EP1395565A1 - Benzoylpyrazoles substitues a action herbicide - Google Patents

Benzoylpyrazoles substitues a action herbicide

Info

Publication number
EP1395565A1
EP1395565A1 EP02738036A EP02738036A EP1395565A1 EP 1395565 A1 EP1395565 A1 EP 1395565A1 EP 02738036 A EP02738036 A EP 02738036A EP 02738036 A EP02738036 A EP 02738036A EP 1395565 A1 EP1395565 A1 EP 1395565A1
Authority
EP
European Patent Office
Prior art keywords
methyl
cyano
fluorine
chlorine
substituted
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP02738036A
Other languages
German (de)
English (en)
Inventor
Hans-Georg Schwarz
Klaus-Helmut Müller
Stefan Herrmann
Dorothee Hoischen
Kristian Kather
Stefan Lehr
Otto Schallner
Mark Wilhelm Drewes
Peter Dahmen
Dieter Feucht
Rolf Pontzen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1395565A1 publication Critical patent/EP1395565A1/fr
Withdrawn legal-status Critical Current

Links

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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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<
    • 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
    • A01N47/08—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<
    • A01N47/32—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing >N—CO—N< or >N—CS—N< groups directly attached to a cycloaliphatic ring
    • 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<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • 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<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; 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
    • A01N47/28—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
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to new substituted benzoylpyrazoles, processes for their preparation and their use as herbicides.
  • Q represents O (oxygen) or S (sulfur),
  • R 1 represents optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl
  • R 2 stands for hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkoxycarbonyl or cycloalkyl,
  • R 3 , R 4 independently of one another for hydrogen, nitro, cyano, carboxy,
  • R 5 represents hydrogen or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylthio, arylsulfinyl, arylsulfonyl, arylalkyl, or for the grouping -C (Q) -Z .
  • Y represents hydrogen or in each case optionally substituted alkyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenyl, alkenylsulfonyl, alkenylcarbonyl, alkynyl, alkynylcarbonyl, cycloalkyl, cycloalkylcarbonyl, cycloalkylalkyl, phenyl, phenylsulfonyl, phenylalkylphenyl, phenylcarbonyl, phenylcarbonyl, phenylcarbonyl, Phenylalkylcarbonyl or phenylcarbonylalkyl, and
  • alkyl for alkyl, alkoxy, alkylthio or alkylamino each substituted by cyano, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl,
  • alkylcarbonyl alkoxycarbonyl, alkoxyamino, alkylhydrazino, alkylcarbonylhydrazino, alkoxycarbonylhydrazino, alkylsulfonylhydrazino, N-alkylalkoxyamino, dialkylhydrazino, alkenyloxy, alkenylamino, alkenyloxyamino, alkynyloxy, alkynylaminoalkyl, cycloalkylo, cycloalkyl, cycloalkylo, cycloalkyl, cycloalkylo, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl,
  • Arylalkoxy, arylalkylthio, arylalkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, the grouping -N (heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio or heterocyclic, - Including all possible tautomeric forms of the compounds of the general formula (I) and the possible salts of the compounds of the general formula (I) -
  • Q is preferably O.
  • R 1 preferably represents alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen, -C - alkoxy, C ⁇ - C 4 alkylthio, dC 4 - alkylsulfinyl or dC 4 - alkylsulfonyl, for each alkenyl optionally substituted by cyano or halogen or alkynyl each having 2 to 6 carbon atoms, or for cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or C 1 -C 4 -alkyl.
  • R 2 preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, each alkyl, alkoxy or alkoxycarbonyl optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, each having up to 6 carbon atoms, alkylthio optionally substituted by halogen with 1 to 6 carbon atoms, or for cycloalkyl with 3 to 6 carbon atoms optionally substituted by cyano, halogen or QQ-alkyl.
  • R 3 , R 4 preferably independently of one another represent hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, each optionally by halogen, C_-C4-alkoxy, C1-C4-alkylthio, C_-C_ ⁇ - alkylsulfinyl or C1 - C4- alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having up to 4 carbon atoms in the alkyl groups, or for alkylamino, dialkylamino, dialkylaminocarbonyl or di- alkylaminosulfonyl with up to 4 carbon atoms in each of the alkyl groups.
  • R 5 preferably represents hydrogen, in each case optionally substituted by cyano, halogen or -CC 4 -alkoxy alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl optionally substituted by cyano or halogen or alkynyl each having 3 to 6 carbon atoms in the alkenyl or alkynyl groups, for cycloalkyl or cycloalkylalkyl each having 3 to 4 substituted by cyano, halogen or dC 4 alkyl
  • Y preferably represents hydrogen, alkyl optionally substituted by cyano, carbamoyl, halogen, Cj-C 4 -alkoxy or d-Gralkoxy-carbonyl having 1 to 6 carbon atoms, optionally substituted by halogen alkylsulfonyl having 1 to 6 carbon atoms, each optionally in each case alkylcarbonyl substituted by cyano, halogen or -CC 4 alkoxy,
  • Alkoxycarbonyl or alkylaminocarbonyl each with 1 to 6 carbon atoms in the alkyl groups, for dialkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl groups, for alkenyl, alkenylcarbonyl, alkynyl or alkynylcarbonyl, each optionally substituted by cyano or halogen, each with up to 6 carbon atoms, for optionally by
  • Halogen substituted alkenylsulfonyl with up to 6 carbon atoms for in each case optionally substituted by cyano, halogen or -CC 4 -alkyl cycloalkyl, cycloalkylcarbonyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 3 carbon atoms in the alkyl part, or for in each case optionally by nitro, cyano, carbamoyl, halogen, C ⁇ -C 4 -alkyl, C 4 haloalkyl, dC -
  • alkenyloxy, alkenylamino, alkenyloxyamino, alkynyloxy or alkynylamino each optionally substituted by halogen, each having 2 to 6 carbon atoms,
  • cycloalkyl for cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylhydrazino, each optionally substituted by cyano, halogen or C 1 -C 4 -alkyl,
  • N (heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkylamino, where the heterocyclyl group in each case up to 10 carbon atoms and additionally at least one heteroatom selected from the series nitrogen (but not more than 5 N atoms), oxygen (at most however 2 O atoms), sulfur (at most however 2 S-
  • R 2 particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, in each case optionally by cyano, fluorine,
  • R 3 , R 4 are particularly preferably, independently of one another, hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, each in each case by fluorine, chlorine, methoxy, ethoxy, methylthio,
  • Ethylthio methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- , s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, for methylamin
  • R 5 particularly preferably represents hydrogen, in each case optionally by
  • methoxyamino, ethoxyamino each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl or ethylsulfonyl , n- or i-propoxyamino, n-, i-, s- or t-butoxyamino, methylhydrazino, ethylhydrazino, n- or i-propylhydrazino, n-, i-, s- or t-butylhydrazino, for N- Methyl methoxyamino or dimethylhydrazino,
  • Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t- Butylthio, difluoromethylthio, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted monocyclic or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylamino, the grouping -N (heterocyclyl), heteroxyclylalkyl, cyclylalkylamino from the series Furyl, Furyloxy, Furylamino, Furylmethyl, Furylmethoxy, Furylmethylamino, Tetrahydrofuryl, Tetrahydrofuryloxy, Tetrahydrofu
  • R 1 very particularly preferably represents methyl, ethyl, n- or i-propyl, cyclopropyl, cyclopentyl or cyclohexyl.
  • R 2 very particularly preferably represents hydrogen, in each case methyl, ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy,
  • Methoxycarbonyl or ethoxycarbonyl each optionally by Fluorine and / or chlorine substituted methylthio or ethylthio, or for cyclopropyl optionally substituted by fluorine, chlorine or methyl.
  • R 3 , R 4 are particularly preferably independently of one another hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl,
  • Trifluoromethyl dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylaminosulfonyl or dimethyl.
  • R 5 very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl, n- or i-butyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, and methoxy, ethoxy, n- or i - Propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino or dimethylamino, each optionally with fluorine and / or chlorine-substituted propenyl, butenyl, propynyl or butynyl, for each cyclopropy
  • Cyclohexylmethyl or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-Propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylmethyl or phenylethyl, or for the grouping -C (Q) -Z.
  • Y very particularly preferably represents hydrogen, in each case methyl or ethyl optionally substituted by cyano, fluorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, for methylsulfonyl or ethylsulfonyl optionally substituted by fluorine and / or chlorine, in each case optionally by cyano, fluorine, Chlorine, methoxy or ethoxy substituted tes acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl or ethylaminocarbonyl, for dimethylaminocarbonyl, for propenyl optionally substituted by fluorine, chlorine or bromine, propenylcarbonyl, propynyl or propynylcarbonyl, each optionally substituted by cyano, fluorine, chlorine or methyl cyclopropylcarbonyl,
  • -N (heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkylamino from the series furyl, furyloxy, furylamino, furylmethyl, furylmethoxy, furylmethylamino, tetrahydrofuryl, tetrahydrofuryloxy, tetra-hydrofurylamino, methyl, furl Dioxolanylmethoxy,
  • a very particularly preferred group are those compounds of the general formula (I) in which
  • R 1 represents methyl, ethyl, n- or i-propyl
  • R 2 represents hydrogen, methyl, ethyl, methoxycarbonyl, ethoxycarbonyl, methylthio or ethylthio,
  • R 3 , R 4 independently of one another for hydrogen, nitro, cyano, fluorine, chlorine, bromine,
  • R 5 for hydrogen, for methyl, ethyl, n- or i-propyl, for methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl or ethylsulfonyl, each optionally with fluorine and / or chlorine-substituted propenyl, butenyl, propynyl or butynyl, or stands for cyclopropyl,
  • Y for hydrogen, for each methyl or ethyl optionally substituted by cyano, fluorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, for each methylsulfonyl or ethylsulfonyl optionally substituted by fluorine and / or chlorine, each in each case optionally by cyano,
  • radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • Saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl, also in combination with heteroatoms, such as, for example, in alkoxy, alkylthio or alkylamino, are each straight-chain or branched. Unless otherwise stated, preference is given to hydrocarbon chains having 1 to 6 carbon atoms.
  • Aryl stands for aromatic, mono- or polycyclic hydrocarbon rings, e.g. Phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, especially phenyl.
  • Heterocyclyl stands for saturated, unsaturated or aromatic, ring-shaped compounds in which at least one ring member has a hetero atom, i.e. is an atom other than carbon. If the ring contains several heteroatoms, these can be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur. If this ring contains several oxygen atoms, they are not adjacent. If appropriate, the ring-shaped compounds together with further carbocyclic or heterocyclic, fused or bridged rings together form a polycyclic ring system. A polycyclic ring system can be linked via the heterocyclic ring or a fused-on carbocyclic ring. Mono- or bicyclic ring systems are preferred, in particular monocyclic ring systems with 5 or 6 ring members and bicyclic ring systems with 7 to 9 ring members.
  • Cycloalkyl stands for saturated, carbocyclic compounds which optionally form a polycyclic ring system with further carbocyclic, fused or bridged rings. Unless otherwise stated, cyclopropyl, cyclopentyl and cyclohexyl are preferred.
  • the new substituted benzoylpyrazoles of the general formula (I) are notable for strong and selective herbicidal activity.
  • the new substituted benzoylpyrazoles of the general formula (I) are obtained if
  • R 1 , R 2 and Y have the meaning given above,
  • Formula (II) provides a general definition of the pyrazoles to be used as starting materials in process (a) according to the invention for the preparation of compounds of the general formula (I).
  • R 1 , R 2 and Y preferably have those meanings which are preferred, particularly preferred or very particularly preferred for R 1 , R already in connection with the description of the compounds of the general formula (I) according to the invention 2 and Y have been specified.
  • the starting materials of the general formula (II) are known and or can be prepared by processes known per se (cf. EP-A-240 001).
  • Formula (III) provides a general definition of the substituted benzoic acids to be used further as starting materials in process (a) according to the invention.
  • Q, R 3 , R 4 , R 5 and Z preferably have those meanings which are preferred, particularly preferred or very particularly preferred for Q in connection with the description of the compounds of the formula (I) according to the invention , R 3 , R 4 , R 5 and Z were specified.
  • the starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf. JP-A-112 92 849 and preparation examples).
  • R represents alkyl, in particular methyl or ethyl
  • benzoic esters of the general formula (purple) required as products are known and / or can be prepared by processes known per se
  • R represents alkyl, in particular methyl or ethyl
  • X represents halogen, in particular fluorine, chlorine or bromine, - or, if appropriate, with corresponding iso (thio) cyanates -
  • an acid acceptor e.g. Potassium carbonate or triethylamine
  • a diluent such as e.g.
  • R represents alkyl, in particular methyl or ethyl
  • reaction auxiliary such as triethylamine
  • a diluent such as acetonitrile or Toluene
  • Formula (Ia) provides a general definition of the substituted benzoylpyrazoles to be used as starting materials in process (b) according to the invention for the preparation of compounds of the general formula (I).
  • Q, R 1 , R 2 , R 3 , R 4 , R 5 and Z preferably have those meanings which are already preferred above in connection with the description of the compounds of the general formula (I) according to the invention, have been specified particularly preferably or very particularly preferably for Q, R 1 , R 2 , R 3 , R 4 , R 5 and Z.
  • the starting materials of the general formula (Ia) are new compounds according to the invention; they can be prepared by process (a) according to the invention.
  • Formula (IV) provides a general definition of the compounds to be used further as starting materials in process (b) according to the invention.
  • Y preferably has the meaning which has already been given as preferred, particularly preferred or very particularly preferred for Y in connection with the description of the compounds of the general formula (I) according to the invention;
  • X preferably represents fluorine, chlorine, bromine or iodine, in particular chlorine or bromine.
  • the starting materials of the general formula (IV) are known synthetic chemicals.
  • the formulas (V) and (VI) generally define the compounds to be used further as starting materials in process (c) for the preparation of compounds of the general formula (I).
  • Q, R 1 , R 2 , R 3 , R 4 , R 5 , X and Z preferably have the meaning already given above in connection with the description of the general Formula (I) has been given as preferred, particularly preferred or very particularly preferred for Q, R 1 , R 2 , R 3 , R 4 , R 5 , X and Z.
  • the starting materials of the general formula (VI) are known organic compounds.
  • the starting materials of the general formula (V) can be prepared by processes known per se.
  • the compounds to be used as starting materials in process (d) according to the invention for the preparation of compounds of the general formula (I) are generally defined by the formulas (VII) and (VIII).
  • Q, R 1 , R 2 , R 3 , R 4 , R 5 , Y and Z preferably have that
  • the starting materials of the general formula (VIII) are known synthetic chemicals.
  • the starting materials of the general formula (VII) can be prepared by processes known per se.
  • Formula (IX) provides a general definition of the compounds to be used as starting materials in process ( ⁇ ) according to the invention for the preparation of compounds of the general formula (purple).
  • R 3 , R 4 or R 5 preferably have the meaning which has already been given as preferred, particularly preferred or very particularly preferred in connection with the description of the general formula (I).
  • Formula (X) provides a general definition of the compounds to be used as starting materials in process ( ⁇ ) according to the invention for the preparation of compounds of the formula (purple).
  • Q, R 3 and R 4 preferably have the meaning which has already been given as preferred, particularly preferred or very particularly preferred in connection with the description of the general formula (I).
  • the starting materials of the general formula (X) can be prepared by processes known per se.
  • Process (a) according to the invention for the preparation of the new substituted benzoylpyrazoles of the general formula (I) is preferably carried out using a dehydrating agent.
  • a dehydrating agent The usual chemicals suitable for binding water can be considered.
  • Examples include dicyclohexylcarbodiimide, propanephosphonic anhydride and carbonyl-bis-imidazole.
  • Dicyclohexylcarbodiimide and propanephosphonic anhydride may be mentioned as particularly suitable dehydrating agents.
  • Process (a) according to the invention for the preparation of the new substituted benzoylpyrazoles of the general formula (I) is optionally carried out using a reaction auxiliary.
  • Examples include sodium cyanide, potassium cyanide, acetone cyanohydrin, 2-
  • Trimethylsilyl cyanide may be mentioned as a particularly suitable reaction auxiliary.
  • Processes (a) and (b) according to the invention are preferably carried out using one or more reaction auxiliaries.
  • Suitable reaction auxiliaries for processes (a) and (b) according to the invention are generally the customary inorganic or organic bases or acid acceptors.
  • alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates such as sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, Sodium or potassium - methanolate, ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; basic organic nitrogen compounds, such as trimethylamine,
  • Phase transfer catalysts are also suitable as further reaction auxiliaries for processes (a) and (b) according to the invention. As examples of such
  • Tetrabutylammonium bromide Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyl trioctylammonium chloride, hexadecyl trimethylammonium chloride, hexadecyl trimethylammonium bromide,
  • the processes according to the invention for the preparation of the compounds of the general formula (I) are preferably carried out in each case using one or more diluents.
  • the main diluents for carrying out processes (a) and (b) according to the invention are inert organic solvents.
  • 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 butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Esters such as
  • reaction temperatures can be carried out when the inventive compounds
  • Processes (a) and (b) can be varied over a wide range. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • the processes according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that 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:
  • Dactyloctenium Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Sagaria, Setaria, Setaria. Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.
  • the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the active compounds according to the invention 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 show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.
  • the active compounds according to the invention can also be used to control animal pests and fungal or bacterial plant diseases. If necessary, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • Plants are understood to mean all plants and plant populations, such as desired and undesirable wild plants or cultivated plants (including naturally occurring cultivated plants).
  • Cultivated plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and or dispersants and / or foam-generating agents.
  • water is used as an extender, e.g. also organic
  • Solvents are used as auxiliary solvents.
  • aromatics such as xylene, toluene, or alkyl naphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as
  • Possible solid carriers are: e.g. 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, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,
  • natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
  • synthetic rock powders such as highly disperse silica, aluminum oxide and silicates
  • coconut shells, corn cobs and tobacco stems as emulsifying and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite waste liquor and
  • 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, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds as a mixture with known herbicides and / or with substances which improve the compatibility with crop plants (“safeners”), finished formulations or tank mixes being possible mixtures with weed control compositions which contain one or more known herbicides and a safener are also possible.
  • safeners substances which improve the compatibility with crop plants
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflubutamid, Benazolin (-ethyl), Benulfureson -methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxime,
  • Imazethapyr Imazosulfuron, Iodosulfuron (-methyl, -sodium), Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Motrioneacetametha , Metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron, metribuzin, metsulfuron (-methyl), molinate, monolinuron,
  • Known safeners are also suitable for the mixtures, for example AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA-24, Dichlormid, Dymron, Fenclorim, Fenchlorazole (-ethyl), Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl ), MCPA, Mecoprop (-P), Mefenpyr (-diethyl), MG-191, Oxabetrinil, PPG-1292, R-29148.
  • 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 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • plants and their parts can be treated according to the invention.
  • transgenic plants and plant cultivars which may be obtained by genetic engineering methods Combination with conventional methods have been obtained (Genetically Modified Organisms) and their parts treated.
  • the term "parts” or “parts of plants” or “plant parts” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with certain properties (“traits”) which have been obtained both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening of the activity spectrum and / or an enhancement of the effect of the substances and agents which can be used according to the invention - also in combination with other agrochemical active substances - better plant growth of the cultivated plants, increased tolerance of the cultivated plants to high or low temperatures Tolerance of cultivated plants against drought or against water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which is beyond the actual expected effects go beyond.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous, valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering performance, easier harvesting, easier acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products.
  • transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits of apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted.
  • the traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • the traits that are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example the “PAT” gene).
  • herbicidal active compounds for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example the “PAT” gene).
  • the genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants. Examples of “Bt plants” are maize, cotton, soybean and
  • Potato varieties named under the trade names YIELD GARD® e.g. corn, cotton, soy
  • KnockOut® e.g. corn
  • StarLink® e.g. corn
  • Bollgard® cotton
  • Nucotn® cotton
  • NewLeaf® potato
  • herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties which are sold under the trade names Roundup Ready® (tolerance against glyphosate, for example corn, cotton, soybeans), Liberty Link® (tolerance against Phosphinotricin, such as rapeseed), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas such as corn) are sold.
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (eg maize). It goes without saying that these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the plants listed can be treated according to the invention particularly advantageously with the compounds of the general formula I or the active compound mixtures according to the invention, the above-mentioned synergistic effects also occurring with the transgenic plants or plant cultivars in addition to the good control of the weed plants.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values using the
  • the lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • Example (IIIa-1) Analogously to Example (IIIa-1), it is also possible, for example, to prepare the compounds of the general formula (purple) listed in Table 3 below.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area.
  • the active ingredient concentration in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.
  • Example B the compounds according to Preparation Example 1, 2, 3, 4, 5 and 6, with good tolerance to cultivated plants, such as, for example, maize, show a strong action against weeds.
  • Example B the compounds according to Preparation Example 1, 2, 3, 4, 5 and 6, with good tolerance to cultivated plants, such as, for example, maize, show a strong action against weeds.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants 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 in
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

Landscapes

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

Abstract

Benzoylpyrazoles de formule générale (I) dans laquelle Q, R<1>, R<2>, R<3>, R<4>, R<5>, Y et Z possèdent la signification figurant dans le descriptif. La présente invention concerne également des procédés et des produits intermédiaires pour la production desdits benzoylpyrazoles et l'utilisation de ces derniers en tant qu'herbicides.
EP02738036A 2001-05-21 2002-05-08 Benzoylpyrazoles substitues a action herbicide Withdrawn EP1395565A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE10124578 2001-05-21
DE10124578 2001-05-21
DE10138577 2001-08-06
DE10138577A DE10138577A1 (de) 2001-05-21 2001-08-06 Substituierte Benzoylpyrazole
PCT/EP2002/005046 WO2002094792A1 (fr) 2001-05-21 2002-05-08 Benzoylpyrazoles substitues a action herbicide

Publications (1)

Publication Number Publication Date
EP1395565A1 true EP1395565A1 (fr) 2004-03-10

Family

ID=26009347

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02738036A Withdrawn EP1395565A1 (fr) 2001-05-21 2002-05-08 Benzoylpyrazoles substitues a action herbicide

Country Status (15)

Country Link
US (1) US7635664B2 (fr)
EP (1) EP1395565A1 (fr)
JP (1) JP4549023B2 (fr)
KR (1) KR100868564B1 (fr)
CN (1) CN1256329C (fr)
AR (1) AR035241A1 (fr)
AU (1) AU2002312882B2 (fr)
BR (1) BR0209949A (fr)
CA (1) CA2447674A1 (fr)
DE (1) DE10138577A1 (fr)
MX (1) MXPA03010613A (fr)
PL (1) PL363842A1 (fr)
RU (1) RU2301226C2 (fr)
UA (1) UA75657C2 (fr)
WO (1) WO2002094792A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL2688885T3 (pl) * 2011-03-22 2016-12-30 Amidy kwasu N-(1,3,4-oksdiazol-2-ilo)arylokarboksylowego i ich zastosowanie jako herbicydów
EP3508480A1 (fr) * 2018-01-08 2019-07-10 Basf Se Composés de benzadine et leur utilisation comme herbicides
CN109438287A (zh) * 2018-12-10 2019-03-08 武汉罗化科技有限公司 一种绿谷隆的制备方法
CN112624973B (zh) * 2019-10-08 2024-01-30 沈阳中化农药化工研发有限公司 一种羧酸酯类化合物及其应用
CN113801079B (zh) * 2021-10-11 2024-01-09 上海安谱实验科技股份有限公司 一种呋虫胺代谢物uf的合成方法

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3431272A1 (de) * 1984-08-25 1986-03-06 Bayer Ag, 5090 Leverkusen Substituierte phenylharnstoffe
JPH0730031B2 (ja) 1986-04-02 1995-04-05 日産化学工業株式会社 ２―ピラゾリン―５―オン類の製造法
US4986845A (en) 1988-07-15 1991-01-22 Nissan Chemical Industries Ltd. Pyrazole derivatives and herbicides containing them
JPH01292849A (ja) 1988-08-05 1989-11-27 Semiconductor Energy Lab Co Ltd 電子装置作製方法
DE4417837A1 (de) * 1994-05-20 1995-11-23 Basf Ag Substituierte 3-Phenylpyrazole
DE59605056D1 (de) 1995-02-24 2000-05-31 Basf Ag Phenyldiketon-derivate als herbizide
WO1997018196A1 (fr) * 1995-11-15 1997-05-22 Zeneca Limited Composes herbicides a base de pyrazole substitue
DE19542520A1 (de) * 1995-11-15 1997-05-22 Basf Ag Substituierte 1-Methyl-3-phenylpyrazole
DE69728761T2 (de) 1996-04-26 2004-08-12 Nippon Soda Co. Ltd. Heterocyclisch substituierte benzolderivate und herbizide
EP0922032A1 (fr) * 1996-06-06 1999-06-16 E.I. Du Pont De Nemours And Company Pyridinylcetones et pyrazolylphenylcetones herbicides
BR9806778B1 (pt) 1997-01-17 2009-12-01 derivado de benzoìla substituìda por 3-heterociclila, composto, processo para a preparação do dito derivado de benzoìla substituìda por 3-heterociclila, derivado de ácido benzóico substituìdo por 3-heterociclila, composição e uso do referido derivado de benzoìla substutuìda por 3-heterociclila.
WO1998031676A1 (fr) 1997-01-17 1998-07-23 Basf Aktiengesellschaft Procede de preparation de 2-chloro-3-(4,5-dihydroisoxazol-3-yle)-acides benzoiques contenant du soufre
US6165944A (en) 1997-01-17 2000-12-26 Basf Aktiengesellschaft 4-(3-heterocyclyl-1-benzoyl) pyrazoles and their use as herbicides
EP1003736B1 (fr) 1997-08-07 2006-04-12 Basf Aktiengesellschaft 4-benzoyl-pyrazoles substitues
WO1999010328A1 (fr) * 1997-08-07 1999-03-04 Basf Aktiengesellschaft 4-benzoyl-pyrazole heterocycliquement substitue comme herbicides
JPH11292849A (ja) * 1998-04-03 1999-10-26 Nippon Soda Co Ltd ベンゾイルピラゾール化合物および除草剤
DE19914140A1 (de) 1999-03-27 2000-09-28 Bayer Ag Substituierte Benzoylpyrazole
US7546055B2 (en) 2006-03-09 2009-06-09 Kabushiki Kaisha Toshiba Image forming apparatus

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO02094792A1 *

Also Published As

Publication number Publication date
RU2003136829A (ru) 2005-05-27
DE10138577A1 (de) 2002-11-28
PL363842A1 (en) 2004-11-29
KR100868564B1 (ko) 2008-11-13
KR20030096350A (ko) 2003-12-24
UA75657C2 (en) 2006-05-15
BR0209949A (pt) 2004-04-06
CA2447674A1 (fr) 2002-11-28
CN1511143A (zh) 2004-07-07
AR035241A1 (es) 2004-05-05
WO2002094792A1 (fr) 2002-11-28
MXPA03010613A (es) 2004-03-09
RU2301226C2 (ru) 2007-06-20
AU2002312882B2 (en) 2008-06-05
CN1256329C (zh) 2006-05-17
US20040110640A1 (en) 2004-06-10
US7635664B2 (en) 2009-12-22
JP2004536806A (ja) 2004-12-09
JP4549023B2 (ja) 2010-09-22

Similar Documents

Publication Publication Date Title
EP1504005A2 (fr) Pyrazolopyrimidine-4-one substituee
WO2004067518A1 (fr) Procede et appareil de collage en surface d&#39;une bande de papier ou de carton
DE10116399A1 (de) Substituierte Azolazin(thi)one
WO2002006244A1 (fr) Anilide de l&#39;acide sulfonique herbicide heterocycliquement substitue
DE10034800A1 (de) Substituierte Benzostickstoffheterocyclen
EP1263738B1 (fr) Benzoylcyclohexenones substituees
EP1373228A1 (fr) Fluoroalcoxyphenylsulfonylurees substituees
EP1387831A1 (fr) Arylcetones substituees
WO2001090102A2 (fr) 6-heteroclyclyl-3-oxo-3,4-dihydro-quinoxalines
EP1395565A1 (fr) Benzoylpyrazoles substitues a action herbicide
EP1480944A2 (fr) Arylcetone substituee
WO2002096884A2 (fr) Benzoyl-cetones substituees
EP1773825B1 (fr) Composes thienylsulfonylaminocarbonyles substitues par dioxazinyle
WO2002034725A1 (fr) Phenyluraciles substitues
WO2004048348A1 (fr) 2-aryl-1,2,4-triazine-3,5-di(thi)ones substitues utilises en tant qu&#39;herbicides
WO2002020487A1 (fr) 1-aryl-pyridin-2-(thi)ones substituees
WO2003070696A2 (fr) Arylcetones substituees
WO2003006461A1 (fr) Heterocycles benzo-azotes substitues
DE10037149A1 (de) Substituierte Arylketone
DE10117673A1 (de) Substituierte Fluoralkoxyphenylsulfonylamino(thio)carbonyl-triazolin(thi)one
EP1392660B1 (fr) Benzoylcyclohexenone substituees et leur utilisation en tant qu&#39;herbicides
WO2003092380A1 (fr) Derives de pyridin-3-carbonyle 2,6 substitues utilises comme produits phytosanitaires a action herbicide
DE10138576A1 (de) Substituierte Benzoylcyclohexenone
DE10028687A1 (de) Substituierte Benzoylcyclohexenone
DE10136449A1 (de) Substituierte Arylketone

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20031222

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Effective date: 20111213