WO1997003980A1 - Arylsulfonylamino(thio)carbonyltriazolin(thi)ones substituees - Google Patents

Arylsulfonylamino(thio)carbonyltriazolin(thi)ones substituees Download PDF

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Publication number
WO1997003980A1
WO1997003980A1 PCT/EP1996/002932 EP9602932W WO9703980A1 WO 1997003980 A1 WO1997003980 A1 WO 1997003980A1 EP 9602932 W EP9602932 W EP 9602932W WO 9703980 A1 WO9703980 A1 WO 9703980A1
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WIPO (PCT)
Prior art keywords
alkyl
chlorine
fluorine
alkoxy
substituted
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PCT/EP1996/002932
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German (de)
English (en)
Inventor
Klaus-Helmut Müller
Rolf Kirsten
Joachim Kluth
Ernst Rudolf F. Gesing
Kurt Findeisen
Johannes Rudolf Jansen
Klaus König
Mark Wilhelm Drewes
Hans-Jochem Riebel
Markus Dollinger
Hans-Joachim Santel
Original Assignee
Bayer Aktiengesellschaft
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Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU65188/96A priority Critical patent/AU6518896A/en
Priority to JP9506228A priority patent/JPH11509219A/ja
Priority to EP96924877A priority patent/EP0840734A1/fr
Publication of WO1997003980A1 publication Critical patent/WO1997003980A1/fr

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Classifications

    • 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to new substituted arylsulfonylamino (thio) carbonyltriazolin (thi) one, several processes for their preparation and their use as
  • Ar represents optionally substituted arylene or heteroarylene
  • Q 1 represents oxygen or sulfur
  • Q 2 represents oxygen or sulfur
  • R 1 represents hydrogen, hydroxy, amino, alkylidene amino or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl,
  • R 2 is hydrogen, hydroxyl, mercapto, amino, halogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, alkenylamino, alkynylamino, dialkylamino, alkanoylamino, Aziridino, Pyrrolidino, Piperidino, Morpholino, Cycloalkyl, Cyclo alkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio, Cycloalkylalkylamino, aryl, aryloxy, arylthio, arylamino, arylalkyl, aryl
  • R 3 represents optionally substituted heterocyclyl, and salts of the compounds of the formula (I) have been found.
  • Q 1 , Q 2 , R 1 and R 2 have the meanings given above and Z represents halogen, alkoxy, aryloxy or arylalkoxy, with sulfonamides of the general formula (V)
  • Ar and R 3 have the meanings given above, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or if
  • Z represents halogen, alkoxy, aryloxy or arylalkoxy, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or if (d) triazolin (thi) ones of the general formula (II)
  • Q 1 , R 1 and R 2 have the meanings given above, with substituted arylsulfonic acid halides of the general formula (VII) R 3 -O-CO-Ar-SO 2 -X (VII) in which Ar and R 3 have the meanings indicated above and X represents halogen, and metal (thio) cyanates of the general formula (VIII)
  • M represents an alkali metal or an alkaline earth metal equivalent, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and if appropriate the compounds of the formula (I) obtained by processes (a), (b), (c) or (d) ) converted into salts by conventional methods.
  • the new sulfonylamino (thio) carbonyl-triazolin (thi) ones of the general formula (I) are notable for their strong herbicidal activity.
  • Subject of the invention are preferably compounds of formula (I) in which Ar is optionally substituted by halogen, cyano, nitro, C 1 -C 4 - alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfionyl, C 1 -C 4 alkyl sulfonyl, di (C 1 -C 4 alkyl) amino sulfonyl or NC 1 -C 4 alkoxy-NC 1 -C 4 alkyl- aminosulfonyl (which are each optionally substituted by fluorine and / or chlorine) substituted phenylene or naphthylene, or for optionally by halogen, cyano, nitro, by C 1 -C 4 -alkyl or C 1 - C 4 -alkoxy (which in each case optionally substituted by fluorine and / or chlorine) substituted heteroarylene having 5 or 6 ring members, at least
  • R 1 for hydrogen, hydroxy, amino, for C 2 -C 10 alkylidene amino, for optionally by 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 each optionally substituted by fluorine, chlorine and / or bromine substituted C 2 - C 6 alkenyl or C 2 -C 6 alkynyl, each optionally substituted by fluorine, chlorine, cyano , C 1 -C 4 alkoxy or C 1 -C 4 alkoxy-carbonyl substituted C 1 -C 6 alkoxy, C 1 -C 8 alkylamino or C 1 -C 6 alkanoylamino, for C 3 -C 6 - Alkenyloxy, for di (C 1 -C 4 alkyl) amino, for C 3 -C 6 cycloal
  • R 2 for hydrogen, hydroxy, mercapto, amino, fluorine, chlorine, bromine, iodine, for optionally by fluorine, chlorine, bromine, cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkyl carbonyl or C 1 -C 4 -alkoxy-carbonyl-substituted C 1 -C 6 -alkyl, represents in each case optionally substituted by fluorine, chlorine and / or bromine, C 2 - C 6 alkenyl or C 2 -C 6 -alkynyl, represents in each case optionally fluorine-, Chlorine, cyano, C 1 -C 4 alkoxy or C 1 -C 4 alkoxy-carbonyl substituted C 1 - C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino or C 1 -C 6 alkanoylamino, C 2 -C 6 alkenyloxy, C
  • R 1 and R 2 together represent optionally branched alkanediyl having 3 to 11 carbon atoms
  • R 3 represents oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl or tetrahydrothienyl, each optionally substituted by halogen or C 1 -C 4 alkyl.
  • 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, tetra (C 1 -C 4 alkyl) ammonium, tri (C 1 -C 4 alkyl) sulfonium, 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 Ar, Q 1 , Q 2 , R 1 , R 2 and R 3 preferably do the above have the meanings given.
  • the invention relates in particular to compounds of the formula (I) in which
  • Q 1 represents oxygen or sulfur
  • Q 2 represents oxygen or sulfur
  • R 1 for hydrogen, hydroxy, amino, for C 3 -C 8 -alkylideneamino, for methyl, ethyl, n- or i-propyl, n-, i-, s, which are each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy - or t-butyl, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine, chlorine or bromine, for methoxy, ethoxy, n- each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, for propenyloxy or butenyl
  • s- or t-butyl for propenyl, butenyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or bromine, for methoxy, ethoxy, n- or i-propoxy, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy , n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, for propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, butenynylthio, propyny
  • R 3 represents oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl or tetrahydrothienyl, each optionally substituted by fluorine, chlorine, methyl or ethyl.
  • a very particularly preferred group of compounds of the formula (I) are the compounds of the formula (Ia)
  • 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 the preparation. These radical definitions can be combined with one another as desired, that is to say also between the specified ranges of preferred compounds.
  • Formula (II) provides a general definition of the triazolin (thi) ones to be used as starting materials in processes (a), (c) and (d) for the preparation of compounds of the formula (I).
  • Q 1 , 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 Q 1 , R 1 and R 2 have been given.
  • triazolin (thi) ones of the general formula (II) are known and / or can be prepared by processes known per se (cf. Arch. Pharm. 301 (1968), 827; loc. Cit. 307 (1974), 889; Bull. Soc. Chim. France 1962, 1365; loc. Cit. 1975, 1191; Chem. Ber. 90 (1957), 909-921; loc. Cit. 98 (1965), 3025-3099; loc. Cit. 102 (1969), 755; J. Heterocycl. Chem. 15 (1978), 237-240; J. Indian
  • Formula (III) provides a general definition of the substituted arylsulfonyliso (thio) cyanates to be used in the process (a) according to the invention for the preparation of compounds of the formula (I) as starting materials.
  • Ar, Q 2 and R 3 preferably or in particular have the meaning 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 Ar, Q 2 and R. 3 was specified.
  • Q 1 , Q 2 , 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) as preferred or as particularly preferred for Q 1 , Q 2 , R 1 and R 2 have been given;
  • Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy, phenoxy, halogen or nitro-phenoxy, in particular methoxy, phenoxy or 4-nitro-phenoxy.
  • Z 1 represents halogen, alkoxy, aralkoxy or aryloxy (and has the same preferred meanings as Z), optionally in the presence of an acid acceptor, such as sodium or potassium hydroxide, sodium or potassium t-butoxide, and optionally in the presence a diluent, such as methylene chloride, tetrahydrofuran or dimethoxyethane and / or water, at temperatures between 0 ° C and 100 ° C.
  • an acid acceptor such as sodium or potassium hydroxide, sodium or potassium t-butoxide
  • a diluent such as methylene chloride, tetrahydrofuran or dimethoxyethane and / or water
  • Formula (V) provides a general definition of the sulfonamides to be used as starting materials in process (b) according to the invention for the preparation of the compounds of the general formula (I).
  • Ar and R preferably or in particular have the meaning which has already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for Ar and R 3 .
  • the starting materials of the formula (V) are known and / or can be prepared by processes known per se (cf. EP-A 496701, EP-A 558445).
  • Formula (VI) provides a general definition of the substituted arylsulfonic acid amide derivatives to be used as starting materials in process (c) according to the invention for the preparation of the compounds of the formula (I).
  • Ar, Q 2 and R 3 preferably or in particular have the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for Ar, Q 2 and R. 3 was specified;
  • Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy,
  • Formula (VII) provides a general definition of the substituted arylsulfonic acid halides to be used as starting materials in process (d) according to the invention for the preparation of the compounds of the formula (I).
  • Ar and R 3 preferably or in particular have the meaning which has already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for Ar and R;
  • X preferably represents fluorine, chlorine or bromine, especially chlorine.
  • the starting materials of the formula (VII) are known and / or can be prepared by processes known per se (cf. EP-A 496701, EP-A 558445).
  • diluents are preferably carried out using 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 and methyl isobutyl ketone; Esters such as methyl acetate and ethyl acetate; Nitriles such as Acetonitrile and propionitrile; Amides such as Dimethylformamide, dimethylacetamide and N-methylpyrrolidone, as well as dimethyl sulfoxide, tetramethyl ensulfone and hexamethylphosphoric acid triamide.
  • Ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether
  • reaction auxiliaries or as acid acceptors in the processes (a), (b), (c) and (d) according to the invention it is possible to use all acid binders which can customarily 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, and also basic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, are preferably used.
  • DBN 1,5-diazabicyclo [4,3,0] non-5-ene
  • DBU 1,8-diazabicyclo [5,4,0] -undec-7-ene
  • DBUCO 1,4-diazabicy
  • reaction temperatures can be varied within a wide range in processes (a), (b), (c) and (d). In general, temperatures between -20 ° C and + 150 ° C, preferably at
  • Processes (a), (b), (c) and (d) according to the invention are generally carried out under atmospheric 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 becomes several
  • salts can be prepared from the compounds of the general formula (I) according to the invention. Such salts are obtained in a simpler manner
  • salt formation methods for example by dissolving or dispersing a compound of 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. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the one used
  • the active compounds according to the invention can be used, for example, in the following plants:
  • Brassica, lactuca, cucumis, cucurbita Brassica, lactuca, cucumis, cucurbita.
  • Alopecurus apera.
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops e.g. Forest, ornamental trees, fruit, wine,
  • Citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants are used on ornamental and sports turf and pasture land 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 monocotyledonous and dicotyledonous weeds in mono cotyledon and dicotyledon cultures both in the pre-emergence and post-emergence processes.
  • 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.
  • 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 are possible: e.g.
  • suitable emulsifying 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 ether, 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.
  • herbicides for example anilides, such as e.g. Diflufenican and Propanil; Aryl carboxylic acids, e.g. Dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, e.g. 2,4-D,
  • Aryloxy-phenoxyalkanoic acid esters e.g. Diclofop-m ethyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl;
  • Azinones e.g. Chloridazon and norflurazon;
  • Carbamates e.g. Chlorpropham, desmedipham, phenmedipham and propham;
  • Chloroacetanilides e.g.
  • Sethoxydim and tralkoxydim; Imidazolinones such as. Imazethapyr, imazamethabenz, imazapyr and imazaquin; Nitriles, such as bromoxynil, Dichlobenil and ioxynil; Oxyacetamides such as mefenacet; Sulfonylureas such as amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primi sulfuron, pyrazosulfuronethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates, such as butylates, cycloates, dialates, EPTC, Esprocarb, Molinate, prosulfocarb,
  • Triazines e.g. Atrazin, cyanazin, simazin, simetryne, terbutryne and terbutylazin
  • Triazinones e.g. Hexazinone, metamitron and metribuzin
  • Others such as Aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.
  • 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 10 g and 10 kg of active ingredient per hectare of soil, preferably between 50 g and 5 kg per ha.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration. Seeds of the test plants are sown in normal soil. After about 24 hours, the 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%
  • Example B Effect against weeds (see Table A).
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, mix 1
  • 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 1000 l of water / ha.

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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)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne de nouvelles arylsulfonylamino(thio)carbonyltriazolin(thi)ones substituées de la formule (I) où Ar représente arylène ou hétéro-arylène éventuellement substitués ; Q1 représente oxygène ou soufre ; Q2 représente oxygène ou soufre ; R1 représente hydrogène, hydroxy, amino, alkylidénamino ou un reste éventuellement substitué de la série alkyle, alcényle, alcynyle, alcoxy, alcényloxy, alkylamino, dialkylamino, alcanoylamino, cycloalkyle, cycloalkylalkyle, aryle, arylalkyle ; R2 représente hydrogène, hydroxy, mercapto, amino, halogène ou un reste éventuellement substitué de la série alkyle, alcényle, alcynyle, alkoxy, alcényloxy, alcynyloxy, alkylthio, alcénylthio, alcynylthio, alkylamino, alcénylamino, alcynylamino, dialkylamino, alcanoylamino, aziridino, pyrrolidino, pipéridino, morpholino, cycloalkyle, cycloalcényle, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyle, cycloalkylalcoxy, cycloalkylalkylthio, cycloalkylalkylamino, aryle, aryloxy, arylthio, arylamino, arylalkyle, arylalcoxy, arylalkylthio, arylalkylamino, hétérocyclyloxy, hétérocyclylthio ou bien R1 et R2 représentent conjointement alcandiyle éventuellement ramifié et R3 représente hétérocyclyle éventuellement substitué. L'invention concerne également les sels des composés de la formule (I), le procédé de production des nouveaux composés et leur utilisation comme herbicides.
PCT/EP1996/002932 1995-07-17 1996-07-04 Arylsulfonylamino(thio)carbonyltriazolin(thi)ones substituees WO1997003980A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU65188/96A AU6518896A (en) 1995-07-17 1996-07-04 Substituted aryl sulphonyl amino (thio) carbonyl triazolin(thi)ones
JP9506228A JPH11509219A (ja) 1995-07-17 1996-07-04 置換されたアリールスルホニルアミノ（チオ）カルボニルトリアゾリン（チ）オン
EP96924877A EP0840734A1 (fr) 1995-07-17 1996-07-04 Arylsulfonylamino(thio)carbonyltriazolin(thi)ones substituees

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19525974.2 1995-07-17
DE1995125974 DE19525974A1 (de) 1995-07-17 1995-07-17 Substituierte Arylsulfonylamino(thio)carbonyltriazolin(thi)one

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WO1997003980A1 true WO1997003980A1 (fr) 1997-02-06

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EP (1) EP0840734A1 (fr)
JP (1) JPH11509219A (fr)
CN (1) CN1195347A (fr)
AU (1) AU6518896A (fr)
CA (1) CA2227012A1 (fr)
DE (1) DE19525974A1 (fr)
WO (1) WO1997003980A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001005788A1 (fr) * 1999-07-15 2001-01-25 Bayer Aktiengesellschaft Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)ones substituees

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0341489A1 (fr) * 1988-05-09 1989-11-15 Bayer Ag Sulfonylaminocarbonyltriazolinones
EP0422469A2 (fr) * 1989-10-12 1991-04-17 Bayer Ag Sulfonylaminocarbonyltriazolinones
EP0425948A2 (fr) * 1989-11-03 1991-05-08 Bayer Ag Sulfonylaminocarbonyl-triazolinones halogénées
EP0431291A2 (fr) * 1989-11-03 1991-06-12 Bayer Ag Sulfonylaminocarbonyl-triazolinones comportant des substituants attachés par du soufre
EP0507171A1 (fr) * 1991-04-04 1992-10-07 Bayer Ag Sulfonylaminocarbonyltriazolinones avec des substituants liés par l'oxygène
EP0534266A1 (fr) * 1991-09-25 1993-03-31 Bayer Ag Sulfonylaminocarbonyltriazolones ayant deux substituants liés à l'intermédiaire d'un oxygène
DE4435547A1 (de) * 1994-10-05 1996-04-11 Bayer Ag Sulfonylaminocarbonyltriazolinone mit über Sauerstoff und Schwefel gebundenen Substituenten

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0341489A1 (fr) * 1988-05-09 1989-11-15 Bayer Ag Sulfonylaminocarbonyltriazolinones
EP0422469A2 (fr) * 1989-10-12 1991-04-17 Bayer Ag Sulfonylaminocarbonyltriazolinones
EP0425948A2 (fr) * 1989-11-03 1991-05-08 Bayer Ag Sulfonylaminocarbonyl-triazolinones halogénées
EP0431291A2 (fr) * 1989-11-03 1991-06-12 Bayer Ag Sulfonylaminocarbonyl-triazolinones comportant des substituants attachés par du soufre
EP0507171A1 (fr) * 1991-04-04 1992-10-07 Bayer Ag Sulfonylaminocarbonyltriazolinones avec des substituants liés par l'oxygène
EP0534266A1 (fr) * 1991-09-25 1993-03-31 Bayer Ag Sulfonylaminocarbonyltriazolones ayant deux substituants liés à l'intermédiaire d'un oxygène
DE4435547A1 (de) * 1994-10-05 1996-04-11 Bayer Ag Sulfonylaminocarbonyltriazolinone mit über Sauerstoff und Schwefel gebundenen Substituenten

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001005788A1 (fr) * 1999-07-15 2001-01-25 Bayer Aktiengesellschaft Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)ones substituees
AU771414B2 (en) * 1999-07-15 2004-03-18 Bayer Cropscience Aktiengesellschaft Substituted thiene-3-yl-sulfonyl amino(thio)carbonyl-triazolin(thi)ones
US6964939B1 (en) 1999-07-15 2005-11-15 Bayer Aktiengesellschaft Substituted thiene-3-yl-sulfonyl amino(thio)carbonyl-triazolin(thi)ones
US7642221B2 (en) 1999-07-15 2010-01-05 Bayer Aktiengesellschaft Substituted thien-3-yl-sulphonylamino(thio)carbonyl-triazoline(ethi)ones
US7858805B2 (en) 1999-07-15 2010-12-28 Bayer Aktiengesellschaft Substituted thien-3-yl-sulphonylamino(thio)carbonyl-triazolin(ethi)ones

Also Published As

Publication number Publication date
CA2227012A1 (fr) 1997-02-06
CN1195347A (zh) 1998-10-07
AU6518896A (en) 1997-02-18
JPH11509219A (ja) 1999-08-17
DE19525974A1 (de) 1997-01-23
EP0840734A1 (fr) 1998-05-13

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