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WO1998038169A1 - Substituted 3-phenyl pyrazoles - Google Patents

Substituted 3-phenyl pyrazoles Download PDF

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Publication number
WO1998038169A1
WO1998038169A1 PCT/EP1998/000781 EP9800781W WO9838169A1 WO 1998038169 A1 WO1998038169 A1 WO 1998038169A1 EP 9800781 W EP9800781 W EP 9800781W WO 9838169 A1 WO9838169 A1 WO 9838169A1
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WIPO (PCT)
Prior art keywords
alkyl
carbonyl
ethyl
amino
alkoxy
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PCT/EP1998/000781
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German (de)
French (fr)
Inventor
Cyrill Zagar
Gerhard Hamprecht
Markus Menges
Olaf Menke
Robert Reinhard
Peter Schäfer
Karl-Otto Westphalen
Ulf Misslitz
Helmut Walter
Original Assignee
Basf Aktiengesellschaft
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Priority to AU67194/98A priority Critical patent/AU6719498A/en
Publication of WO1998038169A1 publication Critical patent/WO1998038169A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom

Definitions

  • the present invention relates to new substituted 3-phenylpyrazoles of the formula I.
  • R 3 is cyano, halogen, C ⁇ ⁇ C 4 alkyl or C ⁇ -C 4 haloalkyl
  • R 5 cyano, halogen, -CC 4 -alkyl, -C-C 4 -haloalkyl, -C-C 4 -alkoxy or -C-C 4 -haloalkoxy;
  • the invention also relates to herbicidal compositions which comprise the compounds I as active substances,
  • Herbicidally active 3-phenylpyrazoles of the type of the compounds I have been described in particular in DE-A 195 24 623, EP-A 443 059, WO 95/32 188, WO 96/01 255, WO 96/15 115, WO 96/40 643 and WO 97/02251.
  • the object of the present invention was therefore to provide new herbicidally active compounds which can be used to combat undesirable plants better than before.
  • herbicidal compositions which contain the compounds I and have a very good herbicidal action.
  • 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 enantiomeric or diastereomeric bonds.
  • 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.
  • the cations include, in particular, the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, which if desired, can be one to can carry four C 1 -C 4 alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 alkyl) sulfonium and sulfoxonium
  • 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 1 -C 4 alkanoic acids, preferably formate, acetate, propionate and butyrate.
  • Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine or chlorine.
  • C 1 -C 4 alkyl for: CH 3 , C 2 H 5 , n-propyl, CH (CH 3 ) 2 , n-butyl, 1-methylpropyl, CH 2 -CH (CH 3 ) 2 or C (CH 3 ) 3 , especially for CH 3 or CH 5 ;
  • Ci-C ß- alkyl for: -C ⁇ C 4 alkyl as mentioned above, or for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl,
  • -C-C 4 haloalkyl for: a C ⁇ -C 4 alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CH 2 C1, CH (C1) 2 # C ( C1) 3 , CH 2 F, CHF 2 , CF 3 CHFC1, CF (C1) 2 / CF 2 C1, CF 2 Br, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl , CH 2 -CH 2 F, CH 2 -CF 3 , 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 1,2-dichloroethyl, 2,2,2-trichloroethyl, C 2 F 5 , 2-fluoropropyl,
  • Ci-C ⁇ -haloalkyl for: Ci-C ⁇ -alkyl as mentioned above, partially or completely by fluorine, chlorine and / or
  • Bromine is substituted, so for example one of the above -CC. 4 -haloalkyl radicals, or 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-ododyl, 5, 5, 5-trichloropentyl, n-CsFn, 6-fluorohexyl, 6-chlorohexyl, 6-bromhexyl, 6-iodohexyl , 6, 6, 6-trichlorohexyl or nC 6 F ⁇ 3 , in particular for CH 2 F, CHF 2 , CF 3 , CH 2 C1, 2-fluoroethyl, 2-chloroethyl or 2, 2, 2-trifluoroethyl;
  • C 3 -C 6 -cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, in particular for cyclopentyl or cyclohexyl;
  • C 3 -C 8 cycloalkyl which contains a carbonyl or thiocarbonyl ring member, for: for example cyclobutanon-2-yl, cyclobutanon-3-yl, cyclopentanon-2-yl, cyclopentanon-3-yl, cyclohexanone-2 -yl, Cyclohexanon-4-yl, Cycloheptanon-2-yl, Cyclooctanon-2-yl, Cyclobutanthion-2-yl, Cyclobutanthion-3-yl, Cyclopentanthion-2-yl, Cyclopentanthion-3-yl, Cyclohexanthion- 2 -yl, cyclohexanthion-4-yl, cycloheptanthion-2-yl or cyclooctanthion-2-yl;
  • -C -C alkoxy for: OCH 3 , 0C 2 H 5 , 0CH 2 -C 2 H 5 , 0CH (CH 3 ) 2 , n-butoxy, 1-methylpropoxy, OCH 2 -CH (CH 3 ) or OC (CH 3 ) 3 , in particular for OCH 3 , OC 2 H 5 , OCH (CH 3 ) 2 or OC (CH 3 ) 3 ;
  • -C-C 4 haloalkoxy for: -C-C 4 alkoxy as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 0CH 2 C1, 0CH (C1) 2 , 0C (C1 ) 3 , OCH 2 F, OCHF2, OCF 3 , OCHFC1, 0CF (C1) 2 .
  • Cyano-C 1 -C 4 -alkyl for: for example CH 2 CN, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyanoprop-l-yl,
  • Hydroxy-C 1 -C 4 -alkyl for: for example CHOH, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxyprop-l-yl, 2-hydroxyprop-l-yl, 3-hydroxyprop-l-yl, 1-hydroxybut-l -yl, 2-Hydroxybut-l-yl, 3-Hydroxybut-l-yl, 4-Hydroxybut-l-yl, 1-Hydroxybut-2-yl, 2-Hydroxybut-2-yl, 3-Hydroxybut-2-yl , 4-hydroxybut-2-yl, l- (CH 2 OH) eth-l-yl, 1- (CH 2 OH) -1- (CH 3 ) -eth-l-yl or 1- (CH 2 ⁇ H) prop-l-yl, especially for CH 2 OH or 2-hydroxyethyl;
  • Hydroxycarbonyl-C 1 -C alkyl for: e.g. B. CH 2 COOH, 1- (COOH) ethyl, 2- (COOH) ethyl, 1- (COOH) prop-l-yl, 2- (COOH) prop-l-yl, 3- (COOH) prop-l-yl , 1- (COOH) but-l-yl, 2- (COOH) but-l-yl, 3- (COOH) but-l-yl, 4- (COOH) but-l-yl, 1- (COOH) but-2-yl, 2- (COOH) but-2-yl, 3- (C00H) but-2-yl, 4- (COOH) but-2-yl, l- (CH 2 COOH) eth-l- yl, 1- (CH 2 COOH) -1- (CH 3 ) -eth-1-yl or 1- (CH 2 C00H) prop-l-yl, especially for CHCOOH or 2-hydroxycarbonylethyl;
  • Amino -CC 4 -alkyl for: for example CH 2 NH 2 , 1-aminoethyl, 2-aminoethyl, 1-aminoprop-l-yl, 2-aminoprop-l-yl, 3-aminoprop-l-yl, 1-aminobu.tl-yl, 2-aminobut-l-yl, 3-aminobut-l-yl, 4-amino-but-l-yl, l-aminobut-2-yl, 2-aminobut-2-yl, 3-aminobut-2-yl, 4-aminobut-2-yl, 1- (CH 2 NH 2 ) eth-l-yl, 1- (CH 2 NH 2 ) -1- (CH 3 ) - eth-l- yl or 1- (CH 2 NH) prop-l-yl, in particular for CH 2 NH 2 or 2-aminoethyl;
  • Aminocarbonyl -CC-C-alkyl for: for example CH 2 CONH 2 , 1- (CONH 2 ) ethyl, 2- (CONH 2 ) ethyl, 1- (CONH 2 ) prop-l-yl, 2- (CONH 2 ) prop -l-yl, 3- (CONH 2 ) prop-l-yl, 1- (CONH 2 ) but-l-yl, 2- (CONH 2 ) but-l-yl, 3- (CONH 2 ) but-l -yl, 4- (CONH 2 ) but-l-yl, 1- (CONH 2 ) but-2-yl, 2- (CONH 2 ) but-2-yl, 3- (CONH 2 ) but-2-yl , 4- (CONH 2 ) but-2-yl, l- (CH 2 CONH) eth-l-yl, 1- (CH 2 CONH 2 ) -1- (CH 3 ) -eth-l-yl or 1- (CH 2
  • Phenyl-C ⁇ ⁇ C 4 alkyl for: benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-l-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-phenylbut-2-yl, 1- (benzyl) -eth-l-yl, 1- (benzyl) -1- (methyl) -eth-l-yl or 1- (benzyl) prop-1-yl, especially for benzyl or 2-phenylethyl;
  • C 3 -C 8 cycloalkyl -CC 4 -alkyl for: cyclopropylmethyl, 1-cyclopropyl-ethyl, 2-cyclopropyl-ethyl, 1-cyclopropyl-prop-l-yl, 2-cyclopropyl-prop-l- yl, 3-cyclopropyl-prop-l-yl, 1-cyclopropyl-but-1-yl, 2-cyclopropyl-but-l-yl, 3-cyclopropyl-but-l-yl, 4-cyclopropyl-but- l-yl, l-cyclopropyl-but-2-yl, 2-cyclopropyl-but-2-yl, 3-cyclopropyl-but-2-yl, 3-cyclopropyl-but-2-yl, 4-cyclopropyl- but-2-yl, 1- (cyclopropylmethyl) eth-l-yl, 1- (cyclopropylmethyl) -1- (CH 3
  • C 3 -C 8 cycloalkyl-C 4 -C 4 alkyl which contains a carbonyl or thiocarbonyl ring member, for: for example cyclobutanon-2-ylmethyl, cyclobutanon-3-ylmethyl, cyclopentanon-2-ylmethyl, Cyclopentanone-3-ylmethyl, cyclohexanone-2-ylmethyl, cyclohexanone-4-ylmethyl, cycloheptanone-2-ylmethyl, cycloctanon-2-ylmethyl, cyclobutanthion-2-ylmethyl, cyclobutanethion-3-ylmethyl, cyclopentanthione- 2-ylmethyl, cyclopentanethion-3-ylmethyl, cyclohexanthion-2-ylmethyl, cyclohexanethion-4-ylmethyl, cycloheptanthion-2-ylmethyl, cyclooctanethion-2-y
  • C ⁇ -C4-haloalkoxy-C ⁇ -C 4 alkyl by C ⁇ -C ⁇ 4 haloalkoxy as mentioned above substituted C ⁇ -C4 alkyl, eg for 2- (difluoromethoxy) ethyl, 2- (trifluoromethoxy) ethyl or 2- (pentafluoroethoxy) ethyl;
  • C 3 -C 8 cycloalkyloxy-C 4 -C 4 alkyl for: cyclopropyloxymethyl, 1-cyclopropyloxy-ethyl, 2-cyclopropyloxy-ethyl, 1-cyclo-propyloxy-prop-1-yl, 2-cyclopropyloxy-prop-l- yl, 3-cyclopropyloxy-prop-1-yl, 1-cyclopropyloxy-but-l-yl, 2-cyclopropyloxy-but-1-yl, 3-cyclopropyloxy-but-l-yl, 4-cyclopropyl oxy-but-1-yl, l-cyclopropyloxy-but-2-yl, 2-cyclopropyloxy-but-2-yl, 3-cyclopropyloxy-but-2-yl, 3-cyclopropyloxy-but-2-yl, 4- Cyclopropyloxy-but-2-yl, 1- (cyclopropyloxymethyl) - eth-l-
  • C 1 -C 4 alkylthio -CC-C 4 alkyl for: by C ⁇ . -C 4 -Alkylthio as above-substituted -CC 4 -alkyl, for example for CH 2 SCH 3 , CH 2 SC 2 H 5 , n-propylthiomethyl, CH 2 SCH (CH 3 ) 2 , n-butyl-thiomethyl, (1-methylpropylthio) methyl, (2-methylpropylthio) methyl, CH 2 SC (CH 3 ) 3 , 2-methylthioethyl, 2-ethylthioethyl, 2- (n-propylthio) ethyl, 2- (1-methylethylthio) ethyl, 2- (n-butylthio) ethyl, 2- (1-methylpropylthio) ethyl, 2- (2-methylpropylthio) ethyl, 2- (1, 1-dimethyleth
  • C 1 -C 4 -Halogenalkylthio-C 1 -C 4 -alkyl for: C 1 -C 4 -alkyl-substituted C 1 -C 4 -alkyl as mentioned above, for example for 2 - (difluoromethylthio) ethyl, 2 - (SCF 3 ) ethyl or 2- (SC 2 F 5 ) ethyl;
  • COCH (CH 3 ) 2 n-butylcarbonyl, COCH (CH 3 ) -C 2 H 5 , COCH -CH (CH 3 ) 2 or COC (CH 3 ) 3 , especially for COCH 3 , COC 2 H 5 or C0C ( CH 3 ) 3 ;
  • (-C-C 4 -haloalkyl) carbonyl (-C-C 4 -alkyl) carbonyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example C0CH (C1) 2 , C0C (C1) 3 , COCH 2 F, COCHF2, COCF 3 , C0CH 2 C1, COCHFC1, C0CF (C1), C0CF 2 C1, COCF 2 Br, 1-fluoroethylcarbonyl, C0CH 2 -CH 2 F, COCH 2 -CHF 2 , COCH 2 -CF 3 , 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2, 2-difluoroethylcarbonyl, 2, 2-dichloro-2-fluoroethylcarbonyl, 1, 2-dichloroethylcarbonyl, COCH 2 -C (Cl) 3 , COC 2 F 5
  • (C 1 -C 4 alkyl) carbonyl -CC 4 -alkyl for: C 1 -C 4 -alkyl substituted by (-C 4 -alkyl) carbonyl as mentioned above, for example for CH 2 COCH 3 , CH 2 COC 2 H 5 or CH 2 COC (CH 3 ) 3 ;
  • (C ⁇ -C 4 haloalkyl) carbonyl-C ⁇ -C4 alkyl for: by (C ⁇ -C 4 haloalkyl) carbonyl as mentioned above substituted C 1 -C 4 alkyl, eg CH 2 COCF 3 or CH 2 C0CH 2 C1;
  • C 1 -C 4 alkylcarbonyloxy for: O-COCH 3 , 0-COC 2 H 5 , 0-COCH 2 -C 2 H 5 , 0-COCH (CH 3 ) 2 , n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, O- COCH 2 -CH (CH 3 ) 2 or 0-COC (CH 3 ) 3 , in particular for 0-COCH 3 , 0-COC 2 H 5 or 0-COC (CH 3 ) 3 ;
  • (-C-C 4 haloalkyl) carbonyloxy for: (C 1 -C 4 alkyl) carbonyloxy as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for 0-COCH 2 F , 0-COCHF 2 , O-COCF 3 , 0-COCH 2 Cl, 0-COCH (Cl) 2 , 0-COC (C1) 3 , O-COCHFCl, 0 ⁇ C0CF (C1) 2 , 0-COCF 2 Cl , 0-COCF 2 Br, 1-fluoroethylcarbonyloxy, 0-COCH 2 -CH 2 F, 0-COCH 2 -CHF 2 , 0-C0CH 2 -CF 3 , 2-chloro-2-fluoroethylcarbonyloxy, 2-chloro-2, 2-difluoroethylcarbonyloxy, 2, 2-dichloro-2-fluoroethy
  • (-CC 4 alkoxy) carbonyl for: COOCH 3 , COOC 2 H 5 , n-propoxycarbonyl, COOCH (CH 3 ) 2 , n-butoxycarbonyl, 1- (methylpropoxy) carbonyl, COOCH 2 -CH (CH 3 ) 2 or COOC (CH 3 ) 3 , especially for COOCH 3 , COOC 2 H 5 or COOC (CH 3 ) 3 ;
  • (-CC 4 alkoxy) carbonyl -CC 4 -alkyl for: C 1 -C 4 -alkoxy-carbonyl substituted as above-mentioned C 1 -C 4 -alkyl, for example for CH 2 COOCH 3 , CH 2 COOC 2 H 5 , CH 2 CH 2 COOCH 3 , CH 2 CH 2 COOC 2 H 5 , CH (CH 3 ) COOCH 3 or CH (CH 3 ) COOC 2 H 5 ;
  • (-CC 4 haloalkoxy) carbonyl -CC 4 -alkyl for: (C ⁇ -C 4 -alkoxy) - carbonyl -CC 4 -alkyl as mentioned above, the alkoxy part of which is partially or completely by fluorine, chlorine , Bromine and / or iodine is substituted, for example CH 2 COOCH 2 CF 3 or CH (CH 3 ) COCH 2 CF 3 ;
  • Di (C 1 -C 4 alkyl) amino for: for example N (CH 3 ) 2 , N (C 2 H 5 ) 2 , N, N-dipropylamino, N, N-di- (1-methylethyl) amino, N, N-dibutylamino, N, N-di- (1-methylpropyl) amino, N, N-di- (2-methylpropyl) amino, N, N-di- (1, 1-dimethylethyl) amino, N-ethyl -N-methylamino, N-methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino, N-methyl -N- (2-methylpropyl) amino, N- (l, 1-dimethylethyl) -N-methylamino, N-ethyl-N-propylamino
  • Di (-C 4 alkyl) amino -C 4 alkyl for: by di (C 4 alkyl) amino - as mentioned above - substituted C 1 -C 4 alkyl, for example for CH 2 N (CH 3 ) 2, CHN (C 2 H5) 2, N, N-dipropylaminomethyl, N, N-di (1-methylethyl) aminomethyl, N, N-dibutylaminomethyl, N, N-di (1-methylpropyl) minomethyl , N, N-Di (2-methylpropyl) aminomethyl, N, N-Di (1, 1-dimethylethyl) aminomethyl, N-ethyl-N-methylaminomethyl, N-methyl-N-propylaminomethyl, N-methyl-N- (1-methylethyl) aminomethyl, N-butyl-N-methylaminomethyl, N-methyl-N- (1-methylpropyl) aminomethyl, N-methyl-N- (2-methylpropyl) amino
  • Di (C 1 -C 4 alkyl) aminocarbonyl for: a di (C ⁇ -C 4 alkyl) amino radical bonded via a carbonyl bridge, as mentioned above;
  • Di (C 3 -C 4 alkyl) aminocarbonyl - as mentioned above - substituted C 1 -C 4 alkyl for example for CH 2 -CON (CH 3 ) 2 , CH 2 -CON (C 2 H 5 ) 2 , N, N-dipropylamino-COCH-, N, N-di- (1-methylethyl) amino-COCH 2 -, N, N-dibutylamino-COCH 2 -, N, N-di- (l-methylpropyl) arrtino- COCH 2 -, N, N-di- (2-methylpropyl) amino-COCH 2 -, N, N-di- [1, 1-dimethylethyl] amino-COCH 2 -, N-ethyl-N-methylamino- COCH 2 -, N-methyl-N-propylamino-COCH 2 -, N-methyl-N- (1-methylethyl) amino-COCH 2
  • -C-C 4 alkylamino -CC 4 -alkyl for: by -C-C 4 alkylamino such as -NH-CH 3 , -NH-C2H5, -NH- (n-propyl), -NH-CH (CH 3 ) 2 / -NH- (n-butyl), -NH-CH (CH 3 ) -C 2 H 5 , -NH-CH 2 -CH (CH 3 ) and -NH-C (CH 3 ) 3 , preferably - NH-CH 3 or -NH-C 2 H 5 , substituted C 1 -C 4 alkyl, for example for CH 2 CH 2 -NH-CH 3 or CH 2 CH 2 -NH-C 2 H 5 ;
  • C 3 -C 6 ⁇ alkenyl for: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl , n-buten-3-yl, 1-methyl-prop-1-en-l-yl, 2-methylprop-l-en-l-yl, l-methylprop-2-en-1-yl, 2-methylprop -2-en-l-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methylbut-l-en-l -yl, 2-methylbut-l-en-l-yl, 3-methylbut-l-en-l-yl, 1-methylbut- 2-en-l-yl, 2-methylbut-2-en-l-yl, 3-methylbut-2-en-l-yl, l-methylbut-3-en-l-yl, 2-
  • C 3 -C 6 haloalkenyl for: C 3 -C ⁇ alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for 2-chloroallyl, 3-chloroallyl, 2, 3-dichlorallyl, 3, 3-dichlorallyl, 2,3,3-trichlorallyl, 2, 3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2, 3-dibromoallyl, 3, 3-dibromoallyl, 2, 3, 3-tribromo-allyl or 2,3-dibromobut-2-enyl, in particular for 2-chloro-allyl, 3-chloroallyl or 3,3-dichloroallyl;
  • Cyano-C 3 -C 6 -alkenyl for: eg 2-cyanoallyl, 3-cyanoallyl, 4-cyanobut-2-enyl, 4-cyanobut-3-enyl or 5-cyanopent-4-enyl, in particular for 3-cyanoallyl or 4-cyanobut-2-enyl;
  • C 3 -C 6 alkynyl for: prop-1-in-1-yl, propargyl, n-but-1-in-1-yl, n-but-1-in-3-yl, n-but-1 -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-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-1-yl, n-hex-l-in -3-yl, n-hex-1-in-4-yl, n-hex-1-in-5-yl,
  • C 3 -C 6 -Ha-logenalkynyl for: C 3 -C 6 ⁇ alkynyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for 1,1-di-fluoroprop- 2-in-l-yl, 4-fluorobut-2-in-l-yl, 4-chlorobut-2-in-1-yl, 1,1-difluorobut-2-in-l-yl, 5-fluoropentyl 3-in-l-yl or
  • Cyano-C 3 -C 6 -alkynyl for: e.g. 3-cyanopropargyl, 4-cyano-but-2-in-l-yl, 5-cyanopent-3-in-l-yl and 6-cyanohex-4-in 1-yl;
  • C 3 -C 4 alkenyloxy -CC-C 4 alkyl for: by C 3 -C 4 alkenyloxy such as allyloxy, but-l-en-3-yloxy, but-l-en-4-yloxy, but-2 -en-l-yl-oxy, l-methylprop-2-enyloxy and 2-methylprop-2-enyloxy, substituted C 1 -C 4 alkyl, for example for allyloxy-methyl, 2-allyloxyethyl or but-l-ene -4-yloxymethyl, especially for 2-allyloxyethyl;
  • C 3 -C 4 alkynyloxy -CC-C 4 alkyl for: by C 3 -C 4 ⁇ alkynyloxy such as propargyloxy, but-l-in-3-yloxy, but-l-in-4-yloxy, but-2 -in-l-yloxy, l-methylprop-2-ynyloxy and 2-methylprop-2-ynyloxy, preferably propargyloxy, substituted C 1 -C 4 -alkyl, so for example for propargyloxymethyl or 2-propargyloxyethyl, especially for 2-propargyloxyethyl ;
  • C 3 -C 4 alkenylthio -CC-C 4 alkyl for: by C 3 -C 4 ⁇ alkenylthio such as allylthio, but-l-en-3-ylthio, but-l-en-4-ylthio, but-2 -en-l-ylthio, l-methylprop-2-enylthio and 2-methylprop-2-enylthio, substituted C 1 -C 4 -alkyl, for example for allylthio-methyl, 2-allylthioethyl or but-l-en-4- ylthiomethyl, especially for 2- (allylthio) ethyl;
  • C 3 -C 4 alkynylthio -CC-C 4 alkyl for: by C 3 -C 4 alkynylthio such as propargylthio, but-l-in-3-ylthio, but-l-in-4-ylthio, but-2 -in-l-ylthio, l-methylprop-2-ynylthio and 2-methyl-prop-2-ynylthio, preferably propargylthio, substituted C 1 -C 4 alkyl, for example for propargylthiomethyl or 2-propargylthioethyl, especially for 2- (Propargyl hio) - ethyl. All phenyl or cycloalkyl rings are preferably unsubstituted or have a substituent.
  • R 1 C 1 -C 4 alkyl, especially methyl
  • R 2 C ⁇ -C 4 haloalkyl, especially difluoromethyl
  • R 3 cyano, halogen or -CC 4 ⁇ haloalkyl, especially halogen; chlorine is particularly preferred;
  • R 4 fluorine or chlorine, especially fluorine
  • R 5 halogen or -CC 4 haloalkyl, especially chlorine, bromine or trifluoromethyl; chlorine is particularly preferred;
  • (C ⁇ -C 4 -alkoxy) imino group may bear, phenyl or benzyl, in particular Ci-Ce-alkyl, C ⁇ -C4-alkoxy-C ⁇ -C 4 alkyl, C 3 -C 6 alkenyl, C 3 - C ⁇ -alkynyl or (-CC 4 alkoxy) carbonyl - C 1 -C 4 alkyl.
  • the substituted 3-phenylpyrazoles of the formula I can be obtained in various ways, in particular by one of the following processes:
  • One embodiment consists in first preparing the corresponding acid chloride from II and then in the presence of a base, e.g. an amine such as triethylamine or pyridine, an alkali metal carbonate such as potassium carbonate, an alkali metal hydride such as sodium hydride or an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide - to react with an oxyamine IV.
  • a base e.g. an amine such as triethylamine or pyridine
  • an alkali metal carbonate such as potassium carbonate
  • an alkali metal hydride such as sodium hydride or an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide - to react with an oxyamine IV.
  • Suitable chlorinating agents are, for example, phosgene, oxalyl chloride, phosphorus oxychloride and thionyl chloride.
  • the chlorination is generally carried out in an inert organic solvent, for example aliphatic or aromatic hydrocarbons such as n-hexane and toluene, halogenated hydrocarbons such as dichloromethane, ethers such as diethyl ether and tetrahydrofuran, and aprotic solvents such as dimethylformamide and acetonitrile.
  • an inert organic solvent for example aliphatic or aromatic hydrocarbons such as n-hexane and toluene, halogenated hydrocarbons such as dichloromethane, ethers such as diethyl ether and tetrahydrofuran, and aprotic solvents such as dimethylformamide and acetonitrile.
  • Solvents are also generally suitable, as well as their
  • a second embodiment consists of reacting II directly with the oxyamine I-y in one of the above-mentioned organic solvents. This is preferably carried out in the presence of a coupling reagent such as carbonyldiimidazole and dicyclohexylcarbodiimide.
  • a coupling reagent such as carbonyldiimidazole and dicyclohexylcarbodiimide.
  • L stands for a common leaving group such as halogen, methylsulfonyloxy, trifluoromethylsulfonyloxy and p-tolylsulfonyloxy.
  • a base e.g. an amine such as triethylamine and pyridine, an alkali metal carbonyl such as potassium carbonate, an alkali metal hydride such as sodium hydride or an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide.
  • a base e.g. an amine such as triethylamine and pyridine, an alkali metal carbonyl such as potassium carbonate, an alkali metal hydride such as sodium hydride or an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide.
  • Suitable solvents are aliphatic or aromatic hydrocarbons such as n-hexane and toluene, halogenated hydrocarbons such as dichloromethane, ethers such as diethyl ether and tetrahydrofuran, aprotic solvents such as dimethylformamide and acetonitrile and mixtures of the solvents mentioned.
  • the isomer III can form as a by-product of the reaction; it can be separated off in the usual way, for example by means of extraction, crystallization, distillation or chromatography. All of the reactions mentioned are carried out at temperatures between the melting and boiling point of the solvent, in particular at 0 to 100 ° C.
  • the reactants are preferably in approximately equimolar amounts or in an excess of up to about ten times the molar amount, based on the amount
  • the substituted 3-phenylpyrazoles I can normally 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 3-phenylpyrazoles, but which differ in particular in the meaning of the radical R 6 or R 7 , in a manner known per se, for example by alkylation, Acetal hydrolysis, acetalization, amidation, ester hydrolysis, condensation reaction, oxidation, Peterson olefination, reduction, etherification, esterification or Wittig reaction.
  • the starting compounds specified for the individual processes are either known or are obtainable in a manner known per se or in analogy to one of the processes described.
  • 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
  • the substituted 3-phenylpyrazoles I can be obtained in the preparation as isomer mixtures, which, however, if desired, can be separated into the largely 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.
  • Salts of the compounds I which can be used commercially can be reacted with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride, or by reacting tion with an acid of the corresponding anion, preferably the
  • 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, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
  • the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are suitable: Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var.
  • the compounds I or the herbicidal compositions comprising them can be sprayed, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, spreading agents or granules , Atomizing, dusting, scattering or pouring can be used.
  • directly sprayable aqueous solutions, powders, suspensions including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, spreading agents or granules , Atomizing, dusting, scattering or pouring can be used.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, also coal tarols and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, also coal tarols and oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivative
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the substituted 3-phenylpyrazoles 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, tributylpheny
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral earths such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral earths such as silica, 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 s
  • the concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
  • the formulations contain from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • Benzene 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide in 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide in 1 mole of castor oil.
  • an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
  • the active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
  • the application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.), depending on the control target, season, target plants and growth stage.
  • the substituted 3-phenylpyrazoles I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • Non-phytotoxic oils and oil concentrates can also be added.
  • Example 1 2 -Chlor- 5- (4-chloro-5-difluoromethoxy-1-methyl -1H-pyrazol-3 -yl) -4- luorboic acid (ethoxy) amide (No. Ia.45)
  • 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 covers 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. 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 post-emergence treatment was 7.8 g / ha a.S. (active substance).
  • the plants were kept in a species-specific manner at temperatures of 10 to 25 ° C and 20 to 35 ° C.
  • the trial period lasted 2 to 4 weeks. During this time, the plants maintained, 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.
  • the plants used in the greenhouse experiments are composed of the following types:

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Abstract

The invention relates to compounds (I) and the salts thereof, wherein {R?1,R2 = C¿1-C4-alkyl, C1-C4-halogen alkyl; R3 = CN, halogen, C¿1?-C4-alkyl, C1-C4-halogen alkyl; R?4¿ = halogen; R5 = CN, halogen, C¿1?-C4-alkyl, C1-C4-halogen alkyl, C1-C4-alkoxy, C1-C4-halogen alkoxy; R?6,R7¿ = H, C¿1?-C6-alkyl, C1-C6-halogen alkyl, hydroxy-C1-C4-alkyl, cyano-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-halogen alkoxy-C1-C4-alkyl, C3-C4-alkenyloxy-C1-C4-alkyl, C3-C4-alkinyloxy-C1-C4-alkyl, C3-C8-cycloalkyloxy-C1-C4-alkyl, amino-C1-C4-alkyl, C1-C4-alkyl amino-C1-C4-alkyl, Di(C1-C4-alkyl)amino-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-halogenalkyl thio-C1-C4-alkyl, C3-C4-alkenylthio-C1-C4-alkyl, C3-C4-alkinylthio-C1-C4-alkyl, C3-C6-alkenyl, cyano-C3-C6-alkenyl, C3-C6-halogenalkenyl, C3-C6-alkinyl, cyano-C3-C6-alkinyl, C3-C6-halogenalkinyl, C1-C4-alkyl-carbonyl, C1-C4-halogenalkyl carbonyl, Di(C1-C4-alkyl)-aminocarbonyl, (C1-C4-alkoxy-C1-C4-alkyl)carbonyl, C1-C4-alkyl-SO2-,C1-C4-halogenalkyl-SO2-, (C1-C4-alkyl)carbonyl-C1-C4-alkyl, (C1-C4-halogenalkyl)carbonyl-C1-C4-alkyl, (C3-C8-cycloalkyl)carbonyl-C1-C4-alkyl, hydroxycarbonyl-C1-C4-alkyl, optionally substituted (C1-C4-alkoxy)carbonyl-C1-C4-alkyl, (C1-C4-halogen-alkoxy)carbonyl-C1-C4-alkyl, (C1-C4-alkylthio)carbonyl-C1-C4-alkyl, H2NCO-C1-C4-alkyl, (C1-C4-alkylamino)-carbonyl-C1-C4-alkyl, Di(C1-C4-alkyl)aminocarbonyl-C1-C4-alkyl, optionally substituted phenyl, phenyl-C1-C4-alkyl, C3-C8-cycloalkyl or C3-C8-cycloalkyl-C1-C4-alkyl, wherein all cycloalkyl rings can contain CO or CS}, excluded 2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole-3-yl)-4-fluorobenzoic acid (methoxy) amide and 2,4-Di-chloro-5-(5-difluoromethoxy-4-fluro-1-methyl-1H-pyrazol-3-yl), benzoic acid (methoxy) amide; and also relates to the use of (I) and the excluded compounds as herbicides.

Description

Substituierte 3-P enylpyrazoleSubstituted 3-P enylpyrazoles
Beschreibungdescription
Die vorliegende Erfindung betrifft neue substituierte 3-Phenyl- pyrazole der Formel IThe present invention relates to new substituted 3-phenylpyrazoles 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:
R1, R2 unabhängig voneinanderR 1 , R 2 independently of one another
Cι-C4-Alkyl oder Cι-C4-Halogenalkyl;Cι-C 4 alkyl or Cι-C 4 haloalkyl;
R3 Cyano, Halogen, Cι~C4-Alkyl oder Cι-C4-Halogenalkyl;R 3 is cyano, halogen, Cι ~ C 4 alkyl or Cι-C 4 haloalkyl;
R4 Halogen;R 4 halogen;
R5 Cyano, Halogen, Cι-C4-Alkyl , Cι-C4-Halogenalkyl, Cι-C4-Alkoxy oder Cι-C4-Halogenalkoxy;R 5 cyano, halogen, -CC 4 -alkyl, -C-C 4 -haloalkyl, -C-C 4 -alkoxy or -C-C 4 -haloalkoxy;
R6 , R7 unabhängig voneinanderR 6 , R 7 independently of one another
Wasserstoff , Ci-Cβ-Alkyl , Ci-Cβ-Halogenalkyl , Hydroxy- Cι-C4-alkyl , Cyano-Cι-C4-alkyl , Cι-C4-Alkoxy-Cι-C4-alkyl , Cι-C4-Halogenalkoxy-Cι-C4-alkyl, C3-C4-Alkenyloxy-Cι-C4- alkyl, C3-C4-Alkinyloxy-Cι-C4-alkyl, C3-C8-Cycloalkyl - oxy-Cι-C4-alkyl, Amino-Cι-C4-alkyl , Cι-C4-Alkyl - amino-Cι-C4-alkyl , Di- (C].-C4-alkyl) a ino-Cι-C4-alkyl, C1-C4 -Alkyl thio-Cι-C4-alkyl , Cι-C4-Halogenalkyl thio-Cι-C4-alkyl , C3-C4-Alkenylthio-Cι-C4-alkyl,Hydrogen, Ci-Cβ-alkyl, Ci-Cβ-haloalkyl, hydroxy -CC-C 4 -alkyl, cyano-Cι-C 4 -alkyl, Cι-C 4 -alkoxy-Cι-C 4 -alkyl, Cι-C 4 -haloalkoxy-Cι-C 4 alkyl, C 3 -C 4 alkenyloxy-Cι-C 4 - alkyl, C 3 -C 4 alkynyloxy-Cι-C 4 alkyl, C 3 -C 8 cycloalkyl - oxy- Cι-C 4 alkyl, amino-Cι-C 4 -alkyl, C 4 alkyl - amino-Cι-C 4 -alkyl, di- (C] -C4 alkyl.) a ino-Cι-C 4- alkyl, C 1 -C 4 -alkyl thio -CC 4 -alkyl, -C-C 4 -haloalkyl thio -CC-C 4 -alkyl, C 3 -C 4 -alkenylthio -CC 4 -alkyl,
C3-C4-Alkinylthio-Cι-C4-alkyl, C3-C6~Alkenyl, Cyano-C3-C6-alkenyl, C3-C6-Halogenalkenyl, C3-C6-Alkinyl, Cyano-C3-C6-alkinyl , C3-C6-Halogenalkinyl , (C1-C4 -Alkyl ) carbonyl, (Cι-C4-Halogenalkyl) carbonyl , Di (C1 - C4 - alkyl ) aminocarbonyl , (Cι-C4-Alkoxy- C1 -C4 - alkyl ) - carbonyl , Cι-C4-Alkylsulfonyl , Cι-C4-Halogenalkylsulfonyl, (C1-C4 -Alkyl ) carbonyl-Cι-C -alkyl, (Cι-C4-Halogenalkyl) - carbonyl-Cι-C4-alkyl , (C3-Ca-Cycloalkyl ) carbonyl-Cι-C4- alkyl , Hydroxycarbonyl-Cι-C4-alkyl, (Cι-C4-Alkoxy) carbonyl- Cι-C4-alkyl , das eine (Cι -C4 -Alkoxy) imino-Gruppe tragen kann,C 3 -C 4 alkynylthio -CC 4 alkyl, C 3 -C 6 ~ alkenyl, cyano-C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, cyano -C 3 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, (C 1 -C 4 -alkyl) carbonyl, (-C-C 4 -haloalkyl) carbonyl, di (C 1 - C 4 -alkyl) aminocarbonyl, (Cι-C 4 alkoxy C 1 -C 4 - alkyl) - carbonyl, Cι-C 4 alkylsulfonyl, Cι-C4-haloalkylsulfonyl, (C 1 -C 4 alkyl) carbonyl-Cι-C alkyl, (-C-C 4 -haloalkyl) - carbonyl-Cι-C 4 -alkyl, (C 3 -Ca-cycloalkyl) carbonyl-Cι-C 4 - alkyl, hydroxycarbonyl-Cι-C 4 alkyl, (Cι-C 4 - Alkoxy) carbonyl -CC 4 -alkyl which can carry a (-C 4 -alkoxy) imino group,
(Cι~C4-Halogenalkoxy ) carbonyl-Cι-C4-alkyl , (C1-C4 -Alkyl - thio) carbonyl-Cι-C4-alkyl, Arninocarbonyl-Cι-C4-alkyl, (Cι-C4-Alkylamino) carbonyl-Cι-C4-alkyl, Di (Cι-C4-alkyl) amino- carbonyl-Cι-C-alkyl, Phenyl, Phenyl-Cι-C4-alkyl, C3-C8-Cyclo- alkyl oder C3-C8-Cycloalkyl-Cι-C4-alkyl, wobei alle Cyclo- alkylringe gewünschtenfalls ein Carbonyl- oder Thiöcarbonyl- Ringglied enthalten können, und wobei, jeder Phenyl- oder Cycloalkylring unsubstituiert sein oder ein bis vier Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Amino, Hydroxy, Carboxy, Halogen, Cχ-C4-Alkyl, Cι-C4-Halogenalkyl, Cι-C4-Alkoxy, Cι-C4-Halogenalkoxy, Cι-C4-Alkylthio,(-C ~ C 4 -haloalkoxy) carbonyl -CC-C 4 -alkyl, (C 1 -C 4 -alkyl-thio) carbonyl -CC-C 4 -alkyl, arninocarbonyl -CC-C4-alkyl, (-CC 4 -alkylamino) carbonyl -CC-C 4 -alkyl, di (-C-C 4 -alkyl) amino-carbonyl-Cι-C-alkyl, phenyl, phenyl-Cι-C 4 -alkyl, C 3 - C 8 -cycloalkyl or C 3 -C 8 -cycloalkyl -CC 4 -alkyl, where all cycloalkyl rings can optionally contain a carbonyl or thioecarbonyl ring member, and wherein, each phenyl or cycloalkyl ring may be unsubstituted or a Cχ-C Cι-C can carry one to four substituents, each selected from the group consisting of cyano, nitro, amino, hydroxy, carboxy, halogen, 4 -alkyl, C 4 haloalkyl, 4 -alkoxy, C 4 -Halogenalkoxy, -C-C 4 alkylthio,
Cι-C4-Halogenalkylthio, Cχ-C-Alkylsulfonyl, Cχ-C4-Halogen- alkylsulfonyl, (Cι-C4-Alkoxy) carbonyl, (Cι-C4-Alkyl) carbonyl, (Cι-C4-Halogenalkyl) carbonyl, (C1-C4-Alkyl) carbonyloxy, (Cι-C4-Halogenalkyl)carbonyloxy und Di (Cι-C4-alkyl) amino;-C-C 4 -haloalkylthio, Cχ-C-alkylsulfonyl, Cχ-C 4 -halo-alkylsulfonyl, (Cι-C 4 -alkoxy) carbonyl, (Cι-C 4 -alkyl) carbonyl, (Cι-C 4 -haloalkyl) carbonyl, (C 1 -C 4 -alkyl) carbonyloxy, (Cι-C 4 -haloalkyl) carbonyloxy and di (Cι-C4 alkyl) amino;
sowie die landwirtschaftlich brauchbaren Salze derand the agriculturally useful salts of
Verbindungen I, ausgenommen 2-Chlor-5- (4 -chlor-5-difluormethoxy-1-methyl-lH- pyrazol-3 -yl) -4 -fluorbenzoesäure (methoxy) amid und 2,4-Di- chlor-5- (5-difluormethoxy-4-fluor-l-methyl-lH-pyrazol-3-yl) - benzoesäure (methoxy) amid.Compounds I, except 2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -4-fluorobenzoic acid (methoxy) amide and 2,4-dichloro-5- (5-difluoromethoxy-4-fluoro-1-methyl-1H-pyrazol-3-yl) benzoic acid (methoxy) amide.
Außerdem betrifft die Erfindung herbizide Mittel, welche die Verbindungen I als wirksame Substanzen enthalten,The invention also relates to herbicidal compositions which comprise the compounds I as active substances,
Verfahren zur Herstellung dieser herbiziden Mittel, die Verwendung von Verbindungen I' als Herbizide sowie Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs mit den Verbindungen I', wobei I' der Definition von I, jedoch ohne die Ausnahmebestimmung, entspricht.A process for the preparation of these herbicidal compositions, the use of compounds I 'as herbicides and a process for controlling unwanted vegetation with the compounds I', where I 'corresponds to the definition of I, but without the exception.
Herbizid wirksame 3-Phenylpyrazole vom Typ der Verbindungen I wurden bisher insbesondere in der DE-A 195 24 623, EP-A 443 059, WO 95/32 188, WO 96/01 255, WO 96/15 115, WO 96/40 643 und der WO 97/02251 beschrieben.Herbicidally active 3-phenylpyrazoles of the type of the compounds I have been described in particular in DE-A 195 24 623, EP-A 443 059, WO 95/32 188, WO 96/01 255, WO 96/15 115, WO 96/40 643 and WO 97/02251.
2 -Chlor- 5 - (4 -chlor- 5 -difluormethoxy-1-methyl-1H-pyrazol-3 -yl) - 4 -fluorbenzoesäure (methoxy) amid und 2, 4-Dichlor-5- (5-difluor- methoxy- 4 - fluor- 1-methyl -1H-pyrazol-3-yl)benzoesäure (methoxy) - amid sind bereits aus der älteren deutschen Patentanmeldung DE-A 19 631 008 bekannt.2-Chloro-5 - (4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) - 4-fluorobenzoic acid (methoxy) amide and 2,4-dichloro-5- (5-difluoromethoxy 4-fluoro-1-methyl-1H-pyrazol-3-yl) benzoic acid (methoxy) amide are already known from the earlier German patent application DE-A 19 631 008.
Die herbiziden Eigenschaften der bekannten Herbizide bezüglich der Schadpflanzen sind jedoch nicht immer völlig befriedigend. Aufgabe der vorliegenden Erfindung war es deshalb, neue herbizid wirksame Verbindungen bereitzustellen, mit denen sich unerwünschte Pflanzen besser als bisher bekämpfen lassen.However, the herbicidal properties of the known herbicides with regard to the harmful plants are not always completely satisfactory. The object of the present invention was therefore to provide new herbicidally active compounds which can be used to combat undesirable plants better than before.
Demgemäß wurden die vorliegenden substituierten 3-Phenylpyrazole der Formel I- sowie deren herbizide Wirkung gefunden.Accordingly, the present substituted 3-phenylpyrazoles of the formula I and their herbicidal activity have been found.
Ferner wurde 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.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 Diastereomerengendsehe vor. Gegenstand der Erfindung sind sowohl die reinen Enantiomeren oder Diastereomeren als auch deren Gemische.Depending on the substitution pattern, the compounds of the formula I can contain one or more centers of chirality and are then present as enantiomeric or diastereomeric bonds. 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 Alkali- metalle, vorzugsweise Natrium und Kalium, der Erdalkalimetalle, vorzugsweise Calcium, Magnesium und Barium, und der Übergangs- metalle, vorzugsweise Mangan, Kupfer, Zink und Eisen, sowie das Ammoniumion, das gewünschtenfalls ein bis vier Cι-C4-Alkyl- substituenten und/oder einen Phenyl- oder Benzylsubstituenten tragen kann, vorzugsweise Diisopropylammonium, Tetramethyl- ammonium, Tetrabutylammonium, Trimethylbenzylammonium, des weiteren Phosphoniumionen, Sulfoniumionen, vorzugsweise Tri (Cι-C4-alkyl) sulfonium und Sulfoxoniumionen, vorzugsweise Tri (Cι-C4-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. The cations include, in particular, the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, which if desired, can be one to can carry four C 1 -C 4 alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 alkyl) sulfonium and sulfoxonium ions preferably tri (-C 4 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 C1-C4-Alkansäuren, vorzugsweise Formiat, Acetat, Propionat und Butyrat.Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C 1 -C 4 alkanoic acids, preferably formate, acetate, propionate and butyrate.
Die für die Substituenten R1 bis R3 und R5 bis R8 oder als Reste an Phenyl- oder Cycloalkylringen genannten organischen Molekül - teile stellen Sammelbegriffe für individuelle Aufzählungen der einzelnen Gruppenmitglieder dar. Sämtliche Kohlenstoffketten, also alle Alkyl-, Halogenalkyl-, Alkoxy-, Halogenalkoxy-, Alkyl- thio-, Halogenalkylthio-, Alkylsulfonyl-, Halogenalkylsulfonyl-, Cyanoalkyl-, Hydroxyalkyl- , Hydroxycarbonylalkyl-, Aminoalkyl-, Aminocarbonylalkyl-, Phenylalkyl-, Alkylcarbonyl-, Halogenalkyl- carbonyl-, Alkylcarbonyloxy-, Halogenalkylcarbonyloxy- ," Alkoxy- carbonyl-, Halogenalkoxycarbonyl-, Alkylthiocarbonyl-, Alkyl - amino-, Alkenyl-, Halogenalkenyl-, Cyanoalkenyl-, Alkinyl-, Halogenalkinyl-, Cyanoalkinyl- , Alkenyloxy-, Alkinyloxy-, Alkenylthio- und Alkinylthio-Teile können geradkettig oder verzweigt sein. Halogenierte Substituenten tragen vorzugsweise ein bis fünf gleiche oder verschiedene Halogenatome.The organic molecule parts mentioned for the substituents R 1 to R 3 and R 5 to R 8 or as residues on phenyl or cycloalkyl rings are collective terms for individual lists of the individual group members. All carbon chains, that is to say all alkyl, haloalkyl and alkoxy -, haloalkoxy, alkyl thio, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, cyanoalkyl, hydroxyalkyl, hydroxycarbonylalkyl, aminoalkyl, aminocarbonylalkyl, phenylalkyl, alkylcarbonyl, haloalkylcarbonyl, alkylcarbonyloxy, haloalkylcarbonyloxy, " alkoxycarbonyl " , Haloalkoxycarbonyl, alkylthiocarbonyl, alkylamino, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl, alkenyloxy, alkynyloxy, alkenylthio and alkynylthio parts can be straight-chain or branched and carry halogenated substituents preferably one to five identical or different halogen atoms.
Die Bedeutung Halogen steht jeweils für Fluor, Chlor, Brom oder Jod, insbesondere für Fluor oder Chlor.Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine or chlorine.
Ferner stehen beispielsweise:Furthermore, for example:
C1-C4-Alkyl für: CH3, C2H5, n-Propyl, CH(CH3)2, n-Butyl, 1-Methylpropyl, CH2-CH(CH3)2 oder C(CH3)3, insbesondere für CH3 oder CH5;C 1 -C 4 alkyl for: CH 3 , C 2 H 5 , n-propyl, CH (CH 3 ) 2 , n-butyl, 1-methylpropyl, CH 2 -CH (CH 3 ) 2 or C (CH 3 ) 3 , especially for CH 3 or CH 5 ;
Ci-Cß-Alkyl für: Cι~C4-Alkyl wie vorstehend genannt, oder 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-Dirnethylbutyl,Ci-C ß- alkyl for: -C ~ C 4 alkyl as mentioned above, or for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl,
1, 2-Dimethylbutyl, 1, 3-Dimethylbutyl, 2,2-Dimethylbutyl, 2, 3-Dirnethylbutyl, 3, 3-Dimethylbutyl, 1-Ethylbutyl, 2-Ethyl- butyl, 1,1,2-Trimethylpropyl, 1, 2, 2-Trimethylpropyl, 1-Ethyl- 1-methylpropyl und 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-1-methylpropyl and 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;
Cι-C4-Halogenalkyl für: einen Cχ-C4-Alkylrest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. CH2C1, CH(C1)2# C(C1)3, CH2F, CHF2, CF3 CHFC1, CF(C1)2/ CF2C1, CF2Br, 1-Fluor- ethyl, 2-Fluorethyl, 2-Chlorethyl, 2-Bromethyl, 2-Iodethyl, CH2-CH2F, CH2-CF3, 2-Chlor-2-fluorethyl, 2-Chlor-2, 2-difluor- ethyl, 2, 2-Dichlor-2-fluorethyl, 1,2-Dichlorethyl, 2,2,2-Tri- chlorethyl, C2F5, 2-Fluorpropyl, 3-Fluorpropyl, 2,2-Difluor- propyl, 2, 3-Difluorpropyl, 2-Chlorpropyl, 3-Chlorpropyl, 2,3-Dichlorpropyl, 2-Brompropyl, 3-Brompropyl, 3, 3, 3-Trifluorpropyl, 3,3,3-Trichlorpropyl, CH2-C2F5, CF2-C2F5, 1- (Fluormethyl) -2-fluorethyl, 1- (Chlormethyl) -2-chlorethyl, l-(Brom- methyl)-2-bromethyl, 4-Fluorbutyl, 4-Chlorbutyl, 4-Brombutyl D oder n-C4F9 , insbesondere für CH2F, CHF2 , CF3 , CH C1 , 2-Fluor- ethyl, 2 -Chlorethyl, 1, 2-Dichlorethyl , CH2 -CF3 oder C2F5;-C-C 4 haloalkyl for: a Cχ-C 4 alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CH 2 C1, CH (C1) 2 # C ( C1) 3 , CH 2 F, CHF 2 , CF 3 CHFC1, CF (C1) 2 / CF 2 C1, CF 2 Br, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl , CH 2 -CH 2 F, CH 2 -CF 3 , 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 1,2-dichloroethyl, 2,2,2-trichloroethyl, C 2 F 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, CH 2 -C 2 F 5 , CF 2 -C 2 F 5 , 1- (fluoromethyl) -2-fluoroethyl , 1- (chloromethyl) -2-chloroethyl, l- (bromomethyl) -2-bromethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl D or nC 4 F 9 , in particular for CH 2 F, CHF 2 , CF 3 , CH C1, 2-fluoroethyl, 2-chloroethyl, 1, 2-dichloroethyl, CH 2 -CF 3 or C 2 F 5 ;
Ci-Cβ-Halogenalkyl für: Ci-Cβ-Alkyl wie vorste rhend genannt, das partiell oder vollständig durch Fluor, Chlor und/oderCi-Cβ-haloalkyl for: Ci-Cβ-alkyl as mentioned above, partially or completely by fluorine, chlorine and / or
Brom substituiert ist, also z.B. einen der vorstehend genannten Cι-C.4-Halogenalkylreste, oder 5-Fluorpentyl, 5-Chlor- pentyl, 5-Brompentyl, 5-ϊodpentyl, 5, 5, 5-Trichlorpentyl, n-CsFn, 6-Fluorhexyl, 6-Chlorhexyl, 6-Bromhexyl, 6-Iodhexyl, 6, 6, 6-Trichlorhexyl oder n-C6Fχ3, insbesondere für CH2F, CHF2, CF3, CH2C1, 2-Fluorethyl, 2-Chlorethyl oder 2, 2, 2-Trifluorethyl;Bromine is substituted, so for example one of the above -CC. 4 -haloalkyl radicals, or 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-ododyl, 5, 5, 5-trichloropentyl, n-CsFn, 6-fluorohexyl, 6-chlorohexyl, 6-bromhexyl, 6-iodohexyl , 6, 6, 6-trichlorohexyl or nC 6 Fχ 3 , in particular for CH 2 F, CHF 2 , CF 3 , CH 2 C1, 2-fluoroethyl, 2-chloroethyl or 2, 2, 2-trifluoroethyl;
C3-Cβ-Cycloalkyl für: Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cycloheptyl oder Cyclooctyl, insbesondere für Cyclopentyl oder Cyclohexyl;C 3 -C 6 -cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, in particular for cyclopentyl or cyclohexyl;
C3-C8-Cycloalkyl, das ein Carbonyl- oder Thiocarbonyl-Ring- glied enthält, für: z.B. Cyclobutanon-2-yl, Cyclobutanon- 3-yl, Cyclopentanon-2-yl, Cyclopentanon-3-yl, Cyclohexanon- 2-yl, Cyclohexanon-4-yl, Cycloheptanon-2-yl, Cyclooctanon- 2-yl, Cyclobutanthion-2-yl, Cyclobutanthion-3-yl, Cyclo- pentanthion-2-yl, Cyclopentanthion-3-yl, Cyclohexanthion- 2-yl, Cyclohexanthion-4-yl, Cycloheptanthion-2-yl oder Cyclooctanthion-2-yl;C 3 -C 8 cycloalkyl, which contains a carbonyl or thiocarbonyl ring member, for: for example cyclobutanon-2-yl, cyclobutanon-3-yl, cyclopentanon-2-yl, cyclopentanon-3-yl, cyclohexanone-2 -yl, Cyclohexanon-4-yl, Cycloheptanon-2-yl, Cyclooctanon-2-yl, Cyclobutanthion-2-yl, Cyclobutanthion-3-yl, Cyclopentanthion-2-yl, Cyclopentanthion-3-yl, Cyclohexanthion- 2 -yl, cyclohexanthion-4-yl, cycloheptanthion-2-yl or cyclooctanthion-2-yl;
Cι-C-Alkoxy für: OCH3, 0C2H5, 0CH2-C2H5, 0CH(CH3)2, n-Butoxy, 1-Methylpropoxy, OCH2-CH(CH3) oder OC(CH3)3, insbesondere für OCH3, OC2H5, OCH(CH3)2 oder OC(CH3)3;-C -C alkoxy for: OCH 3 , 0C 2 H 5 , 0CH 2 -C 2 H 5 , 0CH (CH 3 ) 2 , n-butoxy, 1-methylpropoxy, OCH 2 -CH (CH 3 ) or OC (CH 3 ) 3 , in particular for OCH 3 , OC 2 H 5 , OCH (CH 3 ) 2 or OC (CH 3 ) 3 ;
Cι-C4-Halogenalkoxy für: Cι-C4-Alkoxy wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor, Brom und/ oder Jod substituiert ist, also z.B. 0CH2C1, 0CH(C1)2, 0C(C1)3, OCH2F, OCHF2, OCF3, OCHFC1, 0CF(C1)2. OCF2Cl, OCF2Br, 1-Fluorethoxy, 2-Fluorethoxy, 2-Bromethoxy, 2-Iodethoxy,-C-C 4 haloalkoxy for: -C-C 4 alkoxy as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 0CH 2 C1, 0CH (C1) 2 , 0C (C1 ) 3 , OCH 2 F, OCHF2, OCF 3 , OCHFC1, 0CF (C1) 2 . OCF 2 Cl, OCF 2 Br, 1-fluoroethoxy, 2-fluoroethoxy, 2-bromoethoxy, 2-iodoethoxy,
OCH2-CH2F, OCH2-CF3, 2-Chlor-2-fluorethoxy, 2-Chlor-2, 2-di- fluorethoxy, 2, 2-Dichlor-2-fluorethoxy, 1,2-Dichlorethoxy, 2,2,2-Trichlorethoxy, OC2F5, 2-Fluorpropoxy, 3-Fluorpropoxy, 2-Chlorpropoxy, 3-Chlorpropoxy, 2-Brompropoxy, 3-Brompropoxy, 2,2-Difluorpropoxy, 2, 3-Difluorpropoxy, 2 , 3-Dichlorpropoxy, 3,3,3-Trifluorpropoxy, 3,3,3-Trichlorpropoxy, OCH -C2F5, OCF2-C2F5, 1- (Fluormethyl) -2-fluorethoxy, 1- (Chlormethyl) - 2-chlorethoxy, 1- (Brommethyl) -2-bromethoxy, 4-Fluorbutoxy, 4-Chlorbutoxy, 4-Brombutoxy oder Nonafluorbutoxy, ins- besondere für OCH2F, OCHF2, OCF3, 0CH2C1, 2-Fluorethoxy, 2-Chlorethoxy, 1, 2-Dichlorethoxy, OCH -CF3 oder OC2F5; Cι-C4-Alkylthio für: SCH3, SC2H5, n-Propylthio, SCH(CH3)2, n-Butylthio, 1-Methylpropylthio, SCH2-CH (CH3) 2 oder SC(CH3)3, insbesondere für SCH3 oder SC2H5;OCH 2 -CH 2 F, OCH 2 -CF 3 , 2-chloro-2-fluoroethoxy, 2-chloro-2, 2-di-fluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 1,2-dichloroethoxy, 2 , 2,2-trichloroethoxy, OC 2 F 5 , 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2, 3-difluoropropoxy, 2, 3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH -C 2 F 5 , OCF 2 -C 2 F 5 , 1- (fluoromethyl) -2-fluoroethoxy, 1- (chloromethyl) - 2-chloroethoxy, 1- (bromomethyl) -2-bromethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, especially for OCH 2 F, OCHF 2 , OCF 3 , 0CH 2 C1, 2-fluoroethoxy , 2-chloroethoxy, 1, 2-dichloroethoxy, OCH -CF 3 or OC 2 F 5 ; Cι-C 4 alkylthio for: SCH 3 , SC 2 H 5 , n-propylthio, SCH (CH 3 ) 2 , n-butylthio, 1-methylpropylthio, SCH 2 -CH (CH 3 ) 2 or SC (CH 3 ) 3 , especially for SCH 3 or SC 2 H 5 ;
Cι-C4-Halogenalkylthio für: Cι-C4-Alkylthio wie vorstehend genannt, da_s partiell oder vollständig durch Fluor, Chlor, Brom und/oder Jod substituiert ist, also z.B. SCH2C1, SCH(C1) , SC(C1)3, SCHF, SCHF2, SCF3, SCHFC1, SCF(C1) , SCF2C1, SCF2Br, 1-Fluorethylthio, 2-Fluorethylthio, 2-Chlorethylthio, 2-Brom- ethylthio, 2-Iodethylthio, SCH2-CH2F, SCH2-CF3, 1,2-Dichlor- ethylthio, 2, 2 , 2-Trichlorethylthio, 2-Chlor-2-fluorethylthio, 2-Chlor-2,2-difluorethylthio, 2 , 2-Dichlor-2-fluorethylthio, SC2F5, 2-Fluorpropylthio, 3-Fluorpropylthio, 2-Chlorpropyl- thio, 3-Chlorpropylthio, 2-Brompropylthio, 3-Brompropylthio, 2,2-Difluorpropylthio, 2, 3-Difluorpropylthio, 2,3-Dichlor- propylthio, 3 , 3,3-Trifluorpropylthio, 3, 3, 3-Trichlorpropyl- thio, SCH2-C2F5, SCF2-C2F5, 1- (Fluormethyl) -2-fluorethylthio, 1- (Chlormethyl) -2-chlorethylthio, 1- (Brommethyl) -2-bromethyl- thio, 4-Fluorbutylthio, 4-Chlorbutylthio, 4-Brombutylthio oder Nonafluorbutylthio, insbesondere für SCH2F, SCHF , SCF3, SCH2C1, 2-Fluorethylthio, 2-Chlorethylthio, 1, 2-Dichlorethyl- thio, SCH2-CF3 oder SC2F5;Is Cι-C 4 -alkylthio as mentioned above, da_s partially or fully by fluorine, chlorine, bromine and / or iodine substituted, eg SCH 2 C1, SCH (C1), SC (C1): Cι-C4-haloalkylthio for 3 , SCHF, SCHF 2 , SCF 3 , SCHFC1, SCF (C1), SCF 2 C1, SCF 2 Br, 1-fluoroethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, SCH 2 - CH 2 F, SCH 2 -CF 3 , 1,2-dichloroethylthio, 2, 2, 2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2, 2-dichloro 2-fluoroethylthio, SC 2 F 5 , 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2, 3-difluoropropylthio, 2,3 -Dichloropropylthio, 3, 3,3-trifluoropropylthio, 3, 3, 3-trichloropropylthio, SCH 2 -C 2 F 5 , SCF 2 -C 2 F 5 , 1- (fluoromethyl) -2-fluoroethylthio, 1 - (Chloromethyl) -2-chloroethylthio, 1- (bromomethyl) -2-bromomethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio, esp especially for SCH 2 F, SCHF, SCF 3 , SCH 2 C1, 2-fluoroethylthio, 2-chloroethylthio, 1, 2-dichloroethylthio, SCH 2 -CF 3 or SC 2 F 5 ;
Cyano-Cι-C4-alkyl für: z.B. CH2CN, 1-Cyanoethyl, 2-Cyanoethy1, 1-Cyanoprop-l-yl, 2-Cyanoprop-l-yl, 3-Cyanoprop-l-yl,Cyano-C 1 -C 4 -alkyl for: for example CH 2 CN, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyanoprop-l-yl,
1-Cyanobut-l-yl, 2-Cyanobut-l-yl, 3-Cyanobut-l-yl, 4-Cyano- but-l-yl, l-Cyanobut-2-yl, 2-Cyanobut-2-yl, 3 -Cyanobut-2-yl, 4-Cyanobut-2-yl, 1- (CH2CN) -eth-l-yl, l-(CH2CN)-l-(CH3)-eth-l-yl oder 1- (CH2CN) -prop-1-yl, insbesondere für CH2CN oder 2-Cyanoethy1;1-cyanobut-l-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4-cyano-but-l-yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, 3-cyanobut-2-yl, 4-cyanobut-2-yl, 1- (CH 2 CN) -eth-l-yl, l- (CH 2 CN) -l- (CH 3 ) -eth-l-yl or 1- (CH 2 CN) -prop-1-yl, in particular for CH 2 CN or 2-cyanoethy1;
Hydroxy-Cι-C4-alkyl für: z.B. CHOH, 1-Hydroxyethyl, 2-Hydroxyethyl, 1-Hydroxyprop-l-yl, 2-Hydroxyprop-l-yl, 3-Hydroxyprop-l-yl, 1-Hydroxybut-l-yl, 2-Hydroxybut-l-yl, 3-Hydroxybut-l-yl, 4-Hydroxybut-l-yl, l-Hydroxybut-2-yl, 2-Hydroxybut-2-yl, 3-Hydroxybut-2-yl, 4-Hydroxybut-2-yl, l-(CH2OH) eth-l-yl, 1- (CH2OH) -1- (CH3) -eth-l-yl oder 1- (CH2θH)prop-l-yl, insbesondere für CH2OH oder 2-Hydroxy- ethyl;Hydroxy-C 1 -C 4 -alkyl for: for example CHOH, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxyprop-l-yl, 2-hydroxyprop-l-yl, 3-hydroxyprop-l-yl, 1-hydroxybut-l -yl, 2-Hydroxybut-l-yl, 3-Hydroxybut-l-yl, 4-Hydroxybut-l-yl, 1-Hydroxybut-2-yl, 2-Hydroxybut-2-yl, 3-Hydroxybut-2-yl , 4-hydroxybut-2-yl, l- (CH 2 OH) eth-l-yl, 1- (CH 2 OH) -1- (CH 3 ) -eth-l-yl or 1- (CH 2 θH) prop-l-yl, especially for CH 2 OH or 2-hydroxyethyl;
Hydroxycarbonyl-C1-C -alkyl für : z . B . CH2COOH, 1- (COOH) ethyl, 2- (COOH) ethyl , 1- (COOH) prop-l-yl, 2- (COOH) prop-l-yl , 3- (COOH) prop-l-yl , 1- (COOH) but-l-yl , 2- (COOH) but-l-yl, 3- (COOH) but-l-yl , 4- (COOH)but-l-yl, 1- (COOH) but-2-yl , 2- (COOH) but-2-yl , 3- (C00H) but-2-yl , 4- (COOH) but-2-yl , l- (CH2COOH) eth-l-yl , 1- (CH2COOH) -1- (CH3 ) -eth-l-yl oder 1- (CH2C00H)prop-l-yl, insbesondere für CHCOOH oder 2-Hydroxy- carbonylethyl ;Hydroxycarbonyl-C 1 -C alkyl for: e.g. B. CH 2 COOH, 1- (COOH) ethyl, 2- (COOH) ethyl, 1- (COOH) prop-l-yl, 2- (COOH) prop-l-yl, 3- (COOH) prop-l-yl , 1- (COOH) but-l-yl, 2- (COOH) but-l-yl, 3- (COOH) but-l-yl, 4- (COOH) but-l-yl, 1- (COOH) but-2-yl, 2- (COOH) but-2-yl, 3- (C00H) but-2-yl, 4- (COOH) but-2-yl, l- (CH 2 COOH) eth-l- yl, 1- (CH 2 COOH) -1- (CH 3 ) -eth-1-yl or 1- (CH 2 C00H) prop-l-yl, especially for CHCOOH or 2-hydroxycarbonylethyl;
Amino-Cι-C4-alkyl für: z.B. CH2NH2, 1-Aminoethyl, 2-Amino- ethyl, 1-Aminoprop-l-yl, 2-Aminoprop-l-yl, 3-Aminoprop-l-yl, 1-Aminobu.t-l-yl, 2-Aminobut-l-yl, 3-Aminobut-l-yl, 4-Amino- but-l-yl, l-Aminobut-2-yl, 2-Aminobut-2-yl, 3-Aminobut-2-yl, 4-Aminobut-2-yl, 1- (CH2NH2) eth-l-yl, 1- (CH2NH2) -1- (CH3) - eth-l-yl oder 1- (CH2NH)prop-l-yl, insbesondere für CH2NH2 oder 2-Aminoethyl;Amino -CC 4 -alkyl for: for example CH 2 NH 2 , 1-aminoethyl, 2-aminoethyl, 1-aminoprop-l-yl, 2-aminoprop-l-yl, 3-aminoprop-l-yl, 1-aminobu.tl-yl, 2-aminobut-l-yl, 3-aminobut-l-yl, 4-amino-but-l-yl, l-aminobut-2-yl, 2-aminobut-2-yl, 3-aminobut-2-yl, 4-aminobut-2-yl, 1- (CH 2 NH 2 ) eth-l-yl, 1- (CH 2 NH 2 ) -1- (CH 3 ) - eth-l- yl or 1- (CH 2 NH) prop-l-yl, in particular for CH 2 NH 2 or 2-aminoethyl;
Aminocarbonyl-Cι-C-alkyl für: z.B. CH2CONH2, 1- (CONH2) ethyl, 2-(CONH2)ethyl, 1- (CONH2)prop-l-yl, 2- (CONH2)prop-l-yl, 3-(CONH2)prop-l-yl, 1- (CONH2)but-l-yl, 2- (CONH2)but-l-yl, 3-(CONH2)but-l-yl, 4- (CONH2)but-l-yl, 1- (CONH2)but-2-yl, 2-(CONH2)but-2-yl, 3- (CONH2)but-2-yl, 4- (CONH2)but-2-yl, l-(CH2CONH ) eth-l-yl, 1- (CH2CONH2) -1- (CH3) -eth-l-yl oder 1- (CH2CONH2)prop-l-yl, insbesondere für CH2CONH2 oder 2-Amino- carbonylethyl;Aminocarbonyl -CC-C-alkyl for: for example CH 2 CONH 2 , 1- (CONH 2 ) ethyl, 2- (CONH 2 ) ethyl, 1- (CONH 2 ) prop-l-yl, 2- (CONH 2 ) prop -l-yl, 3- (CONH 2 ) prop-l-yl, 1- (CONH 2 ) but-l-yl, 2- (CONH 2 ) but-l-yl, 3- (CONH 2 ) but-l -yl, 4- (CONH 2 ) but-l-yl, 1- (CONH 2 ) but-2-yl, 2- (CONH 2 ) but-2-yl, 3- (CONH 2 ) but-2-yl , 4- (CONH 2 ) but-2-yl, l- (CH 2 CONH) eth-l-yl, 1- (CH 2 CONH 2 ) -1- (CH 3 ) -eth-l-yl or 1- (CH 2 CONH 2 ) prop-l-yl, in particular for CH 2 CONH 2 or 2-aminocarbonylethyl;
Phenyl-Cι~C4-alkyl für: Benzyl, 1-Phenylethyl, 2-Phenylethyl, 1-Phenylprop-l-yl, 2-Phenylprop-l-yl, 3-Phenylprop-l-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-Phenylbut-2-yl, 1- (Benzyl) -eth-l-yl, 1- (Benzyl) -1- (methyl) -eth-l-yl oder 1- (Benzyl) -prop-1-yl, insbesondere für Benzyl oder 2-Phenylethyl;Phenyl-Cι ~ C 4 alkyl for: benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-l-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-phenylbut-2-yl, 1- (benzyl) -eth-l-yl, 1- (benzyl) -1- (methyl) -eth-l-yl or 1- (benzyl) prop-1-yl, especially for benzyl or 2-phenylethyl;
C3-C8-Cycloalkyl-Cι-C4-alkyl für: Cyclopropylmethyl, 1-Cyclo- propyl-ethyl, 2-Cyclopropyl-ethyl, 1-Cyclopropyl-prop-l-yl, 2-Cyclopropyl-prop-l-yl, 3-Cyclopropyl-prop-l-yl, 1-Cyclo- propyl-but-1-yl, 2-Cyclopropyl-but-l-yl, 3-Cyclopropyl- but-l-yl, 4-Cyclopropyl-but-l-yl, l-Cyclopropyl-but-2-yl, 2-Cyclopropyl-but-2-yl, 3-Cyclopropyl-but-2-yl, 3-Cyclo- propyl-but-2-yl, 4-Cyclopropyl-but-2-yl, 1- (Cyclopropylmethyl) eth-l-yl, 1- (Cyclopropylmethyl) -1-(CH3) -eth-l-yl, 1- (Cyclopropylmethyl)prop-l-yl, Cyclobutylmethyl, 1-Cyclo- butyl-ethyl, 2-Cyclobutyl-ethyl, 1-Cyclobutyl-prop-l-yl, 2-Cyclobutyl-prop-l-yl, 3-Cyclobutyl-prop-l-yl, 1-Cyclobutyl- but-l-yl, 2-Cyclobutyl-but-l-yl, 3-Cyclobutyl-but-l-yl,C 3 -C 8 cycloalkyl -CC 4 -alkyl for: cyclopropylmethyl, 1-cyclopropyl-ethyl, 2-cyclopropyl-ethyl, 1-cyclopropyl-prop-l-yl, 2-cyclopropyl-prop-l- yl, 3-cyclopropyl-prop-l-yl, 1-cyclopropyl-but-1-yl, 2-cyclopropyl-but-l-yl, 3-cyclopropyl-but-l-yl, 4-cyclopropyl-but- l-yl, l-cyclopropyl-but-2-yl, 2-cyclopropyl-but-2-yl, 3-cyclopropyl-but-2-yl, 3-cyclopropyl-but-2-yl, 4-cyclopropyl- but-2-yl, 1- (cyclopropylmethyl) eth-l-yl, 1- (cyclopropylmethyl) -1- (CH 3 ) -eth-l-yl, 1- (cyclopropylmethyl) prop-l-yl, cyclobutylmethyl, 1 -Cyclobutyl-ethyl, 2-cyclobutyl-ethyl, 1-cyclobutyl-prop-l-yl, 2-cyclobutyl-prop-l-yl, 3-cyclobutyl-prop-l-yl, 1-cyclobutyl-but-l -yl, 2-cyclobutyl-but-l-yl, 3-cyclobutyl-but-l-yl,
4-Cyclobutyl-but-l-yl, l-Cyclobutyl-but-2-yl, 2-Cyclobutyl- but-2-yl, 3-Cyclobutyl-but-2-yl, 3-Cyclobutyl-but-2-yl, 4-Cyclobutyl-but-2-yl, 1- (Cyclobutylmethyl)eth-l-yl, 1- (Cyclobutylmethyl) -1- (CH3) -eth-l-yl, 1- (Cyclobutylmethyl) - prop-1-yl, Cyclopentylmethyl, 1-Cyclopentyl-ethyl, 2-Cyclo- pentyl-ethyl, 1-Cyclopentyl-prop-l-yl, 2-Cyclopentyl-prop- 1-yl, 3-Cyclopentyl-prop-l-yl, 1-Cyclopentyl-but-l-yl. 2-Cyclopentyl-but-l-yl, 3-Cyclopentyl-but-l-yl, 4-Cyclo- pentyl-but-l-yl, l-Cyclopentyl-but-2-yl, 2-Cyclopentyl- but-2-yl, 3-Cyclopentyl-but-2-yl, 3-Cyclopentyl-but-2-yl,4-cyclobutyl-but-l-yl, l-cyclobutyl-but-2-yl, 2-cyclobutyl-but-2-yl, 3-cyclobutyl-but-2-yl, 3-cyclobutyl-but-2-yl, 4-cyclobutyl-but-2-yl, 1- (cyclobutylmethyl) eth-l-yl, 1- (cyclobutylmethyl) -1- (CH 3 ) -eth-l-yl, 1- (cyclobutylmethyl) - prop-1- yl, cyclopentylmethyl, 1-cyclopentyl-ethyl, 2-cyclopentyl-ethyl, 1-cyclopentyl-prop-l-yl, 2-cyclopentyl-prop-1-yl, 3-cyclopentyl-prop-l-yl, 1- Cyclopentyl-but-l-yl. 2-cyclopentyl-but-l-yl, 3-cyclopentyl-but-l-yl, 4-cyclopentyl-but-l-yl, l-cyclopentyl-but-2-yl, 2-cyclopentyl-but-2- yl, 3-cyclopentyl-but-2-yl, 3-cyclopentyl-but-2-yl,
4-Cyclopentyl-but-2-yl, 1- (Cyclopentylmethyl) eth-l-yl, 1- (Cyclopentylmethyl) -1- (CH3) -eth-l-yl, 1- (Cyclopentyl - methyl)prpp-l-yl, Cyclohexylmethyl, 1-Cyclohexyl-ethyl,4-Cyclopentyl-but-2-yl, 1- (cyclopentylmethyl) eth-l-yl, 1- (cyclopentylmethyl) -1- (CH 3 ) -eth-l-yl, 1- (cyclopentylmethyl) prpp-l -yl, cyclohexylmethyl, 1-cyclohexyl-ethyl,
2-Cyclohexyl-ethyl, 1-Cyclohexyl-prop-l-yl, 2-Cyclohexyl- prop-1-yl, 3-Cyclohexyl-prop-l-yl, 1-Cyclohexyl-but-l-yl,2-cyclohexyl-ethyl, 1-cyclohexyl-prop-l-yl, 2-cyclohexyl-prop-1-yl, 3-cyclohexyl-prop-l-yl, 1-cyclohexyl-but-l-yl,
2-Cyclohexyl-but-l-yl, 3-Cyclohexyl-but-l-yl, 4-Cyclohexyl- but-l-yl, l-Cyclohexyl-but-2-yl, 2-Cyclohexyl-but-2-yl,2-cyclohexyl-but-l-yl, 3-cyclohexyl-but-l-yl, 4-cyclohexyl-but-l-yl, l-cyclohexyl-but-2-yl, 2-cyclohexyl-but-2-yl,
3-Cyclohexyl-but-2-yl, 3-Cyclohexyl-but-2-yl, 4-Cyclohexyl- but-2-yl, 1- (Cyclohexylmethyl) eth-l-yl, 1- (Cyclohexylmethyl) ■ 1- (CH3) -eth-l-yl, 1- (Cyclohexylmethyl) prop-1-yl, Cycloheptyl- methyl, 1-Cycloheptyl-ethyl, 2-Cycloheptyl-ethyl, 1-Cyclo- heptyl-prop-1-yl, 2-Cycloheptyl-prop-l-yl, 3-Cycloheptyl- prop-1-yl, 1-Cycloheptyl-but-l-yl, 2-Cycloheptyl-but-l-yl, 3-Cycloheptyl-but-l-yl, 4-Cycloheptyl-but-l-yl, 1-Cyclo- heptyl-but-2-yl, 2-Cycloheptyl-but-2-yl, 3-Cycloheptyl- but-2-yl, 3-Cycloheptyl-but-2-yl, 4-Cycloheptyl-but-2-yl, 1- (Cycloheptylmethyl) eth-l-yl, 1- (Cycloheptylmethyl) -1-3-cyclohexyl-but-2-yl, 3-cyclohexyl-but-2-yl, 4-cyclohexyl-but-2-yl, 1- (cyclohexylmethyl) eth-l-yl, 1- (cyclohexylmethyl) ■ 1- ( CH 3 ) -eth-1-yl, 1- (cyclohexylmethyl) prop-1-yl, cycloheptylmethyl, 1-cycloheptyl-ethyl, 2-cycloheptyl-ethyl, 1-cycloheptyl-prop-1-yl, 2 -Cycloheptyl-prop-l-yl, 3-cycloheptyl-prop-1-yl, 1-cycloheptyl-but-l-yl, 2-cycloheptyl-but-l-yl, 3-cycloheptyl-but-l-yl, 4 -Cycloheptyl-but-l-yl, 1-cycloheptyl-but-2-yl, 2-cycloheptyl-but-2-yl, 3-cycloheptyl-but-2-yl, 3-cycloheptyl-but-2-yl , 4-Cycloheptyl-but-2-yl, 1- (cycloheptylmethyl) eth-l-yl, 1- (cycloheptylmethyl) -1-
(CH3) -eth-l-yl, 1- (Cycloheptylmethyl)prop-l-yl, Cyclooctyl- methyl, 1-Cyclooctyl-ethyl, 2-Cyclooctyl-ethyl, 1-Cyclooctyl- prop-1-yl, 2-Cyclooctyl-prop-l-yl, 3-Cyclooctyl-prop-l-yl, 1-Cyclooctyl-but-l-yl, 2-Cyclooctyl-but-l-yl, 3-Cyclooctyl- but-l-yl, 4-Cyclooctyl-but-l-yl, l-Cyclooctyl-but-2-yl,(CH 3 ) -eth-l-yl, 1- (cycloheptylmethyl) prop-l-yl, cyclooctyl-methyl, 1-cyclooctyl-ethyl, 2-cyclooctyl-ethyl, 1-cyclooctyl-prop-1-yl, 2- Cyclooctyl-prop-l-yl, 3-cyclooctyl-prop-l-yl, 1-cyclooctyl-but-l-yl, 2-cyclooctyl-but-l-yl, 3-cyclooctyl-but-l-yl, 4- Cyclooctyl-but-l-yl, l-cyclooctyl-but-2-yl,
2-Cyclooctyl-but-2-yl , 3-Cyclooctyl-but-2-yl , 3-Cyclooctyl- but-2-yl , 4-Cyclooctyl-but-2-yl , 1- (Cyclooctylmethyl) eth- l-yl , l- (Cyclooctylmethyl) -l- (CH3) -eth-l-yl oder 1- (Cyclooctylmethyl ) prop-l-yl , insbesondere für C3 -C6 -Cycloalkyl- methyl ;2-cyclooctyl-but-2-yl, 3-cyclooctyl-but-2-yl, 3-cyclooctyl-but-2-yl, 4-cyclooctyl-but-2-yl, 1- (cyclooctylmethyl) eth-l-yl , l- (Cyclooctylmethyl) -l- (CH 3 ) -eth-l-yl or 1- (cyclooctylmethyl) prop-l-yl, especially for C 3 -C 6 cycloalkyl-methyl;
C3-C8-Cycloalkyl-Cι-C4-alkyl, das ein Carbonyl- oder Thio- carbonyl-Ringglied enthält, für: z.B. Cyclobutanon-2-yl- methyl, Cyclobutanon-3-ylmethyl, Cyclopentanon-2-ylmethyl, Cyclopentanon-3-ylmethyl, Cyclohexanon-2-ylmethyl, Cyclo- hexanon-4-ylmethyl, Cycloheptanon-2-ylmethyl, Cyclo- octanon-2-ylmethyl, Cyclobutanthion-2-ylmethyl, Cyclobutan- thion-3-ylmethyl, Cyclopentanthion-2-ylmethyl, Cyclopentan- thion-3-ylmethyl, Cyclohexanthion-2-ylmethyl, Cyclohexan- thion-4-ylmethyl, Cycloheptanthion-2-ylmethyl, Cyclooctan- thion-2-ylmethyl, 1- (Cyclobutanon-2-yl) ethyl, l-(Cyclo- butanon-3-yl) ethyl, 1- (Cyclopentanon-2-yl) ethyl, l-(Cyclo- pentanon-3-yl) ethyl, 1- (Cyclohexanon-2-yl) ethyl, l-(Cyclo- hexanon-4-yl) ethyl, 1- (Cycloheptanon-2-yl) ethyl, 1- (Cyclo- octanon-2-yl)ethyl, 1- (Cyclobutanthion-2-yl) ethyl, 1- (Cyclo- butanthion-3-yl) ethyl, 1- (Cyclopentanthion-2-yl) ethyl, 1- (Cyclopentanthion-3-yl) ethyl, 1- (Cyclohexanthion-2-yl) - ethyl, 1- (Cyclohexanthion-4-yl) ethyl, 1- (Cycloheptanthion- 2-yl)ethyl, 1- (Cyclooctanthion-2-yl) ethyl, 2 (Cyclobutanon- 2-yl) ethyl, 2- (Cyclobutanon-3-yl) ethyl, 2-4Cyclopentanon-2- yl) ethyl, 2- (Cyclopentanon-3-yl) ethyl, 2- (Cyclohexanon-2-yl) - ethyl, 2- (Cyclohexanon-4-yl) ethyl, 2- (Cycloheptanon-2-yl) - ethyl, 2--(Cyclooctanon-2-yl)ethyl, 2- (Cyclobutanthion-2-yl) - ethyl, 2- (Cyclobutanthion-3-yl) ethyl, 2- (Cyclopentanthion- 2-yl) ethyl, 2- (Cyclopentanthion-3-yl) ethyl, 2- (Cyclohexan- thion-2-yl) ethyl, 2- (Cyclohexanthion-4-yl) ethyl, 2-(Cyclo- heptanthion-2-yl) ethyl, 2- (Cyclooctanthion-2-yl) ethyl,C 3 -C 8 cycloalkyl-C 4 -C 4 alkyl, which contains a carbonyl or thiocarbonyl ring member, for: for example cyclobutanon-2-ylmethyl, cyclobutanon-3-ylmethyl, cyclopentanon-2-ylmethyl, Cyclopentanone-3-ylmethyl, cyclohexanone-2-ylmethyl, cyclohexanone-4-ylmethyl, cycloheptanone-2-ylmethyl, cycloctanon-2-ylmethyl, cyclobutanthion-2-ylmethyl, cyclobutanethion-3-ylmethyl, cyclopentanthione- 2-ylmethyl, cyclopentanethion-3-ylmethyl, cyclohexanthion-2-ylmethyl, cyclohexanethion-4-ylmethyl, cycloheptanthion-2-ylmethyl, cyclooctanethion-2-ylmethyl, 1- (cyclobutanon-2-yl) ethyl , 1- (Cyclopentanon-3-yl) ethyl, 1- (cyclopentanon-2-yl) ethyl, 1- (cyclopentanon-3-yl) ethyl, 1- (cyclohexanon-2-yl) ethyl, l - (Cyclohexanon-4-yl) ethyl, 1- (Cycloheptanon-2-yl) ethyl, 1- (Cycloctanon-2-yl) ethyl, 1- (Cyclobutanthion-2-yl) ethyl, 1- ( Cyclobutanthion-3-yl) ethyl, 1- (Cyclopentanthion-2-yl) ethyl, 1- (Cyclopentanthion-3-yl) ethyl, 1- (Cyclohexanthion-2-yl) - ethyl, 1- (cyclohexanthion-4-yl) ethyl, 1- (cycloheptanthion-2-yl) ethyl, 1- (cyclooctanthion-2-yl) ethyl, 2 (cyclobutanon-2-yl) ethyl, 2- (cyclobutanone- 3-yl) ethyl, 2-4Cyclopentanon-2-yl) ethyl, 2- (Cyclopentanon-3-yl) ethyl, 2- (Cyclohexanon-2-yl) ethyl, 2- (Cyclohexanon-4-yl) ethyl, 2- (Cycloheptanon-2-yl) - ethyl, 2 - (Cyclooctanon-2-yl) ethyl, 2- (Cyclobutanthion-2-yl) - ethyl, 2- (Cyclobutanthion-3-yl) ethyl, 2- ( Cyclopentanthion-2-yl) ethyl, 2- (cyclopentanthion-3-yl) ethyl, 2- (cyclohexanethion-2-yl) ethyl, 2- (cyclohexanthion-4-yl) ethyl, 2- (cyclo-heptanthion- 2-yl) ethyl, 2- (cyclooctanthion-2-yl) ethyl,
3- (Cyclobutanon-2-yl)propyl, 3- (Cyclobutanon-3-yl)propyl, 3- (Cyclopentanon-2-yl)propyl, 3- (Cyclopentanon-3-yl)propyl, 3- (Cyclohexanon-2-yl)propyl, 3- (Cyclohexanon-4-yl)propyl,3- (Cyclobutanon-2-yl) propyl, 3- (Cyclobutanon-3-yl) propyl, 3- (Cyclopentanon-2-yl) propyl, 3- (Cyclopentanon-3-yl) propyl, 3- (Cyclohexanon-2 -yl) propyl, 3- (cyclohexanon-4-yl) propyl,
3- (Cycloheptanon-2-yl)propyl, 3- (Cyclooctanon-2-yl)propyl, 3- (Cyclobutanthion-2-yDpropyl, 3- (Cyclobutanthion-3-yl) - propyl, 3- (Cyclopentanthion-2-yl)propyl, 3- (Cyclopentan- thion-3-yl)propyl, 3- (Cyclohexanthion-2-yl) propyl, 3- (Cyclo- hexanthion-4-y1) propyl , 3- (Cycloheptanthion-2-y1) propyl, 3- (Cyclooctanthion-2-yl) propyl, 4- (Cyclobutanon-2-yl)butyl, 4- (Cyclobutanon-3-yl)butyl, 4- (Cyclopentanon-2-yl)butyl, 4- (Cyclopentanon-3-yl)butyl, 4- (Cyclohexanon-2-yl)butyl, 4- (Cyclohexanon-4-yl)butyl, 4- (Cycloheptanon-2-yl)butyl, 4- (Cyclooctanon-2-yl)butyl, 4- (Cyclobutanthion-2-yl)butyl,3- (Cycloheptanon-2-yl) propyl, 3- (Cyclooctanon-2-yl) propyl, 3- (Cyclobutanthion-2-yDpropyl, 3- (Cyclobutanthion-3-yl) propyl, 3- (Cyclopentanthion-2- yl) propyl, 3- (cyclopentanethion-3-yl) propyl, 3- (cyclohexanthion-2-yl) propyl, 3- (cyclohexanthion-4-y1) propyl, 3- (cycloheptanthion-2-y1) propyl, 3- (cyclooctanthion-2-yl) propyl, 4- (cyclobutanon-2-yl) butyl, 4- (cyclobutanon-3-yl) butyl, 4- (cyclopentanon-2-yl) butyl, 4- (cyclopentanone -3-yl) butyl, 4- (cyclohexanon-2-yl) butyl, 4- (cyclohexanon-4-yl) butyl, 4- (cycloheptanon-2-yl) butyl, 4- (cyclooctanon-2-yl) butyl , 4- (Cyclobutanthion-2-yl) butyl,
4- (Cyclobutanthion-3-yl)butyl, 4- (Cyclopentanthion-2-yl) - butyl, 4- (Cyclopentanthion-3-yl)butyl, 4- (Cyclohexan- thion-2-yl)butyl, 4- (Cyclohexanthion-4-yl)butyl, 4-(Cyclo- heptanthion-2-yl)butyl oder 4- (Cyclooctanthion-2-yl)butyl;4- (cyclobutanthion-3-yl) butyl, 4- (cyclopentanthion-2-yl) butyl, 4- (cyclopentanthion-3-yl) butyl, 4- (cyclohexanethion-2-yl) butyl, 4- ( Cyclohexanthion-4-yl) butyl, 4- (cycloheptanthion-2-yl) butyl or 4- (cyclooctanthion-2-yl) butyl;
Cι-C4-Alkoxy-Cι-C4-alkyl sowie der Alkoxyalkyl-Teil von (Cι-C4-Alkoxy-Cι-C-alkyl) carbonyl für: durch Cι-C4-Alkoxy wie vorstehend genannt substituiertes Cι-C4-Alkyl, also z.B. für CH2OCH3, CH2OC2H5, CH2OCH2-C2H5, CH2OCH(CH3)2, n-Butoxymethyl, (1-Methylpropoxy)methyl, (2-Methylpropoxy)methyl, CH2OC(CH3)3, 2- (OCH3)ethyl, 2- (OC2H5) ethyl, 2- (n-Propoxy) ethyl, 2-(l-Methylethoxy)ethyl, 2- (n-Butoxy) ethyl, 2- (1-Methyl- propoxy) ethyl, 2- (2-Methylpropoxy)ethyl, 2- [1, 1-Dimethyl- ethoxy] ethyl, 2- (OCH3)propyl, 2- (OC2H5) propyl, 2- (n-Prop- oxy)propyl, 2- (1-Methylethoxy)propyl, 2- (n-Butoxy)propyl, 2- (1-Methylpropoxy)propyl, 2- (2-Methylpropoxy) ropyl, 2- [1,1-Dimethylethoxy] propyl, 3- (OCH3)propyl, 3- (OC2H5)propyl, 3- (n-Propoxy)propyl, 3- (1-Methylethoxy)propyl, 3- (n-Butoxy) - propyl, 3- (1-Methylpropoxy) propyl, 3- (2-Methylpropoxy)propyl, 3- [1,1-Dimethylethoxy] propyl, 2- (OCH3)butyl, 2- (OC2H5)butyl, 2- (n-Propoxy)butyl, 2- (1-Methylethoxy)butyl, 2- (n-Butoxy) - butyl, 2- (1-Methylpropoxy)butyl, 2- (2-Methylpropoxy)butyl, 2- [1,1-Dimethylethoxy] butyl, 3- (OCH3)butyl, 3- (OC2H5)butyl, 3- (n-Propoxy)butyl, 3- (1-Methylethoxy)butyl, 3- (n-Butoxy) - butyl, 3- (l-Methylpropoxy)butyl, 3- (2-Methylpropoxy)butyl, 3-[l,l-Dimethylethoxy]butyl, 4- (OCH3)butyl, 4- (OCH5)butyl, 4- (n-Propoxy)butyl, 4- (1-Methylethoxy)butyl, 4- (n-Butoxy) - butyl, 4- (1-Methylpropoxy)butyl, 4- (2-Methylpropoxy)butyl oder 4- [1, 1-Dimethylethoxy] butyl, insbesondere für Methoxy- methyl oder 2-Methoxyethyl;C 1 -C 4 -alkoxy-C 4 -alkyl and the alkoxyalkyl part of (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) carbonyl for: C 1 -C 4 -alkoxy substituted as mentioned above -CC 4 alkyl, e.g. for CH 2 OCH 3 , CH 2 OC 2 H 5 , CH 2 OCH 2 -C 2 H 5 , CH 2 OCH (CH 3 ) 2 , n-butoxymethyl, (1-methylpropoxy) methyl, ( 2-methylpropoxy) methyl, CH 2 OC (CH 3 ) 3 , 2- (OCH 3 ) ethyl, 2- (OC 2 H 5 ) ethyl, 2- (n-propoxy) ethyl, 2- (l-methylethoxy) ethyl , 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methylpropoxy) ethyl, 2- [1, 1-dimethylethoxy] ethyl, 2- (OCH 3 ) propyl , 2- (OC 2 H 5 ) propyl, 2- (n-propoxy) propyl, 2- (1-methylethoxy) propyl, 2- (n-butoxy) propyl, 2- (1-methylpropoxy) propyl, 2nd - (2-Methylpropoxy) ropyl, 2- [1,1-dimethylethoxy] propyl, 3- (OCH 3 ) propyl, 3- (OC 2 H 5 ) propyl, 3- (n-propoxy) propyl, 3- (1 -Methylethoxy) propyl, 3- (n-butoxy) propyl, 3- (1-methylpropoxy) propyl, 3- (2-methylpropoxy) propyl, 3- [1,1-dimethylethoxy] propyl, 2- (OCH 3 ) butyl, 2- (OC 2 H 5 ) butyl, 2- (n -Propoxy) butyl, 2- (1-methylethoxy) butyl, 2- (n-butoxy) butyl, 2- (1-methylpropoxy) butyl, 2- (2-methylpropoxy) butyl, 2- [1,1-dimethylethoxy ] butyl, 3- (OCH 3 ) butyl, 3- (OC 2 H 5 ) butyl, 3- (n-propoxy) butyl, 3- (1-methylethoxy) butyl, 3- (n-butoxy) - butyl, 3- (l-methylpropoxy) butyl, 3- (2-methylpropoxy) butyl, 3- [l, l-dimethylethoxy] butyl, 4- (OCH 3 ) butyl, 4- (OCH 5 ) 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 methoxymethyl or 2-methoxyethyl;
Cι-C4-Halogenalkoxy-Cι-C4-alkyl für: durch Cι-C4~Halogenalkoxy wie vorstehend genannt substituiertes Cι-C4-Alkyl, also z.B. für 2- (Difluormethoxy) ethyl, 2- (Trifluormethoxy) ethyl oder 2- (Pentafluorethoxy) ethyl; Cι-C4-haloalkoxy-Cι-C 4 alkyl: by Cι-C ~ 4 haloalkoxy as mentioned above substituted Cι-C4 alkyl, eg for 2- (difluoromethoxy) ethyl, 2- (trifluoromethoxy) ethyl or 2- (pentafluoroethoxy) ethyl;
C3-C8-Cycloalkyloxy-Cι-C4-alkyl für: Cyclopropyloxymethyl, 1-Cyclopropyloxy-ethyl, 2-Cyclopropyloxy-ethyl, 1-Cyclo- propyloxy-prop-1-yl, 2-Cyclopropyloxy-prop-l-yl, 3-Cyclo- propyloxy-prop-1-yl, 1-Cyclopropyloxy-but-l-yl, 2-Cyclo- propyloxy-but-1-yl, 3-Cyclopropyloxy-but-l-yl, 4-Cyclopropyl- oxy-but-1-yl, l-Cyclopropyloxy-but-2-yl, 2-Cyclopropyloxy- but-2-yl, 3-Cyclopropyloxy-but-2-yl, 3-Cyclopropyloxy-but- 2-yl, 4-Cyclopropyloxy-but-2-yl, 1- (Cyclopropyloxymethyl) - eth-l-yl, 1- (Cyclopropyloxymethyl) -1- (CH3) -eth-l-yl, 1- (Cyclopropylmethyloxy) prop-1-yl, Cyclobutyloxymethyl, 1-Cyclobutyloxy-ethyl, 2-Cyclobutyloxy-ethyl, 1-Cyclobutyl- oxy-prop-1-yl, 2-Cyclobutyloxy-prop-l-yl, 3-Cyclobutyloxy- prop-1-yl, 1-Cyclobutyloxy-but-l-yl, 2-Cyclobutyloxy-but- 1-yl, 3-Cyclobutyloxy-but-l-yl, 4-Cyclobutyloxy-but-l-yl, l-Cyclobutyloxy-but-2-yl, 2-Cyclobutyloxy-but-2-yl, 3-Cyclo- butyloxy-but-2-yl, 3-Cyclobutyloxy-but-2-yl, 4-Cyclobutyloxy- but-2-yl, 1- (Cyclobutyloxymethyl) eth-l-yl, 1- (Cyclobutyloxy- methyl) -1-(CH3) -eth-l-yl, 1- (Cyclobutyloxymethyl)prop-l-yl, Cyclopentyloxymethyl, 1-Cyclopentyloxy-ethyl, 2-Cyclopentyl- oxy-ethyl, 1-Cyclopentyloxy-prop-l-yl, 2-Cyclopentyloxy-prop- 1-yl, 3-Cyclopentyloxy-prop-l-yl, 1-Cyclopentyloxy-but-l-yl, 2-Cyclopentyloxy-but-l-yl, 3-Cyclopentyloxy-but-l-yl, 4-Cyclopentyloxy-but-l-yl, l-Cyclopentyloxy-but-2-yl, 2-Cyclopentyloxy-but-2-yl, 3-Cyclopentyloxy-but-2-yl, 3-Cyclopentyloxy-but-2-yl, 4-Cyclopentyloxy-but-2-yl, 1- (Cyclopentyloxymethyl) eth-l-yl, 1- (Cyclopentyloxymethyl) - 1- (CH3) -eth-l-yl, 1- (Cyclopentyloxymethyl)prop-l-yl, Cyclo- hexyloxymethyl , 1-Cyclohexyloxy-ethyl, 2-Cyclohexyloxy-ethyl, 1-Cyclohexyloxy-prop-l-yl, 2-Cyclohexyloxy-prop-l-yl, 3-Cyclohexyloxy-prop-l-yl, 1-Cyclohexyloxy-but-l-yl, 2-Cyclo- hexyloxy-but-1-yl, 3-Cyclohexyloxy-but-l-yl, 4-Cyclohexyloxy- but-l-yl, l-Cyclohexyloxy-but-2-yl, 2-Cyclohexyloxy-but-2-yl, 3-Cyclohexyloxy-but-2-yl, 3-Cyclohexyloxy-but-2-yl, 4-Cyclo- hexyloxy-but-2-yl, 1- (Cyclohexyloxymethyl) eth-l-yl, l-(Cyclo- hexyloxymethyl) -1- (CH3) -eth-l-yl, 1- (Cyclohexyloxymethyl) - prop-1-yl, Cycloheptyloxymethyl, 1-Cycloheptyloxy-ethyl, 2-Cycloheptyloxy-ethyl, 1-Cycloheptyloxy-prop-l-yl, 2-Cyclo- heptyloxy-prop-1-yl, 3-Cycloheptyloxy-prop-l-yl, 1-Cyclo- heptyloxy-but-1-yl, 2-Cycloheptyloxy-but-l-yl, 3-Cycloheptyl- oxy-but-1-yl, 4-Cycloheptyloxy-but-l-yl, 1-Cycloheptyloxy- but-2-yl-,_ 2-Cycloheptyloxy-but-2-yl, 3-Cycloheptyloxy- but-2-yl, 3-Cycloheptyloxy-but-2-yl, 4-Cycloheptyloxy- but-2-yl, 1- (Cycloheptyloxymethyl) eth-l-yl, 1- (Cycloheptyloxymethyl) -1- (CH3) -eth-l-yl, 1- (Cycloheptyloxymethyl)prop- 1-yl, Cyclooctyloxymethyl, 1-Cyclooctyloxy-ethyl, 2-Cyclo- octyloxy-ethyl, 1-Cyclooctyloxy-prop-l-yl, 2-Cyclooctyloxy- prop-1-yl, 3-Cyclooctyloxy-prop-l-yl, 1-Cyclooctyloxy-but- l-yl, 2-Cyclooctyloxy-but-l-yl, 3-Cyclooctyloxy-but-l-yl, 4-Cyclooctyloxy-but-l-yl, l-Cyclooctyloxy-but-2-yl, 2-Cyclo- octyloxy-but-2-yl, 3-Cyclooctyloxy-but-2-yl, 3-Cyclooctyloxy- but-2-yl, 4-Cyclooctyloxy-but-2-yl, 1- (Cyclooctyloxymethyl) - eth-l-yl, 1- (Cyclooctyloxymethyl) -1- (CH3) -eth-l-yl oder 1- (Cyclooctyloxymethyl)prop-l-yl, insbesondere für C3-C6-Cycloalkoxymethyl oder 2- (C3-C6-Cycloalkoxy) ethyl;C 3 -C 8 cycloalkyloxy-C 4 -C 4 alkyl for: cyclopropyloxymethyl, 1-cyclopropyloxy-ethyl, 2-cyclopropyloxy-ethyl, 1-cyclo-propyloxy-prop-1-yl, 2-cyclopropyloxy-prop-l- yl, 3-cyclopropyloxy-prop-1-yl, 1-cyclopropyloxy-but-l-yl, 2-cyclopropyloxy-but-1-yl, 3-cyclopropyloxy-but-l-yl, 4-cyclopropyl oxy-but-1-yl, l-cyclopropyloxy-but-2-yl, 2-cyclopropyloxy-but-2-yl, 3-cyclopropyloxy-but-2-yl, 3-cyclopropyloxy-but-2-yl, 4- Cyclopropyloxy-but-2-yl, 1- (cyclopropyloxymethyl) - eth-l-yl, 1- (cyclopropyloxymethyl) -1- (CH 3 ) -eth-l-yl, 1- (cyclopropylmethyloxy) prop-1-yl, Cyclobutyloxymethyl, 1-cyclobutyloxy-ethyl, 2-cyclobutyloxy-ethyl, 1-cyclobutyl-oxy-prop-1-yl, 2-cyclobutyloxy-prop-l-yl, 3-cyclobutyloxy-prop-1-yl, 1-cyclobutyloxy- but-l-yl, 2-cyclobutyloxy-but-1-yl, 3-cyclobutyloxy-but-l-yl, 4-cyclobutyloxy-but-l-yl, l-cyclobutyloxy-but-2-yl, 2-cyclobutyloxy- but-2-yl, 3-cyclobutyloxy-but-2-yl, 3-cyclobutyloxy-but-2-yl, 4-cyclobutyloxy-but-2-yl, 1- (cyclobutyloxymethyl) eth-l-yl, 1- (cyclobutyloxy-methyl) -1- (CH 3 ) -eth-l-yl, 1- (cyclobutyloxymethyl) prop-l-yl, cyclopentyloxymethyl, 1-cyclopentyloxy-ethyl, 2-cyclopentyl-oxy-ethyl, 1- Cyclopentyloxy-prop-l-yl, 2-cyclopentyloxy-prop-1-yl, 3-cyclopentyloxy-prop-l-yl, 1-cyclopentyloxy-but-l-yl, 2-cyclopentyloxy-but-l-yl, 3- Cyclopentyloxy-but-l-yl, 4-cyclopentyloxy-but-l-yl, l-cyclopentyloxy-but-2-yl, 2-cyclopentyloxy-but-2-yl, 3-cyclopentyloxy-but-2-yl, 3- Cyclopentyloxy-but-2-yl, 4-cyclopentyloxy-but-2-yl, 1- (cyclopentyloxymethyl) eth-l-yl, 1- (cyclopentyloxymethyl) - 1- (CH 3 ) -eth-l-yl, 1- (Cyclopentyloxymethyl) prop-l-yl, cyclohexyloxymethyl, 1-cyclohexyloxy-ethyl, 2-cyclohexyloxy-ethyl, 1-cyclohexyloxy-prop-l-yl, 2-cyclohexyloxy-prop-l-yl, 3-cyclohexyloxy-prop -l-yl, 1-cyclohexyloxy-but-l-yl, 2-cyclohexyloxy-but-1-yl, 3-cyclohexyloxy-but-l-yl, 4-cyclohexyloxy-but-l-yl, l-cyclohexyloxy -but-2-yl, 2-cyclohexyloxy-but-2-yl, 3-cyclohexyloxy-but-2-yl, 3-cyclohexyloxy-but-2-yl, 4-cyclohexyloxy-but-2-yl, 1 - ( Cyclohexyloxymethyl) eth-l-yl, l- (cyclohexyloxymethyl) -1- (CH 3 ) -eth-l-yl, 1- (cyclohexyloxymethyl) - prop-1-yl, cycloheptyloxymethyl, 1-cycloheptyloxy-ethyl, 2-cycloheptyloxy-ethyl, 1-cycloheptyloxy-prop-l-yl, 2-cycloheptyloxy-prop-1-yl, 3-cycloheptyloxy-prop-l- yl, 1-cycloheptyloxy-but-1-yl, 2-cycloheptyloxy-but-l-yl, 3-cycloheptyl-oxy-but-1-yl, 4-cycloheptyloxy-but-l-yl, 1-cycloheptyloxy- but-2-yl -, _ 2-cycloheptyloxy-but-2-yl, 3-cycloheptyloxy-but-2-yl, 3-cycloheptyloxy-but-2-yl, 4-cycloheptyloxy-but-2-yl, 1- (Cycloheptyloxymethyl) eth-l-yl, 1- (cycloheptyloxymethyl) -1- (CH 3 ) -eth-l-yl, 1- (cycloheptyloxymethyl) prop-1-yl, cyclooctyloxymethyl, 1-cyclooctyloxy-ethyl, 2-cyclo - octyloxy-ethyl, 1-cyclooctyloxy-prop-l-yl, 2-cyclooctyloxy-prop-1-yl, 3-cyclooctyloxy-prop-l-yl, 1-cyclooctyloxy-but-l-yl, 2-cyclooctyloxy-but -l-yl, 3-cyclooctyloxy-but-l-yl, 4-cyclooctyloxy-but-l-yl, l-cyclooctyloxy-but-2-yl, 2-cycloctyloxy-but-2-yl, 3-cyclooctyloxy -but-2-yl, 3-cyclooctyloxy-but-2-yl, 4-cyclooctyloxy-but-2-yl, 1- (cyclooctyloxymethyl) - eth-l-yl, 1- (cyclooctyloxymethyl) -1- (CH 3 ) -eth-l-yl or 1- (cyclooctyloxymethyl) prop-l-yl, in particular for C 3 -C 6 -cycloalkoxymethyl or 2- (C 3 -C 6 -cycloalkoxy) ethyl;
C1-C4-Alkylthio-Cι-C4-alkyl für: durch Cτ.-C4-Alkylthio wie vorstehend genannt substituiertes Cι-C4-Alkyl, also z.B. für CH2SCH3, CH2SC2H5, n-Propylthiomethyl, CH2SCH(CH3)2, n-Butyl- thiomethyl, (1-Methylpropylthio) methyl, (2-Methylpropylthio) - methyl, CH2SC(CH3)3, 2-Methylthioethyl, 2-Ethylthioethyl, 2-(n-Propylthio)ethyl, 2- (1-Methylethylthio) ethyl, 2- (n-Butylthio) ethyl, 2- (1-Methylpropylthio) ethyl, 2- (2-Methylpropylthio) ethyl, 2- (1, 1-Dimethylethylthio) ethyl, 2- (SCH3) propyl, 3- (SCH3) propyl, 2- (SC2H5) propyl, 3- (SC2H5)propyl, 3- (Propylthio) propyl, 3- (Butylthio) propyl, 4-(SCH3)butyl, 4-(SC2H5)butyl, 4- (n-Propylthio)butyl oder 4- (n-Butylthio)butyl, insbesondere für CH2SCH3 oder 2- (Methyl- thio) ethyl;C 1 -C 4 alkylthio -CC-C 4 alkyl for: by Cτ . -C 4 -Alkylthio as above-substituted -CC 4 -alkyl, for example for CH 2 SCH 3 , CH 2 SC 2 H 5 , n-propylthiomethyl, CH 2 SCH (CH 3 ) 2 , n-butyl-thiomethyl, (1-methylpropylthio) methyl, (2-methylpropylthio) methyl, CH 2 SC (CH 3 ) 3 , 2-methylthioethyl, 2-ethylthioethyl, 2- (n-propylthio) ethyl, 2- (1-methylethylthio) ethyl, 2- (n-butylthio) ethyl, 2- (1-methylpropylthio) ethyl, 2- (2-methylpropylthio) ethyl, 2- (1, 1-dimethylethylthio) ethyl, 2- (SCH 3 ) propyl, 3- (SCH 3 ) propyl, 2- (SC 2 H 5 ) propyl, 3- (SC 2 H 5 ) propyl, 3- (propylthio) propyl, 3- (butylthio) propyl, 4- (SCH 3 ) butyl, 4- (SC 2 H 5 ) butyl, 4- (n-propylthio) butyl or 4- (n-butylthio) butyl, in particular for CH 2 SCH 3 or 2- (methylthio) ethyl;
- Cι-C4-Halogenalkylthio-Cι-C-alkyl für: durch Cι-C-Halogen- alkylthio wie vorstehend genannt substituiertes Cι-C4-Alkyl, also z.B. für 2 - (Difluormethylthio) ethyl, 2 - (SCF3) ethyl oder 2- (SC2F5) ethyl;- C 1 -C 4 -Halogenalkylthio-C 1 -C 4 -alkyl for: C 1 -C 4 -alkyl-substituted C 1 -C 4 -alkyl as mentioned above, for example for 2 - (difluoromethylthio) ethyl, 2 - (SCF 3 ) ethyl or 2- (SC 2 F 5 ) ethyl;
- (C1-C4-Alkyl) carbonyl für: COCH3, COC2H5, COCH2-C2H5,- (C 1 -C 4 alkyl) carbonyl for: COCH 3 , COC 2 H 5 , COCH 2 -C 2 H 5 ,
COCH(CH3)2, n-Butylcarbonyl, COCH(CH3) -C2H5, COCH -CH(CH3) 2 oder COC(CH3)3, insbesondere für COCH3, COC2H5 oder C0C(CH3)3;COCH (CH 3 ) 2 , n-butylcarbonyl, COCH (CH 3 ) -C 2 H 5 , COCH -CH (CH 3 ) 2 or COC (CH 3 ) 3 , especially for COCH 3 , COC 2 H 5 or C0C ( CH 3 ) 3 ;
(Cι-C4-Halogenalkyl) carbonyl: (Cι-C4-Alkyl) carbonyl wie vor- stehend genannt, das partiell oder vollständig durch Fluor, Chlor, Brom und/oder Jod substituiert ist, also z.B. C0CH(C1)2, C0C(C1)3, COCH2F, COCHF2, COCF3, C0CH2C1, COCHFC1, C0CF(C1) , C0CF2C1, COCF2Br, 1-Fluorethylcarbonyl, C0CH2-CH2F, COCH2-CHF2, COCH2-CF3, 2-Chlor-2-fluorethylcarbonyl, 2-Chlor-2 , 2-difluorethylcarbonyl , 2 , 2-Dichlor-2-fluorethyl- carbonyl, 1, 2-Dichlorethylcarbonyl, COCH2-C (Cl) 3, COC2F5, 3-Chlorpropylcarbonyl, COCH2-C2F5, COCF2-C2F5, 1- (Fluormethyl) -2-fluorethylcarbonyl, 1- (Chlormethyl) -2-chlorethyl- carbonyl, 1- (Brommethyl) -2-bromethylcarbonyl, 4-Fluorbutyl- carbonyl, 4-Chlorbutylcarbonyl, 4-Brombutylcarbonyl oder Nonafluorbutylcarbonyl, insbesondere für COCH2F, COCHF2, COCF3, C0CH2C1, 2-Fluorethylcarbonyl, 2-Chlorethylcarbonyl, 1,2-Dichlorethylcarbonyl, COCH -CF3 oder COC2F5;(-C-C 4 -haloalkyl) carbonyl: (-C-C 4 -alkyl) carbonyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example C0CH (C1) 2 , C0C (C1) 3 , COCH 2 F, COCHF2, COCF 3 , C0CH 2 C1, COCHFC1, C0CF (C1), C0CF 2 C1, COCF 2 Br, 1-fluoroethylcarbonyl, C0CH 2 -CH 2 F, COCH 2 -CHF 2 , COCH 2 -CF 3 , 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2, 2-difluoroethylcarbonyl, 2, 2-dichloro-2-fluoroethylcarbonyl, 1, 2-dichloroethylcarbonyl, COCH 2 -C (Cl) 3 , COC 2 F 5 , 3-chloropropylcarbonyl, COCH 2 -C 2 F 5 , COCF 2 -C 2 F 5 , 1- (fluoromethyl) -2-fluoroethylcarbonyl, 1- (chloromethyl) -2-chloroethylcarbonyl, 1- (bromomethyl) -2-bromethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4- Bromobutylcarbonyl or nonafluorobutylcarbonyl, in particular for COCH 2 F, COCHF 2 , COCF 3 , C0CH 2 C1, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 1,2-dichloroethylcarbonyl, COCH -CF 3 or COC 2 F 5 ;
(C1-C4-Alkyl)carbonyl-Cι-C4-alkyl für: durch (Cι-C4-Alkyl) - carbonyl wie vorstehend genannt substituiertes Ci- ^-Alkyl, also z.B. für CH2COCH3, CH2COC2H5 oder CH2COC (CH3)3;(C 1 -C 4 alkyl) carbonyl -CC 4 -alkyl for: C 1 -C 4 -alkyl substituted by (-C 4 -alkyl) carbonyl as mentioned above, for example for CH 2 COCH 3 , CH 2 COC 2 H 5 or CH 2 COC (CH 3 ) 3 ;
(Cι-C4-Halogenalkyl) carbonyl-Cι-C4-alkyl für: durch (Cι-C4-Halogenalkyl) carbonyl wie vorstehend genannt substituiertes C1-C4-Alkyl, also z.B. für CH2COCF3 oder CH2C0CH2C1;(Cι-C 4 haloalkyl) carbonyl-Cι-C4 alkyl for: by (Cι-C 4 haloalkyl) carbonyl as mentioned above substituted C 1 -C 4 alkyl, eg CH 2 COCF 3 or CH 2 C0CH 2 C1;
(C3-C8-Cycloalkyl)carbonyl-Cι-C-alkyl für: Cyclopropyl- CO-CH2-, 1- (Cyclopropyl-CO-) ethyl, 2- (Cyclopropyl-CO-) ethyl, 1- (Cyclopropyl-CO-) rop-1-yl, 2- (Cyclopropyl-CO-)prop-1-yl, 3- (Cyclopropyl-CO-)prop-l-yl, 1- (Cyclopropyl-CO-)but-l-yl, 2- (Cyclopropyl-CO-)but-l-yl, 3- (Cyclopropyl-CO-)but-l-yl, 4- (Cyclopropyl-CO-)but-l-yl, 1- (Cyclopropyl-CO-)but-2-yl, 2- (Cyclopropyl-CO-)but-2-yl, 3- (Cyclopropyl-CO-)but-2-yl, 3- (Cyclopropyl-CO-)but-2-yl, 4- (Cyclopropyl-CO-)but-2-yl, l-(Cyclopropyl-CO-CH2-) eth-l-yl, 1- (Cyclopropyl-CO-CH2-) - 1- (CH3) -eth-l-yl, 1- (Cyclopropyl-CO-CH2-)prop-l-yl, Cyclo- butyl-CO-CH2-, 1- (Cyclobutyl-CO-) ethyl, 2- (Cyclobutyl-CO-) - ethyl, 1- (Cyclobutyl-CO-)prop-l-yl, 2- (Cyclobutyl-CO-)prop- 1-yl, 3- (Cyclobutyl-CO-)prop-1-yl, 1- (Cyclobutyl-CO-)but- 1-yl, 2- (Cyclobutyl-CO-) but-l-yl, 3- (Cyclobutyl-CO-)but-l-yl, 4- (Cyclobutyl-CO-)but-l-yl, 1- (Cyclobutyl-CO-)but-2-yl, 2- (Cyclobutyl-CO-)but-2-yl, 3- (Cyclobutyl-CO-)but-2-yl, 3- (Cyclobutyl-CO-)but-2-yl, 4- (Cyclobutyl-CO-)but-2-yl, 1- (Cyclobutyl-CO-CH2-) eth-l-yl, 1- (Cyclobutyl-CO-CH2-) -1- (CH3) -eth-l-yl, 1- (Cyclobutyl-CO-CH2-)prop-l-yl, Cyclopentyl- CO-CH2-, 1- (Cyclopentyl-CO-) ethyl, 2- (Cyclopentyl-CO-) ethyl, 1- (Cyclopentyl-CO-)prop-l-yl, 2- (Cyclopentyl-CO-)prop-l-yl, 3- (Cyclopentyl-CO-)prop-l-yl, 1- (Cyclopentyl-CO-)but-l-yl, 2- (Cyclopentyl-CO-)but-l-yl, 3- (Cyclopentyl-CO-)but-l-yl, 4- (Cyclopentyl-CO-)but-l-yl, 1- (Cyclopentyl-CO-)but-2-yl, 2- (Cyclopentyl-CO-)but-2-yl, 3- (Cyclopentyl-CO-)but-2-yl, 3- (Cyclopentyl-CO-)but-2-yl, 4- (Cyclopentyl-CO-)but-2-yl. 1- (Cyclopentyl-CO-CH2-) eth-l-yl , 1- (Cyclopentyl-CO-CH2- ) -l- (CH3 ) -eth-l-yl , 1- (Cyclopentyl-CO-CH2- ) prop-l-yl , Cyclohexyl- CO-CH2- , l- (Cyclohexyl-CO- ) ethyl, 2- (Cyclohexyl-CO- ) ethyl , 1- (Cyclohexyl-CO- ) prop-1-yl , 2- (Cyclohexyl-CO- ) prop-1-yl , 3- (Cyclohexyl-CO-) prop-1-yl , 1- (Cyclohexyl-CO-) but-l-yl ,(C 3 -C 8 cycloalkyl) carbonyl -CC-C-alkyl for: cyclopropyl-CO-CH 2 -, 1- (cyclopropyl-CO-) ethyl, 2- (cyclopropyl-CO-) ethyl, 1- (cyclopropyl -CO-) rop-1-yl, 2- (cyclopropyl-CO-) prop-1-yl, 3- (cyclopropyl-CO-) prop-l-yl, 1- (cyclopropyl-CO-) but-l- yl, 2- (cyclopropyl-CO-) but-l-yl, 3- (cyclopropyl-CO-) but-l-yl, 4- (cyclopropyl-CO-) but-l-yl, 1- (cyclopropyl-CO -) but-2-yl, 2- (cyclopropyl-CO-) but-2-yl, 3- (cyclopropyl-CO-) but-2-yl, 3- (cyclopropyl-CO-) but-2-yl, 4- (cyclopropyl-CO-) but-2-yl, l- (cyclopropyl-CO-CH 2 -) eth-l-yl, 1- (cyclopropyl-CO-CH 2 -) - 1- (CH 3 ) - eth-l-yl, 1- (cyclopropyl-CO-CH 2 -) prop-l-yl, cyclobutyl-CO-CH 2 -, 1- (cyclobutyl-CO-) ethyl, 2- (cyclobutyl-CO- ) - ethyl, 1- (cyclobutyl-CO-) prop-l-yl, 2- (cyclobutyl-CO-) prop-1-yl, 3- (cyclobutyl-CO-) prop-1-yl, 1- (cyclobutyl -CO-) but- 1-yl, 2- (cyclobutyl-CO-) but-l-yl, 3- (cyclobutyl-CO-) but-l-yl, 4- (cyclobutyl-CO-) but-l- yl, 1- (cyclobutyl-CO-) but-2-yl, 2- (cyclobutyl-CO-) but-2-yl, 3- (cyclobutyl-CO-) but-2-yl, 3- (cycl obutyl-CO-) but-2-yl, 4- (cyclobutyl-CO-) but-2-yl, 1- (cyclobutyl-CO-CH 2 -) eth-l-yl, 1- (cyclobutyl-CO-CH 2 -) -1- (CH 3 ) -eth-l-yl, 1- (cyclobutyl-CO-CH 2 -) prop-l-yl, cyclopentyl-CO-CH 2 -, 1- (cyclopentyl-CO-) ethyl, 2- (cyclopentyl-CO-) ethyl, 1- (cyclopentyl-CO-) prop-l-yl, 2- (cyclopentyl-CO-) prop-l-yl, 3- (cyclopentyl-CO-) prop- l-yl, 1- (cyclopentyl-CO-) but-l-yl, 2- (cyclopentyl-CO-) but-l-yl, 3- (cyclopentyl-CO-) but-l-yl, 4- (cyclopentyl -CO-) but-l-yl, 1- (cyclopentyl-CO-) but-2-yl, 2- (cyclopentyl-CO-) but-2-yl, 3- (cyclopentyl-CO-) but-2- yl, 3- (cyclopentyl-CO-) but-2-yl, 4- (cyclopentyl-CO-) but-2-yl. 1- (cyclopentyl-CO-CH 2 -) eth-l-yl, 1- (cyclopentyl-CO-CH 2 -) -l- (CH 3 ) -eth-l-yl, 1- (cyclopentyl-CO-CH 2 -) prop-l-yl, cyclohexyl-CO-CH 2 -, l- (cyclohexyl-CO-) ethyl, 2- (cyclohexyl-CO-) ethyl, 1- (cyclohexyl-CO-) prop-1-yl , 2- (cyclohexyl-CO-) prop-1-yl, 3- (cyclohexyl-CO-) prop-1-yl, 1- (cyclohexyl-CO-) but-l-yl,
2- (Cyclohexyl-CO- ) but-l-yl , 3- (Cyclohexyl-CO- ) but-l-yl , 4- (Cyclohexyl-CO- ) but-l-yl , 1- (Cyclohexyl-CO-) but-2-yl , 2- (Cyclohexyl-CO-) but-2-yl , 3- (Cyclohexyl-CO-) but-2-yl , 3- (Cyclohexyl-CO- ) but-2-yl , 4- (Cyclohexyl-CO-) but-2-yl , l- (Cyclohexyl-CO-CH2- ) eth-l-yl , 1- (Cyclohexyl-CO-CH2- ) -l-2- (cyclohexyl-CO-) but-l-yl, 3- (cyclohexyl-CO-) but-l-yl, 4- (cyclohexyl-CO-) but-l-yl, 1- (cyclohexyl-CO-) but-2-yl, 2- (cyclohexyl-CO-) but-2-yl, 3- (cyclohexyl-CO-) but-2-yl, 3- (cyclohexyl-CO-) but-2-yl, 4- (Cyclohexyl-CO-) but-2-yl, l- (cyclohexyl-CO-CH 2 -) eth-l-yl, 1- (cyclohexyl-CO-CH 2 -) -l-
(CH3) -eth-l-yl, 1- (Cyclohexyl-CO-CH2-)prop-l-yl, Cycloheptyl- CO-CH2-, 1- (Cycloheptyl-CO-) ethyl, 2- (Cycloheptyl-CO- ) ethyl, 1- (Cycloheptyl-CO-)prop-l-yl, 2- (Cycloheptyl-CO-) prop-1-yl, 3- (Cycloheptyl-CO-)prop-l-yl, 1- (Cycloheptyl-CO-)but-l-yl, 2- (Cycloheptyl-CO-)but-l-yl, 3- (Cycloheptyl-CO-)but-l-yl, 4- (Cycloheptyl-CO-)but-l-yl, 1- (Cycloheptyl-CO-)but-2-yl, 2- (Cycloheptyl-CO-)but-2-yl, 3- (Cycloheptyl-CO-)but-2-yl, 3- (Cycloheptyl-CO-)but-2-yl, 4- (Cycloheptyl-CO-)but-2-yl, 1- (Cycloheptyl-CO-CH2-) eth-l-yl, 1- (Cycloheptyl-CO-CH2-) -1- (CH3) -eth-l-yl, 1- (Cycloheptyl-CO-CH2-)prop-l-yl, Cyclooctyl- CO-CH2-, l-(Cyclooctyl-CO-) ethyl, 2- (Cyclooctyl-CO-) ethyl, 1- (Cyclooctyl-CO-) prop-1-yl, 2- (Cyclooctyl-CO-) prop-1-yl, 3- (Cyclooctyl-CO-) prop-1-yl, 1- (Cyclooctyl-CO-)but-l-yl, 2- (Cyclooctyl-CO-)but-l-yl, 3- (Cyclooctyl-CO-)but-l-yl, 4-(Cyclooctyl-CO-)but-l-yl, 1- (Cyclooctyl-CO-)but-2-yl, 2- (Cyclooctyl-CO-)but-2-yl, 3- (Cyclooctyl-CO-)but-2-yl, 3- (Cyclooctyl-CO-)but-2-yl, 4- (Cyclooctyl-CO-)but-2-yl, 1- (Cyclooctyl-CO-CH2-) -eth-l-yl, 1- (Cyclooctyl-CO-CH2-) -1- (CH3) -eth-l-yl oder 1- (Cyclooctyl-CO-CH2-)prop-l-yl, insbesondere für (C3-C6-Cycloalkyl) carbonyl ethyl;(CH 3 ) -eth-l-yl, 1- (cyclohexyl-CO-CH 2 -) prop-l-yl, cycloheptyl-CO-CH 2 -, 1- (cycloheptyl-CO-) ethyl, 2- (cycloheptyl -CO-) ethyl, 1- (cycloheptyl-CO-) prop-l-yl, 2- (cycloheptyl-CO-) prop-1-yl, 3- (cycloheptyl-CO-) prop-l-yl, 1- (Cycloheptyl-CO-) but-l-yl, 2- (Cycloheptyl-CO-) but-l-yl, 3- (Cycloheptyl-CO-) but-l-yl, 4- (Cycloheptyl-CO-) but- l-yl, 1- (cycloheptyl-CO-) but-2-yl, 2- (cycloheptyl-CO-) but-2-yl, 3- (cycloheptyl-CO-) but-2-yl, 3- (cycloheptyl -CO-) but-2-yl, 4- (cycloheptyl-CO-) but-2-yl, 1- (cycloheptyl-CO-CH 2 -) eth-l-yl, 1- (cycloheptyl-CO-CH 2 -) -1- (CH 3 ) -eth-l-yl, 1- (cycloheptyl-CO-CH 2 -) prop-l-yl, cyclooctyl-CO-CH 2 -, l- (cyclooctyl-CO-) ethyl , 2- (Cyclooctyl-CO-) ethyl, 1- (Cyclooctyl-CO-) prop-1-yl, 2- (Cyclooctyl-CO-) prop-1-yl, 3- (Cyclooctyl-CO-) prop-1 -yl, 1- (cyclooctyl-CO-) but-l-yl, 2- (cyclooctyl-CO-) but-l-yl, 3- (cyclooctyl-CO-) but-l-yl, 4- (cyclooctyl- CO-) but-l-yl, 1- (cyclooctyl-CO-) but-2-yl, 2- (cyclooctyl-CO-) but-2-yl, 3- (cyclooctyl-CO-) but-2-yl , 3- (C yclooctyl-CO-) but-2-yl, 4- (cyclooctyl-CO-) but-2-yl, 1- (cyclooctyl-CO-CH 2 -) -eth-l-yl, 1- (cyclooctyl-CO- CH 2 -) -1- (CH 3 ) -eth-1-yl or 1- (cyclooctyl-CO-CH 2 -) prop-1-yl, in particular for (C 3 -C 6 -cycloalkyl) carbonyl ethyl;
C1-C4-Alkylcarbonyloxy für: O-COCH3, 0-COC2H5, 0-COCH2-C2H5, 0-COCH(CH3)2, n-Butylcarbonyloxy, 1-Methylpropylcarbonyloxy, O-C0CH2-CH(CH3)2 oder 0-COC(CH3)3, insbesondere für 0-COCH3, 0-COC2H5 oder 0-COC(CH3)3;C 1 -C 4 alkylcarbonyloxy for: O-COCH 3 , 0-COC 2 H 5 , 0-COCH 2 -C 2 H 5 , 0-COCH (CH 3 ) 2 , n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, O- COCH 2 -CH (CH 3 ) 2 or 0-COC (CH 3 ) 3 , in particular for 0-COCH 3 , 0-COC 2 H 5 or 0-COC (CH 3 ) 3 ;
(Cι-C4-Halogenalkyl) carbonyloxy für: (C1-C4-Alkyl) carbonyloxy wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor, Brom und/oder Jod substituiert ist, also z.B. für 0-COCH2F, 0-COCHF2, O-COCF3, 0-COCH2Cl, 0-COCH(Cl)2, 0-COC(C1)3, O-COCHFCl, 0~C0CF(C1)2, 0-COCF2Cl, 0-COCF2Br, 1-Fluorethylcarbonyloxy, 0-COCH2-CH2F, 0-COCH2-CHF2, 0-C0CH2-CF3, 2-Chlor-2-fluorethylcarbonyloxy, 2-Chlor-2, 2-difluorethylcarbonyloxy, 2, 2-Dichlor-2-fluor- ethylcarbonyloxy, 1,2-Dichlorethylcarbonyloxy, 0-C0CH2-C (Cl)3, O-C0C2F5, 3-Chlorpropylcarbonyloxy, 0-COCF2-C2F5, 1- (Fluormethyl) -2-fluorethylcarbonyloxy, 1- (Chlormethyl) -2-chlor- ethylcarbonyloxy, 1- (Brommethyl) -2-bromethylcarbonyloxy, 4-Fluorbutylcarbonyloxy, 4-Chlorbutylcarbonyloxy, 4-Brom- butylcarbonyloxy oder Nonafluorbutylcarbonyloxy, insbesondere für 0-COCH2Cl, 0-COCH2F, 0-COCHF2, 0-COCF3, 2-Fluorethyl - carbonyloxy, 2-Chlorethylcarbonyloxy, 1, 2-Dichlorethyl- carbonyloxy, 0-COCH2-CF3 oder 0-COC2F5;(-C-C 4 haloalkyl) carbonyloxy for: (C 1 -C 4 alkyl) carbonyloxy as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for 0-COCH 2 F , 0-COCHF 2 , O-COCF 3 , 0-COCH 2 Cl, 0-COCH (Cl) 2 , 0-COC (C1) 3 , O-COCHFCl, 0 ~ C0CF (C1) 2 , 0-COCF 2 Cl , 0-COCF 2 Br, 1-fluoroethylcarbonyloxy, 0-COCH 2 -CH 2 F, 0-COCH 2 -CHF 2 , 0-C0CH 2 -CF 3 , 2-chloro-2-fluoroethylcarbonyloxy, 2-chloro-2, 2-difluoroethylcarbonyloxy, 2, 2-dichloro-2-fluoroethylcarbonyloxy, 1,2-dichloroethylcarbonyloxy, 0-C0CH 2 -C (Cl) 3 , O-C0C 2 F 5 , 3-chloropropylcarbonyloxy, 0-COCF 2 -C 2 F 5 , 1- (fluoromethyl) -2-fluoroethylcarbonyloxy, 1- (chloromethyl) -2-chloro ethylcarbonyloxy, 1- (bromomethyl) -2-bromethylcarbonyloxy, 4-fluorobutylcarbonyloxy, 4-chlorobutylcarbonyloxy, 4-bromobutylcarbonyloxy or nonafluorobutylcarbonyloxy, especially for 0-COCH 2 Cl, 0-COCH 2 F, 0-COCHF 2 , 0-COCF 3 , 2-fluoroethyl - carbonyloxy, 2-chloroethylcarbonyloxy, 1, 2-dichloroethylcarbonyloxy, 0-COCH 2 -CF 3 or 0-COC 2 F 5 ;
(Cι-C4-Alkoxy) carbonyl für: COOCH3, COOC2H5, n-Propoxy- carbonyl, COOCH(CH3)2, n-Butoxycarbonyl, 1- (Methylpropoxy) - carbonyl, COOCH2-CH(CH3) 2 oder COOC(CH3)3, insbesondere für COOCH3, COOC2H5 oder COOC(CH3)3;(-CC 4 alkoxy) carbonyl for: COOCH 3 , COOC 2 H 5 , n-propoxycarbonyl, COOCH (CH 3 ) 2 , n-butoxycarbonyl, 1- (methylpropoxy) carbonyl, COOCH 2 -CH (CH 3 ) 2 or COOC (CH 3 ) 3 , especially for COOCH 3 , COOC 2 H 5 or COOC (CH 3 ) 3 ;
(Cι-C4-Alkoxy) carbonyl-Cι-C4-alkyl für: durch (C1-C4~Alkoxy) - carbonyl wie vorstehend genannt substituiertes Cι~C4-Alkyl, also z.B. für CH2COOCH3, CH2COOC2H5, CH2CH2COOCH3, CH2CH2COOC2H5, CH(CH3)COOCH3 oder CH(CH3) COOC2H5;(-CC 4 alkoxy) carbonyl -CC 4 -alkyl for: C 1 -C 4 -alkoxy-carbonyl substituted as above-mentioned C 1 -C 4 -alkyl, for example for CH 2 COOCH 3 , CH 2 COOC 2 H 5 , CH 2 CH 2 COOCH 3 , CH 2 CH 2 COOC 2 H 5 , CH (CH 3 ) COOCH 3 or CH (CH 3 ) COOC 2 H 5 ;
(Cι-C4-Halogenalkoxy)carbonyl-Cι-C4-alkyl für: (Cχ-C4-Alkoxy) - carbonyl-Cι-C4-alkyl wie vorstehend genannt, dessen Alkoxy- Teil partiell oder vollständig durch Fluor, Chlor, Brom und/oder Jod substituiert ist, also z.B. CH2COOCH2CF3 oder CH(CH3)C0OCH2CF3;(-CC 4 haloalkoxy) carbonyl -CC 4 -alkyl for: (Cχ-C 4 -alkoxy) - carbonyl -CC 4 -alkyl as mentioned above, the alkoxy part of which is partially or completely by fluorine, chlorine , Bromine and / or iodine is substituted, for example CH 2 COOCH 2 CF 3 or CH (CH 3 ) COCH 2 CF 3 ;
(C1-C4-Alkylthio)carbonyl-Cι-C4-alkyl für: durch (C1-C4-Alkyl - thio) carbonyl wie COSCH3, COSC2H5, COSCH2-C2H5, COSCH(CH3)2, n-Butylthiocarbonyl , 1-Methylpropylthiocarbonyl, COSCH2-CH(CH3) oder COSC(CH3)3, insbesondere für COSCH3 oder COSC2H5, substituiertes C1-C4-Alkyl, also z.B. für CH2COSCH3 oder CH2COSCH5;(C 1 -C 4 -Alkylthio) carbonyl -CC-C 4 -alkyl for: by (C 1 -C 4 -alkyl-thio) carbonyl such as COSCH 3 , COSC 2 H 5 , COSCH 2 -C 2 H 5 , COSCH (CH 3 ) 2 , n-butylthiocarbonyl, 1-methylpropylthiocarbonyl, COSCH 2 -CH (CH 3 ) or COSC (CH 3 ) 3 , in particular for COSCH 3 or COSC 2 H 5 , substituted C 1 -C 4 alkyl, that is eg for CH 2 COSCH 3 or CH 2 COSCH 5 ;
(Cι-C4-Alkθxy)imino für: =N-OCH3, =N-0C2H5, =N-OCH2-C2H5, =N-OCH(CH3)2, n-Butoxyimino, 1- (Methylpropoxy) imino, =N-OCH2-CH(CH3)2 oder =N-OC(CH3)3, insbesondere für =N-OCH3 oder =N-OC2H5;(Cι-C 4 -alkθxy) imino for: = N-OCH 3 , = N-0C 2 H 5 , = N-OCH 2 -C 2 H 5 , = N-OCH (CH 3 ) 2 , n-butoxyimino, 1- (methylpropoxy) imino, = N-OCH 2 -CH (CH 3 ) 2 or = N-OC (CH 3 ) 3 , especially for = N-OCH 3 or = N-OC 2 H 5 ;
Di (C1-C -alkyl) amino für: z.B. N(CH3)2, N(C2H5)2, N,N-Dipropyl- amino, N,N-Di- (1-methylethyl) amino, N,N-Dibutylamino, N,N-Di- (1-methylpropyl) amino, N,N-Di- (2-methylpropyl) amino, N,N-Di- (1, 1-dimethylethyl) amino, N-Ethyl-N-methylamino, N-Methyl-N-propylamino, N-Methyl-N- (1-methylethyl) amino, N-Butyl-N-methylamino, N-Methyl-N- (1-methylpropyl) amino, N-Methyl-N- (2-methylpropyl) amino, N-(l, 1-Dirnethylethyl) -N- methylamino, N-Ethyl-N-propylamino, N-Ethyl-N- (1-methylethyl) amino, N-Butyl-N-ethylamino, N-Ethyl-N- (1-methyl - propyl) 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-Methyl- ethyl) -N- (1-methylpropyl) amino, N- (1-Methylethyl) -N- (2- methylpropyl) amino, N- (1, 1-Dimethylethyl)-N- (1-methyl - ethyl) amino, N-Butyl-N- (1-methylpropyl) amino, N-Butyl-Di (C 1 -C 4 alkyl) amino for: for example N (CH 3 ) 2 , N (C 2 H 5 ) 2 , N, N-dipropylamino, N, N-di- (1-methylethyl) amino, N, N-dibutylamino, N, N-di- (1-methylpropyl) amino, N, N-di- (2-methylpropyl) amino, N, N-di- (1, 1-dimethylethyl) amino, N-ethyl -N-methylamino, N-methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino, N-methyl -N- (2-methylpropyl) amino, N- (l, 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- (1, 1-dimethylethyl) -N- (1-methylethyl) amino, N-butyl- N- (1-methylpropyl) amino, N-butyl
N- ( -methylpropyl) amino, N-Butyl-N- (1, 1-dimethylethyl) amino, N- (1-Methylpropyl) -N- (2-methylpropyl) amino, N- (1, 1-Dimethyl - ethyl) -N- (1-methylpropyl) amino oder N- (1, 1-Dimethylethyl) - N- (2-methylpropyl) amino, insbesondere für N(CH3)2 oder N(C2H5)2;N- (-methylpropyl) amino, N-butyl-N- (1, 1-dimethylethyl) amino, N- (1-methylpropyl) -N- (2-methylpropyl) amino, N- (1, 1-dimethyl - ethyl ) -N- (1-methylpropyl) amino or N- (1, 1-dimethylethyl) - N- (2-methylpropyl) amino, especially for N (CH 3 ) 2 or N (C 2 H 5 ) 2 ;
Di (Cι-C4-alkyl)amino-Cι-C4-alkyl für: durch Di (Cι-C4-alkyl) - amino - wie vorstehend genannt - substituiertes C1-C4-Alkyl, also z.B. für CH2N(CH3)2, CHN(C2H5)2, N, N-Dipropylaminomethyl, N,N-Di (1-methylethyl) aminomethyl, N,N-Dibutylaminomethyl, N,N-Di (1-methylpropyl) minomethyl, N,N-Di (2-methylpropyl) - aminomethyl, N,N-Di (1, 1-dimethylethyl) aminomethyl, N-Ethyl-N- methylaminomethyl, N-Methyl-N-propylaminomethyl, N-Methyl- N- (1-methylethyl) aminomethyl, N-Butyl-N-methylaminomethyl, N-Methyl-N- (1-methylpropyl) aminomethyl, N-Methyl-N- (2-methyl- propyl) aminomethyl, N- (1, 1-Dimethylethyl) -N-methylaminomethyl, N-Ethyl-N-propylaminomethyl, N-Ethyl-N- (1-methylethyl) aminomethyl, N-Butyl-N-ethylaminomethyl, N-Ethyl-N- (1-methylpropyl) aminomethyl, N-Ethyl-N- (2-methylpropyl) - aminomethyl, N-Ethyl-N- (1, 1-dimethylethyl) aminomethyl,Di (-C 4 alkyl) amino -C 4 alkyl for: by di (C 4 alkyl) amino - as mentioned above - substituted C 1 -C 4 alkyl, for example for CH 2 N (CH 3 ) 2, CHN (C 2 H5) 2, N, N-dipropylaminomethyl, N, N-di (1-methylethyl) aminomethyl, N, N-dibutylaminomethyl, N, N-di (1-methylpropyl) minomethyl , N, N-Di (2-methylpropyl) aminomethyl, N, N-Di (1, 1-dimethylethyl) aminomethyl, N-ethyl-N-methylaminomethyl, N-methyl-N-propylaminomethyl, N-methyl-N- (1-methylethyl) aminomethyl, N-butyl-N-methylaminomethyl, N-methyl-N- (1-methylpropyl) aminomethyl, N-methyl-N- (2-methylpropyl) aminomethyl, N- (1, 1- Dimethylethyl) -N-methylaminomethyl, N-ethyl-N-propylaminomethyl, N-ethyl-N- (1-methylethyl) aminomethyl, N-butyl-N-ethylaminomethyl, N-ethyl-N- (1-methylpropyl) aminomethyl, N -Ethyl-N- (2-methylpropyl) aminomethyl, N-ethyl-N- (1, 1-dimethylethyl) aminomethyl,
N- (1-Methylethyl) -N-propylaminomethyl, N-Butyl-N-propylamino- methyl, N- (1-Methylpropyl) -N-propylaminomethyl, N-(2-Methyl- propyl)-N-propylaminomethyl, N- (1, 1-Dimethylethyl) -N-propylaminomethyl, N-Butyl-N- (1-methylethyl) aminomethyl, N- (1-Methylethyl) -N- (1-methylpropyl) aminomethyl, N- (1-Methyl- ethyl) -N- (2-methylpropyl) aminomethyl, N-(l, 1-Dimethylethyl) - N- (1-methylethyl) aminomethyl, N-Butyl-N- (1-methylpropyl) - aminomethyl, N-Butyl-N- (2-methylpropyl) minomethyl, N-Butyl- N- (1, 1-dimethylethyl) aminomethyl, N- (1-Methylpropyl) -N- (2- methylpropyl) aminomethyl, N- (1, 1-Dimethylethyl) -N- (1-methyl - propyl) aminomethyl, N- (1, 1-Dimethylethyl) -N- (2-methyl- propyl) aminomethyl, N,N-Dimethylaminoethyl, N,N-Diethylamino- ethyl, N,N-Di (n-propyl) aminoethyl, N,N-Di- (1-methylethyl) - aminoethyl, N,N-Dibutylaminoethyl, N,N-Di (1-methylpropyl) - aminoethyl, N,N-Di- (2-methylpropyl) aminoethyl, N,N-Di(l,l- dimethylethyl) aminoethyl, N-Ethyl-N-methylaminoethyl, N-Methyl-N-propylaminoethyl, N-Methyl-N- (1-methylethyl) minoethyl, N-Butyl-N-methylaminoethyl , N-Methyl-N- (1-methyl- propyl) aminoethyl, N-Methyl-N- (2-methylpropyl) aminoethyl, N- (1, 1-Dimethylethyl) -N-methylaminoethyl, N-Ethyl-N-propyl- aminoethyl, N-Ethyl-N- (1-methyl-ethyl) aminoethyl, N-Butyl- N-ethylaminoethyl, N-Ethyl-N- (1-methylpropyl) aminoethyl , N-Ethyl-N- (2-methylpropyl) aminoethyl, N-Ethyl-N- (1, 1-di- methylethyl) aminoethyl, N- (1-Methylethyl) -N-propylaminoethyl, N-Butyl-N-propylaminoethyl, N- (1-Methylpropyl) -N-propylaminoethyl, N- (2-Methylpropyl) -N-propylaminoethyl, N-(l, 1-Di- methylethyl) -N-propylaminoethyl, N-Butyl-N- (1-methylethyl) - aminoethyl, N- (1-Methylethyl) -N- (1-methylpropyl) aminoethyl, N- (1-Methylethyl) -N- (2-methylpropyl) aminoethyl, N- (1, 1-Di - methylethyl) -N- (1-methylethyl) aminoethyl , N-Butyl-N- (1- methylpropyl) aminoethyl, N-Butyl-N- (2-methylpropyl) amino- ethyl, N-Butyl-N- (1, 1-dimethylethyl) aminoethyl, N-(1-Methyl- propyl) -N- (2-methyl-propyl) aminoethyl, N- (1, 1-Dimethylethyl) -N- (1-methylpropyl) aminoethyl oder N- (1, 1-Dimethylethyl) -N- (2-methylpropyl) aminoethyl, insbesondere für N,N-Di- methylaminoethyl oder N,N-Diethylaminoethyl;N- (1-methylethyl) -N-propylaminomethyl, N-butyl-N-propylamino-methyl, N- (1-methylpropyl) -N-propylaminomethyl, N- (2-methylpropyl) -N-propylaminomethyl, N- (1, 1-dimethylethyl) -N-propylaminomethyl, N-butyl-N- (1-methylethyl) aminomethyl, N- (1-methylethyl) -N- (1-methylpropyl) aminomethyl, N- (1-methylethyl) ) -N- (2-methylpropyl) aminomethyl, N- (l, 1-dimethylethyl) - N- (1-methylethyl) aminomethyl, N-butyl-N- (1-methylpropyl) - aminomethyl, N-butyl-N- (2-methylpropyl) minomethyl, N-butyl-N- (1, 1-dimethylethyl) aminomethyl, N- (1-methylpropyl) -N- (2-methylpropyl) aminomethyl, N- (1, 1-dimethylethyl) -N - (1-methyl-propyl) aminomethyl, N- (1, 1-dimethylethyl) -N- (2-methyl-propyl) aminomethyl, N, N-dimethylaminoethyl, N, N-diethylamino-ethyl, N, N-Di (n-propyl) aminoethyl, N, N-di- (1-methylethyl) - aminoethyl, N, N-dibutylaminoethyl, N, N-di (1-methylpropyl) - aminoethyl, N, N-di- (2-methylpropyl ) aminoethyl, N, N-di (l, l-dimethylethyl) aminoethyl, N-ethyl-N-methylaminoethyl, N-meth yl-N-propylaminoethyl, N-methyl-N- (1-methylethyl) minoethyl, N-butyl-N-methylaminoethyl, N-methyl-N- (1-methylpropyl) aminoethyl, N-methyl-N- (2nd -methylpropyl) aminoethyl, N- (1, 1-dimethylethyl) -N-methylaminoethyl, N-ethyl-N-propyl-aminoethyl, N-ethyl-N- (1-methyl-ethyl) aminoethyl, N-butyl-N- ethylaminoethyl, N-ethyl-N- (1-methylpropyl) aminoethyl, N-ethyl-N- (2-methylpropyl) aminoethyl, N-ethyl-N- (1, 1-dimethylethyl) aminoethyl, N- (1-methylethyl) -N-propylaminoethyl, N-butyl-N-propylaminoethyl, N- (1-methylpropyl) -N-propylaminoethyl, N- (2-methylpropyl) -N-propylaminoethyl, N- (l, 1-dimethylethyl) -N-propylaminoethyl, N-butyl-N- (1-methylethyl ) - aminoethyl, N- (1-methylethyl) -N- (1-methylpropyl) aminoethyl, N- (1-methylethyl) -N- (2-methylpropyl) aminoethyl, N- (1, 1-dimethylethyl) - N- (1-methylethyl) aminoethyl, N-butyl-N- (1-methylpropyl) aminoethyl, N-butyl-N- (2-methylpropyl) aminoethyl, N-butyl-N- (1, 1-dimethylethyl) aminoethyl, N- (1-methylpropyl) -N- (2-methylpropyl) aminoethyl, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) aminoethyl or N- (1, 1-dimethylethyl ) -N- (2-methylpropyl) aminoethyl, in particular for N, N-dimethylaminoethyl or N, N-diethylaminoethyl;
Di (C1-C4-alkyl) aminocarbonyl für: einen über eine Carbonyl- Brücke gebundenen Di (Cχ-C4-alkyl)amino-Rest, wie vorstehend genannt;Di (C 1 -C 4 alkyl) aminocarbonyl for: a di (Cχ-C 4 alkyl) amino radical bonded via a carbonyl bridge, as mentioned above;
Di (Cι-C4-alkyl)aminocarbonyl-Cι-C4-alkyl für: durchDi (-C 4 alkyl) aminocarbonyl -C 4 alkyl for: by
Di (C3.-C4 -alkyl) aminocarbonyl - wie vorstehend genannt - substituiertes C1-C4 -Alkyl, also z.B. für CH2-CON(CH3)2, CH2-CON(C2H5) 2, N,N-Dipropylamino- COCH-, N,N-Di- (1-methylethyl )amino-COCH2-, N, N-Dibutylamino- COCH2-, N,N-Di-(l-methylpropyl)arrtino-COCH2-, N,N-Di- (2-methyl- propyl) amino-COCH2-, N,N-Di- [1, 1-dimethylethyl] amino-COCH2-, N-Ethyl-N-methylamino-COCH2-, N-Methyl-N-propylamino-COCH2-, N-Methyl-N- (1-methylethyl) amino-COCH2-, N-Butyl-N-methyl- amino-COCH2-, N-Methyl-N- (1-methylpropyl) amino-COCH2-, N-Methyl-N- (2-methylpropyl)amino-COCH2-, N- [1, 1-Dimethylethyl] -N-methylamino-COCH2-, N-Ethyl-N-propylamino-COCH2-, N-Ethyl-N- (1-methylethyl) amino-COCH2-, N-Butyl-N-ethylamino- COCH-, N-Ethyl-N- (l-methylpropyl)amino-COCH2-, N-Ethyl-N- (2-methylpropyl) amino-COCH2-, N-Ethyl-N- [1, 1-dimethylethyl] - amino-COCH2-, N- (1-Methylethyl) -N-propylamino-COCH2- , N-Butyl- N-propylamino-COCH2-, N- (1-Methylpropyl) -N-propylamino-COCH2-, N- (2-Methylpropyl) -N-propylamino-COCH2-, N- [1, 1-Dimethyl - ethyl] -N-propylamino-COCH2-, N-Butyl-N- (1-methylethyl) amino- COCH2-, N- (1-Methylethyl) -N- (1-methylpropyl) amino-COCH2-, N- (1-Methylethyl) -N- (2-methylpropyl) amino-COCH2-,Di (C 3 -C 4 alkyl) aminocarbonyl - as mentioned above - substituted C 1 -C 4 alkyl, for example for CH 2 -CON (CH 3 ) 2 , CH 2 -CON (C 2 H 5 ) 2 , N, N-dipropylamino-COCH-, N, N-di- (1-methylethyl) amino-COCH 2 -, N, N-dibutylamino-COCH 2 -, N, N-di- (l-methylpropyl) arrtino- COCH 2 -, N, N-di- (2-methylpropyl) amino-COCH 2 -, N, N-di- [1, 1-dimethylethyl] amino-COCH 2 -, N-ethyl-N-methylamino- COCH 2 -, N-methyl-N-propylamino-COCH 2 -, N-methyl-N- (1-methylethyl) amino-COCH 2 -, N-butyl-N-methyl-amino-COCH 2 -, N-methyl -N- (1-methylpropyl) amino-COCH 2 -, N-methyl-N- (2-methylpropyl) amino-COCH 2 -, N- [1, 1-dimethylethyl] -N-methylamino-COCH 2 -, N -Ethyl-N-propylamino-COCH 2 -, N-ethyl-N- (1-methylethyl) amino-COCH 2 -, N-butyl-N-ethylamino-COCH-, N-ethyl-N- (l-methylpropyl) amino-COCH 2 -, N-ethyl-N- (2-methylpropyl) amino-COCH 2 -, N-ethyl-N- [1, 1-dimethylethyl] - amino-COCH 2 -, N- (1-methylethyl) -N-propylamino-COCH 2 -, N-butyl-N-propylamino-COCH 2 -, N- (1-methylpropyl) -N- propylamino-COCH 2 -, N- (2-methylpropyl) -N-propylamino-COCH 2 -, N- [1, 1-dimethyl-ethyl] -N-propylamino-COCH 2 -, N-butyl-N- (1 -methylethyl) amino- COCH 2 -, N- (1-methylethyl) -N- (1-methylpropyl) amino-COCH 2 -, N- (1-methylethyl) -N- (2-methylpropyl) amino-COCH 2 - ,
N- [1, 1-Dimethylethyl] -N- (1-methylethyl) amino-C0CH2-, N-Butyl-N- (1-methylpropyl) amino-COCH2- , N-Butyl-N- (2-methyl - propyl) amino-COCH2-, N-Butyl-N- [1, 1-dimethylethyl] amino- COCH2-, N- (1-Methylpropyl) -N- (2-methylpropyl) amino-COCH2-, N- [1, 1-Dimethylethyl] -N- (1-methylpropyl) amino-COCH2-, N- [1, 1-Dimethylethyl] -N- (2-methylpropyl) amino-COCH2-, C2H4-CON(CH3) , C2H-CON(C2H5)2, N,N-Di (n-propyl) amino-COC2H4-, N,N-Di- [1-methylethyl] amino-COCH4-, N,N-Dibutylamino-COC2H4-, N,N-Di- (l-methylpropyl)amino-COC2H4-, N,N-Di (2-methylpropyl) - amino-COC2H-, N,N-Di [1, 1-dimethylethyl] amino-COC2H4~ , N-Ethyl-N-methylamino-COC2H4-, N-Methyl-N-propylamino-COC2H4-, N-Methyl-N- (1-methylethyl) amino-COC2H-, N-Butyl-N-methyl- amino-COC2H4-, N-Methyl-N- (1-methylpropyl) amino-COCH4-, N-Methyl-N- (2-methylpropyl)amino-COC2H4-, N- [1, 1-Dimethylethyl] -N-methylamino-COC2H4- , N-Ethyl-N-propylamino-COC2H4-, N-Ethyl-N- (1-methylethyl)amino-COC2H4-, N-Butyl-N-ethylamino- COC2H-, N-Ethyl-N- (l-methylpropyl)amino-COC2H4-, N-Ethyl-N- (2-methylpropyl) amino-COC2H4-, N-Ethyl-N- [1, 1-dimethylethyl] - amino-COC2H4- , N- (1-Methylethyl) -N-propylamino-COC2H4-, N-Butyl-N-propylamino-COC2H4-, N- (1-Methylpropyl) -N-propyl - amino-COC2H4-, N- (2-Methylpropyl) -N-propylamino-COCH4-, N- [1, 1-Dimethylethyl] -N-propylamino-COC2H4-, N-Butyl-N-N- [1, 1-dimethylethyl] -N- (1-methylethyl) amino-COCH 2 -, N-butyl-N- (1-methylpropyl) amino-COCH 2 -, N-butyl-N- (2-methyl - propyl) amino-COCH 2 -, N-butyl-N- [1, 1-dimethylethyl] amino-COCH 2 -, N- (1-methylpropyl) -N- (2-methylpropyl) amino-COCH 2 -, N - [1, 1-dimethylethyl] -N- (1-methylpropyl) amino-COCH 2 -, N- [1, 1-dimethylethyl] -N- (2-methylpropyl) amino-COCH 2 -, C 2 H 4 - CON (CH 3 ), C 2 H-CON (C 2 H 5 ) 2, N, N-Di (n-propyl) amino-COC 2 H 4 -, N, N-Di- [1-methylethyl] amino-COCH 4 -, N, N-dibutylamino-COC 2 H 4 -, N, N-Di- (l-methylpropyl) amino-COC 2 H 4 -, N, N-Di (2-methylpropyl) - amino-COC 2 H-, N, N-Di [1, 1-dimethylethyl] amino-COC 2 H 4 ~, N-ethyl-N-methylamino-COC 2 H 4 -, N-methyl-N-propylamino-COC 2 H 4 -, N-methyl-N- (1-methylethyl) amino-COC 2 H-, N-butyl-N-methyl-amino-COC 2 H 4 -, N- Methyl-N- (1-methylpropyl) amino-COCH 4 -, N-methyl-N- (2-methylpropyl) amino-COC 2 H 4 -, N- [1, 1-dimethylethyl] -N-methylamino-COC 2 H 4 -, N-ethyl-N-propylamino-COC 2 H 4 -, N-ethyl-N- (1-methylethyl) amino-COC 2 H 4 -, N-butyl-N-ethylamino-COC 2 H-, N-ethyl-N- (l-methylpropyl) amino-COC 2 H 4 -, N-ethyl-N- (2-methylpropyl) amino-COC 2 H 4 -, N-ethyl-N- [1, 1-dimethylethyl ] - amino-COC 2 H 4 -, N- (1-methylethyl) -N-propylamino-COC 2 H 4 -, N-butyl-N-propylamino-COC 2 H 4 -, N- (1-methylpropyl) - N-propyl-amino-COC 2 H 4 -, N- (2-methylpropyl) -N-propylamino-COCH 4 -, N- [1, 1-dimethylethyl] -N-propylamino-COC 2 H 4 -, N- Butyl-N-
(l-methylethyl)amino-COC2H4-, N- (1-Methylethyl) -N- (1-methyl- propyl) amino-COC2H4-, N- (1-Methylethyl) -N- (2-methylpropyl) - amino-COC2H4-, N- [1, 1-Dimethylethyl] -N- (1-methylethyl) amino- COC2H4-, N-Butyl-N- (l-methylpropyl)amino-COC2H-, N-Butyl-N- (2-methylpropyl)amino-COC2H4-, N-Butyl-N- (1, 1-dimethylethyl) - amino-COC2H4- , N- (1-Methylpropyl) -N- (2-methyl-propyl) amino- COC2H4-, N- [1, 1-Dimethylethyl] -N- (1-methylpropyl) amino-COC2H4- oder N- [1, 1-Dimethylethyl] -N- (2-methylpropyl)amino-COC2H5-, insbesondere für CH2-CON(CH3)2, CH2-CON(C2H5) 2, CH(CH3) -CON(CH3)2 oder CH(CH3)CON(C2H5) ;(l-methylethyl) amino-COC 2 H 4 -, N- (1-methylethyl) -N- (1-methyl-propyl) amino-COC 2 H 4 -, N- (1-methylethyl) -N- (2nd -methylpropyl) - amino-COC 2 H 4 -, N- [1, 1-dimethylethyl] -N- (1-methylethyl) amino- COC 2 H 4 -, N-butyl-N- (l-methylpropyl) amino- COC 2 H-, N-butyl-N- (2-methylpropyl) amino-COC 2 H 4 -, N-butyl-N- (1, 1-dimethylethyl) - amino-COC 2 H 4 -, N- (1 -methylpropyl) -N- (2-methylpropyl) amino COC 2 H 4 -, N- [1, 1-dimethylethyl] -N- (1-methylpropyl) amino-COC 2 H 4 - or N- [1 , 1-Dimethylethyl] -N- (2-methylpropyl) amino-COC 2 H 5 -, in particular for CH 2 -CON (CH 3 ) 2, CH 2 -CON (C 2 H 5 ) 2, CH (CH 3 ) -CON (CH 3 ) 2 or CH (CH 3 ) CON (C 2 H 5 );
Cι-C4-Alkylamino-Cι-C4-alkyl für: durch Cι-C4-Alkylamino wie -NH-CH3, -NH-C2H5, -NH- (n-Propyl) , -NH-CH(CH3)2/ -NH- (n-Butyl) , -NH-CH(CH3) -C2H5, -NH-CH2-CH(CH3) und -NH-C(CH3)3, vorzugsweise -NH-CH3 oder -NH-C2H5, substituiertes C1-C4 -Alkyl, also beispielsweise für CH2CH2-NH-CH3 oder CH2CH2-NH-C2H5;-C-C 4 alkylamino -CC 4 -alkyl for: by -C-C 4 alkylamino such as -NH-CH 3 , -NH-C2H5, -NH- (n-propyl), -NH-CH (CH 3 ) 2 / -NH- (n-butyl), -NH-CH (CH 3 ) -C 2 H 5 , -NH-CH 2 -CH (CH 3 ) and -NH-C (CH 3 ) 3 , preferably - NH-CH 3 or -NH-C 2 H 5 , substituted C 1 -C 4 alkyl, for example for CH 2 CH 2 -NH-CH 3 or CH 2 CH 2 -NH-C 2 H 5 ;
(Cι-C4-Alkylamino)carbonyl-Cι-C4-alkyl für: durch (C1-C4-Alkylamino) carbonyl wie -CONH-CH3, -CONH-C2Hs, -CONH- (n-Propyl) , -CONH-CH(CH3) 2, -CONH- (n-Butyl) , -CONH- (1-Methylpropyl) , -CONH-CH2-CH(CH3) 2 und -CONH-C (CH3) 2, vorzugsweise -CONH-CH3 oder -CONH-C2H5, substituiertes Cι-C.4-Alkyl, also beispielsweise für CH2-CONH-CH3, CH2-CONH-C2H5, CH(CH3) -CONH-CH3 oder CH(CH3) -CONH-C2H5;(-C-C 4 -alkylamino) carbonyl -CC-C 4 -alkyl for: by (C 1 -C 4 -alkylamino) carbonyl such as -CONH-CH 3 , -CONH-C 2 H s , -CONH- (n- Propyl), -CONH-CH (CH 3 ) 2 , -CONH- (n-butyl), -CONH- (1-methylpropyl), -CONH-CH 2 -CH (CH 3 ) 2 and -CONH-C (CH 3 ) 2 , preferably -CONH-CH 3 or -CONH-C 2 H 5 , substituted Cι-C. 4 alkyl, for example for CH 2 -CONH-CH 3 , CH 2 -CONH-C 2 H 5 , CH (CH 3 ) -CONH-CH 3 or CH (CH 3 ) -CONH-C 2 H 5 ;
C3-C6~Alkenyl für: Prop-1-en-1-yl, Prop-2-en-l-yl, 1-Methyl- ethenyl, n-Buten-1-yl, n-Buten-2-yl, n-Buten-3-yl, 1-Methyl - prop-1-en-l-yl, 2-Methylprop-l-en-l-yl, l-Methylprop-2-en- 1-yl, 2-Methylprop-2-en-l-yl, n-Penten-1-yl, n-Penten-2-yl, n-Penten-3-yl, n-Penten-4-yl, 1-Methylbut-l-en-l-yl, 2-Methylbut-l-en-l-yl, 3-Methylbut-l-en-l-yl, 1-Methylbut- 2-en-l-yl, 2-Methylbut-2-en-l-yl, 3-Methylbut-2-en-l-yl, l-Methylbut-3-en-l-yl, 2-Methylbut-3-en-l-yl, 3-Methyl- but-3-en-l-yl, 1, 1-Dirnethyl-prop-2-en-1-yl, 1, 2-Dimethyl- prop-1-en-l-yl, 1, 2-Dimethyl-prop-2-en-l-yl, 1-Ethylprop- l-en-2-yl, l-Ethylprop-2-en-l-yl, n-Hex-1-en-l-yl, n-Hex-C 3 -C 6 ~ alkenyl for: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl , n-buten-3-yl, 1-methyl-prop-1-en-l-yl, 2-methylprop-l-en-l-yl, l-methylprop-2-en-1-yl, 2-methylprop -2-en-l-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methylbut-l-en-l -yl, 2-methylbut-l-en-l-yl, 3-methylbut-l-en-l-yl, 1-methylbut- 2-en-l-yl, 2-methylbut-2-en-l-yl, 3-methylbut-2-en-l-yl, l-methylbut-3-en-l-yl, 2-methylbut-3- en-l-yl, 3-methyl-but-3-en-l-yl, 1, 1-dirnethyl-prop-2-en-1-yl, 1, 2-dimethyl-prop-1-en-l- yl, 1, 2-dimethyl-prop-2-en-l-yl, 1-ethylprop-l-en-2-yl, l-ethylprop-2-en-l-yl, n-hex-1-en- l-yl, n-hex
2-en-l-y-l n-Hex-3-en-l-yl, n-Hex-4-en-l-yl, n-Hex-5-en-l-yl, 1-Methylpent-l-en-l-yl, 2-Methylpent-l-en-l-yl, 3-Methyl- pent-1-en-l-yl, 4-Methylpent-l-en-l-yl, l-Methylpent-2- en-l-yl, 2-Methylpent-2-en-l-yl, 3-Methylpent-2-en-l-yl, 4-Methylpent-2-en-l-yl, l-Methylpent-3-en-l-yl, 2-Methyl- pent-3-en-l-yl, 3-Methylpent-3-en-l-yl, 4-Methylpent-3- en-l-yl, l-Methylpent-4-en-l-yl, 2-Methylpent-4-en-l-yl, 3-Methylpent-4-en-l-yl, 4-Methylpent-4-en-l-yl, 1, 1-Dimethyl- but-2-en-l-yl, 1, l-Dimethyl-but-3-en-l-yl, 1, 2-Dimethyl-but- 1-en-l-yl, 1, 2-Dimethyl-but-2-en-l-yl, 1, 2-Dimethyl-but-3- en-l-yl, 1, 3-Dimethyl-but-l-en-l-yl, 1, 3-Dimethyl-but-2-en- 1-yl, l,3-Dimethyl-but-3-en-l-yl, 2, 2-Dimethyl-but-3-en-l-yl, 2 , 3-Dimethyl-but-l-en-l-yl , 2 , 3-Dimethyl-but-2-en-l-yl , 2 , 3-Dimethyl-but-3-en-l-yl , 3 , 3-Dimethyl-but-l-en-l-yl , 3,3-Dimethyl-but-2-en-l-yl, 1-Ethylbut-l-en-l-yl, 1-Ethyl- but-2-en-l-yl, l-Ethylbut-3-en-l-yl, 2-Ethylbut-l-en-l-yl, 2-Ethylbut-2-en-l-yl, 2-Ethylbut-3-en-l-yl, 1, 1,2-Trimethyl- prop-2-en-l-yl, l-Ethyl-l-methyl-prop-2-en-l-yl, l-Ethyl-2- methyl-prop-1-en-l-yl oder l-Ethyl-2-methyl-prop-2-en-l-yl, insbesondere für Allyl oder 2 -Buten- 1-yl;2-en-lyl n-hex-3-en-l-yl, n-hex-4-en-l-yl, n-hex-5-en-l-yl, 1-methylpent-l-en-l -yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1 -yl, 2-methylpent-2-en-l-yl, 3-methylpent-2-en-l-yl, 4-methylpent-2-en-l-yl, l-methylpent-3-en-l-yl , 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl , 2-methylpent-4-en-l-yl, 3-methylpent-4-en-l-yl, 4-methylpent-4-en-l-yl, 1, 1-dimethylbut-2-en-l -yl, 1, l-dimethyl-but-3-en-l-yl, 1, 2-dimethyl-but-1-en-l-yl, 1, 2-dimethyl-but-2-en-l-yl , 1, 2-Dimethyl-but-3-en-1-yl, 1, 3-dimethyl-but-1-en-1-yl, 1, 3-dimethyl-but-2-en-1-yl, 1 , 3-Dimethyl-but-3-en-l-yl, 2, 2-dimethyl-but-3-en-l-yl, 2, 3-dimethyl-but-l-en-l-yl, 2, 3 -Dimethyl-but-2-en-l-yl, 2,3-dimethyl-but-3-en-l-yl, 3,3,3-dimethyl-but-l-en-l-yl, 3,3-dimethyl -but-2-en-l-yl, 1-ethylbut-l-en-l-yl, 1-ethyl-but-2-en-l-yl, l-ethylbut-3-en-l-yl, 2 -Ethylbut-l-en-l-yl, 2-ethylbut-2-en-l-yl, 2-ethylbut-3-en-l-yl , 1, 1,2-trimethyl-prop-2-en-l-yl, l-ethyl-l-methyl-prop-2-en-l-yl, l-ethyl-2-methyl-prop-1-ene -l-yl or l-ethyl-2-methyl-prop-2-en-l-yl, especially for allyl or 2-buten-1-yl;
C3-C6-Halogenalkenyl für: C3-Cδ-Alkenyl wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor, Brom und/oder Jod substituiert ist, also z.B. für 2-Chlor- allyl, 3-Chlorallyl, 2, 3-Dichlorallyl, 3, 3-Dichlorallyl, 2,3,3-Trichlorallyl, 2, 3-Dichlorbut-2-enyl, 2-Bromallyl, 3-Bromallyl, 2, 3-Dibromallyl, 3, 3-Dibromallyl, 2, 3, 3-Tribrom- allyl oder 2, 3-Dibrombut-2-enyl, insbesondere für 2-Chlor- allyl, 3-Chlorallyl oder 3,3-Dichlorallyl;C 3 -C 6 haloalkenyl for: C 3 -C δ alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for 2-chloroallyl, 3-chloroallyl, 2, 3-dichlorallyl, 3, 3-dichlorallyl, 2,3,3-trichlorallyl, 2, 3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2, 3-dibromoallyl, 3, 3-dibromoallyl, 2, 3, 3-tribromo-allyl or 2,3-dibromobut-2-enyl, in particular for 2-chloro-allyl, 3-chloroallyl or 3,3-dichloroallyl;
Cyano-C3-C6-alkenyl für: z.B. 2-Cyanoallyl, 3-Cyanoallyl, 4-Cyanobut-2-enyl, 4-Cyanobut-3-enyl oder 5-Cyanopent-4-enyl, insbesondere für 3-Cyanoallyl oder 4-Cyanobut-2-enyl;Cyano-C 3 -C 6 -alkenyl for: eg 2-cyanoallyl, 3-cyanoallyl, 4-cyanobut-2-enyl, 4-cyanobut-3-enyl or 5-cyanopent-4-enyl, in particular for 3-cyanoallyl or 4-cyanobut-2-enyl;
C3-C6-Alkinyl für: Prop-1-in-1-yl, Propargyl, 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-1-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- 1-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 Propargyl;C 3 -C 6 alkynyl for: prop-1-in-1-yl, propargyl, n-but-1-in-1-yl, n-but-1-in-3-yl, n-but-1 -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-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-1-yl, n-hex-l-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-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 or 4-methyl-pent-2-in-5-yl, especially for Propargyl;
C3-C6-Ha-logenalkinyl für: C3-C6~Alkinyl wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor, Brom und/oder Jod substituiert ist, also z.B. für 1,1-Di- fluorprop-2-in-l-yl, 4-Fluorbut-2-in-l-yl, 4-Chlorbut-2-in- 1-yl, 1,1-Difluorbut-2-in-l-yl, 5-Fluorpent-3-in-l-yl oderC 3 -C 6 -Ha-logenalkynyl for: C 3 -C 6 ~ alkynyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for 1,1-di-fluoroprop- 2-in-l-yl, 4-fluorobut-2-in-l-yl, 4-chlorobut-2-in-1-yl, 1,1-difluorobut-2-in-l-yl, 5-fluoropentyl 3-in-l-yl or
6-Fluorhex-4-in-l-yl, insbesondere für 4-Fluorbut-2-in-l-yl;6-fluorohex-4-in-l-yl, especially for 4-fluorobut-2-in-l-yl;
Cyano-C3-C6-alkinyl für: z.B. 3-Cyanopropargyl, 4-Cyano- but-2-in-l-yl, 5-Cyanopent-3-in-l-yl und 6-Cyanohex-4-in- 1-yl;Cyano-C 3 -C 6 -alkynyl for: e.g. 3-cyanopropargyl, 4-cyano-but-2-in-l-yl, 5-cyanopent-3-in-l-yl and 6-cyanohex-4-in 1-yl;
C3-C4-Alkenyloxy-Cι-C4-alkyl für: durch C3-C4-Alkenyloxy wie Allyloxy, But-l-en-3-yloxy, But-l-en-4-yloxy, But-2-en-l-yl- oxy, l-Methylprop-2-enyloxy und 2-Methylprop-2-enyloxy, substituiertes C1-C4-Alkyl, also beispielsweise für Allyloxy- methyl, 2-Allyloxyethyl oder But-l-en-4-yloxymethyl, insbesondere für 2-Allyloxyethyl;C 3 -C 4 alkenyloxy -CC-C 4 alkyl for: by C 3 -C 4 alkenyloxy such as allyloxy, but-l-en-3-yloxy, but-l-en-4-yloxy, but-2 -en-l-yl-oxy, l-methylprop-2-enyloxy and 2-methylprop-2-enyloxy, substituted C 1 -C 4 alkyl, for example for allyloxy-methyl, 2-allyloxyethyl or but-l-ene -4-yloxymethyl, especially for 2-allyloxyethyl;
C3-C4-Alkinyloxy-Cι-C4-alkyl für: durch C3-C4~Alkinyloxy wie Propargyloxy, But-l-in-3-yloxy, But-l-in-4-yloxy, But-2-in-l- yloxy, l-Methylprop-2-inyloxy und 2-Methylprop-2-inyloxy, vorzugsweise Propargyloxy, substituiertes Cι~C4-Alkyl, also beispielsweise für Propargyloxymethyl oder 2-Propargyloxy- ethyl, insbesondere für 2-Propargyloxyethyl;C 3 -C 4 alkynyloxy -CC-C 4 alkyl for: by C 3 -C 4 ~ alkynyloxy such as propargyloxy, but-l-in-3-yloxy, but-l-in-4-yloxy, but-2 -in-l-yloxy, l-methylprop-2-ynyloxy and 2-methylprop-2-ynyloxy, preferably propargyloxy, substituted C 1 -C 4 -alkyl, so for example for propargyloxymethyl or 2-propargyloxyethyl, especially for 2-propargyloxyethyl ;
C3-C4-Alkenylthio-Cι-C4-alkyl für: durch C3-C4~Alkenylthio wie Allylthio, But-l-en-3-ylthio, But-l-en-4-ylthio, But-2-en-l- ylthio, l-Methylprop-2-enylthio und 2-Methylprop-2-enylthio, substituiertes Cι-C4-Alkyl, also beispielsweise für Allylthio- methyl, 2-Allylthioethyl oder But-l-en-4-ylthiomethyl, insbesondere für 2- (Allylthio)ethyl;C 3 -C 4 alkenylthio -CC-C 4 alkyl for: by C 3 -C 4 ~ alkenylthio such as allylthio, but-l-en-3-ylthio, but-l-en-4-ylthio, but-2 -en-l-ylthio, l-methylprop-2-enylthio and 2-methylprop-2-enylthio, substituted C 1 -C 4 -alkyl, for example for allylthio-methyl, 2-allylthioethyl or but-l-en-4- ylthiomethyl, especially for 2- (allylthio) ethyl;
C3-C4-Alkinylthio-Cι-C4-alkyl für: durch C3-C4-Alkinylthio wie Propargylthio, But-l-in-3-ylthio, But-l-in-4-ylthio, But-2-in-l-ylthio, l-Methylprop-2-inylthio und 2-Methyl- prop-2-inylthio, vorzugsweise Propargylthio, substituiertes C1-C4-Alkyl, also beispielsweise für Propargylthiomethyl oder 2-Propargylthioethyl, insbesondere für 2- (Propargyl hio) - ethyl . Alle Phenyl- oder Cycloalkylringe sind vorzugsweise unsubsti- tuiert oder tragen einen Substituenten.C 3 -C 4 alkynylthio -CC-C 4 alkyl for: by C 3 -C 4 alkynylthio such as propargylthio, but-l-in-3-ylthio, but-l-in-4-ylthio, but-2 -in-l-ylthio, l-methylprop-2-ynylthio and 2-methyl-prop-2-ynylthio, preferably propargylthio, substituted C 1 -C 4 alkyl, for example for propargylthiomethyl or 2-propargylthioethyl, especially for 2- (Propargyl hio) - ethyl. All phenyl or cycloalkyl rings are preferably unsubstituted or have a substituent.
Im Hinblick auf die Verwendung der substituierten 3-Phenyl- pyrazole I/I' als Herbizide sind diejenigen Verbindungen 1/1 ' bevorzugt, bejl denen die Variablen folgende Bedeutungen haben, und zwar jeweils für sich allein oder in Kombination:With regard to the use of the substituted 3-phenylpyrazoles I / I 'as herbicides, preference is given to those compounds 1/1' where the variables have the following meanings, individually or in combination:
R1 C1-C4-Alkyl, insbesondere Methyl;R 1 C 1 -C 4 alkyl, especially methyl;
R2 Cχ-C4-Halogenalkyl, insbesondere Difluormethyl;R 2 Cχ-C 4 haloalkyl, especially difluoromethyl;
R3 Cyano, Halogen oder Cι-C4~Halogenalkyl, insbesondere Halogen; besonders bevorzugt ist Chlor;R 3 cyano, halogen or -CC 4 ~ haloalkyl, especially halogen; chlorine is particularly preferred;
R4 Fluor oder Chlor, insbesondere Fluor;R 4 fluorine or chlorine, especially fluorine;
R5 Halogen oder Cι-C4-Halogenalkyl, insbesondere Chlor, Brom oder Trifluormethyl; besonders bevorzugt ist Chlor;R 5 halogen or -CC 4 haloalkyl, especially chlorine, bromine or trifluoromethyl; chlorine is particularly preferred;
R6, R7 unabhängig voneinanderR 6 , R 7 independently of one another
Ci-Cβ-Alkyl, Ci-Cβ-Halogenalkyl, Cι-C -Alkoxy-Cι-C4-alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl, C3-Cg -Alkinyl, (C1-C4 -Alkyl) carbonyl, Di (C1-C4-alkyl) aminocarbonyl, (Ci-C4-Alkoxy) carbonyl -C1-C4-alkyl, das eineCi-Cβ-alkyl, Ci-Cβ-haloalkyl, -CC-alkoxy -CC-C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -Cg alkynyl, (C 1 -C 4 alkyl) carbonyl, di (C 1 -C 4 alkyl) aminocarbonyl, (Ci-C 4 alkoxy) carbonyl -C 1 -C 4 alkyl, the one
(Cι-C4-Alkoxy) imino-Gruppe tragen kann, Phenyl oder Benzyl, insbesondere Ci-Ce-Alkyl, Cι-C4-Alkoxy-Cι-C4-alkyl, C3-C6-Alkenyl, C3-Cβ-Alkinyl oder (Cι-C4-Alkoxy) carbonyl - C1-C4-alkyl.(Cι-C 4 -alkoxy) imino group may bear, phenyl or benzyl, in particular Ci-Ce-alkyl, Cι-C4-alkoxy-Cι-C 4 alkyl, C 3 -C 6 alkenyl, C 3 - Cβ-alkynyl or (-CC 4 alkoxy) carbonyl - C 1 -C 4 alkyl.
Ganz besonders bevorzugt sind die substituierten 3-Phenylpyrazole der Formeln Ia (R1 = Methyl, R2 = Difluormethyl, R3 und R5 = Chlor) und Ib (R1 = Methyl, R2 = Difluormethyl, R3 = Fluor, R5 = Chlor) , insbesondere die in der folgenden Tabelle 1 aufge- führten Verbindungen la.l bis Ia.1453 sowie die Verbindungen Ib.l bis Ib.1453, die sich von den entsprechenden Verbindungen la.l bis la.1453 lediglich dadurch unterscheiden, daß R3 für Fluor steht:The substituted 3-phenylpyrazoles of the formulas Ia (R 1 = methyl, R 2 = difluoromethyl, R 3 and R 5 = chlorine) and Ib (R 1 = methyl, R 2 = difluoromethyl, R 3 = fluorine, R) are very particularly preferred 5 = chlorine), in particular the compounds la.l to Ia.1453 listed in the following Table 1 and the compounds ib.l to Ib.1453, which differ from the corresponding compounds la.l to la.1453 only in that that R 3 represents fluorine:
Figure imgf000022_0001
Tabelle 1
Figure imgf000022_0001
Table 1
Figure imgf000023_0001
Figure imgf000023_0001
Figure imgf000023_0002
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0001
Figure imgf000036_0001
Figure imgf000037_0001
Figure imgf000038_0001
Figure imgf000039_0001
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000055_0001
Figure imgf000056_0001
Figure imgf000057_0001
Figure imgf000058_0001
Figure imgf000059_0001
Figure imgf000060_0001
Figure imgf000023_0002
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0001
Figure imgf000036_0001
Figure imgf000037_0001
Figure imgf000038_0001
Figure imgf000039_0001
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000055_0001
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Figure imgf000057_0001
Figure imgf000058_0001
Figure imgf000059_0001
Figure imgf000060_0001
Die substituierten 3-Phenylpyrazole der Formel I sind auf verschiedene Weise erhältlich, insbesondere nach einem der folgenden Verfahren:The substituted 3-phenylpyrazoles of the formula I can be obtained in various ways, in particular by one of the following processes:
A) Umsetzung- .einer 3-Pyrazolylbenzoesäure II mit einem Oxy- amin IV {siehe z.B. Houben-Weyl, Methoden der organischen Chemie, Bd. E5, Georg Thieme Verlag, Stuttgart 1985, S. 587 ff. und 114 ff.}:A) Reaction of a 3-pyrazolylbenzoic acid II with an oxamine IV {see e.g. Houben-Weyl, Methods of Organic Chemistry, Vol. E5, Georg Thieme Verlag, Stuttgart 1985, pp. 587 ff. And 114 ff.}:
Figure imgf000061_0001
Figure imgf000061_0001
(Base)(Base)
Die Überführung von II in I kann auf zweierlei Arten erfolgen: Eine Ausführungsform besteht darin, aus II zuerst das ent- prechende Säurechlorid herzustellen und dieses anschließend in Gegenwart einer Base - z.B. einem Amin wie Triethylamin oder Pyridin, einem Alkalimetallcarbonat wie Kaliumcarbonat, einem Alkalimetallhydrid wie Natriumhydrid oder einem Alkali- metallhydroxid wie Natriumhydroxid und Kaliumhydroxid - mit einem Oxyamin IV umzusetzen.There are two ways of converting II to I: One embodiment consists in first preparing the corresponding acid chloride from II and then in the presence of a base, e.g. an amine such as triethylamine or pyridine, an alkali metal carbonate such as potassium carbonate, an alkali metal hydride such as sodium hydride or an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide - to react with an oxyamine IV.
Geeignete Chlorierungsmittel sind beispielsweise Phosgen, OxalylChlorid, Phosphoroxychlorid und Thionylchlorid.Suitable chlorinating agents are, for example, phosgene, oxalyl chloride, phosphorus oxychloride and thionyl chloride.
Die Chlorierung erfolgt in der Regel in einem inerten organischen Lösungsmittel, wobei z.B. aliphatische oder aromatische Kohlenwasserstoffe wie n-Hexan und Toluol, Halogenkohlenwasserstoffe wie Dichlormethan, Ether wie Diethylether und Tetrahydrofuran, sowie aprotische Lösungsmittel wie Dimethyl- formamid und Acetonitril in Betracht kommen. Für die Umsetzung des Säurechlorids mit IV sind die genanntenThe chlorination is generally carried out in an inert organic solvent, for example aliphatic or aromatic hydrocarbons such as n-hexane and toluene, halogenated hydrocarbons such as dichloromethane, ethers such as diethyl ether and tetrahydrofuran, and aprotic solvents such as dimethylformamide and acetonitrile. For the implementation of the acid chloride with IV, the above are
Solventien im allgemeinen ebenfalls geeignet, sowie derenSolvents are also generally suitable, as well as their
Mischungen mit Wasser.Mixtures with water.
Eine zweite Ausführungsform besteht darin, II direkt mit dem Oxyamin I-y in einem der vorstehend genannten organischen Lösungsmitteln umzusetzen. Vorzugsweise arbeitet man hierbei in Gegenwart eines Kupplungsreagenzes wie Carbonyldiimidazol und Dicyclohexylcarbodiimid.A second embodiment consists of reacting II directly with the oxyamine I-y in one of the above-mentioned organic solvents. This is preferably carried out in the presence of a coupling reagent such as carbonyldiimidazole and dicyclohexylcarbodiimide.
Alkylierung oder Acylierung eines substituierten 3 -Phenyl - pyrazols der Formel I, wobei R6 für Wasserstoff steht {siehe z.B. Houben-Weyl, Methoden der Organischen Chemie, Bd. E5, Georg-Thieme Verlag, Stuttgart 1985, S. 1148}:Alkylation or acylation of a substituted 3-phenylpyrazole of the formula I, where R 6 is hydrogen {see, for example, Houben-Weyl, Methods of Organic Chemistry, Vol. E5, Georg-Thieme Verlag, Stuttgart 1985, p. 1148}:
IIIIII
L steht für eine übliche Abgangsgruppe wie Halogen, Methyl - sulfonyloxy, Trifluormethylsulfonyloxy und p-Toluylsulfonyl- oxy.L stands for a common leaving group such as halogen, methylsulfonyloxy, trifluoromethylsulfonyloxy and p-tolylsulfonyloxy.
Vorzugsweise arbeitet man in Gegenwart einer Base, z.B. einem Amin wie Triethylamin und Pyridin, einem Alkalimetallcarbonyl wie Kaliumcarbonat, einem Alkalimetallhydrid wie Natriumhydrid oder einem Alkalimetallhydroxid wie Natriumhydroxid und Kaliumhydroxid.Preferably one works in the presence of a base, e.g. an amine such as triethylamine and pyridine, an alkali metal carbonyl such as potassium carbonate, an alkali metal hydride such as sodium hydride or an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide.
Als Lösungsmittel eignen sich beispielsweise aliphatische oder aromatische Kohlenwasserstoffe wie n-Hexan und Toluol, Halogenkohlenwasserstoffe wie Dichlormethan, Ether wie Diethylether und Tetrahydrofuran, aprotische Lösungsmittel wie Dimethylformamid und Acetonitril sowie Mischungen der genannten Solventien.Examples of suitable solvents are aliphatic or aromatic hydrocarbons such as n-hexane and toluene, halogenated hydrocarbons such as dichloromethane, ethers such as diethyl ether and tetrahydrofuran, aprotic solvents such as dimethylformamide and acetonitrile and mixtures of the solvents mentioned.
Bei der Reaktion kann als Nebenprodukt das Isomer III entstehen; es ist auf übliche Weise, z.B. mittels Extraktion, Kristallisation, Destillation oder Chromatographie, abtrennbar. Alle genannten Reaktionen werden bei Temperaturen zwischen dem Schmelz- und Siedepunkt des Lösungsmittels, insbesondere bei 0 bis 100°C, durchge ührt. Die Reaktionspartner werden dabei vorzugsweise in ca. äquimolaren Mengen oder in einem Überschuß bis etwa zur zehnfachen molaren Menge, bezogen auf die Menge anThe isomer III can form as a by-product of the reaction; it can be separated off in the usual way, for example by means of extraction, crystallization, distillation or chromatography. All of the reactions mentioned are carried out at temperatures between the melting and boiling point of the solvent, in particular at 0 to 100 ° C. The reactants are preferably in approximately equimolar amounts or in an excess of up to about ten times the molar amount, based on the amount
Carbonsäure II, deren Säurechlorid oder an I {R6 = H} , eingesetzt.Carboxylic acid II, its acid chloride or at I {R 6 = H}, used.
Sofern nicht anders angegeben werden alle vorstehend beschriebenen Verfahren zweckmäßigerweise bei Atmosphärendruck oder unter dem Eigendruck des jeweiligen Reaktionsgemisches vorgenommen.Unless otherwise stated, all of the processes described above are expediently carried out at atmospheric pressure or under the autogenous pressure of the respective reaction mixture.
Normalerweise sind die substituierten 3-Phenylpyrazole I nach einem der vorstehend genannten Syntheseverfahren herstellbar. Aus wirtschaftlichen oder verfahrenstechnischen Gründen kann es jedoch zweckmäßiger sein, einige Verbindungen I aus ähnlichen 3-Phenylpyrazolen, die sich jedoch insbesondere in der Bedeutung des Restes R6 oder R7 unterscheiden, herzustellen, und zwar auf an sich bekannte Weise, z.B. durch Alkylierung, Acetalhydrolyse, Acetalisierung, Amidierung, Esterhydrolyse, Kondensationsreak- tion, Oxidation, Peterson-Olefinierung, Reduktion, Veretherung, Veresterung oder Wittig-Reaktion.The substituted 3-phenylpyrazoles I can normally 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 3-phenylpyrazoles, but which differ in particular in the meaning of the radical R 6 or R 7 , in a manner known per se, for example by alkylation, Acetal hydrolysis, acetalization, amidation, ester hydrolysis, condensation reaction, oxidation, Peterson olefination, reduction, etherification, esterification or Wittig reaction.
Die für die einzelnen Verfahren angegebenen Ausgangsverbindungen sind entweder bekannt oder auf an sich bekannte Weise oder in Analogie zu einem der beschriebenen Verfahren erhältlich.The starting compounds specified for the individual processes are either known or are obtainable in a manner known per se or in analogy to one of the processes described.
Die Aufarbeitung der Reaktionsgemische erfolgt in der Regel nach an sich bekannten Methoden, beispielsweise durch Verdünnen der Reaktionslösung mit Wasser und anschließender Isolierung des Produktes mittels Filtration, Kristallisation oderThe 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
Lösungsmittelextraktion, oder durch Entfernen des Lösungsmittels, Verteilen des Rückstandes in einem Gemisch aus Wasser und einem geeigneten organischenSolvent extraction, or by removing the solvent, distributing the residue in a mixture of water and a suitable organic
Lösungsmittel und Aufarbeiten der organischen Phase auf das Produkt hin.Solvent and work-up of the organic phase towards the product.
Die substituierten 3-Phenylpyrazole I können bei der Herstellung als Isomerengemische anfallen, die jedoch gewünschtenfalls nach den hierfür üblichen Methoden wie Kristallisation oder Chromato- graphie, auch an einem optisch aktiven Adsorbat, in die weitgehend reinen Isomeren getrennt werden können. Reine optisch aktive Isomere lassen sich vorteilhaft aus entsprechenden optisch aktiven Ausgangsprodukten herstellen.The substituted 3-phenylpyrazoles I can be obtained in the preparation as isomer mixtures, which, however, if desired, can be separated into the largely 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.
Landwirtschftlich brauchbare Salze der Verbindungen I können durch Reaktion mit einer Base des entprechenden Kations, vorzugsweise einem Alkalimetallhydroxid oder -hydrid, oder durch Reak- tion mit einer Säure des entprechenden Anions, vorzugsweise derSalts of the compounds I which can be used commercially can be reacted with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride, or by reacting tion with an acid of the corresponding anion, preferably the
Chlorwasserstoffsäure, Bromwasserstoffsäure, Schwefelsäure,Hydrochloric acid, hydrobromic acid, sulfuric acid,
Phosphorsäure oder Salpetersäure, gebildet werden.Phosphoric acid or nitric acid.
Salze von I, deren Metallion kein Alkalimetallion ist, können auch durch Ums.alzen des entsprechenden Alkalimetallsalzes 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 Schadgräser, 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, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
In Abhängigkeit von der jeweiligen Applikationsmethode können die Verbindungen I bzw. sie enthaltenden herbiziden Mittel noch in einer weiteren Zahl von Kulturpflanzen zur Beseitigung unerwünschter Pflanzen eingesetzt werden. In Betracht kommen beispielsweise folgende Kulturen: 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, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium) , Helianthus annuus, Hevea brasiliensis, Hordeu 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, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera und Zea mays. Darüber hinaus können die Verbindungen I auch in Kulturen, die durch Züchtung einschließlich gentechnischer Methoden gegen dieDepending on the particular application method, the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants. For example, the following crops are suitable: Allium cepa, pineapple 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, Hordeu vulgäre, Humulus lupulus, Ipomoealinarisumisum , 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 pers , Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (see vulgar), Theobroma cacao, Trifolium prate nse, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays. In addition, the compounds I can also be used in crops which have been cultivated against, including by genetic engineering methods
Wirkung von Herbiziden tolerant sind, verwandt werden.The effects of herbicides are tolerant.
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 Granu- laten 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, 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, spreading agents or granules , Atomizing, dusting, scattering or pouring can be used. The application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
Als inerte Hilfsstoffe kommen im Wesentlichen in Betracht: Mineralölfraktionen von mittlerem bis hohem Siedepunkt wie Kerosin und Dieselöl, ferner Kohlenteerole sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromati- sehe 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.The following are essentially considered as inert auxiliaries: mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, also coal tarols and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, 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 substituierten 3-Phenylpyrazole I als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermittel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz, Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.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 substituted 3-phenylpyrazoles 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- oxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylen- oderThe 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 condensates, ethoxylated castor oil, polyoxyethylene or
Polyoxypropylenalkylether, Laurylalkoholpolyglykoletheracetat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose inPolyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol ester, lignin sulfite waste liquor or methyl cellulose in
Betracht.Consideration.
Pulver-, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Feste Trägerstoffe sind Mineralerden wie Kiesel - säuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baum- rinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe.Granules, e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers. Solid carriers are mineral earths such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
Die Konzentrationen der Wirkstoffe I in den anwendungsfertigen Zubereitungen können in weiten Bereichen variiert werden. Im allgemeinen enthalten die Formulierungen etwa von 0,001 bis 98 Gew.-%, vorzugsweise 0,01 bis 95 Gew.-%, mindestens eines Wirkstoffs. Die Wirkstoffe werden dabei in einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach NMR-Spektrum) eingesetzt.The concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range. In general, the formulations contain from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
Die folgenden Formulierungsbeispiele verdeutlichen die Herstellung solcher Zubereitungen:The following formulation examples illustrate the preparation of such preparations:
I. 20 Gewichtsteile der Verbindung Nr. Ia.25 werden in einer Mischung gelöst, die aus 80 Gewichtsteilen alkyliertemI. 20 parts by weight of compound no. Ia.25 are dissolved in a mixture which is alkylated from 80 parts by weight
Benzol, 10 Gewichtsteilen des Anlagerungsproduktes von 8 bis 10 Mol Ethylenoxid an 1 Mol Ölsäure-N-monoethanolamid, 5 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure und 5 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Rizinusöl besteht. Durch Ausgießen und feines Verteilen der Lösung in 100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs enthält. II. 20 Gewichtsteile der Verbindung Nr. Ia.27 werden in einer Mischung gelöst, die aus 40 Gewichtsteilen Cyclohexanon,Benzene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide in 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide in 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient. II. 20 parts by weight of compound no. Ia.27 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 comprises 0.02% by weight of the active ingredient.
III. 20 Gewichtsteile des Wirkstoffs Nr. Ia.677 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. Ia.677 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 comprises 0.02% by weight of the active ingredient.
IV. 20 Gewichtsteile des Wirkstoffs Nr. Ia.27 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 ver- mischt und in einer Hammermühle vermählen. Durch feines Verteilen der Mischung in 20000 Gewichtsteilen Wasser erhält man eine Spritzbrühe, die 0,1 Gew.-% des Wirkstoffs enthält.IV. 20 parts by weight of active ingredient No. Ia.27 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and in a hammer mill marry. 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. Ia.45 werden mitV. 3 parts by weight of active ingredient No. Ia.45 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 dust is obtained which contains 3% by weight of the active ingredient.
VI. 20 Gewichtsteile des Wirkstoffs Nr. Ia.47 werden mitVI. 20 parts by weight of active ingredient No. Ia.47 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.2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.
VII. 1 Gewichtsteil des Wirkstoffs Nr. Ia.379 wird in einer Mischung gelöst, die aus 70 Gewichtsteilen Cyclohexanon, 20 Gewichtsteilen ethoxyliertem Isooctylphenol undVII. 1 part by weight of active ingredient No. Ia.379 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. VIII. 1 Gewichtsteil des Wirkstoffs Nr. Ia.385 wird in einerThere are 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained. VIII. 1 part by weight of active ingredient No. Ia.385 is in a
Mischung gelöst, die aus 80 Gewichtsteilen Cyclohexanon und 20 Gewichtsteilen Wettol® EM 31 (= nichtionischer Emulgator auf der Basis von ethoxyliertem Rizinusöl; BASF AG) be- steht. Man erhält ein stabiles Emulsionskonzentrat.Mixture dissolved, which consists of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol ® EM 31 (= nonionic emulsifier based on ethoxylated castor oil; BASF AG). 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 Bekämpf ngs- 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, season, target plants and growth stage.
Zur Verbreiterung des Wirkungsspektrums und zur Erzielung synergistischer Effekte können die substituierten 3-Phenylpyrazole I mit zahlreichen Vertretern anderer herbizider oder wachstumsregulierender Wirkstoffgruppen gemischt und gemeinsam ausgebracht werden. Beispielsweise kommen als Mischungspartner 1,2,4-Thia- diazole, 1, 3, 4-Thiadiazole, Amide, Aminophosphorsäure und deren Derivate, Aminotriazole, Anilide, Aryloxy-/Heteroaryloxyalkan- säuren und deren Derivate, Benzoesäure und deren Derivate, Benzo- thiadiazinone, 2- (Hetaroyl/Aroyl) -1, 3-cyclohexandione, Hetero- aryl-Aryl-Ketone, Benzylisoxazolidinone, meta-CF3-Phenylderivate, Carbamate, Chinolincarbonsäure und deren Derivate, Chloracet- anilide, Cyclohexan-1, 3-dionderivate, Diazine, Dichlorpropion- säure und deren Derivate, Dihydrobenzofurane, Dihydrofuran-3-one, Dinitroaniline, Dinitrophenole, Diphenylether, Dipyridyle, Halogencarbonsäuren und deren Derivate, Harnstoffe, 3-Phenyl- uracile, Imidazole, Imidazolinone, N-Phenyl-3, 4, 5, 6-tetrahydro- phthalimide, Oxadiazole, Oxirane, Phenole, Aryloxy- und Hetero- aryloxyphenoxypropionsäureester, Phenylessigsäure und deren Derivate, 2-Phenylpropionsäure und deren Derivate, Pyrazole, Phenylpyrazole, Pyridazine, Pyridincarbonsäure und deren Derivate, Pyrimidylether, Sulfonamide, Sulfonylharnstoffe, Triazine, Triazinone, Triazolinone, Triazolcarboxa ide und Uracile in Betracht.To broaden the spectrum of activity and to achieve synergistic effects, the substituted 3-phenylpyrazoles 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, benzo- thiadiazinone, 2- (hetaroyl / aroyl) -1, 3-cyclohexanediones, hetero-aryl-aryl-ketones, benzylisoxazolidinones, meta-CF 3 -phenyl derivatives, carbamates, quinoline carboxylic acid and its derivatives, chloroacetanilides, cyclohexane-1, 3- dione derivatives, diazines, dichloropropionic acid and their derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazylones 3, N 4, 5, 6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy and hetero-aryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarbons acids and their derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxides 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, bei- spielsweise mit Mitteln zur Bekämpfung von Schädlingen oder phytopathogenen Pilzen bzw. Bakterien. Von Interesse ist ferner die Mischbarkeit mit Mineralsalzlösungen, welche zur Behebung vonIt can 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 eliminate
Ernährungs- und Spurenelementmängeln eingesetzt werden. Es können auch nichtphytotoxische Öle und Ölkonzentrate zugesetzt werden.Nutritional and trace element deficiencies are used. Non-phytotoxic oils and oil concentrates can also be added.
HerstellungsbeispieleManufacturing examples
Beispiel 1 2 -Chlor- 5- (4 -chlor-5 -difluormethoxy-1-methyl -1H-pyrazol-3 -yl) -4- luorbenzoesäure (ethoxy)amid (Nr. Ia.45)Example 1 2 -Chlor- 5- (4-chloro-5-difluoromethoxy-1-methyl -1H-pyrazol-3 -yl) -4- luorboic acid (ethoxy) amide (No. Ia.45)
Zu einer Lösung von 10 g (27 mmol) 2-Chlor-5- (4-chlor-5-difluor- methoxy-1 -methyl -IH-pyrazol- 3 -yl) -4-fluorbenzoesäurechlorid in 150 ml Toluol wurden 37 g (0,27 mol) Kaliumcarbonat gegeben und anschließend 16 g (54 mmol) einer 25 %igen wäßrigen Ethoxyamin- Hydrochlorid-Lösung getropft. Nach 5 Std. Rühren bei 45°C verdünnte man die Reaktionsmischung mit 0,5 1 Wasser. Dann wurde die organische Phase abgetrennt, mit gesättigter wäßriger Kochsalz - lösung gewaschen, über Magnesiumsulfat getrocknet und schließlich eingeengt. Ausbeute: 10,4 g.37 g were added to a solution of 10 g (27 mmol) of 2-chloro-5- (4-chloro-5-difluoro-methoxy-1-methyl -IH-pyrazol-3-yl) -4-fluorobenzoic acid chloride in 150 ml of toluene (0.27 mol) of potassium carbonate and then 16 g (54 mmol) of a 25% aqueous ethoxyamine hydrochloride solution were added dropwise. After stirring for 5 hours at 45 ° C., the reaction mixture was diluted with 0.5 l of water. The organic phase was then separated off, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and finally concentrated. Yield: 10.4 g.
Beispiel 2Example 2
2 -Chlor- 5 - (4 -chlor - 5 -difluormethoxy- 1 -methyl - 1H-pyrazol -3 -yl) -4 - fluorbenzoesäuremethyl (methoxy) amid (Nr. Ia.25)2-Chloro-5 - (4-chloro-5-difluoromethoxy-1-methyl - 1H-pyrazole -3 -yl) -4 - fluorobenzoic acid methyl (methoxy) amide (No. Ia.25)
Zu einer Lösung von 1 g (2,6 mmol) 2 -Chlor-5- (4-chlor-5-difluormethoxy- 1-methyl -IH-pyrazol -3 -yl) -4-fluorbenzoesäure (methoxy) amid in 50 ml Aceton wurden 0,43 g (3,1 mmol) Kaliumcarbonat und 0,39 g (3,1 mmol) Dimethylsulfat gegeben. Nach 3 Tagen engte man ein. Der Rückstand wurde mit Wasser versetzt, wonach man zweimal mit Ethylacetat extrahierte. Die vereinigten organischen Phasen wurden mit Wasser und gesättigter wäßriger Kochsalzlösung gewaschen, über Magnesiumsulfat getrocknet und schließlich ein- geengt. Die Reinigung des Rohproduktes erfolgte mittels Säulenchromatographie an Kieselgel (Eluens: Hexan/Ethylacetat = 2:1). Ausbeute: 0,5 g.To a solution of 1 g (2.6 mmol) of 2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl -IH-pyrazole -3 -yl) -4-fluorobenzoic acid (methoxy) amide in 50 ml Acetone was added to 0.43 g (3.1 mmol) of potassium carbonate and 0.39 g (3.1 mmol) of dimethyl sulfate. After 3 days, they were narrowed. Water was added to the residue, followed by extraction twice with ethyl acetate. The combined organic phases were washed with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate and finally concentrated. The crude product was purified by means of column chromatography on silica gel (eluent: hexane / ethyl acetate = 2: 1). Yield: 0.5 g.
Beispiel 3 N-Acetyl- (2-chlor-5- (4 -chlor-5-difluormethoxy- 1-methyl-IH-pyrazol -3 -yl) -4 -fluorbenzoesäure)methoxyamid (Nr. Ia.425)Example 3 N-acetyl- (2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-IH-pyrazole -3 -yl) -4-fluorobenzoic acid) methoxyamide (No. Ia.425)
Zu einer Lösung von l g (2,6 mmol) 2-Chlor-5- (4-chlor-5-difluormethoxy-1-methyl -IH-pyrazol -3 -yl) -4-fluorbenzoesäure (methoxy) amid in 46 ml Dichlormethan wurden nacheinander 0,26 g (2,6 mmol) Triethylamin und 0,23 g (2,9 mmol) Acetylchlorid getropft. Nach 16 Std. Rühren versetzte man die Reaktionsmischung mit Wasser. Anschließend wurde die organische Phase abgetrennt, über Magnesiumsulfat getrocknet und schließlich eingeengt. Die Reinigung des Rohprodukts erfolgte mittels Kieselgelchromatographie (Eluens: Hexan/Ethylacetat = 1:2). Ausbeute: 0,5 g.To a solution of 1 g (2.6 mmol) of 2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl -IH-pyrazole -3 -yl) -4-fluorobenzoic acid (methoxy) amide in 46 ml of dichloromethane 0.26 g (2.6 mmol) of triethylamine and 0.23 g (2.9 mmol) of acetyl chloride were added dropwise in succession. After stirring for 16 hours, the reaction mixture was mixed with water. The organic phase was then separated off, dried over magnesium sulfate and finally concentrated. The crude product was purified by means of silica gel chromatography (eluent: hexane / ethyl acetate = 1: 2). Yield: 0.5 g.
In der folgenden Tabelle 2 sind neben den vorstehend beschriebenen Wirkstoffen noch weitere substituierte 3-Phenylpyrazole I aufgeführt, die auf analoge Weise hergestellt wurden oder herstellbar sind:In addition to the active ingredients described above, Table 2 below lists further substituted 3-phenylpyrazoles I which were prepared or can be prepared in an analogous manner:
Tabelle 2Table 2
Figure imgf000070_0001
Figure imgf000070_0001
Figure imgf000070_0002
Figure imgf000071_0001
Figure imgf000072_0001
Figure imgf000073_0001
iH-NMR-Daten für die ebenfalls hergestellte Verbindung Nr. Ib.26 (R3 = F; R* = Cl; R6,R7 = CH3): 3,36 (s,3H), 3,50 (s,3H), 3,79 (s,3H), 6,68 (t,lH), 7,52 (s,lH), 7,56 (s,lH).
Figure imgf000070_0002
Figure imgf000071_0001
Figure imgf000072_0001
Figure imgf000073_0001
iH-NMR data for the likewise prepared compound No. Ib.26 (R 3 = F; R * = Cl; R6, R 7 = CH 3 ): 3.36 (s, 3H), 3.50 (s, 3H), 3.79 (s, 3H), 6.68 (t, lH), 7.52 (s, lH), 7.56 (s, lH).
AnwendungsbeispieleExamples of use
Die herbizide Wirkung der substituierten 3 -Phenylpyrazole I ließ sich durch die folgenden Gewächshausversuche zeigen:The herbicidal activity of the substituted 3-phenylpyrazoles 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 durch- sichtigen 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 covers 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 Versuchsgef ße verpflanzt. Die Aufwandmenge für die Nachauflaufbehandlung betrug 7,8 g/ha a.S. (aktive Substanz) .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. 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 post-emergence treatment was 7.8 g / ha a.S. (active substance).
Die Pflanzen wurden artenspezifisch bei Temperaturen von 10 bis 25°C bzw. 20 bis 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 in a species-specific manner at temperatures of 10 to 25 ° C and 20 to 35 ° C. The trial period lasted 2 to 4 weeks. During this time, the plants maintained, 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 in den Gewächshausversuchen verwendeten Pflanzen setzten sich aus folgenden Arten zusammen:The plants used in the greenhouse experiments are composed of the following types:
Figure imgf000074_0001
Figure imgf000074_0001
Bei einer Aufwandmenge von 7,8 g/ha a.S. zeigte die Verbindung Nr. Ia.677 im Nachauflaufverfahren eine sehr gute herbizide Wirkung gegen die o.g. breitblättrigen Pflanzen. At an application rate of 7.8 g / ha a.S. Compound No. Ia.677 showed a very good herbicidal activity against the above in the post-emergence process. broad-leaved plants.

Claims

Patentansprüche claims
1. Substituierte 3-Phenylpyrazole der Formel I1. Substituted 3-phenylpyrazoles of the formula I.
Figure imgf000075_0001
in der die Variablen folgende Bedeutungen haben:
Figure imgf000075_0001
in which the variables have the following meanings:
R1, R2 unabhängig voneinanderR 1 , R 2 independently of one another
C1-C4-Alkyl oder Cι-C4-Halogenalkyl;C 1 -C 4 alkyl or Cι-C 4 haloalkyl;
R3 Cyano, Halogen, Cι~C4-Alkyl oder Cι-C4-Halogenalkyl;R 3 is cyano, halogen, Cι ~ C 4 alkyl or Cι-C 4 haloalkyl;
R4 Halogen;R 4 halogen;
R5 Cyano, Halogen, Cι-C4-Alkyl, Cι-C4~Halogenalkyl, Cι-C -Alkoxy oder Cι-C4-Halogenalkoxy;R 5 cyano, halogen, -CC 4 alkyl, -C 4 ~ haloalkyl, -C-alkoxy or -C-C 4 haloalkoxy;
R6, R7 unabhängig voneinanderR 6 , R 7 independently of one another
Wasserstoff, Ci-Cβ-Alkyl, Cι-C6-Halogenalkyl, Hydroxy- Cι-C4-alkyl, Cyano-Cι-C4-alkyl, Cι-C4-Alkoxy-Cι-C4-alkyl, Cι-C4-Halogenalkoxy-Cι-C4-alkyl , C3-C4-Alkenyloxy-Cι-C4~ alkyl, C3-C4-Alkinyloxy-Cι-C -alkyl, C3-C8-Cycloalkyl- oxy-Cι~C4-alkyl, Amino-Cι-C4-alkyl, Cι~C4-Alkyl- amino-Cι-C -alkyl , Di- (Cχ-C4-alkyl ) amino-C].-C4-alkyl , Cι-C4-Alkylthio-Cι-C4-alkyl, Ci-Cα-Halogenalkyl- thio-Ci-C4-alkyl , C3-C4-Alkenylthio-Cι-C4-alkyl , C3-C4-Alkinylthio-Cι-C4-alkyl, C3-C6~Alkenyl, Cyano-C3-C6-alkenyl, C3-C6-Halogenalkenyl, C3-C6-Alkinyl, Cyano-C3-C6-alkinyl , C3-C6-Halogenalkinyl , (Cι-C4-Alkyl) carbonyl, (Cι-C4-Halogenalkyl) carbonyl, Di (C1-C4- alkyl) aminocarbonyl, (Cι-C4-Alko y-Cι-C4 -alkyl) - carbonyl, Cι-C4-Alkylsulfonyl, Cι-C4-Halogenalkylsulfonyl, (Cι-C4-Alkyl) carbonyl-Cι-C4-alkyl,Hydrogen, Ci-Cβ-alkyl, -C-C 6 -haloalkyl, hydroxy-Cι-C 4 -alkyl, cyano-Cι-C 4 -alkyl, Cι-C 4 -alkoxy-Cι-C 4 -alkyl, Cι-C 4 -haloalkoxy -CC 4 -alkyl, C 3 -C 4 -alkenyloxy -CC-C 4 ~ alkyl, C 3 -C 4 -alkynyloxy -CC -alkyl, C 3 -C 8 -cycloalkyl-oxy- C 1 -C 4 -alkyl, amino-C 4 -C 4 -alkyl, C 1 -C 4 -alkyl-amino-C 1 -C 4 -alkyl, di- (Cχ-C 4 -alkyl) amino-C] .- C 4 - alkyl, -CC 4 alkylthio -CC 4 -alkyl, Ci-Cα-haloalkyl-thio-Ci-C 4 -alkyl, C 3 -C 4 -alkenylthio -CC 4 -alkyl, C 3 -C 4 -alkynylthio -CC 4 -alkyl, C 3 -C 6 ~ alkenyl, cyano-C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, cyano-C 3 - C 6 -alkynyl, C 3 -C 6 -haloalkynyl, (-C-C 4 -alkyl) carbonyl, (Cι-C 4 -haloalkyl) carbonyl, di (C 1 -C 4 -alkyl) aminocarbonyl, (Cι-C 4 -Alko y -C-C 4 alkyl) - carbonyl, -CC 4 -alkylsulfonyl, -C-C 4 -haloalkylsulfonyl, (-C-C 4 alkyl) carbonyl -CC-C 4 -alkyl,
(Cι-C4-Halogenalkyl)carbonyl-Cι-C4-alkyl, (C3-C8-Cyclo- alkyl)carbonyl-Cι-C4-alkyl, Hydroxycarbonyl-Cι-C4-alkyl, (Cι-C4-Alkoxy)carbonyl-Cι-C -alkyl, das eine (Cι-C4-Alkoxy) imino -Gruppe tragen kann, (Cι-C4-Halogenalkoxy)carbonyl-Cι-C4-alkyl, (C1-C4-Alkyl - thio) carbonyl-Cι-C4-alkyl, Aminocarbonyl-Cι-C4~alkyl, (Cι-C4-Alkylamino)carbonyl-Cι-C4-alkyl, Di (Cι-C4-alkyl) aminocarbonyl-Cι-C4-alkyl, Phenyl, Phenyl-Cι-C4-alkyl, C3-C8-Cycloalkyl oder C3-C8-Cyclo- alkyl-Cι-C4-alkyl, wobei alle Cycloalkylringe gewünschtenfalls ein Carbonyl- oder Thiocarbonyl- Ringglied enthalten können, und wobei jeder Phenyl- oder Cycloalkylring unsubsti- tuiert sein oder ein bis vier Substituenten tragen kann, jeweils ausgewählt aus der Gruppe bestehend aus Cyano, Nitro, Amino, Hydroxy, Carboxy, Halogen, C1-C4-Alkyl, Cι~C4-Halogenalkyl, Cχ-C4-Alkoxy, Cι-C4-Halogenalkoxy, Cι-C-Alkylthio, Cι-C4-Halogenalkylthio, Cι-C4-Alkyl- sulfonyl, Cι-C4-Halogenalkylsulfonyl, (Cι~C4-Alkoxy) carbonyl, (Cι-C4-Alkyl) carbonyl, (Cι-C4-Halogenalkyl) carbonyl, (Cι-C4-Alkyl) carbonyloxy, (Cι-C4-Halogenalkyl) carbonyloxy und Di (C-C4-alkyl) amino;(-CC 4 haloalkyl) carbonyl -CC 4 -alkyl, (C 3 -C 8 -cycloalkyl) carbonyl -CC 4 -alkyl, hydroxycarbonyl -CC 4 -alkyl, (-C-C 4 -alkoxy) carbonyl -CC-alkyl, which can carry a (-CC 4 -alkoxy) imino group, (-CC 4 -haloalkoxy) carbonyl -CC 4 -alkyl, (C 1 -C 4- alkyl-thio) carbonyl -CC 4 -alkyl, aminocarbonyl -CC 4- alkyl, (-CC 4 -alkylamino) carbonyl -CC 4 -alkyl, Di (C 1 -C 4 alkyl) aminocarbonyl C 1 -C 4 alkyl, phenyl, phenyl C 1 -C 4 alkyl, C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkyl C 1 -C 4 -alkyl, where all cycloalkyl rings can optionally contain a carbonyl or thiocarbonyl ring member, and wherein each phenyl or cycloalkyl ring can be unsubstituted or can carry one to four substituents, each selected from the group consisting of cyano, nitro, amino, hydroxy , carboxy, halogen, C 1 -C 4 -alkyl, C ~ 4 haloalkyl, Cχ-C 4 -alkoxy, C 4 haloalkoxy, Cι-C-alkylthio, Cι-C4-haloalkylthio, Cι-C 4 -alkyl-sulfonyl, -C-C 4 -haloalkylsulfonyl, (-C-C 4 -alkoxy) carbonyl, (-C-C 4 -alkyl) carbonyl, (-C-C 4 -haloalkyl) carbonyl, (-C-C 4 -alkyl) ) carbonyloxy, (-C-C 4 haloalkyl) carbonyloxy and di (CC 4 alkyl) amino;
sowie die landwirtschaftlich brauchbaren Salze der Verbindungen I, ausgenommen 2-Chlor-5- (4-chlor-5-difluormethoxy-1-methyl -1H- pyrazol- 3 -yl) -4-fluorbenzoesäure (methoxy) amid und 2,4-Di- chlor-5- (5-difluormethoxy-4-fluor-l-methyl-lH-pyrazol-3-yl) - benzoesäure (methoxy) amid.and the agriculturally useful salts of the compounds I, with the exception of 2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl -1H-pyrazole-3-yl) -4-fluorobenzoic acid (methoxy) amide and 2,4- Dichloro-5- (5-difluoromethoxy-4-fluoro-1-methyl-1H-pyrazol-3-yl) benzoic acid (methoxy) amide.
2. Verwendung der substituierten 3-Phenylpyrazole I' und ihrer landwirtschaftlich brauchbaren Salze - wobei I' der2. Use of the substituted 3-phenylpyrazoles I 'and their agriculturally useful salts - where I' is the
Definition von I gemäß Anspruch 1, jedoch ohne die Ausnahmebestimmung, entspricht - als Herbizide.Definition of I according to claim 1, but without the exception, corresponds to - as herbicides.
3. Herbizides Mittel, enthaltend eine herbizid wirksame Menge mindestens eines substituierten 3-Phenylpyrazols der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I, gemäß Anspruch 1, und mindestens einen flüssigen und/oder festen Trägerstoff sowie gewünschtenfalls mindestens einen oberflächenaktiven Stoff.3. Herbicidal composition containing a herbicidally effective amount of at least one substituted 3-phenylpyrazole of the formula I or an agriculturally useful salt of I, according to claim 1, and at least one liquid and / or solid carrier and, if desired, at least one surfactant.
4. Verfahren zur Herstellung von herbizid wirksamen Mitteln, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge mindestens eines substituierten 3-Phenylpyrazols der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I, gemäß Anspruch 1, mit mindestens einem flüssigen und/oder festen Trägerstoff sowie gewünschtenfalls mindestens einem oberflächenaktiven Stoff mischt.4. A process for the preparation of herbicidally active agents, characterized in that a herbicidally effective amount of at least one substituted 3-phenylpyrazole of the formula I or an agriculturally useful salt of I, according to claim 1, with at least one liquid and / or solid carrier and if desired mixes at least one surfactant.
5. Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge mindestens eines substituierten 3-Phenylpyrazols der Formel I' oder eines landwirtschaftlich brauchbaren Salzes von I' - wobei I' der Definition von I gemäß Anspruch 1, jedoch ohne die Ausnahmebestimmung, entspricht - auf Pflanzen, deren Lebensraum oder auf Saatgut einwirken läßt. 5. A method for controlling unwanted vegetation, characterized in that a herbicidally effective amount of at least one substituted 3-phenylpyrazole of the formula I 'or an agriculturally useful salt of I '- where I' corresponds to the definition of I according to claim 1, but without the exception, on plants, their habitat or on seeds.
PCT/EP1998/000781 1997-02-27 1998-02-12 Substituted 3-phenyl pyrazoles WO1998038169A1 (en)

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AU67194/98A AU6719498A (en) 1997-02-27 1998-02-12 Substituted 3-phenyl pyrazoles

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DE19707808.7 1997-02-27

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0443059A1 (en) * 1990-02-21 1991-08-28 Nihon Nohyaku Co., Ltd. 3-(Substituted phenyl)pyrazole derivatives, salts thereof, herbicides therefrom, and process for producing said derivatives or salts
EP0619946A1 (en) * 1993-04-04 1994-10-19 Nihon Nohyaku Co., Ltd. Herbicidal composition for upland farming and weeding method
WO1995032188A1 (en) * 1994-05-20 1995-11-30 Basf Aktiengesellschaft Substituted 3-phenylpyrazoles for use as herbicides
DE4419517A1 (en) * 1994-06-03 1995-12-07 Basf Ag Substituted 3-phenylpyrazoles
DE4424791A1 (en) * 1994-07-14 1996-01-18 Basf Ag Substituted cinnamon and cinnamic hydroxamide derivatives
WO1996040643A1 (en) * 1995-06-07 1996-12-19 Monsanto Company Herbicidal substituted 3-aryl-pyrazoles
DE19524623A1 (en) * 1995-07-06 1997-01-09 Basf Ag 5-pyrazolylbenzoic acid derivatives

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0443059A1 (en) * 1990-02-21 1991-08-28 Nihon Nohyaku Co., Ltd. 3-(Substituted phenyl)pyrazole derivatives, salts thereof, herbicides therefrom, and process for producing said derivatives or salts
EP0619946A1 (en) * 1993-04-04 1994-10-19 Nihon Nohyaku Co., Ltd. Herbicidal composition for upland farming and weeding method
WO1995032188A1 (en) * 1994-05-20 1995-11-30 Basf Aktiengesellschaft Substituted 3-phenylpyrazoles for use as herbicides
DE4419517A1 (en) * 1994-06-03 1995-12-07 Basf Ag Substituted 3-phenylpyrazoles
DE4424791A1 (en) * 1994-07-14 1996-01-18 Basf Ag Substituted cinnamon and cinnamic hydroxamide derivatives
WO1996040643A1 (en) * 1995-06-07 1996-12-19 Monsanto Company Herbicidal substituted 3-aryl-pyrazoles
DE19524623A1 (en) * 1995-07-06 1997-01-09 Basf Ag 5-pyrazolylbenzoic acid derivatives

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AR011899A1 (en) 2000-09-13
AU6719498A (en) 1998-09-18

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