WO2001090102A2 - 6-heteroclyclyl-3-oxo-3,4-dihydro-quinoxalines - Google Patents

6-heteroclyclyl-3-oxo-3,4-dihydro-quinoxalines Download PDF

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Publication number
WO2001090102A2
WO2001090102A2 PCT/EP2001/005382 EP0105382W WO0190102A2 WO 2001090102 A2 WO2001090102 A2 WO 2001090102A2 EP 0105382 W EP0105382 W EP 0105382W WO 0190102 A2 WO0190102 A2 WO 0190102A2
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Prior art keywords
chlorine
fluorine
optionally substituted
methyl
cyano
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PCT/EP2001/005382
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German (de)
English (en)
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WO2001090102A3 (fr
Inventor
Hans-Georg Schwarz
Karl-Heinz Linker
Mark Wilhelm Drewes
Peter Dahmen
Dieter Feucht
Rolf Pontzen
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Bayer Aktiengesellschaft
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Priority claimed from DE10055499A external-priority patent/DE10055499A1/de
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU65944/01A priority Critical patent/AU6594401A/en
Publication of WO2001090102A2 publication Critical patent/WO2001090102A2/fr
Publication of WO2001090102A3 publication Critical patent/WO2001090102A3/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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the invention relates to new 6-heterocyclyl-3-oxo-3,4-dmydro-ch - noxaline, a process and new intermediates for their preparation and their use as
  • Plant treatment agents in particular as herbicides.
  • 6-heterocyclyl-3-oxo-l, 2,3,4-tetrahydro-quinoxaline see EP-A-420194
  • 6-heterocyclyl-3-oxo-3,4-dihydro-quinoxaline e.g. the compounds 7- (4-chloro-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl) -6-fluoro-2 (1H) - quinoxalinone (cf.
  • R 1 represents hydrogen or represents optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkenyloxy, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylthio, arylsulfinyl, arylsulfonyl or arylalkyl, R represents hydrogen, cyano, halogen or optionally substituted alkyl,
  • R represents hydrogen or halogen
  • Q 1 represents O (oxygen) or S (sulfur),
  • Q 2 represents O (oxygen) or S (sulfur),
  • R 4 represents hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkenyl, Alkynyl, alkoxy, alkoxycarbonyl, alkenyloxy, alkfnyloxy, alkylthio, alkenylthio, alkynylthio, AU-ylamino, dialkylamino, cycloalkyl or cycloalkylalkyl, and
  • R 5 represents hydrogen, hydroxy, amino, cyano, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl,
  • hydrocarbon chains such as alkyl, alkenyl or alkynyl - also in connection with heteroatoms, such as in alkylamino - are in each case straight-chain or branched.
  • R 1 preferably represents hydrogen, in each case optionally alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or substituted by cyano, halogen, C 1 -C alkoxy or C 1 -C 4 alkoxycarbonyl
  • Alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, for each alkenyl optionally substituted by cyano or halogen, alkenyloxy or alkynyl each having 3 to 6 carbon atoms, for each cycloalkyl optionally substituted by cyano, halogen or C 1 -C 4 alkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the
  • R> 2 preferably represents hydrogen, cyano, halogen or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C 1 -C 4 alkoxy.
  • R preferably represents hydrogen, fluorine or chlorine.
  • Q 1 preferably represents O (oxygen).
  • Q is preferably O (oxygen).
  • R4 preferably represents hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, alkyl optionally substituted by cyano, halogen or C 4 -C 4 -alkoxy having 1 to 6 carbon atoms, alkenyl optionally substituted by halogen or Alkynyl each having 2 to 6 carbon atoms, each for alkoxy or alkoxycarbonyl optionally substituted by cyano, halogen or d - alkoxy or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups, each optionally halogen-substituted alkenyloxy or alkynyloxy each having 3 to 6 carbon atoms, for alkylthio having 1 to 6 carbon atoms optionally substituted by cyano, halogen or C 1 -C 6 -alkoxy, for each optionally substituted by halogen alkenylthio or alkynylthi
  • R5 preferably represents hydrogen, hydroxy, amino, cyano, alkyl, alkoxy, alkoxycarbonyl or alkylamino, each optionally substituted by cyano, halogen or dC 4 -alkoxy, each having up to 6 carbon atoms, each optionally substituted by halogen, alkenyl or alkynyl each up to 6 carbon atoms, for cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or CrC 4 alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by nitro, cyano, Halogen, -CC alkyl, -C 4 - haloalkyl, C 1 -C alkoxy or C 1 -C 4 haloalkoxy substituted
  • Phenyl or phenyl -CC-alkyl Phenyl or phenyl -CC-alkyl.
  • R 1 particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, acetyl,
  • R .2 particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n-, i-, s- or optionally substituted by fluorine, chlorine, methoxy or ethoxy t-butyl.
  • R4 particularly preferably represents hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, n-, i-, s- or t-butyl, for in each case optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl,
  • Ethynyl, propynyl or butynyl for methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for each optionally substituted by fluorine, chlorine or Bromine-substituted propenyloxy, butenyloxy, propynyloxy or butynyloxy, each for methylthio, ethylthio, n- or i-propylthio optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for propenylthio, butenylthio optionally substituted by fluorine, chlorine or bromine , Propynylthio or butynylthio, for methylamino, ethylamino, n- or
  • R5 particularly preferably represents hydrogen, hydroxyl, amino, cyano, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i- Propoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, Ethylamino, n- or i-propylamino, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine, chlorine or bromine, for each optionally by
  • R 1 very particularly preferably represents hydrogen, in each case optionally substituted by fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, methyl, ethyl, n- or i-propyl, acetyl, propionyl, methoxy, ethoxy, n- or i-propoxy , Methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, for propenyl, butenyl optionally substituted by fluorine and / or chlorine , Propinyl or
  • R very particularly preferably represents hydrogen, fluorine, chlorine, bromine, or methyl or ethyl which is in each case optionally substituted by fluorine and / or chlorine.
  • R4 very particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, in each case optionally by fluorine,
  • R5 very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, in each case propenyl optionally substituted by fluorine and / or chlorine, Butenyl, propynyl or butynyl, or for each optionally substituted by fluorine, chlorine or methyl
  • a very particularly preferred group are those compounds of the formula (I) in which
  • R 1 for hydrogen, for in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy methyl, ethyl, n- or i-propyl, for in each case optionally substituted by fluorine and / or chlorine propenyl, butenyl, propynyl or butinyl, or for optionally by Fluorine, chlorine or methyl-substituted cyclopropyl
  • R 2 represents hydrogen or methyl optionally substituted by fluorine and / or chlorine
  • R 3 represents hydrogen, fluorine or chlorine
  • Q 1 represents oxygen or sulfur
  • Q 2 represents oxygen or sulfur
  • R 5 represents in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy, methyl or ethyl, or represents in each case optionally substituted by fluorine and / or chlorine propenyl, butenyl, propynyl or butinyl, the two R 5 groups being identical or different in each individual case could be.
  • Another very particularly preferred group are those compounds of the formula (I) in which
  • R 1 for hydrogen, for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, for propenyl, butenyl, propynyl each optionally substituted by fluorine and / or chlorine or butinyl, or represents cyclopropyl optionally substituted by fluorine, chlorine or methyl,
  • R 2 represents hydrogen or methyl optionally substituted by fluorine and / or chlorine
  • R 3 represents hydrogen, fluorine or chlorine
  • Q 1 represents oxygen or sulfur
  • Q oxygen or sulfur
  • R 4 "1 stands for cyano or for methyl or ethyl optionally substituted by fluorine and / or chlorine,
  • R represents hydrogen, fluorine, chlorine, bromine or in each case optionally substituted by fluorine and / or chlorine methyl or ethyl
  • R 5 for amino or for each optionally by fluorine, chlorine, methoxy or
  • radicals listed above or those specified in preferred ranges apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products 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.
  • Preferred compounds according to the invention are those of the formula (I) in which there is a combination of the meanings listed above as preferred.
  • the new 6-heterocyclyl-3-oxo-3,4-dihydroquinoxalines of the general formula (I) have interesting biological properties. They are particularly characterized by their strong herbicidal activity.
  • R represents alkyl, preferably d-Q-alkyl (e.g. methyl or ethyl),
  • Formula (IT) provides a general definition of the 4-heterocyclyl-1,2-phenylene diamines to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • R 1 , R 3 and Z preferably have those meanings which are preferred, particularly preferred or very particularly preferred for R in connection with the description of the compounds of the general formula (I) according to the invention, R and Z have been specified.
  • R 1 , R 3 and Z have the meanings given above, with a reducing agent, such as iron, in the presence of a diluent, such as acetic acid, at temperatures between 0 ° C and 100 ° C (cf. the preparation examples).
  • a reducing agent such as iron
  • a diluent such as acetic acid
  • Formula (IV) provides a general definition of the 5-heterocyclyl-2-nitro-phenylamines to be used as precursors.
  • R 1 , R and Z preferably have the meanings already given above in connection with the description of the compounds of the general formula according to the invention
  • R and Z have the meanings given above and
  • X 1 represents halogen (in particular fluorine or chlorine),
  • reaction auxiliary e.g. Sodium hydride
  • a diluent e.g. Acetonitrile
  • Formula (III) provides a general definition of the 2-oxocarboxylic acid esters to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • R 2 preferably has the meaning which has already been given for R in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred or very particularly preferred;
  • R preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl.
  • the starting materials of the general formula (III) are known organic synthetic chemicals.
  • the process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out using a reaction auxiliary.
  • the usual reaction aids here are generally the usual organic 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; basic organic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl diisopropylamine, N, N-dimethylcyclohex
  • a diluent inert organic solvents are particularly suitable as diluents. These include in particular aliphatic, ahcyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or
  • Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethyl-phosphoric acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i- Propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether.
  • 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 120 ° C.
  • 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 increased 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.
  • the work-up is carried out using 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 understood to mean all plants that grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can be used, for example, in the following plants: Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Gupopsisia, Euphorbia , Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver,
  • Dactyloctenium Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Pous, Sagaria, Setaria, Rottboell.
  • the active compounds according to the invention are suitable for combating total weeds, for example on industrial and rail tracks and on paths and squares with and without tree growth.
  • the active compounds according to the invention for combating weeds in permanent crops for example forest, ornamental wood, Fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil pan, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land as well as for selective weed control in annual crops be used.
  • the compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also 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 also be used to control animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plants such as shoots, leaves, flowers and roots, are to be understood, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, for example by dipping, spraying, evaporating, atomizing, scattering, spreading and using propagation material, in particular seeds. continue by wrapping one or more layers.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • 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 as well as their ethers and esters, ketones such as
  • Possible solid carriers 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 Silicic acid, aluminum oxide and silicates are suitable as solid carriers for granules: e.g.
  • Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Further,
  • 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 in a mixture with known herbicides and / or with substances which improve crop tolerance (“safeners”) for weed control, ready-to-use formulations or tank mixes being possible. Mixtures are also possible possible with weed control agents which contain one or more known herbicides and a safener.
  • safeners substances which improve crop tolerance
  • herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin (beflubutamide, ethyl), Benfuresate, Bensulfuron (-methyl), Bentazon, Benzfendizone, Benzobicyclon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butafenacil (-allyi , Butroxydim, Butylate, cafenstrole, Caloxydim, Carbetamide, Carfentra
  • Diflufenican Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethofmethyl Sulfur (Ethofmethyl) Sulfur Etobenzanid, Fenoxaprop (-P-ethyl), Fentrazamide, Flamprop (-isopropyl, -isopropyl-L, -methyl), Flazasulfuron, Florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flufen- acet, flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, flu
  • Tribenuron (-methyl), triclopyr, tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl), tritosulfuron.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • the calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).
  • the lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • 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 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area.
  • the active ingredient concentration in the spray liquor is selected so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.
  • 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 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area.
  • the active ingredient concentration in the spray liquor is selected so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Test plants with a height of 5 to 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 in
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

Abstract

L'invention concerne des composés correspondant à la formule générale (I), dans laquelle R?1, R2, R3¿ et Z ont les significations données dans la description, ainsi qu'un procédé et de nouveaux produits intermédiaires permettant de produire ces composés, et leur utilisation comme agents phytosanitaires, en particulier comme herbicides.
PCT/EP2001/005382 2000-05-24 2001-05-11 6-heteroclyclyl-3-oxo-3,4-dihydro-quinoxalines WO2001090102A2 (fr)

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DE10025624.4 2000-05-24
DE10025624 2000-05-24
DE10055499.7 2000-11-09
DE10055499A DE10055499A1 (de) 2000-05-24 2000-11-09 6-Heterocyclyl-3-oxo-3,4-dihydro-chinoxaline

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WO2001090102A2 true WO2001090102A2 (fr) 2001-11-29
WO2001090102A3 WO2001090102A3 (fr) 2002-06-20

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WO2012085648A1 (fr) 2010-12-22 2012-06-28 Purdue Pharma L.P. Composés de pipéridine de type quinoxaline substitués par du phosphore et leurs utilisations
EP2537844A1 (fr) 2008-07-21 2012-12-26 Purdue Pharma L.P. Composés pipéridine à liaison et substitués par une quinoxaline, et leurs utilisations
WO2013080036A1 (fr) 2011-12-01 2013-06-06 Purdue Pharma L.P. Composés de pipéridine de type quinoxaline substituée par une azétidine et leurs utilisations
WO2014020405A1 (fr) 2012-07-30 2014-02-06 Purdue Pharma L.P. Composés de pipéridine cycliques de type quinoxaline substitués par un groupe dérivé d'urée ou un groupe dérivé de lactame et leurs utilisations
WO2014102588A2 (fr) 2012-12-27 2014-07-03 Purdue Pharma L.P. Composés de pipéridine de type indole et indoline et leurs utilisations
WO2014102594A2 (fr) 2012-12-27 2014-07-03 Purdue Pharma L.P. Composés de pipéridine de type benzimidazole substitué et leurs utilisations
WO2014102592A2 (fr) 2012-12-27 2014-07-03 Purdue Pharma L.P. Composés de pipéridine de type quinoxaline substituée par oxime et leurs utilisations
WO2014102589A1 (fr) 2012-12-27 2014-07-03 Purdue Pharma L.P. Composés de pipéridine du type quinazolin-4(3h)-one et utilisations de ceux-ci
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US9676754B2 (en) 2012-12-20 2017-06-13 Inception 2, Inc. Triazolone compounds and uses thereof
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EP0597360A1 (fr) * 1992-11-12 1994-05-18 Bayer Ag N-phényle-triazolin (thi)ones substitués, procédés et produits intermédiaires pour leur préparation et leur utilisation comme herbicides, insecticides et acaricides

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EP2537844A1 (fr) 2008-07-21 2012-12-26 Purdue Pharma L.P. Composés pipéridine à liaison et substitués par une quinoxaline, et leurs utilisations
US8476271B2 (en) 2008-07-21 2013-07-02 Purdue Pharma, L.P. Substituted-quinoxaline-type bridged-piperidine compounds as ORL-1 modulators
US11111246B2 (en) 2008-07-21 2021-09-07 Purdue Pharma L.P. Pharmaceutical salts of substituted-quinoxaline-type bridged-piperidine compounds
US10519156B2 (en) 2008-07-21 2019-12-31 Purdue Pharma L.P. 9′-Aza[3,9′-bi(bicyclo[3.3.1]nonan)]-3′-one and preparation thereof
US9890164B2 (en) 2008-07-21 2018-02-13 Purdue Pharma, L.P. Substituted-quinoxaline-type bridged-piperidine compounds as ORL-1 modulators
US9145408B2 (en) 2008-07-21 2015-09-29 Purdue Pharma L.P. Substituted-quinoxaline-type bridged-piperidine compounds as ORL-1 modulators
WO2012085648A1 (fr) 2010-12-22 2012-06-28 Purdue Pharma L.P. Composés de pipéridine de type quinoxaline substitués par du phosphore et leurs utilisations
US9598447B2 (en) 2010-12-22 2017-03-21 Purdue Pharma L.P. Phosphorus-substituted quinoxaline-type piperidine compounds and uses thereof
WO2013080036A1 (fr) 2011-12-01 2013-06-06 Purdue Pharma L.P. Composés de pipéridine de type quinoxaline substituée par une azétidine et leurs utilisations
US9290488B2 (en) 2011-12-01 2016-03-22 Purdue Pharma L.P. Azetidine-substituted quinoxalines as opioid receptor like-1 modulators
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WO2014020405A1 (fr) 2012-07-30 2014-02-06 Purdue Pharma L.P. Composés de pipéridine cycliques de type quinoxaline substitués par un groupe dérivé d'urée ou un groupe dérivé de lactame et leurs utilisations
US9085561B2 (en) 2012-07-30 2015-07-21 Purdue Pharma L.P. Cyclic urea- or lactam-substituted quinoxaline-type piperidines as ORL-1 modulators
US9676754B2 (en) 2012-12-20 2017-06-13 Inception 2, Inc. Triazolone compounds and uses thereof
US10568871B2 (en) 2012-12-20 2020-02-25 Tempest Therapeutics, Inc. Triazolone compounds and uses thereof
US11666557B2 (en) 2012-12-20 2023-06-06 Tempest Therapeutics, Inc. Triazolone compounds and uses thereof
US9598411B2 (en) 2012-12-27 2017-03-21 Purdue Pharma L.P. Substituted benzimidazole-type piperidine compounds and uses thereof
US9090618B2 (en) 2012-12-27 2015-07-28 Purdue Pharma L.P. Substituted benzimidazole-type piperidine compounds and uses thereof
US9040533B2 (en) 2012-12-27 2015-05-26 Purdue Pharma L.P. Oxime-substituted-quinoxaline-type piperidine compounds as ORL-1 modulators
WO2014102589A1 (fr) 2012-12-27 2014-07-03 Purdue Pharma L.P. Composés de pipéridine du type quinazolin-4(3h)-one et utilisations de ceux-ci
US9951038B2 (en) 2012-12-27 2018-04-24 Purdue Pharma L.P. Quinazolin-4(3H)-one-type piperidine compounds and uses thereof
US9963458B2 (en) 2012-12-27 2018-05-08 Purdue Pharma L.P. Indole and indoline-type piperidine compounds and uses thereof
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