WO1997005117A1 - Derives substitues de 1-phenyluracile, leur preparation et leur utilisation comme herbicides - Google Patents

Derives substitues de 1-phenyluracile, leur preparation et leur utilisation comme herbicides Download PDF

Info

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
Authority
WO
WIPO (PCT)
Prior art keywords
cyano
alkyl
alkoxy
chlorine
fluorine
Prior art date
Application number
PCT/EP1996/003222
Other languages
German (de)
English (en)
Inventor
Karl-Heinz Linker
Kurt Findeisen
Roland Andree
Mark Wilhelm Drewes
Markus Dollinger
Hans-Joachim Santel
Original Assignee
Bayer Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU66585/96A priority Critical patent/AU6658596A/en
Publication of WO1997005117A1 publication Critical patent/WO1997005117A1/fr

Links

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne de nouveaux phényluraciles substitués de formule générale (I), dans laquelle R1 désigne hydrogène, cyano ou halogène; R2 désigne cyano, carbamoyle, thiocarbamoyle, halogène ou alkyle ou alcoxy le cas échéant substitués par un halogène; R3 désigne le groupement A?1-A2-A3, où A1, A2 et A3¿ ont la signification donnée dans la description; R4 désigne hydrogène, cyano, carboxy, carbamoyle, thiocarbamoyle, nitro, halogène, alcoxycarbonyle, alkylamino, dialkylamino ou alkyle, alcényle, alkinyle, alcoxy, alcényloxy, alcinyloxy, alkylthio, alcénylthio ou alcinylthio le cas échéant substitués par hydroxy, nitro, cyano, halogène ou alcoxy; R5 désigne hydrogène, cyano, carboxy, carbamoyle, thiocarbamoyle, nitro, halogène, alcoxycarbonyle, alkylamino, dialkylamino ou alkyle, alcényle, alkinyle, alcoxy, alcényloxy, alkinyloxy, alkylthio, alcénylthio ou alkinylthio le cas échéant substitués par hydroxy, nitro, cyano, halogène ou alcoxy; et R6 désigne hydrogène, hydroxy, amino, cyano, ou alkyle, alcényle, alkinyle, alcoxy, alcényloxy, alkylthio, alkylsulfinyle, alkylsulfonyle le cas échéant substitués par cyano, nitro, halogène ou alcoxy, ou cycloalkyle ou cycloalkylalkyle le cas échéant substitués par cyano, halogène ou alkyle, à l'exception des composés 1-(4-chloro-2-fluorophényl)-1,2,3,4-tétrahydro-2,4-dioxo-pyrimidine-5-carbonitrile, 1-(3-chloro-4-fluorophényl)-1,2,3,4-tétrahydro-2,4-dioxo-pyrimidine-5-carbonitrile, 1-(4-chloro-3-trifluorométhylphényl)-1,2,3,4-tétrahydro-2,4-dioxo-pyrimidine-5-carbonitrile, 1-(3,4-dichlorophényl)-1,2,3,4-tétrahydro-2,4-dioxo-pyrimidine-5-carbonitrile, 1-[4-chloro-2-fluoro-5-(2-propinyloxy)-phényl]-3-méthyl-2,4-(1H,3H)-pyridinedione. L'invention concerne également un procédé de préparation de ces composés et leur utilisation comme herbicides.
PCT/EP1996/003222 1995-08-02 1996-07-22 Derives substitues de 1-phenyluracile, leur preparation et leur utilisation comme herbicides WO1997005117A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU66585/96A AU6658596A (en) 1995-08-02 1996-07-22 Substituted 1-phenyluracil derivatives, their preparation and their use as herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19528305.8 1995-08-02
DE1995128305 DE19528305A1 (de) 1995-08-02 1995-08-02 Substituierte Phenyluracile

Publications (1)

Publication Number Publication Date
WO1997005117A1 true WO1997005117A1 (fr) 1997-02-13

Family

ID=7768458

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/003222 WO1997005117A1 (fr) 1995-08-02 1996-07-22 Derives substitues de 1-phenyluracile, leur preparation et leur utilisation comme herbicides

Country Status (3)

Country Link
AU (1) AU6658596A (fr)
DE (1) DE19528305A1 (fr)
WO (1) WO1997005117A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998054155A1 (fr) * 1997-05-27 1998-12-03 Bayer Aktiengesellschaft Iminoalcoxy-phenyluraciles substitues, leur fabrication et leur utilisation comme herbicides
US6107252A (en) * 1996-05-02 2000-08-22 Bayer Aktiengesellschaft Substituted phenyl uracils and their use as herbicides
US7259277B2 (en) 2003-07-25 2007-08-21 Wyeth Advanced route for the synthesis of cPLA2 inhibitors
US8178548B2 (en) 2007-09-17 2012-05-15 Abbott Laboratories Anti-infective agents and uses thereof
US8188104B2 (en) 2007-09-17 2012-05-29 Abbott Laboratories Anti-infective agents and uses thereof
US8415351B2 (en) 2007-09-17 2013-04-09 Abbott Laboratories Anti-infective agents and uses thereof
US8841487B2 (en) 2010-07-16 2014-09-23 Abbvie Inc. Phosphine ligands for catalytic reactions
US8895737B2 (en) 2010-07-16 2014-11-25 Shashank Shekhar Process for preparing antiviral compounds
US8975443B2 (en) 2010-07-16 2015-03-10 Abbvie Inc. Phosphine ligands for catalytic reactions
US9216952B2 (en) 2010-03-23 2015-12-22 Abbvie Inc. Process for preparing antiviral compound
US9255074B2 (en) 2010-07-16 2016-02-09 Abbvie Inc. Process for preparing antiviral compounds

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19627901A1 (de) * 1996-07-11 1998-01-15 Bayer Ag Substituierte aromatische Carbonylverbindungen und ihre Derivate
BR9808688A (pt) * 1997-04-22 2000-07-11 Du Pont Composto, composição herbicida e método para controlar o crescimento de vegetação indesejada
BR112015031155A2 (pt) 2013-06-20 2017-07-25 Bayer Cropscience Ag derivados de sulfureto de arila e derivados de aril sulfóxido como acaricidas e inseticidas
CN105473558B (zh) 2013-06-20 2019-04-19 拜耳作物科学股份公司 作为杀螨剂和杀昆虫剂的芳基硫化物衍生物和芳基硫氧化物衍生物
JP6423873B2 (ja) 2013-07-08 2018-11-14 バイエル・クロップサイエンス・アクチェンゲゼルシャフト 有害生物防除剤としての６員ｃ−ｎ−結合アリールスルフィド誘導体及びアリールスルホキシド誘導体

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2043628A (en) * 1978-12-14 1980-10-08 Zoecon Corp 1-Phenyl-3-polyhaloalkylthio or polyhalo-vinylthio uracils, useful as biological agents and synthesis thereof
US4266056A (en) * 1978-04-07 1981-05-05 Zoecon Corporation Phenyl uracils
US5153316A (en) * 1991-06-04 1992-10-06 Crouse Gary D Intermediates for herbicidal phenylimidazolones
US5298502A (en) * 1988-12-12 1994-03-29 Fmc Corporation Method and composition for photodynamic treatment and detection of tumors

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4266056A (en) * 1978-04-07 1981-05-05 Zoecon Corporation Phenyl uracils
GB2043628A (en) * 1978-12-14 1980-10-08 Zoecon Corp 1-Phenyl-3-polyhaloalkylthio or polyhalo-vinylthio uracils, useful as biological agents and synthesis thereof
US5298502A (en) * 1988-12-12 1994-03-29 Fmc Corporation Method and composition for photodynamic treatment and detection of tumors
US5153316A (en) * 1991-06-04 1992-10-06 Crouse Gary D Intermediates for herbicidal phenylimidazolones

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6107252A (en) * 1996-05-02 2000-08-22 Bayer Aktiengesellschaft Substituted phenyl uracils and their use as herbicides
US6245715B1 (en) 1997-05-27 2001-06-12 Bayer Aktiengesellschaft Substituted iminoalkoxy-phenyluracils, the production and use thereof as herbicides
WO1998054155A1 (fr) * 1997-05-27 1998-12-03 Bayer Aktiengesellschaft Iminoalcoxy-phenyluraciles substitues, leur fabrication et leur utilisation comme herbicides
US7259277B2 (en) 2003-07-25 2007-08-21 Wyeth Advanced route for the synthesis of cPLA2 inhibitors
US8986740B2 (en) 2007-09-17 2015-03-24 Abbvie Inc. Anti-infective agents and uses thereof
US8178548B2 (en) 2007-09-17 2012-05-15 Abbott Laboratories Anti-infective agents and uses thereof
US8188104B2 (en) 2007-09-17 2012-05-29 Abbott Laboratories Anti-infective agents and uses thereof
US8415351B2 (en) 2007-09-17 2013-04-09 Abbott Laboratories Anti-infective agents and uses thereof
US8685991B2 (en) 2007-09-17 2014-04-01 Abbvie Inc. Anti-infective agents and uses thereof
US9139536B2 (en) 2007-09-17 2015-09-22 Abbvie Inc. Anti-infective agents and uses thereof
US9095590B2 (en) 2007-09-17 2015-08-04 Abbvie Inc. Anti-infective agents and uses thereof
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
US8895737B2 (en) 2010-07-16 2014-11-25 Shashank Shekhar Process for preparing antiviral compounds
US9200021B2 (en) 2010-07-16 2015-12-01 Abbvie Inc. Phosphine ligands for catalytic reactions
US8841487B2 (en) 2010-07-16 2014-09-23 Abbvie Inc. Phosphine ligands for catalytic reactions
US9255074B2 (en) 2010-07-16 2016-02-09 Abbvie Inc. Process for preparing antiviral compounds
US9266913B2 (en) 2010-07-16 2016-02-23 Abbvie Inc. Phosphine ligands for catalytic reactions
US9381508B2 (en) 2010-07-16 2016-07-05 Abbvie Inc. Phosphine ligands for catalytic reactions
US9434698B2 (en) 2010-07-16 2016-09-06 Abbvie Inc. Process for preparing antiviral compounds
US9669399B2 (en) 2010-07-16 2017-06-06 Abbvie Inc. Phosphine ligands for catalytic reactions
US9732045B2 (en) 2010-07-16 2017-08-15 Abbvie Inc. Process for preparing antiviral compounds

Also Published As

Publication number Publication date
AU6658596A (en) 1997-02-26
DE19528305A1 (de) 1997-02-06

Similar Documents

Publication Publication Date Title
EP0832072B1 (fr) Phenylpyridazinones
EP0759908B1 (fr) Diazacyclohexandi(thi)ones substituees
EP0758324B1 (fr) Amides aromatiques substitues d'acides thiocarboxyliques et leur utilisation comme herbicides
EP0648749B1 (fr) N-cyanoaryle hétérocycles azotés
EP0757680B1 (fr) Heterocycles n-cyanoaryle-azote
EP1120411B1 (fr) Dérivés de 4-aryl-1,2,4-triazolidinedione et leur utilisation comme herbicides
WO1997005117A1 (fr) Derives substitues de 1-phenyluracile, leur preparation et leur utilisation comme herbicides
EP0882027B1 (fr) 2-aryl-1,2,4-triazine -3,5-di(thi)ones substituees utilisees comme herbicides
DE4431218A1 (de) Substituierte Pyrimidin(thi)one
DE4424787A1 (de) Substituierte Aryliminoheterocyclen
DE19632005A1 (de) Substituierte p-Trifluormethylphenyluracile
WO1997001542A1 (fr) Carbonylaminophenyluraciles substitues
DE19500439A1 (de) Substituierte aromatische Thiocarbonsäureamide
DE4440914A1 (de) Substituierte Diazacyclohexandi(thi)one
DE19517505A1 (de) Sulfonylamino(thio)carbonyltriazolin(thi)one mit Aryloxy- oder Arylthio-Substituenten
EP0851860A1 (fr) 4-thiocarbamyl-1-(3-pyrazolyl)-pyrazoles et leur utilisation comme herbicides
DE19617532A1 (de) Substituierte Phenyluracile
EP0843667B1 (fr) Phenyluraciles substitues
DE19530451A1 (de) Substituierte Chinazolin(thi)one
DE19525973A1 (de) Sulfonylamino(thio)carbonyltriazolin(thi)one mit Heterocyclyl-(alk)oxy-Substituenten
WO1996036614A1 (fr) Derives du type amino-uracile
DE19702435A1 (de) Arylalkylverbindungen

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BB BG BR BY CA CN CZ HU JP KR KZ LK MX NO NZ PL RO RU SK TR UA US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: CA

122 Ep: pct application non-entry in european phase