WO1992020663A1 - Triazolinones substituees - Google Patents

Triazolinones substituees Download PDF

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Publication number
WO1992020663A1
WO1992020663A1 PCT/EP1992/000968 EP9200968W WO9220663A1 WO 1992020663 A1 WO1992020663 A1 WO 1992020663A1 EP 9200968 W EP9200968 W EP 9200968W WO 9220663 A1 WO9220663 A1 WO 9220663A1
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WIPO (PCT)
Prior art keywords
carbon atoms
phenyl
propyl
methyl
alkyl
Prior art date
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PCT/EP1992/000968
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German (de)
English (en)
Inventor
Kurt Findeisen
Dietmar Kuhnt
Klaus-Helmut Müller
Klaus König
Klaus Lürssen
Hans-Joachim Santel
Robert R. Schmidt
Original Assignee
Bayer Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
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Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to CS932431A priority Critical patent/CZ243193A3/cs
Priority to JP4508977A priority patent/JPH06507606A/ja
Priority to SK1271-93A priority patent/SK127193A3/sk
Priority to AU16800/92A priority patent/AU655019B2/en
Priority to BR9205999A priority patent/BR9205999A/pt
Publication of WO1992020663A1 publication Critical patent/WO1992020663A1/fr

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    • 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
    • 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

Definitions

  • the invention relates to new substituted triazolinones
  • R 1 and R 2 each independently represent alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cyanoalkyl, alkoxyalkyl, alkoxy, cycloalkyl, cycloalkylalkyl, each optionally substituted aryl, aralkyl or heteroaryl or together with the nitrogen atom to which they are attached are an optionally substituted heterocycle,
  • R 3 represents alkyl or cycloalkyl
  • X represents oxygen or sulfur.
  • the compounds of the formula (I) can optionally be present as geometric and / or optical isomers or isomer mixtures of different compositions. Both the pure isomers and the isomer mixtures are claimed according to the invention.
  • R 1 , R 2 and R 3 have the meaning given above, and / or tautomers of these compounds, ie the corresponding hydroxytriszoles, with iso (thio) cyanates of the general formula (III)
  • R 4 and X have the meaning given above, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or if b) chlorocarbonyl-triazolinones of the general formula (IV)
  • R 1 , R 2 and R 3 have the meaning given above, with amines of the general formula (V)
  • halogen means fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • Optionally substituted aryl groups such as aryl, aralkyl, aryloxy can carry one or more, preferably 1 to 5, in particular 1 to 3 and particularly preferably 1 or 2 identical or different substituents.
  • aryl is preferably phenyl or naphthyl.
  • radicals R 1 and R 2 are in the event that they form a heterocycle together with the nitrogen atom to which they are attached, preferably for a heterocycle of the formula which may be monosubstituted, disubstituted or triply, identically or differently
  • Methyl, ethyl, n- or i-propyl, chlorine and trifluoromethyl are particularly preferred as substituents.
  • heterocycle in the meaning of heterocyclyl alkyl for R 4 preferably stands for the following heterocycles:
  • Alkyl in the meaning of heterocyclylalkyl is, for example, methyl, ethyl, n- or isopropyl, n-, iso-, sec. Or tert-butyl.
  • heterocycle in the meaning of heterocyclylalkyl can be single or multiple, preferably single to triple, in particular single or double identical or different by straight-chain or branched alkyl or haloalkyl having 1 to 4, preferably 1 or 2 carbon atoms and 1 to 9, preferably 1 up to 5, in particular 1 to 3 identical or different halogen atoms or in each case doubly linked alkanediyl or alkenediyl having up to 4 carbon atoms.
  • methyl and ethyl are selected as substituents.
  • R 1 and R 2 independently of one another each represent straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkynyl having 2 to 8 carbon atoms, haloalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, Haloalkenyl or haloalkynyl each having 2 to 8 carbon atoms and 1 to 15 or 1 to 13 identical or different halogen atoms, cyanoalkyl,
  • R 1 and R 2 together with the nitrogen atom to which they are attached represent an optionally mono- or polysubstituted or substituted the same or different five- to ten-membered heterocycle, which optionally contains 1 to 2 further heteroatoms, in particular nitrogen, oxygen and / or sulfur may be used, the following being suitable as substituents: halogen and in each case straight-chain or branched alkyl or haloalkyl each having 1 to 4 carbon atoms and optionally 1 to 9 identical or different halogen atoms and 1 to 2 oxo or thiono groups, R 3 represents straight-chain or branched alkyl having 1 to 8 carbon atoms or cycloalkyl having 3 to 8 carbon atoms,
  • R 4 for each straight-chain or branched alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkynyl having 2 to 8 carbon atoms, haloalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, haloalkenyl or haloalkynyl each having 2 to 8 carbon atoms and 1 to 15 or 1 to 13 identical or different halogen atoms, cyanoalkyl with 1 to 8 carbon atoms, hydroxyalkyl with 1 to 8 carbon atoms and 1 to 6 hydroxy groups, for phenoxyalkyl, phenylthioalkyl, phenylsulfinylalkyl, phenylsulfonylalkyl, phenylaminoalkyl, N- (C 1 -C 4 alkyl) phenylaminoalkyl or phenylazoalkyl, each with 1 to 4 carbon atoms
  • R 4 represents benzyl with -O-CH 2 -O- group fused in the phenyl part
  • X represents oxygen or sulfur.
  • R 1 and R 2 are each independently methyl
  • substituents are: methyl, ethyl, n- or i-propyl, chlorine or trifluoromethyl, R 3 for methyl, ethyl, propyl, isopropyl, n-, ⁇ -, s- or t-butyl, cyclopropyl, cyclobutyl, Cyclopentyl or cyclohexyl, R 4 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, in each case straight-chain or branched pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, for allyl, each straight-chain or branched butenyl, pentenyl or hexeny, l propargyl, each straight-chain or branched butinyl, pentinyl or hexin
  • R 4 furthermore stands for heterocyclylmethyl, heterocyclylpropyl or heterocyclylethyl which may be mono- or trisubstituted in the heterocyclyl part and which may be mono- or trisubstituted, the heterocycles in each case being suitable:
  • R 4 also represents in each case straight-chain or branched alkoxy having 1 to 6 carbon atoms, alkenyloxy having 3 to 6 carbon atoms or alkynyloxy having 3 to 6 carbon atoms or for in each case optionally mono- to trisubstituted, identically or differently substituted, optionally straight-chain or branched benzyl, phenylethyl, Phenylpropyl, phenylpropenyl, phenylpropinyl, phenylbutyl, phenylbutenyl, phen
  • R 1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, cyclopropyl, cyclopentyl or cyclohexyl,
  • R 2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl or
  • R 3 represents methyl, ethyl, propyl or isopropyl, in particular methyl, R 4 for 1-methyl-3-phenyl-propyl, 1-ethyl-3-phenyl-propyl, 1-propyl-3-phenyl-propyl, 1-isopropyl-3-phenyl, optionally substituted once to three times, identically or differently -propyl, 2-methyl-3-phenyl-propyl, 1,1-dimethyl-3-phenyl-propyl, 1-methyl-1-ethyl-3-phenyl-propyl, 1,1-diethyl-3-phenyl-propyl , 1-methyl-1-propyl-3-phenyl-propyl,
  • radicals (R 1 , R 2 , X etc.), which are defined in the active compounds of the formula (I), also have the meanings given for the compounds of the formula (I) in the intermediates and precursors for all definition areas. The same applies to the residues that are mentioned several times in preliminary and intermediate products.
  • R represents methyl, ethyl or pheny, l preferably phenyl, is reacted at temperatures between 20 ° C. and 150 ° C. and the chloroformamidine derivatives of the formula (VIII) formed in this way
  • R, R 1 and R 2 have the meaning given above, if necessary after I so i lution by vacuum distillation or by other customary methods, with alkylhydrazines of the formula (IX) R 3 -NH-NH 2 (IX) in which R 3 has the meaning given above, if appropriate in the presence of diluents such as methylene chloride, dioxane and / or diethyl ether, reacted at temperatures between 0 ° C and 100 ° C and worked up using customary methods (cf. the preparation examples,)
  • the starting materials of the formula (III) are known organic synthetic chemicals (cf. e.g. Nouv. J, Chim. 1 (1977), 243-254 - cited in Chem. Abstracts 87:
  • R 1 , R 2 and R 3 have the meaning given above, with phosgene, optionally in the presence of an acid binder, such as triethylamine, and optionally in the presence of a diluent, such as toluene or acetonitrile, at temperatures between 0 ° C and 150 ° C implements.
  • an acid binder such as triethylamine
  • a diluent such as toluene or acetonitrile
  • the starting materials of the formula (V) are known and / or can be prepared by processes known per se (cf. J. Med. Chem. 25 (1982), 1363-1370; Tetrahedron Lett. 29 (1988), 223-224; Chem. Ber. 117 (1984), 856-858; DE-OS 3426919; EP-A 237305; J. Am. Chem. Soc. 71 (1949), 3482-3485; Tetrahedron Lett. 27 (1986), 3957- 3960; Bull. Soc. Chim. France 1974 (3-4, Pt. 2), 615-622; Tetrahedron Lett. 31 (1990), 2661-2664; J. Med.
  • Process (a) according to the invention for the preparation of the new substituted triazolinones of the formula (I) is 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 isopropy
  • B. acetonitrile and propionitrile amides such as. B. dimethylformamide, dimethylacetamide and N-methyl-pyrrolidone and dimethyl sulfoxide, tetramethylene sulfone and hexamethylphosphoric triamide.
  • Process (a) according to the invention can, if appropriate, be carried out in the presence of a basic reaction auxiliary.
  • All common inorganic and organic bases are suitable as such.
  • Tertiary amines such as triethylamine, N, N-dimethylaniline, pyridine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU) 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 0 ° C and + 150 ° C, preferably wise at temperatures between + 40 ° C and + 120 oC.
  • Process (a) according to the invention is usually carried out under normal pressure. However, it is also possible to work under elevated pressure, in particular in the case of gaseous starting compounds.
  • process (a) To carry out process (a) according to the invention, 1 to 5 mol, preferably 1 to 2.5 mol, of iso (thio) cyanate of the formula (III) and, if appropriate, 1 to 2.5, are generally employed per mol of triazolinone of the formula (II) Mole of reaction auxiliary.
  • the reaction is carried out, worked up and isolated in analogy to generally known processes (cf. the preparation examples).
  • Inert organic solvents are also suitable as diluents for carrying out process (b) according to the invention.
  • the diluents mentioned in process (a) are preferably used.
  • Process (b) according to the invention is optionally carried out in the presence of a suitable acid binder. All conventional inorganic or organic bases are suitable as such.
  • alkali metal hydroxides such as sodium hydroxide or potassium hydroxide
  • alkali metal carbonates such as sodium carbonate, potassium carbonate or sodium hydrogen carbonate
  • tertiary amines such as triethylamine, N, N-dimethylaniline, pyridine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicyclo undecen (DBU).
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicyclo undecen
  • reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. Generally works at temperatures between 0 ° C and + 150 ° C, preferably at temperatures between + 10 ° C and + 80 ° C.
  • Process (b) according to the invention is usually carried out under normal pressure, but it is also possible to work under increased pressure.
  • 1 to 5 mol, preferably 1 to 2.5 mol of amine of the formula (V) and, if appropriate, 1 to 2.5 mol of acid binder are generally employed per mol of chlorocarbonyltriazole inone of the formula (IV) on.
  • the reaction is carried out, worked up and isolated in analogy to generally known processes (cf. the preparation examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention as total or selective effective herbicides depend essentially on the amount used.
  • the active compounds according to the invention can e.g. used in the following plants: dicot weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirs Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,
  • 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 palra, 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 compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops in the pre-emergence and post-emergence processes.
  • the active ingredients can be converted into the usual formulations, such as solutions, emulsions, spray powders ver, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. 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.
  • 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
  • ammonium salts and natural rock flour 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, are suitable as solid carriers for granules: 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 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 carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also 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 are used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active ingredient, 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 such as 1-amino-6-ethylthio-3- (2,2-dimethylpropyl) -1,3,5-triazine-2,4 (1H, 3H) -dione (AMETHYDIONE) or N- (2-benzothiazolyl) - N, N - dimethyl urea (METABENZTHIAZURON) for weed control in cereals; 4-amino-3-methyl-6-phenyl-1, 2,4-triazin-5 (4H) -one (METAMITRON) for weed control in sugar beets and 4-amino-6- (1,1-dimethylethyl) -3- methylthio-1,2,4-triazin-5 (4H) -one (METRIBUZIN) for weed control in soybeans, in question; also 2,4-dichlorophenoxyacetic acid (2,4-D); 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB); 2,4-dich
  • CHLORINE PROPHAM 2-chloro-N- ⁇ C (4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino3-carbonyl ⁇ benzenesulfonamide
  • CHLORSULFURON N, N-Dimethyl-N '- (3-chloro-4-methylphenyl) urea
  • exo-1-methyl-4- (1-methylethyl) -2- (2-methylphenyl-methoxy) -7-oxabicyclo- (2,2,1) -heptane CINMETHYLIN
  • CLOPYRALID 2-chloro-4-ethylamino-6- (3-cyanopropylamino) -1,3,5-triazine
  • CYANAZINE N, S-diethyl-N-cyclohexylthiol carbamate
  • 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 both before and can also be applied after emergence of the plants.
  • 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 5 kg per ha.
  • the product can be brought to crystallization by boiling with acetonitrile; Melting point: 222 ° CC.
  • a mixture of 71 g (0.5 mol) of 5-dimethylamino-1-methyl-1, 2-dihydro-3H-1,2,4-triazol-3-one and 800 ml of acetonitrile is heated to the reflux temperature while introducing phosgene urvd phosgenated until the end of the hydrogen chloride evolution. Then nitrogen is blown through the mixture and then the solvent is carefully distilled off. The residue is recrystallized from acetic esters.
  • 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 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.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Seeds of the test plants are sown in normal soil and watered with the active compound preparation after 24 hours.
  • the quantities of water per unit area are 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.
  • 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 the following production examples 7, 9, 12, 65 and 67 show up to 100% activity against Amaranthus, Impomoea, Matricaria and Portulaca combined with an excellent compatibility with barley, corn and soybeans at an application rate of 1000 g / ha .
  • the comparison compound (A) shows only an action against Ipomoea (30%) and Portulaca (50%).
  • the formulas of the compounds of the general formula (I) according to the invention used for the application examples are listed below with the numbering of the preparation examples (“Ex. No.”).

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material 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)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (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 triazolinones substituées, de formule générale (I), dans laquelle R1 et R2 représentent, indépendamment l'un de l'autre, respectivement, un alkyle, alcényle, alkinyle, halogénoalkyle, halogénalcényle, halogénoalkinyle, cyanalkyle, alcoxyalkyle, alcoxy, cycloalkyle, cycloalkylalkyle, ou bien un aryle, aralkyle ou hétéroaryle chacun, éventuellement substitué, ou conjointement avec l'atome d'azote auquel ils sont liés, un hétérocycle éventuellement substitué, R3 est un alkyle ou un cycloalkyle, R4 représente un alkyle, alcényle, alkynyle, halogénoalkyle, halogénoalcényle, halogénoalkinyle, cyanalkyle, hydroxyalkyle, alcoxyalkyle, aryloxyalkyle, arylthioalkyle, arylsulfinylalkyle, arylsulfonylalkyle, arylaminoalkyle, N-alkyl-arylaminoalkyle, arylazoalkyle, alcoxycarbonylalkyle, alcoxycarbonylalcényle, alkylaminoalkyle, dialkylaminoalkyle, ou bien un cycloalkyle, cycloalkylalkyle, cycloalcényle ou cycloalcénylalkyle, chacun éventuellement substitué, un hétérocyclylalkyle éventuellement substitué, ou encore un aralkyle, arylalcényle, arylalkinyle, aroyle, aryle aralkyloxy ou aryloxy, chacun éventuellement substitué, ou un alcoxy, alcényloxy ou alkinyloxy, et X est un oxygène ou un soufre. L'invention concerne également plusieurs procédés de préparation de ces composés, ainsi que leur utilisation comme herbicides.
PCT/EP1992/000968 1991-05-17 1992-05-04 Triazolinones substituees WO1992020663A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CS932431A CZ243193A3 (en) 1991-05-17 1992-05-04 Substituted triazolinones
JP4508977A JPH06507606A (ja) 1991-05-17 1992-05-04 置換されたトリアゾリノン
SK1271-93A SK127193A3 (en) 1991-05-17 1992-05-04 Substituted triazolinones
AU16800/92A AU655019B2 (en) 1991-05-17 1992-05-04 2-amido-1,2,4-triazolinone derivatives
BR9205999A BR9205999A (pt) 1991-05-17 1992-05-04 Triazolinonas substituídas

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4116115.7 1991-05-17
DE19914116115 DE4116115A1 (de) 1991-05-17 1991-05-17 Substituierte triazolinone

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WO1992020663A1 true WO1992020663A1 (fr) 1992-11-26

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JP (1) JPH06507606A (fr)
AU (1) AU655019B2 (fr)
BR (1) BR9205999A (fr)
CZ (1) CZ243193A3 (fr)
DE (1) DE4116115A1 (fr)
PL (1) PL294566A1 (fr)
SK (1) SK127193A3 (fr)
WO (1) WO1992020663A1 (fr)

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BR102018075132A2 (pt) 2018-12-04 2020-06-16 UPL Corporation Limited Composição herbicida sinergística de amplo espectro para o controle de plantas daninhas em culturas agrícolas, uso da dita composição para preparação de produto, produto e método de aplicação

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2042660A1 (en) * 1970-08-28 1972-03-02 Farbenfabriken Bayer Ag, 5090 Lever Kusen 5-amino-triazolone derivs - useful as plant - protection agents
EP0283876A2 (fr) * 1987-03-24 1988-09-28 Bayer Ag Triazolinones substitués
EP0305844A1 (fr) * 1987-09-01 1989-03-08 Bayer Ag Triazolinones substituées
EP0398096A1 (fr) * 1989-05-18 1990-11-22 Bayer Ag Triazolones substituées
EP0431390A1 (fr) * 1989-12-02 1991-06-12 Bayer Ag Triazolinones substituées

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2042660A1 (en) * 1970-08-28 1972-03-02 Farbenfabriken Bayer Ag, 5090 Lever Kusen 5-amino-triazolone derivs - useful as plant - protection agents
EP0283876A2 (fr) * 1987-03-24 1988-09-28 Bayer Ag Triazolinones substitués
EP0305844A1 (fr) * 1987-09-01 1989-03-08 Bayer Ag Triazolinones substituées
EP0398096A1 (fr) * 1989-05-18 1990-11-22 Bayer Ag Triazolones substituées
EP0431390A1 (fr) * 1989-12-02 1991-06-12 Bayer Ag Triazolinones substituées

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AU1680092A (en) 1992-12-30
AU655019B2 (en) 1994-12-01
JPH06507606A (ja) 1994-09-01
EP0586418A1 (fr) 1994-03-16
SK127193A3 (en) 1994-11-09
BR9205999A (pt) 1994-09-27
PL294566A1 (en) 1993-05-17
DE4116115A1 (de) 1992-11-19
CZ243193A3 (en) 1994-03-16

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