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WO1993004050A1 - Triazolinones substituees a proprietes herbicides - Google Patents

Triazolinones substituees a proprietes herbicides Download PDF

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Publication number
WO1993004050A1
WO1993004050A1 PCT/EP1992/001829 EP9201829W WO9304050A1 WO 1993004050 A1 WO1993004050 A1 WO 1993004050A1 EP 9201829 W EP9201829 W EP 9201829W WO 9304050 A1 WO9304050 A1 WO 9304050A1
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Prior art keywords
formula
alkyl
stands
sulfur
hydrogen
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PCT/EP1992/001829
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German (de)
English (en)
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Aktiengesellschaft Bayer
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Bayer AG
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Bayer AG
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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

Definitions

  • the invention relates to new substituted triazolinones, several processes for their preparation and their use as herbicides.
  • R 2 represents in each case optionally substituted cycloalkyl, aryl or heterocyclyl
  • A represents a radical of the formula or (CH 2 ) m -Q- (CH 2 ) n - represents oxygen or sulfur and represents oxygen or sulfur
  • R 3 represents either hydrogen, cyano or alkyl
  • R 4 , R 5 and R 6 each independently represent hydrogen or alkyl or R 3 and R 4 together represent a doubly linked radical of the formula - (CH 2 ) p -,
  • Q represents oxygen, sulfur, a sulfinyl group, a sulfonyl group or a radical of the formula) NR 7 ,
  • R 7 represents hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, cyanoalkyl or alkanoyl, m represents a number 0, 1 or 2, n represents a number 0, 1 or 2 and p represents a number 2, 3, 4, 5 or 6 is found.
  • the compounds of the formula (I) may optionally be present as geometric and / or optical isomers or isomer mixtures of different compositions. Both the pure isomers and the isomeric strain are claimed according to the invention. Furthermore, it was found that the new substituted triazolinones of the general formula (I)
  • R 2 represents in each case optionally substituted cycloalkyl, aryl or heterocyclyl
  • A represents a radical of the formula or (CH 2 ) m -Q- (CH 2 ) n - X stands for oxygen or sulfur and Y stands for oxygen or sulfur
  • R 3 represents either hydrogen, cyano or alkyl
  • R 4 , R 5 and R 6 each independently represent hydrogen or alkyl or
  • R 3 and R 4 together represent a doubly linked radical of the formula - (CH 2 ) p -,
  • Q represents oxygen, sulfur, a sulfinyl group, a sulfonyl group or a radical of the formula> NR 7 ,
  • R 7 represents hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, cyanoalkyl or alkanoyl, m represents a number 0, 1 or 2, n represents a number 0, 1 or 2 and p represents a number 2, 3, 4, 5 or 6 is obtained if a) hydrazones of the formula (II),
  • R 1 , R 2 , A, X and Y have the meaning given above and
  • R 8 and R 9 each independently represent hydrogen, alkyl, aralkyl or aryl, if appropriate with an acid in the presence of a diluent, or if 1H-triazolinones of the formula (III),
  • R 1 and X have the meaning given above, with iso (thio) cyanates of the formula (IV),
  • R 2 , A and Y have the meaning given above, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary.
  • the substituted triazolinones of the general formula (I) according to the invention show a considerably better herbicidal activity against problem weeds and, at the same time, a comparatively good tolerance to important crop plants in comparison to the substituted triazole inones known from the prior art, such as, for example, the compound 1- ( 4-phenyl-2-butylarainocarbonyl) -3-methyl-4-amino-1,2,4-triazolin-5-one or the compound 1- (1-cyclohexyl-1-ethylaminocarbonyl) -3-methyl-4 -amino-1,2,4-triazolin-5-one or the compound 1- (3-phenyl-2-methyl-2-propylaminocarbonyl) -3-ethyl-4-amino-1,2,4-triazolin-5 -on, which are chemically and functionally obvious compounds.
  • the substituted triazolinones according to the invention are generally defined by the formula (I).
  • Compounds of formula (I) are preferred in which
  • R 1 for straight-chain or branched alkyl with 1 to
  • R 2 represents optionally mono- or polysubstituted, identically or differently substituted cycloalkyl having 3 to 7 carbon atoms, the following being suitable as substituents:
  • X represents oxygen or sulfur
  • Y represents oxygen or sulfur
  • R 3 represents either hydrogen, cyano or straight-chain or branched alkyl having 1 to 8 carbon atoms and
  • R 4 , R 5 and R 6 each independently represent hydrogen or straight-chain or branched alkyl having 1 to 6 carbon atoms or
  • R 3 and R 4 together represent a doubly linked radical of the formula - (CH 2 ) p -, Q represents oxygen, sulfur, a sulfinyl group, a sulfonyl group or a radical of the formula> NR,
  • R 7 represents hydrogen or straight-chain or branched alkyl, hydroxyalkyl, alkoxyalkyl, cyanoalkyl or alkanoyl each having 1 to 8 carbon atoms in the individual alkyl parts, m represents a number 0, 1 or 2, n represents a number 0, 1 or 2 stands for and p stands for a number 4, 5 or 6.
  • R 1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
  • X represents oxygen or sulfur
  • Y represents oxygen or sulfur
  • R 3 represents either hydrogen, cyano or straight-chain or branched alkyl having 1 to 6 carbon atoms and
  • R 4 , R 5 and R 6 each independently represent hydrogen or straight-chain or branched alkyl having 1 to 6 carbon atoms or
  • R 3 and R 4 together represent a radical of the formula - (CH 2 ) 5 -,
  • Q represents oxygen, sulfur or a radical of the formula> NR 7 ,
  • R 7 represents hydrogen or represents straight-chain or branched alkyl, hydroxyalkyl, alkoxyalkyl, cyanoalkyl or alkanoyl each having 1 to 4 carbon atoms in the individual alkyl parts, m stands for a number 0 or 1 and n stands for a number 0 or 1.
  • R 1 represents methyl, ethyl, n- or i-propyl or cyclopropyl
  • R 2 represents phenyl which is optionally mono- to trisubstituted by identical or different substituents, the following being suitable in each case:
  • R 3 represents either hydrogen, cyano or straight-chain or branched alkyl having 1 to 4 carbon atoms and
  • R 4 , R 5 and R 6 each independently represent hydrogen or straight-chain or branched alkyl having 1 to 3 carbon atoms or
  • R 3 and R 4 together represent a radical of the formula - (CH 2 ) 5 -,
  • Q represents oxygen, sulfur or a radical of the formula> NR 7 ,
  • R 7 stands for hydrogen or for straight-chain or branched alkyl, hydroxyalkyl, alkoxyalkyl, cyanoalkyl or alkanoyl each having 1 to 3 carbon atoms in the individual alkyl parts, m stands for a number 0 or 1 and n stands for a number 0 or 1.
  • m stands for a number 0 or 1
  • n stands for a number 0 or 1.
  • Formula (II) provides a general definition of the hydrazones required as starting materials for carrying out process (a) according to the invention.
  • R 1 , R 2 , A, X and Y preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the compounds of the formula (I) according to the invention.
  • R 8 and R 9 preferably each independently represent hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, phenyl or benzyl.
  • hydrazones of the formula (II) are not yet known. They are also the subject of the present invention. They are obtained in analogy to known processes (compare, for example, DE-OS 38 03 523 or Acta Pol. Pharm. 38, 153-162 [1981] or CA 95: 203841), for example if 1H-triazole inones are used Formula (III),
  • R 1 and X have the meaning given above, with aldehydes or ketones of the formula (V),
  • R 8 and R 9 have the meaning given above, optionally in the presence of a diluent such as dichloromethane or toluene and optionally in the presence of a reaction auxiliary such as p-toluenesulfonic acid at temperatures between 40 ° C and 120 ° C and the 1 unsubstituted triazole inone hydrazones of the formula (VI),
  • R 1 , R 8 , R 9 and X have the meaning given above, either in a subsequent second stage with iso (thio) cyanates of the formula (IV),
  • R 2 , A and Y have the meaning given above, optionally in the presence of a diluent such as dichloromethane or dioxane and optionally in the presence of a reaction auxiliary such as triethylamine at temperatures between 0 ° C and 150 ° C or alternatively in a subsequent 2nd Stage with (thio) chloroformate esters of the formula (VII),
  • R 10 represents alkyl, aralkyl or aryl
  • Y has the meaning given above, or with (thio) phosgene optionally in the presence of a diluent such as chloroform, dichloromethane or tetrahydrofuran and optionally in the presence of a reaction auxiliary such as triethylamine, sodium hydride or potassium tert-butylate at temperatures between -20 ° C and + 100 ° C and the triazole inone derivatives of the formula (VIII) thus obtainable, (VIII)
  • Z represents a radical -OR 10 or chlorine
  • R 1 , R 8 , R 9 , X and Y have the meaning given above
  • R 2 and A have the meaning given above, optionally in the presence of a diluent such as tetrahydrofuran and optionally in the presence of a reaction auxiliary such as sodium hydroxide or potassium hydroxide at temperatures between 20 ° C and 50 ° C.
  • a diluent such as tetrahydrofuran
  • a reaction auxiliary such as sodium hydroxide or potassium hydroxide at temperatures between 20 ° C and 50 ° C.
  • triazolinone derivatives of the formula (VIII) can also be obtained if triazolinones of the formula (X) (X)
  • R 1 , X and Y have the meaning given above and R 10 represents alkyl, aralkyl or aryl, with aldehydes or ketones of the formula (V),
  • R 8 and R 9 have the meaning given above, optionally in the presence of a diluent such as dichloromethane or toluene and optionally in the presence of a reaction auxiliary such as p-toluene sulphonic acid at temperatures between 40 ° C and 120 ° C implemented.
  • a diluent such as dichloromethane or toluene
  • a reaction auxiliary such as p-toluene sulphonic acid at temperatures between 40 ° C and 120 ° C implemented.
  • R 1 and X preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.
  • the 1H-triazolinones of the formula (III) are known or can be obtained in analogy to known processes (compare, for example, J. Heterocycl. Chem. 16, 403 [1979]; J,
  • Formula (IV) provides a general definition of the iso (thio) cyanates required for carrying out process (b) according to the invention and for synthesizing the precursors of the formula (II) as starting materials.
  • R 2 , A and Y preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.
  • the iso (thio) cyanates of the formula (IV) are known in some cases (compare, for example, JJ med. Chem. 30, 1767-1773
  • the triazolinones of the formula (X) are known or can be obtained by analogy with known processes (compare, for example, DE-OS 37 19 575; DE-OS 38 03 523),
  • Aldehydes and ketones of the formula (V) are generally known compounds of organic chemistry.
  • (Thio) chloroformic acid esters of the formula (VII) are also generally known compounds of organic chemistry.
  • Suitable diluents for carrying out process (a) according to the invention are all customary organic or inorganic solvents.
  • Polar water-miscible organic solvents in particular alcohols, such as methanol, ethanol, propanol or butanol, the mixtures of which are preferably used
  • reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures between + 20 ° C and + 150 ° C, preferably at temperatures between + 50 ° C and + 120 ° C.
  • Process (a) according to the invention is usually carried out under normal pressure or under reduced pressure. If you work under reduced pressure, pressure ranges between 20 and 400 mbar, preferably between 100 and 200 mbar.
  • 1.0 to 50.0 mol, preferably 1.0 to 25 mol, of acid are generally employed per mol of hydrazone of the formula (II).
  • the hydrazone of formula (II) is dissolved in a suitable amount of diluent, then the required amount of acid is added and the mixture is slowly concentrated under reduced pressure over several hours.
  • process (a) according to the invention it is also possible to carry out process (a) according to the invention and the preparation of the precursors of the formula (II) required therefor in one reaction step in a so-called “one-pot process”.
  • process (a) it is also possible to carry out process (a) according to the invention and the preparation of the precursors of the formula (II) required therefor in one reaction step in a so-called “one-pot process”.
  • the starting compounds are selected from the triazolinone derivatives of the formula (VIII) and these are reacted in succession in a "one-pot process” with amines of the formula (IX) and then with acid in accordance with process (a) according to the invention, or alternatively that the first compounds are unsubstituted triazoline hydrazones of the formula (VI) are selected and these are reacted in succession in a "one-pot process” with Ieo (thio) cyanates of the formula (IV) and then with acid in accordance with process (a)
  • reaction is carried out, worked up and isolated by known processes (see, for example, DE-OS 38 03 523 or the preparation examples),
  • Inert organic solvents are suitable as diluents for carrying out process (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; 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-methylform
  • process (b) according to the invention can be carried out in the presence of a suitable reaction auxiliary.
  • All conventional inorganic or organic bases are suitable as such. It is preferred to use tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecenes (DBU)
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecenes
  • reaction temperatures can be increased when carrying out process (b) according to the invention
  • Range can be varied. In general, temperatures between 0 ° C and + 150 ° C, preferably at temperatures between + 10 ° C and + 100 ° C.
  • 1.0 to 2.0 mol, preferably 1.0 to 1.5 mol, of iso (thio) cyanate of the formula are generally employed per mol of 1H-triazole inone of the formula (III) (IV) and optionally 0.001 to 2.0 mol, preferably 0.001 to 1.0 mol, of reaction auxiliary.
  • reaction is carried out, worked up and isolated using known processes (see, for example, DE-OS 38 03 523 or the preparation examples).
  • the end products of the formula (I) are purified using customary methods, for example by column chromatography or by recrystallization.
  • the characterization is carried out using the melting point or, in the case of non-crystalline compounds, using proton nuclear magnetic resonance spectroscopy ( 1 H-NMR).
  • 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 which 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, 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 wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective purposes Weed control can be used in annual crops.
  • the active compounds according to the invention can be used particularly successfully to control monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops such as, for example, wheat, corn or sugar beet.
  • 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 polymeric substances,
  • formulations are prepared in a known manner, for example by mixing the active ingredients with
  • Extenders that is liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene or alkylnaphthalene
  • 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,
  • Solid carriers for granules are possible: for example broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks;
  • 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
  • Adhesives such as carboxymethylcellulose, 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 dyestuffs 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%.
  • active compounds according to the invention as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible *
  • herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil; Aryl carboxylic acids, such as, for example, dichloropicol acid, dicamba and picloram; Aryloxyalkanoic acids, such as, for example, 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 quizalofop-ethyl; Azinones such as chloridazon and norflurazon; Carbamates such as chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides such as alachlor, acetochlor, butachlor, metazachlor, metolachlor,
  • 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.
  • Active substances can never 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 watering, spraying, spraying or scattering.
  • the active compounds according to the invention can be applied both before and after the plants emerge.
  • the amount of active ingredient used can vary over a wide range, it essentially depends on the type of the desired effect. 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.
  • the solvent is distilled off in vacuo, the residue is taken up in dichloromethane, washed with saturated aqueous sodium hydrogen carbonate solution, dried over sodium sulfate and concentrated in vacuo.
  • the residue is crystallized by trituration with petroleum ether, filtered off and dried.
  • 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 and watered with the active ingredient preparation after 24 hours.
  • the amount of water per unit area is expediently kept constant.
  • the concentration of active substance in the preparation is irrelevant, the decisive factor is only the amount of active substance applied per unit area.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
  • the compounds according to preparation examples 10 and 11 show a clear superiority in effectiveness as well as in crop selectivity compared to the prior art.
  • the compounds according to the production examples 10 and 11 show, for example, at an application rate of 1,000 to 2,000 g per hectare in the pre-emergence test, a 70 to 100% activity against problem weeds such as amaranthus, cassia, portulaca and viola with excellent tolerance to useful plants such as wheat , Corn and sugar beet.
  • the comparison compound A shows only little effects on problem weeds at an application rate of 2,000 g per hectare.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants which have 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. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
  • the compounds according to Preparation Examples 1, 3, 11, 12, 13 and 19 show a clear superiority in effectiveness as well as in crop selectivity compared to the prior art.
  • Compounds according to the production examples 1, 3, 11, 12, 13 and 19 show, for example, at application rates between 125 and 500 g per hectare in the post-run test, an 80 to 100% activity against problem weeds such as Amaranthus, Galium, Matricaria, Solanum and Viola with excellent crop selectivity, especially with respect to wheat and corn.
  • the comparison compounds B and C have only a low herbicidal activity.

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

Abstract

L'invention concerne de nouvelles triazolinones substituées ayant la formule générale (I) dans laquelle R1 désigne un alkyle ou un cycloalkyle; R2 désigne un cycloalkyle, un aryle ou un hétérocyclyle, chacun d'eux portant éventuellement des substituants; A désigne un reste ayant la formule (a); (b); (c) ou (d); X désigne un oxygène ou un soufre, et Y désigne un oxygène ou un soufre, R3 représentant un hydrogène, un cyano ou un alkyle, et R4, R5 et R6 représentant respectivement, indépendamment l'un de l'autre, un hydrogène ou un alkyle, ou R3 et R4 formant un reste deux fois lié de formule -(CH2)p; Q désigne un oxygène, un soufre, un groupe sulfinyle, un groupe sulfonyle ou un reste de formule >N-R7; R7 désigne un hydrogène, un alkyle, hydroxyalkyle, alcoxyalkyle, cyanalkyle ou alcanoyle; m est égal à 0, 1 ou 2; n est égal à 0, 1 ou 2, et p est égal à 2, 3, 4, 5 ou 6; ainsi que plusieurs procédés de fabrication de ces composés et leur utilisation comme herbicides et comme nouveaux produits intermédiaires.
PCT/EP1992/001829 1991-08-23 1992-08-11 Triazolinones substituees a proprietes herbicides Ceased WO1993004050A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19914128029 DE4128029A1 (de) 1991-08-23 1991-08-23 Substituierte triazolinone
DEP4128029.6910823 1991-08-23

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WO1993004050A1 true WO1993004050A1 (fr) 1993-03-04

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DE (1) DE4128029A1 (fr)
WO (1) WO1993004050A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012052412A1 (fr) 2010-10-22 2012-04-26 Bayer Cropscience Ag Nouveaux composés hétérocycliques utilisés en tant qu'agents pour lutter contre des nuisibles

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0294666A2 (fr) * 1987-06-12 1988-12-14 Bayer Ag Triazolinones substituées
EP0370293A2 (fr) * 1988-11-19 1990-05-30 Bayer Ag Triazolinones substituées
EP0399294A1 (fr) * 1989-05-24 1990-11-28 Bayer Ag Triazolinones substitués

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0294666A2 (fr) * 1987-06-12 1988-12-14 Bayer Ag Triazolinones substituées
EP0370293A2 (fr) * 1988-11-19 1990-05-30 Bayer Ag Triazolinones substituées
EP0399294A1 (fr) * 1989-05-24 1990-11-28 Bayer Ag Triazolinones substitués

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012052412A1 (fr) 2010-10-22 2012-04-26 Bayer Cropscience Ag Nouveaux composés hétérocycliques utilisés en tant qu'agents pour lutter contre des nuisibles
US9173396B2 (en) 2010-10-22 2015-11-03 Bayer Intellectual Property Gmbh Heterocyclic compounds as pesticides

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