EP1987008A2 - Heteroaroyl-substituted alanines - Google Patents

Heteroaroyl-substituted alanines

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Publication number
EP1987008A2
EP1987008A2 EP07704402A EP07704402A EP1987008A2 EP 1987008 A2 EP1987008 A2 EP 1987008A2 EP 07704402 A EP07704402 A EP 07704402A EP 07704402 A EP07704402 A EP 07704402A EP 1987008 A2 EP1987008 A2 EP 1987008A2
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EP
European Patent Office
Prior art keywords
alkyl
alkoxy
phenyl
heteroaryl
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP07704402A
Other languages
German (de)
French (fr)
Inventor
Matthias Witschel
Cyrill Zagar
Eike Hupe
Toralf KÜHN
William Karl Moberg
Liliana Parra Rapado
Frank Stelzer
Andrea Vescovi
Michael Rack
Robert Reinhard
Bernd Sievernich
Klaus Grossmann
Thomas Ehrhardt
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BASF SE
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BASF SE
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Priority to EP07704402A priority Critical patent/EP1987008A2/en
Publication of EP1987008A2 publication Critical patent/EP1987008A2/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • a 5- or 6-membered heteroaryl having one to four nitrogen atoms, or having one to three nitrogen atoms and one oxygen or sulfur atom, or with a
  • Oxygen or sulfur atom which may be partially or fully halogenated and / or 1 to 3 radicals from the group cyano, -C 6 alkyl, C 3 -C 6 cycloalkyl, -C 6 -haloalkyl, -C 6 alkoxy, -C 6 haloalkoxy, and CrC can carry 6 -alkoxy-Ci-C4-alkyl;
  • R 1 , R 2 are hydrogen, hydroxy or C 1 -C 6 -alkoxy
  • R 3 is C 1 -C 6 -alkyl, C 1 -C 4 -cyanoalkyl or C 1 -C 6 -haloalkyl;
  • R 4 is hydrogen or C 1 -C 6 -alkyl
  • R 5 is hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 kinyl -alkyl, Ci-C 6 haloalkyl, C 2 - C 6 haloalkenyl, C 2 -C 6 haloalkynyl , Ci-C 6 cyanoalkyl, C 2 -C 6 - cyanoalkenyl, C 2 -C 6 -Cyanoalkinyl, Ci-C 6 hydroxyalkyl, C 2 -C 6 -Hydroxyalkenyl, C 2 -C 6 -Hydroxyalkinyl, C3-C 6 cycloalkyl, C3-C6 cycloalkenyl, 3- to 6-membered
  • Heterocyclyl wherein the abovementioned cycloalkyl, cycloalkenyl or 3- to 6-membered heterocyclyl radicals may be partially or completely halogenated and / or one to three radicals from the group consisting of oxo, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 - haloalkyl, hydroxy, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy,
  • Ci-C 6 -alkoxycarbonyl hydroxycarbonyl-Ci-C 6 alkoxy, Ci-C 6 alkoxycarbonyl-alkoxy-Ci-C 6, amino, Ci-C6 alkylamino, di (-C 6 - alkyl) amino, Ci-C 6 alkylsulfonylamino, Ci-C ⁇ -haloalkylsulfonylamino, aminocarbonylamino, (CrC 6 alkylamino) carbonylamino, di (CrC 6 - alkyl) aminocarbonylamino aryl, and (CrC 6 alkyl) may bear, aryl;
  • C 1 -C 6 -alkoxy amino, C 1 -C 6 -alkylamino, di (C 1 -C 6 -alkyl) amino, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -haloalkylsulfonylamino, (C 1 -C 6 -alkylamino) -carbonylamino, di (C 1 -C 6 -alkyl) aminocarbonylamino, aryl and aryl (C 1 -C 6 -alkyl);
  • R 7 is hydrogen, CrC ⁇ alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 kinyl -alkyl, C 3 -C 6 - haloalkenyl, C 3 -C 6 haloalkynyl, hydroxy or C 1 -C 6 -alkoxy;
  • R 8 is d-Ce-alkyl, Ci-C 6 -haloalkyl or phenyl, where the phenyl radical may be partially or fully halogenated and / or may carry one to three of the following groups: Ci-C 6 alkyl, d- C ⁇ -haloalkyl or Ci-CrAlkoxy;
  • the invention relates to processes and intermediates for the preparation of compounds of formula I, compositions containing them and the use of these derivatives or agents containing them for controlling harmful plants.
  • 2, ⁇ -DiaminocarbonylENSen with herbicidal activity are described inter alia in WO 03/045878.
  • heteroaroyl-substituted alanines of the formula I and their herbicidal activity were found.
  • herbicidal agents were found which contain the compounds I and have a very good herbicidal activity.
  • methods for the preparation of these compositions and methods for controlling undesired plant growth with the compounds I have been found.
  • the compounds of the formula I contain two or more chiral centers and are then present as enantiomer or diastereomer mixtures.
  • the invention provides both the pure enantiomers or diastereomers and mixtures thereof.
  • the compounds of the formula I can also be in the form of their agriculturally useful salts, whereby the type of salt generally does not matter.
  • the salts of those cations or the acid addition salts of those acids come into consideration whose cations, or anions, do not adversely affect the herbicidal activity of the compounds I.
  • the cations used are in particular ions of the alkali metals, preferably lithium, sodium and potassium, the alkaline earth metals, preferably calcium and magnesium, and the transition metals, preferably manganese, copper, zinc and iron, and ammonium, where, if desired, one to four hydrogen atoms are replaced by C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl or benzyl preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (2-hydroxyeth-1-oxy) eth-1-ylammonium, di- (2-hydroxyeth-1-yl) -ammonium, trimethylbenzylammonium, of further
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
  • substituents R 1 -R 12 or as radicals on phenyl organic moieties mentioned aryl, heteroaryl or Hetrocyclylringen are collective terms for individual enumerations of the individual group members.
  • All hydrocarbon chains ie all alkyl, alkylsilyl, alkenyl, Alkynyl, cyanoalkyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, alkoxyalkyl, alkoxyalkoxyalkyl, alkylcarbonyl, alkenylcarbonyl, alkynecarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, alkylamino , Alkylsulfonylamino, haloalkylsulfonylamino, alkylalkoxycarbonylamino, alkylaminocarbonyl, alkylamino
  • halogenated substituents preferably carry one to five identical or different halogen atoms.
  • the meaning halogen in each case represents fluorine, chlorine, bromine or iodine.
  • C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl C 2 -C 6 alkenylthio-Ci-C4-alkyl, C2-C6 alkynylthio-Ci-C4-alkyl, Ci-C ⁇ -alkylsulfinyl-Ci-C ⁇ alkyl, Ci-C 6 haloalkyl sulfinyl C 1 -C 4 -alkyl, C 1 -C 6 -alkylsulfonyl-C 1 -C 4 -alkyl, C 1 -C 6 -haloalkylsulfonyl-d- C4-alkyl, amino-Ci-C4-alkyl, Di (C 1 -C 6 -alkyl) amino-C 1 -C 4 -alkyl, formylamino-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonylamin
  • Ci-C4-alkyl as mentioned above, as well as e.g. 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 ethyl-butyl,
  • C 1 -C 4 -alkylcarbonyl e.g. Methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or
  • C 1 -C 4 -alkylcarbonyl as mentioned above, and also, for example, pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2- Dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1, 2-Dimethylbutylcarbonyl, 1, 3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1
  • Ethylbutylcarbonyl 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-i-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl;
  • C 3 -C 6 -cycloalkyl and the cycloalkyl parts of C 3 -C 6 -cycloalkylcarbonyl monocyclic, saturated hydrocarbon having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
  • C3-C6 cycloalkenyl e.g. 1-Cyclopropenyl, 2-Cyclopropenyl, 1-Cyclobutenyl, 2-Cyclobutenyl, 1-Cyclopentenyl, 2-Cyclopentenyl, 1, 3-Cyclopentadienyl, 1, 4-
  • Alkenyl) -N- (C 1 -C 6 alkoxy) aminocarbonyl e.g. 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1 - Methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1- Dimethyl 2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1
  • C2-C6-alkenyl and also the alkenyl moieties of C2-C6-alkenylcarbonyl, C2-C6-alkenyloxy Ci-C 4 alkyl, C 2 -C 6 alkenylthio-Ci-C4-alkyl, phenyl-C 2 -C 4 alkenyl, heteroaryl C 2 -C 4 alkenyl: C 3 -C 6 alkenyl as mentioned above and ethenyl; - C3-C6-alkynyl and the alkynyl moieties of Cs-C ⁇ -alkynyloxycarbonyl, C3-C6-alkynylaminocarbonyl, N- (C3-C6-alkynyl) -N- (Ci-C6-alkyl) -aminocarbonyl, N- (C3-C6 Alkynyl) -N- (C 1 -C 6 -alkoxyamin
  • cyanoalkyl for example, cyanomethyl, 1-cyanoeth-1-yl, 2-cyanoeth-1-yl, 1-cyano-prop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1 -yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl , 1-cyano-but-2-yl, 2-cyanobut-2-yl, 1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-cyano-2-methyl-prop-3-yl, 2 Cyano-2-methyl-prop-3-yl, 3-cyano-2-methyl-prop-3-yl and 2-cyano-methyl-prop-2-yl;
  • C 1 -C 6 -hydroxyalkyl C 1 -C 4 -hydroxyalkyl as mentioned above, and also, for example, 1-hydroxy-pent-5-yl, 2-hydroxy-pent-5-yl, 3-hydroxy-pent-5-yl, 4 -Hydroxy-pent-5-yl, 5-hydroxy-pent-5-yl, 1-hydroxypent-4-yl, 2-hydroxy-4-yl, 3-hydroxypent-4-yl, 4-
  • Hydroxypent-4-yl 1-hydroxy-pent-3-yl, 2-hydroxy-pent-3-yl, 3-hydroxy-pent-3-yl, 1-hydroxy-2-methylbut-3-yl, 2-hydroxy-2-methyl-but-3-yl, 3-hydroxy-2-methyl-but-3-yl, 1-hydroxy-2-methyl-but-4-yl, 2-hydroxy-2-methyl but-4-yl, 3-hydroxy-2-methyl but-4-yl, 4-hydroxy-2-methyl-but-4-yl, 1-hydroxy-3-methyl-but-4-yl, 2-hydroxy-3-methyl-but-4-yl, 3 Hydroxy-3-methylbut-4-yl, 4-hydroxy-3-methyl-but-4-yl, 1-hydroxy-hex-6-yl, 2-hydroxy-hex-6-yl, 3-hydroxy hex-6-yl, 4-hydroxy-hex-6-yl, 5-hydroxy-hex-6-yl, 6-hydroxy-hex-6-yl, 1-hydroxy-2-methyl-pent-5-yl, 2-hydroxy-2-methyl-pent-5-yl, 3-
  • C3-C6-haloalkenyl a C3-C6-alkenyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, e.g. 2-chloro-prop-2-en-1-yl, 3-chloroprop-2-en-1-yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop-2-ene 1-yl, 2,3,3-trichloro-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3
  • C2-C6 cyanoalkenyl e.g. 2-cyanovinyl, 2-cyanoallyl, 3-cyanoallyl, 2,3-dicyanoallyl, 3,3-dicyanoallyl, 2,3,3-tricyanoallyl, 2,3-dicyanobut-2-enyl;
  • C3-C6-haloalkynyl a C3-C6-alkynyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, e.g. 1,1-Difluoro-prop-2-yn-1-yl, 3-iodo-prop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2in-1 yl, 1, 1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1 yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;
  • C2-C6 cyanoalkynyl e.g. 1,1-dicyano-prop-2-yn-1-yl, 3-cyano-prop-2-yn-1-yl, A-cyano-but-2-yn-1-yl, 1,1-dicyanobutyl 2-yn-1-yl, 4-cyanobut-3-yn-1-yl, 5-cyanopent-3-yn-1-yl, 5-cyanopent-4-yn-1-yl, 6-cyanohex-4- in-1-yl or 6-cyanohex-5-yn-1-yl;
  • C 2 -C 6 -hydroxyalkynyl and the hydroxy parts of phenyl-C 2 -C 4 -hydroxyalkynyl e.g. 1, 1-dihydroxy-prop-2-yn-1-yl, 3-hydroxyprop-2-yn-1-yl, 4-hydroxy-but-2-yn-1-yl, 1, 1-dihydroxybutyl 2-yn-1-yl, 4-hydroxybut-3-yn-1-yl, 5-hydroxypent-3-yn-1-yl, 5-hydroxypent-4-yn-1-yl, 6-hydroxyhex-4 in-1-yl or 6-hydroxyhex-5-yn-1-yl;
  • C 1 -C 6 -alkylsulfinyl (C 1 -C 6 -alkyl-S (OO) -) and the C 1 -C 6 -alkylsulfinyl parts of C 1 -C 6 -alkylsulfinyl-C 1 -C 4 -alkyl: for example methylsulfinyl, Ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1 - ethylprop
  • Ci-C ⁇ -haloalkylsulfinyl and the Ci-C6-Halogenalkylsulfinyl parts of Ci-C ⁇ - haloalkylsulfinyl-Ci-C4-alkyl Ci-C ⁇ -Alkylsulfinylrest as mentioned above, which partially or completely by fluorine, chlorine, bromine and / or iodine is substituted, eg Fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2, 2-difluoroethylsulf
  • C 1 -C 6 -alkylsulfonyl (C 1 -C 6 -alkyl-S (O) 2 -) and the C 1 -C 6 -alkylsulfonyl parts of C 1 -C 6 -alkylsulfonyl-C 1 -C 4 -alkyl, C 1 -C 6 -alkylsulfonylamino, Ci-C 6 - alkylsulfonylamino-Ci-C4-alkyl, Ci-C6-alkylsulfonyl (Ci-C6-alkylamino) -C-C4-alkyl: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfony
  • Fluorobutylsulfonyl 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromo-pentylsulfonyl, 5-iodo-pentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl and tridecafluorohexylsulfonyl;
  • C 1 -C 6 -alkoxy and also the alkoxy parts of hydroxycarbonyl-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkoxy, N- (C 1 -C 6 -alkoxy) -N- (C 1 -C 6 -alkyl) aminocarbonyl,
  • 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-1-methylpropoxy and 1-ethyl-2-methylpropoxy;
  • Ci-C4-haloalkoxy a Ci-C4-alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, thus e.g. Fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro 2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-
  • Ethylpropoxycarbonyl hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1, 2-dimethylbutoxycarbonyl, 1, 3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,
  • C 1 -C 4 -alkylthio as mentioned above, and also, for example, pentylthio, 1-methylbutylthio, 2 Methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, 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-
  • Di (C 1 -C 6 -alkyl) aminothiocarbonyl for example N, N-dimethylaminothiocarbonyl, N 1 N-
  • three- to six-membered heterocyclyl monocyclic, saturated or partially unsaturated hydrocarbons having three to six ring members as mentioned above which, in addition to carbon atoms, have one to four nitrogen atoms, or one to three nitrogen atoms and one oxygen or sulfur atom, or one to three oxygen atoms, or may contain one to three sulfur atoms, and which may be linked via a C atom or an N atom, eg
  • Monocycles such as furyl (eg 2-furyl, 3-furyl), thienyl (eg 2-thienyl, 3-thienyl), pyrrolyl (eg pyrrol-2-yl, pyrrol-3-yl), pyrazolyl (eg pyrazol-3-yl , Pyrazol-4-yl), isoxazolyl (eg isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (eg isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl ), Imidazolyl (eg imidazol-2-yl, imidazol-4-yl), oxazolyl (eg oxazol-2-yl, oxazol-4-yl, oxazol-5-yl), thiazolyl (eg thiazol-2-yl, thi
  • pyridyl eg pyridin-2-yl, pyridin-3-yl, pyridine
  • 4-yl pyrazinyl
  • pyrimidinyl eg pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl
  • pyrazine-2-yl Triazinyl (eg, 1, 3,5-triazin-2-yl, 1, 2,4-triazin-3-yl, 1, 2,4-triazin-5-yl, 1, 2,4-triazine-6 yl), tetrazinyl (eg 1, 2,4,5-tetrazine-3-yl); such as
  • Bicyclic compounds such as the benzanellated derivatives of the aforementioned monocycles, e.g. Quinolinyl, isoquinolinyl, indolyl, benzthienyl, benzofuranyl, benzoxazolyl, benzothiazolyl, benzisothiazolyl, benzimidazolyl, benzopyrazolyl, benzthiadiazolyl, benzotriazole IyI.
  • 5- or 6-membered heteroaryl having one to four nitrogen atoms, or one to three nitrogen atoms and one oxygen or sulfur atom, or with an oxygen or sulfur atom: e.g. C-atom linked aromatic 5-membered heterocycles which may contain, besides carbon atoms, one to four nitrogen atoms, or one to three nitrogen atoms and one sulfur or oxygen atom, or a sulfur or oxygen atom as ring members, e.g.
  • Oxadiazol-3-yl 1, 2,4-oxadiazol-5-yl, 1, 2,4-thiadiazol-3-yl, 1, 2,4-thiadiazol-5-yl, 1, 2,4-triazole 3-yl, 1, 3,4-oxadiazol-2-yl, 1, 3,4-thiadiazol-2-yl and 1, 3,4-triazol-2-yl;
  • the variables of the heteroaroyl-substituted alanines of the formula I have the following meanings, these being considered singly and in combination with one another in particular embodiments of the compounds of the formula I:
  • heteroaroyl-substituted alanines of the formula I in which A is 5-membered heteroaryl having one to four nitrogen atoms, or one to three nitrogen atoms and one oxygen or sulfur atom, or having one oxygen or sulfur atom; particularly preferably 5-membered heteroaryl selected from the group of thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl; especially preferred 5-membered heteroaryl selected from the group thienyl, furyl, pyrazolyl and imidazolyl; wherein said heteroaryl radicals are substituted by a Ci-C ⁇ -haloalkyl radical, preferably in the 2-position by a Ci-C ⁇ -haloalkyl radical, and 1 to 3 radicals from the group halogen, cyano, Ci-C ⁇ -alkyl, C3 - Can carry C ⁇ -cycloalkyl, Ci-C ⁇ -alkoxy, Ci-C ⁇ -hal
  • heteroaroyl-substituted alanines of the formula I in which A 5-membered heteroaryl having one to four nitrogen atoms, or one to three nitrogen atoms and one oxygen or sulfur atom, or with an oxygen or sulfur atom; particularly preferably 5-membered heteroaryl selected from the group of thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl; especially preferred 5-membered heteroaryl selected from the group thienyl, furyl, pyrazolyl and imidazolyl; where the said heteroaryl radicals can be partially or completely halogenated and / or 1 to 3 radicals from the group cyano, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 8 -cycloalkyl Halogenoalkoxy and
  • heteroaroyl-substituted alanines of the formula I in which A is 5-membered heteroaryl having one to four nitrogen atoms, or one to three nitrogen atoms and one oxygen or sulfur atom, or having one oxygen atom; particularly preferably 5-membered heteroaryl selected from the group furyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl; especially preferred 5-membered heteroaryl selected from the group furyl, pyrazolyl and imidazolyl; where the heteroaryl radicals mentioned can be partially or completely halogenated and / or 1 to 3 radicals from the group consisting of cyano, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 8 -cycloalkyl, Haloalkoxy and
  • Ci-C6-alkoxy-Ci-C4-alkyl can carry; means.
  • heteroaroyl-substituted alanines of the formula I in which A is 6-membered heteroaryl having one to four nitrogen atoms; particularly preferably pyridyl or pyrimidyl. especially preferred pyrimidyl; where the said heteroaryl radicals can be partially or completely halogenated and / or 1 to 3 radicals from the group cyano, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 8 -cycloalkyl Haloalkoxy and
  • Ci-C6-alkoxy-Ci-C4-alkyl can carry; means.
  • heteroaroyl-substituted alanines of the formula I in which A is 5- or 6-membered heteroaryl having one to four nitrogen atoms, or having one to three nitrogen atoms and one oxygen or sulfur atom, or an oxygen or sulfur atom which is replaced by a Ci-C ⁇ -haloalkyl radical, preferably in the 2-position by a Ci-C ⁇ -haloalkyl radical, is substituted, and 1 to 3 radicals from the group cyano, Ci-C ⁇ -alkyl, C3-C6-cycloalkyl, ci C 8 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy and C 1 -C 6
  • heteroaroyl-substituted alanines of the formula I in which A is 5- or 6-membered heteroaryl selected from the group consisting of pyrrolyl, thienyl,
  • heteroaryl radicals mentioned can be partially or completely halogenated and / or 1 to 3 radicals from the group consisting of C 1 -C 6 -alkyl, C 3 -C 6 -alkyl radicals and
  • cycloalkyl and Ci-C ⁇ -haloalkyl May carry cycloalkyl and Ci-C ⁇ -haloalkyl; particularly preferably 5-membered heteroaryl selected from the group of thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl; where said heteroaryl radicals may be partially halogenated and / or may carry from 1 to 2 radicals selected from the group consisting of C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl;
  • heteroaryl radicals may be partially halogenated and / or may carry from 1 to 2 radicals from the group consisting of C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl.
  • heteroaroyl-substituted alanines of the formula I in which A is 5- or 6-membered heteroaryl selected from the group consisting of pyrrolyl, furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, tetrazolyl, pyridyl and pyrimidinyl; where the said heteroaryl radicals can be partially or completely halogenated and / or 1 to 3 radicals from the group cyano, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 8 -cycloalkyl Haloalkoxy and can carry;
  • heteroaryl radicals mentioned can be partially or completely halogenated and / or 1 to 3 radicals from the group consisting of C 1 -C 6 -alkyl, C 3 -C 6 -alkyl radicals and
  • heteroaryl selected from the group furyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl; wherein said heteroaryl may be partially halogenated and / or may carry from 1 to 2 radicals selected from the group consisting of C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl;
  • heteroaryl radicals may be partially halogenated and / or may carry from 1 to 2 radicals selected from the group consisting of C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl; means.
  • heteroaroyl-substituted alanines of the formula I in which C-linked 5- or 6-membered heteroaryl selected from the group A1 to A14 with
  • R 9 is hydrogen, halogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; particularly preferably hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; particularly preferably hydrogen or C 1 -C 4 -alkyl; most preferably hydrogen;
  • R 10 is halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -haloalkoxy; particularly preferably halogen, C 1 -C 4 -alkyl or C 1 -C 6 -haloalkyl; particularly preferably halogen or Ci-C ⁇ -haloalkyl; very preferably Ci-C ⁇ -haloalkyl; extremely preferably C 1 -C 4 -haloalkyl very particularly preferably CF 3;
  • R 11 is hydrogen, halogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; particularly preferably hydrogen, halogen or C 1 -C 4 -haloalkyl; especially preferably hydrogen or halogen; most preferably hydrogen; and
  • R 12 is hydrogen, C -C alkyl 6 -alkyl, C 3 -C 6 cycloalkyl, Ci-C 6 haloalkyl or C
  • C 6 alkoxy-C 1 -C 4 -alkyl particularly preferably C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; particularly preferably C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; extremely preferably C 1 -C 4 -alkyl; very preferably CH3;
  • R 9 to R 12 are defined as mentioned above;
  • heteroaroyl-substituted alanines of the formula I in which
  • R 1 is hydrogen
  • R 2 is hydrogen or hydroxy; particularly preferably hydrogen; mean.
  • heteroaroyl-substituted alanines of the formula I in which
  • R 3 is C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; particularly preferably C 1 -C 6 -alkyl; especially preferably C 1 -C 4 -alkyl; most preferably CH 3; means.
  • R 4 is hydrogen or C 1 -C 4 -alkyl; preferably hydrogen or CH3; especially preferably hydrogen; means.
  • C 2 -C 6 -Hydroxyalkinyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, 3- to 6-membered heterocyclyl, wherein said precede said cycloalkyl, cycloalkenyl or 3- to 6-membered heterocyclyl radicals may be partially or fully halogenated and / or one to three radicals from the group consisting of oxo, cyano, nitro, CrC 6 -
  • Ci-C 6 haloalkyl hydroxy, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, hydroxycarbonyl-Ci-C 6 alkoxy, Ci-C 6 alkoxycarbonyl Ci-C 6 alkoxy, amino, Ci-C6 alkylamino, di (-C 6 - alkyl) amino, Ci-C 6 alkylsulfonylamino, Ci-C ⁇ -haloalkylsulfonylamino, aminocarbonylamino, (CrC 6 alkylamino) carbonylamino, di ( C 1 -C 6 alkyl) aminocarbonylamino, aryl and aryl (C 1 -C 6 alkyl); Ci-C 6 alkoxy-Ci-C 4 alkyl, C 2 -C 6 alkenyloxy-CrC 4 alkyl, C 2 -C 6 alkyl
  • C -C alkyl are also preferred 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 kinyl -alkyl, Ci-C 6 haloalkyl, C 2 - C ⁇ haloalkenyl, C 2 -C 6 haloalkynyl, Ci-C ⁇ -cyanoalkyl, Ci-C ⁇ -hydroxyalkyl, C 2 -C 6 hydroxyalkenyl, C 2 -C 6 hydroxyalkynyl, C3-C6-cycloalkyl, C3-C6 Cycloalkenyl, 3- to 6-membered heterocyclyl, wherein the above-mentioned cycloalkyl, cycloalkenyl or 3- to 6-membered heterocyclyl radicals may be partially or completely halogenated and / or one to three radicals from the group oxo,
  • Phenyl-Ci-C4-alkyl phenyl-C 2 -C 4 -alkenyl, phenyl-C 2 -C 4 -alkynyl, phenyl-Ci-C 4 - haloalkyl, phenyl-C 2 -C 4 haloalkenyl, phenyl-C -C 4 -hydroxyalkyl, phenyl-C 1 -C 4 -alkyl, phenylthio-C 1 -C 4 -alkyl, phenylsulfinyl-C 1 -C 4 -alkyl, phenylsulfonyl-C 1 -C 4 -alkyl; Heteroaryl, heteroaryl-C 1 -C 4 -alkyl, heteroaryl-C 1 -C 4 -hydroxyalkyl, heteroaryloxy
  • C 1 -C 6 -alkyl particularly preferably hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy-Ci -C 4 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 4 -alkyl, hydroxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 6 -
  • C 1 -C 6 -alkyl particularly preferably hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 1 -C 6 -hydroxyalkyl, hydroxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 4 -alkyl, [di (C 1 -C 6 -alkyl) aminocarbonyl-oxy] C 1 -C 4 -alkyl, formylamino-C 1 -C 4 -alkyl;
  • Ci-C 6 alkyl extraordinarily preferably hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, -C 6 -
  • Haloalkyl C 2 -C 6 -haloalkenyl, C 1 -C 6 -hydroxyalkyl, formylamino-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyl or phenyl-C 1 -C 4 -hydroxyalkyl; means.
  • C -C alkyl are also preferred 6 -alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 -alkyl kinyl , C 3 -C 6 - haloalkenyl, C 3 -C 6 -haloalkynyl, formyl, Ci-C 6 alkylcarbonyl, C 3 -C 6 - cycloalkylcarbonyl, C2-C6 alkenylcarbonyl, C2-C6 alkynylcarbonyl, CrC 6 - alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 -alkynyloxycarbonyl, -C 6 - alkylaminocarbonyl, Cs-Ce-alkenylaminocarbonyl, Cs-Ce-alkenylaminocarbonyl, Cs-Ce-alkenylaminocarbony
  • Ci-Ce-alkylsulphonylaminocarbonyl di (Ci-C 6 alkyl) aminocarbonyl, N- (C 3 -C 6 - alkenyl) -N- (Ci-C 6 alkyl) aminocarbonyl, N- (C 3 -C 6 alkynyl) -N- (Ci-C 6 alkyl) - aminocarbonyl, N- (Ci-C 6 alkoxy) -N- (Ci-C 6 -alkyl) -amino-carbonyl, N- (C 3 -C 6 - Alkenyl) -N- (C 1 -C 6 -alkoxy) -aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (C 1 -C 6 -alkoxy) -aminocarbonyl, di (C 1 -C 6 -alkyl) aminothiocarbonyl, (C 1 -
  • C 1 -C 6 -alkyl particularly preferably hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, formyl, C 1 -C 6 -alkyl-carbonyl, Ci-C ⁇ -alkoxycarbonyl, di (Ci-Ce-alkylJ-amino-carbonyl, N- (Ci-C6-alkoxy) -N- (Ci-C6-alkyl) -aminocarbonyl,
  • the heteroaroyl-substituted alanines of the formula I in which R 6 is hydrogen, Ci-C are also preferred 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 kinyl -alkyl, formyl, -C 6 - alkylcarbonyl, Ca -C ⁇ -alkenylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylaminocarbonyl, di- (C 1 -C 6 -alkyl) aminocarbonyl, N- (C 1 -C 6 -alkoxy) -N- (C 1 -C 6 -alkyl) aminocarbonyl, di- (C 1 -C 6 -alkyl) aminothiocarbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, where the alky
  • heteroaroyl-substituted alanines of the formula I in which R 8 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or phenyl, where the phenyl radical may be partially halogenated and / or represented by C 1 -C 4 -alkyl.
  • Alkyl may be substituted; particularly preferably C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or phenyl; especially preferably methyl, trifluoromethyl or phenyl. means.
  • heteroaroyl-substituted alanines of the formula I in which A is 5- or 6-membered heteroaryl selected from the group consisting of thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl and pyridyl; wherein said heteroaryl may be partially or completely halogenated and / or 1 to 3 radicals from the group Ci-C ⁇ -alkyl, C3-C6-cycloalkyl and Ci-C ⁇ -haloalkyl may carry; R 1 and R 2 are hydrogen; R 3 is C 1 -C 4 -alkyl, particularly preferably CH 3; R 4 is hydrogen;
  • R 5 is hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, Ci-C 6 haloalkyl, C 2 -C 6 - haloalkenyl, Ci-C 6 hydroxyalkyl, hydroxycarbonyl-d ⁇ alkyl, phenyl C 1 -C 4 -alkyl or phenyl-C 1 -C 4 -hydroxyalkyl;
  • R 6 is hydrogen, formyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylaminocarbonyl, di (C 1 -C 4 -alkyl) aminocarbonyl, phenylaminocarbonyl, N- (C 1 -C 4 -alkyl) -N- (phenyl) -aminocarbonyl, SO 2 CH 3 , SO 2 CF 3 or SO 2 (C 6 H 5 ); and R 7 is hydrogen.
  • benzoyl-substituted alanines of the formula I are obtainable in various ways, for example by the following processes:
  • Alanine derivatives of the formula V are first reacted with heteroaryl acid (derivatives) of the formula IV to give corresponding heteroaroyl derivatives of the formula III, which subsequently react with amines of the formula II to give the desired heteroaroyl-substituted alanines of the formula I:
  • L 1 is a nucleophilically displaceable leaving group, for example for hydroxy or C 1 -C 6 -alkoxy.
  • L 2 represents a nucleophilic displaceable leaving group, for example for hydroxy, halogen, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 4 -alkyl, onyl, phosphoryl or iso-ureyl.
  • heteroaroyl derivatives of the formula IM is carried out in the presence of an activating reagent and a base usually at temperatures of 0 0 C to the boiling point of the reaction mixture, preferably O 0 C to 11 O 0 C, particularly preferably at room temperature, in an inert organic solvent [cf. KC Nicolaou et al., J. of the Am. Chem. Soc. (2005), 127 (31), 1176-1 1 183; Shu-Sin Chng et al., Tetrahedron Lett.
  • Suitable activating reagents are condensing agents, e.g. polystyrene-bonded dicyclohexylcarbodiimide, diisopropylcarbodiimide, carbonyldiimidazole, chlorocarbonic acid esters such as methyl chloroformate, ethyl chloroformate, isoropyl chloroformate, isobutyl chloroformate, sec-butyl chloroformate or allyl chloroformate, pivaloyl chloride, polyphosphoric acid, propanephosphonic anhydride, bis (2-oxo-3-oxazolidinyl) phosphoryl chloride (BOPCI) or Sulfonyl chlorides such as methanesulfonyl chloride, toluenesulfonyl chloride or benzenesulfonyl chloride.
  • condensing agents e.g. polystyrene-bonded dicyclohexylcarbodiimi
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as benzene, toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether , Diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide, dimethylformamide (DMF), dimethylacetamide (DMA) and N Methylpyrroli
  • Bases generally include inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, Alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate and alkali metal bicarbonates such as sodium bicarbonate, as well as organic bases, eg tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, N-
  • the bases are generally used in equimolar amounts. But they can also be used in excess or optionally as a solvent.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use IV in an excess relative to V.
  • reaction mixtures are worked up in the usual way, e.g. by mixing with water, separation of the phases and optionally chromatographic purification of the crude products.
  • the intermediate and end products fall z. T. in the form of viscous oils, which are freed or purified under reduced pressure and at moderately elevated temperature of volatile fractions. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.
  • the reaction of the alanine derivatives of the formula V with heteroaryl acid (derivatives) n of the formula IV in which L 2 is halogen, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 4 -alkylsulfonyl, phosphoryl or isoureyl, to give heteroaroyl derivatives of the formula IM is carried out in the presence of a base, usually at temperatures from 0 ° C. to the boiling point of the reaction mixture, preferably from 0 ° C. to 100 ° C., more preferably at room temperature in an inert organic solvent [cf. KC Nicolaou et al., J. of the Am.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as benzene, toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether , Diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and also dimethyl sulfoxide, dimethylformamide (DMF), dimethylacetamide ( DMA) and N-
  • Methylpyrrolidone (NMP) or in water particularly preferred are methylene chloride, THF and water. It is also possible to use mixtures of the solvents mentioned.
  • Bases generally include inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, Alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate and alkali metal bicarbonates such as sodium bicarbonate, as well as organic bases, eg tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, N-
  • Particularly preferred are sodium hydroxide, triethylamine and pyridine.
  • the bases are generally used in equimolar amounts. But they can also be used in excess or optionally as a solvent.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use IV in an excess relative to V.
  • the workup and isolation of the products can be done in a conventional manner.
  • the alanine derivatives of the formula V can first be reacted with amines of the formula II to give the corresponding amides, which then react with heteroaryl acid (derivatives) n of the formula IV to give the desired heteroaroyl-substituted alanines of the formula I.
  • alanine derivatives of the formula V required for the preparation of the heteroaroyl derivatives of the formula III are known in the literature, even in enantiomerically and diastereomerically pure form, or can be prepared according to the cited literature :
  • heteroaryl acid (derivatives) of the formula IV required for the preparation of the heteroaroyl derivatives of the formula III can be purchased or can be prepared analogously to the procedure known from the literature [eg Chang-Ling Liu et al., J. of Fluorine Chem. (2004) , 125 (9), 1287-1290; Manfred Schlosser et al., Europ. J. of Org. Chem. (2002), (17), 2913-2920; Hoh-Gyu Hahn et al., Agricult. Chem. And Biotech. (English Edition) (2002), 45 (1), 37-42; Jonatan O Smith et al., J. of Fluorine Chem. (1997), Vol.
  • Suitable activating reagents are condensing agents, e.g. polystyrene-bonded dicyclohexylcarbodiimide, diisopropylcarbodiimide, carbonyldiimidazole, chlorocarbonic acid esters such as methyl chloroformate, ethyl chloroformate, isoropyl chloroformate, isobutyl chloroformate, sec-butyl chloroformate or allyl chloroformate, pivaloyl chloride, polyphosphoric acid,
  • Propanephosphonic anhydride bis (2-oxo-3-oxazolidinyl) phosphoryl chloride (BOPCI) or sulfonyl chlorides such as methanesulfonyl chloride, toluenesulfonyl chloride or benzenesulfonyl chloride.
  • BOPCI bis (2-oxo-3-oxazolidinyl) phosphoryl chloride
  • sulfonyl chlorides such as methanesulfonyl chloride, toluenesulfonyl chloride or benzenesulfonyl chloride.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as benzene, toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether , Diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and
  • Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and Calcium hydride, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate and alkali metal bicarbonates such as sodium bicarbonate, as well as organic bases, for example tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, N-methylmorpholine, and N-methylpiperidine, pyridine, substituted pyridines such as collidine Lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Especially Preference is given to sodium hydroxide, trieth
  • the bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as solvent.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use II in an excess relative to IM.
  • the workup and isolation of the products can be done in a conventional manner.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as benzene, toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether , Diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n- Butanol and
  • the reaction may optionally be carried out in the presence of a base.
  • bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate, and alkali metal hydrogen carbonate in addition, organic bases, for example tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, N-methylmorpholine, and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Particularly preferred
  • the bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as solvent.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use Il in an excess relative to IM.
  • the workup and isolation of the products can be done in a conventional manner.
  • the amines of the formula II required for the preparation of the heteroaroyl-substituted alanines of the formula I can be purchased.
  • R x is R 6 or a removable protecting group such as C 1 -C 6 -alkyloxycarbonyl (eg tert-butyloxycarbonyl), C 1 -C 6 -alkylsulfinyl (eg tert-butylsulfinyl) or optionally C 1 -C 6 -alkyl-substituted arylsulfinyl ( eg toluylsulfinyl).
  • C 1 -C 6 -alkyloxycarbonyl eg tert-butyloxycarbonyl
  • C 1 -C 6 -alkylsulfinyl eg tert-butylsulfinyl
  • optionally C 1 -C 6 -alkyl-substituted arylsulfinyl eg toluylsulfinyl.
  • L 1 is a nucleophilically displaceable leaving group, for example for hydroxy or C 1 -C 6 -alkoxy.
  • L 2 is a nucleophilically displaceable leaving group, for example hydroxy, halogen, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 4 -alkyl, onyl, phosphoryl or iso-ureyl.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and Tetrahydrofuran, as well as dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably diethyl ether, dioxane and tetrahydrofuran. It is also possible to use mixtures of the solvents mentioned.
  • Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium isopropylamide and lithium hexamethyldisilazide, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, and alkali metal and alkaline earth metal alkoxides such as sodium methoxide, sodium ethanolate, Potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and Dimethoxymagnesium, also organic bases, eg tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bi
  • the bases are generally used in equimolar amounts, but they can also be used catalytically, in excess or optionally as a solvent.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use the base and / or the imino compounds VII in an excess based on the glycine derivatives VIII.
  • the workup and isolation of the products can be done in a conventional manner.
  • L 1 is a nucleophilically displaceable leaving group, for example for hydroxy or C 1 -C 6 -alkoxy.
  • L 3 is a nucleophilically displaceable leaving group, for example halogen, hydroxy, or C 1 -C 6 -alkoxy.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether , tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propinonitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert. Butanol
  • Bases generally include inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, Alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate and also alkali metal hydrogencarbonates such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and also alkali metal and earth metal halides.
  • alkali metal and alkaline earth metal hydroxides such as lithium hydro
  • potassium alcoholates such as sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butanolate, potassium tert-pentoxide and dimethoxy magnesium
  • organic bases for example tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic Amines into consideration.
  • tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine
  • pyridine substituted pyridines
  • collidine lutidine and 4-dimethylaminopyridine and bicyclic Amines into consideration.
  • Particular preference is given to sodium hydroxide, sodium hydride and triethylamine.
  • the bases are generally used in equimolar amounts, but they can also be used catalytically, in excess or optionally as a solvent.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use the base and / or IX in an excess based on IM or I.
  • the workup and isolation of the products can be done in a conventional manner.
  • L 1 is a nucleophilically displaceable leaving group, for example hydroxy or C 1 -C 6 -alkoxy.
  • L 4 represents a nucleophilically displaceable leaving group, for example halogen, such as chlorine or bromine.
  • the reaction of the nitro compound XI with the glycine derivative XM is usually carried out at a temperature of -100 ° C to the boiling point of the reaction mixture, preferably at -80 ° C to 20 ° C, in an inert organic solvent in the presence of a base ( See Vicky A. Burgess et al., Aust. J. of Chem. (1988), 41 (7), 1063-1070).
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether , tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propinonitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert. Butanol
  • Bases generally include inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, Alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate and also alkali metal hydrogencarbonates such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and also alkali metal and earth metal halides.
  • alkali metal and alkaline earth metal hydroxides such as lithium hydro
  • potassium metal alcoholates such as sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert. Butanolate, potassium tertiary pentoxide and dimethoxy magnesium, as well as organic bases, e.g. tertiary amines such as trimethylamine, triethylamine, Diisopropylethy- lamin and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Particularly preferred are sodium hydroxide, sodium hydride and triethylamine.
  • the bases are generally used in equimolar amounts, but they can also be used catalytically, in excess or optionally as a solvent.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use the base and / or XI in an excess based on XII.
  • the workup and isolation of the products can be done in a conventional manner.
  • the required nitro compound of the formula XI can be purchased.
  • the required glycine derivatives of the formula XII can be obtained analogously to methods known from the literature (compare Vicky A. Burgess et al., Aust. J. of Chem. (1988), 41 (7), 1063-1070).
  • the reduction of the nitroaniline derivatives of the formula X is usually carried out at a temperature of -100 ° C to the boiling point of the reaction mixture, preferably -80 ° C to 20 ° C, in an inert organic solvent with a reducing agent, (see Vicky A. Burgess et al., Aust. J. of Chem. (1988), 41 (7), 1063-1070).
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether , tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol,
  • Suitable reducing agents are transition metal catalysts (e.g., Pd / C or Raney Ni) in combination with hydrogen.
  • the workup and isolation of the product can be carried out in a conventional manner.
  • A, R 1 and R 4 , R 5 , R 6 and R 7 have the meanings given above and L 1 is a nucleophilically displaceable leaving group, for example hydroxy or C 1 -C 6 alkoxy, are also an object of the present invention.
  • L 1 is a nucleophilically displaceable leaving group, for example hydroxy or C 1 -C 6 alkoxy.
  • the particularly preferred embodiments of the intermediates with respect to the variables correspond to those of the radicals A, R 1 and R 4 to R 7 of the formula I.
  • heteroaroyl derivatives of the formula III in which A is 5- or 6-membered heteroaryl selected from the group consisting of thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl and pyridyl; wherein said heteroaryl may be partially or fully halogenated and / or 1 to 3 radicals from the group Ci-C ⁇ -alkyl, C3-C6-cycloalkyl, and carry Ci-C ⁇ -haloalkyl; R 1 is hydrogen; R 4 is hydrogen; R 5 is hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, Ci-C 6 haloalkyl, C 2 -C 6 -
  • Haloalkenyl C 1 -C 6 -hydroxyalkyl, hydroxycarbonyl-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyl or phenyl-C 1 -C 4 -hydroxyalkyl;
  • R 6 is hydrogen, formyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylaminocarbonyl, di (C 1 -C 4 -alkyl) aminocarbonyl, phenylaminocarbonyl, N- (C 1 -C 4 -alkyl) -N- (phenyl) -aminocarbonyl, SO 2 CH 31 SO 2 CF 3 or SO 2 (C 6 H 5 ); and
  • R 7 is hydrogen; mean.
  • the heteroaroyl-substituted alanines of the formula I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of pure isomers - as herbicides.
  • the compounds of the formula I containing herbicidal agents control plant growth on non-crop areas very well, especially at high application rates. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crops. This effect occurs especially at low application rates.
  • the compounds of the formula I or herbicidal compositions containing them can be used in a further number of crop plants for the removal of unwanted plants.
  • the following cultures may be considered:
  • the compounds of formula I may also be used in cultures tolerant to the action of herbicides by breeding, including genetic engineering.
  • the compounds of formula I can also be used in cultures tolerant by breeding including genetic engineering against insect or fungal attack.
  • the compounds of the formula I or the herbicidal compositions containing them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, even high-percentage aqueous, oily or other suspensions or dispersants.
  • the forms of application depend on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • the herbicidal compositions contain a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries customary for the formulation of crop protection agents.
  • Suitable inert auxiliaries are essentially:
  • Mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, 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 and cyclohexanol, ketones such as cyclohexanone, strong polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
  • Paraffins etrahydronaphthalene
  • alkylated naphthalenes and their derivatives alkylated benzenes and their derivatives
  • alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol
  • ketones such as cyclohexanone
  • Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding
  • Water to be prepared Water to be prepared.
  • the substrates as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers.
  • wetting agents wetting, adhesion, dispersing or emulsifying agent and possibly solvent or oil, which are suitable for dilution with water.
  • surfactants are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethyl noctylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphen
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules for example coated, impregnated and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are mineral soils such as silicic acids, 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, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral soils such as silicic acids, 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, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour
  • the concentrations of the compounds of the formula I in the ready-to-use formulations can be varied within wide limits.
  • the formulations contain from about 0.001 to 98 wt .-%, preferably 0.01 to 95 wt .-%, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • an active compound of the formula I 20 parts by weight of an active compound of the formula I are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalenesulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill.
  • the mixture By finely distributing the mixture in 20,000 parts by weight of water to obtain a spray mixture containing 0.1 wt .-% of the active ingredient of the formula I.
  • the application of the compounds of the formula I or of the herbicidal compositions can be carried out in the preemergence or postemergence process. If the active ingredients are less compatible with certain crops, application techniques may be used in which the herbicidal agents are sprayed with the help of the sprayers so as not to hit the leaves of the sensitive crops as far as possible, while the active ingredients on the leaves below grow undesirable plants or the uncovered soil surface (post-directed, lay-by).
  • the application rates of compound of the formula I are 0.001 to 3.0, preferably 0.01 to 1.0, kg / ha of active substance (see above).
  • the heteroaroyl-substituted alanines of the formula I can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups and applied together.
  • the culture vessels used were plastic flower pots with loamy sand with about 3.0% humus as the substrate.
  • the seeds of the test plants were sown separately by species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing by means of finely distributing nozzles.
  • the jars were lightly rained to promote germination and growth and then covered with clear plastic hoods until the plants had grown. This cover causes a uniform germination of the test plants, if it was not affected by the active ingredients.
  • the test plants were grown depending on the growth form only to a stature height of 3 to 15 cm and only then treated with the suspended or emulsified in water agents.
  • 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.
  • the application rate for postemergence treatment was 1.0 kg / ha aS (active substance).
  • the plants were kept species-specific at temperatures of 10 to 25 0 C and 20 to 35 0 C.
  • the trial period lasted for 2 to 4 weeks. During this time, the plants were cared for, and their response to each treatment was evaluated.
  • the rating was based on a scale of 0 to 100. 100 means no emergence of the plants or complete destruction of at least the above-ground parts and 0 no damage or normal growth course.
  • the plants used in the greenhouse experiments were composed of the following species:

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Abstract

The present invention relates to heteroaroyl-substituted alanines of the formula I in which the variables A and R1 to R7 have the meanings stated in the description, and to their agriculturally usable salts, methods and intermediates for their preparation, and the use of these compounds or compositions comprising these compounds for controlling unwanted plants.

Description

Heteroaroylsubstituierte AlanineHeteroaroyl-substituted alanines
Beschreibungdescription
Die vorliegende Alanine der Formel IThe present alanines of the formula I
in der die Variablen die folgenden Bedeutungen haben: in which the variables have the following meanings:
A 5- oder 6-gliedriges Heteroaryl mit ein bis vier Stickstoffatomen, oder mit ein bis drei Stickstoffatomen und einem Sauerstoff- oder Schwefelatom, oder mit einemA 5- or 6-membered heteroaryl having one to four nitrogen atoms, or having one to three nitrogen atoms and one oxygen or sulfur atom, or with a
Sauerstoff- oder Schwefelatom, welches partiell oder vollständig halogeniert sein kann und/oder 1 bis 3 Reste aus der Gruppe Cyano, CrC6-Alkyl, C3-C6- Cycloalkyl, CrC6-Halogenalkyl, CrC6-Alkoxy, CrC6-Halogenalkoxy und CrC6- Alkoxy-Ci-C4-alkyl tragen kann;Oxygen or sulfur atom, which may be partially or fully halogenated and / or 1 to 3 radicals from the group cyano, -C 6 alkyl, C 3 -C 6 cycloalkyl, -C 6 -haloalkyl, -C 6 alkoxy, -C 6 haloalkoxy, and CrC can carry 6 -alkoxy-Ci-C4-alkyl;
R1, R2 Wasserstoff, Hydroxy oder Ci-C6-Alkoxy;R 1 , R 2 are hydrogen, hydroxy or C 1 -C 6 -alkoxy;
R3 Ci-Ce-Alkyl, Ci-C4-Cyanoalkyl oder Ci-C6-Halogenalkyl;R 3 is C 1 -C 6 -alkyl, C 1 -C 4 -cyanoalkyl or C 1 -C 6 -haloalkyl;
R4 Wasserstoff oder Ci -C6-Al kyl;R 4 is hydrogen or C 1 -C 6 -alkyl;
R5 Wasserstoff, Ci-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Al kinyl, Ci-C6-Halogenalkyl, C2- C6-Halogenalkenyl, C2-C6-Halogenalkinyl, Ci-C6-Cyanoalkyl, C2-C6- Cyanoalkenyl, C2-C6-Cyanoalkinyl, Ci-C6-Hydroxyalkyl, C2-C6-Hydroxyalkenyl, C2-C6-Hydroxyalkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, 3- bis 6-gliedrigesR 5 is hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 kinyl -alkyl, Ci-C 6 haloalkyl, C 2 - C 6 haloalkenyl, C 2 -C 6 haloalkynyl , Ci-C 6 cyanoalkyl, C 2 -C 6 - cyanoalkenyl, C 2 -C 6 -Cyanoalkinyl, Ci-C 6 hydroxyalkyl, C 2 -C 6 -Hydroxyalkenyl, C 2 -C 6 -Hydroxyalkinyl, C3-C 6 cycloalkyl, C3-C6 cycloalkenyl, 3- to 6-membered
Heterocyclyl, wobei die voranstehen genannten Cycloalkyl, Cycloalkenyl oder 3- bis 6- gliedrigen Heterocyclyl reste partiell oder vollständig halogeniert sein können und/oder ein bis drei Reste aus der Gruppe Oxo, Cyano, Nitro, CrC6- Alkyl, Ci-C6-Halogenalkyl, Hydroxy, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy,Heterocyclyl, wherein the abovementioned cycloalkyl, cycloalkenyl or 3- to 6-membered heterocyclyl radicals may be partially or completely halogenated and / or one to three radicals from the group consisting of oxo, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 - haloalkyl, hydroxy, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy,
Hydroxycarbonyl, Ci-C6-Alkoxycarbonyl, Hydroxycarbonyl-Ci-C6-alkoxy, Ci-C6-Alkoxycarbonyl-Ci-C6-alkoxy, Amino, Ci-C6-Alkylamino, Di(CrC6- alkyl)amino, Ci-C6-Alkylsulfonylamino, Ci-Cδ-Halogenalkylsulfonylamino, Aminocarbonylamino, (CrC6-Alkylamino)carbonylamino, Di(CrC6- alkyl)aminocarbonylamino, Aryl und Aryl(CrC6-alkyl) tragen können;Hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, hydroxycarbonyl-Ci-C 6 alkoxy, Ci-C 6 alkoxycarbonyl-alkoxy-Ci-C 6, amino, Ci-C6 alkylamino, di (-C 6 - alkyl) amino, Ci-C 6 alkylsulfonylamino, Ci-Cδ-haloalkylsulfonylamino, aminocarbonylamino, (CrC 6 alkylamino) carbonylamino, di (CrC 6 - alkyl) aminocarbonylamino aryl, and (CrC 6 alkyl) may bear, aryl;
CrC6-Alkoxy-CrC4-alkyl, C2-C6-Alkenyloxy-CrC4-alkyl, C2-C6-Alkinyloxy-CrC4- alkyl, Ci-C6-Halogenalkoxy-CrC4-alkyl, C2-C6-Halogenalkenyloxy-CrC4-alkyl, C2-C6-Halogenalkinyloxy-CrC4-alkyl, CrC6-AIkOXy-CrC4-BIkOXy-CrC4-B I kyl, Cr C6-Alkylthio-Ci-C4-alkyl, C2-C6-Alkenylthio-Ci-C4-alkyl, C2-C6-Alkinylthio-CrC4- alkyl, CrCδ-Halogenalkyl-Ci^-thioalkyl, C^Cδ-Halogenalkenyl-Ci^-thioalkyl, Ca-Ce-Halogenalkinyl-Ci^-thioalkyl, Ci-Ce-Alkylsulfinyl-Ci-CU-alkyl, CrC6- Halogenalkylsulfinyl-Ci-C4-alkyl, Ci-Ce-Alkylsulfonyl-Ci-CU-alkyl, CrC6- Halogenalkylsulfonyl-CrC4-alkyl, Amino-CrC4-alkyl, C 1 -C6-Al ky I am in 0-CrC4- alkyl, Di(Ci-C6-alkyl)amino-CrC4-alkyl, CrCe-Alkylsulfonylamino-Ci^-alkyl, Cr C6-Alkylsulfonyl(Ci-C6-alkyl)amino-CrC4-alkyl, CrC6-Alkylcarbonyl, Hydroxycar- bonyl, CrC6-Alkoxycarbonyl, Aminocarbonyl, CrCe-Alkylaminocarbonyl, Di(Cr C6-alkyl)aminocarbonyl, Formylamino-CrC4-alkyl, CrC6-Alkoxycarbonylamino- CrC4-alkyl, Ci-C6-Alkylcarbonyl-CrC6-alkyl, Hydroxycarbonyl-CrC4-alkyl, CrC6--C 6 alkoxy-CrC 4 alkyl, C 2 -C 6 alkenyloxy-CrC 4 alkyl, C 2 -C 6 alkynyloxy-CrC 4 - alkyl, Ci-C 6 haloalkoxy CRC4 alkyl, C 2 - C 6 haloalkenyloxy CrC 4 alkyl, C 2 -C 6 haloalkynyloxyCroC 4 alkyl, CrC 6 alkoxy CrC 4 -bikoxy CrC 4 -bylyl, Cr C 6 alkylthio-Ci-C 4 alkyl, C 2 -C 6 alkenylthio-Ci-C 4 alkyl, C 2 -C 6 -alkynylthio--C 4 - alkyl, Ci ^ haloalkyl-CrCδ thioalkyl, C ^ Cδ-haloalkenyl-Ci ^ thioalkyl, Ca-Ce-haloalkynyl-Ci ^ thioalkyl, Ci-Ce-alkylsulfinyl-Ci-CU-alkyl, CrC 6 - haloalkylsulfinyl-Ci-C4-alkyl, Ci-Ce-alkylsulfonyl -C-CU-alkyl, CrC 6 - haloalkylsulfonyl -C 4 alkyl, amino-CRC4 alkyl, C 1 -C 6 -alkyl ky I am in 0 -C 4 - alkyl, di (Ci-C 6 alkyl) amino-C 1 -C 4 -alkyl, C 1 -C 6 -alkylsulfonylamino-C 1 -C 4 -alkyl, C 1 -C 6 -alkylsulfonyl (C 1 -C 6 -alkyl) aminoCrC 4 -alkyl, C 1 -C 6 -alkylcarbonyl, hydroxycarbonyl, C 1 -C 6 -alkoxycarbonyl, aminocarbonyl, CRCE-alkylaminocarbonyl, di (Cr C6 alkyl) aminocarbonyl, formylamino-CRC4 alkyl, -C 6 alkoxycarbonylamino -C 4 -alkyl, Ci-C 6 alkylcarbonyl -C 6 alkyl, hydroxycarbonyl--C 4 -alkyl, CrC 6 -
Alkoxycarbonyl-CrC4-alkyl, Ci-C6-Halogenalkoxycarbonyl-CrC4-alkyl, CrC6- Alkylcarbonyloxy-CrC4-alkyl, Aminocarbonyl-CrC4-alkyl, CrC6- Alkylaminocarbonyl-CrC4-alkyl, Di(Ci-C6-alkyl)aminocarbonyl-CrC4-alkyl, CrC6- Alkylcarbonylamino-CrC4-alkyl, Ci-C6-Alkylcarbonyl-(Ci-C6-alkylamino)-CrC4- alkyl, (Ci-C6-Alkyl)aminocarbonyloxy-Ci-C4-alkyl, Di(CrC6- alkyl)aminocarbonyloxy-CrC4-alkyl, [(Ci-C6-Alkyl)amino-carbonylamino]CrC4- alkyl, [Di^rCe-alkylJamino-carbonylaminolCi^-alkyl; Phenyl-CrC4-alkyl, Phenyl-C2-C4-alkenyl, Phenyl-C2-C4-alkinyl, Phenyl-CrC4- halogenalkyl, Phenyl-C2-C4-halogenalkenyl, Phenyl-C2-C4-halogenalkinyl, Phe- nyl-CrC4-hydroxyalkyl, Phenyl-C2-C4-hydroxyalkenyl, Phenyl-C2-C4- hydroxyalkinyl, Phenylcarbonyl-CrC4-alkyl, Phe- nyloxycarbonyl-CrC4-alkyl, Phenyloxy-CrC4-alkyl, Phenylthio-CrC4-alkyl, Phe- nylsulfinyl-CrC4-alkyl, Phenylsulfonyl-CrC4-alkyl,Alkoxycarbonyl-CrC 4 alkyl, Ci-C 6 haloalkoxycarbonyl-CRC4-alkyl, CrC 6 - alkylcarbonyloxy -C 4 -alkyl, aminocarbonyl-CRC4 alkyl, -C 6 - alkylaminocarbonyl CRC4 alkyl, di (Ci-C 6 - alkyl) aminocarbonyl-CRC4 alkyl, -C 6 - alkylcarbonylamino CRC4-alkyl, Ci-C 6 alkylcarbonyl (Ci-C 6 -alkylamino) -CrC4- alkyl, (Ci-C 6 alkyl) amino carbonyloxy-C 4 alkyl, di (CrC 6 - alkyl) aminocarbonyloxy CRC4 alkyl, [(Ci-C 6 alkyl) amino-carbonylamino] CRC4 alkyl, [di ^ RCE alkylJamino-carbonylaminolCi ^ alkyl; Phenyl-CrC 4 -alkyl, phenyl-C 2 -C 4 -alkenyl, phenyl-C 2 -C 4 -alkynyl, phenyl-CrC 4 - haloalkyl, phenyl-C 2 -C 4 -haloalkenyl, phenyl-C 2 -C 4 -haloalkynyl, phenyl-CrC 4 hydroxyalkyl, phenyl-C 2 -C 4 -hydroxyalkenyl, phenyl-C 2 -C 4 - hydroxyalkynyl, phenylcarbonyl--C 4 alkyl, Phe-nyloxycarbonyl -C 4 alkyl, phenyloxy--C 4 alkyl, phenylthio--C 4 alkyl, Phe nylsulfinyl--C 4 -alkyl, phenylsulfonyl--C 4 alkyl,
Heteroaryl, Heteroaryl-CrC4-alkyl, Heteroaryl-C2-C4-alkenyl, Heteroaryl-C2-C4- alkinyl, Heteroaryl-CrC4-halogenalkyl, Heteroaryl-C2-C4-halogenalkenyl, Hetero- aryl-C2-C4-halogenalkinyl, Heteroaryl-CrC4-hydroxyalkyl, Heteroaryl-C2-C4- hydroxyalkenyl, Heteroaryl-C2-C4-hydroxyalkinyl, Heteroarylcarbonyl-CrC4-alkyl, Heteroarylcarbonyloxy-Ci^-alkyl, Heteroaryloxycarbonyl-CrC4-alkyl, Heteroaryl oxy-CrC4-a I ky I, Heteroarylthio-CrC4-alkyl, Heteroarylsulfinyl-CrC4-alkyl, He- teroarylsulfonyl-CrC4-alkyl, wobei die vorstehend genannten Phenyl- und Heteroarylreste partiell oder vollständig halogeniert sein können und/oder ein bis drei Reste aus der Gruppe Cyano, Nitro, CrC6-Alkyl, CrC6-Halogenalkyl, Hydroxy, d-C-6- Hydroxyalkyl, CrC6-Alkoxy, CrC6-Halogenalkoxy, Hydroxycarbonyl, Cr C6-Alkoxycarbonyl, Hydroxycarbonyl-CrC6-alkoxy, CrC6-Alkoxycarbonyl-Heteroaryl, heteroarylCrC 4 -alkyl, heteroaryl-C 2 -C 4 -alkenyl, heteroaryl-C 2 -C 4 -alkynyl, heteroarylCrC 4 -haloalkyl, heteroaryl-C 2 -C 4 -haloalkenyl, heteroaryl C 2 -C 4 haloalkynyl, heteroaryl-CrC 4 hydroxyalkyl, heteroaryl-C 2 -C 4 - hydroxyalkenyl, heteroaryl-C 2 -C 4 -hydroxyalkinyl, heteroarylcarbonyl CRC4 alkyl, heteroarylcarbonyloxy-Ci ^ alkyl, heteroaryloxycarbonyl -C 4 alkyl, heteroaryl-oxy -C 4 -a I ky I, heteroarylthio -C 4 alkyl, heteroarylsulfinyl--C 4 alkyl, He teroarylsulfonyl--C 4 alkyl, wherein the phenyl and heteroaryl radicals mentioned above partially or fully may be halogenated and / or one to three radicals from the group cyano, nitro, -C 6 alkyl, -C 6 haloalkyl, hydroxy, dC 6 - hydroxyalkyl, -C 6 alkoxy, -C 6 -haloalkoxy, hydroxycarbonyl, C 6 Cr Alkoxycarbonyl, hydroxycarbonyl-CrC 6 -alkoxy, CrC 6 -alkoxycarbonyl-
CrC6-alkoxy, Amino, CrC6-Alkylamino, Di(CrC6-alkyl)amino, CrC6-Alkyl- sulfonylamino, CrCe-Halogenalkylsulfonylamino, (CrC6-Alkylamino)- carbonylamino, Di-(CrC6-alkyl)-aminocarbonylamino, Aryl und Aryl(CrC6- alkyl) tragen können;C 1 -C 6 -alkoxy, amino, C 1 -C 6 -alkylamino, di (C 1 -C 6 -alkyl) amino, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -haloalkylsulfonylamino, (C 1 -C 6 -alkylamino) -carbonylamino, di (C 1 -C 6 -alkyl) aminocarbonylamino, aryl and aryl (C 1 -C 6 -alkyl);
Wasserstoff, d-Cβ-Alkyl, C3-C6-Cycloalkyl, C3-C6-Alkenyl, C3-C6-Al kinyl, C3-C6- Halogenalkenyl, C3-C6-Halogenalkinyl, Formyl, CrC6-Alkylcarbonyl, C3-C6- Cycloalkylcarbonyl, C2-C6-Alkenylcarbonyl, C2-C6-Alkinylcarbonyl, CrC6- Alkoxycarbonyl, Cs-CrAlkenyloxycarbonyl, Cs-CrAlkinyloxycarbonyl, Aminocar- bonyl, Ci-Cδ-Alkylaminocarbonyl, Cs-CrAlkenylaminocarbonyl, C3-C6- Alkinylaminocarbonyl, Ci-CrAlkylsulfonylaminocarbonyl, Di(CrCr alkyl)aminocarbonyl, N-(C3-C6-Alkenyl)-N-(CrC6-alkyl)-aminocarbonyl, N-(C3-Ce- Alkinyl)-N-(Ci-C6-alkyl)-aminocarbonyl, N-(Ci-C6-Alkoxy)-N-(Ci-C6-alkyl)-amino- carbonyl, N-(C3-C6-Alkenyl)-N-(CrC6-alkoxy)-aminocarbonyl, N-(C3-C6-Alkinyl)- N-(Ci-C6-alkoxy)-aminocarbonyl, Di(Ci-C6-alkyl)aminothiocarbonyl, (CrCr Alkyl)cyanoimino, (Amino)cyanoimino, [(CrCrAlkylJaminolcyanoimino, Di(CrCr alkyl)aminocyanoimino, Ci-C6-Alkylcarbonyl-Ci-C6-alkyl, CrC6-Alkoxyimino-Cr Ce-alkyl, N-(Ci-C6-Alkylamino)-imino-Ci-C6-alkyl, N-[Di(Ci-C6-alkyl)amino]imino- d-Cβ-alkyl oder Tιϊ-Ci-C4-alkylsilyl, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Hydroxy, C3-C6-Cycloalkyl, CrCδ-Alkoxy- Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-Alkoxy, CrC4-Is hydrogen, d-Cβ-alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 kinyl -alkyl, C 3 -C 6 - haloalkenyl, C 3 -C 6 haloalkynyl, formyl , C 1 -C 6 -alkylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 2 -C 6 -alkynylcarbonyl, C 1 -C 6 - Alkoxycarbonyl, Cs-Cℓ-alkenyloxycarbonyl, Cs-C-alkynyloxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, C 6 -C 8 -alkenylaminocarbonyl, C 3 -C 6 -alkynylaminocarbonyl, C 1 -C 4 -alkylsulfonylaminocarbonyl, di (C 1 -C 6 -alkyl) aminocarbonyl, N- (C 3 -C 6 -alkenyl) -N- (C 1 -C 6 -alkyl) -aminocarbonyl, N- (C 3 -CE -alkynyl) -N- (C 1 -C 6 -alkyl) -aminocarbonyl, N- (C 1 -C 6 -alkoxy) -N- (C 1 -C 6 -alkyl) -aminocarbonyl, N- (C 3 -C 6 -alkenyl) -N- (C 1 -C 6 -alkoxy) -aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (C 1 -C 6 -alkoxy) - aminocarbonyl, di (C 1 -C 6 -alkyl) aminothiocarbonyl, (C 1 -C 8 -alkyl) cyanoimino, (amino) cyanoimino, [(C 1 -C 6 -alkyl) amino cyanoimino, di (C 1 -C 6 -alkyl) amino cyanoimino, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxyimino C 1 -C 6 -alkyl, N- (C 1 -C 6 -alkylamino) -imino-C 1 -C 6 -alkyl, N- [di (C 1 -C 6 -alkyl) amino] imino-C 1 -C 6 -alkyl or T 1 -C 4 -C 4 alkylsilyl, wherein said alkyl, cycloalkyl and alkoxy radicals may be partially or completely halogenated and / or may carry one to three of the following groups: cyano, hydroxy, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -
Alkylthio, Di(Ci-C4-alkyl)amino, Ci-C4-Alkyl-Ci-C6-alkoxycarbonylamino, CrC4-Alkylcarbonyl, Hydroxycarbonyl, Ci-C4-Alkoxycarbonyl, Aminocar- bonyl, Di(Ci-C4-alkyl)aminocarbonyl oder Cr C4-Al kylcarbonyloxy; Phenyl, Phenyl-Ci-Cδ-alkyl, Phenylcarbonyl-Ci-Cδ-alkyl, Phenoxycarbonyl, Phe- nylaminocarbonyl, Phenylsulfonylaminocarbonyl, N-(Ci-C6-Alkyl)-N-(phenyl)- aminocarbonyl, Phenyl-Ci-Cδ-alkylcarbonyl, wobei der Phenylrest partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann: Nitro, Cyano, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy oder Ci-C4-Halogenalkoxy; oder SO2R8;Alkylthio, di (Ci-C 4 alkyl) amino, Ci-C4-alkyl-Ci-C6-alkoxycarbonylamino, -C 4 alkylcarbonyl, hydroxycarbonyl, Ci-C 4 alkoxycarbonyl carbonyl, aminocarboxylic, Di (C 1 -C 4 -alkyl) aminocarbonyl or C 1 -C 4 -alkylcarbonyloxy; Phenyl, phenyl-C 1 -C 6 -alkyl, phenylcarbonyl-C 1 -C 6 -alkyl, phenoxycarbonyl, phenylaminocarbonyl, phenylsulfonylaminocarbonyl, N- (C 1 -C 6 -alkyl) -N- (phenyl) -aminocarbonyl, phenyl-C 1 -C 6 -cycloalkyl alkylcarbonyl, where the phenyl radical may be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, Ci-C 4 alkyl, Ci-C4-haloalkyl, Ci-C 4 alkoxy or C C 4 haloalkoxy; or SO 2 R 8 ;
R7 Wasserstoff, CrCβ-Alkyl, C3-C6-Cycloalkyl, C3-C6-Alkenyl, C3-C6-Al kinyl, C3-C6- Halogenalkenyl, C3-C6-Halogenalkinyl, Hydroxy oder Ci-C6-Alkoxy;R 7 is hydrogen, CrCβ alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 kinyl -alkyl, C 3 -C 6 - haloalkenyl, C 3 -C 6 haloalkynyl, hydroxy or C 1 -C 6 -alkoxy;
R8 d-Ce-Alkyl, Ci-C6-Halogenalkyl oder Phenyl, wobei der Phenylrest partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann: Ci-C6-Alkyl, d- Cε-Halogenalkyl oder Ci-CrAlkoxy;R 8 is d-Ce-alkyl, Ci-C 6 -haloalkyl or phenyl, where the phenyl radical may be partially or fully halogenated and / or may carry one to three of the following groups: Ci-C 6 alkyl, d- Cε-haloalkyl or Ci-CrAlkoxy;
sowie deren landwirtschaftlich brauchbaren Salze.and their agriculturally useful salts.
Außerdem betrifft die Erfindung Verfahren und Zwischenprodukte zur Herstellung von Verbindungen der Formel I, Mittel welche diese enthalten sowie die Verwendung dieser Derivate oder diese enthaltende Mittel zur Schadpflanzenbekämpfung. 2,ω-Diaminocarbonylverbindungen mit herbizider Wirksamkeit werden u.a. in WO 03/045878 beschrieben.Moreover, the invention relates to processes and intermediates for the preparation of compounds of formula I, compositions containing them and the use of these derivatives or agents containing them for controlling harmful plants. 2, ω-Diaminocarbonylverbindungen with herbicidal activity are described inter alia in WO 03/045878.
Weiterhin sind aus der Literatur (z.B. WO 05/061443 und WO 05/061464) benzoyl- sowie heteroaroyl-substituierte Phenylalanine bekannt, welche in ß-Position eine gegebenenfalls substituierte Aminogruppe tragen können.Furthermore, it is known from the literature (for example WO 05/061443 and WO 05/061464) benzoyl- and heteroaroyl-substituted phenylalanines which can carry an optionally substituted amino group in the β-position.
Die herbiziden Eigenschaften der bisher bekannten Verbindungen bzw. die Verträglichkeiten gegenüber Kulturpflanzen können jedoch nur bedingt befriedigen.However, the herbicidal properties of the previously known compounds or the tolerances towards crop plants can satisfy only conditionally.
Es lag daher dieser Erfindung die Aufgabe zugrunde, neue, insbesondere herbizid wirksame, Verbindungen mit verbesserten Eigenschaften zu finden.It was therefore an object of the present invention to find novel, in particular herbicidally active, compounds having improved properties.
Demgemäß wurden die heteroaroylsubstituierten Alanine der Formel I sowie deren herbizide Wirkung gefunden.Accordingly, the heteroaroyl-substituted alanines of the formula I and their herbicidal activity were found.
Ferner wurden herbizide Mittel gefunden, welche die Verbindungen I enthalten und eine sehr gute herbizide Wirkung besitzen. Außerdem wurden Verfahren zur Herstellung dieser Mittel und Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs mit den Verbindungen I gefunden.Furthermore, herbicidal agents were found which contain the compounds I and have a very good herbicidal activity. In addition, methods for the preparation of these compositions and methods for controlling undesired plant growth with the compounds I have been found.
Die Verbindungen der Formel I enthalten je nach Substitutionsmuster zwei oder mehr Chiralitätszentren und liegen dann als Enantiomeren oder Diastereomerengemische vor. Gegenstand der Erfindung sind sowohl die reinen Enantiomeren oder Diastereo- meren als auch deren Gemische.Depending on the substitution pattern, the compounds of the formula I contain two or more chiral centers and are then present as enantiomer or diastereomer mixtures. The invention provides both the pure enantiomers or diastereomers and mixtures thereof.
Die Verbindungen der Formel I können auch in Form ihrer landwirtschaftlich brauchba- ren Salze vorliegen, wobei es auf die Art des Salzes in der Regel nicht ankommt. Im allgemeinen kommen die Salze derjenigen Kationen oder die Säureadditionssalze derjenigen Säuren in Betracht, deren Kationen, beziehungsweise Anionen, die herbizide Wirkung der Verbindungen I nicht negativ beeinträchtigen.The compounds of the formula I can also be in the form of their agriculturally useful salts, whereby the type of salt generally does not matter. In general, the salts of those cations or the acid addition salts of those acids come into consideration whose cations, or anions, do not adversely affect the herbicidal activity of the compounds I.
Es kommen als Kationen insbesondere Ionen der Alkalimetalle, vorzugsweise Lithium, Natrium und Kalium, der Erdalkalimetalle, vorzugsweise Calcium und Magnesium, und der Übergangsmetalle, vorzugsweise Mangan, Kupfer, Zink und Eisen, sowie Ammonium, wobei hier gewünschtenfalls ein bis vier Wasserstoffatome durch Ci-C4-AIkVl, Hydroxy-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, Phe- nyl oder Benzyl ersetzt sein können, vorzugsweise Ammonium, Dimethylammonium, Diisopropylammonium, Tetramethylammonium, Tetrabutylammonium, 2-(2- Hydroxyeth-1-oxy)eth-1-ylammonium, Di-(2-hydroxyeth-1-yl)-ammonium, Trimethyl- benzylammonium, des weiteren Phosphoniumionen, Sulfoniumionen, vorzugsweise Tri(Ci-C4-alkyl)sulfonium und Sulfoxoniumionen, vorzugsweise Tri(Ci-C4alkyl)- sulfoxonium, in Betracht.The cations used are in particular ions of the alkali metals, preferably lithium, sodium and potassium, the alkaline earth metals, preferably calcium and magnesium, and the transition metals, preferably manganese, copper, zinc and iron, and ammonium, where, if desired, one to four hydrogen atoms are replaced by C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl or benzyl preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (2-hydroxyeth-1-oxy) eth-1-ylammonium, di- (2-hydroxyeth-1-yl) -ammonium, trimethylbenzylammonium, of further phosphonium ions, sulfonium ions, preferably Tri (C 1 -C 4 -alkyl) sulfonium and sulfoxonium ions, preferably tri (C 1 -C 4 -alkyl) sulfoxonium.
Anionen von brauchbaren Säureadditionsalzen sind in erster Linie Chlorid, Bromid, Fluorid, Hydrogensulfat, Sulfat, Dihydrogenphosphat, Hydrogenphosphat, Nitrat, Hydrogencarbonat, Carbonat, Hexafluorosilikat, Hexafluorophosphat, Benzoat sowie die Anionen von Ci-C4-Alkansäuren, vorzugsweise Formiat, Acetat, Propionat und Butyrat.Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
Die für die Substituenten R1-R12 oder als Reste an Phenyl-, Aryl-, Heteroaryl- oder Hetrocyclylringen genannten organischen Molekülteile stellen Sammelbegriffe für individuelle Aufzählungen der einzelnen Gruppenmitglieder dar. Sämtliche Kohlenwasserstoffketten, also alle Alkyl-, Alkylsilyl-, Alkenyl-, Alkinyl-, Cyanoalkyl-, Halogenalkyl-, Halogenalkenyl-, Halogenalkinyl-, Alkoxy-, Halogenalkoxy-, Alkoxyalkyl-, Alkoxyalkoxy- alkyl, Alkylcarbonyl-, Alkenylcarbonyl-, Alkinylcarbonyl-, Alkoxycarbonyl-, Alkenyloxy- carbonyl-, Alkinyloxycarbonyl-, Alkylamino-, Alkylsulfonylamino-, Halogenalkylsulfonyl- amino-, Alkylalkoxycarbonylamino-, Alkylaminocarbonyl-, Alkenylaminocarbonyl-, Alki- nylaminocarbonyl-, Alkylsulfonylaminocarbonyl, Dialkylaminocarbonyl-, N-Alkenyl-N- alkylaminocarbonyl-, N-Alkinyl-N-alkylamino-carbonyl-, N-Alkoxy-N-alkylamino- carbonyl-, N-Alkenyl-N-alkoxyaminocarbonyl-, N-Alkinyl-N-alkoxyaminocarbonyl-, Dial- kylaminothiocarbonyl-, Alkylcarbonylalkyl-, Alkoximinoalkyl-, N-(Alkylamino)-iminoalkyl, N-(Dialkylamino)-iminoalkyl, Formylamino-Ci-C4-alkyl, Ci-C6-Alkoxycarbonylamino-Ci- C4-alkyl, [(Ci-C6-Alkyl)amino-carbonylamino]Ci-C4-alkyl, [Di(Ci-C6-alkyl)amino- carbonylamino]-Ci-C4-alkyl, (Ci-C6-Alkyl)cyanoimino, [(Ci-C6-Alkyl)amino]cyanoimino, [Di(Ci-C6-alkyl)amino]cyanoimino, Phenylalkyl-, Phenylcarbonylalkyl-, N-Alkyl-N- phenylaminocarbonyl-, Phenylalkylcarbonyl-, Arylalkyl-, Heterocyclylcarbonylalkyl-, N- Alkyl-N-heterocyclylaminocarbonyl-, Heterocyclylalkylcarbonyl-, Alkylthio- und Alkylcar- bonyloxy-Teile können geradkettig oder verzweigt sein.Defined for the substituents R 1 -R 12 or as radicals on phenyl, organic moieties mentioned aryl, heteroaryl or Hetrocyclylringen are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, ie all alkyl, alkylsilyl, alkenyl, Alkynyl, cyanoalkyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, alkoxyalkyl, alkoxyalkoxyalkyl, alkylcarbonyl, alkenylcarbonyl, alkynecarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, alkylamino , Alkylsulfonylamino, haloalkylsulfonylamino, alkylalkoxycarbonylamino, alkylaminocarbonyl, alkenylaminocarbonyl, alkynylaminocarbonyl, alkylsulfonylaminocarbonyl, dialkylaminocarbonyl, N-alkenyl-N-alkylaminocarbonyl, N-alkynyl-N-alkylamino-carbonyl-, N- Alkoxy-N-alkylaminocarbonyl, N-alkenyl-N-alkoxyaminocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl, dialkylaminothiocarbonyl, alkylcarbonylalkyl, alkoximinoalk yl, N- (alkylamino) -iminoalkyl, N- (dialkylamino) -iminoalkyl, formylamino-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonylamino-C 1 -C 4 -alkyl, [(C 1 -C 6 -alkyl) amino-carbonylamino ] C 1 -C 4 -alkyl, [di (C 1 -C 6 -alkyl) aminocarbonylamino] -Ci-C 4 -alkyl, (C 1 -C 6 -alkyl) cyanoimino, [(C 1 -C 6 -alkyl) amino] cyanoimino, [Di (C 1 -C 6 -alkyl) amino] cyanoimino, phenylalkyl, phenylcarbonylalkyl, N-alkyl-N-phenylaminocarbonyl, phenylalkylcarbonyl, arylalkyl, heterocyclylcarbonylalkyl, N-alkyl-N-heterocyclylaminocarbonyl, heterocyclylalkylcarbonyl, alkylthio and Alkylcarbonyloxy moieties may be straight-chain or branched.
Sofern nicht anders angegeben tragen halogenierte Substituenten vorzugsweise ein bis fünf gleiche oder verschiedene Halogenatome. Die Bedeutung Halogen steht jeweils für Fluor, Chlor, Brom oder lod.Unless otherwise indicated, halogenated substituents preferably carry one to five identical or different halogen atoms. The meaning halogen in each case represents fluorine, chlorine, bromine or iodine.
Ferner bedeuten beispielsweise:Furthermore, for example:
- Ci-C4-Alkyl sowie die Alkylteile von Tri-Ci-C4-alkylsilyl, Ci-C4-Alkylcarbonyloxy, d- C4-alkyl-Ci-C4-alkoxycarbonylamino, Ci-C6-Alkyliminooxy-Ci-C4-alkyl, C1-C4- Alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C6-Alkoxy-Ci-C4-alkyl, C2-C6-Alkenyloxy-Ci-C4- alkyl, C2-C6-Alkinyloxy-Ci-C4-alkyl, Ci-C6-Halogenalkoxy-Ci-C4-alkyl, C2-C6- Halogenalkenyloxy-Ci-C4-alkyl, C2-C6-Halogenalkinyloxy-Ci-C4-alkyl, Ci-Cδ-Alkoxy-C 1 -C 4 -alkyl and the alkyl parts of tri-C 1 -C 4 -alkylsilyl, C 1 -C 4 -alkylcarbonyloxy, C 1 -C 4 -alkyl-C 1 -C 4 -alkoxycarbonylamino, C 1 -C 6 -alkyliminooxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsilyl, C4- alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C 6 alkoxy-Ci-C4-alkyl, C2-C6 alkenyloxy-Ci-C 4 - alkyl, C2-C6 alkynyloxy-Ci-C4-alkyl, Ci-C 6 haloalkoxy-Ci-C 4 alkyl, C 2 -C 6 - haloalkenyloxy-Ci-C4-alkyl, C2-C6-haloalkynyloxy-Ci-C4-alkyl, Ci-Cδ alkoxy
Ci-C4-alkoxy-Ci-C4-alkyl, C2-C6-Alkenylthio-Ci-C4-alkyl, C2-C6-Alkinylthio-Ci-C4-alkyl, Ci-Cβ-Alkylsulfinyl-Ci-C^alkyl, Ci-C6-Halogenalkyl- sulfinyl-Ci-C4-alkyl, Ci-Ce-Alkylsulfonyl-Ci^-alkyl, Ci-Ce-Halogenalkylsulfonyl-d- C4-alkyl, Amino-Ci-C4-alkyl, Di(Ci-C6-Alkyl)amino-Ci- C4-alkyl, Formylamino-Ci-C4-alkyl, Ci-C6-Alkoxycarbonylamino-Ci-C4-alkyl, Ci-Cβ- Alkylsulfonylamino-Ci-C4-alkyl, Ci-C6-Alkylsulfonyl-(Ci-C6-alkylamino)-Ci-C4-alkyl, Ci-C6-Alkoxycarbonyl-Ci-C4-alkyl, Ci-Cδ-Halogen- i-C6-Alkylcarbonyloxy-Ci-C4-alkyl, Aminocarbonyl-Ci-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 2 -C 6 alkenylthio-Ci-C4-alkyl, C2-C6 alkynylthio-Ci-C4-alkyl, Ci-Cβ-alkylsulfinyl-Ci-C ^ alkyl, Ci-C 6 haloalkyl sulfinyl C 1 -C 4 -alkyl, C 1 -C 6 -alkylsulfonyl-C 1 -C 4 -alkyl, C 1 -C 6 -haloalkylsulfonyl-d- C4-alkyl, amino-Ci-C4-alkyl, Di (C 1 -C 6 -alkyl) amino-C 1 -C 4 -alkyl, formylamino-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonylamino-C 1 -C 4 -alkyl, C 1 -C 6 -alkylsulfonylamino-C 1 -C 4 -alkyl, C6-alkylsulfonyl- (C 1 -C 6 -alkylamino) C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 6 -halogeno i-C6-alkylcarbonyloxy-C 1 -C 4 -alkyl, aminocarbonyl-ci
C4-alkyl, Ci-C6-Alkylaminocarbonyl-Ci-C4-alkyl, Di(Ci-C6-Alkyl)aminocarbonyl-Ci- C4-alkyl, [(Ci-C6-Alkyl)amino-carbonylamino]Ci-C4-alkyl, [Di(Ci-C6-alkyl)amino- carbonylamino]Ci-C4-alkyl, Ci-C6-Alkylcarbonylamino-Ci-C4-alkyl, Ci-Cβ- Alkylcarbonyl-(Ci-C6-alkylamino)-Ci-C4-alkyl, Ci-C6-Alkylaminocarbonyloxy-Ci-C4- alkyl, [Di(Ci-C6-alkylamino)carbonyloxy]Ci-C4-alkyl, Phenyl-Ci-C4-alkyl, Heteroaryl- carbonyl-Ci-C4-alkyl, Heteroarylcarbonyloxy-d^-alkyl, Heteroaryloxycarbonyl-Ci- C4-alkyl, Heteroaryloxy-Ci-C4-alkyl, Heteroarylthio-Ci-C4-alkyl, Heteroarylsulfinyl-Ci- C4-alkyl, Heteroarylsulfonyl-Ci-C4-alkyl, und Aryl(Ci-C4-alkyl): z.B. Methyl, Ethyl, n-Propyl, 1-Methylethyl, n-Butyl, 1-Methylpropyl, 2-Methylpropyl und 1 ,1-Dimethylethyl;C 4 -alkyl, C 1 -C 6 -alkylaminocarbonyl-C 1 -C 4 -alkyl, di (C 1 -C 6 -alkyl) aminocarbonyl-C 1 -C 4 -alkyl, [(C 1 -C 6 -alkyl) amino-carbonylamino] C 1 -C 4 -alkyl, [Di (C 1 -C 6 -alkyl) amino-carbonylamino] C 1 -C 4 -alkyl, C 1 -C 6 -alkylcarbonylamino-C 1 -C 4 -alkyl, C 1 -C 6 -alkylcarbonyl (C 1 -C 6 -alkylamino) C 1 -C 4 -alkyl , C 1 -C 6 -alkylaminocarbonyloxy-C 1 -C 4 -alkyl, [di (C 1 -C 6 -alkylamino) carbonyloxy] C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyl, heteroarylcarbonyl-C 1 -C 4 -alkyl, heteroarylcarbonyloxy d ^ -alkyl, heteroaryloxycarbonyl-C 1 -C 4 -alkyl, heteroaryloxy-C 1 -C 4 -alkyl, heteroarylthio-C 1 -C 4 -alkyl, heteroarylsulfinyl-C 1 -C 4 -alkyl, heteroarylsulfonyl-C 1 -C 4 -alkyl, and aryl ( C 1 -C 4 -alkyl): for example, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl and 1, 1-dimethylethyl;
- Ci-Cβ-Alkyl sowie die Alkylteile von Ci-Cβ-Cyanoalkyl, Ci-C6-Alkoxycarbonyl-Ci-C6- alkyl, Ci-C6-Alkylsulfonylamino, Ci-Ce-Alkylsulfonylaminocarbonyl, N-(C3-C6- Alkenyl)-N-(Ci-C6-alkyl)-aminocarbonyl, (C3-C6-Alkinyl)-N-(Ci-C6-alkyl)-amino- carbonyl, N-(Ci-C6-Alkoxy)-N-(Ci-C6-alkyl)-aminocarbonyl, Ci-Cδ-Alkylcarbonyl-C 1 -C 6 -alkyl and the alkyl parts of C 1 -C 6 -cycloalkyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -alkylsulfonylaminocarbonyl, N- (C 3 -C 6 -alkenyl) - N- (C 1 -C 6 -alkyl) -aminocarbonyl, (C 3 -C 6 -alkynyl) -N- (C 1 -C 6 -alkyl) -aminocarbonyl, N- (C 1 -C 6 -alkoxy) -N- (C 1 -C 6 alkyl) aminocarbonyl, Ci-Cδ-Alkylcarbonyl-
Ci-Cδ-alkyl, Ci-C6-Alkoxyimino-Ci-C6-alkyl, N-(Ci-C6-Alkylamino)-imino-Ci-C6- alkyl, N-(Di-Ci-C6-alkyl-amino)-imino-Ci-C6-alkyl, (Ci-C6-Alkyl)cyanoimino, Phe- nyl-Ci-C6-alkyl, Phenylcarbonyl-Ci-Ce-alkyl, N-(Ci-C6-Alkyl)-N-phenylamino- carbonyl, Hetrocyclyl-carbonyl-Ci-C6-alkyl und N-(Ci-C6-Alkyl)-N-hetero- cyclylaminocarbonyl:C 1 -C 6 -alkyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, N- (C 1 -C 6 -alkylamino) -imino-C 1 -C 6 -alkyl, N- (C 1 -C-C 6 -alkyl-amino) - imino-C 1 -C 6 -alkyl, (C 1 -C 6 -alkyl) cyanoimino, phenyl-C 1 -C 6 -alkyl, phenylcarbonyl-C 1 -C 6 -alkyl, N- (C 1 -C 6 -alkyl) -N-phenylamino carbonyl, heterocyclylcarbonyl-C 1 -C 6 -alkyl and N- (C 1 -C 6 -alkyl) -N-heterocyclylaminocarbonyl:
Ci-C4-Alkyl, wie voranstehend genannt, sowie z.B. n-Pentyl, 1-Methyl-butyl, 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-Di- methylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1-Ethyl-butyl,Ci-C4-alkyl, as mentioned above, as well as e.g. 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 ethyl-butyl,
2-Ethylbutyl, 1 ,1 ,2-Trimethylpropyl, 1-Ethyl-1-methylpropyl und 1-Ethyl-3- methylpropyl;2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;
- Ci-C4-Alkylcarbonyl: z.B. Methylcarbonyl, Ethylcarbonyl, Propylcarbonyl, 1-Methyl- ethylcarbonyl, Butylcarbonyl, 1-Methylpropylcarbonyl, 2-Methylpropylcarbonyl oderC 1 -C 4 -alkylcarbonyl: e.g. Methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or
1 ,1-Dimethylethylcarbonyl;1, 1-dimethylethylcarbonyl;
- Ci-Cδ-Alkylcarbonyl sowie die Alkylcarbonylreste von Ci-C6-Alkylcarbonyl-Ci-C6- alkyl, Ci-C6-Alkylcarbonyloxy-Ci-C6-alkyl, Ci-C6-Alkylcarbonylamino-Ci-C4-alkyl, Phenyl-Ci-Cδ-alkylcarbonyl und Heterocyclyl-Ci-Cδ-alkylcarbonyl, Ci-Cβ-C 1 -C 6 -alkylcarbonyl and the alkylcarbonyl radicals of C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonylamino-C 1 -C 4 -alkyl, phenylcyclo Cδ-alkylcarbonyl and heterocyclyl-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkyl
Alkylcarbonyl-^i-Ce-alkylaminoJ-Ci^-alkyl:Alkylcarbonyl ^ i-Ce-alkylaminoJ-Ci ^ alkyl:
Ci-C4-Alkylcarbonyl, wie voranstehend genannt, sowie z.B. Pentylcarbonyl, 1- Methylbutylcarbonyl, 2-Methylbutylcarbonyl, 3-Methylbutylcarbonyl, 2,2- Dimethylpropylcarbonyl, 1-Ethylpropylcarbonyl, Hexylcarbonyl, 1 ,1-Dimethyl- propylcarbonyl, 1 ,2-Dimethylpropylcarbonyl, 1-Methylpentylcarbonyl, 2-Methyl- pentylcarbonyl, 3-Methylpentylcarbonyl, 4-Methylpentylcarbonyl, 1 ,1-Dimethyl- butylcarbonyl, 1 ,2-Dimethylbutylcarbonyl, 1 ,3-Dimethylbutylcarbonyl, 2,2-Di- methylbutylcarbonyl, 2,3-Dimethylbutylcarbonyl, 3,3-Dimethylbutylcarbonyl, 1-C 1 -C 4 -alkylcarbonyl, as mentioned above, and also, for example, pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2- Dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1, 2-Dimethylbutylcarbonyl, 1, 3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1
Ethylbutylcarbonyl, 2-Ethylbutylcarbonyl, 1 ,1 ,2-Trimethylpropylcarbonyl, 1 ,2,2- Trimethylpropylcarbonyl, 1-Ethyl-i-methylpropylcarbonyl oder 1-Ethyl-2-methyl- propylcarbonyl;Ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-i-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl;
- C3-C6-Cycloalkyl sowie die Cycloalkylteile von C3-C6-Cycloalkylcarbonyl: monocyc- lischer, gesättigter Kohlenwasserstoff mit 3 bis 6 Ringgliedern, wie Cyclopropyl, Cyclobutyl, Cyclopentyl und Cyclohexyl;C 3 -C 6 -cycloalkyl and the cycloalkyl parts of C 3 -C 6 -cycloalkylcarbonyl: monocyclic, saturated hydrocarbon having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
- C3-C6-Cycloalkenyl: z.B. 1-Cyclopropenyl, 2-Cyclopropenyl, 1-Cyclobutenyl, 2- Cyclobutenyl, 1-Cyclopentenyl, 2-Cyclopentenyl, 1 ,3-Cyclopentadienyl, 1 ,4-C3-C6 cycloalkenyl: e.g. 1-Cyclopropenyl, 2-Cyclopropenyl, 1-Cyclobutenyl, 2-Cyclobutenyl, 1-Cyclopentenyl, 2-Cyclopentenyl, 1, 3-Cyclopentadienyl, 1, 4-
Cyclopentadienyl, 2,4-Cyclopentadienyl, 1-Cyclohexenyl, 2-Cyclohexenyl, 3- Cyclohexenyl, 1 ,3-Cyclohexadienyl, 1 ,4-Cyclohexadienyl, 2,5-Cyclohexadienyl;Cyclopentadienyl, 2,4-cyclopentadienyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl, 1, 4-cyclohexadienyl, 2,5-cyclohexadienyl;
- C3-C6-Alkenyl sowie die Alkenylteile von C3-C6-Alkenyloxycarbonyl, C3-C6-Alkenyl- aminocarbonyl, N-(C3-C6-Alkenyl)-N-(Ci-C6-alkyl)aminocarbonyl und N-(C3-C6-C3-C6-alkenyl and the alkenyl moieties of C3-C6-alkenyloxycarbonyl, C3-C6-alkenyl-aminocarbonyl, N- (C3-C6-alkenyl) -N- (C1-C6-alkyl) -aminocarbonyl and N- (C3-C6-alkenyl) C6
Alkenyl)-N-(Ci-C6-alkoxy)aminocarbonyl: z.B. 1-Propenyl, 2-Propenyl, 1-Methyl- ethenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1-Methyl-1-propenyl, 2-Methyl-1-propenyl, 1-Methyl-2-propenyl, 2-Methyl-2-propenyl, 1-Pentenyl, 2-Pentenyl, 3-Pentenyl, 4- Pentenyl, 1-Methyl-1-butenyl, 2-Methyl-1-butenyl, 3-Methyl-1-butenyl, 1 -Methyl-2- butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, 1-Methyl-3-butenyl, 2-Methyl-3- butenyl, 3-Methyl-3-butenyl, 1 ,1-Dimethyl-2-propenyl, 1 ,2-Dimethyl-1-propenyl, 1 ,2- Dimethyl-2-propenyl, 1-Ethyl-1-propenyl, 1-Ethyl-2-propenyl, 1-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl, 1-Methyl-1-pentenyl, 2-Methyl-1-pentenyl, 3-Methyl-1-pentenyl, 4-Methyl-1-pentenyl, 1-Methyl-2-pentenyl, 2-Methyl-2-pente- nyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, 1-Methyl-3-pentenyl, 2-Methyl-3- pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1-Methyl-4-pentenyl, 2-Methyl- 4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 ,1-Dimethyl-2-butenyl, 1 ,1- Dimethyl-3-butenyl, 1 ,2-Dimethyl-1 -butenyl, 1 ,2-Dimethyl-2-butenyl, 1 ,2-Dimethyl-3- butenyl, 1 ,3-Dimethyl-1 -butenyl, 1 ,3-Dimethyl-2-butenyl, 1 ,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2, 3-Dimethyl-1 -butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Alkenyl) -N- (C 1 -C 6 alkoxy) aminocarbonyl: e.g. 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1 - Methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1- Dimethyl 2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2- pentenyl, 2-methyl-2-pentynyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3- pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2 butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-b utenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2-dimethyl-3 butenyl, 2, 3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-
Dimethyl-3-butenyl, 3, 3-Dimethyl-1 -butenyl, 3,3-Dimethyl-2-butenyl, 1-Ethyl-1- butenyl, 1-Ethyl-2-butenyl, 1-Ethyl-3-butenyl, 2-Ethyl-1 -butenyl, 2-Ethyl-2-butenyl, 2- Ethyl-3-butenyl, 1 ,1 ,2-Trimethyl-2-propenyl, 1-Ethyl-1-methyl-2-propenyl, 1-Ethyl-2- methyl-1-propenyl und 1-Ethyl-2-methyl-2-propenyl;Dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1 Ethyl 2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
- C2-C6-Alkenyl sowie die Alkenylteile von C2-C6-Alkenylcarbonyl, C2-C6-Alkenyloxy- Ci-C4-alkyl, C2-C6-Alkenylthio-Ci-C4-alkyl, Phenyl-C2-C4-alkenyl, Heteroary-C2-C4- alkenyl: C3-C6-Alkenyl wie voranstehend genannt sowie Ethenyl; - C3-C6-Alkinyl sowie die Alkinylteile von Cs-Cδ-Alkinyloxycarbonyl, C3-C6- Alkinylaminocarbonyl, N-(C3-C6-Alkinyl)-N-(Ci-C6-alkyl)-aminocarbonyl, N-(C3- C6-Alkinyl)-N-(Ci-C6-alkoxyaminocarbonyl: z.B. 1-Propinyl, 2-Propinyl, 1-Butinyl, 2-Butinyl, 3-Butinyl, 1-Methyl-2-propinyl, 1-Pentinyl, 2-Pentinyl, 3-Pentinyl,- C2-C6-alkenyl and also the alkenyl moieties of C2-C6-alkenylcarbonyl, C2-C6-alkenyloxy Ci-C 4 alkyl, C 2 -C 6 alkenylthio-Ci-C4-alkyl, phenyl-C 2 -C 4 alkenyl, heteroaryl C 2 -C 4 alkenyl: C 3 -C 6 alkenyl as mentioned above and ethenyl; - C3-C6-alkynyl and the alkynyl moieties of Cs-Cδ-alkynyloxycarbonyl, C3-C6-alkynylaminocarbonyl, N- (C3-C6-alkynyl) -N- (Ci-C6-alkyl) -aminocarbonyl, N- (C3-C6 Alkynyl) -N- (C 1 -C 6 -alkoxyaminocarbonyl: eg 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl,
4-Pentinyl, 1-Methyl-2-butinyl, 1 -Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1- butinyl, 1 ,1-Dimethyl-2-propinyl, 1 -Ethyl-2-propinyl, 1-Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1-Methyl-2-pentinyl, 1-Methyl-3-pentinyl, 1-Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-1-pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-1-pentinyl, 4-Methyl-2-pentinyl, 1 ,1-Dimethyl-2-butinyl, 1 ,1-Dimethyl-3- butinyl, 1 ,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-1-butinyl, 1-Ethyl-2-butinyl, 1 -Ethyl-3-butinyl, 2-Ethyl-3-butinyl und 1-Ethyl-1-methyl-2- propinyl;4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl 2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2- Methyl 3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1 Dimethyl-2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl 2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;
- C2-C6-Alkinyl sowie die Alkinylteile von C2-C6-Alkinylcarbonyl, C2-C2-Alkinyloxy-Ci- C4-alkyl, C2-C6-Alkinylthio-Ci-C4-alkyl, Phenyl-C2-C4-alkinyl, Heteroaryl-C2-C4- alkinyl: C3-C6-Alkinyl wie voranstehend genannt sowie Ethinyl;C 2 -C 6 -alkynyl and the alkynyl moieties of C 2 -C 6 -alkynylcarbonyl, C 2 -C 2 -alkynyloxy-C 1 -C 4 -alkyl, C 2 -C 6 -alkynylthio-C 1 -C 4 -alkyl, phenyl-C 2 -C 4 -alkynyl, heteroaryl-C 2 -C 4 -alkynyl: C 3 -C 6 -alkynyl as mentioned above as well as ethynyl;
- Ci-C4-Cyanoalkyl: z.B. Cyanomethyl, 1-Cyanoeth-1-yl, 2-Cyanoeth-1-yl, 1-Cyano- prop-1-yl, 2-Cyanoprop-1-yl, 3-Cyanoprop-1-yl, 1-Cyanoprop-2-yl, 2-Cyanoprop-2- yl, 1-Cyanobut-1-yl, 2-Cyanobut-1-yl, 3-Cyanobut-1-yl, 4-Cyanobut-1-yl, 1-Cyano- but-2-yl, 2-Cyanobut-2-yl, 1-Cyanobut-3-yl, 2-Cyanobut-3-yl, 1-Cyano-2-methyl- prop-3-yl, 2-Cyano-2-methyl-prop-3-yl, 3-Cyano-2-methyl-prop-3-yl und 2-Cyano- methyl-prop-2-yl;- C 1 -C 4 cyanoalkyl: for example, cyanomethyl, 1-cyanoeth-1-yl, 2-cyanoeth-1-yl, 1-cyano-prop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1 -yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl , 1-cyano-but-2-yl, 2-cyanobut-2-yl, 1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-cyano-2-methyl-prop-3-yl, 2 Cyano-2-methyl-prop-3-yl, 3-cyano-2-methyl-prop-3-yl and 2-cyano-methyl-prop-2-yl;
- Ci-C4-Hydroxyalkyl sowie die Ci-C4-Hydroxyalkyl-Teile von Phenyl-Ci-C4- hydroxyalkyl, Heteroaryl-Ci-C4-hydroxyalkyl: z.B. Hydroxymethyl, 1-Hydroxyeth-1-yl, 2-Hydroxyeth-1-yl, 1-Hydroxyprop-1-yl, 2-Hydroxyprop-1-yl, 3-Hydroxyprop-1-yl, 1- Hydroxyprop-2-yl, 2-Hydroxyprop-2-yl, 1-Hydroxybut-1-yl, 2-Hydroxybut-1-yl, 3- Hydroxybut-1-yl, 4-Hydroxybut-1-yl, 1-Hydroxybut-2-yl, 2-Hydroxybut-2-yl, 1-- Ci-C4-hydroxyalkyl and Ci-C4-hydroxyalkyl moieties of phenyl-Ci-C 4 - hydroxyalkyl, heteroaryl-Ci-C4-hydroxyalkyl: for example hydroxymethyl, 1-hydroxyeth-1-yl, 2-hydroxyeth 1-yl, 1-hydroxyprop-1-yl, 2-hydroxyprop-1-yl, 3-hydroxyprop-1-yl, 1-hydroxyprop-2-yl, 2-hydroxyprop-2-yl, 1-hydroxybut-1 1-hydroxybut-2-yl, 2-hydroxybut-2-yl,
Hydroxybut-3-yl, 2-Hydroxybut-3-yl, 1-Hydroxy -2-methyl-prop-3-yl, 2-Hydroxy -2- methyl-prop-3-yl, 3-Hydroxy -2-methyl-prop-3-yl und 2-Hydroxymethyl-prop-2-yl, 1 ,2-Diydroxyethyl, 1 ,2-Dihydroxyprop-3-yl, 2,3-Dihydroxyprop-3-yl, 1 ,2-Dihydroxy- prop-2-yl, 1 ,2-Diydroxybut-4-yl, 2,3-Diydroxybut-4-yl, 3,4-Diydroxybut-4-yl, 1 ,2- Diydroxybut-2-yl, 1 ,2-Diydroxybut-3-yl, 2,3-Diydroxybut-3-yl, 1 ,2-Dihydroxy-2- methyl-prop-3-yl , 2 ,3-Di hyd roxy-2-methyl-prop-3-yl ;Hydroxybut-3-yl, 2-hydroxybut-3-yl, 1-hydroxy-2-methyl-prop-3-yl, 2-hydroxy-2-methylprop-3-yl, 3-hydroxy-2-methyl prop-3-yl and 2-hydroxymethyl-prop-2-yl, 1, 2-dihydroxyethyl, 1, 2-dihydroxyprop-3-yl, 2,3-dihydroxyprop-3-yl, 1, 2-dihydroxypropyl 2-yl, 1, 2-dihydroxybut-4-yl, 2,3-dihydroxybut-4-yl, 3,4-dihydroxybut-4-yl, 1, 2-dihydroxybut-2-yl, 1, 2-dihydroxybutyl 3-yl, 2,3-dihydroxybut-3-yl, 1, 2-dihydroxy-2-methyl-prop-3-yl, 2,3-dihydroxy-2-methyl-prop-3-yl;
- Ci-Cδ-Hydroxyalkyl: Ci-C4-Hydroxyalkyl wie voranstehend genannt, sowie z.B. 1- Hydroxy-pent-5-yl, 2-Hydroxy-pent-5-yl, 3-Hydroxy-pent-5-yl, 4-Hydroxy-pent-5-yl, 5-Hydroxy-pent-5-yl, 1-Hydroxypent-4-yl, 2-Hydroxypen-4-tyl, 3-Hydroxypent-4-yl, 4-C 1 -C 6 -hydroxyalkyl: C 1 -C 4 -hydroxyalkyl as mentioned above, and also, for example, 1-hydroxy-pent-5-yl, 2-hydroxy-pent-5-yl, 3-hydroxy-pent-5-yl, 4 -Hydroxy-pent-5-yl, 5-hydroxy-pent-5-yl, 1-hydroxypent-4-yl, 2-hydroxy-4-yl, 3-hydroxypent-4-yl, 4-
Hydroxypent-4-yl, 1-Hydroxy-pent-3-yl, 2-Hydroxy-pent-3-yl, 3-Hydroxy-pent-3-yl, 1- Hydroxy-2-methyl-but-3-yl, 2-Hydroxy-2-methyl-but-3-yl, 3-Hydroxy-2-methyl-but-3- yl, 1-Hydroxy-2-methyl-but-4-yl, 2-Hydroxy-2-methyl-but-4-yl, 3-Hydroxy-2-methyl- but-4-yl, 4-Hydroxy-2-methyl-but-4-yl, 1-Hydroxy-3-methyl-but-4-yl, 2-Hydroxy-3- methyl-but-4-yl, 3-Hydroxy-3-methyl-but-4-yl, 4-Hydroxy-3-methyl-but-4-yl, 1- Hydroxy-hex-6-yl, 2-Hydroxy-hex-6-yl, 3-Hydroxy-hex-6-yl, 4-Hydroxy-hex-6-yl, 5- Hydroxy-hex-6-yl, 6-Hydroxy-hex-6-yl, 1-Hydroxy-2-methyl-pent-5-yl, 2-Hydroxy-2- methyl-pent-5-yl, 3-Hydroxy-2-methyl-pent-5-yl, 4-Hydroxy-2-methyl-pent-5-yl, 5-Hydroxypent-4-yl, 1-hydroxy-pent-3-yl, 2-hydroxy-pent-3-yl, 3-hydroxy-pent-3-yl, 1-hydroxy-2-methylbut-3-yl, 2-hydroxy-2-methyl-but-3-yl, 3-hydroxy-2-methyl-but-3-yl, 1-hydroxy-2-methyl-but-4-yl, 2-hydroxy-2-methyl but-4-yl, 3-hydroxy-2-methyl but-4-yl, 4-hydroxy-2-methyl-but-4-yl, 1-hydroxy-3-methyl-but-4-yl, 2-hydroxy-3-methyl-but-4-yl, 3 Hydroxy-3-methylbut-4-yl, 4-hydroxy-3-methyl-but-4-yl, 1-hydroxy-hex-6-yl, 2-hydroxy-hex-6-yl, 3-hydroxy hex-6-yl, 4-hydroxy-hex-6-yl, 5-hydroxy-hex-6-yl, 6-hydroxy-hex-6-yl, 1-hydroxy-2-methyl-pent-5-yl, 2-hydroxy-2-methyl-pent-5-yl, 3-hydroxy-2-methyl-pent-5-yl, 4-hydroxy-2-methyl-pent-5-yl, 5
Hydroxy-2-methyl-pent-5-yl, 1 -Hydroxy-3-methyl-pent-5-yl, 2-Hydroxy-3-methyl- pent-5-yl, 3-Hydroxy-3-methyl-pent-5-yl, 4-Hydroxy-3-methyl-pent-5-yl, 5-Hydroxy-3- methyl-pent-5-yl, 1-Hydroxy-4-methyl-pent-5-yl, 2-Hydroxy-4-methyl-pent-5-yl, 3- Hydroxy-4-methyl-pent-5-yl, 4-Hydroxy-4-methyl-pent-5-yl, 5-Hydroxy-4-methyl- pent-5-yl, 1-Hydroxy-5-methyl-pent-5-yl, 2-Hydroxy-5-methyl-pent-5-yl, 3-Hydroxy-5- methyl-pent-5-yl, 4-Hydroxy-5-methyl-pent-5-yl, 5-Hydroxy-5-methyl-pent-5-yl, 1- Hydroxy-2,3-dimethyl-but-4-yl, 2-Hydroxy-2,3-dimethyl-but-4-yl, 3-Hydroxy-2,3- dimethyl-but-4-yl, 4-Hydroxy-2,3-dimethyl-but-4-yl, 1 ,2-Dihydroxy-pent-5-yl, 2,3- Dihydroxy-pent-5-yl, 3,4-Dihydroxy-pent-5-yl, 4,5-Dihydroxy-pent-5-yl, 1 ,2- Diydroxypent-4-yl, 2,3-Diydroxypent-4-yl, 3,4-Diydroxypent-4-yl, 4,5-Diydroxypent-4- yl, 1 ,2-Dihydroxy-pent-3-yl, 2,3-Dihydroxy-pent-3-yl, 1 ,2-Dihydroxy-2-methyl-but-3- yl, 2,3-Dihydroxy-2-methyl-but-3-yl, 3,4-Dihydroxy-2-methyl-but-3-yl, 2-Hydroxy-2- hdroxymethyl-but-3-yl, 1 ,2-Dihydroxy-2-methyl-but-4-yl, 2,3-Dihydroxy-2-methyl-but- 4-yl, 3,4-Dihydroxy-2-methyl-but-4-yl, 1 ,2-Dihydroxy-3-methyl-but-4-yl, 2,3- Dihydroxy-3-methyl-but-4-yl, 3,4-Dihydroxy-3-methyl-but-4-yl, 3-Hydroxy-3- hydroxymethyl-but-4-yl, 1 ,2-Diydroxy-hex-6-yl, 2,3-Diydroxy-hex-6-yl, 3,4-Diydroxy- hex-6-yl, 4,5-Diydroxy-hex-6-yl, 5,6-Diydroxy-hex-6-yl, 1 ,2-Dihydroxy-2-methyl-pent- 5-yl, 2,3-Dihydroxy-2-methyl-pent-5-yl, 3,4-Dihydroxy-2-methyl-pent-5-yl, 4,5- Dihydroxy-2-methyl-pent-5-yl, 2-Hydroxy-2-hdroxymethyl-pent-5-yl, 1 ,2-Dihydroxy- 3-methyl-pent-5-yl, 2,3-Dihydroxy-3-methyl-pent-5-yl, 3,4-Dihydroxy-3-methyl-pent-Hydroxy-2-methylpent-5-yl, 1-hydroxy-3-methyl-pent-5-yl, 2-hydroxy-3-methyl-pent-5-yl, 3-hydroxy-3-methylpentane 5-yl, 4-hydroxy-3-methyl-pent-5-yl, 5-hydroxy-3-methyl-pent-5-yl, 1-hydroxy-4-methyl-pent-5-yl, 2-hydroxy 4-methyl-pent-5-yl, 3-hydroxy-4-methyl-pent-5-yl, 4-hydroxy-4-methyl-pent-5-yl, 5-hydroxy-4-methyl-pent-5-yl yl, 1-hydroxy-5-methyl-pent-5-yl, 2-hydroxy-5-methyl-pent-5-yl, 3-hydroxy-5-methyl-pent-5-yl, 4-hydroxy-5 methyl-pent-5-yl, 5-hydroxy-5-methylpent-5-yl, 1-hydroxy-2,3-dimethyl-but-4-yl, 2-hydroxy-2,3-dimethylbutane 4-yl, 3-hydroxy-2,3-dimethylbut-4-yl, 4-hydroxy-2,3-dimethylbut-4-yl, 1, 2-dihydroxy-pent-5-yl, 2, 3-Dihydroxy-pent-5-yl, 3,4-dihydroxy-pent-5-yl, 4,5-dihydroxy-pent-5-yl, 1,2-dihydroxypent-4-yl, 2,3-dihydroxypentyl 4-yl, 3,4-dihydroxypent-4-yl, 4,5-dihydroxypent-4-yl, 1, 2-dihydroxy-pent-3-yl, 2,3-dihydroxy-pent-3-yl, 1, 2-Dihydroxy-2-methyl-but-3-yl, 2,3-dihydroxy-2-methyl-but-3-yl, 3,4-dihydroxy-2-methyl-but-3-yl, 2-hydroxy 2-hydroxymethyl-but-3-y l, 1, 2-dihydroxy-2-methylbut-4-yl, 2,3-dihydroxy-2-methyl-but-4-yl, 3,4-dihydroxy-2-methyl-but-4-yl, 1,2-dihydroxy-3-methyl-but-4-yl, 2,3-dihydroxy-3-methyl-but-4-yl, 3,4-dihydroxy-3-methyl-but-4-yl, 3 Hydroxy-3-hydroxymethyl-but-4-yl, 1, 2-dihydroxy-hex-6-yl, 2,3-dihydroxy-hex-6-yl, 3,4-dihydroxy-hex-6-yl, 4, 5-dihydroxy-hex-6-yl, 5,6-dihydroxy-hex-6-yl, 1, 2-dihydroxy-2-methyl-pent-5-yl, 2,3-dihydroxy-2-methylpentane 5-yl, 3,4-dihydroxy-2-methyl-pent-5-yl, 4,5-dihydroxy-2-methyl-pent-5-yl, 2-hydroxy-2-hydroxymethyl-pent-5-yl, 1, 2-dihydroxy-3-methyl-pent-5-yl, 2,3-dihydroxy-3-methyl-pent-5-yl, 3,4-dihydroxy-3-methyl-pentene
5-yl, 4,5-Dihydroxy-3-methyl-pent-5-yl, 3-Hydroxy-3-hdroxymethyl-pent-5-yl, 1 ,2- Dihydroxy-4-methyl-pent-5-yl, 2,3-Dihydroxy-4-methyl-pent-5-yl, 3,4-Dihydroxy-4- methyl-pent-5-yl, 4,5-Dihydroxy-4-methyl-pent-5-yl, 4-Hydroxy-4-hdroxymethyl-pent- 5-yl, 1 ,2-Dihydroxy-5-methyl-pent-5-yl, 2,3-Dihydroxy-5-methyl-pent-5-yl, 3,4- Dihydroxy-5-methyl-pent-5-yl, 4,5-Dihydroxy-5-methyl-pent-5-yl, 5-Hydroxy-5- hdroxymethyl-pent-5-yl, 1 ,2-Diydroxy-2,3-dimethyl-but-4-yl, 2,3-Diydroxy-2,3- dimethyl-but-4-yl, 3,4-Dihydroxy-2,3-dimethyl-but-4-yl, 2-Hydroxy-2-hydroxymethyl- 3-methyl-but-4-yl, 3-Hydroxy-3-hydroxymethyl-2-methyl-but-4-yl;5-yl, 4,5-dihydroxy-3-methyl-pent-5-yl, 3-hydroxy-3-hydroxymethyl-pent-5-yl, 1, 2-dihydroxy-4-methyl-pent-5-yl, 2,3-Dihydroxy-4-methyl-pent-5-yl, 3,4-dihydroxy-4-methyl-pent-5-yl, 4,5-dihydroxy-4-methyl-pent-5-yl, 4- Hydroxy-4-hydroxymethyl-pent-5-yl, 1, 2-dihydroxy-5-methyl-pent-5-yl, 2,3-dihydroxy-5-methyl-pent-5-yl, 3,4-dihydroxy- 5-methyl-pent-5-yl, 4,5-dihydroxy-5-methyl-pent-5-yl, 5-hydroxy-5-hydroxymethyl-pent-5-yl, 1, 2-dihydroxy-2,3- dimethyl-but-4-yl, 2,3-dihydroxy-2,3-dimethyl-but-4-yl, 3,4-dihydroxy-2,3-dimethyl-but-4-yl, 2-hydroxy-2- hydroxymethyl-3-methylbut-4-yl, 3-hydroxy-3-hydroxymethyl-2-methylbut-4-yl;
Ci-C4-Halogenalkyl sowie die Halogenalkylteile von Phenyl-Ci-C4-halogenalkyl, Heteroaryl-Ci-C4-halogenalkyl: ein Ci-C4-Alkylrest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. Chlormethyl, Dichlormethyl, Trichlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, Chlorfluormethyl, Dichlorfluormethyl, Chlordifluormethyl, Brommethyl, lodmethyl, 2-Fluorethyl, 2-Chlorethyl, 2-Bromethyl, 2-lodethyl, 2,2-Difluorethyl,C 1 -C 4 -haloalkyl and the haloalkyl parts of phenyl-C 1 -C 4 -haloalkyl, heteroaryl-C 1 -C 4 -haloalkyl: a C 1 -C 4 -alkyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine is, eg Chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,
2,2,2-Trifluorethyl, 2-Chlor-2-fluorethyl, 2-Chlor-2,2-difluorethyl, 2,2-Dichlor-2- fluorethyl, 2,2,2-Trichlorethyl, Pentafluorethyl, 2-Fluorpropyl, 3-Fluorpropyl, 2,2- Difluorpropyl, 2,3-Difluorpropyl, 2-Chlorpropyl, 3-Chlorpropyl, 2,3-Dichlorpropyl, 2- Brompropyl, 3-Brompropyl, 3,3,3-Trifluorpropyl, 3,3,3-Trichlorpropyl, 2,2,3,3,3- Pentafluorpropyl, Heptafluorpropyl, 1-(Fluormethyl)-2-fluorethyl, 1-(Chlormethyl)-2- chlorethyl, 1-(Brommethyl)-2-bromethyl, 4-Fluorbutyl, 4-Chlorbutyl, 4-Brombutyl, Nonafluorbutyl, 1 ,1 ,2,2-Tetrafluorethyl und 1-Trifluormethyl-1 ,2,2,2,2-tetrafluorethyl;2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2- Bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl ) -2-chloroethyl, 1- (bromomethyl) -2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl, 1,1,2,2-tetrafluoroethyl and 1-trifluoromethyl-1,2,2, 2,2-tetrafluoroethyl;
- Ci-Cδ-Halogenalkyl sowie die Halogenalkylteile von Ci-Cδ-Halogenalkylsulfonyl- amino, Ci-Cδ-Halogenalkyl-Ci^-thioalkyl,: Ci-C4-Halogenalkyl wie voranstehend genannt, sowie z.B. 5-Fluorpentyl, 5-Chlorpentyl, 5-Brompentyl, 5-lodpentyl, Undecafluorpentyl, 6-Fluorhexyl, 6-Chlorhexyl, 6-Bromhexyl, 6-lodhexyl und Tridecafluorhexyl;- Ci-Cδ-haloalkyl and the haloalkyl moieties of Ci-Cδ-haloalkylsulfonyl-amino, Ci-Cδ-haloalkyl-Ci ^ -thioalkyl, Ci-C4-haloalkyl as mentioned above, as well as e.g. 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and tridecafluorohexyl;
- C3-C6-Halogenalkenyl: ein C3-C6-Alkenylrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, z.B. 2-Chlor- prop-2-en-1-yl, 3-Chlorprop-2-en-1-yl, 2,3-Dichlorprop-2-en-1-yl, 3,3-Dichlorprop-2- en-1-yl, 2,3,3-Trichlor-2-en-1-yl, 2,3-Dichlorbut-2-en-1-yl, 2-Bromprop-2-en-1-yl, 3-C3-C6-haloalkenyl: a C3-C6-alkenyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, e.g. 2-chloro-prop-2-en-1-yl, 3-chloroprop-2-en-1-yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop-2-ene 1-yl, 2,3,3-trichloro-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3
Bromprop-2-en-1-yl, 2,3-Dibromprop-2-en-1-yl, 3,3-Dibromprop-2-en-1-yl, 2,3,3- Tribrom-2-en-1 -yl oder 2,3-Dibrombut-2-en-1 -yl;Bromoprop-2-en-1-yl, 2,3-dibromoprop-2-en-1-yl, 3,3-dibromoprop-2-en-1-yl, 2,3,3-tribromo-2-ene 1 -yl or 2,3-dibromobut-2-en-1-yl;
- C2-C6-Halogenalkenyl sowie die C2-C6-Halogenalkenyl-Teile von C2-C6- Halogenalkenyloxy-Ci-C4-alkyl, C2-C6-Halogenalkenyl-Ci-C4-thioalkyl, Phenyl-C2-C4- halogenalkenyl, Heteroaryl-C2-C4-halogenalkenyl,: ein C2-C6-Alkenylrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, z.B. 2-Chlorvinyl, 2-Chlorallyl, 3-Chlorallyl, 2,3- Dichlorallyl, 3,3-Dichlorallyl, 2,3,3-Trichlorallyl, 2,3-Dichlorbut-2-enyl, 2-Bromvinyl, 2- Bromallyl, 3-Bromallyl, 2,3-Dibromallyl, 3,3-Dibromallyl, 2,3,3-Tribromallyl oder 2,3-C 2 -C 6 -haloalkenyl and the C 2 -C 6 -haloalkenyl parts of C 2 -C 6 -haloalkenyloxy-C 1 -C 4 -alkyl, C 2 -C 6 -haloalkenyl-C 1 -C 4 -thioalkyl, phenyl-C 2 -C 4 -haloalkenyl, heteroaryl- C 2 -C 4 -haloalkenyl: a C 2 -C 6 -alkenyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 2-chlorovinyl, 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromovinyl, 2-bromoallyl, 3-bromallyl, 2,3-dibromallyl, 3,3-dibromallyl, 2,3,3-tribromoallyl or 2,3-
Dibrombut-2-enyl;Dibromobut-2-enyl;
- C2-C6-Cyanoalkenyl: z.B. 2-Cyanovinyl, 2-Cyanoallyl, 3-Cyanoallyl, 2,3-Dicyanoallyl, 3,3-Dicyanoallyl, 2,3,3-Tricyanoallyl, 2,3-Dicyanobut-2-enyl;C2-C6 cyanoalkenyl: e.g. 2-cyanovinyl, 2-cyanoallyl, 3-cyanoallyl, 2,3-dicyanoallyl, 3,3-dicyanoallyl, 2,3,3-tricyanoallyl, 2,3-dicyanobut-2-enyl;
- C2-C6-Hydroxyalkenyl sowie die Hydroxy-Teile von Phenyl-Ci-C4-hydroxyalkenyl, Heteroaryl-Ci-C4-hydroxyalkenyl: z.B. 2-Hydroxyvinyl, 2-Hydroxyallyl, 3- Hydroxyallyl, 2,3-Dihydroxyallyl, 3,3-Dihydroxyallyl, 2,3,3-Trihydroxyallyl, 2,3- Dihydroxybut-2-enyl;C 2 -C 6 -hydroxyalkenyl and the hydroxy parts of phenyl-C 1 -C 4 -hydroxyalkenyl, heteroaryl-C 1 -C 4 -hydroxyalkenyl: e.g. 2-hydroxyvinyl, 2-hydroxyallyl, 3-hydroxyallyl, 2,3-dihydroxyallyl, 3,3-dihydroxyallyl, 2,3,3-trihydroxyallyl, 2,3-dihydroxybut-2-enyl;
- C3-C6-Halogenalkinyl: ein C3-C6-Alkinylrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, z.B. 1 ,1- Difluor-prop-2-in-1-yl, 3-lod-prop-2-in-1-yl, 4-Fluorbut-2-in-1-yl, 4-Chlorbut-2in-1-yl, 1 ,1-Difluorbut-2-in-1-yl, 4-lodbut-3-in-1-yl, 5-Fluorpent-3-in-1-yl, 5-lodpent-4-in-1-yl, 6-Fluorhex-4-in-1-yl oder 6-lodhex-5-in-1-yl;C3-C6-haloalkynyl: a C3-C6-alkynyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, e.g. 1,1-Difluoro-prop-2-yn-1-yl, 3-iodo-prop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2in-1 yl, 1, 1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1 yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;
- C2-C6-Halogenalkinyl sowie die C2-C6-Halogenalkinyl-Teile von C2-C6- Halogenalkinyloxy-Ci-C4-alkyl, C2-C6-Halogenalkinyl-Ci-C4-thioalkyl, Phenyl-C2-C4- halogenalkinyl, Heteroaryl-C2-C4-halogenalkinyl: ein C2-C6-Alkinylrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, z.B. 1 ,1-Difluor-prop-2-in-1-yl, 3-lod-prop-2-in-1-yl, A- Fluorbut-2-in-1-yl, 4-Chlorbut-2-in-1-yl, 1 ,1-Difluorbut-2-in-1-yl, 4-lodbut-3-in-1-yl, 5- Fluorpent-3-in-1-yl, 5-lodpent-4-in-1-yl, 6-Fluorhex-4-in-1-yl oder 6-lodhex-5-in-1-yl;C2-C6-haloalkynyl and the C2-C6-haloalkynyl parts of C2-C6-haloalkynyloxy-C1-C4-alkyl, C2-C6-haloalkynyl-C1-C4-thioalkyl, phenyl-C2-C4- haloalkynyl, heteroaryl-C 2 -C 4 -haloalkynyl: a C 2 -C 6 -alkynyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, eg 1, 1-difluoro-prop-2-yn 1-yl, 3-iodo-prop-2-yn-1-yl, A-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1, 1-difluorobut-2 -in-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohex-4-yne -1-yl or 6-iodohex-5-yn-1-yl;
- C2-C6-Cyanoalkinyl: z.B. 1 ,1-Dicyano-prop-2-in-1-yl, 3-Cyano -prop-2-in-1-yl, A- Cyano-but-2-in-1-yl, 1 ,1-Dicyanobut-2-in-1-yl, 4-Cyanobut-3-in-1-yl, 5-Cyanopent-3- in-1-yl, 5-Cyanopent-4-in-1-yl, 6-Cyanohex-4-in-1-yl oder 6-Cyanohex-5-in-1-yl;C2-C6 cyanoalkynyl: e.g. 1,1-dicyano-prop-2-yn-1-yl, 3-cyano-prop-2-yn-1-yl, A-cyano-but-2-yn-1-yl, 1,1-dicyanobutyl 2-yn-1-yl, 4-cyanobut-3-yn-1-yl, 5-cyanopent-3-yn-1-yl, 5-cyanopent-4-yn-1-yl, 6-cyanohex-4- in-1-yl or 6-cyanohex-5-yn-1-yl;
- C2-C6-Hydroxyalkinyl sowie die Hydroxy-Teile von Phenyl-C2-C4-hydroxyalkinyl: z.B. 1 ,1-Dihydroxy-prop-2-in-1-yl, 3-Hydroxy -prop-2-in-1-yl, 4-Hydroxy-but-2-in-1-yl, 1 ,1- Dihydroxybut-2-in-1-yl, 4-Hydroxybut-3-in-1-yl, 5-Hydroxypent-3-in-1-yl, 5- Hydroxypent-4-in-1-yl, 6-Hydroxyhex-4-in-1-yl oder 6-Hydroxyhex-5-in-1-yl;C 2 -C 6 -hydroxyalkynyl and the hydroxy parts of phenyl-C 2 -C 4 -hydroxyalkynyl: e.g. 1, 1-dihydroxy-prop-2-yn-1-yl, 3-hydroxyprop-2-yn-1-yl, 4-hydroxy-but-2-yn-1-yl, 1, 1-dihydroxybutyl 2-yn-1-yl, 4-hydroxybut-3-yn-1-yl, 5-hydroxypent-3-yn-1-yl, 5-hydroxypent-4-yn-1-yl, 6-hydroxyhex-4 in-1-yl or 6-hydroxyhex-5-yn-1-yl;
- Ci-C6-Alkylsulfinyl (Ci-C6-Alkyl-S(=O)-) sowie die Ci-C6-Alkylsulfinyl-Teile von Ci-C6-Alkylsulfinyl-Ci-C4-alkyl: z.B. Methylsulfinyl, Ethylsulfinyl, Propylsulfinyl, 1- Methylethylsulfinyl, Butylsulfinyl, 1-Methylpropylsulfinyl, 2-Methylpropyl-sulfinyl, 1 ,1-Dimethylethylsulfinyl, Pentylsulfinyl, 1-Methylbutylsulfinyl, 2-Methyl- butylsulfinyl, 3-Methylbutylsulfinyl, 2,2-Dimethylpropylsulfinyl, 1 — Ethylpropyl-sulfinyl,C 1 -C 6 -alkylsulfinyl (C 1 -C 6 -alkyl-S (OO) -) and the C 1 -C 6 -alkylsulfinyl parts of C 1 -C 6 -alkylsulfinyl-C 1 -C 4 -alkyl: for example methylsulfinyl, Ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1 - ethylpropyl sulfinyl,
1 ,1-Dimethylpropylsulfinyl, 1 ,2-Dimethylpropylsulfinyl, Hexylsulfinyl, 1- Methylpentylsulfinyl, 2-Methylpentylsulfinyl, 3-Methylpentylsulfinyl, 4-Methyl pentylsulfinyl, 1 ,1-Dimethylbutylsulfinyl, 1 ,2-Dimethylbutylsulfinyl, 1 ,3-Dimethylbutyl- sulfinyl, 2,2-Dimethylbutylsulfinyl, 2,3-Dimethylbutylsulfinyl, 3,3-Dimethylbutyl- sulfinyl, 1— Ethylbutylsulfinyl, 2— Ethylbutylsulfinyl, 1 ,1 ,2-Trimethylpropylsulfinyl,1, 1-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1, 1-dimethylbutylsulfinyl, 1, 2-dimethylbutylsulfinyl, 1, 3-dimethylbutylsulfinyl , 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1, 1, 2-trimethylpropylsulfinyl,
1 ,2,2-Trimethylpropylsulfinyl, 1— Ethyl— 1— methylpropylsulfinyl und 1— Ethyl— 2— methylpropylsulfinyl;1, 2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl;
- Ci-Cδ-Halogenalkylsulfinyl sowie die Ci-C6-Halogenalkylsulfinyl-Teile von Ci-Cβ- Halogenalkylsulfinyl-Ci-C4-alkyl: Ci-Cδ-Alkylsulfinylrest wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. Fluormethylsulfinyl, Difluormethylsulfinyl, Trifluormethylsulfinyl, Chlordifluormethylsulfinyl, Bromdifluormethylsulfinyl, 2-Fluorethylsulfinyl, 2- Chlorethylsulfinyl, 2-Bromethylsulfinyl, 2-lodethylsulfinyl, 2 ,2— Difluorethylsu If inyl , 2,2,2-Trifluor-ethylsulfinyl, 2,2,2-Trichlorethylsulfinyl, 2-Chlor-2-fluorethylsulfinyl,- Ci-Cδ-haloalkylsulfinyl and the Ci-C6-Halogenalkylsulfinyl parts of Ci-Cβ- haloalkylsulfinyl-Ci-C4-alkyl: Ci-Cδ-Alkylsulfinylrest as mentioned above, which partially or completely by fluorine, chlorine, bromine and / or iodine is substituted, eg Fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2, 2-difluoroethylsulfonyl, 2,2,2-trifluoro-ethylsulfinyl, 2,2,2- Trichloroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl,
2-Chlor-2,2-difluorethylsulfinyl, 2,2-Dichlor-2-fluorethylsulfinyl, Pentafluorethylsulfinyl, 2-Fluorpropylsulfinyl, 3-Fluorpropylsulfinyl, 2- Chlorpropylsulfinyl, 3-Chlorpropyl-sulfinyl, 2-Brompropylsulfinyl, 3- Brompropylsulfinyl, 2,2-Difluorpropylsulfinyl, 2,3-Difluorpropylsulfinyl, 2,3- Dichlorpropylsulfinyl, 3,3,3— Trifluorpropylsulfinyl, 3,3,3-Trichlorpropylsulfinyl,2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 2, 2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl,
2,2,3,3,3-Pentafluorpropylsulfinyl, Heptafluorpropylsulfinyl, 1-(Fluormethyl)-2- fluorethylsulfinyl, 1-(Chlormethyl)-2-chlorethylsulfinyl, 1-(Brommethyl)-2- bromethylsulfinyl, 4-Fluorbutylsulfinyl, 4-Chlorbutylsulfinyl, 4-Brombutylsulfinyl, Nonafluorbutylsulfinyl, 5-Fluorpentylsulfinyl, 5-Chlorpentyl-sulfinyl, 5- Brompentylsulfinyl, 5-lodpentylsulfinyl, Undecafluorpentylsulfinyl, 6-Fluorhexyl- sulfinyl, 6-Chlorhexylsulfinyl, 6-Bromhexylsulfinyl, 6-lodhexylsulfinyl und Tridecafluorhexylsulfinyl;2,2,3,3,3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl, 1- (fluoromethyl) -2-fluoroethylsulfinyl, 1- (chloromethyl) -2-chloroethylsulfinyl, 1- (bromomethyl) -2-bromoethylsulfinyl, 4-fluorobutylsulfinyl, 4- Chlorobutylsulfinyl, 4-bromobutylsulfinyl, Nonafluorobutylsulfinyl, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl and tridecafluorohexylsulfinyl;
- Ci-Ce-Alkylsulfonyl (Ci-C6-Alkyl-S(O)2-) sowie die Ci-C6-Alkylsulfonyl-Teile von Ci-Ce-Alkylsulfonyl-Ci^-alkyl, Ci-C6-Alkylsulfonylamino, Ci-C6- Alkylsulfonylamino-Ci-C4-alkyl, Ci-C6-Alkylsulfonyl-(Ci-C6-alkylamino)-Ci-C4-alkyl: z.B. Methylsulfonyl, Ethylsulfonyl, Propylsulfonyl, 1-Methylethylsulfonyl, Butylsulfonyl, 1-Methylpropylsulfonyl, 2-Methyl-propylsulfonyl, 1 ,1-C 1 -C 6 -alkylsulfonyl (C 1 -C 6 -alkyl-S (O) 2 -) and the C 1 -C 6 -alkylsulfonyl parts of C 1 -C 6 -alkylsulfonyl-C 1 -C 4 -alkyl, C 1 -C 6 -alkylsulfonylamino, Ci-C 6 - alkylsulfonylamino-Ci-C4-alkyl, Ci-C6-alkylsulfonyl (Ci-C6-alkylamino) -C-C4-alkyl: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1, 1
Dimethylethylsulfonyl, Pentylsulfonyl, 1-Methylbutylsulfonyl, 2-Methylbutylsulfonyl, 3-Methylbutylsulfonyl, 1 ,1-Dimethylpropylsulfonyl, 1 ,2-Di-methyl propylsulfonyl, 2,2- Dimethylpropylsulfonyl, 1-Ethylpropylsulfonyl, Hexylsulfonyl, 1- Methylpentylsulfonyl, 2-Methylpentylsulfonyl, 3-Methyl pentylsulfonyl, A- Methylpentylsulfonyl, 1 ,1-Dimethylbutylsulfonyl, 1 ,2-Dimethylbutylsulfonyl, 1 ,3-Dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl , 3-methylpentylsulfonyl, A-methylpentylsulfonyl, 1, 1-dimethylbutylsulfonyl, 1, 2-dimethylbutylsulfonyl, 1, 3
Dimethylbutylsulfonyl, 2,2-Dimethylbutylsulfonyl, 2,3-Dimethylbutylsulfonyl, 3,3- Dimethylbutylsulfonyl, 1-Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1 ,1 ,2-Trimethyl- propylsulfonyl, 1 ,2,2-Trimethylpropylsulfonyl, 1-Ethyl-1-methylpropylsulfonyl und 1-Ethyl-2-methylpropylsulfonyl;Dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1, 1, 2-trimethyl-propylsulfonyl, 1, 2,2-trimethyl-propylsulfonyl, 1-ethyl- 1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;
- Ci-Cδ-Halogenalkylsulfonyl sowie die Ci-Cδ-Halogenalkylsulfonyl-Teile von Ci-Cβ- Halogenalkylsulfonyl-Ci-C4-alkyl, Ci-Ce-Halogenalkylsulfonylamino: einen Ci-Cβ- Alkylsulfonylrest wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. Fluormethylsulfonyl, Difluormethylsulfonyl, Trifluormethylsulfonyl, Chlordifluormethylsulfonyl,- Ci-Cδ-haloalkylsulfonyl and the Ci-Cδ-Halogenalkylsulfonyl parts of Ci-Cβ- haloalkylsulfonyl-Ci-C4-alkyl, Ci-Ce-Halogenalkylsulfonylamino: a Ci-Cβ- Alkylsulfonylrest as mentioned above, which partially or completely by fluorine , Chlorine, bromine and / or iodine is substituted, eg Fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl,
Bromdifluormethylsulfonyl, 2-Fluorethylsulfonyl, 2-Chlorethylsulfonyl, 2- Bromethylsulfonyl, 2-lodethylsulfonyl, 2,2-Difluorethyl-sulfonyl, 2,2,2- Trifluorethylsulfonyl, 2-Chlor-2-fluorethylsulfonyl, 2-Chlor-2,2-difluorethylsulfonyl, 2,2-Dichlor-2-fluorethylsulfonyl, 2,2,2-Trichlorethylsulfonyl, Pentafluorethylsulfonyl, 2-Fluorpropylsulfonyl, 3-Fluorpropylsulfonyl, 2-Chlor-propylsulfonyl, 3-Bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2- difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloro-propylsulfonyl, 3
Chlorpropylsulfonyl, 2-Brompropylsulfonyl, 3-Brompropylsulfonyl, 2,2- Difluorpropylsulfonyl, 2,3-Difluorpropylsulfonyl, 2,3-Dichlorpropylsulfonyl, 3,3,3- Trifluorpropylsulfonyl, S.S.S-Trichlorpropylsulfonyl, 2,2,3,3,3-Pentafluor- propylsulfonyl, Heptafluorpropylsulfonyl, 1-(Fluormethyl)-2-fluorethylsulfonyl, 1- (Chlormethyl^-chlorethylsulfonyl, 1-(Brommethyl)-2-bromethylsulfonyl, A-Chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, SSS-trichloropropylsulfonyl, 2,2,3,3,3- Pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1- (fluoromethyl) -2-fluoroethylsulfonyl, 1- (chloromethyl) -chloroethylsulfonyl, 1- (bromomethyl) -2-bromoethylsulfonyl, A-
Fluorbutylsulfonyl, 4-Chlorbutylsulfonyl, 4-Brombutylsulfonyl, Nonafluorbutylsulfonyl, 5-Fluorpentylsulfonyl, 5-Chlorpentylsulfonyl, 5-Brom- pentylsulfonyl, 5-lod-pentylsulfonyl, 6-Fluorhexylsulfonyl, 6-Bromhexylsulfonyl, 6- lodhexylsulfonyl und Tridecafluorhexylsulfonyl;Fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromo-pentylsulfonyl, 5-iodo-pentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl and tridecafluorohexylsulfonyl;
Ci-C4-AIkOXy sowie die Alkoxyteile von Hydroxycarbonyl-Ci-C4-alkoxy, C1-C4- Alkoxycarbonyl-Ci-C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl und C1-C4- alkyl-Ci-C4-alkoxycarbonylamino: z.B. Methoxy, Ethoxy, Propoxy, 1-Methyl-ethoxy, Butoxy, 1-Methylpropoxy, 2-Methylpropoxy und 1 ,1-Dimethylethoxy;C 1 -C 4 -alkoxy and the alkoxy moieties of hydroxycarbonyl-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy C4 alkyl-Ci-C4-alkoxycarbonylamino: for example, methoxy, ethoxy, propoxy, 1-methyl-ethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1, 1-dimethylethoxy;
- Ci-Cδ-Alkoxy sowie die Alkoxyteile von Hydroxycarbonyl-Ci-Cδ-alkoxy, Ci-Cβ- Alkoxycarbonyl-Ci-Cδ-alkoxy, N-(Ci-C6-Alkoxy)-N-(Ci-C6-alkyl)-aminocarbonyl,C 1 -C 6 -alkoxy and also the alkoxy parts of hydroxycarbonyl-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkoxy, N- (C 1 -C 6 -alkoxy) -N- (C 1 -C 6 -alkyl) aminocarbonyl,
N-(C3-C6-Alkenyl)-N-(Ci-C6-alkoxy)-aminocarbonyl, N-(C3-C6-Alkinyl)-N-(Ci- C6-alkoxy)-aminocarbonyl und Ci-C6-Alkoxyimino-Ci-C6-alkyl: Ci-C4-AIkOXy wie voranstehend genannt, sowie z.B. Pentoxy, 1-Methyl-butoxy, 2-Methylbutoxy, 3-Methoxylbutoxy, 1 ,1-Dimethyl-propoxy, 1 ,2-Dimethyl-propoxy, 2,2-Dimethylpropoxy, 1-Ethylpropoxy, Hexoxy, 1-Methylpentoxy, 2-Methylpentoxy,N- (C 3 -C 6 -alkenyl) -N- (C 1 -C 6 -alkoxy) -aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (C 1 -C 6 -alkoxy) -aminocarbonyl and C 1 -C 6 Alkoxyimino-C 1 -C 6 -alkyl: C 1 -C 4 -alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy, 1, 1-dimethyl-propoxy, 1, 2-dimethyl propoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy,
3-Methylpentoxy, 4-Methylpentoxy, 1 ,1-Di-methylbutoxy,1 ,2-Dimethyl-butoxy, 1 ,3-Dimethylbutoxy, 2,2-Dimethylbutoxy, 2,3-Dimethylbutoxy, 3,3-Dimethyl-butoxy, 1-Ethylbutoxy, 2-Ethylbutoxy, 1 ,1 ,2-Tri-methylpropoxy, 1 ,2,2-Trimethyl-propoxy, 1-Ethyl-1-methylpropoxy und 1-Ethyl-2-methylpropoxy;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-1-methylpropoxy and 1-ethyl-2-methylpropoxy;
- Ci-C4-Halogenalkoxy: ein Ci-C4-Alkoxyrest wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. FIu- ormethoxy, Difluormethoxy, Trifluormethoxy, Chlordifluormethoxy, Bromdifluor- methoxy, 2-Fluorethoxy, 2-Chlorethoxy, 2-Brommethoxy, 2-lodethoxy, 2,2-Difluor- ethoxy, 2,2,2-Trifluorethoxy, 2-Chlor-2-fluorethoxy, 2-Chlor-2,2-difluorethoxy, 2,2-Ci-C4-haloalkoxy: a Ci-C4-alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, thus e.g. Fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro 2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-
Dichlor-2-fluorethoxy, 2,2,2-Trichlorethoxy, Pentafluorethoxy, 2-Fluorpropoxy, 3- Fluorpropoxy, 2-Chlorpropoxy, 3-Chlorpropoxy, 2-Brompropoxy, 3-Brompropoxy, 2,2-Difluorpropoxy, 2,3-Difluorpropoxy, 2,3-Dichlorpropoxy, 3,3,3-Trifluorpropoxy, 3,3,3-Trichlorpropoxy, 2,2,3,3,3-Pentafluorpropoxy, Heptafluorpropoxy, 1- (Fluormethyl)-2-fluorethoxy, 1-(Chlormethyl)-2-chlorethoxy, 1-(Brommethyl)-2- bromethoxy, 4-Fluorbutoxy, 4-Chlorbutoxy, 4-Brombutoxy und Nonafluorbutoxy;Dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3- Difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1- (fluoromethyl) -2-fluoroethoxy, 1- (Chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy;
- Ci-Cδ-Halogenalkoxy sowie die Ci-Cδ-Halogenalkoxy-Teile von Ci-Cβ- Halogenalkoxy-Ci-C4-alkyl, Ci-C6-Halogenalkoxycarbonyl-Ci-C4-alkyl: C1-C4- Halogenalkoxy wie voranstehend genannt, sowie z.B. 5-Fluorpentoxy, 5-- Ci-Cδ-haloalkoxy and the Ci-Cδ-haloalkoxy parts of Ci-Cβ- haloalkoxy-Ci-C4-alkyl, Ci-C6-haloalkoxycarbonyl-Ci-C4-alkyl: C1-C4-haloalkoxy as mentioned above, and eg 5-fluoropentoxy, 5-
Chlorpentoxy, 5-Brompentoxy, 5-lodpentoxy, Undecafluorpentoxy, 6-Fluorhexoxy, 6-Chlorhexoxy, 6-Bromhexoxy, 6-lodhexoxy und Tridecafluorhexoxy;Chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and tridecafluorohexoxy;
Ci-C6-Alkoxy-Ci-C4-alky sowie die Ci-C6-Alkoxy-Ci-C4-alkyl-Teile von Ci-Cβ- Alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl I: durch Ci-Cδ-Alkoxy wie vorstehend genannt substituiertes Ci-C4-Alkyl, also z.B. für Methoxymethyl, Ethoxymethyl, Propoxy- methyl, (I-Methylethoxy)methyl, Butoxymethyl, (I-Methylpropoxy)methyl, (2- Methyl-propoxy)methyl, (1 ,1-Dimethylethoxy)methyl, 2-(Methoxy)ethyl, 2- (Ethoxy)ethyl, 2-(Propoxy)ethyl, 2-(1-Methylethoxy)ethyl, 2-(Butoxy)ethyl, 2-(1- Methylpropoxy)-ethyl, 2-(2-Methylpropoxy)ethyl, 2-(1 ,1-Dimethylethoxy)ethyl, 2-C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl and also the C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl parts of C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl I: by C 1 -C 6 Alkoxy as mentioned above substituted Ci-C4-alkyl, eg for methoxymethyl, ethoxymethyl, propoxymethyl, (1-methylethoxy) methyl, butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, (1, 1-dimethylethoxy) methyl, 2- (methoxy) ethyl, 2- (ethoxy) ethyl, 2- (propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methylpropoxy) ethyl, 2 - (1, 1-dimethylethoxy) ethyl, 2
(Methoxy)-propyl, 2-(Ethoxy)propyl, 2-(Propoxy)propyl, 2-(1-Methylethoxy)propyl, 2-(Butoxy)propyl, 2-(1-Methylpropoxy)propyl, 2-(2-Methylpropoxy)propyl, 2-(1 ,1- Dimethylethoxy)propyl, 3-(Methoxy)propyl, 3-(Ethoxy)-propyl, 3-(Propoxy)propyl, 3-(1-Methylethoxy)-propyl, 3-(Butoxy)propyl, 3-(1-Methylpropoxy)propyl, 3-(2- Methylpropoxy)propyl, 3-(1 ,1-Dimethylethoxy)propyl, 2-(Methoxy)-butyl, 2- (Ethoxy)butyl, 2-(Propoxy)-butyl, 2-(1-Methylethoxy)butyl, 2-(Butoxy)butyl, 2-(1- Methylpropoxy)butyl, 2-(2-Methylpropoxy)butyl, 2-(1 ,1-Dimethylethoxy)butyl, 3- (Methoxy)butyl, 3-(Ethoxy)-butyl, 3-(Propoxy)butyl, 3-(1-Methylethoxy)butyl, 3-(Methoxy) propyl, 2- (ethoxy) propyl, 2- (propoxy) propyl, 2- (1-methylethoxy) propyl, 2- (butoxy) propyl, 2- (1-methylpropoxy) propyl, 2- (2- Methylpropoxy) propyl, 2- (1, 1-dimethylethoxy) propyl, 3- (methoxy) propyl, 3- (ethoxy) propyl, 3- (propoxy) propyl, 3- (1-Methylethoxy) propyl, 3- (Butoxy) propyl, 3- (1-methylpropoxy) propyl, 3- (2-methylpropoxy) propyl, 3- (1,1-dimethylethoxy) propyl, 2- (methoxy ) -butyl, 2- (ethoxy) butyl, 2- (propoxy) -butyl, 2- (1-methylethoxy) butyl, 2- (butoxy) butyl, 2- (1-methylpropoxy) butyl, 2- (2-methylpropoxy butyl, 2- (1,1-dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) -butyl, 3- (propoxy) butyl, 3- (1-methylethoxy) butyl, 3-
(Butoxy)-butyl, 3-(1-Methyl-propoxy)butyl, 3-(2-Methylpropoxy)butyl, 3-(1 ,1- Dimethylethoxy)butyl, 4-(Methoxy)-butyl, 4-(Ethoxy)butyl, 4-(Propoxy)butyl, 4-(1- Methylethoxy)butyl, 4-(Butoxy)butyl, 4-(1-Methylpropoxy)butyl, 4-(2- Methylpropoxy)butyl und 4-(1 ,1-Dimethylethoxy)-butyl;(Butoxy) butyl, 3- (1-methylpropoxy) butyl, 3- (2-methylpropoxy) butyl, 3- (1, 1-dimethylethoxy) butyl, 4- (methoxy) butyl, 4- (ethoxy) butyl, 4- (propoxy) butyl, 4- (1-methylethoxy) butyl, 4- (butoxy) butyl, 4- (1-methylpropoxy) butyl, 4- (2-methylpropoxy) butyl and 4- (1, 1) dimethylethoxy) butyl;
- Ci-C4-Alkoxycarbonyl sowie die Alkoxycarbonylteile von Ci-C4-Alkoxycarbonyl-Ci- C4-alkoxy, Ci-C4-Alkoxy-Ci-C4-alkoxycarbonyl und Di-(Ci-C4-alkyl)-amino-Ci-C4- alkoxycarbonyl: z.B. Methoxycarbonyl, Ethoxycarbonyl, Propoxycarbonyl, 1- Methylethoxycarbonyl, Butoxycarbonyl, 1-Methylpropoxycarbonyl, 2-Methylprop- oxycarbonyl oder 1 ,1-Dimethylethoxycarbonyl;C 1 -C 4 -alkoxycarbonyl and the alkoxycarbonyl moieties of C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxycarbonyl and di- (C 1 -C 4 -alkyl) -amino-C 1 -C 4 -cyclo alkoxycarbonyl: eg Methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1, 1-dimethylethoxycarbonyl;
- Ci-Cδ-Alkoxycarbonyl sowie die Alkoxycarbonylteile von Ci-Cδ-Alkoxycarbonyl-Ci- Cβ-alkoxy und Ci-C6-Alkoxycarbonylamino-Ci-C4-alkyl: Ci-C4-Alkoxycarbonyl, wie voranstehend genannt, sowie z.B. Pentoxycarbonyl, 1-Methylbutoxycarbonyl, 2- Methylbutoxycarbonyl, 3-Methyl-butoxycarbonyl, 2,2-Dimethylpropoxycarbonyl, 1-- Ci-Cδ-alkoxycarbonyl and the Alkoxycarbonylteile of Ci-Cδ-alkoxycarbonyl-Ci- Cβ-alkoxy and Ci-C6-Alkoxycarbonylamino-Ci-C4-alkyl: Ci-C4-Alkoxycarbonyl, as mentioned above, as well as e.g. Pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1
Ethylpropoxycarbonyl, Hexoxy-carbonyl, 1 ,1-Dimethylpropoxycarbonyl, 1 ,2- Dimethylpropoxycarbonyl, 1-Methyl-pentoxycarbonyl, 2-Methylpentoxycarbonyl, 3- Methylpentoxycarbonyl, 4-Methyl-pentoxycarbonyl, 1 ,1-Dimethylbutoxycarbonyl, 1 ,2-Dimethylbutoxycarbonyl, 1 ,3-Dimethylbutoxycarbonyl, 2,2- Dimethylbutoxycarbonyl, 2,3-Dimethylbutoxycarbonyl, 3,3-Dimethylbutoxycarbonyl,Ethylpropoxycarbonyl, hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1, 2-dimethylbutoxycarbonyl, 1, 3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,
1-Ethylbutoxycarbonyl, 2-Ethylbutoxycarbonyl, 1 ,1 ,2-Trimethylpropoxycarbonyl, 1 ,2,2-Trimethylpropoxycarbonyl, 1-Ethyl-1-methyl-propoxycarbonyl oder 1 -Ethyl-2- methyl-propoxycarbonyl;1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1, 1, 2-trimethylpropoxycarbonyl, 1, 2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methyl-propoxycarbonyl or 1-ethyl-2-methyl-propoxycarbonyl;
- Ci-C4-Alkylthio sowie die Ci-C4-Alkylthio-Teile von Ci-C6-Halogenalkyl-Ci-C4- thioalkyl, Ca-Cδ-Halogenalkenyl-Ci^-thioalkyl, C2-C6-Halogenalkinyl-Ci-C4- thioalkyl: z.B. Methylthio, Ethylthio, Propylthio, 1-Methylethylthio, Butylthio, 1-Methylpropylthio, 2-Methylpropylthio und 1 ,1-Dimethylethylthio;- Ci-C 4 alkylthio and Ci-C4-alkylthio moieties of Ci-C 6 haloalkyl-Ci-C 4 - thioalkyl, Ca-Cδ-haloalkenyl-Ci ^ thioalkyl, C2-C6-haloalkynyl-Ci -C 4 thioalkyl: for example, methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1, 1-dimethylethylthio;
- Ci-C6-Alkylthio sowie die Ci-C6-Alkylthio-Teile von Ci-C6-Alkylthio-Ci-C4-alkyl: Ci- C4-Alkylthio wie voranstehend genannt, sowie z.B. Pentylthio, 1-Methylbutylthio, 2- Methylbutylthio, 3-Methylbutylthio, 2,2-Dimethylpropylthio, 1-Ethylpropylthio, He- xylthio, 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-Dimethylbutyl-thio, 2,3-- C 1 -C 6 -alkylthio and the C 1 -C 6 -alkylthio parts of C 1 -C 6 -alkylthio-C 1 -C 4 -alkyl: C 1 -C 4 -alkylthio as mentioned above, and also, for example, pentylthio, 1-methylbutylthio, 2 Methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, 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-Ethyl butyl-th io , 1 ,1 ,2- Trimethylpropylthio, 1 ,2,2-Trimethylpropylthio, 1-Ethyl-1-methylpropyl-thio und 1- Ethyl-2-methylpropylthio; - Ci-C6-Alkylamino sowie die Ci-C6-Alkylaminoreste von N(Ci-C6-Alkylamino)imino- Ci-C6-alkyl, Ci-C6-Alkylamino-Ci-C4-alkyl, Ci-C6-Alkylsulfonyl-(Ci-C6-alkylamino)- Ci-C4-alkyl, Ci-C6-Alkylcarbonyl-(Ci-C6-alkylamino)-Ci-C4-alkyl, [(CrC6- Alkyl)amino]cyanoimino und CrC6-Alkylaminocarbonyloxy-CrC4-alkyl: z.B. Methy- lamino, Ethylamino, Propylamino, 1-Methylethylamino, Butylamino, 1- Methylpropylamino, 2-Methylpropylamino, 1 ,1-Dimethylethylamino, Pentylamino, 1- Methylbutylamino, 2-Methylbutylamino, 3-Methylbutylamino, 2,2-Dimethylpropyl- amino, 1-Ethylpropylamino, Hexylamino, 1 ,1-Dimethylpropylamino, 1 ,2- Dimethylpropylamino, 1-Methylpentylamino, 2-Methylpentylamino, 3-Methyl- pentylamino, 4-Methylpentylamino, 1 ,1-Dimethylbutylamino, 1 ,2-Dimethylbutyl- amino, 1 ,3-Dimethylbutylamino, 2,2-Dimethylbutylamino, 2,3-Dimethylbutylamino, 3,3-Dimethylbutylamino, 1-Ethylbutylamino, 2-Ethylbutylamino, 1 ,1 ,2-Trimethyl- propylamino, 1 ,2,2-Trimethylpropylamino, 1-Ethyl-1-methylpropylamino oder 1- Ethyl-2-methylpropylamino;Dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1, 1, 2-trimethylpropylthio, 1, 2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl- 2-methylpropylthio; - C 1 -C 6 -alkylamino and the C 1 -C 6 -alkylamino radicals of N (C 1 -C 6 -alkylamino) -imino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino-C 1 -C 4 -alkyl, C 1 -C 6 -alkylsulfonyl - (Ci-C 6 -alkylamino) - Ci-C4-alkyl, Ci-C6-alkylcarbonyl (Ci-C 6 -alkylamino) -C-C 4 alkyl, [(-C 6 - alkyl) amino] cyanoimino, and C 1 -C 6 -alkylaminocarbonyloxy-C 1 -C 4 -alkyl: for example methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1, 1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3 Methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, 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-trimethyl- propylamino, 1, 2,2-trimethylpropylamino, 1-ethyl-1-methyl propylamino or 1-ethyl-2-methylpropylamino;
- Di(Ci-C4-alkyl)amino: z.B. N,N-Dimethylamino, N,N-Diethylamino, N1N- Dipropylamino, N1N-Di-(I -methylethyl)-amino, N,N-Dibutylamino, N1N-Di-(I- methylpropyl)amino, N,N-Di-(2-methylpropyl)-amino, N1N-Di-(1 ,1-dimethylethyl)- amino, N-Ethyl-N-methylamino, N-Methyl-N-propylamino, N-Methyl-N-(1- methylethyl)amino, N-Butyl-N-methylamino, N-Methyl-N-(1-methylpropyl)amino, N- Methyl-N-(2-methylpropyl)amino, N-(1 ,1-Dimethyl-ethyl)-N-methylamino, N-Ethyl-N- propylamino, N-Ethyl-N-(1-methylethyl)amino, N-Butyl-N-ethylamino, N-Ethyl-N-(1- methylpropyl)amino, N-Ethyl-N-(2-methylpropyl)-amino, N-Ethyl-N-(1 ,1-dimethyl- ethyl)amino, N-(1-Methylethyl)-N-propylamino, N-Butyl-N-propylamino, N-(1-- di (C 1 -C 4 -alkyl) amino: for example N, N-dimethylamino, N, N-diethylamino, N 1 N-dipropylamino, N 1 N -di (1-methylethyl) amino, N, N-dibutylamino, N 1 N-di- (I-methylpropyl) amino, N, N-di- (2-methylpropyl) amino, N 1 N-di (1, 1-dimethylethyl) - amino, N-ethyl-N-methylamino , N-methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino, N-methyl-N- ( 2-methylpropyl) amino, N- (1, 1-dimethylethyl) -N-methylamino, N-ethyl-N-propylamino, N-ethyl-N- (1-methylethyl) amino, N -butyl-N-ethylamino , N-ethyl-N- (1-methylpropyl) amino, N-ethyl-N- (2-methylpropyl) -amino, N-ethyl-N- (1, 1-dimethyl-ethyl) -amino, N- (1-) Methylethyl) -N-propylamino, N-butyl-N-propylamino, N- (1-
Methylpropyl)-N-propylamino, N-(2-Methylpropyl)-N-propylamino, N-(1 ,1-Dimethyl- ethyl)-N-propylamino, N-Butyl-N-(1 -methylethyl-)amino, N-(1 -Methylethyl)-N-(1 - methylpropyl)amino, N-(1-Methylethyl)-N-(2-methyl-propyl)amino, N-(1 ,1-Dimethyl- ethyl)-N-(1 -methylethyl)amino, N-Butyl-N-(1 -methylpropyl)amino, N-Butyl-N-(2- methylpropyl)amino, N-Butyl-N-(1 ,1-dimethyl-ethyl)amino, N-(1-Methylpropyl)-N-(2- methylpropyl)amino, N-(1 ,1-Dimethylethyl)-N-(1-methylpropyl)amino und N-(1 ,1 -Di- methylethyl)-N-(2-methylpropyl)amino;Methylpropyl) -N-propylamino, N- (2-methylpropyl) -N-propylamino, N- (1, 1-dimethyl-ethyl) -N-propylamino, N -butyl-N- (1-methylethyl) -amino, N - (1-methylethyl) -N- (1-methylpropyl) amino, N- (1-methylethyl) -N- (2-methyl-propyl) amino, N- (1, 1-dimethyl-ethyl) -N- ( 1-methylethyl) amino, N-butyl-N- (1-methylpropyl) amino, N-butyl-N- (2-methylpropyl) amino, N-butyl-N- (1, 1-dimethyl-ethyl) -amino, N - (1-methylpropyl) -N- (2-methylpropyl) amino, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) amino and N- (1, 1-dimethylethyl) -N- ( 2-methylpropyl) amino;
- Di(Ci-C6-alkyl)amino sowie die Dialkylaminoreste von N-(Di-Ci-C6-alkylamino)- imino-Ci-Ce-alkyl, Di(Ci-C6-alkyl)amino-Ci-C4-alkyl, [Di(CrC6- alkylamino)cabonyloxy]-Ci-C4-alkyl und [Di(Ci-C6-alkyl)amino]cyanoimino: Di(CrC4- alkyl)amino wie voranstehend genannt sowie: z.B. N,N-Dipentylamino, N1N- Dihexylamino, N-Methyl-N-pentylamino, N-Ethyl-N-pentylamino, N-Methyl-N- hexylamino und N-Ethyl-N-hexylamino;Di (C 1 -C 6 -alkyl) amino and the dialkylamino radicals of N- (di-C 1 -C 6 -alkylamino) -imino-C 1 -C 6 -alkyl, di (C 1 -C 6 -alkyl) amino-C 1 -C 4 - alkyl, [di (C 1 -C 6 -alkylamino) cabonyloxy] -Ci-C 4 -alkyl and [di (C 1 -C 6 -alkyl) amino] cyanoimino: di (C 1 -C 4 -alkyl) amino as mentioned above and also: for example N, N- dipentylamino, N 1 N- dihexylamino, N-methyl-N-pentylamino, N-ethyl-N-pentylamino, N-methyl-N-hexylamino and N-ethyl-N-hexylamino;
- (Ci-C4-Alkylamino)carbonyl sowie die (Ci-C4-Alkylamino)carbonyl-Teile von (Ci- C4-Alkylamino)carbonylamino: z.B. Methylaminocarbonyl, Ethylaminocarbonyl, Pro- pylaminocarbonyl, 1-Methylethylaminocarbonyl, Butylaminocarbonyl, 1-Methyl- propylaminocarbonyl, 2-Methylpropylaminocarbonyl oder 1 ,1-Dimethylethylamino- carbonyl;(C 1 -C 4 -alkylamino) carbonyl and the (C 1 -C 4 -alkylamino) carbonyl parts of (C 1 -C 4 -alkylamino) carbonylamino: for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylcyclo propylaminocarbonyl, 2-methylpropylaminocarbonyl or 1, 1-dimethylethylaminocarbonyl;
- Di(Ci-C4-alkyl)aminocarbonyl sowie die Di(Ci-C4-alkyl)aminocarbonyl-Teile von Di(Ci-C4-alkyl)aminocarbonylamino: z.B. N,N-Dimethylaminocarbonyl, N,N-Diethyl- aminocarbonyl, N1N-Di-(I -methylethyl)aminocarbonyl, N,N-Dipropylaminocarbonyl, N,N-Dibutylaminocarbonyl, N1N-Di-(I -methylpropyl)aminocarbonyl, N,N-Di-(2- methylpropyl)aminocarbonyl, N1N-Di-(1 ,1-dimethylethyl)aminocarbonyl, N-Ethyl-N- methylaminocarbonyl, N-Methyl-N-propylaminocarbonyl, N-Methyl-N-(1 -methyl- ethyl)aminocarbonyl, N-Butyl-N-methylaminocarbonyl, N-Methyl-N-(1-methyl- propyl)aminocarbonyl, N-Methyl-N-(2-methylpropyl)aminocarbonyl, N-(1 ,1-Dimethyl- ethyl)-N-methylaminocarbonyl, N-Ethyl-N-propylaminocarbonyl, N-Ethyl-N-(1- methylethyl)aminocarbonyl, N-Butyl-N-ethylaminocarbonyl, N-Ethyl-N-(1 -methyl- propyl)aminocarbonyl, N-Ethyl-N-(2-methylpropyl)aminocarbonyl, N-Ethyl-N-(1 ,1- dimethylethyl)aminocarbonyl, N-(1-Methylethyl)-N-propylaminocarbonyl, N-Butyl-N- propylaminocarbonyl, N-(1 -Methylpropyl)-N-propylaminocarbonyl, N-(2-Methyl- propyl)-N-propylaminocarbonyl, N-(1 ,1-Dimethylethyl)-N-propylaminocarbonyl, N- Butyl-N-(1-methylethyl)aminocarbonyl, N-(1-Methylethyl)-N-(1-methylpropyl)- aminocarbonyl, N-(1-Methylethyl)-N-(2-methylpropyl)aminocarbonyl, N-(1 ,1- Dimethylethyl)-N-(1-methylethyl)aminocarbonyl, N-Butyl-N-(i-methylpropyl)- aminocarbonyl, N-Butyl-N-(2-methylpropyl)aminocarbonyl, N-Butyl-N-(1 ,1-dimethyl- ethyl)aminocarbonyl, N-(1-Methylpropyl)-N-(2-methylpropyl)aminocarbonyl, N-(1 ,1- Dimethylethyl)-N-(1-methylpropyl)aminocarbonyl oder N-(1 ,1-Dimethylethyl)-N-(2- methylpropyl)aminocarbonyl;- Di (Ci-C4-alkyl) aminocarbonyl and the di (Ci-C4-alkyl) aminocarbonyl parts of di (Ci-C4-alkyl) aminocarbonylamino: for example, N, N-dimethylaminocarbonyl, N, N-diethyl-aminocarbonyl, N 1 N-di- (I-methylethyl) aminocarbonyl, N, N-dipropylaminocarbonyl, N, N-Dibutylaminocarbonyl, N 1 N-di- (I -methylpropyl) aminocarbonyl, N, N-di- (2-methylpropyl) aminocarbonyl, N 1 N -di (1, 1-dimethylethyl) aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N- (1-methylethyl) aminocarbonyl, N-butyl N-methylaminocarbonyl, N-methyl-N- (1-methyl-propyl) -aminocarbonyl, N-methyl-N- (2-methylpropyl) -aminocarbonyl, N- (1, 1-dimethyl-ethyl) -N-methylaminocarbonyl, N- Ethyl N-propylaminocarbonyl, N-ethyl-N- (1-methylethyl) aminocarbonyl, N -butyl-N-ethylaminocarbonyl, N-ethyl-N- (1-methyl-propyl) -aminocarbonyl, N-ethyl-N- (2 -methylpropyl) aminocarbonyl, N-ethyl-N- (1, 1-dimethylethyl) aminocarbonyl, N- (1-methylethyl) -N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N- (1-methylpropyl) -N- propylami nocarbonyl, N- (2-methylpropyl) -N-propylaminocarbonyl, N- (1, 1-dimethylethyl) -N-propylaminocarbonyl, N-butyl-N- (1-methylethyl) aminocarbonyl, N- (1-methylethyl) -N- (1-methylpropyl) -aminocarbonyl, N- (1-methylethyl) -N- (2-methylpropyl) aminocarbonyl, N- (1, 1-dimethylethyl) -N- (1-methylethyl) aminocarbonyl, N -butyl N- (i-methylpropyl) aminocarbonyl, N-butyl-N- (2-methylpropyl) aminocarbonyl, N-butyl-N- (1, 1-dimethyl-ethyl) aminocarbonyl, N- (1-methylpropyl) -N - (2-methylpropyl) aminocarbonyl, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) aminocarbonyl or N- (1, 1-dimethylethyl) -N- (2-methylpropyl) aminocarbonyl;
- (Ci-C6-Alkylamino)carbonyl sowie die (Ci-C6-Alkylamino)carbonyl-Teile von (Ci- C6-Alkylamino)carbonylamino, Ci-C6-Alkylaminocarbonyl-Ci-C4-alkyl und [(C-i-Cδ- Alkyl)amino-carbonylamino]Ci-C4-alkyl,: (Ci-C4-Alkylamino)carbonyl, wie voranstehend genannt, sowie z.B. Pentylaminocarbonyl, 1-Methylbutylaminocarbonyl, 2- Methyl-butylaminocarbonyl, 3-Methylbutylaminocarbonyl, 2,2-Dimethylpropylamino- carbonyl, 1-Ethylpropylaminocarbonyl, Hexylaminocarbonyl, 1 ,1-Dimethylpropyl- aminocarbonyl, 1 ,2-Dimethylpropylaminocarbonyl, 1-Methylpentylaminocarbonyl, 2- Methylpentylaminocarbonyl, 3-Methylpentylaminocarbonyl, 4-Methylpentylamino- carbonyl, 1 ,1-Dimethylbutylaminocarbonyl, 1 ,2-Dimethylbutylaminocarbonyl, 1 ,3- Dimethylbutylaminocarbonyl, 2,2-Dimethylbutylaminocarbonyl, 2,3-Dimethylbutyl- aminocarbonyl, 3,3-Dimethylbutylaminocarbonyl, 1-Ethylbutylaminocarbonyl, 2- Ethylbutylaminocarbonyl, 1 ,1 ,2-Trimethylpropylaminocarbonyl, 1 ,2,2-Trimethyl- propylaminocarbonyl, 1-Ethyl-1-methylpropylaminocarbonyl oder 1-Ethyl-2- methylpropylaminocarbonyl;- (C 1 -C 6 -alkylamino) carbonyl and the (C 1 -C 6 -alkylamino) carbonyl parts of (C 1 -C 6 -alkylamino) carbonylamino, C 1 -C 6 -alkylaminocarbonyl-C 1 -C 4 -alkyl and [(C 1 -C 6 -alkyl ) amino-carbonylamino] C 1 -C 4 -alkyl ,: (C 1 -C 4 -alkylamino) carbonyl, as mentioned above, and, for example Pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, hexylaminocarbonyl, 1, 1-dimethylpropylaminocarbonyl, 1, 2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2 Methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1, 1-dimethylbutylaminocarbonyl, 1, 2-dimethylbutylaminocarbonyl, 1, 3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1, 1, 2-trimethylpropylaminocarbonyl, 1, 2,2-trimethyl-propylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl or 1-ethyl-2-methylpropylaminocarbonyl;
- Di(Ci-C6-alkyl)aminocarbonyl sowie die Di(Ci-C6-alkyl)aminocarbonyl-Teile von Di(Ci-C6-alkyl)aminocarbonylamino, Di(Ci-C6-alkyl)aminocarbonyl-Ci-C4-alkyl und [Di^i-Ce-alkylJaminocarbonylaminolCi^-alkyl: Di(Ci-C4-alkyl)aminocarbonyl, wie voranstehend genannt, sowie z.B. N-Methyl-N-pentylaminocarbonyl, N-Methyl-N- (1 -methylbutyl)-aminocarbonyl, N-Methyl-N-(2-methylbutyl)-aminocarbonyl, N- Methyl-N-(3-methylbutyl)-aminocarbonyl, N-Methyl-N-(2,2-dimethylpropyl)- aminocarbonyl, N-Methyl-N-(1 -ethylpropyl)-aminocarbonyl, N-Methyl-N- hexylaminocarbonyl, N-Methyl-N-(1 ,1-dimethylpropyl)-aminocarbonyl, N-Methyl-- di (Ci-C6-alkyl) aminocarbonyl and the di (Ci-C6-alkyl) aminocarbonyl parts of di (Ci-C6-alkyl) aminocarbonylamino, di (Ci-C6-alkyl) aminocarbonyl-Ci-C4-alkyl and [Di (i-Ce-alkyl-aminocarbonylaminolCi ^ -alkyl: di (Ci-C4-alkyl) aminocarbonyl, as mentioned above, and also, for example, N-methyl-N-pentylaminocarbonyl, N-methyl-N- (1-methylbutyl) aminocarbonyl, N-methyl-N- (2-methylbutyl) aminocarbonyl, N-methyl-N- (3 methylbutyl) aminocarbonyl, N-methyl-N- (2,2-dimethylpropyl) aminocarbonyl, N -methyl-N- (1-ethylpropyl) aminocarbonyl, N -methyl-N-hexylaminocarbonyl, N -methyl-N- ( 1, 1-dimethylpropyl) aminocarbonyl, N-methyl
N-(1 ,2-dimethylpropyl)-aminocarbonyl, N-Methyl-N-(1 -methylpentyl)- aminocarbonyl, N-Methyl-N-(2-methylpentyl)-aminocarbonyl, N-Methyl-N-(3- methylpentyl)-aminocarbonyl, N-Methyl-N-(4-methylpentyl)-aminocarbonyl, N- Methyl-N-(1 ,1-dimethylbutyl)-aminocarbonyl, N-Methyl-N-(1 ,2-dimethylbutyl)- aminocarbonyl, N-Methyl-N-(1 ,3-dimethylbutyl)-aminocarbonyl, N-Methyl-N-(2,2- dimethylbutyl)-aminocarbonyl, N-Methyl-N-(2,3-dimethylbutyl)- amino-carbonyl, N- Methyl-N-(3,3-dimethylbutyl)-aminocarbonyl, N-Methyl-N-(i-ethyl-butyl)- aminocarbonyl, N-Methyl-N-(2-ethylbutyl)-aminocarbonyl, N-Methyl-N-(1 ,1 ,2- trimethylpropyl)-aminocarbonyl, N-Methyl-N-(1 ,2,2-trimethylpropyl)-amino- carbonyl, N-Methyl-N-(1-ethyl-1-methylpropyl)-aminocarbonyl, N-Methyl-N-(1- ethyl-2-methylpropyl)-aminocarbonyl, N-Ethyl-N-pentylaminocarbonyl, N-Ethyl-N- (1 -methylbutyl)-aminocarbonyl, N-Ethyl-N-(2-methylbutyl)-aminocarbonyl, N- Ethyl-N-(3-methylbutyl)-aminocarbonyl, N-Ethyl-N-(2,2-dimethylpropyl)- aminocarbonyl, N-Ethyl-N-(1 -ethylpropyl)-aminocarbonyl, N-Ethyl-N- hexylaminocarbonyl, N-Ethyl-N-(1 ,1-dimethylpropyl)-aminocarbonyl, N-Ethyl-N-N- (1, 2-dimethylpropyl) aminocarbonyl, N-methyl-N- (1-methylpentyl) aminocarbonyl, N -methyl-N- (2-methylpentyl) aminocarbonyl, N -methyl-N- (3-methylpentyl ) -aminocarbonyl, N-methyl-N- (4-methylpentyl) -aminocarbonyl, N-methyl-N- (1, 1-dimethylbutyl) -aminocarbonyl, N-methyl-N- (1, 2-dimethylbutyl) -aminocarbonyl, N-methyl-N- (1,3-dimethylbutyl) -aminocarbonyl, N-methyl-N- (2,2-dimethylbutyl) -aminocarbonyl, N-methyl-N- (2,3-dimethylbutyl) -amino-carbonyl, N-methyl-N- (3,3-dimethylbutyl) -aminocarbonyl, N -methyl-N- (i-ethyl-butyl) -aminocarbonyl, N-methyl-N- (2-ethyl-butyl) -aminocarbonyl, N-methyl- N- (1,1,2-trimethylpropyl) -aminocarbonyl, N-methyl-N- (1,2,2-trimethylpropyl) -aminocarbonyl, N-methyl-N- (1-ethyl-1-methylpropyl) - aminocarbonyl, N-methyl-N- (1-ethyl-2-methylpropyl) -aminocarbonyl, N-ethyl-N-pentylaminocarbonyl, N-ethyl-N- (1-methylbutyl) -aminocarbonyl, N-ethyl-N- (2 -methylbutyl) -aminocarbonyl, N-ethyl-N- (3-methylbutyl) -aminocarbonyl, N-ethyl-N- (2,2-dimethylpropyl) -aminocarbonyl, N-Et hyl-N- (1-ethyl-propyl) -aminocarbonyl, N-ethyl-N-hexylaminocarbonyl, N-ethyl-N- (1, 1-dimethyl-propyl) -aminocarbonyl, N-ethyl-N-
(1 ,2-dimethylpropyl)-aminocarbonyl, N-Ethyl-N-(1 -methylpentyl)-aminocarbonyl, N-Ethyl-N-(2-methylpentyl)-aminocarbonyl, N-Ethyl-N-(3-methylpentyl)- aminocarbonyl, N-Ethyl-N-(4-methylpentyl)-aminocarbonyl, N-Ethyl-N-(1 ,1- dimethylbutyl)-aminocarbonyl, N-Ethyl-N-(1 ,2-dimethylbutyl)-aminocarbonyl, N- Ethyl-N-(1 ,3-dimethylbutyl)-aminocarbonyl, N-Ethyl-N-(2,2-dimethylbutyl)- aminocarbonyl, N-Ethyl-N-(2,3-dimethylbutyl)-aminocarbonyl, N-Ethyl-N-(3,3- dimethylbutyl)-aminocarbonyl, N-Ethyl-N-(1 -ethylbutyl)-amino-carbonyl, N-Ethyl- N-(2-ethylbutyl)-aminocarbonyl, N-Ethyl-N-(1 ,1 ,2-trimethyl-propyl)-aminocarbonyl, N-Ethyl-N-(1 ,2,2-trimethylpropyl)-aminocarbonyl, N-Ethyl-N- (1 -ethyl-1 - methylpropyl)-aminocarbonyl, N-Ethyl-N-(1 -ethyl-2-methylpropyl)-aminocarbonyl,(1, 2-dimethylpropyl) aminocarbonyl, N-ethyl-N- (1-methylpentyl) aminocarbonyl, N-ethyl-N- (2-methylpentyl) aminocarbonyl, N-ethyl-N- (3-methylpentyl) - aminocarbonyl, N-ethyl-N- (4-methylpentyl) aminocarbonyl, N-ethyl-N- (1, 1-dimethylbutyl) aminocarbonyl, N-ethyl-N- (1, 2-dimethylbutyl) aminocarbonyl, N- Ethyl N- (1,3-dimethylbutyl) aminocarbonyl, N-ethyl-N- (2,2-dimethylbutyl) aminocarbonyl, N-ethyl-N- (2,3-dimethylbutyl) aminocarbonyl, N-ethyl N- (3,3-dimethylbutyl) -aminocarbonyl, N-ethyl-N- (1-ethyl-butyl) -amino-carbonyl, N-ethyl-N- (2-ethyl-butyl) -aminocarbonyl, N-ethyl-N- (1 , 1, 2-trimethyl-propyl) -aminocarbonyl, N-ethyl-N- (1, 2,2-trimethyl-propyl) -aminocarbonyl, N-ethyl-N- (1-ethyl-1-methyl-propyl) -aminocarbonyl, N- Ethyl N- (1-ethyl-2-methylpropyl) aminocarbonyl,
N-Propyl-N-pentylaminocarbonyl, N-Butyl-N-pentylaminocarbonyl, N1N- Dipentylaminocarbonyl, N-Propyl-N-hexyl-aminocarbonyl, N-Butyl-N- hexylaminocarbonyl, N-Pentyl-N-hexylaminocarbonyl oder N,N-Dihexylamino- carbonyl;N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl, N 1 N- Dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl, N-butyl-N- hexylaminocarbonyl, N-pentyl-N-hexylaminocarbonyl or N, N-dihexylaminocarbonyl;
Di(Ci-C6-alkyl)aminothiocarbonyl: z.B. N,N-Dimethylaminothiocarbonyl, N1N-Di (C 1 -C 6 -alkyl) aminothiocarbonyl: for example N, N-dimethylaminothiocarbonyl, N 1 N-
Diethylaminothiocarbonyl, N1N-Di-(I -methylethyl)aminothiocarbonyl, N,N-Dipropyl- aminothiocarbonyl, N,N-Dibutylaminothiocarbonyl, N1N-Di-(I -methylpropyl)-amino- thiocarbonyl, N,N-Di-(2-methylpropyl)-aminothiocarbonyl, N1N-Di-(1 ,1-dimethyl- ethyl)-aminothiocarbonyl, N-Ethyl-N-methylaminothiocarbonyl, N-Methyl-N-propyl- aminothiocarbonyl, N-Methyl-N-(1-methylethyl)-aminothiocarbonyl, N-Butyl-N- methylaminothiocarbonyl, N-Methyl-N-(1 -methylpropyl)-aminothiocarbonyl, N- Methyl-N-(2-methylpropyl)aminothiocarbonyl, N-(1 ,1-Dimethylethyl)-N- methylaminothiocarbonyl, N-Ethyl-N-propylaminothiocarbonyl, N-Ethyl-N-(1 - methylethyl)-aminothiocarbonyl, N-Butyl-N-ethylaminothiocarbonyl, N-Ethyl-N-(1- methylpropyl)-aminothiocarbonyl, N-Ethyl-N-(2-methylpropyl)-aminothiocarbonyl, N-Ethyl-N-(1 ,1-dimethylethyl)-aminothiocarbonyl, N-(1-Methylethyl)-N- propylaminothiocarbonyl, N-Butyl-N-propylaminothiocarbonyl, N-(1-Methylpropyl)-N- propylaminothiocarbonyl, N-(2-Methylpropyl)-N-propylamino-thiocarbonyl, N-(1 ,1- Dimethylethyl)-N-propylaminothiocarbonyl, N-Butyl-N-(i-methylethyl)- aminothiocarbonyl, N-(1 -Methylethyl)-N-(1 -methylpropyl)-aminothiocarbonyl, N-(1 - Methylethyl)-N-(2-methylpropyl)-aminothiocarbonyl, N-(1 ,1-Dimethylethyl)-N-(1- methylethyl)-aminothiocarbonyl, N-Butyl-N-(1-methylpropyl)-aminothiocarbonyl, N-Diethylaminothiocarbonyl, N 1 N -di (1-methylethyl) aminothiocarbonyl, N, N-dipropylaminothiocarbonyl, N, N-dibutylaminothiocarbonyl, N 1 N -di (1-methylpropyl) aminoethiocarbonyl, N, N-di - (2-methylpropyl) -aminothiocarbonyl, N 1 N -di (1, 1-dimethyl-ethyl) -aminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminothiocarbonyl, N-methyl-N - (1-methylethyl) aminothiocarbonyl, N-butyl-N-methylaminothiocarbonyl, N -methyl-N- (1-methylpropyl) -aminothiocarbonyl, N-methyl-N- (2-methylpropyl) aminothiocarbonyl, N- (1,1-d dimethylethyl) -N- methylaminothiocarbonyl, N-ethyl-N-propylaminothiocarbonyl, N-ethyl-N- (1-methylethyl) -aminothiocarbonyl, N-butyl-N-ethylaminothiocarbonyl, N-ethyl-N- (1-methylpropyl) -aminothiocarbonyl, N-ethyl- N- (2-methylpropyl) -aminothiocarbonyl, N-ethyl-N- (1, 1-dimethylethyl) -aminothiocarbonyl, N- (1-methylethyl) -N-propylaminothiocarbonyl, N-butyl-N-propylaminothiocarbonyl, N- (1 Methylpropyl) -N-propylaminothiocarbonyl, N- (2-methylpropyl) -N-propylamino-thiocarbonyl, N- (1, 1-dimethylethyl) -N-propylaminothiocarbonyl, N-butyl-N- (i-methylethyl) -aminothiocarbonyl, N- (1-methylethyl) -N- (1-methylpropyl) -aminothiocarbonyl, N- (1-methylethyl) -N- (2-methylpropyl) -aminothiocarbonyl, N- (1, 1-dimethylethyl) -N- (1 - methylethyl) -aminothiocarbonyl, N-butyl-N- (1-methylpropyl) -aminothiocarbonyl, N-
Butyl-N-(2-methylpropyl)-aminothiocarbonyl, N-Butyl-N-(1 ,1-dimethylethyl)- aminothiocarbonyl, N-(1-Methylpropyl)-N-(2-methylpropyl)-aminothiocarbonyl, N- (1 ,1-Dimethylethyl)-N-(1-methylpropyl)-aminothiocarbonyl, N-(1 ,1-Dimethylethyl)-N- (2-methylpropyl)-aminothiocarbonyl, N-Methyl-N-pentylaminothiocarbonyl, N- Methyl-N-(1 -methylbutyl)-aminothio-carbonyl, N-Methyl-N-(2-methylbutyl)- aminothiocarbonyl, N-Methyl-N-(3-methylbutyl)-aminothiocarbonyl, N-Methyl-N- (2,2-dimethylpropyl)-aminothio-carbonyl, N-Methyl-N-(i-ethylpropyl)- aminothiocarbonyl, N-Methyl-N-hexyl-aminothiocarbonyl, N-Methyl-N- (1 ,1- dimethylpropyl)-aminothiocarbonyl, N-Methyl-N-(1 ,2-dimethylpropyl)- aminothiocarbonyl, N-Methyl-N-(1-methylpentyl)-aminothiocarbonyl, N-Methyl-N-Butyl N- (2-methylpropyl) aminothiocarbonyl, N-butyl-N- (1, 1-dimethylethyl) aminothiocarbonyl, N- (1-methylpropyl) -N- (2-methylpropyl) aminothiocarbonyl, N- (1 , 1-dimethylethyl) -N- (1-methylpropyl) -aminothiocarbonyl, N- (1, 1-dimethylethyl) -N- (2-methylpropyl) -aminothiocarbonyl, N-methyl-N-pentylaminothiocarbonyl, N-methyl-N- (1-methylbutyl) -aminothio-carbonyl, N-methyl-N- (2-methylbutyl) -aminothiocarbonyl, N-methyl-N- (3-methylbutyl) -aminothiocarbonyl, N -methyl-N- (2,2-dimethylpropyl ) -aminothio-carbonyl, N-methyl-N- (i-ethylpropyl) -aminothiocarbonyl, N-methyl-N-hexyl-aminothiocarbonyl, N-methyl-N- (1, 1-dimethylpropyl) -aminothiocarbonyl, N-methyl- N- (1,2-dimethylpropyl) aminothiocarbonyl, N-methyl-N- (1-methylpentyl) -aminothiocarbonyl, N-methyl-N-
(2-methylpentyl)-aminothiocarbonyl, N-Methyl-N-(3-methylpentyl)- aminothiocarbonyl, N-Methyl-N-(4-methylpentyl)-aminothio-carbonyl, N-Methyl-N- (1 ,1-dimethylbutyl)-aminothiocarbonyl, N-Methyl-N-(1 ,2-dimethylbutyl)- aminothiocarbonyl, N-Methyl-N-(1 ,3-dimethylbutyl)-aminothiocarbonyl, N-Methyl- N-(2,2-dimethylbutyl)- aminothiocarbonyl, N-Methyl-N-(2,3-dimethylbutyl)- aminothiocarbonyl, N-Methyl-N-(3,3-dimethylbutyl)-aminothiocarbonyl, N-Methyl- N-(1-ethylbutyl)-aminothiocarbonyl, N-Methyl-N-(2-ethylbutyl)-aminothiocarbonyl, N-Methyl-N-ethyl-N-(1 ,1 ,2-trimethylpropyl)-aminothiocarbonyl, N-Methyl-N- (1 ,2,2-trimethylpropyl)-aminothiocarbonyl, N-Methyl-N-(1-ethyl-1-methylpropyl)- aminothiocarbonyl, N-Methyl-N-(1-ethyl-2-methylpropyl)-aminothiocarbonyl, N-(2-methylpentyl) -aminothiocarbonyl, N-methyl-N- (3-methylpentyl) -aminothiocarbonyl, N-methyl-N- (4-methylpentyl) -aminothio-carbonyl, N-methyl-N- (1, 1-dimethylbutyl ) -aminothiocarbonyl, N-methyl-N- (1, 2-dimethylbutyl) -aminothiocarbonyl, N-methyl-N- (1, 3-dimethylbutyl) -aminothiocarbonyl, N-methyl-N- (2,2-dimethylbutyl) - aminothiocarbonyl, N-methyl-N- (2,3-dimethylbutyl) -aminothiocarbonyl, N-methyl-N- (3,3-dimethylbutyl) -aminothiocarbonyl, N-methyl-N- (1-ethylbutyl) -aminothiocarbonyl, N- Methyl-N- (2-ethylbutyl) -aminothiocarbonyl, N-methyl-N-ethyl-N- (1, 1, 2-trimethylpropyl) -aminothiocarbonyl, N-methyl-N- (1, 2,2-trimethylpropyl) - aminothiocarbonyl, N-methyl-N- (1-ethyl-1-methylpropyl) -aminothiocarbonyl, N-methyl-N- (1-ethyl-2-methylpropyl) -aminothiocarbonyl, N-
Ethyl-N-pentyl-aminothiocarbonyl, N-Ethyl-N-(1-methylbutyl)-aminothiocarbonyl, N-Ethyl-N-(2-methylbutyl)-aminothiocarbonyl, N-Ethyl-N-(3-methylbutyl)- aminothiocarbonyl, N-Ethyl-N-(2,2-dimethylpropyl)-aminothiocarbonyl, N-Ethyl-N-(1- ethylpropyl)-aminothiocarbonyl, N-Ethyl-N-hexylaminothiocarbonyl, N-Ethyl-N- (1 ,1-dimethyl-propyl)-aminothiocarbonyl, N-Ethyl-N-(1 ,2-dimethylpropyl)- aminothiocarbonyl, N-Ethyl-N-(1-methylpentyl)-aminothiocarbonyl, N-Ethyl-N-(2- methylpentyl)-aminothiocarbonyl, N-Ethyl-N-(3-methylpentyl)-aminothiocarbonyl, N-Ethyl-N-(4-methylpentyl)-aminothiocarbonyl, N-Ethyl-N-(1 ,1-dimethylbutyl)- amino-thiocarbonyl, N-Ethyl-N-(1 ,2-dimethylbutyl)- aminothiocarbonyl, N-Ethyl- N-(1 ,3-dimethylbutyl)-aminothiocarbonyl, N-Ethyl-N-(2,2-dimethylbutyl)-aminothio- carbonyl, N-Ethyl-N-(2,3-dimethylbutyl)-aminothiocarbonyl, N-Ethyl-N-(3,3- dimethylbutyl)-aminothiocarbonyl, N-Ethyl-N-(1 -ethylbutyl)-aminothiocarbonyl, N- Ethyl-N-(2-ethylbutyl)-aminothiocarbonyl, N-Ethyl-N-(1 ,1 ,2-trimethylpropyl)- aminothiocarbonyl, N-Ethyl-N-(1 ,2,2-trimethylpropyl)-aminothiocarbonyl, N-Ethyl- N-(1 -ethyl-1 -methylpropyl)-aιminothiocarbonyl, N-Ethyl-N-(1 -ethyl-2-methylpropyl)- aminothiocarbonyl, N-Propyl-N-pentylaminothiocarbonyl, N-Butyl-N- pentylaminothiocarbonyl, N,N-Dipentylaminothiocarbonyl, N-Propyl-N-hexyl- aminothiocarbonyl, N-Butyl-N-hexylaminothiocarbonyl, N-Pentyl-N-hexyl- aminothiocarbonyl oder N,N-Dihexylaminothiocarbonyl;Ethyl N-pentylaminothiocarbonyl, N-ethyl-N- (1-methylbutyl) aminothiocarbonyl, N-ethyl-N- (2-methylbutyl) aminothiocarbonyl, N-ethyl-N- (3-methylbutyl) aminothiocarbonyl, N-ethyl-N- (2,2-dimethylpropyl) -aminothiocarbonyl, N-ethyl-N- (1-ethyl-propyl) -aminothiocarbonyl, N-ethyl-N-hexylaminothiocarbonyl, N-ethyl-N- (1, 1-dimethyl -propyl) -aminothiocarbonyl, N-ethyl-N- (1, 2-dimethylpropyl) -aminothiocarbonyl, N-ethyl-N- (1-methylpentyl) -aminothiocarbonyl, N-ethyl-N- (2-methylpentyl) -aminothiocarbonyl, N-ethyl-N- (3-methylpentyl) -aminothiocarbonyl, N-ethyl-N- (4-methylpentyl) -aminothiocarbonyl, N-ethyl-N- (1, 1-dimethylbutyl) -amino-thiocarbonyl, N-ethyl- N- (1,2-dimethylbutyl) aminothiocarbonyl, N-ethyl-N- (1,3-dimethylbutyl) -aminothiocarbonyl, N-ethyl-N- (2,2-dimethylbutyl) aminothio-carbonyl, N-ethyl- N- (2,3-dimethylbutyl) -aminothiocarbonyl, N-ethyl-N- (3,3-dimethylbutyl) -aminothiocarbonyl, N-ethyl-N- (1-ethylbutyl) -aminothiocarbonyl, N-ethyl-N- (2 ethylbutyl) aminothiocarbonyl, N-ethyl-N- (1, 1 , 2-trimethyl-propyl) - aminothiocarbonyl, N-ethyl-N- (1, 2,2-trimethylpropyl) -aminothiocarbonyl, N-ethyl-N- (1-ethyl-1-methylpropyl) -aminothiocarbonyl, N-ethyl-N- (1-ethyl-2 -methylpropyl) - aminothiocarbonyl, N-propyl-N-pentylaminothiocarbonyl, N-butyl-N-pentylaminothiocarbonyl, N, N-dipentylaminothiocarbonyl, N-propyl-N-hexylaminothiocarbonyl, N-butyl-N-hexylaminothiocarbonyl, N-pentyl- N-hexylaminothiocarbonyl or N, N-dihexylaminothiocarbonyl;
drei- bis sechsgliedriges Heterocyclyl: monocyclische, gesättigte oder partiell ungesättigte Kohlenwasserstoffe mit drei bis sechs Ringgliedern wie voranstehend ge- nannt, welche neben Kohlenstoffatomen ein bis vier Stickstoffatome, oder ein bis drei Stickstoffatome und ein Sauerstoff- oder Schwefelatom, oder ein bis drei Sauerstoffatome, oder ein bis drei Schwefelatome enthalten können, und welche über ein C-Atom oder ein N-Atom verknüpft sein können, z.B.three- to six-membered heterocyclyl: monocyclic, saturated or partially unsaturated hydrocarbons having three to six ring members as mentioned above which, in addition to carbon atoms, have one to four nitrogen atoms, or one to three nitrogen atoms and one oxygen or sulfur atom, or one to three oxygen atoms, or may contain one to three sulfur atoms, and which may be linked via a C atom or an N atom, eg
z.B. 2-Oxiranyl, 2-Oxetanyl, 3-Oxetanyl, 2-Aziridinyl, 3-Thiethanyl, 1-Azetidinyl, 2-e.g. 2-oxiranyl, 2-oxetanyl, 3-oxetanyl, 2-aziridinyl, 3-thiethanyl, 1-azetidinyl, 2-
Azetidinyl,azetidinyl,
z.B. 2-Tetrahydrofuranyl, 3-Tetrahydrofuranyl, 2-Tetrahydrothienyl, 3-Tetra- hydrothienyl, 2-Pyrrolidinyl, 3-Pyrrolidinyl, 3-lsoxazolidinyl, 4-lsoxazolidinyl, 5- Isoxazolidinyl, 3-lsothiazolidinyl, 4-lsothiazolidinyl, 5-lsothiazolidinyl, 3-Pyrazolidinyl,e.g. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl,
4-Pyrazolidinyl, 5-Pyrazolidinyl, 2-Oxazolidinyl, 4-Oxazolidinyl, 5-Oxazolidinyl, 2- Thiazolidinyl, 4-Thiazolidinyl, 5-Thiazolidinyl, 2-lmidazolidinyl, 4-lmidazolidinyl, 1 ,2,4-Oxadiazolidin-3-yl, 1 ,2,4-Oxadiazolidin-5-yl, 1 ,2,4-Thiadiazolidin-3-yl, 1 ,2,4- Thiadiazolidin-5-yl, 1 ,2,4-Triazolidin-3-yl, 1 ,3,4-Oxadiazolidin-2-yl, 1 ,3,4-Thia- diazolidin-2-yl, 1 ,3,4-Triazolidin-2-yl, 1 ,2,3,4-Tetrazolidin-5-yl;4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1, 2,4-oxadiazolidine-3 yl, 1, 2,4-oxadiazolidin-5-yl, 1, 2,4-thiadiazolidin-3-yl, 1, 2,4-thiadiazolidin-5-yl, 1, 2,4-triazolidin-3-yl, 1, 3,4-oxadiazolidin-2-yl, 1, 3,4-thiadiazolidin-2-yl, 1, 3,4-triazolidin-2-yl, 1, 2,3,4-tetrazolidine-5 yl;
z.B. 1-Pyrrolidinyl, 2-lsothiazolidinyl, 2-lsothiazolidinyl, 1-Pyrazolidinyl, 3-Oxazoli- dinyl, 3-Thiazolidinyl, 1-lmidazolidinyl, 1 ,2,4-Triazolidin-1-yl, 1 ,2,4-Oxadiazolidin-2- yl, 1 ,2,4-Oxadiazolidin-4-yl, 1 ,2,4-Thiadiazolidin-2-yl, 1 ,2,4-Thiadiazolidin-4-yl, 1 ,2,3,4-Tetrazolidin-1-yl,e.g. 1-pyrrolidinyl, 2-isothiazolidinyl, 2-isothiazolidinyl, 1-pyrazolidinyl, 3-oxazolidinyl, 3-thiazolidinyl, 1-imidazolidinyl, 1, 2,4-triazolidin-1-yl, 1, 2,4-oxadiazolidine 2-yl, 1, 2,4-oxadiazolidin-4-yl, 1, 2,4-thiadiazolidin-2-yl, 1, 2,4-thiadiazolidin-4-yl, 1, 2,3,4-tetrazolidine 1-yl,
z.B. 2,3-Dihydrofur-2-yl, 2,3-Dihydrofur-3-yl, 2,4-Dihydrofur-2-yl, 2,4-Dihydrofur-3-yl, 2,3-Dihydrothien-2-yl, 2,3-Dihydrothien-3-yl, 2,4-Dihydrothien-2-yl, 2,4-Dihydrothien- 3-yl, 4,5-Dihydropyrrol-2-yl, 4,5-Dihydropyrrol-3-yl, 2,5-Dihydropyrrol-2-yl, 2,5- Dihydropyrrol-3-yl, 4,5-Dihydroisoxazol-3-yl, 2,5-Dihydroisoxazol-3-yl, 2,3-Di- hydroisoxazol-3-yl, 4,5-Dihydroisoxazol-4-yl, 2,5-Dihydroisoxazol-4-yl, 2,3-Dihydro- isoxazol-4-yl, 4,5-Dihydroisoxazol-5-yl, 2,5-Dihydroisoxazol-5-yl, 2,3-Dihydro- isoxazol-5-yl, 4,5-Dihydroisothiazol-3-yl, 2,5-Dihydroisothiazol-3-yl, 2,3-Dihydro- isothiazol-3-yl, 4,5-Dihydroisothiazol-4-yl, 2,5-Dihydroisothiazol-4-yl, 2,3-Dihydro- isothiazol-4-yl, 4,5-Dihydroisothiazol-5-yl, 2,5-Dihydroisothiazol-5-yl, 2,3-Dihydro- isothiazol -5-yl, 2,3-Dihydropyrazol-2-yl, 2,3-Dihydropyrazol-3-yl, 2,3-Dihydro- pyrazol-4-yl, 2,3-Dihydropyrazol-5-yl, 3,4-Dihydropyrazol-3-yl, 3,4-Dihydropyrazol-4- yl, 3,4-Dihydropyrazol-5-yl, 4,5-Dihydropyrazol-3-yl, 4,5-Dihydropyrazol-4-yl, 4,5- Dihydropyrazol-5-yl, 2,3-Dihydroimidazol-2-yl, 2,3-Dihydroimidazol-3-yl ,2,3-Di- hydroimidazol-4-yl, 2,3-Dihydroimidazol-5-yl, 4,5-Dihydroimidazol-2-yl, 4,5-Di- hydroimidazol-4-yl, 4,5-Dihydroimidazol-5-yl, 2,5-Dihydroimidazol-2-yl, 2,5-Di- hydroimidazol-4-yl, 2,5-Dihydroimidazol-5-yl, 2,3-Dihydrooxazol-3-yl, 2,3-Dihydro- oxazol-4-yl, 2,3-Dihydrooxazol-5-yl, 3,4-Dihydrooxazol-3-yl, 3,4-Dihydrooxazol-4-yl,For example, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydro-2-yl , 2,3-dihydro-thien-3-yl, 2,4-dihydro-thien-2-yl, 2,4-dihydro-thien-3-yl, 4,5-dihydropyrrol-2-yl, 4,5-dihydropyrrol-3-yl , 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 4,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-3-yl, 2,3-dihydroisoxazole-3 -yl, 4,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazole -5-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-3-yl, 4 , 5-Dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-5-yl , 2,3-dihydroisothiazol-5-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazole -5-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazole -4- yl, 4,5- Dihydropyrazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-3-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4, 5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazole-4 yl, 2,5-dihydroimidazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazole 3-yl, 3,4-dihydrooxazol-4-yl,
3,4-Dihydrooxazol-5-yl, 2,3-Dihydrothiazol-3-yl, 2,3-Dihydrothiazol-4-yl, 2,3-Di- hydrothiazol-5-yl, 3,4-Dihydrothiazol-3-yl, 3,4-Dihydrothiazol-4-yl, 3,4-Dihydro- thiazol-5-yl, 3,4-Dihydrothiazol-2-yl, 3,4-Dihydrothiazol-3-yl, 3,4-Dihydrothiazol-4-yl,3,4-Dihydrooxazol-5-yl, 2,3-dihydrothiazol-3-yl, 2,3-dihydrothiazol-4-yl, 2,3-di-hydrothiazol-5-yl, 3,4-dihydrothiazole-3 yl, 3,4-dihydrothiazol-4-yl, 3,4-dihydro-thiazol-5-yl, 3,4-dihydrothiazol-2-yl, 3,4-dihydrothiazol-3-yl, 3,4-dihydrothiazole 4-yl,
z.B. 4,5-Dihydropyrrol-1-yl, 2,5-Dihydropyrrol-1-yl, 4,5-Dihydroisoxazol-2-yl, 2,3-e.g. 4,5-dihydropyrrol-1-yl, 2,5-dihydropyrrol-1-yl, 4,5-dihydroisoxazol-2-yl, 2,3-
Dihydroisoxazol-1-yl, 4,5-Dihydroisothiazol-1-yl, 2,3-Dihydroisothiazol-1-yl, 2,3-Di- hydropyrazol-1-yl, 4,5-Dihydropyrazol-1-yl, 3,4-Dihydropyrazol-1-yl, 2,3-Dihydro- imidazol-1-yl, 4,5-Dihydroimidazol-1-yl, 2,5-Dihydroimidazol-1-yl, 2,3-Dihydrooxazol- 2-yl, 3,4-Dihydrooxazol-2-yl, 2,3-Dihydrothiazol-2-yl, 3,4-Dihydrothiazol-2-yl;Dihydroisoxazol-1-yl, 4,5-dihydroisothiazol-1-yl, 2,3-dihydroisothiazol-1-yl, 2,3-dihydropyrazol-1-yl, 4,5-dihydropyrazol-1-yl, 3, 4-dihydropyrazol-1-yl, 2,3-dihydroimidazol-1-yl, 4,5-dihydroimidazol-1-yl, 2,5-dihydroimidazol-1-yl, 2,3-dihydrooxazol-2-yl, 3,4-dihydrooxazol-2-yl, 2,3-dihydrothiazol-2-yl, 3,4-dihydrothiazol-2-yl;
z.B. 2-Piperidinyl, 3-Piperidinyl, 4-Piperidinyl, 1 ,3-Dioxan-2-yl 1 ,3-Dioxan-4-yl, 1 ,3- Dioxan-5-yl, 1 ,4-Dioxan-2-yl, 1 ,3-Dithian-2-yl, 1 ,4-Dithian-3-yl, 1 ,3-Dithian-4-yl, 1 ,4- Dithian-2-yl, 2-Tetrahydropyranyl, 3-Tetrahydropyranyl, 4-Tetrahydropyranyl, 2- Tetrahydrothiopyranyl, 3-Tetrahydrothiopyranyl, 4-Tetrahydro-thiopyranyl 3- Hexahydropyridazinyl, 4-Hexahydropyridazinyl, 2-Hexahydropyrimidinyl, 4-e.g. 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1, 3-dioxan-2-yl, 3-dioxan-4-yl, 1, 3-dioxan-5-yl, 1, 4-dioxan-2-yl 1,1,3-Dithian-2-yl, 1,4-dithian-3-yl, 1,3-dithian-4-yl, 1,4-dithian-2-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4 -Tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl, 4-tetrahydro-thiopyranyl 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-
Hexahydropyrimidinyl, 5-Hexahydropyrimidinyl, 2-Piperazinyl, 1 ,3,5-Hexa- hydrotriazin-2-yl, 1 ,2,4-Hexahydrotriazin-3-yl, Tetrahydro-1 ,3-oxazin-2-yl, Tetra- hydro-1 ,3-oxazin-6-yl, 2-Morpholinyl, 3-Morpholinyl, 1 ,3,5-Trioxan-2-yl;Hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1, 3,5-hexa-hydrotriazin-2-yl, 1, 2,4-hexahydrotriazin-3-yl, tetrahydro-1,3-oxazin-2-yl, tetra-3-yl hydro-1, 3-oxazin-6-yl, 2-morpholinyl, 3-morpholinyl, 1, 3,5-trioxan-2-yl;
z.B. 1-Piperidinyl, 1 -Hexahydropyridazinyl, 1-Hexahydropyrimidinyl, 1-Piperazinyl,e.g. 1-piperidinyl, 1-hexahydropyridazinyl, 1-hexahydropyrimidinyl, 1-piperazinyl,
1 ,3,5-Hexahydrotriazin-1 -yl, 1 ,2,4-Hexahydrotriazin-1 -yl, Tetrahydro-1 ,3-oxazin-1 -yl, 1-Morpholinyl;1, 3,5-hexahydrotriazine-1-yl, 1, 2,4-hexahydrotriazine-1-yl, tetrahydro-1,3-oxazin-1-yl, 1-morpholinyl;
z.B. 2H-Pyran-2-yl, 2H-Pyran-3-yl, 2H-Pyran-4-yl, 2H-Pyran-5-yl, 2H-Pyran-6-yl, 3,6-Dihydro-2H-pyran-2-yl, 3,6-Dihydro-2H-pyran-3-yl, 3,6-Dihydro-2H-pyran-4-yl,e.g. 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 3,6-dihydro-2H-pyranyl 2-yl, 3,6-dihydro-2H-pyran-3-yl, 3,6-dihydro-2H-pyran-4-yl,
3,6-Dihydro-2H-pyran-5-yl, 3,6-Dihydro-2H-pyran-6-yl, 3,4-Dihydro-2H-pyran-3-yl, 3,4-Dihydro-2H-pyran-4-yl, 3,4-Dihydro-2H-pyran-6-yl, 2H-Thiopyran-2-yl, 2H- Thiopyran-3-yl, 2H-Thiopyran-4-yl, 2H-Thiopyran-5-yl, 2H-Thiopyran-6-yl, 5,6- Dihydro-4H-1 ,3-oxazin-2-yl;3,6-Dihydro-2H-pyran-5-yl, 3,6-dihydro-2H-pyran-6-yl, 3,4-dihydro-2H-pyran-3-yl, 3,4-dihydro-2H- pyran-4-yl, 3,4-dihydro-2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5 yl, 2H-thiopyran-6-yl, 5,6-dihydro-4H-1,3-oxazin-2-yl;
- Aryl sowie der Arylteil von Aryl(Ci-C4-alkyl): ein- bis dreikerniger aromatischer Car- bocyclus mit 6 bis 14 Ringgliedern, wie z.B. Phenyl, Naphthyl und Anthracenyl;Aryl and the aryl part of aryl (C 1 -C 4 -alkyl): a mono- to trinuclear aromatic carbocyclic having 6 to 14 ring members, such as, for example, Phenyl, naphthyl and anthracenyl;
- Heteroaryl sowie die Heteroarylreste in Heteroaryl-Ci-C4-alkyl, Heteroaryl-Ci-C4- alkyl, Heteroaryl-C2-C4-alkenyl, Heteroaryl-C2-C4-alkinyl, Heteroaryl-Ci-C4- halogenalkyl, Heteroaryl-C2-C4-halogenalkenyl, Heteroaryl-C2-C4-halogenalkinyl, Heteroaryl-Ci-C4-hydroxyalkyl, Heteroaryl-C2-C4-hydroxyalkenyl, Heteroaryl-C2-C4- hydroxyalkinyl, Heteroarylcarbonyl-Ci-C4-alkyl, Heteroarylcarbonyloxy-Ci-C4-alkyl, Heteroaryloxycarbonyl-Ci^-alkyl, Heteroaryloxy-Ci-C4-alkyl, Heteroarylthio-Ci-C4- alkyl, Heteroarylsulfinyl-Ci-C4-alkyl, Heteroarylsulfonyl-Ci-C4-alkyl : mono- oder bicyclisches aromatisches Heteroaryl mit 5 bis 10 Ringgliedern, welches neben Kohlenstoffatomen 1 bis 4 Stickstoffatome, oder 1 bis 3 Stickstoffatome und ein Sauerstoff- oder ein Schwefelatom, oder ein Sauerstoff- oder ein Schwefelatom enthält, z.B.Heteroaryl and the heteroaryl radicals in heteroaryl-C 1 -C 4 -alkyl, heteroaryl-C 1 -C 4 -alkyl, heteroaryl-C 2 -C 4 -alkenyl, heteroaryl-C 2 -C 4 -alkynyl, heteroaryl-C 1 -C 4 -haloalkyl, heteroarylC 2 -alkyl C 4 -haloalkenyl, heteroaryl-C 2 -C 4 -haloalkynyl, heteroaryl-C 1 -C 4 -hydroxyalkyl, heteroaryl-C 2 -C 4 -hydroxyalkenyl, heteroarylC 2 -C 4 -hydroxyalkynyl, heteroarylcarbonyl-C 1 -C 4 -alkyl, heteroarylcarbonyloxy-C 1 -C 4 -alkyl alkyl, Heteroaryloxycarbonyl-C 1-8 -alkyl, heteroaryloxy-C 1 -C 4 -alkyl, heteroarylthio-C 1 -C 4 -alkyl, heteroarylsulfinyl-C 1 -C 4 -alkyl, heteroarylsulfonyl-C 1 -C 4 -alkyl: mono- or bicyclic aromatic heteroaryl having 5 to 10 ring members , which contains in addition to carbon atoms 1 to 4 nitrogen atoms, or 1 to 3 nitrogen atoms and an oxygen or sulfur atom, or an oxygen or sulfur atom, for example
Monocyclen wie Furyl (z.B. 2-Furyl, 3-Furyl), Thienyl (z.B. 2-Thienyl, 3-Thienyl), Pyrrolyl (z.B. Pyrrol-2-yl, Pyrrol-3-yl), Pyrazolyl (z.B. Pyrazol-3-yl, Pyrazol-4-yl), Isoxazolyl (z.B. lsoxazol-3-yl, lsoxazol-4-yl, lsoxazol-5-yl), Isothiazolyl (z.B. lsothiazol-3-yl, lsothiazol-4-yl, lsothiazol-5-yl), Imidazolyl (z.B. lmidazol-2-yl, lmidazol-4-yl), Oxazolyl (z.B. Oxazol-2-yl, Oxazol-4-yl, Oxazol-5-yl), Thiazolyl (z.B. Thiazol-2-yl, Thiazol-4-yl, Thiazol-5-yl), Oxadiazolyl (z.B. 1 ,2,3-Oxadiazol- 4-yl, 1 ,2,3-Oxadiazol-5-yl, 1 ,2,4-Oxadiazol-3-yl, 1 ,2,4,-Oxadiazol-5-yl, 1 ,3,4- Oxadiazol-2-yl), Thiadiazolyl (z.B. 1 ,2,3-Thiadiazol-4-yl, 1 ,2,3-Thiadiazol-5-yl, 1 ,2,4-Thiadiazol-3-yl, 1 ,2,4-Thiadiazol-5-yl, 1 ,3,4-Thiadiazolyl-2-yl), TriazolylMonocycles such as furyl (eg 2-furyl, 3-furyl), thienyl (eg 2-thienyl, 3-thienyl), pyrrolyl (eg pyrrol-2-yl, pyrrol-3-yl), pyrazolyl (eg pyrazol-3-yl , Pyrazol-4-yl), isoxazolyl (eg isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (eg isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl ), Imidazolyl (eg imidazol-2-yl, imidazol-4-yl), oxazolyl (eg oxazol-2-yl, oxazol-4-yl, oxazol-5-yl), thiazolyl (eg thiazol-2-yl, thiazole 4-yl, thiazol-5-yl), oxadiazolyl (eg, 1, 2,3-oxadiazol-4-yl, 1, 2,3-oxadiazol-5-yl, 1, 2,4-oxadiazol-3-yl , 1, 2,4, -oxadiazol-5-yl, 1, 3,4-oxadiazol-2-yl), thiadiazolyl (eg 1, 2,3-thiadiazol-4-yl, 1, 2,3-thiadiazole) 5-yl, 1, 2,4-thiadiazol-3-yl, 1, 2,4-thiadiazol-5-yl, 1, 3,4-thiadiazolyl-2-yl), triazolyl
(z.B. 1 ,2,3-Triazol-4-yl, 1 ,2,4-Triazol-3-yl), Tetrazol-5-yl, Pyridyl (z.B. Pyridin-2- yl, Pyridin— 3— yl, Pyridin— 4— yl), Pyrazinyl (z.B. Pyridazin-3-yl, Pyridazin-4-yl), Pyri- midinyl (z.B. Pyrimidin-2-yl, Pyrimidin-4-yl, Pyrimidin-5-yl), Pyrazin-2-yl, Triazinyl (z.B. 1 ,3,5-Triazin-2-yl, 1 ,2,4-Triazin-3-yl, 1 ,2,4-Triazin-5-yl, 1 ,2,4-Triazin-6-yl), Tetrazinyl (z.B. 1 ,2,4,5-Tetrazin-3-yl); sowie(eg 1, 2,3-triazol-4-yl, 1, 2,4-triazol-3-yl), tetrazol-5-yl, pyridyl (eg pyridin-2-yl, pyridin-3-yl, pyridine) 4-yl), pyrazinyl (eg pyridazin-3-yl, pyridazin-4-yl), pyrimidinyl (eg pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl), pyrazine-2-yl , Triazinyl (eg, 1, 3,5-triazin-2-yl, 1, 2,4-triazin-3-yl, 1, 2,4-triazin-5-yl, 1, 2,4-triazine-6 yl), tetrazinyl (eg 1, 2,4,5-tetrazine-3-yl); such as
Bicyclen wie die benzanellierten Derivate der vorgenannten Monocyclen, z.B. Chi- nolinyl, Isochinolinyl, Indolyl, Benzthienyl, Benzofuranyl, Benzoxazolyl, Benzthiazo- IyI, Benzisothiazolyl, Benzimidazolyl, Benzopyrazolyl, Benzthiadiazolyl, Benzotriazo- IyI.Bicyclic compounds such as the benzanellated derivatives of the aforementioned monocycles, e.g. Quinolinyl, isoquinolinyl, indolyl, benzthienyl, benzofuranyl, benzoxazolyl, benzothiazolyl, benzisothiazolyl, benzimidazolyl, benzopyrazolyl, benzthiadiazolyl, benzotriazole IyI.
5- oder 6-gliedriges Heteroaryl mit ein bis vier Stickstoffatomen, oder ein bis drei Stickstoffatomen und einem Sauerstoff- oder Schwefelatom, oder mit einem Sauerstoff- oder Schwefelatom: z.B. über ein C-Atom verknüpfte aromatische 5-Ring-Heterocyclen, welche neben Kohlenstoffatomen ein bis vier Stickstoffatome, oder ein bis drei Stickstoffatome und ein Schwefel- oder Sauerstoffatom, oder ein Schwefel- oder Sauerstoffatom als Ringglieder enthalten können, z.B. 2-Furyl, 3-Furyl, 2-Thienyl, 3-Thienyl, 2-Pyrrolyl, 3-Pyrrolyl, 3-lsoxazolyl, 4-lsoxazolyl, 5-lsoxazolyl, 3-lsothiazolyl, 4-lsothiazolyl, 5- Isothiazolyl, 3-Pyrazolyl, 4-Pyrazolyl, 5-Pyrazolyl, 2-Oxazolyl, 4-Oxazolyl, 5- Oxazolyl, 2-Thiazolyl, 4-Thiazolyl, 5-Thiazolyl, 2-lmidazolyl, 4-lmidazolyl, 1 ,2,4-5- or 6-membered heteroaryl having one to four nitrogen atoms, or one to three nitrogen atoms and one oxygen or sulfur atom, or with an oxygen or sulfur atom: e.g. C-atom linked aromatic 5-membered heterocycles which may contain, besides carbon atoms, one to four nitrogen atoms, or one to three nitrogen atoms and one sulfur or oxygen atom, or a sulfur or oxygen atom as ring members, e.g. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3 Pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2,4-
Oxadiazol-3-yl, 1 ,2,4-Oxadiazol-5-yl, 1 ,2,4-Thiadiazol-3-yl, 1 ,2,4-Thiadiazol-5-yl, 1 ,2,4-Triazol-3-yl, 1 ,3,4-Oxadiazol-2-yl, 1 ,3,4-Thiadiazol-2-yl und 1 ,3,4-Triazol-2-yl;Oxadiazol-3-yl, 1, 2,4-oxadiazol-5-yl, 1, 2,4-thiadiazol-3-yl, 1, 2,4-thiadiazol-5-yl, 1, 2,4-triazole 3-yl, 1, 3,4-oxadiazol-2-yl, 1, 3,4-thiadiazol-2-yl and 1, 3,4-triazol-2-yl;
z.B. über ein C-Atom verknüpfte aromatische 6-Ring Heterocyclen, welche neben Kohlenstoffatomen ein bis vier, vorzugsweise ein bis drei Stickstoffatome als Ringglieder enthalten können, z.B. 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 3-Pyridazinyl, 4- Pyridazinyl, 2-Pyrimidinyl, 4-Pyrimidinyl, 5-Pyrimidinyl, 2-Pyrazinyl, 1 ,3,5-Triazin-2-yl und 1 ,2,4-Triazin-3-yl; In einer besonderen Ausführungsform haben die Variablen der heteroaroylsubstituier- ten Alanine der Formel I folgende Bedeutungen, wobei diese für sich allein betrachtet als auch in Kombination miteinander besondere Ausgestaltungen der Verbindungen der Formel I darstellen:for example, via a carbon atom-linked aromatic 6-membered ring heterocycles, which in addition to carbon atoms may contain one to four, preferably one to three nitrogen atoms as ring members, for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl , 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3,5-triazin-2-yl and 1, 2,4-triazin-3-yl; In a particular embodiment, the variables of the heteroaroyl-substituted alanines of the formula I have the following meanings, these being considered singly and in combination with one another in particular embodiments of the compounds of the formula I:
Bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der A 5-gliedriges Heteroaryl mit ein bis vier Stickstoffatomen, oder ein bis drei Stick- stoffatomen und einem Sauerstoff- oder Schwefelatom, oder mit einem Sauerstoff oder Schwefelatom; besonders bevorzugt 5-gliedriges Heteroaryl ausgewählt aus der Gruppe Thie- nyl, Furyl, Pyrazolyl, Imidazolyl, Thiazolyl und Oxazolyl; insbesonders bevorzugt 5-gliedriges Heteroaryl ausgewählt aus der Gruppe Thienyl, Furyl, Pyrazolyl und Imidazolyl; wobei die genannten Heteroarylreste durch einen Ci-Cβ-Halogenalkyl-Rest, bevorzugt in 2-Position durch einen Ci-Cβ-Halogenalkyl-Rest substituiert sind, und 1 bis 3 Reste aus der Gruppe Halogen, Cyano, Ci-Cδ-Alkyl, C3- Cδ-Cycloalkyl, Ci-Cδ-Alkoxy, Ci-Cδ-Halogenalkoxy und C 1 -Ce-AIkOXy-Ci-C4- alkyl tragen können; bedeutet.Preference is given to the heteroaroyl-substituted alanines of the formula I in which A is 5-membered heteroaryl having one to four nitrogen atoms, or one to three nitrogen atoms and one oxygen or sulfur atom, or having one oxygen or sulfur atom; particularly preferably 5-membered heteroaryl selected from the group of thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl; especially preferred 5-membered heteroaryl selected from the group thienyl, furyl, pyrazolyl and imidazolyl; wherein said heteroaryl radicals are substituted by a Ci-Cβ-haloalkyl radical, preferably in the 2-position by a Ci-Cβ-haloalkyl radical, and 1 to 3 radicals from the group halogen, cyano, Ci-Cδ-alkyl, C3 - Can carry Cδ-cycloalkyl, Ci-Cδ-alkoxy, Ci-Cδ-haloalkoxy and C 1 -Ce-AIkOXy-Ci-C 4 - alkyl; means.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der A 5-gliedriges Heteroaryl mit ein bis vier Stickstoffatomen, oder ein bis drei Stick- stoffatomen und einem Sauerstoff- oder Schwefelatom, oder mit einem Sauerstoff oder Schwefelatom; besonders bevorzugt 5-gliedriges Heteroaryl ausgewählt aus der Gruppe Thienyl, Furyl, Pyrazolyl, Imidazolyl, Thiazolyl und Oxazolyl; insbesonders bevorzugt 5-gliedriges Heteroaryl ausgewählt aus der Gruppe Thienyl, Furyl, Pyrazolyl und Imidazolyl; wobei die genannten Heteroarylreste partiell oder vollständig halogeniert sein können und/oder 1 bis 3 Reste aus der Gruppe Cyano, Ci-Cδ-Alkyl, C3- Cδ-Cycloalkyl, Ci-Cβ-Halogenalkyl, Ci-Cδ-Alkoxy, Ci-Cδ-Halogenalkoxy und Ci-C6-Alkoxy-Ci-C4-alkyl tragen können; bedeutet.Likewise preferred are the heteroaroyl-substituted alanines of the formula I in which A 5-membered heteroaryl having one to four nitrogen atoms, or one to three nitrogen atoms and one oxygen or sulfur atom, or with an oxygen or sulfur atom; particularly preferably 5-membered heteroaryl selected from the group of thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl; especially preferred 5-membered heteroaryl selected from the group thienyl, furyl, pyrazolyl and imidazolyl; where the said heteroaryl radicals can be partially or completely halogenated and / or 1 to 3 radicals from the group cyano, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 8 -cycloalkyl Halogenoalkoxy and Ci-C6-alkoxy-Ci-C 4 alkyl can carry; means.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der A 5-gliedriges Heteroaryl mit ein bis vier Stickstoffatomen, oder ein bis drei Stick- stoffatomen und einem Sauerstoff- oder Schwefelatom, oder mit einem Sauerstoffatom; besonders bevorzugt 5-gliedriges Heteroaryl ausgewählt aus der Gruppe Furyl, Pyrazolyl, Imidazolyl, Thiazolyl und Oxazolyl; insbesonders bevorzugt 5-gliedriges Heteroaryl ausgewählt aus der Gruppe Fu- ryl, Pyrazolyl und Imidazolyl; wobei die genannten Heteroarylreste partiell oder vollständig halogeniert sein können und/oder 1 bis 3 Reste aus der Gruppe Cyano, Ci-Cδ-Alkyl, C3- Cβ-Cycloalkyl, Ci-Cδ-Halogenalkyl, Ci-Cδ-Alkoxy, Ci-Cδ-Halogenalkoxy undEqually preferred are the heteroaroyl-substituted alanines of the formula I in which A is 5-membered heteroaryl having one to four nitrogen atoms, or one to three nitrogen atoms and one oxygen or sulfur atom, or having one oxygen atom; particularly preferably 5-membered heteroaryl selected from the group furyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl; especially preferred 5-membered heteroaryl selected from the group furyl, pyrazolyl and imidazolyl; where the heteroaryl radicals mentioned can be partially or completely halogenated and / or 1 to 3 radicals from the group consisting of cyano, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 8 -cycloalkyl, Haloalkoxy and
Ci-C6-Alkoxy-Ci-C4-alkyl tragen können; bedeutet.Ci-C6-alkoxy-Ci-C4-alkyl can carry; means.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der A 6-gliedriges Heteroaryl mit ein bis vier Stickstoffatomen; besonders bevorzugt Pyridyl oder Pyrimidyl. insbesondere bevorzugt Pyrimidyl; wobei die genannten Heteroarylreste partiell oder vollständig halogeniert sein können und/oder 1 bis 3 Reste aus der Gruppe Cyano, Ci-Cβ-Alkyl, C3- Cβ-Cycloalkyl, Ci-Cβ-Halogenalkyl, Ci-Cδ-Alkoxy, Ci-Cδ-Halogenalkoxy undLikewise preferred are the heteroaroyl-substituted alanines of the formula I in which A is 6-membered heteroaryl having one to four nitrogen atoms; particularly preferably pyridyl or pyrimidyl. especially preferred pyrimidyl; where the said heteroaryl radicals can be partially or completely halogenated and / or 1 to 3 radicals from the group cyano, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 8 -cycloalkyl Haloalkoxy and
Ci-C6-Alkoxy-Ci-C4-alkyl tragen können; bedeutet.Ci-C6-alkoxy-Ci-C4-alkyl can carry; means.
Ebenso bevorzugt sind die heteroaroylsubstituierten Alanine der Formel I, in der A 5- oder 6-gliedriges Heteroaryl mit ein bis vier Stickstoffatomen, oder mit ein bis drei Stickstoffatomen und einem Sauerstoff- oder Schwefelatom, oder mit einem Sauerstoff- oder Schwefelatom, welches durch einen Ci-Cβ-Halogenalkyl-Rest, bevorzugt in 2-Position durch einen Ci-Cβ-Halogenalkyl-Rest, substituiert ist, und 1 bis 3 Reste aus der Gruppe Cyano, Ci-Cδ-Alkyl, C3-C6- Cycloalkyl, Ci-Cδ-Halogenalkyl, Ci-Cδ-Alkoxy, Ci-Cδ-Halogenalkoxy und Ci-Cβ-Likewise preferred are the heteroaroyl-substituted alanines of the formula I in which A is 5- or 6-membered heteroaryl having one to four nitrogen atoms, or having one to three nitrogen atoms and one oxygen or sulfur atom, or an oxygen or sulfur atom which is replaced by a Ci-Cβ-haloalkyl radical, preferably in the 2-position by a Ci-Cβ-haloalkyl radical, is substituted, and 1 to 3 radicals from the group cyano, Ci-Cδ-alkyl, C3-C6-cycloalkyl, ci C 8 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy and C 1 -C 6
Alkoxy-Ci-C4-alkyl tragen kann; bedeutet.Can carry alkoxy-Ci-C4-alkyl; means.
Ebenso bevorzugt sind die heteroaroylsubstituierten Alanine der Formel I, in der A 5- oder 6-gliedriges Heteroaryl ausgewählt aus der Gruppe Pyrrolyl, Thienyl,Likewise preferred are the heteroaroyl-substituted alanines of the formula I in which A is 5- or 6-membered heteroaryl selected from the group consisting of pyrrolyl, thienyl,
Furyl, Pyrazolyl, Imidazolyl, Thiazolyl, Oxazolyl, Tetrazolyl, Pyridyl und Pyrimidi- nyl; wobei die genannten Heteroarylreste partiell oder vollständig halogeniert sein können und/oder 1 bis 3 Reste aus der Gruppe Cyano, Ci-Cδ-Alkyl, C3- Cδ-Cycloalkyl, Ci-Cδ-Halogenalkyl, Ci-Cδ-Alkoxy, Ci-Cδ-Halogenalkoxy und Ci-C6-Alkoxy-Ci-C4-alkyl tragen können;Furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, tetrazolyl, pyridyl and pyrimidinyl; where the said heteroaryl radicals can be partially or completely halogenated and / or 1 to 3 radicals from the group cyano, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 8 -cycloalkyl Haloalkoxy and Ci-C6-alkoxy-Ci-C4-alkyl can carry;
besonders bevorzugt 5- oder 6-gliedriges Heteroaryl ausgewählt aus der Gruppe Thienyl, Furyl, Pyrazolyl, Imidazolyl, Thiazolyl, Oxazolyl und Pyridyl; wobei die genannten Heteroarylreste partiell oder vollständig halogeniert sein können und/oder 1 bis 3 Reste aus der Gruppe Ci-Cβ-Alkyl, C3-C6-particularly preferably 5- or 6-membered heteroaryl selected from the group of thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl and pyridyl; where the heteroaryl radicals mentioned can be partially or completely halogenated and / or 1 to 3 radicals from the group consisting of C 1 -C 6 -alkyl, C 3 -C 6 -alkyl radicals and
Cycloalkyl und Ci-Cβ-Halogenalkyl tragen können; insbesondere bevorzugt 5-gliedriges Heteroaryl ausgewählt aus der Gruppe Thienyl, Furyl, Pyrazolyl, Imidazolyl, Thiazolyl und Oxazolyl; wobei die genannten Heteroarylreste partiell halogeniert sein können und/oder 1 bis 2 Reste aus der Gruppe Ci-Cβ-Alkyl und Ci-C4-Halogenalkyl tragen können;May carry cycloalkyl and Ci-Cβ-haloalkyl; particularly preferably 5-membered heteroaryl selected from the group of thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl; where said heteroaryl radicals may be partially halogenated and / or may carry from 1 to 2 radicals selected from the group consisting of C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl;
außerordentlich bevorzugt 5-gliedriges Heteroaryl ausgewählt aus der Gruppe Thienyl, Furyl, Pyrazolyl und Imidazolyl; wobei die genannten Heteroarylreste partiell halogeniert sein können und/oder 1 bis 2 Reste aus der Gruppe Ci-Cε-Alkyl und Ci-C4-Halogenalkyl tragen können, bedeutet.most preferably 5-membered heteroaryl selected from the group of thienyl, furyl, pyrazolyl and imidazolyl; where the said heteroaryl radicals may be partially halogenated and / or may carry from 1 to 2 radicals from the group consisting of C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl.
Ebenso bevorzugt sind die heteroaroylsubstituierten Alanine der Formel I, in der A 5- oder 6-gliedriges Heteroaryl ausgewählt aus der Gruppe Pyrrolyl, Furyl, Pyrazolyl, Imidazolyl, Thiazolyl, Oxazolyl, Tetrazolyl, Pyridyl und Pyrimidinyl; wobei die genannten Heteroarylreste partiell oder vollständig halogeniert sein können und/oder 1 bis 3 Reste aus der Gruppe Cyano, Ci-Cδ-Alkyl, C3- Cδ-Cycloalkyl, Ci-Cβ-Halogenalkyl, Ci-Cδ-Alkoxy, Ci-Cδ-Halogenalkoxy und tragen können;Likewise preferred are the heteroaroyl-substituted alanines of the formula I in which A is 5- or 6-membered heteroaryl selected from the group consisting of pyrrolyl, furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, tetrazolyl, pyridyl and pyrimidinyl; where the said heteroaryl radicals can be partially or completely halogenated and / or 1 to 3 radicals from the group cyano, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 8 -cycloalkyl Haloalkoxy and can carry;
besonders bevorzugt 5- oder 6-gliedriges Heteroaryl ausgewählt aus der Gruppe Furyl, Pyrazolyl, Imidazolyl, Thiazolyl, Oxazolyl und Pyridyl; wobei die genannten Heteroarylreste partiell oder vollständig halogeniert sein können und/oder 1 bis 3 Reste aus der Gruppe Ci-Cβ-Alkyl, C3-C6-particularly preferably 5- or 6-membered heteroaryl selected from the group furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl and pyridyl; where the heteroaryl radicals mentioned can be partially or completely halogenated and / or 1 to 3 radicals from the group consisting of C 1 -C 6 -alkyl, C 3 -C 6 -alkyl radicals and
Cycloalkyl und Ci-Cβ-Halogenalkyl tragen können;May carry cycloalkyl and Ci-Cβ-haloalkyl;
insbesondere bevorzugt 5-gliedriges Heteroaryl ausgewählt aus der Gruppe Furyl, Pyrazolyl, Imidazolyl, Thiazolyl und Oxazolyl; wobei die genannten Heteroarylreste partiell halogeniert sein können und/oder 1 bis 2 Reste aus der Gruppe Ci-Cβ-Alkyl und C1-C4- Halogenalkyl tragen können;particularly preferably 5-membered heteroaryl selected from the group furyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl; wherein said heteroaryl may be partially halogenated and / or may carry from 1 to 2 radicals selected from the group consisting of C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl;
außerordentlich bevorzugt 5-gliedriges Heteroaryl ausgewählt aus der Gruppe Furyl, Pyrazolyl und Imidazolyl; wobei die genannten Heteroarylreste partiell halogeniert sein können und/oder 1 bis 2 Reste aus der Gruppe Ci-Cβ-Alkyl und Ci-C4-Halogenalkyl tragen können; bedeutet.most preferably 5-membered heteroaryl selected from the group furyl, pyrazolyl and imidazolyl; where said heteroaryl radicals may be partially halogenated and / or may carry from 1 to 2 radicals selected from the group consisting of C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl; means.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der C-verknüpftes 5-oder 6-gliedriges Heteroaryl ausgewählt aus der Gruppe A1 bis A14 mitLikewise preferred are the heteroaroyl-substituted alanines of the formula I in which C-linked 5- or 6-membered heteroaryl selected from the group A1 to A14 with
A12 A13 A14 wobei der Pfeil die Verknüpfungsposition anzeigt undA12 A13 A14 where the arrow indicates the linking position and
R9 Wasserstoff, Halogen, Ci -Ce-Al kyl oder Ci-Ce-Halogenalkyl; besonders bevorzugt Wasserstoff, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl; insbesondere bevorzugt Wasserstoff oder Ci-C4-Al kyl; außerordentlich bevorzugt Wasserstoff;R 9 is hydrogen, halogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; particularly preferably hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; particularly preferably hydrogen or C 1 -C 4 -alkyl; most preferably hydrogen;
R10 Halogen, Ci-Cβ-Alkyl, Ci-Cβ-Halogenalkyl oder Ci-Cδ-Halogenalkoxy; besonders bevorzugt Halogen, Ci-C4-Al kyl oder Ci-Cβ-Halogenalkyl; insbesondere bevorzugt Halogen oder Ci-Cβ-Halogenalkyl; sehr bevorzugt Ci-Cβ-Halogenalkyl; außerordentlich bevorzugt Ci-C4-Halogenalkyl sehr außerordentlich bevorzugt CF3;R 10 is halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -haloalkoxy; particularly preferably halogen, C 1 -C 4 -alkyl or C 1 -C 6 -haloalkyl; particularly preferably halogen or Ci-Cβ-haloalkyl; very preferably Ci-Cβ-haloalkyl; extremely preferably C 1 -C 4 -haloalkyl very particularly preferably CF 3;
R11 Wasserstoff, Halogen, Ci-Ce-Al kyl oder Ci-Ce-Halogenalkyl; besonders bevorzugt Wasserstoff, Halogen oder Ci-C4-Halogenalkyl; insbesondere bevorzugt Wasserstoff oder Halogen; außerordentlich bevorzugt Wasserstoff; undR 11 is hydrogen, halogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; particularly preferably hydrogen, halogen or C 1 -C 4 -haloalkyl; especially preferably hydrogen or halogen; most preferably hydrogen; and
R12 Wasserstoff, Ci -C6-Al kyl, C3-C6-Cycloalkyl, Ci-C6-Halogenalkyl oder d-R 12 is hydrogen, C -C alkyl 6 -alkyl, C 3 -C 6 cycloalkyl, Ci-C 6 haloalkyl or C
C6-Alkoxy-Ci-C4-alkyl; besonders bevorzugt Ci-C4-Alkyl, C3-C6-Cycloalkyl, Ci-C4-Halogenalkyl oder Ci-C4-Alkoxy-Ci-C4-alkyl; insbesondere bevorzugt Ci-C4-Alkyl oder Ci-C4-Halogenalkyl; außerordentlich bevorzugt Ci-C4-Alkyl; sehr außerordentlich bevorzugt CH3;C 6 alkoxy-C 1 -C 4 -alkyl; particularly preferably C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; particularly preferably C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; extremely preferably C 1 -C 4 -alkyl; very preferably CH3;
bedeuten;mean;
besonders bevorzugt A1 , A2, A3, A4, A5, A6, A8 oder A9; wobei R9 bis R12 wie voranstehend genannt definiert werden;particularly preferably A1, A2, A3, A4, A5, A6, A8 or A9; wherein R 9 to R 12 are defined as mentioned above;
außerordentlich bevorzugt A1 , A2, A5 oder A6; wobei R9 bis R12 wie voranstehend genannt definiert werden; bedeutet.most preferably A1, A2, A5 or A6; wherein R 9 to R 12 are defined as mentioned above; means.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der R1 Wasserstoff; bedeutet.Likewise preferred are the heteroaroyl-substituted alanines of the formula I in which R 1 is hydrogen; means.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der R2 Wasserstoff oder Hydroxy; besonders bevorzugt Wasserstoff; bedeutet.Likewise preferred are the heteroaroyl-substituted alanines of the formula I in which R 2 is hydrogen or hydroxyl; particularly preferably hydrogen; means.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in derLikewise preferred are the heteroaroyl-substituted alanines of the formula I in which
R1 Wasserstoff; undR 1 is hydrogen; and
R2 Wasserstoff oder Hydroxy; besonders bevorzugt Wasserstoff; bedeuten.R 2 is hydrogen or hydroxy; particularly preferably hydrogen; mean.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in derLikewise preferred are the heteroaroyl-substituted alanines of the formula I in which
R3 Ci-Ce-Alkyl oder Ci-C6-Halogenalkyl; besonders bevorzugt Ci-Cβ-Alkyl; insbesondere bevorzugt Ci-C4-Alkyl; außerordentlich bevorzugt CH3; bedeutet. Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der R4 Wasserstoff oder Ci -C4-Al kyl; bevorzugt Wasserstoff oder CH3; insbesondere bevorzugt Wasserstoff; bedeutet.R 3 is C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; particularly preferably C 1 -C 6 -alkyl; especially preferably C 1 -C 4 -alkyl; most preferably CH 3; means. Likewise preferred are the heteroaroyl-substituted alanines of the formula I in which R 4 is hydrogen or C 1 -C 4 -alkyl; preferably hydrogen or CH3; especially preferably hydrogen; means.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der R5 Wasserstoff, Ci-C6-Al kyl, C2-C6-Alkenyl, C2-C6-Al kinyl, Ci-C6-Halogenalkyl, C2-Also preferred are the heteroaroyl-substituted alanines of the formula I in which R 5 is hydrogen, Ci-C 6 alkyl-Al, C 2 -C 6 alkenyl, C 2 -C 6 kinyl -alkyl, Ci-C 6 haloalkyl, C 2 -
C6-Halogenalkenyl, C2-C6-Halogenalkinyl, Ci-C6-Cyanoalkyl, C2-C6- Cyanoalkenyl, C2-C6-Cyanoalkinyl, Ci-C6-Hydroxyalkyl, C2-C6-Hydroxyalkenyl,C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 6 cyanoalkyl, C 2 -C 6 - cyanoalkenyl, C 2 -C 6 -Cyanoalkinyl, Ci-C 6 hydroxyalkyl, C 2 -C 6 -Hydroxyalkenyl .
C2-C6-Hydroxyalkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, 3- bis 6-gliedriges Heterocyclyl, wobei die voranstehen genannten Cycloalkyl, Cycloalkenyl oder 3- bis 6- gliedrigen Heterocyclylreste partiell oder vollständig halogeniert sein kön- nen und/oder ein bis drei Reste aus der Gruppe Oxo, Cyano, Nitro, CrC6-C 2 -C 6 -Hydroxyalkinyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, 3- to 6-membered heterocyclyl, wherein said precede said cycloalkyl, cycloalkenyl or 3- to 6-membered heterocyclyl radicals may be partially or fully halogenated and / or one to three radicals from the group consisting of oxo, cyano, nitro, CrC 6 -
Alkyl, Ci-C6-Halogenalkyl, Hydroxy, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy, Hydroxycarbonyl, Ci-C6-Alkoxycarbonyl, Hydroxycarbonyl-Ci-C6-alkoxy, Ci-C6-Alkoxycarbonyl-Ci-C6-alkoxy, Amino, Ci-C6-Alkylamino, Di(CrC6- alkyl)amino, Ci-C6-Alkylsulfonylamino, Ci-Cδ-Halogenalkylsulfonylamino, Aminocarbonylamino, (CrC6-Alkylamino)carbonylamino, Di(CrC6- alkyl)aminocarbonylamino, Aryl und Aryl(CrC6-alkyl) tragen können; Ci-C6-Alkoxy-Ci-C4-alkyl, C2-C6-Alkenyloxy-CrC4-alkyl, C2-C6-Alkinyloxy-CrC4- alkyl, Ci-C6-Halogenalkoxy-CrC4-alkyl, C2-C6-Halogenalkenyloxy-CrC4-alkyl, C2-C6-Halogenalkinyloxy-CrC4-alkyl, Ci-C6-Alkoxy-Ci-C4-alkoxy-CrC4-alkyl, Cr C6-Alkylthio-CrC4-alkyl, C2-C6-Alkenylthio-CrC4-alkyl, C2-C6-Alkinylthio-CrC4- alkyl, Ci-C6-Halogenalkyl-CrC4-thioalkyl, C2-C6-Halogenalkenyl-CrC4-thioalkyl, C2-C6-Halogenalkinyl-CrC4-thioalkyl, CrCe-Alkylsulfinyl-CrCralkyl, CrC6- Halogenalkylsulfinyl-CrC4-alkyl, Ci-C6-Alkylsulfonyl-CrC4-alkyl, CrC6- Halogenalkylsulfonyl-CrC4-alkyl, Amino-CrC4-alkyl, CrC6-AI kyla mino-Cr C4- alkyl, Di(Ci-C6-alkyl)amino-CrC4-alkyl, Ci-C6-Alkylsulfonylamino-CrC4-alkyl, CrAlkyl, Ci-C 6 haloalkyl, hydroxy, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, hydroxycarbonyl-Ci-C 6 alkoxy, Ci-C 6 alkoxycarbonyl Ci-C 6 alkoxy, amino, Ci-C6 alkylamino, di (-C 6 - alkyl) amino, Ci-C 6 alkylsulfonylamino, Ci-Cδ-haloalkylsulfonylamino, aminocarbonylamino, (CrC 6 alkylamino) carbonylamino, di ( C 1 -C 6 alkyl) aminocarbonylamino, aryl and aryl (C 1 -C 6 alkyl); Ci-C 6 alkoxy-Ci-C 4 alkyl, C 2 -C 6 alkenyloxy-CrC 4 alkyl, C 2 -C 6 alkynyloxy-CrC 4 - alkyl, Ci-C 6 haloalkoxy-CrC 4 - alkyl, C 2 -C 6 haloalkenyloxy--C 4 alkyl, C 2 -C 6 haloalkynyloxy--C 4 -alkyl, Ci-C 6 alkoxy-Ci-C4-alkoxy-CrC 4 alkyl, Cr C 6 alkylthio-CrC 4 alkyl, C 2 -C 6 -alkenylthio--C 4 alkyl, C 2 -C 6 -alkynylthio--C 4 - alkyl, Ci-C 6 haloalkyl--C 4 thioalkyl, C 2 -C 6 haloalkenyl--C 4 thioalkyl, C 2 -C 6 haloalkynyl--C 4 thioalkyl, alkylsulfinyl CRCE-CrCralkyl, CrC 6 - haloalkylsulfinyl--C 4 alkyl, C 6 alkylsulfonyl--C 4 alkyl, CrC 6 - haloalkylsulfonyl -C 4 alkyl, amino-CrC 4 alkyl, -C 6 -AI kyla mino-Cr C 4 - alkyl, di (Ci-C 6 alkyl) amino-CrC 4 alkyl, Ci-C 6 Alkylsulfonylamino-CrC 4 -alkyl, Cr
C6-Alkylsulfonyl(Ci-C6-alkyl)amino-CrC4-alkyl, CrC6-Alkylcarbonyl, Hydroxycarbonyl, CrC6-Alkoxycarbonyl, Aminocarbonyl, CrCe-Alkylaminocarbonyl, Di(Cr C6-alkyl)aminocarbonyl, Formylamino-CrC4-alkyl, CrC6-Alkoxycarbonylamino- CrC4-alkyl, Ci-C6-Alkylcarbonyl-CrC6-alkyl, Hydroxycarbonyl-CrCralkyl, CrC6- Alkoxycarbonyl-CrCralkyl, Ci-C6-Halogenalkoxycarbonyl-CrC4-alkyl, CrC6-C 6 alkylsulfonyl (C 1 -C 6 alkyl) aminoCrC 4 alkyl, C 1 -C 6 alkylcarbonyl, hydroxycarbonyl, C 1 -C 6 alkoxycarbonyl, aminocarbonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 -alkyl) aminocarbonyl, formylamino CrC 4 alkyl, -C 6 alkoxycarbonylamino -C 4 -alkyl, Ci-C 6 alkylcarbonyl -C 6 alkyl, hydroxycarbonyl-CrCralkyl, -C 6 - alkoxycarbonyl-CrCralkyl, Ci-C 6 haloalkoxycarbonyl--C 4 -alkyl, CrC 6 -
Alkylcarbonyloxy-CrC4-alkyl, Aminocarbonyl-CrC^alkyl, CrC6- Alkylaminocarbonyl-CrC4-alkyl, Di(Ci-C6-alkyl)aminocarbonyl-CrC4-alkyl, CrC6- Alkylcarbonylamino-CrC4-alkyl, Ci-C6-Alkylcarbonyl-(Ci-C6-alkylamino)-CrC4- alkyl, Di(Ci-C6-alkyl)aminocarbonyloxy-CrC4-alkyl, [(CrC6-Alkyl)amino- carbonylamino]CrC4-alkyl, [Di(Ci-C6-alkyl)amino-carbonylamino]CrC4-alkyl;Alkylcarbonyloxy -C 4 -alkyl, aminocarbonyl-CrC ^ alkyl, CrC 6 - alkylaminocarbonyl -C 4 alkyl, di (Ci-C 6 alkyl) aminocarbonyl--C 4 alkyl, -C 6 - alkylcarbonylamino -C 4 alkyl, C -C 6 alkylcarbonyl (Ci-C 6 -alkylamino) CRC 4 - alkyl, di (Ci-C 6 alkyl) aminocarbonyloxy -C 4 alkyl, [(-C 6 alkyl) amino- carbonylamino] CrC 4 - alkyl, [di (C 1 -C 6 -alkyl) amino-carbonylamino] C 1 -C 4 -alkyl;
Phenyl-CrC4-alkyl, Phenyl-C2-C4-alkenyl, Phenyl-C2-C4-alkinyl, Phenyl-d-C4- halogenalkyl, Phenyl-C2-C4-halogenalkenyl, Phenyl-C2-C4-halogenalkinyl, Phe- nyl-CrC4-hydroxyalkyl, Phenyl-C2-C4-hydroxyalkenyl, Phenyl-C2-C4- hydroxyalkinyl, Phenylcarbonyl-Ci-C4-alkyl, Phe- nyloxycarbonyl-Ci-C4-alkyl, Phenyloxy-Ci-C4-alkyl, Phenylthio-Ci-C4-alkyl, Phe- nylsulfinyl-Ci-C4-alkyl, Phenylsulfonyl-Ci-C4-alkyl,Phenyl-CrC 4 -alkyl, phenyl-C 2 -C 4 -alkenyl, phenyl-C 2 -C 4 -alkynyl, phenyl-dC 4 - haloalkyl, phenyl-C 2 -C 4 -haloalkenyl, phenyl-C 2 -C 4 -haloalkynyl, phenyl-CrC 4 hydroxyalkyl, phenyl-C 2 -C 4 -hydroxyalkenyl, phenyl-C 2 -C 4 - hydroxyalkynyl, phenylcarbonyl-C 1 -C 4 -alkyl, Phenyloxycarbonyl-C 1 -C 4 -alkyl, phenyloxy-C 1 -C 4 -alkyl, phenylthio-C 1 -C 4 -alkyl, phenylsulfinyl-C 1 -C 4 -alkyl, phenylsulfonyl-C 1 -C 4 -alkyl,
Heteroaryl, Heteroaryl-Ci-C4-alkyl, Heteroaryl-C2-C4-alkenyl, Heteroaryl-C2-C4- alkinyl, Heteroaryl-Ci-C4-halogenalkyl, Heteroaryl-C2-C4-halogenalkenyl, Hetero- aryl-C2-C4-halogenalkinyl, Heteroaryl-Ci-C4-hydroxyalkyl, Heteroaryl-C2-C4- hydroxyalkenyl, Heteroaryl-C2-C4-hydroxyalkinyl, Heteroarylcarbonyloxy-Ci^-alkyl, Heteroaryloxycarbonyl-Ci^-alkyl, Heteroaryl oxy-Ci-C4-a I ky I, Heteroarylthio-Ci-C4-alkyl, Heteroarylsulfinyl-Ci-C4-alkyl, He- teroarylsulfonyl-Ci-C4-alkyl, wobei die vorstehend genannten Phenyl- und Heteroarylreste partiell oder vollständig halogeniert sein können und/oder ein bis drei Reste aus der Gruppe Cyano, Nitro, Ci- Ce-Alkyl, d-Cβ-Halogenalkyl, Hydroxy, Ci-C-6-Hydroxyalkyl, Ci-C6-Alkoxy, CrC6- Halogenalkoxy, Hydroxycarbonyl, Ci-Cδ-Alkoxycarbonyl, Hydroxycarbonyl-Ci-Cδ- alkoxy, Ci-C6-Alkoxycarbonyl-Ci-C6-alkoxy, Amino, Ci-C6-Alkylamino, Di(Ci-C6-alkyl)- amino, Ci-C6-Alkylsulfonylamino, Ci-C6-Halogenalkylsulfonylamino, (C-i-Cδ- Alkylamino)carbonylamino, Di-(Ci-C6-alkyl)-aminocarbonylamino, Aryl und Aryl(Ci-C6- alkyl) tragen können.Heteroaryl, heteroaryl-C 1 -C 4 -alkyl, heteroaryl-C 2 -C 4 -alkenyl, heteroaryl-C 2 -C 4 -alkynyl, heteroaryl-C 1 -C 4 -haloalkyl, heteroaryl-C 2 -C 4 -haloalkenyl, heteroaryl-C 2 -C 4 -haloalkynyl, heteroaryl-C 1 -C 4 -hydroxyalkyl, heteroaryl-C 2 -C 4 -hydroxyalkenyl, heteroaryl-C 2 -C 4 -hydroxyalkynyl, Heteroarylcarbonyloxy-C 1-8 -alkyl, heteroaryloxycarbonyl-C 1-4 -alkyl, heteroaryl-oxy-C 1 -C 4 -alkyl, heteroarylthio-C 1 -C 4 -alkyl, heteroarylsulfinyl-C 1 -C 4 -alkyl, heteroarylsulfonyl-C 1 -C 4 -alkyl alkyl, where the abovementioned phenyl and heteroaryl radicals may be partially or completely halogenated and / or one to three radicals from the group of cyano, nitro, ci-C 1 -alkyl, C 1 -C 6 -haloalkyl, hydroxy, C 1 -C 6 -alkyl, hydroxyalkyl, Ci-C 6 alkoxy, -C 6 - haloalkoxy, hydroxycarbonyl, Ci-Cδ alkoxycarbonyl, hydroxycarbonyl-Ci-Cδ- alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, amino, Ci-C6-alkylamino, Di (C 1 -C 6 -alkyl) amino, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -haloalkylsulfonylamino, (C 1 -C 6 -alkylamino) carbonylamino, di (C 1 -C 6 -alkyl) aminocarbonylamino, aryl and aryl (C 1 -C 4 -alkyl) C6 alkyl) can carry.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der R5 Wasserstoff, Ci -C6-Al kyl, C2-C6-Alkenyl, C2-C6-Al kinyl, Ci-C6-Halogenalkyl, C2- Cδ-Halogenalkenyl, C2-C6-Halogenalkinyl, Ci-Cβ-Cyanoalkyl, Ci-Cδ-Hydroxyalkyl, C2-C6-Hydroxyalkenyl, C2-C6-Hydroxyalkinyl, C3-C6-Cycloalkyl, C3-C6- Cycloalkenyl, 3- bis 6-gliedriges Heterocyclyl, wobei die voranstehen genannten Cycloalkyl, Cycloalkenyl oder 3- bis 6- gliedrigen Heterocyclyl reste partiell oder vollständig halogeniert sein können und/oder einen bis drei Reste aus der Gruppe Oxo, Ci-Cβ-Alkyl, C-i-Cδ- Halogenalkyl, Hydroxycarbonyl und Ci-Cδ-Alkoxycarbonyl tragen können; Ci-C6-Alkoxy-Ci-C4-alkyl, Ci-C6-Halogenalkoxy-Ci-C4-alkyl, Ci-C6-Alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C6-Alkylthio-Ci-C4-alkyl, Ci-C6-Alkylsulfonylamino-Ci-C4- alkyl, Hydroxycarbonyl, Ci-Cδ-Alkoxycarbonyl, Hydroxycarbonyl-Ci-C4-alkyl, d- C6-Alkoxycarbonyl-Ci-C4-alkyl, Ci-C6-Halogenalkoxycarbonyl-Ci-C4-alkyl, Ci-Cβ- Alkylcarbonyloxy-Ci-C4-alkyl, Ci-C6-Alkylcarbonylamino-Ci-C4-alkyl, [(Ci-Cβ- Alkyl)aminocarbonylamino]Ci-C4-alkyl, Di^i-Ce-Alkyljaminocarbonylamino-Ci- C4-alkyl, [Di(Ci-C6-alkylamino)carbonyloxy]Ci-C4-alkyl, Formylamino-Ci-C4-alkyl;The heteroaroyl-substituted alanines of the formula I in which R 5 is hydrogen, C -C alkyl are also preferred 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 kinyl -alkyl, Ci-C 6 haloalkyl, C 2 - Cδ haloalkenyl, C 2 -C 6 haloalkynyl, Ci-Cβ-cyanoalkyl, Ci-Cδ-hydroxyalkyl, C 2 -C 6 hydroxyalkenyl, C 2 -C 6 hydroxyalkynyl, C3-C6-cycloalkyl, C3-C6 Cycloalkenyl, 3- to 6-membered heterocyclyl, wherein the above-mentioned cycloalkyl, cycloalkenyl or 3- to 6-membered heterocyclyl radicals may be partially or completely halogenated and / or one to three radicals from the group oxo, Ci-Cβ-alkyl, Ci-Cδ- halogenoalkyl, hydroxycarbonyl and Ci-Cδ-alkoxycarbonyl can carry; Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-haloalkoxy-Ci-C4-alkyl, Ci-C 6 alkoxy-Ci-C 4 - alkoxy-Ci-C4-alkyl, Ci-C 6- alkylthio-C 1 -C 4 -alkyl, C 1 -C 6 -alkylsulfonylamino-C 1 -C 4 -alkyl, hydroxycarbonyl, C 1 -C 6 -alkoxycarbonyl, hydroxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 4 -alkyl alkyl, C 1 -C 6 -haloalkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 6 -alkylcarbonyloxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkylcarbonylamino-C 1 -C 4 -alkyl, [(C 1 -C 6 -alkyl) aminocarbonyl-amino] ci C4-alkyl, di-1-C5-alkylaminocarbonylamino-C4-C4-alkyl, [di (C5-C6-alkylamino) carbonyloxy] C4-C4-alkyl, formylamino-C4-C4-alkyl;
Phenyl-Ci-C4-alkyl, Phenyl-C2-C4-alkenyl, Phenyl-C2-C4-alkinyl, Phenyl-Ci-C4- halogenalkyl, Phenyl-C2-C4-halogenalkenyl, Phenyl-Ci-C4-hydroxyalkyl, Pheny- loxy-Ci-C4-alkyl, Phenylthio-Ci-C4-alkyl, Phenylsulfinyl-Ci-C4-alkyl, Phenylsulfo- nyl-Ci-C4-alkyl; Heteroaryl, Heteroaryl-Ci-C4-alkyl, Heteroaryl-Ci-C4-hydroxyalkyl, Heteroaryloxy- Phenyl-Ci-C4-alkyl, phenyl-C 2 -C 4 -alkenyl, phenyl-C 2 -C 4 -alkynyl, phenyl-Ci-C 4 - haloalkyl, phenyl-C 2 -C 4 haloalkenyl, phenyl-C -C 4 -hydroxyalkyl, phenyl-C 1 -C 4 -alkyl, phenylthio-C 1 -C 4 -alkyl, phenylsulfinyl-C 1 -C 4 -alkyl, phenylsulfonyl-C 1 -C 4 -alkyl; Heteroaryl, heteroaryl-C 1 -C 4 -alkyl, heteroaryl-C 1 -C 4 -hydroxyalkyl, heteroaryloxy
Ci-C4-alkyl, Heteroarylthio-Ci-C4-alkyl, Heteroarylsulfinyl-Ci-C4-alkyl oder Hete- roarylsulfonyl-Ci-C4-alkyl, wobei die vorstehend genannten Phenyl- und Heteroarylreste partiell oder vollständig halogeniert sein können und/oder ein bis drei Reste aus der Gruppe Cyano, Nitro, Ci-C6-Alkyl, Ci-C6-Halogenalkyl, Hydroxy, CrC6- Alkoxy, Ci-Cδ-Halogenalkoxy, Hydroxycarbonyl, Ci-C6-Alkoxycarbonyl, Hydroxycarbonyl-Ci-Cδ-alkoxy, Ci-C6-Alkylsulfonylamino und CrC6-C 1 -C 4 -alkyl, heteroarylthio-C 1 -C 4 -alkyl, heteroarylsulfinyl-C 1 -C 4 -alkyl or heteroarylsulfonyl-C 1 -C 4 -alkyl, wherein the aforesaid phenyl and heteroaryl radicals may be partially or fully halogenated and / or a 6 alkyl to three radicals from the group cyano, nitro, Ci-C, C-C 6 haloalkyl, hydroxy, -C 6 - alkoxy, C -Cδ -haloalkoxy, hydroxycarbonyl, C 1 -C 6 -alkoxycarbonyl, hydroxycarbonyl-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylsulfonylamino and C 1 -C 6 -
Halogenalkylsulfonylamino tragen können;Can carry halogenoalkylsulfonylamino;
besonders bevorzugt Wasserstoff, Ci-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, d- Cδ-Halogenalkyl, C2-C6-Halogenalkenyl, Ci-C6-Hydroxyalkyl, Ci-C6-Alkoxy-Ci-C4- alkyl, Ci-C6-Halogenalkoxy-Ci-C4-alkyl, Hydroxycarbonyl-Ci-C4-alkyl, CrC6-particularly preferably hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy-Ci -C 4 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 4 -alkyl, hydroxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 6 -
Alkoxycarbonyl-Ci-C4-alkyl, Ci-Cδ-Alkylcarbonyloxy-Ci^-alkyl, CrC6- Alkylcarbonylamino-Ci-C4-alkyl, [Di(Ci-C6-alkyl)amino)carbonyloxy]Ci-C4-alkyl, Formylamino-Ci-C4-alkyl, Phenyl-Ci-C4-alkyl, Phenyl-C2-C4-alkenyl, Phenyl-C2- C4-Alkinyl, Phenyl-Ci-C4-halogenalkyl, Phenyl-C2-C4-halogenalkenyl, Phenyl-Ci- C4-hydroxyalkyl, Phenyloxy-Ci-C4-alkyl, Phenylthio-Ci-C4-alkyl, Phenylsulfinyl-Alkoxycarbonyl-Ci-C4-alkyl, Ci-Cδ-alkylcarbonyloxy-Ci ^ alkyl, -C 6 - alkylcarbonylamino-Ci-C4-alkyl, [di (Ci-C 6 alkyl) amino) carbonyloxy] Ci-C4-alkyl, Formylamino-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyl, phenyl-C 2 -C 4 -alkenyl, phenyl-C 2 -C 4 -alkynyl, phenyl-C 1 -C 4 -haloalkyl, phenyl-C 2 -C 4 -haloalkenyl, phenyl- C 1 -C 4 -hydroxyalkyl, phenyloxy-C 1 -C 4 -alkyl, phenylthio-C 1 -C 4 -alkyl, phenylsulfinyl
Ci-C4-alkyl oder Phenylsulfonyl-Ci-C4-alkyl, wobei die vorstehend genannten Phenylreste partiell oder vollständig halogeniert sein können und/oder ein bis drei Reste aus der Gruppe CrC6- Alkyl, Ci-Cδ-Halogenalkyl, Ci-C6-Alkoxy, Hydroxycarbonyl, Ci-C6-Alkoxy- carbonyl, Ci-C6-Alkylsulfonylamino und Ci-Ce-Halogenalkylsulfonylamino tragen können;C 1 -C 4 -alkyl or phenylsulfonyl-C 1 -C 4 -alkyl, where the abovementioned phenyl radicals may be partially or completely halogenated and / or one to three radicals from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 Alkoxy, hydroxycarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylsulfonylamino and C 1 -C 6 -haloalkylsulfonylamino;
insbesondere bevorzugt Wasserstoff, Ci-Cβ-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Ci-Cδ-Halogenalkyl, C2-C6-Halogenalkenyl, Ci-Cδ-Hydroxyalkyl, Hydroxycarbo- nyl-Ci-C4-alkyl, Ci-C6-Alkoxycarbonyl-Ci-C4-alkyl, [Di(Ci-C6-alkyl)aminocarbonyl- oxy]Ci-C4-alkyl, Formylamino-Ci-C4-alkyl;particularly preferably hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 1 -C 6 -hydroxyalkyl, hydroxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 4 -alkyl, [di (C 1 -C 6 -alkyl) aminocarbonyl-oxy] C 1 -C 4 -alkyl, formylamino-C 1 -C 4 -alkyl;
Phenyl-Ci-C4-alkyl, Phenyl-C2-C4-alkenyl, Phenyl-Ci-C4-hydroxyalkyl oder Phe- nylthio-Ci-C4-alkyl;Phenyl-C 1 -C 4 -alkyl, phenyl-C 2 -C 4 -alkenyl, phenyl-C 1 -C 4 -hydroxyalkyl or phenylthio-C 1 -C 4 -alkyl;
außerordentlich bevorzugt Wasserstoff, Ci-C6-Alkyl, C2-C6-Alkenyl, CrC6-extraordinarily preferably hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, -C 6 -
Halogenalkyl, C2-C6-Halogenalkenyl, Ci-Cδ-Hydroxyalkyl, Formylamino-Ci-C4- alkyl, Phenyl-Ci-C4-alkyl oder Phenyl-Ci-C4-hydroxyalkyl; bedeutet.Haloalkyl, C 2 -C 6 -haloalkenyl, C 1 -C 6 -hydroxyalkyl, formylamino-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyl or phenyl-C 1 -C 4 -hydroxyalkyl; means.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der R6 Wasserstoff, Ci -C6-Al kyl, C3-C6-Cycloalkyl, C3-C6-Alkenyl, C3-C6-Al kinyl, C3-C6- Halogenalkenyl, C3-C6-Halogenalkinyl, Formyl, Ci-C6-Alkylcarbonyl, C3-C6- Cycloalkylcarbonyl, C2-C6-Alkenylcarbonyl, C2-C6-Alkinylcarbonyl, CrC6- Alkoxycarbonyl, C3-C6-Alkenyloxycarbonyl, C3-C6-Alkinyloxycarbonyl, CrC6- Alkylaminocarbonyl, Cs-Ce-Alkenylaminocarbonyl, Cs-Ce-Alkinylaminocarbonyl,The heteroaroyl-substituted alanines of the formula I in which R 6 is hydrogen, C -C alkyl are also preferred 6 -alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 -alkyl kinyl , C 3 -C 6 - haloalkenyl, C 3 -C 6 -haloalkynyl, formyl, Ci-C 6 alkylcarbonyl, C 3 -C 6 - cycloalkylcarbonyl, C2-C6 alkenylcarbonyl, C2-C6 alkynylcarbonyl, CrC 6 - alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 -alkynyloxycarbonyl, -C 6 - alkylaminocarbonyl, Cs-Ce-alkenylaminocarbonyl, Cs-Ce alkynylaminocarbonyl,
Ci-Ce-Alkylsulfonylaminocarbonyl, Di(Ci-C6-alkyl)aminocarbonyl, N-(C3-C6- Alkenyl)-N-(Ci-C6-alkyl)-aminocarbonyl, N-(C3-C6-Alkinyl)-N-(Ci-C6-alkyl)- aminocarbonyl, N-(Ci-C6-Alkoxy)-N-(Ci-C6-alkyl)-amino-carbonyl, N-(C3-C6- Alkenyl)-N-(Ci-C6-alkoxy)-aminocarbonyl, N-(C3-C6-Alkinyl)-N-(Ci-C6-alkoxy)- aminocarbonyl, Di(Ci-C6-alkyl)aminothiocarbonyl, (CrCe-AlkylJcyanoimino, (A- mino)cyanoimino, [(CrCe-AlkylJaminolcyanoimino, Di(d-C6- alkyl)aminocyanoimino, Ci-C6-Alkylcarbonyl-Ci-C6-alkyl, Ci-C6-Alkoxyimino-Ci- Cβ-alkyl, N-(CrC6-Alkylamino)-imino-Ci-C6-alkyl, N-[Di(Ci-C6-alkyl)amino]imino-Ci-Ce-alkylsulphonylaminocarbonyl, di (Ci-C 6 alkyl) aminocarbonyl, N- (C 3 -C 6 - alkenyl) -N- (Ci-C 6 alkyl) aminocarbonyl, N- (C 3 -C 6 alkynyl) -N- (Ci-C 6 alkyl) - aminocarbonyl, N- (Ci-C 6 alkoxy) -N- (Ci-C 6 -alkyl) -amino-carbonyl, N- (C 3 -C 6 - Alkenyl) -N- (C 1 -C 6 -alkoxy) -aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (C 1 -C 6 -alkoxy) -aminocarbonyl, di (C 1 -C 6 -alkyl) aminothiocarbonyl, (C 1 -C 6 -alkyl-cyanoimino, (amino) cyanoimino, [(C 1 -C 6 -alkyl-amino-cyanoimino, di (C 1 -C 6 -alkyl) aminocyanoimino, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxyimino-C 1 -C 8 -cyclo alkyl, N- (C 1 -C 6 -alkylamino) -imino-C 1 -C 6 -alkyl, N- [di (C 1 -C 6 -alkyl) amino] imino
Ci-Ce-alkyl oder Tri-Ci-C4-alkylsilyl, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Hydroxy, C3-C6-Cycloalkyl, CrCδ-Alkoxy- Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkoxy-CrC4-alkyl, Ci-C4-Alkoxy, CrC4-C 1 -C 6 -alkyl or tri-C 1 -C 4 -alkylsilyl, where the said alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and / or may carry one to three of the following groups: cyano, hydroxy, C 3 -C 6 cycloalkyl, CrCδ-alkoxy- Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-CrC 4 alkyl, Ci-C4-alkoxy, CrC 4 -
Alkylthio, Di(Ci-C4-alkyl)amino, Ci-C4-Alkyl-Ci-C6-alkoxycarbonylamino, CrC4-Alkylcarbonyl, Hydroxycarbonyl, d-C4-Alkoxycarbonyl, Aminocar- bonyl, d-CrAlkylaminocarbonyl, Di(Ci-C4-alkyl)aminocarbonyl oder Cr C4-Al kylcarbonyloxy; Phenyl, Phenyl-CrCδ-alkyl, Phenylcarbonyl-Ci-Cδ-alkyl, Phenoxycarbonyl, Phe- nylaminocarbonyl, Phenylsulfonylaminocarbonyl, N-(d-C6-Alkyl)-N-(phenyl)- aminocarbonyl, Phenyl-Ci-Cδ-alkylcarbonyl, wobei der Phenylrest partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann: Nitro, Cyano, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy oder Ci-C4-Halogenalkoxy; oder SO2R8.Alkylthio, di (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkyl-C 1 -C 6 -alkoxycarbonylamino, C 1 -C 4 -alkylcarbonyl, hydroxycarbonyl, C 1 -C 4 -alkoxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, di (C 1 -C 4 -alkyl) C 4 alkyl) aminocarbonyl or C 1 -C 4 alkylcarbonyloxy; Phenyl, phenyl-C 1 -C 6 -alkyl, phenylcarbonyl-C 1 -C 6 -alkyl, phenoxycarbonyl, phenylaminocarbonyl, phenylsulfonylaminocarbonyl, N- (C 1 -C 6 -alkyl) -N- (phenyl) -aminocarbonyl, phenyl-C 1 -C 6 -alkylcarbonyl, where the phenyl radical may be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, Ci-C 4 alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C 4 haloalkoxy; or SO 2 R 8 .
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der R6 Wasserstoff, Ci-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Al kinyl, Formyl, CrC6- Alkylcarbonyl, Ca-Cδ-Alkenylcarbonyl, C3-C6-Cycloalkylcarbonyl, CrC6- Alkoxycarbonyl, CrCe-Alkylaminocarbonyl, CrCe-Alkylsulfonylaminocarbonyl, Di-(CrC6-alkyl)-aminocarbonyl, N-^rCe-AlkoxyJ-N-^rCe-alkylJ-aminocarbonyl, Di-(CrC6-alkyl)-aminothicarbonyl, Ci-C6-Alkoxyimino-CrC6-alkyl, wobei die genannten Alkyl, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Hydroxy, C3-C6-Cycloalkyl, CrC4-Alkoxy, CrC4- Alkylthio, Di-(CrC4-alkyl)-amino, CrC4-Alkylcarbonyl, Hydroxycarbonyl, Cr C4-Alkoxycarbonyl, Aminocarbonyl, CrCrAlkylaminocarbonyl, Di-(CrC4- alkyl)-aminocarbonyl, oder CrC^Alkylcarbonyloxy;The heteroaroyl-substituted alanines of the formula I in which R 6 is hydrogen, Ci-C are also preferred 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 kinyl -alkyl, formyl, -C 6 - alkylcarbonyl, Ca -Cδ-alkenylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylsulfonylaminocarbonyl, di- (C 1 -C 6 -alkyl) aminocarbonyl, N- C 1 -C 6 -alkoxy-N, C 1 -C 6 -alkyl-aminocarbonyl, Di- (C 1 -C 6 -alkyl) aminotharbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, where said alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and / or may carry one to three of the following groups: cyano, hydroxy , C3-C6-cycloalkyl, -C 4 alkoxy, -C 4 - alkylthio, di- (CrC 4 alkyl) amino, -C 4 alkylcarbonyl, hydroxycarbonyl, C Cr 4 alkoxycarbonyl, aminocarbonyl, CrCrAlkylaminocarbonyl, di- (CrC 4 - alkyl) -aminocarbonyl, or CrC ^ alkylcarbonyloxy;
Phenyl, Phenyl-CrCδ-alkyl, Phenylcarbonyl-CrCδ-alkyl, Phenylsulfonylaminocarbonyl oder Phenyl-CrCδ-alkylcarbonyl, wobei der Phenylring partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann: Nitro, Cyano, CrC4-Alkyl, CrC4-Halogenalkyl, CrC4-Alkoxy oder CrC4-Halogenalkoxy; oder SO2R8 besonders bevorzugt Wasserstoff, Ci-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, Formyl, Ci-Cδ-Alkylcarbonyl, Ci-Cδ-Alkoxycarbonyl, d- C6-Alkylsulfonylaminocarbonyl, Di-(Ci-C6-alkyl)-aminocarbonyl, N-(Ci-C6- Alkoxy)-N-(Ci-C6-alkyl)-aminocarbonyl oder Di-(Ci-C6-alkyl)-aminothiocarbonyl, wobei die genannten Alkyl- oder Alkoxyreste partiell oder vollständig halo- geniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Ci-C4-AIkOXy, C1-C4- Alkylaminocarbonyl, Di-(Ci-C4-alkyl)-aminocarbonyl oder C1-C4- Alkylcarbonyloxy; Phenyl-Ci-Cδ-alkyl, Phenylcarbonyl-Ci-Cδ-alkyl, Phenylsulfonyl-aminocarbonyl oder Phenyl-Ci-Cδ-alkylcarbonyl, wobei der Phenylring partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann: Nitro, Cyano, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy oder Ci-C4-Halogenalkoxy; oderPhenyl, phenyl-C 1 -C 6 -alkyl, phenylcarbonyl-C 1 -C 6 -alkyl, phenylsulfonylaminocarbonyl or phenyl-C 1 -C 6 -alkylcarbonyl, where the phenyl ring can be partially or fully halogenated and / or can carry one to three of the following groups: nitro, cyano, C 1 -C 4 - alkyl, -C 4 haloalkyl, -C 4 alkoxy or -C 4 -haloalkoxy; or SO 2 R 8 particularly preferably hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, formyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylsulfonylaminocarbonyl, di- (C 1 -C 6 -alkyl) aminocarbonyl, N- (C 1 -C 6 -alkoxy) -N- (C 1 -C 6 -alkyl) aminocarbonyl or di (Ci C 6 -alkyl) -aminothiocarbonyl, where the alkyl or alkoxy radicals mentioned may be partially or completely halogenated and / or may carry one to three of the following groups: cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylaminocarbonyl, di (C 1 -C 4 -alkyl) aminocarbonyl or C 1 -C 4 -alkylcarbonyloxy; Phenyl-Ci-Cδ-alkyl, phenylcarbonyl-Ci-Cδ-alkyl, phenylsulfonyl-aminocarbonyl or phenyl-Ci-Cδ-alkylcarbonyl, wherein the phenyl ring may be partially or fully halogenated and / or may carry one to three of the following groups: nitro , Cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; or
SO2R8;SO 2 R 8 ;
insbesondere bevorzugt Wasserstoff, Ci-Cβ-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, Formyl, Ci-Cδ-Alkyl-carbonyl, Ci-Cδ-Alkoxycarbonyl, Di- (Ci-Ce-alkylJ-amino-carbonyl, N-(Ci-C6-Alkoxy)-N-(Ci-C6-alkyl)-aminocarbonyl,particularly preferably hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, formyl, C 1 -C 6 -alkyl-carbonyl, Ci-Cδ-alkoxycarbonyl, di (Ci-Ce-alkylJ-amino-carbonyl, N- (Ci-C6-alkoxy) -N- (Ci-C6-alkyl) -aminocarbonyl,
Di-(Ci-C6-alkyl)-aminothiocarbonyl, Phenyl-Ci-Cδ-alkyl, Phenylcarbonyl-Ci-Cδ- alkyl oder Phenyl-Ci-Cδ-alkylcarbonyl, wobei der Phenylring partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann: Nitro, Cyano, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy oder Ci-C4-Halogenalkoxy; oder SO2R8; bedeutet.Di- (Ci-C6-alkyl) -aminothiocarbonyl, phenyl-Ci-Cδ-alkyl, phenylcarbonyl-Ci-Cδ- alkyl or phenyl-Ci-Cδ-alkylcarbonyl, wherein the phenyl ring can be partially or completely halogenated and / or a bis may carry three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; or SO 2 R 8 ; means.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der R6 Wasserstoff, Ci-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Al kinyl, Formyl, CrC6- Alkylcarbonyl, Ca-Cδ-Alkenylcarbonyl, C3-C6-Cycloalkylcarbonyl, Ci-C6- Alkoxycarbonyl, Ci-Cδ-Alkylaminocarbonyl, Di-(Ci-C6-alkyl)-aminocarbonyl, N- (Ci-C6-Alkoxy)-N-(Ci-C6-alkyl)-aminocarbonyl, Di-(Ci-Ce-alkyl)- aminothiocarbonyl, Ci-C6-Alkoxyimino-Ci-C6-alkyl, wobei die genannten Alkyl-, Cycloalkyl- oder Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Hydroxy, C3-C6-Cycloalkyl, Ci-C4-Alkoxy, C1-C4- Alkylthio, Di-(Ci-C4-alkyl)-amino, Ci-C4-Alkylcarbonyl, Hydroxycarbonyl, d- C4-Alkoxycarbonyl, Aminocarbonyl, Ci-C4-Alkylaminocarbonyl, Di-(Ci-C4- alkyl)-aminocarbonyl oder Ci-C4-Alkylcarbonyloxy; oder SO2R8; bedeutet. Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der R6 Wasserstoff, Ci -C6-Al kyl, C3-C6-Alkenyl, C3-C6-Al kinyl, Formyl, CrC6-The heteroaroyl-substituted alanines of the formula I in which R 6 is hydrogen, Ci-C are also preferred 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 kinyl -alkyl, formyl, -C 6 - alkylcarbonyl, Ca -Cδ-alkenylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylaminocarbonyl, di- (C 1 -C 6 -alkyl) aminocarbonyl, N- (C 1 -C 6 -alkoxy) -N- (C 1 -C 6 -alkyl) aminocarbonyl, di- (C 1 -C 6 -alkyl) aminothiocarbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, where the alkyl, cycloalkyl or alkoxy radicals mentioned are partially or completely may be halogenated and / or may carry one to three of the following groups: cyano, hydroxy, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, di- (C 1 -C 4 -alkyl) -amino, C 1 -C 4 -alkylcarbonyl, hydroxycarbonyl, C 1 -C 4 -alkoxycarbonyl, aminocarbonyl, C 1 -C 4 -alkylaminocarbonyl, di- (C 1 -C 4 -alkyl) aminocarbonyl or C 1 -C 4 -alkylcarbonyloxy; or SO 2 R 8 ; means. Also preferred are the heteroaroyl-substituted alanines of the formula I in which R 6 is hydrogen, Ci -C 6 -alkyl, C 3 -C 6 alkenyl, C 3 -C 6 -alkyl kinyl, formyl, CrC 6 are -
Alkylcarbonyl, Ci-C6-Alkoxycarbonyl, Ci-Ce-Alkylaminocarbonyl, Di-(Ci-C6-alkyl)- aminocarbonyl, N-(Ci-C6-Alkoxy)-N-(CrC6-alkyl)-amino-carbonyl, insbesondere bevorzugt Wasserstoff oder Ci-C4-Alkyl; wobei die genannten Alkyl-,und Alkoxyreste partiell oder vollständig halo- geniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, CrC4-AIkOXy, Ci-C4-Alkylaminocarbonyl oder Di-(Ci-C4- alkyl)-aminocarbonyl;Alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylaminocarbonyl, di- (C 1 -C 6 -alkyl) -aminocarbonyl, N- (C 1 -C 6 -alkoxy) -N- (C 1 -C 6 -alkyl) -amino carbonyl, particularly preferably hydrogen or C 1 -C 4 -alkyl; where the alkyl and alkoxy radicals may be partially or fully halogenated halo- and / or may carry one to three of the following groups: cyano, -C 4 -alkoxy, Ci-C4-alkylaminocarbonyl or di- (Ci-C 4 - alkyl ) aminocarbonyl;
Phenyl-Ci-C6-alkyl, Phenylcarbonyl-Ci-C6-alkyl, Phenylaminocarbonyl oder N- (Ci-C6-Al kyl)-N-(phenyl)-aminocarbonyl, wobei der Phenylring partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann: Cyano, C1-C4- Alkyl oder Ci-C4-Halogenalkyl; oderPhenyl-C 1 -C 6 -alkyl, phenylcarbonyl-C 1 -C 6 -alkyl, phenylaminocarbonyl or N- (C 1 -C 6 -alkyl) -N- (phenyl) -aminocarbonyl, it being possible for the phenyl ring to be partially or completely halogenated, and or one to three of the following groups: cyano, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; or
SO2R8;SO 2 R 8 ;
besonders bevorzugt Wasserstoff, Formyl, Ci-C4-Alkylcarbonyl, C1-C4- Alkylaminocarbonyl, Di-(Ci-C4-alkyl)-aminocarbonyl, Phenylaminocarbonyl, N- (Ci-C4-Alkyl)-N-(phenyl)-aminocarbonyl, SO2CH3, SO2CF3 oder SO2(C6H5); bedeutet.particularly preferably hydrogen, formyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylaminocarbonyl, di- (C 1 -C 4 -alkyl) aminocarbonyl, phenylaminocarbonyl, N- (C 1 -C 4 -alkyl) -N- (phenyl) aminocarbonyl , SO 2 CH 3 , SO 2 CF 3 or SO 2 (C 6 H 5 ); means.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der R7 Wasserstoff, Ci-C6-Alkyl, Hydroxy oder Ci-C6-Alkoxy; besonders bevorzugt Wasserstoff oder Ci-C6-Alkyl; insbesondere bevorzugt Wasserstoff oder Methyl; außerordentlich bevorzugt Wasserstoff; bedeutet.Likewise preferred are the heteroaroyl-substituted alanines of the formula I in which R 7 is hydrogen, C 1 -C 6 -alkyl, hydroxy or C 1 -C 6 -alkoxy; particularly preferably hydrogen or C 1 -C 6 -alkyl; especially preferably hydrogen or methyl; most preferably hydrogen; means.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der R8 d-Cβ-Alkyl, Ci-C6-Halogenalkyl oder Phenyl, wobei der Phenylrest partiell oder vollständig halogeniert sein kann und/oder durch Ci-C4-Alkyl substituiert sein kann; besonders bevorzugt Ci-C4-Alkyl, Ci-C4-Halogenalkyl oder Phenyl; insbesondere bevorzugt Methyl, Trifluormethyl oder Phenyl. bedeutet.Likewise preferred are the heteroaroyl-substituted alanines of the formula I in which R 8 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or phenyl, where the phenyl radical may be partially or completely halogenated and / or substituted by C 1 -C 4 -alkyl can be; particularly preferably C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or phenyl; especially preferably methyl, trifluoromethyl or phenyl. means.
Ebenso bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der R8 Ci-Ce-Alkyl, Ci-C6-Halogenalkyl oder Phenyl, wobei der Phenylrest partiell halogeniert sein kann und/oder durch C1-C4-Likewise preferred are the heteroaroyl-substituted alanines of the formula I in which R 8 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or phenyl, where the phenyl radical may be partially halogenated and / or represented by C 1 -C 4 -alkyl.
Alkyl substituiert sein kann; besonders bevorzugt Ci-C4-Alkyl, Ci-C4-Halogenalkyl oder Phenyl; insbesondere bevorzugt Methyl, Trifluormethyl oder Phenyl. bedeutet.Alkyl may be substituted; particularly preferably C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or phenyl; especially preferably methyl, trifluoromethyl or phenyl. means.
Besonders bevorzugt sind die heteroaroyl-substituierten Alanine der Formel I, in der A 5- oder 6-gliedriges Heteroaryl ausgewählt aus der Gruppe Thienyl, Furyl, Pyra- zolyl, Imidazolyl, Thiazolyl, Oxazolyl und Pyridyl; wobei die genannten Heteroarylreste partiell oder vollständig halogeniert sein können und/oder 1 bis 3 Reste aus der Gruppe Ci-Cδ-Alkyl, C3-C6-Cycloalkyl und Ci-Cβ-Halogenalkyl tragen können; R1 und R2 Wasserstoff; R3 Ci-C4-Alkyl, besonders bevorzugt CH3; R4 Wasserstoff;Particular preference is given to the heteroaroyl-substituted alanines of the formula I in which A is 5- or 6-membered heteroaryl selected from the group consisting of thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl and pyridyl; wherein said heteroaryl may be partially or completely halogenated and / or 1 to 3 radicals from the group Ci-Cδ-alkyl, C3-C6-cycloalkyl and Ci-Cβ-haloalkyl may carry; R 1 and R 2 are hydrogen; R 3 is C 1 -C 4 -alkyl, particularly preferably CH 3; R 4 is hydrogen;
R5 Wasserstoff, Ci-C6-Alkyl, C2-C6-Alkenyl, Ci-C6-Halogenalkyl, C2-C6- Halogenalkenyl, Ci-C6-Hydroxyalkyl, Hydroxycarbonyl-d^-alkyl, Phenyl-Ci-C4- alkyl oder Phenyl-Ci-C4-hydroxyalkyl;R 5 is hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, Ci-C 6 haloalkyl, C 2 -C 6 - haloalkenyl, Ci-C 6 hydroxyalkyl, hydroxycarbonyl-d ^ alkyl, phenyl C 1 -C 4 -alkyl or phenyl-C 1 -C 4 -hydroxyalkyl;
R6 Wasserstoff, Formyl, Ci-C4-Alkylcarbonyl, Ci-C4-Alkylaminocarbonyl, Di-(Ci-C4- Alkyl)-aminocarbonyl, Phenylaminocarbonyl, N-(CI -C4-alkyl)-N-(phenyl)- aminocarbonyl, SO2CH3, SO2CF3 oder SO2(C6H5); und R7 Wasserstoff bedeuten.R 6 is hydrogen, formyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylaminocarbonyl, di (C 1 -C 4 -alkyl) aminocarbonyl, phenylaminocarbonyl, N- (C 1 -C 4 -alkyl) -N- (phenyl) -aminocarbonyl, SO 2 CH 3 , SO 2 CF 3 or SO 2 (C 6 H 5 ); and R 7 is hydrogen.
Außerordentlich bevorzugt sind die Verbindungen der Formel La (entspricht Formel I mit A = A-1 mit R9 = H, R10 = CF3, R1, R2, R4 und R7 = H; R3 = CH3), insbesondere die Verbindungen der Formel l.a.1 bis La.210 der Tabelle 1 , wobei die Definitionen der Variablen A und R1 bis R7 nicht nur in Kombination miteinander, sondern auch jeweils für sich allein betrachtet für die erfindungsgemäßen Verbindungen eine besondere Rolle spielen.Very particular preference is given to the compounds of the formula La (corresponding to formula I where A = A-1 where R 9 = H, R 10 = CF 3 , R 1 , R 2 , R 4 and R 7 = H; R 3 = CH 3 ) , in particular the compounds of the formula Ia1 to La.210 of Table 1, wherein the definitions of the variables A and R 1 to R 7 not only in combination with each other, but also considered in each case for the compounds according to the invention play a special role.
Tabelle 1Table 1
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel l.b, insbesondere die Verbindungen der Formel l.b.1 bis l.b.210, die sich von den entsprechenden Verbindungen der Formel l.a.1 bis La.210 dadurch unterscheiden, daß A für A1 mit R9 = CH3 und R10 = CF3 steht:Equally extremely preferred are the compounds of the formula Ib, in particular the compounds of the formulas Ib 1 to Ib 2 O, which differ from the corresponding compounds of the formulas Ia1 to La.210 in that A is Al with R 9 = CH 3 and R 10 = CF 3 stands:
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel l.c, insbesondere die Verbindungen der Formel l.c.1 bis I.e.210, die sich von den entsprechenden Verbindungen der Formel l.a.1 bis La.210 dadurch unterscheiden, daß A für A2 mit R9 = H und R10 =CF3 steht:Equally exceptionally preferred are the compounds of the formula Ic, in particular the compounds of the formulas Ic1 to Ie210, which differ from the corresponding compounds of the formulas Ia1 to La.210 in that A is A2 where R 9 = H and R 10 = CF 3 stands:
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel Ld, insbesondere die Verbindungen der Formel Ld.1 bis Ld.210, die sich von den entsprechenden Verbindungen der Formel l.a.1 bis La.210 dadurch unterscheiden, daß A für A3 mit R9 = H und R10 = CF3 steht:Equally extraordinarily preferred are the compounds of the formula Ld, in particular the compounds of the formula Ld.1 to Ld.210, which differ from the corresponding compounds of the formula Ia1 to La.210 in that A for A3 with R 9 = H and R 10 = CF 3 is:
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel l.e, insbesondere die Verbindungen der Formel l.e.1 bis I.e.210, die sich von den entsprechenden Verbindungen der Formel l.a.1 bis La.210 dadurch unterscheiden, daß A für A3 mit R9 = CH3 und R10 = CF3 steht: Equally exceptionally preferred are the compounds of the formula Ie, in particular the compounds of the formula Ie1 to Ie210, which differ from the corresponding compounds of the formula Ia1 to La.210 in that A is A3 with R 9 = CH 3 and R 10 = CF 3 stands:
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel l.f, insbesondere die Verbindungen der Formel l.f.1 bis l.f.210, die sich von den entsprechenden Verbindungen der Formel l.a.1 bis La.210 dadurch unterscheiden, daß A für A4 mit R9 = H und R10 = CF3 steht:Equally extraordinarily preferred are the compounds of the formula If, in particular the compounds of the formulas If1 to If210, which differ from the corresponding compounds of the formulas Ia1 to La.210 in that A is A4 with R 9 = H and R 10 = CF 3 stands:
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel Lg, insbesondere die Verbindungen der Formel Lg.1 bis Lg.210, die sich von den entsprechenden Verbindungen der Formel l.a.1 bis La.210 dadurch unterscheiden, daß A für A5 mit R10 = CF3, sowie R11 und R12 = H steht:Equally extraordinarily preferred are the compounds of the formula Lg, in particular the compounds of the formula Lg.1 to Lg.210, which differ from the corresponding compounds of the formula Ia1 to La.210 in that A is A5 with R 10 = CF 3 , and R 11 and R 12 = H:
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel Lh, insbesondere die Verbindungen der Formel Lh.1 bis Lh.210, die sich von den entsprechenden Verbindungen der Formel l.a.1 bis La.210 dadurch unterscheiden, daß A für A5 mit R10 = CF3, R11 = H und R12 = CH3 steht: Equally extraordinarily preferred are the compounds of the formula Lh, in particular the compounds of the formula Lh.1 to Lh.210, which differ from the corresponding compounds of the formula Ia1 to La.210 in that A is A5 with R 10 = CF 3 , R 11 = H and R 12 = CH 3 is:
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel l.j, insbesondere die Verbindungen der Formel l.j.1 bis l.j.210, die sich von den entsprechenden Verbindungen der Formel l.a.1 bis La.210 dadurch unterscheiden, daß A für A8 mit R9 = H und R10 = CF3 steht:Equally exceptionally preferred are the compounds of the formula Ij, in particular the compounds of the formulas Ij1 to Ij210, which differ from the corresponding compounds of the formulas Ia1 to La.210 in that A is A 8 where R 9 = H and R 10 = CF 3 stands:
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel Lk, insbesondere die Verbindungen der Formel Lk.1 bis Lk.210, die sich von den entsprechenden Verbindungen der Formel l.a.1 bis La.210 dadurch unterscheiden, daß A für A8 mit R9 = CH3 und R10 = CF3 steht:Equally exceptionally preferred are the compounds of the formula Lk, in particular the compounds of the formula Lk.1 to Lk.210, which differ from the corresponding compounds of the formula Ia1 to La.210 in that A is A8 with R 9 = CH 3 and R 10 = CF 3 is:
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel LI, insbesondere die Verbindungen der Formel 1.1.1 bis 1.1.210, die sich von den entsprechenden Verbindungen der Formel l.a.1 bis La.210 dadurch unterscheiden, daß A für A10 mit R9 = CH3 und R10 = CF3 steht:Equally extraordinarily preferred are the compounds of the formula LI, in particular the compounds of the formula 1.1.1 to 1.1.210, which differ from the corresponding compounds of the formula Ia1 to La.210 in that A is A10 with R 9 = CH 3 and R 10 = CF 3 is:
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel l.m, insbesondere die Verbindungen der Formel l.m.1 bis l.m.210, die sich von den entsprechenden Verbindungen der Formel l.a.1 bis La.210 dadurch unterscheiden, daß A für A1 1 mit R9 = CH3 und R10 = CF3 steht: Equally extraordinarily preferred are the compounds of the formula III, in particular the compounds of the formula Im1 to Im210, which differ from the corresponding compounds of the formula Ia1 to La.210 in that A is Al 1 with R 9 = CH 3 and R 10 = CF 3 is:
Die benzoylsubstituierten Alanine der Formel I sind auf verschiedene Art und Weise erhältlich, beispielsweise nach folgenden Verfahren:The benzoyl-substituted alanines of the formula I are obtainable in various ways, for example by the following processes:
Verfahren AMethod A
Alaninderivate der Formel V werden zunächst mit Heteroarylsäure(derivate)n der For- mel IV zu entsprechenden Heteroaroylderivaten der Formel IM umgesetzt, welche anschließend mit Aminen der Formel Il zu den gewünschten heteroaroyl-substituierten Alaninen der Formel I reagieren:Alanine derivatives of the formula V are first reacted with heteroaryl acid (derivatives) of the formula IV to give corresponding heteroaroyl derivatives of the formula III, which subsequently react with amines of the formula II to give the desired heteroaroyl-substituted alanines of the formula I:
V IV I
L1 steht für eine nucleophil verdrängbare Abgangsgruppe, z.B. für Hydroxy oder Ci-Cβ- Alkoxy.L 1 is a nucleophilically displaceable leaving group, for example for hydroxy or C 1 -C 6 -alkoxy.
L2 steht für eine nucleophil verdrängbare Abgangsgruppe, z.B. für Hydroxy, Halogen, Ci-C6-Alkylcarbonyl, Ci-Cδ-Alkoxycarbonyl, Ci -C4-Al kylsu If onyl, Phosphoryl oder Iso- ureyl.L 2 represents a nucleophilic displaceable leaving group, for example for hydroxy, halogen, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 4 -alkyl, onyl, phosphoryl or iso-ureyl.
Die Umsetzung der Alaninderivate der Formel V mit Heteroarylsäure(derivate)n der Formel IV, wobei L2 für Hydroxy steht, zu Heteroaroylderivaten der Formel IM erfolgt in Gegenwart eines Aktivierungsreagenz und einer Base üblicherweise bei Temperaturen von 0 0C bis zum Siedepunkt des Reaktionsgemisches, vorzugsweise O0C bis 11 O0C, besonders bevorzugt bei Raumtemperatur, in einem inerten organischen Lösungsmittel [vgl. K. C. Nicolaou et al., J. of the Am. Chem. Soc. (2005), 127(31 ), 1 1 176-1 1 183; Shu-Sin Chng et al., Tetrahedron Lett. (2004), 45(52), 9501-9504; Werner W. K. R. Mederski et al., Bioorganic & Medicinal Chemistry Letters (2004), 14 (23), 5817-5822; Romano Silvestri et al., J. of Med. Chem. (2004), 47(15), 3892-3896; P. Rzepecki et al., J. of Org. Chem. (2004), 69(16), 5168-5178; Justin Bower et al., Bioorg. and Med. Chem. Lett. (2003), 13(15), 2455-2458; JiII Arrowsmith et al., J. of Med. Chem. (2002), 45(25), 5458-5470; Ashraf Briket al., Chemistry and Biology (2002), 9(8), 891-896; Andrew D.Abell et al., Tetrahedron Lett. (2002), 43(20), 3673-3675; John F. Okonya et al., J. of Org. Chem. (2002), 67(4), 1 102-1 108; George R. Pettit et al., J. of Org. Chem. (1985), 50(15), 2654-2659].The reaction of the alanine derivatives of the formula V with heteroaryl acid (derivatives) n of the formula IV, where L 2 is hydroxyl, to heteroaroyl derivatives of the formula IM is carried out in the presence of an activating reagent and a base usually at temperatures of 0 0 C to the boiling point of the reaction mixture, preferably O 0 C to 11 O 0 C, particularly preferably at room temperature, in an inert organic solvent [cf. KC Nicolaou et al., J. of the Am. Chem. Soc. (2005), 127 (31), 1176-1 1 183; Shu-Sin Chng et al., Tetrahedron Lett. (2004), 45 (52), 9501-9504; Werner WKR Mederski et al., Bioorganic & Medicinal Chemistry Letters (2004), 14 (23), 5817-5822; Romano Silvestri et al., J. of Med. Chem. (2004), 47 (15), 3892-3896; P. Rzepecki et al., J. of Org. Chem. (2004) 69 (16), 5168-5178; Justin Bower et al., Bioorg. and Med. Chem. Lett. (2003), 13 (15), 2455-2458; JiII Arrowsmith et al., J. of Med. Chem. (2002), 45 (25), 5458-5470; Ashraf Brik et al., Chemistry and Biology (2002), 9 (8), 891-896; Andrew D. Bell et al., Tetrahedron Lett. (2002), 43 (20), 3673-3675; John F. Okonya et al., J. of Org. Chem. (2002), 67 (4), 1 102-1 108; George R. Pettit et al., J. of Org. Chem. (1985), 50 (15), 2654-2659].
Geeignete Aktivierungsreagenzien sind Kondensationsmittel wie z.B. polystyrolgebundenes Dicyclohexylcarbodiimid, Diisopropylcarbodiimid, Carbonyldiimidazol, Chlorkoh- lensäureesterwie Methylchloroformiat, Ethylchloroformiat, Isoropylchloroformiat, Isobu- tylchloroformiat, sec-Butylchloroformiat oder Allylchloroformiat, Pivaloylchlorid, PoIy- phosphorsäure, Propanphosphonsäureanhydrid, Bis(2-oxo-3-oxazolidinyl)- phosphorylchlorid (BOPCI) oder Sulfonylchloride wie Methansulfonylchlorid, Toluolsul- fonylchlorid oder Benzolsulfonylchlorid.Suitable activating reagents are condensing agents, e.g. polystyrene-bonded dicyclohexylcarbodiimide, diisopropylcarbodiimide, carbonyldiimidazole, chlorocarbonic acid esters such as methyl chloroformate, ethyl chloroformate, isoropyl chloroformate, isobutyl chloroformate, sec-butyl chloroformate or allyl chloroformate, pivaloyl chloride, polyphosphoric acid, propanephosphonic anhydride, bis (2-oxo-3-oxazolidinyl) phosphoryl chloride (BOPCI) or Sulfonyl chlorides such as methanesulfonyl chloride, toluenesulfonyl chloride or benzenesulfonyl chloride.
Geeignete Lösungsmittel sind aliphatische Kohlenwasserstoffe wie Pentan, Hexan, Cyclohexan und Gemische von Cs-Cs-Al kanen, aromatische Kohlenwasserstoffe wie Benzol, Toluol, o-, m- und p-Xylol, halogenierte Kohlenwasserstoffe wie Methylenchlorid, Chloroform und Chlorbenzol, Ether wie Diethylether, Diisopropylether, tert- Butylmethylether, Dioxan, Anisol und Tetra hydrofu ran (THF), Nitrile wie Acetonitril und Propionitril, Ketone wie Aceton, Methylethylketon, Diethylketon und tert- Butylmethylketon, sowie Dimethylsulfoxid, Dimethylformamid (DMF), Dimethylacetamid (DMA) und N-Methylpyrrolidon (NMP) oder auch in Wasser, besonders bevorzugt sind Methylenchlorid, THF und Wasser.Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as benzene, toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether , Diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide, dimethylformamide (DMF), dimethylacetamide (DMA) and N Methylpyrrolidone (NMP) or in water, particularly preferred are methylene chloride, THF and water.
Es können auch Gemische der genannten Lösungsmittel verwendet werden.It is also possible to use mixtures of the solvents mentioned.
Als Basen kommen allgemein anorganische Verbindungen wie Alkalimetall- und Erdalkalimetallhydroxide wie Lithiumhydroxid, Natriumhydroxid, Kaliumhydroxid und Calci- umhydroxid, Alkalimetall- und Erdalkalimetalloxide wie Lithiumoxid, Natriumoxid, Calci- umoxid und Magnesiumoxid, Alkalimetall- und Erdalkalimetallhydride wie Lithiumhydrid, Natriumhydrid, Kaliumhydrid und Calciumhydrid, Alkalimetall- und Erdalkalimetall- carbonate wie Lithiumcarbonat, Kaliumcarbonat und Calciumcarbonat sowie Alkalime- tallhydrogencarbonate wie Natriumhydrogencarbonat, außerdem organische Basen, z.B. tertiäre Amine wie Trimethylamin, Triethylamin, Diisopropylethylamin, N-Bases generally include inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, Alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate and alkali metal bicarbonates such as sodium bicarbonate, as well as organic bases, eg tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, N-
Methylmorpholin, und N-Methylpiperidin, Pyridin, substituierte Pyridine wie Collidin, Lutidin und 4-Dimethylaminopyridin sowie bicyclische Amine in Betracht. Besonders bevorzugt werden Natriumhydroxid, Triethylamin und Pyridin. Die Basen werden im allgemeinen in äquimolar Mengen eingesetzt. Sie können aber auch im Überschuß oder gegebenenfalls als Lösungsmittel verwendet werden.Methylmorpholine, and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Particularly preferred are sodium hydroxide, triethylamine and pyridine. The bases are generally used in equimolar amounts. But they can also be used in excess or optionally as a solvent.
Die Edukte werden im allgemeinen in äquimolaren Mengen miteinander umgesetzt. Es kann vorteilhaft sein, IV in einem Überschuß bezogen auf V einzusetzen.The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use IV in an excess relative to V.
Die Reaktionsgemische werden in üblicher weise aufgearbeitet, z.B. durch Mischen mit Wasser, Trennung der Phasen und gegebenenfalls chromatographische Reinigung der Rohprodukte. Die Zwischen- und Endprodukte fallen z. T. in Form zäher Öle an, die unter vermindertem Druck und bei mäßig erhöhter Temperatur von flüchtigen Anteilen befreit oder gereinigt werden. Sofern die Zwischen- und Endprodukte als Feststoffe erhalten werden, kann die Reinigung auch durch Umkristallisieren oder Digerieren erfolgen.The reaction mixtures are worked up in the usual way, e.g. by mixing with water, separation of the phases and optionally chromatographic purification of the crude products. The intermediate and end products fall z. T. in the form of viscous oils, which are freed or purified under reduced pressure and at moderately elevated temperature of volatile fractions. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.
Die Umsetzung der Alaninderivate der Formel V mit Heteroarylsäure(derivate)n der Formel IV, wobei L2 für Halogen, Ci-Cδ-Alkylcarbonyl, Ci-Cδ-Alkoxycarbonyl, C1-C4- Alkylsulfonyl, Phosphoryl oder Isoureyl steht, zu Heteroaroylderivaten der Formel IM erfolgt in Gegenwart einer Base üblicherweise bei Temperaturen von 0 0C bis zum Siedepunkt des Reaktionsgemisches, vorzugsweise O0C bis 1000C, besonders bevorzugt bei Raumtemperatur in einem inerten organischen Lösungsmittel [vgl. K. C. Nico- laou et al., J. of the Am. Chem. Soc. (2005), 127(31 ), 11 176-1 1 183;Shu-Sin Chng et al., Tetrahedron Lett. (2004), 45(52), 9501-9504; Werner W. K. R. Mederski et al., Bioorganic & Medicinal Chemistry Letters (2004), 14 (23), 5817-5822; Romano Silvestri et al., J. of Med. Chem. (2004), 47(15), 3892-3896; P. Rzepecki et al., J. of Org. Chem. (2004), 69(16), 5168-5178; Justin Bower et al., Bioorg. and Med. Chem. Lett. (2003), 13(15), 2455-2458; JiII Arrowsmith et al., J. of Med. Chem. (2002), 45(25), 5458-5470; Ashraf Briket al., Chemistry and Biology (2002), 9(8), 891-896; Andrew D.Abell et al., Tetrahedron Lett. (2002), 43(20), 3673-3675; John F. Okonya et al., J. of Org. Chem. (2002), 67(4), 1 102-1 108; George R. Pettit et al., J. of Org. Chem. (1985), 50(15), 2654-2659].The reaction of the alanine derivatives of the formula V with heteroaryl acid (derivatives) n of the formula IV in which L 2 is halogen, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 4 -alkylsulfonyl, phosphoryl or isoureyl, to give heteroaroyl derivatives of the formula IM is carried out in the presence of a base, usually at temperatures from 0 ° C. to the boiling point of the reaction mixture, preferably from 0 ° C. to 100 ° C., more preferably at room temperature in an inert organic solvent [cf. KC Nicolaou et al., J. of the Am. Chem. Soc. (2005), 127 (31), 11 176-1, 183; Shu-Sin Chng et al., Tetrahedron Lett. (2004), 45 (52), 9501-9504; Werner WKR Mederski et al., Bioorganic & Medicinal Chemistry Letters (2004), 14 (23), 5817-5822; Romano Silvestri et al., J. of Med. Chem. (2004), 47 (15), 3892-3896; P. Rzepecki et al., J. of Org. Chem. (2004) 69 (16), 5168-5178; Justin Bower et al., Bioorg. and Med. Chem. Lett. (2003), 13 (15), 2455-2458; JiII Arrowsmith et al., J. of Med. Chem. (2002), 45 (25), 5458-5470; Ashraf Brik et al., Chemistry and Biology (2002), 9 (8), 891-896; Andrew D. Bell et al., Tetrahedron Lett. (2002), 43 (20), 3673-3675; John F. Okonya et al., J. of Org. Chem. (2002), 67 (4), 1 102-1 108; George R. Pettit et al., J. of Org. Chem. (1985), 50 (15), 2654-2659].
Geeignete Lösungsmittel sind aliphatische Kohlenwasserstoffe wie Pentan, Hexan, Cyclohexan und Gemische von Cs-Cs-Al kanen, aromatische Kohlenwasserstoffe wie Benzol, Toluol, o-, m- und p-Xylol, halogenierte Kohlenwasserstoffe wie Methylenchlorid, Chloroform und Chlorbenzol, Ether wie Diethylether, Diisopropylether, tert.-Butyl- methylether, Dioxan, Anisol und Tetrahydrofuran (THF), Nitrile wie Acetonitril und Pro- pionitril, Ketone wie Aceton, Methylethylketon, Diethylketon und tert.-Butylmethylketon, sowie Dimethylsulfoxid, Dimethylformamid (DMF), Dimethylacetamid (DMA) und N-Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as benzene, toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether , Diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and also dimethyl sulfoxide, dimethylformamide (DMF), dimethylacetamide ( DMA) and N-
Methylpyrrolidon (NMP) oder auch in Wasser, besonders bevorzugt sind Methylenchlorid, THF und Wasser. Es können auch Gemische der genannten Lösungsmittel verwendet werden.Methylpyrrolidone (NMP) or in water, particularly preferred are methylene chloride, THF and water. It is also possible to use mixtures of the solvents mentioned.
Als Basen kommen allgemein anorganische Verbindungen wie Alkalimetall- und Erdalkalimetallhydroxide wie Lithiumhydroxid, Natriumhydroxid, Kaliumhydroxid und Calci- umhydroxid, Alkalimetall- und Erdalkalimetalloxide wie Lithiumoxid, Natriumoxid, Calci- umoxid und Magnesiumoxid, Alkalimetall- und Erdalkalimetallhydride wie Lithiumhydrid, Natriumhydrid, Kaliumhydrid und Calciumhydrid, Alkalimetall- und Erdalkalimetall- carbonate wie Lithiumcarbonat, Kaliumcarbonat und Calciumcarbonat sowie Alkalime- tallhydrogencarbonate wie Natriumhydrogencarbonat, außerdem organische Basen, z.B. tertiäre Amine wie Trimethylamin, Triethylamin, Diisopropylethylamin, N-Bases generally include inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, Alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate and alkali metal bicarbonates such as sodium bicarbonate, as well as organic bases, eg tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, N-
Methylmorpholin, und N-Methylpiperidin, Pyridin, substituierte Pyridine wie Collidin, Lutidin und 4-Dimethylaminopyridin sowie bicyclische Amine in Betracht. Besonders bevorzugt werden Natriumhydroxid, Triethylamin und Pyridin.Methylmorpholine, and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Particularly preferred are sodium hydroxide, triethylamine and pyridine.
Die Basen werden im allgemeinen in äquimolar Mengen eingesetzt. Sie können aber auch im Überschuß oder gegebenenfalls als Lösungsmittel verwendet werden.The bases are generally used in equimolar amounts. But they can also be used in excess or optionally as a solvent.
Die Edukte werden im allgemeinen in äquimolaren Mengen miteinander umgesetzt. Es kann vorteilhaft sein, IV in einem Überschuß bezogen auf V einzusetzen.The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use IV in an excess relative to V.
Die Aufarbeitung und Isolierung der Produkte kann in an sich bekannter Weise erfolgen.The workup and isolation of the products can be done in a conventional manner.
Natürlich können auch in analoger Weise zunächst die Alaninderivate der Formel V mit Aminen der Formel Il zu den entsprechenden Amiden umgesetzt werden, welche dann mit Heteroarylsäure(derivate)n der Formel IV zu den gewünschten heteroaroyl- substituierten Alaninen der Formel I reagieren.Of course, in analogous manner, the alanine derivatives of the formula V can first be reacted with amines of the formula II to give the corresponding amides, which then react with heteroaryl acid (derivatives) n of the formula IV to give the desired heteroaroyl-substituted alanines of the formula I.
Die für die Herstellung der Heteroaroylderivate der Formel III benötigten Alaninderivate der Formel V (z.B. mit L1 = Hydroxy oder Ci-Cδ-Alkoxy) sind, auch in enantiomeren- und diastereomerenreiner Form, in der Literatur bekannt oder können gemäß der zitierten Literatur hergestellt werden:The alanine derivatives of the formula V required for the preparation of the heteroaroyl derivatives of the formula III (for example with L 1 = hydroxy or C 1 -C 6 -alkoxy) are known in the literature, even in enantiomerically and diastereomerically pure form, or can be prepared according to the cited literature :
1. Kondensation von dem Enolat eines Glycin-Derivates mit einem Imin-Derivat [vgl. Franklin A. Davis et al., Org. Lett. (2004), 6(14), 2397-2399; Alma Viso et al., J. of Org. Chem. (2004), 69(5), 1542-1547; Luca Bernardi et al., J. of Org. Chem. (2003), 68(7), 2583-2591 ; Ivanka K. Kavrakova et al, J. of Chem. Res., Synopses (1993), (5), 186-187.]1. Condensation of the enolate of a glycine derivative with an imine derivative [cf. Franklin A. Davis et al., Org. Lett. (2004), 6 (14), 2397-2399; Alma Viso et al., J. of Org. Chem. (2004), 69 (5), 1542-1547; Luca Bernardi et al., J. of Org. Chem. (2003), 68 (7), 2583-2591; Ivanka K. Kavrakova et al, J. of Chem. Res., Synopses (1993), (5), 186-187.]
2. Reduktion eines Azids2. Reduction of an azide
[vgl. Mark E. Bunnage et al., Organ, and Biomol. Chem. (2003), 1 (21 ), 3708-3715; Anthony J. Burke et al., Synlett (1996), (7), 621-622.] 3. Nucleophile Öffnung eines Aziridins[see. Mark E. Bunnage et al., Organ, and Biomol. Chem. (2003), 1 (21), 3708-3715; Anthony J. Burke et al., Synlett (1996), (7), 621-622.] 3. Nucleophilic opening of an aziridine
[vgl. Michael A. Letavic et al., Bioorg. and Med. Chem. Lett. (2003), 13(19), 3243-3246; Tushar K.Chakraborty et al., Chem. Lett. (2003), 32(1 ), 82-83; K.-D. Lee et al., Tetrahedron (2001), 57(39), 8267-8276; Luciano Antolini et al., J. of Org. Chem. (1997), 62(25), 8784-8789; Johan Legters et al., Rec. des Trav. Chim. Pays-Bas (1992), 1 1 1 (2), 59-68 ][see. Michael A. Letavic et al., Bioorg. and Med. Chem. Lett. (2003), 13 (19), 3243-3246; Tushar K. Chakraborty et al., Chem. Lett. (2003), 32 (1), 82-83; K.-D. Lee et al., Tetrahedron (2001), 57 (39), 8267-8276; Luciano Antolini et al., J. of Org. Chem. (1997), 62 (25), 8784-8789; Johan Legters et al., Rec. Chim. Pays-Bas (1992), 1 1 1 (2), 59-68]
4. Addition von Nitroenolaten an Glycinimine und anschließende Reduktion:4. Addition of Nitroenolates to Glycinimines and Subsequent Reduction:
[vgl. Nagatoshi Nishiwaki et al., Angew. Chem., Int. Ed. (2001 ), 40(16), 2992-2995; Kristian Rahbek Knudsen et al., J. of the Am. Chem. Soc. (2001 ), 123(24), 5843-5844][see. Nagatoshi Nishiwaki et al., Angew. Chem., Int. Ed. (2001), 40 (16), 2992-2995; Kristian Rahbek Knudsen et al., J. of the Am. Chem. Soc. (2001), 123 (24), 5843-5844]
5. Hydrierung von Diaminoacrylaten5. Hydrogenation of diaminoacrylates
[vgl. Andrea J.Robinson et al., J. of Org. Chem. (2001 ), 66(12), 4148-4152; Ryoichi Kuwano et al., Tetrahedron Asym. (1998), 9(16), 2773-2775; Hiroyuki Setoi et al., Chem. and Pharm. Bull. (1989), 37(4), 1 126-1 127;[see. Andrea J. Robinson et al., J. of Org. Chem. (2001) 66 (12), 4148-4152; Ryoichi Kuwano et al., Tetrahedron Asym. (1998), 9 (16), 2773-2775; Hiroyuki Setoi et al., Chem. And Pharm. Bull. (1989), 37 (4), 1 126-1 127;
Piedad Fernandez-Resa et al., J. of the Chem. Soc. Perkin Trans. 1 (1989), (1 ), 67-71]Piedad Fernandez-Resa et al., J. of the Chem. Soc. Perkin Trans. 1 (1989), (1), 67-71]
6. Oxidative Diaminierung von Acrylaten6. Oxidative diamination of acrylates
[vgl. Guigen Li et al., Tetrahedron Lett. (2000), 41 (45), 8699-8703][see. Guigen Li et al., Tetrahedron Lett. (2000), 41 (45), 8699-8703]
7. Öffnung von Imidazolinen7. Opening of imidazolines
[vgl. Tamio Hayashi et al., Tetrahedron Lett. (1996), 37(28), 4969-4972; Peter J. Dünn et al., J. of Org. Chem. (1990), 55(17), 5017-5025.][see. Tamio Hayashi et al., Tetrahedron Lett. (1996), 37 (28), 4969-4972; Peter J. Dunn et al., J. of Org. Chem. (1990), 55 (17), 5017-5025.]
8. Addition eines N-Nucleophils an ein Aminoacrylat8. Addition of an N-nucleophile to an aminoacrylate
[vgl. B. Narasimhulu Naidu et al., J. of Org. Chem. (2003), 68(26), 10098-10102;[see. B. Narasimhulu Naidu et al., J. of Org. Chem. (2003), 68 (26), 10098-10102;
Daeock Choi et al., Tetrahedron Lett. (1995), 36(41 ), 7371-7374; Montserrat Perez et al., Tetrahedron (1995), 51 (30), 8355-8362 ; Rolf Meyer et al., Justus Liebigs Ann.Daeock Choi et al., Tetrahedron Lett. (1995), 36 (41), 7371-7374; Montserrat Perez et al., Tetrahedron (1995), 51 (30), 8355-8362; Rolf Meyer et al., Justus Liebigs Ann.
Chem. (1977), (7), 1183-1 193.]Chem. (1977), (7), 1183-1 193.]
Die für die Herstellung der Heteroaroylderivate der Formel IM benötigten Heteroaryl- säure(derivate) der Formel IV können käuflich erworben werden oder können analog zu literaturbekannten Vorschrift hergestellt werden [z.B. Chang-Ling Liu et al., J. of Fluorine Chem. (2004), 125(9), 1287-1290; Manfred Schlosser et al., Europ. J. of Org. Chem. (2002), (17), 2913-2920; Hoh-Gyu Hahn et al., Agricult. Chem. and Biotech. (English Edition) (2002), 45(1 ), 37-42; Jonatan O Smith et a., J. of Fluorine Chem. (1997), Vol. 1996-1997, 81 (2), 123-128 ; Etsuji Okada et al., Heterocycles (1992), 34(4), 791-798; Aliyu B.Abubakar et al., J. of Fluorine Chem. (1991 ), 55(2), 189-198; J. Leroy, J of Fluorine Chem. (1991 ), 53(1 ), 61-70; Len F. Lee et al., J. of Heterocyclic Chem. (1990), 27(2), 243-245; Len F. Lee et al., J. of Heterocyclic Chem. (1985), 22(6), 1621-1630; Jacques Leroy et al., Synthesis (1982), (4), 313-315 ] Die Umsetzung der Heteroaroylderivate der Formel IM mit L1 = Hydroxy bzw. deren Salze mit Aminen der Formel Il zu den gewünschten heteroaroyl-substituierten Alaninen der Formel I erfolgt in Gegenwart eines Aktivierungsreagenz und gegebenenfalls in Gegenwart einer Base üblicherweise bei Temperaturen von 0 °C bis zum Siedepunkt des Reaktionsgemisches, vorzugsweise O0C bis 1000C, besonders bevorzugt bei Raumtemperatur in einem inerten organischen Lösungsmittel, [vgl. Perich, J. W., Johns, R. B., J. Org. Chem. 53 (17), 4103-4105 (1988); Somlai, C. et al., Synthesis (3), 285-287 (1992) ; Gupta, A. et al., J. Chem. Soc. Perkin Trans. 2, 191 1 (1990); Guan et al., J. Comb. Chem. 2, 297 (2000)].The heteroaryl acid (derivatives) of the formula IV required for the preparation of the heteroaroyl derivatives of the formula III can be purchased or can be prepared analogously to the procedure known from the literature [eg Chang-Ling Liu et al., J. of Fluorine Chem. (2004) , 125 (9), 1287-1290; Manfred Schlosser et al., Europ. J. of Org. Chem. (2002), (17), 2913-2920; Hoh-Gyu Hahn et al., Agricult. Chem. And Biotech. (English Edition) (2002), 45 (1), 37-42; Jonatan O Smith et al., J. of Fluorine Chem. (1997), Vol. 1996-1997, 81 (2), 123-128; Etsuji Okada et al., Heterocycles (1992), 34 (4), 791-798; Aliyu B. Abubakar et al., J. of Fluorine Chem. (1991), 55 (2), 189-198; J. Leroy, J of Fluorine Chem. (1991), 53 (1), 61-70; Len F. Lee et al., J. of Heterocyclic Chem. (1990), 27 (2), 243-245; Len F. Lee et al., J. of Heterocyclic Chem. (1985), 22 (6), 1621-1630; Jacques Leroy et al., Synthesis (1982), (4), 313-315] The reaction of the heteroaroyl derivatives of the formula III where L 1 = hydroxyl or their salts with amines of the formula II to give the desired heteroaroyl-substituted alanines of the formula I is carried out in the presence of an activating reagent and optionally in the presence of a base, usually at from 0 ° C. to to the boiling point of the reaction mixture, preferably O 0 C to 100 0 C, particularly preferably at room temperature in an inert organic solvent, [see. Perich, JW, Johns, RB, J. Org. Chem. 53 (17), 4103-4105 (1988); Somlai, C. et al., Synthesis (3), 285-287 (1992); Gupta, A. et al., J. Chem. Soc. Perkin Trans. 2, 1911 (1990); Guan et al., J. Comb. Chem. 2, 297 (2000)].
Geeignete Aktivierungsreagenzien sind Kondensationsmittel wie z.B. polystyrolgebundenes Dicyclohexylcarbodiimid, Diisopropylcarbodiimid, Carbonyldiimidazol, Chlorkohlensäureester wie Methylchloroformiat, Ethylchloroformiat, Isoropylchloroformiat, Isobutylchloroformiat, sec-Butylchloroformiat oder Allylchloroformiat, Pivaloylchlorid, Polyphosphorsäure,Suitable activating reagents are condensing agents, e.g. polystyrene-bonded dicyclohexylcarbodiimide, diisopropylcarbodiimide, carbonyldiimidazole, chlorocarbonic acid esters such as methyl chloroformate, ethyl chloroformate, isoropyl chloroformate, isobutyl chloroformate, sec-butyl chloroformate or allyl chloroformate, pivaloyl chloride, polyphosphoric acid,
Propanphosphonsäureanhydrid, Bis(2-oxo-3-oxazolidinyl)-phosphorylchlorid (BOPCI) oder Sulfonylchloride wie Methansulfonylchlorid, Toluolsulfonylchlorid oder Benzolsulfonylchlorid.Propanephosphonic anhydride, bis (2-oxo-3-oxazolidinyl) phosphoryl chloride (BOPCI) or sulfonyl chlorides such as methanesulfonyl chloride, toluenesulfonyl chloride or benzenesulfonyl chloride.
Geeignete Lösungsmittel sind aliphatische Kohlenwasserstoffe wie Pentan, Hexan, Cyclohexan und Gemische von Cs-Cs-Al kanen, aromatische Kohlenwasserstoffe wie Benzol, Toluol, o-, m- und p-Xylol, halogenierte Kohlenwasserstoffe wie Methylenchlorid, Chloroform und Chlorbenzol, Ether wie Diethylether, Diisopropylether, tert.-Butylmethylether, Dioxan, Anisol und Tetrahydrofuran (THF), Nitrile wie Acetonitril und Propionitril, Ketone wie Aceton, Methylethylketon, Diethylketon und tert- Butylmethylketon, Alkohole wie Methanol, Ethanol, n-Propanol, Isopropanol, n-Butanol und tert.-Butanol, sowie Dimethylsulfoxid, Dimethylformamid (DMF), Dimethylacetamid (DMA) und N-Methylpyrrolidon (NMP) oder auch in Wasser, besonders bevorzugt sind Methylenchlorid, THF, Methanol, Ethanol und Wasser.Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as benzene, toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether , Diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, as well as dimethyl sulfoxide, dimethylformamide (DMF), dimethylacetamide (DMA) and N-methylpyrrolidone (NMP) or in water, particularly preferred are methylene chloride, THF, methanol, ethanol and water.
Es können auch Gemische der genannten Lösungsmittel verwendet werden.It is also possible to use mixtures of the solvents mentioned.
Als Basen kommen allgemein anorganische Verbindungen wie Alkalimetall- und Erdal- kalimetallhydroxide wie Lithiumhydroxid, Natriumhydroxid, Kaliumhydroxid und Calci- umhydroxid, Alkalimetall- und Erdalkalimetalloxide wie Lithiumoxid, Natriumoxid, Calci- umoxid und Magnesiumoxid, Alkalimetall- und Erdalkalimetallhydride wie Lithiumhydrid, Natriumhydrid, Kaliumhydrid und Calciumhydrid, Alkalimetall- und Erdalkalimetall- carbonate wie Lithiumcarbonat, Kaliumcarbonat und Calciumcarbonat sowie Alkalime- tallhydrogencarbonate wie Natriumhydrogencarbonat, außerdem organische Basen, z.B. tertiäre Amine wie Trimethylamin, Triethylamin, Diisopropylethylamin, N- Methylmorpholin, und N-Methylpiperidin, Pyridin, substituierte Pyridine wie Collidin, Lutidin und 4-Dimethylaminopyridin sowie bicyclische Amine in Betracht. Besonders bevorzugt werden Natriumhydroxid, Triethylamin, Ethyldiisopropylamin, N- methylmorpholin und Pyridin.Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and Calcium hydride, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate and alkali metal bicarbonates such as sodium bicarbonate, as well as organic bases, for example tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, N-methylmorpholine, and N-methylpiperidine, pyridine, substituted pyridines such as collidine Lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Especially Preference is given to sodium hydroxide, triethylamine, ethyldiisopropylamine, N-methylmorpholine and pyridine.
Die Basen werden im allgemeinen in katalytischen Mengen eingesetzt, sie können a- ber auch äquimolar, im Überschuß oder gegebenenfalls als Lösungsmittel verwendet werden.The bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as solvent.
Die Edukte werden im allgemeinen in äquimolaren Mengen miteinander umgesetzt. Es kann vorteilhaft sein Il in einem Überschuß bezogen auf IM einzusetzen.The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use II in an excess relative to IM.
Die Aufarbeitung und Isolierung der Produkte kann in an sich bekannter Weise erfolgen.The workup and isolation of the products can be done in a conventional manner.
Die Umsetzung der Heteroaroylderivate der Formel IM mit L1 = Ci-Cδ-Alkoxy mit Aminen der Formel Il zu den gewünschten heteroaroyl-substituierten Alaninen der Formel I erfolgt üblicherweise bei Temperaturen von 0 °C bis zum Siedepunkt des Reaktionsgemisches, vorzugsweise O0C bis 1000C, besonders bevorzugt bei Raumtemperatur in einem inerten organischen Lösungsmittel gegebenenfalls in Gegenwart einer Base [vgl. Kawahata, N. H. et al., Tetrahedron Lett. 43 (40), 7221-7223 (2002); Takahashi, K. et al., J. Org. Chem. 50 (18), 3414-3415 (1985); Lee, Y. et al., J. Am. Chem. Soc. 121 (36), 8407-8408 (1999)].The reaction of the heteroaroyl of the formula III with L 1 = Ci-Cδ-alkoxy with an amine of the formula II to give the desired heteroaroyl-substituted alanines of the formula I is usually carried out at temperatures from 0 ° C to the boiling point of the reaction mixture, O is preferably 0 C to 100 ° C., more preferably at room temperature in an inert organic solvent, if appropriate in the presence of a base [cf. Kawahata, NH et al., Tetrahedron Lett. 43 (40), 7221-7223 (2002); Takahashi, K. et al., J. Org. Chem. 50 (18), 3414-3415 (1985); Lee, Y. et al., J. Am. Chem. Soc. 121 (36), 8407-8408 (1999)].
Geeignete Lösungsmittel sind aliphatische Kohlenwasserstoffe wie Pentan, Hexan, Cyclohexan und Gemische von Cs-Cs-Al kanen, aromatische Kohlenwasserstoffe wie Benzol, Toluol, o-, m- und p-Xylol, halogenierte Kohlenwasserstoffe wie Methylenchlorid, Chloroform und Chlorbenzol, Ether wie Diethylether, Diisopropylether, tert- Butylmethylether, Dioxan, Anisol und Tetra hydrofu ran (THF), Nitrile wie Acetonitril und Propionitril, Ketone wie Aceton, Methylethylketon, Diethylketon und tert- Butylmethylketon, Alkohole wie Methanol, Ethanol, n-Propanol, Isopropanol, n-Butanol und tert.-Butanol, sowie Dimethylsulfoxid, Dimethylformamid (DMF), Dimethylacetamid (DMA) und N-Methylpyrrolidon (NMP) oder auch in Wasser, besonders bevorzugt sind Methylenchlorid, THF, Methanol, Ethanol und Wasser.Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as benzene, toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether , Diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n- Butanol and tert-butanol, and dimethyl sulfoxide, dimethylformamide (DMF), dimethylacetamide (DMA) and N-methylpyrrolidone (NMP) or in water, particularly preferred are methylene chloride, THF, methanol, ethanol and water.
Es können auch Gemische der genannten Lösungsmittel verwendet werden.It is also possible to use mixtures of the solvents mentioned.
Die Umsetzung kann gegebenenfalls in Gegenwart einer Base erfolgen. Als Basen kommen allgemein anorganische Verbindungen wie Alkalimetall- und Erdalkalimetallhydroxide wie Lithiumhydroxid, Natriumhydroxid, Kaliumhydroxid und Calciumhydroxid, Alkalimetall- und Erdalkalimetalloxide wie Lithiumoxid, Natriumoxid, Calciumoxid und Magnesiumoxid, Alkalimetall- und Erdalkalimetallhydride wie Lithiumhydrid, Natriumhydrid, Kaliumhydrid und Calciumhydrid, Alkalimetall- und Erdalkalimetallcarbonate wie Lithiumcarbonat, Kaliumcarbonat und Calciumcarbonat sowie Alkalimetallhydrogencar- bonate wie Natriumhydrogencarbonat, außerdem organische Basen, z.B. tertiäre Amine wie Trimethylamin, Triethylamin, Diisopropylethylamin, N-Methylmorpholin, und N- Methylpiperidin, Pyridin, substituierte Pyridine wie Collidin, Lutidin und 4- Dimethylaminopyridin sowie bicyclische Amine in Betracht. Besonders bevorzugt wer- den Natriumhydroxid, Triethylamin, Ethyldiisopropylamin, N-methylmorpholin und Pyridin.The reaction may optionally be carried out in the presence of a base. As bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate, and alkali metal hydrogen carbonate in addition, organic bases, for example tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, N-methylmorpholine, and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Particularly preferred are sodium hydroxide, triethylamine, ethyldiisopropylamine, N-methylmorpholine and pyridine.
Die Basen werden im allgemeinen in katalytischen Mengen eingesetzt, sie können a- ber auch äquimolar, im Überschuß oder gegebenenfalls als Lösungsmittel verwendet werden.The bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as solvent.
Die Edukte werden im allgemeinen in äquimolaren Mengen miteinander umgesetzt. Es kann vorteilhaft sein, Il in einem Überschuß bezogen auf IM einzusetzen.The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use Il in an excess relative to IM.
Die Aufarbeitung und Isolierung der Produkte kann in an sich bekannter Weise erfolgen.The workup and isolation of the products can be done in a conventional manner.
Die für die Herstellung der heteroaroyl-substituierten Alanine der Formel I benötigten Amine der Formel Il können käuflich erworben werden.The amines of the formula II required for the preparation of the heteroaroyl-substituted alanines of the formula I can be purchased.
Verfahren BMethod B
Heteroaroylderivate der Formel IM mit R6 = Rx und R7 = Wasserstoff können auch er- halten werden, indem acylierte Glycin-Derivate der Formel VIII, wobei die Acylgruppe eine abspaltbare Schutzgruppe wie Benzyloxycarbonyl (vgl. Villa mit Σ = Benzyl) oder tert.-Butyloxycarbonyl (vgl. Villa mit Σ = tert-Butyl) sein kann, mit Iminoverbindungen VII zu entsprechenden Aldolprodukten VI mit R6 = Rx und R7 = Wasserstoff kondensiert werden. Anschließend wird die Schutzgruppe abgespalten und das so entstandene Alaninderivat der Formel V mit R6 = Rx und R7 = Wasserstoff mit Heteroarylsäu- re(derivate)n der Formel IV acyliert.Heteroaroyl of the formula III with R 6 = R x and R 7 = hydrogen can also keep ER- by acylated glycine derivatives of the formula VIII, wherein the acyl group is tert-cleavable protecting group such as benzyloxycarbonyl (see FIG. Villa with Σ = benzyl), or Butyloxycarbonyl (see Villa with Σ = tert-butyl) may be condensed with imino compounds VII to give corresponding aldol VI with R 6 = R x and R 7 = hydrogen. Subsequently, the protective group is cleaved off and the resulting alanine derivative of the formula V is acylated with R 6 = R x and R 7 = hydrogen with heteroaryl (derivatives) n of the formula IV.
Analog kann auch ein acyliertes Glycin-Derivat der Formel VIII, wobei die Acylgruppe ein substituierter Heteroarolyrest (vgl. VIIIb) ist, unter Baseneinfluß mit einer Iminover- bindung VII zum Heteroaroylderivat IM mit R6 = Rx und R7 = Wasserstoff umgesetzt werden: Analogously, it is also possible to react an acylated glycine derivative of the formula VIII where the acyl group is a substituted heteroarol radical (cf., VIIIb) under base influence with an imino compound VII to give the heteroaroyl derivative IM where R 6 = R x and R 7 = hydrogen.
Villa VI V mit R6 = = Rx und R7 = H mit R6 = Rx und R7 = HVilla VI V with R 6 = = R x and R 7 = H with R 6 = R x and R 7 = H
OO
+ AAL! iv + A A L! iv
mit R6 = Rx und R7 = H with R 6 = R x and R 7 = H
Rx steht für R6 oder für eine abspaltbare Schutzgruppe wie Ci-Cδ-Alkyloxycarbonyl (z.B. tert.-Butyloxycarbonyl), Ci-Cβ-Alkylsulfinyl (z.B. tert.-Butylsulfinyl) oder gegebe- nenfalls durch Ci-Cβ-Alkyl substituiertes Arylsulfinyl (z.B. Toluylsulfinyl).R x is R 6 or a removable protecting group such as C 1 -C 6 -alkyloxycarbonyl (eg tert-butyloxycarbonyl), C 1 -C 6 -alkylsulfinyl (eg tert-butylsulfinyl) or optionally C 1 -C 6 -alkyl-substituted arylsulfinyl ( eg toluylsulfinyl).
L1 steht für eine nucleophil verdrängbare Abgangsgruppe, z.B. für Hydroxy oder Ci-Cβ- Alkoxy.L 1 is a nucleophilically displaceable leaving group, for example for hydroxy or C 1 -C 6 -alkoxy.
L2 steht für eine nucleophil verdrängbare Abgangsgruppe, z.B. für Hydroxy, Halogen, Ci-Cδ-Alkylcarbonyl, Ci-Cδ-Alkoxycarbonyl, Ci -C4-Al kylsu If onyl, Phosphoryl oder Iso- ureyl.L 2 is a nucleophilically displaceable leaving group, for example hydroxy, halogen, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 4 -alkyl, onyl, phosphoryl or iso-ureyl.
Die Umsetzung der Glycinderivate VIII mit Iminoverbindungen VII zum entsprechenden Aldolprodukt VI mit R6 = Rx und R7 = Wasserstoff bzw. Heteroaroylderivat IM mit R6 = Rx und R7 = Wasserstoff erfolgt üblicherweise bei Temperaturen von -1000C bis zum Siedepunkt der Reaktionsmischung, bevorzugt -8O0C bis 2O0C, insbesondere bevorzugt -8O0C bis -2O0C, in einem inerten organischen Lösungsmittel in Gegenwart einer Base [vgl. F. A. Davis, Organic letters (2004) 6 (16), 2789 - 2792].The reaction of the glycine derivatives VIII with imino compounds VII to the corresponding aldol product VI with R 6 = R x and R 7 = hydrogen or heteroaroyl derivative IM with R 6 = R x and R 7 = hydrogen is usually carried out at temperatures from -100 0 C to the boiling point the reaction mixture, preferably -8O 0 C to 2O 0 C, particularly preferably -8O 0 C to -2O 0 C, in an inert organic solvent in the presence of a base [see. FA Davis, Organic letters (2004) 6 (16), 2789-2792].
Geeignete Lösungsmittel sind aliphatische Kohlenwasserstoffe wie Pentan, Hexan, Cyclohexan und Gemische von Cs-Cs-Al kanen, aromatische Kohlenwasserstoffe wie Toluol, o-, m- und p-Xylol, Ether wie Diethylether, Diisopropylether, tert- Butylmethylether, Dioxan, Anisol und Tetra hydrofu ran, sowie Dimethylsulfoxid, Di- methylformamid und Dimethylacetamid, besonders bevorzugt Diethylether, Dioxan und Tetra hydrofu ran. Es können auch Gemische der genannten Lösungsmittel verwendet werden.Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and Tetrahydrofuran, as well as dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably diethyl ether, dioxane and tetrahydrofuran. It is also possible to use mixtures of the solvents mentioned.
Als Basen kommen allgemein anorganische Verbindungen wie Alkalimetall- und Erdalkalimetallhydride wie Lithiumhydrid, Natriumhydrid, Kaliumhydrid und Calciumhydrid, Alkalimetallamide wie Lithiumisopropylamid und Lithiumhexamethyldisilazid, metallorganische Verbindungen, insbesondere Alkalimetallalkyle wie Methyllithium, Butyllithium und Phenyllithium, sowie Alkalimetall- und Erdalkalimetallalkoholate wie Natrium- methanolat, Natriumethanolat, Kaliumethanolat, Kalium- tert.-Butanolat, Kalium-tert.- Pentanolat und Dimethoxymagnesium, außerdem organische Basen, z.B. tertiäre Ami- ne wie Trimethylamin, Triethylamin, Diisopropylethylamin und N-Methylpiperidin, Pyri- din, substituierte Pyridine wie Collidin, Lutidin und 4-Dimethylaminopyridin sowie bicyc- lische Amine in Betracht. Besonders bevorzugt werden Natriumhydrid, Lithiumhexamethyldisilazid und Lithiumdiisopropylamid.Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium isopropylamide and lithium hexamethyldisilazide, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, and alkali metal and alkaline earth metal alkoxides such as sodium methoxide, sodium ethanolate, Potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and Dimethoxymagnesium, also organic bases, eg tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Particularly preferred are sodium hydride, lithium hexamethyldisilazide and lithium diisopropylamide.
Die Basen werden im allgemeinen in äquimolaren Mengen eingesetzt, sie können aber auch katalytisch, im Überschuß oder gegebenenfalls als Lösungsmittel verwendet werden.The bases are generally used in equimolar amounts, but they can also be used catalytically, in excess or optionally as a solvent.
Die Edukte werden im allgemeinen in äquimolaren Mengen miteinander umgesetzt. Es kann vorteilhaft sein, die Base und/oder die Iminoverbindungen VII in einem Überschuß bezogen auf die Glycinderivate VIII einzusetzen.The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use the base and / or the imino compounds VII in an excess based on the glycine derivatives VIII.
Die Aufarbeitung und Isolierung der Produkte kann in an sich bekannter Weise erfolgen.The workup and isolation of the products can be done in a conventional manner.
Die für die Herstellung der Heteroaroylderivate IM mit R6 = Rx und R7 = Wasserstoff benötigten Glycinderivate der Formel VIII können käuflich erworben werden, sind in der Literatur bekannt [z. B. H. Pessoa-Mahana et al., Synth. Comm. 32, 1437 (2002] oder können gemäß der zitierten Literatur hergestellt werden.The glycine derivatives of the formula VIII required for the preparation of the heteroaroyl derivatives IM with R 6 = R x and R 7 = hydrogen can be purchased, are known in the literature [z. BH Pessoa-Mahana et al., Synth. Comm. 32, 1437 (2002) or can be prepared according to the cited literature.
Die Abspaltung der Schutzgruppe Σ zu Alaninderivaten der Formel V mit R6 = Rx und R7 = Wasserstoff erfolgt nach literaturbekannten Methoden [vgl. J. -F. Rousseau et al., J. Org. Chem. 63, 2731-2737 (1998) ); J. M. Andres, Tetrahedron 56, 1523 (2000)]; im Fall von Σ = Benzyl durch Hydrogenolyse, bevorzugt durch Wasserstoff und Pd/C in Methanol; im Fall von Σ = tert.-Butyl durch Säure, bevorzugt Salzsäure in Dioxan.The cleavage of the protective group Σ to alanine derivatives of the formula V with R 6 = R x and R 7 = hydrogen is carried out by methods known from the literature [cf. J. -F. Rousseau et al., J. Org. Chem. 63, 2731-2737 (1998)); JM Andres, Tetrahedron 56, 1523 (2000)]; in the case of Σ = benzyl by hydrogenolysis, preferably by hydrogen and Pd / C in methanol; in the case of Σ = tert-butyl by acid, preferably hydrochloric acid in dioxane.
Die Umsetzung der Alaninderivate V mit R6 = Rx und R7= Wasserstoff mit Heteroaryl- säure(derivate)n IV zu Heteroaroylderivaten IM mit R6 = Rx und R7 = Wasserstoff erfolgt üblicherweise analog der unter Verfahren A genannten Umsetzung der Alaninderivate der Formel V mit Heteroarylsäure(derivate)n der Formel IV zu Heteroaroylderivaten IM.The reaction of the alanine derivatives V with R 6 = R x and R 7 = hydrogen with heteroaryl acid (derivatives) n IV to Heteroaroylderivaten IM with R 6 = R x and R 7 = hydrogen is usually carried out analogously to the reaction of the Alaninderivate mentioned under process A. of the formula V with heteroaryl acid (derivatives) n of the formula IV to heteroaroyl derivatives IM.
Die, falls Rx für eine abspaltbare Schutzgruppe steht, gegebenenfalls notwendige Abspaltung dieser Schutzgruppe Rx erfolgt nach literaturbekannten Methoden [vgl. J. -F. Rousseau et al., J. Org. Chem. 63, 2731-2737 (1998) ); J. M. Andres, Tetrahedron 56, 1523 (2000)]; im Fall von Σ = Benzyl durch Hydrogenolyse, bevorzugt durch Wasserstoff und Pd/C in Methanol; im Fall von Σ = tert.-Butyl durch Säure, bevorzugt Salzsäure in Dioxan.Which, if R x is a removable protecting group, optionally necessary cleavage of this protective group R x is carried out by literature methods [see. J. -F. Rousseau et al., J. Org. Chem. 63, 2731-2737 (1998)); JM Andres, Tetrahedron 56, 1523 (2000)]; in the case of Σ = benzyl by hydrogenolysis, preferably by hydrogen and Pd / C in methanol; in the case of Σ = tert-butyl by acid, preferably hydrochloric acid in dioxane.
Die auf diesem Weg erhältlichen Heteroaroylderivate der Formel IM mit R6 und R7 = Wasserstoff lassen sich mit Aminen der Formel Il analog zu Verfahren A zu den gewünschten heteroaroyl-substituierten Alaninen der Formel I mit R7 = Wasserstoff umsetzen, welche dann mit Verbindungen der Formel IX zu heteroaroyl-substituierten Alaninen der Formel I derivatisiert werden können [vgl. z.B. Yokokawa, F. et al., Tetrahedron Lett. 42 (34), 5903-5908 (2001 ); Arrault, A. et al., Tetrahedron Lett. 43( 22), 4041-4044 (2002)].The heteroaroyl derivatives of the formula III with R 6 and R 7 = hydrogen which can be obtained in this way can be reacted with amines of the formula II analogously to process A to give the desired heteroaroyl-substituted alanines of the formula I where R 7 = hydrogen, which is then reacted with compounds of the formula Formula IX can be derivatized to heteroaroyl-substituted alanines of the formula I [see. eg Yokokawa, F. et al., Tetrahedron Lett. 42 (34), 5903-5908 (2001); Arrault, A. et al., Tetrahedron Lett. 43 (22), 4041-4044 (2002)].
Ebenso können die Heteroaroylderivate der Formel IM mit R6 und R7 = Wasserstoff zunächst mit Verbindungen der Formel IX zu weiteren Heteroaroylderivaten der Formel IM mit R7 = Wasserstoff derivatisiert werden [vgl. z.B. Jung-Hui Sun et al., Heterocycles (2004), 63(7), 585-1599; Christian Lherbet et al., Bioorg. and Med. Chem. Lett. (2003), 13(6), 997-1000; Masami Otsuka et al., Chem. and Pharm. Bull. (1985), 33(2), 509- 514; J. R Piper et al., J. of Med. Chem. (1985), 28(8), 1016-1025] und anschließend analog zu Verfahren A mit Aminen der Formel Il zu den gewünschten heteroaroyl- substituierten Alaninen der Formel I mit R7 = Wasserstoff umgesetzt werden:Likewise, the heteroaroyl derivatives of the formula III where R 6 and R 7 = hydrogen can first be derivatized with compounds of the formula IX to form further heteroaroyl derivatives of the formula III where R 7 = hydrogen [cf. eg, Jung-Hui Sun et al., Heterocycles (2004), 63 (7), 585-1599; Christian Lherbet et al., Bioorg. and Med. Chem. Lett. (2003), 13 (6), 997-1000; Masami Otsuka et al., Chem. And Pharm. Bull. (1985), 33 (2), 509-514; J. R Piper et al., J. of Med. Chem. (1985), 28 (8), 1016-1025] and then analogously to process A with amines of the formula II to give the desired heteroaroyl-substituted alanines of the formula I R 7 = hydrogen are reacted:
I mit R6 und R7 = H mit R6 und R7 = HI with R 6 and R 7 = H with R 6 and R 7 = H
I mit R7 = H mit R7 = HI with R 7 = H with R 7 = H
L1 steht für eine nucleophil verdrängbare Abgangsgruppe, z.B. für Hydroxy oder Ci-Cβ- Alkoxy. L3 steht für eine nucleophil verdrängbare Abgangsgruppe, z.B. für Halogen, Hydroxy, oder Ci-Cδ-Alkoxy.L 1 is a nucleophilically displaceable leaving group, for example for hydroxy or C 1 -C 6 -alkoxy. L 3 is a nucleophilically displaceable leaving group, for example halogen, hydroxy, or C 1 -C 6 -alkoxy.
Die Umsetzung der Heteroaroylderivate der Formel IM (mit R7 = Wasserstoff und gege- benenfalls mit R6 = Wasserstoff) mit Aminen der Formel Il zu heteroaroyl-substituierten Alaninen der Formel I (mit R7 = Wasserstoff und gegebenenfalls mit R6 = Wasserstoff) erfolgt üblicherweise analog der unter Verfahren A geschilderten Umsetzung der Heteroaroylderivate der Formel IM mit Aminen der Formel M.The reaction of the heteroaroyl derivatives of the formula III (where R 7 = hydrogen and optionally R 6 = hydrogen) with amines of the formula II to give heteroaroyl-substituted alanines of the formula I (where R 7 = hydrogen and optionally R 6 = hydrogen) usually carried out analogously to the reaction of the heteroaroyl derivatives of the formula III described under process A with amines of the formula M.
Die Umsetzung der Heteroaroylderivate der Formel IM mit R6 und R7 = Wasserstoff bzw. der heteroaroyl-substituierten Alaninen der Formel I mit R6 und R7 = Wasserstoff mit Verbindungen der Formel IX zu Heteroaroylderivaten der Formel IM mit R7 = Wasserstoff bzw. heteroaroyl-substituierten Alaninen der Formel I mit R7 = Wasserstoff erfolgt üblicherweise bei Temperaturen von O0C bis 1000C, vorzugsweise 1 O0C bis 5O0C, in einem inerten organischen Lösungsmittel in Gegenwart einer Base [vgl. z.B. Jung- Hui Sun et al., Heterocycles (2004), 63(7), 585-1599; Christian Lherbet et al., Bioorg. and Med. Chem. Lett. (2003), 13(6), 997-1000; Masami Otsuka et al., Chem. and Pharm. Bull. (1985), 33(2), 509-514; J. R Piper et al., J. of Med. Chem. (1985), 28(8), 1016-1025].The reaction of the heteroaroyl derivatives of the formula III where R 6 and R 7 = hydrogen or the heteroaroyl-substituted alanines of the formula I with R 6 and R 7 = hydrogen with compounds of the formula IX to heteroaroyl derivatives of the formula III where R 7 = hydrogen or heteroaroyl-substituted alanines of the formula I with R 7 = hydrogen is usually carried out at temperatures of from 0 C to 100 0 C, preferably from 1 O 0 C to 5O 0 C, in an inert organic solvent in the presence of a base [cp. eg Jung-Hui Sun et al., Heterocycles (2004), 63 (7), 585-1599; Christian Lherbet et al., Bioorg. and Med. Chem. Lett. (2003), 13 (6), 997-1000; Masami Otsuka et al., Chem. And Pharm. Bull. (1985), 33 (2), 509-514; J. R Piper et al., J. of Med. Chem. (1985), 28 (8), 1016-1025].
Geeignete Lösungsmittel sind aliphatische Kohlenwasserstoffe wie Pentan, Hexan, Cyclohexan und Gemische von Cs-Cs-Al kanen, aromatische Kohlenwasserstoffe wie Toluol, o-, m- und p-Xylol, halogenierte Kohlenwasserstoffe wie Methylenchlorid, Chloroform und Chlorbenzol, Ether wie Diethylether, Diisopropylether, tert- Butylmethylether, Dioxan, Anisol und Tetrahydrofuran, Nitrile wie Acetonitril und Propi- onitril, Ketone wie Aceton, Methylethylketon, Diethylketon und tert.-Butylmethylketon, Alkohole wie Methanol, Ethanol, n-Propanol, Isopropanol, n-Butanol und tert.-Butanol, sowie Dimethylsulfoxid, Dimethylformamid und Dimethylacetamid, besonders bevorzugt Dichlormethan, tert. -Butylmethylether, Dioxan und Tetrahydrofuran.Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether , tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propinonitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert. Butanol, and dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably dichloromethane, tert. Butyl methyl ether, dioxane and tetrahydrofuran.
Es können auch Gemische der genannten Lösungsmittel verwendet werden.It is also possible to use mixtures of the solvents mentioned.
Als Basen kommen allgemein anorganische Verbindungen wie Alkalimetall- und Erdalkalimetallhydroxide wie Lithiumhydroxid, Natriumhydroxid, Kaliumhydroxid und Calci- umhydroxid, Alkalimetall- und Erdalkalimetalloxide wie Lithiumoxid, Natriumoxid, Calci- umoxid und Magnesiumoxid, Alkalimetall- und Erdalkalimetallhydride wie Lithiumhydrid, Natriumhydrid, Kaliumhydrid und Calciumhydrid, Alkalimetallamide wie Lithiuma- mid, Natriumamid und Kaliumamid, Alkalimetall- und Erdalkalimetallcarbonate wie Lithiumcarbonat, Kaliumcarbonat und Calciumcarbonat sowie Alkalimetall- hydrogencarbonate wie Natriumhydrogencarbonat, metallorganische Verbindungen, insbesondere Alkalimetallalkyle wie Methyllithium, Butyllithium und Phenyllithium, Al- kylmagnesiumhalogenide wie Methylmagnesiumchlorid sowie Alkalimetall- und Erdal- kalimetallalkoholate wie Natriummethanolat, Natriumethanolat, Kaliumethanolat, Kali- um- tert.-Butanolat, Kalium-tert.-Pentanolat und Dimethoxymagnesium, außerdem organische Basen, z.B. tertiäre Amine wie Trimethylamin, Triethylamin, Diisopropylethy- lamin und N-Methylpiperidin, Pyridin, substituierte Pyridine wie Collidin, Lutidin und 4- Dimethylaminopyridin sowie bicyclische Amine in Betracht. Besonders bevorzugt wer- den Natriumhydroxid, Natriumhydrid und Triethylamin.Bases generally include inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, Alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate and also alkali metal hydrogencarbonates such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and also alkali metal and earth metal halides. potassium alcoholates such as sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butanolate, potassium tert-pentoxide and dimethoxy magnesium, as well as organic bases, for example tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic Amines into consideration. Particular preference is given to sodium hydroxide, sodium hydride and triethylamine.
Die Basen werden im allgemeinen in äquimolaren Mengen eingesetzt, sie können aber auchkatalytisch, im Überschuß oder gegebenenfalls als Lösungsmittel verwendet werden.The bases are generally used in equimolar amounts, but they can also be used catalytically, in excess or optionally as a solvent.
Die Edukte werden im allgemeinen in äquimolaren Mengen miteinander umgesetzt. Es kann vorteilhaft sein, die Base und/oder IX in einem Überschuß bezogen auf IM bzw. I einzusetzen.The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use the base and / or IX in an excess based on IM or I.
Die Aufarbeitung und Isolierung der Produkte kann in an sich bekannter Weise erfolgen.The workup and isolation of the products can be done in a conventional manner.
Verfahren CMethod C
Heteroaroxyl-Derivate der Formel IM mit R6 und R7 = Wasserstoff können auch erhalten werden, indem Glycin-Derivate der Formel XII mit einer Nitroverbindung der Formel Xl zu Nitro-Anilinderivaten der Formel X umgesetzt und anschließend reduziert werden:Heteroaroxyl derivatives of the formula III where R 6 and R 7 = hydrogen can also be obtained by reacting glycine derivatives of the formula XII with a nitro compound of the formula XI to give nitroaniline derivatives of the formula X and then reducing them:
XII X III mit R6 und R7 = HXII X III with R 6 and R 7 = H
L1 steht für eine nucleophil verdrängbare Abgangsgruppe, z.B. Hydroxy oder Ci-Cβ- Alkoxy.L 1 is a nucleophilically displaceable leaving group, for example hydroxy or C 1 -C 6 -alkoxy.
L4 steht für eine nucleophil verdrängbare Abgangsgruppe, z.B. Halogen wie Chlor oder Brom.L 4 represents a nucleophilically displaceable leaving group, for example halogen, such as chlorine or bromine.
Die Umsetzung der Nitroverbindung Xl mit dem Glycin-Derivat XM erfolgt üblicherweise bei einer Temperatur von -100°C bis zum Siedepunkt der Reaktionsmischung, bevor- zugt bei -80°C bis 20°C, in einem inerten organischen Lösungsmittel in Gegenwart einer Base (vgl. Vicky A. Burgess et al., Aust. J. of Chem. (1988), 41 (7), 1063-1070). Geeignete Lösungsmittel sind aliphatische Kohlenwasserstoffe wie Pentan, Hexan, Cyclohexan und Gemische von Cs-Cs-Al kanen, aromatische Kohlenwasserstoffe wie Toluol, o-, m- und p-Xylol, halogenierte Kohlenwasserstoffe wie Methylenchlorid, Chloroform und Chlorbenzol, Ether wie Diethylether, Diisopropylether, tert- Butylmethylether, Dioxan, Anisol und Tetrahydrofuran, Nitrile wie Acetonitril und Propi- onitril, Ketone wie Aceton, Methylethylketon, Diethylketon und tert.-Butylmethylketon, Alkohole wie Methanol, Ethanol, n-Propanol, Isopropanol, n-Butanol und tert.-Butanol, sowie Dimethylsulfoxid, Dimethylformamid und Dimethylacetamid, besonders bevorzugt Dichlormethan, tert. -Butylmethylether, Dioxan und Tetrahydrofuran.The reaction of the nitro compound XI with the glycine derivative XM is usually carried out at a temperature of -100 ° C to the boiling point of the reaction mixture, preferably at -80 ° C to 20 ° C, in an inert organic solvent in the presence of a base ( See Vicky A. Burgess et al., Aust. J. of Chem. (1988), 41 (7), 1063-1070). Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether , tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propinonitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert. Butanol, and dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably dichloromethane, tert. Butyl methyl ether, dioxane and tetrahydrofuran.
Es können auch Gemische der genannten Lösungsmittel verwendet werden.It is also possible to use mixtures of the solvents mentioned.
Als Basen kommen allgemein anorganische Verbindungen wie Alkalimetall- und Erdalkalimetallhydroxide wie Lithiumhydroxid, Natriumhydroxid, Kaliumhydroxid und Calci- umhydroxid, Alkalimetall- und Erdalkalimetalloxide wie Lithiumoxid, Natriumoxid, Calci- umoxid und Magnesiumoxid, Alkalimetall- und Erdalkalimetallhydride wie Lithiumhydrid, Natriumhydrid, Kaliumhydrid und Calciumhydrid, Alkalimetallamide wie Lithiuma- mid, Natriumamid und Kaliumamid, Alkalimetall- und Erdalkalimetallcarbonate wie Lithiumcarbonat, Kaliumcarbonat und Calciumcarbonat sowie Alkalimetall- hydrogencarbonate wie Natriumhydrogencarbonat, metallorganische Verbindungen, insbesondere Alkalimetallalkyle wie Methyllithium, Butyllithium und Phenyllithium, Al- kylmagnesiumhalogenide wie Methylmagnesiumchlorid sowie Alkalimetall- und Erdal- kalimetallalkoholate wie Natriummethanolat, Natriumethanolat, Kaliumethanolat, Kalium- tert. -Butanolat, Kalium-tert.-Pentanolat und Dimethoxymagnesium, außerdem or- ganische Basen, z.B. tertiäre Amine wie Trimethylamin, Triethylamin, Diisopropylethy- lamin und N-Methylpiperidin, Pyridin, substituierte Pyridine wie Collidin, Lutidin und 4- Dimethylaminopyridin sowie bicyclische Amine in Betracht. Besonders bevorzugt werden Natriumhydroxid, Natriumhydrid und Triethylamin.Bases generally include inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, Alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate and also alkali metal hydrogencarbonates such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and also alkali metal and earth metal halides. potassium metal alcoholates, such as sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert. Butanolate, potassium tertiary pentoxide and dimethoxy magnesium, as well as organic bases, e.g. tertiary amines such as trimethylamine, triethylamine, Diisopropylethy- lamin and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Particularly preferred are sodium hydroxide, sodium hydride and triethylamine.
Die Basen werden im allgemeinen in äquimolaren Mengen eingesetzt, sie können aber auchkatalytisch, im Überschuß oder gegebenenfalls als Lösungsmittel verwendet werden.The bases are generally used in equimolar amounts, but they can also be used catalytically, in excess or optionally as a solvent.
Die Edukte werden im allgemeinen in äquimolaren Mengen miteinander umgesetzt. Es kann vorteilhaft sein, die Base und/oder Xl in einem Überschuß bezogen auf XII einzusetzen.The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use the base and / or XI in an excess based on XII.
Die Aufarbeitung und Isolierung der Produkte kann in an sich bekannter Weise erfolgen.The workup and isolation of the products can be done in a conventional manner.
Die benötigten Nitroverbindung der Formel Xl können käuflich erworben werden. Die benötigten Glycin-Derivate der Formel XII können analog literaturbekannter Methoden (vgl. Vicky A. Burgess et al., Aust. J. of Chem. (1988), 41 (7), 1063-1070) erhalten werden.The required nitro compound of the formula XI can be purchased. The required glycine derivatives of the formula XII can be obtained analogously to methods known from the literature (compare Vicky A. Burgess et al., Aust. J. of Chem. (1988), 41 (7), 1063-1070).
Die Reduktion der Nitro-Anilinderivate der Formel X erfolgt üblicherweise bei einer Temperatur von -100°C bis zum Siedepunkt der Reaktionsmischung, bevorzugt -80°C bis 20°C, in einem inerten organischen Lösungsmittel mit einem Reduktionsmittel, (vgl. Vicky A. Burgess et al., Aust. J. of Chem. (1988), 41 (7), 1063-1070).The reduction of the nitroaniline derivatives of the formula X is usually carried out at a temperature of -100 ° C to the boiling point of the reaction mixture, preferably -80 ° C to 20 ° C, in an inert organic solvent with a reducing agent, (see Vicky A. Burgess et al., Aust. J. of Chem. (1988), 41 (7), 1063-1070).
Geeignete Lösungsmittel sind aliphatische Kohlenwasserstoffe wie Pentan, Hexan, Cyclohexan und Gemische von Cs-Cs-Al kanen, aromatische Kohlenwasserstoffe wie Toluol, o-, m- und p-Xylol, halogenierte Kohlenwasserstoffe wie Methylenchlorid, Chloroform und Chlorbenzol, Ether wie Diethylether, Diisopropylether, tert- Butylmethylether, Dioxan, Anisol und Tetrahydrofuran, Nitrile wie Acetonitril und Propionitril, Ketone wie Aceton, Methylethylketon, Diethylketon und tert- Butylmethylketon, Alkohole wie Methanol, Ethanol, n-Propanol, Isopropanol, n-Butanol und tert.-Butanol, sowie Dimethylsulfoxid, Dimethylformamid und Dimethylacetamid, besonders bevorzugt Toluol, Methylenchlorid oder tert. Butylmethylether.Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether , tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably toluene, methylene chloride or tert. Butyl methyl ether.
Geeignete Reduktionsmittel sind Übergangsmetall-Katalysatoren (z.B. Pd/C oder Ra- ney-Ni) in Kombination mit Wasserstoff.Suitable reducing agents are transition metal catalysts (e.g., Pd / C or Raney Ni) in combination with hydrogen.
Die Aufarbeitung und Isolierung des Produkts kann in an sich bekannter Weise erfolgen.The workup and isolation of the product can be carried out in a conventional manner.
Heteroaroylderivate der Formel IMHeteroaroyl derivatives of the formula III
wobei A, R1 sowie R4, R5, R6 und R7 die voanstehend genannten Bedeutungen haben und L1 für eine nucleophil verdrängbare Abgangsgruppe, z.B. für Hydroxy oder Ci-Cβ- Alkoxy steht, sind ebenfalls ein Gegenstand der vorliegenden Erfindung. Die besonders bevorzugten Ausführungsformen der Zwischenprodukte in Bezug auf die Variablen entsprechen denen der Reste A, R1 sowie R4 bis R7 der Formel I.where A, R 1 and R 4 , R 5 , R 6 and R 7 have the meanings given above and L 1 is a nucleophilically displaceable leaving group, for example hydroxy or C 1 -C 6 alkoxy, are also an object of the present invention. The particularly preferred embodiments of the intermediates with respect to the variables correspond to those of the radicals A, R 1 and R 4 to R 7 of the formula I.
Besonders bevorzugt werden Heteroaroylderivate der Formel IM, in der A 5- oder 6-gliedriges Heteroaryl ausgewählt aus der Gruppe Thienyl, Furyl, Pyra- zolyl, Imidazolyl, Thiazolyl, Oxazolyl und Pyridyl; wobei die genannten Heteroarylreste partiell oder vollständig halogeniert sein können und/oder 1 bis 3 Reste aus der Gruppe Ci-Cβ-Alkyl, C3-C6-Cycloalkyl, und Ci-Cβ-Halogenalkyl tragen können; R1 Wasserstoff; R4 Wasserstoff; R5 Wasserstoff, Ci-C6-Alkyl, C2-C6-Alkenyl, Ci-C6-Halogenalkyl, C2-C6-Particular preference is given to heteroaroyl derivatives of the formula III in which A is 5- or 6-membered heteroaryl selected from the group consisting of thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl and pyridyl; wherein said heteroaryl may be partially or fully halogenated and / or 1 to 3 radicals from the group Ci-Cβ-alkyl, C3-C6-cycloalkyl, and carry Ci-Cβ-haloalkyl; R 1 is hydrogen; R 4 is hydrogen; R 5 is hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, Ci-C 6 haloalkyl, C 2 -C 6 -
Halogenalkenyl, Ci-C6-Hydroxyalkyl, Hydroxycarbonyl-Ci-C4-alkyl, Phenyl-Ci-C4- alkyl oder Phenyl-Ci-C4-hydroxyalkyl; R6 Wasserstoff, Formyl, Ci-C4-Alkylcarbonyl, Ci-C4-Alkylaminocarbonyl, Di-(Ci-C4- Alkyl)-aminocarbonyl, Phenylaminocarbonyl, N-(CI -C4-alkyl)-N-(phenyl)- aminocarbonyl, SO2CH31 SO2CF3 oder SO2(C6H5); und R7 Wasserstoff; bedeuten.Haloalkenyl, C 1 -C 6 -hydroxyalkyl, hydroxycarbonyl-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyl or phenyl-C 1 -C 4 -hydroxyalkyl; R 6 is hydrogen, formyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylaminocarbonyl, di (C 1 -C 4 -alkyl) aminocarbonyl, phenylaminocarbonyl, N- (C 1 -C 4 -alkyl) -N- (phenyl) -aminocarbonyl, SO 2 CH 31 SO 2 CF 3 or SO 2 (C 6 H 5 ); and R 7 is hydrogen; mean.
Die folgenden Beispiele dienen der Erläuterung der Erfindung.The following examples serve to illustrate the invention.
HerstellungsbeispielePreparation Examples
Beispiel 1example 1
N-[(2S)-3-(Methylamino)-2-({[1-methyl-3-(trifluormethyl)-1 H-pyrazol-4-yl]carbonyl}- amino)-3-oxopropyl]-O-tert-butylcarbamat (Nr. 3.11 )N - [(2S) -3- (methylamino) -2 - ({[1-methyl-3- (trifluoromethyl) -1H-pyrazol-4-yl] carbonyl} -amino) -3-oxopropyl] -O- tert-butylcarbamate (No 3.11)
1.1) (2S)-3-[(tert-Butoxycarbonyl)amino]-2-({[1-methyl-3-(trifluormethyl)-1 H-pyrazol-4-1.1) (2S) -3 - [(tert-butoxycarbonyl) amino] -2 - ({[1-methyl-3- (trifluoromethyl) -1H-pyrazole-4]
Zu einer Lösung von 14.7 g (57.8 mmol) (2S)-2-Amino-3-[(tert-butoxycarbonyl)amino]- propionsäuremethylester-Hydrochlorid und 9.9 g (125.3 mmol) Pyridin in Dichlor- methan wurden 12.3 g (57.9 mmol) 1-Methyl-3-(trifluormethyl)-1 H-pyrazol-4- carbonsäurechlorid bei einer Temperatur von 0 °C zugetropft. Das erhaltene Reaktionsgemisch wurde für weitere 16 Stunden bei Raumtemperatur gerührt und anschließend mit verdünnter Salzsäure (2 M) versetzt. Anschließend wurden die Phasen getrennt und die organische Phase mit Natriumcarbonatlösung gewaschen und getrocknet. Nach Entfernen des Lösungsmittels erhielt man 16.6 g der Titelverbindung als Feststoff, der ohne weitere Reinigung in die nachfolgende Reaktion eingesetzt wurde. 1H-NMR (DMSO): δ = 1.35 (s, 9H); 3.25-3.45 (m, 2H); 3.60 (s, 3H); 3.95 (s, 3H); 4.45 (q, 1 H); 6.95 (br t, 1 H); 8.35-8.45 (m, 2H).To a solution of 14.7 g (57.8 mmol) of (2S) -2-amino-3 - [(tert-butoxycarbonyl) amino] propionic acid methyl ester hydrochloride and 9.9 g (125.3 mmol) of pyridine in dichloromethane. methane, 12.3 g (57.9 mmol) of 1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxylic acid chloride was added dropwise at a temperature of 0 ° C. The resulting reaction mixture was stirred for a further 16 hours at room temperature and then treated with dilute hydrochloric acid (2 M). Subsequently, the phases were separated and the organic phase washed with sodium carbonate solution and dried. After removal of the solvent, 16.6 g of the title compound were obtained as a solid, which was used without further purification in the subsequent reaction. 1 H-NMR (DMSO): δ = 1.35 (s, 9H); 3.25-3.45 (m, 2H); 3.60 (s, 3H); 3.95 (s, 3H); 4.45 (q, 1H); 6.95 (br t, 1 H); 8.35-8.45 (m, 2H).
1.2) N-[(2S)-3-(Methylamino)-2-({[1-methyl-3-(trifluormethyl)-1 H-pyrazol-4-yl]carbonyl}- amino)-3-oxopropyl]-O-tert-butylcarbamat (Nr. 3.11 )1.2) N - [(2S) -3- (Methylamino) -2 - ({[1-methyl-3- (trifluoromethyl) -1H-pyrazol-4-yl] carbonyl} -amino) -3-oxopropyl] - O-tert-butylcarbamate (3.11)
In eine Lösung von 16.6 g (42.1 mmol) (2S)-3-[(tert-Butoxycarbonyl)amino]-2-({[1- methyl-3-(trifluormethyl)-1 H-pyrazol-4-yl]carbonyl}amino)propionsäuremethylester in Methanol wurde über eine Stunde Methylamin bei Raumtemperatur eingeleitet. Nach anschließender Entfernung des Lösungsmittels wurden 15.7 g der Titelverbindung in Form eines weißen Feststoffs erhalten, der ohne weitere Aufreinigung in Beispiel 2 eingesetzt wurde.In a solution of 16.6 g (42.1 mmol) of (2S) -3 - [(tert-butoxycarbonyl) amino] -2 - ({[1-methyl-3- (trifluoromethyl) -1H-pyrazol-4-yl] carbonyl methyl} -propionate in methanol was introduced at room temperature over one hour of methylamine. After subsequent removal of the solvent, 15.7 g of the title compound were obtained in the form of a white solid, which was used in Example 2 without further purification.
1H-NMR (CDCI3): δ = 1.40 (s, 9H); 2.80 (d, 3H); 3.50-3.65 (m, 2H); 3.95 (s, 3H); 4.60 (q, 1 H); 5.40 (t, 1 H); 7.10 (br s, 1 H); 7.70 (d, 1 H); 7.95 (s, 1 H). 1 H-NMR (CDCl 3 ): δ = 1.40 (s, 9H); 2.80 (d, 3H); 3.50-3.65 (m, 2H); 3.95 (s, 3H); 4.60 (q, 1H); 5.40 (t, 1H); 7.10 (br s, 1 H); 7.70 (d, 1H); 7.95 (s, 1H).
Beispiel 2Example 2
N-[(1 S)- 1 -(Aminomethyl)-2-(methylamino)-2-oxoethyl]-1 -methyl-3-(trifluormethyl)-1 H- pyrazol-4-carboxamid (Nr. 3N - [(1S) -1- (Aminomethyl) -2- (methylamino) -2-oxoethyl] -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide (No. 3
Zu einer Lösung von 15.7 g (39.9 mmol) N-[(2S)-3-(Methylamino)-2-({[1-methyl-3- (trifluormethylJ-I H-pyrazol^-yOcarbonylJaminoJ-S-oxopropyö-O-tert-butylcarbamat in 1 ,4-Dioxan wurden 40 ml_ einer Lösung von Chlorwasserstoff in 1 ,4-Dioxan (4 M) zugetropft. Das Reaktionsgemisch wurde für weitere 16 Stunden bei Raumtemperatur gerührt und im Anschluss eingeengt. Der Rückstand wurde in gesättigter Natriumcar- bonat-Lösung aufgenommen und mit Essigsäureethylester versetzt. Nach Trocknen der organischen Phase über Natriumsulfat und Entfernen des Lösungsmittels erhielt man 7.6 g der Titelverbindung in Form eines weißen Feststoffs, der ohne weitere Aufreinigung in Beispiel 3 eingesetzt wurde.To a solution of 15.7 g (39.9 mmol) of N - [(2S) -3- (methylamino) -2 - ({[1-methyl-3- (trifluoromethyl) -1H-pyrazole] -cyocarbonyl-amino-S-oxo-propyl-O tert-butylcarbamate in 1, 4-dioxane was added dropwise 40 ml_ of a solution of hydrogen chloride in 1, 4-dioxane (4 M). The reaction mixture was stirred for a further 16 hours at room temperature and then concentrated. The residue was taken up in saturated sodium carbonate solution and admixed with ethyl acetate. Drying of the organic phase over sodium sulfate and removal of the solvent gave 7.6 g of the title compound as a white solid, which was used in Example 3 without further purification.
1H-NMR (CDCI3): δ = 2.75 (dd, 1 H); 2.80 (d, 3H); 3.40 (dd, 1 H); 3.95 (s, 3H); 4.40-4.50 (m, 1 H); 7.40 (br s, 2H); 7.95 (s, 1 H). 1 H-NMR (CDCl 3 ): δ = 2.75 (dd, 1 H); 2.80 (d, 3H); 3.40 (dd, 1H); 3.95 (s, 3H); 4.40-4.50 (m, 1H); 7.40 (br s, 2H); 7.95 (s, 1H).
Beispiel 3Example 3
N-[(2S)-3-(Methylamino)-2-({[1-methyl-3-(trifluormethyl)-1 H-pyrazol-4-yl]carbonyl}- amino)-3-oxopropyl]-O-methylcarbamat (Nr. 3.10)N - [(2S) -3- (methylamino) -2 - ({[1-methyl-3- (trifluoromethyl) -1H-pyrazol-4-yl] carbonyl} -amino) -3-oxopropyl] -O- methyl carbamate (# 3.10)
Eine Lösung von 0.80 g (2.73 mmol) N-[(1 S)-1-(Aminomethyl)-2-(methylamino)-2- oxoethyl]-1-methyl-3-(trifluormethyl)-1 H-pyrazol-4-carboxamid und 0.25 g (3.16 mmol) Pyridin in Dichlormethan wurde mit 0.25 g (2.65 mmol) Chlorameisensäuremethyl-ester versetzt. Das Reaktionsgemisch wurde über Nacht bei Raumtemperatur gerührt. Nach Abfiltrieren und Trocknen des ausgefallenen Niederschlags erhielt man 0.35 g der Titelverbindung in Form eines weißen Feststoffs. 1H-NMR (DMSO): δ = 2.60 (d, 3H); 3.20-3.40 (m, 2H); 3.55 (s, 3H); 3.95 (s, 3H); 4.40 (q, 1 H); 7.10 (t, 1 H); 7.90 (br q, 1 H); 8.15 (d, 1 H); 8.40 (s, 1 H).A solution of 0.80 g (2.73 mmol) of N - [(1S) -1- (aminomethyl) -2- (methylamino) -2-oxoethyl] -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4 -carboxamide and 0.25 g (3.16 mmol) of pyridine in dichloromethane was treated with 0.25 g (2.65 mmol) of methyl chloroformate. The reaction mixture was stirred at room temperature overnight. Filtration and drying of the precipitate gave 0.35 g of the title compound as a white solid. 1 H-NMR (DMSO): δ = 2.60 (d, 3H); 3.20-3.40 (m, 2H); 3.55 (s, 3H); 3.95 (s, 3H); 4.40 (q, 1H); 7.10 (t, 1H); 7.90 (brq, 1H); 8.15 (d, 1H); 8.40 (s, 1H).
In den nachfolgenden Tabellen 2 und 3 werden neben den voranstehenden Verbindungen noch weitere Heteroaroylderivate der Formel IM sowie heteroaroyl-substituierte Alanine der Formel I aufgeführt, die in analoger Weise nach den voranstehend beschriebenen Verfahren hergestellt wurden oder herstellbar sind. In the following Tables 2 and 3, in addition to the above compounds, further heteroaroyl derivatives of the formula III and heteroaroyl-substituted alanines of the formula I are listed, which were prepared in an analogous manner by the methods described above or can be prepared.
Tabelle 2Table 2
OO
Tabelle 3Table 3
O)O)
K)K)
Biologische WirksamkeitBiological effectiveness
Die heteroaroylsubstituierten Alanine der Formel I und deren landwirtschaftlich brauchbaren Salze eignen sich - sowohl als Isomerengemische als auch in Form der reinen Isomeren - als Herbizide. Die Verbindungen der Formel I enthaltenden herbiziden Mittel bekämpfen Pflanzenwuchs auf Nichtkulturflächen sehr gut, besonders bei hohen Aufwandmengen. 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 heteroaroyl-substituted alanines of the formula I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of pure isomers - as herbicides. The compounds of the formula I containing herbicidal agents control plant growth on non-crop areas very well, especially at high application rates. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crops. This effect occurs especially at low application rates.
In Abhängigkeit von der jeweiligen Applikationsmethode können die Verbindungen der Formel I bzw. sie enthaltenden herbiziden Mittel noch in einer weiteren Zahl von Kulturpflanzen zur Beseitigung unerwünschter Pflanzen eingesetzt werden. In Betracht kommen beispielsweise folgende Kulturen:Depending on the particular application method, the compounds of the formula I or herbicidal compositions containing them can be used in a further number of crop plants for the removal of unwanted plants. For example, the following cultures may 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. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctori- us, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineen- sis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossy- pium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hor- deum vulgäre, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Pha- seolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccha- rum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgäre), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera und Zea mays.Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapeseed, Brassica napus var. napobrassica, 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 guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgaris, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phasolus 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 vulgaris), Theobroma cacao, Trifol ium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
Darüber hinaus können die Verbindungen der Formel I auch in Kulturen, die durch Züchtung einschließlich gentechnischer Methoden gegen die Wirkung von Herbiziden tolerant sind, verwandt werden.In addition, the compounds of formula I may also be used in cultures tolerant to the action of herbicides by breeding, including genetic engineering.
Darüber hinaus können die Verbindungen der Formel I auch in Kulturen, die durch Züchtung einschließlich gentechnischer Methoden gegen Insekten- oder Pilzbefall tolerant sind, verwandt werden.In addition, the compounds of formula I can also be used in cultures tolerant by breeding including genetic engineering against insect or fungal attack.
Die Verbindungen der Formel I bzw. die sie enthaltenden herbiziden Mittel können beispielsweise in Form von direkt versprühbaren wäßrigen Lösungen, Pulvern, Suspensionen, auch hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen oder Dis- persionen, Emulsionen, Öldispersionen, 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 of the formula I or the herbicidal compositions containing them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, even high-percentage aqueous, oily or other suspensions or dispersants. dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules by spraying, atomizing, dusting, scattering or pouring. The forms of application depend on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
Die herbiziden Mittel enthalten eine herbizid wirksame Menge mindestens einer Verbindung der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I und für die Formulierung von Pflanzenschutzmitteln übliche Hilfsmittel.The herbicidal compositions contain a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries customary for the formulation of crop protection agents.
Als inerte Hilfsstoffe kommen im Wesentlichen in Betracht:Suitable inert auxiliaries are essentially:
Mineralölfraktionen von mittlerem bis hohem Siedepunkt wie Kerosin und Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyc- lische und aromatische Kohlenwasserstoffe, z.B. Paraffine, Tetrahydronaphthalin, alky- lierte Naphthaline und deren Derivate, alkylierte Benzole und deren Derivate, Alkohole wie Methanol, Ethanol, Propanol, Butanol und Cyclohexanol, Ketone wie Cyclohexa- non, stark polare Lösungsmittel, z.B. Amine wie N-Methylpyrrolidon und Wasser.Mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, 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 and cyclohexanol, ketones such as cyclohexanone, strong polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Suspensionen, Pas- ten, netzbaren Pulvern oder wasserdispergierbaren Granulaten durch Zusatz vonAqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding
Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Substrate als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermittel 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.Water to be prepared. To prepare emulsions, pastes or oil dispersions, the substrates, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. However, it is also possible to prepare concentrates consisting of active substance, wetting, adhesion, dispersing or emulsifying agent and possibly solvent or oil, which are suitable for dilution with water.
Als oberflächenaktive Stoffe (Adjuvantien) kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Lignin-, Phenol-, Naphthalin- und Dibutyl- naphthalinsulfonsäure, sowie von Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octa- decanolen sowie von Fettalkoholglykolether, Kondensationsprodukte von sulfoniertem Naphthalin und seiner Derivate mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxyethyle- noctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenyl-, Tribu- tylphenylpolyglykolether, Alkylarylpolyetheralkohole, Isotridecylalkohol, Fettal koholethy- lenoxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylen- oder Polyoxypropylenal- kylether, Laurylalkoholpolyglykoletheracetat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht.As surfactants (adjuvants) are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethyl noctylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenylpolyglykolether, Alkylarylpolyetheralkohole, Isotridecylalkohol, Fettal koholethy- lenoxid condensates, ethoxylated Castor oil, polyoxyethylene or Polyoxypropylenal- kylether, Laurylalkoholpolyglykoletheracetat, sorbitol esters, lignin-Sulphatablaugen or methyl cellulose into consideration.
Pulver-, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden. 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.Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier. Granules, for example coated, impregnated and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral soils such as silicic acids, 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, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
Die Konzentrationen der Verbindungen der Formel I in den anwendungsfertigen Zubereitungen können in weiten Bereichen variiert werden. Im allgemeinen enthalten die Formulierungen 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 compounds of the formula I in the ready-to-use formulations can be varied within wide limits. In general, the formulations contain from about 0.001 to 98 wt .-%, preferably 0.01 to 95 wt .-%, of at least one active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
Die folgenden Formulierungsbeispiele verdeutlichen die Herstellung solcher Zubereitungen:The following formulation examples illustrate the preparation of such preparations:
I. 20 Gewichtsteile eines Wirkstoffs der Formel I werden in einer Mischung gelöst, die aus 80 Gewichtsteilen alkyliertem Benzol, 10 Gewichtsteilen des Anlagerungsproduktes von 8 bis 10 Mol Ethylenoxid an 1 Mol Ölsäure-N- monoethanolamid, 5 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure und 5 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Rizinusöl besteht. Durch Ausgießen und feines Verteilen der Lösung inI. 20 parts by weight of an active compound of formula I are dissolved in a mixture of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide with 1 mole of oleic N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of Addition product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in
100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs der Formel I enthält.100,000 parts by weight of water to obtain an aqueous dispersion containing 0.02 wt .-% of the active ingredient of the formula I.
II. 20 Gewichtsteile eines Wirkstoffs der Formel I werden in einer Mischung gelöst, die aus 40 Gewichtsteilen Cyclohexanon, 30 Gewichtsteilen Isobutanol, 20 Gewichtsteilen des Anlagerungsproduktes von 7 Mol Ethylenoxid an 1 Mol Isooc- tylphenol und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Rizinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs der Formel I enthält.II. 20 parts by weight of an active compound of the formula I are dissolved in a mixture of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 mole of isoac-tylphenol and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 Mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water to obtain an aqueous dispersion containing 0.02 wt .-% of the active ingredient of the formula I.
IM. 20 Gewichtsteile eines Wirkstoffs der Formel I werden in einer Mischung gelöst, die aus 25 Gewichtsteilen Cyclohexanon, 65 Gewichtsteilen einer Mineralölfraktion vom Siedepunkt 210 bis 28O0C und 10 Gewichtsteilen des Anlagerungs- Produktes 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 der Formel I enthält. IV. 20 Gewichtsteile eines Wirkstoffs der Formel I werden mit 3 Gewichtsteilen des Natriumsalzes der Diisobutylnaphthalinsulfonsäure, 17 Gewichtsteilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 60 Gewichtsteilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermählen. Durch feines Verteilen der Mischung in 20000 Gewichtsteilen Wasser erhält man eine Spritzbrühe, die 0,1 Gew.-% des Wirkstoffs der Formel I enthält.IN THE. 20 parts by weight of an active compound of the formula I are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 28O 0 C and 10 parts by weight of the addition product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water to obtain an aqueous dispersion containing 0.02 wt .-% of the active ingredient of the formula I. IV. 20 parts by weight of an active compound of the formula I are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalenesulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water to obtain a spray mixture containing 0.1 wt .-% of the active ingredient of the formula I.
V. 3 Gewichtsteile eines Wirkstoffs der Formel I werden mit 97 Gewichtsteilen fein- teiligem Kaolin vermischt. Man erhält auf diese Weise ein Stäubemittel, das 3 Gew.-% des Wirkstoffs der Formel I enthält.V. 3 parts by weight of an active compound of the formula I are mixed with 97 parts by weight of finely divided kaolin. Obtained in this way a dust containing 3 wt .-% of the active ingredient of the formula I.
VI. 20 Gewichtsteile eines Wirkstoffs der Formel I werden mit 2 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure, 8 Gewichtsteilen Fettalkoholpoly- glykolether, 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 an active compound of the formula I are intimately mixed with 2 parts by weight of calcium 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. This gives a stable oily dispersion.
VII. 1 Gewichtsteil eines Wirkstoffs der Formel I wird in einer Mischung gelöst, die aus 70 Gewichtsteilen Cyclohexanon, 20 Gewichtsteilen ethoxyliertem Isooc- tylphenol und 10 Gewichtsteilen ethoxyliertem Rizinusöl besteht. Man erhält ein stabiles Emulsionskonzentrat.VII. 1 part by weight of an active compound of the formula I is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isoacylphenol and 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.
VIII. 1 Gewichtsteil eines Wirkstoffs der Formel I wird in einer Mischung gelöst, die aus 80 Gewichtsteilen Cyclohexanon und 20 Gewichtsteilen WettolR EM 31 (= nichtionischer Emulgator auf der Basis von ethoxyliertem Rizinusöl) besteht. Man erhält ein stabiles Emulsionskonzentrat.VIII. 1 part by weight of an active compound of the formula I is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol R EM 31 (= nonionic emulsifier based on ethoxylated castor oil). A stable emulsion concentrate is obtained.
Die Applikation der Verbindungen der Formel 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, wäh- rend die Wirkstoffe auf die Blätter darunter wachsender unerwünschter Pflanzen oder die unbedeckte Bodenfläche gelangen (post-directed, lay-by).The application of the compounds of the formula I or of the herbicidal compositions can be carried out in the preemergence or postemergence process. If the active ingredients are less compatible with certain crops, application techniques may be used in which the herbicidal agents are sprayed with the help of the sprayers so as not to hit the leaves of the sensitive crops as far as possible, while the active ingredients on the leaves below grow undesirable plants or the uncovered soil surface (post-directed, lay-by).
Die Aufwandmengen an Verbindung der Formel 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.). Zur Verbreiterung des Wirkungsspektrums und zur Erzielung synergistischer Effekte können die heteroaroylsubstituierten Alanine der Formel I mit zahlreichen Vertretern anderer herbizider oder wachstumsregulierender Wirkstoffgruppen gemischt und gemeinsam ausgebracht werden. Beispielsweise kommen als Mischungspartner 1 ,2,4- Thiadiazole, 1 ,3,4-Thiadiazole, Amide, Aminophosphorsäure und deren Derivate, Ami- notriazole, Anilide, Aryloxy-/Heteroaryloxyalkansäuren und deren Derivate, Benzoesäure und deren Derivate, Benzothiadiazinone, 2-(Hetaroyl/Aroyl)-1 ,3- cyclohexandione, Heteroaryl-Aryl-Ketone, Benzylisoxazolidinone, meta-CF3-Phenylderivate, Carbamate, Chinolincarbonsäure und deren Derivate, Chloracetanilide, Cyclohexenonoximetherde- rivate, Diazine, Dichlorpropionsäure und deren Derivate, Dihydrobenzofurane, Dihydro- furan-3-one, Dinitroaniline, Dinitrophenole, Diphenylether, Dipyridyle, Halogencarbonsäuren und deren Derivate, Harnstoffe, 3-Phenyluracile, Imidazole, Imidazolinone, N- Phenyl-3,4,5,6-tetrahydrophthalimide, Oxadiazole, Oxirane, Phenole, Aryloxy- und He- teroaryloxyphenoxypropionsäureester, Phenylessigsäure und deren Derivate, 2- Phenylpropionsäure und deren Derivate, Pyrazole, Phenylpyrazole, Pyridazine, Pyri- dincarbonsäure und deren Derivate, Pyrimidylether, Sulfonamide, Sulfonylharnstoffe, Triazine, Triazinone, Triazolinone, Triazolcarboxamide und Uracile in Betracht.Depending on the control target, season, target plants and growth stage, the application rates of compound of the formula I are 0.001 to 3.0, preferably 0.01 to 1.0, kg / ha of active substance (see above). To broaden the spectrum of action and to achieve synergistic effects, the heteroaroyl-substituted alanines of the formula I can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups and applied together. For example, 1, 2,4-thiadiazoles, 1, 3,4-thiadiazoles, amides, aminophosphoric acid and derivatives thereof, aminotriazoles, anilides, aryloxy / heteroaryloxyalkanoic acids and their derivatives, benzoic acid and derivatives thereof, benzothiadiazinones, (Hetaroyl / aroyl) -1, 3-cyclohexanediones, heteroaryl-aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and derivatives thereof, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydroxy furan-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 heteroaryloxyphenoxypropionic acid esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and derivatives thereof, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and their derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, Triazolcarboxamide and uracils into consideration.
Außerdem kann es von Nutzen sein, die Verbindungen der Formel 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.In addition, it may be useful to use the compounds of the formula I alone or in combination with other herbicides mixed with other pesticides, apply together, 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 for the elimination of nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.
Anwendungsbeispieleapplications
Die herbizide Wirkung der heteroaroylsubstituierten Alanine der Formel I ließ sich durch die folgenden Gewächshausversuche zeigen:The herbicidal action of the heteroaroyl-substituted alanines of the formula I was demonstrated by the following greenhouse experiments:
Als Kulturgefäße dienten Plastikblumentöpfe mit lehmigem Sand mit etwa 3,0 % Hu- mus als Substrat. Die Samen der Testpflanzen wurden nach Arten getrennt eingesät.The culture vessels used were plastic flower pots with loamy sand with about 3.0% humus as the substrate. The seeds of the test plants were sown separately by species.
Bei Vorauflaufbehandlung wurden die in Wasser suspendierten oder emulgierten Wirkstoffe direkt nach Einsaat mittels fein verteilender Düsen aufgebracht. Die Gefäße wurden leicht beregnet, um Keimung und Wachstum zu fördern, und anschließend mit durchsichtigen Plastikhauben abgedeckt, bis die Pflanzen angewachsen waren. Diese Abdeckung bewirkt ein gleichmäßiges Keimen der Testpflanzen, sofern dies nicht durch die Wirkstoffe beeinträchtigt wurde. 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 oder 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. Die Aufwandmenge für die Nachauflaufbehandlung betrug 1 ,0 kg/ha a.S. (aktive Substanz).In pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing by means of finely distributing nozzles. The jars were lightly rained to promote germination and growth and then covered with clear plastic hoods until the plants had grown. This cover causes a uniform germination of the test plants, if it was not affected by the active ingredients. For the purpose of postemergence treatment, the test plants were grown depending on the growth form only to a stature height of 3 to 15 cm and only then treated with the suspended or emulsified in water agents. 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. The application rate for postemergence treatment was 1.0 kg / ha aS (active substance).
Die Pflanzen wurden artenspezifisch bei Temperaturen von 10 bis 250C bzw. 20 bis 350C gehalten. Die Versuchsperiode erstreckte sich über 2 bis 4 Wochen. Während dieser Zeit wurden die Pflanzen gepflegt, und ihre Reaktion auf die einzelnen Behandlungen wurde ausgewertet.The plants were kept species-specific at temperatures of 10 to 25 0 C and 20 to 35 0 C. The trial period lasted for 2 to 4 weeks. During this time, the plants were cared for, 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.The rating was based on a scale of 0 to 100. 100 means no emergence of the plants or complete destruction of at least the above-ground parts and 0 no damage or normal growth course.
Die in den Gewächshausversuchen verwendeten Pflanzen setzten sich aus folgenden Arten zusammen:The plants used in the greenhouse experiments were composed of the following species:
Bei Aufwandmengen von 1 ,0 kg/ha zeigten die Verbindungen 3.4, 3.5, 3.9, 3.10, 3.12, 3.13 und 3.15 (Tabelle 3) im Nachauflauf eine sehr gute Wirkung gegen die unerwünschten Pflanzen Krummer Fuchsschwanz, Weißer Gänsefuß und Grüne Borsten- hirse. At application rates of 1.0 kg / ha, the compounds 3.4, 3.5, 3.9, 3.10, 3.12, 3.13 and 3.15 (Table 3) in postemergence showed a very good action against the unwanted plants Krummer Foxtail, White Goosefoot and Green Bristlecot.

Claims

Patentansprüche: claims:
1. Heteroaroylsubstituierte Alanine der Formel I1. heteroaroyl-substituted alanines of the formula I.
in der die Variablen die folgenden Bedeutungen haben:in which the variables have the following meanings:
A 5- oder 6-gliedriges Heteroaryl mit ein bis vier Stickstoffatomen, oder mit ein bis drei Stickstoffatomen und einem Sauerstoff- oder Schwefelatom, oder mit einem Sauerstoff- oder Schwefelatom, welches partiell oder vollständig halogeniert sein kann und/oder 1 bis 3 Reste aus der Gruppe Cyano, CrC6- Alkyl, C3-C6-CyClOaIkVl, Ci-C6-Halogenalkyl, Ci-C6-Alkoxy, CrC6- Halogenalkoxy und Ci-C6-Alkoxy-Ci-C4-alkyl tragen kann;A 5- or 6-membered heteroaryl having one to four nitrogen atoms, or having one to three nitrogen atoms and one oxygen or sulfur atom, or having one oxygen or sulfur atom which may be partially or completely halogenated and / or 1 to 3 radicals the group consisting of cyano, CrC 6 - alkyl, C 3 -C 6 -CyClOaIkVl, Ci-C 6 haloalkyl, Ci-C 6 alkoxy, -C 6 - haloalkoxy and Ci-C can carry 6 alkoxy-Ci-C4-alkyl ;
R1, R2 Wasserstoff, Hydroxy oder Ci-C6-Alkoxy;R 1 , R 2 are hydrogen, hydroxy or C 1 -C 6 -alkoxy;
R3 Ci-C6-Alkyl, Ci-C4-Cyanoalkyl oder Ci-C6-Halogenalkyl;R 3 Ci-C 6 alkyl, Ci-C4-cyanoalkyl or Ci-C 6 haloalkyl;
R4 Wasserstoff oder Ci -C6-Al kyl;R 4 is hydrogen or C 1 -C 6 -alkyl;
R5 Wasserstoff, d-Cβ-Alkyl, C2-C6-Alkenyl, C2-C6-Al kinyl, Ci-C6-Halogenalkyl, C2-C6-Halogenalkenyl, C2-C6-Halogenalkinyl, Ci-C6-Cyanoalkyl, C2-C6- Cyanoalkenyl, C2-C6-Cyanoalkinyl, Ci-C6-Hydroxyalkyl, C2-C6- Hydroxyalkenyl, C2-C6-Hydroxyalkinyl, C3-C6-Cycloalkyl, C3-C6- Cycloalkenyl, 3- bis 6-gliedriges Heterocyclyl, wobei die voranstehen genannten Cycloalkyl, Cycloalkenyl oder 3- bis 6- gliedrigen Heterocyclyl reste partiell oder vollständig halogeniert sein können und/oder ein bis drei Reste aus der Gruppe Oxo, Cyano, Nitro, Ci-Ce-Alkyl, Ci-C6-Halogenalkyl, Hydroxy, Ci-C6-Alkoxy, CrC6- Halogenalkoxy, Hydroxycarbonyl, CrC6-Alkoxycarbonyl, Hydroxycarbo- nyl-CrC6-alkoxy, Ci-C6-Alkoxycarbonyl-CrC6-alkoxy, Amino, CrC6- Alkylamino, Di(CrC6-alkyl)amino, CrC6-Alkylsulfonylamino, CrC6- Halogenalkylsulfonylamino, Aminocarbonylamino, (CrC6-Alkylamino)- carbonylamino, Di(CrC6-alkyl)aminocarbonylamino, Aryl und Aryl(CrC6- alkyl) tragen können; Ci-C6-Alkoxy-Ci-C4-alkyl, C2-C6-Alkenyloxy-Ci-C4-alkyl, C2-C6-Alkinyloxy- Ci-C4-alkyl, Ci-C6-Halogenalkoxy-Ci-C4-alkyl, C2-C6-Halogenalkenyloxy-d- C4-alkyl, C2-C6-Halogenalkinyloxy-Ci-C4-alkyl, Ci-C6-Alkoxy-Ci-C4-alkoxy- Ci-C4-alkyl, Ci-C6-Alkylthio-Ci-C4-alkyl, C2-C6-Alkenylthio-Ci-C4-alkyl, C2- C6-Alkinylthio-Ci-C4-alkyl, CrCe-Halogenalkyl-CrGrthioalkyl, C2-C6-R 5 is hydrogen, d-Cβ-alkyl, C 2 -C 6 alkenyl, C 2 -C 6 kinyl -alkyl, Ci-C 6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, Ci- C 6 cyanoalkyl, C 2 -C 6 - cyanoalkenyl, C2-C6 -Cyanoalkinyl, Ci-C 6 hydroxyalkyl, C 2 -C 6 - hydroxyalkenyl, C 2 -C 6 -Hydroxyalkinyl, C3-C 6 cycloalkyl, C 3 -C 6 -cycloalkenyl, 3- to 6-membered heterocyclyl, where the abovementioned cycloalkyl, cycloalkenyl or 3- to 6-membered heterocyclyl radicals may be partially or completely halogenated and / or one to three radicals from the group consisting of oxo, cyano, nitro, Ci-Ce-alkyl, Ci-C 6 haloalkyl, hydroxy, Ci-C 6 alkoxy, -C 6 - haloalkoxy, hydroxycarbonyl, CrC 6 -alkoxycarbonyl, hydroxycarbonyl--C 6 alkoxy, C 6 -alkoxycarbonyl-CrC 6 alkoxy, amino, -C 6 - alkylamino, di (-C 6 alkyl) amino, -C 6 alkylsulfonylamino, CrC 6 - haloalkylsulfonylamino, aminocarbonylamino, (CrC 6 alkylamino) - carbonylamino, di (CrC 6 alkyl) aminocarbonylamino, aryl and aryl (CrC 6 -alky l) can carry; Ci-C 6 alkoxy-Ci-C 4 alkyl, C 2 -C 6 alkenyloxy-Ci-C4-alkyl, C 2 -C 6 alkynyloxy Ci-C4-alkyl, Ci-C6-haloalkoxy-Ci C 4 -alkyl, C 2 -C 6 -haloalkenyloxy-C 1 -C 4 -alkyl, C 2 -C 6 -haloalkynyloxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl -C 6 alkylthio-Ci-C 4 alkyl, C 2 -C 6 alkenylthio-Ci-C 4 alkyl, C 2 - C 6 alkynylthio-Ci-C4 alkyl, haloalkyl CRCE CrGrthioalkyl, C 2 -C 6 -
Halogenalkenyl-Ci-C4-thioalkyl, C2-C6-Halogenalkinyl-Ci-C4-thioalkyl, Ci-Cβ- Alkylsulfinyl-Ci-C4-alkyl, Ci-Ce-Halogenalkylsulfinyl-Ci-CU-alkyl, CrC6- Alkylsulfonyl-Ci-C4-alkyl, Ci-C6-Halogenalkylsulfonyl-CrC4-alkyl, Amino-Cr C4-alkyl, Ci-C6-Alkylamino-Ci-C4-alkyl, Di(Ci-C6-alkyl)amino-Ci-C4-alkyl, Cr Ce-Alkylsulfonylamino-CrGralkyl, Ci-C6-Alkylsulfonyl(Ci-C6-alkyl)amino-CrHaloalkenyl-Ci-C4-thioalkyl, C2-C6-haloalkynyl-Ci-C4-thioalkyl, Ci-Cβ- alkylsulfinyl-Ci-C4-alkyl, Ci-Ce-haloalkylsulfinyl-Ci-CU-alkyl, -C 6 - alkylsulphonyl -C 1 -C 4 -alkyl, C 1 -C 6 -haloalkylsulphonyl-C 1 -C 4 -alkyl, amino-C 1 -C 4 -alkyl, C 1 -C 6 -alkylamino-C 1 -C 4 -alkyl, di (C 1 -C 6 -alkyl) -amino C 1 -C 4 -alkyl, C 1 -C -alkylsulfonylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonyl (C 1 -C 6 -alkyl) -amino-Cr
C4-alkyl, CrCδ-Alkylcarbonyl, Hydroxycarbonyl, Ci-Cδ-Alkoxycarbonyl, Ami- nocarbonyl, CrCe-Alkylaminocarbonyl, Di(Ci-C6-alkyl)aminocarbonyl, For- mylamino-Ci-C4-alkyl, Ci-C6-Alkoxycarbonylamino-Ci-C4-alkyl, Ci-Cβ- Alkylcarbonyl-Ci-Cδ-alkyl, Hydroxycarbonyl-Ci-C4-alkyl, Ci-Cβ- Alkoxycarbonyl-Ci-C4-alkyl, Ci-C6-Halogenalkoxycarbonyl-Ci-C4-alkyl, d-C 4 -alkyl, C 1 -C 6 -alkylcarbonyl, hydroxycarbonyl, C 1 -C 6 -alkoxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, di (C 1 -C 6 -alkyl ) aminocarbonyl, formylamino-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonylamino -C 1 -C 4 -alkyl, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkyl, hydroxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 6 -halogenalkoxycarbonyl-C 1 -C 4 -alkyl ,
C6-Alkylcarbonyloxy-Ci-C4-alkyl, Aminocarbonyl-Ci-C4-alkyl, CrCβ- Alkylaminocarbonyl-CrC4-alkyl, Di(Ci-C6-alkyl)aminocarbonyl-CrC4-alkyl, Ci-C6-Alkylcarbonylamino-CrC4-alkyl, Ci-C6-Alkylcarbonyl-(Ci-C6- alkylamino)-CrC4-alkyl, (Ci-C6-Alkyl)aminocarbonyloxy-CrC4-alkyl, Di(Cr C6-alkyl)aminocarbonyloxy-CrC4-alkyl, [(Ci-C6-Alkyl)amino- carbonylamino]CrC4-alkyl, [Di(Ci-C6-alkyl)amino-carbonylamino]CrC4- alkyl;C 6 -alkylcarbonyloxy-C 1 -C 4 -alkyl, aminocarbonyl-C 1 -C 4 -alkyl, C 1 -C 6 -alkylaminocarbonyl-C 1 -C 4 -alkyl, di (C 1 -C 6 -alkyl) aminocarbonyl-C 1 -C 4 -alkyl, C 1 -C 6 -alkylcarbonylaminoCrC 4 alkyl, C 1 -C 6 -alkylcarbonyl- (C 1 -C 6 -alkylamino) C 1 -C 4 -alkyl, (C 1 -C 6 -alkyl) aminocarbonyloxyCrC 4 -alkyl, di (C 1 -C 6 -alkyl) aminocarbonyloxyCrC 4 -alkyl, [(C 1 -C 6 -alkyl) amino-carbonylamino] C 1 -C 4 -alkyl, [di (C 1 -C 6 -alkyl) amino-carbonylamino] C 1 -C 4 -alkyl;
Phenyl-CrC4-alkyl, Phenyl-C2-C4-alkenyl, Phenyl-C2-C4-alkinyl, Phenyl-d-Phenyl-CrC 4 -alkyl, phenyl-C 2 -C 4 -alkenyl, phenyl-C 2 -C 4 -alkynyl, phenyl-d-
C4-halogenalkyl, Phenyl-C2-C4-halogenalkenyl, Phenyl-C2-C4- halogenalkinyl, Phenyl-CrC4-hydroxyalkyl, Phenyl-C2-C4-hydroxyalkenyl,C4-haloalkyl, phenyl-C 2 -C 4 haloalkenyl, phenyl-C2 -C4- haloalkynyl, phenyl-CRC4-hydroxyalkyl, phenyl-C2-C4-hydroxyalkenyl,
Phenyl-C2-C4-hydroxyalkinyl, Phenylcarbonyl-CrC4-alkyl, Phenylcarbonylo- xy-CrC4-alkyl, Phenyloxycarbonyl-CrC4-alkyl, Phenyloxy-CrC4-alkyl, Phe- nylthio-CrC4-alkyl, Phenylsulfinyl-CrC4-alkyl, Phenylsulfonyl-CrC4-alkyl, Heteroaryl, Heteroaryl-CrC4-alkyl, Heteroaryl-C2-C4-alkenyl, Heteroaryl-C2- C4-alkinyl, Heteroaryl-CrC4-halogenalkyl, Heteroaryl-C2-C4-halogenalkenyl,Phenyl-C 2 -C 4 -hydroxyalkynyl, phenylcarbonyl-C 1 -C 4 -alkyl, phenylcarbonyloxy-C 1 -C 4 -alkyl, phenyloxycarbonyl-C 1 -C 4 -alkyl, phenyloxyCrC 4 -alkyl, phenylthio-C 1 -C 4 -alkyl, phenylsulfinyl-C 1 -C 4 -alkyl , phenylsulfonyl -C 4 alkyl, heteroaryl, heteroaryl-CRC4-alkyl, heteroaryl-C 2 -C 4 alkenyl, heteroaryl-C 2 - C 4 alkynyl, heteroaryl-CRC4 haloalkyl, heteroaryl-C 2 -C 4 haloalkenyl,
Heteroaryl-C2-C4-halogenalkinyl, Heteroaryl-CrC4-hydroxyalkyl, Heteroaryl- C2-C4-hydroxyalkenyl, Heteroaryl-C2-C4-hydroxyalkinyl, Heteroarylcarbonyl- CrC4-alkyl, Heteroarylcarbonyloxy-Ci^-alkyl, Heteroaryloxycarbonyl-Cr C4-alkyl, Heteroaryloxy-CrC4-alkyl, Heteroarylthio-CrC4-alkyl, Heteroaryl- sulfinyl-CrC4-alkyl, Heteroarylsulfonyl-CrC4-alkyl, wobei die vorstehend genannten Phenyl- und Heteroarylreste partiell oder vollständig halogeniert sein können und/oder ein bis drei Reste aus der Gruppe Cyano, Nitro, CrCβ-Alkyl, CrCδ-Halogenalkyl, Hy- droxy, CrCβ-Hydroxyalkyl, CrCδ-Alkoxy, CrCδ-Halogenalkoxy, Hydroxycarbonyl, CrCδ-Alkoxycarbonyl, Hydroxycarbonyl-Ci-Cδ- alkoxy, Ci-C6-Alkoxycarbonyl-CrC6-alkoxy, Amino, CrC6-Alkylamino, Di(CrC6-alkyl)amino, CrC6-Alkylsulfonylamino, CrCδ-Halogenalkyl- sulfonylamino, (CrC6-Alkylamino)carbonylamino, Di-(CrC6-alkyl)- aminocarbonylamino, Aryl und Aryl(Ci-C6-alkyl) tragen können;Heteroaryl-C 2 -C 4 haloalkynyl, heteroaryl-CRC4-hydroxyalkyl, heteroaryl- C2-C4-hydroxyalkenyl, heteroaryl-C2-C4-hydroxyalkynyl, heteroarylcarbonyl -C 4 alkyl, heteroarylcarbonyloxy-Ci ^ alkyl, heteroaryloxy-Cr C 4 alkyl, heteroaryloxy-CRC4-alkyl, heteroarylthio--C 4 -alkyl, heteroaryl-sulfinyl -C 4 alkyl, heteroarylsulfonyl-CRC4-alkyl, wherein the foregoing phenyl and heteroaryl radicals may be partially or fully halogenated and / or one to three radicals from the group cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, hydroxyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, hydroxycarbonyl, C 1 -C 6 -alkoxycarbonyl, hydroxycarbonyl-C 1 -C 6 -alkoxy, C 1 -C 4 -alkyl -C 6 -alkoxycarbonyl-C 1 -C 6 -alkoxy, amino, C 1 -C 6 -alkylamino, di (C 1 -C 6 -alkyl) amino, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -haloalkyl sulfonylamino, (C 1 -C 6 -alkylamino) carbonylamino, di- (C 1 -C 6 -alkyl) -aminocarbonylamino, aryl and aryl (C 1 -C 6 -alkyl);
R6 Wasserstoff, Ci -C6-Al kyl, C3-C6-Cycloalkyl, C3-C6-Alkenyl, C3-C6-Al kinyl,R 6 is hydrogen, C -C alkyl 6 -alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 kinyl Al,
C3-C6-Halogenalkenyl, C3-C6-Halogenalkinyl, Formyl, Ci-C6-Alkylcarbonyl, C3-C6-Cycloalkylcarbonyl, C2-C6-Alkenylcarbonyl, Ca-Cε-Alkinylcarbonyl, Cr C6-Alkoxycarbonyl, C3-C6-Alkenyloxycarbonyl, C3-C6-Alkinyloxycarbonyl, Aminocarbonyl, Ci-Ce-Alkylaminocarbonyl, Cs-Ce-Alkenylaminocarbonyl, Cs-Cδ-Alkinylaminocarbonyl, Ci-Ce-Alkylsulfonylaminocarbonyl, Di(CrC6- alkyl)aminocarbonyl, N-(C3-C6-Alkenyl)-N-(CrC6-alkyl)-aminocarbonyl, N- (C3-C6-Alkinyl)-N-(Ci-C6-alkyl)-aminocarbonyl, N-(Ci-C6-Alkoxy)-N-(Ci-C6- alkyl)-amino-carbonyl, N-(C3-C6-Alkenyl)-N-(CrC6-alkoxy)-aminocarbonyl, N-(C3-C6-Alkinyl)-N-(Ci-C6-alkoxy)-aminocarbonyl, Di(Ci-C6-alkyl)amino- thiocarbonyl, (CrCe-AlkylJcyanoimino, (Amino)cyanoimino, [(CrC6-C 3 -C 6 haloalkenyl, C 3 -C 6 haloalkynyl, formyl, Ci-C 6 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C2-C6 alkenylcarbonyl, Ca-Cε-alkynylcarbonyl, Cr C 6 - Alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 alkynyloxycarbonyl, aminocarbonyl, Ci-Ce-alkylaminocarbonyl, Cs-Ce-alkenylaminocarbonyl, Cs-Cδ-alkynylaminocarbonyl, Ci-Ce-alkylsulfonylaminocarbonyl, di (CrC 6 - alkyl aminocarbonyl), N- (C 3 -C 6 -alkenyl) -N- (-C 6 alkyl) aminocarbonyl, N- (C 3 -C 6 alkynyl) -N- (Ci-C 6 alkyl) aminocarbonyl , N- (Ci-C 6 alkoxy) -N- (Ci-C 6 - alkyl) -amino-carbonyl, N- (C 3 -C 6 -alkenyl) -N- (-C 6 -alkoxy) aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (C 1 -C 6 -alkoxy) -aminocarbonyl, di (C 1 -C 6 -alkyl) amino-thiocarbonyl, (C 1 -C 6 -alkyl-cyanoimino, (amino) cyanoimino, [(CrC 6 -
Alkyl)amino]cyanoimino, Di(Ci-C6-alkyl)aminocyanoimino, CrC6- Alkylcarbonyl-Ci-C6-alkyl, Ci-C6-Alkoxyimino-Ci-C6-alkyl, N-(CrC6- Alkylamino)-imino-Ci-C6-alkyl, N-[Di(Ci-C6-alkyl)amino]imino-Ci-C6-alkyl oder Tri-Ci-C4-alkylsilyl, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Hydroxy, C3-C6-Cycloalkyl, Cr C6-Alkoxy-Ci-C4-alkyl, C 1 -C4-Alkoxy-Ci-C4-alkoxy-Ci-C4-a I kyl, CrC4- Alkoxy, CrC4-Alkylthio, Di(CrC4-alkyl)amino, Ci-C4-Alkyl-CrC6- alkoxycarbonylamino, CrC4-Alkylcarbonyl, Hydroxycarbonyl, CrC4-Alkyl) amino] cyanoimino, di (Ci-C 6 alkyl) aminocyanoimino, -C 6 - alkylcarbonyl-Ci-C 6 alkyl, Ci-C 6 alkoxyimino-Ci-C 6 alkyl, N- (CrC 6 - alkylamino ) -imino-C 1 -C 6 -alkyl, N- [di (C 1 -C 6 -alkyl) amino] imino-C 1 -C 6 -alkyl or tri-C 1 -C 4 -alkylsilyl, where the alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and / or may carry one to three of the following groups: cyano, hydroxyl, C3-C6 cycloalkyl, Cr C 6 alkoxy-Ci-C 4 alkyl, C 1 -C 4 alkoxy -C-C4-alkoxy-Ci-C4-a I kyl, -C 4 - alkoxy, -C 4 alkylthio, di (CRC-4 alkyl) amino, Ci-C 4 -alkyl-CrC 6 - alkoxycarbonylamino, -C 4 -alkylcarbonyl , Hydroxycarbonyl, CrC 4 -
Alkoxycarbonyl, Aminocarbonyl, CrC4-Alkylaminocarbonyl, Di(CrC4- alkyl)aminocarbonyl oder CrC4-Alkylcarbonyloxy;Alkoxycarbonyl, aminocarbonyl, CRC4 alkylaminocarbonyl, di (CrC 4 - alkyl) aminocarbonyl or -C 4 alkylcarbonyloxy;
Phenyl, Phenyl-CrC6-alkyl, Phenylcarbonyl-Ci-Cδ-alkyl, Phenoxycarbonyl, Phenylaminocarbonyl, Phenylsulfonylaminocarbonyl, N-(CrC6-Alkyl)-N- (phenyl)aminocarbonyl, Phenyl-Ci-Cδ-alkylcarbonyl, wobei der Phenylrest partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann: Nitro, Cyano, CrC4-Alkyl, CrC4-Halogenalkyl, CrC4-Alkoxy oder CrC4- Halogenalkoxy; oder SO2R8;Phenyl, phenyl-C 1 -C 6 -alkyl, phenylcarbonyl-C 1 -C 6 -alkyl, phenoxycarbonyl, phenylaminocarbonyl, phenylsulfonylaminocarbonyl, N- (C 1 -C 6 -alkyl) -N- (phenyl) aminocarbonyl, phenyl-C 1 -C 6 -alkylcarbonyl, where the phenyl radical may be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, -C 4 alkyl, -C 4 haloalkyl, -C 4 alkoxy or -C 4 - haloalkoxy; or SO 2 R 8 ;
R7 Wasserstoff, CrC6-Alkyl, C3-C6-Cycloalkyl, C3-C6-Alkenyl, C3-C6-Al kinyl, C3- C6-Halogenalkenyl, C3-C6-Halogenalkinyl, Hydroxy oder CrC6-Alkoxy;R 7 is hydrogen, -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 kinyl -alkyl, C 3 - C 6 haloalkenyl, C 3 -C 6 haloalkynyl, Hydroxy or C 1 -C 6 alkoxy;
R8 CrC6-Alkyl, CrC6-Halogenalkyl oder Phenyl, wobei der Phenylrest partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann: CrC6- Alkyl, Ci-Cδ-Halogenalkyl oder Ci-C6-Alkoxy;R 8 -C 6 alkyl, -C 6 -haloalkyl or phenyl, where the phenyl radical can be partially or fully halogenated and / or may carry one to three of the following groups: -C 6 - alkyl, Ci-Cδ-haloalkyl or Ci-C 6 alkoxy;
sowie deren landwirtschaftlich brauchbaren Salze.and their agriculturally useful salts.
2. Heteroaroylsubstituierte Alanine der Formel I gemäß Anspruch 1 wobei A für 5- oder 6-gliedriges Heteroaryl ausgewählt aus der Gruppe Pyrrolyl, Thienyl, Furyl, Pyrazolyl, Imidazolyl, Thiazolyl, Oxazolyl, Tetrazolyl, Pyridyl und Pyrimidinyl; wo- bei die genannten Heteroarylreste partiell oder vollständig halogeniert sein können und/oder 1 bis 3 Reste aus der Gruppe Cyano, Ci-C6-Alkyl, C3-C6-CyClOaIkVl, Ci-C6-Halogenalkyl, Ci-C6-Alkoxy, Ci-C6-Halogenalkoxy und Ci-C6-Alkoxy-Ci-C4-alkyl tragen können, steht.2. Heteroaroylsubstituierte alanines of the formula I according to claim 1 wherein A is 5- or 6-membered heteroaryl selected from the group pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, tetrazolyl, pyridyl and pyrimidinyl; WO may be halogenated, partially or fully in the above-mentioned heteroaryl groups and / or 1 to 3 radicals from the group cyano, Ci-C 6 alkyl, C 3 -C 6 -CyClOaIkVl, Ci-C 6 haloalkyl, Ci-C 6 Alkoxy, Ci-C 6 -haloalkoxy and Ci-C6-alkoxy-Ci-C4-alkyl, is.
3. Heteroaroylsubstituierte Alanine der Formel I gemäß Anspruch 1 oder 2, wobei R1, R2, R4 und R7 für Wasserstoff stehen.3. heteroaroyl-substituted alanines of the formula I according to claim 1 or 2, wherein R 1 , R 2 , R 4 and R 7 are hydrogen.
4. Heteroaroylsubstituierte Alanine der Formel I gemäß einem der Ansprüche 1 bis 3, wobei R5 für Ci -C6-Al kyl, C2-C6-Alkenyl, C2-C6-Al kinyl, d-Ce-Halogenalkyl, C2-4. Heteroaroylsubstituierte alanines of the formula I as claimed in one of claims 1 to 3, wherein R 5 is C -C alkyl 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 kinyl -alkyl, d-Ce-haloalkyl, C 2 -
Ce-Halogenalkenyl, C2-C6-Halogenalkinyl, Ci-C6-Cyanoalkyl, Ci-C6-Hydroxyalkyl, C2-C6-Hydroxyalkenyl, C2-C6-Hydroxyalkinyl, C3-C6-Cycloalkyl, C3-C6- Cycloalkenyl, 3- bis 6-gliedriges Heterocyclyl, wobei die voranstehen genannten Cycloalkyl, Cycloalkenyl oder 3- bis 6- gliedrigen Heterocyclyl reste partiell oder vollständig halogeniert sein können und/oder einen bis drei Rest aus der Gruppe Oxo, Ci-C6-Alkyl, CrC6- Halogenalkyl, Hydroxycarbonyl und Ci-C6-Alkoxycarbonyl tragen können, Ci-C6-Alkoxy-Ci-C4-alkyl, Ci-C6-Halogenalkoxy-Ci-C4-alkyl, C 1 -C6-AIkOXy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C6-Alkylthio-Ci-C4-alkyl, Ci-C6-Alkylsulfonylamino-Ci-C4- alkyl, Hydroxycarbonyl, Ci-C6-Alkoxycarbonyl, Hydroxycarbonyl-Ci-C4-alkyl, d-Ce-haloalkenyl, C 2 -C 6 haloalkynyl, C 6 cyanoalkyl, Ci-C 6 hydroxyalkyl, C 2 -C 6 -Hydroxyalkenyl, C 2 -C 6 -Hydroxyalkinyl, C3-C 6 cycloalkyl, C C 3 -C 6 -cycloalkenyl, 3- to 6-membered heterocyclyl, where the above-mentioned cycloalkyl, cycloalkenyl or 3- to 6-membered heterocyclyl radicals may be partially or completely halogenated and / or one to three radicals from the group of oxo, Ci can carry 6 alkoxycarbonyl haloalkyl, hydroxycarbonyl and C-C, C-C 6 alkoxy-Ci-C4-alkyl, Ci-C 6 haloalkoxy-Ci-C4 alkyl, - C6 alkyl, CrC 6 C 1 -C 6 -alkoxy-Ci-C 4 - alkoxy-Ci-C4-alkyl, Ci-C6 alkylthio-Ci-C4-alkyl, Ci-C 6 alkylsulfonylamino-Ci-C 4 - alkyl, Hydroxycarbonyl, C 1 -C 6 -alkoxycarbonyl, hydroxycarbonyl-C 1 -C 4 -alkyl, d-
C6-Alkoxycarbonyl-Ci-C4-alkyl, Ci-C6-Halogenalkoxycarbonyl-Ci-C4-alkyl, CrC6- Alkylcarbonyloxy-Ci-C4-alkyl, Ci-Cδ-Alkylcarbonylamino-Ci^-alkyl, Di(CrC6- Alkyl)carbonylamino-Ci-C4-alkyl, [Di(Ci-C6-alkylamino)carbonyloxy]Ci-C4-alkyl, {Di[di(Ci-C6-alkyl)amino]carbonyloxy}Ci-C4-alkyl, Phenyl-Ci-C4-alkyl, Phenyl-C2-C4-alkenyl, Phenyl-C2-C4-alkinyl, Phenyl-Ci-C4- halogenalkyl, Phenyl-C2-C4-halogenalkenyl, Phenyl-Ci-C4-hydroxyalkyl, Pheny- loxy-Ci-C4-alkyl, Phenylthio-Ci-C4-alkyl, Phenylsulfinyl-Ci-C4-alkyl, Phenylsulfo- nyl-Ci-C4-alkyl, Heteroaryl, Heteroaryl-Ci-C4-alkyl, Heteroaryl-Ci-C4-hydroxyalkyl, Heteroaryloxy- Ci-C4-alkyl, Heteroarylthio-Ci-C4-alkyl, Heteroarylsulfinyl-Ci-C4-alkyl, Heteroaryl- sulfonyl-Ci-C4-alkyl, wobei die vorstehend genannten Phenyl- und Heteroarylreste oder vollständig halogeniert sein können und/oder ein bis drei Reste aus der Gruppe Cyano, Nitro, Ci-C6-Alkyl, Ci-C6-Halogenalkyl, Hydroxy, Ci-C6-Alkoxy, d- Cδ-Halogenalkoxy, Hydroxycarbonyl, Ci-Cδ-Alkoxycarbonyl, Hydroxycarbo- nyl-Ci-Cδ-alkoxy, Ci-C6-Alkylsulfonylamino und Ci-Cβ-C 6 alkoxycarbonyl-Ci-C4-alkyl, Ci-C 6 haloalkoxycarbonyl-Ci-C4-alkyl, CrC 6 - alkylcarbonyloxy-Ci-C4-alkyl, Ci-Cδ-alkylcarbonylamino-Ci ^ alkyl, di (-C 6 - alkyl) carbonylamino-Ci-C4-alkyl, [di (Ci-C 6 -alkylamino) carbonyloxy] Ci-C4-alkyl, {di [di (Ci-C 6 alkyl) amino] carbonyloxy} Ci C4-alkyl, phenyl-Ci-C4-alkyl, phenyl-C 2 -C 4 -alkenyl, phenyl-C 2 -C 4 -alkynyl, phenyl-Ci-C 4 - haloalkyl, phenyl-C 2 -C 4 haloalkenyl, phenyl-C 1 -C 4 -hydroxyalkyl, phenyl-C 1 -C 4 -alkyl, phenylthio-C 1 -C 4 -alkyl, phenylsulfinyl-C 1 -C 4 -alkyl, phenylsulfonyl-C 1 -C 4 - alkyl, heteroaryl, heteroaryl-Ci-C4-alkyl, heteroaryl-Ci-C4-hydroxyalkyl, heteroaryloxy- Ci-C4-alkyl, heteroarylthio-Ci-C4-alkyl, heteroarylsulfinyl-Ci-C4-alkyl, heteroaryl sulfonyl-C 1 -C 4 -alkyl, wherein the aforesaid phenyl and heteroaryl radicals may be or fully halogenated and / or a 6 alkyl to three radicals from the group cyano, nitro, Ci-C, C-C 6 haloalkyl, hydroxy, Ci-C 6 alkoxy, C 1 -C 6 -haloalkoxy, hydroxycarbonyl, C 1 -C 6 -alkoxycarbonyl, hydroxycarbonyl-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylsulfonylamino and C 1 -C 6 -cycloalkyl
Halogenalkylsulfonylamino tragen können; steht.Can carry halogenoalkylsulfonylamino; stands.
5. Verfahren zur Herstellung von heteroaroylsubstituierten Alaninen der Formel I gemäß Anspruch 1 , dad Alaninderivate der Formel V5. A process for the preparation of heteroaroyl-substituted alanines of the formula I according to claim 1, dad alanine derivatives of the formula V
wobei R1, R4, R5, R6 und R7 die unter Anspruch 1 genannten Bedeutungen haben und L1 für Hydroxy oder Ci-Cδ-Alkoxy steht, where R 1 , R 4 , R 5 , R 6 and R 7 have the meanings mentioned under claim 1 and L 1 is hydroxy or C 1 -C 6 -alkoxy,
mit Heteroarylsäure(derivate)n der Formel IVwith heteroaryl acid (derivatives) n of the formula IV
OO
A L wobei A die unter Anspruch 1 genannten Bedeutung hat und L2 für Hydroxy, Halogen, Ci-Cδ-Alkylcarbonyl, Ci-Cδ-Alkoxycarbonyl, Ci -C4-Al kylsu If onyl, Phospho- ryl oder Isoureyl steht,AL where A has the meaning given in claim 1 and L 2 is hydroxyl, halogen, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 4 -alkyl, onyl, phosphoryl or isoureyl,
zu entsprechenden Heteroaroylderivaten der Formel IIIto corresponding Heteroaroylderivaten of formula III
wobei A, R1, R4, R5, R6 und R7 die unter Anspruch 1 genannten Bedeutungen haben und L1 für Hydroxy oder Ci-Cδ-Alkoxy steht, und anschließend die erhaltenen Heteroaroylderivate der Formel IM mit einem where A, R 1 , R 4 , R 5 , R 6 and R 7 have the meanings mentioned under claim 1 and L 1 is hydroxy or C 1 -C 6 alkoxy, and then the resulting heteroaroyl derivatives of the formula III with a
Amin der Formel IlAmine of the formula II
HNR2R3 II, wobei R2 und R3 die unter Anspruch 1 genannten Bedeutungen haben, umgesetzt werden. HNR 2 R 3 II, wherein R 2 and R 3 have the meanings mentioned under claim 1, are reacted.
6. Heteroaroylderivate der Formel6. Heteroaroyl derivatives of the formula
wobei A, R1, R4, R5, R6 und R7 die unter Anspruch 1 genannten Bedeutungen haben und L1 für Hydroxy oder Ci-Cδ-Alkoxy steht. where A, R 1 , R 4 , R 5 , R 6 and R 7 have the meanings mentioned under claim 1 and L 1 is hydroxy or C 1 -C 6 alkoxy.
7. Mittel, enthaltend eine herbizid wirksame Menge mindestens eines heteroaroyl- substituierten Alanins der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I gemäß einem der Ansprüche 1 bis 4 und für die Formulierung von Pflanzenschutzmitteln übliche Hilfsmittel.7. A composition comprising a herbicidally effective amount of at least one heteroaroyl-substituted alanine of the formula I or an agriculturally useful salt of I according to any one of claims 1 to 4 and for the formulation of pesticides customary auxiliaries.
8. Verfahren zur Herstellung von Mitteln gemäß Anspruch 7, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge mindestens eines heteroaroyl- substituierten Alanins der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I gemäß einem der Ansprüche 1 bis 4 und für die Formulierung von Pflanzenschutzmitteln übliche Hilfsmittel mischt.8. A process for the preparation of agents according to claim 7, characterized in that a herbicidally effective amount of at least one heteroaroyl-substituted alanine of formula I or an agriculturally useful salt of I according to one of claims 1 to 4 and for the formulation of pesticides usual Remedy mixes.
9. Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge mindestens eines hetero- aroylsubstituierten Alanins der Formel I oder eines landwirtschaftlich brauchba- ren Salzes von I gemäß einem der Ansprüche 1 bis 4 auf Pflanzen, deren Lebensraum und/oder auf Samen einwirken läßt.9. A process for controlling undesired plant growth, which comprises reacting a herbicidally effective amount of at least one heteroaryl-substituted alanine of the formula I or an agriculturally useful salt of I according to any one of claims 1 to 4 on plants whose habitat and / or or to act on seeds.
10. Verwendung der heteroaroylsubstituierten Alanine der Formel I und deren landwirtschaftlich brauchbaren Salze gemäß einem der Ansprüche 1 bis 4 als Herbi- zide. 10. Use of the heteroaroyl-substituted alanines of the formula I and their agriculturally useful salts according to any one of claims 1 to 4 as herbicides.
EP07704402A 2006-02-16 2007-02-07 Heteroaroyl-substituted alanines Withdrawn EP1987008A2 (en)

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