EP0754179A1 - Sulfonylaminocarbonyltriazolinones substituees et leur utilisation comme herbicides - Google Patents

Sulfonylaminocarbonyltriazolinones substituees et leur utilisation comme herbicides

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Publication number
EP0754179A1
EP0754179A1 EP95914315A EP95914315A EP0754179A1 EP 0754179 A1 EP0754179 A1 EP 0754179A1 EP 95914315 A EP95914315 A EP 95914315A EP 95914315 A EP95914315 A EP 95914315A EP 0754179 A1 EP0754179 A1 EP 0754179A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
substituted
fluorine
chlorine
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP95914315A
Other languages
German (de)
English (en)
Inventor
Kurt Findeisen
Karl-Heinz Linker
Ernst Rudolf Gesing
Joachim Kluth
Klaus-Helmut Müller
Hans-Jochem Riebel
Klaus König
Hans-Joachim Santel
Markus Dollinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer AG
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 AG filed Critical Bayer AG
Publication of EP0754179A1 publication Critical patent/EP0754179A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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
    • 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
    • C07D249/14—Nitrogen atoms

Definitions

  • the invention relates to new substituted sulfonylaminocarbonyltriazolinones, several processes for their preparation and their use as herbicides.
  • Q represents oxygen, sulfur or the grouping -N (R 4 ) -
  • R 1 represents hydrogen, hydroxy, amino, alkylidene amino or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkylamino, cycloalkylamino, dialkylamino, alkanoylamino,
  • R 2 represents hydrogen, hydroxyl, mercapto, amino, halogen or an optionally substituted radical from the series alkyl, cycloalkyl, alkenyl, cyc loalkenyl, aralkyl, aryl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, aryloxy, aralkyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenylthio, alkynylthio, cycloalkylthio, arylthio, aralkylthio, alkylamino, alkenylamino, arylamino, arylamino, arylamino, arylamino, arylamino, arylamino, arylamino, arylamino, pino Morpholino stands
  • R 3 each represents at least doubly substituted aryl or arylalkyl, one of the substituents being different from alkyl,
  • R 4 represents hydrogen, hydroxy, amino, cyano, alkoxycarbonyl, each optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, aralkoxy, aryloxy or dialkoxy (thio) phosphoryl or the following
  • Grouping Q 1 -R 5 is where
  • Q 1 stands for -CO- or -SO 2 -
  • R 5 represents in each case optionally substituted alkyl, cycloalkyl or aryl, and salts of compounds of the formula (I) have been found.
  • the new sulfonylaminocarbonyltriazolinones of the formula (I) are obtained if
  • R 1 and R 2 have the meaning given above, with nucleophilic compounds of the general formula (III) R 3 -QH (III) in which Q and R 3 have the meaning given above, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or if (b) triazolinones of the general formula (IV)
  • R 3 have the meaning given above:
  • the new sulfonylaminocarbonyltriazolinones of the general formula (I) are notable for strong herbicidal activity.
  • the new compounds of the formula (I) have a considerably stronger herbicidal action than the structurally similar known 4,5-dimethyl-2- (2-chlorophenylsulfonylaminocarbonyl) -2,4-dihydro-3H-1,2,4 -triazol-3-one.
  • the invention preferably relates to compounds of the formula (I) in which
  • R 1 stands for hydrogen, hydroxy, amino, for C 2 -C 10 alkylidene amino, optionally for fluorine, chlorine, bromine, cyano, C 1 -C 4- alkoxy, C 1 -C 4 -alkylcarbonyl or C 1 -C 4 -alkoxy-carbonyl-substituted C 1 -C 6 -alkyl, for in each case optionally substituted by fluorine, chlorine and / or bromine or C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, optionally substituted by fluorine, chlorine, bromine and / or C 1 -C 4 - alkyl-substituted C 3 -C 6 -cycloalkyl which is optionally substituted by fluorine, chlorine,
  • R 4 for hydrogen, hydroxy, amino, cyano, for each optionally by halogen, cyano, carboxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 Alkylsulfonyl, C 1 -C 4 alkylamino, di (C 1 -C 6 alkyl) amino or C 1 -C 4 alkoxycarbonyl substituted C 1 -C 6 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl, for C 1 -C 4 alkoxycarbonyl, for C 1 -C 6 alkoxy, C 3 -C 6 alkenyloxy, benzyloxy, phenoxy or di- (C 1 -C 4 - alkoxy) - (thio) phosphoryl or the following group Q 1 -R 5 , where Q 1 is -CO- or -SO 2
  • R 5 is optionally substituted by halogen or C 1 -C 4 -alkoxy-substituted C 1 - C 6 alkyl, optionally substituted by halogen or C 1 -C 4 alkyl-substituted C 3 -C 6 cycloalkyl, or is optionally substituted by halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy substituted phenyl.
  • the invention further preferably relates to sodium, potassium, magnesium, calcium, ammonium, C 1 -C 4 alkyl ammonium, di (C 1 -C 4 alkyl) ammonium, tri ( C 1 -C 4 alkyl) ammonium, C 5 - or C 6 cycloalkyl ammonium and di (C 1 -C 2 alkyl) benzyl ammonium salts of compounds of the formula (I), in which Q, R 1 , R 2 and R 3 have the meanings preferably given above.
  • the invention relates in particular to compounds of the formula (I) in which
  • Q represents oxygen or the grouping
  • R 1 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, dichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, trifluoroethyl, trichloroethyl, chlorodifluoroethyl, tetrafluoroethyl, cyanomethyl, cyanoethyl, methoxymethyl , Ethoxymethyl, methoxyethyl, ethoxyethyl, for allyl, chlorallyl, dichlorallyl,
  • Methylsulfonyl, ethylsulfonyl, phenylthio or benzylthio for methylamino, ethylamino, n- or i-propylamino, phenylamino or benzylamino, for dimethylamino, diethylamino, dipropylamino, methylethylamino, methylpropylamino, for aziridino or for each optionally substituted by methyl or ethylpiper, p or methylidylino Morpholino stands
  • R 3 for in the 2- and in the 6-position (identical or different) by fluorine, chlorine, bromine, formyl, cyano, carboxy, nitro, by methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio, ethylthio , Methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl (which are each optionally substituted by fluorine, chlorine, Cyano, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl are substituted), by methylsulfonyloxy, ethylsulfonyloxy, methylaminosulfonyloxy, ethylaminosulfonyloxy, dimethylaminosulfonyloxy, diethylaminosulfonyloxy, trifluoromethylsul
  • Chlorine, methyl or ethyl are substituted) by phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonyloxy, phenylamino, phenylcarbonyl, phenylmethyl or phenylethyl (which are each optionally substituted by fluorine, chlorine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy , Difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, trifluoromethylthio, methoxycarbonyl or
  • ethoxycarbonyl are substituted by ethoxycarbonyl), by acetyl, propionyl, n- or i-butyroyl, cyclopropylcarbonyl, methoxycarbonyl or ethoxycarbonyl (which are optionally substituted by fluorine, chlorine, cyclopentyl, cyclohexyl, methoxy or ethoxy), substituted phenyl, phenylmethyl or phenylethyl, where one of the substituents is different from alkyl,
  • R 4 represents hydrogen, cyano, cyanomethyl, cyanoethyl, difluoromethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, allyl, propargyl, methoxycarbonyl, ethoxycarbonyl, methoxy, ethoxy or benzoxy or allyloxy or qoxy or allyloxy for allyloxy or allyloxy 1 -R 5 , wherein
  • Q 1 stands for -CO- or -SO 2 -
  • radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required for the production. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • hydrocarbon radicals mentioned in the radical definitions such as alkyl, alkenyl or alkynyl, also in combinations with heteroatoms, such as in alkoxy, alkylthio or alkylamino, are straight-chain or branched, even if this is not expressly stated.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine. If, for example, 2-chlorosulfonylaminocarbonyl-4-ethoxy-5-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one and 2-amino-3-fluoro-acetophenone are used as starting materials, then the The course of the reaction in process (a) according to the invention can be outlined using the following formula:
  • Formula (II) provides a general definition of the chlorosulfonylaminocarbonyltriazolinones to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I).
  • R 1 and R 2 preferably or in particular have those meanings which have already been mentioned 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 and R 2 .
  • R 1 and R 2 have the meaning given above, with chlorosulfonyl isocyanate, if appropriate in the presence of a diluent, such as methylene chloride, at temperatures between -20 ° C and + 50 ° C and worked up in a conventional manner (cf. the preparation examples) .
  • a diluent such as methylene chloride
  • Formula (III) provides a general definition of the nucleophilic compounds to be used as starting materials in processes (a) and (b) for the preparation of compounds of the formula (I).
  • Q and R-> preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for Q and R 3 .
  • the starting materials of formula (III) are known organic synthetic chemicals.
  • Formula (IV) provides a general definition of the triazolinones to be used as starting materials in processes (a) and (b) according to the invention for the preparation of compounds of the formula (I).
  • R 1 and R 2 preferably or in particular have those meanings which have already been mentioned 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 and R 2 .
  • the starting materials of the formula (IV) are known and / or can be prepared by processes known per se (cf. EP-A 283876, EP-A 294666, EP-A 301946, EP-A 298371, EP-A 341489, EP- A 399294, EP-A 398096, EP-A 422469, EP-A 425948, EP-A 431291, EP-A 477646, DE-OS 4110795).
  • Processes (a) and (b) according to the invention for the preparation of the new compounds of the formula (I) are preferably carried out using diluents.
  • diluents Practically all inert organic solvents can be used as diluents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and Dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl
  • Acid acceptors which can be used in processes (a) and (b) according to the invention are all acid binders which can usually be used for such reactions.
  • Alkali metal hydroxides such as sodium and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, alkali carbonates and alcoholates such as sodium and potassium carbonate, sodium and potassium tert-butoxide, are preferred.
  • basic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N, N-dimethylbenzylamine, N, N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl -, 2,4-dimethyl, 2,6-dimethyl, 2-ethyl, 4-ethyl and 5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo [4,3,0] non -5-ene (DBN), 1,8-diazabicyclo- [5,4,0] - undec-7-ene (DBU) and 1,4-diazabicyclo- [2,2,2] octane (DABCO).
  • DBN 1,5-diazabicyclo [4,3,0] non -5-ene
  • reaction temperatures can be varied within a substantial range in processes (a) and (b) according to the invention. In general, temperatures between -20 ° C and + 80 ° C, preferably at temperatures between -10 ° C and + 50 ° C.
  • Processes (a) and (b) according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use a larger excess of one of the components used in each case.
  • the reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the temperature required in each case.
  • Working up in processes (a) and (b) according to the invention is in each case carried out by customary methods (cf. the preparation examples).
  • salts can be prepared from the compounds of the general formula (I) according to the invention.
  • Such salts are obtained in a simple manner by customary salt formation methods, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base.
  • a suitable solvent e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene
  • the salts can then be isolated - if appropriate after prolonged stirring - by concentration or suction.
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Under Weeds in the broadest sense are to be understood as 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 e.g. can be used 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, rubber, oil palm, cocoa, berry fruit and hop plant genes, on ornamental and sports turf and pastures and for selective weed control in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon crops both in the pre-emergence and in the post-emergence process.
  • the active compounds (I) according to the invention also show interesting side effects, namely a leaf-insecticidal action and fungicidal actions, in particular against Pyricularia oryzae and against Erysiphe graminis.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie 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.
  • 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 Ge Stone powders such as highly disperse silica, aluminum oxide and silicates can be used as solid carriers for granules: e.g.
  • suitable 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.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • known herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil; Aryl carboxylic acids such as dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofopethyl; Azinones such as chloridazon and norflurazon; Carbamates, such as chlorine propham, Desmedipham, Phenmedipham and Prop
  • 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 2 kg per ha.
  • the preparation and use of the active ingredients according to the invention can be seen from the examples below.
  • the mixture is stirred until the solid components dissolve, the organic phase is separated off, dried with sodium sulfate and filtered.
  • the filtrate is concentrated in a water jet vacuum, the residue is crystallized by digesting with ligroin and the product is isolated by suction.
  • 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 active ingredient preparation is poured onto the floor. 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% damage compared to the development of the untreated control. It means:
  • 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 2000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

L'invention concerne de nouvelles sulfonylaminocarbonyltriazolinones de la formule (I) dans laquelle Q désigne oxygène, soufre ou le groupement -N(R4)-, R3 désigne aryle ou arylalkyle substitué au moins deux fois, un des substituants étant différent d'alkyle, et R?1, R2 et R4¿ désignent hydrogène ou différents substituants. L'invention concerne également des sels des composés de la formule (I), des procédés permettant de préparer les nouveaux composés et leur utilisation comme herbicides.
EP95914315A 1994-04-07 1995-03-27 Sulfonylaminocarbonyltriazolinones substituees et leur utilisation comme herbicides Withdrawn EP0754179A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4411913 1994-04-07
DE4411913A DE4411913A1 (de) 1994-04-07 1994-04-07 Substituierte Sulfonylaminocarbonyltriazolinone
PCT/EP1995/001149 WO1995027703A1 (fr) 1994-04-07 1995-03-27 Sulfonylaminocarbonyltriazolinones substituees et leur utilisation comme herbicides

Publications (1)

Publication Number Publication Date
EP0754179A1 true EP0754179A1 (fr) 1997-01-22

Family

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EP95914315A Withdrawn EP0754179A1 (fr) 1994-04-07 1995-03-27 Sulfonylaminocarbonyltriazolinones substituees et leur utilisation comme herbicides

Country Status (10)

Country Link
US (1) US5861358A (fr)
EP (1) EP0754179A1 (fr)
JP (1) JPH09511510A (fr)
CN (1) CN1145068A (fr)
AU (1) AU2136595A (fr)
BR (1) BR9507294A (fr)
CA (1) CA2187215A1 (fr)
DE (1) DE4411913A1 (fr)
HU (1) HUT76496A (fr)
WO (1) WO1995027703A1 (fr)

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DE19525162A1 (de) 1995-07-11 1997-01-16 Bayer Ag Sulfonylamino(thio)carbonylverbindungen
DE19615900A1 (de) * 1996-04-22 1997-10-23 Bayer Ag Substituierte Sulfonylamino(thio)carbonyl-triazolin(thi)one
ZA974703B (en) 1996-05-30 1997-12-30 Bayer Ag Substituted sulfonylamino(thio)carbonyl compounds.
DE19843766A1 (de) * 1998-09-24 2000-03-30 Bayer Ag Substituierte Thiazol(in)ylidenaminosulfonylamino(thio)carbonyl-triazolinone
ME01498B (me) * 2004-11-18 2014-04-20 Synta Pharmaceuticals Corp Jedinjenja triazola koja modulišu aktivnost hsp90
EP1717228A1 (fr) * 2005-04-28 2006-11-02 Bayer CropScience GmbH Dérivés de sulfonylamino(thio)carbonyl comme herbicides et regulateurs de la croissance végétale
WO2007094819A2 (fr) 2005-08-18 2007-08-23 Synta Pharmaceuticals Corp. Dérivés de triazole modulant l'activité de hsp90
CA2653327A1 (fr) * 2006-05-25 2007-12-06 Synta Pharmaceuticals Corp. Composes modulant l'activite de hsp90 et methodes d'identification de ces composes
US9205086B2 (en) 2010-04-19 2015-12-08 Synta Pharmaceuticals Corp. Cancer therapy using a combination of a Hsp90 inhibitory compounds and a EGFR inhibitor
WO2013067165A1 (fr) 2011-11-02 2013-05-10 Synta Pharmaceuticals Corp. Polythérapie d'inhibiteurs de hsp 90 avec des agents contenant du platine
AU2012332421A1 (en) 2011-11-02 2014-06-05 Synta Pharmaceuticals Corp. Cancer therapy using a combination of Hsp90 inhibitors with topoisomerase I inhibitors
WO2013074594A1 (fr) 2011-11-14 2013-05-23 Synta Pharmaceuticals Corp. Association thérapeutique d'inhibiteurs de hsp90 et d'inhibiteurs de braf

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Publication number Priority date Publication date Assignee Title
DE3934081A1 (de) * 1989-10-12 1991-04-18 Bayer Ag Sulfonylaminocarbonyltriazolinone
US5057144A (en) * 1988-05-09 1991-10-15 Bayer Aktiengesellschaft Sulphonylaminocarbonyltriazolinones
DE4217719A1 (de) * 1992-05-29 1993-12-02 Bayer Ag Zweifach heterocyclisch substituierte Sulfonylamino(thio)carbonylverbindungen
DE4234801A1 (de) * 1992-10-15 1994-04-21 Bayer Ag Sulfonylaminocarbonyltriazolinone

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9527703A1 *

Also Published As

Publication number Publication date
WO1995027703A1 (fr) 1995-10-19
CA2187215A1 (fr) 1995-10-19
BR9507294A (pt) 1997-10-07
US5861358A (en) 1999-01-19
CN1145068A (zh) 1997-03-12
DE4411913A1 (de) 1995-10-12
HUT76496A (en) 1997-09-29
JPH09511510A (ja) 1997-11-18
HU9602749D0 (en) 1996-11-28
AU2136595A (en) 1995-10-30

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