WO2002006244A1 - Anilide de l'acide sulfonique herbicide heterocycliquement substitue - Google Patents

Anilide de l'acide sulfonique herbicide heterocycliquement substitue Download PDF

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Publication number
WO2002006244A1
WO2002006244A1 PCT/EP2001/007664 EP0107664W WO0206244A1 WO 2002006244 A1 WO2002006244 A1 WO 2002006244A1 EP 0107664 W EP0107664 W EP 0107664W WO 0206244 A1 WO0206244 A1 WO 0206244A1
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Prior art keywords
chlorine
fluorine
optionally substituted
methyl
bromine
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PCT/EP2001/007664
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German (de)
English (en)
Inventor
Otto Schallner
Roland Andree
Hans-Georg Schwarz
Karl-Heinz Linker
Mark Wilhelm Drewes
Peter Dahmen
Dieter Feucht
Rolf Pontzen
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Bayer Aktiengesellschaft
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Priority to AU2001281954A priority Critical patent/AU2001281954A1/en
Publication of WO2002006244A1 publication Critical patent/WO2002006244A1/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
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20—Quaternary compounds 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
    • C07D231/16—Halogen atoms or nitro radicals
    • 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
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the invention relates to new substituted sulfonic acid anilides, a process for their preparation and their use as plant treatment agents, in particular as
  • R 1 represents hydroxy, nitro, cyano, carbamoyl, thiocarbamoyl, halogen or one of the following groups -R ⁇ , -O ⁇ -R ⁇ , - ⁇ CQ -R,
  • R 2 represents in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
  • R 3 for each optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl,
  • Cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl represents hydrogen, cyano or halogen
  • Q 1 represents O (oxygen) or S (sulfur),
  • Q 2 represents O (oxygen) or S (sulfur),
  • R 4 represents hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkenyl,
  • R 5 represents hydrogen, hydroxy, amino, cyano, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl,
  • Y 1 represents O (oxygen), S (sulfur), SO, SO 2 , NH, N (alkyl) or methylene and
  • Y 2 represents a single bond or O (oxygen), S (sulfur), SO, SO 2 , NH or N (alkyl),
  • hydrocarbon chains such as alkyl or alkanediyl - also in combination with heteroatoms, such as in alkoxy - are each straight-chain or branched.
  • R 1 preferably represents hydroxy, nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or one of the following groups -R 3 , O ⁇ -R 3 ,
  • R 2 preferably represents alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C1-C4-alkoxy, each in each case optionally substituted by halogen alkenyl or alkynyl with 2 to 6 carbon atoms, each in each case optionally 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, C 1 -C 4 -alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 -aloxy or C 1 -C 4 -haloalkoxy-substituted aryl or arylalkyl, each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for in each case optionally substituted by cyano, nitro, halogen, C1-C4-alkyl, -CC-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy-substituted heterocyclyl or heterocyclylalkyl each having 2 to 6 carbon atoms and 1 to 3 nitrogen atoms and / or 1 or 2 oxygen atoms in the heterocyclyl group and optionally 1 to 4 carbon atoms in the al
  • R preferably represents optionally substituted by cyano, formyl (CHO), halogen, C 1 -C 4 alkoxy or C 1 -C 4 alkoximino-C 1 -C 4 alkyl with 1 to 6 carbon atoms, each optionally substituted by halogen or alkenyl Alkynyl each having 2 to 6 carbon atoms, each substituted by cyano, halogen or C1-C4-alkyl
  • 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, -C-C4-Al yl, -C-C4-haloalkyl, C ⁇ -C4-alkoxy or C ⁇ ⁇ C4-haloalkoxy-substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by cyano, nitro, halogen, C ⁇ -C4-alkyl, C1-C4- Haloalkyl, C1-C4-alkoxy or -CC-C4-haloalkoxy substituted heterocyclyl or heterocyclylalkyl each having 1 to 6 carbon atoms, optionally up to 4 nitrogen
  • X preferably represents hydrogen, cyano, fluorine, chlorine or bromine.
  • Z preferably represents one of the heterocyclic groupings below
  • Q 1 preferably represents O (oxygen).
  • Q 2 preferably represents O (oxygen).
  • R preferably represents hydrogen, Arnino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, represents optionally cyano-, halogen- or C1-C 4 - alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyl or alkynyl with each
  • R 5 preferably represents hydrogen, hydroxy, amino, cyano, each optionally by cyano, halogen or C ⁇ .
  • Cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by nitro, cyano, halogen, Cr-alkyl, C1-C4-haloalkyl, -C -alkoxy or C 1 -C 4 -Halogenalkoxy substituted phenyl or phenyl-C 1 -C 4 alkyl.
  • Two adjacent radicals - R 4 and R 4 , R 5 and R 5 or R 4 and R 5 - optionally together preferably represent optionally substituted by halogen and / or optionally by O (oxygen), S (sulfur) or a group from the Series -SO-, -SO2-, -NH- or -N (Cj . -C 4 - alkyl) - At the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl, each with up to 5 carbon atoms.
  • Y 1 preferably represents O (oxygen), S (sulfur), SO, SO 2 , NH, N (C 1 -C 4 alkyl) or methylene.
  • Y 2 preferably represents a single bond or O (oxygen), S (sulfur), SO, SO 2 , NH or N (C 1 -C 4 alkyl).
  • Y and Y are different in each individual case.
  • R 1 particularly preferably represents cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl.
  • R 2 particularly preferably represents methyl optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy,
  • Cyano nitro, 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 heterocyclyl or heterocyclylalkyl from the series furyl, tetrahydrofuryl, thienyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, furylmethyl,
  • X particularly preferably represents hydrogen, fluorine or chlorine.
  • Z particularly preferably represents one of the heterocyclic groupings below
  • R 4 particularly preferably represents hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, and in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , n-, i-, s- or t-butyl, for in each case optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl,
  • Ethynyl, propynyl or butynyl for each methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy propenyloxy, butenyloxy, propynyloxy or butynyloxy, optionally substituted by fluorine, chlorine or bromine, for methylthio, ethylthio, n- or i-propylthio, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for each optionally substituted by fluorine, Chlorine or bromine substituted propenylthio, butenylthio, propynylthio or
  • Butynylthio for me ylarnino, ethylamino, n- or i-propylamino, dimethylamino or diemylamino, or for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylethyl, optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, Cyclobutylmethyl, Cyclopentylmethyl or Cyclohexylmethyl.
  • cyano particularly preferably stands for hydrogen, hydroxy, amino, cyano, for methyl, ethyl, n- or i-propyl, n-, i-, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i-propylamino, each optionally substituted by fluorine, chlorine or bromine Propenyl, butenyl, propynyl or butynyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylethyl, cyclobutylmethyl,
  • Cyclopentylmethyl or 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, benzyl or phenylethyl.
  • Two adjacent radicals - R 4 and R 4 , R 5 and R 5 or R 4 and R ⁇ - optionally together are particularly preferably optionally substituted by fluorine or chlorine and / or optionally by O (oxygen), S (sulfur) or one Grouping from the series -SO-, -SO2-, -NH- or
  • Y 1 particularly preferably represents O (oxygen), S (sulfur), SO, SO2, NH, N (methyl) or methylene.
  • Y 2 particularly preferably represents a single bond or O (oxygen), S (sulfur), SO, SO 2 , NH or N (methyl).
  • Y and Y are different in each individual case.
  • R 1 very particularly preferably represents cyano, thiocarbamoyl, chlorine or bromine.
  • R 2 very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine or bromine, each optionally substituted by fluorine, chlorine or bromine Ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, for each cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by fluorine, chlorine, bromine or methyl, each for optionally by
  • R 3 very particularly preferably represents in each case optionally, cyano
  • X very particularly preferably represents fluorine or chlorine.
  • R 4 very particularly preferably represents hydrogen, amino, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s-, which are each optionally substituted by fluorine, chlorine, methoxy or ethoxy.
  • ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl each optionally substituted by fluorine, chlorine or bromine, for methoxy, ethoxy, n- or i-propoxy, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, Methylthio, ethylthio, n- or i-propylthio, for propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio or butynylthio, each optionally substituted by fluorine, chlorine or bromine, or for each optionally by fluorine, chlorine or Methyl substituted cyclopropyl or cyclopropylethyl.
  • R 5 very particularly preferably represents hydrogen, amino, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, each optionally propenyl, butenyl, propynyl or butmyl substituted by fluorine, chlorine or bromine, for each cyclopropyl or cyclopropylethyl substituted by fluorine, chlorine or methyl.
  • the individual radicals R 4 and R ⁇ - insofar as they are connected to the same heterocyclic grouping more than once - can have the same or different meanings in the context of the above definitions given as preferred, particularly preferred or very particularly preferred.
  • Preferred compounds according to the invention are those of the formula (I) in which there is a combination of the meanings listed above as preferred.
  • R 1 represents cyano, thiocarbamoyl, chlorine or bromine
  • R 2 for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by fluorine or chlorine, for cyclopropyl optionally substituted by fluorine, chlorine, bromine or methyl, for each optionally phenyl substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy Heterocyclyl or heterocyclylalkyl from the series thienyl, pyrazolyl,
  • Isoxazolyl, pyridinyl, R 3 represents in each case optionally substituted by fluorine or chlorine methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl .
  • X represents hydrogen, fluorine or chlorine
  • R 4 for hydrogen, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, for ethenyl, propenyl, butenyl, ethynyl optionally substituted by fluorine or chlorine, Propynyl or butynyl, for methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, for propenyloxy optionally substituted by fluorine or chlorine, butenyloxy,
  • R 5 represents hydrogen, amino, each optionally by fluorine, chlorine,
  • R 1 represents cyano, thiocarbamoyl, chlorine or bromine
  • R 2 for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by fluorine or chlorine, for optionally substituted by fluorine,
  • Chlorine, bromine or methyl substituted cyclopropyl for each phenyl optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifraor methyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy substituted heterocyclyl or heterocyclylalkyl from the series thienyl, pyrazolyl, isoxazolyl, pyridinyl,
  • R 3 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine or chlorine, or for optionally by
  • X represents hydrogen, fluorine or chlorine
  • R 4 "1 represents hydrogen, chlorine, bromine or methyl
  • R 4 "2 represents in each case optionally substituted by fluorine and / or chlorine methyl or ethyl
  • R 5 represents hydrogen, amino, each represents methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, or represents propenyl or propynyl which is optionally substituted by fluorine or chlorine.
  • R 1 represents cyano, thiocarbamoyl, chlorine or bromine
  • R 2 for methyl optionally substituted by fluorine or chlorine
  • R 3 represents in each case optionally substituted by fluorine or chlorine methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl .
  • X represents hydrogen, fluorine or chlorine
  • R 4 "1 represents hydrogen, chlorine, bromine or methyl
  • R 4 "2 represents in each case optionally substituted by fluorine and / or chlorine methyl, ethyl, methoxy or ethoxy, and
  • R 5 stands for methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, or for propenyl or propynyl, each optionally substituted by fluorine or chlorine.
  • R 1 represents cyano, thiocarbamoyl, chlorine or bromine
  • R 2 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine or chlorine, for cyclopropyl optionally substituted by fluorine, chlorine, bromine or methyl, for each given - if phenyl substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy tes heterocyclyl or heterocyclylalkyl from the series thienyl, pyrazolyl,
  • R 3 represents in each case optionally substituted by fluorine or chlorine methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl .
  • X represents hydrogen, fluorine or chlorine
  • R 5 "1 stands for methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, or for propenyl or propynyl, each optionally substituted by fluorine or chlorine
  • R 5 "2 stands for methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, or for propenyl or propinyl, each optionally substituted by fluorine or chlorine.
  • R 1 represents cyano, thiocarbamoyl, chlorine or bromine
  • R 2 for methyl optionally substituted by fluorine or chlorine
  • R 3 represents in each case optionally substituted by fluorine or chlorine methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl .
  • X represents hydrogen, fluorine or chlorine
  • R 4 represents hydrogen, fluorine, chlorine, bromine, or methyl or substituted in each case by fluorine, chlorine, methoxy or ethoxy
  • R 1 represents cyano, thiocarbamoyl, chlorine or bromine
  • R 2 for methyl optionally substituted by fluorine or chlorine
  • R 3 for methyl optionally substituted by fluorine or chlorine
  • R 4 represents hydrogen, fluorine, chlorine, bromine, each represents methyl or ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or represents methoxy or ethoxy optionally substituted by fluorine, chlorine, methoxy or ethoxy, and
  • R 5 represents methyl or ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy.
  • the general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • the new substituted sulfonic acid anilides of the general formula (I) have interesting biological properties. They are particularly characterized by their strong herbicidal activity.
  • R 1, R, X and Z have the meaning given above, with sulfenoalogemides of the general formula (III)
  • R 3 has the meaning given above and X 1 represents halogen
  • the sulfonic acid amides to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I) are generally defined by the formula (H).
  • R 1 , R 2 , X and Z preferably or in particular have those meanings which are preferred or particularly preferred in connection with the description of the compounds of the general formula (I) according to the invention
  • the starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. EP-A-408382, EP-A-563384, EP-A-609734, EP-A-648749, US Pat. A-4818275, US-A-4909831, WO-A-95/17391, WO-A-95/29158, WO-A-95/29168, WO-A-95/30661, WO-A-96/18618, WO-A-99/52878).
  • Formula (III) provides a general definition of the sulfenic acid halides to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • R 3 preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the general formula (I) according to the invention preferably or as particularly preferred for R 3 ;
  • X 1 preferably represents fluorine, chlorine or bromine, especially chlorine.
  • the starting materials of the general formula (TIT) are known organic synthetic chemicals.
  • reaction auxiliaries 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; basic organic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl diisopropylamine, N, N-dimethylcyclohexy
  • a diluent inert organic solvents are particularly suitable as diluents. 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-
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -60 ° C and + 60 ° C, preferably between -40 ° C and + 40 ° 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 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 all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can be used, for example, in the following plants:
  • the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.
  • the active compounds according to the invention are suitable for combating total weeds, for example on industrial and rail tracks and on paths and squares with and without tree growth.
  • the active compounds according to the invention for combating weeds in permanent crops for example forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm,
  • 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 appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesirable wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated plants can be plants which 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 cultivars which can or cannot be protected by plant breeders' rights.
  • Parts and organs of plants such as shoot, leaf, flower and root understood are, for example leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes are listed.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • all plants and their parts can be treated according to the invention.
  • wild plants weeds, harmful plants
  • conventional organic breeding methods such as e.g. Crossing or protoplast fusion, preserved plant species and plant varieties (crop plants) and their parts treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms) and their parts are treated.
  • the term "parts” or "parts of plants” or "plant parts” was explained above.
  • Plant varieties are cultivated 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.
  • transgenic 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
  • Harvested products are an increased defense of the plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
  • the important crop plants such as cereals (including rice), maize, soybeans, potatoes, cotton, beets, rape,
  • Cultivated grasses such as golf and ornamental turf, fruit plants (with the fruits apples, pears, citrus fruits and grapes) and plantation crops such as olive and rubber trees are mentioned, whereby cereals (including rice), corn, soybeans, potatoes, cotton, beets and rapeseed are particularly emphasized become.
  • 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), CryIA (b), Cry ⁇ A (c), CryHA, CrylUA, CryIITB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • the traits that are particularly emphasized are the elevated ones
  • Glufosinate / phosphinotricin eg "PAT” gene
  • ALS inhibitors such as imidazoline, sulfonylureas and others
  • PPO inhibitors eg plants with acuron genes
  • 4-HPD inhibitors such as isoxazoles (eg isoxaflutole)
  • ACCase - Inhibitors such as Sethoxydim, as well as Bromoxynil.
  • genes imparting the desired properties can also occur in combinations with one another in the transgenic plants.
  • “Bt plants” are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard®
  • herbicide-tolerant plants are maize varieties, cotton varieties, soy varieties, cereals including rice varieties, beet varieties and rapeseed varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosates e.g. corn, cotton, soybean, beet, rapeseed), Liberty Link® (tolerance against glufosinates, eg rapeseed, maize, beets), TMI® (tolerance against imidazolinones) and STS® (tolerance against sulfonylureas eg maize).
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (for example maize, rice).
  • 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 crop plants, increased tolerance of the crop plants to high or low temperatures, Increased tolerance of the crop plants against drought or against water salt or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products, which is possible via the effects that are actually to be expected.
  • 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, in addition to the good control of the Weed plants have the above-mentioned synergistic effects with the plants or plant cultivars described above.
  • 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 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.
  • the following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable
  • Oils 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.
  • ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide
  • solid carriers there are suitable: for example Ammom 'umsalze and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granulates are possible: eg 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,
  • 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 leaching and methyl cellulose.
  • 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 sulfit
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • active compounds according to the invention can also be used in a mixture with known herbicides and / or with substances which improve crop tolerance (“safeners”) for weed control, finished formulations or tank mixes being possible. Mixtures are also possible possible with weed control agents which contain one or more known herbicides and a safener.
  • herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium), ametryne, amicarbazones, amidochlor, amidosulfuron, anilofos, asulam, atrazine,
  • Pelargonic acid Pendimethalin, Pendralin, Pentoxazone, Phenmedipham, Picolinafen, Piperophos, Pretilachlor, Primisulfuron (-methyl), Profluazol, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone (-sodium), Propyzarbonethyl, Prosulfuronamide, Prosulfuron ), Pyrazogyl, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxime, pyributicarb, pyridate, pyridatol, pyriftalid,
  • Pyriminobac (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl, -P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl) , Sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamides, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydiasulfonuron, tronuronyluron (triallonyl), triallonyluron, triallon
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil conditions, 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 become. They are used in the customary manner, for example by watering, spraying, spraying or scattering.
  • the active compounds according to the invention can be applied both before and after 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.
  • the reaction mixture is stirred at room temperature for 18 hours, diluted with 10 ml of dichloromethane and washed successively with 2N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate and largely freed from the solvent under reduced pressure.
  • the crude product thus obtained is purified by column chromatography on silica gel using dichloromethane as the eluent.
  • reaction mixture After a reaction time of 20 minutes, in which the reaction temperature rises to -5 ° C., the reaction mixture is mixed with 30 ml of ethyl acetate, washed successively with water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent is largely removed under reduced pressure and the crude product thus obtained is purified by column chromatography over silica gel using dichloromethane as the eluent.
  • the calibration was carried out with 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.
  • 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 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.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Test plants which have a height of 5 to 15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound 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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

L'invention concerne un anilide de l'acide sulfonique substitué de formule (I), dans laquelle R<1> signifie hydroxy, nitro, cyano, carbamoyle, thiocarbamoyle, halogène ou un des groupes suivants R<3>, Q<1> R<3>, Q<1> CQ<2> R<3>, R<2> signifie alkyle, alcényle, alkinyle, cycloalkyle, cycloalkylalkyle, aryle, arylalkyle, hétérocyclyle ou hétérocyclylalkyle, chacun étant éventuellement substitué, R<3> signifie alkyle, alcényle, alkinyle, cycloalkyle, cycloalkylalkyle, aryle, arylalkyle, hétérocyclyle ou hétérocyclylalkyle, chacun étant éventuellement substitué, X est hydrogène, cyano ou halogène, et Z représente un des groupes hétérocycliques indiqués dans la description. L'invention concerne également son procédé de production et son utilisation comme agent de traitement des plantes.
PCT/EP2001/007664 2000-07-18 2001-07-05 Anilide de l'acide sulfonique herbicide heterocycliquement substitue WO2002006244A1 (fr)

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AU2001281954A AU2001281954A1 (en) 2000-07-18 2001-07-05 Heterocyclic substituted herbicidal sulphonic acid anilides

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DE10034803.3 2000-07-18
DE2000134803 DE10034803A1 (de) 2000-07-18 2000-07-18 Substituierte Sulfonsäureanilide

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US8598160B2 (en) 2008-02-15 2013-12-03 Vitae Pharmaceuticals, Inc. Cycloalkyl lactame derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1
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