WO1995022532A1 - Triazolinones substituees et leur utilisation comme herbicides - Google Patents

Triazolinones substituees et leur utilisation comme herbicides Download PDF

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Publication number
WO1995022532A1
WO1995022532A1 PCT/EP1995/000466 EP9500466W WO9522532A1 WO 1995022532 A1 WO1995022532 A1 WO 1995022532A1 EP 9500466 W EP9500466 W EP 9500466W WO 9522532 A1 WO9522532 A1 WO 9522532A1
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Prior art keywords
carbon atoms
alkyl
chain
straight
branched
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PCT/EP1995/000466
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German (de)
English (en)
Inventor
Karl-Heinz Linker
Kurt Findeisen
Wilhelm Haas
Otto Schallner
Heinz-Jürgen Wroblowsky
Markus Dollinger
Hans-Joachim Santel
Original Assignee
Bayer Aktiengesellschaft
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Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU18084/95A priority Critical patent/AU1808495A/en
Priority to EP95909695A priority patent/EP0746550A1/fr
Priority to PL95315970A priority patent/PL315970A1/xx
Priority to BR9506928A priority patent/BR9506928A/pt
Priority to JP7521556A priority patent/JPH09509923A/ja
Publication of WO1995022532A1 publication Critical patent/WO1995022532A1/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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • 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<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • 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
    • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
    • C07F9/6518—Five-membered rings

Definitions

  • the invention relates to new substituted triazolinones, processes for their preparation and their use as herbicides.
  • Q oxygen or sulfur
  • R 1 represents haloalkyl
  • R ⁇ stands for hydrogen, amino, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkylidenimino or for optionally substituted cycloalkyl or cycloalkylalkyl,
  • R J represents hydrogen or halogen
  • R 4 represents cyano or nitro, and stands for isocyano, thiocyanato, sulfo, halosulfonyl, alkylaminooxy, dialkylaminooxy, alkylideneaminooxy, cycloalkylideneaminooxy, for optionally substituted cycloalkenyloxy or heterocyclyloxy, or for one of the following groups linked via nitrogen or oxygen
  • R 6 represents hydrogen, in each case optionally substituted by halogen, alkyl, alkenyl or alkynyl, or the grouping -CO- R 13 , in which
  • R 13 for hydrogen, each optionally by halogen or
  • R 7 represents the grouping - (CO) n -R 13 , wherein
  • R 13 has the meaning given above and
  • n the numbers 1 or 2
  • R 8 represents hydrogen, alkyl or alkoxy
  • R 9 represents alkoxy, alkylamino or dialkylamino
  • R 10 represents alkyl optionally substituted by halogen, alkoxy, alkylamino, dialkylamino or optionally substituted aryl,
  • R 11 for each optionally substituted by halogen alkyl or cycloalkyl or for each optionally substituted aryl or
  • R 12 represents alkyl
  • R 1 , R 2 , R 3 , R 4 and R 6 have the meanings given above,
  • n and R 13 have the meaning given above and
  • X 1 represents halogen
  • R 8 and R 9 have the meanings given above,
  • R 10 has the meaning given above and
  • X 2 represents halogen
  • R 1 , R 2 , R 3 and R 4 have the meanings given above and
  • X 3 represents halogen
  • R 11 and R 12 have the meanings given above,
  • the substituted triazolinones of the general formula (I) according to the invention show a considerably better herbicidal activity against problem weeds in comparison with the substituted triazolinones known from the prior art, such as, for example, the compound 2- (4-cyano-2,5-difluorophenyl) ) -5-methyl-4-propargyl-2,4-dihydro-3H-l, 2,4-triazol-3-one.
  • the invention preferably relates to compounds of the formula (I) in which
  • R 1 represents straight-chain or branched haloalkyl with 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms - in particular fluorine, chlorine, bromine or iodine,
  • R 2 for hydrogen, amino, cyano, for straight-chain or branched alkyl having 1 to 8 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each with 2 to 6 carbon atoms, for straight-chain saturated or branched haloalkyl with 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms - in particular fluorine, chlorine, bromine or iodine - for each straight-chain or branched haloalkenyl or haloalkynyl each with 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms - in particular
  • Chlorine, bromine and / or iodine-substituted cycloalkyl or cycloalkylalkyl each having 3 to 8 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl part,
  • R 3 represents hydrogen, fluorine, chlorine, bromine or iodine
  • R 4 represents cyano or nitro
  • R 5 for isocyano, thiocyanato, sulfo, halosulfonyl, C j -Cg alkylaminooxy, di (C ] -C 4 alkyl) aminooxy, C ⁇ -C 6 alkylidene aminooxy or C 5 -C 6 cycloalkylidene aminooxy, for each optionally by halogen, or C ] -C 4 alkoxy-substituted C 5 -C 6 cycloalkenyloxy, perhydrofuranyloxy or perhydropyranyloxy, or for one of the following groups bonded via nitrogen or oxygen
  • R 6 is for Hydrogen, for each optionally by fluorine and / or
  • R 13 for hydrogen, each optionally by fluorine,
  • Alkylamino or dialkylamino each with 1 to 6 carbon atoms Share atoms in the alkyl, or for each optionally substituted C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C r C 4 -alkyl, phenyl, naphthyl, phenyl-C r C 4 -alkyl, furyl , Thienyl or pyridyl, where in each case the following are suitable as substituents:
  • R 7 represents the grouping - (CO) n -R 13 , wherein
  • R 13 has the meaning given above as preferred and n represents the numbers 1 or 2,
  • R 8 for hydrogen or for alkyl or alkoxy each with 1 to 6
  • R 9 represents alkoxy, alkylamino or dialkylamino, each having 1 to 6 carbon atoms in the alkyl groups,
  • R 10 for optionally substituted by fluorine and / or chlorine alkyl having 1 to 6 carbon atoms, for alkoxy or alkylamino or
  • Dialkylamino each with 1 to 6 carbon atoms in the
  • R 11 is in each case optionally substituted by fluorine and / or chlorine alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms or in each case optionally substituted
  • R 12 represents alkyl having 1 to 6 carbon atoms.
  • the invention relates in particular to compounds of the formula (I) in which
  • Q oxygen or sulfur
  • R 1 represents straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms - in particular fluorine, chlorine, bromine or iodine,
  • R 2 for hydrogen, amino, cyano, for straight-chain or branched alkyl having 1 to 4 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each having 3 to 4 carbon atoms, for straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms - especially fluorine or chlorine - for each straight-chain or branched haloalkenyl or haloalkynyl each with 3 to 4 carbon atoms and 1 to 5 identical or different halogen atoms - especially fluorine or chlorine - for straight-chain or branched alkoxyalkyl each with 1 to 3 carbon atoms in the individual alkyl parts, for straight-chain or branched alkylidene imino with 1 to 4 carbon atoms or for each optionally in the cycloalkyl part singly or repeatedly, identically or differently by halogen - in particular fluorine or chlorine
  • R 4 represents cyano or nitro
  • R 5 for isocyano, thiocyanato, sulfo, chlorosulfonyl, C 1 -C 4 alkylaminooxy,
  • R 6 represents hydrogen, optionally substituted by fluorine-substituted alkyl having 1 to 4 carbon atoms or the grouping -CO-R 13 , in which
  • R 13 for hydrogen, for in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy alkyl or alkoxy each having 1 to 4 carbon atoms, for amino, for alkylamino or dialkylamino each with 1 to 4 carbon atoms in the alkyl parts, or for each counter ⁇ also substituted cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, phenyl, benzyl, phenylethyl, furyl, thienyl or
  • Haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in particular fluorine and / or chlorine atoms, substituted phenyl;
  • R 7 represents the grouping - (CO) n -R 13 , wherein
  • R 13 has the meaning given above as being particularly preferred and
  • n the numbers 1 or 2
  • R 8 represents hydrogen or alkyl or alkoxy each having 1 to 4 carbon atoms
  • R 9 represents alkoxy, alkylamino or dialkylamino each having 1 to 4 carbon atoms in the alkyl groups
  • R 10 for optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms, for alkoxy or alkylamino or dialkylamino, each having 1 to 4 carbon atoms in the
  • R 11 is in each case optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 6
  • Formula (II) provides a general definition of the aminoaryltriazolinones to be used as starting materials in process (a) according to the invention for the preparation of the compounds of the general formula (I).
  • Q, R 1 , R 2 , R 3 , R 4 and R 6 preferably or in particular have those meanings which have already been described as preferred or in connection with the description of the compounds of the formula (I) as particularly preferred for Q, R 1 , R 2 , R 3 , R 4 and R 6 .
  • aminoaryltriazolinones of the general formula (II) are obtained if halogenaryltriazolinones of the general formula (VIII) - above - are reacted with ammonia, if appropriate in the presence of a diluent such as dimethyl sulfoxide, at temperatures between 0 ° C. and 150 ° C. (cf. the manufacturing examples).
  • a diluent such as dimethyl sulfoxide
  • n and R preferably or in particular have those meanings which have already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for n and R 13 ;
  • X 1 preferably represents fluorine, chlorine or bromine, especially chlorine.
  • the starting materials of the formula (LU) are known organic synthetic chemicals.
  • Formula (IV) provides a general definition of the orthoesters to be used further as starting materials in process (a) according to the invention.
  • R 8 and R 9 preferably or in particular have those meanings which have already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R 8 and R 9 were.
  • the starting materials of the formula (IV) are known organic synthetic chemicals.
  • Formula (V) provides a general definition of the hydroxyaryltriazolinones to be used as starting materials in process (b) according to the invention for the preparation of the compounds of the general formula (I).
  • Q, R 1 , R 2 , R 3 and R 4 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, R 1 , R 2 , R 3 and R 4 have been given.
  • R 1 , R 2 , R 3 and R 4 have the meanings given above and
  • R represents alkyl (preferably methyl or ethyl)
  • a dealkylating agent e.g. Boron (III) bromide
  • a diluent e.g. Methyl enchloride
  • Formula (VI) provides a general definition of the acid halides to be used further as starting materials in process (b) according to the invention.
  • R 10 preferably or in particular has 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 R 10 ;
  • X 2 preferably represents fluorine, chlorine or bromine, especially chlorine.
  • the starting materials of the formula (VI) are known organic synthetic chemicals.
  • Formula (VII) provides a general definition of the haloaryltriazolinones to be used as starting materials in process (c) according to the invention for the preparation of the compounds of the general formula (I).
  • Q, R 1 , R 2 , R 3 and R 4 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, R 1 , R 2 , R 3 and R 4 have been given;
  • X 3 preferably represents fluorine or chlorine, in particular fluorine.
  • R 3 , R 4 and R 5 have the meanings given above and
  • X 4 represents halogen, preferably fluorine or chlorine, in particular fluorine, in the presence of a diluent, such as, for example, dimethyl sulfoxide and in the presence of an acid acceptor, such as, for example, potassium carbonate, at temperatures between 0 ° C. and 150 ° C. and to conventional Worked up way (see. The manufacturing examples).
  • a diluent such as, for example, dimethyl sulfoxide
  • an acid acceptor such as, for example, potassium carbonate
  • the starting materials of the formula (VHI) are known organic synthetic chemicals.
  • organic solvents are suitable as diluents for carrying out processes (a), (b) and (c) 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-dimethylace
  • Process (a) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
  • a suitable reaction auxiliary all customary inorganic or organic bases are suitable for the reaction with the acid halides of the formula (III).
  • these include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide , Ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and basic organic nitrogen Compounds such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-
  • Acidic catalysts are generally used as reaction aids for the reaction with the orthoesters of the formula (IV). Strong protonic acids such as e.g. Hydrochloric acid or hydrogen chloride, sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.
  • Strong protonic acids such as e.g. Hydrochloric acid or hydrogen chloride, sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.
  • 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 at temperatures between 10 ° C and 100 ° C.
  • Process (a) according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess.
  • the reactions are generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is stirred for several hours at the temperature required in each case.
  • Working up in the process according to the invention is carried out in each case by customary methods (cf. the production examples).
  • Processes (b) and (c) according to the invention are preferably carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium ⁇ hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, Ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and basic organic nitrogen compounds, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicy
  • reaction temperatures can be varied within a substantial range when carrying out processes (b) and (c) according to the invention. In general, temperatures between 0 ° C and 100 ° C, preferably at temperatures between 10 ° C and 80 ° C.
  • Processes (b) and (c) according to the invention are generally carried out under normal conditions. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess.
  • the reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the temperature required in each case.
  • Working up in the process according to the invention is carried out in each case by customary methods (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 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: Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
  • 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 compounds of formula (I) according to the invention are particularly suitable for the selective control of monocot and dicot weeds in monocot and dicot crops, such as. For example, in wheat and barley both in the pre-emergence and in the post-emergence process. To a certain extent, the compounds of the formula (I) also show fungicidal activity, for example against pyricularia oryzae, phytophthora infestans and venturia inaequalis.
  • 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 polymers Fabrics.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is liquid solvents and / or solid carriers
  • 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 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 emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used 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; Aryl carboxylic acids, such as, for example, di chlorpi colinic 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, for example, alachlor, acetochlor, butachlor, metazachach
  • 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 and watered with the active compound 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 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:

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

De nouvelles triazolinones substituées répondent à la formule générale (I), dans laquelle Q désigne oxygène ou soufre, R1 désigne alkyle halogéné, R3 désigne hydrogène ou halogène, R4 désigne cyano ou nitro, R2 désigne hydrogène ou des substituants divers, et R5 désigne des substituants divers. L'invention concerne également des procédés de préparation de ces triazolinones et leur utilisation comme herbicides.
PCT/EP1995/000466 1994-02-22 1995-02-09 Triazolinones substituees et leur utilisation comme herbicides WO1995022532A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU18084/95A AU1808495A (en) 1994-02-22 1995-02-09 Substituted triazolinones and their use as herbicides
EP95909695A EP0746550A1 (fr) 1994-02-22 1995-02-09 Triazolinones substituees et leur utilisation comme herbicides
PL95315970A PL315970A1 (en) 1994-02-22 1995-02-09 Substituted triazolynones and their application as herbicides
BR9506928A BR9506928A (pt) 1994-02-22 1995-02-09 Triazolinonas substituídas e seu uso como herbicidas
JP7521556A JPH09509923A (ja) 1994-02-22 1995-02-09 置換されたトリアゾリノン類及びその除草剤としての使用

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4405614.1 1994-02-22
DE4405614A DE4405614A1 (de) 1994-02-22 1994-02-22 Substituierte Triazolinone

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WO1995022532A1 true WO1995022532A1 (fr) 1995-08-24

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EP (1) EP0746550A1 (fr)
JP (1) JPH09509923A (fr)
CN (1) CN1150421A (fr)
AU (1) AU1808495A (fr)
BR (1) BR9506928A (fr)
CA (1) CA2183641A1 (fr)
DE (1) DE4405614A1 (fr)
HU (1) HU9602306D0 (fr)
PL (1) PL315970A1 (fr)
WO (1) WO1995022532A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000046184A1 (fr) * 1999-02-06 2000-08-10 Aventis Cropscience Gmbh Derive n2-phenylamidine
EP1178037A1 (fr) * 2000-08-04 2002-02-06 Aventis Cropscience S.A. Dérivés de phénylimidates fongicides
WO2003042191A1 (fr) * 2001-11-12 2003-05-22 Pfizer Products Inc. Benzamide et heteroarylamide utilises comme antagonistes du recepteur p2x7
US7071223B1 (en) 2002-12-31 2006-07-04 Pfizer, Inc. Benzamide inhibitors of the P2X7 receptor
US7176202B2 (en) 2002-12-31 2007-02-13 Pfizer Inc. Benzamide inhibitors of the P2X7 receptor
US7235657B2 (en) 2004-06-29 2007-06-26 Pfizer Inc. Methods for preparing P2X7 inhibitors
US8933107B2 (en) 2005-09-13 2015-01-13 Bayer Cropscience Ag Pesticide thiazolyloxy substituted phenylamidine derivatives

Families Citing this family (7)

* Cited by examiner, † Cited by third party
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EP1100789B1 (fr) * 1998-07-24 2005-02-09 Bayer CropScience AG Benzoylcyclohexanediones substituees
DE19914140A1 (de) 1999-03-27 2000-09-28 Bayer Ag Substituierte Benzoylpyrazole
DE19920791A1 (de) 1999-05-06 2000-11-09 Bayer Ag Substituierte Benzoylisoxazole
DE19921424A1 (de) 1999-05-08 2000-11-09 Bayer Ag Substituierte Benzoylketone
MXPA05007130A (es) * 2002-12-31 2005-08-26 Pfizer Prod Inc Inhibidores benzamida del receptor p2x7.
CN110950811B (zh) * 2018-09-27 2022-01-11 东莞市东阳光农药研发有限公司 三氮唑化合物及其在农业中的应用
US20230148602A1 (en) * 2020-03-23 2023-05-18 Nippon Soda Co., Ltd. Benzamide compound and herbicide

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EP0370332A1 (fr) * 1988-11-23 1990-05-30 Bayer Ag Hétérocycles contenant de l'azote N-arylés, procédés et produits intermédiaires pour leur préparation et leur application à titre d'herbicides et de régulateurs de croissance de végétaux
EP0597360A1 (fr) * 1992-11-12 1994-05-18 Bayer Ag N-phényle-triazolin (thi)ones substitués, procédés et produits intermédiaires pour leur préparation et leur utilisation comme herbicides, insecticides et acaricides
EP0609734A1 (fr) * 1993-02-05 1994-08-10 Bayer Ag Triazolinones substituées et leur utilisation comme herbicides
EP0617026A1 (fr) * 1993-03-26 1994-09-28 Bayer Ag 1-aryltriazolinones substitués

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
EP0370332A1 (fr) * 1988-11-23 1990-05-30 Bayer Ag Hétérocycles contenant de l'azote N-arylés, procédés et produits intermédiaires pour leur préparation et leur application à titre d'herbicides et de régulateurs de croissance de végétaux
EP0597360A1 (fr) * 1992-11-12 1994-05-18 Bayer Ag N-phényle-triazolin (thi)ones substitués, procédés et produits intermédiaires pour leur préparation et leur utilisation comme herbicides, insecticides et acaricides
EP0609734A1 (fr) * 1993-02-05 1994-08-10 Bayer Ag Triazolinones substituées et leur utilisation comme herbicides
EP0617026A1 (fr) * 1993-03-26 1994-09-28 Bayer Ag 1-aryltriazolinones substitués

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6893650B1 (en) 1999-02-06 2005-05-17 Bayer Cropscience Gmbh N2-phenylamidine derivatives
WO2000046184A1 (fr) * 1999-02-06 2000-08-10 Aventis Cropscience Gmbh Derive n2-phenylamidine
EP1178037A1 (fr) * 2000-08-04 2002-02-06 Aventis Cropscience S.A. Dérivés de phénylimidates fongicides
EP1178036A1 (fr) * 2000-08-04 2002-02-06 Aventis Cropscience S.A. Dérivés de phénylimidates fongicides
US6656967B2 (en) 2000-08-04 2003-12-02 Bayer Cropscience Sa Fungicidal phenylimidate derivatives
US7214677B2 (en) 2001-11-12 2007-05-08 Pfizer Inc. Benzamide, heteroarylamide and reverse amides
WO2003042191A1 (fr) * 2001-11-12 2003-05-22 Pfizer Products Inc. Benzamide et heteroarylamide utilises comme antagonistes du recepteur p2x7
US7235549B2 (en) 2001-11-12 2007-06-26 Pfizer Inc. Benzamide, heteroarylamide and reverse amides
US7071223B1 (en) 2002-12-31 2006-07-04 Pfizer, Inc. Benzamide inhibitors of the P2X7 receptor
US7176202B2 (en) 2002-12-31 2007-02-13 Pfizer Inc. Benzamide inhibitors of the P2X7 receptor
US7407956B2 (en) 2002-12-31 2008-08-05 Pfizer, Inc. Benzamide inhibitors of the P2X7 receptor
US7235657B2 (en) 2004-06-29 2007-06-26 Pfizer Inc. Methods for preparing P2X7 inhibitors
US8933107B2 (en) 2005-09-13 2015-01-13 Bayer Cropscience Ag Pesticide thiazolyloxy substituted phenylamidine derivatives

Also Published As

Publication number Publication date
CN1150421A (zh) 1997-05-21
DE4405614A1 (de) 1995-08-24
BR9506928A (pt) 1997-09-09
HU9602306D0 (en) 1996-10-28
CA2183641A1 (fr) 1995-08-24
PL315970A1 (en) 1996-12-23
JPH09509923A (ja) 1997-10-07
EP0746550A1 (fr) 1996-12-11
AU1808495A (en) 1995-09-04

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