EP1066256A1 - The use of derivatives of 2-oxopyrrole as crop protection agents and novel 2-oxopyrroles - Google Patents

The use of derivatives of 2-oxopyrrole as crop protection agents and novel 2-oxopyrroles

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Publication number
EP1066256A1
EP1066256A1 EP99919137A EP99919137A EP1066256A1 EP 1066256 A1 EP1066256 A1 EP 1066256A1 EP 99919137 A EP99919137 A EP 99919137A EP 99919137 A EP99919137 A EP 99919137A EP 1066256 A1 EP1066256 A1 EP 1066256A1
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Prior art keywords
alkyl
aryl
alkoxy
heteroaryl
alkenyl
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German (de)
French (fr)
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Oliver Wagner
Martina Otten
Karl-Otto Westphalen
Helmut Walter
Volker Harries
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/38—2-Pyrrolones
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D403/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D403/10—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 carbon chain containing aromatic rings
    • 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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—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
    • C07D409/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D413/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D417/06—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 carbon chain containing only aliphatic carbon atoms

Definitions

  • the present invention relates to the use of derivatives of 2-oxopyrrole of the formula I as crop protection agents
  • the invention further relates to new derivatives of 2-oxopyrrole of the general formula I.
  • 2-Oxoppyyrols of the general formula I in which R 1 is phenyl, 4-dimethylaminophenyl and 2-nitrophenyl, R 2 is methyl and A is COOC 2 H 5 are from Z. Physiol. Chem. 132 (1924), 72 known. A possible use as a crop protection agent is not possible
  • the object of the present invention was to provide active compounds as crop protection agents.
  • R 1 aryl or heteroaryl where these radicals can independently carry one to five of the following groups: hydrogen, halogen, cyano, nitro, hydroxy, mercapto, thio 2 cyanato, carboxy, amino, C ⁇ -C 6 -alkyl, C 6 cyanoalkyl, C 2 -C 6 - alkenyl, C ⁇ -C 6 -alkoxy-C 2 -C 6 alkenyl, C 3 -C 6 - Alkynyl, -CC 6 -alkoxy-C 3 -C 6 -alkynyl, C 3 -C 6 -alkynyl-C ⁇ -C 6 alkoxy, C 3 -C 7 cycloalkyl, -C-C 6 alkyl -C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy-C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyloxy, C 3 -C
  • C 2 -C 6 haloalkyl C 2 -C 6 haloalkenyl, C 3 -C 6 haloalkynyl, C 2 -C 6 cyanoalkenyl, C 3 -C 6 cyanoalkynyl, C 1 -C 6 alkoxy, C ⁇ -C 6 -Cyanoalkoxy, -C-C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -cyanoalkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C ⁇ -C 6 -alkylthio, -C-C 6 -cyanoalkylthio, -C-C 6 -haloalkylthio, -C-C 6 -alkoxy-C ⁇ -C 6 -alkylthio, C ⁇ -C 6 -alkoxycarbonyl
  • aryl or heteroaryl radical with a fused-on penyl ring, a fused-on C 3 -C 6 carbocycle or a 5- or 6-membered heterocycle forms a bicyclic system, the fused-on ring system optionally carrying one to three of the substituents mentioned above for aryl can.
  • R 2 Ci-Cg-alkyl or aryl or heteroaryl, where aryl or heteroaryl can carry one to three of the substituents mentioned under R 1 for aryl; C 3 -C cycloalkyl or Ci-C ⁇ -alkylaryl;
  • a COOR 3 or CONR 3 R 4 where R 3 and R 4 are independently hydrogen, -CC 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 7 cycloalkyl or Ci-Cg-alkyl-aryl may be, which optionally partially or fully halogenated or substituents to three Sub ⁇ selected from C ⁇ -C4-alkoxy, C ⁇ -C4-haloalkoxy, C ⁇ -C 4 alkylthio, C 3 -C cycloalkyl, C 5 - C can carry cycloalkenyl;
  • the 2-oxopyrrole derivatives to be used according to the invention can be used with respect to the position of the substituent R 1 as E or as Z isomers or a mixture of both isomers.
  • the organic molecule parts mentioned in the definition of R 1 , R 2 and A are collective terms for individual enumeration of the individual meanings.
  • All carbon chains ie all alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, cyanoalkoxy, , Alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkyloximino, alkyliminooxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy and alkynylthio parts can be straight-chain or branched.
  • Halogenated substituents preferably carry one to five identical or different halogen atoms.
  • Halogen is fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
  • -CC 6 alkyl for: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2- Methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2- Trimethylpropyl, 1,2, 2-trimethylpropyl, 1-
  • C ⁇ -C 6 -haloalkyl as mentioned above C ⁇ -C6 alkyl which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine is substituted, eg one of the under C ⁇ -C 4 haloalkyl radicals or 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6- Fluoro-l-hexyl, 6-chloro-1-hexyl, 6-bromo-l-hexyl, 6-iodo-l-hexyl, 6, 6, 6-trichloro-l-hexyl or dodecafluorohexyl, especially for chloromethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroeth
  • C ⁇ -C 6 alkylamino for: methylamino, ethylamino, n-propylamino, 1-methylethylamino, n-butylamino, 1-methylpropylamino, 2-methylpropylamino, 1, 1-dimethylethylamino, n-pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino,
  • Cyano-C ⁇ -C 6 alkyl for: for example cyanomethyl, 1-cyanoeth-l-yl, 2-cyanoeth-l-yl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyano-prop -1-yl, l-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4-cyanobut-l -yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, l-cyanobut-3-yl, 2-cyano-but-3-yl, l-cyano-2-methyl-prop-3-yl , 2-cyano-2-methyl-prop-3-yl, 3-cyano-2-methyl-prop-3-yl or 2-cyanomethyl-prop-2-yl, in particular for cyanomethyl or 2-cyanoethyl;
  • (-CC 6 -alkyl) carbonyl for: methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1, 1-dimethylethylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl ,
  • (-C 6 -alkyl) carbonyl -CC 6 -alkyl for: Ci-Cg-alkyl substituted by (C ⁇ -C 6 -alkyl) carbonyl as mentioned above, for example for methylcarbonyImethy1;
  • (-C 6 alkyl) carboxyl for: C ! -C 6 alkyl as defined above, substituted with a carboxyl group, for example methylcarboxyl, ethylcarboxyl, n-propylcarboxyl, 1-methylethylcarboxyl, n-butylcarboxyl, 1-methylpropylcarboxyl, 2-methylpropylcarboxyl or 1, 1-dimethylethylcarboxyl , especially for methyl carboxyl;
  • C ⁇ -C 6 alkoxy for: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy, for example n-pentoxy, 1-methylbutoxy, 2nd -Methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimeth lpropoxy, 2, 2-dieth lpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2, 2-dimethylbutoxy, 2, 3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1,2, 2-trimethylpropoxy, 1-ethyl-l-methylpropoxy and 1-ethyl-1-2-methylprop
  • C ⁇ -C 6 -haloalkoxy for: a C -Cg alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example one of the radicals mentioned under -C 4 -haloalkoxy or for 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5, 5,5-trichloro-1-pentoxy, undecafluoropentoxy, 6- Fluoro-l-hexoxy, 6-chloro-l-hexoxy, 6-bromo-l-hexoxy, 6-iodine-l-hexoxy, 6, 6, 6-trichloro-l-hexoxy or dodecafluorohexoxy, especially for chloromethoxy, fluoromethoxy, Difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy or 2,2,
  • (-C-C 6 -alkoxy) carbonyl for: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1, 1-dimethylethoxycarbonyl, n-pentoxycarbonyl, 1-methylbutoxycarbonyl , 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl -Methy1- pentoxycarbonyl, 1, 1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1, 3-dimethylbutoxycarbonyl, 2, 2-dimeth
  • Cx-Cg-alkylthio for: methylthio, ethylthio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio,
  • Ci-C ⁇ -alkylthio as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for example one of those under C ! -C 4 -Halogenalkylthio radicals or for 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodo-pentylthio, ündecafluorpentylthio, 6-fluorhexylthio or 6-chlorohexylthio, especially for chloromethylthio, fluoromethylthioethyl, difluor , 2-fluoroethylthio, 2-chloroethylthio or 2,2, 2-trifluoroethylthio;
  • C ⁇ -C 6 alkylsulfinyl for: methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methyl propylsulfinyl, 1, 1-dimethylethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfyl, 1-methylbutylsulfinyl Methylbutylsulfinyl, 3-methylbutylsulfinyl, 1, 1-dimethyl 8 propylsulfinyl, 1, 2-dimethylpropylsulfinyl, 2, 2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-
  • C ⁇ -C 6 alkylsulfonyl for: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methyl propylsulfonyl, 2-methyl propylsulfonyl, 1, 1-dimethyl ethylsulfonyl, n-pentyl Methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonylsulfonyl, 2-methyl 4-methylpentylsulf
  • C 2 -C 6 alkenyl for: e.g. ethenyl, prop-2-en-l-yl, n-buten-4-yl, l-methyl-prop-2-en-l-yl, 2-methyl-prop- 2-en-l-yl, 2-butene-1-yl, n-penten-3-yl, n-penten-4-yl, l-methyl-but-2-en-l-yl, 2-methyl but-2-en-l-yl, 3-methyl-but-2-en-l-yl, 1-methyl-but-3-en-l-yl, 2-methyl-but-3-en-l- yl, 3-methyl-but-3-en-1-yl, 1, l-dimethyl-prop-2-en-l-yl, 1, 2-dimethyl-prop-2-en-1-yl, l- Ethyl-prop-2-en-l-yl, n-hex-3-en-l-yl, n-hex-4-en-1
  • C 2 -C 6 alkenylsulfinyl for: C 2 -C 6 alkenyl as defined above, substituted with a sulfinyl group, for example ethenylsulfinyl, prop-2-en-l-ylsulfinyl, n-buten-4-ylsulfinyl, l- Methyl-prop-2-en-l-ylsulfinyl, 2-methyl-prop-2-en-l-ylsulfinyl, 2-buten-l-ylsulfinyl, n-penten-3-ylsulfinyl, n-pentene- 4-ylsulfinyl, l-methyl-but-2-en-l-ylsulfinyl, 2-methyl-but-2-en-l-ylsulfinyl, 3-methyl-but-2-en-l-ylsulfinyl, 1-Me- thyl-but-3
  • C 2 -C 6 alkenylsulfonyl for: C 2 -C 6 alkenyl as defined above, substituted with a sulfonyl group, for example ethenylsulfonyl, prop-2-en-l-ylsulfonyl, n-buten-4-ylsulfonyl, l- Methyl-prop-2-en-l-ylsulfonyl, 2-methyl-prop-2-en-l-ylsulfonyl, 2-buten-l-ylsulfonyl, n-pentene-3-ylsulfonyl, n-pentene 4-ylsulfonyl, l-methyl-but-2-en-l-ylsulfonyl, 2-methyl-but-2-en-l-ylsulfonyl, 3-methyl-but-2-en-l-ylsulfonyl, 1-Me- thyl-but-3
  • C 2 -C 6 haloalkenyl for: C 3 -C 6 alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for example 2-chloroallyl,
  • C 2 -C 6 alkenyloxy for: ethenyloxy, prop-1-en-l-yloxy, prop-2-en-l-yloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2 -yloxy, n-buten-3-yloxy, 1-methyl-prop-1-en-1-yloxy, 2-methyl-prop-1-en-1-yloxy, 1-methyl-prop-2-en-1 -yloxy, 2-methyl-prop-2-en-l-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy , 1-methyl-but-l-en-l-yloxy, 2-methyl-but-l-en-l-yloxy, 3-methyl-but-l-en-l-yloxy, 1-methyl-but -2-en-l-yloxy, 2-methyl-but-2-en-l
  • C 3 -C 6 alkynyl for: ethynyl, prop-1-in-l-yl, prop-2-in-l-yl, n-but-1-in-l-yl, n-but-l-in -3-yl, n-but-l-in-4-yl, n-but-2-in-l-yl, n-pent-1-in-l-yl, n-pent-l-in-3 -yl, n-pent-1-in-4-yl, n-pent-1-in-5-yl, n-pent-2-in-1-yl, n-pent-2-in-4-yl , n-Pent-2-in-5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n-hex-1-in-l -yl, n-hex-1-in-3-yl, n-hex-1-in-4-y
  • C 2 -C 6 alkynyloxy for: ethynyloxy, prop-1-in-1-yloxy,
  • C 3 -C 7 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, in particular for cyclopentyl or cyclohexyl;
  • C 7 -C 7 cycloalkyloxy for: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy or cycloheptyloxy;
  • C 5 -C 7 cycloalkenyl for: cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3-enyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohept-1-enyl , Cyclohept-2-enyl, cyclohept-3-enyl or cyclohept-4-enyl;
  • Heteroaryl aromatic heterocycles with one to three heteroatoms selected from a group consisting of - one to three nitrogen atoms, one or two oxygen and one or two sulfur atoms, e.g. Furyl such as 2-furyl and 3-furyl, thienyl such as 2-thienyl and 3-thienyl, pyrrolyl such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl such as 2-0xazolyl, 4-oxazolyl and 5-0xazolyl, thiazolyl such as 2-thiazolyl, 4-thiazolyl and 5-thiazolyl, Imidazolyl such as
  • the 2-0xopyrrole derivatives can be obtained by processes known per se to the person skilled in the art and described in the literature, so that further details are unnecessary here. Just as an example here is that in the Z. Physiol. Chem. 132 (1924), 72 and J.Org. Che. 57, 1992, 6032. 13
  • a further synthesis can drive in analogy to known per se Ver ⁇ on the intermediates of formulas Ha, IIb or IIC effected, which form a further subject of the invention.
  • R 2 is methyl, ethyl or propyl and A is COOCH 3 or COOC 2 H 5 and R 1 has one of the meanings given in Tables A and B below for aryl or heteroaryl Has.
  • Compounds in which R 2 is methyl and A is COOCH 3 and R 2 is an aryl radical which is substituted in the 2- or 2,6-position and which can be substituted by one or more halogen, alkyl or haloalkyl groups are particularly preferred.
  • R 1 represents a heteroaromatic radical, in particular a substituted pyrazole radical, which can optionally carry one or more halogen substituents.
  • the 2-0xopyrrole I and their agriculturally useful salts are suitable as herbicides.
  • the herbicidal compositions containing I control plant growth very well on non-cultivated areas. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
  • the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following cultures can be considered:
  • the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • the 2-oxopyrroles I are also suitable for the desiccation and / or defoliation of plants.
  • desiccants are particularly suitable for drying out the above-ground parts of crops such as potatoes, rapeseed, sunflower and soybeans. This enables fully mechanical harvesting of these important crops.
  • the compounds of the formula I are also used for combating animal pests from the class of the insects, arachnids and nematodes. They can be used in crop protection as well as in the hygiene, storage protection and veterinary sectors to control animal pests. They are particularly suitable for controlling the following animal pests: 24
  • Beetles (Coleoptera), e.g. Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruechus pisorum, Bruchus lentisu- losa, Byiscus , Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorr- hynchus napi, Chaetocne a tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punc- tata, Diabrotica virgiferisisobutisisobirisisinobisisinobisisobutisis, Epilachinitris,
  • Two-winged birds e.g. Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, 25th
  • Chrysomya bezziana Chrysomya hominivorax, Chrysomya macella- ria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pi- piens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fan- nia canicularis, Gasterophilus intestinalis, glipidisisisisodisisisodisis, glossina misplantis, glossina metrisis, feminine equilibrium, glossina morphisis, glossina misplantis, glossina misoblus Hylemyia platura, Hypoder a lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus
  • Thrips e.g. Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,
  • Dermatoptera e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta,
  • Heteroptera e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara quadrantulais, Pyanma viridula, Pies
  • Plant suckers e.g. Acyrthosiphon onobrychis
  • Adelges laricis Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Ce- rosipha gossypii, Dreyfusia nordmannianae, Dreyfusiaipheae, Macyosophiosumiabia, Macysoleosumiaumia, Macysapiaumia, Macys Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopa- lomyzus ascalonicus, Rhopalosiphum tenuis, glabra, buci
  • Termites e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis,
  • Arachnoid such as arachnids (Acarina), e.g. Amblyomma america- nu, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Rubusus Iodinobusinusnobin, Ialodiaxus tris me- gnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllo- coptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabieus, Tetranychus cinnabarinus taw
  • Nematodes such as root gall nematodes, e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stick and leaf wholes, e.g.
  • Belonolaimus longicaudatus Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multi- ticinctus, Longidorus elongatus, Radopholus similis, Rotylen- chus robustus, Trichodorus primitivus, Tylenchorhynchus clay- toni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.
  • the compounds I or the compositions comprising them can be sprayed, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules. Nebulization, dusting, scattering or pouring can be used.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Mineral oil fractions from medium to high boiling point such as kerosene and diesel oil, also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, Ethanol, propanol, butanol 27 and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, eg amines such as N-methylpyrrolidone and water.
  • paraffins e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives
  • alcohols such as methanol, Ethanol, propanol, butanol 27 and cyclohexan
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • emulsions, pastes or oldispersions the l-amino-3-benzyluracils as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols as well as of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formalins Condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylpheny
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • the concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
  • the formulations generally contain from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • Distributing the mixture in 20,000 parts by weight of water contains a spray mixture which contains 0.1% by weight of the active ingredient.
  • the active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
  • the application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.) depending on the control target, season, target plants and growth stage.
  • the 2-oxopyrroles I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • test plants For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then with those suspended in water or
  • test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for, 37 and their response to each treatment was evaluated.
  • Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
  • ABUTH Chinese hemp (Abuthilon theophrasti)
  • SETIT Italian millet (Setaria italica)
  • siNAL White mustard (Sinapis alba)

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Abstract

The invention relates to the use of 2-oxopyrroles of general formula (I) and their agriculturally usable salts as crop protection agents and to novel 2-oxopyrroles of formula (I). The substituents have the following meanings: R<1> represents aryl or heteroaryl and these radicals may carry one to five groups independently of each other or alternatively, the aryl or heteroaryl radical forms a bicyclical system with a fused-on phenyl ring, a fused-on C3-C6 carbocyclic compound or a 5- or 6-membered heterocyclic compound and R<2> represents C2-C6-alkyl or aryl or heteroaryl, COOR<3> or CONR<3>R<4>, R<3> and R<4> representing, independently of each other, hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C3-C7-cycloalkyl or C2-C6-alkyl-aryl which can optionally be partially or fully halogenated or can carry one to three substituents chosen from the following: C1-C4-alkoxy, C1-C4-halogenalkoxy, C1-C4-alkylthio, C3-C7-cycloalkyl, C5-C7-cycloalkenyl.

Description

Verwendung von Derivaten des 2-Oxopyrrols als Pflanzenschutzmittel und neue 2-Oxopyrrole Use of derivatives of 2-oxopyrrole as crop protection agents and new 2-oxopyrroles
5 B E S C H R E I B U N G5 B E S C H R E I B U N G
Die vorliegende Erfindung betrifft die Verwendung von Derivaten des 2-Oxopyrrols der Formel I als PflanzenschutzmittelThe present invention relates to the use of derivatives of 2-oxopyrrole of the formula I as crop protection agents
1010
(I)(I)
15 15
Weiterhin betrifft die Erfindung neue Derivate des 2-Oxopyrrols der allgemeinen Formel I.The invention further relates to new derivatives of 2-oxopyrrole of the general formula I.
2020th
2-Oxoppyyrole der allgemeinen Formel I, in denen R1 für Phenyl, 4-Dimethylaminophenyl und 2-Nitrophenyl, R2 für Methyl und A für COOC2H5 steht sind aus Z. Physiol. Chem. 132 (1924), 72 bekannt. Eine mögliche Verwendung als Pflanzenschutzmittel wird nicht er¬2-Oxoppyyrols of the general formula I in which R 1 is phenyl, 4-dimethylaminophenyl and 2-nitrophenyl, R 2 is methyl and A is COOC 2 H 5 are from Z. Physiol. Chem. 132 (1924), 72 known. A possible use as a crop protection agent is not possible
25 wähnt.25 thinks.
Der vorliegenden Erfindung lag die Aufgabe zugrunde, als Pflanzenschutzmittel wirksame Verbindungen zur Verfügung zu stellen.The object of the present invention was to provide active compounds as crop protection agents.
,0 Diese Aufgabe wurde durch die erfindungsgemäße Verwendung gemäß Anspruch 1 gelöst., 0 This object was achieved by the use according to the invention as claimed in claim 1.
Ein Teil der erfindungsgemäß zu verwendenden 2-Oxopyrrol-Derivate sind neu und stellen als solche einen weiteren Gegenstand der Er- ,5 findung dar.A part of the present invention to be used 2-Oxopyrrol derivatives are novel and as such a further aspect of the Er, 5 represents the invention.
Bevorzugte Ausführungsformen der Erfindung sind den Unteransprüchen und der nachfolgenden detaillierten Beschreibung zu entnehmen.Preferred embodiments of the invention can be found in the subclaims and the detailed description below.
4040
In den erfindungsgemäß zu verwendende 2-Oxopyrrolderivaten derIn the 2-oxopyrrole derivatives to be used according to the invention
Formel I haben die Substituenten R1, R2 und A die folgenden Bedeutungen :Formula I have the substituents R 1 , R 2 and A have the following meanings:
. - R1 Aryl oder Heteroaryl, wobei diese Reste unabhängig voneinander eine bis fünf der folgenden Gruppen tragen können: Wasserstoff, Halogen, Cyano, Nitro, Hydroxy, Mercapto, Thio- 2 cyanato, Carboxy, Amino,Cι-C6-Alkyl, Cι-C6-Cyanoalkyl, C2-C6- Alkenyl, Cι-C6-Alkoxy-C2-C6-Alkenyl, C3-C6-Alkinyl, Cι-C6-Al- koxy-C3-C6-Alkinyl, C3-C6-Alkinyl-Cι-C6-Alkoxy, C3-C7-Cycloal- kyl, Cι-C6-Alkyl-C3-C7-Cycloalkyl, C1-C6-Alkoxy-C3-C7-Cycloal- kyl, C3-C7-Cycloalkyloxy, C3-C7-Cyanocycloalkyloxy, Cι-C6-Al- kyl-C3-C7-Cycloalkyloxy, C3-C -Halogencycloalkyl, C3-C7-Cyano- cycloalkyl, C3-C7-Halogencycloalkyloxy, C5-C7-Cycloalkenyl, Cι-C6-Alkyl-C5-C7-Cycloalkenyl, Cι-C6-Alkoxy-C5-C7-Cycloalke- nyl, C5-C7-Cyanocycloalkenyl, C5-C7-Halogencycloalkenyl, Cι-C6-Alkoxy-Cι-C6-Alkyl, C!-C6-Halogenalkyl, C2-C6-Halogenal- kenyl, C3-C6-Halogenalkinyl, C2-C6-Cyanoalkenyl, C3-C6-Cyano- alkinyl, Cι-C6-Alkoxy, Cι-C6-Cyanoalkoxy, Cι-C6-Halogenalkoxy, C2-C6-Alkenyloxy, C2-C6-Cyanoalkenyloxy, C2-C6-Halogenalkeny- loxy, C2-C6-Alkinyloxy, Cι-C6-Alkylthio, Cι-C6-Cyanoalkylthio, Cι-C6-Halogenalkylthio, Cι-C6-Alkoxy-Cι-C6-Alkylthio, Cι-C6-Al- koxycarbonyl, Cι-C6-Alkylcarbonyl, Cι-C6-Alkylcarboxy-Cι-C6- Alkyl, Ci-Cδ-Alkylcarbonyl-Ci-Ce-Alkyl, Cx-Cö-Alkylcarbonyla- mino, Arylcarbonylamino, Arylsulphinyl, Arylsulphonyl, Hete- roarylsulphinyl, Heteroarylsulphonyl, Aryl-Cx-Cg-Alkyl, Aryl- C2-C6-Alkenyl, Aryl-C3-C6-Alkinyl, Heteroaryl-Cι-C6-alkyl, He- teroaryl-C -C6-Alkenyl, Heteroaryl-C3-C6-Alkinyl, Aryl- Cι-C6-Alkoxy, Aryl-C2-C6-Alkenyloxy, Aryl-C3-C6-Alkinyloxy, Heteroaryl-CxCg-alkoxy, Heteroaryl-C2-C6-Alkenyloxy, Heteroa- ryl-C3-C6-alkinyloxy, Cι-C6-Alkylsulphinyl, Cx-Ce-Alkylsulpho- nyl, C2-C6-Alkenylsulphinyl, C2-C6-Alkenylsulphonyl, Cι-C6-Al- kylamino, Di-Cι-C6-Alkylamino, HC=N0H, C1-C6-Alkyl-C=NOH, HC=N-0-C1-C6-Alkyl, HC=N-0-Cι-C6-Alkyl-Aryl, Cι-C6-Alkyl-C=N- O-Cx-Cö-Alkyl, HC=N-0-C2-C6-Alkenyl, Cι-C6-Alkyl-C=N-0-C2-C6- Alkenyl, HC=N-0-Aryl, C1-C6-Alkyl-C=N-0-Aryl, Aryl, Aryloxy, Heteroaryl, Heteroaryloxy, Arylthio, Heteroarylthio, wobei die cyclischen Substituenten ihrerseits unabhängig voneinander einen bis fünf der nachfolgenden Substituenten tragen können: Wasserstoff, Halogen, Cyano, Nitro, Hydroxy, Mer- capto, Thiocyanato, Carboxy, Amino,Cι-C6-Alkyl, Cι-C6-Cyanoal- kyl, C2-C6-Alkenyl, Cι-C6-Alkoxy-C2-C6-Alkenyl, C3-C6-Alkinyl, Cι-C6-Alkoxy-C3-C6-Alkinyl, C3-C6-Alkinyl-Cι-C6-Alkoxy, C3-C7- Cycloalkyl, Cι-C6-Alkyl-C3-C7-Cycloalkyl, Cι-C6-Alkoxy-C3-C7- Cycloalkyl, C3-C7-Cycloalkyloxy, C3-C -Cyanocycloalkyloxy, C -Cö-Alkyl-Cs-C-y-Cycloalkyloxy, C3-C7-Halogencycloalkyl, C3-C7-Cyanocycloalkyl, C3-C -Halogencycloalkyloxy, C5-C7-Cy- cloalkenyl, Cι-C6-Alkyl-C5-C7-Cycloalkenyl, Cι-C6-Alkoxy-C5-C7- Cycloalkenyl, C5-C7-Cyanocycloalkenyl, C5-C7-Halogencycloalke- nyl, Cι-C6-Alkoxy-Cι-C6-Alkyl, Cι-C6-Halogenalkyl, C2-C6-Halo- genalkenyl, C3-C6-Halogenalkinyl, C2-C6-Cyanoalkenyl, C3-C6- Cyanoalkinyl, Cι-C6-Alkoxy, Cι-C6-Cyanoalkoxy, Ci-Cö-Haloge- nalkoxy, C2-C6-Alkenyloxy, C2-C6-Cyanoalkenyloxy, C2-C6-Halo- genalkenyloxy, C -C6-Alkinyloxy, Cι-C6-Alkylthio, Cι-C6-Cyano- 3 alkylthio , Ci-Cg-Halogenalkylt io , Cι-C6-Alkoxy-Cι-C6-Alkylt - hio , Ci-Cg-Alkoxycarbonyl , Cι-C6-Alkylcarbonyl , Ci-Cg-Alkyl - carboxy-Cι-C6-Alkyl , Ci-Cg-Alkylcarbonyl-Ci-Cg-Alkyl , Cj-Cg-Al - kylcarbonylarαino , Arylcarbonylamino , Arylsulphinyl , Arylsul - phonyl , Heteroarylsulphinyl , Heteroarylsulphonyl , Aryl-, R 1 aryl or heteroaryl, where these radicals can independently carry one to five of the following groups: hydrogen, halogen, cyano, nitro, hydroxy, mercapto, thio 2 cyanato, carboxy, amino, Cι-C 6 -alkyl, C 6 cyanoalkyl, C 2 -C 6 - alkenyl, Cι-C 6 -alkoxy-C 2 -C 6 alkenyl, C 3 -C 6 - Alkynyl, -CC 6 -alkoxy-C 3 -C 6 -alkynyl, C 3 -C 6 -alkynyl-Cι-C 6 alkoxy, C 3 -C 7 cycloalkyl, -C-C 6 alkyl -C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy-C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyloxy, C 3 -C 7 cyanocycloalkyloxy, Cι-C 6 -Al- alkyl-C 3 -C 7 cycloalkyloxy, C 3 -C halocycloalkyl, C 3 -C 7 cycloalkyl cyano, C 3 -C 7 -Halogencycloalkyloxy, C 5 -C 7 cycloalkenyl, Cι-C 6 alkyl C 5 -C 7 cycloalkenyl, C 1 -C 6 alkoxy-C 5 -C 7 cycloalkenyl, C 5 -C 7 cyanocycloalkenyl, C 5 -C 7 halocycloalkenyl, C 1 -C 6 alkoxy-Cι- C 6 alkyl, C ! -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 6 haloalkynyl, C 2 -C 6 cyanoalkenyl, C 3 -C 6 cyanoalkynyl, C 1 -C 6 alkoxy, Cι -C 6 -Cyanoalkoxy, -C-C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -cyanoalkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, Cι-C 6 -alkylthio, -C-C 6 -cyanoalkylthio, -C-C 6 -haloalkylthio, -C-C 6 -alkoxy-Cι-C 6 -alkylthio, Cι-C 6 -alkoxycarbonyl, Cι-C 6 -alkylcarbonyl, Cι- C 6 -alkyl carboxy-Cι-C 6 - alkyl, Ci-C δ alkylcarbonyl-Ci-Ce-alkyl, Cx-C ö -Alkylcarbonyla- mino, arylcarbonylamino, Arylsulphinyl, arylsulphonyl, hetero- roarylsulphinyl, Heteroarylsulphonyl, aryl-Cx Cg-alkyl, aryl-C 2 -C 6 -alkenyl, aryl-C 3 -C 6 -alkynyl, heteroaryl -CC-C 6 -alkyl, heteroaryl-C -C 6 -alkenyl, heteroaryl-C 3 -C 6 -alkynyl, aryl -CC 6 alkoxy, aryl-C 2 -C 6 -alkenyloxy, aryl-C 3 -C 6 -alkynyloxy, heteroaryl-CxCg-alkoxy, heteroaryl-C 2 -C 6 -alkenyloxy, heteroa - Ryl-C 3 -C 6 alkynyloxy, -C-C 6 alkylsulphinyl, Cx-Ce -Alkylsulphonyl, C 2 -C 6 -Alkenylsulphinyl, C 2 -C 6 -Alkenylsulphonyl, Cι-C 6 -Alkylamino, Di-Cι-C 6 -alkylamino, HC = N0H, C 1 -C 6 alkyl -C = NOH, HC = N-0-C 1 -C 6 -alkyl, HC = N-0-Cι-C 6 -alkyl-aryl, Cι-C 6 -alkyl-C = N- O-Cx-C ö -alkyl, HC = N-0-C 2 -C 6 -alkenyl, -C-C 6 -alkyl-C = N-0-C 2 -C 6 - alkenyl, HC = N-0-aryl, C 1 - C 6 -alkyl-C = N-0-aryl, aryl, aryloxy, heteroaryl, heteroaryloxy, arylthio, heteroarylthio, where the cyclic substituents can in turn independently carry one to five of the following substituents: hydrogen, halogen, cyano, nitro, hydroxy , Mercapto, thiocyanato, carboxy, amino, -C 6 alkyl, C 6 -C cyanoalkyl, C 2 -C 6 alkenyl, C 6 alkoxy-C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, -CC 6 alkoxy-C 3 -C 6 -alkynyl, C 3 -C 6 -alkynyl-C 6 -C alkoxy, C 3 -C 7 - cycloalkyl, -C- 6 -Alkyl-C 3 -C 7 -cycloalkyl, -C-C 6 -alkoxy-C 3 -C 7 - cycloalkyl, C 3 -C 7 -cycloalkyloxy, C 3 -C -cyanocycloalkyloxy, C -C ö -alkyl-Cs- Cy-cycloal kyloxy, C 3 -C 7 halocycloalkyl, C 3 -C 7 -Cyanocycloalkyl, C 3 -C -Halogencycloalkyloxy, C 5 -C 7 cloalkenyl -Cy-, Cι-C 6 -alkyl-C 5 -C 7 cycloalkenyl, C 1 -C 6 alkoxy-C 5 -C 7 cycloalkenyl, C 5 -C 7 cyanocycloalkenyl, C 5 -C 7 halocycloalkenyl, C 1 -C 6 alkoxy-C 6 -C 6 alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 3 -C 6 -haloalkynyl, C 2 -C 6 -cyanoalkenyl, C 3 -C 6 - cyanoalkynyl, -C-C 6 -alkoxy, Cι-C 6 - cyanoalkoxy, C ö -Haloge- nalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 -Cyanoalkenyloxy, C 2 -C 6 genalkenyloxy -Halo-, C -C 6 alkynyloxy, Cι-C 6 -alkylthio , Cι-C 6 -Cyano- 3 alkylthio, Ci-Cg-haloalkylt io, -C-C 6 -alkoxy-Cι-C 6 -alkylt - hio, Ci-Cg-alkoxycarbonyl, Cι-C 6 -alkylcarbonyl, Ci-Cg-alkyl - carboxy-Cι-C 6- alkyl, Ci-Cg-alkylcarbonyl-Ci-Cg-alkyl, Cj-Cg-Al - alkylcarbonylarαino, arylcarbonylamino, arylsulphinyl, arylsul - phonyl, heteroarylsulphinyl, heteroarylsulphonyl, aryl-
Cι-C6-Alkyl , Aryl-C2-C6-Alkenyl , Aryl-C3-C6-Alkinyl , Heteroa - ryl-Ci-Cs-alkyl , Heteroaryl-C -C6-Alkenyl , Heteroaryl-C3- Cß-Alkinyl , Aryl-Ci-Cg-Alkoxy, Aryl-C2-C6-Alkenyloxy , Aryl- C3-C6-Alkinyloxy, Heteroaryl-CiCg-alkoxy, Heteroaryl-C -Cg-Al - kenyloxy, Heteroaryl-C3-Cg-alkinyloxy, Ci-Cg-Alkylsulphinyl ,C 1 -C 6 -alkyl, aryl-C 2 -C 6 -alkenyl, aryl-C 3 -C 6 -alkynyl, heteroaryl-Ci-Cs-alkyl, heteroaryl-C -C 6 -alkenyl, heteroaryl-C 3 - C ß- alkynyl, aryl-Ci-Cg-alkoxy, aryl-C 2 -C 6 -alkenyloxy, aryl-C 3 -C 6 -alkynyloxy, heteroaryl-CiCg-alkoxy, heteroaryl-C -Cg-alkynyloxy, Heteroaryl-C 3 -Cg-alkynyloxy, Ci-Cg-alkylsulphinyl,
Ci-Cg-Alkylsulphonyl , C -C6-Alkenylsulphinyl , C2-C6-Alkenyl - sulphonyl , Ci-Cg-Alkylamino , Di-Ci-Cg-Alkylamino , HC=NOH, Cι-C5-Alkyl-C=NOH, HC=N-0-Cι-C5-Alkyl , HC=N-0-Cι-C6-Alkyl- Aryl , Cι-C6-Alkyl-C=N-0-Cι-C6-Alkyl , HC=N-0-C -Cg-Alkenyl , Cι-C6-Alkyl-C=N-0-C2-C6-Alkenyl , HC=N-0-Aryl , Cι-C6-Al - kyl-C=N-0-Aryl, Aryl, Aryloxy, Heteroaryl, Heteroaryloxy, Arylthio, Heteroarylthio; oderCi-Cg-alkylsulphonyl, C -C 6 alkenylsulphinyl, C 2 -C 6 alkenylsulfonyl, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, HC = NOH, -C-C 5 alkyl-C = NOH, HC = N-0 -C-C 5 alkyl, HC = N-0-Cι-C 6 -alkyl-aryl, Cι-C 6 -alkyl-C = N-0-Cι-C 6 -alkyl, HC = N-0-C -Cg-alkenyl, -C-C 6 -alkyl-C = N-0-C 2 -C 6 -alkenyl, HC = N-0-aryl, Cι-C 6 -Al - kyl- C = N-0-aryl, aryl, aryloxy, heteroaryl, heteroaryloxy, arylthio, heteroarylthio; or
wobei der Aryl- oder Heteroarylrest mit einem ankondensierten P enylring, einem ankondensierten C3-C6-Carbocyclus oder einem 5- oder 6-gliedrigen Heterocyclus ein bicyclisches System ausbildet, wobei das ankondensierte Ringsystem gegebenenfalls einen bis drei der vorstehend für Aryl genannten Substituenten tragen kann.wherein the aryl or heteroaryl radical with a fused-on penyl ring, a fused-on C 3 -C 6 carbocycle or a 5- or 6-membered heterocycle forms a bicyclic system, the fused-on ring system optionally carrying one to three of the substituents mentioned above for aryl can.
R2 Ci-Cg-Alkyl oder Aryl oder Heteroaryl, wobei Aryl oder Heteroaryl einen bis drei der unter R1 für Aryl genannten Substituenten tragen können; C3 -C -Cycloalkyl oder Ci-Cε-Alkylaryl;R 2 Ci-Cg-alkyl or aryl or heteroaryl, where aryl or heteroaryl can carry one to three of the substituents mentioned under R 1 for aryl; C 3 -C cycloalkyl or Ci-Cε-alkylaryl;
A COOR3 oder CONR3R4, wobei R3 und R4 unabhängig voneinander Wasserstoff, Cι-C6-Alkyl, C2-C6-Alkenyl , C3-C7-Cycloalkyl oder Ci-Cg-Alkyl-Aryl bedeuten, welche ggf. teilweise oder vollständig halogeniert sein können oder einen bis drei Sub¬ stituenten ausgewählt aus Cι-C4-Alkoxy, Cχ-C4-Halogenalkoxy, Cι-C4-Alkylthio, C3-C -Cycloalkyl, C5-C -Cycloalkenyl tragen können;A COOR 3 or CONR 3 R 4 , where R 3 and R 4 are independently hydrogen, -CC 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 7 cycloalkyl or Ci-Cg-alkyl-aryl may be, which optionally partially or fully halogenated or substituents to three Sub ¬ selected from Cι-C4-alkoxy, Cχ-C4-haloalkoxy, Cι-C 4 alkylthio, C 3 -C cycloalkyl, C 5 - C can carry cycloalkenyl;
sowie deren landwirtschaftlich brauchbare Salze.and their agriculturally useful salts.
Die erfindungsgemäß zu verwendenden 2-Oxopyrrolderivate können hinsichtlich der Position des Substituenten R1 als E- oder als Z- Isomere oder Mischung aus beiden Isomeren eingesetzt werden.The 2-oxopyrrole derivatives to be used according to the invention can be used with respect to the position of the substituent R 1 as E or as Z isomers or a mixture of both isomers.
Die erfindungsgemäß zu verwendenden 2-Oxopyrrolderivate der For- mel I mit Ausnahme der folgenden Verbindungen sind neu und bilden einen eigenen Gegenstand der Erfindung: l R2 AThe 2-oxopyrrole derivatives of the formula I to be used according to the invention, with the exception of the following compounds, are new and form a separate subject of the invention: l R 2 A
C6H5 CH3 COOC2H5 C 6 H 5 CH 3 COOC 2 H 5
4 - ( CH3 ) 2N-C6H4 CH3 COOC2H5 4 - (CH 3 ) 2 NC 6 H 4 CH 3 COOC 2 H 5
2 -N02-C6H4 CH3 COOC H5 2 -N0 2 -C 6 H 4 CH 3 COOC H 5
4-N02-C6H4 CH3 COOC2H5 4-N0 2 -C 6 H 4 CH 3 COOC 2 H 5
4-Cl-C6H4 CH3 COOC2H5 4-Cl-C 6 H 4 CH 3 COOC 2 H 5
4 -Br-C6H4 CH3 COOC2H5 4 -Br-C 6 H 4 CH 3 COOC 2 H 5
4-CH3-C6H4 CH3 COOC2H5 4-CH 3 -C 6 H 4 CH 3 COOC 2 H 5
4-HO-C6H4 CH3 COOC2H5 4-HO-C 6 H 4 CH 3 COOC 2 H 5
2 , 4 - ( CH3 ) 2-5-COOCH2CH3-pyrrol-3-yl CH3 COOC2H5 2, 4 - (CH 3 ) 2 -5-COOCH 2 CH 3 -pyrrol-3-yl CH 3 COOC 2 H 5
3 , 5- ( CH3 ) 2-4-COOCH2CH3-pyrrol-2 -yl CH3 COOC2H5 3, 5- (CH 3 ) 2 -4-COOCH 2 CH 3 -pyrrol-2 -yl CH 3 COOC 2 H 5
C6H5 C6H5 COOCH3 C 6 H 5 C6H 5 COOCH 3
2 -COOCH2CH3-5-CH30-indol-3-yl CH3 COOC2H5 2 -COOCH 2 CH 3 -5-CH 3 0-indol-3-yl CH 3 COOC 2 H 5
4-CH30-C6H4 CH3 COOC2H5 4-CH 3 0-C 6 H 4 CH 3 COOC 2 H 5
Die bei der Definition von R1, R2 und A genannten organischen Molekülteile stellen Sammelbegriffe für individuelle Aufzählungen der einzelnen Bedeutungen dar. Sämtliche Kohlenstoff etten, also alle Alkyl-, Halogenalkyl-, Cyanoalkyl-, Alkoxy-, Halogen- alkoxy-, Cyanoalkoxy-, Alkylthio-, Alkylsulfinyl-, Alkyl- sulfonyl-, Alkylamino-, Dialkylamino-, Alkyloximino-, Alkylimi- nooxy-, Alkenyl-, Alkenyloxy-, Alkinyl-, Alkinyloxy- und Alki- nylthio-Teile können geradkettig oder verzweigt sein. Halogenierte Substituenten tragen vorzugsweise ein bis fünf gleiche oder verschiedene Halogenatome .The organic molecule parts mentioned in the definition of R 1 , R 2 and A are collective terms for individual enumeration of the individual meanings. All carbon chains, ie all alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, cyanoalkoxy, , Alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkyloximino, alkyliminooxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy and alkynylthio parts can be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms.
Die Bedeutung Halogen steht jeweils für Fluor, Brom, Chlor oder Iod, insbesondere für Fluor oder Chlor.Halogen is fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
Ferner stehen beispielsweise:Furthermore, for example:
Cι-C6-Alkyl für: Methyl, Ethyl, n-Propyl, 1-Methylethyl, n-Butyl, 1-Methylpropyl, 2-Methylpropyl oder 1, 1-Dimethyl- ethyl, n-Pentyl, 1-Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 2,2-Dimethylpropyl, 1-Ethylpropyl, n-Hexyl, 1, 1-Dimethyl- propyl, 1, 2-Dimethylpropyl, 1-Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1, 1-Dimethylbutyl, 1,2-Dimethylbutyl, 1, 3-Dimethylbutyl, 2 , 2-Dimethylbutyl, 2,3-Dimethylbutyl, 3, 3-Dimethylbutyl, 1-Ethylbutyl, 2-Ethylbutyl, 1, 1, 2-Trimethylpropyl, 1,2, 2-Trimethylpropyl, 1-Ethyl-l-methylpropyl oder l-Ethyl-2-methylpropyl, insbesondere für Methyl, Ethyl, n-Propyl, 1-Methylethyl, n-Butyl, 1, 1-Dimethylethyl, n-Pentyl oder n-Hexyl; 5-CC 6 alkyl for: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2- Methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2- Trimethylpropyl, 1,2, 2-trimethylpropyl, 1-ethyl-l-methylpropyl or l-ethyl-2-methylpropyl, especially for methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1, 1-dimethylethyl, n-pentyl or n-hexyl; 5
Cι-C6-Halogenalkyl für: Cι-C6-Alkyl wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. einen der unter Cι-C4-Halogenalkyl genannten Reste oder für 5-Fluor-l-pentyl, 5-Chlor-l-pentyl, 5-Brom-l-pentyl, 5-Iod-l-pentyl, 5,5,5-Tri- chlor-1-pentyl, Undecafluorpentyl, 6-Fluor-l-hexyl, 6-Chlor- 1-hexyl, 6-Brom-l-hexyl, 6-Iod-l-hexyl, 6, 6, 6-Trichlor-l- hexyl oder Dodecafluorhexyl, insbesondere für Chlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, 2-Fluorethyl, 2-Chlorethyl oder 2,2,2-Trifluorethyl;Cι-C 6 -haloalkyl: as mentioned above Cι-C6 alkyl which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine is substituted, eg one of the under Cι-C 4 haloalkyl radicals or 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6- Fluoro-l-hexyl, 6-chloro-1-hexyl, 6-bromo-l-hexyl, 6-iodo-l-hexyl, 6, 6, 6-trichloro-l-hexyl or dodecafluorohexyl, especially for chloromethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;
Cι-C6-Alkylamino für:Methylamino, Ethylamino, n-Propylamino, 1-Methylethylamino, n-Butylamino, 1-Methylpropylamino, 2-Me- thylpropylamino, 1, 1-Dimethylethylamino, n-Pentylamino, 1-Me- thylbutylamino, 2-Methylbutylamino, 3-Methylbutylamino,Cι-C 6 alkylamino for: methylamino, ethylamino, n-propylamino, 1-methylethylamino, n-butylamino, 1-methylpropylamino, 2-methylpropylamino, 1, 1-dimethylethylamino, n-pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino,
2,2-Dimethylpropylamino, 1-Ethylpropylamino, n-Hexylamino, 1, 1-Dimethylpropylamino, 1, 2-Dimethylpropylamino, 1-Methyl- pentylamino, 2-Methylpentylamino, 3-Methylpentylamino, 4-Me- thylpentylamino, 1, 1-Dimethylbutylamino, 1,2-Dimethylbutyla- mino, 1, 3-Dimethylbutylamino, 2,2-Dimethylbutylamino, 2,3-Di- methylbutylamino, 3, 3-Dimethylbutylamino, 1-Ethylbutylamino, 2-Ethylbutylamino, 1, 1,2-Trimethylpropylamino, 1,2,2-Trime- thylpropylamino, 1-Ethyl-1-methylpropylamino oder l-Ethyl-2-methylpropylamino, insbesondere für Methylamino, Ethylamino, n-Propylamino, 1-Methylethylamino, n-Butylamino, 1, 1-Dimethylethylamino, n-Pentylamino oder n-Hexylamino;2,2-dimethylpropylamino, 1-ethylpropylamino, n-hexylamino, 1, 1-dimethylpropylamino, 1, 2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1, 1- Dimethylbutylamino, 1,2-dimethylbutylamino, 1, 3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3, 3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1, 1,2- Trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino or l-ethyl-2-methylpropylamino, especially for methylamino, ethylamino, n-propylamino, 1-methylethylamino, n-butylamino, 1, 1- Dimethylethylamino, n-pentylamino or n-hexylamino;
Cyano-Cι-C6-alkyl für: z.B. Cyanomethyl, 1-Cyanoeth-l-yl, 2-Cyanoeth-l-yl, 1-Cyanoprop-l-yl, 2-Cyanoprop-l-yl, 3-Cyano- prop-1-yl, l-Cyanoprop-2-yl, 2-Cyanoprop-2-yl, 1-Cyanobut- 1-yl, 2-Cyanobut-l-yl, 3-Cyanobut-l-yl, 4-Cyanobut-l-yl, l-Cyanobut-2-yl, 2-Cyanobut-2-yl, l-Cyanobut-3-yl, 2-Cyano- but-3-yl, l-Cyano-2-methyl-prop-3-yl, 2-Cyano-2-methyl- prop-3-yl, 3-Cyano-2-methyl-prop-3-yl oder 2-Cyanomethyl- prop-2-yl, insbesondere für Cyanomethyl oder 2-Cyanoethyl;Cyano-Cι-C 6 alkyl for: for example cyanomethyl, 1-cyanoeth-l-yl, 2-cyanoeth-l-yl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyano-prop -1-yl, l-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4-cyanobut-l -yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, l-cyanobut-3-yl, 2-cyano-but-3-yl, l-cyano-2-methyl-prop-3-yl , 2-cyano-2-methyl-prop-3-yl, 3-cyano-2-methyl-prop-3-yl or 2-cyanomethyl-prop-2-yl, in particular for cyanomethyl or 2-cyanoethyl;
(Cι-C6-Alkyl)carbonyl für: Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, 1-Methylethylcarbonyl, n-Butylcarbonyl, 1-Methylpropylcarbonyl, 2-Methylpropylcarbonyl, 1, 1-Dimethyl- ethylcarbonyl, n-Pentylcarbonyl, 1-Methylbutylcarbonyl,(-CC 6 -alkyl) carbonyl for: methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1, 1-dimethylethylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl ,
2-Methylbutylcarbonyl, 3-Methylbutylcarbonyl, 1, 1-Dimethyl- propylcarbonyl, 1,2-Dimethylpropylcarbonyl, 2 ,2-Dimethyl- propylcarbonyl , 1-Ethylpropylcarbonyl, n-Hexylcarbonyl, 1-Methylpentylcarbonyl, 2-Methylpentylcarbonyl, 3-Methyl- pentylcarbonyl, 4-Methylpentylcarbonyl, 1, 1-Dimethylbutyl- carbonyl, 1, 2-Dimethylbutylcarbonyl, 1, 3-Dimethylbutyl- carbonyl, 2 ,2-Dimethylbutylcarbonyl, 2 , 3-Dimethylbutyl- 6 carbonyl, 3, 3-Dimethylbutylcarbonyl, 1-Ethylbutylcarbonyl, 2-Ethylbutylcarbony1, 1,1,2-Trimethylpropylcarbony1, 1,2, 2-Trimethylpropylcarbony1, 1-Ethyl-l-methylpropylcarbonyl oder 1-Ethy1-2-methylpropylcarbony1, insbesondere für Methyl- carbonyl, Ethylcarbonyl oder 1-Methylethylcarbony1;2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1, 1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2, 2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methyl- pentylcarbonyl, 4-methylpentylcarbonyl, 1, 1-dimethylbutylcarbonyl, 1, 2-dimethylbutylcarbonyl, 1, 3-dimethylbutylcarbonyl, 2, 2-dimethylbutylcarbonyl, 2, 3-dimethylbutyl- 6 carbonyl, 3, 3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbony1, 1,1,2-trimethylpropylcarbony1, 1,2, 2-trimethylpropylcarbonyl1, 1-ethyl-l-methylpropylcarbonyl or 1-ethyl1-2-methylpropylcarbony1, in particular for methylcarbonyl, ethylcarbonyl or 1-methylethylcarbony1;
(Cι-C6-Alkyl)carbonyl-Cι-C6-alkyl für: durch (Cχ-C6-Alkyl)- carbonyl wie vorstehend genannt substituiertes Ci-Cg-Alkyl, also z.B. für MethylcarbonyImethy1;(-C 6 -alkyl) carbonyl -CC 6 -alkyl for: Ci-Cg-alkyl substituted by (Cχ-C 6 -alkyl) carbonyl as mentioned above, for example for methylcarbonyImethy1;
(Cι-C6-Alkyl)carboxyl für: C!-C6-Alkyl wie vorstehend definiert, substituiert mit einer Carboxylgruppe, z.B. Methylcar- boxyl, Ethylcarboxyl, n-Propylcarboxyl, 1-Methylethylcarbo- xyl, n-Butylcarboxyl, 1-Methylpropylcarboxyl, 2-Methylpropyl- carboxyl oder 1, 1-Dimethylethylcarboxyl, insbesondere für Me- thylcarboxyl ;(-C 6 alkyl) carboxyl for: C ! -C 6 alkyl as defined above, substituted with a carboxyl group, for example methylcarboxyl, ethylcarboxyl, n-propylcarboxyl, 1-methylethylcarboxyl, n-butylcarboxyl, 1-methylpropylcarboxyl, 2-methylpropylcarboxyl or 1, 1-dimethylethylcarboxyl , especially for methyl carboxyl;
(C1-C6-Alkylcarboxyl)-Cι-C6-alkyl: für Cι-C6-Alkylcarboxyl wie vorstehend definiert, substituiert mit einer Cχ-C6-Alkylgruppe wie vorstehend definiert;(C 1 -C 6 -Alkylcarboxyl) -Cι-C 6 -alkyl: for -C-C 6 -alkylcarboxyl as defined above, substituted with a Cχ-C 6 -alkyl group as defined above;
Cι-C6-Alkoxy für: Methoxy, Ethoxy, n-Propoxy, 1-Methylethoxy, n-Butoxy, 1-Methylpropoxy, 2-Methylpropoxy oder 1, 1-Dimethyl- ethoxy, z.B. n-Pentoxy, 1-Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1, 1-Dimethylpropoxy, 1, 2-Dimeth lpropoxy, 2, 2-Di eth lpropoxy, 1-Ethylpropoxy, n-Hexoxy, 1-Methyl- pentoxy, 2-Methylpentoxy, 3-Methylpentoxy, 4-Methylpentoxy, 1, 1-Dimethylbutoxy, 1, 2-Dimethylbutoxy, 1, 3-Dimethylbutoxy, 2, 2-Dimethylbutoxy, 2, 3-Dimethylbutoxy, 3 , 3-Dimethylbutoxy, 1-Ethylbutoxy, 2-Ethylbutoxy, 1, 1, 2-Trimethylpropoxy, 1,2, 2-Trimethylpropoxy, 1-Ethyl-l-methylpropoxy und 1-Ethy1-2-methylpropoxy, insbesondere für Methoxy, Ethoxy oder 1-Methylethoxy;Cι-C 6 alkoxy for: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy, for example n-pentoxy, 1-methylbutoxy, 2nd -Methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimeth lpropoxy, 2, 2-dieth lpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2, 2-dimethylbutoxy, 2, 3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1,2, 2-trimethylpropoxy, 1-ethyl-l-methylpropoxy and 1-ethyl-1-2-methylpropoxy, in particular for methoxy, ethoxy or 1-methylethoxy;
Cχ-C6-Halogenalkoxy für: einen C -Cg-Alkoxyrest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. einen der unter Cι-C4-Halogenalkoxy genannten Reste oder für 5-Fluor-l-pent- oxy, 5-Chlor-l-pentoxy, 5-Brom-l-pentoxy, 5-Iod-l-pentoxy, 5, 5,5-Trichlor-l-pentoxy, Undecafluorpentoxy, 6-Fluor-l- hexoxy, 6-Chlor-l-hexoxy, 6-Brom-l-hexoxy, 6-Iod-l-hexoxy, 6, 6, 6-Trichlor-l-hexoxy oder Dodecafluorhexoxy, insbesondere für Chlormethoxy, Fluormethoxy, Difluormethoxy, Trifluormeth- oxy, 2-Fluorethoxy, 2-Chlorethoxy oder 2,2,2-Trifluorethoxy; 7Cχ-C 6 -haloalkoxy for: a C -Cg alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example one of the radicals mentioned under -C 4 -haloalkoxy or for 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5, 5,5-trichloro-1-pentoxy, undecafluoropentoxy, 6- Fluoro-l-hexoxy, 6-chloro-l-hexoxy, 6-bromo-l-hexoxy, 6-iodine-l-hexoxy, 6, 6, 6-trichloro-l-hexoxy or dodecafluorohexoxy, especially for chloromethoxy, fluoromethoxy, Difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy or 2,2,2-trifluoroethoxy; 7
(Cι-C6-Alkoxy)carbonyl für: Methoxycarbonyl, Ethoxycarbonyl, n-Propoxycarbonyl, 1-Methylethoxycarbonyl, n-Butoxycarbonyl, 1-Methylpropoxycarbonyl, 2-Methylpropoxycarbonyl oder 1, 1-Dimethylethoxycarbonyl, n-Pentoxycarbonyl, 1-Methyl- butoxycarbonyl, 2-Methylbutoxycarbonyl, 3-Methylbutoxy- carbonyl, 2, 2-Dimethylpropoxycarbonyl, 1-Ethylpropoxycarbonyl, n-Hexoxycarbonyl, 1, 1-Dimethylpropoxycarbonyl, 1 , 2-Dimethylpropoxycarbonyl, 1-Methylpentoxycarbonyl, 2-Methylpentoxycarbonyl, 3-Methylpentoxycarbonyl, 4-Methy1- pentoxycarbonyl, 1, 1-Dimethylbutoxycarbonyl, 1,2-Dimethyl- butoxycarbonyl , 1, 3-Dimethylbutoxycarbonyl, 2, 2-Dimethy1- butoxycarbonyl, 2 , 3-Dimethylbutoxycarbonyl, 3, 3-Dimethyl- butoxycarbonyl , 1-Ethylbutoxycarbonyl, 2-Ethylbutoxycarbonyl, 1, 1,2-Trimethylpropoxycarbonyl, 1,2 ,2-Trimethylpropoxy- carbonyl, 1-Ethyl-l-methyl-propoxycarbonyl oder l-Ethyl-2- methyl-propoxycarbonyl, insbesondere für Methoxycarbonyl, Ethoxycarbonyl oder 1-Methylethoxycarbonyl;(-C-C 6 -alkoxy) carbonyl for: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1, 1-dimethylethoxycarbonyl, n-pentoxycarbonyl, 1-methylbutoxycarbonyl , 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl -Methy1- pentoxycarbonyl, 1, 1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1, 3-dimethylbutoxycarbonyl, 2, 2-dimethy1-butoxycarbonyl, 2, 3-dimethylbutoxycarbonyl, 3, 3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl , 2-ethylbutoxycarbonyl, 1, 1,2-trimethylpropoxycarbonyl, 1,2, 2-trimethylpropoxycarbonyl, 1-ethyl-l-methyl-propoxycarbonyl or l-ethyl-2-methyl-propoxycarbonyl, in particular for methoxycarbonyl, ethoxycarbonyl or 1 -Methylethoxycarbonyl;
Cx-Cg-Alkylthio für: Methylthio, Ethylthio, n-Propylthio, 1-Methylethylthio, n-Butylthio, 1-Methylpropylthio,Cx-Cg-alkylthio for: methylthio, ethylthio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio,
2-Methylpropylthio, 1, 1-Dimethylethylthio, n-Pentylthio, 1-Methylbutylthio, 2-Methylbutylthio, 3-Methylbutylthio, 2, 2-Dimethylpropylthio, 1-Ethylpropylthio, n-Hexylthio, 1, 1-Dimethylpropylthio, 1,2-Dimethylpropylthio, 1-Methyl- pentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methyl- pentylthio, 1, 1-Dimethylbutylthio, 1, 2-Dimethylbutylthio, 1,3-Dimethylbutylthio, 2, 2-Dimethylbutylthio, 2, 3-Dimethyl- butylthio, 3, 3-Dimethylbutylthio, 1-Ethylbutylthio, 2-Ethyl- butylthio, 1, 1,2-Trimethylpropylthio, 1,2 ,2-Trimethylpropy1- thio, 1-Ethyl-1-methylpropylthio und 1-Eth 1-2-methylpropy1- thio, insbesondere für Methylthio oder Ethylthio;2-methylpropylthio, 1, 1-dimethylethylthio, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1, 1-dimethylpropylthio, 1,2- Dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1, 2-dimethylbutylthio, 1,3-dimethylbutylthio, 2, 2-dimethylbutylthio, 2, 3- Dimethylbutylthio, 3, 3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1, 1,2-trimethylpropylthio, 1,2, 2-trimethylpropy1thio, 1-ethyl-1-methylpropylthio and 1-eth 1 -2-methylpropy1- thio, especially for methylthio or ethylthio;
Cι-C6-Halogenalkylthio für: Ci-Cβ-Alkylthio wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor und/oder Brom substituiert ist, also z.B. einen der unter C!-C4-Halogenalkylthio genannten Reste oder für 5-Fluor- pentylthio, 5-Chlorpentylthio, 5-Brompentylthio, 5-Iod- pentylthio, ündecafluorpentylthio, 6-Fluorhexylthio oder 6-Chlorhexylthio, insbesondere für Chlormethylthio, Fluor- methylthio, Difluormethylthio, Trifluormethylthio, 2-Fluor- ethylthio, 2-Chlorethylthio oder 2,2 , 2-Trifluorethylthio;-C-C 6 -Halogenalkylthio for: Ci-Cβ-alkylthio as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for example one of those under C ! -C 4 -Halogenalkylthio radicals or for 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodo-pentylthio, ündecafluorpentylthio, 6-fluorhexylthio or 6-chlorohexylthio, especially for chloromethylthio, fluoromethylthioethyl, difluor , 2-fluoroethylthio, 2-chloroethylthio or 2,2, 2-trifluoroethylthio;
Cι-C6-Alkylsulfinyl für: Methylsulfinyl, Ethylsulfinyl, n-Propylsulfinyl, 1-Methylethylsulfinyl, n-Butylsulfinyl, 1-MethyIpropylsulfinyl, 2-MethyIpropylsulfinyl, 1, 1-Dimethyl- ethylsulfinyl, n-Pentylsulfinyl, 1-Methylbutylsulfinyl, 2-Methylbutylsulfinyl, 3-Methylbutylsulfinyl, 1, 1-Dimethyl- 8 propylsulfinyl, 1, 2-DimethyIpropylsulfinyl, 2, 2-Dimethyl- propylsulfinyl, 1-EthyIpropylsulfinyl, n-Hexylsulfinyl, 1-Methylpentylsulfinyl, 2-Methylpentylsulfinyl, 3-Methyl- pentylsulfinyl, 4-Methylpentylsulfinyl, 1, 1-Dimethylbuty1- sulfinyl, 1, 2-Dimethylbutylsulfinyl, 1, 3-Dimethylbutylsulfinyl, 2, 2-Dimethylbutylsulfinyl, 2 , 3-Dimeth lbutylsulfinyl, 3, 3-Dimethylbutylsulfinyl, 1-Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl, 1, 1, 2-TrimethyIpropylsulfinyl, 1 , 2 , 2-TrimethyIpropylsulfinyl, 1-Ethyl-1-methyIpropylsulfinyl oder l-Ethyl-2-methyIpropylsulfinyl, insbesondere für Methylsulfinyl;Cι-C 6 alkylsulfinyl for: methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methyl propylsulfinyl, 1, 1-dimethylethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfyl, 1-methylbutylsulfinyl Methylbutylsulfinyl, 3-methylbutylsulfinyl, 1, 1-dimethyl 8 propylsulfinyl, 1, 2-dimethylpropylsulfinyl, 2, 2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1, 1-sulfonyl , 1, 2-Dimethylbutylsulfinyl, 1, 3-Dimethylbutylsulfinyl, 2, 2-Dimethylbutylsulfinyl, 2, 3-Dimeth lbutylsulfinyl, 3, 3-Dimethylbutylsulfinyl, 1-Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl, 1, 1, 2-Trimethsulfinyl 2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl, in particular for methylsulfinyl;
Cι-C6-Alkylsulfonyl für: Methylsulfonyl, Ethylsulfonyl, n-Propylsulfonyl, 1-Methylethylsulfonyl, n-Butylsulfonyl, 1-MethyIpropylsulfonyl, 2-MethyIpropylsulfonyl, 1, 1-Dimethyl- ethylsulfonyl, n-Pentylsulfonyl, 1-Methylbutylsulfonyl, 2-Methylbutylsulfonyl, 3-Methylbutylsulfonyl, 1, 1-Dimethyl- propylsulfonyl, 1, 2-DimethyIpropylsulfonyl, 2,2-Dimethyl- propylsulfonyl, 1-EthyIpropylsulfonyl, n-Hexylsulfonyl, 1-Methylpentylsulfonyl, 2-Methylpentylsulfonyl, 3-Methyl- pentylsulfonyl, 4-Methylpentylsulfonyl, 1, 1-Dimethylbutylsulfonyl, 1, 2-Dimethylbutylsulfonyl, 1, 3-Dimethylbutyl- sulfonyl, 2, 2-Dimethylbutylsulfonyl, 2 ,3-Dimethylbutylsulfonyl, 3, 3-Dimethylbutylsulfonyl, 1-Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1, 1,2-TrimethyIpropylsulfonyl,Cι-C 6 alkylsulfonyl for: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methyl propylsulfonyl, 2-methyl propylsulfonyl, 1, 1-dimethyl ethylsulfonyl, n-pentyl Methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonylsulfonyl, 2-methyl 4-methylpentylsulfonyl, 1, 1-dimethylbutylsulfonyl, 1, 2-dimethylbutylsulfonyl, 1, 3-dimethylbutylsulfonyl, 2, 2-dimethylbutylsulfonyl, 2, 3-dimethylbutylsulfonyl, 3, 3-dimethylbutylsulfonyl, 1-ethylsulfonyl, 1-ethylsulfonyl 1, 1,2-trimethylpropylsulfonyl,
1,2, 2-TrimethyIpropylsulfonyl, 1-Ethyl-l-methyIpropylsulfonyl oder l-Ethyl-2-methylpropylsulfonyl, insbesondere für Methylsulfonyl;1,2, 2-trimethylpropylsulfonyl, 1-ethyl-l-methylpropylsulfonyl or l-ethyl-2-methylpropylsulfonyl, in particular for methylsulfonyl;
C2-C6-Alkenyl für: z.B. Ethenyl, Prop-2-en-l-yl, n-Buten-4-yl, l-Methyl-prop-2-en-l-yl, 2-Methyl-prop-2-en-l-yl, 2-Buten- 1-yl, n-Penten-3-yl, n-Penten-4-yl, l-Methyl-but-2-en-l-yl, 2-Methyl-but-2-en-l-yl, 3-Methyl-but-2-en-l-yl, 1-Methyl- but-3-en-l-yl, 2-Methyl-but-3-en-l-yl, 3-Methyl-but-3-en- 1-yl, 1, l-Dimethyl-prop-2-en-l-yl, 1, 2-Dimethyl-prop-2-en- 1-yl, l-Ethyl-prop-2-en-l-yl, n-Hex-3-en-l-yl, n-Hex-4-en- 1-yl, n-Hex-5-en-l-yl, l-Methyl-pent-3-en-l-yl, 2-Methyl- pent-3-en-l-yl, 3-Methyl-pent-3-en-l-yl, 4-Methyl-pent-3- en-l-yl, l-Methyl-pent-4-en-l-yl, 2-Methyl-pent-4-en-l-yl, 3-Methyl-pent-4-en-l-yl, 4-Methyl-pent-4-en-l-yl,C 2 -C 6 alkenyl for: e.g. ethenyl, prop-2-en-l-yl, n-buten-4-yl, l-methyl-prop-2-en-l-yl, 2-methyl-prop- 2-en-l-yl, 2-butene-1-yl, n-penten-3-yl, n-penten-4-yl, l-methyl-but-2-en-l-yl, 2-methyl but-2-en-l-yl, 3-methyl-but-2-en-l-yl, 1-methyl-but-3-en-l-yl, 2-methyl-but-3-en-l- yl, 3-methyl-but-3-en-1-yl, 1, l-dimethyl-prop-2-en-l-yl, 1, 2-dimethyl-prop-2-en-1-yl, l- Ethyl-prop-2-en-l-yl, n-hex-3-en-l-yl, n-hex-4-en-1-yl, n-hex-5-en-l-yl, l- Methyl-pent-3-en-l-yl, 2-methyl-pent-3-en-l-yl, 3-methyl-pent-3-en-l-yl, 4-methyl-pent-3-en- l-yl, l-methyl-pent-4-en-l-yl, 2-methyl-pent-4-en-l-yl, 3-methyl-pent-4-en-l-yl, 4-methyl pent-4-en-l-yl,
1, l-Dimethyl-but-2-en-l-yl, 1, l-Dimethyl-but-3-en-l-yl, 1 , 2-Dimethyl-but-2-en-l-yl, 1 , 2-Dimethyl-but-3-en-l-yl , 1, 3-Dimethyl-but-2-en-l-yl, 1, 3-Dimethyl-but-3-en-l-yl, 2 , 2-Dimethyl-but-3-en-1-y1, 2,3-Dimethyl-but-2-en-1-y1, 2,3-Dimethyl-but-3-en-l-yl, 3,3-Dimethyl-but-2-en-l-yl, l-Ethyl-but-2-en-l-yl, l-Ethyl-but-3-en-l-yl, 2-Ethyl-but-2- en-l-yl, 2-Ethyl-but-3-en-l-yl, 1, 1, 2-Trimethyl-prop-2-en- 91, l-dimethyl-but-2-en-l-yl, 1, l-dimethyl-but-3-en-l-yl, 1, 2-dimethyl-but-2-en-l-yl, 1, 2-dimethyl-but-3-en-l-yl, 1, 3-dimethyl-but-2-en-l-yl, 1, 3-dimethyl-but-3-en-l-yl, 2, 2- Dimethyl-but-3-en-1-y1, 2,3-dimethyl-but-2-en-1-y1, 2,3-dimethyl-but-3-en-1-yl, 3,3-dimethyl but-2-en-l-yl, l-ethyl-but-2-en-l-yl, l-ethyl-but-3-en-l-yl, 2-ethyl-but-2-en-l- yl, 2-ethyl-but-3-en-l-yl, 1, 1, 2-trimethyl-prop-2-en- 9
1-yl, l-Ethyl-l-methyl-prop-2-en-l-yl oder 1-Ethy1-2-methyl- prop-2-en-l-yl, insbesondere für Ethenyl, Prop-2-en-l-yl oder n-Buten-4-yl;1-yl, l-ethyl-l-methyl-prop-2-en-l-yl or 1-ethyl-1-2-methyl-prop-2-en-l-yl, especially for ethenyl, prop-2-ene l-yl or n-buten-4-yl;
C2-C6-Alkenylsulfinyl für : C2-C6-Alkenyl wie vorstehend definiert, substituiert mit einer Sulfinylgruppe, z.B. Ethenyl- sulfinyl, Prop-2-en-l-ylsulfinyl, n-Buten-4-ylsulfinyl, l-Methyl-prop-2-en-l-ylsulfinyl, 2-Methyl-prop-2-en-l-ylsul- finyl, 2-Buten-l-ylsulfinyl, n-Penten-3-ylsulfinyl, n-Pen- ten-4-ylsulfinyl, l-Methyl-but-2-en-l-ylsulfinyl, 2-Methyl- but-2-en-l-ylsulfinyl, 3-Methyl-but-2-en-l-ylsulfinyl, 1-Me- thyl-but-3-en-l-ylsulfinyl, 2-Methyl-but-3-en-l-ylsulfinyl, 3-Methyl-but-3-en-l-ylsulfinyl, 1, l-Dimethyl-prop-2-en-l-yl- sulfinyl, l,2-Dimethyl-prop-2-en-l-ylsulfinyl, 1-Ethyl- prop-2-en-l-ylsulfinyl, n-Hex-3-en-l-ylsulfinyl, n-C 2 -C 6 alkenylsulfinyl for: C 2 -C 6 alkenyl as defined above, substituted with a sulfinyl group, for example ethenylsulfinyl, prop-2-en-l-ylsulfinyl, n-buten-4-ylsulfinyl, l- Methyl-prop-2-en-l-ylsulfinyl, 2-methyl-prop-2-en-l-ylsulfinyl, 2-buten-l-ylsulfinyl, n-penten-3-ylsulfinyl, n-pentene- 4-ylsulfinyl, l-methyl-but-2-en-l-ylsulfinyl, 2-methyl-but-2-en-l-ylsulfinyl, 3-methyl-but-2-en-l-ylsulfinyl, 1-Me- thyl-but-3-en-l-ylsulfinyl, 2-methyl-but-3-en-l-ylsulfinyl, 3-methyl-but-3-en-l-ylsulfinyl, 1, l-dimethyl-prop-2- en-l-yl-sulfinyl, l, 2-dimethyl-prop-2-en-l-ylsulfinyl, 1-ethyl-prop-2-en-l-ylsulfinyl, n-hex-3-en-l-ylsulfinyl, n-
Hex-4-en-l-ylsulfinyl, n-Hex-5-en-l-ylsulfinyl, 1-Methyl- pent-3-en-l-ylsulfinyl, 2-Methyl-pent-3-en-l-ylsulfinyl, 3-Methyl-pent-3-en-l-ylsulfinyl, 4-Methyl-pent-3- en-1-ylsulfinyl, l-Methyl-pent-4-en-l-ylsulfinyl, 2-Methyl- pent-4-en-l-ylsulfinyl, 3-Methyl-pent-4-en-l-ylsulfinyl,Hex-4-en-l-ylsulfinyl, n-hex-5-en-l-ylsulfinyl, 1-methyl-pent-3-en-l-ylsulfinyl, 2-methyl-pent-3-en-l-ylsulfinyl, 3-methyl-pent-3-en-l-ylsulfinyl, 4-methyl-pent-3-en-1-ylsulfinyl, l-methyl-pent-4-en-l-ylsulfinyl, 2-methyl-pent-4- en-l-ylsulfinyl, 3-methyl-pent-4-en-l-ylsulfinyl,
4-Methyl-pent-4-en-l-ylsulfinyl, 1, l-Dimethyl-but-2-en-l-yl, 1, l-Dimethyl-but-3-en-l-ylsulfinyl, 1, 2-Dimethyl- but-2-en-l-ylsulfinyl, l,2-Dimethyl-but-3-en-l-ylsulfinyl, l,3-Dimethyl-but-2-en-l-ylsulfinyl, 1, 3-Dimethyl- but-3-en-l-ylsulfinyl, 2,2-Dimethyl-but-3-en-l-ylsulfinyl, 2 , 3-Dimethyl-but-2-en-l-ylsulfinyl, 2 , 3-Dimethyl- but-3-en-l-ylsulfinyl, 3,3-Dimethyl-but-2-en-l-ylsulfinyl, l-Ethyl-but-2-en-l-ylsulfinyl, l-Ethyl-but-3-en-l-ylsulfinyl, 2-Ethyl-but-2-, 2-Ethyl-but-3-en-l-ylsulfinyl, 1,1,2-Tri- methyl-prop-2-en-, l-Ethyl-l-methyl-prop-2-en-l-ylsulfinyl oder l-Ethyl-2-methyl-prop-2-en-l-ylsulfinyl, insbesondere für Ethenylsulfinyl, Prop-2-en-l-ylsulfinyl oder n-Buten-4-ylsulfinyl;4-methyl-pent-4-en-l-ylsulfinyl, 1, l-dimethyl-but-2-en-l-yl, 1, l-dimethyl-but-3-en-l-ylsulfinyl, 1, 2- Dimethyl-but-2-en-l-ylsulfinyl, l, 2-dimethyl-but-3-en-l-ylsulfinyl, l, 3-dimethyl-but-2-en-l-ylsulfinyl, 1, 3-dimethyl- but-3-en-l-ylsulfinyl, 2,2-dimethyl-but-3-en-l-ylsulfinyl, 2, 3-dimethyl-but-2-en-l-ylsulfinyl, 2, 3-dimethyl-but- 3-en-l-ylsulfinyl, 3,3-dimethyl-but-2-en-l-ylsulfinyl, l-ethyl-but-2-en-l-ylsulfinyl, l-ethyl-but-3-en-l- ylsulfinyl, 2-ethyl-but-2-, 2-ethyl-but-3-en-l-ylsulfinyl, 1,1,2-trimethyl-prop-2-en-, l-ethyl-l-methyl- prop-2-en-l-ylsulfinyl or l-ethyl-2-methyl-prop-2-en-l-ylsulfinyl, especially for ethenylsulfinyl, prop-2-en-l-ylsulfinyl or n-buten-4-ylsulfinyl;
C2-C6-Alkenylsulfonyl für: C2-C6-Alkenyl wie vorstehend definiert, substituiert mit einer Sulfonylgruppe, z.B. Ethenyl- sulfonyl, Prop-2-en-l-ylsulfonyl, n-Buten-4-ylsulfonyl, l-Methyl-prop-2-en-l-ylsulfonyl, 2-Methyl-prop-2-en-l-ylsul- fonyl, 2-Buten-l-ylsulfonyl, n-Penten-3-ylsulfonyl, n-Pen- ten-4-ylsulfonyl, l-Methyl-but-2-en-l-ylsulfonyl, 2-Methyl- but-2-en-l-ylsulfonyl, 3-Methyl-but-2-en-l-ylsulfonyl, 1-Me- thyl-but-3-en-l-ylsulfonyl, 2-Methyl-but-3-en-l-ylsulfonyl, 3-Methyl-but-3-en-l-ylsulfonyl, 1 , l-Dimethyl-prop-2-en-l-yl- sulfonyl, l,2-Dimethyl-prop-2-en-l-ylsulfonyl, 1-Ethyl- prop-2-en-l-ylsulfonyl, n-Hex-3-en-l-ylsulfonyl, n-C 2 -C 6 alkenylsulfonyl for: C 2 -C 6 alkenyl as defined above, substituted with a sulfonyl group, for example ethenylsulfonyl, prop-2-en-l-ylsulfonyl, n-buten-4-ylsulfonyl, l- Methyl-prop-2-en-l-ylsulfonyl, 2-methyl-prop-2-en-l-ylsulfonyl, 2-buten-l-ylsulfonyl, n-pentene-3-ylsulfonyl, n-pentene 4-ylsulfonyl, l-methyl-but-2-en-l-ylsulfonyl, 2-methyl-but-2-en-l-ylsulfonyl, 3-methyl-but-2-en-l-ylsulfonyl, 1-Me- thyl-but-3-en-l-ylsulfonyl, 2-methyl-but-3-en-l-ylsulfonyl, 3-methyl-but-3-en-l-ylsulfonyl, 1, l-dimethyl-prop-2- en-l-yl-sulfonyl, l, 2-dimethyl-prop-2-en-l-ylsulfonyl, 1-ethyl-prop-2-en-l-ylsulfonyl, n-hex-3-en-l-ylsulfonyl, n-
Hex-4-en-l-ylsulfonyl, n-Hex-5-en-l-ylsulfonyl, 1-Methyl- pent-3-en-l-ylsulfonyl, 2-Methyl-pent-3-en-l-ylsulfonyl, 10Hex-4-en-l-ylsulfonyl, n-hex-5-en-l-ylsulfonyl, 1-methyl-pent-3-en-l-ylsulfonyl, 2-methyl-pent-3-en-l-ylsulfonyl, 10
3-Methyl-pent-3-en-l-ylsulfonyl, 4-Methyl-pent-3- en-1-ylsulfonyl, l-Methyl-pent-4-en-l-ylsulfonyl, 2-Methyl- pent-4-en-l-ylsulfonyl, 3-Methyl-pent-4-en-l-ylsulfonyl, 4-Methyl-pent-4-en-l-ylsulfonyl, 1, l-Dimethyl-but-2-en-l-yl, 1, l-Dimethyl-but-3-en-l-ylsulfonyl, 1,2-Dimethyl- but-2-en-l-ylsulfonyl, 1 , 2-Dimethyl-but-3-en-l-ylsulfonyl, 1, 3-Dimethyl-but-2-en-l-ylsulfonyl, 1, 3-Dimethyl- but-3-en-l-ylsulfonyl, 2 ,2-Dimethyl-but-3-en-l-ylsulfonyl, 2 , 3-Dimethyl-but-2-en-l-ylsulfonyl, 2 , 3-Dimethyl- but-3-en-l-ylsulfonyl, 3, 3-Dimethyl-but-2-en-l-ylsulfonyl, l-Ethyl-but-2-en-l-ylsulfonyl, l-Ethyl-but-3-en-l-ylsulfonyl, 2-Ethyl-but-2-, 2-Ethyl-but-3-en-l-ylsulfonyl, 1,1,2-Tri- methyl-prop-2-en-, l-Ethyl-l-methyl-prop-2-en-l-ylsulfonyl oder l-Ethyl-2-methyl-prop-2-en-l-ylsulfonyl, insbesondere für Ethenylsulfonyl, Prop-2-en-l-ylsulfonyl oder n-Buten-4-ylsulfonyl;3-methyl-pent-3-en-l-ylsulfonyl, 4-methyl-pent-3-en-1-ylsulfonyl, l-methyl-pent-4-en-l-ylsulfonyl, 2-methyl-pent-4- en-l-ylsulfonyl, 3-methyl-pent-4-en-l-ylsulfonyl, 4-methyl-pent-4-en-l-ylsulfonyl, 1, l-dimethyl-but-2-en-l-yl, 1, l-dimethyl-but-3-en-l-ylsulfonyl, 1,2-dimethyl-but-2-en-l-ylsulfonyl, 1, 2-dimethyl-but-3-en-l-ylsulfonyl, 1, 3-dimethyl-but-2-en-l-ylsulfonyl, 1, 3-dimethyl-but-3-en-l-ylsulfonyl, 2, 2-dimethyl-but-3-en-l-ylsulfonyl, 2, 3- Dimethyl-but-2-en-l-ylsulfonyl, 2, 3-dimethyl-but-3-en-l-ylsulfonyl, 3, 3-dimethyl-but-2-en-l-ylsulfonyl, l-ethyl-but- 2-en-l-ylsulfonyl, l-ethyl-but-3-en-l-ylsulfonyl, 2-ethyl-but-2-, 2-ethyl-but-3-en-l-ylsulfonyl, 1,1,2 -Trimethyl-prop-2-en-, l-ethyl-l-methyl-prop-2-en-l-ylsulfonyl or l-ethyl-2-methyl-prop-2-en-l-ylsulfonyl, especially for Ethenylsulfonyl, prop-2-en-1-ylsulfonyl or n-buten-4-ylsulfonyl;
C2-C6-Halogenalkenyl für: C3-C6-Alkenyl wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor und/oder Brom substituiert ist, also z.B. 2-Chlorallyl,C 2 -C 6 haloalkenyl for: C 3 -C 6 alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for example 2-chloroallyl,
3-Chlorallyl, 2 ,3-Dichlorallyl, 3, 3-Dichlorallyl, 2,3,3-Tri- chlorallyl, 2 , 3-Dichlorbut-2-enyl, 2-Bromallyl, 3-Bromallyl, 2,3-Dibromallyl, 3,3-Dibromallyl, 2 , 3 , 3-Tribromallyl oder 2, 3-Dibrombut-2-enyl, insbesondere für 2-Chlorallyl oder 3,3-Dichlorallyl;3-chloroallyl, 2, 3-dichlorallyl, 3, 3-dichlorallyl, 2,3,3-trichlorallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2, 3, 3-tribromoallyl or 2,3-dibromobut-2-enyl, in particular for 2-chloroallyl or 3,3-dichlorallyl;
C2-C6-Alkenyloxy für: Ethenyloxy, Prop-1-en-l-yloxy, Prop-2-en-l-yloxy, 1-Methylethenyloxy, n-Buten-1-yloxy, n-Bu- ten-2-yloxy, n-Buten-3-yloxy, 1-Methyl-prop-l-en-l-yloxy, 2-Methyl-prop-l-en-l-yloxy, l-Methyl-prop-2-en-l-yloxy, 2-Me- thyl-prop-2-en-l-yloxy, n-Penten-1-yloxy, n-Penten-2-yloxy, n-Penten-3-yloxy, n-Penten-4-yloxy, 1-Methyl-but-l-en-l-yl- oxy, 2-Methyl-but-l-en-l-yloxy, 3-Methyl-but-l-en-l-yloxy, 1-Methyl-but-2-en-l-yloxy, 2-Methyl-but-2-en-l-yloxy, 3-Methyl-but-2-en-l-yloxy, l-Methyl-but-3-en-l-yloxy, 2-Methyl-but-3-en-1-yloxy, 3-Methyl-but-3-en-1-yloxy, 1 , l-Dimethyl-prop-2-en-l-yloxy, 1 , 2-Dimethyl-prop-l-en-l-yl- oxy, l,2-Dimethyl-prop-2-en-l-yloxy, l-Ethyl-prop-l-en-2-yl- oxy, l-Ethyl-prop-2-en-l-yloxy, n-Hex-1-en-l-yloxy, n-Hex-2- en-1-yloxy, n-Hex-3-en-l-yloxy, n-Hex-4-en-l-yloxy, n-Hex-5- en-1-yloxy, 1-Methy1-pent-l-en-l-yloxy, 2-Methyl-pent-l-en- 1-yloxy, 3-Methyl-pent-l-en-l-yloxy, 4-Methyl-pent-l-en-l-yl- oxy, l-Methyl-pent-2-en-l-yloxy, 2-Methyl-pent-2-en-l-yloxy, 3-Methyl-pent-2-en-1-yloxy, 4-Methyl-pent-2-en-1-yloxy, l-Methyl-pent-3-en-l-yloxy, 2-Methyl-pent-3-en-l-yloxy, 3-Methyl-pent-3-en-l-yloxy, 4-Methyl-pent-3-en-l-yloxy, l-Methyl-pent-4-en-l-yloxy, 2-Methyl-pent-4-en-l-yloxy, 11C 2 -C 6 alkenyloxy for: ethenyloxy, prop-1-en-l-yloxy, prop-2-en-l-yloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2 -yloxy, n-buten-3-yloxy, 1-methyl-prop-1-en-1-yloxy, 2-methyl-prop-1-en-1-yloxy, 1-methyl-prop-2-en-1 -yloxy, 2-methyl-prop-2-en-l-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy , 1-methyl-but-l-en-l-yloxy, 2-methyl-but-l-en-l-yloxy, 3-methyl-but-l-en-l-yloxy, 1-methyl-but -2-en-l-yloxy, 2-methyl-but-2-en-l-yloxy, 3-methyl-but-2-en-l-yloxy, l-methyl-but-3-en-l-yloxy , 2-methyl-but-3-en-1-yloxy, 3-methyl-but-3-en-1-yloxy, 1, l-dimethyl-prop-2-en-1-yloxy, 1, 2-dimethyl -prop-l-en-l-yl-oxy, l, 2-dimethyl-prop-2-en-l-yloxy, l-ethyl-prop-l-en-2-yl-oxy, l-ethyl-prop -2-en-l-yloxy, n-hex-1-en-l-yloxy, n-hex-2-en-1-yloxy, n-hex-3-en-l-yloxy, n-hex-4 -en-1-yloxy, n-hex-5-en-1-yloxy, 1-methyl-pent-1-en-1-yloxy, 2-methyl-pent-1-en-1-yloxy, 3-methyl -pent-l-en-l-yloxy, 4-methyl-pent-l-en-l-yl-oxy, l-methyl-pent-2-en-l-yloxy, 2-methyl-pent-2- en-l-yloxy, 3-methyl-pent-2-en-1-yloxy, 4-methyl-pent-2-en-1-yloxy, l-methyl-pent-3-en-l-yloxy, 2- Methyl-pent-3-en-l-yloxy, 3-methyl-pent-3-en-l-yloxy, 4-methyl-pent-3-en-l-yloxy, l-methyl-pent-4-en- l-yloxy, 2-methyl-pent-4-en-l-yloxy, 11
3-Methyl-pent-4-en-l-yloxy, 4-Methyl-pent-4-en-l-yloxy, l,l-Dimethyl-but-2-en-l-yloxy, 1, l-Dimethyl-but-3-en-l-yloxy, 1,2-Dimethyl-but-l-en-l-yloxy, 1, 2-Dimethyl-but-2-en-l-yloxy, 1 , 2-Dimethyl-but-3-en-1-yloxy, 1 , 3-Dimethy1-but-1-en-1-yloxy, l,3-Dimethyl-but-2-en-l-yloxy, l,3-Dimethyl-but-3-en-l-yloxy, 2 , 2-Dimethyl-but-3-en-l-yloxy, 2 , 3-Dimethyl-but-l-en-l-yloxy, 2 , 3-Dimethyl-but-2-en-l-yloxy, 2 , 3-Dimethyl-but-3-en-l-yloxy, 3 , 3-Dimethy1-but-1-en-1-yloxy, 3,3-Dimethyl-but-2-en-1-yloxy, 1-Ethyl-but-l-en-l-yloxy, l-Ethyl-but-2-en-l-yloxy, 1-Ethyl- but-3-en-l-yloxy, 2-Ethyl-but-l-en-l-yloxy, 2-Ethyl-but-2- en-1-yloxy, 2-Ethyl-but-3-en-l-yloxy, 1, 1,2-Trimethyl-prop-2- en-1-yloxy, l-Ethyl-l-methyl-prop-2-en-l-yloxy, l-Ethyl-2- methyl-prop-1-en-l-yloxy oder l-Ethyl-2-methyl-prop-2-en-l- yloxy, insbesondere für Ethenyloxy oder Prop-2-en-l-yloxy;3-methyl-pent-4-en-l-yloxy, 4-methyl-pent-4-en-l-yloxy, l, l-dimethyl-but-2-en-l-yloxy, 1, l-dimethyl but-3-en-l-yloxy, 1,2-dimethyl-but-l-en-l-yloxy, 1, 2-dimethyl-but-2-en-l-yloxy, 1, 2-dimethyl-but- 3-en-1-yloxy, 1,3-dimethyl-1-but-1-en-1-yloxy, 1,3-dimethyl-but-2-en-1-yloxy, 1,3-dimethyl-but-3- en-l-yloxy, 2, 2-dimethyl-but-3-en-l-yloxy, 2, 3-dimethyl-but-l-en-l-yloxy, 2, 3-dimethyl-but-2-en- l-yloxy, 2, 3-dimethyl-but-3-en-l-yloxy, 3, 3-dimethy1-but-1-en-1-yloxy, 3,3-dimethyl-but-2-en-1- yloxy, 1-ethyl-but-l-en-l-yloxy, l-ethyl-but-2-en-l-yloxy, 1-ethyl-but-3-en-l-yloxy, 2-ethyl-but- l-en-l-yloxy, 2-ethyl-but-2-en-1-yloxy, 2-ethyl-but-3-en-l-yloxy, 1, 1,2-trimethyl-prop-2-en- 1-yloxy, l-ethyl-l-methyl-prop-2-en-l-yloxy, l-ethyl-2-methyl-prop-1-en-l-yloxy or l-ethyl-2-methyl-prop- 2-en-1-yloxy, in particular for ethenyloxy or prop-2-en-1-yloxy;
C3-C6-Alkinyl für: Ethinyl, Prop-1-in-l-yl, Prop-2-in-l-yl, n-But-1-in-l-yl, n-But-l-in-3-yl, n-But-l-in-4-yl, n-But-2-in-l-yl, n-Pent-1-in-l-yl, n-Pent-l-in-3-yl, n-Pent-l-in-4-yl, n-Pent-l-in-5-yl, n-Pent-2-in-l-yl, n-Pent-2-in-4-yl, n-Pent-2-in-5-yl, 3-Methyl-but-l-in-3-yl, 3-Methyl-but-l-in-4-yl, n-Hex-1-in-l-yl, n-Hex-l-in-3-yl, n-Hex-l-in-4-yl, n-Hex-l-in-5-yl, n-Hex-l-in-6-yl, n-Hex-2-in-l-yl, n-Hex-2-in-4-yl, n-Hex-2-in-5-yl, n-Hex-2-in-6-yl, n-Hex-3-in-l-yl, n-Hex-3-in-2-yl, 3-Methyl- pent-1-in-l-yl, 3-Methyl-pent-l-in-3-yl, 3-Methyl- pent-l-in-4-yl, 3-Methyl-pent-l-in-5-yl, 4-Methyl-pent-l-in- 1-yl, 4-Methyl-pent-2-in-4-yl oder 4-Methyl-pent-2-in-5-yl, insbesondere für Ethinyl oder Prop-2-in-l-yl;C 3 -C 6 alkynyl for: ethynyl, prop-1-in-l-yl, prop-2-in-l-yl, n-but-1-in-l-yl, n-but-l-in -3-yl, n-but-l-in-4-yl, n-but-2-in-l-yl, n-pent-1-in-l-yl, n-pent-l-in-3 -yl, n-pent-1-in-4-yl, n-pent-1-in-5-yl, n-pent-2-in-1-yl, n-pent-2-in-4-yl , n-Pent-2-in-5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n-hex-1-in-l -yl, n-hex-1-in-3-yl, n-hex-1-in-4-yl, n-hex-1-in-5-yl, n-hex-1-in-6-yl , n-Hex-2-in-l-yl, n-Hex-2-in-4-yl, n-Hex-2-in-5-yl, n-Hex-2-in-6-yl, n -Hex-3-in-1-yl, n-hex-3-in-2-yl, 3-methyl-pent-1-in-1-yl, 3-methyl-pent-1-in-3-yl , 3-methyl-pent-l-in-4-yl, 3-methyl-pent-1-in-5-yl, 4-methyl-pent-1-in-1-yl, 4-methyl-pent-2 -in-4-yl or 4-methyl-pent-2-yn-5-yl, especially for ethynyl or prop-2-yn-l-yl;
C2-C6-Alkinyloxy für: Ethinyloxy, Prop-1-in-l-yloxy,C 2 -C 6 alkynyloxy for: ethynyloxy, prop-1-in-1-yloxy,
Prop-2-in-l-yloxy, n-But-1-in-l-yloxy, n-But-l-in-3-yloxy, n- But-l-in-4-yloxy, n-But-2-in-l-yloxy, n-Pent-1-in-l-yloxy, n- Pent-l-in-3-yloxy, n-Pent-l-in-4-yloxy, n-Pent-l-in-5-yloxy, n-Pent-2-in-l-yloxy, n-Pent-2-in-4-yloxy, n-Pent-2-in-5-yl- oxy, 3-Methyl-but-l-in-3-yloxy, 3-Methyl-but-l-in-4-yloxy, n- Hex-1-in-l-yloxy, n-Hex-l-in-3-yloxy, n-Hex-l-in-4-yloxy, n- Hex-l-in-5-yloxy, n-Hex-l-in-6-yloxy, n-Hex-2-in-l-yloxy, n- Hex-2-in-4-yloxy, n-Hex-2-in-5-yloxy, n-Hex-2-in-6-yloxy, n- Hex-3-in-l-yloxy, n-Hex-3-in-2-yloxy, 3-Methylpent-l-in-l-yl- oxy, 3-Methyl-pent-l-in-3-yloxy, 3-Methyl-pent-l-in-4-yloxy, 3-Methyl-pent-l-in-5-yloxy, 4-Methyl-pent-l-in-l-yloxy, 4-Me- thyl-pent-2-in-4-yloxy oder 4-Methylpent-2-in-5-yloxy, insbesondere für Ethinyloxy oder Prop-2-in-l-yloxy; 12Prop-2-in-l-yloxy, n-but-1-in-l-yloxy, n-but-l-in-3-yloxy, n-but-l-in-4-yloxy, n-but- 2-in-l-yloxy, n-pent-1-in-l-yloxy, n-pent-l-in-3-yloxy, n-pent-l-in-4-yloxy, n-pent-l- in-5-yloxy, n-pent-2-in-l-yloxy, n-pent-2-in-4-yloxy, n-pent-2-in-5-yl-oxy, 3-methyl-but- l-in-3-yloxy, 3-methyl-but-l-in-4-yloxy, n-hex-1-in-l-yloxy, n-hex-l-in-3-yloxy, n-hex l-in-4-yloxy, n-hex-l-in-5-yloxy, n-hex-l-in-6-yloxy, n-hex-2-in-l-yloxy, n-hex-2- in-4-yloxy, n-hex-2-in-5-yloxy, n-hex-2-in-6-yloxy, n-hex-3-in-l-yloxy, n-hex-3-in- 2-yloxy, 3-methylpent-1-in-1-yloxy, 3-methylpent-1-in-3-yloxy, 3-methylpent-1-in-4-yloxy, 3-methyl- pent-l-in-5-yloxy, 4-methyl-pent-l-in-l-yloxy, 4-methyl-pent-2-in-4-yloxy or 4-methylpent-2-in-5- yloxy, especially for ethynyloxy or prop-2-yn-l-yloxy; 12
C3-C7-Cycloalkyl für: Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl oder Cycloheptyl, insbesondere für Cyclopentyl oder Cyclohexyl;C 3 -C 7 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, in particular for cyclopentyl or cyclohexyl;
- C -C7-Cycloalkyloxy für: Cyclopropyloxy, Cyclobutyloxy, Cyclo- pentyloxy, Cyclohexyloxy oder Cycloheptyloxy;C 7 -C 7 cycloalkyloxy for: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy or cycloheptyloxy;
C5-C7-Cycloalkenyl für: Cyclopent-1-enyl, Cyclopent- 2-enyl, Cylopent-3-enyl, Cyclohex-1-enyl, Cyclohex-2-enyl, Cyclohex-3-enyl, Cyclohept-1-enyl, Cyclohept-2-enyl, Cyclo- hept-3-enyl oder Cyclohept-4-enyl;C 5 -C 7 cycloalkenyl for: cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3-enyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohept-1-enyl , Cyclohept-2-enyl, cyclohept-3-enyl or cyclohept-4-enyl;
Heteroaryl: aromatische Heterocyclen mit ein bis drei Hetero- atomen, ausgewählt aus einer Gruppe bestehend aus - ein bis drei Stickstoffatomen, einem oder zwei Sauerstoff- und einem oder zwei Schwefelatomen, z.B. Furyl wie 2-Furyl und 3-Furyl, Thienyl wie 2-Thienyl und 3-Thienyl, Pyrrolyl wie 2-Pyrrolyl und 3-Pyrrolyl, Isoxazolyl wie 3-Isoxazolyl, 4-Isoxazolyl und 5-Isoxazolyl, Isothiazolyl wie 3-Isothiazolyl, 4-Isothiazolyl und 5-Isothiazolyl, Pyrazolyl wie 3-Pyrazolyl, 4-Pyrazolyl und 5-Pyrazolyl, Oxazolyl wie 2-0xazolyl, 4-Oxazolyl und 5-0xazolyl, Thiazolyl wie 2-Thiazolyl, 4-Thiazolyl und 5-Thiazolyl, Imidazolyl wie 2-Imidazolyl und 4-lmidazolyl, Oxadiazolyl wie l,2,4-Oxadiazol-3-yl, l,2,4-Oxadiazol-5-yl und 1,3, 4-Oxadiazol-2-yl, Thiadiazolyl wie l,2,4-Thiadiazol-3-yl, 1,2 ,4-Thiadiazol-5-yl und l,3,4-Thiadiazol-2-yl, Triazolyl wie 1,2 ,4-Triazol-l-yl, l,2,4-Triazol-3-yl und l,2,4-Triazol-4-yl, Pyridinyl wie 2-Pyridinyl, 3-Pyridinyl und 4-Pyridinyl, Pyridazinyl wie 3-Pyridazinyl und 4-Pyridazinyl, Pyrimidinyl wie 2-Pyrimidinyl, 4-Pyrimidinyl und 5-Pyrimidinyl, des weiteren 2-Pyrazinyl, l,3,5-Triazin-2-yl und 1,2 ,4-Triazin-3-yl, insbesondere Pyridyl, Pyri idyl, Furanyl und Thienyl;Heteroaryl: aromatic heterocycles with one to three heteroatoms selected from a group consisting of - one to three nitrogen atoms, one or two oxygen and one or two sulfur atoms, e.g. Furyl such as 2-furyl and 3-furyl, thienyl such as 2-thienyl and 3-thienyl, pyrrolyl such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl such as 2-0xazolyl, 4-oxazolyl and 5-0xazolyl, thiazolyl such as 2-thiazolyl, 4-thiazolyl and 5-thiazolyl, Imidazolyl such as 2-imidazolyl and 4-imidazolyl, oxadiazolyl such as 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,3,4-oxadiazol-2-yl, thiadiazolyl such l, 2,4-thiadiazol-3-yl, 1,2, 4-thiadiazol-5-yl and l, 3,4-thiadiazol-2-yl, triazolyl such as 1,2,4-triazol-l-yl, l, 2,4-triazol-3-yl and l, 2,4-triazol-4-yl, pyridinyl such as 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl such as 3-pyridazinyl and 4-pyridazinyl, pyrimidinyl such as 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, furthermore 2-pyrazinyl, l, 3,5-triazin-2-yl and 1,2, 4-triazin-3-yl, in particular pyridyl, pyridyl, furanyl and Thienyl;
Aryl für: C6-Ci4-Aryl wie Phenyl, Naphthyl, Anthracenyl vorzugsweise Phenyl.Aryl for: C 6 -C 4 aryl such as phenyl, naphthyl, anthracenyl, preferably phenyl.
Die 2-0xopyrrolderivate sind nach an sich dem Fachmann bekannten und in der Literatur beschriebenen Verfahren erhältlich, so daß sich hier nähere Angaben erübrigen. Nur beipielsweise sei hier auf die in der Z. Physiol. Chem. 132 (1924), 72 und J.Org. Che . 57, 1992, 6032 beschriebenen Verfahren verwiesen. 13The 2-0xopyrrole derivatives can be obtained by processes known per se to the person skilled in the art and described in the literature, so that further details are unnecessary here. Just as an example here is that in the Z. Physiol. Chem. 132 (1924), 72 and J.Org. Che. 57, 1992, 6032. 13
Eine bevorzugte Verfahrensvariante ist dem nachstehenden Reaktionsschema 1 zu entnehmen. Die detaillierten Reaktionsbedingungen sind dem Fachmann bekannt:A preferred process variant is shown in Reaction Scheme 1 below. The detailed reaction conditions are known to the person skilled in the art:
Nl-L 4 Nl-L 4th
R ΗH2 R ΗH 2
R RR R
\\
0 o \0 o \
00
0= \ / ^ 0- 0 = \ / ^ 0-
R1- ΗR 1 - Η
^y^ ^o Ru N^ y ^ ^ o R u N
H H HH
: ID: ID
Eine weitere Synthese kann in Analogie zu an sich bekannten Ver¬ fahren über die Zwischenprodukte der Formeln Ha, Ilb oder IIC erfolgen, die einen weiteren Gegenstand der Erfindung bilden.A further synthesis can drive in analogy to known per se Ver ¬ on the intermediates of formulas Ha, IIb or IIC effected, which form a further subject of the invention.
AA
CF, ^M ^, 0 CF, ^ M ^, 0
Ha Ilb llcHa Ilb llc
Synthese von 2 -Trifluormethyl- 5- 0x0-4, 5-dihydropyrrol-3-carbon- säuremethylester (Ilb)Synthesis of 2-trifluoromethyl-5- 0x0-4, 5-dihydropyrrole-3-carbonic acid methyl ester (Ilb)
2 g (8,2 mmol) Trifluoracetylbutandicarbonsäuredimethylester wurden in 100ml Methanol gelöst und bei 0 bis 5°C mit Ammoniakgas gesättigt. Anschließend wurde bei Raumtemperatur 12 h gerührt, eingeengt, der Rückstand in 50 ml Xylol yufgenommen und nach Zugabe einer Spatelspitze p-Toluolsulfonsäure 6 h am Rückfluß erhitzt. 142 g (8.2 mmol) of dimethyl trifluoroacetylbutanedicarboxylate were dissolved in 100 ml of methanol and saturated at 0 to 5 ° C. with ammonia gas. The mixture was then stirred at room temperature for 12 h, concentrated, the residue was taken up in 50 ml of xylene and, after the addition of a spatula tip, p-toluenesulfonic acid was heated under reflux for 6 h. 14
Die Mischung wurde filtriert, das erhaltene Filtrat mit Wasser verdünnt und mit Essigsäureethylester extrahiert. Anschließend wurde die organische Phase eingeengt und getrocknet. (MH+ 210)The mixture was filtered, the filtrate obtained was diluted with water and extracted with ethyl acetate. The organic phase was then concentrated and dried. (MH + 210)
Synthese von 2-Methyl -5-oxo-4 , 5 -dihydropyrrol -3 -carbonsäurenitril IIcSynthesis of 2-methyl -5-oxo-4, 5-dihydropyrrole -3-carbonsitrile IIc
Eine Mischung von 0,9g (4,6 mmol) 2 -Methyl -5 -oxo-4 , 5 -dihydropyrrol -3 -carboxamid, 1,4g (9,2 mmol) Phosphoroxychlorid und 0,9g (6,4 mmol) Kaliumcarbonat wurde in 50 ml Aceton 6 h am Rückfluß erhitzt. Anschließend wurde eingeengt und der erhaltene Rückstand an Kieselgel chromatographiert (LM: Cyclohexan:Essigsäureethyle- ster 10:1 bis 1:1). Es wurden 0,15g (19 % d.Th.) des gewünschten Produktes erhalten (IR: 2220 cm'1) .A mixture of 0.9g (4.6 mmol) 2-methyl -5-oxo-4, 5-dihydropyrrole -3-carboxamide, 1.4g (9.2 mmol) phosphorus oxychloride and 0.9g (6.4 mmol) Potassium carbonate was refluxed in 50 ml acetone for 6 hours. The mixture was then concentrated and the residue obtained was chromatographed on silica gel (LM: cyclohexane: ethyl acetate 10: 1 to 1: 1). 0.15 g (19% of theory) of the desired product were obtained (IR: 2220 cm '1 ).
Bevorzugt werden erfindungsgemäß 2-Oxopyrrolderivate verwendet, in denen R2 für eine Ci-Cς-Alkylgruppe, A für eine Gruppierung COO-Cι-C6-Alkyl und R1 die in den nachfolgenden Tabellen A und B angegebenen Bedeutungen hat.According to the invention, preference is given to using 2-oxopyrrole derivatives in which R 2 for a C 1 -C 8 -alkyl group, A for a COO-C 6 -C 6 alkyl group and R 1 have the meanings given in Tables A and B below.
Besonders bevorzugt werden die Verbindungen der Formel I, in denen R2 für Methyl, Ethyl oder Propyl und A für COOCH3 bzw. COOC2H5 steht und R1 eine der in den nachfolgenden Tabellen A und B angegebenen Bedeutungen für Aryl bzw. Heteroaryl hat. Insbesondere bevorzugt werden Verbindungen, in denen R2 für Methyl und A für COOCH3 steht und R2 ein in 2- oder 2, 6 -Stellung substituierter Arylrest ist, welcher durch einen oder mehrere Halogen-, Alkyl - oder Halogenalkylgruppen substituiert sein kann.Particular preference is given to the compounds of the formula I in which R 2 is methyl, ethyl or propyl and A is COOCH 3 or COOC 2 H 5 and R 1 has one of the meanings given in Tables A and B below for aryl or heteroaryl Has. Compounds in which R 2 is methyl and A is COOCH 3 and R 2 is an aryl radical which is substituted in the 2- or 2,6-position and which can be substituted by one or more halogen, alkyl or haloalkyl groups are particularly preferred.
Des weiteren werden Verbindungen bevorzugt, in denen R1 für einen heteroaromatischen Rest, insbesondere einen substituierten Pyra- zolrest steht, der ggf. einen oder mehrere Halogensubstituenten tragen kann.Furthermore, compounds are preferred in which R 1 represents a heteroaromatic radical, in particular a substituted pyrazole radical, which can optionally carry one or more halogen substituents.
Tabelle A: R1 = ArylTable A: R 1 = aryl
Nr. Bedeutung R1 No. Meaning R 1
A.l. C6H5 Al C 6 H 5
A.2. 4-CCl3-C6H4 A.2. 4-CCl 3 -C 6 H 4
A.3. 1-NaphthylA.3. 1-naphthyl
A.4. 2-NaphthylA.4. 2-naphthyl
A.5. 2-CH3-C6H4 A.5. 2-CH 3 -C 6 H 4
A.6. 3-CH3-C6H4 A.6. 3-CH 3 -C 6 H 4
A.7. 4-CH3-C6H4 A.7. 4-CH 3 -C 6 H 4
A.8. 3,5-(CH3)2-C6H3 A.8. 3,5- (CH 3 ) 2 -C 6 H 3
A.9. 2,4-(CH3)2-C6H3 15A.9. 2,4- (CH 3 ) 2 -C 6 H 3 15
Nr. Bedeutung R1 No. Meaning R 1
A.10. 3,4-(CH3)2-C6H3 A.10. 3,4- (CH 3 ) 2 -C 6 H 3
A.ll. 2,4,6-(CH3)3-C6H2 Alles. 2,4,6- (CH 3 ) 3 -C 6 H 2
A.12. 2-C2H5-C6H4 A.12. 2-C 2 H 5 -C 6 H 4
A.13. 4-C2H5-C6H4 A.13. 4-C 2 H 5 -C 6 H 4
A.14. 4-(C2H5)C(CH3)2_C6H4 A.14. 4- (C 2 H 5 ) C (CH 3 ) 2 _C 6 H 4
A.15. 2-CH3-4-C4H9-C6H3 A.15. 2-CH 3 -4-C 4 H 9 -C 6 H 3
A.16. 2-CH3-4-CH30-C6H3 A.16. 2-CH 3 -4-CH 3 0-C 6 H 3
A.17. 2-CH3-4-C6H5-C6H3 A.17. 2-CH 3 -4-C 6 H 5 -C 6 H 3
A.18. 3,5-(Cl)2-4-CH3-C6H2 A.18. 3,5- (Cl) 2 -4-CH 3 -C 6 H 2
A.19. 4-t-C4H9-C6H4A.19. 4-tC 4 H 9 -C 6 H4
A.20. 4-(cH3)2CH-C6H4 A.20. 4- (cH 3 ) 2 CH-C 6 H 4
A.21. 4-CH2=C(CH3)-C6H4 A.21. 4-CH 2 = C (CH 3 ) -C 6 H 4
A.22. 3-t-C4H9-4-CH3-C6H3 A.22. 3-tC 4 H 9 -4-CH 3 -C 6 H 3
A.23. 2-CH3-3-C4H9-C6H3 A.23. 2-CH 3 -3-C 4 H 9 -C 6 H 3
A.24. 2,5-(CH3)2-4-CH30-C6H2 A.24. 2,5- (CH 3 ) 2 -4-CH 3 0-C 6 H 2
A.25. 2-Cl-C6H4 A.25. 2-Cl-C 6 H 4
A.26. 4-Cl-C6H4 A.26. 4-Cl-C 6 H 4
A.27. 3-Cl-C6H4 A.27. 3-Cl-C 6 H 4
A.28. 3,5-(Cl)2-C6H3 A.28. 3,5- (Cl) 2 -C 6 H 3
A.29. 2,4-(Cl)2-C6H3 A.29. 2,4- (Cl) 2 -C 6 H 3
A.30. 2,3-(Cl)2-C6H3 A.30. 2,3- (Cl) 2 -C 6 H 3
A.31. 3,4-(Cl)2-C6H3 A.31. 3,4- (Cl) 2 -C 6 H 3
A.32. 2-Cl-4-F-C6H3 A.32. 2-Cl-4-FC 6 H 3
A.33. 2-Cl-6-F-C6H3 A.33. 2-Cl-6-FC 6 H 3
A.34. 2-Cl-5-N02-C6H3 A.34. 2-Cl-5-N0 2 -C 6 H 3
A.35. 3-Cl-6-N02-C6H3 A.35. 3-Cl-6-N0 2 -C 6 H 3
A.36. 2-Br-C6H4 A.36. 2-Br-C 6 H 4
A.37. 3-Br-C6H4 A.37. 3-Br-C 6 H 4
A.38. 4-Br-C6H4 A.38. 4-Br-C 6 H 4
A.39. 4-CF2Cl-C6H4 A.39. 4-CF 2 Cl-C 6 H 4
A.40. 2-CF3-C6H4 A.40. 2-CF 3 -C 6 H 4
A.41. 4-CF3-C6H4 A.41. 4-CF 3 -C 6 H 4
A.42. 2,5-(CF3)2-C6H3 A.42. 2.5- (CF 3 ) 2 -C 6 H 3
A.43. 4-CH30-C6H4 A.43. 4-CH 3 0-C 6 H 4
A.44. 2-CH30-C6H4 A.44. 2-CH 3 0-C 6 H 4
A.45. 2,4-(CH30)2-C6H3 A.45. 2,4- (CH 3 0) 2 -C 6 H 3
A.46. 2,5-(CH30)2-C6H3 A.46. 2,5- (CH3 0) 2 -C 6 H 3
A.47. 3,5-(CH30)2-C6H3 A.47. 3,5- (CH3 0) 2 -C 6 H 3
A.48. 2,4,6-(CH30)3-C6H2 16A.48. 2,4,6- (CH 3 0) 3 -C 6 H 2 16
Nr. Bedeutung R1 No. Meaning R 1
A.49. 2,3,4-(CH30)3-C6H2 A.49. 2,3,4- (CH 3 0) 3 -C 6 H 2
A.50. 3,4,5-(CH30)3-C6H2 A.50. 3,4,5- (CH 3 0) 3 -C 6 H 2
5 A.51. 2,4,5-(CH30)3-C6H2 5 A.51. 2,4,5- (CH 3 0) 3 -C 6 H 2
A.52. 3-Br-4,5-(CH30)2-C6H2 A.52. 3-Br-4,5- (CH 3 0) 2 -C 6 H 2
A.53. 4-C2H50-C6H4 A.53. 4-C 2 H 5 0-C 6 H 4
A.54. 3-C2H50-C6H4 A.54. 3-C 2 H 5 0-C 6 H 4
A.55. 2-C2H50-C6H4 A.55. 2-C 2 H 5 0-C 6 H 4
1010
A.56. 4-C3H70-C6H4 A.56. 4-C 3 H 7 0-C 6 H 4
A.57. 4-C6Hι30-C6H4 A.57. 4-C 6 Hι 3 0-C 6 H 4
A.58. 3-C6H50-C6H4 A.58. 3-C 6 H 5 0-C 6 H 4
A.59. 4-CH3S-C6H4 A.59. 4-CH 3 SC 6 H 4
15 A.60. 2-OH-C6H4 15 A.60. 2-OH-C 6 H 4
A.61. 4-OH-C6H4 A.61. 4-OH-C 6 H 4
A.62. 2-OH-5-Br-C6H3 A.62. 2-OH-5-Br-C 6 H 3
A.63. 2,3-(OH)2-C6H3 A.63. 2,3- (OH) 2 -C 6 H 3
20 A.64. 3,4-(OH)2-C6H3 20 A.64. 3,4- (OH) 2 -C 6 H 3
A.65. 2-OH-3-CH30-C6H3 A.65. 2-OH-3-CH 3 0-C 6 H 3
A.66. 2-OH-5-CH30-C6H3 A.66. 2-OH-5-CH 3 0-C 6 H 3
A.67. 3-OH-4-CH30-C6H3 A.67. 3-OH-4-CH 3 0-C 6 H 3
A.68. 3-OH-4-C2H50-C6H3 A.68. 3-OH-4-C 2 H 5 0-C 6 H 3
?5? 5
A.69. 3-C2H50-4-CH30-C6H3 A.69. 3-C 2 H 5 0-4-CH 3 0-C 6 H 3
A.70. 2-CH30-5-Br-C6H3 A.70. 2-CH 3 0-5-Br-C 6 H 3
A.71. 2,3-(CH3)2-4-CH30-C6H2 A.71. 2,3- (CH 3 ) 2 -4-CH 3 0-C 6 H 2
A.72. 3-Br-4-CH30-C6H3 A.72. 3-Br-4-CH 3 0-C 6 H 3
3030
A.73. 3-CH30-4-OH-5-Br-C6H2 A.73. 3-CH 3 0-4-OH-5-Br-C 6 H 2
A.74. 2-OH-5-Cl-C6H3 A.74. 2-OH-5-Cl-C 6 H 3
A.75. 2-OH-3-N02-C6H3 A.75. 2-OH-3-N0 2 -C 6 H 3
A.76. 2-N02-4,5-(CH30)2-C6H2 A.76. 2-N0 2 -4.5- (CH 3 0) 2 -C 6 H 2
35 A.77. 4-n-C H9-C6H4 35 A.77. 4-nC H 9 -C6H 4
A.78. 4-CH2=CH-CH20-C6H4 A.78. 4-CH 2 = CH-CH 2 0-C 6 H 4
A.79. 2-F-C6H4 A.79. 2-FC 6 H 4
A.80. 3-F-C6H4 A.80. 3-FC 6 H 4
40 A.81. 4-F-C6H4 40 A.81. 4-FC 6 H 4
A.82. 2,4-F2-C6H4 A.82. 2,4-F 2 -C 6 H 4
A.83. 2,6-F2-C6H4 A.83. 2,6-F 2 -C 6 H 4
A.84. 2-F-5-N02-C6H3 A.84. 2-F-5-N0 2 -C 6 H 3
A.85. 3-F-6-N02-C6H3 5A.85. 3-F-6-N0 2 -C 6 H 3 5
A.86. 2-Br-4-F-C6H3 A.86. 2-Br-4-FC 6 H 3
A.87. 4-CN-C6H4 17A.87. 4-CN-C 6 H 4 17
Nr. Bedeutung R1 No. Meaning R 1
A.88. 2-CN-C5H4A.88. 2-CN-C5H4
A.89. 3-CN-C6H4 A.89. 3-CN-C 6 H 4
A.90. 2-N02-C6H4 A.90. 2-N0 2 -C 6 H 4
A.91. 3-N02-C6H4 A.91. 3-N0 2 -C 6 H 4
A.92. 4-N02-C6H4 A.92. 4-N0 2 -C 6 H 4
A.93. 4-COOH-C6H4 A.93. 4-COOH-C 6 H 4
A.94. 2-OH-3-N02-C6H3 A.94. 2-OH-3-N0 2 -C 6 H 3
A.95. 3,4-(CH3)2-6-Br-C6H2 A.95. 3,4- (CH 3 ) 2 -6-Br-C 6 H 2
A.96. 3-CH3-4-CH30-C6H3 A.96. 3-CH 3 -4-CH 3 0-C 6 H 3
A.97. 3-N02-4-Cl-C6H3 A.97. 3-N0 2 -4-Cl-C 6 H 3
A.98. 4-C6H40-C6H4 A.98. 4-C 6 H 4 0-C 6 H 4
A.99. 4-Cl-C6H4-C6H4 A.99. 4-Cl-C 6 H 4 -C 6 H 4
A.100. 4-(2,3-Cl2-C6H30)-C6H4 A.100. 4- (2,3-Cl 2 -C 6 H 3 0) -C 6 H 4
A.101. 4-(3,4-Cl2-C6H30)-C6H4 A.101. 4- (3,4-Cl 2 -C 6 H 3 0) -C 6 H 4
A.102. 4-(3-C2H5-C6H30)-C6H4 A.102. 4- (3-C 2 H 5 -C 6 H 3 0) -C 6 H 4
A.103. 4-(4-C2H5-C6H30)-C6H4A.103. 4- (4-C 2 H 5 -C 6 H 3 0) -C 6 H4
A.104. 4-(4-Cl-C6H30)-C6H4 A.104. 4- (4-Cl-C 6 H 3 0) -C 6 H 4
A.105. 4_( -Br-C6H30)-C6H4 A.105. 4_ ( -Br-C 6 H 3 0) -C 6 H 4
A.106. 4- ( 2-Cl-5-CH3-C6H30 ) -C6H4 A.106. 4- (2-Cl-5-CH 3 -C 6 H 3 0) -C 6 H 4
A.107. 4-(2,5-Cl2-C6H30)-C6HA.107. 4- (2,5-Cl 2 -C 6 H 3 0) -C 6 H
A.108. 4-(2-Cl-C6H30)-C6H4 A.108. 4- (2-Cl-C 6 H 3 0) -C 6 H 4
A.109. 4-(2-F-C6H30)-C6H4 A.109. 4- (2-FC 6 H 3 0) -C 6 H 4
A.110. 4-(2-Br-C6H30)-C6H4 A.110. 4- (2-Br-C 6 H 3 0) -C 6 H 4
A.lll. 4-(3,5-Cl2-C6H30)-C6H4 A.lll. 4- (3,5-Cl 2 -C 6 H 3 0) -C 6 H 4
A.112. 4-(3-CF3-C6H30)-C6H4 A.112. 4- (3-CF 3 -C 6 H 3 0) -C 6 H 4
A.113. 4-(3-Cl-C6H30)-C6H4 A.113. 4- (3-Cl-C 6 H 3 0) -C 6 H 4
A.114. 4- ( 3-Br-C6H30) -C6H4 A.114. 4- (3-Br-C 6 H 3 0) -C 6 H 4
A.115. 4- ( 4-CH30-C6H40) -C6H4 A.115. 4- (4-CH 3 0-C 6 H 4 0) -C 6 H 4
A.116. 2-Cl-4-N02-C6H3 A.116. 2-Cl-4-N0 2 -C 6 H 3
A.117. 3-Br-4-CH30-C6H3 A.117. 3-Br-4-CH 3 0-C 6 H 3
A.118. 3-(CH3)2N-C6H4 A.118. 3- (CH 3 ) 2 NC 6 H 4
A.119. 4-(C2H5)2N-C6H4 A.119. 4- (C 2 H 5 ) 2 NC 6 H 4
A.120. 4-CH2=CH-C6H4 A.120. 4-CH 2 = CH-C 6 H 4
A.121. 2-N02-4-(CH3)2N-C6H3 A.121. 2-N0 2 -4- (CH 3 ) 2 NC 6 H 3
A.122. 2- ( 2-Cl-C6H4 )CH20-C6H4 A.122. 2- (2-Cl-C 6 H 4 ) CH 2 0-C 6 H 4
A.123. 2- ( 2-CH3-C6H4 ) CH20-C6HA.123. 2- (2-CH 3 -C 6 H 4 ) CH 2 0-C 6 H
A.124. 2- ( 3-CH3-C6H4 ) CH20-C6H4 A.124. 2- (3-CH 3 -C 6 H 4 ) CH 2 0-C 6 H 4
A.125. 2-C6H4-CH20-C6H4 A.125. 2-C 6 H 4 -CH 2 0-C 6 H 4
A.126. 4-C6H4-CH20-C6H4 18A.126. 4-C 6 H 4 -CH 2 0-C 6 H 4 18th
Nr. Bedeutung R1 No. Meaning R 1
A.127. 4-(COOC2H5)-C6H4 A.127. 4- (COOC 2 H 5 ) -C 6 H 4
A.128. 2-N02-4- ( 2-Br-4-CF3-C6H30) -C6H3 A.128. 2-N0 2 -4- (2-Br-4-CF 3 -C 6 H 3 0) -C 6 H 3
A.129. 3,5-I2-4-OH-C6H2 A.129. 3,5-I 2 -4-OH-C 6 H 2
A.130. 2-CH30-5-COOCH3-C6H3 A.130. 2-CH 3 0-5-COOCH 3 -C 6 H 3
A.131. 2-OH-4-(C2H5)N-C6H3 A.131. 2-OH-4- (C 2 H 5 ) NC 6 H 3
A.132. 3-CH30-4-OCOCH3-C6H3 A.132. 3-CH 3 0-4-OCOCH 3 -C 6 H 3
A.133. 3,5,-I2-2-OH-C6H2 A.133. 3,5, -I 2 -2-OH-C 6 H 2
A.134. 2-(Cyclohexyl-2-en)-C6H4 A.134. 2- (cyclohexyl-2-ene) -C 6 H 4
A.135. 3-C6H4-CH2-0-C6H4 A.135. 3-C 6 H 4 -CH 2 -0-C 6 H 4
A.136. 2-NH2-5-N02-C6H3 A.136. 2-NH 2 -5-N0 2 -C 6 H 3
A.137. 2-(4-Cl-C6H4)S-C6H4 A.137. 2- (4-Cl-C 6 H 4 ) SC 6 H 4
A.138. 3-CH3COOCH -C6H4 A.138. 3-CH 3 COOCH -C 6 H 4
A.139. 4-CH30-3-(C6H5)CH20-C6H3 A.139. 4-CH 3 0-3- (C 6 H 5 ) CH 2 0-C 6 H 3
A.140. 3-CH30-2- ( C6H5 ) CH20-C6H3 A.140. 3-CH 3 0-2- (C 6 H 5 ) CH 2 0-C 6 H 3
A.141. 3-CH30-2-(C6H5)CH20-4-OH-C6H2 A.141. 3-CH 3 0-2- (C 6 H 5) CH 2 0-4-OH-C 6 H 2
A.142. 2-OH-3,5-Br2-C6HA.142. 2-OH-3,5-Br 2 -C 6 H
A.143. 3-CH30-4-(C6H4)CH20-C6H3 A.143. 3-CH 3 0-4- (C 6 H 4) CH 2 0-C 6 H 3
A.144. 2-CH30-NapthylA.144. 2-CH 3 0-naphthyl
A.145. 4-NH2-C6H4 A.145. 4-NH 2 -C 6 H 4
A.146. 4-CH30-3-(3-CH3-C6H4)CH20-C6H3 A.146. 4-CH 3 0-3- (3-CH 3 -C 6 H 4) CH 2 0-C 6 H 3
A.147. 2-OH-3-C6H5-C6H3 A.147. 2-OH-3-C 6 H 5 -C 6 H 3
A.148. 4-CH3CONH-C6HA.148. 4-CH 3 CONH-C 6 H
A.149. 4-CH3ON=C-C6H4 A.149. 4-CH 3 ON = CC 6 H 4
A.150. 4-C6H5-C6H4 A.150. 4-C 6 H 5 -C 6 H 4
A.151. 4-CH≡C-CH20-C6H4 A.151. 4-CH≡C-CH 2 0-C 6 H 4
A.152. 4-CH3SO-C6H4 A.152. 4-CH 3 SO-C 6 H 4
A.153. 2-S03H-4-Cl-C6H3 A.153. 2-S0 3 H-4-Cl-C 6 H 3
A.154. 4-N≡C-CH20-C6H4 A.154. 4-N≡C-CH 2 0-C 6 H 4
A.155. 3- ( 5-Pyrimidyl ) -C6H4 A.155. 3- (5-pyrimidyl) -C 6 H 4
A.156. 3 , 5-di-C4H9-4-OH-C6H2 A.156. 3, 5-di-C 4 H 9 -4-OH-C 6 H 2
A.157. 4-t-C4H90-C6H4A.157. 4-tC 4 H 9 0-C 6 H4
A.158. 1,1,2,3, 3-penta-CH3-indan-5-ylA.158. 1,1,2,3, 3-penta-CH 3 -indan-5-yl
A.159. 4- ( 2-CN-C6H4-CH=CH ) -C6H4 A.159. 4- (2-CN-C 6 H 4 -CH = CH) -C 6 H 4
A.160. 2 -N-Phthalimid-C6H4 A.160. 2 -N-phthalimide-C 6 H 4
A.161. 2-NH2-C6H4 A.161. 2-NH 2 -C 6 H 4
A.162. 4-( (C1CH2CH2) (CH3CH2)N) )-C6H4 A.162. 4- ((C1CH 2 CH 2 ) (CH 3 CH 2 ) N)) -C 6 H 4
A.163. 4-CH3OCOO-C6H4 A.163. 4-CH 3 OCOO-C 6 H 4
A.164. 2-NH2-5-N02-C6H3 A.164. 2-NH 2 -5-N0 2 -C 6 H 3
A.165. 2-N-phthalimid-5-N02-C6H3 19A.165. 2-N-phthalimide-5-NO 2 -C 6 H 3 19
Nr. Bedeutung R1 No. Meaning R 1
A.166. 3 , 5-di-CH3OCO-4-OH-C6H2 A.166. 3, 5-di-CH 3 OCO-4-OH-C 6 H 2
A.167. 2-OH-5- (CH2=CHCONCH2 ) -C6H3 A.167. 2-OH-5- (CH 2 = CHCONCH 2 ) -C 6 H 3
A.168. 4-CH30-3- ( CH2=CHCONCH2 ) -C6H3 A.168. 4-CH 3 0-3- (CH 2 = CHCONCH 2 ) -C 6 H 3
A.169. 3-N(CH3)2-C6H4 A.169. 3-N (CH 3 ) 2 -C 6 H 4
A.170. 2- ( CH3COOCH2 ) -4- ( N ( CH3 ) 2 ) -C6H3 A.170. 2- (CH 3 COOCH 2 ) -4- (N (CH 3 ) 2 ) -C 6 H 3
A.171. 4-(CH30-C(CH3)2)C-C6H4 A.171. 4- (CH 3 0-C (CH 3 ) 2 ) CC 6 H 4
A.172. 2-COOH-C6H4 A.172. 2-COOH-C 6 H 4
A.173. 4-( ( (CH3)2-N-CH2-CH2-N(CH3)2-C6H4 A.173. 4- (((CH 3 ) 2 -N-CH 2 -CH 2 -N (CH 3 ) 2 -C 6 H 4
A.174. 2-N02-4-N(CH3)2-C6H3 A.174. 2-N0 2 -4-N (CH 3 ) 2 -C 6 H 3
A.175. 2-COOH-4-N(CH3)2-C6H3 A.175. 2-COOH-4-N (CH 3 ) 2 -C 6 H 3
A.176. 2-C6H5CH2S-4-N(CH3)2-C6H3 A.176. 2-C 6 H 5 CH 2 S-4-N (CH 3 ) 2 -C 6 H 3
A.177. ( (4-CNC6H4-CH2-CH2-N(CH3) )-C6H4 A.177. ((4-CNC 6 H 4 -CH 2 -CH 2 -N (CH 3 )) -C 6 H 4
A.178. 4-ClCH2-C6H4 A.178. 4-ClCH 2 -C 6 H 4
A.179. 2-CH3-4-t-C4H9-C6H3 A.179. 2-CH 3 -4-tC 4 H 9 -C 6 H 3
A.180. 3-t-C4H9-4-CH30-C6H3 A.180. 3-tC 4 H 9 -4-CH 3 0-C 6 H 3
A.181. 4-(CH3)2C(OH)-C6H4 A.181. 4- (CH 3 ) 2 C (OH) -C 6 H 4
A.182. 4-(t-C4H9-COO)-C6HA.182. 4- (tC 4 H 9 -COO) -C 6 H
A.183. 3 , 5-di-t-C4H9-4-CH30-C6H2 A.183. 3, 5-di-tC 4 H 9 -4-CH 3 0-C 6 H 2
A.184. 4-CH3CH20-C(CH3)CH2-C6H4 A.184. 4-CH 3 CH 2 0-C (CH 3 ) CH 2 -C 6 H 4
A.185. 3 , 5-di-CH3-4-OH-C6H2 A.185. 3, 5-di-CH 3 -4-OH-C 6 H 2
A.186. 3- ( CH2=C ( CH3 ) CONHCH2 ) -6-OH-C6H3 A.186. 3- (CH 2 = C (CH 3 ) CONHCH 2 ) -6-OH-C 6 H 3
A.187. 3 , 5-di-t-C4H9-4-OH-C6H2 A.187. 3,5-di-tC 4 H 9 -4-OH-C 6 H 2
A.188. 4-CH3CH2C(CH3)2-C6H4 A.188. 4-CH 3 CH 2 C (CH 3 ) 2 -C 6 H 4
A.189. 2-CH3-4-CH3CH2C (CH3 ) 2-C6H3A.189. 2-CH 3 -4-CH 3 CH 2 C (CH 3 ) 2 -C 6 H3
A.190. 2-CH3-4-CH30-C6H3 A.190. 2-CH 3 -4-CH 3 0-C 6 H 3
A.191. 1,1,3,4 , 4-penta-CH3-tetralin-6-ylA.191. 1,1,3,4,4-penta-CH 3 -tetralin-6-yl
A.192. 1,1, 3-tri-CH3-3- ( (CH3 ) 3CCH2-indan-5- -ylA.192. 1,1,3-tri-CH 3 -3- ((CH 3 ) 3 CCH 2 -indan-5- -yl
A.193. 1 , 1 , 3-tri-CH3-4- ( (CH3 ) 3CCH2-indan-5 -ylA.193. 1, 1, 3-tri-CH 3 -4- ((CH 3 ) 3 CCH 2 -indan-5 -yl
A.194. 2-CH3S-C6H4 A.194. 2-CH 3 SC 6 H 4
A.195. 2-CF3S-C6H4 A.195. 2-CF 3 SC 6 H 4
A.196. 3-CF3S-C6H4 A.196. 3-CF 3 SC 6 H 4
A.197. 4-CF3S-C6H4 A.197. 4-CF 3 SC 6 H 4
A.198. 4-CH3S02-C6H4 A.198. 4-CH 3 S0 2 -C 6 H 4
A.199. 2-Cl-4-CH3S02-C6H3 A.199. 2-Cl-4-CH 3 S0 2 -C 6 H 3
A.200. 4-(C6H5-C≡C)-C6H4 A.200. 4- (C 6 H 5 -C≡C) -C 6 H 4
A.201. 4- ( 2-CN-thiophen-3-yl ) -CH2-0-C6H4 A.201. 4- (2-CN-thiophene-3-yl) -CH 2 -0-C 6 H 4
A.202. 4- ( CH3OCO-CH=CH ) -C6H4 A.202. 4- (CH 3 OCO-CH = CH) -C 6 H 4
A.203. 4- ( 4-t-C4H9-thiazol-2-yl ) -C6H4 A.203. 4- (4-tC 4 H 9 -thiazol-2-yl) -C 6 H 4
A.204. 4- ( 2 , 5 , -di-CH3-pyrrol-l-yl ) -C6H4 20A.204. 4- (2, 5, -di-CH 3 -pyrrol-l-yl) -C 6 H 4 20th
Nr. Bedeutung R1 No. Meaning R 1
A.205. 4- ( 1 , 2 , 3-thidiazol-4-yl ) -C6H4 A.205. 4- (1, 2, 3-thidiazol-4-yl) -C 6 H 4
A.206. 2- ( 5-Cl-l , 2 , 3-thiadiazol-4-yl ) CH20-C6H4 A.206. 2- (5-Cl-1,2,3-thiadiazol-4-yl) CH 2 O-C 6 H 4
A.207. 4- (C6H5_NH-N=CH) -C6H4 A.207. 4- (C 6 H 5 _NH-N = CH) -C 6 H 4
A.208. 2,3-(-OCF20-)-C6H3 A.208. 2.3 - (- OCF 2 0 -) - C 6 H 3
A.209. 3,4-(-OCF20-)-C6H3 A.209. 3.4 - (- OCF 2 0 -) - C 6 H 3
A.210. 3-c-C5H90-4-CH30-C6H3 A.210. 3-cC 5 H 9 0-4-CH 3 0-C 6 H 3
A.211. 5-Indanyl A.211. 5-indanyl
Tabelle B : R1 = HeteroarylTable B: R 1 = heteroaryl
Nr. Bedeutung R1 No. Meaning R 1
B.l. 2-PyridylB.l. 2-pyridyl
B.2. 6-Methyl-2-pyridylB.2. 6-methyl-2-pyridyl
B.3. 3-Cl-5-CF3-2-pyridylB.3. 3-Cl-5-CF 3 -2-pyridyl
B.4. 4 , 6- (CH3 ) 2-2-pyridylB.4. 4, 6- (CH 3 ) 2 -2-pyridyl
B.5. 5-CN-6-CH3S-2-pyridylB.5. 5-CN-6-CH 3 S-2-pyridyl
B.6. 3-PyridylB.6. 3-pyridyl
B.7. 6-Br-3-pyridylB.7. 6-Br-3-pyridyl
B.8. 4-PyridylB.8. 4-pyridyl
B.9. 2 , 6-Cl2-4-pyridylB.9. 2,6-Cl 2 -4-pyridyl
B.10. 2-C6H5S-3-pyridylB.10. 2-C 6 H 5 S-3-pyridyl
B.ll. 2 ( 4-Cl-C6H4 ) S-3-pyridylB.ll. 2 (4-Cl-C 6 H 4 ) S-3-pyridyl
B.12. 4-ChinolinylB.12. 4-quinolinyl
B.13. 4 , 6-Br2-4-chinolinylB.13. 4, 6-Br 2 -4-quinolinyl
B.14. 2-Cl-3-chinolinylB.14. 2-Cl-3-quinolinyl
B.15. 3-ChinolinylB.15. 3-quinolinyl
B.16. 6-CH30-2-Cl-3-chinolinylB.16. 6-CH 3 0-2-Cl-3-quinolinyl
B.17. 8-OH-2-chinolinylB.17. 8-OH-2-quinolinyl
B.18. 2-NH2-4 , 6-Cl2-5-pyrimidylB.18. 2-NH 2 -4, 6-Cl 2 -5-pyrimidyl
B.19. 4-NH2-2 , 6- (CH3 ) 2-5-pyrimidylB.19. 4-NH 2 -2, 6- (CH 3 ) 2 -5-pyrimidyl
B.20. 4 , 6- (CH30 ) 2-2-CH3S-5-pyrimidylB.20. 4, 6- (CH 3 0) 2 -2-CH 3 S-5-pyrimidyl
B.21. 2 , 4- (CH30) -5-pyrimidylB.21. 2, 4- (CH 3 0) -5-pyrimidyl
B.22. 2-QuinoxalinylB.22. 2-quinoxalinyl
B.23. 2-PyrrylB.23. 2-pyrryl
B.24. l-CH3-2-PyrrylB.24. 1-CH 3 -2-pyrryl
B.25. 3-FuranylB.25. 3-furanyl
B.26. 5-N02-Füran-2-y1B.26. 5-N0 2 -Füran-2-y1
B.27. l-C6H5-3-CH3-5-Cl-pyrazolylB.27. IC 6 H 5 -3-CH 3 -5-Cl-pyrazolyl
B.28. 1- ( 4-Cl-C6H4 ) -2-pyrazolylB.28. 1- (4-Cl-C 6 H 4 ) -2-pyrazolyl
B.29. 1- ( 2-Cl-C6H4 ) -5-CF3-4-pyrazolyl 21B.29. 1- (2-Cl-C 6 H 4 ) -5-CF 3 -4-pyrazolyl 21
Nr. Bedeutung R1 No. Meaning R 1
B.30. 1-( 3-CH3-C6H4 ) -5-CF3-4-pyrazolylB.30. 1- (3-CH 3 -C 6 H 4 ) -5-CF 3 -4-pyrazolyl
B.31. 3-C2H5OCO-5-pyrrazolylB.31. 3-C 2 H 5 OCO-5-pyrrazolyl
B.32. 1-( 4-Br-C6H4) -2-pyrrolylB.32. 1- (4-Br-C 6 H 4 ) -2-pyrrolyl
B.33. 1-( 4-CH30-C6H4 ) -3-pyrrolylB.33. 1- (4-CH 3 0-C 6 H 4 ) -3-pyrrolyl
B.34. 1,2, 5-tri-Methyl-pyrrolylB.34. 1,2,5-tri-methyl-pyrrolyl
B.35. 1- ( 2 , 3 , 4-Cl3-C6H2 ) -3-pyrrolylB.35. 1- (2, 3, 4-Cl 3 -C 6 H 2 ) -3-pyrrolyl
B.36. 1- ( 2 , 4-Cl2-C6H3 ) -3-pyrrolylB.36. 1- (2,4-Cl 2 -C 6 H 3 ) -3-pyrrolyl
B.37. l-(2-N02-4-Cl-C6H3)-3-pyrrolylB.37. 1- (2-NO 2 -4-Cl-C 6 H 3 ) -3-pyrrolyl
B.38. 3-C3H7-5-isoxazolylB.38. 3-C 3 H 7 -5-isoxazolyl
B.39. 3-lndolylB.39. 3-indolyl
B.40. l-CH3-2-Cl-3-indolylB.40. 1-CH 3 -2-Cl-3-indolyl
B.41. 4-Cl-5-Nitro-2-benzothiophenylB.41. 4-Cl-5-nitro-2-benzothiophenyl
B.42. 5-CH3-4-imidazolylB.42. 5-CH 3 -4-imidazolyl
B.43. 2- ( -CH30-C6H4 ) -4-oxazolylB.43. 2- (-CH 3 0-C 6 H 4 ) -4-oxazolyl
B.44. 1- ( 2 , 6- (CH3 ) 2-C6H3 ) -pyrrolylB.44. 1- (2, 6- (CH 3 ) 2 -C 6 H 3 ) pyrrolyl
B.45. 2-ThiazolylB.45. 2-thiazolyl
B.46. 1- ( 4-Cl-C6H4 ) -3-pyrrolylB.46. 1- (4-Cl-C 6 H 4 ) -3-pyrrolyl
B.47. 3-( 4-tC4H9-C6H4 ) -5-isoxazolylB.47. 3- (4-tC 4 H 9 -C 6 H 4 ) -5-isoxazolyl
B.48. 3-CgHs-5-isoxazolylB.48. 3-CgHs-5-isoxazolyl
B.49. l-CH3-4-pyrrazolylB.49. l-CH 3 -4-pyrrazolyl
B.50. 1- (4-Cl-C6H4 ) -5-CH3-4-pyrazolylB.50. 1- (4-Cl-C 6 H 4 ) -5-CH 3 -4-pyrazolyl
B.51. 1- ( 4-F-C6H4 ) -5-CH3-4-pyrazolylB.51. 1- (4-FC 6 H 4 ) -5-CH 3 -4-pyrazolyl
B.52. 1-( 4-Cl-C6H4 ) -3-CH3-4-pyrazolylB.52. 1- (4-Cl-C 6 H 4 ) -3-CH 3 -4-pyrazolyl
B.53. 1- ( 4-Br-C6H ) -4-pyrazolylB.53. 1- (4-Br-C 6 H) -4-pyrazolyl
B.54. 1- ( 4-Cl-C6H4 ) 3 , 5- (CH3 >2-4-pyrazolylB.54. 1- (4-Cl-C 6 H 4 ) 3, 5- (CH 3 > 2-4-pyrazolyl
B.55. 1- ( 4-CH30-C6H4 ) -5-CF3-4-pyrazolylB.55. 1- (4-CH 3 0-C 6 H 4 ) -5-CF 3 -4-pyrazolyl
B.56. l-C6H5-4-pyrazolylB.56. IC 6 H 5 -4-pyrazolyl
B.57. 1-( 4-Cl-C6H4 ) -4-pyrazolylB.57. 1- (4-Cl-C 6 H 4 ) -4-pyrazolyl
B.58. l-(C6H5-5-CH3-4-pyrrazolylB.58. 1- (C 6 H 5 -5-CH 3 -4-pyrrazolyl
B.59. 2-C6H5-4-oxazolylB.59. 2-C 6 H 5 -4-oxazolyl
B.60. 2- ( 4-Cl-C6H5 ) -4-oxazolylB.60. 2- (4-Cl-C 6 H 5 ) -4-oxazolyl
B.61. 4-CH3C6H4-4-oxazolylB.61. 4-CH 3 C 6 H 4 -4-oxazolyl
B.62. 4-CH3-5-C6H5-3-isoxazolylB.62. 4-CH 3 -5-C 6 H 5 -3-isoxazolyl
B.63. 3- ( 4-CI-C6H4 ) -5-isoxazolylB.63. 3- (4-CI-C 6 H 4 ) -5-isoxazolyl
B.64. 3-i-C3H7-5-isoxazolylB.64. 3-iC 3 H 7 -5-isoxazolyl
B.65. 3-t-CH9-5-isoxazolylB.65. 3-t-CH 9 -5-isoxazolyl
B.66. 3-sec-C4H9-5-isoxazolylB.66. 3-sec-C 4 H 9 -5-isoxazolyl
B.67. 3- ( 2-CH3-C3H6 ) -5-isoazolylB.67. 3- (2-CH 3 -C 3 H 6 ) -5-isoazolyl
B.68. 3-tC4H9-5-C6H5-4-isoxazolyl 22B.68. 3-tC 4 H 9 -5-C 6 H 5 -4-isoxazolyl 22
Nr. Bedeutung R1 No. Meaning R 1
B.69. 4-CH3-5- ( 4-CF3-C6H4 ) -3-isoxazolylB.69. 4-CH 3 -5- (4-CF 3 -C 6 H 4 ) -3-isoxazolyl
B.70. 3-ThiophenylB.70. 3-thiophenyl
B.71. 5-CH3-2-thiophenylB.71. 5-CH 3 -2-thiophenyl
B.72. 3-CH3-2-thiopheny1B.72. 3-CH 3 -2-thiopheny1
B.73. 5-Nitro-2-thiophenylB.73. 5-nitro-2-thiophenyl
B.74. 5-Cl-2-thiopheny1B.74. 5-Cl-2-thiopheny1
B.75. 5- ( 4-F-C6H4 ) -2-thiophenylB.75. 5- (4-FC 6 H 4 ) -2-thiophenyl
B.76. 5- ( 4-Cl-C6H4 ) -2-thiophenylB.76. 5- (4-Cl-C 6 H 4 ) -2-thiophenyl
B.77. 5-Br-2-thiopheny1B.77. 5-Br-2-thiopheny1
B.78. 4 , 5-Cl2-3-thiophenylB.78. 4, 5-Cl 2 -3-thiophenyl
B.79. 2 , 5-Br2-3-thiophenylB.79. 2, 5-Br 2 -3-thiophenyl
B.80. 5-N02-3-thiopheny1B.80. 5-N0 2 -3-thiopheny1
B.81. 4-CH3-5-imidazolylB.81. 4-CH 3 -5-imidazolyl
B.82. l-C6H5CH2-2-imidazolylB.82. IC 6 H 5 CH 2 -2-imidazolyl
B.83. 2- (CH3 ) 2N-5-thiazolylB.83. 2- (CH3) 2 N-5-thiazolyl
B.84. 2- ( 4-Cl-C6H4 ) -4-thiazolylB.84. 2- (4-Cl-C 6 H 4 ) -4-thiazolyl
B.85. 5-CH3COCH2-2-furylB.85. 5-CH 3 COCH 2 -2-furyl
B.86. 3-Br-5-CH3-2-benzo-b-thiophenylB.86. 3-Br-5-CH 3 -2-benzo-b-thiophenyl
B.87. 3 , 6-Cl2-2-benzo-b-thiophenylB.87. 3, 6-Cl 2 -2-benzo-b-thiophenyl
B.88. 2-NH2-3-CN-4-Cl-thiophenylB.88. 2-NH 2 -3-CN-4-Cl-thiophenyl
B.89. l-t-C4H9-4-pyrrazolyl B.89. ltC 4 H 9 -4-pyrrazolyl
Die 2-0xopyrrole I und deren landwirtschaftlich brauchbaren Salze eignen sich als Herbizide. Die I enthaltenden herbiziden Mittel bekämpfen Pflanzenwuchs auf Nichtkulturflächen sehr gut. In Kulturen wie Weizen, Reis, Mais, Soja und Baumwolle wirken sie gegen Unkräuter und Schadgräser, ohne die Kulturpflanzen nennenswert zu schädigen. Dieser Effekt tritt vor allem bei niedrigen Aufwandmengen auf.The 2-0xopyrrole I and their agriculturally useful salts are suitable as herbicides. The herbicidal compositions containing I control plant growth very well on non-cultivated areas. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
In Abhängigkeit von der jeweiligen Applikationsmethode können die Verbindungen I bzw. sie enthaltenden herbiziden Mittel noch in einer weiteren Zahl von Kulturpflanzen zur Beseitigung unerwünschter Pflanzen eingesetzt werden. In Betracht kommen bei- spielsweise folgende Kulturen:Depending on the particular application method, the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants. For example, the following cultures can be considered:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. napus, Brassica napus var. napo- brassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis 23 guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium) , Helianthus annuus, Hevea brasiliensis, Hordeum vulgäre, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacu (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgäre), Theobroma cacao, Tri- folium pratense, Triticum aestivum, Triticum duru , Vicia faba, Vitis vinifera und Zea mays .Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. Napus, Brassica napus var. Napos-brassica, Brassica rapa var. Silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis 23 guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgäre, Humulus lupulus, Ipomoea batatas, Juglinarissisumum, Lensulinaricisum, Lyulinarisisumusers, Lyulinarisisum, Lyulinarisisumum Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacu (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (see vulgar), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum duru, Vicia faba, Vitis vinifera and Zea mays.
Darüber hinaus können die Verbindungen I auch in Kulturen, die durch Züchtung einschließlich gentechnischer Methoden gegen die Wirkung von Herbiziden tolerant sind, verwandt werden.In addition, the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
Des weiteren eignen sich die 2-Oxopyrrole I auch zur Desikkation und/oder Defoliation von Pflanzen.The 2-oxopyrroles I are also suitable for the desiccation and / or defoliation of plants.
Als Desikkantien eignen sie sich insbesondere zur Austrocknung der oberirdischen Teile von Kulturpflanzen wie Kartoffel, Raps, Sonnenblume und Sojabohne. Damit wird ein vollständig mechani- sches Beernten dieser wichtigen Kulturpflanzen ermöglicht.As desiccants, they are particularly suitable for drying out the above-ground parts of crops such as potatoes, rapeseed, sunflower and soybeans. This enables fully mechanical harvesting of these important crops.
Von wirtschaftlichem Interesse ist ferner die Ernteerleichterung, die durch das zeitlich konzentrierte Abfallen oder Vermindern der Haftfestigkeit am Baum bei Zitrusfruchten, Oliven oder bei anderen Arten und Sorten von Kern-, Stein- und Schalenobst ermöglicht wird. Derselbe Mechanismus, das heißt die Förderung der Ausbildung von Trenngewebe zwischen Frucht- oder Blatt- und Sproßteil der Pflanzen ist auch für ein gut kontrollierbares Entblättern von Nutzpflanzen, insbesondere Baumwolle, wesentlich.Also of economic interest is the ease of harvesting, which is made possible by the temporally concentrated decrease or decrease in the adhesive strength on the tree in the case of citrus fruits, olives or other types and varieties of pome, stone and nuts. The same mechanism, that is to say the promotion of the formation of separating tissue between the fruit or leaf and shoot part of the plants, is also essential for a well controllable defoliation of useful plants, in particular cotton.
Außerdem führt die Verkürzung des Zeitintervalls, in dem die einzelnen Baumwollpflanzen reif werden, zu einer erhöhten Faserqualität nach der Ernte.In addition, the shortening of the time interval in which the individual cotton plants ripen leads to increased fiber quality after the harvest.
Erfindungsgemäß werden die Verbindungen der Formel I auch zur Be- kämfung von tierischen Schädlingen aus der Klasse der Insekten, Spinnentiere und Nematoden eingesetzt. Sie können im Pflanzenschutz sowie auf dem Hygiene-, Vorratsschutz- und Veterinärsektor zur Bekämpfung tierischer Schädlinge eingesetzt werden. Insbeson- dere eignen sie sich zur Bekämpfung der folgenden tierischen Schädlinge: 24According to the invention, the compounds of the formula I are also used for combating animal pests from the class of the insects, arachnids and nematodes. They can be used in crop protection as well as in the hygiene, storage protection and veterinary sectors to control animal pests. They are particularly suitable for controlling the following animal pests: 24
• Insekten aus der Ordnung der Schmetterlinge (Lepidoptera) beispielsweise Agrotis ypsilon, Agrotis segetum, Alabama argilla- cea, Anticarsia gemmatalis , Argyresthia conjugella, Autographa ga ma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia bru ata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insu- lana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersi- cella, Labdina fiscellaria, Laphygma exigua, Leucoptera cof- feella, Leucoptera scitella, Lithocolletis blancardella, Lobe- sia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseu- doplusia includens, Rhyacionia frustrana, Scrobipalpula abso- luta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumato- poea pityocampa, Tortrix viridana, Trichoplusia ni und Zeira- phera canadensis,• Insects from the order of the butterflies (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argilla- cea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa ga ma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobistura choreisurauraura bruisturaura auraoneura choroidura choroidura choroidal bruise aura , Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonothisis, Armolithiothaisella, Grapholithaiothaisana, Grapholithaioleisole, Grapholithaiolesaoles, Grapholithaioleisole, Grapholithaiolesaoles, Grapholithaioleisole , Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersi- cella, Labdina fiscellaria, Laphygma exigua, Leucoptera COF feella, Leucoptera scitella, Lithocolletis blancardella, Lobe- sia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestr a brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xyloplanaia, Putella xyloplanaia, Putella xyloplana abs cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoe pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis,
• Käfer (Coleoptera) , z.B. Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Bla- stophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bru- chus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebu- losa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorr- hynchus napi, Chaetocne a tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punc- tata, Diabrotica virgifera, Epilachna varivestis, Epitrix hir- tipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis , Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa dece lineata, Limonius californi- cus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyl- lopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus und Sitophilus granaria,Beetles (Coleoptera), e.g. Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruechus pisorum, Bruchus lentisu- losa, Byiscus , Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorr- hynchus napi, Chaetocne a tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punc- tata, Diabrotica virgiferisisobutisisobirisisinobisisinobisisobutisis, Epilachinitris, Epilachinisis, Epilachilisna, epilachinisis, epilachinisis, epilachinis, histobis brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa dece lineata, Limonius californi- cus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolonche, melolonthaulolonhychon Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha hortic ola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria,
Zweiflügler (Diptera), z.B. Aedes aegypti, Aedes vexans, Anas- trepha ludens, Anopheles maculipennis, Ceratitis capitata, 25Two-winged birds (Diptera), e.g. Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, 25th
Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macella- ria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pi- piens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fan- nia canicularis, Gasterophilus intestinalis, Glossina morsi- tans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoder a lineata, Liriomyza sativae, Liriomyza trifo- lii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lyco- ria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagole- tis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula ole- racea und Tipula paludosa,Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macella- ria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pi- piens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fan- nia canicularis, Gasterophilus intestinalis, glipidisisisisisodisisisodisis, glossina misplantis, glossina metrisis, feminine equilibrium, glossina morphisis, glossina misplantis, glossina misoblus Hylemyia platura, Hypoder a lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella hysophilia, Pegomya Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula ole-racea and Tipula paludosa,
• Thripse (Thysanoptera), z.B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi und Thrips tabaci,Thrips (Thysanoptera), e.g. Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,
• Hautflügler (Hymenoptera) , z.B. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testu- dinea, Monomorium pharaonis, Solenopsis geminata und Solenopsis invicta,Dermatoptera (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta,
• Wanzen (Heteroptera) , z.B. Acrosternum hilare, Blissus leucop- terus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus in- termedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Ne- zara viridula, Piesma quadrata, Solubea insularis und Thyanta perditor,Bugs (Heteroptera), e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara quadrantulais, Pyanma viridula, Pies
• Pflanzensauger (Homoptera), z.B. Acyrthosiphon onobrychis,Plant suckers (Homoptera), e.g. Acyrthosiphon onobrychis,
Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Ce- rosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopa- lomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sap- paphis mali, Schizaphis graminum, Schizoneura lanuginosa, Tria- leurodes vaporariorum und Viteus vitifolii,Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Ce- rosipha gossypii, Dreyfusia nordmannianae, Dreyfusiaipheae, Macyosophiosumiabia, Macysoleosumiaumia, Macysapiaumia, Macys Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopa- lomyzus ascalonicus, Rhopalosiphum maisisapalisapalis malapis malapia malapia, Sap lanuginosa, Tria- leurodes vaporariorum and Viteus vitifolii,
• Termiten (Isoptera), z.B. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus und Termes natalensis,Termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis,
• Geradflügler (Orthoptera) , z.B. Acheta domestica, Blatta orien- talis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melano- 26 plus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguini- pes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus und Tachycines asynamorus,• Straight wing (Orthoptera), e.g. Acheta domestica, Blatta orien- talis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melano- 26 plus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus,
• Arachnoidea wie Spinnentiere (Acarina) , z.B. Amblyomma america- nu , Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoeni- cis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius me- gnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllo- coptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus , Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetra- nychus pacificus, Tetranychus telarius und Tetranychus urticae,Arachnoid such as arachnids (Acarina), e.g. Amblyomma america- nu, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Rubusus Iodinobusinusnobin, Ialodiaxus tris me- gnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllo- coptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabieus, Tetranychus cinnabarinus tawchychanyus tawchychanyus tawchychanyus tawchychanyus, Tetranych
• Nematoden wie Wurzelgallennematoden, z.B. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Zysten bildende Nematoden, z.B. Globodera rostochiensis, Heterodera avenae, He- terodera glycines, Heterodera schachtii, Heterodera trifolii, Stock- und Blattälchen, z.B. Belonolaimus longicaudatus, Dity- lenchus destructor, Ditylenchus dipsaci, Heliocotylenchus mul- ticinctus, Longidorus elongatus, Radopholus similis, Rotylen- chus robustus, Trichodorus primitivus, Tylenchorhynchus clay- toni, Tylenchorhynchus dubius, Pratylenchus neglectus, Praty- lenchus penetrans, Pratylenchus curvitatus und Pratylenchus goodeyi .Nematodes such as root gall nematodes, e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stick and leaf wholes, e.g. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multi- ticinctus, Longidorus elongatus, Radopholus similis, Rotylen- chus robustus, Trichodorus primitivus, Tylenchorhynchus clay- toni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.
Die Verbindungen I bzw. die sie enthaltenden Mittel können beispielsweise in Form von direkt versprühbaren wäßrigen Lösungen, Pulvern, Suspensionen, auch hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen oder Dispersionen, Emulsionen, Öldisper- sionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsformen richten sich nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten.The compounds I or the compositions comprising them can be sprayed, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules. Nebulization, dusting, scattering or pouring can be used. The application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
Als inerte Hilfsstoffe kommen im Wesentlichen in Betracht:The following are essentially considered as inert auxiliaries:
Mineralölfraktionen von mittlerem bis hohem Siedepunkt wie Kero- sin und Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z.B. Paraffine, Tetrahydronaphthalin, alkylierte Naphthaline und deren Derivate, alkylierte Benzole und deren Derivate, Alkohole wie Methanol, Ethanol, Propanol, Butanol 27 und Cyclohexanol, Ketone wie Cyclohexanon, stark polare Lösungsmittel, z.B. Amine wie N-Methylpyrrolidon und Wasser.Mineral oil fractions from medium to high boiling point such as kerosene and diesel oil, also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, Ethanol, propanol, butanol 27 and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, eg amines such as N-methylpyrrolidone and water.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Suspensionen, Pasten, netzbaren Pulvern oder wasserdispergier- baren Granulaten durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Oldispersionen können die l-Amino-3-benzyluracile als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgier- mittel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz, Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oldispersions, the l-amino-3-benzyluracils as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, it is also possible to prepare concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Lignin-, Phenol-, Naphthalin- und Dibutylnaphthalinsulfonsäure, sowie von Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Lauryletherund Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanolen sowie von Fettalkoholglykolether, Kondensationsprodukte von sulfoniertem Naphthalin und seiner Derivate mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxy- ethylenoctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenyl-, Tributylphenylpolyglykolether, Alkyl- arylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethylen- oxid-Kondensate, ethoxyliertes Ricinusöl, Polyoxyethylen- oder Polyoxypropylenalkylether, Laurylalkoholpolyglykoletheracetat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht.The alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols as well as of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formalins Condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl polyglycol ether, alkyl aryl polyether alcohols, isotridecyl alcohol, fatty alcohol, polyethylenethylene, ethylene oxide, oxyethylene, ethylene oxide, oxyethylene, oxyethylene, oxyethylene, oxyethylene, oxyethylene, oxyethylene, ethylene oxide Lauryl alcohol polyglycol ether acetate, sorbitol ester, lignin sulfite waste liquor or methyl cellulose.
Pulver-, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Feste Trägerstoffe sind Mineralerden wie Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe. 28Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers. 28
Die Konzentrationen der Wirkstoffe I in den anwendungsfertigen Zubereitungen können in weiten Bereichen variiert werden. Die Formulierungen enthalten im allgemeinen etwa von 0,001 bis 98 Gew.-%, vorzugsweise 0,01 bis 95 Gew.-%, mindestens eines Wirkstoffs. Die Wirkstoffe werden dabei in einer Reinheit von 90 % bis 100%, vorzugsweise 95 % bis 100 % (nach NMR-Spektrum) eingesetzt.The concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range. The formulations generally contain from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
Die folgenden Formulierungsbeispiele verdeutlichen die Her- Stellung solcher Zubereitungen:The following formulation examples illustrate the preparation of such preparations:
I. 20 Gewichtsteile einer Verbindung der Formel I werden in einer Mischung gelöst, die aus 80 Gewichtsteilen alkylier- te Benzol, 10 Gewichtsteilen des Anlagerungsproduktes von 8 bis 10 Mol Ethylenoxid an 1 Mol Ölsäure-N-monoethanol- amid, 5 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfon- säure und 5 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht. Durch Ausgießen und feines Verteilen der Lösung in 100000 Gewichts- teilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs enthält.I. 20 parts by weight of a compound of formula I are dissolved in a mixture consisting of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfone - Acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
II. 20 Gewichtsteile einer Verbindung der Formel I werden in einer Mischung gelöst, die aus 40 Gewichtsteilen Cyclo- hexanon, 30 Gewichtsteilen Isobutanol, 20 Gewichtsteilen des Anlagerungsproduktes von 7 Mol Ethylenoxid an 1 Mol Isooctylphenol und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs enthält.II. 20 parts by weight of a compound of the formula I are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide on 1 Mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.
III. 20 Gewichtsteile einer Verbindung der Formel I werden in einer Mischung gelöst, die aus 25 Gewichtsteilen Cyclo- hexanon, 65 Gewichtsteilen einer Mineralölfraktion vom Siedepunkt 210 bis 280°C und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs enthält.III. 20 parts by weight of a compound of formula I are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction from the boiling point 210 to 280 ° C and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.
IV. 20 Gewichtsteile einer Verbindung der Formel I werden mit 3 Gewichtsteilen des Natriumsalzes der Diisobutyl- naphthalin-α-sulfonsäure, 17 Gewichtsteilen des Natriu - salzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 60 Gewichtsteilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermählen. Durch feines 29IV. 20 parts by weight of a compound of formula I are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill. By fine 29
Verteilen der Mischung in 20000 Gewichtsteilen Wasser enthält man eine Spritzbrühe, die 0,1 Gew.-% des Wirkstoffs enthält.Distributing the mixture in 20,000 parts by weight of water contains a spray mixture which contains 0.1% by weight of the active ingredient.
V. 3 Gewichtsteile einer Verbindung der Formel I werden mit 97 Gewichtsteilen feinteiligem Kaolin vermischt. Man erhält auf diese Weise ein Stäubemittel, das 3 Gew.-% des Wirkstoffs enthält.V. 3 parts by weight of a compound of formula I are mixed with 97 parts by weight of finely divided kaolin. In this way, a dust is obtained which contains 3% by weight of the active ingredient.
VI. 20 Gewichtsteile einer Verbindung der Formel I werden mit 2 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure, 8 Gewichtsteilen Fettalkohol-polyglykolether, 2 Gewichtsteilen Natriumsalz eines Phenol-Harnstoff-Formaldehyd- Kondensates und 68 Gewichtsteilen eines paraffinischen Mineralöls innig vermischt. Man erhält eine stabile ölige Dispersion.VI. 20 parts by weight of a compound of formula I are intimately mixed with 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.
VII. 1 Gewichtsteil einer Verbindung der Formel I wird in einer Mischung gelöst, die aus 70 Gewichtsteilen Cyclohexanon, 20 Gewichtsteilen ethoxyliertem Isooctylphenol undVII. 1 part by weight of a compound of formula I is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and
10 Gewichtsteilen ethoxyliertem Ricinusöl besteht. Man erhält ein stabiles Emulsionskonzentrat.There are 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.
VIII. 1 Gewichtsteil einer Verbindung der Formel I wird in einer Mischung gelöst, die aus 80 Gewichtsteilen Cyclohexanon und 20 Gewichtsteilen Wettol® EM 31 (= nichtionischer Emulgator auf der Basis von ethoxyliertem Ricinusöl) besteht. Man erhält ein stabiles Emulsionskonzentrat.VIII. 1 part by weight of a compound of formula I is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol ® EM 31 (= nonionic emulsifier based on ethoxylated castor oil). A stable emulsion concentrate is obtained.
Die Applikation der Wirkstoffe I bzw. der herbiziden Mittel kann im Vorauflauf- oder im Nachauflaufverfahren erfolgen. Sind die Wirkstoffe für gewisse Kulturpflanzen weniger verträglich, so können Ausbringungstechniken angewandt werden, bei welchen die herbiziden Mittel mit Hilfe der Spritzgeräte so gespritzt werden, daß die Blätter der empfindlichen Kulturpflanzen nach Möglichkeit nicht getroffen werden, während die Wirkstoffe auf die Blätter darunter wachsender unerwünschter Pflanzen oder die unbedeckte Bodenfläche gelangen (post-directed, lay-by) .The active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
Die Aufwandmengen an Wirkstoff I betragen je nach Bekämpfungsziel, Jahreszeit, Zielpflanzen und WachstumsStadium 0,001 bis 3,0, vorzugsweise 0,01 bis 1,0 kg/ha aktive Substanz (a.S.).The application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.) depending on the control target, season, target plants and growth stage.
Zur Verbreiterung des Wirkungsspektrums und zur Erzielung synergistischer Effekte können die 2-Oxopyrrole I mit zahlreichen Vertretern anderer herbizider oder wachstumsregulierender Wirkstoffgruppen gemischt und gemeinsam ausgebracht werden. 30To widen the spectrum of activity and to achieve synergistic effects, the 2-oxopyrroles I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together. 30th
Beispielsweise kommen als Mischungspartner 1,2 , 4-Thiadiazole, 1, 3 , 4-Thiadiazole, Amide, Aminophosphorsäure und deren Derivate, Aminotriazole, Anilide, Aryloxy-/Heteroaryloxyalkansäuren und deren Derivate, Benzoesäure und deren Derivate, Benzothia- diazinone, 2-(Hetaroyl/Aroyl)-l,3-cyclohexandione, Heteroaryl- Aryl-Ketone, Benzylisoxazolidinone, meta-CF3-Phenylderivate, Carbamate, Chinolincarbonsäure und deren Derivate, Chloracet- anilide, Cyclohexan-1, 3-dionderivate, Diazine, Dichlorpropion- säure und deren Derivate, Dihydrobenzofurane, Dihydrofuran-3-one, Dinitroaniline, Dinitrophenole, Diphenylether, Dipyridyle, Halogencarbonsäuren und deren Derivate, Harnstoffe, 3-Phenyl- uracile, Imidazole, Imidazolinone, N-Phenyl-3 ,4 , 5, 6-tetrahydro- phthalimide, Oxadiazole, Oxirane, Phenole, Aryloxy- und Hetero- aryloxyphenoxypropionsäureester, Phenylessigsäure und deren Derivate, 2-Phenylpropionsäure und deren Derivate, Pyrazole, Phenylpyrazole, Pyridazine, Pyridincarbonsäure und deren Derivate, Pyrimidylether, Sulfonamide, Sulfonylharnstoffe, Triazine, Triazinone, Triazolinone, Triazolcarboxamide und Uracile in Betracht.For example, 1,2, 4-thiadiazoles, 1, 3, 4-thiadiazoles, amides, aminophosphoric acid and their derivatives, aminotriazoles, anilides, aryloxy / heteroaryloxyalkanoic acids and their derivatives, benzoic acid and their derivatives, benzothidadiazinones, 2- (Hetaroyl / aroyl) -l, 3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF 3 phenyl derivatives, carbamates, quinolinecarboxylic acids and their derivatives, chloroacetanilides, cyclohexane-1, 3-dione derivatives, diazine dichloro acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3, 4, 5, 6- tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetero-aryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid e and their derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.
Außerdem kann es von Nutzen sein, die Verbindungen I allein oder in Kombination mit anderen Herbiziden auch noch mit weiteren Pflanzenschutzmitteln gemischt, gemeinsam auszubringen, beispielsweise mit Mitteln zur Bekämpfung von Schädlingen oder phytopathogenen Pilzen bzw. Bakterien. Von Interesse ist ferner die Mischbarkeit mit Mineralsalzlösungen, welche zur Behebung von Ernährungs- und Spurenelementmängeln eingesetzt werden. Es können auch nichtphytotoxische Öle und Ölkonzentrate zugesetzt werden.It may also be useful to apply the compounds I alone or in combination with other herbicides, mixed with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used to remedy nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.
Beispiel: Herstellung von E/Z-4-(2-Ethylbenzyliden)-2-me- thyl-5-oxo-4 , 5-dihydropyrrol-3-carbonsäureethylesterExample: Preparation of E / Z-4- (2-ethylbenzylidene) -2-methyl-5-oxo-4, 5-dihydropyrrole-3-carboxylic acid ethyl ester
Eine Lösung von 1,5 g (0,009 mol) 2-Methyl-5-oxo-4,5-dihydropyrr- rol-3-cabonsäureethylester und 2,6 g (0,02 mol) 2-Ethylbenzalde- hyd in 20 ml Ethanol wurde in Gegenwart weniger Tropfen HCl bei Raumtemperatur gerührt.A solution of 1.5 g (0.009 mol) of 2-methyl-5-oxo-4,5-dihydropyrrole-3-cabonic acid ethyl ester and 2.6 g (0.02 mol) of 2-ethylbenzaldehyde in 20 ml of ethanol was stirred in the presence of a few drops of HCl at room temperature.
Anschließend wurde eingeengt und der erhaltene Rückstand an Kieselgel chromatoraphiert . Man erhielt nacheinander 0,5 g (19 %) Z-4-(2-Ethylbenzyliden)-2-methyl-5-oxo-4,5-dihydropyrrol-3-car- bonsäureethylester ( lh-NMR (DMSO) 8,14 ppm (=CH-Ph) und 0,37 g (14 %) E-4-(2-Ethylbenzyliden)-2-methyl-5-oxo-4,5-dihydropyr- rol-3-carbonsäureethylester (lh-NMR (DMSO) 7,45 ppm (=CH-Ph) .The mixture was then concentrated and the residue obtained was chromatoraphed on silica gel. 0.5 g (19%) of Z-4- (2-ethylbenzylidene) -2-methyl-5-oxo-4,5-dihydropyrrol-3-carboxylic acid ethyl ester were obtained in succession (1 H-NMR (DMSO) 8.14 ppm (= CH-Ph) and 0.37 g (14%) of E-4- (2-ethylbenzylidene) -2-methyl-5-oxo-4,5-dihydropyrrole-3-carboxylic acid ethyl ester (1-NMR ( DMSO) 7.45 ppm (= CH-Ph).
Auf analoge Art und Weise wurden die in den nachfolgenden Tabellen 1 bis 9 aufgeführten Verbindungen hergestellt. 31The compounds listed in Tables 1 to 9 below were prepared in an analogous manner. 31
Tabelle 1: A= COOCH3, R2 = CH3 Table 1: A = COOCH 3 , R 2 = CH 3
Nr. Bedeutung R1 Fp (°C)No.Meaning R 1 Fp (° C)
1. C6H5 201 (Z)1. C 6 H 5 201 (Z)
2. 1-Naphthyl 227 (Z)2. 1-naphthyl 227 (Z)
3. 2-CH3-C6H4 178 (Z)3. 2-CH 3 -C 6 H 4 178 (Z)
4. 3-CH3-C6H4 192 (Z)4. 3-CH 3 -C 6 H 4 192 (Z)
5. 4-CH3-C6H4 207 (Z)5. 4-CH 3 -C 6 H 4 207 (Z)
6. 2,4-(CH3)2-C6H3 202 (Z)6. 2,4- (CH 3 ) 2 -C 6 H 3 202 (Z)
7. 3,4-(CH3)2-C6H3 214 (Z)7. 3,4- (CH 3 ) 2 -C 6 H 3 214 (Z)
8. 2,4,6-(CH3)3-C6H2 227 (Z)8. 2,4,6- (CH 3 ) 3 -C 6 H 2 227 (Z)
9. 2-C2H5-C6H4 120 (Z)9. 2-C 2 H 5 -C 6 H4 120 (Z)
10. 4-t-C H9-C6H4 160 (Z)10. 4-tC H 9 -C 6 H 4 160 (Z)
11. 2-Cl-C6H4 196 (Z)11. 2-Cl-C 6 H 4 196 (Z)
12. 4-Cl-C6H4 192 (Z)12. 4-Cl-C 6 H 4 192 (Z)
13. 3-Cl-C6H4 202 (Z)13. 3-Cl-C 6 H 4 202 (Z)
14. 3,5-(Cl)2-C6H3 24814. 3,5- (Cl) 2 -C 6 H 3 248
E:Z 35:65)E: Z 35:65)
15. 2,4-(Cl)2-C6H3 230 (Z)15. 2,4- (Cl) 2 -C 6 H 3 230 (Z)
16. 2,3-(Cl)2-C6H3 244 (Z)16. 2,3- (Cl) 2 -C 6 H 3 244 (Z)
17. 3,4-(Cl)2-C6H3 216 (Z)17. 3,4- (Cl) 2 -C 6 H 3 216 (Z)
18. 2-Cl-4-F-C6H3 225 (Z)18. 2-Cl-4-FC 6 H 3 225 (Z)
19. 2-Cl-6-F-C6H3 178 (Z)19. 2-Cl-6-FC 6 H 3 178 (Z)
20. 3-Cl-6-N02-C6H3 268 (Z)20. 3-Cl-6-N0 2 -C 6 H 3 268 (Z)
21. 2-Br-C6H4 212-214 (Z)21. 2-Br-C 6 H 4 212-214 (Z)
22. 2-CF3-C6H4 145-150 (Z)22. 2-CF 3 -C 6 H 4 145-150 (Z)
23. 4-CF3-C6H4 203-204 (Z)23. 4-CF 3 -C 6 H 4 203-204 (Z)
24. 2,5-(CF3)2-C6H3 206 (Z)24. 2.5- (CF 3 ) 2 -C 6 H 3 206 (Z)
25. 4-CH30-C6H4 148 (Z)25. 4-CH 3 0-C 6 H 4 148 (Z)
26. 3,5-(CH30)2-C6H3 188 (Z)26. 3,5- (CH 3 0) 2 -C 6 H 3 188 (Z)
27. 2-C2H50-C6H4 172 (Z)27. 2-C 2 H 5 0-C 6 H 4 172 (Z)
28. 2-OH-C6H4 198 (Z)28. 2-OH-C 6 H 4 198 (Z)
29. 4-CH2=CH-CH20-C6H4 180 (Z)29. 4-CH 2 = CH-CH 2 0-C 6 H 4 180 (Z)
30. 2-F-C6H4 178 (Z)30. 2-FC 6 H 4 178 (Z)
31. 4-F-C6H4 177 (Z)31. 4-FC 6 H 4 177 (Z)
32. 2,4-F2-C6H4 166-167 (Z)32.2,4-F 2 -C 6 H 4 166-167 (Z)
33. 2,6-F2-C6H4 203 (Z)33. 2,6-F 2 -C 6 H 4 203 (Z)
34. 2-Br-4-F-C6H3 237 (Z)34. 2-Br-4-FC 6 H 3 237 (Z)
35. 4-CN-C6H4 255 (Z)35. 4-CN-C 6 H 4 255 (Z)
36. 2-CN-C6H4 223 (Z)36. 2-CN-C 6 H 4 223 (Z)
37. 2-N02-C6H4 234 (Z) 3237. 2-N0 2 -C 6 H 4 234 (Z) 32
Nr. Bedeutung R1 Fp (°C)No.Meaning R 1 Fp (° C)
38. 2- ( 2-Cl-C6H4 )CH20-C6H4 165 (Z)38. 2- (2-Cl-C 6 H 4 ) CH 2 0-C 6 H 4 165 (Z)
39. 2- ( 2-CH3-C6H ) CH20-C6H4 158 (Z)39. 2- (2-CH 3 -C 6 H) CH 2 0-C 6 H 4 158 (Z)
40. 2- ( 3-CH3-C6H4 ) CH20-C6H4 120-128 (Z)40. 2- (3-CH 3 -C 6 H 4 ) CH 2 0-C 6 H 4 120-128 (Z)
41. 2-C6H4-CH20-C6H4 176 (Z)41. 2-C 6 H 4 -CH 2 0-C 6 H4 176 (Z)
42. 4-CH3C0NH-C6H4 260 (Z)42. 4-CH 3 C0NH-C 6 H 4 260 (Z)
43. 4-CH30N=C-C6H4 190 (Z)43. 4-CH 3 0N = CC 6 H 4 190 (Z)
44. 4-CH=C-CH20-C6H 179 (Z)44. 4-CH = C-CH 2 0-C 6 H 179 (Z)
45. 2-S03H-4-Cl-C6H3 318 (Z)45. 2-S0 3 H-4-Cl-C 6 H 3 318 (Z)
46. 2-CH3S-C6H4 17946. 2-CH 3 SC 6 H 4 179
47. 2-CF3S-C6H4 102-123 E:Z 50:5047. 2-CF 3 SC 6 H 4 102-123 E: Z 50:50
48. 3 , 5-Dif luorphenyl 17548, 3,5-difluorophenyl 175
(E:Z 30:70)(E: Z 30:70)
49. 3,5-OCH2-C6H3 217 (Z)49.3,5-OCH 2 -C 6 H 3 217 (Z)
50. 3,5-Br2-C6H3 248-250 (Z)50.3,5-Br 2 -C 6 H 3 248-250 (Z)
51. 2-F-4-Cl-C6H3 200 (Z)51. 2-F-4-Cl-C 6 H 3 200 (Z)
52. 2-F-4-C1-5-OCH (CH3 ) 2-C6H2 206 (Z)52. 2-F-4-C1-5-OCH (CH 3 ) 2 -C 6 H 2 206 (Z)
53. 2-(OCH2CO-NH-C6H5)-C6H4 206-208 (Z)53. 2- (OCH 2 CO-NH-C 6 H 5 ) -C 6 H 4 206-208 (Z)
54. 2-OCH2CCH-C6H4 173-175 (Z)54. 2-OCH 2 CCH-C 6 H 4 173-175 (Z)
55. 2-C1-4-F-5 ( l-methyl-4-Cl-dif luormethoxy- 169-170 (Z) pyrazol-3-yl ) -C6H2 55. 2-C1-4-F-5 (l-methyl-4-Cl-difluoromethoxy-169-170 (Z) pyrazol-3-yl) -C 6 H 2
56. 2,5.F2-C6H3 Öl (Z)56. 2,5.F 2 -C 6 H 3 oil (Z)
57. 2-OCHF2-CHF2-C6H4 135-137 (Z)57. 2-OCHF 2 -CHF 2 -C 6 H 4 135-137 (Z)
58. 2-OCF2H-C6H4 170 (Z)58. 2-OCF 2 HC 6 H 4 170 (Z)
59. 2,6-(OCH3)2-C6H3 182 (Z)59. 2,6- (OCH 3 ) 2 -C 6 H 3 182 (Z)
60. 2-COOCH3-C6H4 189-191 (Z)60. 2-COOCH 3 -C 6 H 4 189-191 (Z)
61. 2-OCF3-C6H4 150-154 (Z)61. 2-OCF 3 -C 6 H 4 150-154 (Z)
62. 2-Cl-6-SCH3-C6H3 199 (Z)62. 2-Cl-6-SCH 3 -C 6 H 3 199 (Z)
63. 2,5-Cl2-C6H3 268-269 (Z)63. 2,5-Cl 2 -C 6 H 3 268-269 (Z)
64. 2-Cl-6-OCH3-C6H3 211-212 (Z)64. 2-Cl-6-OCH 3 -C 6 H 3 211-212 (Z)
65. 2 -OCH2-CH=CH ( CH3 ) -C6H4 123-124 (Z)65. 2 -OCH 2 -CH = CH (CH 3 ) -C 6 H 4 123-124 (Z)
66. 2, 6-Cl2-C6H3 118-119 (Z)66. 2, 6-Cl 2 -C 6 H 3 118-119 (Z)
67. 2,6-(CH3S)2-C6H3 156-157 (Z)67. 2,6- (CH 3 S) 2 -C 6 H 3 156-157 (Z)
68. 2-SCH3-3-Cl-C6H3 193-195 (Z)68. 2-SCH 3 -3-Cl-C 6 H 3 193-195 (Z)
69. 2-SCH3-6-F-C6H3 3369. 2-SCH 3 -6-FC 6 H 3 33
Tabelle 2: A= COOCH2CH3, R2 = CH3 Table 2: A = COOCH 2 CH 3 , R 2 = CH 3
Nr. Bedeutung R1 Fp (°C)No.Meaning R 1 Fp (° C)
1. C6 H5 179 (Z)1. C 6 H 5 179 (Z)
5 2. 2-CH3-C6H4 165 (Z)5 2. 2-CH 3 -C 6 H 4 165 (Z)
3. 4-CH3-C6H4 195 (Z)3. 4-CH 3 -C 6 H 4 195 (Z)
4. 2,4-(CH3)2-C6H3 180 (Z)4. 2,4- (CH 3 ) 2 -C 6 H 3 180 (Z)
5. 3,4-(CH3)2-C6H3 223 (Z)5. 3,4- (CH 3 ) 2 -C 6 H 3 223 (Z)
6. 2,4,6-(CH3)3-C6H2 140 (Z) 0 173 (E)6. 2,4,6- (CH 3 ) 3 -C 6 H 2 140 (Z) 0 173 (E)
7. 4-t-C4H9-C6H4 132 (Z)7. 4-tC 4 H 9 -C 6 H4 132 (Z)
132132
(E:Z 75:25)(E: Z 75:25)
8. 2-Cl-C6H4 196 (Z) 58. 2-Cl-C 6 H 4 196 (Z) 5
9. 4-Cl-C6H4 193 (Z)9. 4-Cl-C 6 H 4 193 (Z)
10. 5-Cl-C6H4 172 (Z)10. 5-Cl-C 6 H 4 172 (Z)
11. 3,5-(Cl)2-C6H3 208 (Z)11. 3,5- (Cl) 2 -C 6 H 3 208 (Z)
202202
(E:Z 60:40) 0(E: Z 60:40) 0
12. 2,4-(Cl)2-C6H3 235 (Z)12. 2,4- (Cl) 2 -C 6 H 3 235 (Z)
13. 2,3-(Cl)2-C6H3 230 (Z)13. 2,3- (Cl) 2 -C 6 H 3 230 (Z)
14. 3,4-(Cl)2-C6H3 230 (Z)14. 3,4- (Cl) 2 -C 6 H 3 230 (Z)
15. 2-Cl-4-F-C6H3 231 (Z) b 16. 2-Cl-6-F-C6H3 157 (Z)15. 2-Cl-4-FC 6 H 3 231 (Z) b 16. 2-Cl-6-FC 6 H 3 157 (Z)
17. 2-Cl-5-N02-C6H3 238 (Z)17. 2-Cl-5-N0 2 -C 6 H 3 238 (Z)
18. 3-Cl-6-N02-C6H3 235 (Z)18. 3-Cl-6-N0 2 -C 6 H 3 235 (Z)
19. 2-Br-C6H4 195 (Z) 0 20. 2-CF3-C6H4 131-135 (Z)19. 2-Br-C 6 H 4 195 (Z) 0 20. 2-CF 3 -C 6 H 4 131-135 (Z)
21. 4-CF3-C6H4 206 (Z)21. 4-CF 3 -C 6 H 4 206 (Z)
22. 4-CH2=CH-CH20-C6H 148 (Z)22. 4-CH 2 = CH-CH 2 0-C 6 H 148 (Z)
23. 2-Br-4-F-C6H3 215 (Z)23. 2-Br-4-FC 6 H 3 215 (Z)
24. 4-CN-C6H4 238 (Z) 524. 4-CN-C 6 H 4 238 (Z) 5
25. 2-N02-C6H4 200 (Z)25. 2-N0 2 -C 6 H 4 200 (Z)
164164
(E:Z 85:15)(E: Z 85:15)
26. 2- ( 2-Cl-C6H4 ) CH20-C6H4 180 (Z) 0 27. 4-CH3CONH-C6H4 210 (Z)26. 2- (2-Cl-C 6 H 4 ) CH 2 0-C 6 H 4 180 (Z) 0 27. 4-CH 3 CONH-C 6 H 4 210 (Z)
28. 4-CH3ON=C-C6H4 192 (Z)28. 4-CH 3 ON = CC 6 H 4 192 (Z)
29. 4-CH≡≡C-CH20-C6H4 183 (Z)29. 4-CH≡≡C-CH 2 0-C 6 H 4 183 (Z)
30. 2-S03H-4-Cl-C6H3 357 (Zers.) (Z) 5 3430. 2-S0 3 H-4-Cl-C 6 H 3 357 (dec.) (Z) 5 34
Tabelle 3: A= COOC2H5, R2 = CH2CH2CH3 Table 3: A = COOC 2 H 5 , R 2 = CH 2 CH 2 CH 3
Nr. Bedeutung R1 Fp (°C)No.Meaning R 1 Fp (° C)
1. C6H5 134 (Z)1. C 6 H 5 134 (Z)
5 2. 2-CH3-C6H4 121,5 (Z)5 2. 2-CH 3 -C 6 H 4 121.5 (Z)
3. 3-CH3-C6H4 140 (Z)3. 3-CH 3 -C 6 H 4 140 (Z)
4. 4-CH3-C6H4 176 (Z)4. 4-CH 3 -C 6 H 4 176 (Z)
5. 2,4-(CH3)2-C6H3 159 (Z)5. 2,4- (CH 3 ) 2 -C 6 H 3 159 (Z)
6. 2-Cl-C6H4 129 (Z) 06. 2-Cl-C 6 H 4 129 (Z) 0
7. 2-Cl-4-F-C6H3 154 (Z)7. 2-Cl-4-FC 6 H 3 154 (Z)
8. 2-Cl-6-F-C6H3 127-129 (Z)8. 2-Cl-6-FC 6 H 3 127-129 (Z)
9. 2-Cl-5-N02-C6H3 193 (Z) 59. 2-Cl-5-N0 2 -C 6 H 3 193 (Z) 5
Tabelle 4: A= COOCH3, R2 = CH2CH3 Table 4: A = COOCH 3 , R 2 = CH 2 CH 3
Nr. Bedeutung R1 Fp (°C)No.Meaning R 1 Fp (° C)
1. C6H5 158-159 (Z) 0 2. 2-CH3-C6H4 175-176(Z)1. C 6 H 5 158-159 (Z) 0 2. 2-CH 3 -C 6 H4 175-176 (Z)
3. 2— C2H5~ CgH4 Öl (E) 126-128 (Z)3. 2 - C 2 H5 ~ CgH 4 oil (E) 126-128 (Z)
4. 2-Cl-C6H4 178 (Z)4. 2-Cl-C 6 H 4 178 (Z)
5. 2-Cl-4-F-C6H3 221 (Z) ^5. 2-Cl-4-FC 6 H 3 221 (Z) ^
6. 2-Cl-6-F-C6H3 184 (Z)6.2-Cl-6-FC 6 H 3 184 (Z)
7. 2-Br-C6H4 185 (Z)7. 2-Br-C 6 H 4 185 (Z)
8. 2-CF3-C6H4 142-145 (Z)8. 2-CF 3 -C 6 H 4 142-145 (Z)
9. 2-F-C6H4 169 (Z) 0 10. 4-F-C6H4 208 (Z)9.2-FC 6 H 4 169 (Z) 0 10. 4-FC 6 H 4 208 (Z)
11. 2-Br-4-F-C6H3 220 (Z)11. 2-Br-4-FC 6 H 3 220 (Z)
12. 2-F-4-Cl-C6H3 190 (Z)12. 2-F-4-Cl-C 6 H 3 190 (Z)
13. 2-F-4-C1-5- (OCH(CH3 ) 2-C6H2 188 (Z) 5 14. 2-C1-4-F-5 ( l-methyl-4-Cl-dif luormethoxy- 173-175 (Z) pyrazol-3-yl ) -C6H2 13. 2-F-4-C1-5- (OCH (CH 3 ) 2 -C 6 H 2 188 (Z) 5 14. 2-C1-4-F-5 (l-methyl-4-Cl-dif luormethoxy-173-175 (Z) pyrazol-3-yl) -C 6 H 2
Tabelle . >: A= CONH2, R2 = CH3 Table . >: A = CONH 2 , R 2 = CH 3
Nr. Bedeutung R1 Fp (°C) 0No.Meaning R 1 Fp (° C) 0
1. 2-Cl-C6H4 253 (Z)1. 2-Cl-C 6 H 4 253 (Z)
2. 2-Cl-6-F-C6H3 208-211 (Z)2. 2-Cl-6-FC 6 H 3 208-211 (Z)
3. 2-F-C6H4 200 (Zers.) (Z) 5 4. 2-Br-4-F-C6H3 248-249 (Z) 353. 2-FC 6 H 4 200 (dec.) (Z) 5 4. 2-Br-4-FC 6 H 3 248-249 (Z) 35
Tabelle 6 :Table 6:
Nr. Bedeutung R1 Bedeutung R2 Bedeutung A Fp (°C)No. Meaning R 1 meaning R 2 meaning A Fp (° C)
1. 2-CH3-C6H4 CH3 COO-t-C4H9 149-151 (Z)1. 2-CH 3 -C 6 H 4 CH 3 COO-tC 4 H 9 149-151 (Z)
2. 2-Cl-C6H4 CH3 COO-t-C4H9 175-176 (Z)2. 2-Cl-C 6 H 4 CH 3 COO-tC 4 H 9 175-176 (Z)
3. 2-Cl-6-F-C6H3 CH3 COO-t-C4H9 75-78 (Z)3. 2-Cl-6-FC 6 H 3 CH 3 COO-tC 4 H 9 75-78 (Z)
4. 2-Cl-6-F-C6H3 cyclo-C3H5 COOCH3 MH+ 3044. 2-Cl-6-FC 6 H 3 cyclo-C 3 H 5 COOCH 3 MH + 304
5. 2-Cl-6-F-C6H3 cyclo-C3H5 COOC2H5 MH+ 318 5. 2-Cl-6-FC 6 H 3 cyclo-C 3 H 5 COOC 2 H 5 MH + 318
Des weiteren wurden die folgenden Verbindungen hergestellt, in denen R1 für einen Heteroarylrest steht.The following compounds were also prepared, in which R 1 represents a heteroaryl radical.
Tabelle 7: A= COOCH3; R2= CH3 Table 7: A = COOCH 3 ; R 2 = CH 3
Nr. Bedeutung R1 Fp (°C)No.Meaning R 1 Fp (° C)
1. 3-Pyridyl 180 (Z)1.3-pyridyl 180 (Z)
2. 4-Pyridyl 182-184 (Z)2. 4-pyridyl 182-184 (Z)
3. 4 , 6- (CH30) 2-2-CH3S-5-pyrimidyl 214-216 (Z)3.4, 6- (CH 3 0) 2 -2-CH 3 S-5-pyrimidyl 214-216 (Z)
4. 2-Pyrryl 217 (Z)4.2-pyrryl 217 (Z)
5. l-CH3-2-Pyrryl 280-282 (Z)5. l-CH 3 -2-pyrryl 280-282 (Z)
6. 3-Furanyl 200-201 (Z)6. 3-furanyl 200-201 (Z)
7. 5-N02-Furan-2-yl 235 (Z)7. 5-N0 2 -Furan-2-yl 235 (Z)
8. 1- ( 2 , 4-Cl2-C6H3 ) -3-pyrrolyl 202 (Z)8. 1- (2, 4-Cl 2 -C 6 H 3 ) -3-pyrrolyl 202 (Z)
9. 3-C3H7-2-isoxazolyl9. 3-C 3 H 7 -2-isoxazolyl
10. 3-Indolyl 245-248 (Z)10. 3-indolyl 245-248 (Z)
11. l-CH3-4-pyrazolyl 196 (Z)11. l-CH 3 -4-pyrazolyl 196 (Z)
12. 1- ( 4-Cl-C6H4 ) -4-pyrazolyl 273-275 (Z)12. 1- (4-Cl-C 6 H 4 ) -4-pyrazolyl 273-275 (Z)
13. 2-C6H5-4-oxazolyl 260 (Z)13. 2-C 6 H 5 -4-oxazolyl 260 (Z)
14. 3- ( 4-CI-C6H4 ) -5-isoxazolyl 245-246 (Z)14. 3- (4-CI-C 6 H 4 ) -5-isoxazolyl 245-246 (Z)
15. 3-i-C3H7-5-isoxazolyl 210-211 (Z)15. 3-iC 3 H 7 -5-isoxazolyl 210-211 (Z)
16. 3-Thiopheny1 206 (Z)16. 3-thiopheny1 206 (Z)
17. 5-CH3-2-thiophenyl 234 (Z)17. 5-CH 3 -2-thiophenyl 234 (Z)
18. 3-CH3-2-thiophenyl 248 (Z)18. 3-CH 3 -2-thiophenyl 248 (Z)
19. 5-Cl-2-thiophenyl 219 (Z)19. 5-Cl-2-thiophenyl 219 (Z)
20. 2 , 5-Br2-3-thiophenyl 236-238 (Z)20. 2, 5-Br 2 -3-thiophenyl 236-238 (Z)
21. 4-CH3-5-imidazolyl 250 (Zers.) (Z)21. 4-CH 3 -5-imidazolyl 250 (dec.) (Z)
22. 2-(CH3)2N-5-thiazolyl 252-255 (Z)22. 2- (CH3) 2 N-5-thiazolyl 252-255 (Z)
23. 3-Br-5-CH3-2-benzo-b-thiophenyl 240 (Z)23. 3-Br-5-CH 3 -2-benzo-b-thiophenyl 240 (Z)
24. 2-Furyl 180 (Z)24. 2-furyl 180 (Z)
25. 2-Hydroxychinolin 291 (Z)25. 2-hydroxyquinoline 291 (Z)
26. 2-Thiopheny1 223-225 (Z) 3626. 2-thiopheny1 223-225 (Z) 36
Nr. Bedeutung R1 Fp (°C)No.Meaning R 1 Fp (° C)
27. 4-Br-2-thiopheny1 247 (Z)27. 4-Br-2-thiopheny1 247 (Z)
28. 3-Br-2-thiopheny1 257-258 (Z)28. 3-Br-2-thiopheny1 257-258 (Z)
29. 4-CN-2-thiophenyl 291-293 (Z) 29. 4-CN-2-thiophenyl 291-293 (Z)
Tabelle 8: A = C==C2H5, R2 = CH3 Table 8: A = C == C 2 H 5 , R 2 = CH 3
Nr. Bedeutung R1 Fp (°C)No.Meaning R 1 Fp (° C)
10 1. 3-Pyridyl 210 (Z)10 1. 3-pyridyl 210 (Z)
2. 4-Pyridyl 178-180 (Z)2. 4-pyridyl 178-180 (Z)
3. 4,6-(CH30)2-2-CH3S-5-pyrimidyl 226 (Z)3. 4,6- (CH 3 0) 2 -2-CH 3 S-5-pyrimidyl 226 (Z)
4. 2-Pyrryl 197 (Z)4.2-pyrryl 197 (Z)
15 5. 5-N02-Furanyl 240 (Z)15 5. 5-N0 2 -Furanyl 240 (Z)
6. 1,2, 5-tri-Methyl-pyrrolyl 181 (Z)6. 1,2,5-tri-methyl-pyrrolyl 181 (Z)
7. 3-C3H7-2-isoxazolyl 259 (Z)7. 3-C 3 H 7 -2-isoxazolyl 259 (Z)
8. l-CH3-4-pyrrazolyl 213 (Z)8. l-CH 3 -4-pyrrazolyl 213 (Z)
9. 1- ( 4-Cl-C6H ) -4-pyrazolyl 258 (Z)9. 1- (4-Cl-C 6 H) -4-pyrazolyl 258 (Z)
2020th
10. 2-C6H5-4-oxazolyl 252 (Z)10. 2-C 6 H 5 -4-oxazolyl 252 (Z)
11. 3- ( 4-Cl-C6H ) -5-isoxazolyl 273(Z)11. 3- (4-Cl-C 6 H) -5-isoxazolyl 273 (Z)
12. 3-i-C3H7-5-isoxazolyl 226 (Z)12. 3-iC 3 H 7 -5-isoxazolyl 226 (Z)
13. 4-CH3-5-imidazolyl 114 (Z)13. 4-CH 3 -5-imidazolyl 114 (Z)
25 14. 2- (CH3 ) -2N-5-thiazolyl 284 (Z)25 14. 2- (CH 3 ) - 2 N-5-thiazolyl 284 (Z)
15. 2- Furyl 218 (Z)15. 2- furyl 218 (Z)
16. 2-Hydroxychinolin >295 (Z) 16. 2-hydroxyquinoline> 295 (Z)
30 Tabelle 9:30 Table 9:
Nr. Bedeutung R1 R2 Bedeutung A Fp (°C)No. Meaning R 1 R 2 meaning A Fp (° C)
1. 3-C3H7-5-isoxazolyl CH3 C0NH2 149-151 (Z) 1. 3-C 3 H 7 -5-isoxazolyl CH 3 C0NH 2 149-151 (Z)
35 Beispiele zur herbiziden Aktivität35 examples of herbicidal activity
Zum Zweck der Nachauflaufbehandlung wurden die Testpflanzen je nach Wuchsform erst bis zu einer Wuchshöhe von 3 bis 15 cm angezogen und erst dann mit den in Wasser suspendierten oderFor the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then with those suspended in water or
40 emulgierten Wirkstoffen behandelt. Die Testpflanzen wurden dafür entweder direkt gesät und in den gleichen Gefäßen aufgezogen oder sie wurden erst als Keimpflanzen getrennt angezogen und einige Tage vor der Behandlung in die Versuchsgefäße verpflanzt.40 emulsified active ingredients treated. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
^5 Die Pflanzen wurden artenspezifisch bei Temperaturen von 10 - 25°C bzw. 20 - 35°C gehalten. Die Versuchsperiode erstreckte sich über 2 bis 4 Wochen. Während dieser Zeit wurden die Pflanzen gepflegt, 37 und ihre Reaktion auf die einzelnen Behandlungen wurde ausgewertet.^ 5 Depending on the species, the plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C. The trial period lasted 2 to 4 weeks. During this time, the plants were cared for, 37 and their response to each treatment was evaluated.
Bewertet wurde nach einer Skala von 0 bis 100. Dabei bedeutet 100 kein Aufgang der Pflanzen bzw. völlige Zerstörung zumindest der oberirdischen Teile und 0 keine Schädigung oder normaler Wachstumsverlauf .Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
Die Ergebnisse sind der nachstehenden Tabellen zu entnehmen:The results are shown in the tables below:
Tabelle 10: Aufwandmenge jeweils 3,0 g a.S./haTable 10: Application rate each 3.0 g a.S./ha
Nr. getestete Verbindung Wirkungsgrad gegen ABUTH SETIT SINALNo. tested connection efficiency against ABUTH SETIT SINAL
1 Tabelle 1 ,Nr. 1 90 1001 Table 1, no. 1 90 100
2 Tabelle 1, Nr. 3 100 95 1002 Table 1, No. 3 100 95 100
3 Tabelle 1, Nr.9 90 1003 Table 1, No. 9 90 100
4 Tabelle 1, Nr. 13 100 1004 Table 1, No. 13 100 100
5 Tabelle 1, Nr. 18 100 100 6 Tabelle 1, Nr. 19 95 100 1005 Table 1, No. 18 100 100 6 Table 1, No. 19 95 100 100
ABUTH: Chinesischer Hanf (Abuthilon theophrasti) SETIT: Italienische Borstenhirse (Setaria italica) siNAL: Weisser Senf (Sinapis alba) ABUTH: Chinese hemp (Abuthilon theophrasti) SETIT: Italian millet (Setaria italica) siNAL: White mustard (Sinapis alba)

Claims

38P a t e n t a n s p r ü c h e 38 patent claims
1 . Verwendung von 2 -Oxopyrrolen der allgemeinen Formel I1 . Use of 2 -oxopyrroles of the general formula I
55
10 ( i :10 (i:
wobei die Substituenten die folgenden Bedeutungen haben: where the substituents have the following meanings:
1515
R1 Aryl oder Heteroaryl, wobei diese Reste unabhängig voneinander eine bis fünf der folgenden Gruppen tragen können: Wasserstoff, Halogen, Cyano, Nitro, Hydroxy, Mercapto, Thiocyanato, Carboxy, Amino,Cι-C6-Alkyl, Cx-Cg-Cyanoalkyl, C2-C6-R 1 aryl or heteroaryl, where these radicals can independently carry one to five of the following groups: hydrogen, halogen, cyano, nitro, hydroxy, mercapto, thiocyanato, carboxy, amino, C 1 -C 6 alkyl, Cx-Cg-cyanoalkyl , C 2 -C 6 -
20 Alkenyl, Cι-C6-Alkoxy-C2-C6-Alkenyl, C3-C6-Alkinyl, Cχ-C6-Al- koxy-C3-C6-Alkinyl, C3-C6-Alkinyl-Cι-C6-Alkoxy, C3-C7-Cycloal- kyl, Cι-C6-Alkyl-C3-C7-Cycloalkyl, Cι-C6-Alkoxy-C3-C7-Cycloal- kyl, C3-C7-Cycloalk loxy, C3-C7-Cyanocycloalkyloxy, Cι-C6-Al- kyl-C3-C7-Cycloalkyloxy, C3-C7-Halogencycloalkyl, C3-C7-Cyano-20 alkenyl, -CC 6 alkoxy-C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, Cχ-C 6 alkoxy-C 3 -C 6 alkynyl, C 3 -C 6 alkynyl -C-C 6 -alkoxy, C 3 -C 7 -cycloalkyl-, -C-C 6 -alkyl-C 3 -C 7 -cycloalkyl, -C-C 6 -alkoxy-C 3 -C 7 -cycloalkyl, C 3 -C 7 cycloalk loxy, C 3 -C 7 cyanocycloalkyloxy, Cι-C 6 alkyl-C 3 -C 7 cycloalkyloxy, C 3 -C 7 halocycloalkyl, C 3 -C 7 cyano-
2g cycloalkyl, C3-C7-Halogencycloalkyloxy, C5-C7-Cycloalkenyl, Cι-C6-Alkyl-C5-C7-Cycloalkenyl, C1-C6-Alkoxy-C5-C7-Cycloalke- nyl, C5-C -Cyanocycloalkenyl, C5-C -Halogencycloalkenyl, Cι-C6-Alkoxy-Cι-C6-Alkyl, Ci-Cg-Halogenalkyl, C2-C6-Halogenal- kenyl, C3-C6-Halogenalkinyl, C2-Cg-Cyanoalkenyl, C3-C6-Cyano- 2g cycloalkyl, C 3 -C 7 halocycloalkyloxy, C 5 -C 7 cycloalkenyl, Cι-C 6 alkyl-C 5 -C 7 cycloalkenyl, C 1 -C 6 alkoxy-C 5 -C 7 cycloalkene- nyl, C 5 -C cyanocycloalkenyl, C 5 -C halocycloalkenyl, C 6 -C 6 alkoxy-C 6 -C 6 alkyl, Ci-Cg haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 6 -haloalkynyl, C 2 -Cg-cyanoalkenyl, C 3 -C 6 -cyano-
3Q alkinyl, Cι-C6-Alkoxy, Cx-Cg-Cyanoalkoxy, Cι-C6-Halogenalkoxy, C2-Cg-Alkenyloxy, C2-Cg-Cyanoalkenyloxy, C2-Cg-Halogenalkeny- loxy, C2-C6-Alkinyloxy, Cι-C6-Alkylthio, Cι-C6-Cyanoalkylthio, Cι-C6-Halogenalkylthio, Ci-Ce-Al ox -Ci-Cg-Al ylthio, Cι-C6-Al- koxycarbonyl, Ci-Cg-Alkylcarbonyl, Ci-Cg-Alkylcarboxy-Ci-Cg- 3Q alkynyl, -C-C 6 alkoxy, Cx-Cg-cyanoalkoxy, Cι-C 6 -haloalkoxy, C 2 -Cg-alkenyloxy, C 2 -Cg-cyanoalkenyloxy, C 2 -Cg-haloalkenyloxy, C 2 -C 6 -alkynyloxy, -C-C 6 -alkylthio, -C-C 6 -cyanoalkylthio, Cι-C 6 -haloalkylthio, Ci-Ce-Al ox -Ci-Cg-Al ylthio, Cι-C 6 -alkoxycarbonyl, Ci Cg-alkylcarbonyl, Ci-Cg-alkylcarboxy-Ci-Cg-
-5 Alkyl, Ci-Cg-Alkylcarbonyl-Ci-Cδ-Alkyl, Ci-Cg-Alkylcarbonyla- mino, Arylcarbonylamino, Arylsulphinyl, Arylsulphonyl, Hete- roarylsulphinyl, Heteroarylsulphonyl, Aryl-Ci-Cg-Alkyl, Aryl- C2-C6-Alkenyl, Aryl-C3-C6-Alkinyl, Heteroaryl-Cι-C6-alkyl, He- teroaryl-C2-C6-Alkenyl, Heteroaryl-C3-Cg-Alkinyl, Aryl-- 5 alkyl, Ci-Cg-alkylcarbonyl-Ci-C δ- alkyl, Ci-Cg-alkylcarbonylamino, arylcarbonylamino, arylsulphinyl, arylsulphonyl, heteroarylsulphinyl, heteroarylsulphonyl, aryl-Ci-Cg-alkyl, aryl- C 2 - C 6 -alkenyl, aryl-C 3 -C 6 -alkynyl, heteroaryl -CC-C 6 -alkyl, heteroaryl-C 2 -C 6 -alkenyl, heteroaryl-C 3 -Cg-alkynyl, aryl-
._ Ci-Cg-Alkoxy, Aryl-C2-Cδ-Alkenyloxy, Aryl-C3-C6-Alkinyloxy,._ Ci-Cg-alkoxy, aryl-C 2 -C δ- alkenyloxy, aryl-C 3 -C 6 -alkynyloxy,
Heteroaryl-CχC6-alkoxy, Heteroaryl-C2-Cg-Alkenyloxy, Heteroa- ryl-C3-C6-alkinyloxy, Cι-C6-Alkylsulphinyl, Cι-C6-Alkylsulpho- nyl, C2-Cg-Alkenylsulphinyl, C2-C6-Alkenylsulphonyl, Ci-Cg-Al- kylamino, Di-Ci-Cg-Alkylamino, HC=NOH, Cι-C6-Alkyl-C=NOH,Heteroaryl-CχC 6 -alkoxy, heteroaryl-C 2 -Cg-alkenyloxy, heteroaryl-C 3 -C 6 -alkynyloxy, -C-C 6 -alkylsulphinyl, -C-C 6 -alkylsulphonyl, C 2 -Cg-alkenylsulphinyl , C 2 -C 6 alkenylsulphonyl, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, HC = NOH, -C-C 6 alkyl-C = NOH,
45 3945 39
HC=N-0-Cι-C6-Alkyl, HC=N-0-Cι-C6-Alkyl-Aryl, Cx-Cg-Alkyl-C^N- O-Ci-C -Alkyl, HC=N-0-C2-C6-Alkenyl, C1-C6-Alkyl-C=N-0-C2-C6- Alkenyl, HC=N-0-Aryl, C1-C6-Alkyl-C=N-0-Aryl, Aryl, Aryloxy, Heteroaryl, Heteroaryloxy, Arylthio, Heteroarylthio, wobei die cyclischen Substituenten ihrerseits unabhängig voneinander einen bis fünf der nachfolgenden Substituenten tragen können: Wasserstoff, Halogen, Cyano, Nitro, Hydroxy, Mer- capto, Thiocyanato, Carboxy, Amino,C_-C6-Alkyl, Ci-Cg-Cyanoal- kyl, C2-C6-Alkenyl, Cι-C6-Alkoxy-C2-C6-Alkenyl, C3-C6-Alkinyl, Cι-C6-Alkoxy-C3-C6-Alkinyl, C3-Cg-Alkinyl-Cι-C6-Alkoxy, C3-C7- Cycloalkyl, Cι-C6-Alkyl-C3-C7-Cycloalkyl, Cι-C6-Alkoxy-C3-C7- Cycloalkyl, C3-C7-Cycloalkyloxy, C3-C7-Cyanocycloalkyloxy, Cι-C6-Alkyl-C-C7-Cycloalkyloxy, C3-C7-Halogencycloalkyl, C3-C -Cyanocycloalkyl, C3-C7-Halogencycloalkyloxy, C5-C7-Cy- cloalkenyl, Cι-C6-Alkyl-C5-C7-Cycloalkenyl, Cι-C6-Alkoxy-C5-C7- Cycloalkenyl, C5-C -Cyanocycloalkenyl, C5-C7-Halogencycloalke- nyl, Ci-Cg-Alkoxy-Cx-Ce-Alkyl, Cι-C6-Halogenalkyl, C2-C6-Halo- genalkenyl, C3-Cg-Halogenalkinyl, C2-C6-Cyanoalkenyl, C3-C6- Cyanoalkinyl, Cι-C6-Alkoxy, Ci-Cg-Cyanoalkoxy, Cι-C6-Haloge- nalkoxy, C2-C6-Alkenyloxy, C2-C6-Cyanoalkenyloxy, C2-C6-Halo- genalkenyloxy, C2-C6-Alkinyloxy, Ci-Cg-Al ylthio, Cι-C6-Cyano- alkylthio, Cι-C6-Halogenalkylthio, C -Cg-Alkoxy-Ci-Cg-Alkylthio, Cι-C6-Alkoxycarbonyl, Ci-Cg-Alkylcarbonyl, Cι-C6-Alkyl- carboxy-Cι-C6-Alkyl, Cι-C6-Alkylcarbonyl-Cι-C6-Alkyl, Cι-C6-Al- kylcarbonylamino, Arylcarbonylamino, Arylsulphinyl, Arylsul- phonyl, Heteroarylsulphinyl, Heteroarylsulphonyl, Aryl- Ci-Cg-Alkyl, Aryl-C2-C6-Alkenyl, Aryl-C3-C6-Alkinyl, Heteroa- ryl-Cι-C6-alkyl, Heteroaryl-C2-Cg-Alkenyl, Heteroary1-C3- C6-Alkinyl, Aryl-Ci-Cg-Alkoxy, Aryl-C2-C6-Alkenyloxy, Aryl- C3-C6-Alkinyloxy, Heteroaryl-CiCg-alkoxy, Heteroaryl-C2-C6-Al- kenyloxy, Heteroaryl-C3-C6-alkinyloxy, Cι-C6-Alkylsulphinyl, Cx-Cg-Alkylsulphonyl, C2-C6-Alkenylsulphinyl, C2-C6-Alkenyl- sulphonyl, Ci-Cg-Alkylamino, Di-Cι-C6-Alkylamino, HC=N0H, C1-C6-Alkyl-C=N0H, HC=N-0-C1-C6-Alkyl, HC=N-0-Cι-C6-Alkyl- Aryl, C1-C6-Alkyl-C=N-0-Cι-C6-Alkyl, HC=N-0-C2-C6-Alkenyl, C1-C6-Alkyl-C=N-0-C2-C6-Alkenyl, HC=N-0-Aryl, Ci-C -Al- kyl-C=N-0-Aryl, Aryl, Aryloxy, Heteroaryl, Heteroaryloxy, Ar lthio, Heteroarylthio; oderHC = N-0 -C 6 -alkyl, HC = N-0 -C 6 -alkyl aryl, Cx-Cg-alkyl-C ^ N- O-Ci-C-alkyl, HC = N- 0-C 2 -C 6 -alkenyl, C 1 -C 6 -alkyl-C = N-0-C 2 -C 6 -alkenyl, HC = N-0-aryl, C 1 -C 6 -alkyl-C = N-0-aryl, aryl, aryloxy, heteroaryl, heteroaryloxy, arylthio, heteroarylthio, where the cyclic substituents in turn can independently carry one to five of the following substituents: hydrogen, halogen, cyano, nitro, hydroxy, mercapto, thiocyanato, Carboxy, amino, C_-C 6 -alkyl, Ci-Cg-cyanoalkyl, C 2 -C 6 -alkenyl, -C-C 6 -alkoxy-C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, -C 6 -alkoxy-C 3 -C 6 -alkynyl, C 3 -Cg-alkynyl-Cι-C 6 -alkoxy, C 3 -C 7 - cycloalkyl, Cι-C 6 -alkyl-C 3 -C 7 - Cycloalkyl, -C-C 6 alkoxy-C 3 -C 7 - cycloalkyl, C 3 -C 7 -cycloalkyloxy, C 3 -C 7 -cyanocycloalkyloxy, Cι-C 6 -alkyl-CC 7 -cycloalkyloxy, C 3 -C 7 -Halogencycloalkyl, C 3 -C -Cyanocycloalkyl, C 3 -C 7 -Halogencycloalkyloxy, C 5 -C 7 -Cy- cloalkenyl, Cι-C 6 -alkyl-C 5 -C 7 -cycloalkenyl, Cι- C 6 alkoxy-C 5 -C 7 cycloalkenyl, C 5 -C cyanocycloalkenyl, C 5 -C 7 halocycloalkenyl, Ci-Cg-alkoxy-Cx-Ce-alkyl, -C-C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -Cg haloalkynyl, C 2 -C 6 cyanoalkenyl, C 3 -C 6 - cyanoalkynyl, -C-C 6 alkoxy, Ci-Cg-cyanoalkoxy, Cι-C 6 - Halogenalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 cyanoalkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, Ci-Cg-Al ylthio, Cι-C 6 - cyano alkylthio, Cι-C 6 haloalkylthio, C -CG-alkoxy-Ci-Cg-alkylthio, Cι-C 6 alkoxycarbonyl, Ci-Cg-alkylcarbonyl, Cι-C 6 -alkyl carboxy-Cι-C 6 - Alkyl, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonylamino, arylcarbonylamino, arylsulphinyl, arylsulphonyl, heteroarylsulphinyl, heteroarylsulphonyl, aryl- Ci-Cg-alkyl, aryl-C 2 - C 6 -alkenyl, aryl-C 3 -C 6 -alkynyl, heteroaryl -CC-C 6 -alkyl, heteroaryl-C 2 -Cg-alkenyl, heteroaryl-C 3 - C 6 -alkynyl, aryl-Ci-Cg -Alkoxy, aryl-C 2 -C 6 -alkenyloxy, aryl-C 3 -C 6 -alkynyloxy, heteroaryl -CiCg-alkoxy, heteroaryl-C 2 -C 6 -alkenyloxy, heteroaryl-C 3 -C 6 -alkynyloxy, -C-C 6 -alkylsulphinyl, Cx-Cg-alkylsulphonyl, C 2 -C 6 -alkenylsulphinyl, C 2 -C 6 -alkenyl sulphonyl, Ci-Cg-alkylamino, di-Cι-C 6 -alkylamino, HC = N0H, C 1 -C 6 -alkyl-C = N0H, HC = N-0-C 1 -C 6 -Alkyl, HC = N-0-C 6 -alkyl-aryl, C 1 -C 6 -alkyl-C = N-0-C-C 6 -alkyl, HC = N-0-C 2 -C 6 -Alkenyl, C 1 -C 6 alkyl-C = N-0-C 2 -C 6 -alkenyl, HC = N-0-aryl, Ci-C-alkyl-C = N-0-aryl, aryl , Aryloxy, heteroaryl, heteroaryloxy, ar lthio, heteroarylthio; or
wobei der Aryl- oder Heteroarylrest mit einem ankondensierten Phenylring, einem ankondensierten C3-Cg-Carbocyclus oder einem 5- oder 6-gliedrigen Heterocyclus ein bicyclisches System ausbildet, wobei das ankondensierte Ringsystem gegebenenfalls einen bis drei der vorstehend für Aryl genannten Substituen- ten tragen kann. 40wherein the aryl or heteroaryl radical with a fused-on phenyl ring, a fused-on C 3 -Cg carbocycle or a 5- or 6-membered heterocycle forms a bicyclic system, the fused-on ring system optionally carrying one to three of the substituents mentioned above for aryl can. 40
R2 Ci-Cg-Alkyl oder Aryl oder Heteroaryl, wobei Aryl, Heteroaryl einen bis drei der unter R1 für Aryl genannten Substituenten tragen können, C3-C -Cycloalkyl oder Ci-Cg-Alkylaryl;R 2 Ci-Cg-alkyl or aryl or heteroaryl, where aryl, heteroaryl can carry one to three of the substituents mentioned under R 1 for aryl, C 3 -C cycloalkyl or Ci-Cg-alkylaryl;
5 A COOR3 oder CONR3R4, wobei R3 und R4 unabhängig voneinander Wasserstoff, Cι-C6-Alkyl, C2-C6-Alkenyl, C3-C7-Cycloalkyl oder Ci-Cg-Alkyl-Aryl bedeuten, welche ggf. teilweise oder vollständig halogeniert sein können oder einen bis drei Substituenten ausgewählt aus Cι-C4-Alkoxy, Cχ-C4-Halogenalkoxy, 0 Cι-C4-Alkylthio, C3-C7-Cycloalkyl, C5-C7-Cycloalkenyl tragen können;5 A COOR 3 or CONR 3 R 4 , where R 3 and R 4 independently of one another hydrogen, -CC 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 7 cycloalkyl or Ci-Cg-alkyl-aryl mean which may be partially or completely halogenated or one to three substituents selected from C 1 -C 4 -alkoxy, Cχ-C 4 -haloalkoxy, 0 C 1 -C 4 -alkylthio, C 3 -C 7 -cycloalkyl, C 5 -C 7 -Cycloalkenyl can wear;
sowie deren landwirtschaftlich brauchbare Salze als Pflanzenschutzmittel . 5and their agriculturally useful salts as crop protection agents. 5
2. Verwendung von 2-Oxopyrrolen der Formel I nach Anspruch 1 als Herbizide.2. Use of 2-oxopyrroles of the formula I according to claim 1 as herbicides.
3. Verwendung von 2-Oxopyrrolen der Formel I nach Anspruch 1 als 0 Insektizide.3. Use of 2-oxopyrroles of the formula I according to claim 1 as 0 insecticides.
4. 2-Oxopyyrole der Formel I4. 2-oxopyyroles of the formula I.
A 5 \— * R1 A 5 \ - * R 1
RARA
I - C ° (I ) H 0I - C ° (I) H 0
R1 Aryl oder Heteroaryl, wobei diese Reste unabhängig voneinander eine bis fünf der folgenden Gruppen tragen können: Wasserstoff, Halogen, Cyano, Nitro, Hydroxy, Mercapto, Thiocyanato, Carboxy, Amino,Ci-Cg-Alkyl, Ci-Cg-Cyanoalkyl, C2-C6- 5 Alkenyl, Cι-C6-Alkoxy-C2-C6-Alkenyl, C3-C6-Alkinyl, Ci-Cg-Al- koxy-C3-Cg-Alkinyl, C3-Cg-Alkinyl-Cι-Cg-Alkoxy, C3-C7-Cycloal- kyl, Cι-C6-Alkyl-C3-C7-Cycloalkyl, C1-Cg-Alkoxy-C3-C7-Cycloal- kyl, C3-C -Cycloalkyloxy, C3-C -Cyanocycloalkyloxy, Ci-Cg-Al- kyl-C3-C7-Cycloalkyloxy, C3-C7-Halogencycloalkyl, C3-C7-Cyano- 0 cycloalkyl, C3-C7-Halogencycloalkyloxy, C5-C -Cycloalkenyl, Cι-Cg-Alkyl-C5-C7-Cycloalkenyl, Cι-Cg-Alkoxy-C5-C -Cycloalke- nyl, C5-C7-Cyanocycloalkenyl, C5-C7-Halogencycloalkenyl, Cι-C6-Alkoxy-Cχ-Cg-Alkyl, Ci-Cg-Halogenalkyl, C2-C6-Halogenal- kenyl, C3-C6-Halogenalkinyl, C2-Cg-Cyanoalkenyl, C3-C6-Cyano- g alkinyl, Ci-Cg-Alkoxy, Cι-C6-Cyanoalkoxy, Ci-Cg-Halogenalkoxy, C2-C6-Alkenyloxy, C2-C6-Cyanoalkenyloxy, C -C6-Halogenalkeny- loxy, C2-C6-Alkinyloxy, Cx-Cg-Alkylthio, Cχ-C6-Cyanoalkylthio, 41R 1 aryl or heteroaryl, where these radicals can independently carry one to five of the following groups: hydrogen, halogen, cyano, nitro, hydroxy, mercapto, thiocyanato, carboxy, amino, Ci-Cg-alkyl, Ci-Cg-cyanoalkyl, C 2 -C 6 - 5 alkenyl, -C-C 6 alkoxy-C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, Ci-Cg-alkoxy-C 3 -Cg alkynyl, C 3 - Cg-alkynyl-Cι-Cg-alkoxy, C 3 -C 7 cycloalkyl, Cι-C 6 alkyl-C 3 -C 7 cycloalkyl, C 1 -Cg alkoxy-C 3 -C 7 cycloal- kyl, C 3 -C cycloalkyloxy, C 3 -C cyano cycloalkyloxy, Ci-Cg-alkyl-C 3 -C 7 cycloalkyloxy, C 3 -C 7 halocycloalkyl, C 3 -C 7 cyano-0 cycloalkyl , C 3 -C 7 -Halogencycloalkyloxy, C 5 -C -cycloalkenyl, -C-Cg-alkyl-C 5 -C 7 -cycloalkenyl, Cι-Cg-alkoxy-C 5 -C -cycloalkenyl, C 5 -C 7 -Cyanocycloalkenyl, C 5 -C 7 halocycloalkenyl, Cι-C 6 alkoxy-Cχ-Cg-alkyl, Ci-Cg-haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 6 haloalkynyl, C 2 -Cg-cyanoalkenyl, C 3 -C 6 -cyano- g alkynyl, Ci-Cg-alkoxy, -C-C 6 cyanoalkox y, Ci-Cg haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 cyanoalkenyloxy, C -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, Cx-Cg-alkylthio, Cχ-C 6- cyanoalkylthio, 41
Cx-Cg-Halogenalkylthio, Ci-Cg-Alkoxy-Ci-Cg-Alkylthio, Cχ-Cg-Al- koxycarbonyl, Ci-Cg-Alkylcarbonyl, Cχ-Cg-Alkylcarboxy-Cχ-Cg- Alkyl, Cι-Cg-Alkylcarbonyl-Cι-C6-Alkyl, Cχ-C6-Alkylcarbonyla- mino, Arylcarbonylamino, Arylsulphinyl, Arylsulphonyl, Hete- roarylsulphinyl, Heteroarylsulphonyl, Aryl-Ci-Cg-Alkyl, Aryl- C2-Cg-Alkenyl, Aryl-C3-Cg-Alkinyl, Heteroaryl-Cχ-C6-alkyl, He- teroaryl-C2-C6-Alkenyl, Heteroaryl-C3-Cg-Alkinyl, Aryl- Cχ-Cg-Alkoxy, Aryl-C2-Cg-Alkenyloxy, Aryl-C3-C6-Alkinyloxy, Heteroaryl-CχCg-alkoxy, Heteroary1-C2-Cg-Alkenyloxy, Heteroa- ryl-C3-C6-alkinyloxy, Ci-Cg-Alkylsulphinyl, Cχ-C6-Alkylsulpho- nyl, C2-C6-Alkenylsulphinyl, C2-C6-Alkenylsulphonyl, Cχ-C6-Al- kyla ino, Di-Cχ-C6-Alkylamino, HC=N0H, Cι-C6-Alkyl-C=NOH, HC=N-0-Cι-C6-Alkyl, HC=N-0-Cχ-C6-Alkyl-Aryl, C1-Cg-Alkyl-C=N- O-Ci-Cg-Alkyl, HC=N-0-C2-Cg-Alkenyl, Cχ-Cg-Alkyl-C=N-0-C2-C6- Alkenyl, HC=N-0-Aryl, Cι-C6-Alkyl-C=N-0-Aryl, Aryl, Aryloxy, Heteroaryl, Heteroaryloxy, Arylthio, Heteroarylthio, wobei die cyclischen Substituenten ihrerseits unabhängig voneinander einen bis fünf der nachfolgenden Substituenten tragen können: Wasserstoff, Halogen, Cyano, Nitro, Hydroxy, Mer- capto, Thiocyanato, Carboxy, Amino,Cχ-C6-Alkyl, Cx-Cg-Cyanoal- kyl, C2-C6-Alkenyl, C1-C6-Alkoxy-C2-Cg-Alkenyl, C3-Cg-Alkinyl, Cx-Cg-Alkoxy-Cs-Cg-Alkinyl, C3-C6-Alkinyl-Cι-C6-Alkoxy, C3-C7- Cycloalkyl, C1-C6-Alkyl-C3-C7-Cycloalkyl, Cι-C6-Alkoxy-C3-C7- Cycloalkyl, C3-C -Cycloalkyloxy, C3-C7-Cyanocycloalkyloxy, Cι-C6-Alkyl-C3-C7-Cycloalkyloxy, C3-C7-Halogencycloalkyl,Cx-Cg-haloalkylthio, Ci-Cg-alkoxy-Ci-Cg-alkylthio, Cχ-Cg-alkoxycarbonyl, Ci-Cg-alkylcarbonyl, Cχ-Cg-alkylcarboxy-Cχ-Cg- alkyl, Cι-Cg-alkylcarbonyl- Cι-C 6 alkyl, Cχ-C 6 alkylcarbonylamino, arylcarbonylamino, arylsulphinyl, arylsulphonyl, heteroarylsulphinyl, heteroarylsulphonyl, aryl-Ci-Cg-alkyl, aryl-C 2 -Cg-alkenyl, aryl-C 3 - Cg-alkynyl, heteroaryl-Cχ-C 6 -alkyl, heteroaryl-C 2 -C 6 -alkenyl, heteroaryl-C 3 -Cg-alkynyl, aryl-Cχ-Cg-alkoxy, aryl-C 2 -Cg-alkenyloxy , Aryl-C 3 -C 6 -alkynyloxy, heteroaryl-CχCg-alkoxy, heteroary1-C 2 -cg-alkenyloxy, heteroaryl-C 3 -C 6 -alkynyloxy, Ci-Cg-alkylsulphinyl, Cχ-C 6 -alkylsulpho - nyl, C 2 -C 6 alkenylsulphinyl, C 2 -C 6 alkenylsulphonyl, Cχ-C 6 -alkyla ino, di-Cχ-C 6 -alkylamino, HC = N0H, Cι-C 6 -alkyl-C = NOH, HC = N-C 1 -C 6 -alkyl, HC = N-0-Cχ-C 6 alkyl aryl, C 1 -Cg-alkyl-C = N- O-Ci-Cg-alkyl, HC = N-0-C 2 -Cg-alkenyl, Cχ-Cg-alkyl-C = N-0-C 2 -C 6 -alkenyl, HC = N-0-aryl, Cι-C 6 -alkyl-C = N-0-aryl, aryl, aryloxy, hetero oaryl, heteroaryloxy, arylthio, heteroarylthio, where the cyclic substituents in turn can independently carry one to five of the following substituents: hydrogen, halogen, cyano, nitro, hydroxy, mercapto, thiocyanato, carboxy, amino, Cχ-C 6 -alkyl , Cx-Cg-cyanoalkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkoxy-C 2 -Cg alkenyl, C 3 -Cg alkynyl, Cx-Cg-alkoxy-Cs-Cg-alkynyl , C 3 -C 6 alkynyl-Cι-C 6 alkoxy, C 3 -C 7 - cycloalkyl, C 1 -C 6 alkyl-C 3 -C 7 cycloalkyl, Cι-C 6 -alkoxy-C 3 - C 7 - cycloalkyl, C 3 -C cycloalkyloxy, C 3 -C 7 cyanocycloalkyloxy, Cι-C 6 alkyl-C 3 -C 7 cycloalkyloxy, C 3 -C 7 halocycloalkyl,
C3_c7-Cyanocycloalkyl, C3-C7-Halogencycloalkyloxy, C5-C -Cy- cloalkenyl, Cx-Cg-Alkyl-Cs-C--Cycloalkenyl, Cι-Cg-Alkoxy-C5-C7- Cycloalkenyl, C5-C7-Cyanocycloalkenyl, C5-C7-Halogencycloalke- nyl, Cι-C6-Alkoxy-Cι-C6-Alkyl, Ci-Cg-Halogenalkyl, C -C6-Halo- genalkenyl, C3-Cg-Halogenalkinyl, C2-C6-Cyanoalkenyl, C3-C6- Cyanoalkinyl, Ci-Cg-Alkoxy, Cx-Cg-Cyanoalkoxy, Cχ-Cg-Haloge- nalkoxy, C2-C6-Alkenyloxy, C2-Cg-Cyanoalkenyloxy, C2-Cg-Halo- genalkenyloxy, C2-C6-Alkinyloxy, Ci-Cg-Alkylthio, Ci-Cg-Cyano- alkylthio, Ci-Cg-Halogenalkylthio, Ci-Cg-Alkoxy-Cx-Cg-Alkylt- hio, Cx-Cg-Alkoxycarbonyl, Cχ-Cg-Alkylcarbonyl, Cχ-C6-Alkyl- carboxy-Cχ-Cg-Alkyl, Cχ-C6-Alkylcarbonyl-Cχ-Cg-Alkyl, Cχ-C6-Al- kylcarbonylamino, Arylcarbonylamino, Arylsulphinyl, Arylsulphonyl, Heteroarylsulphinyl, Heteroarylsulphonyl, Aryl- Cχ-C6-Alkyl, Aryl-C2-Cg-Alkenyl, Aryl-C3-C6-Alkinyl, Heteroa- ryl-Cχ-Cg-alkyl, Heteroaryl-C2-Cg-Alkenyl, Heteroaryl-C3-C 3 _c 7 cyanocycloalkyl, C 3 -C 7 halocycloalkyloxy, C 5 -C cycloalkenyl, Cx-Cg-alkyl-Cs-C - cycloalkenyl, -C-Cg-alkoxy-C 5 -C 7 - cycloalkenyl , C 5 -C 7 cyanocycloalkenyl, C 5 -C 7 halocycloalkenyl, C 1 -C 6 alkoxy-C 6 -C 6 alkyl, C 1 -C 6 -haloalkyl, C -C 6 haloalkenyl, C 3 -Cg-haloalkynyl, C 2 -C 6 -cyanoalkenyl, C 3 -C 6 -cyanoalkynyl, Ci-Cg-alkoxy, Cx-Cg-cyanoalkoxy, Cχ-Cg-haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -Cg-cyanoalkenyloxy, C 2 -Cg -halogenalkenyloxy, C 2 -C 6 -alkynyloxy, Ci-Cg-alkylthio, Ci-Cg-cyanoalkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkoxy-Cx -Cg-alkylt- hio, Cx-Cg-alkoxycarbonyl, Cχ-Cg-alkylcarbonyl, Cχ-C 6 -alkyl-carboxy-Cχ-Cg-alkyl, Cχ-C 6 -alkylcarbonyl-Cχ-Cg-alkyl, Cχ-C 6 -alkylcarbonylamino, arylcarbonylamino, arylsulphinyl, arylsulphonyl, heteroarylsulphinyl, heteroarylsulphonyl, aryl-Cχ-C 6 -alkyl, aryl-C 2 -Cg-alkenyl, aryl-C 3 -C 6 -alkynyl, heteroaryl-caryl Cg-alkyl, heteroaryl-C 2 -Cg-alkenyl, heteroaryl-C 3 -
Cg-Alkinyl, Aryl-Cχ-C6-Alkoxy, Aryl-C2-Cg-Alkenyloxy, Aryl- C3-Cg-Alkinyloxy, Heteroaryl-CχCg-alkoxy, Heteroaryl-C2-C6-Al- kenyloxy, Heteroaryl-C3-C6-alkinyloxy, Cχ-Cg-Alkylsulphinyl, Cχ-Cg-Alkylsulphonyl, C2-C6-Alkenylsulphinyl, C2-Cg-Alkenyl- sulphonyl, Cχ-Cg-Alkylamino, Di-Cχ-C6-Alkylamino, HC=NOH, Cχ-C6-Alkyl-C=NOH, HC=N-0-Cχ-C6-Alkyl, HC=N-0-Cχ-C6-Alkyl- Aryl, Cχ-C6-Alkyl-C=N-0-Cχ-C6-Alkyl, HC=N-0-C2-C6-Alkenyl, 42Cg-alkynyl, aryl-Cχ-C 6 -alkoxy, aryl-C 2 -Cg-alkenyloxy, aryl-C 3 -Cg-alkynyloxy, heteroaryl-CχCg-alkoxy, heteroaryl-C 2 -C 6 -alkenyloxy, heteroaryl -C 3 -C 6 alkynyloxy, Cχ-Cg-alkylsulphinyl, Cχ-Cg-alkylsulphonyl, C 2 -C 6 -alkenylsulphinyl, C 2 -Cg-alkenylsulfonyl, Cχ-Cg-alkylamino, di-Cχ-C 6 -Alkylamino, HC = NOH, Cχ-C 6 -alkyl-C = NOH, HC = N-0-Cχ-C 6 -alkyl, HC = N-0-C C-C 6 -alkyl aryl, Cχ-C 6 -Alkyl-C = N-0-Cχ-C 6 -alkyl, HC = N-0-C 2 -C 6 -alkenyl, 42
Cι-C6-Alkyl-C=N-0-C2-C6-Alkenyl, HC=N-0-Aryl , Cχ-C6-Al- kyl-C=N-0-Aryl, Aryl, Aryloxy, Heteroaryl, Heteroaryloxy, Arylthio, Heteroarylthio; oder-C-C 6 alkyl-C = N-0-C 2 -C 6 -alkenyl, HC = N-0-aryl, Cχ-C 6 -alkyl-C = N-0-aryl, aryl, aryloxy, Heteroaryl, heteroaryloxy, arylthio, heteroarylthio; or
wobei der Aryl- oder Heteroarylrest mit einem ankondensierten Phenylring, einem ankondensierten C3-C6-Carbocyclus oder einem 5- oder 6-gliedrigen Heterocyclus ein bicyclisches System ausbildet, wobei das ankondensierte Ringsystem gegebenenfalls einen bis drei der vorstehend für Aryl genannten Substituenten tragen kann.wherein the aryl or heteroaryl radical with a fused-on phenyl ring, a fused-on C 3 -C 6 carbocycle or a 5- or 6-membered heterocycle forms a bicyclic system, the fused-on ring system optionally being able to carry one to three of the substituents mentioned above for aryl .
R2 Cχ-C6-Alkyl oder Aryl oder Heteroaryl, wobei Aryl oder Heteroaryl einen bis drei der unter R1 für Aryl genannten Substi' t enten tragen können;R 2 is Cχ-C 6 alkyl or aryl or heteroaryl, where aryl or heteroaryl can carry one to three of the substituents mentioned under R 1 for aryl;
A COOR3 oder C0NR3R4, wobei R3 und R4 unabhängig voneinander Wasserstoff, Cχ-C6-Alkyl, C2-C6-Alkenyl , C3-C7-Cycloalkyl oder Cχ-Cg-Alkyl-Aryl bedeuten, welche ggf. teilweise oder vollständig halogeniert sein können oder einen bis drei Sub- stituenten ausgewählt aus Cι-C4-Alkoxy, Cχ-C4-Halogenalkoxy, C1-C4-Alkylthio, C3-C7-Cycloalkyl, C5-C -Cycloalkenyl tragen können; ausgenommen die Verbindungen der nachfolgenden Tabelle:A COOR 3 or C0NR 3 R 4 , where R 3 and R 4 independently of one another are hydrogen, Cχ-C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 7 cycloalkyl or Cχ-Cg-alkyl-aryl which optionally partially or fully halogenated or may be one to three sub-substituents selected from Cι-C 4 alkoxy, Cχ-C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 3 -C 7 cycloalkyl, C Can wear 5 -C cycloalkenyl; except the connections in the table below:
Rl R2 ARl R 2 A
C6H5 CH3 COOC2H5 C 6 H 5 CH 3 COOC 2 H 5
4- (CH3)2N-C6H4 CH3 COOC2H54- (CH 3 ) 2 NC 6 H 4 CH 3 COOC2H5
2-NO2-C5H4 CH3 COOC2H52-NO2-C5H4 CH3 COOC2H5
4-N02-C6H4 CH3 COOC2H54-N0 2 -C 6 H 4 CH 3 COOC2H5
4-Cl-C6H4 CH3 COOC2H54-Cl-C 6 H 4 CH 3 COOC2H5
4-Br-C6H4 CH3 COOC2H5 4-Br-C 6 H 4 CH 3 COOC 2 H 5
4-CH3-C6H4 CH3 COOC2H5 4-CH 3 -C 6 H 4 CH 3 COOC 2 H 5
4-H0-CgH4 CH3 COOC2H5 4-H0-CgH 4 CH 3 COOC 2 H 5
2 , 4- (CH3) 2-5-C00CH2CH3-pyrrol-3-yl CH3 COOC2H5 2, 4- (CH 3 ) 2 -5-C00CH 2 CH 3 -pyrrol-3-yl CH 3 COOC 2 H 5
3, 5-(CH3)2-4-COOCH2CH3-pyrrol-2-yl CH3 COOC2H5 3, 5- (CH 3 ) 2 -4-COOCH 2 CH 3 -pyrrol-2-yl CH 3 COOC 2 H 5
C6H5 C6H5 COOCH3 C 6 H 5 C 6 H 5 COOCH 3
2-COOCH2CH3-5-CH30-indol-3-yl CH3 COOC2H52-COOCH 2 CH 3 -5-CH 3 0-indol-3-yl CH 3 COOC2H5
4-CH30-C6H4 CH3 COOC2H5 434-CH 3 0-C 6 H 4 CH 3 COOC 2 H 5 43
5. Verbindungen der Formeln Ha - IIc5. Compounds of the formulas Ha - IIc
AA
CF, ^N^ 0 CF, ^ N ^ 0
Ha Ilb IIcHa Ilb IIc
wobei A und R2 die in Anspruch 1 genannte Bedeutung haben. Synthese von 2 -Trifluormethyl -5-0x0 -4 , 5 -dihydropyrrol-3 -car- bonsäuremethylester (Ilb)wherein A and R 2 have the meaning given in claim 1. Synthesis of 2-trifluoromethyl -5-0x0 -4, 5 -dihydropyrrol-3 -carboxylic acid methyl ester (Ilb)
2 g (8,2 mmol) Trifluoracetylbutandicarbonsäuredimethylester wurden in 100ml Methanol gelöst und bei 0 bis 5°C mit Ammoniakgas gesättigt. Anschließend wurde bei Raumtemperatur 12 h gerührt, eingeengt, der Rückstand in 50 ml Xylol yufgenommen und nach Zugabe einer Spatelspitze p-Toluolsulfonsäure 6 h am Rückfluß erhitzt.2 g (8.2 mmol) of dimethyl trifluoroacetylbutanedicarboxylate were dissolved in 100 ml of methanol and saturated at 0 to 5 ° C. with ammonia gas. The mixture was then stirred at room temperature for 12 h, concentrated, the residue was taken up in 50 ml of xylene and, after the addition of a spatula tip, p-toluenesulfonic acid was heated under reflux for 6 h.
Die Mischung wurde filtriert, das erhltene Filtrat mit Wasser verdünnt und mit Essigsäureethylester extrahiert. Anschließend wurde die organische Phase eingeengt und getrocknet. (MH+ 210)The mixture was filtered, the filtrate obtained was diluted with water and extracted with ethyl acetate. The organic phase was then concentrated and dried. (MH + 210)
Synthese von 2 -Methyl -5 -oxo-4 , 5 -dihydropyrrol -3 -carbonsäurenitril IICSynthesis of 2-methyl -5-oxo-4, 5 -dihydropyrrole -3-carbonsitrile IIC
Eine Mischung von 0,9 g (4,6 mmol) 2 -Methyl -5 -oxo-4 , 5 -dihydropyrrol- 3 -carboxamid, 1,4 g (9,2 mmol) Phosphoroxychlorid und 0,9 g (6,4 mmol) Kaliumcarbonat wurde in 50 ml Aceton 6 h am Rückfluß erhitzt. Anschließend wurde eingeengt und der erhaltene Rückstand an Kieselgel chromatographiert (LM: Cyclo- hexan:Essigsäureethylester 10:1 bis 1:1). Es wurden 0,15 g (19 % d.Th.) des gewünschten Produktes erhalten (IR: 2220 cm -1' A mixture of 0.9 g (4.6 mmol) 2-methyl -5-oxo-4,5-dihydropyrrole-3-carboxamide, 1.4 g (9.2 mmol) phosphorus oxychloride and 0.9 g (6, 4 mmol) of potassium carbonate was refluxed in 50 ml of acetone for 6 h. The mixture was then concentrated and the residue obtained was chromatographed on silica gel (LM: cyclohexane: ethyl acetate 10: 1 to 1: 1). 0.15 g (19% of theory) of the desired product was obtained (IR: 2220 cm -1 '
EP99919137A 1998-03-30 1999-03-24 The use of derivatives of 2-oxopyrrole as crop protection agents and novel 2-oxopyrroles Withdrawn EP1066256A1 (en)

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DE2928305A1 (en) 1979-07-13 1981-02-05 Hoechst Ag 2-DIHALOGENMETHYLEN-3-HALOGEN-3-CARBOALKOXY-5-OXOPYRROLIDINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES, BACTERICIDES AND ALGICIDES Pesticides
DE3147638A1 (en) 1981-12-02 1983-06-16 Hoechst Ag, 6230 Frankfurt "FUNGICIDES AND BEACTERICIDES 2-DIHALOGENMETHYLENEPYRROLINONE"
US4681971A (en) 1984-11-07 1987-07-21 Ciba-Geigy Corporation Phenyl substituted aminodicarboxylate esters
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