WO1998002422A1 - Composes aromatiques substitues de carbonyle et leurs derives - Google Patents

Composes aromatiques substitues de carbonyle et leurs derives Download PDF

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Publication number
WO1998002422A1
WO1998002422A1 PCT/EP1997/003433 EP9703433W WO9802422A1 WO 1998002422 A1 WO1998002422 A1 WO 1998002422A1 EP 9703433 W EP9703433 W EP 9703433W WO 9802422 A1 WO9802422 A1 WO 9802422A1
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WO
WIPO (PCT)
Prior art keywords
series
alkyl
methoxy
radical
diyl
Prior art date
Application number
PCT/EP1997/003433
Other languages
German (de)
English (en)
Inventor
Roland Andree
Mark Wilhelm Drewes
Wilhelm Haas
Andreas Lender
Karl-Heinz Linker
Otto Schallner
Markus Dollinger
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 JP10505556A priority Critical patent/JP2000514805A/ja
Priority to BR9710238A priority patent/BR9710238A/pt
Priority to EP97930469A priority patent/EP0912527A1/fr
Priority to IL12780297A priority patent/IL127802A0/xx
Priority to AU34412/97A priority patent/AU3441297A/en
Publication of WO1998002422A1 publication Critical patent/WO1998002422A1/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
    • 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
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D253/075—Two hetero atoms, in positions 3 and 5

Definitions

  • the invention relates to new substituted aromatic carbonyiver compounds and their derivatives, processes for their preparation and their use as herbicides
  • Q represents oxygen, sulfur or imino (NH),
  • R represents hydrogen or halogen
  • R> 2 represents the grouping below
  • a 1 furthermore represents an optionally substituted radical from the series alkanediyl, alkenediyi, alkindiyl, cycloalkanediyl, cycloalkenediyl or arenediyl,
  • a 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO -, -, -CO- or the group -NR 5 -, in which R 5 represents hydrogen,
  • Hydroxyl or a radical of the series alkyl, aryl, alkoxy, alkylsulfonyl or arylsulfonyl,
  • a ⁇ furthermore represents an optionally substituted radical from the series alkanediyl, alkenediyi, alkindiyl, cycloalkanediyl, cycloalkenediyl or arenediyl, and
  • R 3 represents hydrogen, hydroxy, mercapto, amino (in which case Q does not represent sulfur) or an optionally substituted radical from the series alkyl, alkoxy, alkylthio or alkylamino, and
  • Z represents an optionally substituted monocyclic or bicyclic, saturated or unsaturated radical from the heterocyclyl series (exception: piperazinyl), heterocyclylamino or heterocyclylimino,
  • the new substituted aromatic carbonyi compounds of the general formula (I) are notable for their strong herbicidal activity
  • saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl - also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino - are each straight-chain or branched
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably
  • the invention preferably relates to compounds of the formula (1) in which
  • Q represents oxygen, sulfur or imino (NH),
  • R 1 represents hydrogen, fluorine, chlorine or bromine
  • R 2 represents the grouping below
  • a 1 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 -, -CO- or the group -NR 4 -, in which R 4 represents hydrogen,
  • a 1 furthermore represents a substituted each optionally substituted by fluorine or chlorine radical from the group C r C 6 - alkanediyl, C 2 -C 6 - Alkendiyi, C 2 - C 6 alkynediyl, C -C 6 -cycloalkanediyl, C r C 6 - Cycloalkenediyl or
  • Phenyl is A 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO -, -, -CO- or the grouping -NR 5 -, wherein R 5 represents hydrogen, hydroxy or a radical of the series C, -C 4 -Alkyl, CC 4 -alkoxy, phenyl, C ] -C 4 -alkylsulfonyl or phenylsulfonyl,
  • a 2 continues for a each is optionally substituted by fluorine or chlorine radical from the series C, -C 6 -Alkand ⁇ yl, C 2 -C 6 -Alkend ⁇ yl, C, - C 6 alkynediyl, C 6 -C -Cycloalkandtyl, C 3 -C 6 -Cycloalkend ⁇ yl or phenyl is,
  • Halogen or for a radical of the series alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialalkoxy (th ⁇ o) phosphoryl which is optionally substituted by halogen, C, - C 4 -alkoxy or C, -C 4 -alkox ⁇ m ⁇ no each has 1 to 6 carbon atoms in the alkyl groups,
  • a 3 furthermore represents an optionally substituted by halogen radical from the series alkenyl, alkenyloxy, alkenylamino, alkylene amine, alkenyloxycarbonyl, alkynyl, alkynyl oxy, alkynylamino or alkynyloxycarbonyl, each having 2 to 6 carbon atoms in the alkenyl, alkylene or alkynyl groups stands,
  • a 3 further for each optionally by nitro, cyano, carboxy, halogen, C r C 4 alkyl, C r C 4 haloalkyl, C, -C 4 alkyloxy, C ] -C 4 haloalkyloxy and / or C, -C 4 alkoxy-carbonyl substituted radical of the series phenyl, phenyl oxy, phenyl-C r C 4 -alkyl, phenyl-C, -C 4 -alkoxy, phenyl oxy carbonyl or phenyl-C, -C 4 -alkoxy - carbonyl, (in each case optionally completely or partly hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, Isothiazoiyl, oxadiazolyl, thiadiazoly
  • R ' represents hydrogen, hydroxy, mercapto, amino (in which case Q does not represent sulfur) or one in each case optionally by hydroxy,
  • Z represents a respective monocyclic or bicyclic, saturated or unsaturated radical from the heterocyclyl series (except piperazinyl), heterocycliclamino or heterocyclylimino, each with 2 to 6 carbon atoms and 1 to 4 nitrogen atoms in the heterocyclic ring system, which optionally also contains an oxygen or Contains sulfur atom and / or optionally up to three groups from the series -CO-, -CS-, -SO- and / or SO 2 -, and which is optionally substituted by one or more groups from the series nitro, hydroxy, amino, Cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C, -C -alkyl (which in turn is optionally substituted by halogen or C, -C 4 -alkoxy), C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl (which in turn are optionally substituted by halogen), C, -C
  • Alkoxycarbonyl (which in turn are each optionally substituted by halogen or C 1 -C 4 -alkoxy), C 2 -C 6 alkenyloxy or C- > C 6 -alkynyloxy (which in turn are each optionally substituted by halogen), C , -C 6 alkylthio, C 2 -C 6 alkenylthio or C 2 -C 6 alkynylthio (which in turn are each optionally substituted by halogen),
  • the invention relates in particular to compounds of the formula (I) in which
  • Q represents oxygen, sulfur or imino (NH),
  • R 1 represents hydrogen, fluorine or chlorine
  • R 2 represents the grouping below
  • Hydroxyl or a radical of the series methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methyl sulfonyl or ethyl sulfonyl,
  • a 1 furthermore for a radical of the series methylene, ethane-l, l-diyl, ethane-1,2-diyl, propane-l, l-diyl, propane-l, 2-diyl, propane-l, 3-diyl, Ethen-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl,
  • a 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO -, -CO- or the grouping -NR 5 -, in which R 5 represents hydrogen, Hydroxyl or a radical of the series methyl, ethyl, n- or l-propyl, methoxy, ethoxy, n- or l-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenyl sulfonyl,
  • a 2 furthermore for a radical of the series methylene, ethane-1, 1-d ⁇ yl, ethane-1, 2-diyl, propane-l, l-d ⁇ yl, propane-1,2-diyl, propane-1,3-diyl, Ethen
  • a 3 furthermore for one each optionally by fluorine, chlorine,
  • a 1 furthermore for one in each case optionally by nitro, cyano,
  • R 3 represents hydrogen, hydroxyl, mercapto, amino (in which case Q does not represent sulfur) or a radical of the series methyl, ethyl, n- which is optionally substituted by hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl. or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or l-propylamino, and
  • Z stands for a monocychic or bicyclic, saturated or unsaturated residue of the heterocyclyl series (exception: piperazinyl), heterocycliclamino or heterocyclylimino, each with 2 to 5 carbon atoms and 1 to 3 nitrogen atoms in the heterocyclic ring system, which optionally also contains an oxygen or Contains sulfur atom and / or optionally up to two groups from the series -CO-, -CS-, -SO- and / or SO -, -, which is optionally substituted by one or more groupings from the series nitro, hydroxy, amino , Cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or l-propyl, n-, 1-, s- or t-butyl, (which in turn may be replaced by fluorine, chlorine, methoxy or Are substituted ethoxy), Propenyl, buten
  • R 6 for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, cyclopropyl, difluoromethyl, T ⁇ -fluoromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i -Propoxy, difluoromethoxy, t ⁇ fluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, tifluoromethylthio, chlorodifluoromethylthio, methylammo, ethyl ino, n- or l-propylamino, dimethylamino, diethylamino, diethylamino, diethylamino, diethylamino, diethylamino, dieth
  • R represents hydrogen, hydroxy, amino, cyano, methyl, ethyl, n- or i-propyl
  • 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 combined with one another as desired, that is to say also between the specified ranges of preferred compounds
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 1 have, for example, those given above in Group 1
  • R, R ⁇ and R J have, for example, those given in Group 1 above
  • R 1 , R 2 and R J have, for example, the meanings given above in Group 1.
  • R. 1, R r> 2 ⁇ and R ' have, for example, those given in Group 1 above
  • substituted aromatic nitriles to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (II).
  • R 1 , R 2 and Z preferably or in particular those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R 1 , R 2 and Z.
  • the process according to the invention for the preparation of the new compounds of the formula (I) is preferably carried out in the presence of a reaction auxiliary.
  • a reaction auxiliary include water and the customary organic diluents,
  • Oxidizing agents such as hydrogen peroxide or sodium chloride, as well as amidosulfonic acid
  • 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 20 ° 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 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 for several hours at the required temperature. Working up is carried out by customary methods (cf. the preparation 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 be used, for example, in the following plants
  • the compounds are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops for example forest, ornamental wood, fruit, wine , Citrus, nut, banana, coffee, tea, gum, 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 onocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence
  • 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
  • formulations are prepared in a known manner, for example 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-producing agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • Liquid solvents are essentially suitable.
  • Aromatics such as xylene, toluene or alkyl naphthalenes, 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
  • Solid carrier materials are suitable.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural ones, can be used in the formulations
  • Phospholipids such as cephalins and lecithins and synthetic phosphohpides.
  • Other 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 alizine, 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 for weed control, finished formulations or tank mixes being possible
  • herbicides are suitable for the mixtures, for example aceto-chlorine, acifluorfen (-sod ⁇ um), aclonifene, alachlor, alloxyd ⁇ m (-sod ⁇ um), ametryne, amidochlor, amidosulfuron, asulam, atrazine, azimsulfuron, benazohn, benfuresate, bensulfuron ( -methyl), bentazone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bromobutide, bromofenoxime, bromoxynil, butachlor, butylates, cafenstrole, carbetamides, chloromethoxyfen, chloramben, chlorodazone, chloromuron (-ethyl), chloron Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodina
  • 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.
  • the use is carried out in a customary manner, for example by pouring, spraying, spraying, Scatter
  • the active compounds according to the invention can be applied both before and after the plants emerge. They can also be incorporated into the soil before sowing
  • the amount of active ingredient used can vary over a wide range. It depends essentially 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
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the active ingredient preparation is sprayed onto the soil, so that the desired amounts of active ingredient are applied per unit area.
  • the concentration of the concentrated boil is chosen so that in 1 000 l of water / ha each desired amounts of active ingredient are applied
  • the compound according to production example 2 at a rate of 60 g / ha shows a very strong action against weeds such as Avena fatua (80%), Seta ⁇ a (95%), Abutilon (100%), Amaranthus (100%), Galium (95% and Sinapis (100%)
  • weeds such as Avena fatua (80%), Seta ⁇ a (95%), Abutilon (100%), Amaranthus (100%), Galium (95% and Sinapis (100%)
  • Test plants which have a height of 5-15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area.
  • the concentration of the spray is chosen so that the respectively desired amounts of active compound are applied in 1000 l of water / ha.
  • the compound according to Preparation Example 2 shows a very strong action against weeds such as Abutilon (100%), Amaranthus (100%), Galium (90%) and Sinapis (100%) at an application rate of 60 g / ha.

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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)

Abstract

Ces nouveaux composés aromatiques substitués de carbonyle et leurs dérivés répondent à la formule générale (I), dans laquelle Q désigne oxygène, soufre ou imino (NH); R1 désigne hydrogène ou halogène; et R2 désigne le groupe -A?1-A2-A3, où A1, A2 et A3¿ ont la signification donnée dans la description. L'invention concerne également leur procédé de préparation et leur utilisation comme herbicides.
PCT/EP1997/003433 1996-07-11 1997-07-01 Composes aromatiques substitues de carbonyle et leurs derives WO1998002422A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP10505556A JP2000514805A (ja) 1996-07-11 1997-07-01 置換芳香族カルボニル化合物及びそれらの誘導体
BR9710238A BR9710238A (pt) 1996-07-11 1997-07-01 Composto carbonila aromaticos e derivados dos mesmos
EP97930469A EP0912527A1 (fr) 1996-07-11 1997-07-01 Composes aromatiques substitues de carbonyle et leurs derives
IL12780297A IL127802A0 (en) 1996-07-11 1997-07-01 Substituted aromatic carbonyl compounds and derivatives thereof
AU34412/97A AU3441297A (en) 1996-07-11 1997-07-01 Substituted aromatic carbonyl compounds and their derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19627901A DE19627901A1 (de) 1996-07-11 1996-07-11 Substituierte aromatische Carbonylverbindungen und ihre Derivate
DE19627901.1 1996-07-11

Publications (1)

Publication Number Publication Date
WO1998002422A1 true WO1998002422A1 (fr) 1998-01-22

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PCT/EP1997/003433 WO1998002422A1 (fr) 1996-07-11 1997-07-01 Composes aromatiques substitues de carbonyle et leurs derives

Country Status (8)

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EP (1) EP0912527A1 (fr)
JP (1) JP2000514805A (fr)
AU (1) AU3441297A (fr)
BR (1) BR9710238A (fr)
CA (1) CA2260201A1 (fr)
DE (1) DE19627901A1 (fr)
IL (1) IL127802A0 (fr)
WO (1) WO1998002422A1 (fr)

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WO2018077923A1 (fr) 2016-10-27 2018-05-03 Bayer Aktiengesellschaft 1,2,4-triazolones trisubstituées en position 2, 4 et 5, utiles en tant qu'inhibiteurs de dhodh
WO2018077944A2 (fr) 2016-10-27 2018-05-03 Bayer Aktiengesellschaft 1,2,4-triazolones 4,5-annelées
EP3553052A1 (fr) 2018-04-10 2019-10-16 Bayer AG Dérivés de 5-oxo-4,5-dihydro-1h-1,2,4-triazole pour le traitement du cancer
WO2019197239A1 (fr) 2018-04-10 2019-10-17 Bayer Aktiengesellschaft Procédé de préparation d'une 1,2,4-triazolone 2,4,5-trisubstituée

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DE19929348A1 (de) * 1999-06-26 2000-12-28 Bayer Ag Verfahren zur Herstellung von 2-Heterocyclylmethyl-benzoesäurederivaten
DE19946853A1 (de) 1999-09-30 2001-04-05 Bayer Ag Substituierte Arylketone
SI1226127T1 (sl) * 2000-05-04 2009-10-31 Basf Se Substituirani fenilsulfamoil karboksamidi
CN100368392C (zh) * 2002-10-30 2008-02-13 巴斯福股份公司 双官能异(硫)氰酸苯酯、其制备方法和中间体

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DE19531152A1 (de) * 1994-12-15 1996-06-20 Bayer Ag Substituierte N-Aryl-Stickstoffheterocyclen
DE19516785A1 (de) * 1995-05-08 1996-11-14 Bayer Ag Substituierte Aminophenyluracile
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DE19528305A1 (de) * 1995-08-02 1997-02-06 Bayer Ag Substituierte Phenyluracile
DE19528186A1 (de) * 1995-08-01 1997-02-06 Bayer Ag Substituierte Phenyluracile

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Publication number Priority date Publication date Assignee Title
DE19500439A1 (de) * 1994-05-04 1995-11-09 Bayer Ag Substituierte aromatische Thiocarbonsäureamide
DE19531152A1 (de) * 1994-12-15 1996-06-20 Bayer Ag Substituierte N-Aryl-Stickstoffheterocyclen
DE19516785A1 (de) * 1995-05-08 1996-11-14 Bayer Ag Substituierte Aminophenyluracile
DE19527570A1 (de) * 1995-07-28 1997-01-30 Bayer Ag Substituierte Aminouracile
DE19528186A1 (de) * 1995-08-01 1997-02-06 Bayer Ag Substituierte Phenyluracile
DE19528305A1 (de) * 1995-08-02 1997-02-06 Bayer Ag Substituierte Phenyluracile

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018077923A1 (fr) 2016-10-27 2018-05-03 Bayer Aktiengesellschaft 1,2,4-triazolones trisubstituées en position 2, 4 et 5, utiles en tant qu'inhibiteurs de dhodh
WO2018077944A2 (fr) 2016-10-27 2018-05-03 Bayer Aktiengesellschaft 1,2,4-triazolones 4,5-annelées
US10968216B2 (en) 2016-10-27 2021-04-06 Bayer Aktiengesellschaft 4,5-annulated 1,2,4-triazolones
US11130745B2 (en) 2016-10-27 2021-09-28 Bayer Aktiengellschaft 2,4,5-trisubstituted 1,2,4-triazolones useful as inhibitors of DHODH
US11713304B2 (en) 2016-10-27 2023-08-01 Bayer Aktiengesellschaft 2,4,5-trisubstituted 1,2,4-triazolones useful as inhibitors of DHODH
US11787797B2 (en) 2016-10-27 2023-10-17 Bayer Aktiengesellschaft 4,5-annulated 1,2,4-triazolones
EP3553052A1 (fr) 2018-04-10 2019-10-16 Bayer AG Dérivés de 5-oxo-4,5-dihydro-1h-1,2,4-triazole pour le traitement du cancer
WO2019197239A1 (fr) 2018-04-10 2019-10-17 Bayer Aktiengesellschaft Procédé de préparation d'une 1,2,4-triazolone 2,4,5-trisubstituée
US11365179B2 (en) 2018-04-10 2022-06-21 Bayer Aktiengesellschaft Method for the preparation of a 2,4,5-trisubstituted 1,2,4-triazolone

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AU3441297A (en) 1998-02-09
BR9710238A (pt) 1999-08-10
DE19627901A1 (de) 1998-01-15
EP0912527A1 (fr) 1999-05-06
CA2260201A1 (fr) 1998-01-22
IL127802A0 (en) 1999-10-28
JP2000514805A (ja) 2000-11-07

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