WO1997040026A1 - Sulfonylamino(thio) carbonyltriazolin(thi)ones substituees et leur utilisation comme herbicides - Google Patents

Sulfonylamino(thio) carbonyltriazolin(thi)ones substituees et leur utilisation comme herbicides Download PDF

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Publication number
WO1997040026A1
WO1997040026A1 PCT/EP1997/001751 EP9701751W WO9740026A1 WO 1997040026 A1 WO1997040026 A1 WO 1997040026A1 EP 9701751 W EP9701751 W EP 9701751W WO 9740026 A1 WO9740026 A1 WO 9740026A1
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Prior art keywords
alkyl
optionally substituted
chlorine
fluorine
alkoxy
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PCT/EP1997/001751
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German (de)
English (en)
Inventor
Karl-Heinz Linker
Kurt Findeisen
Mark Wilhelm Drewes
Ernst Rudolf F. Gesing
Johannes Rudolf Jansen
Rolf Kirsten
Joachim Kluth
Klaus König
Klaus-Helmut Müller
Ulrich Philipp
Hans-Jochem Riebel
Otto Schallner
Markus Dollinger
Hans-Joachim Santel
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Bayer Aktiengesellschaft
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Priority to AU25691/97A priority Critical patent/AU2569197A/en
Publication of WO1997040026A1 publication Critical patent/WO1997040026A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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

Definitions

  • the invention relates to new substituted sulfonylamino (thio) carbonyl-triazoline (thi) - one, processes for their preparation and their use as herbicides.
  • A stands for oxygen, sulfur or the grouping -N- (A ') -, in which A 1 stands for hydrogen, hydroxy, amino, cyano, alkoxycarbonyl, for optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, arylalkoxy, Aryloxy or the grouping -A 2 -A 3 , where A 2 is -CO- or -SO 2 - and A 3 is in each case optionally substituted alkyl, cycloalkyl or aryl,
  • Q 1 and Q 2 are the same or different and represent oxygen or sulfur
  • Q 3 and Q 4 are the same or different and represent O, S, SO or SO 2 ,
  • R 1 represents hydrogen, hydroxyl, amino, alkylidene amino or, in each case optionally substituted alkyl, alkoxy, alkylamino, dialkylamino, Alkanoylamino, alkenyl, alkenyloxy, alkynyl, cycloalkyl, cycloalkyl ⁇ amino, aryl or arylalkyl,
  • R 2 represents hydrogen, hydroxyl, mercapto, amino, halogen or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkenyl, alkenyloxy, alkenylthio,
  • R 3 represents hydrogen, halogen or optionally substituted in each case
  • R 4 represents hydrogen or represents optionally substituted alkyl or cycloalkyl
  • R 5 represents optionally substituted alkyl
  • R 6 represents optionally substituted alkyl or together with R 5 represents alkanediyl
  • chlorosulfonyl iso (thio) cyanate if appropriate in the presence of a diluent, and the chlorosulfonylamino (thio) carbonyl-triazoline (thi) ones of the formula (II) formed above are substituted with intermediate isolation without intermediate isolation
  • the new substituted sulfonylamino (thio) carbonyl-triazolin (thi) ones of the general formula (I) are notable for strong and selective herbicidal activity.
  • the invention preferably relates to compounds of the formula (I) in which
  • A stands for oxygen or the grouping -N ⁇ A 1 ) -, wherein A 1 stands for
  • Alkenyloxy stands for benzyloxy, phenoxy or the group -A 2 -A 3 , in which A 2 stands for -CO- or -SO 2 - and A 3 for C, -C optionally substituted by halogen or C, -C 4 alkoxy 6 alkyl, optionally substituted by halogen or C, -C 4 alkyl C 3 -C 6 cycloalkyl, or is optionally substituted by halogen, C 1 -C 4 alkyl or C] -C 4 alkoxy phenyl sub ⁇ stitutechnischs ,
  • Q 1 and Q 2 are the same or different and represent oxygen or sulfur
  • Q 3 and Q 4 are the same or different and represent O, S, SO or SO 2 ,
  • R 1 for hydrogen, hydroxy, amino, for C 2 -C 10 -alkyl idenamino, for each optionally by fluorine, chlorine, bromine, cyano, C 1 -C 4 -alkoxy, C ] -C 4 -
  • R 2 for hydrogen, hydroxy, mercapto, amino, fluorine, chlorine, bromine, iodine, for each optionally by fluorine, chlorine, bromine, cyano, C r C 4 alkoxy, C r C 4 alkylthio, C r C 4 - Alkylsulfinyl, C r C 4 -alkylsulfonyl, C r C 4 -alkylcarbonyl, CC 4 -alkoxy-carbonyI or C 3 -C 6 -cycloalkyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or
  • Dialkylamino each with 1 to 6 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylthio or alkenylamino, each optionally substituted by fluorine, chlorine and / or bromine, each with 2 to 6 carbon atoms in the alkenyl groups, for alkynyl, alkynyloxy or alkynylthio, each with 2 to 6 carbon atoms in the alkinyl groups, represents in each case optionally fluorine, chlorine, bromine, cyano and / or C r C 4 alkyl substituted cycloalkyl, cycloalkenyl, cycloalkyloxy, Cyclo ⁇ alkylthio having in each case 3 to 6 carbon atoms in the cycloalkyl or cycloalkenyl groups, represents in each case optionally fluorine-, chlorine, bromine, cyano, nitro, C r C 4 alkyl, trifluoromethyl, C,
  • R 3 for hydrogen, fluorine, chlorine, bromine, or for each optionally by
  • R 4 for hydrogen, optionally substituted by fluorine, chlorine, C r C 4 -alkoxy, C, - C 4 -alkylthio, C r C 4 -alkylsulfinyl or C r C 4 -alkylsulfonyI
  • R 5 represents optionally substituted by fluorine, chlorine or C, -C 4 alkoxy alkyl having 1 to 6 carbon atoms and
  • R 6 represents optionally substituted by fluorine, chlorine or C ] -C 4 alkoxy alkyl having 1 to 6 carbon atoms or together with R 5 represents alkanediyl having 2 to 5 carbon atoms.
  • the invention sium- more preferably sodium, potassium, Magne ⁇ , calcium, ammonium, alkyl-ammonium, 4 C, -C, di- (C r C 4 alkyl) -ammo- nium-, Tri (C 1 -C 4 alkyl) ammonium, tetra (C 1 -C 4 alkyl) ammonium, tri (C r C 4 alkyl) sulfonium, C 5 or C 6 -Cycloalkyl-ammonium and di- (C r C 2 -alkyl) - benzyl-ammonium salts of compounds of the formula (I) in which A, Q 1 , Q 2 , Q 3 , Q 4 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the meaning preferably given above.
  • 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.
  • the invention relates in particular to compounds of the formula (I) in which
  • A represents an NH group
  • Q 1 and Q 2 are the same or different and represent oxygen or sulfur
  • Q 3 and Q 4 are the same or different and represent O, S, SO or SO 2 ,
  • R 1 is in each case optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, n- or i-propyl amino, dimethylamino or diethylamino, each optionally with fluorine,
  • Chlorine and / or bromine substituted propenyl or propenyloxy, for Propinyl represents in each case optionally substituted by fluorine, chlorine, bromine, cyano or methyl cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or represents in each case optionally substituted by fluorine, chlorine, bromine, cyano, methyl or methoxy, phenyl or benzyl,
  • R 2 for chlorine or bromine, each optionally by fluorine, chlorine, bromine,
  • R 3 for hydrogen, fluorine, chlorine, bromine, or for each optionally by
  • R 4 represents hydrogen, methyl, ethyl, n- or i-propyl optionally substituted by fluorine and / or chlorine or cyclopropyl
  • R 5 represents methyl, ethyl, n- or i-propyl optionally substituted by fluorine and / or chlorine and
  • R 6 stands for methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine or together with R 5 stands for ethane-1,2-diyl (dimethylene) or propane-1,3-diyl (trimethylene ) stands.
  • the chlorosulfonylamino (thio) carbonyltriazoline (th ⁇ ) one to be used as starting materials in the process (a) according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (II).
  • Q, Q , R and R preferably or in particular 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 being particularly preferred for Q 1 , Q 2 , R 1 and R 2 were
  • the starting materials of the formula (II) are known and / or can be prepared by processes known per se (cf. WO 94/08979, WO 95/27703)
  • the substituted arenes to be used as starting materials in processes (a) and (b) according to the invention are generally defined by the formula (III).
  • A, Q 3 , Q 4 , R 3 , R 4 , R 5 and R 6 preferably or in particular 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 A, Q 3 , Q 4 , R 3 , R 4 , R 5 and R 6 were given
  • T ⁇ azohn (thi) ones to be used as starting materials in process (b) according to the invention for the preparation of compounds of the formula (I) are characterized by Formula (IV) generally defined.
  • Q 1 , R 1 and R 2 preferably or in particular have those meanings which are preferred or particularly preferred for Q already in connection with the description of the compounds of the formula (I) according to the invention 1 , R 1 and R 2 were specified.
  • the starting materials of the formula (IV) are known and / or can be prepared by processes known per se (cf. EP 283876; EP 294666; EP 298371; EP 301946; EP 341489; EP 399294; EP 398096; EP 422469; EP 425948; EP 431291; EP 477646; DE 4110795).
  • Inert organic solvents are suitable as diluents for carrying out processes (a) and (b) according to the invention.
  • These include, in particular, aliphatic, alicyclic 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 diethyl ether Tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides, such as
  • Processes (a) and (b) according to the invention for the preparation of the compounds of the formula (I) are preferably carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor The usual inorganic or organic bases are generally suitable as acid acceptors. These preferably include
  • Alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates such as 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,
  • reaction temperatures can be varied within a substantial range when carrying out processes (a) and (b) according to the invention. In general, temperatures between -20 ° C and + 100 ° C, preferably between 0 ° C and 80 ° C.
  • Processes (a) and (b) according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).
  • 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, such as e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base.
  • a suitable solvent such as 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. Weeds in the broadest sense are understood to mean all plants that are in places grow up 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
  • Trifolium Ranunculus, Taraxacum.
  • 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 pasture land and for selective purposes
  • 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 method. They show strong herbicidal activity and a broad spectrum of activity when applied to the soil and above-ground parts of plants.
  • 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 poly - other fabrics
  • 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, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents
  • organic solvents can also be used as auxiliary solvents.
  • Liquid solvents are essentially suitable.
  • 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.
  • Solid carrier materials that come into question are: for example ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granules Question.
  • natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granules Question.
  • Eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam-
  • Eg nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, eg alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates, are suitable as dispersants. eg lignin sulfite liquor and methyl cellulose.
  • 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 phospholipids such as cephalins and lecithins and synthetic phospholipids, and other additives can be mineral and vegetable Be Ole
  • Dyes such as inorganic pigments, for example 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 for combating weeds, finished formulations or tank mixes being possible.
  • herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil, arylcarboxylic acids, such as, for example, Dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, e.g.
  • ureas such as chlorotoluron, diuron, fiuometuron,
  • Cinosulfuron Metsulfuron-methyl, Nicosulfuron, Primisulfuron, Pyrazosulfuron-ethyl, Thifensulfuron-methyl, Triasulfuron and Tribenuron-methyl, Thiolcarbamate, such as Butylate, Cycloate, Diallate, EPTC, Esprocarb, Molinate, Prosulfocarbine, Thi e.g. atrazin, cyanazin, simazin, Simetryne, terbutryne and terbutylazin, triazinones, such as hexazinone,
  • Metamitron and metribuzin others, e.g. Aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.
  • Aminotriazole Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.
  • Insecticides Insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure are 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 customary manner, for example by pouring, spraying or spraying , Scatter
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing
  • the amount of active ingredient used can vary within a substantial 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
  • Solvent 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • Seeds of the test plants are sown in normal soil. After approx.
  • the compounds according to Preparation 1 and 2 show very good tolerance to crop plants, such as Wheat, very strong against weeds; the compounds according to preparation examples 68 and 75 also show strong activity against weeds
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants which have a height of 5-15 cm are sprayed with the active substance preparation, so 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 1,000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • the compounds according to Preparation 1 and 2 with very good tolerance to crop plants, such as, for example, wheat, show very strong activity against weeds; the compounds according to preparation examples 68 and 75 also show strong activity against weeds.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (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)

Abstract

L'invention concerne de nouvelles sulfonylamino(thio) carbonyltriazolin(thi)ones substituées de formule (I) dans laquelle A est oxygène, soufre ou le groupement -N-(A1)- (où A1 est hydrogène, hydroxy, amino, cyano, alkoxycarbonyle), alkyle, alcényle, alcynyle, alcoxy, alcényloxy, arylalcoxy, aryloxy dans chaque cas éventuellement substitué ou bien le groupement -A?2-A3 où A2¿ est -CO- ou -SO¿2?- et A?3¿ est alkyle, cycloalkyle ou aryle dans chaque cas éventuellement substitué; Q1 et Q2 sont identiques ou différents et désignent oxygène ou SO¿2?; Q?3 et Q4¿ sont identiques ou différents et désignent O, S, SO, ou bien SO¿2; R?1 est hydrogène, hydroxy, amino, alkylidène amino ou bien alkyle, alcoxy, alkylamino, dialkylamino, alcanoylamino, alcényle, alcényloxy, alcinyle, cycloalkyle, cycloalkylamino, aryle ou arylalkyle dans chaque cas éventuellement substitué; R2 est hydrogène, hydroxy, mercapto, amino, halogène, ou bien alkyle, alcoxy, alkylthio, alkylsulfinyle, alkylsulfonyle, alkylamino, dialkylamino, alcényle, alcényloxy, alcénylthio, alcénylamino, alcinyle, alcinyloxy, alcinylthio, cycloalkyle, cycloalcényle, cycloalcoxy, cycloalkylthio, aryle, aryloxy, arylthio, arylamino, arylalkyle, arylalcoxy, alylalkylthio, arylalkylamino, aziridino, pyrrolino, piperidino ou morpholino dans chaque cas éventuellement substitué; R3 est hydrogène, halogène ou bien alkyle, alcoxy, alkylthio, alkylsulfinyle, alkylsulfonyle ou alcoxycarbonyle dans chaque cas éventuellement substitué; R4 est hydrogène ou bien alkyle ou cycloalkyle dans chaque cas éventuellement substitué; R5 est alkyle éventuellement substitué, et R6 est alkyle éventuellement substitué ou bien, conjointement avec R5, alcandiyle. L'invention concerne également des sels des composés de la formule (I), des procédés pour préparer ces nouveaux composés et leur utilisation comme herbicides.
PCT/EP1997/001751 1996-04-22 1997-04-09 Sulfonylamino(thio) carbonyltriazolin(thi)ones substituees et leur utilisation comme herbicides WO1997040026A1 (fr)

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AU25691/97A AU2569197A (en) 1996-04-22 1997-04-09 Substituted sulfonylamino(thio)carbonyltriazolin(thi)ones and their use as herbicides

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DE1996115900 DE19615900A1 (de) 1996-04-22 1996-04-22 Substituierte Sulfonylamino(thio)carbonyl-triazolin(thi)one
DE19615900.8 1996-04-22

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EP1717228A1 (fr) 2005-04-28 2006-11-02 Bayer CropScience GmbH Dérivés de sulfonylamino(thio)carbonyl comme herbicides et regulateurs de la croissance végétale

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4234801A1 (de) * 1992-10-15 1994-04-21 Bayer Ag Sulfonylaminocarbonyltriazolinone
DE4411913A1 (de) * 1994-04-07 1995-10-12 Bayer Ag Substituierte Sulfonylaminocarbonyltriazolinone
DE4435470A1 (de) * 1994-10-04 1996-04-11 Bayer Ag Substituierte Phenylaminosulfonylharnstoffe

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4234801A1 (de) * 1992-10-15 1994-04-21 Bayer Ag Sulfonylaminocarbonyltriazolinone
WO1994008979A1 (fr) * 1992-10-15 1994-04-28 Bayer Aktiengesellschaft Sulfonylaminocarbonyltrazolinones utilisees comme herbicides
DE4411913A1 (de) * 1994-04-07 1995-10-12 Bayer Ag Substituierte Sulfonylaminocarbonyltriazolinone
WO1995027703A1 (fr) * 1994-04-07 1995-10-19 Bayer Aktiengesellschaft Sulfonylaminocarbonyltriazolinones substituees et leur utilisation comme herbicides
DE4435470A1 (de) * 1994-10-04 1996-04-11 Bayer Ag Substituierte Phenylaminosulfonylharnstoffe

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DE19615900A1 (de) 1997-10-23
AU2569197A (en) 1997-11-12

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