WO1997001542A1 - Carbonylaminophenyluraciles substitues - Google Patents

Carbonylaminophenyluraciles substitues Download PDF

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Publication number
WO1997001542A1
WO1997001542A1 PCT/EP1996/002612 EP9602612W WO9701542A1 WO 1997001542 A1 WO1997001542 A1 WO 1997001542A1 EP 9602612 W EP9602612 W EP 9602612W WO 9701542 A1 WO9701542 A1 WO 9701542A1
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WO
WIPO (PCT)
Prior art keywords
fluorine
chlorine
cyano
optionally substituted
alkyl
Prior art date
Application number
PCT/EP1996/002612
Other languages
German (de)
English (en)
Inventor
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 AU63043/96A priority Critical patent/AU6304396A/en
Priority to BR9609319A priority patent/BR9609319A/pt
Priority to JP9504139A priority patent/JPH11508545A/ja
Priority to EP96922007A priority patent/EP0835247A1/fr
Publication of WO1997001542A1 publication Critical patent/WO1997001542A1/fr

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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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Definitions

  • the invention relates to new substituted carbonylaminophenyluracils, processes for their preparation and their use as herbicides.
  • R 1 represents hydrogen, cyano or halogen
  • R 2 represents cyano or halogen
  • R 3 represents in each case optionally substituted cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
  • R 4 stands for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl or for the grouping -CO-R 3 , in which R 3 has the meaning given above, R 5 represents hydrogen, halogen or optionally substituted alkyl or alkoxy,
  • R 6 represents optionally substituted alkyl
  • R 7 stands for hydrogen or for optionally substituted alkyl, alkoxy, alkenyl or alkynyl.
  • R 1 , R 2 , R 4 , R 5 , R 6 and R 7 have the meanings given above, and
  • R 8 represents hydrogen, trifluoroacetyl or alkylsulfonyl, with acid derivatives of the general formula (III)
  • R 3 has the meaning given above and
  • X represents halogen or the grouping -O-CO-R 3 , if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
  • the new substituted carbonylaminophenyluracils of the general formula (I) are notable for strong herbicidal activity.
  • the starting materials of the formula (II) are also herbicidally active to a certain extent.
  • saturated or unsaturated hydrocarbon chains such as alkyl, alkenyl or alkynyl, are each straight-chain or branched.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • the invention preferably relates to compounds of the formula (I) in which
  • R 1 represents hydrogen, cyano, fluorine or chlorine
  • R 2 represents cyano, fluorine, chlorine or bromine
  • R 3 represents in each case cycloalkyl or cycloalkylalkyl which is optionally substituted by cyano, fluorine, chlorine, bromine or C 1 -C 4 -alkyl and has 3 to 8 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the alkyl part,
  • R 3 furthermore for each optionally by fluorine, chlorine, bromine, cyano, roitro, carboxy, carbamoyl, thiocarbamoyl, by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfionyl or C 1 -C 4 alkylsulfonyl
  • Cyano, methyl, methoxy, trifluoromethyl and / or trifluoromethoxy are substituted) substituted phenyl, ⁇ aphthyl, benzyl, phenylethyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridinyl or quinolinyl
  • R 4 represents hydrogen, in each case optionally substituted by cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxycarbonyl alkyl, alkenyl or alkynyl each having up to 10 carbon atoms
  • R 4 furthermore represents cycloalkyl or cycloalkylalkyl which is optionally substituted by cyano, fluorine, chlorine, bromine or C 1 -
  • R 4 furthermore for each optionally by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl (which are each optionally substituted by fluorine and / or chlorine), by dimethylaminosulfonyl or diethylaminosulfonyl, by C 1 - C 4 alkoxycarbonyl (which is optionally substituted by fluorine, chlorine, Bromine, cyano, methoxy or ethoxy is substituted) by phenyl, phenyloxy or phenylthio (which are each optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and / or trifluo
  • R 5 represents hydrogen, fluorine, chlorine, bromine or alkyl or alkoxy each optionally substituted by fluorine and / or chlorine, each having 1 to 4 carbon atoms
  • R 6 represents alkyl optionally substituted by fluorine and / or chlorine having 1 to 4 carbon atoms and
  • R 7 stands for hydrogen or for alkyl, alkoxy, alkenyl or alkynyl, each optionally substituted by cyano, fluorine, chlorine or C 1 -C 4 -alkoxy, each having up to 6 carbon atoms.
  • the invention relates in particular to compounds of the formula (I) in which
  • R 1 represents hydrogen, fluorine or chlorine
  • R 2 represents cyano, fluorine, chlorine or bromine
  • R 3 represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl,
  • R 3 for each optionally by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, by dimethylaminosulfonyl or diethylaminosulfonyl, by methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, by phenyl, phenyloxy or phenylthio substituted phenyl, naphthyl, furyl, benzyl, benzyl
  • R 4 for hydrogen, for each methyl, ethyl, n- or i-propyl, n- substituted by cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy-carbonyl , i-, s- or t-butyl, n-, i-, s- or t-pentyl, propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl,
  • R 4 also represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, R 4 also represents in each case optionally by Fluorine, chlorine, bromine, cyano,
  • R 3 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy
  • R 6 represents methyl, ethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, chlorofluoroethyl, trifluoroethyl , Trichloroethyl, chlorodifluoroethyl, fluorodichloroethyl, tetrafiuorethyl, chlorotrifluoroethyl or pentafluoroethyl and R 7 represents hydrogen or methyl, ethyl, n- or i-propyl, n-, i- or optionally substituted by cyano, fluorine, chlorine, meth
  • radicals listed above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • Formula (II) provides a general definition of the aminophenyluracils to be used as starting materials in the process according to the invention for the preparation of the compounds of the formula (I).
  • R 1 , R 2 , R 4 , R 5 , R 6 and R 7 preferably or in particular have the meaning which, as described above, in the description of the compounds of the formula (I) to be prepared according to the invention are preferred or was particularly preferably indicated for R 1 , R 2 , R 4 , R 5 , R 6 and R 7 ;
  • R 8 preferably represents hydrogen, trifluoroacetyl or C 1 -C 4 alkylsulfonyl.
  • the starting materials of the formula (II) are known and / or can be prepared by processes known per se (cf. EP 408382, EP 648749, production examples).
  • the acid derivatives to be used further as starting materials in the process according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (III).
  • R 3 preferably or in particular has 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 3 ;
  • X preferably represents fluorine, chlorine or bromine, in particular fluorine.
  • the starting materials of the formula (III) are known synthetic chemicals.
  • the process according to the invention for the preparation of the compounds of the formula (I) is preferably carried out in the presence of a suitable reaction auxiliary.
  • the usual inorganic auxiliaries generally come see or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or
  • Calcium hydrogen carbonate lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n- or i-propanolate, n-, i- , s- or t-butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, 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
  • the process according to the invention for the preparation of the compounds of the formula (I) is preferably carried out in the presence of a diluent.
  • a diluent is generally suitable as diluents. These preferably include aliphatic, alicyclic 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 ethers, such as, for example, diethyl ether, diisopropyl ether, methyl t-butyl ether (MTBE), ethyl t-butyl ether, methyl
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger 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.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Trifolium Ranunculus, Taraxacum. Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
  • Sorghum Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
  • the active compounds according to the invention are suitable for combating total weeds e.g. on industrial and track systems and on
  • the compounds for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective purposes Weed control can be used in annual crops.
  • the active compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.
  • the active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders,
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is 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.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • 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 silicic acid, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well
  • Granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates
  • Possible dispersants are: e
  • 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.
  • additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalates can be used cyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, 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
  • 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, butachlor, 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, e.g. Chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; Hydroxylamines, e.g.
  • Amidosulfuron bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuronmethyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl,
  • Triasulfuron and tribenuron-methyl Triasulfuron and tribenuron-methyl; Thiol carbamates such as butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates; Triazines such as atrazine, cyanazine, simazin, simetryne, terbutryne and terbutylazine; Triazinones such as hexazinone, metamitron and metribuzin; Others such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tri
  • Solutions, suspensions, emulsions, powders, pastes and granules are used. 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 the plants emerge. 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 10 g and 10 kg of active ingredient per hectare of soil, preferably between 50 g and 5 kg per ha.
  • Example A The compound to be prepared according to Example (II-3) is not yet known from the literature; it is the subject of the present application as a new compound.
  • 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.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is watered or sprayed with the active ingredient preparation. The amount of water per unit area is expediently kept constant. The concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area. After three weeks, the degree of damage to the plants is rated in%
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, mix 1 part by weight of active compound with the stated amount of solvent, add the stated amount of emulsifier and dilute the concentrate 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 liquor is chosen so that the desired amounts of active compound are applied in about 1000 l / ha.
  • the compounds according to Preparation Examples 1, 2, 3 and 4 and (II-1) and (II-2) show a strong action against weeds such as abutilone (100%), amaranthus ( 90-100%) and Sinapis (80-100%).

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  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catching Or Destruction (AREA)

Abstract

L'invention concerne de nouveaux carbonylaminophényluraciles de la formule générale (I) où R?1, R2, R3, R4, R5, R6 et R7¿ ont la signification donnée dans la description, leur procédé de production ainsi que leur utilisation comme herbicides.
PCT/EP1996/002612 1995-06-29 1996-06-17 Carbonylaminophenyluraciles substitues WO1997001542A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU63043/96A AU6304396A (en) 1995-06-29 1996-06-17 Substituted carbonylaminophenyluracils
BR9609319A BR9609319A (pt) 1995-06-29 1996-06-17 Carbonilaminofeniluracilas substituídas
JP9504139A JPH11508545A (ja) 1995-06-29 1996-06-17 置換されたカルボニルアミノフェニルウラシル類
EP96922007A EP0835247A1 (fr) 1995-06-29 1996-06-17 Carbonylaminophenyluraciles substitues

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19523640.8 1995-06-29
DE19523640A DE19523640A1 (de) 1995-06-29 1995-06-29 Substituierte Carbonylaminophenyluracile

Publications (1)

Publication Number Publication Date
WO1997001542A1 true WO1997001542A1 (fr) 1997-01-16

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/002612 WO1997001542A1 (fr) 1995-06-29 1996-06-17 Carbonylaminophenyluraciles substitues

Country Status (10)

Country Link
EP (1) EP0835247A1 (fr)
JP (1) JPH11508545A (fr)
KR (1) KR19990028225A (fr)
CN (1) CN1193319A (fr)
AR (2) AR002596A1 (fr)
AU (1) AU6304396A (fr)
BR (1) BR9609319A (fr)
CA (1) CA2225828A1 (fr)
DE (1) DE19523640A1 (fr)
WO (1) WO1997001542A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002521001A (ja) * 1997-02-26 2002-07-09 エフ エム シー コーポレーション シクロイミド置換ベンゾ縮合ヘテロ環状除草剤
US6451740B2 (en) 1999-12-07 2002-09-17 Sumitomo Chemical Company, Limited Uracil compounds and use thereof
US6537948B1 (en) 2000-02-04 2003-03-25 Sumitomo Chemical Company, Limited Uracil compounds and use thereof
US6617281B1 (en) 1998-07-09 2003-09-09 Bayer Aktiengesellschaft Substituted acylamino phenyl uracils
US10647661B2 (en) 2017-07-11 2020-05-12 Vertex Pharmaceuticals Incorporated Carboxamides as modulators of sodium channels

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MY138097A (en) * 2000-03-22 2009-04-30 Du Pont Insecticidal anthranilamides
CN101704790B (zh) * 2006-10-19 2011-09-28 湖南化工研究院 除草的n3-取代苯基脲嘧啶类化合物
CN101165057B (zh) * 2006-10-19 2011-04-27 湖南化工研究院 除草的n3-取代苯基脲嘧啶类化合物

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0563384A1 (fr) * 1990-12-17 1993-10-06 Nissan Chemical Industries, Limited Derive d'uracile

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0563384A1 (fr) * 1990-12-17 1993-10-06 Nissan Chemical Industries, Limited Derive d'uracile

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002521001A (ja) * 1997-02-26 2002-07-09 エフ エム シー コーポレーション シクロイミド置換ベンゾ縮合ヘテロ環状除草剤
US6617281B1 (en) 1998-07-09 2003-09-09 Bayer Aktiengesellschaft Substituted acylamino phenyl uracils
US6451740B2 (en) 1999-12-07 2002-09-17 Sumitomo Chemical Company, Limited Uracil compounds and use thereof
US6667413B2 (en) 1999-12-07 2003-12-23 Sumitomo Chemical Company, Limited Uracil compounds and use thereof
US6537948B1 (en) 2000-02-04 2003-03-25 Sumitomo Chemical Company, Limited Uracil compounds and use thereof
US10647661B2 (en) 2017-07-11 2020-05-12 Vertex Pharmaceuticals Incorporated Carboxamides as modulators of sodium channels
US11603351B2 (en) 2017-07-11 2023-03-14 Vertex Pharmaceuticals Incorporated Carboxamides as modulators of sodium channels

Also Published As

Publication number Publication date
CN1193319A (zh) 1998-09-16
AR002596A1 (es) 1998-03-25
BR9609319A (pt) 1999-07-06
CA2225828A1 (fr) 1997-01-16
JPH11508545A (ja) 1999-07-27
AR006084A1 (es) 1999-08-11
AU6304396A (en) 1997-01-30
EP0835247A1 (fr) 1998-04-15
DE19523640A1 (de) 1997-01-02
KR19990028225A (ko) 1999-04-15

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