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WO2000026194A1 - Novel 1-aryl-4-thiouracils - Google Patents

Novel 1-aryl-4-thiouracils Download PDF

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Publication number
WO2000026194A1
WO2000026194A1 PCT/EP1999/008266 EP9908266W WO0026194A1 WO 2000026194 A1 WO2000026194 A1 WO 2000026194A1 EP 9908266 W EP9908266 W EP 9908266W WO 0026194 A1 WO0026194 A1 WO 0026194A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
alkoxy
carbonyl
methyl
halogen
Prior art date
Application number
PCT/EP1999/008266
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German (de)
French (fr)
Inventor
Olaf Menke
Gerhard Hamprecht
Robert Reinhard
Peter Schäfer
Cyrill Zagar
Karl-Otto Westphalen
Martina Otten
Helmut Walter
Original Assignee
Basf Aktiengesellschaft
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Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to JP2000579583A priority Critical patent/JP2002528532A/en
Priority to EP99955917A priority patent/EP1127053A1/en
Priority to CA002349386A priority patent/CA2349386A1/en
Publication of WO2000026194A1 publication Critical patent/WO2000026194A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to novel l-aryl-4-thiouracils of the formula I.
  • R 1 is hydrogen, amino or Ci-C ⁇ alkyl
  • R 2 is hydrogen, halogen, -CC alkyl or -C-haloalkyl
  • R 3 is hydrogen, halogen, Ci-C ⁇ alkyl or halomethyl
  • R 4 is hydrogen or halogen
  • R 5 cyano, halogen, -CO-NH 2 , -CS-NH 2 or -OC (R 8 , R 9 ) -CO-0 (-C-C 6 alkyl);
  • R 6 together with R 5 is a radical -N (R 7 ) -CZ 1 -C (R 8 ', R 9 ') -0- which is bonded to R 5 via the oxygen, or
  • phenyl, phenoxy or phenylsulfonyl group which may be unsubstituted or bear one to three substituents, in each case selected from the group consisting of halogen, nitro, cyano, C 1 -C 6 -alkyl,
  • Ci-C ⁇ -haloalkyl Ci-Cg-alkoxy and (C ⁇ -C 6 -alkoxy) carbonyl
  • Z 1 , Z 2 , Z 3 , Z 4 independently of one another oxygen or sulfur;
  • Ci-C ß- alkyl Ci-Cg-haloalkyl, C 3 -C 6 cycloalkyl, C 3 -Ce alkenyl, C 3 -C 6 alkynyl, hydroxy-C ⁇ -C 6 alkyl, Ci -C ⁇ -alkoxy-Ci-Ce-alkyl, C; ⁇ .
  • phenyl ring can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and (C 1 -C 6 alkoxy) ) carbon
  • R 13 is hydrogen, hydroxyl, -CC 6 -alkyl, C 3 -C 6 -cycloalkyl, -C-C 6 -alkoxy, (Ci -Ce -alkoxy) carbonyl -Cx -C 6 -alkoxy, C 3 -C 6 - Alkenyl or C 3 -C 6 alkenyloxy;
  • R 14 , R 14 ', R 14 "independently of one another - hydrogen, halogen,
  • Phenyl- (Ci-Cg-alkyl) sulfonyloxy where the phenyl rings of the latter 10 residues may be unsubstituted or in turn may carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-C ⁇ - alkyl, Ci -C ⁇ haloalkyl,
  • R 15 is hydrogen, cyano, Ci-C ⁇ - alkyl, Ci-C ⁇ -haloalkyl,
  • R 16 is hydrogen, hydroxy, Ci-Cg-alkyl, C 3 -C ⁇ - alkenyl,
  • R 19 is hydrogen, cyano, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, (Ci-Cg-alkyl) carbonyl or (Ci-Cg-alkoxy) carbonyl;
  • R 20 is hydrogen, OR 29 , SR 29 , Ci-Cg-alkyl, which can also carry one or two Ci-Cg-alkoxy substituents, C 2 -Cg-alkenyl, C -Cg-alkynyl, Ci-Cg-haloalkyl, C 3 -Cg-cycloalkyl, Ci-C ⁇ -alkylthio-Ci-C ⁇ -alkyl, Ci-Cg-alkyliminooxy, -N (R 25 ) R 26 or phenyl, which may be unsubstituted or carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-Cg-alkyl, C 2 -C ⁇ - alkenyl, Ci-Cg-haloalkyl, Ci-C ⁇ -alkoxy and (C ⁇ ⁇ Cg-alkoxy) carbonyl;
  • R 21 is hydrogen, cyano, halogen, Ci-C ⁇ - alkyl, C 3 -C ⁇ - alkenyl, C 3 -C 6 -alkynyl, Ci-Cg-alkoxy-Ci-Cg-alkyl, (Ci-C ⁇ - alkyl ) - carbonyl, (Ci-C ⁇ -alkoxy) carbonyl, -N (R 25 ) R 26 or phenyl, which in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci C ⁇ alkyl, Ci-C ⁇ haloalkyl, C 3 -C ⁇ alkenyl, Ci-C ⁇ alkoxy and (Ci-Cg-alkoxy) carbonyl;
  • R 22 is hydrogen, cyano, halogen, Ci-Cg-alkyl, Ci-Cg-alkoxy,
  • Ci-Cg-haloalkyl (Ci-C ⁇ - alkyl) carbonyl or (Ci-Cg-alkoxy) carbonyl;
  • R 23 is hydrogen, cyano, Ci-Cg-alkyl or (Ci-Cg-alkoxy) carbonyl;
  • R 24 , R 29 independently of one another are hydrogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, C -Cg-alkenyl or C -C ⁇ - alkynyl, where the latter 4 groups can each carry one or two of the following radicals: cyano , Halogen, hydroxy, hydroxycarbonyl, Ci-C ⁇ - alkoxy, Ci-Cg-alkyl-thio, (Ci-C ⁇ - alkyl) carbonyl, (C ⁇ ⁇ Cg-alkoxy) carbonyl, (Ci-Cg-alkyl) carbonyloxy, (C -Cg alkenyloxy) carbonyl or one bonded to the nitrogen atom via a carbonyl bridge those 3- to 7-membered azaheterocycle which, in addition to carbon ring members, may also contain an oxygen or sulfur atom as the ring member; or (Ci-Cg-alkyl) carbonyl, (Ci-Cg-
  • Ci -Cg alkyl aminocarbonyl Ci -Cg alkyloximino Ci -Cg alkyl, C 3 -Cg cycloalkyl,
  • R 25 , R 26 , R 27 , R 28 independently of one another are hydrogen, Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 2 -Cg-alkynyl,
  • Ci-C ⁇ haloalkyl -C-Cg-alkoxy-C ⁇ -Cg-alkyl, (Ci-Cg-alkyl) carbonyl, (Ci-Cg-alkoxy) carbonyl, (Ci-Cg- Alkoxy) - carbonyl-C -Cg-alkyl, (Ci-Cg-alkoxy) carbonyl-C 2 -Cg-alkenyl, where the alkenyl chain can additionally carry one to three halogen and / or cyano radicals, or Ci-Cg- Alkylsulfonyl, (Ci-C ⁇ - alkoxy) carbonyl-Ci-Cg-alkyl-sulfonyl, phenyl or phenylsulfonyl, where the two phenyl rings can be unsubstituted or in turn can carry one to three substituents, each selected from the group
  • Ci-Cg-haloalkyl C 3 -Cg-alkenyl, Ci-Cg-alkoxy and (Ci-Cg-alkoxy) carbonyl, or R 25 and R 26 and / or R 27 and R 28 together with the respective common nitrogen atom for a saturated or unsaturated 4- to 7-membered azaheterocycle, which besides
  • the invention also relates to the use of the compounds I as herbicides, herbicidal compositions which contain the compounds I as active substances,
  • the object of the present invention was therefore to provide new herbicidally active 1-aryluracils which can be used to combat undesirable plants better than before.
  • the l-aryl-4-thiouracils of the formula I defined at the outset were found. Furthermore, herbicidal compositions have been found which contain the compounds I and have a very good herbicidal action. In addition, processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.
  • the compounds of the formula I can contain one or more centers of chirality and are then present as mixtures of enantiomers or diastereomers.
  • E / Z isomers may also be possible.
  • the invention relates both to the pure enantiomers or diastereomers and to their mixtures.
  • Agriculturally useful salts include, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the herbicidal activity of the compounds I. So come as cations in particular the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, as well as the airanonium ion, if desired one to four C ⁇ -C-alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (-C-alkyl) sulfonium and sulfoxonium ions, preferably tri ( -CC al
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of -C-alkanoic acids, preferably formate, acetate, propionate and butyrate.
  • organic molecule parts mentioned in the definition of R 1 to R 3 , R 5 to R 29 and on phenyl, cycloalkyl and heterocyclyl rings are collective terms for individual lists of the individual group members. All carbon chains, that is to say all (optionally substituted) alkyl -, Alkenyl or alkynyl parts can be straight-chain or branched.
  • Halogenated substituents preferably carry one to five identical or different halogen atoms.
  • Halogen is fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
  • -C-C 4 alkyl for: CH 3 , C 2 H 5 , n-propyl, CH (CH 3 ) 2 , n-butyl, CH (CH 3 ) -CH 5 , 2-methylpropyl or C (CH 3 ) 3 , in particular for CH 3 , C 2 H 5 or CH (CH 3 ) 2 ;
  • C 1 -C 6 -haloalkyl for: a C 1 -C 4 -alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CHF, CHF, CF 3 , CH 2 C1, dichloromethyl, trichloromethyl , Chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2 , 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl, CF 5 , 2-fluoropropyl, 3-fluoropropy
  • Ci-Cg-alkyl for: -CC 4 -alkyl as mentioned above, and for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1st , 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl,
  • Ci-Cg-haloalkyl for: Ci-Cg-alkyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for example, one of the radicals mentioned under C 1 -C 4 -haloalkyl or for 5- Fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6-fluoro l-hexyl, 6-chloro-1-hexyl, 6-bromo-l-hexyl, 6-iodo-l-hexyl, 6, 6, 6-trichloro-l-hexyl or dodecafluorohexyl, in particular for chloromethyl, fluoromethyl, difluoromethyl, Trifluoromethyl, 2-fluoroethyl,
  • Hydroxy-Ci-C -alkyl for: e.g. Hydroxymethyl, 2-hydroxyeth-1-yl, 2-hydroxy-prop-l-yl, 3-hydroxy-prop-l-yl, 1-hydroxy-prop-2-yl, 2-hydroxy-but-l-yl, 3-hydroxy-but-l-yl, 4-hydroxy-but-l-yl, l-hydroxy-but-2-yl, l-hydroxy-but-3-yl, 2-hydroxy-but-3-yl, 1-hydroxy-2-methyl-prop-3-yl, 2-hydroxy-2-methyl-prop-3-yl or 2-hydroxymethyl-prop-2-yl, in particular for 2-hydroxyethyl;
  • Cyano-Ci-Cg-alkyl for: e.g. Cyanomethyl, 1-cyanoeth-l-yl,
  • 2-cyanoeth-l-yl 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyano-prop-1-yl, l-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4-cyanobut-l-yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, l- Cyanobut-3-yl, 2-cyano-but-3-yl, l-cyano-2-methyl-prop-3-yl, 2-cyano-2-methyl-prop-3-yl, 3-cyano-2- methyl-prop-3-yl or 2-cyanomethyl-prop-2-yl, especially for cyanomethyl or 2-cyanoethyl;
  • Phenyl-Ci-C ⁇ - alkyl for: e.g. benzyl, 1-phenylethyl, 2-phenyl-ethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-1-yl, 1-phenylbut -l-yl, 2-phenylbut-l-yl, 3-phenylbut-l-yl, 4-phenylbut-l-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2 -yl, 4-phenylb t-2-yl, l- (phenylmethyl) -eth-1-yl, l- (phenylmethyl) -l- (methyl) -eth-l-yl or 1- (phenylmethyl) - prop-1-yl, especially for benzyl or 2-phenylethyl;
  • Phenyl- (Ci-Cg-alkyl) carbonyloxy for: e.g. benzylcarbonyloxy, 1-phenylethylcarbonyloxy, 2-phenylethylcarbonyloxy, 1-phenylprop-1-ylcarbonyloxy, 2-phenylprop-l-ylcarbonyloxy, 3-phenylprop-1-ylcarbonyloxy , 1-phenylbut-l-ylcarbonyloxy, 2-phenylbut-1-ylcarbonyloxy, 3-phenylbut-l-ylcarbonyloxy, 4-phenyl- but-1-ylcarbonyloxy, l-phenylbut-2-ylcarbonyloxy, 2-phenylbut-2-ylcarbonyloxy, 3-phenylbut-2-ylcarbonyloxy, 4-phenylbut-2-ylcarbonyloxy, 1- (phenylmethyl) -eth- 1-ylcarbonyloxy, 1- (phenylmethyl) -1- (methyl)
  • Phenyl-Ci-Cg-alkylsulfonyloxy for: e.g. Benzylsulfonyloxy, 1-phenylethylsulfonyloxy, 2-phenylethylsulfonyloxy, 1-pheny1-prop-1-ylsulfonyloxy, 2-phenylprop-l-ylsulfonyloxy, 3-phenylprop-1-ylsulfonyloxy, 1-phenylbut-l-ylsulfonyloxy, 2-phenyl but-1-ylsulfonyloxy, 3-phenylbut-l-ylsulfonyloxy, 4-phenyl-but-1-ylsulfonyloxy, l-phenylbut-2-ylsulfonyloxy, 2-phenylbut-2-ylsulfonyloxy, 3-phenylbut-2-ylsulfonyloxy, 4-phenyl-but-2
  • - (Ci-Cg-alkyl) carbonyl for: for example CO-CH 3 , CO-C 2 H 5 , CO-CH 2 -C 2 H 5 ,
  • Ci-C-alkyl carbonyl -Ci-Cg-alkyl for: Ci-C-alkyl substituted by (Ci-Cg-alkyl) carbonyl as mentioned above, e.g. for methylcarbonylmethyl;
  • - (Ci-Cg-haloalkyl) carbonyl for: a (Ci-Cg-alkyl) carbonyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloroacetyl, dichloroacetyl, trichloroacetyl , Fluoroacetyl, difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2, 2-difluoroethylcarbonyl, 2, 2, 2-trif carbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2, 2-difluor
  • (C ⁇ ⁇ Cg-alkyl) carbonyloxy for: acetyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1, 1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1, 1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2, 2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n-hexylcarbonyloxy, 1-methylpentyl-methylpentoxycarbonyloxy Methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, 1, 1-dimethylbuty
  • (Ci-Cg-haloalkyl) carbonyloxy for: a (Ci-Cg-alkyl) carbonyloxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloroacetyloxy, dichloroacetyloxy, trichloroacetyloxy , Fluoroacetyloxy, difluoroacetyloxy, trifluoroacetyloxy, chlorofluoroacetyloxy, dichlorofluoroacetyloxy, chlorodifluoroacetyloxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 2-bromoethylcarbonyloxy, 2-iodoethylcarbonyloxy, 2, 2-difluoroethylcarbonyl.
  • 2-chloro-2-fluoroethylcarbonyloxy 2-chloro-2, 2-difluoroethylcarbonyloxy, 2, 2-dichloro-2-fluoroethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy, pentafluoroethylcarbonyloxy, 2-fluoropropylcarbonyloxy, 3- Fluoropropylcarbonyloxy, 2,2-difluoropropylcarbonyloxy, 2, 3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyloxy, 3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyloxy, 2-bromopropylcarbonyloxy, 3-bromopropylcarbonyloxy, 3, 3, 3- Trifluoropropylcarbonyloxy, 3, 3, 3-trichloropropylcarbonyloxy, 2,2,3,3, 3-pentafluoropropylcarbonyloxy
  • (C -C ⁇ alkyl) carbonylthio for acetylthio, ethylcarbonylthio, n-propylcarbonylthio, 1-methylethylcarbonylthio, n-butylcarbonylthio, 1-methylpropylcarbonylthio, 2-methylpropylcarbonylthio, 1, 1-dimethylethylcarbonylthio, n-pentylcarbonylthio, n-pentylcarbonylthio 2-methylbutylcarbonylthio, 3-methylbutylcarbonylthio, 1, 1-dimethylpropylcarbonylthio, 1, 2-dimethylpropylcarbonylthio, 2, 2-dimethylpropylcarbonylthio, 1-ethylpropylcarbonylthio, n-hexylcarbonylthio, 1-methylpentylcarbonylthio - carbonylthio, 3-methylpentylcarbonylthi
  • (Ci-C ⁇ -haloalkyl) carbonylthio for: a (Ci-Cg-alkyl) carbonylthio radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloroacetylthio, dichloroacetylthio, Trichloroacetylthio, fluoroacetylthio, difluoroacetylthio, tri- fluoroacetylthio, chlorofluoroacetylthio, dichlorofluoroacetylthio, chlorodifluoroacetylthio, 2-fluoroethylcarbonylthio, 2-chloroethylcarbonylthio, 2-bromoethylcarbonylthio, 2-iodo-ethylcarbonylthio, 2, 2-difluoroethylcarbonylthio, 2,2,2-tri-
  • (Ci-Cg-alkyl) carbamoyloxy for: methylcarbamoyloxy, ethylcarbamoyloxy, n-propylcarbamoyloxy, 1-methylethylcarbamoyloxy, n-butylcarbamoyloxy, 1-methylpropylcarbamoyloxy, 2-methylpropylcarbamoyloxy, 1, 1-dimethylethyl-pamoyloxy, pentamoyloxy, 1-Methylbutylcarbamoyloxy, 2-Methylbutylcarbamoyloxy, 3-Methylbutylcarbamoyloxy, 1, 1-Dirnethylpropylcarbamoyloxy, 1, 2-Dimethylpropylcarbamoyloxy, 2, 2-Dirnethylpropyl-carbamoyloxy, 1-Ethylpropylcarbamoyla
  • (Ci-Cg-haloalkyl) carbamoyloxy for: a (Ci-Cg-alkyl) -carbamoyloxy radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethylcarbamoyloxy, dichloromethylcarbamoyloxy , Trichloromethyl carbamoyloxy, fluoromethyl carbamoyloxy, difluoromethyl carbamoyloxy, trifluoromethyl carbamoyloxy, chlorofluoromethyl carbamoyloxy, dichlorofluoromethyl carbamoyloxy, chlorodifluoromethyl carbamoyloxy, • 2-fluoroethyl carbamoyloxy, 2-chloroethylcarbamoyloxy, 2-bromoethylcarbamoyloxy, 2-iodoethylcarbamoyloxy, 2,
  • Ci-Cg-alkoxy for: for example OCH 3 , 0C 2 H 5 , OCH 2 -C 2 H 5 , OCH (CH 3 ) 2 , n-butoxy, OCH (CH 3 ) -C 2 H 5 , OCH 2 -CH (CH 3 ) 2 , OC (CH 3 ) 3 , n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylb toxy, 1, 1-dirnethyl-propoxy, 1, 2-dimethylpropoxy, 2, 2-dimethylpropoxy, 1-ethyl-propoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dirnethylb toxy,
  • C ⁇ -C for 4 -haloalkoxy a C ⁇ -C 4 alkoxy as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, ie, for example chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, Difluormeth- oxy, Trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2, 2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2- Chloro-2,2-difluoroethoxy, 2,2-di-chloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy
  • Ci-Cg-haloalkoxy for: a Ci-Cg-alkoxy radical as mentioned above, partially or completely by fluorine, chlorine,
  • Bromine and / or iodine is substituted, for example one of the radicals mentioned under C 1 -C 4 -haloalkoxy or for 5 -fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5 Iodine-l-pentoxy,
  • Hydroxy-Ci-Cg -alkoxy for: e.g. OCH 2 -OH, OCH (CH 3 ) -OH,
  • Cyano-Ci-Cg-alkoxy for: e.g. OCH-CN, OCH (CH 3 ) -CN, OCH 2 -CH 2 -CN, OCH (C 2 H 5 ) -OH, OCH 2 -CH (CH 3 ) -CN , 3-cyanoprop-l-yl-oxy, 1-cyanobut-l-yloxy, 2-cyanobut-l-yloxy, 3-cyanobut-l-yl-oxy, 4-cyanobut-l-yloxy, l-cyanobut-2 -yloxy, 2-cyanobut-2-yloxy, 3-cyanobut-2-yloxy, 4-cyanobut-2-yloxy, 1- (CH 2 -CN) -eth- 1-yloxy, 1- (CH 2 - CN) -1- (CH 3 ) -eth-1-yloxy or 1- (CH 2 -CN) prop-1-yloxy, in particular for OCH 2 -CN or OCH-CH 2 -CN
  • Phenyl-Ci-Cg-alkoxy for: e.g. Benzyloxy, 1-phenylethoxy, 2-phenylethoxy, 1-phenylprop-l-yloxy, 2-phenylprop-l-yloxy, 3-phenylprop-l-yloxy, 1-phenylbut-l-yloxy, 2-phenylbut-l-yl- oxy, 3-phenylb tl-yloxy, 4-phenylbut-l-yloxy, 1-phenylbut-2-yloxy, 2-phenylbut-2-yloxy, 3-phenylbut-2-yloxy, 4-phenylbut-2-yloxy , 1- (benzyl) -eth-1-yloxy, 1- (benzyl) -1- (methyl) -eth-1-yloxy or 1- (benzyl) -prop-1-yloxy, especially for benzyloxy or 2-phenylethoxy ;
  • Heterocyclyl-Ci-Cg-alkoxy for: e.g. heterocyclylmethoxy, 1- (heterocyclyl) ethoxy, 2- (heterocyclyl) ethoxy, l- (heterocyclicl) prop-l-yloxy, 2- (heterocyclyl) prop-1-yloxy, 3- (heterocyclyl) prop-1-yloxy, 1- (heterocyclyl) but-1-yloxy, 2- (heterocyclyl) but-l-yloxy, 3- (heterocyclyl) but-1-yloxy, 4- (heterocyclyl ) but-1-yloxy, 1- (heterocyclyl) but-2-yloxy, 2- (heterocyclyl) but-2-yloxy, 3- (heterocyclyl) but-2-yloxy, 4- (hetero- cyclyl) but-2-yloxy, 1- (heterocyclylmethyl) -
  • Phenyl-Ci-Cg-alkylthio for: e.g. Benzylthio, 1-phenylethy1-thio, 2-phenylethylthio, 1-phenylprop-l-ylthio, 2-phenylprop-1-ylthio, 3-phenylprop-l-ylthio, 1-phenylbut-l-ylthio, 2-phenylbut- l-ylthio, 3-phenylbut-l-ylthio, 4-phenylbut-l-ylthio, l-phenylbut-2-ylthio, 2-phenylbut-2-ylthio, 3-phenylbut-2-ylthio, 4-phenylbut- 2-ylthio, 1- (phenylmethyl) -eth-1-ylthio, 1- (phenylmethyl) -1- (methyl) -eth-1-ylthio or 1- (phenylmethyl) prop-1-ylthio, especially for benzy
  • (Ci-Cg-alkoxy) carbonyl for: e.g. CO-OCH 3 , CO-OC 2 H 5 , CO-CH 2 -C 2 H 5 , CO-OCH (CH 3 ) 2 , n-butoxycarbonyl, CO-OCH ( CH 3 ) -C 2 H 5 , CO-OCH 2 -CH (CH 3 ) 2 , CO-OC (CH 3 ) 3 , n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylb toxycarbonyl , 2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1 -Dimethylbutoxycarbonyl, 1, 2-
  • (Ci-C ⁇ -alkoxy) carbonyloxy for: methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy, 1-methylpropoxycarbonyloxy, 2-methylprooxycarbonyloxy, 1, 1-dimethylethoxycarbonyloxy, n-pentoxycarbonyloxy , 1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy, 3-methylbutoxycarbonyloxy, 2, 2-dimethylpropoxycarbonyloxy, 1-ethylpropoxycarbonyloxy, n-hexoxycarbonyloxy, 1, 1-dimethylpropoxycarbonyloxy, 1, 2-dimethylpropoxycarbonyloxyoxy, 1-methylpentoxy -Methylpentoxycarbonyloxy, 3-methylpentoxycarbonyloxy, 4-methylpentoxycarbonyloxy, 1, 1-dimethylbutoxycarbonyloxy, 1, 2-dimethylbutoxy
  • (Ci-Cg -alkoxy) carbonylthio for: methoxycarbonylthio, ethoxycarbonylthio, n-propoxycarbonylthio, 1-methylethoxycarbonylthio, n-butoxycarbonylthio, 1-methylpropoxycarbonylthio, 2-methylpropoxycarbonylthio, 1, 1-dimethylthoxycarbonylthio, n-propoxycarbonylthio Methylbutoxycarbonylthio, 2-methylbutoxycarbonylthio, 3-methylbutoxycarbonylthio, 2, 2-dimethylpropoxycarbonylthio, 1-ethylpropoxycarbonylthio, n-hexoxycarbonylthio, 1, 1-dimethylpropoxycarbonylthio, 1, 2-dimethylpropoxycarbonylthioyl, 1-2 Methyl-pentoxycarbonylthio, 3-methylpentoxycarbonylthio, 4-methyl-pentoxycarbonylthio, 1, 1-d
  • Ci-Cg-alkylthio for: SCH 3 , SC 2 H 5 , SCH 2 -CH 5 , SCH (CH 3 ), n-butylthio, 1-methylpropylthio, 2-methylpropylthio, SC (CH 3 ) 3 , n-pentylthio, 1-Methylb tylthio, 2-Methylbutylthio, 3-Methylbutylthio, 2, 2-Dimethylpropylthio, 1-Ethylpropylthio, n-Hexylthio, 1, 1-Dimethylpropylthio, 1, 2-Dirnethylpropylthio, 1-Methylpentylthio, 2-Methylpentylthio -Methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1, 2-dimethylbutylthio, 1, 3-dimethylbutylthio,
  • Ci-Cg-haloalkylthio for: Ci-Cg-alkylthio as mentioned above, partially or completely by fluorine, chlorine,
  • Bromine and / or iodine is substituted, for example for SCHF 2 , SCF 3 , chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2, 2-difluoroethylthio, 2, 2, 2 -Trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2, 2-di-fluoroethylthio, 2, 2-dichloro-2-fluoroethylthio, SC 2 F 5 , 2- Fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloro propylthio, 2-bromopropylthio, 3-bromoprop
  • Ci-Cg-alkylsulfinyl for: S0-CH 3 , SO-C 2 Hs, n-propylsulfinyl, 1-methylethylsulfinyl, nB tylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethylethylsulfinyl, n-pentylsulfinyl, 1 -Methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1, 1-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, 2, 2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 1-methylp
  • Ci-Cg-alkylsulfonyl for: S0 2 -CH 3 , S0 2 -C 2 H 5 , n-propylsulfonyl, S0 2 -CH (CH 3 ) 2 , n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, S0 2 - C (CH 3 ) 3 , n-pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dirnethylpropylsulfonyl, 2, 2-dimethylpropylsulfonyls, hexylsulfonyl, 1-ethylsulfonyl, 1-ethylsulfonyls , 1-methylpent
  • C -C 6 haloalkylsulfonyloxy for: Ci-C ⁇ - alkylsulfonyloxy as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example ClCH 2 -S0 2 -0-, CH (Cl) 2 -S0 2 -0-, C (CD 3 -S0 2 -0-, FCH 2 -S0 2 -0-, CHF 2 -S0 2 -0-, CF 3 -S0-0-, chlorofluoromethyl-S0 2 - 0-, dichlorofluoromethyl-S0-0-, chlorodifluoromethyl-S0 2 -0-, 1-fluoroethyl- S0 2 -0-, 2-fluoroethyl-S0 2 -0-, 2-chloroethyl-S0 2 -0-, 2-bromoethyl-S0 2 -0-, 2-iodo-
  • (Ci-C ⁇ alkyl) aminocarbonyl for: (C 1 -C 4 alkyl) aminocarbonyl as mentioned above and, for example, n-pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2, 2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1, 2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1, 1-dimethylnetyl butyl 1, 3-dimethylbutylaminocarbonyl, 2, 2-dimethylbutylaminocarbonyl, 2, 3-diethylbutylamino
  • Di (Ci-C ⁇ -alkyl) aminocarbonyl for: for example N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N, N-dipropylaminocarbonyl,
  • N-butyl-N-methylaminocarbonyl N-methyl-N- (1-methylpropyl) aminocarbonyl, N-methyl-N- (2-methylpropyl) aminocarbonyl, N- (1, 1-dirnethy1ethyl) -N-methylaminocarbonyl, N -Ethyl-N-propylaminocarbonyl, N-ethyl-N- (1-methylethyl) aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N- (1-methylpropyl) - aminocarbonyl, N-ethyl-N- (2nd -methylpropyl) aminocarbonyl, N-ethyl-N- (1, 1-dimethylethyl) aminocarbonyl, N- (1-methyl-ethyl) -N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N- (1-methyl
  • (Ci -C ⁇ - alkyl) iminooxycarbonyl for: methyliminooxycarbonyl, ethyliminooxycarbonyl, n-propyliminooxycarbonyl, 1-methyl-ethyliminooxycarbonyl, n-butyliminooxycarbonyl, 1-methyl-propyliminooxycarbonyl, 2-methylpropyliminooxycarbonyl, 1, 1-dimethyloxycarbonyl, pentane 1-methylbutyliminooxycarbonyl, 2-methylbutyliminooxycarbonyl, 3-methylbutyliminooxycarbonyl, 1, 1-dirnethylpropyliminooxycarbonyl, 1, 2-dirnethylpropyliminooxycarbonyl, 2, 2-dimethylpropyliminooxycarbonyl, 1-ethylpropyliminooxyoxyylyl, 3-methylyloxy-methyloxycarbonyl, 3 Methylpentyliminooxycarbonyl, 4-methyl
  • Ci-C ⁇ - alkylidene aminoxy for: acetylidene aminoxy, 1-propylidene aminoxy, 2-propylidene aminoxy, 1-butylidene aminoxy, 2-tylidene aminoxy or 2-hexylidene aminoxy, in particular for acetylidene aminoxy or 2-propylidene aminoxy;
  • Ci-Cg-alkyliminooxy for: methyliminooxy, ethyliminooxy, n-propyliminooxy, 1-methylethyliminooxy, n-butyliminooxy, 1-methylpropyliminooxy, 2-methylpropyliminooxy, n-pentyliminooxy, n-hexyliminooxy, 1-methylpentyliminooxy, 2-methylpentyloxy -Methylpentyliminooxy or 4 -Methylpentyl - iminooxy, especially for methyliminooxy, ethyliminooxy or 1 -Methylethyliminooxy;
  • Ci-Cg-alkoxy- (Ci-Cg-alkyl) aminocarbonyl for: (Ci-Cg-alkyl) - aminocarbonyl such as CO-NH-CH 3 , CO-NH-CHs, CO-NH-CH 2 -C 2 H 5 , CO-NH-CH (CH 3 ).
  • Ci-C ⁇ -alkoxyamino-Ci-C ⁇ -alkyl for: e.g. CH 2 -NH-OCH 3 , CH 2 -NH-OC 2 H 5 , CH 2 -NH-OCH 2 -C 2 H 5 , CH 2 - NH-OCH (CH 3 ) 2 , CH 2 -NH-OCH 2 -CH 2 -C 2 H 5 , CH 2 -NH-OCH (CH 3 ) -C 2 H 5 ,
  • Ci-C ⁇ -alkoxy-Ci-C ⁇ -alkylamino-Ci-C ⁇ -alkyl for: Ci-C ⁇ -alkylamino-Ci-C ⁇ -alkyl such as CH 2 -NH-CH 3 , CH 2 -NH -C 2 H 5 , CH 2 -NH-CH 2 -C 2 H 5 , CH 2 -NH-CH (CH 3 ) 2 , CH 2 -NH- (CH 2 ) 3 -CH 3 , CH 2 -NH- CH (CH 3 ) -C 2 H 5 , CH 2 -NH-CH 2 -CH (CH 3 ) 2 , CH 2 -NH-C (CH 3 ) 3 , CH 2 -NH- (CH 2 ) 4 -CH 3 ,
  • Ci-Cg-alkyloximino such as methoxyimino, ethoxyi ino, 1-propoxyimino, 2-propoxyimino, 1-methylethoxyimino, n-butoxyimino, sec.-butoxyimino, tert.
  • Ci-Cg-Alkoxy-Ci-C ⁇ - alkyl for: Ci-C ⁇ - alkoxy - as mentioned above - substituted Ci-Cg-alkyl, e.g. for CH 2 -OCH 3 , CH 2 -OCH 5 , n- Propoxymethyl, CH 2 -OCH (CH 3 ) 2 , n-butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, CH 2 -OC (CH 3 ) 3 , 2- (methoxy) ethyl, 2 - (Ethoxy) ethyl, 2- (n-propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methylpropoxy ) ethyl, 2- (1,1-dimethylethoxy) ethyl, 2- (methoxy) propyl, 2-
  • Ci-C ⁇ - alkoxy-Ci-C ⁇ - alkoxy for: Ci-Cg-alkoxy substituted by Ci-Cg-alkoxy as mentioned above, for example for OCH 2 -OCH 3 , OCH 2 -OC 2 H 5 , n-propoxymethoxy, OCH 2 -OCH (CH 3 ) 2 , n-butoxymethoxy, (1-methylpropoxy) methoxy, (2-methylprooxy) methoxy, OCH -OC (CH 3 ) 3 , 2- (methoxy) ethoxy, 2- (ethoxy) ethoxy, 2- (n-propoxy) ethoxy, 2- (l-methylethoxy) ethoxy, 2- (n-butoxy) ethoxy, 2- (1-methylpropoxy) ethoxy, 2- (2- Methylpropoxy) ethoxy, 2- (1, 1-dimethylethoxy) ethoxy, 2- (methoxy) propoxy, 2- (ethoxy) prop
  • (Ci-C ⁇ - alkyl) carbonyl-Ci-Cg-alkoxy for: Ci-Cg-alkoxy substituted by (Ci-C ⁇ - alkyl) carbonyl as mentioned above, for example for OCH 2 -CO-CH 3 , OCH 2 -CO-C 2 H 5 , OCH 2 -CO-CH 2 -C 2 H 5 ,
  • Ci-Cg-alkoxy carbonyl-Ci-Cg-alkoxy for: Ci-Cg-alkoxy substituted by (Ci-Cg-alkoxy) carbonyl as mentioned above, e.g. for OCH 2 -CO-OCH 3 , 0CH 2 -CO-OC 2 H 5 , 0CH -CO-OCH 2 -C 2 H 5 , OCH 2 -CO-OCH (CH 3 ) 2 , n-butoxycarbonyl-methoxy, 1- (methoxycarbonyl) ethoxy, 2- ( Methoxycarbonyl) ethoxy, 2- (ethoxycarbonyl) ethoxy, 2- (n-propoxycarbonyl) ethoxy, 2- (n-butoxycarbonyl) ethoxy, 3- (methoxycarbonyl) ropoxy, 3- (ethoxycarbonyl) propoxy, 3 - (n-Propoxycarbonyl) propoxy, 3- (n-but
  • Ci-Cg-alkoxy carbonyl-Ci-Cg-alkyl for: Ci-Cg-alkyl substituted by (Ci-Cg-alkoxy) carbonyl as mentioned above, e.g. for methoxycarbonylmethyl, ethoxycarbonylmethyl, 1 - (methoxycarbonyl) ethyl, 2 - (methoxycarbonyl) ethyl,
  • Ci-Cg-alkoxy carbonyl as substituted Ci-Cg-alkylsulfonyl as mentioned above, e.g. for methoxycarbonylmethylsulfonyl, ethoxycarbonylmethylsulfonyl, 1- (methoxycarbonyl) ethylsulfonyl, 2- (methoxycarbonyl) ethylsulfonyl, 2- (ethoxycarbonyl) ethylsulfonyl, 3 - (methoxycarbonyl) propylsulfonyl,
  • Ci-Cg-alkylthio-Ci-C ⁇ alkoxy viewed by Ci-Cg-alkylthio as mentioned above substituted C ⁇ alkoxy, eg for 0CH 2 -SCH 3, -SC 2 H 5 0CH 2, 2 0CH -SCH 2 -C 2 H 5 , 0CH 2 - SCH (CH 3 ) 2 , n-butylthiomethoxy, 0CH 2 -SCH (CH 3 ) -CH 5 , 0CH 2 -SCH 2 -CH (CH 3 ) 2 , OCH 2 -SC (CH 3 ) 3 , 2- (SCH 3 ) ethoxy, 2- (SC 2 H 5 ) ethoxy, 2- (SCH 2 -C 2 H 5 ) - ethoxy, 2- [SCH (CH 3 ) 2 1 ethoxy, 2- (n-butylthio) ethoxy, 2- [SCH (CH 3 ) -C 2 H 5 ] ethoxy
  • Ci-Cg-alkylthio- (Ci-Cg-alkyl) carbonyl for: by C ⁇ ⁇ Cg-alkyl- thio as mentioned above, preferably SCH 3 or SC 2 Hs, substituted (Ci-Cg-alkyl) carbonyl, so for example for methyl - thiomethylcarbonyl, ethylthiomethylcarbonyl, 1- (methylthio) ethylcarbonyl, 2 - (methylthio) ethylcarbonyl, 3 - (methylthio) propylcarbonyl, 4 - (methylthio) butylcarbonyl, 5 (methylthio) pentylcarbonyl or 6 - (methylthio) hexylcarbonyl, especially for CO-CH 2 -SCH 3 or CO-CH (CH 3 ) -SCH 3 ;
  • Di (Ci-Cg-alkyl) amino-Ci-Cg-alkoxy by di- (Ci-C ⁇ - alkyl) - amino such as N (CH 3 ) 2 , N (C 2 Hs) 2 , N, N-dipropylamino , N, N-di- (1-methylethyl) mino, N, N-dibutylamino, N, N-di- (1-methylpropyl) amino, N, N-di- (2-methylpropyl) amino, N [ C (CH 3 ) 3 ], 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-methylamin
  • OCH 2 -N (CH 3 ) 2 OCH 2 -N (C 2 H 5 ) 2 , OCH (CH 3 ) -N (CH 3 ) 2 , 2- (dimethylamino) ethoxy, OCH (CH 3 ) -N (C 2 H 5 ) 2 , 3 - (dimethylamino) propoxy, 4 - (dimethylamino) butoxy, 5- (dimethylamino) pentoxy or 6- (dimethylamino) hexoxy, especially for OCH 2 -N (CH 3 ) 2 or OCH (CH 3 ) -N (CH 3 ) 2 ;
  • C 3 -C ⁇ - alkenyl for: eg prop-2-en-l-yl, n-buten-4-yl, l-methyl-prop-2-en-l-yl, 2-methyl-prop-2- en-l-yl, 2-butene-1-yl, n-penten-3-yl, n-penten-4-yl, l-methyl-but-2-en-l-yl, 2-methyl-but- 2-en-l-yl, 3-methyl-but-2-en-l-yl, 1-methyl-but-3-en-l-yl, 2-methyl-but-3-en-l-yl, 3-methyl-but-3-en-1-yl, 1, l-dimethyl-prop-2-en-l-yl, 1, 2-dimethyl-prop-2-en-1-yl, l-ethyl- prop-2-en-l-yl, n-hex-3-en-l-yl, n-hex-4-en-1-yl, n
  • C 2 -Cg alkenyl for: ethenyl or one of the radicals mentioned under C 3 -Cg alkenyl, in particular for ethenyl or prop-2-en-yl;
  • C 3 -Cg alkenyloxy for: prop-1-en-l-yloxy, prop-2-en-l-yloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n- Buten-3-yloxy, 1-methyl-prop-l-en-l-yloxy, 2-methyl-prop-1-en-l-yloxy, l-methyl-prop-2-en-l-yloxy, 2- Methyl-prop-2-en-l-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, 1-methyl-but- 1-en-l-yl-oxy, 2-methyl-but-l-en-l-yloxy, 3-methyl-but-l-en-l-yloxy, l-methyl-but-2-en-l- yloxy, 2-methyl-but-2-en-l
  • C 2 -Cg alkenyloxy for: ethenyloxy or one of the radicals mentioned under C 3 -Cg alkenyloxy, in particular for ethenyloxy or prop-2-en-l-yloxy;
  • C 3 -Cg haloalkenyloxy for: C -C alkenyloxy as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for example 2-chloroallyloxy, 3-chloroallyloxy, 2, 3-dichloroallyloxy, 3, 3-dichloroallyloxy, 2, 3, 3-trichlorallyloxy, 2, 3-dichlorobut-2-enyloxy, 2-bromo-allyloxy, 3-bromoallyloxy, 2, 3-dibrornallyloxy, 3,3-dibromo-allyloxy, 2, 3, 3-tribromoallyloxy or 2,3-dibromobut-2-enyloxy, in particular for 2-chloroallyloxy or 3,3-dichloroallyloxy;
  • Phenyl-C 3 -Cg-alkenyloxy for: eg 3-phenyl-allyloxy, 4-phenyl-but-2-enyloxy, 4-phenyl-but-3-enyloxy or 5-phenyl-pent-4-enyloxy, preferably 3 -Phenylallyloxy or 4-phenyl-but-2-enyloxy, especially for 3 -phenylallyloxy;
  • C 3 -C ⁇ alkynyl for: prop-1-in-l-yl, prop-2-in-l-yl, n-but-1-in-l-yl, n-but-l-in-3 -yl, n-but-l-in-4-yl, n-but-2-in-l-yl, n-pent-1-in-l-yl, n-pent-l-in-3-yl , n-pent-1-in-4-yl, n-pent-1-in-5-yl, n-pent-2-in-1-yl, n-pent-2-in-4-yl, n Pent-2-in-5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n-hex-1-in-l-yl , n-hex-1-in-3-yl, n-hex-1-in-4-yl, n-hex-1-
  • - C -C ⁇ alkynyl for: ethynyl or one of the radicals mentioned under C 3 -C 6 -alkynyl, in particular for ethynyl or prop-2-yn-1-yl;
  • C 3 -Cg alkynyloxy for: prop-1-in-l-yloxy, prop-2-in-l-yloxy, n-but-1-in-l-yloxy, n-but-l-in-3- yloxy, n-but-l-in-4-yloxy, n-but-2-in-l-yloxy, n-pent-1-in-l-yloxy, n-pent-l-in-3-yloxy, n-pent-l-in-4-yloxy, n-pent-l-in-5-yloxy, n-pent-2-in-l-yl-oxy, n-pent-2-in-4-yloxy, n-pent-2-in-5-yloxy, 3-methyl-but-l-in-3-yloxy, 3-methyl-but-l-in-4-yloxy, n-hex-1-in-l- yl-oxy, n-hex-l-in-3-y
  • C 2 -Cg alkynyloxy for: ethynyloxy or one of the radicals mentioned under C 3 -Cg alkynyloxy, in particular for ethynyloxy or prop-2-yn-l-yloxy;
  • Phenyl-C 3 -Cg-alkynyloxy for: e.g. 3-phenylprop-2-in-1-yloxy, 4-phenylbut-2-in-1-yloxy, 3-phenylbut-3-in-2-yloxy, 5-phenyl pent-3-in-1-yloxy or 6-phenylhex-4-in-1-yloxy, in particular for 3-phenylprop-2-in-1-yloxy or 3-phenylbut-3-in-2-yloxy;
  • Heterocyclyl-C 3 -Cg-alkynyloxy for: e.g. 3- (heterocyclyl) prop- 2-in-l-yloxy, 4- (heterocyclyl) but-2-in-l-yloxy, 3- (heterocyclic) but- 3-in-2-yloxy, 5- (heterocyclyl) pent-3-in-l-yloxy or 6- (heterocyclyl) hex-4-in-l-yloxy, especially for 3- (heterocyclyl) prop-2-in -l-yloxy or 3- (heterocyclyl) but-3-in-2-yloxy;
  • C -C ⁇ alkynylthio for: ethynylthio or one of the radicals mentioned under C 3 -C ⁇ alkynylthio, in particular for ethynylthio or prop-2-yn-l-ylthio;
  • (C 3 -C ⁇ - alkenyloxy) carbonyl for: prop-1-en-l-yloxycarbonyl, prop-2-en-l-yloxycarbonyl, 1-methylethenyloxycarbonyl, n-buten-1-yloxycarbonyl, n-butene-2- yloxycarbonyl, n-butene-3-yloxycarbonyl, 1-methyl-prop-l-en-l-yloxycarbonyl, 2-methyl-prop-1-en-l-yloxycarbonyl, 1-methyl-prop-2-en-l- yloxycarbonyl, 2-methyl-prop-2-en-l-yloxycarbonyl, n-pentene-1-yloxycarbonyl, n-pentene-2-yloxycarbonyl, n-pentene-3-yloxycarbonyl, n-pentene-4- yloxycarbonyl, 1-methyl-but-l-en-l-yloxycarbonyl,
  • (C 3 -Cg-Alkenyloxy) carbonyl-Ci-Cg-alkyl for: by (C 3 -Cg-Alkenyloxy) carbonyl as mentioned above, preferably - Prop-2-en-l-yl-oxycarbonyl, substituted Ci-C ⁇ - alkyl, for example prop-2-en-1-yl-oxycarbonyl -methyl;
  • (C 2 -C ⁇ - alkenyl) carbonyloxy for: ethenylcarbonyloxy, prop-1-en-l-ylcarbonyloxy, prop-2-en-l-ylcarbonyloxy, 1-methyl-ethenylcarbonyloxy, n-buten-1-ylcarbonyloxy, n- Buten-2-ylcarbonyloxy, n-buten-3-ylcarbonyloxy, 1-methyl-prop-l-en-1-ylcarbonyloxy, 2-methyl-prop-1-en-l-ylcarbonyloxy, l-methyl-prop- 2-en-l-ylcarbonyloxy, 2-methyl-prop-2-en-l-yl-carbonyloxy, n-penten-1-ylcarbonyloxy, n-penten-2-ylcarbonyl-oxy, n-penten-3-ylcarbonyloxy, n-penten-4-ylcarbonyloxy,
  • (C -C ⁇ - alkenyl) carbonylthio for: ethenylcarbonylthio, prop-1-en-l-ylcarbonylthio, prop-2-en-l-ylcarbonylthio, 1-methylethenylcarbonylthio, n-buten-1-ylcarbonylthio, n-butene -2-yl-carbonylthio, n-buten-3-ylcarbonylthio, 1-methyl-prop-l-en-1-ylcarbonylthio, 2-methyl-prop-l-en-l-ylcarbonylthio, l-methyl-prop-2 -en-l-ylcarbonylthio, 2-methyl-prop-2-en-l-yl-carbonylthio, n-penten-1-ylcarbonylthio, n-penten-2-yl-carbonylthio, n-penten-3-ylcarbonylthio, n -Pentene
  • (C 2 -C 6 alkynyl) carbonyloxy for: ethynylcarbonyloxy, prop-1-in-1-ylcarbonyloxy, prop-2-in-1-ylcarbonyloxy, n-but-1-in-1-ylcarbonyloxy, n-but-1 -in-3-ylcarbonyloxy, n-but-l-in-4-ylcarbonyloxy, n-but-2-in-l-ylcarbonyloxy, n-pent-1-in-l-ylcarbonyloxy, n-pent-l-in -3-ylcarbonyloxy, n-pent-l-in-4-ylcarbonyloxy, n-pent-l-in-5-ylcarbonyloxy, n-pent-2-in-l-ylcarbonyloxy, n-pent-2-in-4 -ylcarbonyloxy, n-pent-2-in-5-ylcarbonyloxy, n-p
  • C 3 -Cg alkynylsulfonyloxy for: prop-1-in-l-ylsulfonyloxy, prop-2-in-l-ylsulfonyloxy, n-but-1-in-1-ylsulfonyloxy, n-but-l-in-3- ylsulfonyloxy, n-but-l-in-4-ylsulfonyloxy, n-but-2-in-l-ylsulfonyloxy, n-pent-1-in-l-ylsulfonyloxy, n-pent-l-in-3-ylsulfonyloxy, n-pent-l-in-4-ylsulfonyloxy, n-pent-l-in-5-ylsulfonyloxy, n-pent-2-in-1-ylsulfonyloxy, n-pent-2-in-4-ylsulfon
  • (Ci-Cg-alkoxy) carbonyl -C -Cg alkenyl for: C 2 -Cg alkenyl substituted by (Ci-Cg-alkoxy) carbonyl as mentioned above, for example for methoxycarbonyl-prop-2 -en- 1 -yl;
  • Ci-Cg-alkenyloxy for: C 3 -Cg -alkenyloxy substituted by Ci-Cg-alkoxy as mentioned above, for example for methylprop-2-en-l-yloxy;
  • C 3 -Cg-alkenyloxy-C ⁇ -Cg-alkyl for: by C 3 -Cg-alkenyloxy as mentioned above, preferably allyloxy, 2-methyl-prop-2-en-l-yloxy, but-l-en-3- yloxy, but-l-en-4-yloxy or but-2-en-l-yloxy-substituted Ci-Cg-alkyl, for example for allyloxymethyl, 2-allyloxyethyl or but-l-en-4-yloxymethyl;
  • C 3 -C alkynyloxy ⁇ -C ⁇ -C alkyl ⁇ viewed by C 3 -C 6 alkynyloxy as mentioned above, preferably propargyloxy, but-l-yn-3-yl-oxy, but-l-yn-4 -yloxy or but-2-yn-l-yloxy, substituted Ci-C ⁇ alkyl, for example for propargyloxymethyl or 2-propargyloxyethyl;
  • C -C 6 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
  • C 3 -Cg cycloalkyloxy for: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy;
  • C 3 -Cg cycloalkylthio for: cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio;
  • C 3 -Cg cycloalkylcarbonyloxy for: cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy or cyclohexylcarbonyloxy;
  • C 3 -Cg cycloalkylsulfonyloxy for: cyclopropylsulfonyloxy, cyclobutylsulfonyloxy, cyclopentylsulfonyloxy or cyclohexylsulfonyloxy;
  • C 5 -C 7 cycloalkenyloxy for: cyclopent-1-enyloxy, cyclopent-2-enyloxy, cyclopent-3-enyloxy, cyclohex-1-enyloxy, cyclohex-2-enyloxy, cyclohex-3-enyloxy, cyclohept-1 - enyloxy. Cyclohept-2-enyloxy, Cyclohept-3-enyloxy or Cyclohept -4-enyloxy.
  • 3- to 7-membered azaheterocycles which in addition to carbon ring members may also contain an oxygen or sulfur atom as a ring member, are e.g.
  • saturated heterocycles which can contain a carbonyl or thiocarbonyl ring member are:
  • unsaturated heterocycles which can contain a carbonyl or thiocarbonyl ring member are:
  • heteroaromatics the 5- and 6-membered ones are preferred, e.g.
  • Furyl such as 2-furyl and 3-furyl, thienyl such as 2-thienyl and 3-thienyl, pyrrolyl such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl such as
  • 2-oxazolyl 4-oxazolyl and 5-oxazolyl
  • thiazolyl such as 2-thiazolyl
  • 4-thiazolyl and 5-thiazolyl imidazolyl such as 2-imidazolyl and 4-imidazolyl, oxadiazolyl such as 1, 2, 4-oxadiazol-3-yl,
  • the variables preferably have the following meanings, in each case individually or in combination:
  • R 1 is hydrogen, amino or methyl, especially methyl
  • R 2 is hydrogen, halogen or methyl
  • R 3 is hydrogen, halogen or methyl, in particular a) hydrogen or halogen, particularly preferably hydrogen; b) hydrogen or methyl, particularly preferably methyl; c) halogen or methyl, particularly preferably halogen;
  • R 5 cyano or halogen, in particular a) cyano; b) chlorine;
  • R 6 on the one hand, together with R 5, a radical -N (R 7 ) -CO-C (R 8 ', R 9 ') -0- bonded to R 5 via oxygen;
  • Ci-Cg-alkoxy Ci-C-alkylthio, C 3 -Cg-cycloalkoxy, C 3 -Cg-cycloalkylthio, C 2 -Cg-alkenyloxy, C 2 -Cg-alkenylthio, C 2 -Cg-alkynyloxy, C 2 -Cg-alkynylthio, (Ci-Cg-alkyl) - carbonyloxy, (Ci-Cg-alkyl) carbonylthio, (C -C ⁇ - alkoxy) - carbonyloxy, (C 2 -Cg-alkenyl) carbonyloxy, (C 2 - Cg-alkenyl) - carbonylthio, (C 2 -Cg-alkynyl) carbonyloxy, (C 2 -Cg-alkynyl) - carbonylthio, Ci-Cg-alkylsulfonyloxy or Ci-
  • Halogen, nitro, cyano, hydroxyl, C 3 -Cg-cycloalkyl, Ci-Cg-alkoxy, C 3 -Cg-cycloalkoxy, C -Cg-alkenyloxy, C 3 -Cg-alkynyloxy, C ⁇ -Cg-alkoxy-C ⁇ -Cg -alkoxy, Ci-Cg-alkylthio, Ci-Cg-alkylsulfinyl, Ci-Cg-alkyl - sulfonyl, Ci-C ⁇ -alkylidenaminoxy, oxo, N-0R 11 , the phenyl, phenoxy or phenylsulfonyl group, which are unsubstituted or can carry one to three substituents each selected from the group consisting of halogen, nitro, cyano, Ci-C ⁇ -alkyl, C ⁇ haloalkyl, C ⁇ -C 6 -al
  • R 6 in particular 2) Ci-Cg-alkoxy, C -Cg-alkenyloxy or C-Cg-alkynyloxy, where each of the latter 3 radicals can optionally carry one to three substituents, each selected from the group consisting of halogen, Ci-Cg- Alkoxy, C 3 -C ⁇ - alkenyloxy, C 3 -Cg-alkynyloxy, Ci-Cg-alkylsulfonyl, -CO-R 12 , -CO-OR 12 , -CO-N (R 12 ) R 13 , -N (R 12 ) -R 13 and
  • -C (R 14 ) N-OR 1: L ; 3) -CO-R 15, -C (NR ") -R l5, -C (R 15) (OR 17) (OR 18),
  • R 8 , R 9 , R 8 ', R 9 ' hydrogen.
  • the l-aryl-4-thiouracils of the formula I can be obtained in various ways, in particular by one of the following processes:
  • the sulfurization is usually carried out in an inert solvent or diluent, for example in an aromatic hydrocarbon such as toluene and the xylenes, in an ether such as diethyl ether, 1, 2-dimethoxyethane and tetrahydrofuran, or in an organic amine such as pyridine.
  • an inert solvent or diluent for example in an aromatic hydrocarbon such as toluene and the xylenes, in an ether such as diethyl ether, 1, 2-dimethoxyethane and tetrahydrofuran, or in an organic amine such as pyridine.
  • Phosphorus (V) sulfide and 2,4-bis (4-methoxyphenyl) -1,3,4,4-dithiadiphosphetane-2,4-dithione are particularly suitable as the sulfurization reagent.
  • the reaction temperature is normally 20 to 200 ° C, preferably 40 ° C to the boiling point of the reaction mixture.
  • the preliminary products II are known from WO 97/05117 or can be produced in an analogous manner by one of the processes described there.
  • the reaction is particularly successful when IV carries an electron-withdrawing group ortho or para to the fluorine atom.
  • a fluoroaromatic which can be converted into IV can also be used.
  • L 1 , L 2 , L 3 each represent customary hydroxyl protective groups such as methyl, ethyl, methylsulfonyl, benzyl and trimethylsilyl.
  • the usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, for example sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium -, potassium or calcium carbonate, sodium, Potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n- or iso-propanolate, n-, iso-, sec- or tert-butoxide; also basic organic nitrogen compounds, for example trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexy
  • the processes (B)) and (C)) according to the invention for the preparation of the compound of the formula (I) are preferably carried out in the presence of a diluent.
  • a diluent is generally suitable as diluents. These preferably include aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons, for example pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane (methylene chloride), trichloromethane (chloroform) Tetrachloromethane, dialkyl ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether (MTBE), ethyl tert-butyl ether,
  • TAME pentyl ether
  • THF tetrahydrofuran
  • 1,4-dioxane 1,4-dioxane
  • ethylene glycol dimethyl ether ethylene glycol diethyl ether, diethylene glycol dimethyl ether and diethyl ether
  • Dialkyl ketones such as acetone, butanone (methyl ethyl ketone), methyl isopropyl ketone and methyl isobutyl ketone
  • Nitriles such as acetonitrile, propionitrile, butyronitrile and benzonitrile
  • Amides such as N, N-dimethylformamide (DMF), N, N-dimethyl-acetamide, N-methylformanilide, N-methylpyrrolidone and hexamethylphosphoric acid triamide
  • Esters such as methyl acetate, ethyl ester, n-propyl ester, isopropyl ester, n
  • reaction temperatures can be varied within a substantial range when carrying out processes (B)) and (C)). In general, temperatures from 0 to 200 ° C, preferably at 10 to 150 ° C, especially at 20 ° C to the boiling point of the respective reaction mixture.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess, for example up to twice the molar amount of the other component. In process A), for example, it is advisable to use the sulfurization reagent in excess.
  • the processes (A>), (B)) and (C)) are advantageously carried out at atmospheric pressure or under the autogenous pressure of the respective reaction mixture. However, it is also possible to carry out the processes under increased or reduced pressure - generally at 0.1 to 10 bar.
  • the respective reaction mixtures are generally worked up by methods known per se, for example by diluting the reaction solution with water and then isolating the product by means of filtration, crystallization or solvent extraction, or by removing the solvent, and distributing the residue in a mixture of water and a suitable organic solvent and working up the organic phase on the product.
  • the l-aryl-4-thiouracile I can be prepared by one of the synthesis methods mentioned above.
  • the l-aryl-4-thiouracils I can be obtained in the preparation as isomer mixtures, which, however, can, if desired, be separated into the pure isomers by the customary methods such as crystallization or chromatography, including on an optically active adsorbate. Pure optically active isomers can advantageously be prepared from corresponding optically active starting products.
  • Agricultural salts of the compounds I can be formed by reaction with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride, or by reaction with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • Salts of I can also be prepared in a conventional manner by salting the corresponding alkali metal salt, as can ammonium, phosphonium, sulfonium and sulfoxonium salts using ammonia, phosphonium, sulfonium or sulfoxonium hydroxides.
  • the compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, maize, soybeans and cotton, they work against weeds and grass weeds without causing any significant damage to crops. This effect occurs especially at low application rates.
  • the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are considered, for example:
  • Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarle, Seeale Solanum tuberosum, Sorghum bicolor (S. vulgäre), Theobroma cacao, Tri- folium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea ays.
  • the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • the compounds I or the herbicidal compositions comprising them can be sprayed or atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • mineral oil fractions of medium to high boiling point such as
  • Kerosene and diesel oil also coal tar oils as well as 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, strongly 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
  • strongly polar solvents e.g.
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the l-aryl-4-thiouracile I as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • the surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols and of fatty alcohol glycol ether, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl poly
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coating, impregnation and homogeneous granules 15 can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate , Ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • the concentrations of the active ingredients I in the ready-to-use preparations can be varied within a wide range.
  • the formulations contain about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are in a purity of
  • the active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
  • the application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.) depending on the control target, the season, the target plants and the growth stage.
  • the l-aryl-4-thiouracile I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels.
  • the seeds of the test plants were sown separately according to species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
  • the tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.
  • test plants For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. 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 the post-emergence application was only 31.3 and 15.6 g / ha a.s.
  • the plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
  • Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
  • Table 2 shows the superior herbicidal activity of the compound No. Ib.3 in comparison to the comparative compound A known from WO 97/05117 (Example 3 there)

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Abstract

The invention relates to novel 1-aryl-4-thiouracils of formula (I), to their salts/enolethers used as herbicides, whereby R1 = H, NH¿2?, C1-C6-alkyl; R?2¿ = H, halogen, C¿1?-C4-alkyl, C1-C4-alkyl halide; R?3¿ = H, halogen, C¿1?-C6-alkyl, methyl halide; R?4¿ = H, halogen; R5 = CN, halogen, -CO-NH¿2?, -CS-NH2, -OC(R?8,R9¿)-CO-O(C¿1?-C6-alkyl); Y = N, CH, or together with R?6¿, a bridge ⊃C-O-C(R?10)=N-; R6¿, together with R5, = a radical -N(R7)-C(O/S)-C(R8',R9')-O- bound to R5 via the oxygen, or 1) H, OH, SH, CN, NO¿2?, halogen, C1-C6-alkyl, C1-C6-alkyl halide, C1-C6-alkoxy halide, C1-C6-alkylthio halide, C1-C6-alkylthio-(C1-C6-alkyl)carbonyl, (C1-C6-alkyl)imino-oxycarbonyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxyamino-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkylamino-C1-C6-alkyl, 2) optionally substituted C1-C6-alkoxy, C1-C6-alkylthio, C3-C6-cycloalkoxy, C3-C6-cycloalkylthio, C2-C6-alkenyloxy, C2-C6-alkenylthio, C2-C6-alkynyloxy, C2-C6-alkynylthio, (C1-C6-alkyl)carbonyloxy, (C1-C6-alkyl)carbonylthio, (C1-C6-alkoxy)carbonyloxy, (C2-C6-alkenyl)carbonyloxy, (C2-C6-alkenyl)carbonylthio, (C2-C6-alkynyl)carbonyloxy, (C2-C6-alkynyl)carbonylthio, C1-C6-alkylsulfonyloxy or C1-C6-alkylsulfonyl, 3) 28 additional radicals; R?7¿ = H, optionally substituted C¿1?-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl or C3-C6-cycloalkoxy; R?8, R9, R8', R9'¿ = H, CN, C¿1?-C6-alkyl; R?10¿ = H, halogen, optionally substituted C¿1?-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl or C3-C6-cycloalkoxy.

Description

Neue l-Aryl-4-thiouracileNew l-aryl-4-thiouracile
Beschreibungdescription
Die vorliegende Erfindung betrifft neue l-Aryl-4-thiouracile der Formel IThe present invention relates to novel l-aryl-4-thiouracils of the formula I.
Figure imgf000003_0001
in der die Variablen folgende Bedeutungen haben:
Figure imgf000003_0001
in which the variables have the following meanings:
X Sauerstoff oder Schwefel;X oxygen or sulfur;
R1 Wasserstoff, Amino oder Ci-Cδ-Alkyl;R 1 is hydrogen, amino or Ci-C δ alkyl;
R2 Wasserstoff, Halogen, Cι-C-Alkyl oder Cι-C-Halogenalkyl;R 2 is hydrogen, halogen, -CC alkyl or -C-haloalkyl;
R3 Wasserstoff, Halogen, Ci-Cδ-Alkyl oder Halogenmethyl;R 3 is hydrogen, halogen, Ci-C δ alkyl or halomethyl;
R4 Wasserstoff oder Halogen;R 4 is hydrogen or halogen;
R5 Cyano, Halogen, -CO-NH2, -CS-NH2 oder -OC (R8 , R9) -CO-0 (Cι-C6-Alkyl) ;R 5 cyano, halogen, -CO-NH 2 , -CS-NH 2 or -OC (R 8 , R 9 ) -CO-0 (-C-C 6 alkyl);
Y Stickstoff, die Methingruppe oder zusammen mit R6 eine Brücke >C-O-C(R10)=N-;Y nitrogen, the methine group or together with R 6 a bridge> COC (R 10 ) = N-;
R6 zusammen mit R5 einen über den Sauerstoff an R5 gebundenen Rest -N(R7)-CZ1-C(R8',R9')-0-, oderR 6 together with R 5 is a radical -N (R 7 ) -CZ 1 -C (R 8 ', R 9 ') -0- which is bonded to R 5 via the oxygen, or
1) Wasserstoff, Hydroxy, Mercapto, Cyano, Nitro, Halogen, Ci-Cβ-Alkyl, Ci-Cß-Halogenalkyl, Cχ-C6-Halogenalkoxy, Ci-Cδ-Halogenalkylthio, Ci-Cδ-Alkylthio- (Cι-C6-alkyl) - carbonyl, (Ci-Cδ-Alkyl) i inooxycarbonyl, Cχ-C6-Alkoxy- Cι-C6-al yl, Cx-Ce-Alkoxyamino-Ci-Cδ-alkyl, Ci-Ce-Alk- oxy-Ci-Cß -alkylamino-Ci - Cζ -alkyl,1) hydrogen, hydroxy, mercapto, cyano, nitro, halogen, Ci-Cβ-alkyl, Ci-C ß -haloalkyl, Cχ-C 6 -haloalkoxy, Ci-C δ -haloalkylthio, Ci-C δ -alkylthio- (Cι -C 6 -alkyl) - carbonyl, (Ci-C δ- alkyl) i inooxycarbonyl, Cχ-C 6 -alkoxy- Cι-C 6 -al yl, Cx-Ce-alkoxyamino-Ci-C δ -alkyl, Ci- Ce-alkoxy-Ci-C ß -alkylamino-Ci - Cζ -alkyl,
2) Ci-Cδ-Alkoxy, Cι-C6 -Alkylthio, C3-C6-Cycloalkoxy, C3-C6- Cycloalkylthio, C2-C6-Alkenyloxy, C -C6-Alkenylthio, C2-C6-Alkinyloxy, C2-C6-Alkinylthio, (Ci-Cδ-Alkyl) - carbonyloxy, (Ci-Cδ-Alkyl) carbonylthio, (Ci-Cβ-Alkoxy) - carbonyloxy, (C -C6-Alkenyl) carbonyloxy, (C -C6-Alkenyl) - carbonylthio, (C -C6-Alkinyl) carbonyloxy, • (C2-C6-Alkinyl) - carbonylthio, Cι-C6-Alkylsulfonyloxy oder Ci -C6 -Alkyl - sulfonyl, wobei jeder dieser 17 Reste gewünschtenfalls einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus2) Ci-C δ alkoxy, Cι-C 6 alkylthio, C 3 -C 6 cycloalkoxy, C 3 -C 6 - cycloalkylthio, C 2 -C 6 alkenyloxy, C -C 6 alkenylthio, C 2 - C 6 -alkynyloxy, C 2 -C 6 -alkynylthio, (Ci-C δ- alkyl) - carbonyloxy, (Ci-C δ- alkyl) carbonylthio, (Ci-Cβ-alkoxy) - carbonyloxy, (C -C 6 - Alkenyl) carbonyloxy, (C -C 6 -alkenyl) - carbonylthio, (C -C 6 -alkynyl) carbonyloxy, • (C 2 -C 6 -alkynyl) - carbonylthio, -CC 6 alkylsulfonyloxy or C 1 -C 6 alkylsulfonyl, where each of these 17 radicals can optionally carry one to three substituents, each selected from the group consisting of
Halogen, Nitro, Cyano, Hydroxy, C3-C6-Cycloalkyl, Ci-Cδ-Alkoxy, C3-C6~Cycloalkoxy, C3-C6-Alkenyloxy, C3-C6-Alkinyloxy, Ci-Cg-Alkoxy-Ci-Cδ-alkoxy, Cι-C6-Alkylthio, Cι-C6-Alkylsulfinyl, Cι-C6-Alkyl- sulfonyl, Ci-Cδ-Alkylidenaminoxy, Oxo, =N-OR1:L,Halogen, nitro, cyano, hydroxy, C 3 -C 6 cycloalkyl, Ci-C δ alkoxy, C 3 -C6 ~ cycloalkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, Ci-Cg- alkoxy-Ci-C δ -alkoxy, C 6 alkylthio, Cι-C 6 alkylsulfinyl, Cι-C 6 alkyl sulfonyl, Ci-C δ -Alkylidenaminoxy, oxo, = N-OR 1: L,
der Phenyl-, Phenoxy- oder Phenylsulfonylgruppe, die unsubstituiert sein oder ein bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Halogen, Nitro, Cyano, Cι-C6-Alkyl,the phenyl, phenoxy or phenylsulfonyl group, which may be unsubstituted or bear one to three substituents, in each case selected from the group consisting of halogen, nitro, cyano, C 1 -C 6 -alkyl,
Ci-Cδ-Halogenalkyl, Ci-Cg-Alkoxy und (Cι-C6-Alkoxy) - carbonyl ,Ci-C δ -haloalkyl, Ci-Cg-alkoxy and (Cι-C 6 -alkoxy) carbonyl,
einer Gruppe -CO-R12, -CO-OR12, -CO-SR12, -CO-N(R12)-R13, -OCO-R12, -OCO-OR12, -OCO-SR12,a group -CO-R 12 , -CO-OR 12 , -CO-SR 12 , -CO-N (R 12 ) -R 13 , -OCO-R 12 , -OCO-OR 12 , -OCO-SR 12 ,
-OCO-N(R12) -R13, -N(R12)-R13 oder -C (R14) =N-ORι:L;-OCO-N (R 12 ) -R 13 , -N (R 12 ) -R 13 or -C (R 14 ) = N-OR ι: L ;
3) -CZ2-R15, -C(NR16) -R", -C(R15) (ZR17) (Z R18) , -C (R15) =C (R19) -CN, -C (R15) =C (R19) -CO-R20, -CH(R15)-CH(R19)-CO-R20, -C (R15) =C (R19) -CH2-CO-R20,3) -CZ 2 -R 15 , -C (NR 16 ) -R ", -C (R 15 ) (ZR 17 ) (ZR 18 ), -C (R 15 ) = C (R 19 ) -CN, - C (R 15 ) = C (R 19 ) -CO-R 20 , -CH (R 15 ) -CH (R 19 ) -CO-R 20 , -C (R 15 ) = C (R 19 ) -CH 2 -CO-R 20 ,
-C (R15) =C (R19) -C (R21) =C (R22) -CO-R20,-C (R 15 ) = C (R 19 ) -C (R 21 ) = C (R 22 ) -CO-R 20 ,
-C(R15)=C(R19)-CH2-CH(R23)-CO-R20, -CO-OR24, -CO-SR24, -CO-N(R24) -OR11, -C≡C-CO-NH-OR11, -C-≡C-CO-N(R24) -OR11, -C≡C-CS-NH-OR11, -C≡C-CS-N(R24) -OR11, -C(R15)=C(R19)-CO-NH-OR11, -C (R15) =C (R19) -CO-N (R24) -OR11,-C (R 15 ) = C (R 19 ) -CH 2 -CH (R 23 ) -CO-R 20 , -CO-OR 24 , -CO-SR 24 , -CO-N (R 24 ) -OR 11 , -C≡C-CO-NH-OR 11 , -C-≡C-CO-N (R 24 ) -OR 11 , -C≡C-CS-NH-OR 11 , -C≡C-CS-N (R 24 ) -OR 11 , -C (R 15 ) = C (R 19 ) -CO-NH-OR 11 , -C (R 15 ) = C (R 19 ) -CO-N (R 24 ) -OR 11 ,
-C(R15)=C(R19) -CS-NH-OR11, -C (R15) =C (R19) -CS-N(R24) -OR11, -C (R15) =C (R19) -C (R14) =N-OR", -C (R14) =N-OR11, -C≡C-C(R1 )=N-OR1:L, -C(Z3R17) (Z R18) -OR24, -C(ZR17) (ZR18) -SR24, -C(ZR17) (Z R18) -N(R25)R26, -N{R25)-R26 oder -CO-N(R25) -R26;-C (R 15 ) = C (R 19 ) -CS-NH-OR 11 , -C (R 15 ) = C (R 19 ) -CS-N (R 24 ) -OR 11 , -C (R 15 ) = C (R 19 ) -C (R 14 ) = N-OR ", -C (R 14 ) = N-OR 11 , -C≡CC (R 1 ) = N-OR 1: L , -C (Z 3 R 17 ) (ZR 18 ) -OR 24 , -C (ZR 17 ) (ZR 18 ) -SR 24 , -C (ZR 17 ) (ZR 18 ) -N (R 25 ) R 26 , -N {R 25 ) -R 26 or -CO-N (R 25 ) -R 26 ;
Z1, Z2, Z3, Z4 unabhängig voneinander Sauerstoff oder Schwefel;Z 1 , Z 2 , Z 3 , Z 4 independently of one another oxygen or sulfur;
R7 Wasserstoff, Ci-Ce-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, Ci-Cδ-Alkoxy, C3-C6~Alkenyloxy, C3-C6-Alkinyloxy, C3-Cg-Cyclo- alkyl oder C3-Cg-Cycloalkoxy, wobei jeder der letztgenannten 8 Reste gewünschtenfalls einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Nitro, Cyano, Halogen, =0, =N-OR1:L' , Cι-C6-Alkoxy, -CO-R12', -CO-OR12', -CO-SR12' und -C (R14' ) =N-OR1:L' ; R8, R9, R8', R9' unabhängig voneinander Wasserstoff, Cyano oderR 7 is hydrogen, Ci-Ce-alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, Ci-C δ alkoxy, C 3 -C 6 ~ alkenyloxy, C 3 -C 6 alkynyloxy, C 3 -Cg-cycloalkyl or C 3 -Cg-cycloalkoxy, where each of the latter 8 radicals can optionally carry one to three substituents, each selected from the group consisting of nitro, cyano, halogen, = 0, = N-OR 1 : L ', -CC 6 alkoxy, -CO-R 12 ', -CO-OR 12 ', -CO-SR 12 ' and -C (R 14 ') = N-OR 1: L '; R 8 , R 9 , R 8 ', R 9 ' independently of one another are hydrogen, cyano or
Ci-Cδ-Alkyl;Ci-C δ alkyl;
R10 Wasserstoff, Halogen, Cι-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, Ci-Cδ-Alkoxy, C3-C6~Alkenyloxy, C3-C6-Alkinyl- oxy, C3-C6-Cycloalkyl oder C3-C6-Cycloalkoxy, wobei jeder der letztgenannten 8 Reste gewünschtenfalls einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Nitro, Cyano, Halogen, =0, =N-0R1:L", Ca-Ce-Alkoxy, -CO-R12", -CO-OR12", -CO-SR12" und -C(R14' ')=N-0R1:L' ' ;R 10 is hydrogen, halogen, -CC 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, Ci-Cδ alkoxy, C 3 -C 6 ~ alkenyloxy, C 3 -C 6 alkynyl - oxy, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkoxy, where each of the latter 8 radicals can optionally carry one to three substituents, each selected from the group consisting of nitro, cyano, halogen, = 0, = N-0R 1: L ", Ca-Ce alkoxy, -CO-R 12 ", -CO-OR 12 ", -CO-SR 12 " and -C (R 14 '') = N-0R 1: L '';
R11, R11', R11" unabhängig voneinanderR 11 , R 11 ', R 11 "independently of one another
Wasserstoff, Ci-Cß-Alkyl, Ci-Cg-Halogenalkyl, C3-C6-Cyclo- alkyl, C3-Ce-Alkenyl, C3-C6-Alkinyl, Hydroxy-Cι-C6-alkyl, Ci-Cε-Alkoxy-Ci-Ce-alkyl , C;ι.-C6-Alkylthio-Cι-C6-alkyl , Cyano-Ci-Cδ-alkyl, (Ci-Cδ-Alkyl) carbonyl-Ci-Cδ-alkyl, (Ci-Cδ-Alkoxy) carbonyl-Ci-Cδ-alkyl, (Ci-Cδ-Alkoxy) carbonyl - C2-C6-alkenyl, (Ci-Cg-Alkyl) carbonyloxy-Cι-C6-alkyl oder Phenyl-Ci-Cδ-alkyl, wobei der Phenylring gewünschtenfalls ein bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Cι-C6-Alkyl, Cι-C6-Halogenalkyl, Ci-Cg-Alkoxy und (Cι-C6-Alkoxy) carbonyl;Hydrogen, Ci-C ß- alkyl, Ci-Cg-haloalkyl, C 3 -C 6 cycloalkyl, C 3 -Ce alkenyl, C 3 -C 6 alkynyl, hydroxy-Cι-C 6 alkyl, Ci -Cε-alkoxy-Ci-Ce-alkyl, C; ι . -C 6 -Alkylthio -CC 6 -alkyl, cyano-Ci-C δ -alkyl, (Ci-C δ- alkyl) carbonyl-Ci-C δ -alkyl, (Ci-C δ -alkoxy) carbonyl-Ci -C δ- alkyl, (Ci-C δ -alkoxy) carbonyl - C 2 -C 6 -alkenyl, (Ci-Cg-alkyl) carbonyloxy -CC 6 -alkyl or phenyl-Ci-C δ -alkyl, where if desired, the phenyl ring can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and (C 1 -C 6 alkoxy) ) carbonyl;
R12, R12', R12'' unabhängig voneinanderR 12 , R 12 ', R 12 ''independently of each other
Wasserstoff, Ci-Cδ-Alkyl, C3-C6-Cycloalkyl, C3-Cδ-Alkenyl, C3-C6-Alkinyl, Cι-C6-Alkoxy-Cι-C6-alkyl, (Cι-C6-Alkoxy) - carbonyl-Cι-C6~alkyl , (C3 -C6 -Alkenyloxy) carbonyl -Ci -C6 -alkyl , Phenyl oder Phenyl-Cι-C6-alkyl, wobei die Phenylgruppe und der Phenyl-Ring der Phenylalkylgruppe unsubstituiert sein oder einen bis drei Reste tragen können, jeweils ausgewählt aus der Gruppe bestehend aus Halogen, Nitro, Cyano, Ci-Cδ-Alkyl, Ci-Cö-Halogenalkyl, Ci-Cδ-Alkoxy und (Ci-Cg-Alkyl) carbonyl;Hydrogen, Ci-C δ- alkyl, C 3 -C 6 cycloalkyl, C 3 -C δ- alkenyl, C 3 -C 6 -alkynyl, Cι-C 6 -alkoxy-Cι-C 6 -alkyl, (Cι- C 6 alkoxy) - carbonyl -CC 6 ~ alkyl, (C 3 -C 6 alkenyloxy) carbonyl -Ci -C 6 alkyl, phenyl or phenyl -CC 6 alkyl, the phenyl group and the phenyl -Ring the phenylalkyl group may be unsubstituted or may carry one to three radicals, each selected from the group consisting of halogen, nitro, cyano, Ci-C δ alkyl, Ci-C ö haloalkyl, Ci-C δ alkoxy and (Ci -Cg-alkyl) carbonyl;
R13 Wasserstoff, Hydroxy, Cι-C6-Alkyl, C3-C6-Cycloalkyl, Cι-C6-Alkoxy, (Ci -Ce -Alkoxy) carbonyl -Cx -C6 -alkoxy, C3-C6-Alkenyl oder C3 -C6-Alkenyloxy;R 13 is hydrogen, hydroxyl, -CC 6 -alkyl, C 3 -C 6 -cycloalkyl, -C-C 6 -alkoxy, (Ci -Ce -alkoxy) carbonyl -Cx -C 6 -alkoxy, C 3 -C 6 - Alkenyl or C 3 -C 6 alkenyloxy;
R14, R14', R14" unabhängig voneinander - Wasserstoff, Halogen,R 14 , R 14 ', R 14 "independently of one another - hydrogen, halogen,
Ci-Cß-Alkyl, Ci-Cδ-Halogenalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, C3-C6-Alkenyloxy, Ci-Cδ-Alkylthio, Ci-Cδ-Halogenalkylthio, (Cι-C6-Alkyl) carbonyloxy, (Ci-Cδ-Halogenalkyl) carbonyloxy, Ci-Cδ-Alkylsulfonyloxy oder Ci-Cδ-Halogenalkylsulfonyloxy, wobei die letztgenannten 11 Reste einen der folgenden Substituenten tragen können: Hydroxy, Cyano, Hydroxy- carbonyl, Cι-C6-Alkoxy, Cι-C6-Alkylthio, (C -C6-Alkyl) - carbonyl, (Cι-C6-Alkoxy) carbonyl, (Ci -C6 -Alkyl) mino- carbonyl, Di (Ci-Cß-alkyl) aminocarbonyl , (Ci-Cg-Alkyl) - carbonyloxy, Ci-Cδ -Alkoxy- (Ci-Cß-alkyl) aminocarbonyl; - einen mit dem Stickstoffatom über eine Carbonylbrücke gebundenen 3- bis 7gliedrigen Azaheterocyclus, der neben Kohlenstoffringgliedern noch ein Sauerstoff- oder Schwefelatom als Ringglied enthalten kann; (Ci-Cδ-Alkyl) carbonyl, (Ci-Cδ-Halogenalkyl) carbonyl, (Ci-Cδ-Alkoxy) carbonyl, (Ci-Cδ-Alkoxy) carbonyloxy,Ci-C ß- alkyl, Ci-C δ -haloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, C 3 -C 6 -alkenyloxy, Ci-C δ -alkylthio, Ci-C δ -haloalkylthio, (Cι -C 6 -alkyl) carbonyloxy, (Ci-C δ -haloalkyl) carbonyloxy, Ci-C δ -alkylsulfonyloxy or Ci-C δ -haloalkylsulfonyloxy, where the latter 11 radicals can carry one of the following substituents: hydroxy, cyano, hydroxy- carbonyl, -C 6 alkoxy, -C 6 alkylthio, (C 6 -C 6 alkyl) carbonyl, (C 6 -C alkoxy) carbonyl, (C 1 -C 6 alkyl) minocarbonyl, di (Ci-C ß- alkyl) aminocarbonyl, (Ci-Cg-alkyl) -carbonyloxy, Ci-C δ -alkoxy- (Ci-C ß- alkyl) aminocarbonyl; - A 3- to 7-membered azaheterocycle bonded to the nitrogen atom via a carbonyl bridge, which in addition to carbon ring members may also contain an oxygen or sulfur atom as a ring member; (Ci-C δ- alkyl) carbonyl, (Ci-C δ -haloalkyl) carbonyl, (Ci-C δ -alkoxy) carbonyl, (Ci-C δ -alkoxy) carbonyloxy,
(Ci-Cδ-Alkyl) carbonylthio, (Ci-Cδ-Halogenalkyl) carbonyl- thio, (Ci-Cδ-Alkoxy) carbonylthio, C -Cδ-Alkenyl, C -Cδ-Alkenylthio, C3-C6-Alkinyl, C3-Cδ-Alkinyloxy, C3-Cδ-Alkinylthio, (C -Cδ-Alkinyl) carbonyloxy, C3-Cδ-Alkinylsulfonyloxy, C3-Cδ-Cycloalkyl, C3-Cδ-Cyclo- alkyloxy, C3-Cδ-Cycloalkylthio, (C3-Cδ-Cycloalkyl) - carbonyloxy, C3-Cδ-Cycloalkylsulfonyloxy;(Ci-C δ- alkyl) carbonylthio, (Ci-C δ -haloalkyl) carbonyl-thio, (Ci-C δ- alkoxy) carbonylthio, C -C δ- alkenyl, C -C δ- alkenylthio, C 3 -C 6 alkynyl, C 3 -C δ alkynyloxy, C 3 -C δ alkynylthio, (C -C δ alkynyl) carbonyloxy, C 3 -C δ alkynylsulfonyloxy, C 3 -C δ cycloalkyl, C 3 -C δ -cycloalkyloxy, C 3 -C δ- cycloalkylthio, (C 3 -C δ- cycloalkyl) carbonyloxy, C 3 -C δ- cycloalkylsulfonyloxy;
Phenyl, Phenoxy, Phenylthio, Benzoyloxy, Phenylsulfonyloxy, Phenyl-Ci-Cδ-alkyl, Phenyl-Ci-Cg-alkoxy, Phenyl- Ci-Cδ-alkylthio, Phenyl- (Ci-Cδ-alkyl) carbonyloxy oderPhenyl, phenoxy, phenylthio, benzoyloxy, phenylsulfonyloxy, phenyl-Ci-C δ- alkyl, phenyl-Ci-Cg-alkoxy, phenyl-Ci-C δ- alkylthio, phenyl- (Ci-C δ- alkyl) carbonyloxy or
Phenyl- (Ci-Cg-alkyl) sulfonyloxy, wobei die Phenylringe der letztgenannten 10 Reste unsubstituiert sein oder ihrerseits ein bis drei Substituenten tragen können, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cδ-Alkyl, Ci-Cδ-Halogenalkyl,Phenyl- (Ci-Cg-alkyl) sulfonyloxy, where the phenyl rings of the latter 10 residues may be unsubstituted or in turn may carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-C δ- alkyl, Ci -C δ haloalkyl,
Ci-Cδ-Alkoxy und (Ci-Cδ-Alkoxy) carbonyl;Ci-C δ alkoxy and (Ci-C δ alkoxy) carbonyl;
R15 Wasserstoff, Cyano, Ci-Cδ-Alkyl, Ci-Cδ-Halogenalkyl,R 15 is hydrogen, cyano, Ci-C δ- alkyl, Ci-C δ -haloalkyl,
C -C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, Cι-C6-Alk- oxy-Ci-Cδ-alkyl oder (Ci-Cg-Alkoxy) carbonyl;C -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, Cι-C 6 -alk- oxy-Ci-C δ -alkyl or (Ci-Cg alkoxy) carbonyl;
R16 Wasserstoff, Hydroxy, Ci-Cg-Alkyl, C3-Cδ-Alkenyl,R 16 is hydrogen, hydroxy, Ci-Cg-alkyl, C 3 -C δ- alkenyl,
C3-Ce-Alkinyl, C3-Cδ-Cycloalkyl, Ci-Cß-Halogenalkyl, Ci-Cδ-Alkoxy-Ci-Cε-alkyl, Ci-Cß-Alkoxy, C3-Cδ-Alkenyloxy, C3-Cδ-Alkinyloxy, C3-Cδ-Cycloalkoxy, C5-C7-Cycloalkenyloxy, Ci-Cδ-Halogenalkoxy, C3-C6-Halogenalkenyloxy, Hydroxy- Ci-Cδ-alkoxy, Cyano-Ci-Cδ-alkoxy, C3-C6-Cyclalkyl-Cχ-Cδ-alkoxy, Ci-Cδ-Alkoxy-Ci-Cδ-alkoxy, Cι-C6-Alkoxy-C3-Cδ-alkenyloxy, (Ci-Cδ-Alkyl) carbonyloxy, (Ci-Cδ-Halogenalkyl) carbonyloxy, (Ci-Cδ-Alkyl) carbamoyloxy, (Ci-Cg-Halogenalkyl) carbamoyloxy, (Ci-Cδ-Alkyl) carbonyl-Ci-Cδ-alkyl, (Ci-Cδ-Alkyl) carbonyl- Ci-Cδ-alkoxy, (Cι-C6-Alkoxy) carbonyl-Ci-Cδ-alkyl, (Ci-Cδ-Alk- oxy) carbonyl-Ci-Cδ-alkoxy, Ci-Cδ-Alkylthio-Ci-Cδ -alkoxy, Di- (Cι-C6-alkyl)amino-Cι-Cδ-alkoxy, -N(R7)R28, Phenyl, das seinerseits noch einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, C -Cδ-Alkenyl, Cι-C6-Alkoxy und (Ci-Cδ-Alkoxy) carbonyl, Phenyl-Ci-Cδ-alkoxy, Phenyl-C3-Cδ-alkenyloxy oder Phenyl-C 3 -Ce alkynyl, C 3 -C δ cycloalkyl, Ci-C ß haloalkyl, Ci-C δ alkoxy-Ci-Cε-alkyl, Ci-C ß alkoxy, C 3 -C δ alkenyloxy, δ C 3 -C alkynyloxy, C 3 -C δ cycloalkoxy, C 5 -C 7 -cycloalkenyloxy, C δ haloalkoxy, C 3 -C 6 -haloalkenyloxy, hydroxy Ci-C δ alkoxy, cyano Ci-C δ -alkoxy, C 3 -C 6 -cyclalkyl-Cχ-C δ- alkoxy, Ci-C δ -alkoxy-Ci-C δ -alkoxy, -C-C 6 -alkoxy-C 3 -C δ -alkenyloxy , (Ci-C δ- alkyl) carbonyloxy, (Ci-C δ -haloalkyl) carbonyloxy, (Ci-C δ- alkyl) carbamoyloxy, (Ci-Cg-haloalkyl) carbamoyloxy, (Ci-C δ- alkyl) carbonyl- Ci-C δ- alkyl, (Ci-C δ- alkyl) carbonyl- Ci-C δ -alkoxy, (Cι-C 6 -alkoxy) carbonyl-Ci-C δ -alkyl, (Ci-C δ -alkoxy) ) carbonyl-Ci-C δ- alkoxy, Ci-C δ- alkylthio-Ci-C δ -alkoxy, di- (-C-C 6 -alkyl) amino-Cι-C δ -alkoxy, -N (R 7 ) R 28 , Phenyl, which in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, C -C δ alkenyl, Cι-C 6 alkoxy and (Ci-C δ- alkoxy) carbonyl, phenyl-Ci-C δ- alkoxy, phenyl-C 3 -C δ- alkenyloxy or phenyl-
C3-Cδ-alkinyloxy, wobei jeweils eine oder zwei Methylengruppen der Kohlenstoffketten durch -0- , -S- oder -N(Cι-Cg-Alkyl) - ersetzt sein können und wobei jeder Phenylring unsubstituiert sein oder seinerseits einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, C2-C6-Alkenyl, Ci-Cg-Alkoxy und (Ci-Cδ-Alkoxy) carbonyl , Heterocyclyl, Heterocyclyl-Ci-Cδ-alkoxy, Heterocyclyl- C3-Cδ-alkenyloxy oder Heterocyclyl-C3-Cδ-alkinyloxy, wobei jeweils eine oder zwei Methylengruppen der Kohlenstoffketten durch -0- , -S- oder -N(Cι-Cg-Alkyl) - ersetzt sein können und wobei jeder Heterocyclus 3- bis 7gliedrig, gesättigt, ungesättigt oder aromatisch sein kann und ein bis vier Hetero- atome enthält, ausgewählt aus der Gruppe bestehend aus zwei Sauerstoffatomen, zwei Schwefelatomen und 4 Stickstoffatomen, und entweder unsubstituiert ist oder seinerseits einen bis drei Substituenten trägt, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, C -Cg-Alkenyl, Ci-Cg-Alkoxy und (Ci-Cδ-Alkoxy) carbonyl;C 3 -C δ- alkynyloxy, where one or two methylene groups of the carbon chains can be replaced by -0-, -S- or -N (-C-Cg-alkyl) - and each phenyl ring may be unsubstituted or in turn one to three substituents can wear, each selected from the group consisting of cyano, nitro, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, C 2 -C 6 alkenyl, Ci-Cg-alkoxy and (Ci-C δ- alkoxy) carbonyl, heterocyclyl, heterocyclyl-Ci-C δ- alkoxy, heterocyclyl-C 3 -C δ- alkenyloxy or heterocyclyl-C 3 -C δ- alkynyloxy, where in each case one or two methylene groups of the carbon chains by -0-, -S- or -N (-C-Cg-alkyl) - can be replaced and each heterocycle can be 3- to 7-membered, saturated, unsaturated or aromatic and contains one to four hetero atoms selected from the group consisting of two oxygen atoms, two sulfur atoms and 4 nitrogen atoms, and is either unsubstituted or in turn one to three substituents carries, each selected from the group consisting of cyano, nitro, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, C -Cg-alkenyl, Ci-Cg-alkoxy and (Ci-C δ- alkoxy) carbonyl;
R17, R18 unabhängig voneinanderR 17 , R 18 independently of one another
Ci-Cδ-Alkyl, Ci-Cδ-Halogenalkyl, C3-Cδ-Alkenyl, C3-C6-Alkinyl, Ci-Cδ-Alkoxy-Ci-Cδ-alkyl oder zusammen für eine gesättigte oder ungesättigte, 2- bisCi-C δ- alkyl, Ci-C δ -haloalkyl, C 3 -C δ- alkenyl, C 3 -C 6 -alkynyl, Ci-C δ- alkoxy-Ci-C δ -alkyl or together for a saturated or unsaturated , 2- to
4-gliedrige Kohlenstoffkette, die einen Oxosubstituenten tragen kann, wobei ein Glied dieser Kette durch ein den Variablen Z3 und Z4 nicht benachbarte Brücke -0-, -S-, -N=, -NH- oder -N(Cι-Cg-Alkyl) - ersetzt sein kann, und wobei die Kohlenstoffkette noch ein bis drei Reste tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Amino, Halogen, Ci-Cg-Alkyl, C2-Cg-Alkenyl, Ci-Cg-Alk- oxy, C -Cg-Alkenyloxy, C2-Cg-Alkinyloxy, Ci-Cg-Halogenalkyl, Cyano-Ci-Cg-alkyl, Hydroxy-Ci-Cδ-alkyl, Ci-Cδ-Alkoxy- Ci-Cg-alkyl, C3-Cδ-Alkenyloxy-Cι-Cδ -alkyl, C3-Cδ-Alkinyloxy- Ci-Cg-alkyl, C3-Cδ-Cycloalkyl, C3-Cδ-Cycloalkoxy, Carboxy, (Ci-Cδ-Alkoxy) carbonyl, (Ci-Cδ-Alkyl) carbonyloxy-Ci-Cβ-alkyl und Phenyl, das seinerseits unsubstituiert sein oder einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Amino, Halogen, Ci-Cδ-Alkyl, Ci-Cδ-Halogenalkyl, Ci-Cg-Alkoxy und (Cι~Cg-Alk- oxy) carbonyl , und wobei die Kohlenstoffkette auch durch einen ankondensierten oder spiroverknüpften 3- bis 7gliedrigen Ring substituiert sein kann, der ein oder zwei Heteroatome als Ringglieder enthalten kann, ausgewählt aus Sauerstoff, Schwefel, Stickstoff und durch Ci-Cg-Alkyl substituiertem Stickstoff, und der gewünschtenfalls seinerseits einen oder zwei der folgenden Substituenten tragen kann: Cyano, Ci-Cg-Alkyl, C2-Cδ-Alkenyl, Cι-C6-Alkoxy, Cyano-Ci-Cδ-alkyl, Ci-Cg-Halogenalkyl und (Ci-Cg-Alkoxy) carbonyl;4-link carbon chain, which can carry an oxo substituent, one link of this chain through a bridge not adjacent to the variables Z 3 and Z 4 -0-, -S-, -N =, -NH- or -N (Cι-Cg -Alkyl) - can be replaced, and wherein the carbon chain can still carry one to three residues, each selected from the group consisting of cyano, nitro, amino, halogen, Ci-Cg-alkyl, C 2 -Cg-alkenyl, Ci Cg-alkoxy, C -Cg-alkenyloxy, C 2 -Cg-alkynyloxy, Ci-Cg-haloalkyl, cyano-Ci-Cg-alkyl, hydroxy-Ci-C δ- alkyl, Ci-C δ- alkoxy-Ci -Cg-alkyl, C 3 -C δ -alkenoxy-Cι-C δ -alkyl, C 3 -C δ -alkynyloxy-Ci-Cg-alkyl, C 3 -C δ -cycloalkyl, C 3 -C δ -cycloalkoxy, Carboxy, (Ci-C δ- alkoxy) carbonyl, (Ci-C δ- alkyl) carbonyloxy-Ci-Cβ-alkyl and phenyl, which in turn may be unsubstituted or carry one to three substituents, each selected from the group consisting of cyano , Nitro, amino, halogen, Ci-C δ- alkyl, Ci-C δ -haloalkyl, Ci-Cg-alkoxy and (Cι ~ Cg-alkoxy) car bonyl, and wherein the carbon chain can also be substituted by a fused or spiro-linked 3- to 7-membered ring, which can contain one or two heteroatoms as ring members, selected from oxygen, sulfur, nitrogen and nitrogen substituted by Ci-Cg-alkyl, and if desired, in turn can carry one or two of the following substituents: cyano, Ci-Cg-alkyl, C 2 -C δ- alkenyl, Cι-C 6 -alkoxy, cyano-Ci-C δ- alkyl, Ci-Cg-haloalkyl and (Ci Cg alkoxy) carbonyl;
R19 Wasserstoff, Cyano, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy, (Ci-Cg-Alkyl) carbonyl oder (Ci-Cg-Alkoxy) - carbonyl ;R 19 is hydrogen, cyano, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, (Ci-Cg-alkyl) carbonyl or (Ci-Cg-alkoxy) carbonyl;
R20 Wasserstoff, O-R29, S-R29, Ci-Cg-Alkyl, das noch einen oder zwei Ci-Cg-Alkoxysubstituenten tragen kann, C2-Cg-Alkenyl, C -Cg-Alkinyl, Ci-Cg-Halogenalkyl, C3-Cg-Cycloalkyl , Ci-Cδ-Alkylthio-Ci-Cδ-alkyl, Ci-Cg-Alkyliminooxy, -N(R25)R26 oder Phenyl, das unsubstituiert sein oder ein bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cg-Alkyl, C2-Cδ-Alkenyl, Ci-Cg-Halogenalkyl, Ci-Cδ-Alkoxy und (Cι~Cg-Alk- oxy) carbonyl;R 20 is hydrogen, OR 29 , SR 29 , Ci-Cg-alkyl, which can also carry one or two Ci-Cg-alkoxy substituents, C 2 -Cg-alkenyl, C -Cg-alkynyl, Ci-Cg-haloalkyl, C 3 -Cg-cycloalkyl, Ci-C δ -alkylthio-Ci-C δ -alkyl, Ci-Cg-alkyliminooxy, -N (R 25 ) R 26 or phenyl, which may be unsubstituted or carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-Cg-alkyl, C 2 -C δ- alkenyl, Ci-Cg-haloalkyl, Ci-C δ -alkoxy and (Cι ~ Cg-alkoxy) carbonyl;
R21 Wasserstoff, Cyano, Halogen, Ci-Cδ-Alkyl, C3-Cδ-Alkenyl, C3-C6-Alkinyl, Ci-Cg-Alkoxy-Ci-Cg-alkyl, (Ci-Cδ-Alkyl) - carbonyl, (Ci-Cδ-Alkoxy) carbonyl, -N(R25)R26 oder Phenyl, das seinerseits noch einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cδ-Alkyl, Ci-Cδ-Halogenalkyl, C3-Cδ-Alkenyl, Ci-Cδ-Alkoxy und (Ci-Cg-Alkoxy) carbonyl;R 21 is hydrogen, cyano, halogen, Ci-C δ- alkyl, C 3 -C δ- alkenyl, C 3 -C 6 -alkynyl, Ci-Cg-alkoxy-Ci-Cg-alkyl, (Ci-C δ- alkyl ) - carbonyl, (Ci-C δ -alkoxy) carbonyl, -N (R 25 ) R 26 or phenyl, which in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci C δ alkyl, Ci-C δ haloalkyl, C 3 -C δ alkenyl, Ci-C δ alkoxy and (Ci-Cg-alkoxy) carbonyl;
R22 Wasserstoff, Cyano, Halogen, Ci-Cg-Alkyl, Ci-Cg-Alkoxy,R 22 is hydrogen, cyano, halogen, Ci-Cg-alkyl, Ci-Cg-alkoxy,
Ci-Cg-Halogenalkyl, (Ci-Cδ-Alkyl) carbonyl oder (Ci-Cg-Alkoxy) - carbonyl;Ci-Cg-haloalkyl, (Ci-C δ- alkyl) carbonyl or (Ci-Cg-alkoxy) carbonyl;
R23 Wasserstoff, Cyano, Ci-Cg-Alkyl oder (Ci-Cg-Alkoxy) carbonyl;R 23 is hydrogen, cyano, Ci-Cg-alkyl or (Ci-Cg-alkoxy) carbonyl;
R24, R29 unabhängig voneinander Wasserstoff, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, C -Cg-Alkenyl oder C -Cδ-Alkinyl, wobei die letztgenannten 4 Gruppen jeweils einen oder zwei der folgenden Reste tragen können: Cyano, Halogen, Hydroxy, Hydroxycarbonyl , Ci-Cδ-Alkoxy, Ci-Cg-Alkyl- thio, (Ci-Cδ-Alkyl) carbonyl, (Cι~Cg-Alkoxy) carbonyl, (Ci-Cg-Alkyl) carbonyloxy, (C -Cg-Alkenyloxy) carbonyl oder einen mit dem Stickstoffatom über eine Carbonylbrücke gebun- denen 3- bis 7gliedrigen Azaheterocyclus, der neben Kohlenstoffringgliedern noch ein Sauerstoff- oder Schwefelatom als Ringglied enthalten kann; oder (Ci-Cg-Alkyl) carbonyl, (Ci-Cg-Halogenalkyl) carbonyl, (Ci-Cg-Alkoxy) carbonyl, Ci-Cg-Alkylaminocarbonyl, Di-R 24 , R 29 independently of one another are hydrogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, C -Cg-alkenyl or C -C δ- alkynyl, where the latter 4 groups can each carry one or two of the following radicals: cyano , Halogen, hydroxy, hydroxycarbonyl, Ci-C δ- alkoxy, Ci-Cg-alkyl-thio, (Ci-C δ- alkyl) carbonyl, (Cι ~ Cg-alkoxy) carbonyl, (Ci-Cg-alkyl) carbonyloxy, (C -Cg alkenyloxy) carbonyl or one bonded to the nitrogen atom via a carbonyl bridge those 3- to 7-membered azaheterocycle which, in addition to carbon ring members, may also contain an oxygen or sulfur atom as the ring member; or (Ci-Cg-alkyl) carbonyl, (Ci-Cg-haloalkyl) carbonyl, (Ci-Cg-alkoxy) carbonyl, Ci-Cg-alkylaminocarbonyl, di-
(Ci -Cg -alkyl) aminocarbonyl , Ci -Cg -Alkyloximino-Ci -Cg -alkyl , C3-Cg-Cycloalkyl ,(Ci -Cg alkyl) aminocarbonyl, Ci -Cg alkyloximino Ci -Cg alkyl, C 3 -Cg cycloalkyl,
Phenyl oder Phenyl-Ci-Cδ-alkyl, wobei die Phenylringe unsubstituiert sein oder ihrerseits ein bis drei Substituenten tragen können, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cδ-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy und (Ci-Cg-Alkoxy) carbonyl;Phenyl or phenyl-Ci-C δ- alkyl, where the phenyl rings may be unsubstituted or in turn may carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-C δ- alkyl, Ci-Cg-haloalkyl , Ci-Cg-alkoxy and (Ci-Cg-alkoxy) carbonyl;
R25, R26, R27, R28 unabhängig voneinander Wasserstoff, Ci-Cg-Alkyl, C3-Cg-Alkenyl, C2-Cg-Alkinyl,R 25 , R 26 , R 27 , R 28 independently of one another are hydrogen, Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 2 -Cg-alkynyl,
C3-Cδ-Cycloalkyl, Ci-Cδ-Halogenalkyl, Cι-Cg-Alkoxy-Cι-Cg-alkyl, (Ci-Cg-Alkyl) carbonyl, (Ci-Cg-Alkoxy) carbonyl, (Ci-Cg-Alkoxy) - carbonyl- C -Cg-alkyl, (Ci-Cg-Alkoxy) carbonyl-C2-Cg-alkenyl, wobei die Alkenylkette zusätzlich ein bis drei Halogen- und/oder Cyano-Reste tragen kann, oder Ci-Cg-Alkylsulfonyl, (Ci-Cδ -Alkoxy) carbonyl -Ci-Cg-alkyl - sulfonyl, Phenyl oder Phenylsulfonyl, wobei die beiden Phenylringe unsubstituiert sein oder ihrerseits einen bis drei Substituenten tragen können, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cδ-Alkyl,C 3 -C δ cycloalkyl, Ci-C δ haloalkyl, -C-Cg-alkoxy-Cι-Cg-alkyl, (Ci-Cg-alkyl) carbonyl, (Ci-Cg-alkoxy) carbonyl, (Ci-Cg- Alkoxy) - carbonyl-C -Cg-alkyl, (Ci-Cg-alkoxy) carbonyl-C 2 -Cg-alkenyl, where the alkenyl chain can additionally carry one to three halogen and / or cyano radicals, or Ci-Cg- Alkylsulfonyl, (Ci-C δ- alkoxy) carbonyl-Ci-Cg-alkyl-sulfonyl, phenyl or phenylsulfonyl, where the two phenyl rings can be unsubstituted or in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, Halogen, Ci-C δ alkyl,
Ci-Cg-Halogenalkyl, C3-Cg-Alkenyl, Ci-Cg-Alkoxy und (Ci-Cg-Alk- oxy) carbonyl , oder R25 und R26 und/oder R27 und R28 zusammen mit dem jeweils gemeinsamen Stickstoffatom für einen gesättigten oder un- gesättigten 4- bis 7gliedrigen Azaheterocyclus, der nebenCi-Cg-haloalkyl, C 3 -Cg-alkenyl, Ci-Cg-alkoxy and (Ci-Cg-alkoxy) carbonyl, or R 25 and R 26 and / or R 27 and R 28 together with the respective common nitrogen atom for a saturated or unsaturated 4- to 7-membered azaheterocycle, which besides
Kohlenstoffringgliedern gewünschtenf lls eines der folgenden Glieder enthalten kann: -0-, -S-, -N=, -NH- oder -N(Cι-Cg-Alkyl)-;If desired, carbon ring members can contain one of the following members: -0-, -S-, -N =, -NH- or -N (-C-Cg-alkyl) -;
sowie die landwirtschaftlich brauchbaren Salze und Enolether der Verbindungen I.and the agriculturally useful salts and enol ethers of the compounds I.
Außerdem betrifft die Erfindung die Verwendung der Verbindungen I als Herbizide, - herbizide Mittel, welche die Verbindungen I als wirksame Substanzen enthalten,The invention also relates to the use of the compounds I as herbicides, herbicidal compositions which contain the compounds I as active substances,
Verfahren zur Herstellung der Verbindungen I und von herbiziden Mitteln unter Verwendung der Verbindungen I, sowie Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs mit den Verbindungen I . Substituierte 1-Phenyluracil-Derivate sind bereits Gegenstand der WO 97/05117, denen dort eine herbizide Wirkung zugeschrieben wird.Process for the preparation of the compounds I and herbicidal compositions using the compounds I, and process for controlling unwanted vegetation with the compounds I. Substituted 1-phenyluracil derivatives are already the subject of WO 97/05117, which are said to have a herbicidal action there.
Die herbiziden Eigenschaften der bisher bekannten herbizid wirksamen 1-Phenyluracile bezüglich der Schadpflanzen sind jedoch nicht immer völlig befriedigend. Aufgabe der vorliegenden Erfindung war es deshalb, neue herbizid wirksame 1-Aryluracile bereitzustellen, mit denen sich unerwünschte Pflanzen besser als bisher gezielt bekämpfen lassen.However, the herbicidal properties of the herbicidally active 1-phenyluracils known to date regarding the harmful plants are not always completely satisfactory. The object of the present invention was therefore to provide new herbicidally active 1-aryluracils which can be used to combat undesirable plants better than before.
Demgemäß wurden die eingangs definierten l-Aryl-4-thiouracile der Formel I gefunden. Ferner wurden herbizide Mittel gefunden, die 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.Accordingly, the l-aryl-4-thiouracils of the formula I defined at the outset were found. Furthermore, herbicidal compositions have been found which contain the compounds I and have a very good herbicidal action. In addition, processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.
Die Verbindungen der Formel I können je nach Substitutionsmuster ein oder mehrere Chiralitätszentren enthalten und liegen dann als Enantiomeren- oder Diastereomerengemische vor. Bei Verbindungen I mit mindestens einem olefinischen Rest sind gegebenenfalls auch E-/Z-Isomere möglich. Gegenstand der Erfindung sind sowohl die reinen Enantiomeren oder Diastereomeren als auch deren Gemi- sehe.Depending on the substitution pattern, the compounds of the formula I can contain one or more centers of chirality and are then present as mixtures of enantiomers or diastereomers. In the case of compounds I with at least one olefinic radical, E / Z isomers may also be possible. The invention relates both to the pure enantiomers or diastereomers and to their mixtures.
Unter landwirtschaftlich brauchbaren Salzen kommen vor allem die Salze derjenigen Kationen oder die Säureadditionssalze derjenigen Säuren in Betracht, deren Kationen beziehungsweise Anionen die herbizide Wirkung der Verbindungen I nicht negativ beeinträchtigen. So kommen als Kationen insbesondere die Ionen der Alkalimetalle, vorzugsweise Natrium und Kalium, der Erdalkalimetalle, vorzugsweise Calcium, Magnesium und Barium, und der Übergangs - metalle, vorzugsweise Mangan, Kupfer, Zink und Eisen, sowie das Airanoniumion, das gewünschtenfalls ein bis vier Cι-C-Alkyl- substituenten und/oder einen Phenyl- oder Benzylsubstituenten tragen kann, vorzugsweise Diisopropylammonium, Tetramethyl - ammonium, Tetrabutylammonium, Trimethylbenzylammonium, des weiteren Phosphoniumionen, Sulfoniumionen, vorzugsweise Tri (Cι-C -alkyl) sulfonium und Sulfoxoniumionen, vorzugsweise Tri (Cι-C -alkyl) sulfoxonium, in Betracht.Agriculturally useful salts include, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the herbicidal activity of the compounds I. So come as cations in particular the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, as well as the airanonium ion, if desired one to four Cι -C-alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (-C-alkyl) sulfonium and sulfoxonium ions, preferably tri ( -CC alkyl) sulfoxonium, into consideration.
Anionen von brauchbaren Säureadditionssalzen sind in erster Linie Chlorid, Bromid, Fluorid, Hydrogensulfat, Sulfat, Dihydrogen- phosphat, Hydrogenphosphat, Phosphat, Nitrat, Hydrogencarbonat, Carbonat, Hexafluorosilikat, Hexafluorophosphat, Benzoat, sowie die Anionen von Cι-C -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, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of -C-alkanoic acids, preferably formate, acetate, propionate and butyrate.
Die bei der Definition von R1 bis R3, R5 bis R29 sowie an Phenyl-, Cycloalkyl- und Heterocyclylringen genannten organischen Molekül - teile stellen Sammelbegriffe für individuelle Aufzählungen der einzelnen Gruppenmitglieder dar. Sämtliche Kohlenstoffketten, also alle (gegebenenfalls substituiertem) Alkyl-, Alkenyl- oder Alkinyl-Teile können geradkettig oder verzweigt sein.The organic molecule parts mentioned in the definition of R 1 to R 3 , R 5 to R 29 and on phenyl, cycloalkyl and heterocyclyl rings are collective terms for individual lists of the individual group members. All carbon chains, that is to say all (optionally substituted) alkyl -, Alkenyl or alkynyl parts can be straight-chain or branched.
Halogenierte Substituenten tragen vorzugsweise ein bis fünf gleiche oder verschiedene Halogenatome.Halogenated substituents preferably carry one to five identical or different halogen atoms.
Die Bedeutung Halogen steht jeweils für Fluor, Brom, Chlor oder Iod, insbesondere für Fluor oder Chlor.Halogen is fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
Ferner stehen beispielsweise:Furthermore, for example:
Cι-C4-Alkyl für: CH3 , C2H5, n-Propyl, CH(CH3)2, n-Butyl, CH(CH3) -CH5, 2-Methylpropyl oder C(CH3)3, insbesondere für CH3, C2H5 oder CH(CH3)2;-C-C 4 alkyl for: CH 3 , C 2 H 5 , n-propyl, CH (CH 3 ) 2 , n-butyl, CH (CH 3 ) -CH 5 , 2-methylpropyl or C (CH 3 ) 3 , in particular for CH 3 , C 2 H 5 or CH (CH 3 ) 2 ;
Cι-C -Halogenalkyl für: einen Cι-C -Alkylrest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. CHF, CHF , CF3 , CH2C1, Dichlormethyl, Trichlormethyl, Chlorfluormethyl, Dichlorfluormethyl, Chlordifluormethyl, 2-Fluorethyl, 2-Chlorethyl, 2-Bromethyl, 2-Iodethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, 2-Chlor-2-fluorethyl, 2-Chlor-2,2- difluorethyl, 2, 2-Dichlor-2-fluorethyl, 2, 2, 2-Trichlorethyl, CF5, 2-Fluorpropyl, 3-Fluorpropyl, 2, 2-Difluorpropyl, 2, 3-Difluorpropyl, 2-Chlorpropyl, 3-Chlorpropyl, 2,3-Dichlor- propyl , 2-Brompropyl , 3-Brompropyl , 3,3, 3-Trifluorpropyl , 3, 3 , 3-Trichlorpropyl, 2, 2, 3 , 3, 3-Pentafluorpropyl, Heptafluor- propyl, 1- (Fluormethyl) -2-fluorethyl, 1- (Chlormethyl) -2- chlorethyl, 1- (Brommethyl) -2-bromethyl, 4-Fluorbutyl, 4-Chlorbutyl, 4-Brombutyl oder Nonafluorbutyl, insbesondere für CH2F, CHF2, CF3, CH2C1, 2-Fluorethyl, 2-Chlorethyl oder 2,2, 2-Trifluorethyl;C 1 -C 6 -haloalkyl for: a C 1 -C 4 -alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CHF, CHF, CF 3 , CH 2 C1, dichloromethyl, trichloromethyl , Chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2 , 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl, CF 5 , 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, heptafluoro- propyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl, especially for CH 2 F, CHF 2 , CF 3 , CH 2 C1, 2-fluoroethyl, 2-chloroethyl or 2,2, 2-trifluoroethyl;
Ci-Cg-Alkyl für: Cι-C4-Alkyl wie vorstehend genannt, sowie z.B. n-Pentyl, 1-Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 2, 2-Dimethylpropyl, 1-Ethylpropyl, n-Hexyl, 1, 1-Dimethyl- propyl, 1, 2-Dimethylpropyl, 1-Methylpentyl , 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1, 1-Dimethylbutyl,Ci-Cg-alkyl for: -CC 4 -alkyl as mentioned above, and for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1st , 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl,
1,2-Dirnethylbutyl, 1, 3-Dimethylbutyl, 2, 2-Dimethylbutyl, 2,3-Dimethylbutyl, 3 , 3-Dimethylbutyl, 1-Ethylbutyl, 2-Ethylbutyl, 1, 1, 2-Trimethylpropyl, 1, 2 , 2-Trimethylpropyl, 1-Ethyl-l-methylproρyl oder l-Ethyl-2-methylpropyl, insbesondere für CH3, C2H5, n-Propyl, CH(CH3)2, n-Butyl, C(CH3)3, n-Pentyl oder n-Hexyl;1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2, 2-trimethylpropyl, 1-ethyl-l-methylpropyl or l-ethyl-2-methylpropyl, in particular for CH 3 , C 2 H 5 , n-propyl, CH (CH 3 ) 2 , n-butyl, C (CH 3 ) 3 , n-pentyl or n-hexyl;
Ci-Cg-Halogenalkyl für: Ci-Cg-Alkyl wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. einen der unter Cι-C4-Halogenalkyl genannten Reste oder für 5-Fluor-l-pentyl, 5-Chlor-l-pentyl, 5-Brom-l-pentyl, 5-Iod-l-pentyl, 5,5,5-Tri- chlor-1-pentyl, Undecafluorpentyl, 6-Fluor-l-hexyl, 6-Chlor- 1-hexyl, 6-Brom-l-hexyl, 6-Iod-l-hexyl, 6, 6, 6-Trichlor-l- hexyl oder Dodecafluorhexyl, insbesondere für Chlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, 2-Fluorethyl, 2-Chlorethyl oder 2, 2, 2-Trifluorethyl ;Ci-Cg-haloalkyl for: Ci-Cg-alkyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for example, one of the radicals mentioned under C 1 -C 4 -haloalkyl or for 5- Fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6-fluoro l-hexyl, 6-chloro-1-hexyl, 6-bromo-l-hexyl, 6-iodo-l-hexyl, 6, 6, 6-trichloro-l-hexyl or dodecafluorohexyl, in particular for chloromethyl, fluoromethyl, difluoromethyl, Trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;
Hydroxy-Ci-C -alkyl für: z.B. Hydroxymethyl , 2-Hydroxyeth- 1-yl, 2-Hydroxy-prop-l-yl, 3-Hydroxy-prop-l-yl, 1-Hydroxy- prop-2-yl, 2-Hydroxy-but-l-yl, 3-Hydroxy-but-l-yl, 4-Hydroxy- but-l-yl, l-Hydroxy-but-2-yl, l-Hydroxy-but-3-yl, 2-Hydroxy- but-3-yl, l-Hydroxy-2-methyl-prop-3-yl, 2-Hydroxy-2-methyl- prop-3-yl oder 2-Hydroxymethyl-prop-2-yl, insbesondere für 2 -Hydroxyethyl ;Hydroxy-Ci-C -alkyl for: e.g. Hydroxymethyl, 2-hydroxyeth-1-yl, 2-hydroxy-prop-l-yl, 3-hydroxy-prop-l-yl, 1-hydroxy-prop-2-yl, 2-hydroxy-but-l-yl, 3-hydroxy-but-l-yl, 4-hydroxy-but-l-yl, l-hydroxy-but-2-yl, l-hydroxy-but-3-yl, 2-hydroxy-but-3-yl, 1-hydroxy-2-methyl-prop-3-yl, 2-hydroxy-2-methyl-prop-3-yl or 2-hydroxymethyl-prop-2-yl, in particular for 2-hydroxyethyl;
Cyano-Ci-Cg-alkyl für: z.B. Cyanomethyl, 1-Cyanoeth-l-yl,Cyano-Ci-Cg-alkyl for: e.g. Cyanomethyl, 1-cyanoeth-l-yl,
2-Cyanoeth-l-yl, 1-Cyanoprop-l-yl, 2-Cyanoprop-l-yl, 3-Cyano- prop-1-yl, l-Cyanoprop-2-yl, 2-Cyanoprop-2-yl, 1-Cyanobut- 1-yl, 2-Cyanobut-l-yl, 3-Cyanobut-l-yl, 4-Cyanobut-l-yl, l-Cyanobut-2-yl, 2-Cyanobut-2-yl, l-Cyanobut-3-yl, 2-Cyano- but-3-yl, l-Cyano-2-methyl-prop-3-yl, 2-Cyano-2-methyl- prop-3-yl, 3-Cyano-2-methyl-prop-3-yl oder 2-Cyanomethyl- prop-2-yl, insbesondere für Cyanomethyl oder 2 -Cyanoethyl ;2-cyanoeth-l-yl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyano-prop-1-yl, l-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4-cyanobut-l-yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, l- Cyanobut-3-yl, 2-cyano-but-3-yl, l-cyano-2-methyl-prop-3-yl, 2-cyano-2-methyl-prop-3-yl, 3-cyano-2- methyl-prop-3-yl or 2-cyanomethyl-prop-2-yl, especially for cyanomethyl or 2-cyanoethyl;
Phenyl-Ci-Cδ-alkyl für: z.B. Benzyl, 1-Phenylethyl, 2-Phenyl - ethyl, 1-Phenylprop-l-yl, 2-Phenylprop-l-yl, 3-Phenylprop- 1-yl, 1-Phenylbut-l-yl, 2-Phenylbut-l-yl, 3-Phenylbut-l-yl, 4-Phenylbut-l-yl, l-Phenylbut-2-yl, 2-Phenylbut-2-yl, 3-Phenylbut-2-yl, 4-Phenylb t-2-yl, l-(Phenylmethy1) -eth- 1-yl, l-(Phenylmethyl)-l-(methyl)-eth-l-yl oder 1- (Phenyl - methyl) -prop-1-yl, insbesondere für Benzyl oder 2-Phenyl- ethyl ;Phenyl-Ci-C δ- alkyl for: e.g. benzyl, 1-phenylethyl, 2-phenyl-ethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-1-yl, 1-phenylbut -l-yl, 2-phenylbut-l-yl, 3-phenylbut-l-yl, 4-phenylbut-l-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2 -yl, 4-phenylb t-2-yl, l- (phenylmethyl) -eth-1-yl, l- (phenylmethyl) -l- (methyl) -eth-l-yl or 1- (phenylmethyl) - prop-1-yl, especially for benzyl or 2-phenylethyl;
Phenyl- (Ci-Cg -alkyl) carbonyloxy für: z.B. Benzylcarbonyloxy, 1-Phenylethylcarbonyloxy, 2-Phenylethylcarbonyloxy, 1-Phenyl- prop-1-ylcarbonyloxy, 2-Phenylprop-l-ylcarbonyloxy, 3-Phenyl- prop-1-ylcarbonyloxy, 1-Phenylbut-l-ylcarbonyloxy, 2-Phenyl- but-1-ylcarbonyloxy, 3-Phenylbut-l-ylcarbonyloxy, 4-Phenyl- but-1-ylcarbonyloxy, l-Phenylbut-2-ylcarbonyloxy, 2-Phenyl- but-2-ylcarbonyloxy, 3-Phenylbut-2-ylcarbonyloxy, 4-Phenyl- but-2-ylcarbonyloxy, 1- (Phenylmethyl) -eth-1-ylcarbonyloxy, 1- (Phenylmethyl) -1- (methyl) -eth-1-ylcarbonyloxy oder 1- (Phenylmethyl) -prop-1-ylcarbonyloxy, insbesondere für Benzylcarbonyloxy oder 2-Phenylethylcarbonyloxy;Phenyl- (Ci-Cg-alkyl) carbonyloxy for: e.g. benzylcarbonyloxy, 1-phenylethylcarbonyloxy, 2-phenylethylcarbonyloxy, 1-phenylprop-1-ylcarbonyloxy, 2-phenylprop-l-ylcarbonyloxy, 3-phenylprop-1-ylcarbonyloxy , 1-phenylbut-l-ylcarbonyloxy, 2-phenylbut-1-ylcarbonyloxy, 3-phenylbut-l-ylcarbonyloxy, 4-phenyl- but-1-ylcarbonyloxy, l-phenylbut-2-ylcarbonyloxy, 2-phenylbut-2-ylcarbonyloxy, 3-phenylbut-2-ylcarbonyloxy, 4-phenylbut-2-ylcarbonyloxy, 1- (phenylmethyl) -eth- 1-ylcarbonyloxy, 1- (phenylmethyl) -1- (methyl) -eth-1-ylcarbonyloxy or 1- (phenylmethyl) prop-1-ylcarbonyloxy, especially for benzylcarbonyloxy or 2-phenylethylcarbonyloxy;
Phenyl -Ci-Cg-alkylsulfonyloxy für: z.B. Benzylsulfonyloxy, 1-Phenylethylsulfonyloxy, 2-Phenylethylsulfonyloxy, 1-Pheny1- prop-1-ylsulfonyloxy, 2-Phenylprop-l-ylsulfonyloxy, 3-Phenyl- prop-1-ylsulfonyloxy, 1-Phenylbut-l-ylsulfonyloxy, 2-Phenyl- but-1-ylsulfonyloxy, 3-Phenylbut-l-ylsulfonyloxy, 4-Phenyl- but-1-ylsulfonyloxy, l-Phenylbut-2-ylsulfonyloxy, 2-Phenyl- but-2-ylsulfonyloxy, 3-Phenylbut-2-ylsulfonyloxy, 4-Phenyl- but-2-ylsulfonyloxy, 1- (Phenylmethyl) -eth-l-ylsulfonyloxy, 1- (Phenylmethyl) -1- (methyl) -eth-1-ylsulfonyloxy oder 1- (Phenylmethyl) -prop-1-ylsulfonyloxy, insbesondere für Benzylsulfonyloxy oder 2-Phenylethylsulfonyloxy;Phenyl-Ci-Cg-alkylsulfonyloxy for: e.g. Benzylsulfonyloxy, 1-phenylethylsulfonyloxy, 2-phenylethylsulfonyloxy, 1-pheny1-prop-1-ylsulfonyloxy, 2-phenylprop-l-ylsulfonyloxy, 3-phenylprop-1-ylsulfonyloxy, 1-phenylbut-l-ylsulfonyloxy, 2-phenyl but-1-ylsulfonyloxy, 3-phenylbut-l-ylsulfonyloxy, 4-phenyl-but-1-ylsulfonyloxy, l-phenylbut-2-ylsulfonyloxy, 2-phenylbut-2-ylsulfonyloxy, 3-phenylbut-2-ylsulfonyloxy, 4-phenyl-but-2-ylsulfonyloxy, 1- (phenylmethyl) -eth-1-ylsulfonyloxy, 1- (phenylmethyl) -1- (methyl) -eth-1-ylsulfonyloxy or 1- (phenylmethyl) prop-1- ylsulfonyloxy, especially for benzylsulfonyloxy or 2-phenylethylsulfonyloxy;
- (Ci-Cg-Alkyl) carbonyl für: z.B. CO-CH3, CO-C2H5, CO-CH2-C2H5,- (Ci-Cg-alkyl) carbonyl for: for example CO-CH 3 , CO-C 2 H 5 , CO-CH 2 -C 2 H 5 ,
CO-CH(CH3)2, n-Butylcarbonyl, CO-CH (CH3) -C2H5, CO-CH2-CH (CH3) 2, CO-C(CH3)3, n-Pentylcarbonyl, 1-Methylbutylcarbonyl, 2-Methyl- butylcarbonyl, 3-Methylbutylcarbonyl, 1, 1-Dimethylpropyl- carbonyl , 1 , 2-Dimethylpropylcarbonyl , 2 , 2-Dimethylpropyl - carbonyl, 1-Ethylpropylcarbonyl, n-Hexylcarbonyl , 1-Methyl - pentylcarbonyl, 2-Methylpentylcarbonyl, 3-Methylpentyl- carbonyl, 4-Methylpentylcarbonyl, 1, 1-Dimethylbutylcarbonyl, 1 , 2-Dimethylbutylcarbonyl , 1 , 3-Dimethylb tylcarbonyl , 2 , 2-Dimethylbutylcarbonyl , 2 , 3-Dimethylbutylcarbonyl, 3,3-Dimethylbutylcarbonyl, 1-Ethylbutylcarbonyl, 2-Ethyl- butylcarbonyl, 1, 1, 2-Trimethylpropylcarbonyl, 1,2,2-Tri- methylpropylcarbonyl, 1-Ethyl-l-methylpropylcarbonyl oder l-Ethyl-2-methylpropylcarbonyl, insbesondere für CO-CH3, CO-C2H5 oder CO-CH (CH3)2;CO-CH (CH 3 ) 2 , n-butylcarbonyl, CO-CH (CH 3 ) -C 2 H 5 , CO-CH 2 -CH (CH 3 ) 2 , CO-C (CH 3 ) 3 , n-pentylcarbonyl , 1-Methylbutylcarbonyl, 2-Methylbutylcarbonyl, 3-Methylbutylcarbonyl, 1, 1-Dimethylpropylcarbonyl, 1, 2-Dimethylpropylcarbonyl, 2, 2-Dimethylpropyl - carbonyl, 1-Ethylpropylcarbonyl, n-Hexylcarbonyl, 1-Methyl - pentylcarbonyl , 2-Methylpentylcarbonyl, 3-Methylpentylcarbonyl, 4-Methylpentylcarbonyl, 1, 1-Dimethylbutylcarbonyl, 1, 2-Dimethylbutylcarbonyl, 1, 3-Dimethylb tylcarbonyl, 2, 2-Dimethylbutylcarbonyl, 2, 3-Dimethylbutylcarbonyl, 3,3- Dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1, 1, 2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-l-methylpropylcarbonyl or l-ethyl-2-methylpropylcarbonyl, especially for CO- CH 3 , CO-C 2 H 5 or CO-CH (CH 3 ) 2 ;
(Ci -C -Alkyl) carbonyl -Ci-Cg -alkyl für: durch (Ci-Cg-Alkyl) - carbonyl wie vorstehend genannt substituiertes Ci-C -Alkyl, also z.B. für Methylcarbonylmethyl ;(Ci -C-alkyl) carbonyl -Ci-Cg-alkyl for: Ci-C-alkyl substituted by (Ci-Cg-alkyl) carbonyl as mentioned above, e.g. for methylcarbonylmethyl;
- (Ci-Cg-Halogenalkyl) carbonyl für: einen (Ci-Cg-Alkyl) carbonyl- rest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Chloracetyl, Dichloracetyl, Trichloracetyl, Fluoracetyl, Difluoracetyl, Trifluoracetyl, Chlorfluoracetyl, Dichlor- fluoracetyl, Chlordifluoracetyl, 2-Fluorethylcarbonyl, 2-Chlorethylcarbonyl, 2-Bromethylcarbonyl, 2-Iodethyl- carbonyl, 2, 2-Difluorethylcarbonyl, 2, 2 , 2-Trifluorethyl- carbonyl, 2-Chlor-2-fluorethylcarbonyl, 2-Chlor-2, 2-difluor- ethylcarbonyl, 2 , 2-Dichlor-2-fluorethylcarbonyl, 2,2,2-Tri- chlorethylcarbonyl, Pentafluorethylcarbonyl, 2-Fluorpropyl- carbonyl, 3-Fluorpropylcarbonyl, 2, 2-Difluorpropylcarbonyl, 2, 3-Difluorpropylcarbonyl, 2-Chlorpropylcarbonyl, 3-Chlor- propylcarbonyl , 2, 3-Dichlorpropylcarbonyl, 2-Brompropyl- carbonyl, 3-Brompropylcarbonyl, 3, 3, 3-Trifluorpropylcarbonyl, 3,3, 3-Trichlorpropylcarbonyl, 2,2,3,3, 3-Pentafluorpropylcarbonyl, Heptafluorpropylcarbonyl, 1- (Fluormethyl) -2-fluor- ethylcarbonyl, 1- (Chlormethyl) -2-chlorethylcarbonyl, 1- (Brommethyl) -2-bromethylcarbonyl, 4-Fluorbutylcarbonyl, 4-Chlor- butylcarbonyl , 4-Brombutylcarbonyl, Nonafluorbutylcarbonyl, (5-Fluor-l-pentyl) carbonyl, (5-Chlor-l-pentyl) carbonyl, (5 -Brom-1-pentyl) carbonyl, (5-Iod-l-pentyl) carbonyl, (5,5,5 -Trichlor-1-pentyl) carbonyl, Undecafluorpentylcarbonyl, (6 -Fluor- 1 -hexy1) carbonyl , (6 -Chlor- 1 -hexyl) carbonyl , (6 -Brom- 1 -hexyl) carbonyl, (6 - Iod- 1-hexyl) carbonyl, (6, 6, 6-Trichlor-1 -hexyl) carbonyl oder Dodecafluorhexyl- carbonyl, insbesondere für Trifluoracetyl;- (Ci-Cg-haloalkyl) carbonyl for: a (Ci-Cg-alkyl) carbonyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloroacetyl, dichloroacetyl, trichloroacetyl , Fluoroacetyl, difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2, 2-difluoroethylcarbonyl, 2, 2, 2-trif carbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2, 2-difluoroethylcarbonyl, 2, 2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2, 2-difluoropropylcarbonyl, 2, 3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2, 3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3, 3, 3-trifluoropropylcarbonyl 3,3,3-trichloropropylcarbonyl, 2,2,3,3,3-pentafluoropropylcarbonyl, heptafluoropropylcarbonyl, 1- (fluoromethyl) -2-fluoroethylcarbonyl, 1- (chloromethyl) -2-chloroethylcarbonyl, 1- (bromomethyl) - 2-bromethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl, nonafluorobutylcarbonyl, (5-fluoro-1-pentyl) carbonyl, (5-chloro-1-pentyl) carbonyl, (5-bromo-1-pentyl ) carbonyl, (5-iodo-l-pentyl) carbonyl, (5,5,5-trichloro-1-pentyl) carbonyl, undecafluoropentylcarbonyl, (6-fluoro-1-hexy1) carbonyl, (6-chloro-1-hexyl ) carbonyl, (6-bromo-1-hexyl) carb onyl, (6 - iodo-1-hexyl) carbonyl, (6, 6, 6-trichloro-1-hexyl) carbonyl or dodecafluorohexylcarbonyl, especially for trifluoroacetyl;
(Cι~Cg-Alkyl) carbonyloxy für: Acetyloxy, Ethylcarbonyloxy, n-Propylcarbonyloxy, 1-Methylethylcarbonyloxy, n-Butyl- carbonyloxy, 1-Methylpropylcarbonyloxy, 2-Methylpropyl- carbonyloxy, 1, 1-Dimethylethylcarbonyloxy, n-Pentylcarbonyl - oxy, 1-Methylbutylcarbonyloxy, 2-Methylbutylcarbonyloxy, 3-Methylbutylcarbonyloxy, 1, 1-Dimethylpropylcarbonyloxy, 1, 2-Dimethylpropylcarbonyloxy, 2 , 2-Dimethylpropylcarbonyloxy, 1-Ethylpropylcarbonyloxy, n-Hexylcarbonyloxy, 1-Methylpentyl- carbonyloxy, 2-Methylpentylcarbonyloxy, 3-Methylpentyl- carbonyloxy, 4-Methylpentylcarbonyloxy, 1, 1-Dimethylbutyl- carbonyloxy, 1, 2-Dimethylbutylcarbonyloxy, 1, 3-Dimethylbutyl - carbonyloxy, 2, 2-Dimethylbutylcarbonyloxy, 2, 3-Dimethylbutyl - carbonyloxy, 3 , 3-Dimethylbutylcarbonyloxy, 1-Ethylbutyl- carbonyloxy, 2-Ethylbutylcarbonyloxy, 1,1, 2-Trimethylpropyl - carbonyloxy, 1, 2, 2-Trimethylpropylcarbonyloxy, 1-Ethyl-l- methylpropylcarbonyloxy oder l-Ethyl-2-methylpropylcarbonyl- oxy, insbesondere für Acetyloxy;(Cι ~ Cg-alkyl) carbonyloxy for: acetyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1, 1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1, 1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2, 2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n-hexylcarbonyloxy, 1-methylpentyl-methylpentoxycarbonyloxy Methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, 1, 1-dimethylbutylcarbonyloxy, 1, 2-dimethylbutylcarbonyloxy, 1, 3-dimethylbutyl - carbonyloxy, 2, 2-dimethylbutylcarbonyloxy, 2, 3-dimethylbutyl - carbonyloxy, 3, 3-dimethylbutylcarbonyloxy 1-ethylbutylcarbonyloxy, 2-ethylbutylcarbonyloxy, 1,1, 2-trimethylpropylcarbonyloxy, 1, 2, 2-trimethylpropylcarbonyloxy, 1-ethyl-l-methylpropylcarbonyloxy or l-ethyl-2-methylpropylcarbonyloxy, especially for acetyloxy ;
(Ci-Cg-Halogenalkyl) carbonyloxy für: einen (Ci-Cg-Alkyl) - carbonyloxy-Rest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Chloracetyloxy, Dichloracetyloxy, Trichloracetyloxy, Fluoracetyloxy, Difluoracetyloxy, Tri- fluoracetyloxy, Chlorfluoracetyloxy, Dichlorfluoracetyloxy, Chlordifluoracetyloxy, 2-Fluorethylcarbonyloxy, 2-Chlorethyl- carbonyloxy, 2-Bromethylcarbonyloxy, 2-Iodethylcarbonyloxy, 2 , 2-Difluorethylcarbonyloxy, 2,2, 2-Trifluorethylcarbonyloxy. 2-Chlor-2-fluorethylcarbonyloxy, 2-Chlor-2 , 2-difluorethyl - carbonyloxy, 2, 2-Dichlor-2-fluorethylcarbonyloxy, 2,2,2-Tri- chlorethylcarbonyloxy, Pentafluorethylcarbonyloxy, 2-Fluor- propylcarbonyloxy, 3-Fluorpropylcarbonyloxy, 2,2-Difluor- propylcarbonyloxy, 2, 3-Difluorpropylcarbonyloxy, 2-Chlor- propylcarbonyloxy, 3-Chlorpropylcarbonyloxy, 2,3-Dichlor- propylcarbonyloxy, 2-Brompropylcarbonyloxy, 3-Brompropyl- carbonyloxy, 3 , 3, 3-Trifluorpropylcarbonyloxy, 3 , 3 , 3-Trichlor- propylcarbonyloxy, 2,2,3,3, 3-Pentafluorpropylcarbonyloxy, Heptafluorpropylcarbonyloxy, 1- (Fluormethyl) -2-fluorethylcarbonyloxy, 1- (Chlormethyl) -2-chlorethylcarbonyloxy, 1- (Brommethyl) -2-bromethylcarbonyloxy, 4-Fluorbutylcarbonyl - oxy, 4-Chlorbutylcarbonyloxy, 4-Brombutyl oder Nonafluor- butyl, insbesondere für Trifluoracetoxy;(Ci-Cg-haloalkyl) carbonyloxy for: a (Ci-Cg-alkyl) carbonyloxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloroacetyloxy, dichloroacetyloxy, trichloroacetyloxy , Fluoroacetyloxy, difluoroacetyloxy, trifluoroacetyloxy, chlorofluoroacetyloxy, dichlorofluoroacetyloxy, chlorodifluoroacetyloxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 2-bromoethylcarbonyloxy, 2-iodoethylcarbonyloxy, 2, 2-difluoroethylcarbonyl. 2-chloro-2-fluoroethylcarbonyloxy, 2-chloro-2, 2-difluoroethylcarbonyloxy, 2, 2-dichloro-2-fluoroethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy, pentafluoroethylcarbonyloxy, 2-fluoropropylcarbonyloxy, 3- Fluoropropylcarbonyloxy, 2,2-difluoropropylcarbonyloxy, 2, 3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyloxy, 3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyloxy, 2-bromopropylcarbonyloxy, 3-bromopropylcarbonyloxy, 3, 3, 3- Trifluoropropylcarbonyloxy, 3, 3, 3-trichloropropylcarbonyloxy, 2,2,3,3, 3-pentafluoropropylcarbonyloxy, heptafluoropropylcarbonyloxy, 1- (fluoromethyl) -2-fluoroethylcarbonyloxy, 1- (chloromethyl) -2-chloroethylcarbonyloxy, 1- (bromomethyl ) -2-bromethylcarbonyloxy, 4-fluorobutylcarbonyloxy, 4-chlorobutylcarbonyloxy, 4-bromobutyl or nonafluorobutyl, especially for trifluoroacetoxy;
(Ci-Cδ-Alkyl) carbonyloxy-Ci-Cδ"alkyl für: durch (Ci-Cδ-Alkyl) - carbonyloxy wie vorstehend genannt substituiertes Cι-C6 -Alkyl, also z.B. für Methylcarbonyloxymethyl , Ethylcarbonyloxy- methyl, 1- (Methylcarbonyloxy) ethyl, 2 - (Methylcarbonyloxy) - ethyl, 2 - (Ethylcarbonyloxy) ethyl , 3 - (Methylcarbonyloxy) - propyl , 4 - (Methoxycarbonyloxy) butyl , 5 - (Methoxycarbonyloxy) - pentyl oder 6 - (Methoxycarbonyloxy) hexyl ;(Ci-C δ- alkyl) carbonyloxy-Ci-C δ "alkyl for: C 1 -C 6 -alkyl substituted by (Ci-C δ- alkyl) carbonyloxy as mentioned above, that is, for example for methylcarbonyloxymethyl, ethylcarbonyloxy-methyl, 1st - (Methylcarbonyloxy) ethyl, 2 - (methylcarbonyloxy) ethyl, 2 - (ethylcarbonyloxy) ethyl, 3 - (methylcarbonyloxy) propyl, 4 - (methoxycarbonyloxy) butyl, 5 - (methoxycarbonyloxy) pentyl or 6 - (methoxycarbonyloxy) hexyl ;
(C -Cδ-Alkyl) carbonylthio für Acetylthio, Ethylcarbonylthio, n-Propylcarbonylthio, 1-Methylethylcarbonylthio, n-Butylcarbonylthio, 1-Methylpropylcarbonylthio, 2-Methylpropyl- carbonylthio, 1, 1-Dimethylethylcarbonylthio, n-Pentylcarbonylthio, 1-Methylbutylcarbonylthio, 2-Methylb tyl- carbonylthio, 3-Methylbutylcarbonylthio, 1, 1-Dimethylpropyl- carbonylthio, 1, 2-Dirnethylpropylcarbonylthio, 2, 2-Dimethyl- propylcarbonylthio, 1-Ethylpropylcarbonylthio, n-Hexyl- carbonylthio, 1-Methylpentylcarbonylthio, 2-Methylpentyl- carbonylthio, 3-Methylpentylcarbonylthio, 4-Methylpentyl- carbonylthio, 1, 1-Dimethylbutylcarbonylthio, 1, 2-Dimethyl- butylcarbonylthio, 1, 3-Dirnethylbutylcarbonylthio,(C -C δ alkyl) carbonylthio for acetylthio, ethylcarbonylthio, n-propylcarbonylthio, 1-methylethylcarbonylthio, n-butylcarbonylthio, 1-methylpropylcarbonylthio, 2-methylpropylcarbonylthio, 1, 1-dimethylethylcarbonylthio, n-pentylcarbonylthio, n-pentylcarbonylthio 2-methylbutylcarbonylthio, 3-methylbutylcarbonylthio, 1, 1-dimethylpropylcarbonylthio, 1, 2-dimethylpropylcarbonylthio, 2, 2-dimethylpropylcarbonylthio, 1-ethylpropylcarbonylthio, n-hexylcarbonylthio, 1-methylpentylcarbonylthio - carbonylthio, 3-methylpentylcarbonylthio, 4-methylpentylcarbonylthio, 1, 1-dimethylbutylcarbonylthio, 1, 2-dimethylbutylcarbonylthio, 1, 3-dimethylbutylcarbonylthio,
2 , 2-Dirnethylbutylcarbonylthio, 2, 3-Dirnethylbutylcarbonylthio,2,2-dimethylbutylcarbonylthio, 2,3-dimethylbutylcarbonylthio,
3 , 3-Dirnethylb tylcarbonylthio, 1-Ethylbutylcarbonylthio,3, 3-dirnethylb tylcarbonylthio, 1-ethylbutylcarbonylthio,
2-Ethylbutylcarbonylthio, 1,1, 2-Trimethylpropylcarbonylthio, 1,2, 2-Trimethylpropylcarbonylthio, 1-Ethyl-l-methylpropyl - carbonylthio oder l-Ethyl-2-methylpropylcarbonylthio, insbesondere für Acetylthio;2-ethylbutylcarbonylthio, 1,1, 2-trimethylpropylcarbonylthio, 1,2, 2-trimethylpropylcarbonylthio, 1-ethyl-l-methylpropylcarbonylthio or l-ethyl-2-methylpropylcarbonylthio, especially for acetylthio;
(Ci-Cδ-Halogenalkyl) carbonylthio für: einen (Ci -Cg -Alkyl) - carbonylthio-Rest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Chloracetylthio, Dichloracetylthio, Trichloracetylthio, Fluoracetylthio, Difluoracetylthio, Tri- fluoracetylthio, Chlorfluoracetylthio, Dichlorfluoracetyl - thio, Chlordifluoracetylthio, 2-Fluorethylcarbonylthio, 2-Chlorethylcarbonylthio, 2-Bromethylcarbonylthio, 2-Iod- ethylcarbonylthio, 2 , 2-Difluorethylcarbonylthio, 2,2,2-Tri- fluorethylcarbonylthio, 2-Chlor-2-fluorethylcarbonylthio, 2-Chlor-2 , 2-difluorethylcarbonylthio, 2 , 2-Dichlor-2-fluorethylcarbonylthio, 2 , 2, 2-Trichlorethylcarbonylthio, Penta- fluorethylcarbonylthio, 2-Fluorpropylcarbonylthio, 3-Fluor- propylcarbonylthio, 2 , 2-Difluorpropylcarbonylthio, 2,3-Di- fluorpropylcarbonylthio, 2-Chlorpropylcarbonylthio, 3-Chlor- propylcarbonylthio, 2 , 3-Dichlorpropylcarbonylthio, 2-Brom- propylcarbonylthio, 3-Brompropylcarbonylthio, 3 , 3 , 3-Trifluorpropylcarbonylthio, 3,3, 3-Trichlorpropylcarbonylthio, 2,2,3,3, 3-Pentafluorpropylcarbonylthio, Heptafluorpropyl - carbonylthio, 1- (Fluormethyl) -2-fluorethylcarbonylthio,(Ci-C δ -haloalkyl) carbonylthio for: a (Ci-Cg-alkyl) carbonylthio radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloroacetylthio, dichloroacetylthio, Trichloroacetylthio, fluoroacetylthio, difluoroacetylthio, tri- fluoroacetylthio, chlorofluoroacetylthio, dichlorofluoroacetylthio, chlorodifluoroacetylthio, 2-fluoroethylcarbonylthio, 2-chloroethylcarbonylthio, 2-bromoethylcarbonylthio, 2-iodo-ethylcarbonylthio, 2, 2-difluoroethylcarbonylthio, 2,2,2-tri-fluoro, 2,2,2-tri-fluoro fluoroethylcarbonylthio, 2-chloro-2, 2-difluoroethylcarbonylthio, 2, 2-dichloro-2-fluoroethylcarbonylthio, 2, 2, 2-trichloroethylcarbonylthio, pentafluoroethylcarbonylthio, 2-fluoropropylcarbonylthio, 3-fluoropropylcarbonylthio, 2, 2-difluoropropylcarbonylthio 2,3-di-fluoropropylcarbonylthio, 2-chloropropylcarbonylthio, 3-chloropropylcarbonylthio, 2, 3-dichloropropylcarbonylthio, 2-bromopropylcarbonylthio, 3-bromopropylcarbonylthio, 3, 3, 3-trifluoropropylcarbonylthio, 3,3, 3-trichloropropyl 2,2,3,3,3-pentafluoropropylcarbonylthio, heptafluoropropylcarbonylthio, 1- (fluoromethyl) -2-fluoroethylcarbonylthio,
1- (Chlormethyl) -2-chlorethylcarbonylthio, 1- (Brommethyl) - 2-bromethylcarbonylthio, 4-Fluorbutylcarbonylthio, 4-Chlor- butylcarbonylthio, 4-Brombutylthio oder Nonafluorbutylthio, insbesondere für Trifluoracetylthio;1- (chloromethyl) -2-chloroethylcarbonylthio, 1- (bromomethyl) - 2-bromethylcarbonylthio, 4-fluorobutylcarbonylthio, 4-chlorobutylcarbonylthio, 4-bromobutylthio or nonafluorobutylthio, especially for trifluoroacetylthio;
(Ci-Cg-Alkyl) carbamoyloxy für: Methylcarbamoyloxy, Ethylcarb- amoyloxy, n-Propylcarbamoyloxy, 1-Methylethylcarbamoyloxy, n-Butylcarbamoyloxy, 1-Methylpropylcarbamoyloxy, 2-Methyl- propylcarbamoyloxy, 1, 1-Dimethylethylcarbamoyloxy, n-Pentyl- carbamoyloxy, 1-Methylbutylcarbamoyloxy, 2-Methylbutylcarb- amoyloxy, 3-Methylbutylcarbamoyloxy, 1, 1-Dirnethylpropylcarbamoyloxy, 1, 2-Dimethylpropylcarbamoyloxy, 2, 2-Dirnethylpropyl - carbamoyloxy, 1-Ethylpropylcarbamoyloxy, n-Hexylcarbamoyloxy, 1-Methylpentylcarbamoyloxy, 2-Methylpentylcarbamoyloxy, 3-Methylpentylcarbamoyloxy, 4-Methylpentylcarbamoyloxy,(Ci-Cg-alkyl) carbamoyloxy for: methylcarbamoyloxy, ethylcarbamoyloxy, n-propylcarbamoyloxy, 1-methylethylcarbamoyloxy, n-butylcarbamoyloxy, 1-methylpropylcarbamoyloxy, 2-methylpropylcarbamoyloxy, 1, 1-dimethylethyl-pamoyloxy, pentamoyloxy, 1-Methylbutylcarbamoyloxy, 2-Methylbutylcarbamoyloxy, 3-Methylbutylcarbamoyloxy, 1, 1-Dirnethylpropylcarbamoyloxy, 1, 2-Dimethylpropylcarbamoyloxy, 2, 2-Dirnethylpropyl-carbamoyloxy, 1-Ethylpropylcarbamoylamyllamyloxamoyloxamyloxamyloxamoylamyllamyloxamyloxyamoyloxy, 1-methyl-hexamoyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxyamyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxamyloxy 3-methylpentylcarbamoyloxy, 4-methylpentylcarbamoyloxy,
1 , 1-Dimethylbutylcarbamoyloxy, 1 , 2-Dimethylbutylcarbamoyloxy,1, 1-dimethylbutylcarbamoyloxy, 1, 2-dimethylbutylcarbamoyloxy,
1, 3-Dimethylb tylcarbamoyloxy, 2, 2-Dimethylbutylcarbamoyloxy,1, 3-dimethylb tylcarbamoyloxy, 2, 2-dimethylbutylcarbamoyloxy,
2 , 3-Dimethylb tylcarbamoyloxy, 3 , 3-Dimethylb tylcarbamoyloxy, 1-Ethylbutylcarbamoyloxy, 2-Ethylbutylcarbamoyloxy, 1,1, 2-Trimethylpropylcarbamoyloxy, 1,2, 2-Trimethylpropyl - carbamoyloxy, 1-Ethyl-l-methylpropylcarbamoyloxy oder l-Ethyl-2-methylpropylcarbamoyloxy, insbesondere für Methylcarbamoyloxy;2, 3-dimethylb tylcarbamoyloxy, 3, 3-dimethylb tylcarbamoyloxy, 1-ethylbutylcarbamoyloxy, 2-ethylbutylcarbamoyloxy, 1,1, 2-trimethylpropylcarbamoyloxy, 1,2, 2-trimethylpropyl-carbamoyloxy, 1-ethyl-l-methylloxy propyl Ethyl 2-methylpropylcarbamoyloxy, especially for methylcarbamoyloxy;
(Ci-Cg-Halogenalkyl) carbamoyloxy für: einen (Ci-Cg-Alkyl) - carbamoyloxy-Rest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Chlormethylcarbamoyloxy, Dichlor- methylcarbamoyloxy, Trichlormethylcarbamoyloxy, Fluormethyl - carbamoyloxy, Difluormethylcarbamoyloxy, Trifluormethylcarb- amoyloxy, Chlorfluormethylcarbamoyloxy, Dichlorfluormethylcarbamoyloxy, Chlordifluormethylcarbamoyloxy, • 2-Fluorethyl- carbamoyloxy, 2-Chlorethylcarbamoyloxy, 2-Bromethylcarbamoyloxy, 2-Iodethylcarbamoyloxy, 2, 2-Difluorethylcarbamoyloxy, 2, 2, 2-Trifluorethylcarbamoyloxy, 2-Chlor-2-fluorethylcarbamoyloxy, 2-Chlor-2, 2-difluorethylcarbamoyloxy, 2,2-Di- chlor-2-fluorethylcarbamoyloxy, 2, 2, 2-Trichlorethylcarb- amoyloxy, Pentafluorethylcarbamoyloxy, 2-Fluorpropylcarb- amoyloxy, 3-Fluorpropylcarbamoyloxy, 2, 2-Difluorpropylcarb- amoyloxy, 2, 3-Difluorpropylcarbamoyloxy, 2-Chlorpropylcarb- amoyloxy, 3-Chlorpropylcarbamoyloxy, 2, 3-Dichlorpropylcarb- amoyloxy, 2-Brompropylcarbamoyloxy, 3-Brompropylcarbamoyloxy, 3,3, 3-Trifluorpropylcarbamoyloxy, 3,3, 3-Trichlorpropylcarb- amoyloxy, 2, 2, 3 , 3 , 3-Pentafluorpropylcarbamoyloxy, Heptafluorpropylcarbamoyloxy, 1- (Fluormethyl) -2-fluorethylcarbamoyloxy, 1- (Chlormethyl) -2-chlorethylcarbamoyloxy, 1- (Brommethyl) - 2-bromethylcarbamoyloxy, 4-Fluorbutylcarbamoyloxy, 4-Chlor- butylcarbamoyloxy, 4-Brombutylcarbamoyloxy oder Nonafluor- butylcarbamoyloxy, insbesondere für Trifluormethylcarbamoyloxy;(Ci-Cg-haloalkyl) carbamoyloxy for: a (Ci-Cg-alkyl) -carbamoyloxy radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethylcarbamoyloxy, dichloromethylcarbamoyloxy , Trichloromethyl carbamoyloxy, fluoromethyl carbamoyloxy, difluoromethyl carbamoyloxy, trifluoromethyl carbamoyloxy, chlorofluoromethyl carbamoyloxy, dichlorofluoromethyl carbamoyloxy, chlorodifluoromethyl carbamoyloxy, • 2-fluoroethyl carbamoyloxy, 2-chloroethylcarbamoyloxy, 2-bromoethylcarbamoyloxy, 2-iodoethylcarbamoyloxy, 2, 2-difluoroethylcarbamoyloxy, 2, 2, 2-trifluoroethylcarbamoyloxy, 2-chloro-2-fluoroethylcarbamoyloxy, 2-chloro-2, 2-difluoroethylcarbamoyloxy Di-chloro-2-fluoroethylcarbamoyloxy, 2, 2, 2-trichloroethylcarbamoyloxy, pentafluoroethylcarbamoyloxy, 2-fluoropropylcarbamoyloxy, 3-fluoropropylcarbamoyloxy, 2, 2-difluoropropylcarbamoyloxy, 2, 3-difluoropropylcarboxoyloxy 3-chloropropylcarbamoyloxy, 2, 3-dichloropropylcarbamoyloxy, 2-bromopropylcarbamoyloxy, 3-bromopropylcarbamoyloxy, 3,3, 3-trifluoropropylcarbamoyloxy, 3,3, 3-trichloropropylcarbamoyloxy, 2, 2, 3, 3, 3-pylafluoroyloxy Heptafluoropropylcarbamoyloxy, 1- (fluoromethyl) -2-fluoroethylcarbamoyloxy, 1- (chloromethyl) -2-chloroethylcarbamoyloxy, 1- (bromomethyl) - 2-bromethylcarbamoyloxy, 4-fluorobutylcarbamoyloxy, 4-chlorobutylcarbamoyloxy, 4-bromobutylcarbamoyloxy, nonoxybutylcarbamoyloxy, especially re for trifluoromethylcarbamoyloxy;
Ci-Cg-Alkoxy für: z.B. OCH3 , 0C2H5, OCH2-C2H5, OCH(CH3)2, n-Butoxy, OCH(CH3)-C2H5, OCH2-CH (CH3) 2, OC(CH3)3, n-Pentoxy, 1-Methylbutoxy, 2-Methylbutoxy, 3-Methylb toxy, 1, 1-Dirnethyl- propoxy, 1, 2-Dimethylpropoxy, 2, 2-Dimethylpropoxy, 1-Ethyl- propoxy, n-Hexoxy, 1-Methylpentoxy, 2-Methylpentoxy, 3-Methylpentoxy, 4-Methylpentoxy, 1, 1-Dirnethylb toxy,Ci-Cg-alkoxy for: for example OCH 3 , 0C 2 H 5 , OCH 2 -C 2 H 5 , OCH (CH 3 ) 2 , n-butoxy, OCH (CH 3 ) -C 2 H 5 , OCH 2 -CH (CH 3 ) 2 , OC (CH 3 ) 3 , n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylb toxy, 1, 1-dirnethyl-propoxy, 1, 2-dimethylpropoxy, 2, 2-dimethylpropoxy, 1-ethyl-propoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dirnethylb toxy,
1, 2-Dimethylbutoxy, 1, 3-Dimethylbutoxy, 2, 2-Dimethylbutoxy, 2, 3-Dirnethylbutoxy, 3 , 3-Dimethylbutoxy, 1-Ethylbutoxy, 2-Ethylbutoxy, 1, 1, 2-Trimethylpropoxy, 1, 2, 2-Trimethylprop- oxy, 1-Ethyl-l-methylpropoxy und l-Ethyl-2-methylpropoxy, insbesondere für OCH3, OC2H5 oder OCH(CH3) ;1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2, 2-dimethylbutoxy, 2, 3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2, 2-trimethylpropoxy, 1-ethyl-l-methylpropoxy and l-ethyl-2-methylpropoxy, in particular for OCH 3 , OC 2 H 5 or OCH (CH 3 );
Cι-C4-Halogenalkoxy für: einen Cι-C4-Alkoxyrest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Chlormethoxy, Dichlormethoxy, Trichlormethoxy, Fluormethoxy, Difluormeth- oxy, Trifluormethoxy, Chlorfluormethoxy, Dichlorfluormethoxy, Chlordifluormethoxy, 2-Fluorethoxy, 2-Chlorethoxy, 2-Brom- ethoxy, 2-Iodethoxy, 2, 2-Difluorethoxy, 2, 2, 2-Trifluorethoxy, 2-Chlor-2-fluorethoxy, 2-Chlor-2, 2-difluorethoxy, 2,2-Di- chlor-2-fluorethoxy, 2 , 2, 2-Trichlorethoxy, Pentafluorethoxy, 2-Fluorpropoxy, 3-Fluorpropoxy, 2, 2-Difluorpropoxy, 2,3-Di- fluorpropoxy, 2-Chlorpropoxy, 3-Chlorpropoxy, 2,3-Dichlor- propoxy, 2-Brompropoxy, 3-Brompropoxy, 3 , 3 , 3-Trifluorpropoxy, 3 , 3 , 3-Trichlorpropoxy, 2, 2, 3 , 3 , 3-Pentafluorpropoxy, Hepta- fluorpropoxy, 1- (Fluormethyl) -2-fluorethoxy, 1- (Chlormethyl) -2-chlorethoxy, 1- (Brommethyl) -2-bromethoxy, 4-Fluor- butoxy, 4-Chlorbutoxy, 4-Brombutoxy oder Nonafluorbutoxy, insbesondere für 2 -Chlorethoxy oder 2 , 2 , 2 -Trifluorethoxy;Cι-C for 4 -haloalkoxy: a Cι-C 4 alkoxy as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, ie, for example chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, Difluormeth- oxy, Trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2, 2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2- Chloro-2,2-difluoroethoxy, 2,2-di-chloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-di- fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3, 3, 3-trifluoropropoxy, 3, 3, 3-trichloropropoxy, 2, 2, 3, 3, 3-pentafluoropropoxy, hepta-fluoropropoxy, 1- (fluoromethyl) -2-fluoroethoxy, 1- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2-bromoethoxy, 4-fluoro- butoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, especially for 2-chloroethoxy or 2, 2, 2-trifluoroethoxy;
Ci-Cg-Halogenalkoxy für: einen Ci-Cg-Alkoxyrest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor,Ci-Cg-haloalkoxy for: a Ci-Cg-alkoxy radical as mentioned above, partially or completely by fluorine, chlorine,
Brom und/oder Iod substituiert ist, also z.B. einen der unter Cι-C4-Halogenalkoxy genannten Reste oder für 5 -Fluor-1-pent- oxy, 5-Chlor-l-pentoxy, 5-Brom-l-pentoxy, 5-Iod-l-pentoxy,Bromine and / or iodine is substituted, for example one of the radicals mentioned under C 1 -C 4 -haloalkoxy or for 5 -fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5 Iodine-l-pentoxy,
5, 5, 5-Trichlor-l-pentoxy, Undecafluorpentoxy, 6-Fluor-l- hexoxy, 6-Chlor-l-hexoxy, 6-Brom-l-hexoxy, 6-Iod-l-hexoxy,5, 5, 5-trichloro-1-pentoxy, undecafluoropentoxy, 6-fluoro-1-hexoxy, 6-chloro-1-hexoxy, 6-bromo-1-hexoxy, 6-iodo-1-hexoxy,
6, 6, 6-Trichlor-l-hexoxy oder Dodecafluorhexoxy, insbesondere für Chlormethoxy, Fluormethoxy, Difluormethoxy, Trifluormethoxy, 2-Fluorethoxy, 2-Chlorethoxy oder 2, 2, 2-Trifluorethoxy;6, 6, 6-trichloro-l-hexoxy or dodecafluorohexoxy, in particular for chloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy or 2,2,2-trifluoroethoxy;
Hydroxy-Ci-Cg -alkoxy für: z.B. OCH2-OH, OCH(CH3)-OH,Hydroxy-Ci-Cg -alkoxy for: e.g. OCH 2 -OH, OCH (CH 3 ) -OH,
OCH2-CH2-OH, OCH(C2H5)-OH, OCH2-CH (CH3) -OH, 3-Hydroxy- prop-1-yloxy, 1-Hydroxybut-l-yloxy, 2-Hydroxybut-l-yloxy, 3-Hydroxybut-l-yloxy, 4-Hydroxybut-l-yloxy, 1-Hydroxy- but-2-yloxy, 2-Hydroxybut-2-yloxy, 3-Hydroxybut-2-yloxy, 4-Hydroxybut-2-yloxy, 1- (CH2-OH) -eth-1-yloxy, l-(CH2-OH)-OCH 2 -CH 2 -OH, OCH (C 2 H 5 ) -OH, OCH 2 -CH (CH 3 ) -OH, 3-hydroxy-prop-1-yloxy, 1-hydroxybut-l-yloxy, 2-hydroxybut -l-yloxy, 3-hydroxybut-l-yloxy, 4-hydroxybut-l-yloxy, 1-hydroxybut-2-yloxy, 2-hydroxybut-2-yloxy, 3-hydroxybut-2-yloxy, 4-hydroxybut -2-yloxy, 1- (CH 2 -OH) -eth-1-yloxy, l- (CH 2 -OH) -
1- (CH3) -eth-1-yloxy oder 1- (CH-OH) -prop-1-yloxy, insbesondere für OCH2-OH oder OCH2-CH2-OH;1- (CH 3 ) -eth-1-yloxy or 1- (CH-OH) -prop-1-yloxy, especially for OCH 2 -OH or OCH 2 -CH 2 -OH;
Cyano-Ci-Cg-alkoxy für: z.B. OCH-CN, OCH(CH3)-CN, OCH2-CH2-CN, OCH (C2H5) -OH, OCH2-CH (CH3) -CN, 3-Cyanoprop-l-yl - oxy, 1-Cyanobut-l-yloxy, 2-Cyanobut-l-yloxy, 3-Cyanobut-l-yl- oxy, 4-Cyanobut-l-yloxy, l-Cyanobut-2-yloxy, 2-Cyanobut-2-yl- oxy, 3-Cyanobut-2-yloxy, 4-Cyanobut-2-yloxy, 1- (CH2-CN) -eth- 1-yloxy, 1- (CH2-CN) -1- (CH3) -eth-1-yloxy oder 1- (CH2-CN) -prop- 1-yloxy, insbesondere für OCH2-CN oder OCH-CH2-CN;Cyano-Ci-Cg-alkoxy for: e.g. OCH-CN, OCH (CH 3 ) -CN, OCH 2 -CH 2 -CN, OCH (C 2 H 5 ) -OH, OCH 2 -CH (CH 3 ) -CN , 3-cyanoprop-l-yl-oxy, 1-cyanobut-l-yloxy, 2-cyanobut-l-yloxy, 3-cyanobut-l-yl-oxy, 4-cyanobut-l-yloxy, l-cyanobut-2 -yloxy, 2-cyanobut-2-yloxy, 3-cyanobut-2-yloxy, 4-cyanobut-2-yloxy, 1- (CH 2 -CN) -eth- 1-yloxy, 1- (CH 2 - CN) -1- (CH 3 ) -eth-1-yloxy or 1- (CH 2 -CN) prop-1-yloxy, in particular for OCH 2 -CN or OCH-CH 2 -CN;
Phenyl -Ci-Cg-alkoxy für: z.B. Benzyloxy, 1-Phenylethoxy, 2-Phenylethoxy, 1-Phenylprop-l-yloxy, 2-Phenylprop-l-yloxy, 3-Phenylprop-l-yloxy, 1-Phenylbut-l-yloxy, 2-Phenylbut-l-yl- oxy, 3-Phenylb t-l-yloxy, 4-Phenylbut-l-yloxy, 1-Phenyl- but-2-yloxy, 2-Phenylbut-2-yloxy, 3-Phenylbut-2-yloxy, 4-Phenylbut-2-yloxy, 1- (Benzyl) -eth-1-yloxy, 1- (Benzyl) -1- (methyl) -eth-1-yloxy oder 1- (Benzyl) -prop-1-yloxy, insbesondere für Benzyloxy oder 2-Phenylethoxy;Phenyl-Ci-Cg-alkoxy for: e.g. Benzyloxy, 1-phenylethoxy, 2-phenylethoxy, 1-phenylprop-l-yloxy, 2-phenylprop-l-yloxy, 3-phenylprop-l-yloxy, 1-phenylbut-l-yloxy, 2-phenylbut-l-yl- oxy, 3-phenylb tl-yloxy, 4-phenylbut-l-yloxy, 1-phenylbut-2-yloxy, 2-phenylbut-2-yloxy, 3-phenylbut-2-yloxy, 4-phenylbut-2-yloxy , 1- (benzyl) -eth-1-yloxy, 1- (benzyl) -1- (methyl) -eth-1-yloxy or 1- (benzyl) -prop-1-yloxy, especially for benzyloxy or 2-phenylethoxy ;
Heterocyclyl-Ci-Cg-alkoxy für: z.B. Heterocyclylmethoxy, 1- (Heterocyclyl) ethoxy, 2- (Heterocyclyl) ethoxy, l-(Hetero- cyclyl)prop-l-yloxy, 2- (Heterocyclyl) prop-1-yloxy, 3- (Heterocyclyl)prop-1-yloxy, 1- (Heterocyclyl) but-1-yloxy, 2-(Hetero- cyclyl)but-l-yloxy, 3- (Heterocyclyl) but-1-yloxy, 4- (Heterocyclyl) but-1-yloxy, 1- (Heterocyclyl) but-2-yloxy, 2- (Heterocyclyl) but-2-yloxy, 3- (Heterocyclyl) but-2-yloxy, 4-(Hetero- cyclyl)but-2-yloxy, 1- (Heterocyclylmethyl) -eth-1-yloxy, 1- (Heterocyclylmethyl) -1- (methyl) -eth-1-yloxy oder 1- (Heterocyclylmethyl) -prop-1-yloxy, insbesondere für Heterocyclyl - methoxy oder 2- (Heterocyclyl) ethoxy;Heterocyclyl-Ci-Cg-alkoxy for: e.g. heterocyclylmethoxy, 1- (heterocyclyl) ethoxy, 2- (heterocyclyl) ethoxy, l- (heterocyclicl) prop-l-yloxy, 2- (heterocyclyl) prop-1-yloxy, 3- (heterocyclyl) prop-1-yloxy, 1- (heterocyclyl) but-1-yloxy, 2- (heterocyclyl) but-l-yloxy, 3- (heterocyclyl) but-1-yloxy, 4- (heterocyclyl ) but-1-yloxy, 1- (heterocyclyl) but-2-yloxy, 2- (heterocyclyl) but-2-yloxy, 3- (heterocyclyl) but-2-yloxy, 4- (hetero- cyclyl) but-2-yloxy, 1- (heterocyclylmethyl) -eth-1-yloxy, 1- (heterocyclylmethyl) -1- (methyl) -eth-1-yloxy or 1- (heterocyclylmethyl) prop-1-yloxy, especially for heterocyclyl methoxy or 2- (heterocyclyl) ethoxy;
Phenyl -Ci-Cg-alkylthio für: z.B. Benzylthio, 1-Pheny1ethy1- thio, 2-Phenylethylthio, 1-Phenylprop-l-ylthio, 2-Phenyl- prop-1-ylthio, 3-Phenylprop-l-ylthio, 1-Phenylbut-l-ylthio, 2-Phenylbut-l-ylthio, 3-Phenylbut-l-ylthio, 4-Phenylbut-l- ylthio, l-Phenylbut-2-ylthio, 2-Phenylbut-2-ylthio, 3-Phenyl- but-2-ylthio, 4-Phenylbut-2-ylthio, 1- (Phenylmethyl) -eth-1- ylthio, 1- (Phenylmethyl) -1- (methyl) -eth-1-ylthio oder 1- (Phenylmethyl) -prop-1-ylthio, insbesondere für Benzylthio oder 2-Pheny1ethy1thio;Phenyl-Ci-Cg-alkylthio for: e.g. Benzylthio, 1-phenylethy1-thio, 2-phenylethylthio, 1-phenylprop-l-ylthio, 2-phenylprop-1-ylthio, 3-phenylprop-l-ylthio, 1-phenylbut-l-ylthio, 2-phenylbut- l-ylthio, 3-phenylbut-l-ylthio, 4-phenylbut-l-ylthio, l-phenylbut-2-ylthio, 2-phenylbut-2-ylthio, 3-phenylbut-2-ylthio, 4-phenylbut- 2-ylthio, 1- (phenylmethyl) -eth-1-ylthio, 1- (phenylmethyl) -1- (methyl) -eth-1-ylthio or 1- (phenylmethyl) prop-1-ylthio, especially for benzylthio or 2-phenylethy1thio;
(Ci-Cg-Alkoxy) carbonyl für: z.B. CO-OCH3, CO-OC2H5, CO-CH2-C2H5, CO-OCH(CH3)2, n-Butoxycarbonyl , CO-OCH (CH3) -C2H5, CO-OCH2-CH(CH3)2, CO-OC(CH3)3, n-Pentoxycarbonyl , 1-Methyl- butoxycarbonyl , 2-Methylbutoxycarbonyl, 3-Methylb toxy- carbonyl, 2 , 2-Dimethylpropoxycarbonyl, 1-Ethylpropoxy- carbonyl, n-Hexoxycarbonyl , 1, 1-Dimethylpropoxycarbonyl, 1 , 2-Dimethylpropoxycarbonyl , 1-Methylpentoxycarbonyl , 2-Methylpentoxycarbonyl, 3-Methylpentoxycarbonyl, 4-Methyl - pentoxycarbonyl , 1 , 1-Dimethylbutoxycarbonyl , 1 , 2-Dimethyl - butoxycarbonyl , 1, 3-Dimethylbutoxycarbonyl, 2, 2-Dimethyl - butoxycarbonyl , 2,3-Dirnethylbutoxycarbonyl , 3,3-Dirnethyl - butoxycarbonyl, 1-Ethylbutoxycarbonyl, 2-Ethylbutoxycarbonyl, 1,1, 2-Trimethylpropoxycarbonyl , 1,2, 2-Trimethylpropoxy- carbonyl, 1-Ethyl-l-methyl-propoxycarbonyl oder l-Ethyl-2- methyl-propoxycarbonyl, insbesondere für CO-OCH3, CO-OCH5, CO-OCH(CH3)2 oder CO-CH2-CH (CH3) 2;(Ci-Cg-alkoxy) carbonyl for: e.g. CO-OCH 3 , CO-OC 2 H 5 , CO-CH 2 -C 2 H 5 , CO-OCH (CH 3 ) 2 , n-butoxycarbonyl, CO-OCH ( CH 3 ) -C 2 H 5 , CO-OCH 2 -CH (CH 3 ) 2 , CO-OC (CH 3 ) 3 , n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylb toxycarbonyl , 2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1 -Dimethylbutoxycarbonyl, 1, 2-dimethyl-butoxycarbonyl, 1, 3-dimethylbutoxycarbonyl, 2, 2-dimethyl-butoxycarbonyl, 2,3-dirnethylbutoxycarbonyl, 3,3-dirnethyl-butoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1 , 2-trimethylpropoxycarbonyl, 1,2, 2-trimethylpropoxycarbonyl, 1-ethyl-l-methyl-propoxycarbonyl or l-ethyl-2-methyl-propoxycarbonyl, in particular for CO-OCH 3 , CO-OCH 5 , CO-OCH (CH 3 ) 2 or CO-CH 2 -CH (CH 3 ) 2 ;
(Ci-Cδ -Alkoxy) carbonyloxy für: Methoxycarbonyloxy, Ethoxy- carbonyloxy, n-Propoxycarbonyloxy, 1-Methylethoxycarbonyloxy, n-Butoxycarbonyloxy, 1-Methylpropoxycarbonyloxy, 2-Methyl- propoxycarbonyloxy, 1, 1-Dimethylethoxycarbonyloxy, n-Pentoxy- carbonyloxy, 1-Methylbutoxycarbonyloxy, 2-Methylbutoxy- carbonyloxy, 3-Methylbutoxycarbonyloxy, 2, 2-Dimethylpropoxy- carbonyloxy, 1-Ethylpropoxycarbonyloxy, n-Hexoxycarbonyloxy, 1, 1-Dimethylpropoxycarbonyloxy, 1, 2-Dimethylpropoxycarbonyl- oxy, 1-Methylpentoxycarbonyloxy, 2-Methylpentoxycarbonyloxy, 3-Methylpentoxycarbonyloxy, 4-Methylpentoxycarbonyloxy, 1, 1-Dimethylbutoxycarbonyloxy, 1 , 2-Dimethylbutoxycarbonyloxy, 1 , 3-Dimethylbutoxycarbonyloxy, 2 , 2-Dimethylbutoxycarbonyloxy, 2 , 3-Dimethylbutoxycarbonyloxy, 3 , 3-Dimethylbutoxycarbonyloxy, 1-Ethylb toxycarbonyloxy, 2-Ethylbutoxycarbonyloxy, 1, 1, 2-Trimethylpropoxycarbonyloxy, 1,2, 2-Trimethylprop- oxycarbonyloxy, 1-Ethyl-l-methyl-propoxycarbonyloxy oder l-Ethyl-2-methyl-propoxycarbonyloxy, insbesondere für Methoxycarbonyloxy, Ethoxycarbonyloxy oder 1 -Methylethoxy- carbonyloxy;(Ci-C δ -alkoxy) carbonyloxy for: methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy, 1-methylpropoxycarbonyloxy, 2-methylprooxycarbonyloxy, 1, 1-dimethylethoxycarbonyloxy, n-pentoxycarbonyloxy , 1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy, 3-methylbutoxycarbonyloxy, 2, 2-dimethylpropoxycarbonyloxy, 1-ethylpropoxycarbonyloxy, n-hexoxycarbonyloxy, 1, 1-dimethylpropoxycarbonyloxy, 1, 2-dimethylpropoxycarbonyloxyoxy, 1-methylpentoxy -Methylpentoxycarbonyloxy, 3-methylpentoxycarbonyloxy, 4-methylpentoxycarbonyloxy, 1, 1-dimethylbutoxycarbonyloxy, 1, 2-dimethylbutoxycarbonyloxy, 1, 3-dimethylbutoxycarbonyloxy, 2, 2-dimethylbutoxycarbonyloxy, 2, 3-dimethylbutoxycarbonyloxy, 3, 3-dimethyl toxycarbonyloxy, 2-ethylbutoxycarbonyloxy, 1, 1, 2-trimethylpropoxycarbonyloxy, 1,2, 2-trimethylprop oxycarbonyloxy, 1-ethyl-l-methyl-propoxycarbonyloxy or l-ethyl-2-methyl-propoxycarbonyloxy, especially for methoxycarbonyloxy, ethoxycarbonyloxy or 1-methylethoxycarbonyloxy;
(Ci-Cg -Alkoxy) carbonylthio für: Methoxycarbonylthio, Ethoxy- carbonylthio, n-Propoxycarbonylthio, 1-Methylethoxycarbonyl- thio, n-Butoxycarbonylthio, 1-Methylpropoxycarbonylthio, 2-Methylpropoxycarbonylthio, 1, 1-Dimethylethoxycarbonylthio, n-Pentoxycarbonylthio, 1-Methylbutoxycarbonylthio, 2-Methyl- butoxycarbonylthio, 3-Methylbutoxycarbonylthio, 2 , 2-Dimethyl - propoxycarbonylthio, 1-Ethylpropoxycarbonylthio, n-Hexoxy- carbonylthio, 1, 1-Dimethylpropoxycarbonylthio, 1, 2-Dimethyl - propoxycarbonylthio, 1-Methylpentoxycarbonylthio, 2-Methyl- pentoxycarbonylthio, 3-Methylpentoxycarbonylthio, 4-Methyl - pentoxycarbonylthio, 1, 1-Dimethylbutoxycarbonylthio, 1,2-Di- methylbutoxycarbonylthio, 1, 3-Dirnethylbutoxycarbonylthio, 2 , 2-Dirnethylbutoxycarbonylthio, 2 , 3-Dirnethylbutoxycarbonyl - thio, 3 , 3-Dimethylbutoxycarbonylthio, 1-Ethylbutoxycarbonyl- thio, 2-Ethylbutoxycarbonylthio, 1, 1, 2-Trimethylpropoxy- carbonylthio, 1, 2, 2-Trimethylpropoxycarbonylthio, 1-Ethyl- 1-methyl-propoxycarbonylthio oder 1-Ethy1-2-methyl-propoxycarbonylthio, insbesondere für Methoxycarbonylthio, Ethoxy- carbonylthio oder 1-Methylethoxycarbonylthio;(Ci-Cg -alkoxy) carbonylthio for: methoxycarbonylthio, ethoxycarbonylthio, n-propoxycarbonylthio, 1-methylethoxycarbonylthio, n-butoxycarbonylthio, 1-methylpropoxycarbonylthio, 2-methylpropoxycarbonylthio, 1, 1-dimethylthoxycarbonylthio, n-propoxycarbonylthio Methylbutoxycarbonylthio, 2-methylbutoxycarbonylthio, 3-methylbutoxycarbonylthio, 2, 2-dimethylpropoxycarbonylthio, 1-ethylpropoxycarbonylthio, n-hexoxycarbonylthio, 1, 1-dimethylpropoxycarbonylthio, 1, 2-dimethylpropoxycarbonylthioyl, 1-2 Methyl-pentoxycarbonylthio, 3-methylpentoxycarbonylthio, 4-methyl-pentoxycarbonylthio, 1, 1-dimethylbutoxycarbonylthio, 1,2-dimethylbutoxycarbonylthio, 1, 3-dirnethylbutoxycarbonylthio, 2, 2-dirnethylbutoxycarbonylthio, 2, 3-dirnethylbio 3-dimethylbutoxycarbonylthio, 1-ethylbutoxycarbonylthio, 2-ethylbutoxycarbonylthio, 1, 1, 2-trimethylpropoxycarbonylthio, 1, 2, 2-trimethylpropoxycarbonylthio, 1-ethyl-1-methyl-propo xycarbonylthio or 1-Ethy1-2-methyl-propoxycarbonylthio, especially for methoxycarbonylthio, ethoxycarbonylthio or 1-methylethoxycarbonylthio;
Ci-Cg-Alkylthio für: SCH3 , SC2H5, SCH2-C H5, SCH(CH3) , n-Butylthio, 1-Methylpropylthio, 2-Methylpropylthio, SC(CH3)3, n-Pentylthio, 1-Methylb tylthio, 2-Methylbutylthio, 3-Methyl- butylthio, 2, 2-Dimethylpropylthio, 1-Ethylpropylthio, n-Hexylthio, 1, 1-Dimethylpropylthio, 1, 2-Dirnethylpropylthio, 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methylpentylthio, 1, 1-Dimethylbutylthio, 1, 2-Dimethylbutyl- thio, 1, 3-Dimethylbutylthio, 2, 2-Dimethylbutylthio, 2, 3-Dimethylbutylthio, 3 , 3-Dimethylbutylthio, 1-Ethylbutyl- thio, 2-Ethylbutylthio, 1, 1, 2-Trimethylpropylthio, 1,2, 2-Trimethylpropylthio, 1-Ethyl-l-methylpropylthio und 1-Ethyl- 2-methylpropylthio, insbesondere für SCH3 oder SC2H5;Ci-Cg-alkylthio for: SCH 3 , SC 2 H 5 , SCH 2 -CH 5 , SCH (CH 3 ), n-butylthio, 1-methylpropylthio, 2-methylpropylthio, SC (CH 3 ) 3 , n-pentylthio, 1-Methylb tylthio, 2-Methylbutylthio, 3-Methylbutylthio, 2, 2-Dimethylpropylthio, 1-Ethylpropylthio, n-Hexylthio, 1, 1-Dimethylpropylthio, 1, 2-Dirnethylpropylthio, 1-Methylpentylthio, 2-Methylpentylthio -Methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1, 2-dimethylbutylthio, 1, 3-dimethylbutylthio, 2, 2-dimethylbutylthio, 2, 3-dimethylbutylthio, 3, 3-dimethylbutylthio, 1-ethylbutylthio , 2-ethylbutylthio, 1, 1, 2-trimethylpropylthio, 1,2, 2-trimethylpropylthio, 1-ethyl-l-methylpropylthio and 1-ethyl-2-methylpropylthio, especially for SCH 3 or SC 2 H 5 ;
Ci-Cg-Halogenalkylthio für: Ci-Cg-Alkylthio wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor,Ci-Cg-haloalkylthio for: Ci-Cg-alkylthio as mentioned above, partially or completely by fluorine, chlorine,
Brom und/oder Iod substituiert ist, also z.B. für SCHF2, SCF3, Chlordifluormethylthio, Bromdifluormethylthio, 2-Fluorethyl- thio, 2-Chlorethylthio, 2-Bromethylthio, 2-Iodethylthio, 2, 2-Difluorethylthio, 2, 2, 2-Trifluorethylthio, 2,2,2-Tri- chlorethylthio, 2-Chlor-2-fluorethylthio, 2-Chlor-2, 2-di- fluorethylthio, 2 , 2-Dichlor-2-fluorethylthio, SC2F5, 2-Fluor- propylthio, 3-Fluorpropylthio, 2-Chlorpropylthio, 3-Chlor- propylthio, 2-Brompropylthio, 3-Brompropylthio, 2,2-Difluor- propylthio, 2, 3-Difluorpropylthio, 2, 3-Dichlorpropylthio, 3,3, 3-Trifluorpropylthio, 3,3, 3-Trichlorpropylthio, 2,2,3,3, 3-Pentafluorpropylthio, Heptafluorpropylthio, 1- (Fluormethyl) -2-fluorethylthio, 1- (Chlormethyl) -2-chlor- ethylthio, 1- (Brommethyl) -2-bromethylthio, 4-Fluorbutylthio, 4-Chlorbutylthio, 4-Brombutylthio, Nonafluorbutylthio, 5-Fluorpentylthio, 5-Chlorpentylthio, 5-Brompentylthio, 5-Iodpentylthio, Undecafluorpentylthio, 6-Fluorhexylthio oder 6-Chlorhexylthio, insbesondere für SCHF, SCHF2, SCF3, SCH2C1, 2-Fluorethylthio, 2-Chlorethylthio oder 2, 2, 2-Trifluorethyl - thio;Bromine and / or iodine is substituted, for example for SCHF 2 , SCF 3 , chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2, 2-difluoroethylthio, 2, 2, 2 -Trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2, 2-di-fluoroethylthio, 2, 2-dichloro-2-fluoroethylthio, SC 2 F 5 , 2- Fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloro propylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2, 3-difluoropropylthio, 2, 3-dichloropropylthio, 3,3, 3-trifluoropropylthio, 3,3, 3-trichloropropylthio, 2,2, 3,3, 3-pentafluoropropylthio, heptafluoropropylthio, 1- (fluoromethyl) -2-fluoroethylthio, 1- (chloromethyl) -2-chloroethylthio, 1- (bromomethyl) -2-bromethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-Brombutylthio, Nonafluorbutylthio, 5-fluoropentylthio, 5-Chlorpentylthio, 5-Brompentylthio, 5-Iodpentylthio, Undecafluorpentylthio, 6-Fluorhexylthio or 6-Chlorhexylthio, in particular for SCHF, SCHF 2, SCF 3, SCH 2 C1, 2-fluoroethylthio, 2-chloroethylthio or 2, 2, 2-trifluoroethyl - thio;
Ci-Cg-Alkylsulfinyl für: S0-CH3, SO-C2Hs, n-Propylsulfinyl, 1-Methylethylsulfinyl, n-B tylsulfinyl, 1-Methylpropyl - sulfinyl, 2-Methylpropylsulfinyl, 1, 1-Dimethylethylsulfinyl, n-Pentylsulfinyl, 1-Methylbutylsulfinyl, 2-Methylbutylsulfi- nyl, 3-Methylbutylsulfinyl, 1, 1-Dimethylpropylsulfinyl , 1, 2-Dimethylpropylsulfinyl, 2, 2-Dimethylpropylsulfinyl, 1-Ethylpropylsulfinyl, n-Hexylsulfinyl, 1-Methylpentylsulfi - nyl, 2-Methylpentylsulfinyl, 3-Methylpentylsulfinyl, 4-Methylpentylsulfinyl, 1, 1-Dimethylbutylsulfinyl , 1,2-Di- methylbutylsulfinyl, 1, 3-Dimethylbutylsulfinyl, 2, 2-Dimethyl - butylsulfinyl, 2, 3-Dimethylbutylsulfinyl, 3 , 3-Dimethylbutyl - sulfinyl, 1-Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl,Ci-Cg-alkylsulfinyl for: S0-CH 3 , SO-C 2 Hs, n-propylsulfinyl, 1-methylethylsulfinyl, nB tylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethylethylsulfinyl, n-pentylsulfinyl, 1 -Methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1, 1-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, 2, 2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 1-methylpentylsulfinyl -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-l-methylpropylsulfinyl oder l-Ethyl-2-methylpropyl- sulfinyl, insbesondere für SO-CH3;1,1, 2-trimethylpropylsulfinyl, 1,2, 2-trimethylpropylsulfinyl, 1-ethyl-l-methylpropylsulfinyl or l-ethyl-2-methylpropylsulfinyl, in particular for SO-CH 3 ;
Ci-Cg-Alkylsulfonyl für: S02-CH3, S02-C2H5, n-Propylsulfonyl , S02-CH(CH3)2, n-Butylsulfonyl, 1-Methylpropylsulfonyl, 2-Methylpropylsulfonyl, S02-C(CH3)3, n-Pentylsulfonyl, 1-Methylbutylsulfonyl, 2-Methylbutylsulfonyl, 3-Methylbutylsulfonyl, 1, 1-Dimethylpropylsulfonyl, 1, 2-Dirnethylpropyl - sulfonyl, 2 , 2-Dimethylpropylsulfonyl, 1-Ethylpropylsulfonyl, n-Hexylsulfonyl, 1-Methylpentylsulfonyl, 2-Methylpentyl - sulfonyl, 3-Methylpentylsulfonyl, 4-Methylpentylsulfonyl, 1, 1-Dimethylbutylsulfonyl, 1, 2-Dirnethylbutylsulfonyl, 1, 3-Dimethylbutylsulfonyl, 2, 2-Dimethylbutylsulfonyl, 2, 3-Dimethylbutylsulfonyl, 3 , 3-Dimethylbutylsulfonyl,Ci-Cg-alkylsulfonyl for: S0 2 -CH 3 , S0 2 -C 2 H 5 , n-propylsulfonyl, S0 2 -CH (CH 3 ) 2 , n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, S0 2 - C (CH 3 ) 3 , n-pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dirnethylpropylsulfonyl, 2, 2-dimethylpropylsulfonyls, hexylsulfonyl, 1-ethylsulfonyl, 1-ethylsulfonyls , 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1, 1-dimethylbutylsulfonyl, 1, 2-dimethylbutylsulfonyl, 1, 3-dimethylbutylsulfonyl, 2, 2-dimethylbutylsulfonyl , 3-dimethylbutylsulfonyl,
1-Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1, 1, 2-Trimethyl- propylsulfonyl, 1,2, 2-Trimethylpropylsulfonyl , 1-Ethyl-l-methylpropylsulfonyl oder l-Ethyl-2-methylpropyl- sulfonyl, insbesondere für S02-CH3; Ci-Cδ-Alkylsulfonyloxy für: 0-S02-CH3, 0-S0 -C2H5, n-Propyl- sulfonyloxy, 0-S02-CH (CH3) 2, n-Butylsulfonyloxy, 1-Methyl- propylsulfonyloxy, 2-Methylpropylsulfonyloxy, 0-SO2-C (CH3) 3, n-Pentylsulfonyloxy, 1-Methylbutylsulfonyloxy, 2-Methylbutyl- sulfonyloxy, 3-Methylbutylsulfonyloxy, 1, 1-Dimethylpropyl- sulfonyloxy, 1, 2-Dimethylpropylsulfonyloxy, 2, 2-Dimethyl - propylsulfonyloxy, 1-Ethylpropylsulfonyloxy, n-Hexylsulfonyloxy, 1-Methylpentylsulfonyloxy, 2-Methylpentylsulfonyloxy, 3-Methylpentylsulfonyloxy, 4-Methylpentylsulfonyloxy, 1, 1-Dimethylbutylsulfonyloxy, 1, 2-Dimethylbutylsulfonyloxy, 1, 3-Dimethylbutylsulfonyloxy, 2, 2-Dimethylbutylsulfonyloxy, 2 , 3-Dimethylbutylsulfonyloxy, 3 , 3-Dimethylbutylsulfonyloxy, 1-Ethylbutylsulfonyloxy, 2-Ethylbutylsulfonyloxy, 1,1,2-Tri- methylpropylsulfonyloxy, 1,2, 2-Trimethylpropylsulfonyloxy, 1-Ethyl-l-methylpropylsulfonyloxy oder 1-Ethyl-2-methyl - propylsulfonyloxy, insbesondere für Methylsulfonyloxy;1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1, 1, 2-trimethylpropylsulfonyl, 1,2, 2-trimethylpropylsulfonyl, 1-ethyl-l-methylpropylsulfonyl or l-ethyl-2-methylpropylsulfonyl, especially for S0 2 -CH 3 ; Ci-C δ- alkylsulfonyloxy for: 0-S0 2 -CH 3 , 0-S0-C 2 H 5 , n-propylsulfonyloxy, 0-S0 2 -CH (CH 3 ) 2 , n-butylsulfonyloxy, 1-methyl - propylsulfonyloxy, 2-methylpropylsulfonyloxy, 0-SO 2 -C (CH 3 ) 3 , n-pentylsulfonyloxy, 1-methylbutylsulfonyloxy, 2-methylbutylsulfonyloxy, 3-methylbutylsulfonyloxy, 1, 1-dimethylpropylsulfonyloxyprop. 1, 2 , 2, 2-dimethyl-propylsulfonyloxy, 1-ethylpropylsulfonyloxy, n-hexylsulfonyloxy, 1-methylpentylsulfonyloxy, 2-methylpentylsulfonyloxy, 3-methylpentylsulfonyloxy, 4-methylpentylsulfonyloxy, 1, 1-dimethylbutylsulfylyloxy sulfonyloxy sulfonyloxy sulfonyloxy, 1 , 2, 2-dimethylbutylsulfonyloxy, 2, 3-dimethylbutylsulfonyloxy, 3, 3-dimethylbutylsulfonyloxy, 1-ethylbutylsulfonyloxy, 2-ethylbutylsulfonyloxy, 1,1,2-trimethylpropylsulfonyloxy, 1,2, 2-trimethyl-1-propylsulfonyloxy -methylpropylsulfonyloxy or 1-ethyl-2-methyl-propylsulfonyloxy, especially for methylsulfonyloxy;
C -C6-Halogenalkylsulfonyloxy für: Ci-Cδ-Alkylsulfonyloxy wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. ClCH2-S02-0-, CH(Cl)2-S02-0-, C (CD 3-S02-0-, FCH2-S02-0-, CHF2-S02-0-, CF3-S0-0-, Chlorfluormethyl-S02-0- , Dichlor- fluormethyl-S0-0-, Chlordifluormethyl-S02-0-, 1-Fluorethyl- S02-0-, 2-Fluorethyl-S02-0-, 2-Chlorethyl-S02-0-, 2-Brom- ethyl-S02-0-, 2-Iodethyl-S0-0-, 2 , 2-Difluorethyl-S02-0-, 2,2, 2-Trifluorethyl-S02-0-, 2-Chlor-2-fluorethyl-S02-0- , 2-Chlor-2 , 2-difluorethyl-S02-0-, 2 , 2-Dichlor-2-fluorethyl- S02-0-, 2,2,2-Trichlorethyl-S02-0-, C2F5-S02-0-, 2-Fluor- propyl-S0-0-, 3-Fluorpropyl-S0-0-, 2, 2-Difluorpropyl-S0-0-, 2,3-Difluorpropyl-S02-0-, 2-Chlorpropyl-S02-0-, 3-Chlor- propyl-S0-0-, 2 , 3-Dichlorpropyl-S02-0-, 2-Brompropyl-S0-0-, 3-Brompropyl-S02-0-, 3 , 3 , 3-Trifluorpropyl-S0-0-, 3,3,3-Tri- chlorpropyl-S02-0-, 2,2,3,3, 3-Pentafluorpropyl-S0-0-, C2F5-CF-S02-0-, 1- (Fluormethyl) -2-fluorethyl-S02-0-, 1- (Chlormethyl) -2-chlorethyl-S02-0-, 1- (Brommethyl) -2-brom- ethyl-S02-0-, 4-Fluorbutyl-S02-0-, 4-Chlorbutyl-S02-0-, 4-Bromb tyl-S02-0-, C2F5-CF2-CF2-S02-0-, 5-Fluorpentyl-S0-0-, 5-Chlorpentyl-S0-0-, 5-Brompentyl-S02-0-, 5-Iodpentyl-S02-0-, 5,5,5-Trichlorpentyl-S02-0-, C2F5-CF-CF2-CF2-S02-0-, 6-Fluor- hexyl-S02-0-, 6-Chlorhexyl-S0-0-, 6-Bromhexyl-S02-0-, 6-Iod- hexyl-S0-0-, 6, 6, 6-Trichlorhexyl-S02-0- oder Dodecafluor- hexyl-S02-0-, insbesondere für CF3-S02-0-;C -C 6 haloalkylsulfonyloxy for: Ci-C δ- alkylsulfonyloxy as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example ClCH 2 -S0 2 -0-, CH (Cl) 2 -S0 2 -0-, C (CD 3 -S0 2 -0-, FCH 2 -S0 2 -0-, CHF 2 -S0 2 -0-, CF 3 -S0-0-, chlorofluoromethyl-S0 2 - 0-, dichlorofluoromethyl-S0-0-, chlorodifluoromethyl-S0 2 -0-, 1-fluoroethyl- S0 2 -0-, 2-fluoroethyl-S0 2 -0-, 2-chloroethyl-S0 2 -0-, 2-bromoethyl-S0 2 -0-, 2-iodo-ethyl-S0-0-, 2,2-difluoroethyl-S0 2 -0-, 2,2, 2-trifluoroethyl-S0 2 -0-, 2-chlorine -2-fluoroethyl-S0 2 -0-, 2-chloro-2, 2-difluoroethyl-S0 2 -0-, 2, 2-dichloro-2-fluoroethyl-S0 2 -0-, 2,2,2-trichloroethyl -S0 2 -0-, C 2 F 5 -S0 2 -0-, 2-fluoropropyl-S0-0-, 3-fluoropropyl-S0-0-, 2,2-difluoropropyl-S0-0-, 2nd , 3-difluoropropyl-S0 2 -0-, 2-chloropropyl-S0 2 -0-, 3-chloropropyl-S0-0-, 2, 3-dichloropropyl-S0 2 -0-, 2-bromopropyl-S0- 0-, 3-bromopropyl-S0 2 -0-, 3, 3, 3-trifluoropropyl-S0-0-, 3,3,3-trichloropropyl-S0 2 -0-, 2,2,3,3, 3-pentaf luorpropyl-S0-0-, C 2 F 5 -CF-S0 2 -0-, 1- (fluoromethyl) -2-fluoroethyl-S0 2 -0-, 1- (chloromethyl) -2-chloroethyl-S0 2 -0 -, 1- (bromomethyl) -2-bromoethyl-S0 2 -0-, 4-fluorobutyl-S0 2 -0-, 4-chlorobutyl-S0 2 -0-, 4-bromotyl-S0 2 -0- , C 2 F 5 -CF 2 -CF 2 -S0 2 -0-, 5-fluoropentyl-S0-0-, 5-chloropentyl-S0-0-, 5-bromopentyl-S0 2 -0-, 5-iodopentyl- S0 2 -0-, 5,5,5-trichloropentyl-S0 2 -0-, C 2 F 5 -CF-CF 2 -CF 2 -S0 2 -0-, 6-fluoro-hexyl-S0 2 -0- , 6-chlorohexyl-S0-0-, 6-bromohexyl-S0 2 -0-, 6-iodo-hexyl-S0-0-, 6, 6, 6-trichlorohexyl-S0 2 -0- or dodecafluoro-hexyl-S0 2 -0-, in particular for CF 3 -S0 2 -0-;
(Ci-Cδ-Alkyl) aminocarbonyl für: (C1-C4 -Alkyl) aminocarbonyl wie vorstehend genannt sowie z.B. n-Pentylaminocarbonyl, 1-Methylbutylaminocarbonyl , 2-Methylbutylaminocarbonyl , 3-Methylbutylaminocarbonyl , 2 , 2-Dimethylpropylaminocarbonyl , 1-Ethylpropylaminocarbonyl, n-Hexylaminocarbonyl, 1,1-Di- methylpropylaminocarbonyl , 1 , 2-Dimethylpropylaminocarbonyl , 1-Methylpentylaminocarbonyl , 2-Methylpentylaminocarbonyl , 3-Methylpentylaminocarbonyl , 4-Methylpentylaminocarbonyl , 1, 1-Dimethylbutylaminocarbonyl, 1, 2-Dirnethylbutylaminocarbonyl, 1, 3-Dirnethylbutylaminocarbonyl, 2, 2-Dirnethylbutylaminocarbonyl , 2, 3-Di ethylbutylaminocarbonyl, 3 , 3-Dimethyl- butylaminocarbonyl , 1-Ethylbutylaminocarbonyl, 2-Ethylbutyl- aminocarbonyl , 1, 1, 2-Trimethylpropylaminocarbonyl, 1,2,2-Tri- methylpropylaminocarbonyl , 1-Ethyl-l-methylpropylamino- carbonyl oder l-Ethyl-2-methylpropylaminocarbonyl, insbesondere für C0-NH-CH3, CO-NH-C2H5 oder CO-NH-CH (CH3) 2;(Ci-C δ alkyl) aminocarbonyl for: (C 1 -C 4 alkyl) aminocarbonyl as mentioned above and, for example, n-pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2, 2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1, 2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1, 1-dimethylnetyl butyl 1, 3-dimethylbutylaminocarbonyl, 2, 2-dimethylbutylaminocarbonyl, 2, 3-diethylbutylaminocarbonyl, 3, 3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1, 1, 2-trimethylpropylamine -Trimethylpropylaminocarbonyl, 1-ethyl-l-methylpropylamino-carbonyl or l-ethyl-2-methylpropylaminocarbonyl, especially for CO-NH-CH 3 , CO-NH-C 2 H 5 or CO-NH-CH (CH 3 ) 2 ;
Di (Ci-Cδ-alkyl) aminocarbonyl für: z.B. N,N-Dimethylaminocarbo- nyl, N,N-Diethylaminocarbonyl, N,N-Dipropylaminocarbonyl,Di (Ci-C δ -alkyl) aminocarbonyl for: for example N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N, N-dipropylaminocarbonyl,
N,N-Di- (1-methylethyl) aminocarbonyl, N,N-Dibutylaminocarbonyl, N,N-Di- (1-methylpropyl) aminocarbonyl, N,N-Di- (2-methyl - propyl) aminocarbonyl, N,N-Di- (1, 1-dimethylethyl) aminocarbonyl, N-Ethyl-N-methylaminocarbonyl, N-Methyl-N-propyl - aminocarbonyl, N-Methyl-N- (1-methylethyl) aminocarbonyl,N, N-di- (1-methylethyl) aminocarbonyl, N, N-dibutylaminocarbonyl, N, N-di- (1-methylpropyl) aminocarbonyl, N, N-di- (2-methylpropyl) aminocarbonyl, N, N Di (1, 1-dimethylethyl) aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propyl-aminocarbonyl, N-methyl-N- (1-methylethyl) aminocarbonyl,
N-Butyl-N-methylaminocarbonyl, N-Methyl-N- (1-methylpropyl) - aminocarbonyl , N-Methyl-N- (2-methylpropyl) aminocarbonyl , N- (1 , 1-Dirnethy1ethyl) -N-methylaminocarbonyl , N-Ethyl-N- propylaminocarbonyl , N-Ethyl-N- (1-methylethyl) aminocarbonyl , N-Butyl-N-ethylaminocarbonyl, N-Ethyl-N- (1-methylpropyl) - aminocarbonyl , N-Ethyl-N- (2-methylpropyl) aminocarbonyl , N-Ethyl-N- (1, 1-dimethylethyl) aminocarbonyl , N- (1-Methyl - ethyl) -N-propylaminocarbonyl , N-Butyl-N-propylaminocarbonyl, N- (1-Methylpropyl) -N-propylaminocarbonyl, 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- (1- methylpropyl) minocarbonyl, N-Butyl-N- (2-methylpropyl) aminocarbonyl , N-Butyl-N- (1 , 1-dimethylethyl) 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, insbesondere für N,N-Dirnethylaminocarbonyl oder N,N-Diethyl- aminocarbonyl ;N-butyl-N-methylaminocarbonyl, N-methyl-N- (1-methylpropyl) aminocarbonyl, N-methyl-N- (2-methylpropyl) aminocarbonyl, N- (1, 1-dirnethy1ethyl) -N-methylaminocarbonyl, N -Ethyl-N-propylaminocarbonyl, N-ethyl-N- (1-methylethyl) aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N- (1-methylpropyl) - aminocarbonyl, N-ethyl-N- (2nd -methylpropyl) aminocarbonyl, N-ethyl-N- (1, 1-dimethylethyl) aminocarbonyl, N- (1-methyl-ethyl) -N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N- (1-methylpropyl) - N-propylaminocarbonyl, 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- (1-methylpropyl) minocarbonyl, N-butyl-N- (2-methylpropyl) aminocarbonyl, N-butyl-N- (1, 1-dimethylethyl) 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, in particular for N, N-dirnethylaminocarbonyl or N, N-diethylaminocarbonyl;
(Ci -Cδ -Alkyl) iminooxycarbonyl für: Methyliminooxycarbonyl, Ethyliminooxycarbonyl, n-Propyliminooxycarbonyl, 1-Methyl - ethyliminooxycarbonyl, n-Butyliminooxycarbonyl, 1-Methyl - propyliminooxycarbonyl , 2-Methylpropyliminooxycarbonyl , 1, 1-Dimethylethyliminooxycarbonyl , n-Pentyliminooxycarbonyl , 1-Methylbutyliminooxycarbonyl , 2-Methylbutyliminooxycarbonyl , 3-Methylbutyliminooxycarbonyl, 1, 1-Dirnethylpropyliminooxycarbonyl, 1, 2-Dirnethylpropyliminooxycarbonyl, 2 , 2-Dimethyl - propyliminooxycarbonyl , 1-Ethylpropyliminooxycarbonyl , n-Hexyliminooxycarbonyl, 1-Methylpentyliminooxycarbonyl, 2-Methylpentyliminooxycarbonyl , 3-Methylpentyliminooxycarbonyl, 4-Methylpentyliminooxycarbonyl, 1, 1-Dimethylbutyl- iminooxycarbonyl , 1, 2-Dimethylbutyliminooxycarbonyl, 1,3-Di- methylbutyliminooxycarbonyl , 2 , 2-Dimethylbutyliminooxy- carbonyl, 2 , 3-Dimethylbutyliminooxycarbonyl, 3 , 3-Dimethylbutyliminooxycarbonyl, 1-Ethylbutyliminooxycarbonyl, 2-Ethyl- butyliminooxycarbonyl , 1,1, 2-Trimethylpropyliminooxycarbonyl , 1,2, 2-Trimethylpropyliminooxycarbonyl, 1-Ethyl-1-methylpropyliminooxycarbonyl oder l-Ethyl-2-methylpropyliminooxy- carbonyl, insbesondere für Methyliminooxycarbonyl, Ethyliminooxycarbonyl oder 1-Methylethyliminooxycarbonyl;(Ci -C δ- alkyl) iminooxycarbonyl for: methyliminooxycarbonyl, ethyliminooxycarbonyl, n-propyliminooxycarbonyl, 1-methyl-ethyliminooxycarbonyl, n-butyliminooxycarbonyl, 1-methyl-propyliminooxycarbonyl, 2-methylpropyliminooxycarbonyl, 1, 1-dimethyloxycarbonyl, pentane 1-methylbutyliminooxycarbonyl, 2-methylbutyliminooxycarbonyl, 3-methylbutyliminooxycarbonyl, 1, 1-dirnethylpropyliminooxycarbonyl, 1, 2-dirnethylpropyliminooxycarbonyl, 2, 2-dimethylpropyliminooxycarbonyl, 1-ethylpropyliminooxyoxyylyl, 3-methylyloxy-methyloxycarbonyl, 3 Methylpentyliminooxycarbonyl, 4-methylpentyliminooxycarbonyl, 1, 1-dimethylbutyliminooxycarbonyl, 1, 2-dimethylbutyliminooxycarbonyl, 1,3-dimethylbutyliminooxycarbonyl, 2, 2-dimethylbutyliminooxycarbonyl, 2, 3-dimethylbutyliminooxycarbonyl, 3 Ethylbutyliminooxycarbonyl, 2-ethylbutyliminooxycarbonyl, 1,1, 2-trimethylpropyliminooxycarbonyl, 1,2, 2-trimethylpropyliminooxycarbonyl, 1-ethyl-1-methylpropyliminooxycarbonyl or l-ethyl-2-methylpropyliminooxycarbonyl, especially for methyliminooxycarbonyl Methylethyliminooxycarbonyl;
Ci-Cδ-Alkylidenaminoxy für: Acetylidenaminoxy, 1-Propyliden- aminoxy, 2-Propylidenaminoxy, 1-Butylidenaminoxy, 2 -B tylidenaminoxy oder 2-Hexylidenaminoxy, insbesondere für Acetylidenaminoxy oder 2 -Propylidenaminoxy;Ci-C δ- alkylidene aminoxy for: acetylidene aminoxy, 1-propylidene aminoxy, 2-propylidene aminoxy, 1-butylidene aminoxy, 2-tylidene aminoxy or 2-hexylidene aminoxy, in particular for acetylidene aminoxy or 2-propylidene aminoxy;
Ci-Cg-Alkyliminooxy für: Methyliminooxy, Ethyliminooxy, n-Propyliminooxy, 1-Methylethyliminooxy, n-Butyliminooxy, 1-Methylpropyliminooxy, 2 -Methylpropyliminooxy, n-Pentyl- iminooxy, n-Hexyliminooxy, 1 -Methylpentyliminooxy, 2 -Methylpentyliminooxy, 3 -Methylpentyliminooxy oder 4 -Methylpentyl - iminooxy, insbesondere für Methyliminooxy, Ethyliminooxy oder 1 -Methylethyliminooxy;Ci-Cg-alkyliminooxy for: methyliminooxy, ethyliminooxy, n-propyliminooxy, 1-methylethyliminooxy, n-butyliminooxy, 1-methylpropyliminooxy, 2-methylpropyliminooxy, n-pentyliminooxy, n-hexyliminooxy, 1-methylpentyliminooxy, 2-methylpentyloxy -Methylpentyliminooxy or 4 -Methylpentyl - iminooxy, especially for methyliminooxy, ethyliminooxy or 1 -Methylethyliminooxy;
Ci-Cg-Alkoxy- (Ci-Cg-alkyl) aminocarbonyl für: (Ci-Cg-Alkyl) - aminocarbonyl wie CO-NH-CH3, CO-NH-CHs, CO-NH-CH2-C2H5, CO-NH-CH(CH3) . CO-NH-(CH2)3-CH3, CO-NH-CH (CH3) -C2H5 , CO-NH-CH2-CH(CH3)2, CO-NH-C (CH3) 3 , CO-NH- (CH2) 4-CH3 , 1-Methyl - butylaminocarbonyl , 2-Methylb tylaminocarbonyl, 3-Methyl- butylaminocarbonyl , 2, 2-Dimethylpropylaminocarbonyl, 1-Ethyl- propylaminocarbonyl , n-Hexylaminocarbonyl , 1, 1-Dimethyl- propylaminocarbonyl , 1, 2-Dimethylpropylaminocarbonyl , 1-Methylpentylaminocarbonyl , 2-Methylpentylaminocarbonyl, 3-Methylpentylaminocarbonyl, 4-Methylpentylaminocarbonyl, 1, 1-Dimethylbutylaminocarbonyl, 1, 2-Dirnethylbutylaminocarbonyl, 1, 3-Dirnethylbutylaminocarbonyl, 2, 2-Dimethylbutyl- aminocarbonyl , 2, 3-Dirnethylbutylaminocarbonyl, 3 , 3-Dimethyl- b tylaminocarbonyl, 1-Ethylbutylaminocarbonyl, 2-Ethylbutyl- aminocarbonyl, 1, 1, 2-Trimethylpropylaminocarbonyl, 1,2,2-Tri- methylpropylaminocarbonyl , 1-Ethyl-l-methylpropylamino- carbonyl und l-Ethyl-2-methylpropylaminocarbonyl, Vorzugs- weise (Cι-C -Alkyl) aminocarbonyl, das durch Ci-Cg-Alkoxy - wie vorstehend genannt - substituiert ist, also z.B. für CO-NH-CH2-OCH3 oder CO-NH-CH2-OC2H5;Ci-Cg-alkoxy- (Ci-Cg-alkyl) aminocarbonyl for: (Ci-Cg-alkyl) - aminocarbonyl such as CO-NH-CH 3 , CO-NH-CHs, CO-NH-CH 2 -C 2 H 5 , CO-NH-CH (CH 3 ). CO-NH- (CH 2 ) 3 -CH 3 , CO-NH-CH (CH 3 ) -C 2 H 5 , CO-NH-CH 2 -CH (CH 3 ) 2 , CO-NH-C (CH 3 ) 3 , CO-NH- (CH 2 ) 4 -CH 3 , 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2, 2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl, 1 , 1-dimethylpropylaminocarbonyl, 1, 2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1, 1-dimethylbutylaminocarbonyl, 1, 2-dirnethylbutylaminylcarbonyl, 1 -Dimethylbutyl-aminocarbonyl, 2, 3-dirnethylbutylaminocarbonyl, 3, 3-dimethyl-b tylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1, 1, 2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl Ethyl-l-methylpropylamino-carbonyl and l-ethyl-2-methylpropylaminocarbonyl, preferred as (-C-alkyl) aminocarbonyl, which is substituted by Ci-Cg-alkoxy - as mentioned above - so for example for CO-NH-CH 2 -OCH 3 or CO-NH-CH 2 -OC 2 H 5 ;
Ci-Cδ-Alkoxyamino-Ci-Cδ-alkyl für: z.B. CH2-NH-OCH3, CH2-NH-OC2H5, CH2-NH-OCH2-C2H5, CH2-NH-OCH (CH3) 2 , CH2-NH-OCH2-CH2-C2H5, CH2-NH-OCH (CH3) -C2H5 ,Ci-C δ -alkoxyamino-Ci-C δ -alkyl for: e.g. CH 2 -NH-OCH 3 , CH 2 -NH-OC 2 H 5 , CH 2 -NH-OCH 2 -C 2 H 5 , CH 2 - NH-OCH (CH 3 ) 2 , CH 2 -NH-OCH 2 -CH 2 -C 2 H 5 , CH 2 -NH-OCH (CH 3 ) -C 2 H 5 ,
CH2-NH-OCH2-CH(CH3)2, CH2-NH-OC (CH3) 3 , CH2-NH-OCH2- (CH2) 3-CH3 , (1-Methylbutoxyamino) ethyl , (2-Methylbutoxyamino) methyl , (3-Methylbutoxyamino) methyl, (2, 2-Dirnethylpropoxyamino)methyl, (1-Ethylpropoxyamino) methyl, n-Hexoxyamino-methyl , (1, 1-Dimethylpropoxyamino) methyl, (1, 2-Dirnethylpropoxyamino) - methyl, (1-Methylpentoxyamino) methyl, (2-Methylpentoxy- amino) methyl, (3-Methylpentoxyamino) methyl, (4-Methylpentoxy- amino) methyl, (1, 1-Dimethylbutoxyamino) methyl, (1, 2-Dirnethylbutoxyamino) methyl, (1, 3-Dimethylbutoxyamino) methyl, (2,2-Di- methylbutoxyamino) methyl, (2, 3-Dirnethylbutoxyamino) ethyl, (3 , 3-Dimethylbutoxyamino) methyl, (1-Ethylbutoxyamino) methyl , (2-Ethylbutoxyamino) methyl, (1, 1, 2-Trimethylpropoxyamino) - methyl, (1, 2, 2-Trimethylpropoxyamino) methyl, (1-Ethyl-l- me hylpropoxyamino) methyl, (l-Ethyl-2-methylpropoxyamino) - methyl, Methoxyamino-ethyl, Ethoxyamino-ethyl, n-Propoxy- amino-ethyl, (1-Methylethoxyamino) ethyl, n-Butoxyamino-ethyl , (1-Methylpropoxyamino) ethyl, (2-Methylpropoxyamino) ethyl, (1 , 1-Dimethylethoxyamino) ethyl , n-Pentoxyaminoethyl ,CH 2 -NH-OCH 2 -CH (CH 3 ) 2 , CH 2 -NH-OC (CH 3 ) 3 , CH 2 -NH-OCH 2 - (CH 2 ) 3 -CH 3 , (1-methylbutoxyamino) ethyl , (2-Methylbutoxyamino) methyl, (3-Methylbutoxyamino) methyl, (2, 2-Dirnethylpropoxyamino) methyl, (1-Ethylpropoxyamino) methyl, n-Hexoxyamino-methyl, (1, 1-Dimethylpropoxyamino) methyl, (1, 2 -Dirnethylpropoxyamino) - methyl, (1-methylpentoxyamino) methyl, (2-methylpentoxyamino) methyl, (3-methylpentoxyamino) methyl, (4-methylpentoxyamino) methyl, (1, 1-dimethylbutoxyamino) methyl, (1, 2-dimethylbutoxyamino) methyl, (1, 3-dimethylbutoxyamino) methyl, (2,2-dimethylbutoxyamino) methyl, (2, 3-dimethylbutoxyamino) ethyl, (3, 3-dimethylbutoxyamino) methyl, (1-ethylbutoxyamino) methyl , (2-ethylbutoxyamino) methyl, (1, 1, 2-trimethylpropoxyamino) methyl, (1, 2, 2-trimethylpropoxyamino) methyl, (1-ethyl-l-methylpropoxyamino) methyl, (l-ethyl-2- methylpropoxyamino) - methyl, methoxyamino-ethyl, ethoxyamino-ethyl, n-propoxy-amino-ethyl, (1-methylethoxyamino) ethyl, n -Butoxyamino-ethyl, (1-methylpropoxyamino) ethyl, (2-methylpropoxyamino) ethyl, (1, 1-dimethylethoxyamino) ethyl, n-pentoxyaminoethyl,
(1-Methylbutoxyamino) ethyl , (2-Methylbutoxyamino) ethyl , (3-Methylbutoxyamino) ethyl , (2 , 2-Dirnethylpropoxyamino) ethyl , (1-Ethylpropoxyamino) ethyl , n-Hexoxyamino-ethyl, (1, 1-Di - methylpropoxyamino) ethyl , (1 , 2-Dirnethylpropoxyamino) ethyl , (1-Methylpentoxyamino) ethyl, (2-Methylpentoxyamino) ethyl, (3-Methylpentoxyamino) ethyl, (4-Methylpentoxyamino) ethyl, (1, 1-Dimethylbutoxyamino) ethyl, (1, 2-Dimethylbutoxyamino) - ethyl, (1, 3-Dimethylbutoxyamino) ethyl, (2, 2-Dimethylbutoxy- amino) ethyl, (2, 3-Dirnethylbutoxyamino) ethyl, (3 , 3-Dimethyl- butoxyamino) ethyl, (1-Ethylbutoxyamino) ethyl, (2-Ethylbutoxyamino) ethyl, (1, 1, 2-Trimethylpropoxyamino) ethyl, (1,2,2-Tri- methylpropoxyamino) ethyl, (1-Ethyl-l-methylpropoxyamino) - ethyl, (l-Ethyl-2-methylpropoxyamino) ethyl, 2- (Methoxyamino) - propyl, 3- (Methoxyamino) propyl oder 2- (Ethoxyamino) propyl, vorzugsweise Cι-Cδ-Alkoxyamino-Cι-C2-alkyl;(1-methylbutoxyamino) ethyl, (2-methylbutoxyamino) ethyl, (3-methylbutoxyamino) ethyl, (2, 2-dirnethylpropoxyamino) ethyl, (1-ethylpropoxyamino) ethyl, n-hexoxyamino-ethyl, (1, 1-di - methylpropoxyamino) ethyl, (1, 2-dimethylpropoxyamino) ethyl, (1-methylpentoxyamino) ethyl, (2-methylpentoxyamino) ethyl, (3-methylpentoxyamino) ethyl, (4-methylpentoxyamino) ethyl, (1, 1-dimethylbutoxyamino) ethyl, (1, 2-dimethylbutoxyamino) ethyl, (1, 3-dimethylbutoxyamino) ethyl, (2, 2-dimethylbutoxyamino) ethyl, (2, 3-dimethylbutoxyamino) ethyl, (3, 3-dimethylbutoxyamino) ethyl, (1-ethylbutoxyamino) ethyl, (2-ethylbutoxyamino) ethyl, (1, 1, 2-trimethylpropoxyamino) ethyl, (1,2,2-trimethylpropoxyamino) ethyl, (1-ethyl-l-methylpropoxyamino) ethyl, (l-ethyl-2-methylpropoxyamino) ethyl, 2- (methoxyamino) - propyl, 3- (methoxyamino) propyl or 2- (ethoxyamino) propyl, preferably Cι-C δ -Alkoxyamino-Cι-C 2 alkyl;
Ci-Cδ-Alkoxy-Ci-Cδ-alkylamino-Ci-Cδ-alkyl für: Ci-Cδ-Alkyl- amino-Ci-Cδ-alkyl wie CH2-NH-CH3, CH2-NH-C2H5, CH2-NH-CH2-C2H5, CH2-NH-CH(CH3)2, CH2-NH-(CH2)3-CH3, CH2-NH-CH (CH3) -C2H5 , CH2-NH-CH2-CH(CH3)2, CH2-NH-C (CH3) 3 , CH2-NH- (CH2) 4-CH3 ,Ci-C δ -alkoxy-Ci-C δ -alkylamino-Ci-C δ -alkyl for: Ci-C δ -alkylamino-Ci-C δ -alkyl such as CH 2 -NH-CH 3 , CH 2 -NH -C 2 H 5 , CH 2 -NH-CH 2 -C 2 H 5 , CH 2 -NH-CH (CH 3 ) 2 , CH 2 -NH- (CH 2 ) 3 -CH 3 , CH 2 -NH- CH (CH 3 ) -C 2 H 5 , CH 2 -NH-CH 2 -CH (CH 3 ) 2 , CH 2 -NH-C (CH 3 ) 3 , CH 2 -NH- (CH 2 ) 4 -CH 3 ,
(1-Methylbutylamino) methyl , (2-Methylbutylamino) methyl , (3-Methylbutylamino) methyl, (2, 2-Dirnethylpropylamino) methyl, (1-Ethylpropylamino) methyl, n-Hexylamino-methyl, (1,1-Di- methylpropylamino) methyl , (1 , 2-Dimethylpropylamino) ethyl ,(1-methylbutylamino) methyl, (2-methylbutylamino) methyl, (3-methylbutylamino) methyl, (2, 2-dimethylpropylamino) methyl, (1-ethylpropylamino) methyl, n-hexylamino-methyl, (1,1-dimethylpropylamino) methyl, (1, 2-dimethylpropylamino) ethyl,
( 1-Methylpentylamino) methyl , (2-Methylpentylamino) methyl ,(1-methylpentylamino) methyl, (2-methylpentylamino) methyl,
(3-Methylpentylamino) methyl , (4-Methylpentylamino) methyl , (1, 1-Dimethylbutylamino) methyl, (1, 2-Dimethylbutylamino) - methyl, (1, 3-Dirnethylbutylamino) methyl, (2, 2-Dirnethylbutyl - amino)methyl, (2, 3-Dimethylbutylamino)methyl, (3 , 3-Dimethyl- butylamino)methyl, (1-Ethylbutylamino) methyl, (2-Ethylbutyl- amino) methyl, (1, 1, 2-Trimethylpropylamino) methyl, (1,2, 2-Tri - methylpropylamino) methyl, (1-Ethyl-l-methylpropylamino) - methyl, (l-Ethyl-2-methylpropylamino) methyl, Methylamino- ethyl, Ethylamino-ethyl, n-Propylamino-ethyl, (1-Methylethyl- amino) ethyl, n-Butylamino-ethyl , (1-Methylpropylamino) ethyl, (2-Methylpropylamino) ethyl, (1, 1-Dimethylethylamino) ethyl, n-Pentylaminoethyl, (1-Methylbutylamino) ethyl, (2-Methyl- butylamino) ethyl, (3-Methylbutylamino) ethyl, (2 , 2-Dimethyl - propylamino) ethyl, (1-Ethylpropylamino) ethyl, n-Hexylamino- ethyl, (1, 1-Dimethylpropylamino) ethyl, (1, 2-Dirnethylpropylamino) ethyl, (1-Methylpentylamino) ethyl, (2-Methylpentyl- amino) ethyl, (3-Methylpentylamino) ethyl, (4-Methylpentyl - amino) ethyl, (1, 1-Dimethylbutylamino) ethyl, (1, 2-Dimethyl - butylamino) ethyl, (1, 3-Dirnethylbutylamino) ethyl, (2,2-Di- methylbutylamino) ethyl, (2, 3-Dimethylbutylamino) ethyl, (3 , 3-Dirnethylbutylamino) ethyl, (1-Ethylbutylamino) ethyl, (2-Ethylbutylamino) ethyl, (1, 1, 2-Trimethylpropylamino) ethyl, (1, 2, 2-Trimethylpropylamino) ethyl, (1-Ethyl-l-methylpropylamino) ethyl, (l-Ethyl-2-methylpropylamino) ethyl, 2- (Methyl - amino)propyl, 3- (Methylamino) propyl und 2- (Ethylamino) propyl, vorzugsweise Cι-Cg-Alkylamino-Cι-C2-alkyl, das durch Ci-Cδ-Alkoxy - wie vorstehend genannt - substituiert ist, also z.B. für CH2-NH-CH2-OCH3 oder CH2-NH-CH2-OC2H5;(3-methylpentylamino) methyl, (4-methylpentylamino) methyl, (1, 1-dimethylbutylamino) methyl, (1, 2-dimethylbutylamino) methyl, (1, 3-dimethylbutylamino) methyl, (2, 2-dimethylbutylamino) methyl ) methyl, (2, 3-dimethylbutylamino) methyl, (3, 3-dimethylbutylamino) methyl, (1-ethylbutylamino) methyl, (2-ethylbutylamino) methyl, (1, 1, 2-trimethylpropylamino) methyl, (1,2,2-tri-methylpropylamino) methyl, (1-ethyl-l-methylpropylamino) methyl, (l-ethyl-2-methylpropylamino) methyl, methylaminoethyl, ethylaminoethyl, n-propylaminoethyl, (1-methylethylamino) ethyl, n-butylaminoethyl, (1-methylpropylamino) ethyl, (2-methylpropylamino) ethyl, (1, 1-dimethylethylamino) ethyl, n-pentylaminoethyl, (1-methylbutylamino) ethyl, ( 2-methylbutylamino) ethyl, (3-methylbutylamino) ethyl, (2, 2-dimethylpropylamino) ethyl, (1-ethylpropylamino) ethyl, n-hexylaminoethyl, (1, 1-dimethylpropylamino) ethyl, (1 , 2-Dirnethylpropylamino) ethyl, (1-Methylpentylamino) ethyl, (2-Methylpentyl- am ino) ethyl, (3-methylpentylamino) ethyl, (4-methylpentylamino) ethyl, (1, 1-dimethylbutylamino) ethyl, (1, 2-dimethylbutylamino) ethyl, (1, 3-dirnethylbutylamino) ethyl, ( 2,2-dimethylbutylamino) ethyl, (2, 3-dimethylbutylamino) ethyl, (3, 3-dimethylbutylamino) ethyl, (1-ethylbutylamino) ethyl, (2-ethylbutylamino) ethyl, (1, 1, 2-trimethylpropylamino ) ethyl, (1, 2, 2-trimethylpropylamino) ethyl, (1-ethyl-l-methylpropylamino) ethyl, (l-ethyl-2-methylpropylamino) ethyl, 2- (methylamino) propyl, 3- (methylamino) propyl and 2- (ethylamino) propyl, preferably -C-Cg-alkylamino-Cι-C 2 alkyl, which is substituted by Ci-C δ -alkoxy - as mentioned above - so for example for CH 2 -NH-CH 2 - OCH 3 or CH 2 -NH-CH 2 -OC 2 H 5 ;
Cι-Cg-Alkyloximino-Cι-Cg-alkyl für: durch Ci-Cg-Alkyloximino wie Methoxyimino, Ethoxyi ino, 1-Propoxyimino, 2-Propoxy- imino, 1-Methylethoxyimino, n-Butoxyimino, sec.-Butoxyimino, tert.-Butoxyimino, 1-Methyl-l-propoxyimino, 2-Methyl-1-prop- oxyimino, l-Methyl-2-propoxyimino, 2-Methyl-2-propoxyimino, n-Pentoxyimino, 2-Pentoxyimino, 3-Pentoxyimino, 4-Pentoxy- imino, 1-Methyl-l-butoxyimino, 2-Methyl-l-butoxyimino, 3-Methyl-l-butoxyimino, l-Methyl-2-butoxyimino, 2-Methyl- 2-butoxyimino, 3-Methyl-2-butoxyimino, l-Methyl-3-butoxy- imino, 2-Methyl-3-butoxyimino, 3-Methyl-3-butoxyimino, 1, l-Dimethyl-2-propoxyimino, 1, 2-Dimethyl-l-propoxyimino, 1, 2-Dimethyl-2-propoxyimino, 1-Ethyl-l-propoxyimino, l-Ethyl-2-propoxyimino, n-Hexoxyimino, 2-Hexoxyimino, 3-Hexoxyimino, 4-Hexoxyimino, 5-Hexoxyimino, 1-Methyl-l-pent- oxyimino, 2-Methyl-l-pentoxyimino, 3-Methyl-l-pentoxyimino, 4-Methyl-l-pentoxyimino, l-Methyl-2-pentoxyimino, 2-Methyl- 2-pentoxyimino, 3-Methyl-2-pentoxyimino, 4-Methyl-2-pentoxy- imino, l-Methyl-3-pentoxyimino, 2-Methyl-3-pentoxyimino, 3-Methyl-3-pentoxyimino, 4-Methyl-3-pentoxyimino, l-Methyl-4- pentoxyimino, 2-Methyl-4-pentoxyimino, 3-Methyl-4-pentoxy- imino, 4-Methyl-4-pentoxyimino, 1, l-Dimethyl-2-butoxyimino, 1, l-Dimethyl-3-butoxyimino, 1, 2-Dimethyl-l-butoxyimino, 1, 2-Dimethyl-2-butoxyimino, 1, 2-Dimethyl-3-butoxyimino, 1, 3-Dimethyl-l-butoxyimino, 1, 3-Dimethyl-2-butoxyimino, 1, 3-Dimethyl-3-butoxyimino, 2, 2-Dimethyl-3-butoxyimino, 2 , 3-Dimethyl-l-butoxyimino, 2 , 3-Dimethyl-2-butoxyimino,-C-Cg-Alkyloximino-Cι-Cg-alkyl for: by Ci-Cg-alkyloximino such as methoxyimino, ethoxyi ino, 1-propoxyimino, 2-propoxyimino, 1-methylethoxyimino, n-butoxyimino, sec.-butoxyimino, tert. -Butoxyimino, 1-methyl-l-propoxyimino, 2-methyl-1-prop-oxyimino, l-methyl-2-propoxyimino, 2-methyl-2-propoxyimino, n-pentoxyimino, 2-pentoxyimino, 3-pentoxyimino, 4 Pentoxy imino, 1-methyl-l-butoxyimino, 2-methyl-l-butoxyimino, 3-methyl-l-butoxyimino, l-methyl-2-butoxyimino, 2-methyl-2-butoxyimino, 3-methyl-2 -butoxyimino, l-methyl-3-butoxyimino, 2-methyl-3-butoxyimino, 3-methyl-3-butoxyimino, 1, l-dimethyl-2-propoxyimino, 1, 2-dimethyl-l-propoxyimino, 1 , 2-dimethyl-2-propoxyimino, 1-ethyl-l-propoxyimino, l-ethyl-2-propoxyimino, n-hexoxyimino, 2-hexoxyimino, 3-hexoxyimino, 4-hexoxyimino, 5-hexoxyimino, 1-methyl-l pent oxyimino, 2-methyl-l-pentoxyimino, 3-methyl-l-pentoxyimino, 4-methyl-1-pentoxyimino, 1-methyl-2-pentoxyimino, 2-methyl-2-pentoxyimino, 3-methyl-2-pentoxyimino, 4-methyl-2-pentoxyimino, 1-methyl-3-pentoxyimino, 2-methyl-3-pentoxyimino, 3-methyl-3-pentoxyimino, 4-methyl-3-pentoxyimino, l-methyl-4-pentoxyimino, 2-methyl-4-pentoxyimino, 3-methyl-4-pentoxyimino, 4-methyl-4-pentoxyimino, 1, l-dimethyl-2-butoxyimino, 1, l-dimethyl-3-butoxyimino, 1, 2-dimethyl-l-butoxyimino, 1, 2-dimethyl-2-butoxyimino, 1, 2-dimethyl-3-butoxyimino, 1, 3-dimethyl-l-butoxyimino, 1, 3-dimethyl-2-butoxyimino, 1, 3-dimethyl-3-butoxyimino, 2, 2-dimethyl-3-butoxyimino, 2, 3-dimethyl-l-butoxyimino, 2, 3-dimethyl-2-butoxyimino,
2 , 3-Dirnethyl-3-butoxyimino, 3 , 3-Dimethyl-l-butoxyimino,2, 3-dimethyl-3-butoxyimino, 3, 3-dimethyl-1-butoxyimino,
3 , 3-Dimethyl-2-butoxyimino, 1-Ethyl-l-butoxyimino, 1-Ethyl- 2-butoxyimino, l-Ethyl-3-butoxyimino, 2-Ethyl-l-butoxyimino, 2-Ethyl-2-butoxyimino, 2-Ethyl-3-butoxyimino, 1,1,2-Tri- methyl-2-propoxyimino, 1-Ethyl-1-methyl-2-propoxyimino, l-Ethyl-2-methyl-l-propoxyimino und l-Ethyl-2-methyl-2- propoxyimino, substituiertes Ci-Cg-Alkyl, also z.B. für Methoxyiminomethyl ;3,3-dimethyl-2-butoxyimino, 1-ethyl-1-butoxyimino, 1-ethyl-2-butoxyimino, 1-ethyl-3-butoxyimino, 2-ethyl-1-butoxyimino, 2-ethyl-2-butoxyimino, 2-ethyl-3-butoxyimino, 1,1,2-trimethyl-2-propoxyimino, 1-ethyl-1-methyl-2-propoxyimino, l-ethyl-2-methyl-l-propoxyimino and l-ethyl- 2-methyl-2-propoxyimino, substituted Ci-Cg-alkyl, e.g. for methoxyiminomethyl;
Ci-Cg-Alkoxy-Ci-Cδ-alkyl für: durch Ci-Cδ-Alkoxy - wie vorstehend genannt - substituiertes Ci-Cg-Alkyl, also z.B. für CH2-OCH3, CH2-OCH5, n-Propoxymethyl , CH2 -OCH (CH3) 2, n-Butoxy- methyl, (1-Methylpropoxy) methyl, (2-Methylpropoxy) methyl, CH2-OC(CH3)3, 2- (Methoxy) ethyl, 2- (Ethoxy) ethyl, 2-(n-Prop- oxy) ethyl , 2- ( 1-Methylethoxy) ethyl , 2- (n-Butoxy) ethyl , 2- (1-Methylpropoxy) ethyl, 2- (2-Methylpropoxy) ethyl, 2- (1,1-Dimethylethoxy) ethyl, 2- (Methoxy) propyl, 2- (Ethoxy) - propyl, 2- (n-Propoxy) propyl, 2- (1-Methylethoxy) propyl, 2- (n-Butoxy) propyl, 2- (1-Methylpropoxy) propyl, 2-(2-Methyl- propoxy) propyl , 2- (1, 1-Dimethylethoxy) propyl, 3- (Methoxy) - propyl, 3- (Ethoxy) -propyl, 3- (n-Propoxy) propyl, 3-(l-Methyl- ethoxy) propyl, 3- (n-Butoxy) propyl, 3- (1-Methylpropoxy) propyl, 3- (2-Methylpropoxy) propyl, 3- (1, 1-Dirnethylethoxy) propyl, 2- (Methoxy) -butyl, 2- (Ethoxy) butyl, 2- (n-Propoxy) butyl, 2- (1-Methylethoxy) butyl, 2- (n-Butoxy) butyl, 2-(l-Methyl- propoxy) butyl , 2- (2-Methylpropoxy) butyl, 2- (1, 1-Dimethyl- ethoxy) butyl, 3- (Methoxy) butyl, 3- (Ethoxy) butyl, 3- (n-Propoxy) butyl, 3- (1-Methylethoxy) butyl, 3- (n-Butoxy) - butyl, 3- (1-Methylpropoxy) butyl, 3- (2-Methylpropoxy) butyl, 3- (1, 1-Dimethylethoxy) butyl, 4- (Methoxy) butyl, 4- (Ethoxy) - butyl, 4- (n-Propoxy) butyl, 4- (1-Methylethoxy) butyl, 4- (n-Butoxy) butyl, 4- (1-Methylpropoxy) butyl, 4-(2-Methyl- propoxy) butyl oder 4- (1, 1-Dimethylethoxy) butyl, insbesondere für CH2-OCH3 oder 2 -Methoxyethyl; Di (Ci-Cg-Alkoxy) -Ci-Cδ-alkyl für: z.B. 2 , 2-Dimethoxyethyl oder 2, 2-Diethoxyethyl;Ci-Cg-Alkoxy-Ci-C δ- alkyl for: Ci-C δ- alkoxy - as mentioned above - substituted Ci-Cg-alkyl, e.g. for CH 2 -OCH 3 , CH 2 -OCH 5 , n- Propoxymethyl, CH 2 -OCH (CH 3 ) 2 , n-butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, CH 2 -OC (CH 3 ) 3 , 2- (methoxy) ethyl, 2 - (Ethoxy) ethyl, 2- (n-propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methylpropoxy ) ethyl, 2- (1,1-dimethylethoxy) ethyl, 2- (methoxy) propyl, 2- (ethoxy) propyl, 2- (n-propoxy) propyl, 2- (1-methylethoxy) propyl, 2- ( n-butoxy) propyl, 2- (1-methylpropoxy) propyl, 2- (2-methylpropoxy) propyl, 2- (1, 1-dimethylethoxy) propyl, 3- (methoxy) propyl, 3- (ethoxy) propyl, 3- (n-propoxy) propyl, 3- (l-methylethoxy) propyl, 3- (n-butoxy) propyl, 3- (1-methylpropoxy) propyl, 3- (2-methylpropoxy) propyl, 3- (1, 1-dimethylethoxy) propyl, 2- (methoxy) butyl, 2- (ethoxy) butyl, 2- (n-propoxy) butyl, 2- (1-methylethoxy) butyl, 2- (n-but oxy) butyl, 2- (l-methylpropoxy) butyl, 2- (2-methylpropoxy) butyl, 2- (1, 1-dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl , 3- (n-propoxy) butyl, 3- (1-methylethoxy) butyl, 3- (n-butoxy) butyl, 3- (1-methylpropoxy) butyl, 3- (2-methylpropoxy) butyl, 3- ( 1, 1-dimethylethoxy) butyl, 4- (methoxy) butyl, 4- (ethoxy) butyl, 4- (n-propoxy) butyl, 4- (1-methylethoxy) butyl, 4- (n-butoxy) butyl, 4- (1-methylpropoxy) butyl, 4- (2-methylpropoxy) butyl or 4- (1, 1-dimethylethoxy) butyl, especially for CH 2 -OCH 3 or 2-methoxyethyl; Di (Ci-Cg-alkoxy) -Ci-C δ- alkyl for: for example 2, 2-dimethoxyethyl or 2, 2-diethoxyethyl;
Ci-Cδ-Alkoxy-Ci-Cδ-alkoxy für: durch Ci-Cg-Alkoxy wie vor- stehend genannt substituiertes Ci-Cg-Alkoxy, also z.B. für OCH2-OCH3, OCH2-OC2H5, n-Propoxymethoxy, OCH2-OCH(CH3) 2, n-Butoxymethoxy, (1-Methylpropoxy) methoxy, (2-Methyl- propoxy) methoxy, OCH -OC (CH3) 3, 2- (Methoxy) ethoxy, 2- (Ethoxy) ethoxy, 2- (n-Propoxy) ethoxy, 2-(l-Methyl- ethoxy) ethoxy, 2- (n-Butoxy) ethoxy, 2- (1-Methylpropoxy) ethoxy, 2- (2-Methylpropoxy) ethoxy, 2- (1, 1-Dimethylethoxy) ethoxy, 2- (Methoxy) propoxy, 2- (Ethoxy) propoxy, 2- (n-Propoxy) propoxy, 2- (l-Methylethoxy)propoxy, 2- (n-Butoxy) propoxy, 2-(l-Methyl- propoxy) propoxy, 2- (2-Methylpropoxy) propoxy, 2- (1, 1-Dimethyl- ethoxy) propoxy, 3- (Methoxy) -propoxy, 3- (Ethoxy) propoxy, 3- (n-Propoxy) propoxy, 3- (1-Methylethoxy) propoxy, 3- (n-Butoxy) propoxy, 3- (1-Methylpropoxy) propoxy, 3-(2-Methyl- propoxy) propoxy, 3- (1, 1-Dimethylethoxy) propoxy, 2- (Methoxy) - butoxy, 2- (Ethoxy) butoxy, 2- (n-Propoxy) butoxy, 2-(l-Methyl- ethoxy) butoxy, 2- (n-Butoxy) -butoxy, 2- (1-Methylpropoxy) - butoxy, 2- (2-Methylpropoxy) butoxy, 2- (1, 1-Dirnethylethoxy) - butoxy, 3- (Methoxy) butoxy, 3- (Ethoxy) butoxy, 3- (n-Propoxy) - butoxy, 3- (1-Methylethoxy) butoxy, 3- (n-Butoxy) butoxy, 3- (1-Methylpropoxy) butoxy, 3- (2-Methylpropoxy) butoxy, 3- (1, 1-Dimethylethoxy) butoxy, 4- (Methoxy) butoxy, 4- (Ethoxy) - butoxy, 4- (n-Propoxy) butoxy, 4- (1-Methylethoxy) butoxy, 4- (n-Butoxy) butoxy, 4- (1-Methylpropoxy) butoxy, 4-(2-Methyl- propoxy) butoxy, 4- (1, 1-Dirnethylethoxy) butoxy, 5- (Methoxy) - pentoxy, 5- (Ethoxy) pentoxy, 5- (n-Propoxy) pentoxy, 5- (1-Methylethoxy) pentoxy, 5- (n-Butoxy) pentoxy, 5-(l-Methyl- propoxy) pentoxy, 5- (2-Methylpropoxy) pentoxy, 5- (1, 1-Dimethyl- ethoxy) pentoxy, 6- (Methoxy) hexoxy, 6- (Ethoxy) hexoxy, 6- (n-Propoxy) hexoxy, 6- (1-Methylethoxy) hexoxy, 6- (n-Butoxy) - hexoxy, 6- (1-Methylpropoxy) hexoxy, 6- (2-Methylpropoxy) hexoxy oder 6- (1, 1-Dimethylethoxy) exoxy, insbesondere für OCH2-OCH3 oder OCH2-OC2H5;Ci-C δ- alkoxy-Ci-C δ- alkoxy for: Ci-Cg-alkoxy substituted by Ci-Cg-alkoxy as mentioned above, for example for OCH 2 -OCH 3 , OCH 2 -OC 2 H 5 , n-propoxymethoxy, OCH 2 -OCH (CH 3 ) 2 , n-butoxymethoxy, (1-methylpropoxy) methoxy, (2-methylprooxy) methoxy, OCH -OC (CH 3 ) 3 , 2- (methoxy) ethoxy, 2- (ethoxy) ethoxy, 2- (n-propoxy) ethoxy, 2- (l-methylethoxy) ethoxy, 2- (n-butoxy) ethoxy, 2- (1-methylpropoxy) ethoxy, 2- (2- Methylpropoxy) ethoxy, 2- (1, 1-dimethylethoxy) ethoxy, 2- (methoxy) propoxy, 2- (ethoxy) propoxy, 2- (n-propoxy) propoxy, 2- (l-methylethoxy) propoxy, 2- ( n-butoxy) propoxy, 2- (l-methylpropoxy) propoxy, 2- (2-methylpropoxy) propoxy, 2- (1, 1-dimethylethoxy) propoxy, 3- (methoxy) propoxy, 3- ( Ethoxy) propoxy, 3- (n-propoxy) propoxy, 3- (1-methylethoxy) propoxy, 3- (n-butoxy) propoxy, 3- (1-methylpropoxy) propoxy, 3- (2-methylprooxy) propoxy , 3- (1, 1-dimethylethoxy) propoxy, 2- (methoxy) butoxy, 2- (ethoxy) butoxy, 2- (n-propoxy) butoxy, 2- (l-met hyl-ethoxy) butoxy, 2- (n-butoxy) butoxy, 2- (1-methylpropoxy) butoxy, 2- (2-methylpropoxy) butoxy, 2- (1, 1-dimethylethyloxy) butoxy, 3- ( Methoxy) butoxy, 3- (ethoxy) butoxy, 3- (n-propoxy) butoxy, 3- (1-methylethoxy) butoxy, 3- (n-butoxy) butoxy, 3- (1-methylpropoxy) butoxy, 3- (2-methylpropoxy) butoxy, 3- (1, 1-dimethylethoxy) butoxy, 4- (methoxy) butoxy, 4- (ethoxy) butoxy, 4- (n-propoxy) butoxy, 4- (1-methylethoxy) butoxy , 4- (n-butoxy) butoxy, 4- (1-methylpropoxy) butoxy, 4- (2-methylpropoxy) butoxy, 4- (1, 1-dimethylethoxy) butoxy, 5- (methoxy) pentoxy, 5 - (Ethoxy) pentoxy, 5- (n-propoxy) pentoxy, 5- (1-methylethoxy) pentoxy, 5- (n-butoxy) pentoxy, 5- (l-methylpropoxy) pentoxy, 5- (2-methylpropoxy ) pentoxy, 5- (1, 1-dimethylethoxy) pentoxy, 6- (methoxy) hexoxy, 6- (ethoxy) hexoxy, 6- (n-propoxy) hexoxy, 6- (1-methylethoxy) hexoxy, 6- (n-Butoxy) - hexoxy, 6- (1-methylpropoxy) hexoxy, 6- (2-methylpropoxy) hexoxy or 6- (1, 1-dimethylethoxy) exoxy, especially for r OCH 2 -OCH 3 or OCH 2 -OC 2 H 5 ;
(Ci-Cδ-Alkyl) carbonyl-Ci-Cg-alkoxy für: durch (Ci-Cδ-Alkyl) - carbonyl wie vorstehend genannt substituiertes Ci-Cg-Alkoxy, also z.B. für OCH2-CO-CH3, OCH2-CO-C2H5, OCH2-CO-CH2-C2H5,(Ci-C δ- alkyl) carbonyl-Ci-Cg-alkoxy for: Ci-Cg-alkoxy substituted by (Ci-C δ- alkyl) carbonyl as mentioned above, for example for OCH 2 -CO-CH 3 , OCH 2 -CO-C 2 H 5 , OCH 2 -CO-CH 2 -C 2 H 5 ,
OCH2-CO-CH(CH3)2, n-Butylcarbonyl-methoxy, 1- (CO-CH3) ethoxy, 2- (CO-CH3) ethoxy, 2- (CO-C2H5) ethoxy, 2- (CO-CH2-C2H5) ethoxy, 2- (n-Butylcarbonyl) ethoxy, 3- (CO-CH3) propoxy, 3-(CO-C2Hs)- propoxy, 3- (CO-CH2-C2Hs) propoxy, 3- (n-Butylcarbonyl) propoxy, 4- (CO-CH3) butoxy, 4- (CO-C2H5) butoxy, 4- (CO-CH2-CH5) butoxy, 4- (n-Butylcarbonyl) butoxy, 5- (CO-CH3) pentoxy, 5-(CO-C2H5)- pentoxy, 5- (CO-CH2-C2H5) pentoxy, 5- (n-Butylcarbonyl) butoxy. 6- (CO-CH3) hexoxy, 6- (CO-C2H5) hexoxy, 6- (CO-CH2-C2H5) hexoxy oder 6- (n-Butylcarbonyl) hexoxy, insbesondere für OCH2-CO-OCH3 oder 1- (C0-CH3) ethoxy;OCH 2 -CO-CH (CH 3 ) 2 , n-butylcarbonyl-methoxy, 1- (CO-CH 3 ) ethoxy, 2- (CO-CH 3 ) ethoxy, 2- (CO-C 2 H 5 ) ethoxy, 2- (CO-CH 2 -C 2 H 5 ) ethoxy, 2- (n-butylcarbonyl) ethoxy, 3- (CO-CH 3 ) propoxy, 3- (CO-C 2 Hs) propoxy, 3- (CO -CH 2 -C 2 Hs) propoxy, 3- (n-butylcarbonyl) propoxy, 4- (CO-CH 3 ) butoxy, 4- (CO-C 2 H 5 ) butoxy, 4- (CO-CH 2 -CH 5 ) butoxy, 4- (n-butylcarbonyl) butoxy, 5- (CO-CH 3 ) pentoxy, 5- (CO-C 2 H 5 ) pentoxy, 5- (CO-CH 2 -C 2 H 5 ) pentoxy , 5- (n-Butylcarbonyl) butoxy. 6- (CO-CH 3 ) hexoxy, 6- (CO-C 2 H 5 ) hexoxy, 6- (CO-CH 2 -C 2 H 5 ) hexoxy or 6- (n-butylcarbonyl) hexoxy, especially for OCH 2 -CO-OCH 3 or 1- (CO-CH 3 ) ethoxy;
- (Ci-Cg-Alkoxy) carbonyl-Ci-Cg-alkoxy für: durch (Ci-Cg-Alkoxy) - carbonyl wie vorstehend genannt substituiertes Ci-Cg-Alkoxy, also z.B. für OCH2-CO-OCH3, 0CH2 -CO-OC2H5, 0CH -CO-OCH2-C2H5, OCH2-CO-OCH(CH3) 2, n-Butoxycarbonyl-methoxy, 1- (Methoxy- carbonyl) ethoxy, 2- (Methoxycarbonyl) ethoxy, 2-(Ethoxy- carbonyl) ethoxy, 2- (n-Propoxycarbonyl) ethoxy, 2- (n-Butoxy- carbonyl) ethoxy, 3- (Methoxycarbonyl) ropoxy, 3-(Ethoxy- carbonyl) propoxy, 3- (n-Propoxycarbonyl) propoxy, 3- (n-Butoxy- carbonyl) propoxy, 4- (Methoxycarbonyl) butoxy, 4-(Ethoxy- carbonyl) butoxy, 4- (n-Propoxycarbonyl) butoxy, 4-(n-Butoxy- carbonyl) butoxy, 5- (Methoxycarbonyl) pentoxy, 5- (Ethoxy- carbonyl) pentoxy, 5- (n-Propoxycarbonyl) pentoxy, 5- (n-Butoxy- carbonyl) butoxy, 6- (Methoxycarbonyl) hexoxy, 6- (Ethoxy- carbonyl) hexoxy, 6- (n-Propoxycarbonyl) hexoxy oder 6- (n-Butoxycarbonyl) hexoxy, insbesondere für OCH2-CO-OCH3 oder 1- (Methoxycarbonyl) ethoxy;- (Ci-Cg-alkoxy) carbonyl-Ci-Cg-alkoxy for: Ci-Cg-alkoxy substituted by (Ci-Cg-alkoxy) carbonyl as mentioned above, e.g. for OCH 2 -CO-OCH 3 , 0CH 2 -CO-OC 2 H 5 , 0CH -CO-OCH 2 -C 2 H 5 , OCH 2 -CO-OCH (CH 3 ) 2 , n-butoxycarbonyl-methoxy, 1- (methoxycarbonyl) ethoxy, 2- ( Methoxycarbonyl) ethoxy, 2- (ethoxycarbonyl) ethoxy, 2- (n-propoxycarbonyl) ethoxy, 2- (n-butoxycarbonyl) ethoxy, 3- (methoxycarbonyl) ropoxy, 3- (ethoxycarbonyl) propoxy, 3 - (n-Propoxycarbonyl) propoxy, 3- (n-butoxycarbonyl) propoxy, 4- (methoxycarbonyl) butoxy, 4- (ethoxycarbonyl) butoxy, 4- (n-propoxycarbonyl) butoxy, 4- (n-butoxy - carbonyl) butoxy, 5- (methoxycarbonyl) pentoxy, 5- (ethoxycarbonyl) pentoxy, 5- (n-propoxycarbonyl) pentoxy, 5- (n-butoxycarbonyl) butoxy, 6- (methoxycarbonyl) hexoxy, 6- (Ethoxycarbonyl) hexoxy, 6- (n-propoxycarbonyl) hexoxy or 6- (n-butoxycarbonyl) hexoxy, in particular for OCH 2 -CO-OCH 3 or 1- (methoxycarbonyl) ethoxy;
(Ci-Cg-Alkoxy) carbonyl-Ci-Cg-alkyl für: durch (Ci-Cg-Alkoxy) - carbonyl wie vorstehend genannt substituiertes Ci-Cg-Alkyl, also z.B. für Methoxycarbonylmethyl , Ethoxycarbonylmethyl, 1 - (Methoxycarbonyl) ethyl , 2 - (Methoxycarbonyl) ethyl ,(Ci-Cg-alkoxy) carbonyl-Ci-Cg-alkyl for: Ci-Cg-alkyl substituted by (Ci-Cg-alkoxy) carbonyl as mentioned above, e.g. for methoxycarbonylmethyl, ethoxycarbonylmethyl, 1 - (methoxycarbonyl) ethyl, 2 - (methoxycarbonyl) ethyl,
2 - (Ethoxycarbonyl) ethyl, 3 - (Methoxycarbonyl) propyl, 4- (Methoxycarbonyl) butyl, 5- (Methoxycarbonyl)pentyl oder 6- (Methoxycarbonyl) hexyl ;2 - (ethoxycarbonyl) ethyl, 3 - (methoxycarbonyl) propyl, 4- (methoxycarbonyl) butyl, 5- (methoxycarbonyl) pentyl or 6- (methoxycarbonyl) hexyl;
- (Ci -Cg -Alkoxy) carbonyl -Ci-Cδ-alkylsulfonyl für: durch- (Ci -Cg -alkoxy) carbonyl -Ci-C δ -alkylsulfonyl for: by
(Ci-Cg-Alkoxy) carbonyl wie vorstehend genannt substituiertes Ci-Cg-Alkylsulfonyl, also z.B. für Methoxycarbonylmethylsul- fonyl, Ethoxycarbonylmethylsulfonyl, 1- (Methoxycarbonyl) - ethylsulfonyl, 2- (Methoxycarbonyl) ethylsulfonyl, 2-(Ethoxy- carbonyl) ethylsulfonyl, 3 - (Methoxycarbonyl) propylsulfonyl,(Ci-Cg-alkoxy) carbonyl as substituted Ci-Cg-alkylsulfonyl as mentioned above, e.g. for methoxycarbonylmethylsulfonyl, ethoxycarbonylmethylsulfonyl, 1- (methoxycarbonyl) ethylsulfonyl, 2- (methoxycarbonyl) ethylsulfonyl, 2- (ethoxycarbonyl) ethylsulfonyl, 3 - (methoxycarbonyl) propylsulfonyl,
4- (Methoxycarbonyl)butylsulfonyl, 5- (Methoxycarbonyl)pentyl - sulfonyl oder 6- (MethoxycarbonylJhexylsulfonyl;4- (methoxycarbonyl) butylsulfonyl, 5- (methoxycarbonyl) pentylsulfonyl or 6- (methoxycarbonylhexylsulfonyl;
Ci-Cg-Alkylthio-Ci-Cg-alkyl für: durch Ci-Cδ-Alkylthio wie vorstehend genannt substituiertes Ci-Cδ-Alkyl, also z.B. für CH2-SCH3, CH2-SC2H5, CH2-SCH2-C2H5, CH2-SCH (CH3) 2, n-Butyl- thiomethyl, CH2-SCH (CH3) -C2H5, CH2-SCH2-CH(CH3) 2, CH2-SC (CH3) 3, 2-(SCH3)ethyl, 2- (SC H5) ethyl, 2- (SCH2-C2H5) ethyl, 2-[SCH(CH3)2]ethyl, 2- (n-Butylthio) ethyl, 2- [SCH(CH3) -C2H5] - ethyl, 2- (2-Methylpropylthio) ethyl, 2- [SC (CH3) 3] ethyl,Ci-Cg-alkylthio-Ci-Cg-alkyl viewed by C δ -alkylthio as mentioned above substituted C δ -alkyl, eg CH 2 -SCH 3, CH 2 -SC 2 H 5, CH 2 -SCH 2 -C 2 H 5 , CH 2 -SCH (CH 3 ) 2 , n-butylthiomethyl, CH 2 -SCH (CH 3 ) -C 2 H 5 , CH 2 -SCH 2 -CH (CH 3 ) 2 , CH 2 -SC (CH 3 ) 3 , 2- (SCH 3 ) ethyl, 2- (SC H 5 ) ethyl, 2- (SCH 2 -C 2 H 5 ) ethyl, 2- [SCH (CH 3 ) 2 ] ethyl, 2- (n-butylthio) ethyl, 2- [SCH (CH 3 ) -C 2 H 5 ] ethyl, 2- (2-methylpropylthio) ethyl, 2- [SC (CH 3 ) 3 ] ethyl ,
2- (SCH3) propyl, 3- (SCH3) propyl, 2- (SC2H5) propyl, 3-(SC2H5)- propyl, 3- (SCH2-C2H5) propyl, 3- (Butylthio) propyl, 4-(SCH3)- butyl, 4-(SC2H5)butyl, 4- (SCH2-C2H5) butyl oder 4- (n-Butylthio) butyl, insbesondere für 2- (SCH3) ethyl;2- (SCH 3 ) propyl, 3- (SCH 3 ) propyl, 2- (SC 2 H 5 ) propyl, 3- (SC 2 H 5 ) propyl, 3- (SCH 2 -C 2 H 5 ) propyl, 3- (butylthio) propyl, 4- (SCH 3 ) - butyl, 4- (SC 2 H 5 ) butyl, 4- (SCH 2 -C 2 H 5 ) butyl or 4- (n-butylthio) butyl, especially for 2- (SCH 3 ) ethyl;
Ci-Cg-Alkylthio-Ci-Cδ-alkoxy für: durch Ci-Cg-Alkylthio wie vorstehend genannt substituiertes Ci-Cδ-Alkoxy, also z.B. für 0CH2-SCH3, 0CH2-SC2H5, 0CH2-SCH2-C2H5 , 0CH2 - SCH (CH3) 2 , n-Butylthiomethoxy, 0CH2-SCH (CH3) -CH5, 0CH2 -SCH2 -CH (CH3) 2, OCH2-SC(CH3)3, 2- (SCH3) ethoxy, 2- (SC2H5) ethoxy, 2- (SCH2-C2H5) - ethoxy, 2- [SCH (CH3) 21 ethoxy, 2- (n-Butylthio) ethoxy, 2- [SCH (CH3) -C2H5] ethoxy, 2- (2-Methylpropylthio) ethoxy, 2- [SC(CH3)3] ethoxy, 2- (SCH3) propoxy, 3- (SCH3) propoxy, 2- (SC2H5) propoxy, 3- (SC2H5) propoxy, 3- (SCH2-C2H5) propoxy, 3- (Butylthio) propoxy, 4- (SCH3) butoxy, 4- (SC2H5) butoxy, 4-(CH2- C2H5)butoxy oder 4- (n-Butylthio) butoxy, insbesondere für 2- (SCH3) ethoxy;Ci-Cg-alkylthio-Ci-C δ alkoxy viewed by Ci-Cg-alkylthio as mentioned above substituted C δ alkoxy, eg for 0CH 2 -SCH 3, -SC 2 H 5 0CH 2, 2 0CH -SCH 2 -C 2 H 5 , 0CH 2 - SCH (CH 3 ) 2 , n-butylthiomethoxy, 0CH 2 -SCH (CH 3 ) -CH 5 , 0CH 2 -SCH 2 -CH (CH 3 ) 2 , OCH 2 -SC (CH 3 ) 3 , 2- (SCH 3 ) ethoxy, 2- (SC 2 H 5 ) ethoxy, 2- (SCH 2 -C 2 H 5 ) - ethoxy, 2- [SCH (CH 3 ) 2 1 ethoxy, 2- (n-butylthio) ethoxy, 2- [SCH (CH 3 ) -C 2 H 5 ] ethoxy, 2- (2-methylpropylthio) ethoxy, 2- [SC (CH 3 ) 3 ] ethoxy, 2- (SCH 3 ) propoxy, 3- (SCH 3 ) propoxy, 2- (SC 2 H 5 ) propoxy, 3- (SC 2 H 5 ) propoxy, 3- (SCH 2 -C 2 H 5 ) propoxy, 3- ( Butylthio) propoxy, 4- (SCH 3 ) butoxy, 4- (SC 2 H 5 ) butoxy, 4- (CH 2 - C 2 H 5 ) butoxy or 4- (n-butylthio) butoxy, especially for 2- (SCH 3 ) ethoxy;
Ci-Cg-Alkylthio- (Ci-Cg-alkyl) carbonyl für: durch Cι~Cg-Alkyl- thio wie vorstehend genannt, vorzugsweise SCH3 oder SC2Hs, substituiertes (Ci-Cg-Alkyl) carbonyl, also z.B. für Methyl - thiomethylcarbonyl , Ethylthiomethylcarbonyl, 1- (Methyl - thio) ethylcarbonyl , 2 - (Methylthio) ethylcarbonyl , 3 - (Methyl - thio)propylcarbonyl, 4 - (Methylthio) butylcarbonyl, 5 (Methyl - thio)pentylcarbonyl oder 6 - (Methylthio) hexylcarbonyl, insbesondere für CO-CH2-SCH3 oder CO-CH (CH3) -SCH3;Ci-Cg-alkylthio- (Ci-Cg-alkyl) carbonyl for: by Cι ~ Cg-alkyl- thio as mentioned above, preferably SCH 3 or SC 2 Hs, substituted (Ci-Cg-alkyl) carbonyl, so for example for methyl - thiomethylcarbonyl, ethylthiomethylcarbonyl, 1- (methylthio) ethylcarbonyl, 2 - (methylthio) ethylcarbonyl, 3 - (methylthio) propylcarbonyl, 4 - (methylthio) butylcarbonyl, 5 (methylthio) pentylcarbonyl or 6 - (methylthio) hexylcarbonyl, especially for CO-CH 2 -SCH 3 or CO-CH (CH 3 ) -SCH 3 ;
Di (Ci-Cg-alkyl) amino-Ci-Cg-alkoxy: durch Di- (Ci-Cδ-alkyl) - amino wie N(CH3)2, N(C2Hs)2, N,N-Dipropylamino, N,N-Di- (1-methylethyl) mino, N,N-Dibutylamino, N,N-Di- (1-methyl - propyl) amino, N,N-Di- (2-methylpropyl) amino, N[C(CH3)3] , 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-dimethylethyl) amino, N- (1-Methylethyl) -N-propylamino, N-Butyl-N-propylamino, N- (1-Methylpropyl) -N-propylamino, N- (2-Methylpropyl) -N- propylamino, N- (1, 1-Dimethylethyl) -N-propylamino, N-Butyl- N- (1-methylethyl) amino, N- (1-Methylethyl) -N- (1-methylpropyl) - amino, N- (1-Methylethyl) -N- (2-methylpropyl) amino, N-(l, 1-Dimethylethyl) -N- (1-methylethyl) amino, N-Butyl-N- (1-methyl - propyl) amino, N-Butyl-N- (2-methylpropyl) amino, N-Butyl-N- (1, 1-dimethylethyl) amino, N- (1-Methylpropyl) -N- (2-methyl- propyl) amino, N- (1, 1-Dimethylethyl) -N- (1-methylpropyl) amino oder N- (1, 1-Dimethylethyl) -N- (2-methylpropyl) amino, vorzugsweise N,N-Dimethylamino oder N,N-Diethylamino; substituiertes Ci-Cδ-Alkoxy, also z.B. für OCH2-N (CH3) 2 , OCH2 -N (C2H5) 2, OCH(CH3) -N(CH3)2, 2- (Dimethylamino) ethoxy, OCH (CH3) -N (C2H5) 2 , 3 - (Dimethylamino) propoxy, 4 - (Dimethylamino) butoxy, 5- (Dimethylamino) pentoxy oder 6- (Dimethylamino) hexoxy, ins- besondere für OCH2-N(CH3)2 oder OCH (CH3) -N(CH3) 2;Di (Ci-Cg-alkyl) amino-Ci-Cg-alkoxy: by di- (Ci-C δ- alkyl) - amino such as N (CH 3 ) 2 , N (C 2 Hs) 2 , N, N-dipropylamino , N, N-di- (1-methylethyl) mino, N, N-dibutylamino, N, N-di- (1-methylpropyl) amino, N, N-di- (2-methylpropyl) amino, N [ C (CH 3 ) 3 ], 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 -dimethylethyl) amino, N- (1-methylethyl) -N-propylamino, N-butyl-N-propylamino, N- (1-methylpropyl) -N-propylamino, N- (2-methylpropyl) -N-propylamino, N - (1, 1-Dimethylethyl) -N-propylamino, N-butyl-N- (1-methylethyl) amino, N- (1-methylethyl) -N- (1-methylpropyl) - amino, N- (1-methylethyl ) -N- (2-methylpropyl) amino, N- (l, 1-dimethylethyl) -N- (1-methyl ethyl) amino, N-butyl-N- (1-methylpropyl) amino, N-butyl-N- (2-methylpropyl) amino, N-butyl-N- (1, 1-dimethylethyl) amino, N- ( 1-methylpropyl) -N- (2-methylpropyl) amino, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) amino or N- (1, 1-dimethylethyl) -N- (2- methylpropyl) amino, preferably N, N-dimethylamino or N, N-diethylamino; substituted Ci-C δ alkoxy, e.g. for OCH 2 -N (CH 3 ) 2 , OCH 2 -N (C 2 H 5 ) 2 , OCH (CH 3 ) -N (CH 3 ) 2 , 2- (dimethylamino) ethoxy, OCH (CH 3 ) -N (C 2 H 5 ) 2 , 3 - (dimethylamino) propoxy, 4 - (dimethylamino) butoxy, 5- (dimethylamino) pentoxy or 6- (dimethylamino) hexoxy, especially for OCH 2 -N (CH 3 ) 2 or OCH (CH 3 ) -N (CH 3 ) 2 ;
C3-Cδ-Alkenyl für: z.B. Prop-2-en-l-yl, n-Buten-4-yl , l-Methyl-prop-2-en-l-yl, 2-Methyl-prop-2-en-l-yl, 2-Buten- 1-yl, n-Penten-3-yl, n-Penten-4-yl, l-Methyl-but-2-en-l-yl, 2-Methyl-but-2-en-l-yl, 3-Methyl-but-2-en-l-yl, 1 -Methyl - but-3-en-l-yl, 2-Methyl-but-3-en-l-yl, 3-Methyl-but-3-en- 1-yl, 1, l-Dimethyl-prop-2-en-l-yl, 1, 2-Dimethyl -prop-2-en- 1-yl, l-Ethyl-prop-2-en-l-yl, n-Hex-3-en-l-yl, n-Hex-4-en- 1-yl, n-Hex-5-en-l-yl, l-Methyl-pent-3 -en-l-yl, 2-Methyl- pent-3-en-l-yl, 3-Methyl-pent-3-en-l-yl, 4 -Methyl -pent-3- en-l-yl, l-Methyl-pent-4-en-l-yl, 2-Methyl-pent-4-en-l-yl, 3-Methyl-pent-4-en-l-yl, 4 -Methyl -pent-4-en-l-yl , 1, l-Dimethyl-but-2-en-l-yl, 1, l-Dimethyl-but-3-en-l-yl, 1 , 2-Dimethyl-but-2-en-l-yl , 1 , 2-Dimethyl-but-3-en-l-yl , l,3-Dimethyl-but-2-en-l-yl, 1, 3-Dimethyl-but-3-en-l-yl,C 3 -C δ- alkenyl for: eg prop-2-en-l-yl, n-buten-4-yl, l-methyl-prop-2-en-l-yl, 2-methyl-prop-2- en-l-yl, 2-butene-1-yl, n-penten-3-yl, n-penten-4-yl, l-methyl-but-2-en-l-yl, 2-methyl-but- 2-en-l-yl, 3-methyl-but-2-en-l-yl, 1-methyl-but-3-en-l-yl, 2-methyl-but-3-en-l-yl, 3-methyl-but-3-en-1-yl, 1, l-dimethyl-prop-2-en-l-yl, 1, 2-dimethyl-prop-2-en-1-yl, l-ethyl- prop-2-en-l-yl, n-hex-3-en-l-yl, n-hex-4-en-1-yl, n-hex-5-en-l-yl, l-methyl pent-3-en-l-yl, 2-methyl-pent-3-en-l-yl, 3-methyl-pent-3-en-l-yl, 4-methyl-pent-3-en-l- yl, l-methyl-pent-4-en-l-yl, 2-methyl-pent-4-en-l-yl, 3-methyl-pent-4-en-l-yl, 4-methyl-pent- 4-en-l-yl, 1, l-dimethyl-but-2-en-l-yl, 1, l-dimethyl-but-3-en-l-yl, 1, 2-dimethyl-but-2- en-l-yl, 1, 2-dimethyl-but-3-en-l-yl, l, 3-dimethyl-but-2-en-l-yl, 1, 3-dimethyl-but-3-en- l-yl,
2 , 2-Dimethyl-but-3-en-l-yl , 2 , 3-Dimethyl-but-2-en-l-yl , 2, 3-Dimethyl-but-3-en-l-yl, 3, 3-Dimethyl-but-2-en-l-yl, l-Ethyl-but-2-en-l-yl, l-Ethyl-but-3-en-l-yl, 2-Ethyl-but-2- en-l-yl, 2-Ethyl-but-3-en-l-yl, 1, 1, 2-Trimethyl-prop-2-en- 1-yl, l-Ethyl-l-methyl-prop-2-en-l-yl oder l-Ethyl-2-methyl- prop-2-en-l-yl, insbesondere für Prop-2 -en-l-yl oder n-Buten- 4-yl;2,2-dimethyl-but-3-en-l-yl, 2,3-dimethyl-but-2-en-l-yl, 2,3-dimethyl-but-3-en-l-yl, 3, 3-dimethyl-but-2-en-l-yl, l-ethyl-but-2-en-l-yl, l-ethyl-but-3-en-l-yl, 2-ethyl-but-2- en-l-yl, 2-ethyl-but-3-en-l-yl, 1, 1, 2-trimethyl-prop-2-en-1-yl, l-ethyl-l-methyl-prop-2- en-l-yl or l-ethyl-2-methyl-prop-2-en-l-yl, in particular for prop-2 -en-l-yl or n-buten-4-yl;
C2-Cg-Alkenyl für: Ethenyl oder einen der unter C3-Cg-Alkenyl genannten Reste, insbesondere für Ethenyl oder Prop-2 -en- l-yl ;C 2 -Cg alkenyl for: ethenyl or one of the radicals mentioned under C 3 -Cg alkenyl, in particular for ethenyl or prop-2-en-yl;
C3-Cg-Alkenyloxy für: Prop-1-en-l-yloxy, Prop-2-en-l-yloxy, 1-Methylethenyloxy, n-Buten-1-yloxy, n-Buten-2-yloxy, n-Buten-3-yloxy, 1-Methyl-prop-l-en-l-yloxy, 2-Methyl- prop-1-en-l-yloxy, l-Methyl-prop-2-en-l-yloxy, 2-Methyl- prop-2-en-l-yloxy, n-Penten-1-yloxy, n-Penten-2-yloxy, n-Penten-3-yloxy, n-Penten-4-yloxy, 1-Methyl-but-1-en-l-yl- oxy, 2-Methyl-but-l-en-l-yloxy, 3-Methyl-but-l-en-l-yloxy, l-Methyl-but-2-en-l-yloxy, 2-Methyl-but-2-en-l-yloxy, 3-Methyl-but-2-en-l-yloxy, l-Methyl-but-3-en-l-yloxy, 2-Methyl-but-3-en-l-yloxy, 3-Methyl-but-3-en-l-yloxy, 1, l-Dimethyl-prop-2-en-l-yloxy, 1, 2-Dimethyl-prop-1-en-l-yl- oxy, 1, 2-Dimethyl-prop-2-en-l-yloxy, l-Ethyl-prop-l-en-2-yl- oxy, l-Ethyl-prop-2-en-l-yloxy, n-Hex-1-en-l-yloxy, n-Hex-2- en-1-yloxy, n-Hex-3-en-l-yloxy, n-Hex-4-en-l-yloxy, n-Hex-5- en-1-yloxy, 1-Methyl-pent-l-en-l-yloxy, 2-Methyl-pent-l-en- 1-yloxy, 3-Methyl-pent-l-en-l-yloxy, 4-Methyl-pent-l-en-l-yl - oxy, l-Methyl-pent-2-en-l-yloxy, 2-Methyl-pent-2-en-l-yloxy, 3-Methyl-pent-2-en-l-yloxy, 4-Methyl-pent-2-en-l-yloxy, l-Methyl-pent-3-en-l-yloxy, 2-Methyl-pent-3-en-l-yloxy, 3-Methyl-pent-3-en-l-yloxy, 4-Methyl-pent-3-en-l-yloxy, l-Methyl-pent-4-en-l-yloxy, 2-Methyl-pent-4-en-l-yloxy, 3-Methyl-pent-4-en-l-yloxy, 4-Methyl-pent-4-en-l-yloxy, 1, l-Dimethyl-but-2-en-l-yloxy, 1, l-Dimethyl-but-3-en-l-yloxy, 1, 2-Dimethyl-but-1-en-l-yloxy, 1, 2-Dimethyl-but-2-en-l-yloxy, 1, 2-Dimethyl-but-3-en-l-yloxy, 1, 3-Dimethyl-but-l-en-l-yloxy, 1, 3-Dimethyl-but-2-en-l-yloxy, 1, 3-Dimethyl-but-3-en-l-yloxy, 2 , 2-Dimethyl-but-3-en-l-yloxy, 2 , 3-Dimethyl-but-l-en-l-yloxy, 2, 3-Dimethyl-but-2-en-l-yloxy, 2 , 3-Dimethyl-but-3-en-l-yloxy, 3 , 3-Dimethyl-but-l-en-l-yloxy, 3 , 3-Dimethyl-but-2-en-l-yloxy, 1-Ethyl-but-l-en-l-yloxy, l-Ethyl-but-2-en-l-yloxy, 1-Ethyl- but-3-en-l-yloxy, 2-Ethyl-but-l-en-l-yloxy, 2-Ethyl-but-2- en-1-yloxy, 2-Ethyl-but-3-en-l-yloxy, 1, 1, 2-Trimethyl-prop-2- en-1-yloxy, l-Ethyl-l-methyl-prop-2-en-l-yloxy, l-Ethyl-2- methyl-prop-1-en-l-yloxy oder l-Ethyl-2-methyl-prop-2-en-l- yloxy, insbesondere für Prop-2-en-l-yloxy;C 3 -Cg alkenyloxy for: prop-1-en-l-yloxy, prop-2-en-l-yloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n- Buten-3-yloxy, 1-methyl-prop-l-en-l-yloxy, 2-methyl-prop-1-en-l-yloxy, l-methyl-prop-2-en-l-yloxy, 2- Methyl-prop-2-en-l-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, 1-methyl-but- 1-en-l-yl-oxy, 2-methyl-but-l-en-l-yloxy, 3-methyl-but-l-en-l-yloxy, l-methyl-but-2-en-l- yloxy, 2-methyl-but-2-en-l-yloxy, 3-methyl-but-2-en-l-yloxy, l-methyl-but-3-en-l-yloxy, 2-methyl-but- 3-en-l-yloxy, 3-methyl-but-3-en-l-yloxy, 1, l-dimethyl-prop-2-en-l-yloxy, 1, 2-dimethyl-prop-1-en- l-yl-oxy, 1, 2-dimethyl-prop-2-en-l-yloxy, l-ethyl-prop-l-en-2-yl-oxy, l-ethyl-prop-2-en-l- yloxy, n-hex-1-en-l-yloxy, n-hex-2-en-1-yloxy, n-hex-3-en-l-yloxy, n-hex-4-en-l-yloxy, n-Hex-5- en-1-yloxy, 1-methyl-pent-l-en-l-yloxy, 2-methyl-pent-l-en- 1-yloxy, 3-methyl-pent-l-en-l-yloxy, 4-methyl-pent-l-en-l-yloxy, l-methyl-pent-2-en-l-yloxy, 2- Methyl-pent-2-en-l-yloxy, 3-methyl-pent-2-en-l-yloxy, 4-methyl-pent-2-en-l-yloxy, l-methyl-pent-3-en- l-yloxy, 2-methyl-pent-3-en-l-yloxy, 3-methyl-pent-3-en-l-yloxy, 4-methyl-pent-3-en-l-yloxy, l-methyl pent-4-en-l-yloxy, 2-methyl-pent-4-en-l-yloxy, 3-methyl-pent-4-en-l-yloxy, 4-methyl-pent-4-en-l- yloxy, 1, l-dimethyl-but-2-en-l-yloxy, 1, l-dimethyl-but-3-en-l-yloxy, 1, 2-dimethyl-but-1-en-l-yloxy, 1, 2-dimethyl-but-2-en-l-yloxy, 1, 2-dimethyl-but-3-en-l-yloxy, 1, 3-dimethyl-but-l-en-l-yloxy, 1, 3-dimethyl-but-2-en-l-yloxy, 1, 3-dimethyl-but-3-en-l-yloxy, 2, 2-dimethyl-but-3-en-l-yloxy, 2, 3- Dimethyl-but-l-en-l-yloxy, 2, 3-dimethyl-but-2-en-l-yloxy, 2, 3-dimethyl-but-3-en-l-yloxy, 3, 3-dimethyl but-l-en-l-yloxy, 3, 3-dimethyl-but-2-en-l-yloxy, 1-ethyl-but-l-en-l-yloxy, l-ethyl-but-2-en- l-yloxy, 1-ethyl-but-3-en-l-yloxy, 2-ethyl-but-l-en-l-yloxy, 2-ethyl-but-2-en-1-yloxy, 2-ethyl but -3-en-1-yloxy, 1, 1, 2-trimethyl-prop-2-en-1-yloxy, 1-ethyl-1-methyl-prop-2-en-1-yloxy, 1-ethyl-2 - methyl-prop-1-en-l-yloxy or l-ethyl-2-methyl-prop-2-en-l-yloxy, in particular for prop-2-en-l-yloxy;
C2-Cg-Alkenyloxy für: Ethenyloxy oder einen der unter C3-Cg-Alkenyloxy genannten Reste, insbesondere für Ethenyloxy oder Prop-2-en-l-yloxy;C 2 -Cg alkenyloxy for: ethenyloxy or one of the radicals mentioned under C 3 -Cg alkenyloxy, in particular for ethenyloxy or prop-2-en-l-yloxy;
C3-Cg-Halogenalkenyloxy für: C -C -Alkenyloxy wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor und/oder Brom substituiert ist, also z.B. 2-Chlorallyloxy, 3-Chlorallyloxy, 2, 3-Dichlorallyloxy, 3 , 3-Dichlorallyloxy, 2, 3, 3-Trichlorallyloxy, 2, 3-Dichlorbut-2-enyloxy, 2-Brom- allyloxy, 3-Bromallyloxy, 2, 3-Dibrornallyloxy, 3,3-Dibrom- allyloxy, 2, 3, 3-Tribromallyloxy oder 2, 3-Dibrombut-2-enyloxy, insbesondere für 2-Chlorallyloxy oder 3 , 3-Dichlorallyloxy;C 3 -Cg haloalkenyloxy for: C -C alkenyloxy as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for example 2-chloroallyloxy, 3-chloroallyloxy, 2, 3-dichloroallyloxy, 3, 3-dichloroallyloxy, 2, 3, 3-trichlorallyloxy, 2, 3-dichlorobut-2-enyloxy, 2-bromo-allyloxy, 3-bromoallyloxy, 2, 3-dibrornallyloxy, 3,3-dibromo-allyloxy, 2, 3, 3-tribromoallyloxy or 2,3-dibromobut-2-enyloxy, in particular for 2-chloroallyloxy or 3,3-dichloroallyloxy;
- Phenyl-C3-Cg-alkenyloxy für: z.B. 3-Phenyl-allyloxy, 4-Phenyl- but-2-enyloxy, 4-Phenyl-but-3-enyloxy oder 5-Phenyl-pent-4- enyloxy, vorzugsweise 3-Phenylallyloxy oder 4-Phenyl-but-2- enyloxy, insbesondere für 3 -Phenylallyloxy;- Phenyl-C 3 -Cg-alkenyloxy for: eg 3-phenyl-allyloxy, 4-phenyl-but-2-enyloxy, 4-phenyl-but-3-enyloxy or 5-phenyl-pent-4-enyloxy, preferably 3 -Phenylallyloxy or 4-phenyl-but-2-enyloxy, especially for 3 -phenylallyloxy;
- Heterocyclyl -C3 -Cg-alkenyloxy für: z.B. 3-Heterocyclyl-allyl- oxy, 4-Heterocyclyl-but-2-enyloxy, 4-Heterocyclyl-but-3- enyloxy oder 5-Heterocyclyl-pent-4-enyloxy, vorzugsweise 3-Heterocyclyl -allyloxy oder 4-Heterocyclyl-but-2-enyloxy, insbesondere für 3 -Heterocyclyl -allyloxy; C -Cg-Alkenylthio für: Ethenylthio, Prop-1-en-l-ylthio, Prop-2-en-l-ylthio, 1-Methylethenylthio, n-Buten-1-ylthio, n-Buten-2-ylthio, n-Buten-3-ylthio, 1-Methyl-prop-l-en-l-yl- thio, 2-Methyl-prop-l-en-l-ylthio, 1-Methyl-prop-2-en-l-yl- thio, 2-Methyl-prop-2-en-l-ylthio, n-Penten-1-ylthio, n-Penten-2-ylthio, n-Penten-3-ylthio, n-Penten-4-ylthio, 1-Methyl-but-l-en-l-ylthio, 2-Methyl-but-l-en-l-ylthio, 3-Methyl-but-l-en-l-ylthio, 1-Methyl-but-2-en-l-ylthio, 2-Methyl-but-2-en-l-ylthio, 3-Methyl-but-2-en-l-ylthio, l-Methyl-but-3-en-l-ylthio, 2-Methyl-but-3-en-l-ylthio,- Heterocyclyl -C 3 -Cg-alkenyloxy for: eg 3-heterocyclyl-allyl-oxy, 4-heterocyclyl-but-2-enyloxy, 4-heterocyclyl-but-3-enyloxy or 5-heterocyclyl-pent-4-enyloxy, preferably 3-heterocyclyl -allyloxy or 4-heterocyclyl-but-2-enyloxy, in particular for 3-heterocyclyl -allyloxy; C -Cg alkenylthio for: ethenylthio, prop-1-en-l-ylthio, prop-2-en-l-ylthio, 1-methylethenylthio, n-buten-1-ylthio, n-buten-2-ylthio, n -Butene-3-ylthio, 1-methyl-prop-1-en-1-yl-thio, 2-methyl-prop-1-en-1-ylthio, 1-methyl-prop-2-en-1-yl - thio, 2-methyl-prop-2-en-l-ylthio, n-penten-1-ylthio, n-penten-2-ylthio, n-penten-3-ylthio, n-penten-4-ylthio, 1 -Methyl-but-l-en-l-ylthio, 2-methyl-but-l-en-l-ylthio, 3-methyl-but-l-en-l-ylthio, 1-methyl-but-2-ene -l-ylthio, 2-methyl-but-2-en-l-ylthio, 3-methyl-but-2-en-l-ylthio, l-methyl-but-3-en-l-ylthio, 2-methyl -but-3-en-l-ylthio,
3-Methyl-but-3-en-l-ylthio, 1, l-Dimethyl-prop-2-en-l-ylthio, 1, 2-Dimethyl-prop-l-en-l-ylthio, 1, 2-Dimethyl-prop-2-en- 1-ylthio, l-Ethyl-prop-l-en-2-ylthio, l-Ethyl-prop-2-en- 1-ylthio, n-Hex-1-en-l-ylthio, n-Hex-2-en-l-ylthio, n-Hex- 3-en-l-ylthio, n-Hex-4-en-l-ylthio, n-Hex-5-en-l-ylthio, 1-Methyl-pent-l-en-l-ylthio, 2-Methyl-pent-l-en-l-ylthio, 3-Methyl-pent-1-en-l-ylthio, 4-Methyl-pent-1-en-l-ylthio, 1-Methyl-pent-2-en-l-ylthio, 2-Methyl-pent-2-en-l-ylthio, 3-Methyl-pent-2-en-l-ylthio, 4-Methyl-pent-2-en-l-ylthio, l-Methyl-pent-3-en-l-ylthio, 2-Methyl-pent-3-en-l-ylthio, 3-Methyl-pent-3-en-l-ylthio, 4-Methyl-pent-3-en-l-ylthio, 1-Methyl-pent-4-en-l-ylthio, 2-Methyl-pent-4-en-l-ylthio, 3-Methyl-pent-4-en-l-ylthio, 4-Methyl-pent-4-en-l-ylthio, 1, l-Dimethyl-but-2-en-l-ylthio, 1, l-Dimethyl-but-3-en-l-yl- thio, 1,2-Dimethyl-but-l-en-l-ylthio, 1, 2-Dimethyl-but-3-methyl-but-3-en-l-ylthio, 1, l-dimethyl-prop-2-en-l-ylthio, 1, 2-dimethyl-prop-l-en-l-ylthio, 1, 2- Dimethyl-prop-2-en-1-ylthio, l-ethyl-prop-l-en-2-ylthio, l-ethyl-prop-2-en-1-ylthio, n-hex-1-en-l- ylthio, n-hex-2-en-l-ylthio, n-hex-3-en-l-ylthio, n-hex-4-en-l-ylthio, n-hex-5-en-l-ylthio, 1-methyl-pent-l-en-l-ylthio, 2-methyl-pent-l-en-l-ylthio, 3-methyl-pent-1-en-l-ylthio, 4-methyl-pent-1- en-l-ylthio, 1-methyl-pent-2-en-l-ylthio, 2-methyl-pent-2-en-l-ylthio, 3-methyl-pent-2-en-l-ylthio, 4- Methyl-pent-2-en-l-ylthio, l-methyl-pent-3-en-l-ylthio, 2-methyl-pent-3-en-l-ylthio, 3-methyl-pent-3-en- l-ylthio, 4-methyl-pent-3-en-l-ylthio, 1-methyl-pent-4-en-l-ylthio, 2-methyl-pent-4-en-l-ylthio, 3-methyl pent-4-en-l-ylthio, 4-methyl-pent-4-en-l-ylthio, 1, l-dimethyl-but-2-en-l-ylthio, 1, l-dimethyl-but-3- en-l-yl-thio, 1,2-dimethyl-but-l-en-l-ylthio, 1, 2-dimethyl-but-
2-en-l-ylthio, 1, 2-Dimethyl-but-3-en-l-ylthio, 1, 3-Dimethyl- but-1-en-l-ylthio, 1, 3-Dimethyl-but-2-en-l-ylthio, 1,3-Di- methyl-but-3-en-l-ylthio, 2, 2-Dimethyl-but-3-en-l-ylthio, 2, 3-Dimethyl-but-l-en-l-ylthio, 2, 3-Dimethyl-but-2-en-l-yl- thio, 2 , 3-Dimethyl-but-3-en-l-ylthio, 3, 3-Dimethyl-but-l-en- 1-ylthio, 3,3-Dimethyl-but-2-en-l-ylthio, 1-Ethyl-but-l-en- 1-ylthio, l-Ethyl-but-2-en-l-ylthio, l-Ethyl-but-3-en-l-yl- thio, 2-Ethyl-but-l-en-l-ylthio, 2-Ethyl-but-2-en-l-ylthio, 2-Ethyl-but-3-en-l-ylthio, 1,1, 2-Trimethyl-prop-2-en-l-yl - thio, l-Ethyl-l-methyl-prop-2-en-l-ylthio, l-Ethyl-2-methyl- prop-1-en-l-ylthio oder l-Ethyl-2-methyl-prop-2-en-l-ylthio, insbesondere für Ethenylthio oder Prop-2-en-l-ylthio;2-en-l-ylthio, 1, 2-dimethyl-but-3-en-l-ylthio, 1, 3-dimethyl-but-1-en-l-ylthio, 1, 3-dimethyl-but-2- en-l-ylthio, 1,3-dimethyl-but-3-en-l-ylthio, 2, 2-dimethyl-but-3-en-l-ylthio, 2, 3-dimethyl-but-l- en-l-ylthio, 2, 3-dimethyl-but-2-en-l-yl-thio, 2, 3-dimethyl-but-3-en-l-ylthio, 3, 3-dimethyl-but-l- en-1-ylthio, 3,3-dimethyl-but-2-en-l-ylthio, 1-ethyl-but-l-en-1-ylthio, l-ethyl-but-2-en-l-ylthio, l-ethyl-but-3-en-l-ylthio, 2-ethyl-but-l-en-l-ylthio, 2-ethyl-but-2-en-l-ylthio, 2-ethyl-but- 3-en-l-ylthio, 1,1, 2-trimethyl-prop-2-en-l-yl - thio, l-ethyl-l-methyl-prop-2-en-l-ylthio, l-ethyl- 2-methyl-prop-1-en-l-ylthio or l-ethyl-2-methyl-prop-2-en-l-ylthio, in particular for ethenylthio or prop-2-en-l-ylthio;
C3-Cδ-Alkinyl für: Prop-1-in-l-yl, Prop-2-in-l-yl, n-But-1- in-l-yl, n-But-l-in-3-yl, n-But-l-in-4-yl, n-But-2-in-l-yl, n-Pent-1-in-l-yl, n-Pent-l-in-3-yl, n-Pent-l-in-4-yl, n-Pent- l-in-5-yl, n-Pent-2-in-l-yl, n-Pent-2-in-4-yl, n-Pent-2-in- 5-yl, 3-Methyl-but-l-in-3-yl, 3-Methyl-but-l-in-4-yl, n-Hex- 1-in-l-yl, n-Hex-l-in-3-yl, n-Hex-l-in-4-yl, n-Hex-l-in-5-yl, n-Hex-l-in-6-yl, n-Hex-2-in-l-yl, n-Hex-2-in-4-yl , n-Hex-2- in-5-yl, n-Hex-2-in-6-yl, n-Hex-3-in-l-yl, n-Hex-3-in-2-yl, 3-Methyl-pent-l-in-l-yl, 3-Methyl-pent-l-in-3-yl , 3-Methyl- pent-l-in-4-yl, 3-Methyl-pent-l-in-5-yl, 4-Methyl-pent-l-in- 1-yl, 4-Methyl-pent-2-in-4-yl oder 4-Methyl-pent-2-in-5-yl, insbesondere für Prop-2-in-l-yl;C 3 -C δ alkynyl for: prop-1-in-l-yl, prop-2-in-l-yl, n-but-1-in-l-yl, n-but-l-in-3 -yl, n-but-l-in-4-yl, n-but-2-in-l-yl, n-pent-1-in-l-yl, n-pent-l-in-3-yl , n-pent-1-in-4-yl, n-pent-1-in-5-yl, n-pent-2-in-1-yl, n-pent-2-in-4-yl, n Pent-2-in-5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n-hex-1-in-l-yl , n-hex-1-in-3-yl, n-hex-1-in-4-yl, n-hex-1-in-5-yl, n-hex-1-in-6-yl, n -Hex-2-in-1-yl, n-hex-2-in-4-yl, n-hex-2-in-5-yl, n-hex-2-in-6-yl, n-hex -3-in-1-yl, n-hex-3-in-2-yl, 3-methyl-pent-1-in-1-yl, 3-methyl-pent-1-in-3-yl, 3 -Methyl- pent-l-in-4-yl, 3-methyl-pent-l-in-5-yl, 4-methyl-pent-l-in-1-yl, 4-methyl-pent-2-in-4- yl or 4-methyl-pent-2-in-5-yl, especially for prop-2-in-l-yl;
- C -Cδ-Alkinyl für: Ethinyl oder einen der unter C3-Cg-Alkinyl genannten Reste, insbesondere für Ethinyl oder Prop-2-in- 1-yl;- C -C δ alkynyl for: ethynyl or one of the radicals mentioned under C 3 -C 6 -alkynyl, in particular for ethynyl or prop-2-yn-1-yl;
C3-Cg-Alkinyloxy für: Prop-1-in-l-yloxy, Prop-2-in-l-yloxy, n-But-1-in-l-yloxy, n-But-l-in-3-yloxy, n-But-l-in-4-yloxy, n-But-2-in-l-yloxy, n-Pent-1-in-l-yloxy, n-Pent-l-in-3-yloxy, n-Pent-l-in-4-yloxy, n-Pent-l-in-5-yloxy, n-Pent-2-in-l-yl- oxy, n-Pent-2-in-4-yloxy, n-Pent-2-in-5-yloxy, 3-Methyl- but-l-in-3-yloxy, 3-Methyl-but-l-in-4-yloxy, n-Hex-1-in-l-yl- oxy, n-Hex-l-in-3-yloxy, n-Hex-l-in-4-yloxy, n-Hex-l-in-5-yl- oxy, n-Hex-l-in-6-yloxy, n-Hex-2-in-l-yloxy, n-Hex-2-in-4-yl- oxy, n-Hex-2-in-5-yloxy, n-Hex-2-in-6-yloxy, n-Hex-3-in-l-yl- oxy, n-Hex-3-in-2-yloxy, 3-Methylpent-l-in-l-yloxy, 3-Methyl- pent-l-in-3-yloxy, 3-Methyl-pent-l-in-4-yloxy, 3-Methyl-pent- l-in-5-yloxy, 4-Methyl-pent-l-in-l-yloxy, 4-Methyl-pent-2-in- 4-yloxy oder 4-Methylpent-2-in-5-yloxy, insbesondere für Prop-2-in-l-yloxy;C 3 -Cg alkynyloxy for: prop-1-in-l-yloxy, prop-2-in-l-yloxy, n-but-1-in-l-yloxy, n-but-l-in-3- yloxy, n-but-l-in-4-yloxy, n-but-2-in-l-yloxy, n-pent-1-in-l-yloxy, n-pent-l-in-3-yloxy, n-pent-l-in-4-yloxy, n-pent-l-in-5-yloxy, n-pent-2-in-l-yl-oxy, n-pent-2-in-4-yloxy, n-pent-2-in-5-yloxy, 3-methyl-but-l-in-3-yloxy, 3-methyl-but-l-in-4-yloxy, n-hex-1-in-l- yl-oxy, n-hex-l-in-3-yloxy, n-hex-l-in-4-yloxy, n-hex-l-in-5-yl-oxy, n-hex-l-in- 6-yloxy, n-hex-2-in-1-yloxy, n-hex-2-in-4-yl-oxy, n-hex-2-in-5-yloxy, n-hex-2-in 6-yloxy, n-hex-3-in-l-yloxy, n-hex-3-in-2-yloxy, 3-methylpent-l-in-l-yloxy, 3-methylpent-l- in-3-yloxy, 3-methyl-pent-l-in-4-yloxy, 3-methyl-pent-l-in-5-yloxy, 4-methyl-pent-l-in-l-yloxy, 4- Methyl-pent-2-in-4-yloxy or 4-methylpent-2-in-5-yloxy, especially for prop-2-in-1-yloxy;
C2-Cg-Alkinyloxy für: Ethinyloxy oder einen der unter C3-Cg-Alkinyloxy genannten Reste, insbesondere für Ethinyloxy oder Prop-2-in-l-yloxy;C 2 -Cg alkynyloxy for: ethynyloxy or one of the radicals mentioned under C 3 -Cg alkynyloxy, in particular for ethynyloxy or prop-2-yn-l-yloxy;
Phenyl-C3-Cg-alkinyloxy für: z.B. 3-Phenylprop-2-in-l-yloxy, 4-Phenylbut-2-in-l-yloxy, 3-Phenylbut-3-in-2-yloxy, 5-Phenyl- pent-3-in-l-yloxy oder 6-Phenylhex-4-in-l-yloxy, insbesondere für 3-Phenylprop-2-in-l-yloxy oder 3-Phenylbut-3-in-2-yloxy;Phenyl-C 3 -Cg-alkynyloxy for: e.g. 3-phenylprop-2-in-1-yloxy, 4-phenylbut-2-in-1-yloxy, 3-phenylbut-3-in-2-yloxy, 5-phenyl pent-3-in-1-yloxy or 6-phenylhex-4-in-1-yloxy, in particular for 3-phenylprop-2-in-1-yloxy or 3-phenylbut-3-in-2-yloxy;
Heterocyclyl-C3-Cg-alkinyloxy für: z.B. 3- (Heterocyclyl) prop- 2-in-l-yloxy, 4- (Heterocyclyl) but-2-in-l-yloxy, 3-(Hetero- cyclyl)but-3-in-2-yloxy, 5- (Heterocyclyl) pent-3-in-l-yloxy oder 6- (Heterocyclyl) hex-4-in-l-yloxy, insbesondere für 3- (Heterocyclyl) prop-2-in-l-yloxy oder 3- (Heterocyclyl) but- 3-in-2-yloxy;Heterocyclyl-C 3 -Cg-alkynyloxy for: e.g. 3- (heterocyclyl) prop- 2-in-l-yloxy, 4- (heterocyclyl) but-2-in-l-yloxy, 3- (heterocyclic) but- 3-in-2-yloxy, 5- (heterocyclyl) pent-3-in-l-yloxy or 6- (heterocyclyl) hex-4-in-l-yloxy, especially for 3- (heterocyclyl) prop-2-in -l-yloxy or 3- (heterocyclyl) but-3-in-2-yloxy;
- C -Cδ-Alkinylthio für: Prop-1-in-l-ylthio, Prop-2-in-l-ylthio, n-But-1-in-l-ylthio, n-But-l-in-3-ylthio, n-But-l-in-4- ylthio, n-But-2-in-l-ylthio, n-Pent-1-in-l-ylthio, n-Pent- l-in-3-ylthio, n-Pent-l-in-4-ylthio, n-Pent-l-in-5-ylthio, n-Pent-2-in-l-ylthio, n-Pent-2-in-4-ylthio, n-Pent-2-in-5- ylthio, 3-Methyl-but-l-in-3-ylthio, 3-Methylbut-l-in-4- ylthio, n-Hex-1-in-l-ylthio, n-Hex-l-in-3-ylthio, n-Hex-1- in-4-ylthio, n-Hex-l-in-5-ylthio, n-Hex-l-in-6-ylthio, n-Hex-2-in-l-ylthio, n-Hex-2-in-4-ylthio, n-Hex-2-in-5- ylthio, n-Hex-2-in-6-ylthio, n-Hex-3-in-l-ylthio, n-Hex-3- in-2-ylthio, 3-Methylpent-l-in-l-ylthio, 3-Methyl-pent-l-in- 3-ylthio, 3-Methyl-pent-l-in-4-ylthio, 3-Methylpent-l-in-5- ylthio, 4-Methyl-pent-l-in-l-ylthio, 4-Methyl-pent-2-in-4- ylthio oder 4-Methyl-pent-2-in-5-ylthio, insbesondere für Prop-2-in-l-ylthio;- C -C δ alkynylthio for: prop-1-in-l-ylthio, prop-2-in-l-ylthio, n-but-1-in-l-ylthio, n-but-l-in-3 -ylthio, n-but-1-in-4-ylthio, n-but-2-in-1-ylthio, n-pent-1-in-1-ylthio, n-pent-1-in-3-ylthio , n-pent-1-in-4-ylthio, n-pent-1-in-5-ylthio, n-pent-2-in-1-ylthio, n-pent-2-in-4-ylthio, n Pent-2-in-5-ylthio, 3-methyl-but-l-in-3-ylthio, 3-methylbut-l-in-4-ylthio, n-hex-1-in-l-ylthio, n -Hex-1-in-3-ylthio, n-hex-1-in-4-ylthio, n-hex-1-in-5-ylthio, n-hex-1-in-6-ylthio, n-hex-2-in-ylthio, n-hex-2-in-4-ylthio, n-hex-2-in-5-ylthio, n-hex-2-in-6-ylthio, n- Hex-3-in-l-ylthio, n-hex-3-in-2-ylthio, 3-methylpent-l-in-l-ylthio, 3-methyl-pent-l-in-3-ylthio, 3- Methyl-pent-l-in-4-ylthio, 3-methylpent-l-in-5-ylthio, 4-methyl-pent-l-in-l-ylthio, 4-methyl-pent-2-in-4- ylthio or 4-methyl-pent-2-in-5-ylthio, especially for prop-2-in-l-ylthio;
C -Cδ-Alkinylthio für: Ethinylthio oder einen der unter C3-Cδ-Alkinylthio genannten Reste, insbesondere für Ethinyl - thio oder Prop-2-in-l-ylthiθ;C -C δ alkynylthio for: ethynylthio or one of the radicals mentioned under C 3 -C δ alkynylthio, in particular for ethynylthio or prop-2-yn-l-ylthio;
(C3-Cδ-Alkenyloxy) carbonyl für: Prop-1-en-l-yloxycarbonyl, Prop-2-en-l-yloxycarbonyl , 1-Methylethenyloxycarbonyl , n-Buten-1-yloxycarbonyl, n-Buten-2-yloxycarbonyl, n-Buten-3- yloxycarbonyl , 1-Methyl-prop-l-en-l-yloxycarbonyl, 2-Methyl- prop-1-en-l-yloxycarbonyl, 1-Methyl-prop-2-en-l-yloxy- carbonyl, 2-Methyl-prop-2-en-l-yloxycarbonyl, n-Penten-1- yloxycarbonyl, n-Penten-2-yloxycarbonyl, n-Penten-3-yloxy- carbonyl, n-Penten-4-yloxycarbonyl, 1-Methyl-but-l-en-l- yloxycarbonyl , 2-Methyl-but-l-en-l-yloxycarbonyl, 3-Methyl- but-1-en-l-yloxycarbonyl, l-Methyl-but-2-en-l-yloxycarbonyl, 2-Methyl-but-2-en-l-yloxycarbonyl, 3-Methyl-but-2-en-l-yloxy- carbonyl, l-Methyl-but-3-en-l-yloxycarbonyl, 2-Methyl-but-3- en-1-yloxycarbonyl, 3-Methyl-but-3-en-l-yloxycarbonyl,(C 3 -C δ- alkenyloxy) carbonyl for: prop-1-en-l-yloxycarbonyl, prop-2-en-l-yloxycarbonyl, 1-methylethenyloxycarbonyl, n-buten-1-yloxycarbonyl, n-butene-2- yloxycarbonyl, n-butene-3-yloxycarbonyl, 1-methyl-prop-l-en-l-yloxycarbonyl, 2-methyl-prop-1-en-l-yloxycarbonyl, 1-methyl-prop-2-en-l- yloxycarbonyl, 2-methyl-prop-2-en-l-yloxycarbonyl, n-pentene-1-yloxycarbonyl, n-pentene-2-yloxycarbonyl, n-pentene-3-yloxycarbonyl, n-pentene-4- yloxycarbonyl, 1-methyl-but-l-en-l-yloxycarbonyl, 2-methyl-but-l-en-l-yloxycarbonyl, 3-methyl-but-1-en-l-yloxycarbonyl, l-methyl-but- 2-en-l-yloxycarbonyl, 2-methyl-but-2-en-l-yloxycarbonyl, 3-methyl-but-2-en-l-yloxycarbonyl, l-methyl-but-3-en-l- yloxycarbonyl, 2-methyl-but-3-en-1-yloxycarbonyl, 3-methyl-but-3-en-l-yloxycarbonyl,
1, l-Dimethyl-prop-2-en-l-yloxycarbonyl, 1, 2-Dimethyl-prop-l- en-1-yloxycarbonyl , 1 , 2-Dimethyl-prop-2-en-l-yloxycarbonyl , l-Ethyl-prop-l-en-2-yloxycarbonyl, l-Ethyl-prop-2-en-l-yloxy- carbonyl, n-Hex-1-en-l-yloxycarbonyl, n-Hex-2-en-l-yloxy- carbonyl, n-Hex-3-en-l-yloxycarbonyl, n-Hex-4-en-l-yloxy- carbonyl, n-Hex-5-en-l-yloxycarbonyl, 1-Methyl-pent-l-en-l- yloxycarbonyl , 2-Methyl-pent-l-en-l-yloxycarbonyl, 3-Methyl- pent-1-en-l-yloxycarbonyl , 4-Methyl-pent-l-en-l-yloxy- carbonyl, l-Methyl-pent-2-en-l-yloxycarbonyl, 2-Methyl-pent- 2-en-l-yloxycarbonyl, 3-Methyl-pent-2-en-l-yloxycarbonyl, 4-Methyl-pent-2-en-l-yloxycarbonyl, l-Methyl-pent-3-en-l- yloxycarbonyl , 2-Methyl-pent-3-en-l-yloxycarbonyl, 3-Methyl- pent-3-en-l-yloxycarbonyl, 4-Methyl-pent-3-en-l-yloxy- carbonyl, l-Methyl-pent-4-en-l-yloxycarbonyl, 2-Methyl-pent- 4-en-l-yloxycarbonyl, 3-Methyl-pent-4-en-l-yloxycarbonyl,1, l-dimethyl-prop-2-en-l-yloxycarbonyl, 1, 2-dimethyl-prop-l-en-1-yloxycarbonyl, 1, 2-dimethyl-prop-2-en-l-yloxycarbonyl, l- Ethyl-prop-l-en-2-yloxycarbonyl, l-ethyl-prop-2-en-l-yloxycarbonyl, n-hex-1-en-l-yloxycarbonyl, n-hex-2-en-l- yloxycarbonyl, n-hex-3-en-l-yloxycarbonyl, n-hex-4-en-l-yloxycarbonyl, n-hex-5-en-l-yloxycarbonyl, 1-methyl-pent-l- en-l-yloxycarbonyl, 2-methyl-pent-l-en-l-yloxycarbonyl, 3-methyl-pent-1-en-l-yloxycarbonyl, 4-methyl-pent-l-en-l-yloxycarbonyl, l-methyl-pent-2-en-l-yloxycarbonyl, 2-methyl-pent-2-en-l-yloxycarbonyl, 3-methyl-pent-2-en-l-yloxycarbonyl, 4-methyl-pent-2- en-l-yloxycarbonyl, l-methyl-pent-3-en-l-yloxycarbonyl, 2-methyl-pent-3-en-l-yloxycarbonyl, 3-methyl-pent-3-en-l-yloxycarbonyl, 4- Methyl-pent-3-en-l-yloxycarbonyl, l-methyl-pent-4-en-l-yloxycarbonyl, 2-methyl-pent-4-en-l-yloxycarbonyl, 3-methyl-pent-4- en-l-yloxycarbonyl,
4-Methyl-pent-4-en-l-yloxycarbonyl, 1, l-Dimethyl-but-2-en-l- yloxycarbonyl , 1, l-Dimethyl-but-3-en-l-yloxycarbonyl, 1, 2-Dimethyl-but-1-en-l-yloxycarbonyl, 1, 2-Dimethyl-but-2-en-l- yloxycarbonyl , 1, 2-Dimethyl-but-3-en-l-yloxycarbonyl, 1,3-Di- methyl-but-1-en-l-yloxycarbonyl, 1, 3-Dimethyl-but-2-en-l- yloxycarbonyl , 1, 3-Dimethyl-but-3-en-l-yloxycarbonyl, 2,2-Di- methyl-but-3-en-l-yloxycarbonyl, 2, 3-Dimethyl-but-l-en-l- yloxycarbonyl, 2, 3-Dimethyl-but-2-en-l-yloxycarbonyl, 2,3-Di- methyl-but-3-en-l-yloxycarbonyl, 3, 3-Dimethyl-but-l-en-l- yloxycarbonyl , 3 , 3-Dimethyl-but-2-en-l-yloxycarbonyl, 1-Ethyl-but-l-en-l-yloxycarbonyl , l-Ethyl-but-2-en-l-yloxy- carbonyl, l-Ethyl-but-3-en-l-yloxycarbonyl, 2-Ethyl-but-l- en-1-yloxycarbonyl , 2-Ethyl-but-2-en-l-yloxycarbonyl , 2-Ethyl-but-3-en-l-yloxycarbonyl, 1, 1, 2-Trimethyl-prop-2-en- 1-yloxycarbonyl, l-Ethyl-l-methyl-prop-2-en-l-yloxycarbonyl, l-Ethyl-2-methyl-prop-l-en-l-yloxycarbonyl oder l-Ethyl-2- methyl-prop-2-en-l-yloxycarbonyl, insbesondere für Prop-2- en- 1 -yloxycarbonyl ;4-methyl-pent-4-en-l-yloxycarbonyl, 1, l-dimethyl-but-2-en-l-yloxycarbonyl, 1, l-dimethyl-but-3-en-l-yloxycarbonyl, 1, 2- Dimethyl-but-1-en-l-yloxycarbonyl, 1, 2-dimethyl-but-2-en-l-yloxycarbonyl, 1, 2-dimethyl-but-3-en-l-yloxycarbonyl, 1,3-di- methyl-but-1-en-l-yloxycarbonyl, 1, 3-dimethyl-but-2-en-l-yloxycarbonyl, 1, 3-dimethyl-but-3-en-l-yloxycarbonyl, 2,2-di- methyl-but-3-en-l-yloxycarbonyl, 2,3-dimethyl-but-l-en-l- yloxycarbonyl, 2, 3-dimethyl-but-2-en-l-yloxycarbonyl, 2,3-dimethyl-but-3-en-l-yloxycarbonyl, 3, 3-dimethyl-but-l-en-l- yloxycarbonyl, 3, 3-dimethyl-but-2-en-l-yloxycarbonyl, 1-ethyl-but-l-en-l-yloxycarbonyl, l-ethyl-but-2-en-l-yloxycarbonyl, l- Ethyl-but-3-en-l-yloxycarbonyl, 2-ethyl-but-l-en-1-yloxycarbonyl, 2-ethyl-but-2-en-l-yloxycarbonyl, 2-ethyl-but-3-en- l-yloxycarbonyl, 1, 1, 2-trimethyl-prop-2-en-1-yloxycarbonyl, l-ethyl-l-methyl-prop-2-en-l-yloxycarbonyl, l-ethyl-2-methyl-prop- 1-en-1-yloxycarbonyl or 1-ethyl-2-methyl-prop-2-en-1-yloxycarbonyl, in particular for prop-2-en-1-yloxycarbonyl;
(C3-Cg-Alkenyloxy) carbonyl-Ci-Cg-alkyl für: durch (C3-Cg-Alkenyloxy) carbonyl wie vorstehend genannt, Vorzugs - weise Prop-2-en-l-yl-oxycarbonyl, substituiertes Ci-Cδ-Alkyl, also beispielsweise Prop-2 -en-l-yl -oxycarbonyl -methyl ;(C 3 -Cg-Alkenyloxy) carbonyl-Ci-Cg-alkyl for: by (C 3 -Cg-Alkenyloxy) carbonyl as mentioned above, preferably - Prop-2-en-l-yl-oxycarbonyl, substituted Ci-C δ- alkyl, for example prop-2-en-1-yl-oxycarbonyl -methyl;
(C2-Cδ-Alkenyl) carbonyloxy für: Ethenylcarbonyloxy, Prop- 1-en-l-ylcarbonyloxy, Prop-2-en-l-ylcarbonyloxy, 1-Methyl - ethenylcarbonyloxy, n-Buten-1-ylcarbonyloxy, n-Buten-2-yl- carbonyloxy, n-Buten-3-ylcarbonyloxy, 1-Methyl-prop-l-en- 1-ylcarbonyloxy, 2-Methyl-prop-1-en-l-ylcarbonyloxy, l-Methyl-prop-2-en-l-ylcarbonyloxy, 2-Methyl-prop-2-en-l-yl - carbonyloxy, n-Penten-1-ylcarbonyloxy, n-Penten-2-ylcarbonyl- oxy, n-Penten-3-ylcarbonyloxy, n-Penten-4-ylcarbonyloxy,(C 2 -C δ- alkenyl) carbonyloxy for: ethenylcarbonyloxy, prop-1-en-l-ylcarbonyloxy, prop-2-en-l-ylcarbonyloxy, 1-methyl-ethenylcarbonyloxy, n-buten-1-ylcarbonyloxy, n- Buten-2-ylcarbonyloxy, n-buten-3-ylcarbonyloxy, 1-methyl-prop-l-en-1-ylcarbonyloxy, 2-methyl-prop-1-en-l-ylcarbonyloxy, l-methyl-prop- 2-en-l-ylcarbonyloxy, 2-methyl-prop-2-en-l-yl-carbonyloxy, n-penten-1-ylcarbonyloxy, n-penten-2-ylcarbonyl-oxy, n-penten-3-ylcarbonyloxy, n-penten-4-ylcarbonyloxy,
1-Methyl-but-l-en-l-ylcarbonyloxy, 2-Methyl-but-l-en-l-yl- carbonyloxy, 3-Methyl-but-l-en-l-ylcarbonyloxy, 1-Methyl- but-2-en-l-ylcarbonyloxy, 2-Methyl-but-2-en-l-ylcarbonyloxy, 3-Methyl-but-2-en-l-ylcarbonyloxy, l-Methyl-but-3-en-l-yl - carbonyloxy, 2-Methyl-but-3-en-l-ylcarbonyloxy, 3-Methyl- but-3-en-l-ylcarbonyloxy, 1 , l-Dimethyl-prop-2-en-l-yl - carbonyloxy, 1, 2-Dimethyl-prop-l-en-l-ylcarbonyloxy, 1,2-Di- methyl-prop-2-en-l-ylcarbonyloxy, l-Ethyl-prop-l-en-2-yl - carbonyloxy, l-Ethyl-prop-2-en-l-ylcarbonyloxy, n-Hex-1-en- 1-ylcarbonyloxy, n-Hex-2-en-l-ylcarbonyloxy, n-Hex-3-en-l-yl- carbonyloxy, n-Hex-4-en-l-ylcarbonyloxy, n-Hex-5-en-l-yl- carbonyloxy, 1-Methyl-pent-l-en-l-ylcarbonyloxy, 2-Methyl- pent-1-en-l-ylcarbonyloxy, 3-Methyl-pent-l-en-l-ylcarbonyl - oxy, 4-Methyl-pent-l-en-l-ylcarbonyloxy, l-Methyl-pent-2-en- 1-ylcarbonyloxy, 2-Methyl-pent-2-en-l-ylcarbonyloxy,1-methyl-but-l-en-l-ylcarbonyloxy, 2-methyl-but-l-en-l-ylcarbonyloxy, 3-methyl-but-l-en-l-ylcarbonyloxy, 1-methyl-but- 2-en-l-ylcarbonyloxy, 2-methyl-but-2-en-l-ylcarbonyloxy, 3-methyl-but-2-en-l-ylcarbonyloxy, l-methyl-but-3-en-l-yl - carbonyloxy, 2-methyl-but-3-en-l-ylcarbonyloxy, 3-methyl-but-3-en-l-ylcarbonyloxy, 1, l-dimethyl-prop-2-en-l-yl - carbonyloxy, 1, 2-dimethyl-prop-l-en-l-ylcarbonyloxy, 1,2-dimethyl-prop-2-en-l-ylcarbonyloxy, l-ethyl-prop-l-en-2-yl - carbonyloxy, l- Ethyl-prop-2-en-l-ylcarbonyloxy, n-hex-1-en-1-ylcarbonyloxy, n-hex-2-en-l-ylcarbonyloxy, n-hex-3-en-l-ylcarbonyloxy, n-hex-4-en-l-ylcarbonyloxy, n-hex-5-en-l-ylcarbonyloxy, 1-methyl-pent-l-en-l-ylcarbonyloxy, 2-methyl-pent-1-en- l-ylcarbonyloxy, 3-methyl-pent-l-en-l-ylcarbonyloxy, 4-methyl-pent-l-en-l-ylcarbonyloxy, l-methyl-pent-2-en-1-ylcarbonyloxy, 2- Methyl-pent-2-en-l-ylcarbonyloxy,
3-Methyl-pent-2-en-l-ylcarbonyloxy, 4-Methyl-pent-2-en-l-yl- carbonyloxy, l-Methyl-pent-3-en-l-ylcarbonyloxy, 2-Methyl- pent-3-en-l-ylcarbonyloxy, 3-Methyl-pent-3-en-l-ylcarbonyl- oxy, 4-Methyl-pent-3-en-l-ylcarbonyloxy, l-Methyl-pent-4-en- 1-ylcarbonyloxy, 2-Methyl-pent-4-en-l-ylcarbonyloxy,3-methyl-pent-2-en-l-ylcarbonyloxy, 4-methyl-pent-2-en-l-ylcarbonyloxy, l-methyl-pent-3-en-l-ylcarbonyloxy, 2-methyl-pent- 3-en-l-ylcarbonyloxy, 3-methyl-pent-3-en-l-ylcarbonyloxy, 4-methyl-pent-3-en-l-ylcarbonyloxy, l-methyl-pent-4-ene 1- ylcarbonyloxy, 2-methyl-pent-4-en-l-ylcarbonyloxy,
3-Methyl-pent-4-en-l-ylcarbonyloxy, 4-Methyl-pent-4-en-l-yl - carbonyloxy, 1, l-Dimethyl-but-2-en-l-ylcarbonyloxy, 1,1-Di- methyl-but-3-en-l-ylcarbonyloxy, 1, 2-Dimethyl-but-1-en-l-yl- carbonyloxy, 1, 2-Dimethyl-but-2-en-l-ylcarbonyloxy, 1, 2-Dimethyl-but-3-en-l-ylcarbonyloxy, 1, 3-Dimethyl-but-l-en-l-yl- carbonyloxy, 1, 3-Dimethyl-but-2-en-l-ylcarbonyloxy, 1,3-Di- methyl-but-3-en-l-ylcarbonyloxy, 2, 2-Dimethyl-but-3-en-l-yl- carbonyloxy, 2, 3-Dimethyl-but-l-en-l-ylcarbonyloxy, 2,3-Di- methyl-but-2-en-l-ylcarbonyloxy, 2 , 3-Dimethyl-but-3-en-l-yl - carbonyloxy, 3 , 3-Dimethyl-but-l-en-l-ylcarbonyloxy, 3,3-Di- methyl-but-2-en-l-ylcarbonyloxy, 1-Ethyl-but-l-en-l-yl- carbonyloxy, l-Ethyl-but-2-en-l-ylcarbonyloxy, 1-Ethyl-but- 3-en-l-ylcarbonyloxy, 2-Ethyl-but-l-en-l-ylcarbonyloxy, 2-Ethyl-but-2-en-l-ylcarbonyloxy, 2-Ethyl-but-3-en-l-yl - carbonyloxy, 1, 1, 2-Trimethyl-prop-2-en-l-ylcarbonyloxy, l-Ethyl-l-methyl-prop-2-en-l-ylcarbonyloxy, l-Ethyl-2-methyl- prop-1-en-l-ylcarbonyloxy oder l-Ethyl-2-methyl-prop-2-en- 1-ylcarbonyloxy, insbesondere für Ethenylcarbonyloxy oder Prop- 2 -en- 1 -ylcarbonyloxy;3-methyl-pent-4-en-l-ylcarbonyloxy, 4-methyl-pent-4-en-l-ylcarbonyloxy, 1, l-dimethyl-but-2-en-l-ylcarbonyloxy, 1,1- Di- methyl-but-3-en-l-ylcarbonyloxy, 1, 2-dimethyl-but-1-en-l-ylcarbonyloxy, 1, 2-dimethyl-but-2-en-l-ylcarbonyloxy, 1, 2- Dimethyl-but-3-en-l-ylcarbonyloxy, 1, 3-dimethyl-but-l-en-l-ylcarbonyloxy, 1, 3-dimethyl-but-2-en-l-ylcarbonyloxy, 1,3- Dimethyl-but-3-en-l-ylcarbonyloxy, 2, 2-dimethyl-but-3-en-l-ylcarbonyloxy, 2, 3-dimethyl-but-l-en-l-ylcarbonyloxy, 2, 3-dimethyl-but-2-en-l-ylcarbonyloxy, 2, 3-dimethyl-but-3-en-l-yl-carbonyloxy, 3, 3-dimethyl-but-l-en-l-ylcarbonyloxy, 3,3-dimethyl-but-2-en-l-ylcarbonyloxy, 1-ethyl-but-l-en-l-ylcarbonyloxy, l-ethyl-but-2-en-l-ylcarbonyloxy, 1- Ethyl-but-3-en-l-ylcarbonyloxy, 2-ethyl-but-l-en-l-ylcarbonyloxy, 2-ethyl-but-2-en-l-ylcarbonyloxy, 2-ethyl-but-3-en- l-yl - carbonyloxy, 1, 1, 2-trimethyl-prop-2-en-l-ylcarbonyloxy, l-ethyl-l-methyl-prop-2-en-l-ylcarbonyloxy, l-ethyl-2-methyl- prop-1-en-l-ylcarbonyloxy or l-ethyl-2-methyl-prop-2-en-1-ylcarbonyloxy, in particular for ethenylcarbonyloxy or prop-2-en-1 -ylcarbonyloxy;
(C -Cδ-Alkenyl) carbonylthio für: Ethenylcarbonylthio, Prop- 1-en-l-ylcarbonylthio, Prop-2-en-l-ylcarbonylthio, 1-Methyl- ethenylcarbonylthio, n-Buten-1-ylcarbonylthio, n-Buten-2-yl- carbonylthio, n-Buten-3-ylcarbonylthio, 1-Methyl-prop-l-en- 1-ylcarbonylthio, 2-Methyl-prop-l-en-l-ylcarbonylthio, l-Methyl-prop-2-en-l-ylcarbonylthio, 2-Methyl-prop-2-en-l-yl- carbonylthio, n-Penten-1-ylcarbonylthio, n-Penten-2-yl- carbonylthio, n-Penten-3-ylcarbonylthio, n-Penten-4-yl- carbonylthio, 1-Methyl-but-l-en-l-ylcarbonylthio, 2-Methyl- but-1-en-l-ylcarbonylthio, 3-Methyl-but-l-en-l-ylcarbonyl- thio, l-Methyl-but-2-en-l-ylcarbonylthio, 2-Methyl-but-2-en- 1-ylcarbonylthio, 3-Methyl-but-2-en-l-ylcarbonylthio, l-Methyl-but-3-en-l-ylcarbonylthio, 2-Methyl-but-3-en-l-yl- carbonylthio, 3-Methyl-but-3-en-l-ylcarbonylthio, 1,1-Di- methyl-prop-2-en-l-ylcarbonylthio, 1, 2-Dimethyl-prop-l-en- 1-ylcarbonylthio, 1, 2-Dimethyl-prop-2-en-l-ylcarbonylthio, l-Ethyl-prop-l-en-2-ylcarbonylthio, l-Ethyl-prop-2-en-l-yl- carbonylthio, n-Hex-1-en-l-ylcarbonylthio, n-Hex-2-en-l-yl- carbonylthio, n-Hex-3-en-l-ylcarbonylthio, n-Hex-4-en-l-yl- carbonylthio, n-Hex-5-en-l-ylcarbonylthio, 1-Methyl-pent- 1-en-l-ylcarbonylthio, 2-Methyl-pent-l-en-l-ylcarbonylthio, 3-Methyl-pent-l-en-l-ylcarbonylthio, 4-Methyl-pent-l-en-l-yl- carbonylthio, l-Methyl-pent-2-en-l-ylcarbonylthio, 2-Methyl- pent-2-en-l-ylcarbonylthio, 3-Methyl-pent-2-en-l-ylcarbonyl - thio, 4-Methyl-pent-2-en-l-ylcarbonylthio, 1-Methyl-pent- 3-en-l-ylcarbonylthio, 2-Methyl-pent-3-en-l-ylcarbonylthio, 3-Methyl-pent-3-en-l-ylcarbonylthio, 4-Methyl-pent-3-en-l-yl- carbonylthio, l-Methyl-pent-4-en-l-ylcarbonylthio, 2-Methyl- pent-4-en-l-ylcarbonylthio, 3-Methyl-pent-4-en-l-ylcarbonyl - thio, 4-Methyl-pent-4-en-l-ylcarbonylthio, 1, 1-Dimethyl- but-2-en-l-ylcarbonylthio, 1, l-Dimethyl-but-3-en-l-yl- carbonylthio, 1, 2-Dimethyl-but-1-en-l-ylcarbonylthio, 1, 2-Dimethyl-but-2-en-l-ylcarbonylthio, 1, 2-Dimethyl-but-3-en-l-yl- carbonylthio, 1, 3-Dimethyl-but-l-en-l-ylcarbonylthio, 1,3-Di- methyl-but-2-en-l-ylcarbonylthio, 1, 3-Dimethyl-but-3-en-l-yl- carbonylthio, 2, 2-Dimethyl-but-3-en-l-ylcarbonylthio, 2,3-Di- methyl-but-1-en-l-ylcarbonylthio, 2, 3-Dimethyl-but-2-en-l-yl- carbonylthio, 2, 3-Dimethyl-but-3-en-l-ylcarbonylthio, 3,3-Di- methyl-but-1-en-l-ylcarbonylthio, 3, 3-Dimethyl-but-2-en-l-yl- carbonylthio, 1-Ethyl-but-l-en-l-ylcarbonylthio, 1-Ethyl-but- 2-en-l-ylcarbonylthio, l-Ethyl-but-3-en-l-ylcarbonylthio, 2-Ethyl-but-l-en-l-ylcarbonylthio, 2-Ethyl-but-2-en-l-yl- carbonylthio, 2-Ethyl-but-3-en-l-ylcarbonylthio, 1,1,2-Tri- methyl-prop-2-en-l-ylcarbonylthio, 1-Ethyl-l-methyl-prop- 2-en-l-ylcarbonylthio, l-Ethyl-2-methyl-prop-l-en-l-yl- carbonylthio oder l-Ethyl-2-methyl-prop-2-en-l-ylcarbonyl- thio, insbesondere für Ethenylcarbonylthio oder Prop-2-en- 1 -yl-carbonylthio;(C -C δ- alkenyl) carbonylthio for: ethenylcarbonylthio, prop-1-en-l-ylcarbonylthio, prop-2-en-l-ylcarbonylthio, 1-methylethenylcarbonylthio, n-buten-1-ylcarbonylthio, n-butene -2-yl-carbonylthio, n-buten-3-ylcarbonylthio, 1-methyl-prop-l-en-1-ylcarbonylthio, 2-methyl-prop-l-en-l-ylcarbonylthio, l-methyl-prop-2 -en-l-ylcarbonylthio, 2-methyl-prop-2-en-l-yl-carbonylthio, n-penten-1-ylcarbonylthio, n-penten-2-yl-carbonylthio, n-penten-3-ylcarbonylthio, n -Pentene-4-yl-carbonylthio, 1-methyl-but-l-en-l-ylcarbonylthio, 2-methyl-but-1-en-l-ylcarbonylthio, 3-methyl-but-l-en-l-ylcarbonyl - thio, l-methyl-but-2-en-l-ylcarbonylthio, 2-methyl-but-2-en-1-ylcarbonylthio, 3-methyl-but-2-en-l-ylcarbonylthio, l-methyl-but -3-en-l-ylcarbonylthio, 2-methyl-but-3-en-l-yl-carbonylthio, 3-methyl-but-3-en-l-ylcarbonylthio, 1,1-dimethyl-prop-2 -en-1-ylcarbonylthio, 1, 2-dimethyl-prop-1-en-1-ylcarbonylthio, 1, 2-dimethyl-prop-2-en-1-ylcarbonylthio, 1-ethyl-prop-1-en-2 -ylcarbonylthio, l-ethyl-prop-2-e nl-yl-carbonylthio, n-hex-1-en-l-ylcarbonylthio, n-hex-2-en-l-yl-carbonylthio, n-hex-3-en-l-ylcarbonylthio, n-hex-4- en-l-yl-carbonylthio, n-hex-5-en-l-ylcarbonylthio, 1-methyl-pent-1-en-l-ylcarbonylthio, 2-methyl-pent-l-en-l-ylcarbonylthio, 3- Methyl-pent-l-en-l-ylcarbonylthio, 4-methyl-pent-l-en-l-yl-carbonylthio, l-methyl-pent-2-en-l-ylcarbonylthio, 2-methyl-pent-2- en-l-ylcarbonylthio, 3-methyl-pent-2-en-l-ylcarbonylthio, 4-methyl-pent-2-en-l-ylcarbonylthio, 1-methyl-pent-3-en-l-ylcarbonylthio, 2-methyl-pent-3-en-l-ylcarbonylthio, 3-methyl-pent-3-en-l-ylcarbonylthio, 4-methyl-pent-3-en-l-ylcarbonylthio, l-methyl-pent- 4-en-l-ylcarbonylthio, 2-methyl-pent-4-en-l-ylcarbonylthio, 3-methyl-pent-4-en-l-ylcarbonyl - thio, 4-methyl-pent-4-en-l-ylcarbonylthio, 1, 1-dimethyl-but-2-en-l-ylcarbonylthio, 1, l-dimethyl-but-3-en-l-yl-carbonylthio, 1, 2-dimethyl-but-1-en-l-ylcarbonylthio, 1, 2-dimethyl-but-2-en-l-ylcarbonylthio, 1, 2-dimethyl-but-3-en-l-ylcarbonylthio, 1,3-dimethyl-but-l-en-l-ylcarbonylthio, 1,3-dimethyl-but-2-en-l-ylcarbonylthio, 1,3-dimethyl-but-3-en-l-yl- carbonylthio, 2, 2-dimethyl-but-3-en-l-ylcarbonylthio, 2,3-dimethyl-but-1-en-l-ylcarbonylthio, 2, 3-dimethyl-but-2-en-l- yl-carbonylthio, 2, 3-dimethyl-but-3-en-l-ylcarbonylthio, 3,3-dimethyl-but-1-en-l-ylcarbonylthio, 3, 3-dimethyl-but-2-en- l-yl-carbonylthio, 1-ethyl-but-l-en-l-ylcarbonylthio, 1-ethyl-but-2-en-l-ylcarbonylthio, l-ethyl-but-3-en-l-ylcarbonylthio, 2- Ethyl-but-l-en-l-ylcarbonylthio, 2-ethyl-but-2-en-l-ylcarbonylthio, 2-ethyl-but-3-en-l-ylcarbonylthio, 1,1,2-tri- methyl-prop-2-en-l-ylcarbonylthio, 1-ethyl-l-methyl-prop-2-en-l-ylcarbonylthio, l-ethyl-2-methyl-prop-l-en-l-ylcarbonylthio or l-ethyl-2-met hyl-prop-2-en-l-ylcarbonylthio, in particular for ethenylcarbonylthio or prop-2-en-1 -yl-carbonylthio;
(C2-Cg-Alkinyl) carbonyloxy für: Ethinylcarbonyloxy, Prop- 1-in-l-ylcarbonyloxy, Prop-2-in-l-ylcarbonyloxy, n-But- 1-in-l-ylcarbonyloxy, n-But-l-in-3-ylcarbonyloxy, n-But- l-in-4-ylcarbonyloxy, n-But-2-in-l-ylcarbonyloxy, n-Pent- 1-in-l-ylcarbonyloxy, n-Pent-l-in-3-ylcarbonyloxy, n-Pent- l-in-4-ylcarbonyloxy, n-Pent-l-in-5-ylcarbonyloxy, n-Pent- 2-in-l-ylcarbonyloxy, n-Pent-2-in-4-ylcarbonyloxy, n-Pent- 2-in-5-ylcarbonyloxy, 3-Methyl-but-l-in-3-ylcarbonyloxy, 3-Methyl-but-l-in-4-ylcarbonyloxy, n-Hex-1-in-l-ylcarbonyl - oxy, n-Hex-l-in-3-ylcarbonyloxy, n-Hex-l-in-4-ylcarbonyloxy, n-Hex-l-in-5-ylcarbonyloxy, n-Hex-l-in-6-ylcarbonyloxy, n-Hex-2-in-l-ylcarbonyloxy, n-Hex-2-in-4-ylcarbonyloxy, n-Hex-2-in-5-ylcarbonyloxy, n-Hex-2-in-6-ylcarbonyloxy, n-Hex-3-in-l-ylcarbonyloxy, n-Hex-3-in-2-ylcarbonyloxy, 3-Methylpent-l-in-l-ylcarbonyloxy, 3-Methyl-pent-l-in-3-yl- carbonyloxy, 3-Methyl-pent-l-in-4-ylcarbonyloxy, 3-Methyl- pent-l-in-5-ylcarbonyloxy, 4-Methyl-pent-l-in-l-ylcarbonyl - oxy, 4-Methyl-pent-2-in-4-ylcarbonyloxy oder 4-Methylpent- 2-in-5-ylcarbonyloxy, insbesondere für Ethinylcarbonyloxy oder Prop-2-in-l-ylcarbonyloxy;(C 2 -C 6 alkynyl) carbonyloxy for: ethynylcarbonyloxy, prop-1-in-1-ylcarbonyloxy, prop-2-in-1-ylcarbonyloxy, n-but-1-in-1-ylcarbonyloxy, n-but-1 -in-3-ylcarbonyloxy, n-but-l-in-4-ylcarbonyloxy, n-but-2-in-l-ylcarbonyloxy, n-pent-1-in-l-ylcarbonyloxy, n-pent-l-in -3-ylcarbonyloxy, n-pent-l-in-4-ylcarbonyloxy, n-pent-l-in-5-ylcarbonyloxy, n-pent-2-in-l-ylcarbonyloxy, n-pent-2-in-4 -ylcarbonyloxy, n-pent-2-in-5-ylcarbonyloxy, 3-methyl-but-l-in-3-ylcarbonyloxy, 3-methyl-but-l-in-4-ylcarbonyloxy, n-hex-1-in -l-ylcarbonyl-oxy, n-hex-l-in-3-ylcarbonyloxy, n-hex-l-in-4-ylcarbonyloxy, n-hex-l-in-5-ylcarbonyloxy, n-hex-l-in -6-ylcarbonyloxy, n-Hex-2-in-1-ylcarbonyloxy, n-Hex-2-in-4-ylcarbonyloxy, n-Hex-2-in-5-ylcarbonyloxy, n-Hex-2-in-6 -ylcarbonyloxy, n-hex-3-in-1-ylcarbonyloxy, n-hex-3-in-2-ylcarbonyloxy, 3-methylpent-1-in-1-ylcarbonyloxy, 3-methyl-pent-1-in-3 -yl-carbonyloxy, 3-methyl-pent-l-in-4-ylcarbonyloxy, 3-methyl-pent-l-in-5-ylcarbonyloxy, 4-methyl-pent-l-in-l-ylcarbonyloxy, 4 - Methyl-pent-2-in-4-ylcarbonyloxy or 4-methylpent-2-in-5-ylcarbonyloxy, in particular for ethynylcarbonyloxy or prop-2-in-1-ylcarbonyloxy;
C3-Cg-Alkinylsulfonyloxy für: Prop-1-in-l-ylsulfonyloxy, Prop-2-in-l-ylsulfonyloxy, n-But-1-in-1-ylsulfonyloxy, n-But-l-in-3-ylsulfonyloxy, n-But-l-in-4-ylsulfonyloxy, n-But-2-in-l-ylsulfonyloxy, n-Pent-1-in-l-ylsulfonyloxy, n-Pent-l-in-3-ylsulfonyloxy, n-Pent-l-in-4-ylsulfonyloxy, n-Pent-l-in-5-ylsulfonyloxy, n-Pent-2-in-1-ylsulfonyloxy, n-Pent-2-in-4-ylsulfonyloxy, n-Pent-2-in-5-ylsulfonyloxy, 3-Methyl-but-l-in-3-ylsulfonyloxy, 3-Methyl-but-l-in-4-yl- sulfonyloxy, n-Hex-1-in-l-ylsulfonyloxy, n-Hex-l-in-3-yl- sulfonyloxy, n-Hex-l-in-4-ylsulfonyloxy, n-Hex-l-in-5-yl- sulfonyloxy, n-Hex-l-in-6-ylsulfonyloxy, n-Hex-2-in-l-yl- sulfonyloxy, n-Hex-2-in-4-ylsulfonyloxy, n-Hex-2-in-5-yl- sulfonyloxy, n-Hex-2-in-6-ylsulfonyloxy, n-Hex-3-in-l-yl- sulfonyloxy, n-Hex-3-in-2-ylsulfonyloxy, 3-Methylpent-l- in-1-ylsulfonyloxy, 3-Methyl-pent-l-in-3-ylsulfonyloxy, 3-Methyl-pent-l-in-4-ylsulfonyloxy, 3-Methyl-pent-l-in-5-yl- sulfonyloxy, 4-Methyl-pent-l-in-l-ylsulfonyloxy, 4-Methyl- pent-2-in-4-ylsulfonyloxy oder 4-Methylpent-2-in-5-yl- sulfonyloxy, insbesonere für Prop-2-in-l-ylsulfonyloxy;C 3 -Cg alkynylsulfonyloxy for: prop-1-in-l-ylsulfonyloxy, prop-2-in-l-ylsulfonyloxy, n-but-1-in-1-ylsulfonyloxy, n-but-l-in-3- ylsulfonyloxy, n-but-l-in-4-ylsulfonyloxy, n-but-2-in-l-ylsulfonyloxy, n-pent-1-in-l-ylsulfonyloxy, n-pent-l-in-3-ylsulfonyloxy, n-pent-l-in-4-ylsulfonyloxy, n-pent-l-in-5-ylsulfonyloxy, n-pent-2-in-1-ylsulfonyloxy, n-pent-2-in-4-ylsulfonyloxy, n-pent-2-in-5-ylsulfonyloxy, 3-methyl-but-l-in-3-ylsulfonyloxy, 3-methyl-but-l-in-4- yl-sulfonyloxy, n-hex-1-in-1-ylsulfonyloxy, n-hex-1-in-3-yl-sulfonyloxy, n-hex-1-in-4-ylsulfonyloxy, n-hex-1-in 5-yl-sulfonyloxy, n-hex-l-in-6-ylsulfonyloxy, n-hex-2-in-l-yl-sulfonyloxy, n-hex-2-in-4-ylsulfonyloxy, n-hex-2- in-5-yl-sulfonyloxy, n-hex-2-in-6-ylsulfonyloxy, n-hex-3-in-l-yl-sulfonyloxy, n-hex-3-in-2-ylsulfonyloxy, 3-methylpent- l-in-1-ylsulfonyloxy, 3-methyl-pent-l-in-3-ylsulfonyloxy, 3-methyl-pent-l-in-4-ylsulfonyloxy, 3-methyl-pent-l-in-5-yl- sulfonyloxy, 4-methyl-pent-l-in-l-ylsulfonyloxy, 4-methyl-pent-2-in-4-ylsulfonyloxy or 4-methylpent-2-in-5-yl-sulfonyloxy, especially for prop-2- in-l-ylsulfonyloxy;
(C -Cg-Alkinyl) carbonylthio für: Ethinylcarbonylthio,(C -Cg-alkynyl) carbonylthio for: ethynylcarbonylthio,
Prop-1-in-l-ylcarbonylthio, Prop-2-in-l-ylcarbonylthio, n-But-1-in-l-ylcarbonylthio, n-But-l-in-3-ylcarbonylthio, n-But-l-in-4-ylcarbonylthio, n-But-2-in-l-ylcarbonylthio, n-Pent-1-in-l-ylcarbonylthio, n-Pent-l-in-3-ylcarbonylthio, n-Pent-l-in-4-ylcarbonylthio, n-Pent-l-in-5-ylcarbonylthio, n-Pent-2-in-l-ylcarbonylthio, n-Pent-2-in-4-ylcarbonylthio, n-Pent-2-in-5-ylcarbonylthio, 3-Methyl-but-l-in-3-yl- carbonylthio, 3-Methylbut-l-in-4-ylcarbonylthio, n-Hex-1- in-1-ylcarbonylthio, n-Hex-l-in-3-ylcarbonylthio, n-Hex-1- in-4-ylcarbonylthio, n-Hex-l-in-5-ylcarbonylthio, n-Hex-1- in-6-ylcarbonylthio, n-Hex-2-in-l-ylcarbonylthio, n-Hex-2- in-4-ylcarbonylthio, n-Hex-2-in-5-ylcarbonylthio, n-Hex-2- in-6-ylcarbonylthio, n-Hex-3-in-l-ylcarbonylthio, n-Hex-3- in-2-ylcarbonylthio, 3-Methylpent-l-in-l-ylcarbonylthio, 3-Methyl-pent-l-in-3-ylcarbonylthio, 3-Methyl-pent-l-in-4-yl- carbonylthio, 3-Methylpent-l-in-5-ylcarbonylthio, 4-Methyl- pent-1-in-l-ylcarbonylthio, 4-Methyl-pent-2-in-4-ylcarbonyl- thio oder 4-Methyl-pent-2-in-5-ylcarbonylthio, insbesondere für Prop-2-in-l-ylcarbonylthio;Prop-1-in-l-ylcarbonylthio, prop-2-in-l-ylcarbonylthio, n-but-1-in-l-ylcarbonylthio, n-but-l-in-3-ylcarbonylthio, n-but-l- in-4-ylcarbonylthio, n-but-2-in-l-ylcarbonylthio, n-pent-1-in-l-ylcarbonylthio, n-pent-l-in-3-ylcarbonylthio, n-pent-l-in- 4-ylcarbonylthio, n-pent-l-in-5-ylcarbonylthio, n-pent-2-in-l-ylcarbonylthio, n-pent-2-in-4-ylcarbonylthio, n-pent-2-in-5- ylcarbonylthio, 3-methyl-but-l-in-3-yl-carbonylthio, 3-methylbut-l-in-4-ylcarbonylthio, n-hex-1- in-1-ylcarbonylthio, n-hex-l-in- 3-ylcarbonylthio, n-Hex-1- in-4-ylcarbonylthio, n-Hex-l-in-5-ylcarbonylthio, n-Hex-1- in-6-ylcarbonylthio, n-Hex-2-in-l- ylcarbonylthio, n-hex-2- in-4-ylcarbonylthio, n-hex-2-in-5-ylcarbonylthio, n-hex-2- in-6-ylcarbonylthio, n-hex-3-in-l-ylcarbonylthio, n-hex-3- in-2-ylcarbonylthio, 3-methylpent-l-in-l-ylcarbonylthio, 3-methyl-pent-l-in-3-ylcarbonylthio, 3-methylpent-l-in-4- yl-carbonylthio, 3-methylpent-1-in-5-ylcarbonylthio, 4-methylpent-1-in-1-ylcarbonylthio, 4-methylpent-2-in-4-ylcarbonyl-t hio or 4-methyl-pent-2-in-5-ylcarbonylthio, in particular for prop-2-in-l-ylcarbonylthio;
(Ci-Cg -Alkoxy) carbonyl -C -Cg-alkenyl für: durch (Ci-Cg-Alk- oxy) carbonyl wie vorstehend genannt substituiertes C2-Cg-Alkenyl, also beispielsweise für Methoxycarbonyl - prop-2 -en- 1-yl ;(Ci-Cg-alkoxy) carbonyl -C -Cg alkenyl for: C 2 -Cg alkenyl substituted by (Ci-Cg-alkoxy) carbonyl as mentioned above, for example for methoxycarbonyl-prop-2 -en- 1 -yl;
Cι-Cg-Alkoxy-C3-Cg-alkenyloxy für: durch Ci-Cg-Alkoxy wie vorstehend genannt substituiertes C3-Cg -Alkenyloxy, also beispielsweise für Methylprop-2-en-l-yloxy; C3-Cg-Alkenyloxy-Cι-Cg-alkyl für: durch C3-Cg-Alkenyloxy wie vorstehend genannt, vorzugsweise Allyloxy, 2-Methyl - prop-2-en-l-yloxy, But-l-en-3-yloxy, But-l-en-4-yloxy oder But-2-en-l-yloxy substituiertes Ci-Cg-Alkyl, also beispiels- weise für Allyloxymethyl, 2-Allyloxyethyl oder But-l-en-4- yloxymethyl ;-C-Cg-Alkoxy-C 3 -Cg-alkenyloxy for: C 3 -Cg -alkenyloxy substituted by Ci-Cg-alkoxy as mentioned above, for example for methylprop-2-en-l-yloxy; C 3 -Cg-alkenyloxy-Cι-Cg-alkyl for: by C 3 -Cg-alkenyloxy as mentioned above, preferably allyloxy, 2-methyl-prop-2-en-l-yloxy, but-l-en-3- yloxy, but-l-en-4-yloxy or but-2-en-l-yloxy-substituted Ci-Cg-alkyl, for example for allyloxymethyl, 2-allyloxyethyl or but-l-en-4-yloxymethyl;
C3-Cδ-Alkinyloxy-Cι-Cδ-alkyl für: durch C3-C6-Alkinyloxy wie vorstehend genannt, vorzugsweise Propargyloxy, But-l-in-3-yl- oxy, But-l-in-4-yloxy oder But-2-in-l-yloxy, substituiertes Ci-Cδ-Alkyl, also beispielsweise für Propargyloxymethyl oder 2-Propargyloxyethyl ;C 3 -C alkynyloxy δ-Cι-C alkyl δ viewed by C 3 -C 6 alkynyloxy as mentioned above, preferably propargyloxy, but-l-yn-3-yl-oxy, but-l-yn-4 -yloxy or but-2-yn-l-yloxy, substituted Ci-C δ alkyl, for example for propargyloxymethyl or 2-propargyloxyethyl;
C -C6 -Cycloalkyl für: Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl;C -C 6 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
C3-Cg-Cycloalkyl-Cι-Cg-alkoxy für: z. B. Cyclopropylmethoxy,C 3 -Cg-Cycloalkyl-Cι-Cg-alkoxy for: z. B. cyclopropylmethoxy,
Cyclobutylmethoxy, Cyclopentylmethoxy, Cyclohexylmethoxy,Cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,
1- (Cyclopropyl) ethoxy, 1- (Cyclobutyl) ethoxy, 1- (Cyclopentyl) - ethoxy, 1- (Cyclohexyl) ethoxy, 2- (Cyclopropyl) ethoxy,1- (cyclopropyl) ethoxy, 1- (cyclobutyl) ethoxy, 1- (cyclopentyl) ethoxy, 1- (cyclohexyl) ethoxy, 2- (cyclopropyl) ethoxy,
2- (Cyclobutyl) ethoxy, 2- (Cyclopentyl) ethoxy, 2- (Cyclohexyl) - ethoxy, 3- (Cyclopropyl) propoxy, 3- (Cyclobutyl) propoxy, 3- (Cyclopentyl) propoxy, 3- (Cyclohexyl) propoxy, 4- (Cyclopropyl) butoxy, 4- (Cyclobutyl) butoxy, 4- (Cyclopentyl) butoxy, 4- (Cyclohexyl) butoxy, 5- (Cyclopropyl) pentoxy, 5- (Cyclobutyl) - pentoxy, 5- (Cyclopentyl) pentoxy, 5- (Cyclohexyl) pentoxy, 6- (Cyc1opropy1) hexoxy, 6- (Cyc1obuty1) hexoxy, 6- (Cyc1openty1) - hexoxy oder 6- (Cyclohexyl) hexoxy, insbesondere für Cyclopentylmethoxy oder Cyclohexylmethoxy;2- (cyclobutyl) ethoxy, 2- (cyclopentyl) ethoxy, 2- (cyclohexyl) ethoxy, 3- (cyclopropyl) propoxy, 3- (cyclobutyl) propoxy, 3- (cyclopentyl) propoxy, 3- (cyclohexyl) propoxy, 4- (cyclopropyl) butoxy, 4- (cyclobutyl) butoxy, 4- (cyclopentyl) butoxy, 4- (cyclohexyl) butoxy, 5- (cyclopropyl) pentoxy, 5- (cyclobutyl) pentoxy, 5- (cyclopentyl) pentoxy, 5- (cyclohexyl) pentoxy, 6- (Cyc1opropy1) hexoxy, 6- (Cyc1obuty1) hexoxy, 6- (Cyc1openty1) hexoxy or 6- (cyclohexyl) hexoxy, especially for cyclopentylmethoxy or cyclohexylmethoxy;
C3-Cg-Cycloalkyloxy für: Cyclopropyloxy, Cyclobutyloxy, Cyclo- pentyloxy oder Cyclohexyloxy;C 3 -Cg cycloalkyloxy for: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy;
C3-Cg-Cycloalkylthio für: Cyclopropylthio, Cyclobutylthio, Cyclopentylthio oder Cyclohexylthio;C 3 -Cg cycloalkylthio for: cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio;
C3 -Cg-Cycloalkylcarbonyloxy für: Cyclopropylcarbonyloxy, Cyclobutylcarbonyloxy, Cyclopentylcarbonyloxy oder Cyclo- hexylcarbonyloxy;C 3 -Cg cycloalkylcarbonyloxy for: cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy or cyclohexylcarbonyloxy;
C3-Cg-Cycloalkylsulfonyloxy für: Cyclopropylsulfonyloxy, Cyclobutylsulfonyloxy, Cyclopentylsulfonyloxy oder Cyclohexylsulfonyloxy;C 3 -Cg cycloalkylsulfonyloxy for: cyclopropylsulfonyloxy, cyclobutylsulfonyloxy, cyclopentylsulfonyloxy or cyclohexylsulfonyloxy;
C5-C7-Cycloalkenyloxy für: Cyclopent-1-enyloxy, Cyclopent- 2-enyloxy, Cylopent-3 -enyloxy, Cyclohex-1-enyloxy, Cyclo- hex-2 -enyloxy, Cyclohex- 3 -enyloxy, Cyclohept-1- enyloxy. Cyclohept- 2 -enyloxy, Cyclohept- 3 -enyloxy oder Cyclohept -4- enyloxy.C 5 -C 7 cycloalkenyloxy for: cyclopent-1-enyloxy, cyclopent-2-enyloxy, cyclopent-3-enyloxy, cyclohex-1-enyloxy, cyclohex-2-enyloxy, cyclohex-3-enyloxy, cyclohept-1 - enyloxy. Cyclohept-2-enyloxy, Cyclohept-3-enyloxy or Cyclohept -4-enyloxy.
3- bis 7gliedrige Azaheterocyclen, die neben Kohlenstoffring- gliedern noch ein Sauerstoff- oder Schwefelatom als Ringglied enthalten können, sind z.B.3- to 7-membered azaheterocycles, which in addition to carbon ring members may also contain an oxygen or sulfur atom as a ring member, are e.g.
Pyrrolidin-1-yl, Isoxazolidin-2-yl, Isothiazolidin-2-yl, Ox- azolidin-3-yl, Thiazolidin-3-yl, Piperidin-1-yl, Morpholin-1-yl, Thiomorpholin-1-yl und Azepin-1-yl.Pyrrolidin-1-yl, isoxazolidin-2-yl, isothiazolidin-2-yl, oxazolidin-3-yl, thiazolidin-3-yl, piperidin-1-yl, morpholin-1-yl, thiomorpholin-1-yl and Azepin-1-yl.
Unter 3- bis 7-gliedrigem Heterocyclyl - das direkt oder über eine Sauerstoff-, Alkoxy-, Alkenyloxy- oder Alkinyloxybrücke verknüpft sein kann - sind sowohl gesättigte, partiell oder vollständig ungesättigte als auch aromatische Heterocyclen mit ein bis drei Heteroatomen, ausgewählt aus einer Gruppe bestehend aus ein bis drei Stickstoffatomen, einem oder zwei Sauerstoff- und einem oder zwei Schwefelatomen, zu verstehen.Under 3- to 7-membered heterocyclyl - which can be linked directly or via an oxygen, alkoxy, alkenyloxy or alkynyloxy bridge - are both saturated, partially or completely unsaturated and aromatic heterocycles with one to three heteroatoms selected from a group consisting of one to three nitrogen atoms, one or two oxygen and one or two sulfur atoms.
Beispiele für gesättigte Heterocyclen, die ein Carbonyl- oder Thiocarbonyl-Ringglied enthalten können, sind:Examples of saturated heterocycles which can contain a carbonyl or thiocarbonyl ring member are:
Oxiranyl, Thiiranyl, Aziridin-1-yl, Aziridin-2-yl, Diaziridin- 1-yl, Diaziridin-3-yl, Oxetan-2-yl, Oxetan-3-yl, Thietan-2-yl, Thietan-3-yl, Azetidin-1-yl, Azetidin-2-yl, Azetidin-3-yl, Tetra- hydrofuran-2-yl, Tetrahydrofuran-3-yl, Tetrahydrothiophen-2-yl, Tetrahydrothiophen-3-yl, Pyrrolidin-1-yl, Pyrrolidin-2-yl, Pyrrolidin-3-yl, 1, 3-Dioxolan-2-yl, 1, 3-Dioxolan-4-yl, 1,3-Oxa- thiolan-2-yl, 1, 3-Oxathiolan-4-yl, 1, 3-Oxathiolan-5-yl, 1,3-Ox- azolidin-2-yl, 1, 3-Oxazolidin-3-yl, 1, 3-Oxazolidin-4-yl, 1,3-Ox- azolidin-5-yl, 1, 2-Oxazolidin-2-yl, 1, 2-Oxazolidin-3-yl, 1,2-Ox- azolidin-4-yl, 1, 2-Oxazolidin-5-yl, 1, 3-Dithiolan-2-yl, 1,3-Di- thiolan-4-yl, Pyrrolidin-1-yl, Pyrrolidin-2-yl, Pyrrolidin-5-yl, Tetrahydropyrazol-1-yl, Tetrahydropyrazol-3-yl, Tetrahydropyr- azol-4-yl, Tetrahydropyran-2-yl, Tetrahydropyran-3-yl, Tetra- hydropyran-4-yl, Tetrahydrothiopyran-2-yl, Tetrahydrothiopyran- 3-yl, Tetrahydrothiopyran-4-yl, Piperidin-1-yl, Piperidin-2-yl, Piperidin-3-yl, Piperidin-4-yl, 1, 3-Dioxan-2-yl, 1, 3-Dioxan-4-yl, 1, 3-Dioxan-5-yl, 1, 4-Dioxan-2-yl, 1, 3-Oxathian-2-yl, 1,3-Oxa- thian-4-yl, 1, 3-Oxathian-5-yl, 1, 3-Oxathian-6-yl, 1, 4-Oxathian- 2-yl, 1, 4-Oxathian-3-yl, Morpholin-2-yl, Morpholin-3-yl, Morpholin-4-yl, Hexahydropyridazin-1-yl, Hexahydropyridazin-3-yl, Hexahydropyridazin-4-yl , Hexahydropyrimidin-1-yl , Hexahydropyri - midin-2-yl, Hexahydropyrimidin-4-yl , Hexahydropyrimidin-5-yl, Piperazin-1-yl, Piperazin-2-yl, Piperazin-3-yl, Hexahydro-1, 3 , 5- triazin-1-yl, Hexahydro-1, 3, 5-triazin-2-yl, Oxepan-2-yl, Oxepan- 3-yl, Oxepan-4-yl, Thiepan-2-yl, Thiepan-3-yl, Thiepan-4-yl, 1, 3-Dioxepan-2-yl, 1, 3-Dioxepan-4-yl , 1, 3-Dioxepan-5-yl, 1,3-Di- oxepan-6-yl, 1, 3-Dithiepan-2-yl, 1, 3-Dithiepan-2-yl, 1,3-Dithi- epan-2-yl, 1, 3-Dithiepan-2-yl, 1, 4-Dioxepan-2-yl, 1, 4-Dioxepan- 7-yl, Hexahydroazepin-1-yl, Hexahydroazepin-2-yl, Hexahydro- azepin-3-yl, Hexahydroazepin-4-yl, Hexahydro-1, 3-diazepin-l-yl, Hexahydro-1, 3-diazepin-2-yl, Hexahydro-1, 3-diazepin-4-yl, Hexa- hydro-1, 4-diazepin-l-yl und Hexahydro-1, 4-diazepin-2-yl;Oxiranyl, thiiranyl, aziridin-1-yl, aziridin-2-yl, diaziridin-1-yl, diaziridin-3-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl, thietan-3- yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl, pyrrolidin-1- yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1, 3-dioxolan-2-yl, 1, 3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1, 3- Oxathiolan-4-yl, 1, 3-oxathiolan-5-yl, 1,3-oxazolidin-2-yl, 1, 3-oxazolidin-3-yl, 1, 3-oxazolidin-4-yl, 1, 3-oxazolidin-5-yl, 1,2-oxazolidin-2-yl, 1,2-oxazolidin-3-yl, 1,2-oxazolidin-4-yl, 1,2-oxazolidin-5- yl, 1, 3-dithiolan-2-yl, 1,3-di-thiolan-4-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-5-yl, tetrahydropyrazol-1-yl, tetrahydropyrazole 3-yl, tetrahydropyr-azol-4-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran- 3-yl, tetrahydrothiopyran Piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, 1, 3-dioxan-2-yl, 1, 3-dioxan-4-yl, 1, 3-dioxan-5-yl, 1, 4-dioxan-2-yl, 1, 3-oxathian-2-yl, 1, 3-oxathian-4-yl, 1, 3-oxathian-5-yl, 1, 3-oxathian-6-yl, 1, 4-oxathian-2-yl, 1, 4-oxathian-3-yl, Morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, hexahydropyridazin-1-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl, hexahydropyri - midin-2-yl, Hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl, piperazin-3-yl, hexahydro-1, 3, 5-triazin-1-yl, hexahydro-1, 3, 5-triazin-2-yl, oxepan-2-yl, oxepan-3-yl, oxepan-4-yl, thiepan-2-yl, thiepan-3-yl, thiepan-4-yl, 1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1,3-dioxepan-5-yl, 1,3-dioxoxan-6-yl, 1,3-dithiepan-2- yl, 1,3-dithiepan-2-yl, 1,3-dithi-epan-2-yl, 1,3-dithiepan-2-yl, 1,4-dioxepan-2-yl, 1,4-dioxepane 7-yl, hexahydroazepin-1-yl, hexahydroazepin-2-yl, hexahydro-azepin-3-yl, hexahydroazepin-4-yl, hexahydro-1, 3-diazepin-l-yl, hexahydro-1, 3-diazepine 2-yl, hexahydro-1,3-diazepin-4-yl, hexa- hydro-1,4-diazepin-1-yl and hexahydro-1,4-diazepin-2-yl;
Beispiele für ungesättigte Heterocyclen, die ein Carbonyl- oder Thiocarbonyl-Ringglied enthalten können, sind:Examples of unsaturated heterocycles which can contain a carbonyl or thiocarbonyl ring member are:
Dihydrofuran-2-yl, 1, 2 -Oxazolin-3 -yl, 1, 2 -0xazolin-5 -yl, 1, 3-Oxazolin-2-yl;Dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl, 1,3-oxazolin-2-yl;
Unter den Heteroaromaten sind die 5- und 6-gliedrigen bevorzugt, also z.B.Among the heteroaromatics, the 5- and 6-membered ones are preferred, e.g.
Furyl wie 2-Furyl und 3-Furyl, Thienyl wie 2-Thienyl und 3-Thienyl, Pyrrolyl wie 2-Pyrrolyl und 3-Pyrrolyl, Isoxazolyl wie 3-Isoxazolyl, 4-Isoxazolyl und 5-Isoxazolyl, Isothiazolyl wie 3-Isothiazolyl, 4-Isothiazolyl und 5-Isothiazolyl, Pyrazolyl wie 3-Pyrazolyl, 4-Pyrazolyl und 5-Pyrazolyl, Oxazolyl wieFuryl such as 2-furyl and 3-furyl, thienyl such as 2-thienyl and 3-thienyl, pyrrolyl such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl such as
2-Oxazolyl, 4-Oxazolyl und 5-Oxazolyl, Thiazolyl wie 2-Thiazolyl,2-oxazolyl, 4-oxazolyl and 5-oxazolyl, thiazolyl such as 2-thiazolyl,
4-Thiazolyl und 5-Thiazolyl, Imidazolyl wie 2-Imidazolyl und 4-Imidazolyl, Oxadiazolyl wie 1, 2 , 4-Oxadiazol-3-yl,4-thiazolyl and 5-thiazolyl, imidazolyl such as 2-imidazolyl and 4-imidazolyl, oxadiazolyl such as 1, 2, 4-oxadiazol-3-yl,
1, 2, 4-Oxadiazol-5-yl und 1, 3 , 4-Oxadiazol-2-yl, Thiadiazolyl wie l,2,4-Thiadiazol-3-yl, 1, 2 , 4-Thiadiazol-5-yl und l,3,4-Thiadiazol-2-yl, Triazolyl wie 1, 2 , 4-Triazol-l-yl, 1, 2,4-Triazol-3-yl und 1, 2 , 4-Triazol-4-yl, Pyridinyl wie 2-Pyridinyl, 3-Pyridinyl und 4-Pyridinyl, Pyridazinyl wie 3-Pyridazinyl und 4-Pyridazinyl, Pyrimidinyl wie 2-Pyrimidinyl, 4-Pyrimidinyl und 5-Pyrimidinyl, des weiteren 2-Pyrazinyl,1, 2, 4-oxadiazol-5-yl and 1, 3, 4-oxadiazol-2-yl, thiadiazolyl such as l, 2,4-thiadiazol-3-yl, 1, 2, 4-thiadiazol-5-yl and l, 3,4-thiadiazol-2-yl, triazolyl such as 1, 2, 4-triazol-l-yl, 1, 2,4-triazol-3-yl and 1, 2, 4-triazol-4-yl, Pyridinyl such as 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl such as 3-pyridazinyl and 4-pyridazinyl, pyrimidinyl such as 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, furthermore 2-pyrazinyl,
1, 3 , 5-Triazin-2-yl und 1, 2, 4-Triazin-3-yl, insbesondere Pyridyl, Pyrimidyl, Furanyl und Thienyl.1, 3, 5-triazin-2-yl and 1, 2, 4-triazin-3-yl, especially pyridyl, pyrimidyl, furanyl and thienyl.
Im Hinblick auf die Verwendung der erfindungsgemäßen 1-Aryl- 4-thiouracile der Formel I als Herbizide haben die Variablen vorzugsweise folgende Bedeutungen, und zwar jeweils für sich allein oder in Kombination:With regard to the use of the 1-aryl-4-thiouracils of the formula I according to the invention as herbicides, the variables preferably have the following meanings, in each case individually or in combination:
X Sauerstoff;X oxygen;
R1 Wasserstoff, Amino oder Methyl, insbesondere Methyl;R 1 is hydrogen, amino or methyl, especially methyl;
R2 Wasserstoff, Halogen oder Methyl;R 2 is hydrogen, halogen or methyl;
R3 Wasserstoff, Halogen oder Methyl, insbesondere a) Wasserstoff oder Halogen, besonders bevorzugt Wasserstoff; b) Wasserstoff oder Methyl, besonders bevorzugt Methyl; c) Halogen oder Methyl, besonders bevorzugt Halogen;R 3 is hydrogen, halogen or methyl, in particular a) hydrogen or halogen, particularly preferably hydrogen; b) hydrogen or methyl, particularly preferably methyl; c) halogen or methyl, particularly preferably halogen;
R4 Fluor;R 4 fluorine;
R5 Cyano oder Halogen, insbesondere a) Cyano; b) Chlor;R 5 cyano or halogen, in particular a) cyano; b) chlorine;
Y die Methingruppe oder zusammen mit R6 eine Brücke >C-0-C (R10)=N-, insbesondere a) die Methingruppe; b) zusammen mit R5 eine Brücke >C-0-C (R10) =N-;Y is the methine group or together with R 6 a bridge> C-0-C (R 10 ) = N-, in particular a) the methine group; b) together with R 5 a bridge> C-0-C (R 10 ) = N-;
R6 einerseits zusammen mit R5 einen über den Sauerstoff an R5 gebundenen Rest -N(R7)-CO-C(R8' ,R9' )-0-;R 6, on the one hand, together with R 5, a radical -N (R 7 ) -CO-C (R 8 ', R 9 ') -0- bonded to R 5 via oxygen;
R6 andererseitsR 6 on the other hand
1) Wasserstoff, Hydroxy, Mercapto, Cyano, Nitro, Halogen, Ci-Cg -Alkyl, Ci-Cδ-Halogenalkyl, Ci-Cg-Halogenalkoxy,1) hydrogen, hydroxy, mercapto, cyano, nitro, halogen, Ci-Cg-alkyl, Ci-C δ -haloalkyl, Ci-Cg-haloalkoxy,
Ci-Cg-Halogenalkylthio, Cι-C6 -Alkylthio- (Ci-Cg-alkyl) - carbonyl, (Ci-Cg -Alkyl) iminooxycarbonyl, Ci -Cg-Alkoxy-Ci-Cg-alkyl, Ci -Cg-Alkoxyamino-Ci-Cg -alkyl , Ci-Cg-Alk- oxy-Ci -Cg -alkylamino-Ci -Cg -alkyl ,Ci-Cg-haloalkylthio, -CC 6 -alkylthio- (Ci-Cg-alkyl) carbonyl, (Ci-Cg-alkyl) iminooxycarbonyl, Ci -Cg-alkoxy-Ci-Cg-alkyl, Ci -Cg-alkoxyamino- Ci-Cg-alkyl, Ci-Cg-alkoxy-Ci-Cg -alkylamino-Ci-Cg -alkyl,
2) Ci-Cg-Alkoxy, Ci-C -Alkylthio, C3-Cg-Cycloalkoxy, C3-Cg- Cycloalkylthio, C2-Cg-Alkenyloxy, C2-Cg-Alkenylthio, C2-Cg-Alkinyloxy, C2-Cg-Alkinylthio, (Ci-Cg-Alkyl) - carbonyloxy, (Ci-Cg-Alkyl) carbonylthio, (C -Cδ -Alkoxy) - carbonyloxy, (C2-Cg-Alkenyl) carbonyloxy, (C2-Cg-Alkenyl) - carbonylthio, (C2-Cg-Alkinyl) carbonyloxy, (C2-Cg-Alkinyl) - carbonylthio, Ci-Cg-Alkylsulfonyloxy oder Ci-Cg-Alkyl- sulfonyl, wobei jeder dieser 17 Reste gewünschtenfalls einen bis drei Substituenten tragen kann, jeweils ausge- wählt aus der Gruppe bestehend aus2) Ci-Cg-alkoxy, Ci-C-alkylthio, C 3 -Cg-cycloalkoxy, C 3 -Cg-cycloalkylthio, C 2 -Cg-alkenyloxy, C 2 -Cg-alkenylthio, C 2 -Cg-alkynyloxy, C 2 -Cg-alkynylthio, (Ci-Cg-alkyl) - carbonyloxy, (Ci-Cg-alkyl) carbonylthio, (C -C δ- alkoxy) - carbonyloxy, (C 2 -Cg-alkenyl) carbonyloxy, (C 2 - Cg-alkenyl) - carbonylthio, (C 2 -Cg-alkynyl) carbonyloxy, (C 2 -Cg-alkynyl) - carbonylthio, Ci-Cg-alkylsulfonyloxy or Ci-Cg-alkylsulfonyl, each of these 17 residues if desired one to can carry three substituents, each selected from the group consisting of
Halogen, Nitro, Cyano, Hydroxy, C3-Cg-Cycloalkyl, Ci-Cg-Alkoxy, C3-Cg-Cycloalkoxy, C -Cg-Alkenyloxy, C3-Cg-Alkinyloxy, Cι-Cg-Alkoxy-Cι-Cg-alkoxy, Ci-Cg-Alkylthio, Ci-Cg-Alkylsulfinyl, Ci-Cg-Alkyl - sulfonyl, Ci-Cδ-Alkylidenaminoxy, Oxo, =N-0R11, der Phenyl-, Phenoxy- oder Phenylsulfonylgruppe, die unsubstituiert sein oder ein bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Halogen, Nitro, Cyano, Ci-Cδ-Alkyl, Ci-Cδ-Halogenalkyl, Cι-C6-Alkoxy und (Ci -C -Alkoxy) - carbonyl , -CO-R12, -CO-OR12, -CO-SR12, -CO-N (R12) -R13 , -OCO-R12, -OCO-OR12, -OCO-SR12, -OCO-N(R12) -R13, -N (R12) -R13 und -C(R14)=N-OR1:L;Halogen, nitro, cyano, hydroxyl, C 3 -Cg-cycloalkyl, Ci-Cg-alkoxy, C 3 -Cg-cycloalkoxy, C -Cg-alkenyloxy, C 3 -Cg-alkynyloxy, Cι-Cg-alkoxy-Cι-Cg -alkoxy, Ci-Cg-alkylthio, Ci-Cg-alkylsulfinyl, Ci-Cg-alkyl - sulfonyl, Ci-C δ -alkylidenaminoxy, oxo, = N-0R 11 , the phenyl, phenoxy or phenylsulfonyl group, which are unsubstituted or can carry one to three substituents each selected from the group consisting of halogen, nitro, cyano, Ci-C δ -alkyl, C δ haloalkyl, Cι-C 6 -alkoxy and (C -C alkoxy) - carbonyl, -CO-R 12 , -CO-OR 12 , -CO-SR 12 , -CO-N (R 12 ) -R 13 , -OCO-R 12 , -OCO-OR 12 , -OCO-SR 12 , -OCO -N (R 12 ) -R 13 , -N (R 12 ) -R 13 and -C (R 14 ) = N-OR 1: L ;
3) -CZ2-R15, -C(NR16) -Rl5, -C (R15 ) (Z3R17) (Z4R18) ,3) -CZ 2 -R 15 , -C (NR 1 6) -Rl5, -C (R 15 ) (Z 3 R 17 ) (Z 4 R 18 ),
-C (R15) =C (R19) -CN, -C (R15) =C (R19) -CO-R20, -CH(R15) -CH(R19) -CO-R20, -C (R15) =C (R19) -CH2-CO-R20, -C (R15) =C (R19) -C (R21) =C (R22) -CO-R20, -C(R15)=C(R19)-CH2-CH(R23)-CO-R20, -CO-OR24, -CO-SR24, -CO-N(R24) -OR11, -C≡C-CO-NH-OR11, -C≡C-CO-N (R24) -OR11,-C (R 15 ) = C (R 19 ) -CN, -C (R 15 ) = C (R 19 ) -CO-R 20 , -CH (R 15 ) -CH (R 19 ) -CO-R 20 , -C (R 15 ) = C (R 19 ) -CH 2 -CO-R 20 , -C (R 15 ) = C (R 19 ) -C (R 21 ) = C (R 22 ) -CO-R 20 , -C (R 15 ) = C (R 19 ) -CH 2 -CH (R 23 ) -CO-R 20 , -CO-OR 24 , -CO-SR 24 , -CO-N (R 24 ) - OR 11 , -C≡C-CO-NH-OR 11 , -C≡C-CO-N (R 24 ) -OR 11 ,
-C≡C-CS-NH-OR11, -C≡C-CS-N(R24) -OR11,-C≡C-CS-NH-OR 11 , -C≡C-CS-N (R 24 ) -OR 11 ,
-C(R15)=C(R19)-CO-NH-OR11, -C (R15) =C (R19) -CO-N(R24) -OR11, -C(R15)=C(R19) -CS-NH-OR11, -C (R15) =C (R19) -CS-N(R24) -OR11, -C (R15) =C (R19) -C (R14) »N-OR11, -C (R14) =N-OR11, -C≡C-C(R14)=N-OR11, -C(Z3R17) (Z R18) -OR24,-C (R 15 ) = C (R 19 ) -CO-NH-OR 11 , -C (R 15 ) = C (R 19 ) -CO-N (R 24 ) -OR 11 , -C (R 15 ) = C (R 19 ) -CS-NH-OR 11 , -C (R 15 ) = C (R 19 ) -CS-N (R 24 ) -OR 11 , -C (R 15 ) = C (R 19 ) -C (R 14 ) » N-OR 11 , -C (R 14 ) = N-OR 11 , -C≡CC (R 14 ) = N-OR 11 , -C (Z 3 R 17 ) (ZR 18 ) -OR 24 ,
-C(Z3R17) (Z4R18) -SR24, -C(Z3R17) (Z R18) -N(R25)R2(\ -N(R25) -R26 oder -CO-N (R25) -R26;-C (Z 3 R 17 ) (Z 4 R 18 ) -SR 24 , -C (Z 3 R 17 ) (ZR 18 ) -N (R 25 ) R 2 ( \ -N (R 25 ) -R 26 or -CO-N (R 25 ) -R 26 ;
R6 insbesondere 2) Ci-Cg-Alkoxy, C -Cg-Alkenyloxy oder C -Cg-Alkinyloxy, wobei jeder der letztgenannten 3 Reste gewünschtenfalls ein bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Halogen, Ci-Cg-Alkoxy, C3-Cδ-Alkenyloxy, C3-Cg-Alkinyloxy, Ci-Cg-Alkylsulfonyl, -CO-R12, -CO-OR12, -CO-N(R12)R13, -N (R12) -R13 undR 6 in particular 2) Ci-Cg-alkoxy, C -Cg-alkenyloxy or C-Cg-alkynyloxy, where each of the latter 3 radicals can optionally carry one to three substituents, each selected from the group consisting of halogen, Ci-Cg- Alkoxy, C 3 -C δ- alkenyloxy, C 3 -Cg-alkynyloxy, Ci-Cg-alkylsulfonyl, -CO-R 12 , -CO-OR 12 , -CO-N (R 12 ) R 13 , -N (R 12 ) -R 13 and
-C(R14)=N-OR1:L; 3) -CO-R15, -C(NR") -Rl5, -C(R15) (OR17) (OR18) ,-C (R 14 ) = N-OR 1: L ; 3) -CO-R 15, -C (NR ") -R l5, -C (R 15) (OR 17) (OR 18),
-C(R15)=C(R19)-CO-R20, -CH(R15)-CH(R9)-CO-R20, -CO-OR24, -CO-N(R24) -OR11, -C(R15)=C(R19) -CO-N(R24) -OR11, -C(R14)=N-OR11, -C(OR17) (OR18) -OR24, -N(R 5)R26 oder-C (R 15 ) = C (R 19 ) -CO-R 20 , -CH (R 15 ) -CH (R 9 ) -CO-R 20 , -CO-OR 24 , -CO-N (R 24 ) -OR 11 , -C (R 15 ) = C (R 19 ) -CO-N (R 24 ) -OR 11 , -C (R 14 ) = N-OR 11 , -C (OR 17 ) (OR 18 ) -OR 24 , -N (R 5 ) R 26 or
-CON(R25)R26;-CON (R 25 ) R 26 ;
R8, R9, R8', R9' Wasserstoff. R 8 , R 9 , R 8 ', R 9 ' hydrogen.
Ganz besonders bevorzugt sind die 1-Aryl -4 -thiouracile der Formel Ia (ώ i mit X = Sauerstoff, R2 = Wasserstoff, R3 = Wasserstoff und Y = die Methingruppe)The 1-aryl -4 -thiouracils of the formula Ia are very particularly preferred (ώ i with X = oxygen, R 2 = hydrogen, R 3 = hydrogen and Y = the methine group)
Figure imgf000045_0001
insbesondere die in der folgenden Tabelle 1 aufgeführten Verbindungen la.l bis Ia.160:
Figure imgf000045_0001
in particular the compounds la.l to Ia.160 listed in the following Table 1:
Tabelle 1Table 1
Figure imgf000045_0002
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0003
Figure imgf000045_0002
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0003
Des weiteren sind die l-Aryl-4-thiouracile der Formeln Ib bis Iq besonders bevorzugt, insbesondereFurthermore, the l-aryl-4-thiouracils of the formulas Ib to Iq are particularly preferred, in particular
die Verbindungen Ib.l bis Ib.160, die sich von den entsprechenden Verbindungen la.l bis Ia.160 lediglich dadurch unterscheiden, daß R2 für Fluor steht:the compounds Ib.l to Ib.160, which differ from the corresponding compounds la.l to Ia.160 only in that R 2 is fluorine:
Figure imgf000049_0001
Figure imgf000049_0001
die Verbindungen Ic.l bis Ic.160, die sich von den entsprechenden Verbindungen la.l bis Ia.160 lediglich dadurch unterscheiden, daß R2 für Chlor steht:the compounds Ic.l to Ic.160, which differ from the corresponding compounds la.l to Ia.160 only in that R 2 is chlorine:
Figure imgf000049_0002
die Verbindungen Id.l bis Id.160, die sich von den entsprechenden Verbindungen la.l bis Ia.160 lediglich dadurch unterscheiden, daß R3 für Methyl steht:
Figure imgf000049_0002
the compounds Id.l to Id.160, which differ from the corresponding compounds la.l to Ia.160 only in that R 3 is methyl:
Figure imgf000050_0001
Figure imgf000050_0001
die Verbindungen Ie.l bis Ie.160, die sich von den entsprechenden Verbindungen la.l bis Ia.160 lediglich dadurch unterscheiden, daß R2 für Fluor und R3 für Methyl stehen:the compounds Ie.l to Ie.160, which differ from the corresponding compounds la.l to Ia.160 only in that R 2 is fluorine and R 3 is methyl:
Figure imgf000050_0002
Figure imgf000050_0002
die Verbindungen If .1 bis If .160, die sich von den entsprechenden Verbindungen la.l bis Ia.160 lediglich dadurch unterscheiden, daß R2 für Chlor und R3 für Methyl stehen:the compounds If .1 to If .160, which differ from the corresponding compounds la.l to Ia.160 only in that R 2 is chlorine and R 3 is methyl:
Figure imgf000050_0003
Figure imgf000050_0003
die Verbindungen Ig.l bis Ig.160, die sich von den entsprechenden Verbindungen la.l bis Ia.160 lediglich dadurch unterscheiden, daß R3 für Trifluormethyl steht:the compounds Ig.l to Ig.160, which differ from the corresponding compounds la.l to Ia.160 only in that R 3 is trifluoromethyl:
Figure imgf000050_0004
Figure imgf000050_0004
die Verbindungen Ih.l bis Ih.160, die sich von den entsprechenden Verbindungen la.l bis Ia.160 lediglich dadurch unterscheiden, daß R2 für Fluor und R3 für Trifluormethyl stehen:
Figure imgf000051_0001
the compounds Ih.l to Ih.160, which differ from the corresponding compounds la.l to Ia.160 only in that R 2 is fluorine and R 3 is trifluoromethyl:
Figure imgf000051_0001
die Verbindungen Ii.l bis Ii.160, die sich von den entsprechenden Verbindungen la.l bis Ia.160 lediglich dadurch unterscheiden, daß R2 für Chlor und R3 für Trifluormethyl stehen:the compounds Ii.l to Ii.160, which differ from the corresponding compounds la.l to Ia.160 only in that R 2 is chlorine and R 3 is trifluoromethyl:
Figure imgf000051_0002
Figure imgf000051_0002
die Verbindungen Ik.l bis Ik.160, die sich von den entsprechenden Verbindungen la.l bis Ia.160 lediglich dadurch unterscheiden, daß R3 für Fluor steht:the compounds Ik.l to Ik.160, which differ from the corresponding compounds la.l to Ia.160 only in that R 3 is fluorine:
Figure imgf000051_0003
Figure imgf000051_0003
die Verbindungen Im.l bis Im.160, die sich von den entsprechenden Verbindungen la.l bis Ia.160 lediglich dadurch unterscheiden, daß R2 und R3 für Fluor stehen:the compounds Im.l to Im.160, which differ from the corresponding compounds la.l to Ia.160 only in that R 2 and R 3 are fluorine:
Figure imgf000051_0004
Figure imgf000051_0004
die Verbindungen In.l bis In.160, die sich von den entsprechenden Verbindungen la.l bis Ia.160 lediglich dadurch unterscheiden, daß R2 für Chlor und R3 für Fluor stehen:the compounds In.l to In.160, which differ from the corresponding compounds la.l to Ia.160 only in that R 2 is chlorine and R 3 is fluorine:
Figure imgf000051_0005
die Verbindungen Io.l bis I0.I6O, die sich von den entsprechenden Verbindungen la.l bis Ia.160 lediglich dadurch unterscheiden, daß R3 für Chlor steht:
Figure imgf000051_0005
the compounds Io.l to I0.I6O, which differ from the corresponding compounds la.l to Ia.160 only in that R 3 is chlorine:
Figure imgf000052_0001
Figure imgf000052_0001
die Verbindungen Ip.l bis Ip.160, die sich von den entsprechenden Verbindungen la.l bis Ia.160 lediglich dadurch unterscheiden, daß R2 für Fluor und R3 für Chlor stehen:the compounds Ip.l to Ip.160, which differ from the corresponding compounds la.l to Ia.160 only in that R 2 is fluorine and R 3 is chlorine:
Figure imgf000052_0002
Figure imgf000052_0002
die Verbindungen Iq.l bis Iq.160, die sich von den entsprechenden Verbindungen la.l bis Ia.160 lediglich dadurch unterscheiden, daß R2 und R3 für Chlor stehen:the compounds Iq.l to Iq.160, which differ from the corresponding compounds la.l to Ia.160 only in that R 2 and R 3 are chlorine:
Figure imgf000052_0003
Figure imgf000052_0003
Außerdem sind die 1-Aryl-4-thiouracile der Formel Ir {≤ I mit X = Sauerstoff; Y = Methylen; R5+R6 = -N(R7) -CO-CH2-0-}In addition, the 1-aryl-4-thiouracils of the formula Ir {≤ I with X = oxygen; Y = methylene; R 5 + R 6 = -N (R 7 ) -CO-CH 2 -0-}
Figure imgf000052_0004
besonders bevorzugt, insbesondere die in der folgenden Tabelle 2 aufgeführen Verbindungen Ir.l bis Ir.96:
Figure imgf000052_0004
particularly preferred, in particular the compounds Ir.l to Ir.96 listed in Table 2 below:
Tabelle 2Table 2
Figure imgf000052_0005
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000055_0001
Figure imgf000052_0005
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000055_0001
Die l-Aryl-4-Thiouracile der Formel I sind auf verschiedene Weise erhältlich, insbesondere nach einem der folgenden Verfahren:The l-aryl-4-thiouracils of the formula I can be obtained in various ways, in particular by one of the following processes:
A) Schwefelung eines 1-Aryluracils der Formel II:A ) Sulfurization of a 1-aryluracil of the formula II:
Figure imgf000056_0001
Figure imgf000056_0001
IIII
Die Schwefelung erfolgt in der Regel in einem inerten Lösungs- oder Verdünnungsmittel, beispielsweise in einem aromatischen Kohlenwasserstoff wie Toluol und den Xylolen, in einem Ether wie Diethylether, 1, 2-Dimethoxyethan und Tetrahydrofuran, oder in einem organischen Amin wie Pyridin.The sulfurization is usually carried out in an inert solvent or diluent, for example in an aromatic hydrocarbon such as toluene and the xylenes, in an ether such as diethyl ether, 1, 2-dimethoxyethane and tetrahydrofuran, or in an organic amine such as pyridine.
Als Schwefelungsreagenz eignen sich besonders gut Phosphor (V) -sulfid und 2, 4 -Bis (4 -methoxyphenyl) -1, 3, 2, 4 - dithiadiphosphetan-2, 4 -dithion ("Lawesson-Reagenz") .Phosphorus (V) sulfide and 2,4-bis (4-methoxyphenyl) -1,3,4,4-dithiadiphosphetane-2,4-dithione ("Lawesson's reagent") are particularly suitable as the sulfurization reagent.
Üblicherweise ist die 1- bis 5 -fache molare Menge, bezogen auf die zu schwefelnde Ausgangsverbindung, für eine weitgehend vollständige Umsetzung ausreichend.Usually 1 to 5 times the molar amount, based on the starting compound to be sulfurized, is sufficient for a largely complete reaction.
Die Reaktionstemperatur liegt normalerweise bei 20 bis 200°C, vorzugsweise bei 40°C bis zur Siedetemperatur des Reaktions- gemisches .The reaction temperature is normally 20 to 200 ° C, preferably 40 ° C to the boiling point of the reaction mixture.
Die Vorprodukte II sind aus der WO 97/05117 bekannt oder in analoger Weise nach einem der dort beschriebenen Verfahren herstellbar.The preliminary products II are known from WO 97/05117 or can be produced in an analogous manner by one of the processes described there.
B) Umsetzung eines 4-Thiouracils der Formel III mit einem Fluoraromaten der Formel IV:B) Reaction of a 4-thiouracil of the formula III with a fluoroaromatic compound of the formula IV:
Figure imgf000056_0002
Die Reaktion gelingt besonders gut, wenn IV eine elektronenziehende Gruppe in ortho- oder para-Stellung zum Fluoratom trägt.
Figure imgf000056_0002
The reaction is particularly successful when IV carries an electron-withdrawing group ortho or para to the fluorine atom.
Anstelle von IV kann auch ein Fluoraromat, der sich in IV überführen läßt, eingesetzt werden.Instead of IV, a fluoroaromatic which can be converted into IV can also be used.
C) Umsetzung einer Verbindung Va, Vb oder Vc mit einem Arylamin der Formel VI :C) Reaction of a compound Va, Vb or Vc with an arylamine of the formula VI:
Figure imgf000057_0001
Vc
Figure imgf000057_0001
Vc
L1, L2, L3 stehen jeweils für übliche Hydroxyl-Schutzgruppen wie Methyl, Ethyl, Methylsulfonyl, Benzyl und Trimethylsilyl .L 1 , L 2 , L 3 each represent customary hydroxyl protective groups such as methyl, ethyl, methylsulfonyl, benzyl and trimethylsilyl.
Die erfindungsgemäßen Verfahren (B) ) und (C) ) zur Herstellung der Verbindungen der Formel (I) werden vorzugsweise in Gegenwart eines geeigneten Reaktionshilfsmittels durchgeführt.The processes (B)) and (C)) according to the invention for the preparation of the compounds of the formula (I) are preferably carried out in the presence of a suitable reaction auxiliary.
Als Reaktionshilfsmittel kommen im allgemeinen die üblichen anorganischen oder organischen Basen oder Säureakzeptoren in Betracht. Hierzu gehören vorzugsweise Alkalimetall- oder Erdalkalimetall- -acetate, -amide, -carbonate, -hydrogencarbonate, -hydride, -hydroxide oder -alkanolate, beispielsweise Natrium-, Kalium- oder Calciumacetat, Lithium-, Natrium-, Kalium- oder Calciumamid, Natrium-, Kalium- oder Calciumcarbonat, Natrium-, Kalium- oder Calciumhydrogencarbonat, Lithium-, Natrium-, Kaliumoder Calciumhydrid, Lithium-, Natrium-, Kalium- oder Calcium- hydroxid, Natrium- oder Kaliummethanolat, -ethanolat, n- oder iso-propanolat, n-, iso-, sec- oder tert.-butanolat; weiterhin auch basische organische StickstoffVerbindungen, beispielsweise Trimethylamin, Triethylamin, Tripropylamin, Tributyl- amin, Ethyl-diisopropylamin, N,N-Dimethyl-cyclohexylamin, Di- cyclohexylamin, Ethyl-dicyclohexylamin, N,N-Dimethyl-anilin, N,N-Dimethyl-benzylamin, Pyridin, 2-Methyl-, 3-Methyl-, 4-Methyl-, 2, 4-Dirnethyl-, 2, 6-Dirnethyl-, 3,4-Dimethyl und 3,5-Di- methylpyridin, 5-Ethyl-2-methylpyridin, 4-Dimethylaminopyridin, N-Methylpiperidin, 1, 4-Diazabicyclo [2, 2, 2] -octan (DABCO) , 1,5-Di- azabicyclo [4 , 3 , 0] -non-5-en (DBN) oder 1,8 Diazabicyclo [5, 4 , 0] -un- dec-7-en (DBU) .The usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, for example sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium -, potassium or calcium carbonate, sodium, Potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n- or iso-propanolate, n-, iso-, sec- or tert-butoxide; also basic organic nitrogen compounds, for example trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimethyl -benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2, 4-dimethyl, 2, 6-dimethyl, 3,4-dimethyl and 3,5-dimethylpyridine, 5- Ethyl-2-methylpyridine, 4-dimethylaminopyridine, N-methylpiperidine, 1, 4-diazabicyclo [2, 2, 2] octane (DABCO), 1,5-di-azabicyclo [4, 3, 0] -non-5 -en (DBN) or 1.8 diazabicyclo [5, 4, 0] -un-dec-7-ene (DBU).
Die erfindungsgemäßen Verfahren (B) ) und (C) ) zur Herstellung der Verbindung der Formel (I) werden vorzugsweise in Gegenwart eines Verdünnungsmittels durchgeführt. Als Verdünnungsmittel kommen im allgemeinen die üblichen organischen Lösungsmittel in Betracht. Hierzu gehören vorzugsweise aliphatische, alicyclische und aromatische, gegebenenfalls halogenierte Kohlenwasserstoffe, beispielsweise Pentan, Hexan, Heptan, Petrolether, Ligroin, Benzin, Benzol, Toluol, Xylol, Chlorbenzol, Dichlorbenzol, Cyclohexan, Methylcyclohexan, Dichlormethan (Methylenchlorid) , Trichlormethan (Chloroform) oder Tetrachlormethan, Dialkylether wie Diethylether, Diisopropylether, Methyl-tert .-butyl-ether (MTBE) , Ethyl- tert.-butylether, Methyl-tert . -pentylether (TAME) , Ethyl-tert.- pentylether, Tetrahydrofuran (THF) , 1,4-Dioxan, Ethylenglycol-di- methylether, Ethylenglycol-diethylether, Diethylenglycol-di- methylether und -diethylether; Dialkylketone, wie Aceton, Butanon (Methylethylketon) , Methyl-isopropylketon und Methyl-isobutyl- keton; Nitrile wie Acetonitril, Propionitril, Butyronitril und Benzonitril; Amide wie N,N-Dimethylformamid (DMF) , N,N-Dimethyl- acetamid, N-Methylformanilid, N-Methylpyrrolidon und Hexamethyl- phosphorsäuretriamid; Ester wie Essigsäure-methylester, -ethyl - ester, -n-propylester, -isopropylester, -n-butylester, -isobutyl- ester und -sec-butylester; Sulfoxide wie Dimethylsulfoxid; Alkanole wie Methanol, Ethanol, n-Propanol, Isopropanol, n-, iso-, sec- und tert .-Butanol; Glycolether wie Ethylenglycol- monomethylether, -monoethylether, Diethylenglycol-monomethylether und -monoethylether; deren Gemische mit Wasser oder reines Wasser.The processes (B)) and (C)) according to the invention for the preparation of the compound of the formula (I) are preferably carried out in the presence of a diluent. The usual organic solvents are generally suitable as diluents. These preferably include aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons, for example pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane (methylene chloride), trichloromethane (chloroform) Tetrachloromethane, dialkyl ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether (MTBE), ethyl tert-butyl ether, methyl tert. pentyl ether (TAME), ethyl tert-pentyl ether, tetrahydrofuran (THF), 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether and diethyl ether; Dialkyl ketones such as acetone, butanone (methyl ethyl ketone), methyl isopropyl ketone and methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile, butyronitrile and benzonitrile; Amides such as N, N-dimethylformamide (DMF), N, N-dimethyl-acetamide, N-methylformanilide, N-methylpyrrolidone and hexamethylphosphoric acid triamide; Esters such as methyl acetate, ethyl ester, n-propyl ester, isopropyl ester, n-butyl ester, isobutyl ester and sec-butyl ester; Sulfoxides such as dimethyl sulfoxide; Alkanols such as methanol, ethanol, n-propanol, isopropanol, n-, iso-, sec- and tert-butanol; Glycol ethers such as ethylene glycol monomethyl ether, monoethyl ether, diethylene glycol monomethyl ether and monoethyl ether; their mixtures with water or pure water.
Die Reaktionstemperaturen können bei der Durchführung der Ver- fahren (B) ) und (C) ) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen von 0 bis 200°C, vor- zugsweise bei 10 bis 150°C, insbesondere bei 20°C bis Siedetemperatur des jeweiligen Reaktionsgemisches.The reaction temperatures can be varied within a substantial range when carrying out processes (B)) and (C)). In general, temperatures from 0 to 200 ° C, preferably at 10 to 150 ° C, especially at 20 ° C to the boiling point of the respective reaction mixture.
Zur Durchführung der Verfahren (A) ) , (B) ) und (C>) werden die Aus- gangsstoffe im allgemeinen in angenähert äquimolaren Mengen eingesetzt. Es ist jedoch auch möglich, jeweils eine der Komponenten in einem größeren Überschuß zu verwenden, etwa bis zur 2fachen molaren Menge der andere Komponente. Bei Verfahren A) beispielsweise empfiehlt es sich, das Schwefelungsreagenz im Überschuß einzusetzen.To carry out processes (A)), (B)) and (C>), the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess, for example up to twice the molar amount of the other component. In process A), for example, it is advisable to use the sulfurization reagent in excess.
Die Verfahren (A> ) , (B)) und (C) ) werden zweckmäßigerweise bei Atmosphärendruck oder unter dem Eigendruck des jeweiligen Reaktionsgemisches vorgenommen. Es ist jedoch auch möglich, die Verfah- ren unter erhöhtem oder vermindertem Druck - im allgemeinen bei 0,1 bis 10 bar - durchzuführen.The processes (A>), (B)) and (C)) are advantageously carried out at atmospheric pressure or under the autogenous pressure of the respective reaction mixture. However, it is also possible to carry out the processes under increased or reduced pressure - generally at 0.1 to 10 bar.
Die Aufarbeitung der jeweiligen Reaktionsgemische erfolgt in der Regel nach an sich bekannten Methoden, beispielsweise durch Ver- dünnen der Reaktionslösung mit Wasser und anschließender Isolierung des Produktes mittels Filtration, Kristallisation oder Lösungsmittelextraktion, oder durch Entfernen des Lösungsmittels, Verteilen des Rückstandes in einem Gemisch aus Wasser und einem geeigneten organischen Lösungsmittel und Aufarbeiten der organischen Phase auf das Produkt hin.The respective reaction mixtures are generally worked up by methods known per se, for example by diluting the reaction solution with water and then isolating the product by means of filtration, crystallization or solvent extraction, or by removing the solvent, and distributing the residue in a mixture of water and a suitable organic solvent and working up the organic phase on the product.
Im allgemeinen sind die l-Aryl-4-thiouracile I nach einem der vorstehend genannten Syntheseverfahren herstellbar. Aus wirt- schaftlichen oder verfahrenstechnischen Gründen kann es jedoch zweckmäßiger sein, einige Verbindungen I aus ähnlichen l-Aryl-4-thiouracilen - die sich jedoch insbesondere in der Bedeutung der Reste R5 und/oder R6 unterscheiden - herzustellen, und zwar auf an sich bekannte Weise, z.B. durch Esterhydrolyse, Veresterung, Amidierung, Acetalisierung, Acetalhydrolyse, Kondensationsreaktion, Wittig-Reaktion, Peterson-Olefinierung, Veretherung, Alkylierung, Oxidation oder Reduktion.In general, the l-aryl-4-thiouracile I can be prepared by one of the synthesis methods mentioned above. For economic or procedural reasons, however, it may be more expedient to prepare some compounds I from similar 1-aryl-4-thiouracils - which differ, however, in particular in the meaning of the radicals R 5 and / or R 6 - specifically on known way, for example by ester hydrolysis, esterification, amidation, acetalization, acetal hydrolysis, condensation reaction, Wittig reaction, Peterson olefination, etherification, alkylation, oxidation or reduction.
Die l-Aryl-4-thiouracile I können bei der Herstellung als Isomerengemische anfallen, die jedoch gewünschtenfalls nach den hierfür üblichen Methoden wie Kristallisation oder Chromatographie, auch an einem optisch aktiven Adsorbat, in die reinen Isomeren getrennt werden können. Reine optisch aktive Isomere lassen sich vorteilhaft aus entsprechenden optisch aktiven Ausgangsprodukten herstellen. Landwirtschaftlich brauchbare Salze der Verbindungen I können durch Reaktion mit einer Base des entsprechenden Kations, vorzugsweise einem Alkalimetallhydroxid oder -hydrid, oder durch Reaktion mit einer Säure des entsprechenden Anions, vorzugsweise der Chlorwasserstoffsäure, Bromwasserstoffsäure, Schwefelsäure, Phosphorsäure oder Salpetersäure, gebildet werden.The l-aryl-4-thiouracils I can be obtained in the preparation as isomer mixtures, which, however, can, if desired, be separated into the pure isomers by the customary methods such as crystallization or chromatography, including on an optically active adsorbate. Pure optically active isomers can advantageously be prepared from corresponding optically active starting products. Agricultural salts of the compounds I can be formed by reaction with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride, or by reaction with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
Salze von I, deren Metallion kein Alkalimetallion ist, können auch durch Umsalzen des entsprechenden Alkalimetall - salzes in üblicher Weise hergestellt werden, ebenso Ammonium-, Phosphonium- , Sulfonium- und Sulfoxoniumsalze mittels Ammoniak, Phosphonium- , Sulfonium- oder Sulfoxoniumhydroxiden.Salts of I, the metal ion of which is not an alkali metal ion, can also be prepared in a conventional manner by salting the corresponding alkali metal salt, as can ammonium, phosphonium, sulfonium and sulfoxonium salts using ammonia, phosphonium, sulfonium or sulfoxonium hydroxides.
Die Verbindungen I und deren landwirtschaftlich brauchbaren Salze eignen sich - sowohl als Isomerengemische als auch in Form der reinen Isomeren - als Herbizide. Die 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 Schad- gräser, ohne die Kulturpflanzen nennenswert zu schädigen. Dieser Effekt tritt vor allem bei niedrigen Aufwandmengen auf.The compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides. The herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, maize, soybeans and cotton, they work against weeds and grass weeds without causing any significant damage to crops. This effect occurs especially at low application rates.
In Abhängigkeit von der jeweiligen Applikationsmethode können die Verbindungen I bzw. sie enthaltenden herbiziden Mittel noch in einer weiteren Zahl von Kulturpflanzen zur Beseitigung unerwünschter Pflanzen eingesetzt werden. In Betracht kommen beispielsweise folgende Kulturen:Depending on the particular application method, the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants. The following crops are considered, for example:
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 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,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 tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea libericaus), Cucumodison , Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum,
(Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium) , Helianthus annuus, Hevea brasiliensis, Hordeum vulgäre, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgäre), Theobroma cacao, Tri- folium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera und Zea ays .(Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgäre, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersica, Musus spec, manus spec, Medicinal specimen, Malus spec. Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarle, Seeale Solanum tuberosum, Sorghum bicolor (S. vulgäre), Theobroma cacao, Tri- folium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea ays.
Darüber hinaus können die Verbindungen I auch in Kulturen, die durch Züchtung einschließlich gentechnischer Methoden gegen die Wirkung von Herbiziden tolerant sind, verwandt werden.In addition, the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
Die Verbindungen 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 Dispersionen, Emulsionen, Oldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsformen richten sich nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten.The compounds I or the herbicidal compositions comprising them can be sprayed or atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring. The application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
Als inerte Hilfsstoffe kommen im Wesentlichen in Betracht: Mineralölfraktionen von mittlerem bis hohem Siedepunkt wieThe following are essentially considered as inert auxiliaries: mineral oil fractions of medium to high boiling point such as
Kerosin und Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z.B. Paraffine, Tetrahydronaphthalin, alkylierte Naphthaline und deren Derivate, alkylierte Benzole und deren Derivate, Alkohole wie Methanol, Ethanol, Propanol, Butanol und Cyclohexanol, Ketone wie Cyclohexanon, stark polare Lösungsmittel, z.B. Amine wie N-Methylpyrrolidon und Wasser.Kerosene and diesel oil, also coal tar oils as well as 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, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Suspensionen, Pasten, netzbaren Pulvern oder wasserdispergier- baren Granulaten durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Oldispersionen können die l-Aryl-4-thiouracile I als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgier- mittel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz, Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oldispersions, the l-aryl-4-thiouracile I as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, it is also possible to prepare concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Lignin-, Phenol-, Naphthalin- und Dibutylnaphthalinsulfonsäure, sowie von Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanolen sowie von Fettalkoholglykolether, Kondensationsprodukte von sulfoniertem Naphthalin und seiner Derivate mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxy- ethylenoctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenyl-, Tributylphenylpolyglykolether, Alkyl - arylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethylen- 5 oxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylen- oder Polyoxypropylenalkylether, Laurylalkoholpolyglykoletheracetat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht.The surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols and of fatty alcohol glycol ether, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl polyglycol ether, alkyl aryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide, laurylalkylene glycol, ethoxylated ethoxylated alcohol, polyoxyethylene ethoxylated alcohol, ethoxylated castor oil, ethoxylated castor oil, ethoxylated castor oil, ethoxylated castor oil, ethoxylated castor oil, ethoxylated castor oil -Sulfite waste or methyl cellulose into consideration.
10 Pulver-, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.10 Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate 15 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, Dünge- 20 mittel, wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe.Granules, e.g. Coating, impregnation and homogeneous granules 15 can be produced by binding the active ingredients to solid carriers. Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate , Ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
25 Die Konzentrationen der Wirkstoffe I in den anwendungsfertigen Zubereitungen können in weiten Bereichen variiert werden. Im allgemeinen enthalten die Formulierungen etwa 0,001 bis 98 Gew.-%, vorzugsweise 0,01 bis 95 Gew. -%, mindestens eines Wirkstoffs. Die Wirkstoffe werden dabei in einer Reinheit von25 The concentrations of the active ingredients I in the ready-to-use preparations can be varied within a wide range. In general, the formulations contain about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are in a purity of
30 90 % bis 100 %, vorzugsweise 95 % bis 100 % (nach NMR-Spektrum) eingesetzt.30 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
Die folgenden Formulierungsbeispiele verdeutlichen die Herstellung solcher Zubereitungen: 35The following formulation examples illustrate the preparation of such preparations: 35
I. 20 Gewichtsteile der Verbindung Nr. Ib.3 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-monoethanol- 40 amid, 5 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfon- säure und 5 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Rizinusöl besteht. Durch Ausgießen und feines Verteilen der Lösung in 100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 45 0,02 Gew. -% des Wirkstoffs enthält. II. 20 Gewichtsteile der Verbindung Nr. Ib.3 werden in einer Mischung gelöst, die aus 40 Gewichtsteilen Cyclohexanon,I. 20 parts by weight of compound no. Ib.3 are dissolved in a mixture consisting of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanol-40 amide, 5 parts by weight of calcium salt Dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained which contains 45 0.02% by weight of the active ingredient. II. 20 parts by weight of compound no. Ib.3 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone,
30 Gewichtsteilen Isobutanol, 20 Gewichtsteilen des Anlagerungsproduktes von 7 Mol Ethylenoxid an 1 Mol Isooctyl- phenol 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 enthält.30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 10 parts by weight of the additive of 40 moles of ethylene oxide with 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.
III. 20 Gewichtsteile des Wirkstoffs Nr. Ib.3 werden in einer Mischung gelöst, die aus 25 Gewichtsteilen Cyclohexanon, 65 Gewichtsteilen einer Mineralölfraktion vom Siedepunkt 210 bis 280°C und 10 Gewichtsteilen des Anlagerungs- Produktes 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 enthält.III. 20 parts by weight of active ingredient no. Ib.3 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.
IV. 20 Gewichtsteile des Wirkstoffs Nr. Ib.3 werden mit 3 Gewichtsteilen des Natriumsalzes der Diisobutyl- naphthalin-α-sulfonsäure, 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 20 000 Gewichtsteilen Wasser enthält man eine Spritzbrühe, die 0,1 Gew. -% des Wirkstoffs enthält.IV. 20 parts by weight of active ingredient No. Ib.3 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of 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, a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
V. 3 Gewichtsteile des Wirkstoffs Nr. Ib.3 werden mitV. 3 parts by weight of active ingredient no. Ib.3 are with
97 Gewichtsteilen feinteiligem Kaolin vermischt. Man erhält auf diese Weise ein Stäubemittel, das 3 Gew. -% des Wirkstoffs enthält.97 parts by weight of finely divided kaolin mixed. In this way, a dusting agent is obtained which contains 3% by weight of the active ingredient.
VI. 20 Gewichtsteile des Wirkstoffs Nr. Ib.3 werden mitVI. 20 parts by weight of active ingredient No. Ib.3 are with
2 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure, 8 Gewichtsteilen Fettalkohol-polyglykolether, 2 Gewichtsteilen Natriumsalz eines Phenol-Harnstoff-Formaldehyd- Kondensates und 68 Gewichtsteilen eines paraffinischen Mineralöls innig vermischt. Man erhält eine stabile ölige Dispersion. VII. 1 Gewichtsteil der Verbindung Nr. Ib.3 wird in einer Mischung gelöst, die aus 70 Gewichtsteilen Cyclohexanon, 20 Gewichtsteilen ethoxyliertem Isooctylphenol und2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained. VII. 1 part by weight of compound no. Ib.3 is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and
10 Gewichtsteilen ethoxyliertem Rizinusöl besteht. Man erhält ein stabiles Emulsionskonzentrat.There are 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.
VIII. 1 Gewichtsteil der Verbindung Nr. Ib.3 wird in einer Mischung gelöst, die aus 80 Gewichtsteilen Cyclohexanon und 20 Gewichtsteilen Wettol® EM 31 (= nichtionischer Emulgator auf der Basis von ethoxyliertem Rizinusöl; BASF AG) besteht. Man erhält ein stabiles Emulsionskonzentrat... VIII 1 part by weight of Compound No. Ib.3 is dissolved in a mixture containing 31 (= nonionic emulsifier based on ethoxylated castor oil; BASF AG) 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol ® EM consists. A stable emulsion concentrate is obtained.
Die Applikation der Wirkstoffe I bzw. der herbiziden Mittel kann im Vorauflauf- oder im Nachauflaufverfahren erfolgen. Sind die Wirkstoffe für gewisse Kulturpflanzen weniger verträglich, so können Ausbringungstechniken angewandt werden, bei welchen die herbiziden Mittel mit Hilfe der Spritzgeräte so gespritzt werden, daß die Blätter der empfindlichen Kulturpflanzen nach Möglichkeit nicht getroffen werden, während die Wirkstoffe auf die Blätter darunter wachsender unerwünschter Pflanzen oder die unbedeckte Bodenfläche gelangen (post-directed, lay-by) .The active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
Die Aufwandmengen an Wirkstoff I betragen je nach Bekämpfungs- ziel, Jahreszeit, Zielpflanzen und WachstumsStadium 0,001 bis 3,0, vorzugsweise 0,01 bis 1,0 kg/ha aktive Substanz (a.S.).The application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.) depending on the control target, the season, the target plants and the growth stage.
Zur Verbreiterung des WirkungsSpektrums und zur Erzielung syn- ergistischer Effekte können die l-Aryl-4-thiouracile 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, Aminotriazole, Anilide, Aryloxy-/Heteroaryloxyalkansäuren und deren Derivate, Benzoesäure und deren Derivate, Benzothiadi- azinone, 2 - (Hetaroyl/Aroyl) -1, 3 -cyclohexandione, Heteroaryl-Aryl- Ketone, Benzylisoxazolidinone, meta-CF3-Phenylderivate, Carbamate, Chinolincarbonsäure und deren Derivate, Chloracetanilide, Cyclo- hexan-1, 3-dionderivate, Diazine, Dichlorpropionsäure und deren Derivate, Dihydrobenzofurane, Dihydrofuran-3-one, Dinitroaniline, Dinitrophenole, Diphenylether, Dipyridyle, Halogencarbonsäuren und deren Derivate, Harnstoffe, 3-Phenyluracile, Imidazole, Imidazolinone, N-Phenyl-3 ,4,5, 6-tetrahydrophthalimide, Oxadi - azole, Oxirane, Phenole, Aryloxy- und Heteroaryloxyphenoxy- propionsäureester, Phenylessigsäure und deren Derivate, 2-Phenyl- propionsäure und deren Derivate, Pyrazole, Phenylpyrazole, Pyridazine, Pyridincarbonsäure und deren Derivate, Pyrimidyl- ether, Sulfonamide, Sulfonylharnstoffe, Triazine, Triazinone, Triazolinone, Triazolcarboxamide und Uracile in Betracht.In order to broaden the spectrum of activity and to achieve synergistic effects, the l-aryl-4-thiouracile I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together. For example, 1, 2, 4-thiadiazoles, 1, 3, 4-thiadiazoles, amides, aminophosphoric acid and their derivatives, aminotriazoles, anilides, aryloxy / heteroaryloxyalkanoic acids and their derivatives, benzoic acid and their derivatives, benzothiadiazinones, 2 - (Hetaroyl / aroyl) -1, 3 -cyclohexanediones, heteroaryl-aryl-ketones, benzylisoxazolidinones, meta-CF 3 -phenyl derivatives, carbamates, quinolinecarboxylic acid and their derivatives, chloroacetanilides, cyclohexane-1, 3-dione derivatives, diazines and dichloropropion their derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3, 4,5, 6-tetrahydrophthalimides, oxo azoles, oxiranes, phenols, aryloxy and heteroaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uraciles.
Außerdem kann es von Nutzen sein, die Verbindungen I allein oder in Kombination mit anderen Herbiziden auch noch mit weiteren Pflanzenschutzmitteln gemischt, gemeinsam auszubringen, beispielsweise mit Mitteln zur Bekämpfung von Schädlingen oder phytopathogenen Pilzen bzw. Bakterien. Von Interesse ist ferner die Mischbarkeit mit Mineralsalzlösungen, welche zur Behebung von Ernährungs- und Spurenelementmängeln eingesetzt werden. Es können auch nichtphytotoxische Öle und Ölkonzentrate zugesetzt werden.It may also be useful to apply the compounds I alone or in combination with other herbicides, mixed with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used to remedy nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.
HerstellungsbeispieleManufacturing examples
Beispiel 1 (Verbindung Ib.3)Example 1 (compound Ib.3)
5-Fluor-4- (5-fluor-3-methyl-2-oxo-4-thioxo-3, 4-dihydro-2H-pyrimi- din-l-yl) -2- (1-methyl-prop-2-inyloxy) -benzonitril5-fluoro-4- (5-fluoro-3-methyl-2-oxo-4-thioxo-3,4,4-dihydro-2H-pyrimidin-l-yl) -2- (1-methyl-prop-2 -inyloxy) -benzonitrile
Zu einer Lösung von 1,7 g 5-Fluor-4- (5-fluor-3-methyl-2, 4-dioxo- 3 , 4-dihydro-2H-pyrimidin-l-yl) -2- (1-methyl-prop-2-inyloxy) -benzonitril in 50 ml Toluol wurden bei ca. 20°C 1 g "Lawesson-Reagenz" {2, 4-Bis (4-methoxyphenyl) -1,3,2, 4-dithiadiphosphetan-2, 4-dithion} gegeben. Anschließend rührte man 10 Std. bei Rückflußtemperatur. Dann wurde die Mischung nochmal mit 1 g "Lawesson-Reagenz" ver- setzt, wonach man weitere 10 Std. auf Rückflußtemperatur erhitzte.To a solution of 1.7 g of 5-fluoro-4- (5-fluoro-3-methyl-2, 4-dioxo-3, 4-dihydro-2H-pyrimidin-l-yl) -2- (1-methyl -prop-2-ynyloxy) -benzonitrile in 50 ml of toluene, 1 g of "Lawesson's reagent" {2, 4-bis (4-methoxyphenyl) -1,3,2, 4-dithiadiphosphetan-2 , 4-dithion}. The mixture was then stirred at the reflux temperature for 10 hours. Then the mixture was again mixed with 1 g of "Lawesson reagent", after which it was heated to reflux temperature for a further 10 hours.
Zur Aufarbeitung wurde das abgekühlte Reaktionsgemisch zunächst über Kieselgel chromatographiert (Laufmittel: Toluol). Das hierbei erhaltene Öl verrührte man mit Isopropylether . Der erhaltene Feststoff wurde noch mit Petrolether gewaschen und schließlich getrocknet. Ausbeute: 0,45 g; Smp. : 181-188°C.For working up, the cooled reaction mixture was first chromatographed on silica gel (mobile phase: toluene). The oil obtained was stirred with isopropyl ether. The solid obtained was washed with petroleum ether and finally dried. Yield: 0.45 g; M.p .: 181-188 ° C.
Auf analoge Weise wurden die folgenden l-Aryl-4-thiouracile hergestellt:The following l-aryl-4-thiouracile were prepared in an analogous manner:
Verbindung Nr. Ia.3 Smp.: 184-185°C;Compound No. Ia.3 m.p .: 184-185 ° C;
5-Fluor-4- (3 , 5-dimethyl-2-oxo-4-thioxo- 3,4-dihydro-2H-pyrimidin-l-yl) -2- (1-methyl- prop-2-inyloxy) -benzonitril Smp.: 147-148°C;5-fluoro-4- (3,5-dimethyl-2-oxo-4-thioxo-3,4-dihydro-2H-pyrimidin-l-yl) -2- (1-methyl-prop-2-ynyloxy) - benzonitrile m.p .: 147-148 ° C;
5-Fluor-4- (5-brom-3-methyl-2-oxo-4-thioxo- 3,4-dihydro-2H-pyrimidin-l-yl)-2- (1-methyl- prop-2-inyloxy) -benzonitril Smp.: 175-180°C. Anwendungsbeispiele5-fluoro-4- (5-bromo-3-methyl-2-oxo-4-thioxo-3,4-dihydro-2H-pyrimidin-l-yl) -2- (1-methyl-prop-2-ynyloxy ) -benzonitrile m.p .: 175-180 ° C. Examples of use
Die herbizide Wirkung der l-Aryl-4-thiouracile I ließ sich durch die folgenden Gewächshausversuche zeigen:The herbicidal activity of l-aryl-4-thiouracile I was demonstrated by the following greenhouse tests:
Als Kulturgefäße dienten Plastikblumentöpfe mit lehmigem Sand mit etwa 3,0 % Humus als Substrat. Die Samen der Testpflanzen wurden nach Arten getrennt eingesät.Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels. The seeds of the test plants were sown separately according to 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 Test- pflanzen, sofern dies nicht durch die Wirkstoffe beeinträchtigt wurde.In pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles. The tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.
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 Aufwandsmenge für die Nachauflaufanwendung betrug lediglich 31,3 bzw. 15,6 g/ha a.S..For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. 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 the post-emergence application was only 31.3 and 15.6 g / ha a.s.
Die Pflanzen wurden artenspezifisch bei Temperaturen von 10 - 25°C bzw. 20 - 35°C gehalten. Die Versuchsperiode erstreckte sich über 2 bis 4 Wochen. Während dieser Zeit wurden die Pflanzen gepflegt, und ihre Reaktion auf die einzelnen Behandlungen wurde ausgewertet.The plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species. The trial period lasted 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 .Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
Die folgende Tabelle 2 zeigt die überlegene herbizide Wirkung der Verbindung Nr. Ib.3 im Vergleich zu der aus WO 97/05117 (dort Beispiel 3) bekannten Vergleichsverbindung A
Figure imgf000067_0001
The following Table 2 shows the superior herbicidal activity of the compound No. Ib.3 in comparison to the comparative compound A known from WO 97/05117 (Example 3 there)
Figure imgf000067_0001
Figure imgf000067_0002
Figure imgf000067_0002

Claims

Patentansprüche claims
1. Neue l-Aryl-4-thiouracile der Formel I1. New l-aryl-4-thiouracile of the formula I
Figure imgf000068_0001
wobei die Variablen folgende Bedeutungen haben:
Figure imgf000068_0001
where the variables have the following meanings:
X Sauerstoff oder Schwefel;X oxygen or sulfur;
R1 Wasserstoff, Amino oder Ci-Cg-Alkyl;R 1 is hydrogen, amino or Ci-Cg-alkyl;
R2 Wasserstoff, Halogen, Cι~C -Alkyl oder Cι-C -Halogenalkyl;R 2 is hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 haloalkyl;
R3 Wasserstoff, Halogen, Ci-Cg-Alkyl oder Halogenmethyl ,-R 3 is hydrogen, halogen, Ci-Cg-alkyl or halomethyl,
R4 Wasserstoff oder Halogen;R 4 is hydrogen or halogen;
R5 Cyano, Halogen, -CO-NH2, -CS-NH2 oder -OC(R8,R9)-CO-0(Cι-C6-Alkyl) ;R 5 cyano, halogen, -CO-NH 2 , -CS-NH 2 or -OC (R 8 , R 9 ) -CO-0 (-C-C 6 alkyl);
Y Stickstoff, die Methingruppe oder zusammen mit R6 eine Brücke >C-0-C (R10) =N-;Y nitrogen, the methine group or together with R 6 a bridge> C-0-C (R 10 ) = N-;
R6 zusammen mit R5 einen über den Sauerstoff an R5 gebundenen Rest -N(R )-CZ1-C(R8' ,R9')-0-, oderR 6 together with R 5 is a radical -N (R) -CZ 1 -C (R 8 ', R 9 ') -0- which is bonded to R 5 via the oxygen, or
1) Wasserstoff, Hydroxy, Mercapto, Cyano, Nitro, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cδ-Halogenalkoxy, Ci-Cg-Halogenalkylthio,1) hydrogen, hydroxy, mercapto, cyano, nitro, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-C δ -haloalkoxy, Ci-Cg-haloalkylthio,
Ci-Cδ -Alkylthio- (Cι-C6-alkyl) carbonyl, (Ci-Cg-Alkyl) - iminooxycarbonyl, Ci -Cg -Alkoxy-Ci-Cδ- alkyl, C -Cg-Alk- oxyamino-Ci -Cg - alkyl , Ci -Cg -Alkoxy-Ci -Cg - alkylamino - Ci-Cg- alkyl,Ci-C δ -Alkylthio- (-C-C 6 -alkyl) carbonyl, (Ci-Cg-alkyl) - iminooxycarbonyl, Ci -Cg -alkoxy-Ci-C δ - alkyl, C -Cg-alk- oxyamino-Ci - Cg - alkyl, Ci -Cg alkoxy-Ci -Cg - alkylamino - Ci-Cg- alkyl,
2) Ci-Cδ-Alkoxy, Ci-Cδ -Alkylthio, C3-Cδ-Cycloalkoxy, C3-Cg-Cycloalkylthio, C2-Cg-Alkenyloxy, C2 -Cg-Alkenyl- thio, C2-Cg-Alkinyloxy, C2-Cg-Alkinylthio, (Ci-Cg-Alkyl) carbonyloxy, (Cι-C6 -Alkyl) carbonylthio, (Ci-Cδ-Alkoxy) carbonyloxy, (C2-Cg-Alkenyl) carbonyloxy, (C2-C6-Alkenyl) carbonylthio, (C2-Cg-Alkinyl) - carbonyloxy, (C -Cδ-Alkinyl) carbonylthio, Ci-Cg-Alkylsulfonyloxy oder Ci-Cg-Alkylsulfonyl, wobei jeder dieser 17 Reste gewünschtenfalls einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus - Halogen, Nitro, Cyano, Hydroxy, C3-C6-Cycloalkyl,2) Ci-C δ alkoxy, Ci-C δ alkylthio, C 3 -C δ cycloalkoxy, C 3 -Cg cycloalkylthio, C 2 -Cg alkenyloxy, C 2 -Cg alkenyl thio, C 2 - Cg-alkynyloxy, C 2 -Cg-alkynylthio, (Ci-Cg-alkyl) carbonyloxy, (Cι-C 6 -alkyl) carbonylthio, (Ci-Cδ-alkoxy) carbonyloxy, (C 2 -Cg-alkenyl) carbonyloxy, ( C 2 -C 6 alkenyl) carbonylthio, (C 2 -Cg alkynyl) carbonyloxy, (C -C δ alkynyl) carbonylthio, Ci-Cg-alkylsulfonyloxy or Ci-Cg-alkylsulfonyl, where each of these 17 radicals can optionally carry one to three substituents, each selected from the group consisting of - halogen, nitro, cyano, hydroxy, C 3 -C 6 cycloalkyl,
Ci-Cδ-Alkoxy, C -C6-Cycloalkoxy, C3-Cg-Alkenyl- oxy, C3-C6-Alkinyloxy, Cι-Cg-Alkoxy-Cι-Cg-alkoxy, Ci-Cg-Alkylthio, Ci-Cg-Alkylsulfinyl, Ci-Cg-Alkylsulfonyl, Ci-Cg-Alkylidenaminoxy, Oxo, =N-0R11, der Phenyl-, Phenoxy- oder Phenylsulfonylgruppe, die unsubstituiert sein oder ein bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Halogen, Nitro, Cyano, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy undCi-C δ alkoxy, C -C 6 cycloalkoxy, C 3 -Cg alkenyl oxy, C 3 -C 6 alkynyloxy, -C-Cg-alkoxy-Cι-Cg-alkoxy, Ci-Cg-alkylthio, Ci -Cg-alkylsulfinyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylidenaminoxy, oxo, = N-0R 11 , the phenyl, phenoxy or phenylsulfonyl group, which may be unsubstituted or carry one to three substituents, each selected from the group consisting of halogen, nitro, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy and
(Ci-Cδ -Alkoxy) carbonyl,(Ci-C δ alkoxy) carbonyl,
-CO-R12, -CO-OR12, -CO-SR12, -CO-N (R12) -R , -OCO-R12, -OCO-OR12, -OCO-SR12, -OCO-N (R12) -R13 , -N(R12)-R13 und -C(R1 )=N-OR ;-CO-R 12 , -CO-OR 12 , -CO-SR 12 , -CO-N (R 12 ) -R, -OCO-R 12 , -OCO-OR 12 , -OCO-SR 12 , -OCO- N (R 12 ) -R 13 , -N (R 12 ) -R 13 and -C (R 1 ) = N-OR;
3) -CZ2-R15, -C(NR6) -Rl5, -C(R15) (Z R17) (Z R 8) , -C (R15) =C (R19) -CN, -C (R15) =C (R19) -CO-R20, -CH (R15) -CH (R19) -CO-R20, -C (R15) =C (R19) -CH2-CO-R20, -C (R15) =C (R19) -C (R21) =C (R22) -CO-R20, -C(R15)=C(R19)-CH2-CH(R23)-CO-R20, -CO-OR24, -CO-SR24,3) -CZ 2 -R 15 , -C (NR6) -Rl5, -C (R 1 5) (ZR 17 ) (ZR 8), -C (R 15 ) = C (R 19 ) -CN, -C (R 15 ) = C (R 19 ) -CO-R 20 , -CH (R 15 ) -CH (R 19 ) -CO-R 20 , -C (R 15 ) = C (R 19 ) -CH 2 - CO-R 20 , -C (R 15 ) = C (R 19 ) -C (R 21 ) = C (R 22 ) -CO-R 20 , -C (R 15 ) = C (R 19 ) -CH 2 -CH (R 23 ) -CO-R 20 , -CO-OR 24 , -CO-SR 24 ,
-CO-N(R24) -OR11, -C≡C-CO-NH-OR11, -C≡C-CO-N(R2 )-OR11, -C≡C-CS-NH-OR11, -C≡C-CS-N(R24) -OR11, -C(R15)=C(R19)-CO-NH-OR1:I-, -C(R15)=C(R19) -CO-N(R24) -OR11, -C(R15)=C(R19) -CS-NH-OR11,-CO-N (R 24 ) -OR 11 , -C≡C-CO-NH-OR 11 , -C≡C-CO-N (R 2 ) -OR 11 , -C≡C-CS-NH-OR 11 , -C≡C-CS-N (R 24 ) -OR 11 , -C (R 15 ) = C (R 19 ) -CO-NH-OR 1: I -, -C (R 15 ) = C ( R 19 ) -CO-N (R 24 ) -OR 11 , -C (R 15 ) = C (R 19 ) -CS-NH-OR 11 ,
-C (R5) =C (R19 ) -CS-N (R24 ) -OR11 ,-C (R 5 ) = C (R 19 ) -CS-N (R 24 ) -OR 11 ,
-C (R15) =C (R19) -C (R14) =N-OR1:L, -C (R14) =N-OR11, -C≡C-C(R1 )=N-OR11, -C(Z3R17) (Z4R18) -OR24, -C(Z3R17) (Z4R18) -SR24, -C(Z3R17) (Z4R18) -N(R25)R26, -N(R25)-R26 oder -C0-N(R25) -R2f\--C (R 15 ) = C (R 19 ) -C (R 14 ) = N-OR 1: L , -C (R 14 ) = N-OR 11 , -C≡CC (R 1 ) = N-OR 11 , -C (Z 3 R 17 ) (Z 4 R 18 ) -OR 24 , -C (Z 3 R 17 ) (Z 4 R 18 ) -SR 24 , -C (Z 3 R 17 ) (Z 4 R 18 ) -N (R 25 ) R 26 , -N (R 25 ) -R 26 or -C0-N (R 25 ) -R 2f \ -
Z1, Z2, Z3, Z4 unabhängig voneinander Sauerstoff oderZ 1 , Z 2 , Z 3 , Z 4 independently of one another are oxygen or
Schwefel;Sulfur;
R7 Wasserstoff, Ci-Cg-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, Ci-Cg-Alkoxy, C3-Cg-Alkenyloxy, C3-Cδ-Alkinyloxy, C3-Cg-Cycloalkyl oder C3-Cδ-Cycloalkoxy, wobei jeder der letztgenannten 8 Reste gewünschtenfalls einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Nitro, Cyano, Halogen, =0, =N-OR1:L' , Ci-Cg-Alkoxy, -CO-R12 ' , -CO-OR12 ' , -CO-SR12 ' und - C (R14 ' ) =N-OR11 # ;R 7 is hydrogen, Ci-Cg-alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, Ci-Cg-alkoxy, C 3 -Cg-alkenyloxy, C 3 -C δ -alkynyloxy, C 3 - Cg-cycloalkyl or C 3 -C δ- cycloalkoxy, where each of the latter 8 residues can optionally carry one to three substituents, each selected from the group consisting of nitro, cyano, halogen, = 0, = N-OR 1: L ' , Ci-Cg-alkoxy, -CO-R 12 ', -CO-OR 12 ', -CO-SR 12 'and - C (R 14 ') = N-OR 11 # ;
R8, R9, R8', R9' unabhängig voneinander Wasserstoff, Cyano oder Ci-Cg-Alkyl;R 8 , R 9 , R 8 ', R 9 ' independently of one another are hydrogen, cyano or Ci-Cg-alkyl;
R10 Wasserstoff, Halogen, Ci-Cg-Alkyl, C3-Cg-Alkenyl, C3-Cg-Alkinyl, Ci-Cg-Alkoxy, C3-Cg-Alkenyloxy, C3-Cg-Alkinyloxy, C3-Cg-Cycloalkyl oder C3-C6-Cycloalkoxy, wobei jeder der letztgenannten 8 Reste gewünschtenfalls einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Nitro, Cyano, Halogen, =0, =N-0R11;', Ci-Cg-Alkoxy, -CO-R12", -CO-OR12", -CO-SR12" und -C(R14" )=N-OR1:L" ;R 10 is hydrogen, halogen, Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -Cg-alkynyl, Ci-Cg-alkoxy, C 3 -Cg-alkenyloxy, C 3 -Cg-alkynyloxy, C 3 -Cg -Cycloalkyl or C 3 -C 6 -cycloalkoxy, each of the latter 8 radicals optionally being able to carry one to three substituents, each selected from the group consisting of nitro, cyano, halogen, = 0, = N-0R 11; ', Ci-Cg-alkoxy, -CO-R 12 ", -CO-OR 12 ", -CO-SR 12 "and -C (R 14 ") = N-OR 1: L ";
R11, R11', R11" unabhängig voneinander Wasserstoff,R 11 , R 11 ', R 11 "independently of one another are hydrogen,
Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, C3-C6-Cycloalkyl, C3-Cg-Alkenyl, C3-Cg-Alkinyl, Hydroxy-Ci-Cδ-alkyl, Cι-Cg-Alkoxy-Cι-Cg-alkyl , Cι-C6-Alkylthio-Cι-C6-alkyl , Cyano-Ci-Cg-alkyl, (Ci-Cg-Alkyl) carbonyl-Ci-Cg-alkyl,Ci-Cg-alkyl, Ci-Cg-haloalkyl, C 3 -C 6 cycloalkyl, C 3 -Cg-alkenyl, C 3 -Cg-alkynyl, hydroxy-Ci-C δ- alkyl, Cι-Cg-alkoxy-Cι -Cg-alkyl, -C-C 6 -alkylthio-Cι-C 6 -alkyl, cyano-Ci-Cg-alkyl, (Ci-Cg-alkyl) carbonyl-Ci-Cg-alkyl,
(Ci-Cg-Alkoxy) carbonyl-Ci-Cg-alkyl , (Ci -Cg -Alkoxy) - carbonyl -C2 -Cg -alkenyl , (Ci-Cg-Alkyl) carbonyloxy- Ci-Cg-alkyl oder Phenyl-Ci-Cδ-alkyl, wobei der Phenylring gewünschtenfalls ein bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy und (Ci-Cg-Alkoxy) carbonyl;(Ci-Cg-alkoxy) carbonyl-Ci-Cg-alkyl, (Ci-Cg-alkoxy) - carbonyl -C 2 -Cg -alkenyl, (Ci-Cg-alkyl) carbonyloxy-Ci-Cg-alkyl or phenyl-Ci -C δ- alkyl, where the phenyl ring can optionally carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy and (Ci -Cg-alkoxy) carbonyl;
R12, R12', R12" unabhängig voneinander Wasserstoff, Ci-Cg-Alkyl, C3-Cg-Cycloalkyl, C3-Cg-Alkenyl,R 12 , R 12 ', R 12 "independently of one another are hydrogen, Ci-Cg-alkyl, C 3 -Cg-cycloalkyl, C 3 -Cg-alkenyl,
C3-C6-Alkinyl, Cι-C6-Alkoxy-Cι-C6-alkyl, (Ci-Cg-Alkoxy) - carbonyl-Ci-Cg-alkyl , (C3 -Cg -Alkenyloxy) carbonyl - Ci-Cg-alkyl, Phenyl oder Phenyl-Ci-Cg-alkyl, wobei die Phenylgruppe und der Phenyl-Ring der Phenylalkylgruppe unsubstituiert sein oder einen bis drei Reste tragen können, jeweils ausgewählt aus der Gruppe bestehend aus Halogen, Nitro, Cyano, Ci-Cg-Alkyl, Ci-Cδ-Halogenalkyl, Ci-Cδ-Alkoxy und (Ci-Cg-Alkyl) carbonyl;C 3 -C 6 alkynyl, -C-C 6 -alkoxy-Cι-C 6 -alkyl, (Ci-Cg-alkoxy) - carbonyl-Ci-Cg-alkyl, (C 3 -Cg -alkenoxy) carbonyl - Ci- Cg-alkyl, phenyl or phenyl-Ci-Cg-alkyl, where the phenyl group and the phenyl ring of the phenylalkyl group can be unsubstituted or can carry one to three radicals, each selected from the group consisting of halogen, nitro, cyano, Ci-Cg -Alkyl, Ci-Cδ-haloalkyl, Ci-C δ- alkoxy and (Ci-Cg-alkyl) carbonyl;
R13 Wasserstoff, Hydroxy, Cι-C6-Alkyl, C3-C6-Cycloalkyl, Ci-Cg-Alkoxy, (Ci -Cg -Alkoxy) carbonyl -Ci -C6 -alkoxy, C3-Cg-Alkenyl oder C3-Cg -Alkenyloxy;R 13 is hydrogen, hydroxy, -CC 6 alkyl, C 3 -C 6 cycloalkyl, Ci-Cg alkoxy, (Ci -Cg alkoxy) carbonyl -Ci -C 6 alkoxy, C 3 -Cg alkenyl or C 3 -Cg alkenyloxy;
R14, R14', R14" unabhängig voneinander Wasserstoff, Halogen, - Ci-Cδ-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy,R 14 , R 14 ', R 14 "independently of one another are hydrogen, halogen, - Ci-C δ- alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy,
Ci-Cg-Halogenalkoxy, C3-C6 -Alkenyloxy, Cι-C6-Alkyl- thio, Ci-Cg-Halogenalkylthio, (Ci-Cg-Alkyl) carbonyl- oxy, (Ci-Cg-Halogenalkyl) carbonyloxy, Ci-Cg-Alkyl- sulfonyloxy oder Ci-Cg-Halogenalkylsulfonyloxy, wobei die letztgenannten 11 Reste einen der folgenden Substituenten tragen können: Hydroxy, Cyano, Hydroxy- carbonyl, Ci-Cg-Alkoxy, Cι-C6-Alkylthio,Ci-Cg-haloalkoxy, C 3 -C 6 alkenyloxy, Cι-C 6 -alkyl thio, Ci-Cg-haloalkylthio, (Ci-Cg-alkyl) carbonyl- oxy, (Ci-Cg-haloalkyl) carbonyloxy, Ci-Cg-alkylsulfonyloxy or Ci-Cg-haloalkylsulfonyloxy, where the latter 11 radicals can carry one of the following substituents: hydroxy, cyano, hydroxycarbonyl, Ci-Cg-alkoxy , -CC 6 alkylthio,
(Ci-Cg-Alkyl) carbonyl, (Ci-Cg-Alkoxy) carbonyl, (Ci-C -Alkyl) aminocarbonyl, Di (Ci-Cg- alkyl) aminocarbonyl, (Ci-Cδ-Alkyl) carbonyloxy, Ci-Cg -Alkoxy- (Ci-Cg- alkyl) aminocarbonyl; - einen mit dem Stickstoffatom über eine Carbonylbrücke gebundenen 3- bis 7gliedrigen Azaheterocyclus, der neben Kohlenstoffringgliedern noch ein Sauerstoffoder Schwefelatom als Ringglied enthalten kann; (Ci-Cg-Alkyl) carbonyl, (Ci-Cg-Halogenalkyl) carbonyl, (Ci-Cg-Alkoxy) carbonyl, (Ci-Cg-Alkoxy) carbonyloxy,(Ci-Cg-alkyl) carbonyl, (Ci-Cg-alkoxy) carbonyl, (Ci-C-alkyl) aminocarbonyl, di (Ci-Cg-alkyl) aminocarbonyl, (Ci-C δ- alkyl) carbonyloxy, Ci-Cg -Alkoxy- (Ci-Cg-alkyl) aminocarbonyl; a 3- to 7-membered azaheterocycle which is bonded to the nitrogen atom via a carbonyl bridge and which, in addition to carbon ring members, can also contain an oxygen or sulfur atom as the ring member; (Ci-Cg-alkyl) carbonyl, (Ci-Cg-haloalkyl) carbonyl, (Ci-Cg-alkoxy) carbonyl, (Ci-Cg-alkoxy) carbonyloxy,
(Ci-Cg-Alkyl) carbonylthio, (Ci-Cg-Halogenalkyl) - carbonylthio, (Ci-Cδ-Alkoxy) carbonylthio, C2-C6-Alkenyl, C2-C6-Alkenylthio, C3-Cg-Alkinyl, C3-C6~Alkinyloxy, C3-Cg-Alkinyl hio, (C2-Cg-Alkinyl) carbonyloxy, C3-Cg-Alkinylsulfonyloxy, C3-Cδ-Cycloalkyl, C3-Cg-Cycloalkyloxy, C3-Cg-Cycloalkylthio, (C3-Cg-Cycloalkyl) carbonyloxy, C3-C -Cycloalkylsulfonyloxy; Phenyl, Phenoxy, Phenylthio, Benzoyloxy, Phenyl - sulfonyloxy, Phenyl-Ci-Cg-alkyl, Phenyl-Ci-Cg-alkoxy,(Ci-Cg-alkyl) carbonylthio, (Ci-Cg-haloalkyl) carbonylthio, (Ci-C δ alkoxy) carbonylthio, C 2 -C 6 alkenyl, C 2 -C 6 alkenylthio, C 3 -Cg- Alkynyl, C 3 -C 6 ~ alkynyloxy, C 3 -Cg alkynyl hio, (C 2 -Cg alkynyl) carbonyloxy, C 3 -Cg alkynylsulfonyloxy, C 3 -C δ cycloalkyl, C 3 -Cg cycloalkyloxy, C 3 -Cg cycloalkylthio, (C 3 -Cg cycloalkyl) carbonyloxy, C 3 -C cycloalkylsulfonyloxy; Phenyl, phenoxy, phenylthio, benzoyloxy, phenylsulfonyloxy, phenyl-Ci-Cg-alkyl, phenyl-Ci-Cg-alkoxy,
Phenyl-Cι-C6-alkylthio, Phenyl- (Ci-Cg-alkyl) - carbonyloxy oder Phenyl- (Ci-Cg-alkyl) sulfonyloxy, wobei die Phenylringe der letztgenannten 10 Reste unsubstituiert sein oder ihrerseits ein bis drei Substituenten tragen können, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy und (Ci-Cδ-Alkoxy) carbonyl;Phenyl-C 6 -alkylthio, phenyl- (Ci-Cg-alkyl) carbonyloxy or phenyl- (Ci-Cg-alkyl) sulfonyloxy, where the phenyl rings of the latter 10 radicals may be unsubstituted or in turn may carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy and (Ci-C δ- alkoxy) carbonyl;
R15 Wasserstoff, Cyano, Cι-C6-Alkyl, Cι-C6-Halogenalkyl,R 15 is hydrogen, cyano, C 6 -alkyl, C 6 haloalkyl,
C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, Ci-Cg-Alk- oxy-Ci-Cg-alkyl oder (Ci-Cg-Alkoxy) carbonyl;C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, Ci-Cg-alkoxy-Ci-Cg-alkyl or (Ci-Cg-alkoxy) carbonyl;
R16 Wasserstoff, Hydroxy, Cι-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, C3-Cg-Cycloalkyl, Ci-Cg-Halogenalkyl,R 16 is hydrogen, hydroxyl, -CC 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -Cg-cycloalkyl, Ci-Cg-haloalkyl,
Ci-Cg-Alkoxy-Ci-Cδ-alkyl, Cι-C6-Alkoxy, C3-C6-Alkenyloxy, C3-C6-Alkinyloxy, C3-Cg-Cycloalkoxy, C5-C7-Cycloalkenyl- oxy, Ci-Cg-Halogenalkoxy, C3-Cδ-Halogenalkenyloxy, Hydroxy-Ci-Cg-alkoxy, Cyano-Ci-Cg-alkoxy, C3-Cg-Cyclo- alkyl-Cι-C6-alkoxy, Cι-C6-Alkoxy-Cι-C6-alkoxy, Ci-Cg-Alk- oxy-C3-Cg-alkenyloxy, (Ci-Cδ-Alkyl) carbonyloxy, (Ci-Cδ-Halogenalkyl) carbonyloxy, (Ci-Cg-Alkyl) carbamoyl- oxy, (Ci-Cg-Halogenalkyl) carbamoyloxy, (Ci-Cg-Alkyl) carbo- nyl-Cι-C6-alkyl, (Ci-Cg-Alkyl) carbonyl-Ci-Cg-alkoxy, (Ci-Cg-Alkoxy) carbonyl-Ci-Cg-alkyl , (Ci-Cg-Alkoxy) carbo- nyl-Ci-Cg-alkoxy, Ci-Cg-Alkylthio-Ci-Cβ -alkoxy, Di- (Cι-Cg-alkyl)amino-Cι-Cg-alkoxy, -N(R27)R28,Ci-Cg-alkoxy-Ci-C δ- alkyl, -C-C 6 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 3 -Cg cycloalkoxy, C 5 -C 7 cycloalkenyl - oxy, Ci-Cg-haloalkoxy, C 3 -Cδ-haloalkenyloxy, hydroxy-Ci-Cg-alkoxy, cyano-Ci-Cg-alkoxy, C 3 -Cg-cycloalkyl-Cι-C 6 -alkoxy, Cι- C 6 -alkoxy-C 6 -C 6 -alkoxy, Ci-Cg-alkoxy-C 3 -Cg-alkenyloxy, (Ci-C δ -alkyl) carbonyloxy, (Ci-C δ -haloalkyl) carbonyloxy, (Ci Cg-alkyl) carbamoyl oxy, (Ci-Cg-haloalkyl) carbamoyloxy, (Ci-Cg-alkyl) carbonyl-Cι-C 6 alkyl, (Ci-Cg-alkyl) carbonyl-Ci-Cg-alkoxy, (Ci-Cg-alkoxy ) carbonyl-Ci-Cg-alkyl, (Ci-Cg-alkoxy) carbonyl-Ci-Cg-alkoxy, Ci-Cg-alkylthio-Ci-Cβ-alkoxy, di- (-C-Cg-alkyl) amino-Cι -Cg-alkoxy, -N (R 27 ) R 28 ,
Phenyl, das seinerseits noch einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, C2-C6-Alkenyl, Ci-Cg-Alkoxy und (Cι-C6-Alkoxy) - carbonyl,Phenyl, which in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, C 2 -C 6 alkenyl, Ci-Cg-alkoxy and (-C 6 alkoxy) carbonyl,
Phenyl-Ci-Cg-alkoxy, Phenyl-C3-C6-alkenyloxy oder Phenyl- C3-Cg-alkinyloxy, wobei jeweils eine oder zwei Methylengruppen der Kohlenstoffketten durch -0- , -S- oder -N (Ci-Cg-Alkyl) - ersetzt sein können und wobei jeder Phenylring unsubstituiert sein oder seinerseits einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cδ-Alkyl, Cι-C6-Halogenalkyl, C2-C6-Alkenyl, Ci-Cg-Alk- oxy und (Ci-Cg-Alkoxy) carbonyl, Heterocyclyl, Heterocyclyl-C-Cg-alkoxy, Heterocyclyl-Phenyl-Ci-Cg-alkoxy, phenyl-C 3 -C 6 -alkenyloxy or phenyl-C 3 -Cg-alkynyloxy, where in each case one or two methylene groups of the carbon chains by -0-, -S- or -N (Ci-Cg -Alkyl) - can be replaced and each phenyl ring can be unsubstituted or in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-C δ- alkyl, -C-C 6 -haloalkyl, C 2 -C 6 alkenyl, Ci-Cg-alkoxy and (Ci-Cg-alkoxy) carbonyl, heterocyclyl, heterocyclyl-C-Cg-alkoxy, heterocyclyl-
C3-Cg-alkenyloxy oder Heterocyclyl-C3-Cδ-alkinyloxy, wobei jeweils eine oder zwei Methylengruppen der Kohlenstoff - ketten durch -O- , -S- oder -N(Cι-C6-Alkyl) - ersetzt sein können und wobei jeder Heterocyclus 3- bis 7gliedrig, ge- sättigt, ungesättigt oder aromatisch sein kann und ein bis vier Heteroatome enthält, ausgewählt aus der Gruppe bestehend aus zwei Sauerstoffatomen, zwei Schwefelatomen und 4 Stickstoffatomen, und entweder unsubstituiert ist oder seinerseits einen bis drei Substituenten trägt, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cδ-Alkyl, Ci-Cδ-Halogenalkyl, C-C6-Alkenyl, Ci-Cg-Alkoxy und (Ci-Cg-Alkoxy) carbonyl;C 3 -Cg-alkenyloxy or heterocyclyl-C 3 -C δ- alkynyloxy, where one or two methylene groups of the carbon chains can be replaced by -O-, -S- or -N (-C-C 6 -alkyl) - and wherein each heterocycle can be 3 to 7-membered, saturated, unsaturated or aromatic and contains one to four heteroatoms selected from the group consisting of two oxygen atoms, two sulfur atoms and 4 nitrogen atoms, and is either unsubstituted or in turn one to three substituents bears, each selected from the group consisting of cyano, nitro, halogen, Ci-C δ alkyl, Ci-C δ haloalkyl, CC 6 alkenyl, Ci-Cg-alkoxy and (Ci-Cg-alkoxy) carbonyl;
R17, R18 unabhängig voneinander Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, Ci-Cg-Alk- oxy-Ci-Cg-alkyl oder zusammen für eine gesättigte oder ungesättigte, 2- bis 4-gliedrige Kohlenstoffkette, die einen Oxosubstituenten tragen kann, wobei ein Glied dieser Kette durch ein den Variablen Z3 und Z4 nicht benachbarte Brücke -0-, -S-, -N=, -NH- oder -N (Ci-Cg -Alkyl) - ersetzt sein kann, und wobei die Kohlenstoffkette noch ein bis drei Reste tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Amino, Halogen, Ci-Cg-Alkyl, C2-C6-Alke- nyl, Ci-Cδ-Alkoxy, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, Ci-Cg-Halogenalkyl, Cyano-Ci-Cg-alkyl, Hydroxy-Ci-Cg- alkyl, Cι-Cg-Alkoxy-Cι-Cg-alkyl, C3-Cg-Alkenyloxy-Cι-Cg - alkyl, C3-C6-Alkinyloxy-Cι-C6-alkyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkoxy, Carboxy, (Ci-Cg-Alkoxy) carbonyl, (Ci-Cg-Alkyl) carbonyloxy-Ci-Cg-alkyl und Phenyl, das seinerseits unsubstituiert sein oder einen bis dreiR 17 , R 18 independently of one another Ci-Cg-alkyl, Ci-Cg-haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, Ci-Cg-alkoxy-Ci-Cg-alkyl or together for a saturated or unsaturated, 2- to 4-membered carbon chain which can carry an oxo substituent, one link of this chain being connected by a bridge which is not adjacent to the variables Z 3 and Z 4 -0-, -S-, -N =, - NH- or -N (Ci-Cg-alkyl) - can be replaced, and wherein the carbon chain can still carry one to three residues, each selected from the group consisting of cyano, nitro, amino, halogen, Ci-Cg-alkyl, C 2 -C 6 -alkenyl, Ci-Cδ-alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, Ci-Cg-haloalkyl, cyano-Ci-Cg-alkyl, hydroxy-Ci- Cg- alkyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 3 -Cg alkenyloxy C 1 -C 6 alkyl, C 3 -C 6 alkynyloxy C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkoxy, carboxy, (Ci-Cg-alkoxy) carbonyl, (Ci-Cg-alkyl) carbonyloxy-Ci-Cg-alkyl and phenyl, which in turn may be unsubstituted or one to three
Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Amino, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy und (Ci-Cg-Alkoxy) carbonyl, und wobei die Kohlenstoffkette auch durch einen ankondensierten oder spiroverknüpften 3- bis 7gliedrigen Ring substituiert sein kann, der ein oder zwei Heteroatome als Ringglieder enthalten kann, ausgewählt aus Sauerstoff, Schwefel, Stickstoff und durch Ci-Cg-Alkyl substituiertem Stickstoff, und der gewünschtenfalls seinerseits einen oder zwei der folgenden Substituenten tragen kann: Cyano, Ci-Cδ-Alkyl, C2-C6-Alkenyl, Ci-Cg-Alkoxy, Cyano-Ci-Cg- alkyl, Ci-Cg-Halogenalkyl und (Ci-Cg-Alkoxy) carbonyl;Can carry substituents, each selected from the group consisting of cyano, nitro, amino, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy and (Ci-Cg-alkoxy) carbonyl, and wherein the carbon chain can also be substituted by a fused or spiro-linked 3- to 7-membered ring, which can contain one or two heteroatoms as ring members, selected from oxygen, sulfur, nitrogen and nitrogen substituted by Ci-Cg-alkyl, and if desired one or two of them can carry the following substituents: cyano, Ci-C δ alkyl, C 2 -C 6 alkenyl, Ci-Cg-alkoxy, cyano-Ci-Cg-alkyl, Ci-Cg-haloalkyl and (Ci-Cg-alkoxy) carbonyl ;
R19 Wasserstoff, Cyano, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy, (Ci-Cg-Alkyl) carbonyl oder (Ci-Cg-Alkoxy) carbonyl;R 19 is hydrogen, cyano, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, (Ci-Cg-alkyl) carbonyl or (Ci-Cg-alkoxy) carbonyl;
R20 Wasserstoff, O-R29, S-R29, Ci-Cg-Alkyl, das noch einen oder zwei Cι-C6-Alkoxysubstituenten tragen kann, C2-C6-Alkenyl, C2-C6-Alkinyl, Ci-Cg-Halogenalkyl, C3-C6 -Cycloalkyl, Ci-Cg-Alkylthio-Ci-Cg-alkyl, Ci-Cg-Alkyliminooxy, -N(R25)R26 oder Phenyl, das unsubstituiert sein oder ein bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano,R 20 is hydrogen, OR 29 , SR 29 , Ci-Cg-alkyl, which can also carry one or two -CC 6 alkoxy substituents, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci-Cg- Haloalkyl, C 3 -C 6 -cycloalkyl, Ci-Cg-alkylthio-Ci-Cg-alkyl, Ci-Cg-alkyliminooxy, -N (R 25 ) R 26 or phenyl, which may be unsubstituted or carry one to three substituents, each selected from the group consisting of cyano,
Nitro, Halogen, Ci-Cδ-Alkyl, C -Cδ-Alkenyl, Ci-Cδ-Halogenalkyl, Ci-Cδ-Alkoxy und (Ci-Cg-Alkoxy) carbonyl;Nitro, halogen, Ci-C δ alkyl, C -C δ alkenyl, Ci-C δ haloalkyl, Ci-C δ alkoxy and (Ci-Cg-alkoxy) carbonyl;
R21 Wasserstoff, Cyano, Halogen, Ci-Cg-Alkyl, C3-Cδ-Alkenyl, C3-C5-Alkinyl, Ci-Cg-Alkoxy-Ci-Cg-alkyl, (Ci-Cg-Alkyl) - carbonyl, (Ci-Cg-Alkoxy) carbonyl, -N(R25)R26 oder Phenyl, das seinerseits noch einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, C3-C6-Alkenyl, Ci-Cg-Alkoxy und (Ci-Cg-Alkoxy) carbonyl;R 21 is hydrogen, cyano, halogen, Ci-Cg-alkyl, C 3 -C δ- alkenyl, C 3 -C 5 -alkynyl, Ci-Cg-alkoxy-Ci-Cg-alkyl, (Ci-Cg-alkyl) - carbonyl, (Ci-Cg-alkoxy) carbonyl, -N (R 25 ) R 26 or phenyl, which in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-Cg-alkyl , Ci-Cg-haloalkyl, C 3 -C 6 alkenyl, Ci-Cg-alkoxy and (Ci-Cg-alkoxy) carbonyl;
R22 Wasserstoff, Cyano, Halogen, Ci-Cg-Alkyl, Ci-Cg-Alkoxy,R 22 is hydrogen, cyano, halogen, Ci-Cg-alkyl, Ci-Cg-alkoxy,
Ci-Cg-Halogenalkyl, (Ci-Cg-Alkyl) carbonyl oder (Ci-Cg-Alk- oxy) carbonyl; R23 Wasserstoff, Cyano, Ci-Cg-Alkyl oder (Ci-Cg-Alkoxy) - carbonyl;Ci-Cg-haloalkyl, (Ci-Cg-alkyl) carbonyl or (Ci-Cg-alkoxy) carbonyl; R 23 is hydrogen, cyano, Ci-Cg-alkyl or (Ci-Cg-alkoxy) carbonyl;
R24, R29 unabhängig voneinander Wasserstoff, Ci-Cδ-Alkyl, Ci-Cg-Halogenalkyl, C -C6 -Alkenyl oder C2-C6 -Alkinyl, wobei die letztgenannten 4 Gruppen jeweils einen oder zwei der folgenden Reste tragen können: Cyano, Halogen, Hydroxy, Hydroxycarbonyl , Ci-Cg-Alkoxy, Cι-C6-Alkylthio, (Cι-C6-Alkyl) carbonyl, (Cι-C6-Alk- oxy) carbonyl, (Ci-Cδ-Alkyl) carbonyloxy,R 24 , R 29 independently of one another are hydrogen, Ci-C δ- alkyl, Ci-Cg-haloalkyl, C -C 6 -alkenyl or C 2 -C 6 -alkynyl, the latter 4 groups each carrying one or two of the following radicals can: cyano, halogen, hydroxy, hydroxycarbonyl, Ci-Cg-alkoxy, -C-C 6 -alkylthio, (-C-C 6 -alkyl) carbonyl, (Cι-C 6 -alkoxy) carbonyl, (Ci-C δ -Alkyl) carbonyloxy,
(C3-Cg -Alkenyloxy) carbonyl oder einen mit dem Stickstoffatom über eine Carbonylbrücke gebundenen 3- bis 7gliedrigen Azaheterocyclus, der neben Kohlenstoff - ringgliedern noch ein Sauerstoff- oder Schwefelatom als Ringglied enthalten kann; oder (Ci-Cg-Alkyl) carbonyl, (Ci-Cδ-Halogenalkyl) - carbonyl, (Ci-Cg-Alkoxy) carbonyl, Ci-Cg-Alkylamino- carbonyl, Di (Ci-Cg -alkyl) aminocarbonyl, Ci-Cβ-Alkyl - oximino -Ci -Cg - alkyl, C3-Cδ-Cycloalkyl , Phenyl oder Phenyl-Ci-Cδ-alkyl, wobei die Phenylringe unsubstituiert sein oder ihrerseits ein bis drei Substituenten tragen können, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-Cδ-Alkyl, Ci-Cδ-Halogenalkyl, Ci-Cg-Alkoxy und (Ci-Cδ-Alkoxy) carbonyl;(C 3 -Cg alkenyloxy) carbonyl or a 3- to 7-membered azaheterocycle bonded to the nitrogen atom via a carbonyl bridge, which may contain, in addition to carbon ring members, an oxygen or sulfur atom as the ring member; or (Ci-Cg-alkyl) carbonyl, (Ci-C δ -haloalkyl) -carbonyl, (Ci-Cg-alkoxy) carbonyl, Ci-Cg-alkylamino-carbonyl, di (Ci-Cg-alkyl) aminocarbonyl, Ci Cβ-alkyl-oximino -Ci-Cg-alkyl, C 3 -C δ- cycloalkyl, phenyl or phenyl-Ci-C δ- alkyl, where the phenyl rings can be unsubstituted or in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-C δ- alkyl, Ci-C δ -haloalkyl, Ci-Cg-alkoxy and (Ci-C δ- alkoxy) carbonyl;
R25, R26, R27, R28 unabhängig voneinanderR 25 , R 26 , R 27 , R 28 independently of one another
Wasserstoff, Ci-Cg-Alkyl, C3-Cδ-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, Cι-C6-Halogenalkyl, Cι-C6-Alkoxy-Cι-C6-alkyl, (Ci-Cg-Alkyl) carbonyl,Hydrogen, Ci-Cg-alkyl, C 3 -Cδ-alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, Cι-C 6 -haloalkyl, Cι-C 6 -alkoxy-Cι-C 6 - alkyl, (Ci-Cg-alkyl) carbonyl,
(Ci-Cg-Alkoxy) carbonyl, (Ci-Cg-Alkoxy) carbonyl- Ci-Cg-alkyl, (Ci-Cg-Alkoxy) carbonyl-C-Cδ-alkenyl, wobei die Alkenylkette zusätzlich ein bis drei Halogen- und/oder Cyano-Reste tragen kann, oder Ci-Cg-Alkylsulfonyl, (Ci-Cg -Alkoxy) carbonyl -(Ci-Cg-alkoxy) carbonyl, (Ci-Cg-alkoxy) carbonyl-Ci-Cg-alkyl, (Ci-Cg-alkoxy) carbonyl-CC δ- alkenyl, the alkenyl chain additionally one to three halogen and / or Can carry cyano residues, or Ci-Cg-alkylsulfonyl, (Ci-Cg -alkoxy) carbonyl -
Ci-Cg-alkylsulfonyl, Phenyl oder Phenylsulfonyl, wobei die beiden Phenylringe unsubstituiert sein oder ihrerseits einen bis drei Substituenten tragen können, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Halogen, Ci-C -Alkyl,Ci-Cg-alkylsulfonyl, phenyl or phenylsulfonyl, where the two phenyl rings can be unsubstituted or in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-C-alkyl,
Ci-Cg-Halogenalkyl, C3-C6-Alkenyl, Ci-Cδ-Alkoxy und (Ci-Cg-Alkoxy) carbonyl, oder R25 und R26 und/oder R27 und R28 zusammen mit dem jeweils gemeinsamen Stickstoffatom für einen gesättigten oder ungesättigten 4- bis 7gliedrigen Azaheterocyclus, der neben Kohlenstoffringgliedern gewünschtenfalls eines der folgenden Glieder enthalten kann: -0-, -S-, -N=, -NH- Oder -N (Cι-C6-Alkyl) -;Ci-Cg-haloalkyl, C 3 -C 6 alkenyl, Ci-C δ alkoxy and (Ci-Cg-alkoxy) carbonyl, or R 25 and R 26 and / or R 27 and R 28 together with the respective common nitrogen atom for a saturated or unsaturated 4- to 7-membered azaheterocycle which, if desired, is one of the can contain the following elements: -0-, -S-, -N =, -NH- or -N (-C-C 6 alkyl) -;
sowie die landwirtschaftlich brauchbaren Salze und Enolether der Verbindungen I.and the agriculturally useful salts and enol ethers of the compounds I.
2. l-Aryl-4-thiouracile der Formel I nach Anspruch 1, wobei Y für Stickstoff oder die Methingruppe steht.2. l-aryl-4-thiouracile of formula I according to claim 1, wherein Y is nitrogen or the methine group.
3. l-Aryl-4-thiouracile der Formel I nach Anspruch 1, wobei Y zusammen mit R6 für eine Brücke >C-0-C (R10) =N- steht.3. l-aryl-4-thiouracile of formula I according to claim 1, wherein Y together with R 6 is a bridge> C-0-C (R 10 ) = N-.
4. l-Aryl-4-thiouracile der Formel I nach Anspruch 1, wobei R6 zusammen mit R5 für einen über den Sauerstoff an R5 ge- bundenen Rest -N(R7) -CO-C (R8' , R9' ) -0- steht.4. l-aryl-4-thiouracils of the formula I according to claim 1, wherein R 6 together with R 5 is a 5 out via the oxygen of R-bound radical -N (R 7) -CO-C (R 8 ', R 9 ') -0-.
5. l-Aryl-4-thiouracile der Formel I nach Anspruch 1, wobei R6 für5. l-aryl-4-thiouracile of formula I according to claim 1, wherein R 6 for
2) Ci-Cg-Alkoxy, C2-C6-Alkenyloxy oder C2-C6-Alkinyloxy, wobei jeder dieser 3 Reste gewünschtenfalls einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Halogen, Ci-Cg-Alkoxy, C3-C6-Alkenyloxy, C3-C6-Alkinyloxy, Cι-C6-Alkylsulfonyl, -CO-R12, -CO-OR12, -CO-N(R12)R13, -N(R2)-R13 und -C(R14)=N-0R11;2) Ci-Cg-alkoxy, C 2 -C 6 alkenyloxy or C 2 -C 6 -alkynyloxy, each of these 3 radicals optionally being able to carry one to three substituents, each selected from the group consisting of halogen, Ci-Cg- Alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, -C-C 6 alkylsulfonyl, -CO-R 12 , -CO-OR 12 , -CO-N (R 12 ) R 13 , -N (R 2 ) -R 13 and -C (R 14 ) = N-0R 11 ;
3) -CO-R15, -C(NR16)-R15, -C(R15) (OR17) (OR18) , -C(R15)=C(R19)-CO-R20, -CH(R15)-CH(R19)-CO-R20, -CO-OR24, -CO-N (R24) -OR11, -C (R15) =C (R19) -C (R14) =N-ORlx, -C(R14)=N-OR1:L, -C(OR17) (OR18)-OR24, -N(R25)R26 oder -CO-N(R25)-R26 steht.3) -CO-R 15 , -C (NR 16 ) -R 15 , -C (R 15 ) (OR 17 ) (OR 18 ), -C (R 15 ) = C (R 19 ) -CO-R 20 , -CH (R 15 ) -CH (R 19 ) -CO-R 20 , -CO-OR 24 , -CO-N (R 24 ) -OR 11 , -C (R 15 ) = C (R 19 ) - C (R 14 ) = N-OR lx , -C (R 14 ) = N-OR 1: L , -C (OR 17 ) (OR 18 ) -OR 24 , -N (R 25 ) R 26 or -CO -N (R 25 ) -R 26 is.
6. l-Aryl-4-thiouracile der Formel I nach Anspruch 1, wobei6. l-aryl-4-thiouracile of formula I according to claim 1, wherein
X für Sauerstoff,X for oxygen,
R1 für Wasserstoff, Amino oder Methyl,R 1 represents hydrogen, amino or methyl,
R2 für Wasserstoff, Halogen oder Methyl,R 2 represents hydrogen, halogen or methyl,
R3 für Wasserstoff, Halogen oder Methyl,R 3 represents hydrogen, halogen or methyl,
Y für die Methingruppe oder zusammen mit R6 für eine Brücke >C-O-C(R10)=N-,Y for the methine group or together with R 6 for a bridge> COC (R 10 ) = N-,
R5 für Cyano oder Halogen, R6 zusammen mit R5 für einen über den Sauerstoff an R5 gebundenen Rest -N(R7) -CO-CH2-0-, oder fürR 5 for cyano or halogen, R 6 together with R 5 for a radical -N (R 7 ) -CO-CH 2 -0- bonded via the oxygen to R 5 , or
2) Ci-Cg-Alkoxy, C2-Cδ-Alkenyloxy oder C2-Cδ-Alkinyloxy, wobei jeder dieser 3 Reste gewünschtenfalls einen bis drei Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Halogen, Ci-Cδ-Alkoxy, C3-Cg-Alkenyloxy, C3-Cδ-Alkinyloxy, Ci-Cg-Alkyl- sulfonyl, -CO-R12, -CO-OR12, -CO-N (R12) R13 , -N(R12)-R13 und -C(R14)=N-OR1:L; 3) -CO-R15, -C(NR16)-R15, -C (R15) (OR17) (OR18) ,2) Ci-Cg-alkoxy, C 2 -C δ- alkenyloxy or C 2 -C δ- alkynyloxy, where each of these 3 radicals can optionally carry one to three substituents, each selected from the group consisting of halogen, Ci-C δ -Alkoxy, C 3 -Cg-alkenyloxy, C 3 -C δ -alkynyloxy, Ci-Cg-alkylsulfonyl, -CO-R 12 , -CO-OR 12 , -CO-N (R 12 ) R 13 , - N (R 12 ) -R 13 and -C (R 14 ) = N-OR 1: L ; 3) -CO-R 15 , -C (NR 16 ) -R 15 , -C (R 15 ) (OR 17 ) (OR 18 ),
-C (R15) =C (R9 ) -CO-R20 , -CH (R15 ) -CH (R1 ) -CO-R20 , -CO-OR24, -CO-N(R2 )-OR1]-,-C (R 15 ) = C (R 9 ) -CO-R 20 , -CH (R 15 ) -CH (R 1 ) -CO-R 20 , -CO-OR 24 , -CO-N (R 2 ) -OR 1] -,
-C (R15) =C (R19 ) -C (R14) =N-OR11, -C (R14 ) =N-OR11 , -C(OR17) (OR18)-OR24, -N(R25)R26 oder -CO-N(R25) -R26 stehen.-C (R 15 ) = C (R 19 ) -C (R 14 ) = N-OR 11 , -C (R 14 ) = N-OR 11 , -C (OR 17 ) (OR 18 ) -OR 24 , -N (R 25 ) R 26 or -CO-N (R 25 ) -R 26 .
7. Verwendung der l-Aryl-4-thiouracile der Formel I und ihrer landwirtschaftlich brauchbaren Salze und Enolether, gemäß Anspruch 1, als Herbizide.7. Use of the l-aryl-4-thiouracile of the formula I and their agriculturally useful salts and enol ethers, according to claim 1, as herbicides.
8. Herbizides Mittel, enthaltend eine herbizid wirksame Menge mindestens eines l-Aryl-4-thiouracils der Formel I oder eines landwirtschaftlich brauchbaren Salzes oder Enolethers von I, gemäß Anspruch 1, und mindestens einen inerten flüssigen und/ oder festen Trägerstoff sowie gewünschtenfalls mindestens einen oberflächenaktiven Stoff.8. Herbicidal composition comprising a herbicidally effective amount of at least one l-aryl-4-thiouracil of the formula I or an agriculturally useful salt or enol ether of I, according to claim 1, and at least one inert liquid and / or solid carrier and, if desired, at least one surfactant.
9. verfahren zur Herstellung von herbizid wirksamen Mitteln, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge mindestens eines l-Aryl-4-thiouracils der Formel I oder eines landwirtschaftlich brauchbaren Salzes oder Enolethers von I, gemäß Anspruch 1, und mindestens einen inerten flüssigen und/ oder festen Trägerstoff sowie gewünschtenfalls mindestens einen oberflächenaktiven Stoff mischt.9. A process for the preparation of herbicidally active agents, characterized in that a herbicidally effective amount of at least one l-aryl-4-thiouracil of the formula I or an agriculturally useful salt or enol ether of I, according to claim 1, and at least one inert liquid and / or solid carrier and, if desired, mixes at least one surface-active substance.
10. Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge mindestens eines l-Aryl-4-thiouracils der Formel I oder eines landwirtschaftlich brauchbaren Salzes oder Enolethers von I, gemäß Anspruch 1, auf Pflanzen, deren Lebensraum oder auf Saatgut einwirken läßt.10. A method for controlling unwanted vegetation, characterized in that a herbicidally effective amount of at least one l-aryl-4-thiouracil of the formula I or an agriculturally useful salt or enol ether of I, according to claim 1, on plants, their habitat or can act on seeds.
11. Verfahren zur Herstellung von l-Aryl-4-thiouracilen der Formel I gemäß Anspruch 1, dadurch gekennzeichnet, daß man 1-Aryluracile der Formel II
Figure imgf000077_0001
11. A process for the preparation of l-aryl-4-thiouracils of the formula I according to claim 1, characterized in that 1-aryluracils of the formula II
Figure imgf000077_0001
mit einem Schwefelungsreagenz behandelt.treated with a sulfurization reagent.
1010
1515
2020th
2525
3030
3535
4040
45 45
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WO2014202510A1 (en) 2013-06-20 2014-12-24 Bayer Cropscience Ag Aryl sulfide derivatives and aryl sulfoxide derivatives as acaricides and insecticides
WO2015004028A1 (en) 2013-07-08 2015-01-15 Bayer Cropscience Ag Six-membered c-n-linked aryl sulfide derivatives and aryl sulfoxide derivatives as pest control agents
WO2016091857A1 (en) 2014-12-11 2016-06-16 Bayer Cropscience Aktiengesellschaft Five-membered c-n bonded aryl sulphide and aryl sulphoxide derivatives as pest control agents

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014202505A1 (en) 2013-06-20 2014-12-24 Bayer Cropscience Ag Aryl sulfide derivatives and aryl sulfoxide derivatives as acaricides and insecticides
WO2014202510A1 (en) 2013-06-20 2014-12-24 Bayer Cropscience Ag Aryl sulfide derivatives and aryl sulfoxide derivatives as acaricides and insecticides
WO2015004028A1 (en) 2013-07-08 2015-01-15 Bayer Cropscience Ag Six-membered c-n-linked aryl sulfide derivatives and aryl sulfoxide derivatives as pest control agents
CN105517995A (en) * 2013-07-08 2016-04-20 拜耳作物科学股份公司 Six-membered C-N bonded aryl sulfide and aryl sulfoxide derivatives as pesticides
CN105517995B (en) * 2013-07-08 2018-10-02 拜耳作物科学股份公司 Six-membered C-N bonded aryl sulfide and aryl sulfoxide derivatives as pesticides
WO2016091857A1 (en) 2014-12-11 2016-06-16 Bayer Cropscience Aktiengesellschaft Five-membered c-n bonded aryl sulphide and aryl sulphoxide derivatives as pest control agents

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