiocarbamoyl-5-methoxy- carbonylmethyl-phenyl, 2-Chlor-4-cyano-5-(N-methyl-ethylsulfonylamino)-phenyl, 2-Chlor-4-cyano-5-i-propoxycarbonyl-phenyl, 2-Fluor-4-cyano-5-(bis-ethylsulfonyl- amino)-phenyl, 2-Fluor-4-cyano-5-(N-methylsulfonylethylsulfonylamino)-phenyl, 2- Fluor-4-cyano-5-(l-methoxycarbonyl-ethoxy)-phenyl, 2-Fluor-4-cyano-5-cyclo- propyloxy-phenyl, 2-Chlor-4-cyano-5-dimethylamino-phenyl, 2-Fluor-4-cyano-5- tetrahydrofurylmethoxy-phenyl, 2-Fluor-4-cyano-5-amino-phenyl, 2-Fluor-4-cyano- 5-methylaminocarbonyl-phenyl, 2-Fluor-4-cyano-5-methylsulfonyloxy-phenyl, 2-2-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-
Chlor-4-cyano-5-difluormethoxy-phenyl, 2-Fluor-4-cyano-5-ethoxycarbonyl- methoxy-phenyl, 2-Fluor-4-cyano-5-dimethylaminocarbonyl-phenyl, 2-Fluor-4- cyano-5-cyanomethoxy-phenyl, 2-Fluor-4-cyano-5-(2-chlor-2-propenyloxy)-phenyl, 2-Fluor-4-cyano-5-hydroxy-phenyl, 2-Fluor-4-cyano-5-nitro-phenyl, 2-Fluor-4- cyano-5-diethoxyphosphorylamino-phenyl, 2-Fluor-4-cyano-5-chlorsulfonyl-phenyl, 2-Fluor-4-cyano-5-formylamino-phenyl, 2-Chlor-4-cyano-5-ethoxycarbonyloxy- phenyl, 2-Fluor-4-cyano-5-diethoxyphosphorylmethoxy-phenyl, 2-Chlor-4-cyano-5- hydroxy-phenyl, 2-Fluor-4-cyano-5-(N,N-diacetyl-amino)-phenyl, 2-Fluor-4-cyano- 5-acetylamino-phenyl, 2-Chlor-4-cyano-5-thiocyanato-phenyl, 2-Fluor-4-cyano-5- diethylaminooxy-phenyl, 2-Fluor-4-cyano-5-tetrahydrofuryloxy-phenyl, 2-Fluor-4- cyano-5-ureido-phenyl, 2-Fluor-4-cyano-5-dimethoxymethylenamino-phenyl, 2- Chlor-4-cyano5-ethoxymethylenamino-phenyl, 2-Fluor-4-cyano-5-(2-chlor-ethoxy- carbonyloxy)phenyl, 2-Chlor-4-cyano-5-dimethylaminomethylenamino-phenyl, 2- Chlor-4-cyano-5-(perhydropyran-4-yloxy)-phenyl, 2-Fluor-4-cyano-5-(2-methoxy- carbonyl-ethyI)-phenyl, 2-Chlor-4-cyano-5-(2-carboxy-2-chlor-ethyl)-phenyl, 2- Fluor-4-cyano-5-(2-chlor-2-methoxycarbonyl-ethyl)-phenyl, 2-Fluor-4-cyano-5-(2- chlor-2-s-butoxycarbonyl)-phenyl, 2-Fluor-4-cyano-5-(2-chlor-2-carbamoyl-ethyl)- phenyl, 2-Fluor-4-cyano-5-(2-chlor-2-methoxycarbonyl-l-methyl-ethyl)-phenyl, 2- Fluor-4-cyano-5-(l,2-dibrom-2-methoxycarbonyl-ethyl)-phenyl, 2-Chlor-4-cyano-5- (2-chlor-2-i-propoxycarbonyl-ethyl)-phenyl, 2,4-Dichlor-5-(2-methoxycarbonyl- ethyl)-phenyl, 2-Fluor-4-cyano-5-(2-carboxy-2-chlor-ethyl)-phenyl, 2-Fluor-4- cyano-5-(2-chlor-2-ethylaminocarbonyl-ethyl)-phenyl, 2-Fluor-4-cyano-5-(2-allyl- aminocarbonyl-2-chlor-ethyl)-phenyl, 2-Fluor-4-cy ano-5-(2-ethoxy carbonyl - ethenyl)-phenyl, 2-Fluor-4-cyano-5-(2-chlor-2-cyclopropylaminocarbonyl-ethyl)- phenyl, 2-Fluor-4-cyano-5-(2-chlor-2-dimethylaminocarbonyl-ethyl)-phenyl, 2- Chlor-4-cyano-5-(2-chlor-2-ethylsulfonylaminocarbonyl-ethyl)-phenyl, 2-Fluor-4- chlor-5-(2-carboxy-ethenyl)-phenyl, 2-Fluor-4-thiocarbamoyl-5-(2-ethylamino- carbonyl-ethenyl)-phenyl, 2-Fluor-4-cyano-5-(l-ethoxycarbonyl-ethyl)-phenyl, 2- Chlor-4-cyano-5-(l-ethoxycarbonylethyl)-phenyl, 2-Chlor-4-cyano-5-carboxy- phenyl, 2-Fluor-4-chlor-5-(l-ethoxycarbonyl-ethyl)-phenyl, 2-Fluor-4-chlor-5-(l-i- propoxycarbonyl-ethyl)-phenyl, 2-Fluor-4-cyano-5-i-butoxy-phenyl, 2-Chlor-4- cyano-5-i-butoxy-phenyl, 2-Chlor-4-cyano-5-(2-methoxy-ethoxy)-phenyl, 2-Fluor-4- chlor-5-(2-methoxy-ethoxy)-phenyl, 2-Fluor-4-chlor-5-i-butoxyphenyl, 2-Fluor-4- hydroxy-5-i-propoxycarbonyl-phenyl, 2-Fluor-4-cyano-5-(2-oxetanyloxy)-phenyl, 2- Fluor-4-cy an o-5-(2-oxetanyloxy carbonylmethoxy )-phenyl. Gruppe 2Chloro-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
Figure imgf000018_0001
Figure imgf000018_0001
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 3Group 3
Figure imgf000018_0002
Figure imgf000018_0002
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 4Group 4
Figure imgf000018_0003
Figure imgf000018_0003
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen. Gruppe 5Ar, R 4 and R 6 have, for example, the meanings given above under Group 1. Group 5
Ru R u
Figure imgf000019_0001
Figure imgf000019_0001
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 6Group 6
Rü v
Figure imgf000019_0002
R ü v
Figure imgf000019_0002
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenenAr, R 4 and R 6 have, for example, those given above under Group 1
Bedeutungen.Meanings.
Gruppe 7Group 7
Figure imgf000019_0003
Figure imgf000019_0003
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen. Gruppe 8Ar, R 4 and R 6 have, for example, the meanings given above under Group 1. Group 8
Figure imgf000020_0001
Figure imgf000020_0001
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 9Group 9
Figure imgf000020_0002
Figure imgf000020_0002
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 10Group 10
^^
Figure imgf000020_0003
Figure imgf000020_0003
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen. Gruppe 11Ar, R 4 and R 6 have, for example, the meanings given above under Group 1. Group 11
R°R °
Figure imgf000021_0001
Figure imgf000021_0001
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 12Group 12
Figure imgf000021_0002
Figure imgf000021_0002
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenenAr, R 4 and R 6 have, for example, those given above under Group 1
Bedeutungen.Meanings.
Gruppe 13Group 13
RD R D
Figure imgf000021_0003
Figure imgf000021_0003
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen. Gruppe 14Ar, R 4 and R 6 have, for example, the meanings given above under Group 1. Group 14
Figure imgf000022_0001
Figure imgf000022_0001
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenenAr, R 4 and R 6 have, for example, those given above under Group 1
Bedeutungen.Meanings.
Gruppe 15Group 15
Figure imgf000022_0002
Figure imgf000022_0002
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenenAr, R 4 and R 6 have, for example, those given above under Group 1
Bedeutungen.Meanings.
Gruppe 16Group 16
Figure imgf000022_0003
Figure imgf000022_0003
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenenAr, R 4 and R 6 have, for example, those given above under Group 1
Bedeutungen. Gruppe 17Meanings. Group 17
Figure imgf000023_0001
Figure imgf000023_0001
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 18Group 18
Figure imgf000023_0002
Figure imgf000023_0002
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 19Group 19
Rü R ü
Figure imgf000023_0003
Figure imgf000023_0003
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen. Gruppe 20Ar, R 4 and R 6 have, for example, the meanings given above under Group 1. Group 20
R"R "
Figure imgf000024_0001
Figure imgf000024_0001
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 21Group 21
Figure imgf000024_0002
Figure imgf000024_0002
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenenAr, R 4 and R 6 have, for example, those given above under Group 1
Bedeutungen.Meanings.
Gruppe 22Group 22
Figure imgf000024_0003
Figure imgf000024_0003
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen. Gruppe 23Ar, R 4 and R 6 have, for example, the meanings given above under Group 1. Group 23
R°R °
Figure imgf000025_0001
Figure imgf000025_0001
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 24Group 24
Figure imgf000025_0002
Figure imgf000025_0002
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 25Group 25
;J
Figure imgf000025_0003
 ; J
Figure imgf000025_0003
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen. Gruppe 26Ar, R 4 and R 6 have, for example, the meanings given above under Group 1. Group 26
Ru R u
Figure imgf000026_0001
Figure imgf000026_0001
Ar, R >4 und R haben hierbei beispielhaft die oben unter Gruppe 1 angegebenenAr, R> 4 and R have, for example, those given above under Group 1
Bedeutungen.Meanings.
Gruppe 27Group 27
Figure imgf000026_0002
Figure imgf000026_0002
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 28Group 28
R"R "
Figure imgf000026_0003
Figure imgf000026_0003
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen. Gruppe 29Ar, R 4 and R 6 have, for example, the meanings given above under Group 1. Group 29
R°R °
Figure imgf000027_0001
Figure imgf000027_0001
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 30Group 30
Figure imgf000027_0002
Figure imgf000027_0002
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 31Group 31
Figure imgf000027_0003
Figure imgf000027_0003
Ar, R und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen. Gruppe 32Ar, R and R 6 have, for example, the meanings given above under Group 1. Group 32
Figure imgf000028_0001
Figure imgf000028_0001
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 33Group 33
Figure imgf000028_0002
Figure imgf000028_0002
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Gruppe 34Group 34
Figure imgf000028_0003
Figure imgf000028_0003
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen. Gruppe 35Ar, R 4 and R 6 have, for example, the meanings given above under Group 1. Group 35
Ru R u
Figure imgf000029_0001
Figure imgf000029_0001
Ar, R4 und R6 haben hierbei beispielhaft die oben unter Gruppe 1 angegebenen Bedeutungen.Ar, R 4 and R 6 have, for example, the meanings given above under Group 1.
Verwendet man beispielsweise 2-Chlor-4,5-difluor-benzonitril und 1,2,3,4-Tetra- hydro-2,4-dioxo-pyrimidin-5-carbonitril als Ausgangsstoffe, so kann der Reaktions¬ ablauf beim erfindungsgemäßen Verfahren (a) durch das folgende Formelschema skizziert werden: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:
Figure imgf000029_0002
Figure imgf000029_0002
Verwendet man beispielsweise 2,4-Dichlor-5-methoxy-anilin und 2-Cyano-3 -meth¬ oxy- l-oxo-2-propenyl-carbamidsäure-methyl ester als Ausgangsstoffe, so kann der Reaktionsablauf beim erfindungsgemäßen Verfahren (b) durch das folgende Formelschema skizziert werden: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:
Figure imgf000029_0003
Die beim erfindungsgemaßen Verfahren (a) zur Herstellung der Verbindungen der Formel (I) als Ausgangsstoffe zu verwendenden Halogenarene sind durch die Formel (II) allgemein definiert In der Formel (II) haben R1, R2 und RJ vorzugs¬ weise bzw insbesondere diejenige Bedeutung, die bereits oben bei der Be- Schreibung der erfindungsgemaß herzustellenden Verbindungen der Formel (I) vor¬ zugsweise bzw als insbesondere bevorzugt fur R1, R2 und R3 angegeben wurde, X1 steht vorzugsweise fur Fluor, Chlor oder Brom, insbesondere fur Fluor oder Chlor
Figure imgf000029_0003
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
Die Ausgangsstoffe der Formel (II) sind bekannt und/oder können nach bekannten Verfahren hergestellt werden (vgl EP 191 181, EP 370332, EP 431373, EP 441004The 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
Die beim erfindungsgemaßen Verfahren (a) zur Herstellung der Verbindungen der Formel (I) weiter als Ausgangsstoffe zu verwendenden Uracile sind durch die Formel (III) allgemein definiert In der Formel (III) haben R4, R5 und R6 vorzugs¬ weise bzw insbesondere diejenige Bedeutung, die bereits oben bei der Beschrei- bung der erfindungsgemaß herzustellenden Verbindungen der Formel (I) vorzugs¬ weise bzw als insbesondere bevorzugt fur R4, R und R angegeben wurdeThe 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.
Die Ausgangsstoffe der Formel (III) sind bekannt und/oder können nach bekannten Verfahren hergestellt werden (vgl DE 3402193, Chem Pharm Bull 20 (1972), 1380-1388)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)
Die beim erfindungsgemaßen Verfahren (b) zur Herstellung der Verbindungen derThe process (b) according to the invention for the preparation of the compounds of
Formel (I) als Ausgangsstoffe zu verwendenden Aminoarene sind durch die Formel (IV) allgemein definiert In der Formel (IV) haben R1, R2 und RJ vorzugs¬ weise bzw insbesondere diejenige Bedeutung, die bereits oben bei der Beschrei¬ bung der erfindungsgemaß herzustellenden Verbindungen der Formel (I) Vorzugs- weise bzw als insbesondere bevorzugt für R , R und R angegeben wurdeAminoarenes 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.
Die Ausgangsstoffe der Formel (IV) sind bekannt und/oder können nach bekannten Verfahren hergestellt werden (vgl EP 224001)The starting materials of the formula (IV) are known and / or can be prepared by known processes (cf. EP 224001)
Die beim erfindungsgemaßen Verfahren (b) zur Herstellung der Verbindungen derThe process (b) according to the invention for the preparation of the compounds of
Formel (I) weiter als Ausgangsstoffe zu verwendenden 3-Alkoxy-l-oxo-2-alkenyl- carbamidsaureester sind durch die Formel (V) allgemein definiert In der FormelFormula (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) haben R4, R5 und R6 vorzugsweise bzw insbesondere diejenige Bedeutung, die bereits oben bei der Beschreibung der erfindungsgemaß herzustellenden Ver¬ bindungen der Formel (I) vorzugsweise bzw als insbesondere bevorzugt fur R4, R5 und R6 angegeben wurde(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
Die Ausgangsstoffe der Formel (V) sind bekannt und/oder können nach bekannten Verfahren hergestellt werden (vgl US 4266056, Chem Pharm Bull 20 (1972),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)1380-1388)
Die erfindungsgemaßen Verfahren (a) und (b) zur Herstellung der Verbindungen der Formel (I) werden vorzugsweise in Gegenwart eines geeigneten Reaktionshilfs¬ mittels durchgeführt Als Reaktionshilfsmittel kommen im allgemeinen die üblichen anorganischen oder organischen Basen oder Saureakzeptoren in BetrachtProcesses (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
Hierzu gehören vorzugsweise Alkalimetall- oder Erdalkalimetall- -acetate, -amide, -carbonate, -hydrogencarbonate, -hydride, -hydroxide oder -alkanolate, wie bei¬ spielsweise Natrium-, Kalium- oder Calcium-acetat, Lithium-, Natrium-, Kalium¬ oder Calcium-amid, Natrium-, Kalium- oder Calcium-carbonat, Natrium-, Kalium- oder Calcium-hydrogencarbonat, Lithium-, Natrium-, Kalium- oder Calcium-hy- drid, Lithium-, Natrium-, Kalium- oder Calcium-hydroxid, Natrium- oder Kalium- methanolat, -ethanolat, n- oder i-propanolat, n-, i-, s- oder t-butanolat; weiterhin auch basische organische Stickstoffverbindungen, wie beispielsweise Trimethyl¬ amin, Triethylamin, Tripropylamin, Tributylamin, Ethyl-diisopropylamin, N,N- Dimethyl-cyclohexylamin, Dicyclohexylamin, Ethyl -di cyclohexyl amin, N,N-Dime- thyl-anilin, N,N-Dimethyl-benzylamin, Pyridin, 2-Methyl-, 3-Methyl-, 4-Methyl-, 2,4-Dimethyl-, 2,6-Dimethyl-, 3,4-Dimethyl- und 3,5-Dimethyl-pyridin, 5-Ethyl-2- methyl-pyridin, 4-Dimethylamino-pyridin, N-Methyl-piperidin, 1,4-Diazabicyclo- [2,2,2]-octan (DABCO), l,5-Diazabicyclo[4,3,0]-non-5-en (DBN), und 1,8 Diaza- bicyclo[5,4,0]-undec-7-en (DBU)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)
Die erfindungsgemaßen Verfahren (a) und (b) zur Herstellung der Verbindungen der Formel (I) werden vorzugsweise in Gegenwart eines Verdünnungsmittels durch¬ geführt. Als Verdünnungsmittel kommen im allgemeinen die üblichen organischen Lösungsmittel in Betracht Hierzu gehören vorzugsweise aliphatische, ahcyclische und aromatische, gegebenenfalls halogenierte Kohlenwasserstoffe, wie beispiels¬ weise Pentan, Hexan, Heptan, Petrolether, Ligroin, Benzin, Benzol, Toluol, Xylol, Chlorbenzol, Dichlorbenzol, Cyclohexan, Methylcyclohexan, Dichlormethan (Methylenchlorid), Trichlormethan (Chloroform) oder Tetrachlormethan, Dialkyl- ether, wie beispielsweise Diethylether, Diisopropylether, Methyl-t-butylether (MTBE), Ethyl-t-butylether, Methyl-t-pentylether (TAME), Ethyl-t-pentyl ether, Tetrahydrofuran (THF), 1,4-Dioxan, Ethylenglycol-dimethylether oder -diethyl¬ ether, Diethylenglycol-dimethylether oder -diethylether; Dialkylketone, wie bei¬ spielsweise Aceton, Butanon (Methylethylketon), Methyl-i-propylketon oder Methyl-i-butylketon, Nitrile, wie beispielsweise Acetonitril, Propionitril, Butyro- nitril oder Benzonitril; Amide, wie beispielsweise N,N-Dimethyl-formamid (DMF), N,N-Dimethyl-acetamid, N-Methyl-formanilid, N-Methyl-pyrrolidon oder Hexa- methyl-phosphorsäuretriamid; Ester, wie beispielsweise Essigsäure-methylester, -ethylester, -n- oder -i-propylester, -n-, -i- oder -s-buty lester; Sulfoxide, wie bei- spielsweise Dimethylsulfoxid; Alkanole, wie beispielsweise Methanol, Ethanol, n- oder i-Propanol, n-, i-, s- oder t-Butanol, Ethylenglycol-monomethylether oder -monoethylether, Diethylenglycol-monomethylether oder -monoethylether; deren Gemische mit Wasser oder reines Wasser.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.
Die Reaktionstemperaturen können bei der Durchführung der erfindungsgemäßen Verfahren (a) und (b) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 200°C, vorzugsweise zwischen 10°C und 150°C, insbesondere zwischen 20°C und 120°C.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.
Die erfindungsgemäßen Verfahren (a) und (b) werden im allgemeinen unter Normaldruck durchgeführt. Es ist jedoch auch möglich, die erfindungsgemäßen Verfahren unter erhöhtem oder vermindertem Druck - im allgemeinen zwischenProcesses (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 und 10 bar - durchzuführen.0.1 bar and 10 bar.
Zur Durchführung der erfindungsgemäßen Verfahren (a) und (b) werden die Aus¬ gangsstoffe im allgemeinen in angenähert äquimolaren Mengen eingesetzt. Es ist jedoch auch möglich, jeweils eine der Komponenten in einem größeren Überschuß zu verwenden. Die Umsetzung wird im allgemeinen in einem geeigneten Ver¬ dünnungsmittel in Gegenwart eines Reaktionshilfsmittels durchgeführt und das Re¬ aktionsgemisch wird im allgemeinen mehrere Stunden bei der erforderlichen Tem¬ peratur gerührt. Die Aufarbeitung wird nach üblichen Methoden durchgeführt (vgl. die Herstellungsbeispiele).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).
Die erfindungsgemäßen Wirkstoffe können als Defoliants, Desiccants, Krautab- tötungsmittel und insbesondere als Unkrautvernichtungsmittel verwendet werden. Unter Unkraut im weitesten Sinne sind alle Pflanzen zu verstehen, die an Orten aufwachsen, wo sie unerwünscht sind. Ob die erfindungsgemäßen Stoffe als totale oder selektive Herbizide wirken, hängt im wesentlichen von der angewandten Menge ab.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.
Die erfindungsgemäßen Wirkstoffe können z.B. bei den folgenden Pflanzen ver¬ wendet werden:The active compounds according to the invention can e.g. can be used for the following plants:
Dikotyle Unkräuter der Gattungen: 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.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.
Dikotyle Kulturen der Gattungen: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
Monokotyle Unkräuter der Gattungen: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus,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.Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
Monokotyle Kulturen der Gattungen: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.
Die Verwendung der erfindungsgemäßen Wirkstoffe ist jedoch keineswegs auf diese Gattungen beschränkt, sondern erstreckt sich in gleicher Weise auch auf andere Pflanzen.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.
Die Verbindungen eignen sich in Abhängigkeit von der Konzentration zur Total - Unkrautbekämpfung z.B. auf Industrie- und Gleisanlagen und auf Wegen undDepending on the concentration, the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and
Plätzen mit und ohne Baumbewuchs. Ebenso können die Verbindungen zur Un¬ krautbekämpfung in Dauerkulturen, z.B. Forst, Ziergehölz-, Obst-, Wein-, Citrus-, Nuß-, Bananen-, Kaffee-, Tee-, Gummi-, Ölpalm-, Kakao-, Beerenfrucht- und Hopfenanlagen, auf Zier- und Sportrasen und Weideflächen und zur selektiven Unkrautbekämpfung in einjährigen Kulturen eingesetzt werden. Die erfindungsgemaßen Verbindungen der Formel (I) eignen sich insbesondere zur selektiven Bekämpfung von monokotylen und dikotylen Unkräutern in mono¬ kotylen Kulturen sowohl im Vorauflauf- als auch im Nachauflauf- VerfahrenPlaces 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
In gewissem Umfang zeigen die Verbindungen der Formel (I) auch insektizide und akarizide WirksamkeitTo a certain extent, the compounds of the formula (I) also have insecticidal and acaricidal activity
Die Wirkstoffe können in die üblichen Formulierungen übergeführt werden, wie Losungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Staubemittel, Pasten, losliche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-impräg¬ nierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren StoffenThe 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
Diese Formulierungen werden in bekannter Weise hergestellt, z. B. durch Ver¬ mischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeu-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
» "e^nden Mitteln»" Means
Im Falle der Benutzung von Wasser als Streckmittel können z B. auch organische Losungsmittel als Hilfslosungsmittel verwendet werden Als flüssige Losungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkyl- naphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwas¬ serstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methy lisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie WasserIf 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
Als feste Trägerstoffe kommen in Frage" z.B Ammoniumsalze und naturliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Mont- morillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsaure, Aluminiumoxid und Silikate, als feste Tragerstoffe fur Granulate kommen in Frage z B gebrochene und fraktionierte naturliche Gesteine wieSolid 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
Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Poly oxy ethyl en-Fettsäure-Ester, Polyoxyethylen-Fett- alkohol-Ether, z.B. Alkylarylpolyglykolether, Alkylsulfonate, Alkylsulfate, Aryl- sulfonate sowie Eiweißhydrolysate; als Dispergiermittel kommen in Frage: z.B.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-Sulfitablaugen und Methylcellulose.Lignin sulfite liquor and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexförmige Polymere ver¬ wendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospho¬ lipide. Weitere Additive können mineralische und vegetabile Öle sein.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.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalo- cyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.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.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichts¬ prozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
Die erfindungsgemäßen Wirkstoffe können als solche oder in ihren Formulie¬ rungen auch in Mischung mit bekannten Herbiziden zur Unkrautbekämpfung Ver- wendung finden, wobei Fertigformulierungen oder Tankmischungen möglich sind.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.
Für die Mischungen kommen bekannte Herbizide in Frage, beispielsweise Anilide, wie z.B. Diflufenican und Propanil; Arylcarbonsäuren, wie z.B. Dichlorpicolin- säure, Dicamba und Picloram; Aryloxyalkansäuren, wie z.B. 2,4 D, 2,4 DB, 2,4 DP, Fluroxypyr, MCPA, MCPP und Triclopyr; Aryloxy-phenoxy-alkansäureester, wie z.B. Diclofop-methyl, Fenoxaprop-ethyl, Fluazifop-butyl, Haloxyfop-methyl und Quizalofop-ethyl; Azinone, wie z.B. Chloridazon und Norflurazon; Carbamate, wie z.B. Chlorpropham, Desmedipham, Phenmedipham und Propham; Chloracet¬ anilide, wie z.B. Alachlor, Acetochlor, Butachior, Metazachlor, Metolachlor, Pretilachlor und Propachlor; Dinitroaniline, wie z.B. Oryzalin, Pendimethalin und Trifluralin; Diphenylether, wie z.B. Acifluorfen, Bifenox, Fluoroglycofen,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 und Oxyfluorfen; Harnstoffe, wie z.B. Chlor¬ toluron, Diuron, Fluometuron, Isoproturon, Linuron und Methabenzthiazuron; Hydroxylamine, wie z.B. Alloxydim, Clethodim, Cycloxydim, Sethoxydim und Tralkoxydim; Imidazolinone, wie z.B. Imazethapyr, Imazamethabenz, Imazapyr und Imazaquin; Nitrile, wie z.B. Bromoxynil, Dichlobenil und Ioxynil; Oxy- acetamide, wie z.B. Mefenacet; Sulfonylharnstoffe, wie z.B. Amidosulfuron, Ben- sulfuron-methyl, Chlorimuron-ethyl, Chlorsulfuron, Cinosulfuron, Metsulfuron- methyl, Nicosulfuron, Primisulfuron, Pyrazosulfuron-ethyl, Thifensulfuron-methyl, Triasulfuron und Tribenuron-methyl; Thiolcarbamate, wie z.B. Butylate, Cycloate, Diallate, EPTC, Esprocarb, Molinate, Prosulfocarb, Thiobencarb und Triallate; Triazine, wie z.B. Atrazin, Cyanazin, Simazin, Simetryne, Terbutryne und Terbutylazin; Triazinone, wie z.B. Hexazinon, Metamitron und Metribuzin;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;
Sonstige, wie z.B. Aminotriazol, Benfuresate, Bentazone, Cinmethylin, Clom- azone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate und Tridiphane.Others, such as Aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.
Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Fungiziden, Insek¬ tiziden, Akariziden, Nematiziden, Schutzstoffen gegen Vogelfraß, Pflanzennähr- stoffen und Bodenstrukturverbesserungsmitteln ist möglich.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.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus durch weiteres Verdünnen bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Suspensionen, Emulsionen, Pulver, Pasten und Granulate angewandt werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Spritzen, Sprühen, Streuen.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.
Die erfindungsgemäßen Wirkstoffe können sowohl vor, als auch nach dem Auf¬ laufen der Pflanzen appliziert werden. Sie können auch vor der Saat in den Boden eingearbeitet werden.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.
Die angewandte Wirkstoffmenge kann in einem größeren Bereich schwanken. Sie hängt im wesentlichen von der Art des gewünschten Effektes ab. Im allgemeinen liegen die Aufwandmengen zwischen 1 g und 10 kg Wirkstoff pro Hektar Boden¬ fläche, vorzugsweise zwischen 5 g und 5 kg pro ha.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.
Die Herstellung und die Verwendung der erfindungsgemäßen Wirkstoffe geht aus den nachfolgenden Beispielen hervor. Herstellungsbeispiele:The preparation and use of the active compounds according to the invention can be seen from the examples below. Manufacturing examples:
Beispiel 1example 1
HH
Figure imgf000037_0001
Figure imgf000037_0001
(Verfahren (a))(Method (a))
6,5 g (0,05 mol) 5-Fluor-uracil werden mit 7,6 g (0,055 mol) Kaliumcarbonat in 100 ml Dimethylsulfoxyd vorgelegt, mit 7,9 g (0,05 mol) 2,4,5-Trifluor-benzonitril versetzt und 12 Stunden bei 80°C gerührt. Nach dem Abkühlen auf Raum¬ temperatur wird mit Wasser verrührt, mit konz. Salzsäure auf pH 4 eingestellt und das ausgefallene Produkt durch Filtration isoliert.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.
Man erhält 12 g (90 % der Theorie) an l-(2,5-Difluor-4-cyanophenyl)-5-fluor- uracil vom Schmelzpunkt >250°C. 12 g (90% of theory) of l- (2,5-difluoro-4-cyanophenyl) -5-fluorouracil with a melting point> 250 ° C. are obtained.
Beispiel 2Example 2
HH
Figure imgf000038_0001
Figure imgf000038_0001
Zu 1,1 g (0,015 mol) Butin-l-ol-(3) in 80 ml Acetonitril werden bei 25°C portionsweise 0,45 g (0,015 mol) Natriumhydrid (80%ig in Parafin) eingetragen. Nach einer Nachrührzeit von 15 Minuten bei 25°C werden 2,7 g (0,01 mol) 1- (2,5-Difluor-4-cyano-phenyl)-5-fiuor-uracil zugesetzt und die Reaktionsmischung wird 12 Stunden bei 70°C gerührt. Die auf 25°C abgekühlte Mischung wird unter vermindertem Druck eingeengt, der Rückstand mit Wasser verrührt, mit konz. Salzsäure auf pH 4 eingestellt und das ausgefallene Produkt durch Filtration isoliert.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.
Man erhält 2,0 g (63 % der Theorie) an l-(2-Fluor-4-cyano-5-but-l-in-3-yl-oxy- phenyl)-5-fluor-uracil vom Schmelzpunkt 175°C. 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.
Beispiel 3Example 3
Figure imgf000039_0001
Figure imgf000039_0001
3,2 g (0,01 mol) l-(2-Fluor-4-cyano-5-but-l-in-3-yl-oxy-phenyl)-5-fluor-uracil werden in 100 ml Acetonitril mit 0,36 g (0,012 mol) 80%igem Natriumhydrid eine Stunde bei 60°C gerührt, anschließend mit 1,6 g (0,01 1 mol) Methyliodid versetzt und 12 Stunden bei Rückflußtemperatur gerührt. Die abgekühlte Reaktionsmi¬ schung wird unter vermindertem Druck im Vakuum eingeengt, mit Wasser ver¬ rührt, mit konz. Salzsäure angesäuert und das ausfallende Produkt abfiltriert. Das Rohprodukt wird mittels Säulenchromatographie (Laufmittel: Cyclohexan/Essig- säureethylester 1 : 1) gereinigt.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).
Man erhält 0,5 g (15 % der Theorie) an l-(2-Fluor-4-cyano-5-but-l-in-3-yl-oxy- phenyl)-3-methyl-5-fluor-uracil vom Schmelzpunkt 141°C.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.
Analog Beispiel 1,2 und 3 sowie entsprechend der allgemeinen Beschreibung der erfindungsgemäßen Herstellungsverfahren können beispielsweise auch die in der nachstehenden Tabelle 1 aufgeführten Verbindungen der Formel (I) hergestellt werden.
Figure imgf000040_0001
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.
Figure imgf000040_0001
Tabelle 1: Beispiele für die Verbindungen der Formel (I)Table 1: Examples of the compounds of the formula (I)
Bsp - R1 R2 R3 R4 R> R6 Schmelz¬Example - R 1 R 2 R 3 R 4 R> R 6 Schmelz¬
Nr. punkt (°C)No. point (° C)
4 F CN F H CF3 H >2504 F CN FH CF 3 H> 250
5 F CN F H CF3 CH3 1725 F CN FH CF 3 CH 3 172
6 F CN F H F H 2196 F CN F H F H 219
7 F CN NHSO2C2H5 H F τι H 967 F CN NHSO 2 C 2 H 5 HF τ ι H 96
8 F CN F H CH3 1028 F CN FH CH 3 102
9 F CN NHSO2C3H7-i H F H 1659 F CN NHSO 2 C 3 H 7 -i HFH 165
10 F CN F H CH3 H 21210 F CN FH CH 3 H 212
1 1 F CN F H Cl H 1321 1 F CN F H Cl H 132
Figure imgf000040_0002
Figure imgf000040_0002
Figure imgf000040_0003
Figure imgf000040_0003
14 CN H CH3 CH3 1!
Figure imgf000040_0004
Bsp.- R1 R^ R-1 R4 Rs Rö Schmelz¬14 CN H CH 3 CH 3 1!
Figure imgf000040_0004
Example - R 1 R ^ R- 1 R 4 R s R ö Schmelz¬
Nr. punkt (°C)No. point (° C)
Figure imgf000041_0001
Figure imgf000041_0001
Figure imgf000041_0002
Figure imgf000041_0002
17 F CN NHSO2C2H5 H Cl H 75 18 F CN OCH(CH3)2 H CH, H 22917 F CN NHSO 2 C 2 H 5 H Cl H 75 18 F CN OCH (CH 3 ) 2 H CH, H 229
Figure imgf000041_0003
Figure imgf000041_0003
Figure imgf000041_0004
Figure imgf000041_0004
Figure imgf000041_0005
Figure imgf000041_0005
22 F CN F CF3 F H 11522 F CN F CF 3 FH 115
23 F CN OC2H5 H F H 22923 F CN OC 2 H 5 HFH 229
24 F CN OC3H7-i H CH3 CH3 16324 F CN OC 3 H 7 -i H CH 3 CH 3 163
Figure imgf000041_0006
Figure imgf000041_0006
26 F CN OC3H7-i H F CH3 16226 F CN OC 3 H 7 -i HF CH 3 162
27 F CN OC3Hri H F C2H5 159 Bsp - R1 R2 RJ R4 R5 Rö Schmelz¬ Nr. punkt (°C)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 OC2H5 H CH3 17828 CN OC 2 H 5 H CH 3 178
Figure imgf000042_0001
Figure imgf000042_0001
Figure imgf000042_0002
Figure imgf000042_0002
31 CN OCH, H C2H5 15831 CN OCH, HC 2 H 5 158
32 CN H CH, 15232 CN H CH, 152
33 CN H F C2H5 15433 CN HFC 2 H 5 154
34 F CN H F CH7-i 13834 F CN HF CH 7 -i 138
Figure imgf000042_0003
Figure imgf000042_0003
Figure imgf000042_0004
Figure imgf000042_0004
37 F CN H CF C2H5 154 Bsp, R1 R^ Rj R4 R5 Rü Schmelz¬37 F CN H CF C 2 H 5 154 Example, R 1 R ^ R j R 4 R 5 R ü Schmelz¬
Nr. punkt (°C)No. point (° C)
Figure imgf000043_0001
Figure imgf000043_0001
Figure imgf000043_0002
Figure imgf000043_0002
40 F CN F H CN H 23140 F CN F H CN H 231
41 F CN F H Br H 23041 F CN F H Br H 230
42 F CN F H COOC2H5 n 19442 F CN FH COOC 2 H 5 n 194
Figure imgf000043_0003
Figure imgf000043_0003
Figure imgf000043_0004
Figure imgf000043_0004
45 CN H Br C2H5 19445 CN H Br C 2 H 5 194
CH, Anwendungsbeispiele:CH, Examples of use:
In den Anwendungsbeispielen wird die folgende Verbindung als Vergleichssub¬ stanz herangezogen:In the application examples, the following compound is used as a reference substance:
Figure imgf000044_0001
Figure imgf000044_0001
l-(4-Chlor-2-fluor-phenyl)-l,2,3,4-tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril (be¬ kannt aus US 4266056). 1- (4-Chloro-2-fluorophenyl) -1, 2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile (known from US 4266056).
Beispiel AExample A
P re-em ergence-TestP re-em ergence test
Lösungsmittel: 5 Gewichtsteile AcetonSolvent: 5 parts by weight of acetone
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Ge¬ wichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die ange¬ gebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die ge¬ wünschte Konzentration.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.
Samen der Testpflanzen werden in normalen Boden ausgesät. Nach ca. 24 Stunden wird der Boden mit der Wirkstoffzubereitung begossen. Dabei hält man dieSeeds 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
Wassermenge pro Flächeneinheit zweckmäßigerweise konstant. Die Wirkstoffkon¬ zentration in der Zubereitung spielt keine Rolle, entscheidend ist nur die Aufwand¬ menge des Wirkstoffs pro Flächeneinheit.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.
Nach drei Wochen wird der Schädigungsgrad der Pflanzen bonitiert in % Schädi- gung im Vergleich zur Entwicklung der unbehandelten Kontrolle.After three weeks, the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control.
Es bedeuten:It means:
0 % = keine Wirkung (wie unbehandelte Kontrolle)0% = no effect (like untreated control)
100 % = totale Vernichtung100% = total annihilation
In verschiedenen Tests zeigen beispielsweise die Verbindungen gemäß Her- Stellungsbeispiel 3, 15, 26, 30 und 32 bei weitgehend guter Verträglichkeit gegenüber Kulturpflanzen, wie z.B. Mais (0 - 50 %) und einer Aufwandmenge von 125 g/ha starke Wirkungen gegen Unkräuter wie Setaria (95 - 100 %), Abutilon (100 %), Amaranthus (100 %), Galium (70 - 100 %), Sinapis (70 - 100 %), Alopecurus (90 %), Cyperus (95 %). Beispiel BIn 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-TestPost emergence test
Lösungsmittel: 5 Gewichtsteile AcetonSolvent: 5 parts by weight of acetone
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Ge¬ wichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die ange¬ gebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die ge¬ wünschte Konzentration.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.
Mit der Wirkstoffzubereitung spritzt man Testpflanzen, welche eine Höhe von 5 - 15 cm haben so, daß die jeweils gewünschten Wirkstoffmengen pro Flächeneinheit ausgebracht werden. Die Konzentration der Spritzbrüche wird so gewählt, daß in ca. 1000 1/ha die jeweils gemischten Wirkstoffmengen ausgebracht werden.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.
Nach drei Wochen wird der Schädigungsgrad der Pflanzen bonitiert in % Schädigung im Vergleich zur Entwicklung der unbehandelten Kontrolle.After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
Es bedeuten:It means:
0 % = keine Wirkung (wie unbehandelte Kontrolle)0% = no effect (like untreated control)
100 % = totale Vernichtung100% = total annihilation
In verschiedenen Tests zeigen beispielsweise die Verbindungen gemäß Her¬ stellungsbeispiel 3 und 30 bei teilweise guter Verträglichkeit gegenüber Kultur- pflanzen, wie z.B. Mais (bis 25 %) und einer Aufwandmenge von 125 g/ha starkeIn 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
Wirkung gegen Unkräuter wie Setaria (95 %), Abutilon (90 - 100 %), Amaranthus (80 - 100 %) sowie Sinapis (90 %). Effective against weeds such as Setaria (95%), Abutilon (90 - 100%), Amaranthus (80 - 100%) and Sinapis (90%).

Claims

Patentansprüche claims
Substituierte Phenyluracile der allgemeinen Formel (I)Substituted phenyluracils of the general formula (I)
Figure imgf000047_0001
Figure imgf000047_0001
in welcherin which
R1 für Wasserstoff, Cyano oder Halogen steht,R 1 represents hydrogen, cyano or halogen,
R2 für Cyano, Carbamoyl, Thiocarbamoyl, Halogen oder für jeweils ge¬ gebenenfalls durch Halogen substituiertes Alkyl oder Alkoxy steht,R 2 stands for cyano, carbamoyl, thiocarbamoyl, halogen or for alkyl or alkoxy which is optionally substituted by halogen,
R für die Gruppierung A -A -A steht, worinR represents the grouping A -A -A, wherein
A1 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2-, -CO- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff, Hydroxy, Alkyl, Alkenyl, Alkinyl, Alkoxy, Aryl, Alkylsulfonyl oder Arylsulfonyl steht,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,
weiterhin für jeweils gegebenenfalls durch Halogen substitu¬ iertes Alkandiyl, Alkendiyl, Azaalkendiyl, Alkindiyl, Cyclo¬ alkandiyl, Cycloalkendiyl oder Phenylen steht,furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2-, -CO- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff, Hydroxy, Alkyl, Alkoxy, Aryl, Alkylsulfonyl oder Arylsulfonyl steht, A~ weiterhin für jeweils gegebenenfalls durch Halogen substitu¬ iertes Alkandiyl, Alkendiyl, Azaalkendiyl, Alkindiyl, Cyclo¬ alkandiyl, Cycloalkendiyl oder Phenylen steht,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,
A3 für Wasserstoff steht mit der Maßgabe, daß in diesem FallA 3 represents hydrogen with the proviso that in this case
5 A und/oder A" nicht für eine Einfachbindung stehen5 A and / or A "do not stand for a single bond
A weiterhin für Hydroxy, Amino, Cyano, Isocyano, Thio¬ cyanato, Nitro, Carboxy, Carbamoyl, Thiocarbamoyl, Sulfo, Chlorsulfonyl, Halogen, für jeweils gegebenenfalls durch Halogen oder Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio,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, Alk¬ oxycarbonyl oder Dialkoxy(thio)phosphoryl, für jeweils gege¬ benenfalls durch Halogen substituiertes Alkenyl, Alkenyloxy, Alkenylamino, Alkylidenamino, Alkenyloxycarbonyl, Alki¬ nyl, Alkinyloxy, Alkinylamino oder Alkinyloxycarbonyl, für10 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 jeweils gegebenenfalls durch Halogen, Cyano, Carboxy, Al¬ kyl und/oder Alkoxycarbonyl substituiertes Cycloalkyl, Cyclo¬ alkyloxy, Cycloalkylalkyl, Cycloalkylalkoxy, Cycloalkyliden- amino, Cycloalkyloxycarbonyl oder Cycloalkylalkoxy- carbonyl, oder für jeweils gegebenenfalls durch Nitro, Cyano,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, Halogenalkyl, Alkyloxy, Halogen- alkyloxy und/oder Alkoxy-carbonyl substituiertes Aryl, Aryl¬ oxy, Aralkyl, Arylalkoxy, Aryloxycarbonyl oder Arylalkoxy- carbonyl steht,20 carboxy, halogen, alkyl, haloalkyl, alkyloxy, haloalkyloxy and / or alkoxycarbonyl substituted aryl, aryloxy, aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbonyl,
A weiterhin für jeweils gegebenenfalls ganz oder teilweise 25 hydriertes Pyrrolyl, Pyrazolyl, Imidazolyi, Triazolyl, Furyl,A further for 25 fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyi, triazolyl, furyl,
Oxiranyl, Oxetanyl, Dioxolanyl, Thienyl, Oxazolyl, Isoxa¬ zolyl, Thiazolyl, Isothiazolyl, Oxadiazolyl, Thiadiazolyl, Py¬ ridinyl, Pyrimidinyl, Triazinyl, Pyrazolylalkyl, Furylalkyl, Thienylalkyl, Oxazolylalkyl, Isoxazolalkyl, Thiazolalkyl, 30 Pyridinylalkyl, Pyrimidinylalkyl, Pyrazolylalkoxy, Furylalk- oxy, für Perhydropyranylalkoxy oder Pyridylalkoxy steht,Oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyrimidinyl, triazinyl, pyrazolylalkyl, furylalkyl, thienylalkyl, oxazolylalkyl, isoxazylyl, pyrid oxy represents perhydropyranylalkoxy or pyridylalkoxy,
R4 für Wasserstoff, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Nitro, Halogen, Alkoxycarbonyl, Alkylamino, Dialkylamino, oder für je- weils gegebenenfalls durch Hydroxy, Nitro, Cyano, Halogen oder Alkoxy substituiertes Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Alkylthio, Alkenylthio oder Alkinylthio steht,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,
R5 fur Wasserstoff, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Nitro, Halogen, Alkoxycarbonyl, Alkylamino, Dialkylamino, oder fur je¬ weils gegebenenfalls durch Hydroxy, Nitro, Cyano, Halogen oder Alkoxy substituiertes Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Alkylthio, Alkenylthio oder Alkinylthio steht, undR 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
R6 fur Wasserstoff, Hydroxy, Amino, Cyano, für jeweils gegebenenfalls durch Cyano, Nitro, Halogen oder Alkoxy substituiertes Alkyl,R 6 for hydrogen, hydroxy, amino, cyano, for alkyl optionally substituted by cyano, nitro, halogen or alkoxy,
Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, oder fur jeweils gegebenenfalls durch Cyano, Halo¬ gen oder Alkyl substituiertes Cycloalkyl oder Cycloalkylalkyl steht,Alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, or for cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or alkyl,
ausgenommen die Verbindungen l-(4-Chlor-2-fluor-phenyl)-l,2,3,4-tetrahy- dro-2,4-dioxo-pyrimidin-5-carbonitril, l-(3-Chlor-4-fluor-phenyl)-l,2,3,4- tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril, l-(4-Chlor-3-trifluormethyl- phenyl)-l,2,3,4-tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril, l-(3,4-Dichlor- phenyl)-l,2,3,4-tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril, l-[4-Chlor-2- fluor-5-(2-propinyloxy)-phenyl]-3-methyl-2,4-(lH,3H)-pyridindionexcept 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
Substituierte Phenyluracile der allgemeinen Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, daßSubstituted phenyluracils of the general formula (I) according to Claim 1, characterized in that
R1 fur Wasserstoff, Cyano, Fluor, Chlor oder Brom steht,R 1 represents hydrogen, cyano, fluorine, chlorine or bromine,
R2 fur Cyano, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, oder fur jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Al- kyl oder Alkoxy mit jeweils 1 oder 2 Kohlenstoffatomen steht,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,
R3 fur die Gruppierung -A!-A2-A3 steht,R 3 for the grouping -A ! -A 2 -A 3 stands,
in welcher A1 fur eine Einfachbindung, fur Sauerstoff, Schwefel, -SO-,in which A 1 for a single bond, for oxygen, sulfur, -SO-,
-SO,-, -CO- oder die Gruppierung -N-A4- steht, worin A4 fur-SO, -, -CO- or the grouping -NA 4 -, where A 4 is
Wasserstoff, Hydroxy, C,-C4-Alkyl, C3-C4-Alkenyl, C3-C4-Hydrogen, hydroxy, C, -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 -
Alkinyl, CrC4-Alkoxy, Phenyl, C1-C4-Alkylsulfonyl oderAlkynyl, C r C 4 alkoxy, phenyl, C 1 -C 4 alkylsulfonyl or
5 Phenylsulfonyl steht,5 is phenylsulfonyl,
A1 weiterhin fur jeweils gegebenenfalls durch Fluor, Chlor oder Brom substituiertes C]-C6-Alkandiyl, C-,-C6-Alkendiyl, G,- C6-Azaalkendiyl, C2-C6-Alkindiyl, C3-C6-Cycloalkandiyl, C3- C6-Cycloalkendiyl oder Phenylen steht,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~ fur eine Einfachbindung, fur Sauerstoff, Schwefel, -SO-,10 A ~ for a single bond, for oxygen, sulfur, -SO-,
-SO2-, -CO- oder die Gruppierung -N-A4- steht, worin A4 fur Wasserstoff, Hydroxy, CrC4-Alkyl, CrC4-Alkoxy, Phenyl, Cj-C4- Alkylsulfonyl oder Phenylsulfonyl steht,-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 weiterhin für jeweils gegebenenfalls durch Fluor, Chlor oder 15 Brom substituiertes C,-C6-Alkandiyl, C2-C6- Alkendiyl, C2-A further for C, -C 6 -alkanediyl, C 2 -C 6 -alkenediyl, C 2 -, each optionally substituted by fluorine, chlorine or 15 bromine,
C6-Azaalkendiyl, C2-C6-Alkindiyl, C3-C6-Cycloalkandiyl, C3- C6-Cycloalkendiyl oder Phenylen steht,C 6 -Azaalkendiyl, C 2 -C 6 alkynediyl, C 3 -C 6 -cycloalkanediyl, C 3 - C 6 is cycloalkenediyl or phenylene,
A fur Wasserstoff steht, mit der Maßgabe,daß in diesem Fall A und/oder A~ nicht fur eine Einfachbindung stehen,A represents hydrogen, with the proviso that in this case A and / or A ~ do not represent a single bond,
20 A weitwerhin fur Hydroxy, Amino, Cyano, Isocyano, Thio¬ cyanato, Nitro, Carboxy, Carbamoyl, Thiocarbamoyl, Sulfo, Chlorsulfonyl, Fluor, Chlor, Brom, für jeweils gegebenenfalls durch Fluor, Chlor oder C1-C4-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino,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 oder Dialkoxy(thio)phospho- ryl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkyl¬ gruppen, fur jeweils gegebenenfalls durch Fluor oder Chlor substituiertes Alkenyl, Alkenyloxy, Alkenylamino, Alkyliden- amino, Alkenyloxycarbonyl, Alkinyl, Alkinyloxy, Alkinyl-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 oder Alkinyloxycarbonyl mit jeweils 2 bis 6 Kohlen¬ stoffatomen in den Alkenyl-, Alkyliden- oder Alkinyl- gruppen, fur jeweils gegebenenfalls durch Fluor, Chlor, Cyano, Carboxy, C,-C4-Alkyl und/oder C,-C4-Alkoxy carbo¬ nyl substituiertes Cycloalkyl, Cycloalkyloxy, Cycloalkylalkyl, Cycloalkyl alkoxy, Cycloalkylidenamino, Cycloalkyloxycarbo- nyl oder Cycloalkylalkoxycarbonyl mit jeweils 3 bis 6 Koh- lenstoffatomen in den Cycloalkylgruppen und gegebenenfalls30 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 bis 4 Kohlenstoffatomen in den Alkylgruppen, oder für jeweils gegebenenfalls durch Nitro, Cyano, Carboxy, Fluor, Chlor, Brom, CrC4-Alkyl, C,-C4-Halogenalkyl, CrC4-Alkyl- oxy, CrC4-Halogenalkyloxy und/oder C,-C4-Alkoxy-car- bonyl substituiertes Phenyl, Phenyloxy, Phenyl-CrC4-alkyl,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,-C4-alkoxy, Phenyloxycarbonyl oder Phenyl-C,-C4- alkoxycarbonyl steht,Phenyl-C, -C 4 -alkoxy, phenyloxycarbonyl or phenyl-C, -C 4 - alkoxycarbonyl,
3 weiterhin für jeweils gegebenenfalls ganz oder teilweise hy¬ driertes Pyrrolyl, Pyrazolyl, Imidazolyl, Triazolyl, Furyl, Oxiranyl, Oxetanyl, Dioxolanyl, Thienyl, Oxazolyl, Isoxa¬ zolyl, Thiazolyl, Isothiazolyl, Oxadiazolyl, Thiadiazolyl, Py¬ ridinyl, Pyrimidinyl, Triazinyl, Pyrazolyl -CrC4-al kyl, Furyl- Cj-C4-alkyl, Thienyl-C,-C4-alkyl, Oxazolyl-C]-C4-alkyl, Isoxazol-CrC4-alkyl, Thiazol-C]-C4-alkyl, Pyridinyl-C1-C4- alkyl, Pyrimidinyl-C]-C4-alkyl, Pyrazolylmethoxy, Furyl¬ methoxy, für Perhydropyranylmethoxy oder Pyridylmethoxy steht, oder3 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
R4 für Wasserstoff, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Nitro, Fluor, Chlor, Brom, C]-C4-Alkoxy-carbonyl, C1-C4-Alkylamino, Di- (C,-C4-alkyl)-amino, oder für jeweils gegebenenfalls durch Hy¬ droxy, Nitro, Cyano, Fluor, Chlor, Brom oder C,-C4-Alkoxy substi¬ tuiertes Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Alkylthio, Alkenylthio oder Alkinylthio mit jeweils bis zu 6 Kohlen¬ stoffatomen steht,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,
R5 für Wasserstoff, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Nitro,R 5 for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, nitro,
Fluor, Chlor, Brom, CrC4-Alkoxy-carbonyl, CrC4-Alkylamino, Di- (C,-C4-alkyl)-amino, oder für jeweils gegebenenfalls durch Hy¬ droxy, Nitro, Cyano, Fluor, Chlor, Brom oder C,-^- Alkoxy sub¬ stituiertes Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Alkylthio, Alkenylthio oder Alkinylthio mit jeweils bis zu 6 Kohlen¬ stoffatomen steht, undFluorine, 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
R6 für Wasserstoff, Hydroxy, Amino, Cyano, für jeweils gegebenenfalls durch Cyano, Nitro, Fluor, Chlor, Brom oder C]-C4-Alkoxy sub- stituiertes Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkylthio,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,
Alkylsulfinyl, Alkylsulfonyl mit jeweils bis zu 6 Kohlenstoffatomen, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom oder CrC4-Alkyl substituiertes Cycloalkyl oder Cycloalkylalkyl mit 3 bis 6 Kohlenstoffatomen in den Cycloalkylgruppen und gege- benenfalls 1 bis 4 Kohlenstoffatomen in den Alkylgruppen steht,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,
ausgenommen die Verbindungen l-(4-Chlor-2-fluor-phenyl)- 1,2,3, 4-tetrahy- dro-2,4-dioxo-pyrimidin-5-carbonitril, l-(3-Chlor-4-fluor-phenyl)-l,2,3,4- tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril, l-(4-Chlor-3-trifluormethyl- phenyl)-l,2,3,4-tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril, l-(3,4-Dichlor- phenyl)- l,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-dioxo-pyrimidin-5-carbonitril, l-[4-Chlor-2- fluor-5-(2-propinyloxy)-phenyl]-3-methyl-2,4-(lH,3H)-pyridindion.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. Substituierte Phenyluracile der allgemeinen Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, daß3. Substituted phenyluracils of general formula (I) according to claim 1, characterized in that
R1 für Wasserstoff, Fluor oder Chlor steht,R 1 represents hydrogen, fluorine or chlorine,
R2 für Cyano, Thiocarbamoyl, Fluor, Chlor, Brom, Methyl oder Tri¬ fluormethyl steht,R 2 represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, methyl or trifluoromethyl,
R3 für die Gruppierung -A1-A2-A3 steht,R 3 represents the grouping -A 1 -A 2 -A 3 ,
in welcherin which
A1 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -CO2-, -CO- oder die Gruppierung -N-A4- steht, worin A4 fürA 1 stands for a single bond, for oxygen, sulfur, -SO-, -CO 2 -, -CO- or the grouping -NA 4 -, wherein A 4 stands for
Wasserstoff, Hydroxy, Methyl, Ethyl, n- oder i-Propyl, Meth¬ oxy, Ethoxy, n- oder i-Propoxy, Methylsulfonyl oder Ethyl¬ sulfonyl steht, A1 weiterhin für Methylen, Ethan- 1,1 -diyl, Ethan- 1, 2-diyl, Pro¬ pan- 1,1 -diyl, Propan- 1, 2-diyl, Propan- 1,3-diyl, Ethen- 1, 2-diyl, Propen- 1, 2-diyl, Propen- 1,3-diyl, Ethin-1, 2-diyl oder Propin- 1,3-diyl steht,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,
A2 für eine Einfachbindung, für Sauerstoff, Schwefel, -SO-, -SO2-, -CO- oder die Gruppierung -N-A4- steht, worin A4 für Wasserstoff, Hydroxy, Methyl, Ethyl, n- oder i-Propyl, Meth¬ oxy, Ethoxy, n- oder i-Propoxy, Methylsulfonyl, Ethylsul¬ fonyl, n- oder i-Propylsulfonyl oder Phenylsulfonyl steht,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,
11
10 A~ weiterhin für Methylen, Ethan- 1,1 -diyl, Ethan- 1, 2-diyl, Pro¬ pan- 1,1 -diyl, Propan- 1, 2-diyl, Propan- 1,3-diyl, Ethen- 1, 2-diyl, Propen- 1, 2-diyl, Propen- 1,3-diyl, Ethin-1, 2-diyl oder Propin- 1,3-diyl steht,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,
A3 für Wasserstoff steht, mit der Maßgabe, daß in diesem Fall 15 A1 und/oder A2 nicht für eine Einfachbindung stehen,A 3 represents hydrogen, with the proviso that in this case 15 A 1 and / or A 2 do not represent a single bond,
A3 weiterhin für Hydroxy, Amino, Cyano, Nitro, Carboxy, Carb¬ amoyl, Sulfo, Fluor, Chlor, Brom, für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Me¬ thyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, n-, i-, s- 20 oder t-Pentyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, n-, i-, s- oder t-Pentyloxy, Methylthio, Ethyl¬ thio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Methyl¬ sulfinyl, Ethylsulfinyl, n- oder i-Propylsulfinyl, Methylsul¬ fonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl, Methylamino, 25 Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butyl- amino, Dimethylamino, Diethylamino, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Dimethoxyphos- phoryl, Di ethoxy phosphoryl oder Dipropoxyphosphoryl, Di- isopropoxyphosphoryl, für jeweils gegebenenfalls durch Fluor 30 oder Chlor substituiertes Propenyl, Butenyl, Propenyloxy,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, Propylidenamino, Butylidenamino, Propenyloxycarbonyl, Butenyloxycarbonyl, Propinyl, Butinyl, Propinyloxy, Butinyloxy, Propinylamino, Butinylamino, Propinyloxycarbonyl oder Butinyloxycarbonyl, für jeweils gegebenenfalls durch Fluor, Chlor, Cyano, Carboxy, Methyl, Ethyl, n- oder i-Propyl, Methoxycarbonyl oder Ethoxy carb onyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropyloxy, Cyclobutyloxy,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 iden- amino, Cyclopentyloxycarbonyl, Cyclohexyl oxycarbonyl, Cyc- lopentylmethoxycarbonyl oder Cyclohexylmethoxycarbonyl, oder für jeweils gegebenenfalls durch Nitro, Cyano, Carboxy, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, Trifluor¬ methyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluor- methoxy, Trifluormethoxy, Methoxycarbonyl und/oderCyclopentyloxy, 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 substituiertes Phenyl, Phenyloxy, Benzyl, Phenylethyl, Benzyloxy, Phenyloxycarbonyl, Benzyloxycar¬ bonyl steht,Ethoxycarbonyl substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl,
A'1 weiterhin für (jeweils gegebenenfalls ganz oder teilweise hy- driertes) Pyrrolyl, Pyrazolyl, Imidazolyl, Triazolyl, Furyl,A ' 1 furthermore for (in each case fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl,
Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Oxa- diazolyl, Thiadiazolyl, Pyridinyl, Pyrimidinyl, Triazinyl, Pyrazolylmethyl, Furylmethyl, Thienylmethyl, Oxazolylme- thyl, Isoxazolmethyl, Thiazolmethyl, Pyridinylmethyl, Pyri- midinylmethyl, Pyrazolylmethoxy, Furylmethoxy oder Pyri- dylmethoxy steht,Thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolmethyl, thiazolmethyl, pyridylmethylmethyl, pyridylmethylmethyl, pyridylmethylmethyl, pyridylmethylmethyl, pyridylmethylmethyl ,
R4 für Wasserstoff, Cyano, Fluor, Chlor oder für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, Methoxy oder Ethoxy steht,R 4 represents hydrogen, cyano, fluorine, chlorine or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine,
R5 für Wasserstoff, Cyano, Fluor, Chlor oder für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, Methoxy oder Ethoxy steht, und R6 für Wasserstoff, Amino, Cyano oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Propenyl, Butenyl, Propinyl oder Butinyl steht,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,
ausgenommen die Verbindungen l-(4-Chlor-2-fluor-phenyl)- 1,2,3, 4-tetrahy- dro-2,4-dioxo-pyrimidin-5-carbonitril, l-(3-Chlor-4-fluor-phenyl)-l,2,3,4-te- trahydro-2,4-dioxo-pyrimidin-5-carbonitril, l-(4-Chlor-3-trifluormethyl-phe- nyl)-l,2,3,4-tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril, 1 -(3, 4-Di chlor¬ phenyl)- 1,2,3, 4-tetrahydro-2,4-dioxo-pyrimidin-5-carbonitril, l-[4-Chlor-2- fluor-5-(2-propinyloxy)-phenyl]-3-methyl-2,4-(lH,3H)-pyridindion.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. Verfahren zur Herstellung substituierter Phenyluracile der allgemeinen For¬ mel (I)4. Process for the preparation of substituted phenyluracils of the general formula (I)
V
Figure imgf000055_0001
 V
Figure imgf000055_0001
in welcher R1, R2, R3, R4, R5 und R6 die in Anspruch 1 genannten Bedeutungen haben,in which R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the meanings given in Claim 1,
dadurch gekennzeichnet, daß mancharacterized in that one
(a) Halogenarene der allgemeinen Formel (II)(a) Halogenarenes of the general formula (II)
Figure imgf000055_0002
Figure imgf000055_0002
in welcher R , R" und R" die oben angegebene Bedeutung haben undin which R, R "and R " have the meaning given above and
X1 für Halogen steht,X 1 represents halogen,
mit Uracilen der allgemeinen Formel (III)with uracenes of the general formula (III)
RD R D
Figure imgf000056_0001
Figure imgf000056_0001
in welcherin which
R4, R^1 und R6 die oben angegebene Bedeutung haben,R 4 , R ^ 1 and R 6 have the meaning given above,
gegebenenfalls in Gegenwart eines Reaktionshilfsmittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt,if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
oder daß manor that one
(b) Aminoarene der allgemeinen Formel (IV)(b) aminoarenes of the general formula (IV)
Figure imgf000056_0002
Figure imgf000056_0002
in welcherin which
R1, R2 und R3 die oben angegebene Bedeutung haben,R 1 , R 2 and R 3 have the meaning given above,
mit 3-Alkoxy-l-oxo-2-alkenyl-carbamidsäureestern der allgemeinen Formel (V) RD with 3-alkoxy-l-oxo-2-alkenyl-carbamic acid esters of the general formula (V) R D
Figure imgf000057_0001
Figure imgf000057_0001
in welcherin which
R4, R5 und R6 die oben angegebene Bedeutung haben, undR 4 , R 5 and R 6 have the meaning given above, and
R für Alkyl steht,R represents alkyl,
gegebenenfalls in Gegenwart eines Reaktionshilfsmittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt.if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
5. Herbizide Mittel, gekennzeichnet durch einen Gehalt an mindestens einem substituierten Phenyluracil der allgemeinen Formel (I) gemäß den Ansprü¬ chen 1 bis 4.5. Herbicidal agents, characterized by a content of at least one substituted phenyluracil of the general formula (I) according to claims 1 to 4.
6. Verfahren zur Bekämpfung von unerwünschten Pflanzen, dadurch ge¬ kennzeichnet, daß man substituierte Phenyluracile der allgemeinen Formel (I) gemäß den Ansprüchen 1 bis 4 auf unerwünschte Pflanzen und/oder ihren Lebensraum einwirken läßt.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. Verwendung von substituierten Phenyluracilen der allgemeinen Formel (I) gemäß der Ansprüche 1 bis 4 zur Bekämpfung von unerwünschten Pflan¬ zen.7. Use of substituted phenyluracils of the general formula (I) according to Claims 1 to 4 for combating undesired plants.
8. Verfahren zur Herstellung von herbiziden Mitteln, dadurch gekennzeichnet, daß man substituierte Phenyluracile der allgemeinen Formel (I) gemäß der Ansprüche 1 bis 4 mit Streckmitteln und/oder oberflächenaktiven Substan- zen vermischt. 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.
PCT/EP1996/003222 1995-08-02 1996-07-22 Substituted 1-phenyluracil derivatives, their preparation and their use as herbicides WO1997005117A1 (en)

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US6107252A (en) * 1996-05-02 2000-08-22 Bayer Aktiengesellschaft Substituted phenyl uracils and their use as herbicides
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US6245715B1 (en) 1997-05-27 2001-06-12 Bayer Aktiengesellschaft Substituted iminoalkoxy-phenyluracils, the production and use thereof as herbicides
WO1998054155A1 (en) * 1997-05-27 1998-12-03 Bayer Aktiengesellschaft Substituted iminoalkoxy-phenyluracils, the production and use thereof as herbicides
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US8986740B2 (en) 2007-09-17 2015-03-24 Abbvie Inc. Anti-infective agents and uses thereof
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US9216952B2 (en) 2010-03-23 2015-12-22 Abbvie Inc. Process for preparing antiviral compound
US9802903B2 (en) 2010-03-23 2017-10-31 Abbvie Inc. Process for preparing antiviral compound
US8975443B2 (en) 2010-07-16 2015-03-10 Abbvie Inc. Phosphine ligands for catalytic reactions
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