WO1999005125A1 - N-aryle-n-thioxocarbonyle-sulfonamides substitues s'utilisant comme herbicides - Google Patents

N-aryle-n-thioxocarbonyle-sulfonamides substitues s'utilisant comme herbicides Download PDF

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Publication number
WO1999005125A1
WO1999005125A1 PCT/EP1998/004325 EP9804325W WO9905125A1 WO 1999005125 A1 WO1999005125 A1 WO 1999005125A1 EP 9804325 W EP9804325 W EP 9804325W WO 9905125 A1 WO9905125 A1 WO 9905125A1
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Prior art keywords
cyano
optionally
carbon atoms
optionally substituted
halogen
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PCT/EP1998/004325
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German (de)
English (en)
Inventor
Karl-Heinz Linker
Roland Andree
Otto Schallner
Markus Dollinger
Mark Wilhelm Drewes
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Bayer Aktiengesellschaft
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Priority to AU88608/98A priority Critical patent/AU8860898A/en
Publication of WO1999005125A1 publication Critical patent/WO1999005125A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • 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
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; 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<
    • A01N47/34—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
    • 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
    • C07D231/16—Halogen atoms or nitro radicals
    • 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
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy 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
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having 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
    • C07D253/075—Two hetero atoms, in positions 3 and 5

Definitions

  • the invention relates to new substituted N-aryl-N-thioxocarbonyl-sulfonamides, processes for their preparation and their use as herbicides.
  • the object of the present invention is to provide substituted N-aryl-N-thiocarbonylsulfonamides which have a herbicidal action.
  • R 1 represents hydrogen, cyano or halogen
  • R 2 represents hydroxy, cyano, nitro, thiocarbamoyl, halogen or one of the following groups -R 5 , -OR 5 , -O-CO-R 5 , represents one of the following groups -R 5 , -OR 5 , -SR 5 , -N (R 6 , R 7 ),
  • R 4 represents the grouping -R 5 .
  • R 5 represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
  • R 6 represents hydrogen or alkyl which is optionally substituted
  • R 7 represents hydrogen, in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or together with R 6 represents alkanediyl which may be interrupted by oxygen, and
  • Q 1 and Q 2 represent oxygen or sulfur
  • R 8 for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, Dialkylamino, cycloalkyl or cycloalkylalkyl, and
  • R 9 represents hydrogen, hydroxy, amino, cyano, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylamino, Alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl, where optionally two adjacent radicals - R 8 and R 8 , R 9 and R 9 or R 8 and R 9 - together for optionally substituted and / or optionally by oxygen, sulfur or a group from the series -SO-, SO 2 -, -NH- or -N (alkyl) - at the beginning (or at the end) or interrupted alkanediyl or alkenediyl within the hydrocarbon chain, and
  • the invention preferably relates to compounds of the formula (I) in which
  • R 1 represents hydrogen, cyano or halogen
  • R 2 represents hydroxy, cyano, nitro, thiocarbamoyl, halogen or one of the following groups -R 5 , -OR 5 , -O-CO-R 5 ,
  • R 3 represents one of the following groupings -R 5 , -OR 5 , -SR 5 , -N (R 6 , R 7 ),
  • R 4 represents the grouping -R 5 .
  • R 5 for optionally substituted by cyano, halogen or C1 -C4 alkoxy
  • Alkyl with 1 to 6 carbon atoms each for alkenyl optionally substituted by halogen or alkynyl each with 2 to 6 carbon atoms, for each optionally substituted by cyano, halogen or C1-C4-alkyl
  • Cycloalkyl or cycloalkylalkyl each with 3 to 6 carbon atoms in the Cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each aryl or arylalkyl, each substituted by cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, -C-C4-alkoxy or C1-C4-haloalkoxy or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally substituted by cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 4 -C 4 haloalkoxy Heterocyclyl or heterocyclylalkyl each having 2 to 6 carbon atoms and 1 to 3 nitrogen atoms and / or 1 or 2 oxygen
  • R 6 for hydrogen, for optionally substituted by cyano, halogen or C1-C4-alkoxy alkyl having 1 to 6 carbon atoms, for each optionally substituted by halogen alkenyl or alkynyl each having 2 to 6 carbon atoms, for each optionally substituted by cyano, halogen or C1-C4-
  • R 7 for hydrogen, for alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C1-C4-alkoxy, for each optionally substituted by halogen alkenyl or alkynyl each with 2 to 6 carbon atoms, for each optionally substituted by cyano, halogen or C1 -C4- Alkyl substituted cycloalkyl or cycloalkylalkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by cyano, nitro, halogen, C1-C4-alkyl, C 1 -C 4 -haloalkyl, C1-C4-alkoxy or C1 -C4 haloalkoxy-substituted aryl or arylalkyl each having 6 or 10
  • Q 1 and Q 2 represent oxygen or sulfur
  • R 8 for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, for alkyl optionally substituted by cyano, halogen or C1-C4-alkoxy having 1 to 6 carbon atoms, for alkenyl or alkynyl optionally substituted by halogen in each case 2 to 6 carbon atoms, each for alkoxy or alkoxycarbonyl optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by halogen Alkenyloxy or alkynyloxy each having 3 to 6 carbon atoms, for alkylthio having 1 to 6 carbon atoms optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, for each optionally substituted by halogen alkenylthio or alkynylthio each having 3 to 6
  • the invention particularly relates to the compounds of formula (I) in which
  • R 1 represents hydrogen, cyano, fluorine or chlorine
  • R 2 represents hydroxy, cyano, nitro, thiocarbamoyl, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy,
  • R 3 represents one of the following groupings -R 5 , -OR 5 , -SR 5 , -N (R 6 , R 7 ),
  • R 4 represents the grouping -R 5 .
  • R 5 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for each optionally substituted by fluorine, chlorine or bromine Ethenyl, propenyl,
  • R 6 for hydrogen each optionally by cyano, fluorine, methoxy or
  • Cyclohexylmethyl or for each optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy substituted phenyl or benzyl,
  • R 7 for hydrogen, for each methyl, ethyl, n- or i-propyl, n- or i-butyl optionally substituted by cyano, fluorine, methoxy or ethoxy, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine or chlorine , for in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl cyclopropyl, cyclobutyl, cyclopentyl,
  • Q 1 and Q 2 represent oxygen or sulfur
  • R 8 for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, n- which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , i-, s- or t-butyl, for in each case optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl,
  • R 9 represents hydrogen, hydroxy, amino, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for each 5 methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for each optionally by cyano, fluorine, chlorine, methoxy or ethoxy substituted methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for methylamino, ethylamino, n- or i-propylamino, n
  • the saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl — in each case in connection with heteroatoms, such as in alkoxy, alkylthio or alkylamino — are in each case straight-chain or branched.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • the new substituted N-aryl-N-thioxocarbonylsulfonamides of the general formula (I) are notable for strong and selective herbicidal activity.
  • R 1 , R 2 , R 3 and R 4 have the meanings given in the list below:
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 4
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 10
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 18
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 20
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 22
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 24
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 26
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 28
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 30
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 32
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 34
  • R 1 , R 2 , R 3 and R have, for example, those given above in Group 1
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 38
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 40
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 42
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 44
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 46
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 48
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 50
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 52
  • R 1 , R 2 , R 3 and R have, for example, those given above in Group 1
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 54
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 62
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 64
  • R 1 , R 2 , R 3 and R have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 66
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 68
  • R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • Group 70
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 , R 3 and R 4 have, for example, those given in Group 1 above
  • R 1 , R 2 R 4 and Z have the meaning given above,
  • R 3 has the meaning given above and
  • the starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. EP-A-408 382, EP-A-563 384, EP-A-609 734, EP-A-648 749, US-A-4 818 275, US-A-4 909 831, WO-A-95/17391, WO-A-95/29158, WO-A-95/29168, WO-A-95/30661, WO-A-96/18618).
  • Formula (III) provides a general definition of the halothioxocarbonyl compounds to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I).
  • R 3 preferably or in particular has the meaning already given above in connection with the description of the compounds of the formula according to the invention
  • (I) was preferably or as particularly preferred for R 3 ;
  • X preferably represents fluorine, chlorine, bromine or iodine, in particular chlorine or bromine.
  • the starting materials of the general formula (III) are known synthetic chemicals.
  • Formula (II) provides a general definition of the N-arylsulfonamides to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I).
  • R 1, R 2, R 4 and Z preferably or in particular those meanings which have already been mentioned above in connection with the description of the compounds of formula (I) as preferred or as particularly preferred for R 1, R 2 , R 4 and Z were given.
  • Suitable reaction auxiliaries for carrying out the process according to the invention for the preparation of the compounds of the formula (I) are generally the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as, for example, 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 methoxide, ethanolate, n or i propanolate, n, i, s or t butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl diisopropylamine, N, N-dimethylcyclohexylamine, dicyclo
  • Inert organic solvents are particularly suitable as diluents for carrying out the process 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 butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether.
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 100 ° C, preferably between 10 ° C and 80 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process 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 agitated several hours at the required temperature.
  • 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.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Pisum Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
  • Sorghum Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry moist and hop plants, on ornamental and sports turf and pasture land and for selective purposes Weed control can be used in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.
  • 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, impregnated with active ingredients
  • 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, if appropriate using surface-active agents, that is
  • Emulsifiers and / or dispersants and / or foaming agents Emulsifiers and / or dispersants and / or foaming agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • auxiliary solvents include aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene 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 acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes
  • 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,
  • non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sul
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, 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
  • Active ingredient preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • 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,
  • 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.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amounts of active ingredient are applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • 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.

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

Abstract

L'invention concerne des N-aryle-N-thioxocarbonyle-sulfonamides substitués de la formule générale (I) dans laquelle les restes R1 à R4 ont les significations mentionnées dans la description, ainsi qu'un procédé permettant de les préparer et leur utilisation comme herbicides.
PCT/EP1998/004325 1997-07-24 1998-07-13 N-aryle-n-thioxocarbonyle-sulfonamides substitues s'utilisant comme herbicides WO1999005125A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU88608/98A AU8860898A (en) 1997-07-24 1998-07-13 Substituted n-aryl-n-thioxocarbonyl sulfonamides as herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1997131784 DE19731784A1 (de) 1997-07-24 1997-07-24 Substituierte N-Aryl-N-thioxocarbonyl-sulfonamide
DE19731784.7 1997-07-24

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WO1999005125A1 true WO1999005125A1 (fr) 1999-02-04

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AU (1) AU8860898A (fr)
DE (1) DE19731784A1 (fr)
WO (1) WO1999005125A1 (fr)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000075119A2 (fr) * 1999-06-04 2000-12-14 Bayer Aktiengesellschaft 2-aryl-1,2,4-triazin-3,5-di(thi)ones substituees
WO2002006244A1 (fr) * 2000-07-18 2002-01-24 Bayer Aktiengesellschaft Anilide de l'acide sulfonique herbicide heterocycliquement substitue
US6602825B1 (en) 1999-02-23 2003-08-05 Basf Aktiengesellschaft 1-Aryl-1,3,5-triazine-4-thione-2,6-diones, production thereof and use thereof as herbicides
WO2004048348A1 (fr) * 2002-11-28 2004-06-10 Bayer Cropscience Aktiengesellschaft 2-aryl-1,2,4-triazine-3,5-di(thi)ones substitues utilises en tant qu'herbicides
JP2006504763A (ja) * 2002-10-30 2006-02-09 ビーエーエスエフ アクチェンゲゼルシャフト 二官能性フェニルイソ（チオ）シアナート、それらを製造するための方法および中間体
US8637505B2 (en) 2009-02-04 2014-01-28 Boehringer Ingelheim International Gmbh Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8680093B2 (en) 2009-04-30 2014-03-25 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8748444B2 (en) 2007-12-11 2014-06-10 Vitae Pharmaceuticals, Inc. Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8754076B2 (en) 2008-07-25 2014-06-17 Vitae Pharmaceuticals, Inc./Boehringer-Ingelheim Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8765744B2 (en) 2010-06-25 2014-07-01 Boehringer Ingelheim International Gmbh Azaspirohexanones
US8835426B2 (en) 2007-02-26 2014-09-16 Vitae Pharmaceuticals, Inc. Cyclic urea and carbamate inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8835449B2 (en) 2011-11-11 2014-09-16 Pfizer Inc. 2-thiopyrimidinones
US8846613B2 (en) 2010-11-02 2014-09-30 Boehringer Ingelheim International Gmbh Pharmaceutical combinations for the treatment of metabolic disorders
US8846668B2 (en) 2008-07-25 2014-09-30 Vitae Pharmaceuticals, Inc. Inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8883778B2 (en) 2009-07-01 2014-11-11 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11 beta-hydroxysteroid dehydrogenase 1
US8927539B2 (en) 2009-06-11 2015-01-06 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 based on the 1,3-oxazinan-2-one structure
US8933072B2 (en) 2010-06-16 2015-01-13 Vitae Pharmaceuticals, Inc. Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use
US8969347B2 (en) 2008-06-03 2015-03-03 Intermune, Inc. Compounds and methods for treating inflammatory and fibrotic disorders
US9359379B2 (en) 2012-10-02 2016-06-07 Intermune, Inc. Anti-fibrotic pyridinones
US9404126B2 (en) 2006-06-12 2016-08-02 Kuros Biosciences Ag Processes for packaging aggregated oligonucleotides into virus-like particles of RNA bacteriophages
US9527816B2 (en) 2005-05-10 2016-12-27 Intermune, Inc. Method of modulating stress-activated protein kinase system
US9771332B2 (en) 2015-05-05 2017-09-26 Pfizer Inc. 2-thiopyrimidinones
US10233195B2 (en) 2014-04-02 2019-03-19 Intermune, Inc. Anti-fibrotic pyridinones

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* Cited by examiner, † Cited by third party
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IL148464A0 (en) 2000-05-04 2002-09-12 Basf Ag Uracil substituted phenyl sulfamoyl carboxamides

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EP0408382A2 (fr) * 1989-07-14 1991-01-16 Nissan Chemical Industries, Limited Dérivés d'uraciles et herbicides les contenant comme ingrédient actif
EP0563384A1 (fr) * 1990-12-17 1993-10-06 Nissan Chemical Industries, Limited Derive d'uracile
DE19516785A1 (de) * 1995-05-08 1996-11-14 Bayer Ag Substituierte Aminophenyluracile
WO1997015576A1 (fr) * 1995-10-25 1997-05-01 E.I. Du Pont De Nemours And Company Sulfonamides herbicides

Patent Citations (4)

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EP0408382A2 (fr) * 1989-07-14 1991-01-16 Nissan Chemical Industries, Limited Dérivés d'uraciles et herbicides les contenant comme ingrédient actif
EP0563384A1 (fr) * 1990-12-17 1993-10-06 Nissan Chemical Industries, Limited Derive d'uracile
DE19516785A1 (de) * 1995-05-08 1996-11-14 Bayer Ag Substituierte Aminophenyluracile
WO1997015576A1 (fr) * 1995-10-25 1997-05-01 E.I. Du Pont De Nemours And Company Sulfonamides herbicides

Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6602825B1 (en) 1999-02-23 2003-08-05 Basf Aktiengesellschaft 1-Aryl-1,3,5-triazine-4-thione-2,6-diones, production thereof and use thereof as herbicides
WO2000075119A2 (fr) * 1999-06-04 2000-12-14 Bayer Aktiengesellschaft 2-aryl-1,2,4-triazin-3,5-di(thi)ones substituees
WO2000075119A3 (fr) * 1999-06-04 2001-08-30 Bayer Ag 2-aryl-1,2,4-triazin-3,5-di(thi)ones substituees
AU770424B2 (en) * 1999-06-04 2004-02-19 Bayer Aktiengesellschaft Substituted 2-aryl-1,2,4-triazine-3,5-di(thi)one
WO2002006244A1 (fr) * 2000-07-18 2002-01-24 Bayer Aktiengesellschaft Anilide de l'acide sulfonique herbicide heterocycliquement substitue
JP2006504763A (ja) * 2002-10-30 2006-02-09 ビーエーエスエフ アクチェンゲゼルシャフト 二官能性フェニルイソ（チオ）シアナート、それらを製造するための方法および中間体
JP4738812B2 (ja) * 2002-10-30 2011-08-03 ビーエーエスエフ ソシエタス・ヨーロピア 二官能性フェニルイソ（チオ）シアナート、それらを製造するための方法および中間体
WO2004048348A1 (fr) * 2002-11-28 2004-06-10 Bayer Cropscience Aktiengesellschaft 2-aryl-1,2,4-triazine-3,5-di(thi)ones substitues utilises en tant qu'herbicides
US9527816B2 (en) 2005-05-10 2016-12-27 Intermune, Inc. Method of modulating stress-activated protein kinase system
US10010536B2 (en) 2005-05-10 2018-07-03 Intermune, Inc. Method of modulating stress-activated protein kinase system
US9404126B2 (en) 2006-06-12 2016-08-02 Kuros Biosciences Ag Processes for packaging aggregated oligonucleotides into virus-like particles of RNA bacteriophages
US8835426B2 (en) 2007-02-26 2014-09-16 Vitae Pharmaceuticals, Inc. Cyclic urea and carbamate inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8748444B2 (en) 2007-12-11 2014-06-10 Vitae Pharmaceuticals, Inc. Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1
USRE47142E1 (en) 2008-06-03 2018-11-27 Intermune, Inc. Compounds and methods for treating inflammatory and fibrotic disorders
US8969347B2 (en) 2008-06-03 2015-03-03 Intermune, Inc. Compounds and methods for treating inflammatory and fibrotic disorders
US9290450B2 (en) 2008-06-03 2016-03-22 Intermune, Inc. Compounds and methods for treating inflammatory and fibrotic disorders
US8754076B2 (en) 2008-07-25 2014-06-17 Vitae Pharmaceuticals, Inc./Boehringer-Ingelheim Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8846668B2 (en) 2008-07-25 2014-09-30 Vitae Pharmaceuticals, Inc. Inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8637505B2 (en) 2009-02-04 2014-01-28 Boehringer Ingelheim International Gmbh Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8680093B2 (en) 2009-04-30 2014-03-25 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8927539B2 (en) 2009-06-11 2015-01-06 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 based on the 1,3-oxazinan-2-one structure
US8883778B2 (en) 2009-07-01 2014-11-11 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11 beta-hydroxysteroid dehydrogenase 1
US9090605B2 (en) 2010-06-16 2015-07-28 Vitae Pharmaceuticals, Inc. Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use
US8933072B2 (en) 2010-06-16 2015-01-13 Vitae Pharmaceuticals, Inc. Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use
US8765744B2 (en) 2010-06-25 2014-07-01 Boehringer Ingelheim International Gmbh Azaspirohexanones
US8846613B2 (en) 2010-11-02 2014-09-30 Boehringer Ingelheim International Gmbh Pharmaceutical combinations for the treatment of metabolic disorders
US9873673B2 (en) 2011-11-11 2018-01-23 Pfizer Inc. 2-thiopyrimidinones
US9399626B2 (en) 2011-11-11 2016-07-26 Pfizer Inc. 2-thiopyrimidinones
US8841314B2 (en) 2011-11-11 2014-09-23 Pfizer Inc. 2-Thiopyrimidinones
US8835449B2 (en) 2011-11-11 2014-09-16 Pfizer Inc. 2-thiopyrimidinones
US9359379B2 (en) 2012-10-02 2016-06-07 Intermune, Inc. Anti-fibrotic pyridinones
US9675593B2 (en) 2012-10-02 2017-06-13 Intermune, Inc. Anti-fibrotic pyridinones
US10376497B2 (en) 2012-10-02 2019-08-13 Intermune, Inc. Anti-fibrotic pyridinones
US10898474B2 (en) 2012-10-02 2021-01-26 Intermune, Inc. Anti-fibrotic pyridinones
US10233195B2 (en) 2014-04-02 2019-03-19 Intermune, Inc. Anti-fibrotic pyridinones
US10544161B2 (en) 2014-04-02 2020-01-28 Intermune, Inc. Anti-fibrotic pyridinones
US9771332B2 (en) 2015-05-05 2017-09-26 Pfizer Inc. 2-thiopyrimidinones

Also Published As

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DE19731784A1 (de) 1999-02-04
AU8860898A (en) 1999-02-16

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