EP1546144A2 - Delta1 pyrrolines used as pesticides - Google Patents

Delta1 pyrrolines used as pesticides

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Publication number
EP1546144A2
EP1546144A2 EP03788892A EP03788892A EP1546144A2 EP 1546144 A2 EP1546144 A2 EP 1546144A2 EP 03788892 A EP03788892 A EP 03788892A EP 03788892 A EP03788892 A EP 03788892A EP 1546144 A2 EP1546144 A2 EP 1546144A2
Authority
EP
European Patent Office
Prior art keywords
chlorine
alkyl
fluorine
alkoxy
haloalkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP03788892A
Other languages
German (de)
French (fr)
Inventor
Johannes Rudolf Jansen
Udo Kraatz
Hubertus Stakemeier
Thomas Seitz
Fritz Maurer
Martin FÜSLEIN
Bernd Alig
Christian Funke
Werner Hallenbach
Jörg KONZE
Udo Reckmann
Ulrich Görgens
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
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Bayer CropScience AG
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Filing date
Publication date
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Publication of EP1546144A2 publication Critical patent/EP1546144A2/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings

Definitions

  • the present invention relates to new ⁇ '-pyrrolines, several processes for their preparation and their use as active substances, in particular their use as pesticides.
  • R 1 represents halogen, QC 4 alkyl or CC 4 haloalkyl
  • R 2 represents hydrogen, halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
  • R 3 represents hydrogen, halogen or methyl
  • R 4 represents hydrogen, Ci-Cg-alkyl, (C ⁇ -C 6 alkoxy) carbonyl, (C 3 -C 6 cycloalkyl) - oxycarbonyl, (C ⁇ -C 6 haloalkoxy) carbonyl, optionally mono- or polysubstituted by identical or different from halogen, cyano, nitro, C.-C 4 -alkyl, d-
  • a 1 represents N or CH
  • a 2 represents N or CR 9 ,
  • R 5 for hydrogen, halogen, CC 6 -alkyl, C r C 6 -alkoxy, -C-C 6 -alkylthio, CC 6 - alkylsulfonyl, C ⁇ -C 6 -alkylsulfonyl, C ⁇ -C 6 -haloalkoxy, Cj-C 6 - Haloalkylthio, Ci-C ⁇ -haloalkylsulfinyl or Cj-C 6 -haloalkylsulfonyl, R 6 , R 7 , R 8 and R 9 independently of one another are hydrogen, halogen, cyano, formyl, nitro, tri (CC 6 alkyl) silyl, C r C 6 alkyl, C 6 -C 6 alkoxy, CC 6 -Alkylthio, CC 6 -Alkylsul- finyl, -C-C 6 -Alsulfonyl ,.
  • R 10 represents hydrogen, -Ce-alkyl, C 2 -C 6 alkenyl, C, -C 6 haloalkyl, C 2 -C 6 haloalkenyl or C 3 -C 6 cycloalkyl,
  • R 11 for hydrogen, CC 6 alkyl, C 2 -C 6 alkenyl, CC 6 haloalkyl, C 2 -C 6 halo alkenyl, C 3 -C 6 cycloalkyl -CC 4 -alkyl or optionally simple or is aryl-Ci-Gralkyl substituted several times, identically or differently by R 5 ,
  • R 12 and R 13 independently of one another are hydrogen, C 6 -alkyl, C 6 haloalkyl, optionally substituted singly or multiply, identically or differently, by halogen or C ⁇ -C 6 alkyl
  • C 3 -C 6 cycloalkyl are C 3 -C 6 cycloalkyl-C 4 -C 4 alkyl or aryl-C 1 -C 4 -alkyl which is optionally mono- or polysubstituted identically or differently by R s ,
  • R 12 and R 13 also together for each optionally mono- or polysubstituted, identically or differently, by halogen or -CC 6 -alkyl-substituted C 2 -C 6 -alkylene, (-
  • p 0, 1 or 2
  • W 1 substituted fully unsaturated 5-membered heterocycle having 1 to 3 identical or different heteroatoms from the series consisting of nitrogen, oxygen and / or sulfur, and W 1 for halogen, cyano, d -CC 6 alkyl, d- e-alkoxy, C 6 -C alkylthio, d -C 6 alkyl sulfinyl, C 6 -C alkylsulfonyl, Ci-Cie-haloalkyl, C ⁇ -C ⁇ 6 -Halogenalkoxy, C -C 6 - haloalkylthio, C 6 -C -haloalkylsulfmyl, C ⁇ -C 6 -haloalkylsul, fonyl, C 3 - C ⁇ -cycloalkyl or for each optionally one or more, the same or different by
  • -C (R 10 ) N-OR U , -S0 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 1 R 13 substituted aryl or aryl -CC-C -alkyl.
  • Hydrogen stands for • another stereogenic center, whereby the substituents at the two centers can be ice or trans to each other. The same designation applies to all other formulas in this description.
  • the compounds of formula (I) may optionally depend on the type and
  • R 1 , R 2 , R 3 , R 4 , A 1 and R 5 have the meanings given above,
  • a 2 , R 6 , R 7 , R s and Q have the meanings given above and X 1 represents bromine, iodine or -OSO 2 CF 3 ,
  • the compounds of the formula (T) according to the invention have very good insecticidal properties and can be used both in crop protection and in material protection to control unwanted pests, such as insects, arachnids and mites.
  • the compounds of the invention are generally defined by the formula (I). Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below.
  • R 1 preferably represents fluorine, chlorine, bromine, -CC alkyl or CC 4 haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 1 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, iso-
  • R 1 very particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl or trifluoromethyl.
  • R 1 particularly preferably represents fluorine, chlorine or methyl.
  • R 2 preferably represents hydrogen, fluorine, chlorine, bromine, CC-alkyl or -CC 4 -halogenoalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 2 particularly preferably represents hydrogen, fluorine, chlorine, bromine, .methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl. sec-butyl, tert-butyl or trifluoromethyl.
  • R 2 very particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, isopropyl or tert-butyl.
  • R 2 particularly preferably represents hydrogen, fluorine, chlorine or
  • R 3 preferably represents hydrogen, fluorine, chlorine, bromine or methyl.
  • R 3 particularly preferably represents hydrogen, fluorine, chlorine or methyl.
  • R 3 very particularly preferably represents hydrogen. Fluorine or chlorine.
  • R 3 particularly preferably represents hydrogen or fluorine.
  • R 4 preferably represents hydrogen, -CC alkyl, (-C 6 alkoxy) carbonyl, (C 3 -C 6 cycloalkyl) oxycarbonyl, (-C 4 haloalkoxy) carbonyl with 1 to 9 fluorine and / or chlorine atoms, for optionally up to four times, the same or different by fluorine, chlorine, bromine, iodine, cyano, nitro, CC 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, CC 4 haloalkyl, CC -haloalkoxy and / or dC 4 -haloalkyl-thio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, substituted phenyl.
  • R 4 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, methoxycarbonyl, ethoxycarbonyl, n-prop-oxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, iso-butoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n-pentoxycarbonyl, neopentoxycarbonyl, sec- Isoamyloxycarbonyl, pentan-3-yloxycarbonyl, n-Hexyloxycarbo ⁇ yl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, trifluoromethoxycarbonyl, tri- fluoroethoxycarbonyl, optionally mono- or disubstituted by identical or different fluorine, chlorine
  • R 4 very particularly preferably represents methyl, ethyl, iso-propyl, tert-butyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, iso-butoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n Pentoxycarbonyl, neopentoxycarbonyl, sec-isoamyloxycarbonyl, pentan-3-yloxycarbonyl, n-hexyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, for optionally simply by fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-
  • R 4 particularly preferably represents hydrogen, methyl, ethyl, methoxycarbonyl, ethoxycarbonyl, 4-fluorophenyl or 4-chlorophenyl.
  • a 1 preferably represents N.
  • a 1 preferably represents CH.
  • a 2 preferably represents N.
  • a 2 preferably represents CR 9 .
  • a 2 particularly preferably represents CH.
  • R 5 preferably represents hydrogen, fluorine, chlorine, bromine, -C 4 alkyl, CC alkoxy, C 1 -C alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl; C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, C 4 -C 4 haloalkylsulfonyl or C 1 -C 4 haloalkyl sulfonyl, each having 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 5 particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso- Propoxy, n-butoxy, iso-butoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, iso-butylthio, sek-butylthio, tert-butylthio, methylsulfonyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl, n-butylsulfinyl, iso-butylsulfmyl, sec-buty
  • R s very particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy ,.
  • R 5 particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, methoxy or ethoxy.
  • R 6 , R 7 , R 8 and R 9 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, cyano, formyl, nitro, tri (dC 4 -alkyl) silyl, C, -C -alkyl, dC 4 -alkoxy , -
  • R 6 , R 7 , R 8 and R 9 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, cyano, formyl, trimethylsilyl, dimethyl-tert-butylsilyl, methyl, ethyl, n-propyl, isopropyl, n-butyl , iso-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso -Propylthio, n-butylthio, iso-butylthio, sec-
  • R 6 , R 7 , R 8 and R 9 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, Ethylthio, iso-propylthio, tert-butylthio, methylsulfonyl, ethylsulfinyl, iso-propylsulfinyl, tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl,.
  • R 6 , R 7 , R 8 and R 9 independently of one another are particularly preferably hydrogen, fluorine, chlorine, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, -SO 2 NMe 2 .
  • R 6 , R 7 , R 8 and R 9 stand independently of one another for hydrogen.
  • R 10 preferably represents hydrogen, dC 4 alkyl, C 2 -C alkenyl, CC 4 haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl with 1 to 7 fluorine , Chlorine and / or bromine atoms, cyclopropyl, cyclopentyl or cyclohexyl.
  • R 10 particularly preferably represents hydrogen, methyl, ethyl or cyclopropyl.
  • R 10 very particularly preferably represents hydrogen, methyl or ethyl.
  • R J1 preferably represents hydrogen, -CC 4 alkyl, C 2 -C 4 alkenyl, CC 4 haloalkyl with 1 to 9 fluorine, chlorine and or bromine atoms, C 2 -C haloalkenyl with 1 to 7 fluorine -, Chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl-dC 2 -alkyl or in each case optionally up to four times, identical or differently substituted by R 5, benzyl or phenylethyl.
  • R n particularly preferably represents hydrogen, methyl, ethyl, cyclopropylmethyl or in each case optionally one to three times, identically or differently substituted by R 5, benzyl.
  • R 11 very particularly preferably represents hydrogen, methyl or ethyl.
  • R 12 and R 13 independently of one another preferably represent hydrogen, -CC alkyl, CC 4 - haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl, • d-Ce cycloalkyl -dd-alkyl or in each case optionally up to four times, identically or differently substituted by R 5, benzyl or phenylethyl.
  • R 12 and R 13 also together preferably represent dd-alkylene, - (CH 2 ) 2 -O- (CH 2 ) 2 - or - (CH 2 ) 2 -S- (CH 2 ) 2 -.
  • R 12 and R 13 independently of one another particularly preferably represent hydrogen, methyl,
  • R 12 and R 13 together also particularly preferably represent propylene, butylene,
  • Pentylene - (CH 2 ) 2 -O- (CH 2 ) 2 - or - (CH 2 ) 2 -S- (CH 2 ) 2 -.
  • p is preferably 0 or 1. p is particularly preferably 0.
  • W 1 preferably represents fluorine, chlorine, bromine, cyano, C 1 -C 2 alkyl, C 2 -C alkoxy, Ci
  • R 14 and R 15 are independently hydrogen, chlorine, Cyanö, C ⁇ -C 12 alkyl, C 1 -C 12 -. Alkoxy, dC 12 alkylthio, C ⁇ -C ⁇ 2 alkylsulfinyl, Ci-Ciz-alkylsulfonyl, C ⁇ -C ⁇ 2 -Halo- genalkyl, C 3 -C ⁇ 2 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different fluorine,
  • -C (R 10 ) N-OR ⁇ , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
  • R 16 for hydrogen, cyano, -C-d 2 -alkyl, C ⁇ -C 12 -alkoxy, d-C ⁇ 2 -alkylthio, dC 12 - alkylsulfinyl, C ⁇ -C ⁇ 2 -alkylsulfonyl, C ⁇ -C ⁇ 2 -haloalkyl, C 3 - C ⁇ 2 -cycloalkyl or optionally monosubstituted in each case to four times by identical or different fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C ⁇ -C 4 alkyl, CC 4 -alkoxy, C 1 -C 4 - alkylthio, C ⁇ C 4 alkylsulfinyl, CC 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (-C-C 4 -alkyl) carbonyl
  • R 17 and R 19 independently of one another for hydrogen, cyano, C 1 -C 2 alkyl, d C 2 alkoxy,
  • R 18 for hydrogen, chlorine, cyano, CC 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, C.-
  • R 17 , R 18 , R 19 are not simultaneously hydrogen
  • R 20 and R 23 independently of one another are hydrogen, C 1 -C 2 -alkyl, C 1 -C 2 alkoxy, Cj-C ⁇ - alkylthio, dC , 2 -AlkylsulfinyL C r C ⁇ 2 -Alkylsulfonyl, CC 12 -haloalkyl, C 3 -C 12 - cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C ⁇ -C - alkyl, C ⁇ -C 4 -alkoxy, C 4 - alkylthio, CC 4 alkylsulfinyl, C ⁇ -C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 - alkenyloxy, (C
  • R 21 and R 22 are independently hydrogen, chlorine, cyano, C 12 alkyl, C 1 -C 12 - alkoxy, Cj-d ⁇ alkylthio, C ⁇ -C 12 alkylsulfinyl, alkylsulfonyl dC 12 , C 1 -C 2 -haloalkyl, C 3 -C 2 -cycloalkyl or for each optionally optionally up to four times, identical or different by fluorine,
  • R 25 and R 26 independently of one another for hydrogen, chlorine, cyano, d -CC 2 alkyl, Cj-C 12 -
  • C ⁇ -C -haloalkoxy, C ⁇ -C4-haloalkylthio, C ⁇ -C 4 haloalkylsulfinyl, dC - halogenoalkylsulphonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C haloalkenyl, C 2 -C 4 -Halogenalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) N-OR ⁇ , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - ( CH 2 ) p N (R I2 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have
  • R 24 , R 25 , R 26 , R 27 do not simultaneously stand for hydrogen, R 28 and R 30 independently of one another for hydrogen, -CC 2 alkyl, C 1 -C 2 -alkoxy, Ci-C ⁇ - Haloalkyl, C 3 -C 2 cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C r C 4 alkyl, dC 4 alkoxy, C 1 -C 4 alkylthio, dC 4 alkyl sulfyl, CC 4 -Alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyl oxy, (-C-C-alkyl) carbonyl, (-C-C -alkoxy) carbonyl, CC 4 -haloalkyl, C ⁇ -C - haloalkyl, C ⁇
  • R 29 represents hydrogen, chlorine, cyano, C 12 -alkyl, C 12 -alkoxy, C 12 haloalkyl, C 3 -C ⁇ 2 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different fluorine , chlorine, cyano, formyl, nitro, trimethylsilyl, C r C 4 alkyl, C r C 4 alkoxy, alkylthio CC 4 -Al-, dd alkylsulfinyl, C ⁇ -C 4 alkylsulfonyl, C 2 -C 4 alkenyl , C 2 -C 4 -alkenyloxy, (-C-C 4 -alkyl) carbonyl, (-C-C 4 -alkoxy) carbonyl, CC -haloalkyl, CC - haloalkoxy, CC -haloalkylthio, -C-C 4
  • Haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms
  • -C (R 10 ) N-OR ⁇ , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 ,
  • R 32 and R 34 are independently hydrogen, dd 2 alkyl, -d-rAlkoxy, C ⁇ -C_ 2 - alkylthio, C 2 C ⁇ -Alkylsulfmyl, CC 12 alkylsulfonyl, CC 12 haloalkyl, C 3 -C 12 -
  • '5 cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, CC alkyl, CC 4-alkoxy dd - alkylthio, alkylsulfinyl CC 4, CC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (-C-C 4 -alkyl) carbonyl, (C ⁇ -C -alkoxy) carbonyl, -C-C 4 -haloalkyl, 0 Ci-OrHalogenalkoxy, C ⁇ -C 4 -haloalkylthio, -C-C 4 -haloalkylsulfinyl, CC 4 -
  • R 33 represents hydrogen, chlorine, cyano, dC 12 alkyl, C r C 12 -alkoxy, C ⁇ 2 alkylthio, C C ⁇ -Alkylsulf ⁇ nyl, C ⁇ -C ⁇ C ⁇ -C ⁇ 2 alkylsulfonyl 3 2 haloalkyl, C 3 -C 12 cycloalkyl or 0. for each one optionally up to four times, the same or different by fluorine,
  • -C (R 10 ) N-OR ⁇ , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 is substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
  • R 32 , R 33 , R 34 do not simultaneously represent hydrogen, R 35 and R 36 independently of one another for hydrogen, C 1 -C 2 alkyl, C 1 -C 12 alkoxy, CC 12 alkylthio, C r C 2 alkylsulfinyl, CC 12 alkylsulfonyl, C 1 -C 2 haloalkyl, C 3 - C 12 - cycloalkyl or, in each case optionally up to four times, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C r C 4 alkyl, CC 4 alkoxy, CC 4 alkylthio, C r C 4 alkylsulfinyl, CC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyl oxy, (C 1 -C 4 alkyl) carbonyl, (C 1 -C 4 alkyl
  • R 37 is hydrogen, C ⁇ C 2 alkyl, d-C ⁇ 2 alkoxy, C 2 C ⁇ alkylthio, C ⁇ -d 2 - alkylsulfinyl, C ⁇ -C ⁇ 2 alkylsulfonyl, C ⁇ -C ⁇ 2 -haloalkyl, C 3 -C ⁇ 2 -Cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, CC 4 alkyl, C 1 -C 4 alkoxy, CC 4 -
  • R 39, R 40 and R 41 are each independently hydrogen, C.-Ci ⁇ alkyl, C 1 -C ⁇ 2 -alkoxy, d- C 2 alkylthio, Cj-Ciz-alkylsulfinyl, C C ⁇ 2 alkylsulfonyl, dd 2 -Halogenalkyl, C 3 - C 2 -cycloalkyl or for each optionally single to quadruple, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, dC-alkyl, C 1 -C 4 -alkoxy, CC 4 - alkylthio, -CC 4 alkylsulfinyl, CC -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (-C-C 4 -alkyl) carbonyl, (-C-C -al
  • R 42 and R 43 independently of one another for hydrogen, C 1 -C 2 alkyl, C 1 -C 12 alkoxy, CC 12 -
  • R 44 and R 45 independently of one another are hydrogen, C ⁇ 2 -alkyl, C ⁇ 2 alkoxy, C 1 -C 12 - alkylthio, C C ⁇ 2 alkylsulfinyl, C r C ⁇ 2 alkylsulfonyl, d-C ⁇ 2 - Haloalkyl, C 3 -C 12 -cycloalkyl or for each optionally optionally up to four times, identical or different by fluorine,
  • R 24 , R 44 , R 45 or R 31 , R 44 , R 45 do not simultaneously represent hydrogen
  • R 46 and R 47 independently of one another for hydrogen, C 1 -C 2 alkyl, C 1 -C 4 alkoxy, C 1 -C 12 -
  • R 48 and R 49 independently of one another are hydrogen, C ⁇ 2 -alkyl, C ⁇ 2 -alkoxy, C I2 - alkylthio, C 2 C ⁇ -Alkylsulfjnyl 'Cj-C 12 alkylsulfonyl, Cj-C ⁇ -haloalkyl , C 3 -C 12 cycloalkyl or for each optionally single to fourfold, identical or different by fluorine,
  • R 50 and R 51 independently of one another for hydrogen, Ci-C ⁇ -alkyl, C ⁇ -C ⁇ 2 alkoxy, d-C ⁇ 2 - alkylthio, Cj-C ⁇ 2 alkylsulfinyl, C ⁇ -Ci 2 alkylsulfonyl, d-C ⁇ -haloalkyl, C 3 -C 2 - cycloalkyl or for each optionally single to quadruple, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 -Al- kylthio, C, -C 4 alkylsulfinyl, dd-alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyl oxy, (C 1 -C 4 alkyl) carbonyl, (C 1 -C
  • R 53 for hydrogen, chlorine, cyano, d-C ⁇ -alkyl, C ⁇ -C 12 alkoxy, d-C ⁇ -alkylthio, C C ⁇ 2 -alkylsulfinyl, C ⁇ -C ⁇ 2 -alkylsulfonyl, C ⁇ -C ⁇ 2 -haloalkyl, C 3rd -C ⁇ 2 -cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, -CC alkyl, -C-C 4 alkoxy, -CC 4 - alkylthio, CC 4 -Alkylsulfinyl, dC 4 -Alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (dC 4 -alkyl) carbonyl, (CC -al
  • R 54 for hydrogen, chlorine, cyano, CC 12 -alkyl, dC 12 -alkoxy, d-C ⁇ -alkylthio, C C ⁇ 2 -alkylsulfinyl, C ⁇ -C ⁇ 2 -alkylsulfonyl, C ⁇ -C ⁇ 2 -haloalkyl, C 3 -C ⁇ 2 -Cycloalkyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, -C-C 4 alkyl, CC 4 alkoxy, CC 4 -
  • Alkylthio, -C-C 4 -alkylsulfmyl, CC 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C - alkenyloxy, (-C-C 4 -alkyl) carbonyl, (-C-C -alkoxy) carbonyl, C ⁇ - C 4 -haloalkyl, -C-C -haloalkoxy, C ⁇ -C 4 -haloalkylthio, dC 4 -haloalkylsulfinyl, C ⁇ -C 4 - haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C 4 - Haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) N-OR
  • R 10 to R 13 have the meanings given above, with the proviso that R 54 , R 55 are not simultaneously hydrogen, R 56 and R 57 are independently hydrogen, Ci-C ⁇ -alkyl, C ⁇ -C 12 alkoxy, d-C ⁇ 2 - alkylthio, alkylsulfinyl dd 2, dC ⁇ alkylsulfonyl, C ⁇ -C ⁇ 2 -haloalkyl, C 3 - C.
  • Alkylthio, -CC 4 -alkylsulfinyl, -C-C 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (-C-C 4 -alkyl) carbonyl, (-C-C 4 -alkoxy) carbonyl, C 1 -C 4 -haloalkyl, C 1 -C -haloalkoxy, dC 4 -haloalkylthio, CC -haloalkylsulfinyl, dC 4 - haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - ⁇ C 4 - Haloalkenyl, C -C -haloalkenyloxy, each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 )
  • R 5 and R independently of one another for hydrogen, C 1 -C 2 -alkyl, Ci-C ⁇ -alkoxy, C C 2 -alkylthio, C 1 -C 12 -alkylsulfinyl, CC 12 -alkylsulfonyl, Ci-Cjz-haloalkyl, C 3 -d 2 - Cycloalkyl or for each optionally single to quadruple, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, dC 4 -alkyl, CC 4 -alkoxy, CC - alkylthio, dC 4 -alkylsulfinyl, CC 4 -alkylsulfonyl , C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (CC 4 alkyl) carbonyl ,.
  • R 60 is hydrogen, C ⁇ C 2 alkyl, d-C ⁇ 2 alkoxy, C C ⁇ 2 alkylthio, C C ⁇ 2 - Alkylsulfmyl, CC 12 alkylsulfonyl, C ⁇ -C ⁇ 2 haloalkyl, C 3 -C 12 cycloalkyl, or for in each case optionally up to four times, identically or differently, by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, CC 4 -alkyl, dC 4 -alkoxy, CC 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, dC 4 -alkylsulfonyl , C 2 -C 4 alkenyl, C 2 -C 4 -
  • -C 2 haloalkyl C 3 -C 2 cycloalkyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C 1 -C 4 alkyl, CC 4 alkoxy, CC 4 - Alkylthio, -CC 4 -alkylsulfinyl, CC 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 - alkenyloxy, (-C-C4-alkyl) carbonyl, (-C-C 4 -alkoxy) carbonyl, C 1 -C 4 haloalkyl,
  • Q very particularly preferably represents a completely unsaturated 5-membered
  • Q also very particularly preferably represents a completely unsaturated 5-membered heterocycle from the series
  • Q also very particularly preferably represents a completely unsaturated 5-membered heterocycle from the series
  • Q also very particularly preferably stands for. a fully unsaturated 5-membered heterocycle from the series
  • R 14 and R 15 independently of one another preferably represent hydrogen, chlorine, cyano, C 1 -C 5 -alkyl, -C-C 5 alkoxy, dC 5 -alkylthio, dC 3 -alkylsulfinyl, CC 3 -alkylsulfonyl, C ⁇ -C 5 Haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or for each optionally single to quadruple, identical or different by chlorine,
  • R 14 and R 15 independently of one another particularly preferably represent hydrogen, chlorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neo-
  • Pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methyl t io, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, methyl, ethyl, n-propyl, iso- Propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) N-
  • R 14 and R 15 independently of one another very particularly preferably represent hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or for each optionally single or double, identical or different
  • R 16 preferably represents hydrogen, cyano, dC 5 -alkyl, CC 5 -alkoxy, C 1 -C 5 -alkylthio, Ci-d-alkylsulfinyl, dd-alkylsulfonyl, Ci-d-haloalkyl with 1 to 9
  • Alkylsulfonyl methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, C 1 -C 4 -haloalkyl, CC 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, CC -haloalkylsulfinyl, C ⁇ -C -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine
  • -C (R 10 ) N-OR U , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OS ⁇ 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 the above
  • R 16 particularly preferably represents hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for in each case optionally up to four times, the same or different by fluorine,
  • Chlorine methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-
  • R 16 stands. very particularly preferably for hydrogen, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio, trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
  • R 17 and R 19 independently of one another preferably represent hydrogen, cyano, CC 5 alkyl,
  • R 17 and R 19 independently of one another particularly preferably represent hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy , iso-propoxy, n-butoxy, tert-butoxy, methylthio,
  • R 17 and R 19 independently of one another very particularly preferably represent hydrogen, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, iso- Propylthio, tert-butylthio, trifluoromethyl or for each optionally single or double, identical or different
  • R 18 preferably represents hydrogen, chlorine, cyano, C 5 alkyl, Ci-d-alkoxy, CC 5 - alkylthio, alkylsulfinyl 5 CC, dd alkylsulfonyl, Ci-d-haloalkyl having 1 to 9
  • Fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally single to fourfold, the same or different by chlorine, -C 4 alkyl, dC 4 alkoxy, d- alkylthio, C ⁇ - C 4 -Alkylsulf ⁇ nyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, C ⁇ -C -haloalkyl, C ⁇ -C 4 -halogenalkoxy, C ⁇ -C 4 -haloalkylthio, CC 4 -haloalkylsulfinyl, C ⁇ -C 4 - Haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and or bromine atoms, -C (R 10 ) N-OR ⁇ , - (CH 2 ) p N (R
  • R particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy , n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different by fluorine,
  • R 18 very particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert -Butylthio, trifluoromethyl or phenyl or benzyl, each of which is mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
  • R 20 and R 23 are independently vonemander preferably represents hydrogen, Ci-e-alkyl, C. -d- alkoxy, Ci-Cs-alkylthio, -C-C 5 alkylsulfinyl, dd-alkylsulfonyl, CC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally up to four times, identically or differently by chlorine, -CC 4 -alkyl, CC 4 -alkoxy, CC 4 -alkylthio, CC 4 -alkylsulfinyl, dC 4 -
  • R 20 and R 23 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso -Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-
  • R 20 and R 23 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio,.
  • R 21 and R 22 independently of one another preferably represent hydrogen, chlorine, cyano, Ci-d-alkyl, dd-alkoxy, d-Cj-alkylthio, CC 5 -alkylsulfinyl, dd-alkylsulfonyl,
  • R 21 and R 22 independently of one another are particularly preferably hydrogen, chlorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, eo-pentyl, methoxy, ethoxy, n -Propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally simple to fourfold, identical or different from fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n
  • -C (H) N-OC 2 H 5
  • -C (CH 3 ) N-OC 2 H 5
  • -N (H) SO 2 CH 3 -N (CH 3 ) SO 2 CH 3
  • -N (H) SO 2 CF 3 -N (CH 3 ) SO 2 CF 3
  • R and R 22 independently of one another very particularly preferably represent hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
  • R 24 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or cyclopropyl.
  • R 24 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl or cyclopropyl.
  • R 24 very particularly preferably represents hydrogen.
  • R 25 and R 26 independently of one another preferably represent hydrogen, chlorine, cyano, C 1 -C 5 -alkyl, Ci-d-alkoxy, Ci-d-haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C. 3 -C 6 -cycloalkyl or for each optionally one to four times, identical or different by chlorine,
  • R 25 and R 26 independently of one another particularly preferably represent hydrogen, chlorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neo-
  • Pentyl methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different by fluorine,
  • R 25 and R 26 independently of one another very particularly preferably represent hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl or for each optionally phenyl or benzyl substituted once or twice, identically or differently by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
  • R 27 preferably represents hydrogen, dC 5 -alkyl, Ci-d-alkoxy, dC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or each optionally up to four times , same or different by chlorine,
  • R 27 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n- Butoxy, tert-butoxy, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different by fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n - Propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio,
  • R 27 very particularly preferably represents hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
  • R 28 and R 30 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, C 1 -C 5 -
  • R 28 and R 30 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso -Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different, by fluorine, chlorine, Methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy,
  • -C (H) N-OC 2 H 5
  • -C (CH 3 ) N-OC 2 H s , -N (H) S0 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
  • R 28 and R 30 independently of one another very particularly preferably represent hydrogen
  • R 29 preferably represents hydrogen, chlorine, cyano, CC 5 alkyl, CC 5 alkoxy, CC 5 - haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for j sometimes optionally up to four times, identical or different, by chlorine, dC 4 alkyl, CC alkoxy, C 1 -C 4 alkylthio, dC 4 alkyl sulfinyl, CC 4 alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, C ⁇ -C 4 -Halogenalkyl, CC 4 -haloalkoxy, -C-C 4 -haloalkylthio, Ci-Q-halogeno-alkylsulfinyl, -C-C -haloalkylsulfonyl, each with 1 to
  • R 29 particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso- Propoxy, n-butoxy, tert-butoxy, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different by fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy , Ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio
  • -C (H) N-OC 2 H 5
  • -C (CH 3 ) N-OC 2 H 5
  • -N (H) SO 2 CH 3 -N (CH 3 ) SO 2 CH 3
  • -N (H) SO 2 CF 3 -N (CH 3 ) SO 2 CF 3
  • R 29 very particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, iso-
  • R 31 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or cyclopropyl, or each optionally up to four times, identically or differently, by chlorine , -C-C 4 alkyl, dC 4 alkoxy,.
  • R 31 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl or cyclopropyl, or each in each case optionally up to four times, identically or differently, by fluorine,
  • R 31 very particularly preferably represents hydrogen, methyl or cyclopropyl, or in each case, if appropriate, once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert -Butoxy substituted phenyl or benzyl.
  • R 32 and R 34 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, Ci- - alkoxy, Ci-Cs-alkylthio, C r C 3 -alkylsulfmyl, -C-C 5 -alkylsulfonyl, dC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally single to quadruple, the same or different by chlorine, -C 4 alkyl, CC 4 alkoxy, C 1 -C 4 -Alkylthio, -C-C 4 -alkylsulfinyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, CC -haloalkyl, -C-C 4 -haloalkoxy,
  • R 32 and R 34 independently of one another very particularly preferably represent hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or phenyl substituted by fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy, optionally monosubstituted or disubstituted in each case or benzyl.
  • R 33 preferably represents hydrogen, chlorine, cyano, dC 5 -alkyl, Ci-d-alkoxy, CC 5 - alkylthio, -C-C 5 -alkylsulfinyl, dC 5 -alkylsulfonyl, dC 5 -haloalkyl with 1 to 9 fluoro-, Chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally single to fourfold, identical or different by chlorine,
  • R 33 particularly preferably represents hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso- Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or • for each optionally one to four times, identical or different, by fluorine, chlorine, Methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-
  • R 33 very particularly preferably represents hydrogen, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio , Trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently by fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy.
  • R 35 and R 36 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, C 1 -C 5 -alkoxy, d-Cs-alkylthio, ' d-Cs-alkylsulfonyl, C.-Cs-alkylsulfonyl, C, -C 3 -Halogen- alkyl with 1 to 9 fluorine, chlorine and or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally optionally up to four times, identically or differently by chlorine, -C-C 4 alkyl, CC 4 alkoxy .
  • CC 4 alkylsulfinyl, C r C 4 -Alkylsulfo- nyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, C ⁇ -C logenalkyl 4 -Ha-, CC 4 -haloalkoxy, CC 4 haloalkylthio, C ⁇ -C -Halogenalkylsulfi- nyl, C ⁇ -C -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) N-OR ⁇ , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
  • R 35 and R 36 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy,
  • R 35 and " R 36 independently of one another very particularly preferably represent hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, Ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or for each optionally single or double, identical or different by fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert -Butoxy substituted phenyl or benzyl.
  • R 37 preferably represents hydrogen, Ci-Cs-alkyl, C r C 5 -alkoxy, Ci-d-alkylthio, CC 5 -
  • C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 4 -C 4 haloalkylthio, CC halo alkylsulfinyl, C 1 -C 4 haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, -C ( R 10 ) N-OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OS0 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
  • R 37 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n- Butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally optionally up to four times, identically or differently, by fluorine, chlorine, methyl, ethyl, n -Propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert
  • R 37 very particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert butylthio, trifluoromethyl, or represents in each case optionally monosubstituted or disubstituted by identical or different fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, is ⁇ -propoxy.
  • R 38 preferably represents hydrogen, chlorine, cyano, Ci-Cs-alkyl, dC 5 -alkoxy, C ⁇ -C 5 -alkylthio, Ci-d-alkylsulfinyl, CC 5 -alkylsulfonyl, dd-haloalkyl with 1 to 9 fluoro-, Chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally single to quadruple, identical or different by chlorine, -C 4 alkyl, CC 4 alkoxy, CC 4 alkylthio, CC 4 alkylsulfinyl, CC 4 -
  • R 38 particularly preferably represents hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-Butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different, by fluorine, chlorine, methyl, ethyl , n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy
  • R 38 very particularly preferably represents hydrogen, cyano, methyl ,.
  • R 39 , R 40 and R 41 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, d-Cs-alkoxy, Ci-Cs-alkylthio, dC 5 -allcylsulfinyl, C ⁇ -C 5 -alkylsulfonyl, Ci-d-halo - Genalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or
  • R 39 , R 40 and R 41 independently of one another particularly preferably represent hydrogen
  • R 39 , R 40 and R 41 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-Butoxy, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or for each optionally single or double, identical or different by fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso -Propoxy, tert-butoxy substituted phenyl or benzyl.
  • R 42 and JR 43 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, C 1 -C 5 -alkoxy, Ci-d-alkylthio, -C-C 5 -alkylsulfinyl, CC 5 -alkylsulfonyl, Ci-d-haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally optionally up to four times, identical or different by chlorine,
  • R 42 and R 43 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy,
  • R 42 and R 43 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio, trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
  • R 44 and R 45 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, CC 5 -
  • R 44 and R 45 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso -Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different, by fluorine, chlorine, Methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy,
  • -C (H) N-OC 2 H 5
  • -C (CH 3 ) N-OC 2 H 5
  • -N (H) SO 2 CH 3 -N (CH 3 ) SO 2 CH 3
  • - N (H) SO 2 CF 3 -N (CH 3 ) SO 2 CF 3
  • R 44 and R 4S independently of one another very particularly preferably represent hydrogen
  • R 46 and R 47 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, dC 5 - •
  • R 46 and R 47 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso -Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different by fluorine,
  • Chlorine methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-
  • -C (H) N-OC 2 H 5
  • -C (CH 3 ) N-OC 2 H 5
  • -N (H) SO 2 CH 3 -N (CH 3 ) SO 2 CH 3
  • -N (H) SO 2 CF 3 -N (CH 3 ) SO 2 CF 3
  • R 46 and R 47 independently of one another very particularly preferably represent hydrogen
  • R 48 and R 49 independently of one another preferably represent hydrogen, d-Cs-alkyl, C r C 5 -
  • Ci-Cs-alkylthio dd-alkylsulfinyl, Ci-d-alkylsulfonyl, CC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or for each optionally simple up to fourfold, identical or different by chlorine, -C 4 alkyl, CC 4 alkoxy, -C 4 alkyl thio, CC 4 alkylsulfinyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,
  • R 48 and R 49 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, iso-pentyl, neo-pentyl, methoxy, ethoxy, n -Propoxy, iso-propoxy, n-butoxy, tert-butoxy, n-pentoxy, iso-pentoxy, neo-pentoxy, methylthio,, ethylthio, n-propylthio, iso-propylthio, n-
  • R 48 and R 49 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio, trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
  • R 50 and R 51 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, C 1 -C 5 -
  • Ci-Cj-alkyltbio C, -C 5 -alkylsulfinyl, Ci-Cs-alkylsulfonyl, CC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or in each case optionally mono- to tetrasubstituted by identical or different substituents from chloro, dC 4 -alkyl, C 4 -alkoxy, C 4 alkylthio, d- -All-ylsulfinyl, C, -C 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl , Methoxycarbonyl, ethoxycarbonyl,
  • R 50 and R 51 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso -Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different, by fluorine, chlorine, Methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy,
  • -C (H) N-OC 2 H 5
  • -C (CH 3 ) N-OC 2 H 5
  • -N (H) SO 2 CH 3 -N (CH 3 ) SO 2 CH 3
  • -N (H) SO 2 CF 3 -N (CH 3 ) SO 2 CF 3
  • R 50 and R 51 independently of one another very particularly preferably represent hydrogen
  • R 52 preferably represents hydrogen, C r C 5 alkyl, CC 5 alkoxy, Ci-Cs-alkylthio, dC 5 -
  • R 52 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n- Butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally optionally up to four times, identically or differently, by fluorine, chlorine, methyl, ethyl, n -Propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert
  • R 52 very particularly preferably represents hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio,
  • R 53 preferably represents hydrogen, chlorine, cyano, Ci-Cs-alkyl, dC 5 -alkoxy, C 1 -C 5 -alkylthio, Ci-Cs-alkylsulfinyl, -C-C 5r alkylsulfonyl, -C-C 5 -haloalkyl with 1 up to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally one to four times, identical or different by chlorine, -C 4 alkyl, CC 4 alkoxy, CC 4 alkylthio, -C-C 4 alkylsulfmyl, CC 4 -
  • R 53 particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso- Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-
  • -C (H) N-OC 2 H 5
  • -C (CH 3 ) N-OC 2 H 5
  • -N (H) SO 2 CH 3 -N (CH 3 ) SO 2 CH 3
  • -N (H) SO 2 CF 3 -N (CH 3 ) SO 2 CF 3
  • R 53 very particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, iso-
  • R 54 preferably represents hydrogen, chlorine, cyano, C 1 -C 5 -alkyl, Ci-d-alkoxy, C 1 -C 5 -alkylthio, Cj-Cs-alkylsulfinyl, CC 5 -alkylsulfonyl, dd-haloalkyl with 1 to 9 Fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally one to four times, the same or different, by chlorine, -C 4 alkyl, CC 4 alkoxy, CC alkylthio, C 4 -C 4 alkylsulfmyl, dC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, C ⁇ -C 4 haloalkyl, CC 4 haloalkoxy, CC haloalkylthio,
  • R 54 particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso- Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different, by fluorine, chlorine, methyl , Ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-
  • R 54 very particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert -Butylthio, trifluoromethyl or for each optionally single or double, identical or different by
  • R 55 preferably represents hydrogen, Ci-Cs-alkyl, Ci-d-alkoxy, -C-C 5 alkylthio, C 1 -C 5 -
  • R 55 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n- Butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-.
  • R 55 very particularly preferably represents hydrogen, methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, methoxy, ethoxy, iso-propoxy, "tert-butoxy, methylthio, ethylthio, iso-propylthio, tert-butylthio, Trifluoromethyl or for each optionally single or double, the same or different
  • R 56 and R 57 independently of one another, preferably represent hydrogen, Ci-Cs-alkyl, C 1 -C 5 -alkoxy, Ci-Cs-alkylthio, Ci-Cs-alkylsulfinyl, dC 5 -alkylsulfonyl, dC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or for each optionally single to quadruple, the same or different by chlorine, -CC 4 alkyl.
  • alkylsulfinyl, -C-C 4 haloalkylsulfonyl each with 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) N-OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
  • R 56 and R 57 independently of one another particularly preferably represent hydrogen, methyl,
  • R 56 and R 57 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-Butylthio, trifluoromethyl or phenyl or benzyl, each optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy.
  • R 58 and R 59 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, C 1 -C 5 -alkoxy, Ci-Cs-alkylthio.
  • R 58 and R 59 independently of one another particularly preferably represent hydrogen, methyl,
  • R 58 and R 59 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio, trifluoromethyl or, if appropriate, in each case single or double, identical or different
  • R 60 preferably represents hydrogen, CC 5 -alkyl, Ci-d-alkoxy, -C-C 5 -alkylthio, CC 5 - alkylsulfinyl, Ci-d-alkylsulfonyl, C ⁇ -C 5 -haloalkyl with 1 to 9 fluorine, chlorine - And / or bromine atoms, dd-cycloalkyl or for each optionally single to quadruple, the same or different by chlorine, -C 4 alkyl, C r C 4 alkoxy, C 4 alkylthio, CC 4 alkylsulfinyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, C ⁇ -C haloalkyl, C ⁇ -C4-haloalkoxy, C ⁇ -C haloalkylthio, C r C 4 alky
  • R particularly preferably represents hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy , tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different, by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy , tert-butoxy
  • R 60 very particularly preferably represents hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio,
  • R 61 preferably represents Ci-Cs-alkyl, -C-C 5 -alkoxy, C, -C 5 -alkylthio, -C-C 5 - alkylsulfonyl, -C-C 5 -alkylsulfonyl, Ci-d-haloalkyl with 1 to 9 fluoro -, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different substituents from chloro, CC 4 -alkyl, C 4 -alkoxy, C 4 alkylthio, C ⁇ -C 4 alkylsulfinyl, CC 4 -
  • R 61 particularly preferably represents methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally optionally up to four times, identically or differently, by fluorine, chlorine, methyl, ethyl, n-propyl , iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, ter
  • R 61 very particularly preferably represents methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio, trifluoromethyl or each optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy substituted phenyl or benzyl.
  • R 62 preferably represents cyano, -CC 5 alkyl, Ci-Cs-alkoxy, d-Cs-alkylthio, CC - alkylsulfinyl, CC 3 -alkylsulfonyl, Ci-d-haloalkyl with 1 to 9 fluoro, chloro and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally single to fourfold, identical or different by chlorine, CC 4 alkyl, C r C 4 alkoxy, C 1 -C 4 alkylthio, CC 4 alkylsulfinyl, C r C 4 -alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, C 1 -C 4 -haloalkyl, CC -haloalkoxy, C 1 -C -haloalkylthio, C 1
  • R 62 particularly preferably represents cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n- Butoxy, tert-butoxy, 'methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different, by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-
  • R 62 very particularly preferably represents cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio, trifluoromethyl or for phenyl or benzyl which is optionally monosubstituted or disubstituted, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
  • R 63 preferably represents Ci-Cs-alkyl, CC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, d-Qs-cycloalkyl or for each optionally one to four times, identical or different by chlorine,
  • CC 4 -alkyl, CC 4 -alkoxy, CC 4 -alkylthio, dC 4 -alkylsulfinyl, CC 4 -alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, dC 4 -haloalkyl, C] -C 4 -haloalkoxy, CC 4 haloalkylthio, C ⁇ -C 4 -Halogenalkylsulfi- nyl, atoms, C ⁇ -C 4 haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and / or bromine, -C (R 10) N-oR ⁇ , - (CH 2 ) p N (R 12 ) S0 2 R 13 , or -OSO 2 NR 12 R 13 substituted
  • R 63 particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl,. tert-butyl, n-pentyl, neo-pentyl, trifluoromethyl, cyclopropyl or for each optionally single to fourfold, identical or different by fluorine,
  • R 63 very particularly preferably represents methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, trifluoromethyl or, in each case, in one or two cases, identically or differently
  • R 64 is preferably C ⁇ -C 5 -alkyl, C 5 alkoxy, C Cs-alkylthio, CC ⁇ 5 "alkylsulfinyl, C ⁇ -C 5 alkylsulfonyl, C ⁇ -C 5 haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different substituents from chlorine, C ⁇ -C 4 -alkyl, C 4 -alkoxy, C 4 alkylthio, C ⁇ -C 4 -Alkylsulfmyl, dC 4 -Alkylsul
  • R 64 particularly preferably represents methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio ,.
  • R 64 very particularly preferably represents methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, .ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio, trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
  • R 65 preferably represents Ci-Cs-alkyl. -C-C 5 alkylthio, d-Cs-alkylsulfonyl, Ci-Cs-alkylsulfonyl, Ci-d-haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally simple up to fourfold, the same or different by chlorine, -C 4 alkyl, CC 4 alkoxy, d- alkylthio, -C 4 alkyl sulfinyl, • CC 4 - Alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, C ⁇ -C4 haloalkyl, C ⁇ -C -haloalkoxy, C ⁇ -C4-haloalkylthio, CC 4-halo-alkylsulfinyl,
  • R 65 particularly preferably represents methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert- Butylthio, trifluoromethyl, cyclopropyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso -Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-but
  • R 65 very particularly preferably represents methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or, in each case, optionally single or double, identical or different by fluorine, Chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl.
  • R 66 preferably represents dC 5 alkyl, Ci-Cs-alkylthio, Ci-d-alkylsulfinyl, C r C 5 -
  • R 66 particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different by fluorine
  • R 66 very particularly preferably represents methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or, in each case, in one or more instances, identically or differently
  • R 67 preferably represents CC 5 -alkyl, CC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, dd-cycloalkyl or for in each case optionally up to four times, identically or differently by chlorine, -CC 4 - alkyl, C ⁇ -C 4 -alkoxy, C 4 alkylthio, C ⁇ -C4-alkylsulfinyl, C ⁇ -C 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, C ⁇ -C -Halogenal yl, C ⁇ -C -haloalkoxy , -C-C -haloalkylthio, -C-C -halo-alkylsulfinyl, -C-C -haloalkylsulfonyl each having 1 to ' 9 fluorine
  • R 67 particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-
  • R 67 very particularly preferably represents methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, trifluoromethyl or, if appropriate, in each case once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert- Butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl.
  • R 6S preferably represents Ci-Cs-alkyl, Ci-d-alkoxy, CC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, d-Ce-cycloalkyl or for each optionally one to four times, the same or different from chlorine, dC 4 -alkyl, CC 4 -alkoxy, -C-C 4 -alkylthio, C ⁇ -C 4 -alkylsulfmyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,
  • R 68 particularly preferably represents methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different by fluorine,
  • CH 3 N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted
  • R 68 very particularly preferably represents methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl or for phenyl or benzyl which is optionally monosubstituted or disubstituted, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
  • radical definitions R 14 to R 68 must each be selected so that the heterocycles Ql to Q38 are at least monosubstituted.
  • the possible substitution positions must not simultaneously represent hydrogen. The corresponding requirements are explicitly stated in the general section, but are no longer repeated when the preferred definitions are presented.
  • Chlorine is and R 3 is hydrogen. Also preferred are compounds of formula (I) in which R 1 is fluorine, R 2 is
  • a 1 and A 2 each represent CH and
  • R 4 represents hydrogen, methoxycarbonyl or ethoxycarbonyl
  • a 1 and A 2 each represent CH and
  • R 4 is hydrogen, methoxycarbonyl or ethoxycarbonyl
  • a 1 and A 2 are each CH and Q is an unsaturated aromatic 5-membered heterocycle from the series
  • Q35 Q36 Q37 Q38 and R 62 , R 63 , R 64 , R 65 independently of one another represent methyl, tert-butyl or trifluoromethyl.
  • R 1 represents fluorine, chlorine or methyl
  • R 2 represents hydrogen or fluorine
  • R 3 represents hydrogen or fluorine
  • R 4 represents hydrogen, methoxycarbonyl or ethoxycarbonyl
  • a 1 and A 2 each represent CH and Q represents an unsaturated aromatic 5-membered heterocycle from the series
  • Q35 Q36 Q37 Q38 and R 62 , R 63 , R 64 , R 65 independently of one another represent methyl, tert-butyl or trifluoromethyl.
  • R 1 , R 2 , R 3 , A 1 , A 2 , R 5 , R 6 , R 7 , R 8 and Q have the meanings given above and that
  • R 1 , R 2 , R 3 , A 1 , A 2 , R 5 , R 6 , R 7 , R 8 and Q have the meanings given above, R 4 does not represent hydrogen and the two substituents in 2- and 3 - The position of the 2H pyrrole ring must be in relation to each other.
  • R 1 , R 2 , R 3 , A ⁇ A 2 , R 5 , R 6 , R 7 , R 8 and Q have the meanings given above,
  • R 4 does not represent hydrogen and the two substituents in the 2- and 3-positions of the 2H-pyrrole ring are each Iran.
  • Saturated hydrocarbon radicals such as alkyl
  • heteroatoms e.g. in alkoxy, where possible, be straight-chain or branched.
  • Halogen substituted residues e.g. Haloalkyl
  • Halogen substituted residues are halogenated once or several times up to the maximum possible number of substituents. In the case of multiple halogenation, the halogen atoms can be the same or different.
  • Halogen represents fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
  • Preferred, particularly preferred or very particularly preferred are compounds which each carry the substituents mentioned under preferred, particularly preferred or very particularly preferred.
  • Saturated or unsaturated hydrocarbon residues such as alkyl or alkenyl can also be used in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched.
  • Optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different.
  • the general definitions or explanations of residues or explanations listed above or in preferred areas can, however, also be combined with one another as desired, that is to say between the respective areas and preferred areas. They apply accordingly to the end products as well as to the preliminary and intermediate products.
  • Formula (11) provides a general definition of the ⁇ ⁇ pyrrolines required as starting materials when carrying out process (A) according to the invention.
  • R 1, R 2, R 3, R 4, A 1 and R 5 are preferred, particularly preferred, very particularly preferred or especially preferably has those meanings, which already in connection with the description of the inventive materials Formula (J) for these radicals have been mentioned as preferred, particularly preferred etc.
  • Formula (ID) provides a general definition of the benzene derivatives required as starting materials when carrying out process (A) according to the invention.
  • a 2 , R 6 , R 7 , R 8 and Q preferably, particularly preferably, very particularly preferably or in particular very particularly preferably represent those meanings which have already been associated with the description of the substances of the formula (I) according to the invention were mentioned as preferred, particularly preferred etc. for these radicals.
  • Benzene derivatives of the formula (IH) are known in some cases and / or can be prepared in an analogous manner to known compounds (cf. for Q1: Helv. Chim. Acta 1989, 72, 447-
  • [dba dibenzylidene acetone] or Pd (OAc) 2 , particularly preferably Pd (OAc) 2 .
  • Triarylphosphines Triarylphosphines, trialkylphosphines or arsines are suitable as ligands.
  • dppf, PPh 3 , P (tert-Bu) 3 , Pcy 3 or AsPh 3 Preferably used, dppf, PPh 3 , P (tert-Bu) 3 , Pcy 3 or AsPh 3 , particularly preferably dppf.
  • Suitable diluents for carrying out process (A) according to the invention are all customary inert, organic solvents.
  • Halogenated aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Chlorobenzene, dichlorobenzene, dichloromethane, CWoroform, tetra- chloromethane, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Nitriles, such as acetonitrile, pro
  • Acetone, dimethoxyethane, dioxane, tetrahydrofuran, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, ethanol, toluene or, if appropriate, mixtures of these diluents with water are particularly preferably used.
  • Suitable bases for carrying out process (A) according to the invention are all inorganic and organic bases customary for such reactions.
  • Alkaline earth or alkali metal hydroxides such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or also ammonium hydroxide
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, alkali metal or alkaline earth metal acetates such as sodium acetate, potassium acetate, calcium acetal and alkali metal acetate, and alkali metal acetate
  • Tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimimylarnmopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
  • DABCO
  • Process (A) can be varied over a wide range. In general, temperatures between 0 ° C and 140 ° C, preferably between 20 ° C and 120 ° C, particularly preferably between 60 ° C and 100 ° C.
  • Compound of formula (H) generally 1 mol or a slight excess of a compound of formula (JE), and 0.1 to 50 mol% of a catalyst.
  • JE compound of formula
  • the processing takes place according to usual methods. In general, the procedure is followed by diluting the reaction mixture with water and using an organic diluent. Extracted agent. The organic phase is washed, dried, filtered and concentrated. The residue is optionally after usual. Methods such as chromatography or recrystallization are freed of any impurities that may still be present.
  • the procedure is generally carried out under atmospheric pressure. Abier it is also possible to work under increased or reduced pressure.
  • the active ingredients are suitable for protecting plants and plant organs
  • insects, arachnids and nematodes which are found in agriculture, in forests, in gardens and leisure facilities, in the protection of stocks and materials, and in the hygiene sector. They can preferably be used as plant protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopo ⁇ a e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Diplopoda e.g. Blaniulus guttulatus.
  • Symphyla e.g. Scutigerella imrnaculata.
  • Thysanura e.g. Lep ⁇ sma saccharina.
  • Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp.
  • Linognathus spp. Trichodectes spp., Damalinia spp ..
  • Thysanoptera for example Hercinothrips femoralis, Thrips tabaci, Thrips pal i, FranMiniella occidentalis.
  • Heteroptera for example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phrosiphodumonum.
  • Hymenoptera From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca ., Stomoxys spp., Oestrus spp., Hypoder a spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis
  • Siphonaptera for example Xenopsylla cheopis Ceratophyllus spp ..
  • From the class of the Arachnida for example Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta Roleusppalus, soleivppo, Bo ., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevip ,
  • Plant parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaph.
  • the compounds of the formula (T) according to the invention are distinguished in particular by an excellent action against caterpillars, beetle larvae, spider mites, aphids and leaf miners.
  • the compounds according to the invention can also be used in certain concentrations or application rates as herbicides and microbicides, for example as fungicides, antifungals and bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring plants).
  • Crop plants can be plants which can be obtained by conventional breeding and timing methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Parts and organs of the plants such as sprout, leaf, flower and root, are to be understood, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention takes place directly or by acting on their surroundings, living space. or storage room according to the usual treatment methods. for example by dipping, spraying, vaporizing, misting, scattering, spreading, bijicing and in the case of propagation material, in particular with
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances ,
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and or dispersants and or foam-forming agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents, benzylene, toluene, or alkylnaphthalenes, chlorinated
  • Aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins,
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol as well as their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • solid carriers for example ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granules are possible: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming Suitable agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, ary
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as hecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the bisecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • 2-phenylphenol 8-hydroxyquinoline sulfates; Acibenzolar-S-methyl; Aldimbrph; Amidoflumet; Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole;
  • azoxystrobin benalaxyl; Benodanil; benomyl; Benthiavalicarb-isopropyl; Benzamacril;
  • bromuconazole Bupirimate; Buthiobate; butylamine; Calcium polysulfide; capsimycin;
  • captafol captan; carbendazim; carboxin; carpropamid; carvones; chinomethionat; Chlobenthiazone; Chlorfenazole; chloroneb; chlorothalonil; chlozolinate; Clozylacon; cyazofamid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger " G; Debacarb; dichlofluanid; dichlone; dichlorophene; diclocymet; diclomezine; dicloran;
  • dimoxystrobin dimoxystrobin; diniconazole; Diniconazple-M; dinocap; diphenylamines; Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolon; edifenphos; epoxiconazole; ethaboxam;
  • fluoxastrobin fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcar- banil; Furmecyclox; guazatine; Hexachlorobenzene; hexaconazole; hymexazol; Bnazalil;
  • Bnibenconazole Bninoctadine triacetate; Briinoctadine tris (albesilate); iodocarb; ipconazole;
  • iprobenfos iprodione; iprovalicarb; Bumamycin; isoprothiolane; Isovaledione; Kasugamycin; Kresoxim-methyl; mancozeb; maneb; Meferimzone; mepanipyrim; mepronil; Metaxaxyl; Metalaxyl-M; metconazole; methasulfocarb; Meth neutralam; metiram; Metomino-strobin; Metsulfovax; mildiomycin; myclobutanil; myclozoline; natamycin; nicobifen;
  • propineb proquinazid; prothioconazole; pyraclostrobin; Pyrazohos; pyrifenox; Pyrimethanil; pyroquilon; Pyroxyfur; Pyrrolnitrine; Quinconazole; quinoxyfen; quintozene;
  • tetraconazole thiabendazole; Thicy ⁇ fen; Thifluzamide; Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; Triazbutil; Tri azoxides; Tricyclamide; Tricyclazole; tridemorph; trifloxystrobin; triflumizole; triforine;
  • Chlorfenapyr Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorobenzilate, Chloropicrin, Chlorproxyfen, Chlorpyrifos-methyl, Chlorpyrifos (-ethyl), C ovaporthrin, Chroma-fenozide, Cis-Cypermethrin, Cis-Resmethrin, Clis-Permethrin, Cis-Permethrin - fentezine, Clothianidin, Clothiazoben, Codlemone, Coumaphos, Cyanofenphos, Cyanophos, Cycloprene, Cycloprothrin, Cydia pomonella, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyphenothrin (lR-trans-isomer), Cyromazine,
  • Fenamiphos Fenazaquin, Feributatin oxide, Fenfluthrin, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fensulfothion, Fenthion, Fentrifanil, Fenronfluoronimide, Flenifluoron, Fluvaleron, Fermion , Flubenzimine, remplibrocythrinate, Flucycloxuron, Flucythrinate, Flu- fenerim, Flufenoxuron, Flufenprox, Flimiethrin, Flupyrazofos, Flutenzin (Flufenzine), Fluvalinate, Fonofos, Formetanate, Formothion, Fosmethxate, Fubhoxiazon, Fosthiaxilane, Fosthiazole,
  • Mecarbam Mesulfenfos, Metaldehyde, Metam-sodium, Methacrifos, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methomyl, Methoprene, Methoxychlor, Methoxyfenozide, Metolcarb, Metoxadiazone, Milbeminphinos, Milevinphinin, Mevinphinphin, MKevinphinin, Mevinphinin, Mevinphinphine, Mevinphinin, Mevinphinphine, Mevinphinin, 245 MON-45700, Monocrotophos, Moxidectin, MTI-800,
  • Petroleum PH-6045, phenothrin (IR-trans isomer), phenthoate, phorate, phosalone, phosphate, phosphamidone, phosphocarb, phoxime, piperonyl butoxide, pirimicarb, pirimiphos-methyl, pirimiphos-ethyl, prallethrin, profenofos, promecarb, proppaphos , Propargite, Pro-petamphos, Propoxur, Prothiofos, Prothoate, Protrifenbute, Pymetrozine, Pyraclofos, Pyres-methrin, Pyrelhrum, Pyridaben, Pyridalyl, Pyridaphenthion, Pyridathion, Pyrimidifen, Pyri- proxyfen,
  • a mixture with other known active ingredients such as herbicides, fertilizers,
  • Vigilance regulators for safeners or semiochemicals are possible.
  • the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active.
  • the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in mixtures with inhibitors which break down the active compound after use in the environment of the plant, on the surface of
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the drug concentration of the application molds can range from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active substance When used against hygiene pests and pests of stored products, the active substance is distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
  • plants and their parts can be treated.
  • plant species and plant cultivars and their parts occurring wildly or obtained by conventional organic breeding methods, such as crossbreeding or protoplast fusion are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
  • the term "parts” or “parts of plants” or “plant parts” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant varieties are understood
  • Plants with new traits that have been grown by conventional breeding, mutagenesis or recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also give rise to superadditive (“synergistic”) effects.
  • superadditive for example, reduced application rates and / or widening of the activity spectrum and / or an increase in the action of the substances and agents which can be used according to the invention are better .
  • Plant growth increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the expected effects.
  • the preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, - increased tolerance to dryness or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or Vi ren and an increased tolerance of the plants to certain herbicidal active ingredients.
  • the important crop plants such as cereals (wheat, rice), maize, soybeans, potatoes,
  • Cotton, tobacco, rapeseed and fruit plants are mentioned, whereby maize, soybeans, potatoes, cotton, tobacco and rapeseed are particularly emphasized.
  • the traits are particularly emphasized as the plants' increased defense against insects, arachnids, nematodes and snails due to toxins that arise in the plants, especially those that are caused by the genetic material from Bacillus thuringiensis (eg by the genes Cry ⁇ A (a) , CryIA (b), CryIA (c), CryllA, CryHIA, CryHIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter “Bt plants”).
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR),
  • Plants which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example bnidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example the JPAT gene).
  • the genes conferring the desired properties (“traits”) can also be found in combinations with one another in the transgenic plants. Examples of “Bt plants” are corn varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YDELD GARD® (eg corn , Cotton, soy), KnockOut® (e.g.
  • StarLink® e.g. corn
  • Bollgard® cotton
  • Nucotn® cotton
  • NewLeaf® potato
  • herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties which are marketed under the trade names Roundup Ready® (tolerance against glyphosate, e.g. maize, cotton, soy), Liberty Link® (tolerance against phosphinotricin, e.g. rape), MI® (tolerance against Bnidazolinone) and STS® (tolerance to sulfonylureas such as maize).
  • the herbicide-resistant plants include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the active substances according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tortoise ticks, leather ticks, space mites, running mites,
  • Flies stinging and licking
  • parasitic fly larvae lice, hair lice, featherlings and fleas.
  • lice lice, hair lice, featherlings and fleas.
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
  • Tabanus spp. Haematopota spp., Pbilipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Orriithocheyletia spp., Myobia spp.,. Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.
  • ticks such as Amblyomma hebraeum
  • parasitic flies such as against Lucilia cuprina
  • fleas such as CtenocephaUdes felis
  • the active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals such as Infest hamsters, guinea pigs, rats and mice.
  • arthropods e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals such as Infest hamsters, guinea pigs, rats and mice.
  • the active compounds according to the invention are used in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Bijections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering, and with the aid of shaped articles containing active ingredients, such as collars, ear tags, tails marks, limb straps, holsters, marking devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories
  • parenteral administration for example by Bijections (
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Lyctus brunneus Lyctus africanus
  • Lyc us planicollis Lyctus linearis
  • Lyctus pubescens Trogoxylon aequale
  • Minthes rugicollis Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus rninutus;
  • Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
  • Bristle tails such as Lepisma saccharina.
  • non-living materials such as preferably plastics, adhesives, glues, papers and
  • Cardboard boxes, leather, wood, wood processing products and paints are Cardboard boxes, leather, wood, wood processing products and paints.
  • the material to be protected against bisect infestation is very particularly preferably wood and wood processing products.
  • Wood and wood processing products that can be protected by the agent according to the invention or mixtures containing it are to be understood as examples:
  • Plywood, chipboard, carpentry or wood products that are used in general in house construction or joinery.
  • the active compounds can be used as such, in the form of concentrates or generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes.
  • formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, if appropriate
  • Desiccants and UV stabilizers and, where appropriate, dyes and pigments and other processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and occurrence of the B sects and on the medium. The optimum amount of use can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected.
  • organic-chemical solvent or solvent mixture and or an oily or oil-like low-volatile organic-chemical solvent or solvent mixture and or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent are used as solvents and / or diluents.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Corresponding mineral oils or their aromatic fractions or solvent mixtures containing mineral oil are preferred as such low-volatility, water-insoluble, oily and oily solvents
  • Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, duck oil and the like.
  • organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the sel tizid-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.
  • the known organic-chemical binders are water-thinnable and / or organic-chemical binders
  • Solvent-soluble or dispersible or emulsifiable synthetic resins and / or binding drying oils in particular binders consisting of or containing a Acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as biden-coumarone resin. Silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin are used.
  • binders consisting of or containing a Acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as biden-coumarone resin. Silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and bihibitors or
  • Corrosion protection agents and the like are used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture).
  • a fixing agent mixture
  • a plasticizer mixture
  • additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the used
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl,
  • Dioctyl or benzyl butyl phthalate Dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ether or higher molecular weight glycol ethers, glycerol esters and
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvmylmethylether or ketones such as benzophenone, ethyl dibenzophenone.
  • Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood preservation is achieved by industrial impregnation processes, eg vacuum, double vacuum or pressure processes.
  • the ready-to-use means may also contain other bisecticides and, if appropriate, one or more fungicides.
  • the bisecticides and fungicides mentioned in WO 94/29268 are preferably suitable as additional admixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Bisecticides such as chlorpyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, ijmidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, trifluoridophenone, trifluoridophenone, trifluoridophenone, trifluoridophenone, trifluoridophenone, trifluoridophenone, trifluorophenol, trifluoride, trifluoride .
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, bnazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5 -N-octylisothiazolin-3-one.
  • connections according to the invention can be used to protect objects, in particular hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
  • barnacles Ledamorpha
  • Balanomorpha barnacles
  • Baianus or Pollicipes species increases the frictional resistance of Ships and subsequently leads to a significant increase in operating costs due to increased energy consumption and, moreover, frequent dry dock stays.
  • heavy metals such as e.g. in bis (trialkyltin) sulfides, tri-H-butyltin laurate, tri- ⁇ -butyltin chloride, copper (I) oxide, triethyltin chloride, tri-n-butyl (2-phenyl-4-cU ⁇ henoxy) tin , tributyltin oxide, Molybdändisulf ⁇ d, antimony oxide, polymeric butyl titanate, phenyl- (bispyridine) -wismutchlorid, tri - "- butyltin fluoride, Manganethylenbisthiocarbamat, carbamate zinc dimethyldithiocarbamate, Zinkethylenbisthio-, zinc and copper salts of 2-pyridinethiol-l-oxide, Bisdimethyldithiocarbamoyl- zinkethylen
  • the ready-to-use antifouling paints may also contain other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Algicides such as 2-tert-butylarmno-4-cyclopropylamino-6-methylfhio-l, 3,5-triazine, dichlorophen, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn; Fungicides such as benzo [b] tmophencarbonkladcyclohexylan-id-S, S-dioxide, dichlofluanid, Fluorfolpet, 3-iodo-2-propynyl butylcarbarnat, tolylfluanid and azoles such as azaconazole, cyproconazole, epoxyconazole, hexaconazole, conconazole, metazazole, Molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicar
  • the antifouling agents used contain the active compound according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular 0.01 to 20% by weight.
  • the antifouling agents according to the invention furthermore contain the usual constituents, such as in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
  • antifoulm paints contain in particular binders.
  • Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chloride / vinyl acetate copolymer systems.
  • aqueous dispersions or in the form of organic solvent systems, butadiene / styroVAcrylonitrile rubbers , drying oils, such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in seawater. Paints may also contain materials such as rosin to enable controlled release of the active ingredients.
  • the paints can also contain plasticizers, modifiers that influence the theological properties and other conventional ones
  • the compounds according to the invention or the mixtures mentioned above can also be incorporated into self-polishing antifouling systems.
  • the active ingredients are also suitable for controlling animal pests, in particular bisects, arachnids and mites, which occur in closed spaces, such as, for example, apartments, factory halls, offices, vehicle cabins and others. To combat these pests, they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products. You are sensitive to and resistant species and effective against all stages of development. These pests include:
  • Scorpionidea e.g. Buthus occitanus.
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp ..
  • Dermanyssus gallinae Glyciphagus domesticus, Omithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..
  • Anopheles spp. Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus,
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inte ⁇ unctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • CtenocephaUdes canis, CtenocephaUdes felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera for example Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium phara ⁇ nis, Paravespula spp., Tetramorium caespitum.
  • Example 3 Example 3
  • reaction mixture is then stirred under reflux. After cooling to room temperature, the reaction mixture is stirred into sodium hydroxide solution (45%, 100 ml) / ice water (500 ml) and extracted three times with 400 ml of ethyl acetate each time. The organic phase is separated off, dried over sodium sulfate, filtered and concentrated. The crude product is purified by means of flash chromatography on silica gel (methylene chloride / ethyl acetate 10: 1).
  • reaction mixture is mixed with 100 ml of water and extracted twice with 100 ml of ethyl acetate, the organic phase is separated off, dried over sodium sulfate, filtered and concentrated. The residue is dissolved in 30 ml of dichloromethane and purified by means of flash chromatography on silica gel (gradient methylene chloride / Ethyl acetate 10: 0 - »9: 1).
  • the determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluents; linear gradient from 10% acetonitrile to 90% acetonitrile (marked with a in the tables).
  • the determination is carried out in the neutral range at pH 7.5 with 0.01 molar aqueous
  • the calibration is carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear bitolation between two successive alkanones).
  • the lambda max values were determined on the basis of the UV spectra from 200 ⁇ m to 400 nm in the maxima of the chromatographic signals.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 2 parts by weight of alkylaryl polyglycol ether
  • Active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water containing emulsifier to the desired concentration.
  • Soybean shoots (Glycine max) are obtained by diving in . treated the active ingredient preparation of the desired concentration and with caterpillars of the cotton capsule worm
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: • 2 parts by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish leaf beetle (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the cockroach (Plutella xylostella) while the leaves are still moist.
  • the kill is determined in%: 100% means that all the caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera exigua) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera frugiperda) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Bean plants Phaseolus vulgaris
  • Tetranychus urticae which are heavily infested with all stages of the common spider mite (Tetranychus urticae), are immersed in an active ingredient preparation of the desired concentration.
  • the effect is determined in%. 100% means that all the spils have been killed; 0% means that no spider mites have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • the active ingredient preparation is poured onto the floor.
  • the concentration of the active ingredient in the preparation is practically irrelevant, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm (mg / 1).
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Soybean shoots (Glycine max) of the Roundup Ready variety (trademark of Monsanto Comp. USA) are treated by dipping into the preparation of active compound of the desired concentration and populated with the tobacco bud caterpillar Heliothis virescens while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.

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  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pyrrole Compounds (AREA)

Abstract

Disclosed are novel Delta<1> pyrrolines of formula (I), wherein R<1>, R<2>, R<3>, R<4>, A<1>, A<2>, R<5>, R<6>, R<7>, R<8>, R<9>, and Q have the meanings indicated in the description, a method for producing said substances, and the use thereof for pest control.

Description

Pyrrolinepyrrolines
Die vorliegende Erfindung betrifft neue Δ'-Pyrroline, mehrere Verfahren zu ihrer Herstellung und ihre Verwendung als Wirkstoffe, insbesondere ihre Verwendung als Schädlingsbelämpfungsmittel.The present invention relates to new Δ'-pyrrolines, several processes for their preparation and their use as active substances, in particular their use as pesticides.
Es ist bereits bekannt, dass zahlreiche Δ1 -Pyrroline insektizide Eigenschaften besitzen (vgl. WO 02/064588, WO 02/064561, WO 02/46151, WO 02/24646, WO 02/24644, WO 02/24643, WO 00/21958, WO 99/59968, WO 99/59967 und WO 98/22438). Die Wirksamkeit dieser Stoffe ist gut, lässt aber in manchen Fällen zu wünschen übrig.It is already known that numerous Δ 1 -pyrrolines have insecticidal properties (cf. WO 02/064588, WO 02/064561, WO 02/46151, WO 02/24646, WO 02/24644, WO 02/24643, WO 00 / 21958, WO 99/59968, WO 99/59967 and WO 98/22438). The effectiveness of these substances is good, but leaves something to be desired in some cases.
Es wurden nun neue Δ^Pyrroline der Formel (T)New Δ ^ pyrrolines of the formula (T)
gefunden, in welcher R1 für Halogen, Q-C4-Alkyl oder C C4-Halogenalkyl steht, found in which R 1 represents halogen, QC 4 alkyl or CC 4 haloalkyl,
R2 für Wasserstoff, Halogen, Cι-C4-Alkyl oder Cι-C -Halogenalkyl steht, R3 für Wasserstoff, Halogen oder Methyl steht,R 2 represents hydrogen, halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, R 3 represents hydrogen, halogen or methyl,
R4 für Wasserstoff, Ci-Cg-Alkyl, (Cι-C6-Alkoxy)carbonyl, (C3-C6-Cycloalkyl)- oxycarbonyl, (Cι-C6-Halogenalkoxy)carbonyl, für gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, C.-C4-Alkyl, d-R 4 represents hydrogen, Ci-Cg-alkyl, (Cι-C 6 alkoxy) carbonyl, (C 3 -C 6 cycloalkyl) - oxycarbonyl, (Cι-C 6 haloalkoxy) carbonyl, optionally mono- or polysubstituted by identical or different from halogen, cyano, nitro, C.-C 4 -alkyl, d-
C -Alkoxy, Cι-C -Alkylthio, Cι-C4-Halogenalkyl, Cι-C4-Halogenalkoxy und oderC -alkoxy, C alkylthio, Cι-C4 haloalkyl, Cι-C4 haloalkoxy, and or
Cι-C4-Halogenalkylthio substituiertes Aryl steht,-C-C 4 haloalkylthio substituted aryl,
A1 für N oder CH steht,A 1 represents N or CH,
A2 für N oder CR9 steht,A 2 represents N or CR 9 ,
R5 für Wasserstoff, Halogen, C C6-Alkyl, CrC6-Alkoxy, Cι-C6-Alkylthio, C C6- Alkylsulfϊnyl, Cι-C6-Alkylsulfonyl, Cι-C6-Halogenalkoxy, Cj-C6-Halogenalkylthio, Ci-Cβ-Halogenalkylsulfinyl oder Cj-C6-Halogenalkylsulfonyl steht, R6, R7, R8 und R9 unabhängig voneinander für Wasserstoff, Halogen, Cyano, Formyl, Nitro, Tri(C C6-alkyl)silyl, CrC6-Alkyl, C6-C6-Alkoxy, C C6-Alkylthio, C C6-Alkylsul- finyl, Cι-C6-Alkylsulfonyl,. C2-C6-Alkenyl, C2-C6-Alkenyloxy, (CπC6-Alkyl)- carbonyl, (C1-C6-Alkoxy)carbonyl, Ci-Cg-Halogenalkyl, Cι-C6-Halogenalkoxy, C Ce-Halogenalkylthio, Cι-C6-Halogenalkylsulfϊnyl, Cι-C6-Halogenalkylsulfonyl, C2- C6-Halogenalkenyl, C2-C6-Halogenalkenyloxy, (Cι-C6-Halogenalkyl)carbonyl, ( - C6-Halogenalkoxy)carbonyl, Pentafluorthio, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 stehen,R 5 for hydrogen, halogen, CC 6 -alkyl, C r C 6 -alkoxy, -C-C 6 -alkylthio, CC 6 - alkylsulfonyl, Cι-C 6 -alkylsulfonyl, Cι-C 6 -haloalkoxy, Cj-C 6 - Haloalkylthio, Ci-Cβ-haloalkylsulfinyl or Cj-C 6 -haloalkylsulfonyl, R 6 , R 7 , R 8 and R 9 independently of one another are hydrogen, halogen, cyano, formyl, nitro, tri (CC 6 alkyl) silyl, C r C 6 alkyl, C 6 -C 6 alkoxy, CC 6 -Alkylthio, CC 6 -Alkylsul- finyl, -C-C 6 -Alkylsulfonyl ,. C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, (C π C 6 alkyl) - carbonyl, (C 1 -C 6 alkoxy) carbonyl, Ci-Cg-haloalkyl, -C-C 6 haloalkoxy , C Ce-haloalkylthio, -C-C 6 -haloalkylsulfonyl, Cι-C 6 -haloalkylsulfonyl, C 2 - C 6 -haloalkenyl, C 2 -C 6 -haloalkenyloxy, (-C-C 6 -haloalkyl) carbonyl, (- C 6 -Halogenalkoxy) carbonyl, pentafluorothio, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 ,
R10 für Wasserstoff, -Ce-Alkyl, C2-C6-Alkenyl, C,-C6-Halogenalkyl, C2-C6-Halogen- alkenyl oder C3-C6-Cycloalkyl steht,R 10 represents hydrogen, -Ce-alkyl, C 2 -C 6 alkenyl, C, -C 6 haloalkyl, C 2 -C 6 haloalkenyl or C 3 -C 6 cycloalkyl,
R11 für Wasserstoff, C C6-Alkyl, C2-C6-Alkenyl, C C6-Halogenalkyl, C2-C6-Halogen- alkenyl, C3-C6-Cycloalkyl-Cι-C4-alkyl oder gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch R5 substituiertes Aryl-Ci-Gralkyl steht,R 11 for hydrogen, CC 6 alkyl, C 2 -C 6 alkenyl, CC 6 haloalkyl, C 2 -C 6 halo alkenyl, C 3 -C 6 cycloalkyl -CC 4 -alkyl or optionally simple or is aryl-Ci-Gralkyl substituted several times, identically or differently by R 5 ,
R12 und R13 unabhängig voneinander für Wasserstoff, Cι-C6-Alkyl, Cι-C6-Halogenalkyl, für gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Cι-C6-Alkyl substituiertes C3-C6-Cycloalkyl, für C3-C6-Cycloalkyl-Cι-C4-alkyl oder für gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Rs substituiertes Aryl-Cι-C -alkyl stehen,R 12 and R 13 independently of one another are hydrogen, C 6 -alkyl, C 6 haloalkyl, optionally substituted singly or multiply, identically or differently, by halogen or Cι-C 6 alkyl C 3 -C 6 cycloalkyl are C 3 -C 6 cycloalkyl-C 4 -C 4 alkyl or aryl-C 1 -C 4 -alkyl which is optionally mono- or polysubstituted identically or differently by R s ,
R12 und R13 außerdem gemeinsam für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Cι-C6-Alkyl substituiertes C2-C6-Alkylen, ( -R 12 and R 13 also together for each optionally mono- or polysubstituted, identically or differently, by halogen or -CC 6 -alkyl-substituted C 2 -C 6 -alkylene, (-
C3-Alkoxy)Cι-C3-alkylen oder (Cι-C3-Alkylthio)CrC3-alkylen steht,C 3 alkoxy) -C 3 alkylene or (-C 3 alkylthio) C r C 3 alkylene,
p für 0, 1 oder 2 steht,p represents 0, 1 or 2,
Q für einen einfach oder mehrfach, gleich oder verschieden durch Reste aus der ListeQ for one or more, the same or different from residues from the list
W1 substituierten vollständig ungesättigten 5-gliedrigen Heterocyclus mit 1 bis 3 gleichen oder verschiedenen Heteroatomen aus der Reihe Stickstoff, Sauerstoff und/oder Schwefel steht, und W1 für Halogen, Cyano, d-Cι6-Alkyl, d- e-Alkoxy, C Cι6-Alkylthio, d-Cι6-Alkyl- sulfinyl, C Cι6-Alkylsulfonyl, Ci-Cie-Halogenalkyl, Cι-Cι6-Halogenalkoxy, C Cι6- Halogenalkylthio, C Cι6-Halogenalkylsulfmyl, Cι-Cι6-Halogenalkylsul,fonyl, C3- Cπ-Cycloalkyl oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durchW 1 substituted fully unsaturated 5-membered heterocycle having 1 to 3 identical or different heteroatoms from the series consisting of nitrogen, oxygen and / or sulfur, and W 1 for halogen, cyano, d -CC 6 alkyl, d- e-alkoxy, C 6 -C alkylthio, d -C 6 alkyl sulfinyl, C 6 -C alkylsulfonyl, Ci-Cie-haloalkyl, Cι-Cι 6 -Halogenalkoxy, C -C 6 - haloalkylthio, C 6 -C -haloalkylsulfmyl, Cι-C 6 -haloalkylsul, fonyl, C 3 - Cπ-cycloalkyl or for each optionally one or more, the same or different by
Halogen, Cyano, Formyl, Nitro, Tri(C C6-alkyl)silyl, CrC6-Alkyl, C C6-Alkoxy, d-Ce-Alkylthio, d-C6-Alkylsulfinyl, C C6-Alkylsulfonyl, . C2-C6-Alkenyl, C2-C6- Alkenyloxy, (Cι-C6-Alkyl)carbonyl, (Cι-C6-Alkoxy)carbonyl, d-Cβ-Halogenalkyl, Cι-C6-Halogenalkoxy, Cι-C6-Halogenalkylthio, Cι-C6-Halogenalkylsulfinyl, Cj-C6- Halogenalkylsulfonyl, C2-C6-Halogenalkenyl, C2-C6-Halogenalkenyloxy,Halogen, cyano, formyl, nitro, tri (CC 6 -alkyl) silyl, C r C 6 -alkyl, CC 6 -alkoxy, d-Ce-alkylthio, dC 6 -alkylsulfinyl, CC 6 -alkylsulfonyl,. C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, (-C-C 6 -alkyl) carbonyl, (Cι-C 6 -alkoxy) carbonyl, d-Cβ-haloalkyl, -C-C 6 -haloalkoxy, Cι -C 6 -haloalkylthio, -C-C 6 -haloalkylsulfinyl, Cj-C 6 - haloalkylsulfonyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkenyloxy,
-C(R10)=N-ORU, -S02NRl2R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR1 R13 substituiertes Aryl oder Aryl- Cι-C -alkyl steht.-C (R 10 ) = N-OR U , -S0 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 1 R 13 substituted aryl or aryl -CC-C -alkyl.
In der Formel (T) bezeichnet * ein stereogenes Zentrum. In dem Fall, dass R4 nicht fürIn formula (T), * denotes a stereogenic center. In the event that R 4 is not for
Wasserstoff steht, bezeichnet • ein weiteres stereogenes Zentrum, wobei die Substituenten an den beiden Zentren eis oder trans zueinander stehen können. Die gleiche Bezeichnung gilt für alle anderen Formeln dieser Beschreibung.Hydrogen stands for • another stereogenic center, whereby the substituents at the two centers can be ice or trans to each other. The same designation applies to all other formulas in this description.
Die Verbindungen der Formel (I) können gegebenenfalls in Abhängigkeit von der Art undThe compounds of formula (I) may optionally depend on the type and
Anzahl der Substituenten als geometrische und/oder optische Isomere bzw. Regioisomere oder deren Isomerengemische in unterschiedlicher Zusammensetzung vorliegen. Sowohl die reinen Isomere als auch die Isomerengemische werden erfindungsgemäß beansprucht.The number of substituents as geometric and / or optical isomers or regioisomers or their isomer mixtures are present in different compositions. Both the pure isomers and the isomer mixtures are claimed according to the invention.
Weiterhin wurde gefunden, dass sich Δ1 -Pyrroline der Formel (I) herstellen lassen, indem man ' Furthermore, it was found, that Δ 1 -Pyrrolines of formula (I) can be produced by reacting '
A) Δ^Pyrroline der Formel (H)A) Δ ^ pyrrolines of the formula (H)
in welcher , R1, R2, R3, R4, A1 und R5 die oben angegebenen Bedeutungen haben, in which , R 1 , R 2 , R 3 , R 4 , A 1 and R 5 have the meanings given above,
mit Benzol-Derivaten der Formel (HI)with benzene derivatives of the formula (HI)
in welcher in which
A2, R6, R7, Rs und Q die oben angegebenen Bedeutungen haben und X1 für Brom, Iod oder -OSO2CF3 steht,A 2 , R 6 , R 7 , R s and Q have the meanings given above and X 1 represents bromine, iodine or -OSO 2 CF 3 ,
in Gegenwart eines Katalysators und in Gegenwart eines Verdünnimgsmittels umsetzt.in the presence of a catalyst and in the presence of a diluent.
Schließlich wurde gefunden, dass die erfindungsgemäßen Verbindungen der Formel (T) sehr gute insektizide Eigenschaften besitzen und sich sowohl im Pflanzenschutz als auch im Materialschutz zur Bekämpfung unerwünschter Schädlinge, wie Insekten, Spinnentieren und Milben, verwenden lassen.Finally, it was found that the compounds of the formula (T) according to the invention have very good insecticidal properties and can be used both in crop protection and in material protection to control unwanted pests, such as insects, arachnids and mites.
Die erfindungsgemäßen Verbindungen sind durch die Formel (I) allgemein definiert. Bevorzugte Substituenten bzw. Bereiche der in den oben und nachstehend erwähnten Formeln aufgeführten Reste werden im folgenden erläutert.The compounds of the invention are generally defined by the formula (I). Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below.
R1 steht bevorzugt für Fluor, Chlor, Brom, Cι-C -Alkyl oder C C4-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen. R1 steht besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, n-Propyl, iso-R 1 preferably represents fluorine, chlorine, bromine, -CC alkyl or CC 4 haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms. R 1 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, iso-
Propyl, n-Butyl, iso-Butyl, sek-Butyl, tert-Butyl oder C C4-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen.Propyl, n-butyl, isobutyl, sec-butyl, tert-butyl or CC 4 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms.
R1 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, iso-Propyl, tert-Butyl oder Trifluormethyl. R1 steht insbesondere ganz besonders bevorzugt für Fluor, Chlor oder Methyl.R 1 very particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl or trifluoromethyl. R 1 particularly preferably represents fluorine, chlorine or methyl.
R2 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, C C -Alkyl oder Cι-C4-Halo- genalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen. R2 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, .Methyl, Ethyl, n- Propyl, iso-Propyl, n-Butyl, iso-Butyl. sek-Butyl, tert-Butyl oder Trifluormethyl.R 2 preferably represents hydrogen, fluorine, chlorine, bromine, CC-alkyl or -CC 4 -halogenoalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms. R 2 particularly preferably represents hydrogen, fluorine, chlorine, bromine, .methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl. sec-butyl, tert-butyl or trifluoromethyl.
R2 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Methyl, Ethyl, iso- Propyl oder tert-Butyl. R2 steht insbesondere ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor oderR 2 very particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, isopropyl or tert-butyl. R 2 particularly preferably represents hydrogen, fluorine, chlorine or
Methyl.Methyl.
R3 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom oder Methyl.R 3 preferably represents hydrogen, fluorine, chlorine, bromine or methyl.
R3 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor oder Methyl. R3 steht ganz besonders bevorzugt für Wasserstoff. Fluor oder Chlor.R 3 particularly preferably represents hydrogen, fluorine, chlorine or methyl. R 3 very particularly preferably represents hydrogen. Fluorine or chlorine.
R3 steht insbesondere ganz besonders bevorzugt für Wasserstoff oder Fluor.R 3 particularly preferably represents hydrogen or fluorine.
R4 steht bevorzugt für Wasserstoff, Cι-C -Alkyl, (Cι-C6-Alkoxy)carbonyl, (C3-C6- Cycloalkyl)oxycarbonyl, (Cι-C4-Halogenalkoxy)carbonyl mit 1 bis 9 Fluor- und/oder Chloratomen, für gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Brom, Iod, Cyano, Nitro, C C4-Alkyl, Cι-C4-Alkoxy, Cι-C4- Alkylthio, C C4-Halogenalkyl, C C -Halogenalkoxy und/oder d-C4-Halogenalkyl- thio mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen substituiertes Phenyl.R 4 preferably represents hydrogen, -CC alkyl, (-C 6 alkoxy) carbonyl, (C 3 -C 6 cycloalkyl) oxycarbonyl, (-C 4 haloalkoxy) carbonyl with 1 to 9 fluorine and / or chlorine atoms, for optionally up to four times, the same or different by fluorine, chlorine, bromine, iodine, cyano, nitro, CC 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, CC 4 haloalkyl, CC -haloalkoxy and / or dC 4 -haloalkyl-thio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, substituted phenyl.
R4 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, sek-Butyl, tert-Butyl, Methoxycarbonyl, Ethoxycarbonyl, n-Prop- oxycarbonyl, iso-Propoxycarbonyl, n-Butoxycarbonyl, iso-Butoxycarbonyl, sek-But- oxycarbonyl, tert-Butoxycarbonyl, n-Pentoxycarbonyl, Neopentoxycarbonyl, sec- Isoamyloxycarbonyl, Pentan-3-yloxycarbonyl, n-Hexyloxycarboήyl, Cyclopentyloxycarbonyl, Cyclohexyloxycarbonyl, Trifluormethoxycarbonyl, Tri- fluorethoxycarbonyl, für gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Brom, Iod, Cyano, Nitro, Cι-C4-Alkyl, Cι-C -Alkoxy, Cι-C4-Alkylthio, Cι-C -Halogenalkyl, Cι-C4-Halogenalkoxy und/oder Cι-C4-Halo- genalkylthio mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen substituiertes Phenyl.R 4 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, methoxycarbonyl, ethoxycarbonyl, n-prop-oxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, iso-butoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n-pentoxycarbonyl, neopentoxycarbonyl, sec- Isoamyloxycarbonyl, pentan-3-yloxycarbonyl, n-Hexyloxycarboήyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, trifluoromethoxycarbonyl, tri- fluoroethoxycarbonyl, optionally mono- or disubstituted by identical or different fluorine, chlorine, bromine, iodine, cyano, nitro, Cι-C 4 -alkyl, C -alkoxy, C 4 alkylthio, Cι-C haloalkyl, Cι-C 4 -Halogenalkoxy and / or -C-C 4 -haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted phenyl.
R4 steht ganz besonders bevorzugt für Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxycarbonyl, Ethoxycarbonyl, n-Propoxycarbonyl, iso-Propoxycarbonyl, n-Butoxycar- bonyl, iso-Butoxycarbonyl, sek-Butoxycarbonyl, tert-Butoxycarbonyl, n-Pentoxy- carbonyl, Neopentoxycarbonyl, sec-Isoamyloxycarbonyl, Pentan-3-yloxycarbonyl, n-Hexyloxycarbonyl, Cyclopentyloxycarbonyl, Cyclohexyloxycarbonyl, für gegebenenfalls einfach durch Fluor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, sek-Butyl, tert-Butyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, iso- Butoxy, sek-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso- Propyltbio, n-Butyltiiio, iso-Butylthio, sek-Butylthio, tert-Butylthio, Trifluormethyl oder Trifluormethoxy substituiertes Phenyl.R 4 very particularly preferably represents methyl, ethyl, iso-propyl, tert-butyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, iso-butoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n Pentoxycarbonyl, neopentoxycarbonyl, sec-isoamyloxycarbonyl, pentan-3-yloxycarbonyl, n-hexyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, for optionally simply by fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propyltbio, n-butyltiiio, iso-butylthio, sec-butylthio, tert-butylthio, trifluoromethyl or Trifluoromethoxy substituted phenyl.
R4 steht insbesondere ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, Methoxycarbonyl, Ethoxycarbonyl, 4-Fluorphenyl oder 4-Chlorphenyl.R 4 particularly preferably represents hydrogen, methyl, ethyl, methoxycarbonyl, ethoxycarbonyl, 4-fluorophenyl or 4-chlorophenyl.
A1 steht bevorzugt für N. A1 steht bevorzugt für CH.A 1 preferably represents N. A 1 preferably represents CH.
A2 steht bevorzugt für N. A2 steht bevorzugt für CR9.A 2 preferably represents N. A 2 preferably represents CR 9 .
A2 steht besonders bevorzugt für CH.A 2 particularly preferably represents CH.
R5 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Cι-C4-Alkyl, C C -Alkoxy, Cι-C -Alkylthio, Cι-C -Alkylsulfinyl, Cι-C -Alkylsulfonyl; Cι-C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfϊnyl oder Cι-C -Halogenalkyl- sulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen.R 5 preferably represents hydrogen, fluorine, chlorine, bromine, -C 4 alkyl, CC alkoxy, C 1 -C alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl; C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, C 4 -C 4 haloalkylsulfonyl or C 1 -C 4 haloalkyl sulfonyl, each having 1 to 9 fluorine, chlorine and / or bromine atoms.
R5 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, sek-Butyl, tert-Butyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, iso-Butoxy, sek-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, iso-Butylthio, sek-Butylthio, tert- Butylthio, Methylsulflnyl, Ethylsulfinyl, n-Propylsulfinyl, iso-Propylsulfinyl, n-Butylsulfinyl, iso-Butylsulfmyl, sek-Butylsulfinyl, tert-Butylsulfrnyl, Methyl- sulfonyl, Ethylsulfonyl, n-Propylsulfonyl, iso-Propylsulfonyl, n-Butylsulfonyl, iso- Butylsulfonyl, sek-Butylsulfonyl, tert-Butylsulfonyl, Trifluormethyl, Trifluorethyl,R 5 particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso- Propoxy, n-butoxy, iso-butoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, iso-butylthio, sek-butylthio, tert-butylthio, methylsulfonyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl, n-butylsulfinyl, iso-butylsulfmyl, sec-butylsulfinyl, tert-butylsulfonyl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, iso-propylsulfonyl, n-butylsulfonyl, sulfonyl, iso- tert-butylsulfonyl, trifluoromethyl, trifluoroethyl,
Trifluormethoxy, Trifluorethoxy, Trifluormethylthio, Trifluorethylthio, Trifluorme- thylsulfinyl, Trifluorethylsulfinyl, Trifluormethylsulfonyl oder Trifluorethylsul- fonyl. Rs steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Methyl, Ethyl, iso- Propyl, tert-Butyl, Methoxy, Ethoxy,. iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Methylsulfonyl, Trifluormethyl, Trifluormethoxy, Trifluormethylthio oder Trifluormethylsulfonyl.Trifluoromethoxy, trifluoroethoxy, trifluoromethylthio, trifluoroethylthio, trifluoromethylsulfinyl, trifluoroethylsulfinyl, trifluoromethylsulfonyl or trifluoroethylsulfonyl. R s very particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy ,. iso-propoxy, tert-butoxy, methylthio, ethylthio, iso-propylthio, tert-butylthio, methylsulfonyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio or trifluoromethylsulfonyl.
R5 steht insbesondere ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Methyl, Ethyl, Methoxy oder Ethoxy.R 5 particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, methoxy or ethoxy.
R6, R7, R8 und R9 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Cyano, Formyl, Nitro, Tri(d-C4-alkyl)silyl, C,-C -Alkyl, d-C4-Alkoxy, -R 6 , R 7 , R 8 and R 9 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, cyano, formyl, nitro, tri (dC 4 -alkyl) silyl, C, -C -alkyl, dC 4 -alkoxy , -
C4-Alkylthio, C,-C4-Alkylsulfmyl, Cι-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenylöxy, (Cι-C4-Alkyi)carbonyl, (d-C -Alkoxy)carbonyl Cι-C -Halogenalkyl, Cι-C -Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl oder Ci- C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; C2-C -Halogenalkenyl oder C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-,C 4 -Alkylthio, C, -C 4 -Alkylsulfmyl, -C-C 4 -Alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (-C-C 4 -alkyi) carbonyl, (dC -alkoxy ) carbonyl Cι-C haloalkyl, Cι-C -haloalkoxy, Cι-C4-haloalkylthio, Cι-C 4 haloalkylsulfinyl or C C 4 haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; C 2 -C haloalkenyl or C 2 -C haloalkenyloxy each with 1 to 7 fluorine,
Chlor- undoder Bromatomen, (C C4-Halogenalkyl)carbonyl oder (Cι-C -Halogen- alkoxy)carbonyl, mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, Penta- fluorthio, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13.Chlorine and or bromine atoms, (CC 4 haloalkyl) carbonyl or (C 1 -C halo alkoxy) carbonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, pentafluorothio, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 .
R6, R7, R8 und R9 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Cyano, Formyl, Trimethylsilyl, Dimethyl-tert-butylsilyl, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, sek-Butyl, tert-Butyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, iso-Butoxy, sek-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, iso-Butylthio, sek-R 6 , R 7 , R 8 and R 9 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, cyano, formyl, trimethylsilyl, dimethyl-tert-butylsilyl, methyl, ethyl, n-propyl, isopropyl, n-butyl , iso-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso -Propylthio, n-butylthio, iso-butylthio, sec-
Butylthio, tert-Butylthio, Methylsulfinyl, Ethylsulfinyl, n-Propylsulfinyl, iso-Propylsulfinyl, n-Butylsulfinyl, iso-Butylsulfinyl, sek-Butylsulfinyl, tert-Butylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n-Propylsulfonyl, iso-Propylsulfonyl, n-Butylsulfonyl, iso-Butylsulfonyl, sek-Butylsulfonyl, tert-Butylsulfonyl, Vinyl, Allyl, Vinyloxy, Allyloxy, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, tert-Butylthio, tert-butylthio, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl, n-butylsulfinyl, iso-butylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n-propylsulfonylsulfonyl, iso iso-butylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, vinyl, allyl, vinyloxy, allyloxy, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, tert-
Butoxycarbonyl; Trifluormethyl, Trifluorethyl, Trifluormethoxy, Trifluorethoxy, 1,1,2,2-Tetrafluorethoxy, Trifluormethylthio, Trifluorethylthio, Trifluormethylsul- fϊnyl, Trifluorethylsulfinyl, Trifluormethylsulfonyl, Trifluorethylsulfonyl, 2,2- Difluorvinyl, 2,2-Dichlorvinyl, Trifluorvinyloxy, Trifluormethylcarbonyl, Trifluor- ethylcarbonyl, Trifluormethoxycarbonyl, Trifluorethoxycarbonyl, Pentafluorthio, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSOzNR^R13.butoxycarbonyl; Trifluoromethyl, trifluoroethyl, trifluoromethoxy, trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, trifluoromethylthio, trifluoroethylthio, trifluoromethylsulfonyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trifluorethylsulfonylvinyl, 2,2if ethylcarbonyl, trifluoromethoxycarbonyl, trifluoroethoxycarbonyl, pentafluorothio, -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , - OSO 2 R 12 or -OSOzNR ^ R 13 .
R6, R7, R8 und R9 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Methylsulflnyl, Ethylsulfinyl, iso-Propylsulfinyl, tert-Butylsulfinyl, Methylsulfonyl, Ethylsulfonyl, . iso-Propylsulfonyl, tert-Butylsulfonyl, Vinyl, Allyl, Methylcarbonyl, Methoxycarbo- nyl, Trifluormethyl, Trifluormethoxy, Trifluormethylthio, Dimethylaminosulfonyl, Trifluormethylcarbonyl, Trifluormethoxycarbonyl, Dimethylamino, Diethylamino,R 6 , R 7 , R 8 and R 9 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, Ethylthio, iso-propylthio, tert-butylthio, methylsulfonyl, ethylsulfinyl, iso-propylsulfinyl, tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl,. iso-propylsulfonyl, tert-butylsulfonyl, vinyl, allyl, methylcarbonyl, methoxycarbonyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, dimethylaminosulfonyl, trifluoromethylcarbonyl, trifluoromethoxycarbonyl, dimethylamino, diethylamino,
Diiso-n-propylamino, -N(Me)COMe, -N(Me)COEt, -N(Me)COPr,Diiso-n-propylamino, -N (Me) COMe, -N (Me) COEt, -N (Me) COPr,
-N(Me)CO(tert-Bu), 2-Pyrrolidon-5-yl, 2-Piperidon-6-yl, -N(Me)SO2Me, -N(Me)SO2Et, -N(Me)S02CF3, -N(Et)SO2CF3, -N(Me)SO2(CF2)3CF3 oder -OSO2NMe2.-N (Me) CO (tert-Bu), 2-pyrrolidon-5-yl, 2-piperidon-6-yl, -N (Me) SO 2 Me, -N (Me) SO 2 Et, -N (Me ) S0 2 CF 3 , -N (Et) SO 2 CF 3 , -N (Me) SO 2 (CF 2 ) 3 CF 3 or -OSO 2 NMe 2 .
R6, R7, R8 und R9 stehen unabhängig voneinander insbesondere ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Methyl, Methoxy, Methylthio, Trifluormethyl, Trifluormethoxy, Trifluormethylthio, -SO2NMe2.R 6 , R 7 , R 8 and R 9 independently of one another are particularly preferably hydrogen, fluorine, chlorine, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, -SO 2 NMe 2 .
R6, R7, R8 und R9 stehen unabhängig voneinander herrorjjehoben für Wasserstoff.R 6 , R 7 , R 8 and R 9 stand independently of one another for hydrogen.
R10 steht bevorzugt für Wasserstoff, d-C4-Alkyl, C2-C -Alkenyl, C C4-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl mit 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, Cyclopropyl, Cyclopentyl oder Cyclohexyl.R 10 preferably represents hydrogen, dC 4 alkyl, C 2 -C alkenyl, CC 4 haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl with 1 to 7 fluorine , Chlorine and / or bromine atoms, cyclopropyl, cyclopentyl or cyclohexyl.
R10 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl oder Cyclopropyl.R 10 particularly preferably represents hydrogen, methyl, ethyl or cyclopropyl.
R10 steht ganz besonders bevorzugt für Wasserstoff, Methyl oder Ethyl.R 10 very particularly preferably represents hydrogen, methyl or ethyl.
RJ1 steht bevorzugt für Wasserstoff, Cι-C4-Alkyl, C2-C4-Alkenyl, C C4-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und oder Bromatomen, C2-C -Halogenalkenyl mit 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl-d-C2-alkyl oder jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch R5 substituiertes Benzyl oder Phenylethyl. Rn steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, Cyclopropylmethyl oder jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden durch R5 substituiertes Benzyl.R J1 preferably represents hydrogen, -CC 4 alkyl, C 2 -C 4 alkenyl, CC 4 haloalkyl with 1 to 9 fluorine, chlorine and or bromine atoms, C 2 -C haloalkenyl with 1 to 7 fluorine -, Chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl-dC 2 -alkyl or in each case optionally up to four times, identical or differently substituted by R 5, benzyl or phenylethyl. R n particularly preferably represents hydrogen, methyl, ethyl, cyclopropylmethyl or in each case optionally one to three times, identically or differently substituted by R 5, benzyl.
R11 steht ganz besonders bevorzugt für Wasserstoff, Methyl oder Ethyl.R 11 very particularly preferably represents hydrogen, methyl or ethyl.
R12 und R13 stehen unabhängig voneinander bevorzugt für Wasserstoff, Cι-C -Alkyl, C C4- Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl, •d-Ce-Cycloalkyl-d-d-alkyl oder jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch R5 substituiertes Benzyl oder Phenylethyl.R 12 and R 13 independently of one another preferably represent hydrogen, -CC alkyl, CC 4 - haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl, • d-Ce cycloalkyl -dd-alkyl or in each case optionally up to four times, identically or differently substituted by R 5, benzyl or phenylethyl.
R12 und ,R13 stehen außerdem gemeinsam bevorzugt für d-d-Alkylen, -(CH2)2-O-(CH2)2- oder -(CH2)2-S-(CH2)2-.R 12 and R 13 also together preferably represent dd-alkylene, - (CH 2 ) 2 -O- (CH 2 ) 2 - or - (CH 2 ) 2 -S- (CH 2 ) 2 -.
R12 und R13 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl,R 12 and R 13 independently of one another particularly preferably represent hydrogen, methyl,
Ethyl, n-Propyl, iso-Propyl, tert-Butyl, Trifluormethyl, Cyclopropylmethyl oder jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden durch R5 substituiertes Benzyl.Ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, cyclopropylmethyl or in each case optionally up to three times, identically or differently substituted by R 5, benzyl.
R12 und R13 stehen außerdem gemeinsam besonders bevorzugt für Propylen, Butylen,R 12 and R 13 together also particularly preferably represent propylene, butylene,
Pentylen, -(CH2)2-O-(CH2)2- oder -(CH2)2-S-(CH2)2-.Pentylene, - (CH 2 ) 2 -O- (CH 2 ) 2 - or - (CH 2 ) 2 -S- (CH 2 ) 2 -.
p steht bevorzugt für 0 oder 1. p steht besonders bevorzugt für 0.p is preferably 0 or 1. p is particularly preferably 0.
steht bevorzugt für einen einfach oder mehrfach, gleich oder verschieden durch Reste aus der Liste W1 substituierten vollständig ungesättigten 5-gliedrigen Hetero- cyclus mit 1 bis 3 gleichen oder verschiedenen Heteroatomen aus der Reihe Stickstoff, Sauerstoff und/oder Schwefel, undpreferably represents a single or multiple, identical or different, substituted by radicals from the list W 1, completely unsaturated 5-membered heterocycle having 1 to 3 identical or different heteroatoms from the series nitrogen, oxygen and / or sulfur, and
W1 steht bevorzugt für Fluor, Chlor, Brom, Cyano, Cι-Cι2-Alkyl, C Cι2-Alkoxy, Ci-W 1 preferably represents fluorine, chlorine, bromine, cyano, C 1 -C 2 alkyl, C 2 -C alkoxy, Ci
Ci2-Alkylthio, d-Cι2-Alkylsulfinyl, C Cι2-Alkylsulfonyl, C d2-Halogenalkyl, CCi2-alkylthio, d -CC 2 alkylsulfinyl, C C 2 -alkylsulfonyl, C d 2 haloalkyl, C
Cι2-Halogenalkoxy, d-C12-Halogenalkylthio, d-C12-Halogenalkylsulfinyl, C Cι2-C 2 haloalkoxy, dC 12 haloalkylthio, dC 12 haloalkylsulfinyl, C C 2
Halogenalkylsulfonyl, C3-d2-Cycloalkyl oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-AJlcyl, C C4-Alk- oxy, Cι-C4-Alkylthio, Cι-C4-Alkylsulfinyl,.C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2- C4-Alkenyloxy, (C1-C4-Alkyl)carbonyl, (d-C4-Alkoxy)carbonyl, Ci-Q-Halogen- alkyl, Cι-C -Halogenalkoxy, C1-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, Cι-C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Aryl-C C2-alkyl.Haloalkylsulfonyl, C 3 -d 2 -cycloalkyl or for each optionally optionally one or more times, the same or different Fluorine, chlorine, bromine, cyano, formyl, nitro, trimethylsilyl, C 1 -C 4 alkyl, CC 4 alkoxy, C 1 -C 4 alkylthio, C 4 C alkylsulfinyl, .CC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 - C 4 alkenyloxy, (C 1 -C 4 alkyl) carbonyl, (dC 4 alkoxy) carbonyl, Ci-Q-halo- alkyl, Cι-C -haloalkoxy, C 1 - C 4 haloalkylthio, C 4 -C haloalkylsulfinyl, C 1 -C haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each having 1 up to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or aryl-C C 2 alkyl.
steht besonders bevorzugt für einen vollständig ungesättigten 5-gliedrigen Hetero- cyclus aus der Reiheparticularly preferably represents a completely unsaturated 5-membered heterocycle from the series
Q31 Q32 Q33 Q34Q31 Q32 Q33 Q34
Q35 Q36 Q37 Q38 worin Q35 Q36 Q37 Q38 where
R14 und R15 unabhängig voneinander für Wasserstoff, Chlor, Cyanö, Cι-C12-Alkyl, C1-C12- . Alkoxy, d-C12-Alkylthio, Cι-Cι2-Alkylsulfinyl, Ci-Ciz-Alkylsulfonyl, Cι-Cι2-Halo- genalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,R 14 and R 15 are independently hydrogen, chlorine, Cyanö, Cι-C 12 alkyl, C 1 -C 12 -. Alkoxy, dC 12 alkylthio, Cι-Cι 2 alkylsulfinyl, Ci-Ciz-alkylsulfonyl, Cι-Cι 2 -Halo- genalkyl, C 3 -Cι 2 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different fluorine,
Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-Alkyl, Cι-C4-Alkoxy, CrC4- Alkylthio, C C4-Alkylsulfinyl, Cι-C4-Alkylsulfonyl, . C2-C4-Alkenyl, ■ C2-C4- Alkenyloxy, (Cι-C4-Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl, C C4-Halogenalkyl, Cι-C4-Halogenalkoxy, d-d-Halogenalkylthio, Cι-C -Halogenalkylsulfinyl, d-C4- Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-Chlorine, cyano, formyl, nitro, trimethylsilyl, Cι-C 4 -alkyl, C 4 alkoxy, C r C 4 - alkylthio, CC 4 alkylsulfinyl, Cι-C 4 alkylsulfonyl,. C 2 -C 4 alkenyl, ■ C 2 -C 4 alkenyloxy, (-C-C 4 -alkyl) carbonyl, (-C-C 4 -alkoxy) carbonyl, CC 4 -haloalkyl, -C-C 4 -haloalkoxy, dd -Halogenalkylthio, -C-C -Halogenalkylsulfinyl, dC 4 - haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -
C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each having 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
R16 für Wasserstoff, Cyano, Cι-d2-Alkyl, Cι-C12-Alkoxy, d-Cι2-Alkylthio, d-C12- Alkylsulfinyl, Cι-Cι2-Alkylsulfonyl, Cι-Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-Alkyl, C C4-Alkoxy, C1-C4- Alkylthio, CπC4-Alkylsulfinyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C4-Alkyl)carbonyl, (C C -Alkoxy)carbonyl, C C -Halogenalkyl, Cι-C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, d-C -R 16 for hydrogen, cyano, -C-d 2 -alkyl, Cι-C 12 -alkoxy, d-Cι 2 -alkylthio, dC 12 - alkylsulfinyl, Cι-Cι 2 -alkylsulfonyl, Cι-Cι 2 -haloalkyl, C 3 - Cι 2 -cycloalkyl or optionally monosubstituted in each case to four times by identical or different fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, Cι-C 4 alkyl, CC 4 -alkoxy, C 1 -C 4 - alkylthio, C π C 4 alkylsulfinyl, CC 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (-C-C 4 -alkyl) carbonyl, (CC -alkoxy) carbonyl, CC -haloalkyl, -C-C 4 -haloalkoxy, -Cι -C 4 haloalkylthio, -C-C 4 haloalkylsulfinyl, dC -
Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substitu- iertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenenHaloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy, each with 1 to 7 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) pN (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 are those given above
Bedeutungen haben,Have meanings
mit der Maßgabe, dass R14, R15, R16 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 14 , R 15 , R 16 do not simultaneously represent hydrogen,
R17 und R19 unabhängig voneinander für Wasserstoff, Cyano, Cι-C]2-Alkyl, d-Cι2-Alkoxy,R 17 and R 19 independently of one another for hydrogen, cyano, C 1 -C 2 alkyl, d C 2 alkoxy,
Cι-Cι2-Alkylthio, C C12-Alkylsulfinyl, C Cι2-Alkylsulfonyl, CrCπ-Halogenalkyl, C3-C12-Cycloalkyl oder J für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-Alkyl, Cι-C -Alkoxy, C C - Alkylthio, Cι-C4-Alkylsulfinyl, CrC4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyl- oxy, (Cι-C -Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl5 Cι-C -Halogenalkyl, d-C4-C 1 -C 2 alkylthio, CC 12 alkylsulfinyl, C C 2 alkylsulfonyl, C r C π haloalkyl, C 3 -C 12 cycloalkyl or J for each optionally up to four times, identically or differently, by fluorine, chlorine, cyano , formyl, nitro, trimethylsilyl, Cι-C 4 -alkyl, C alkoxy, C - C alkylthio, Cι-C 4 alkylsulfinyl, C r C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 -alkenyl oxy, (Cι-C alkyl) carbonyl, (Cι-C 4 alkoxy) carbonyl 5 Cι-C haloalkyl, dC 4 -
Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, Cι-C τHalo- genalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Ha-Haloalkoxy, Cι-C 4 haloalkylthio, Cι-C 4 haloalkylsulfinyl, Cι-C τHalo- genalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 -Ha-
• logenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils. 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORU, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13,• logenalkenyl, C 2 -C 4 haloalkenyloxy with each. 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR U , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 ,
-(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder- (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or
Benzyl stehen, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,Are benzyl, where R 10 to R 13 have the meanings given above,
R18 für Wasserstoff, Chlor, Cyano, C C12-Alkyl, Cι-C12-Alkoxy, Cι-C12-Alkylthio, C.-R 18 for hydrogen, chlorine, cyano, CC 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, C.-
Cι2-Alkylsulfinyl, Cι-Cι2-Alkylsulfonyl, Cj-Cπ-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-Alkyl, Cj-C -Alkoxy, Cι-C4-Al- kylthio, C C4-Alkylsulfinyl, Cι-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyl- oxy, (Cι-C4-Alkyl)carbonyl, (d-C4-Alkoxy)carbonyl, C C4-Halogenalkyl, C!-C4- Halogenalkoxy, Cι-C4-Halogenalkylthio, C1-C4-Halogenalkylsulfinyl, C!^C -Halo- genalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C -Ha- logenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(RI0)=N-ORn, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R:2)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,Cι 2 alkylsulfinyl, Cι-Cι 2 alkylsulfonyl, Cj-Cπ haloalkyl, C 3 -Cι 2 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, Cι -C 4 alkyl, Cj-C -alkoxy, C 4 alkylthio -Al-, CC 4 alkylsulfinyl, Cι-C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 -alkenyl oxy , (-C-C 4 alkyl) carbonyl, (dC 4 -alkoxy) carbonyl, CC 4 -haloalkyl, C! -C 4 - haloalkoxy, Cι-C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C ! ^ C -halo genalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C ( R I0 ) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) pNR 12 R 13 , - (CH 2 ) p N (R : 2 ) COR 13 , - (CH 2 ) p N ( R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 is substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
mit der Maßgabe, dass R17, R18, R19 nicht gleichzeitig für Wasserstoff stehen, R20 und R23 unabhängig voneinander für Wasserstoff, Cι-Cι2-Alkyl, Cι-Cι2-Alkoxy, Cj-Cπ- Alkylthio, d-C.2-AlkylsulfinyL CrCι2-Alkylsulfonyl, C C12-Halogenalkyl, C3-C12- Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C -Alkyl, Cι-C4-Alkoxy, Cι-C4- Alkylthio, C C4-Alkylsulfinyl, Cι-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C -Alkyl)carbonyl, (C1-C -Alkoxy)carbonyl, Cι-C4-Halogenalkyl, . Cι-C4-Halogenalkoxy, Cι-C -Halogenalkylthio, d-C4-Halogenalkylsulfinyl, C C -with the proviso that R 17 , R 18 , R 19 are not simultaneously hydrogen, R 20 and R 23 independently of one another are hydrogen, C 1 -C 2 -alkyl, C 1 -C 2 alkoxy, Cj-Cπ- alkylthio, dC , 2 -AlkylsulfinyL C r Cι 2 -Alkylsulfonyl, CC 12 -haloalkyl, C 3 -C 12 - cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, Cι-C - alkyl, Cι-C 4 -alkoxy, C 4 - alkylthio, CC 4 alkylsulfinyl, Cι-C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 - alkenyloxy, (Cι-C alkyl ) carbonyl, (C 1 -C alkoxy) carbonyl, -CC 4 haloalkyl,. C 1 -C 4 haloalkoxy, C 1 -C haloalkylthio, dC 4 haloalkylsulfinyl, CC -
Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C -Halogenalkenyl, C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)PN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substitu- iertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenenHaloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C haloalkenyl, C 2 -C haloalkenyloxy, each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) P N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 are substituted phenyl or benzyl, where R 10 to R 13 are those given above
Bedeutungen haben, R21 und R22 unabhängig voneinander für Wasserstoff, Chlor, Cyano, Cι-C12-Alkyl, C1-C12- Alkoxy, Cj-d∑-Alkylthio, Cι-C12-Alkylsulfinyl, d-C12-Alkylsulfonyl, C Cι2-Halo- genalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,Have meanings R 21 and R 22 are independently hydrogen, chlorine, cyano, C 12 alkyl, C 1 -C 12 - alkoxy, Cj-d Σ alkylthio, Cι-C 12 alkylsulfinyl, alkylsulfonyl dC 12 , C 1 -C 2 -haloalkyl, C 3 -C 2 -cycloalkyl or for each optionally optionally up to four times, identical or different by fluorine,
Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C -Alkyl, Cι-C4-Alkoxy, C C4- Alkylthio, C C4-Alkylsulfmyl, d-Q-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C4-Alkyl)carbonyl, (C1-C -Alkoxy)carbonyl, Cι-C4-Halogenalkyl, Cι-C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, C C4- Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-Chlorine, cyano, formyl, nitro, trimethylsilyl, Cι-C -alkyl, C 4 alkoxy, CC 4 - alkylthio, CC 4 -Alkylsulfmyl, dQ alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 - alkenyloxy, (Cι-C4 alkyl) carbonyl, (C 1 -C -alkoxy) carbonyl, Cι-C4 haloalkyl, Cι-C4-haloalkoxy, Cι-C4-haloalkylthio, Cι-C4 haloalkylsulfinyl , CC 4 - haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -
C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR1 R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenen Bedeutungen haben, mit der Maßgabe, dass R20, R21 , R22, R23 nicht gleichzeitig für Wasserstoff stehen, R24 für Wasserstoff, d-d-Alkyl oder C3-C6-Cycloalkyl steht,C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each having 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 1 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above, with the proviso that R 20 , R 21 , R 22 , R 23 are not simultaneously hydrogen, R 24 is hydrogen, dd-alkyl or C 3 -C 6 -cycloalkyl,
R25 und R26 unabhängig voneinander für Wasserstoff, Chlor, Cyano, d-Cι2-Alkyl, Cj-C12-R 25 and R 26 independently of one another for hydrogen, chlorine, cyano, d -CC 2 alkyl, Cj-C 12 -
Alkoxy, Cι-C12-Halogenalkyl, C3-Ci2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d-C4-Alkyl, C C4-Alkoxy, Cι-C - Alkylthio, d-C4-Alkylsulfmyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2rC4- Alkenyloxy, (C C4-Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl,Alkoxy, -C-C 12 haloalkyl, C 3 -Ci 2 -cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, dC 4 alkyl, CC 4 alkoxy, C 1 -C 4 alkylthio, dC 4 alkylsulfmyl, CC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 rC 4 alkenyloxy, (CC 4 alkyl) carbonyl, (C 1 -C 4 alkoxy) carbonyl, Cι -C 4 haloalkyl,
Cι-C -Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, d-C - Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C -Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(RI2)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenen Bedeutungen haben, R27 für Wasserstoff, d-Cι2-Alkyl, Cι-C12-Alkoxy5 Cι-C12-Halogenalkyl, C3-C12-Cyclo- alkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,Cι-C -haloalkoxy, Cι-C4-haloalkylthio, Cι-C 4 haloalkylsulfinyl, dC - halogenoalkylsulphonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C haloalkenyl, C 2 -C 4 -Halogenalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - ( CH 2 ) p N (R I2 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above, R 27 represents hydrogen, d-Cι 2 -alkyl, C 12 -alkoxy 5 Cι-C 12 haloalkyl, C 3 -C 12 -cycloalkyl or represents in each case optionally mono- to four times, the same or different due to fluorine,
Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d-C4-Alkyl, d-C4-Alkoxy, Cι-C4- Alkylthio, C C4-Alkylsulfinyl, ' d-C4-Alkylsulfonyl, C C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C -Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C -Halogenalkyl, Cι-C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C -Halogenalkylsulfinyl, Cι-C4- Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-Chlorine, cyano, formyl, nitro, trimethylsilyl, dC 4 alkyl, dC 4 -alkoxy, C 4 - alkylthio, CC 4 alkylsulfinyl, 'dC 4 alkylsulfonyl, CC 4 alkenyl, C 2 -C 4 - alkenyloxy , (Cι-C alkyl) carbonyl, (Cι-C 4 alkoxy) carbonyl, Cι-C haloalkyl, Cι-C4-haloalkoxy, Cι-C4-haloalkylthio, Cι-C haloalkylsulfinyl, Cι-C 4 - Haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -
C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each having 1 to 7 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
mit der Maßgabe, dass R24, R25, R26, R27 nicht gleichzeitig für Wasserstoff stehen, R28 und R30 unabhängig vonemander für Wasserstoff, Cι-Cι2-Alkyl, Cι-Cι2-Alkoxy, Ci-Cπ- Halogenalkyl, C3-Cι2-Cycloalkyl oder für-jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, CrC4-Alkyl, d-C4-Alkoxy, Cι-C4- Alkylthio, d-C4-Alkylsulfmyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyl- oxy, (Cι-C -Alkyl)carbonyl, (Cι-C -Alkoxy)carbonyl, C C4-Halogenalkyl, Cι-C - Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, Ci- -Halo- genalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C -Ha- logenalkenyl, C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,with the proviso that R 24 , R 25 , R 26 , R 27 do not simultaneously stand for hydrogen, R 28 and R 30 independently of one another for hydrogen, -CC 2 alkyl, C 1 -C 2 -alkoxy, Ci-Cπ- Haloalkyl, C 3 -C 2 cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C r C 4 alkyl, dC 4 alkoxy, C 1 -C 4 alkylthio, dC 4 alkyl sulfyl, CC 4 -Alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyl oxy, (-C-C-alkyl) carbonyl, (-C-C -alkoxy) carbonyl, CC 4 -haloalkyl, Cι-C - haloalkoxy, Cι-C4-haloalkylthio, Cι-C4-haloalkylsulfinyl, Ci -Halo- genalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C -Ha- logenalkenyl, C 2 -C haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
R29 für Wasserstoff, Chlor, Cyano, Cι-C12-Alkyl, Cι-C12-Alkoxy, Cι-C12-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, CrC4-Alkyl, CrC4-Alkoxy, C C4-Al- kylthio, d-d-Alkylsulfinyl, Cι-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyl- oxy, (Cι-C4-Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl, C C -Halogenalkyl, C C - Halogenalkoxy, C C -Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, Cι-C4-Halo- genalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Ha- logenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13,R 29 represents hydrogen, chlorine, cyano, C 12 -alkyl, C 12 -alkoxy, C 12 haloalkyl, C 3 -Cι 2 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different fluorine , chlorine, cyano, formyl, nitro, trimethylsilyl, C r C 4 alkyl, C r C 4 alkoxy, alkylthio CC 4 -Al-, dd alkylsulfinyl, Cι-C 4 alkylsulfonyl, C 2 -C 4 alkenyl , C 2 -C 4 -alkenyloxy, (-C-C 4 -alkyl) carbonyl, (-C-C 4 -alkoxy) carbonyl, CC -haloalkyl, CC - haloalkoxy, CC -haloalkylthio, -C-C 4 -haloalkylsulfinyl, Cι-C 4 -Halo- genalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 logenalkenyl -Ha-, C 2 -C 4 haloalkenyloxy having in each case 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) pN (R 12 ) COR 13 ,
-(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 is substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
»31 für Wasserstoff, d-C6-Alkyl, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl,»31 for hydrogen, dC 6 -alkyl, C 3 -C 6 -cycloalkyl or for in each case optionally up to four times, identical or different by fluorine, chlorine, cyano, formyl,
Nitro, Trimethylsilyl, Cι-C4-Alkyl, d- -Alkoxy, C,-C4-Alkylthio, d-C4-Alkylsul- finyl, Cι-C -Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, .(C C -Alkyl)car- bonyl, (d-C -Alkoxy)carbonyl, Cι-C4-Halogenalkyl, C C4-Halogenalkoxy, d-C -Nitro, trimethylsilyl, C 1 -C 4 -alkyl, d- alkoxy, C, -C 4 -alkylthio, dC 4 -alkylsul- finyl, C 1 -C 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -Alkenyloxy,. (CC -Alkyl) carbonyl, (dC -alkoxy) carbonyl, -C-C 4 -haloalkyl, CC 4 -haloalkoxy, dC -
Halogenalkylthio, CrC -Halogenalkylsulfinyl, Cι-C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C -C4-Halogenalkenyl, C2-C4-Haloalkylthio, C r C -haloalkylsulfinyl, -C-C -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C -C 4 haloalkenyl, C 2 -C 4 -
Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen,Haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms,
-C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13,-C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 ,
-(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder- (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or
Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben, mit der Maßgabe, dass R28, R29, R30, R31 nicht gleichzeitig für Wasserstoff stehen,Benzyl, where R 10 to R 13 have the meanings given above, with the proviso that R 28 , R 29 , R 30 , R 31 do not simultaneously represent hydrogen,
R32 und R34 unabhängig voneinander für Wasserstoff, d-d2-Alkyl, -d-rAlkoxy, Cι-C_2- Alkylthio, C Cι2-Alkylsulfmyl, C C12-Alkylsulfonyl, C C12-Halogenalkyl, C3-C12-R 32 and R 34 are independently hydrogen, dd 2 alkyl, -d-rAlkoxy, Cι-C_ 2 - alkylthio, C 2 Cι -Alkylsulfmyl, CC 12 alkylsulfonyl, CC 12 haloalkyl, C 3 -C 12 -
' 5 Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C C -Alkyl, d-d-Alkoxy, C C4- Alkylthio, C C4-Alkylsulfinyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C4-Alkyl)carbonyl, (Cι-C -Alkoxy)carbonyl, Cι-C4-Halogenalkyl, 0 Ci-OrHalogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenälkylsulfinyl, C C4- '5 cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, CC alkyl, CC 4-alkoxy dd - alkylthio, alkylsulfinyl CC 4, CC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (-C-C 4 -alkyl) carbonyl, (Cι-C -alkoxy) carbonyl, -C-C 4 -haloalkyl, 0 Ci-OrHalogenalkoxy, Cι-C 4 -haloalkylthio, -C-C 4 -haloalkylsulfinyl, CC 4 -
Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, C2- C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substitu- 5 iertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenenHaloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and or bromine atoms, C 2 - C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy, each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 are those given above
Bedeutungen haben, R33 für Wasserstoff, Chlor, Cyano, d-C12-Alkyl, CrC12-Alkoxy, Cι-Cι2-Alkylthio, C Cπ-Alkylsulfϊnyl, Cι-Cι2-Alkylsulfonyl3 Cι-Cι2-Halogenalkyl, C3-C12-Cycloalkyl oder 0 . für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,Have meanings R 33 represents hydrogen, chlorine, cyano, dC 12 alkyl, C r C 12 -alkoxy, Cι 2 alkylthio, C Cπ-Alkylsulfϊnyl, Cι-Cι Cι-Cι 2 alkylsulfonyl 3 2 haloalkyl, C 3 -C 12 cycloalkyl or 0. for each one optionally up to four times, the same or different by fluorine,
Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-Alkyl, Cι-C4-Alkoxy, Cι-C4- Alkylthio, C C4-Alkylsulfinyl, Cι-C4-Alkylsulfonyl, C2-C -Alkenyl, C2-C4- Alkenyloxy, (Cι-C4-Alkyl)carbonyl, (Cι-C -Alkoxy)carbonyl, C C4-Halogenalkyl, Cι-C -Halogenalkoxy, Cι-C -Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, Cι-C4- 5 Halogenalkylsulfpnyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-Chlorine, cyano, formyl, nitro, trimethylsilyl, Cι-C 4 -alkyl, C 4 -alkoxy, C 4 - alkylthio, CC 4 alkylsulfinyl, Cι-C 4 alkylsulfonyl, C 2 -C alkenyl, C 2 -C 4 - Alkenyloxy, (-C-C 4 -alkyl) carbonyl, (-C-C -alkoxy) carbonyl, CC 4 -haloalkyl, Cι-C -haloalkoxy, Cι-C -haloalkylthio, Cι-C 4 -haloalkylsulfinyl , -CC 4 - 5 haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -
C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen 0 Bedeutungen haben,C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each having 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 is substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
mit der Maßgabe, dass R32, R33, R34 nicht gleichzeitig für Wasserstoff stehen, R35 und R36 unabhängig voneinander für Wasserstoff, Cι-Cι2-Alkyl, Cι-C12-Alkoxy, C C12- Alkylthio, CrCι2-Alkylsulfinyl, C C12-Alkylsulfonyl, C Cι2-Halogenalkyl, C3-C12- Cycloalkyl oder , für jeweils gegebenenfalls einfach bis vierfach, gleich, oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, CrC4-Alkyl, C C4-Alkoxy, C C4-Al- kylthio, CrC4-Alkylsulfinyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyl- oxy, (Cι-C -Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl, C C4-Halogenalkyl, C C - Halogenalkoxy, Cι-C -Halogenalkylthio, C C -Halogenalkylsulfinyl, Cι-C -Halo- genalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C -Ha- logenalkenyl, C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oderwith the proviso that R 32 , R 33 , R 34 do not simultaneously represent hydrogen, R 35 and R 36 independently of one another for hydrogen, C 1 -C 2 alkyl, C 1 -C 12 alkoxy, CC 12 alkylthio, C r C 2 alkylsulfinyl, CC 12 alkylsulfonyl, C 1 -C 2 haloalkyl, C 3 - C 12 - cycloalkyl or, in each case optionally up to four times, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C r C 4 alkyl, CC 4 alkoxy, CC 4 alkylthio, C r C 4 alkylsulfinyl, CC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyl oxy, (C 1 -C 4 alkyl) carbonyl, (C 1 -C 4 alkoxy) carbonyl, CC 4 -Halogenalkyl, CC - haloalkoxy, -C-C -haloalkylthio, CC -haloalkylsulfinyl, Cι-C -halogenoalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C -haloalkenyl, C 2 -C -Halogenalkenyloxy with 1 to 7 fluorine, chlorine and / or
Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,Bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
mit der Maßgabe, dass R31, R35, R36 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 31 , R 35 , R 36 do not simultaneously represent hydrogen,
R37 für Wasserstoff, C Cι2-Alkyl, d-Cι2-Alkoxy, C Cι2-Alkylthio, Cι-d2- Alkylsulfinyl, Cι-Cι2-Alkylsulfonyl, Cι-Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C C4-Alkyl, Cι-C4-Alkoxy, C C4-R 37 is hydrogen, Cι C 2 alkyl, d-Cι 2 alkoxy, C 2 Cι alkylthio, Cι-d 2 - alkylsulfinyl, Cι-Cι 2 alkylsulfonyl, Cι-Cι 2 -haloalkyl, C 3 -Cι 2 -Cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, CC 4 alkyl, C 1 -C 4 alkoxy, CC 4 -
Alkylthio, CrC4-Alkylsulfinyl, CrC4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C4-Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl, d-C4-Halogenalkyl, d-C4-Halogenalkoxy, C C4-Halogenalkylthio, Cι-C -Halogenalkylsulfinyl, Cι-C4- Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C4-Halogenalkenyl, C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben, R38 für Wasserstoff, Chlor, Cyano, Cι-C12-Alkyl, d-C12-Alkoxy, Cι-C12-Alkylthio, d-Alkylthio, C r C 4 alkylsulfinyl, C r C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (C 1 -C 4 alkyl) carbonyl, (C 1 -C 4 alkoxy) carbonyl, dC 4 -haloalkyl, dC 4 -haloalkoxy, CC 4 -haloalkylthio, -C-C -haloalkylsulfinyl, Cι-C 4 - haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C 4 - Haloalkenyl, C 2 -C haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or Benzyl is where R 10 to R 13 have the meanings given above, R 38 is hydrogen, chlorine, cyano, C 1 -C 12 -alkyl, dC 12 -alkoxy, C 1 -C 12 -alkylthio, d-
Cι2-Alkylsulfinyl, Cι-C12-Alkylsulfonyl, d-Cπ-Halogenalkyl, C3-C12-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C -Alkyl, C C -Alkoxy, C C4- Alkylthio, d-C4-Alkylsulfinyl, C C -Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C -Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl, C C4-Halogenalkyl, Cι-C -Halogenalkoxy, C C -Halogenalkylthio, Cι-C4-Halogenalkylsulfϊnyl, C C4- Halogenalkylsulfonyl mit. jeweils 1 bis 9 Fluor-., Chlor- und/oder Bromatomen, C2- C -Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -SO2NR12R13, -(CH2)p R12R13,Cι 2 -alkylsulfinyl, Cι-C 12 alkylsulfonyl, d-Cπ-haloalkyl, C 3 -C 12 cycloalkyl or for each optionally simple to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, Cι -C -alkyl, CC -alkoxy, CC 4 -alkylthio, dC 4 -alkylsulfinyl, CC -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 - Alkenyloxy, (-C-alkyl) carbonyl, (-C-C 4 -alkoxy) carbonyl, CC 4 -haloalkyl, -C-C -haloalkoxy, CC -haloalkylthio, -C-C 4 -haloalkylsulfonyl, CC 4 - haloalkylsulfonyl with. in each case 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -. C haloalkenyl, C 2 -C 4 haloalkenyloxy having in each case 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) p R 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OS02R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OS0 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
mit der Maßgabe, dass R24, R37, R38 oder R31, R37, R38 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 24 , R 37 , R 38 or R 31 , R 37 , R 38 do not simultaneously represent hydrogen,
R39, R40 und R41 unabhängig voneinander für Wasserstoff, C.-Ci∑-Alkyl, C1-Cι2-Alkoxy, d- Ci2-Alkylthio, Cj-Ciz-Alkylsulfinyl, C Cι2-Alkylsulfonyl, d-d2-Halogenalkyl, C3- Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d-C -Alkyl, Cι-C4-Alkoxy, C C4- Alkylthio, Cι-C4-Alkylsulfinyl, C C -Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C4-Alkyl)carbonyl, (Cι-C -Alkoxy)carbonyl5 Cι-C4-Halogenalkyl, Cι-C -Halogenalkoxy, Cι-C -Halogenalkylthio, Cι-C -Halogenalkylsulfinyl, C C4-R 39, R 40 and R 41 are each independently hydrogen, C.-Ci Σ alkyl, C 1 -Cι 2 -alkoxy, d- C 2 alkylthio, Cj-Ciz-alkylsulfinyl, C Cι 2 alkylsulfonyl, dd 2 -Halogenalkyl, C 3 - C 2 -cycloalkyl or for each optionally single to quadruple, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, dC-alkyl, C 1 -C 4 -alkoxy, CC 4 - alkylthio, -CC 4 alkylsulfinyl, CC -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (-C-C 4 -alkyl) carbonyl, (-C-C -alkoxy) carbonyl 5 Cι-C 4 -Halogenalkyl, -C-C -haloalkoxy, Cι-C -haloalkylthio, Cι-C -haloalkylsulfinyl, CC 4 -
Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)S02R13, -OSO2R12 oder -OSO2NR12R13 substitu- iertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenenHaloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy, each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) pN (R 12 ) S0 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 are those given above
Bedeutungen haben,Have meanings
mit der Maßgabe, dass R39, R40, R41 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 39 , R 40 , R 41 do not simultaneously represent hydrogen,
R42 und R43 unabhängig voneinander für Wasserstoff, Cι-Ci2-Alkyl, Cι-C12-Alkoxy, C C12-R 42 and R 43 independently of one another for hydrogen, C 1 -C 2 alkyl, C 1 -C 12 alkoxy, CC 12 -
Alkylthio, Ci-Cn-Alkylsulfinyl, d-C12-Alkylsulfonyl, Cι-Ci2-Halögenalkyl, C3-C12- Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d-C -Alkyl, Cι-C4-Alkoxy, Cι-C4- Alkylthio, C C4-Alkylsulfinyl, C,-C -Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C -Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, Cι-C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, d-C -Halogenalkylsulfinyl, d-C4- Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C -Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, ' -C(R10)=N-ORn, -SO2NR12R13, -(CH2)pNR12R13,Alkylthio, Ci-Cn-alkylsulfinyl, dC 12 -alkylsulfonyl, Cι-Ci 2 -halogenalkyl, C3-C 12 - cycloalkyl or for each optionally up to four times, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, dC -alkyl, -C-C 4 -alkoxy, Cι-C 4 -alkylthio, CC 4 -alkylsulfinyl, C, -C -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 - Alkenyloxy, (-C-alkyl) carbonyl, (-C-C 4 -alkoxy) carbonyl, -C-C 4 -haloalkyl, Cι-C 4 -haloalkoxy, Cι-C 4 -haloalkylthio, dC -haloalkylsulfinyl, dC 4 - haloalkylsulfonyl each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, ' -C (R 10 ) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) pN (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
mit der Maßgabe, dass R24, R42, R43 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 24 , R 42 , R 43 do not simultaneously represent hydrogen,
R44 und R45 unabhängig voneinander für Wasserstoff, Cι-Cι2-Alkyl, Cι-Cι2-Alkoxy, C1-C12- Alkylthio, C Cι2-Alkylsulfinyl, CrCι2-Alkylsulfonyl, d-Cι2-Halogenalkyl, C3-C12- Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,R 44 and R 45 independently of one another are hydrogen, Cι 2 -alkyl, Cι 2 alkoxy, C 1 -C 12 - alkylthio, C Cι 2 alkylsulfinyl, C r Cι 2 alkylsulfonyl, d-Cι 2 - Haloalkyl, C 3 -C 12 -cycloalkyl or for each optionally optionally up to four times, identical or different by fluorine,
Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C,-C4-Alkyl, C C4-Alkoxy, C C4- Alkylthio, Cι-C4-Alkylsulfinyl, Cι-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (C1-C4-Alkyl)carbonyl, (C1-C -Alkoxy)carbonyl, d-C4-Halogenalkyl, Cι-C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C -Halogenalkylsulfinyl, C C4- Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-Chlorine, cyano, formyl, nitro, trimethylsilyl, C, -C 4 alkyl, CC 4 alkoxy, CC 4 alkylthio, C 4 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 - alkenyloxy, (C 1 -C 4 -alkyl) carbonyl, (C 1 -C -alkoxy) carbonyl, dC 4 -haloalkyl, -C-C 4 -haloalkoxy, -C-C 4 -haloalkylthio, Cι- C -haloalkylsulfinyl, CC 4 - haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -
C -Halogenalkenyl, C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substitu-. iertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,C -haloalkenyl, C 2 -C -haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substit -. ized phenyl or benzyl, where R 10 to R 13 have the meanings given above,
mit der Maßgabe, dass R24, R44, R45 oder R31, R44, R45 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 24 , R 44 , R 45 or R 31 , R 44 , R 45 do not simultaneously represent hydrogen,
R46 und R47 unabhängig vonemander für Wasserstoff, Cι-Cι2-Alkyl, Ci-Cπ-Alkoxy, C1-C12-R 46 and R 47 independently of one another for hydrogen, C 1 -C 2 alkyl, C 1 -C 4 alkoxy, C 1 -C 12 -
Alkylthio, d-Cι2-Alkylsulfinyl, Cι-C12-Alkylsulfonyl, Cι-C12-Halogenalkyl, C3-C12- Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d-C -Alkyl, C C -Alkoxy, Cι-C - Alkylthio, Cι-C4-Alkylsulfinyl, Cι-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C4-Älkyl)carbonyl, (C C4-Alkoxy)carbonyl, C C4-Halogenalkyl, Cι-C4-Halogenalkoxy, C1-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, Cι-C4- Halogenalkylsulfonyl mit. jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C4-Halogenalkenyl, C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -S02NR12R13, -(CH2)pNR12R13,Alkylthio, d-Cι 2 alkylsulfinyl, Cι-C 12 alkylsulfonyl, Cι-C 12 haloalkyl, C 3 -C 12 - cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different fluorine, chlorine, cyano, formyl, Nitro, trimethylsilyl, dC -alkyl, CC -alkoxy, Cι-C - alkylthio, Cι-C 4 -alkylsulfinyl, Cι-C 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 - Alkenyloxy, (-C-C 4 -alkyl) carbonyl, (CC 4 -alkoxy) carbonyl, CC 4 -haloalkyl, -C-C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, -C-C 4 -haloalkylsulfinyl, Cι-C 4 - haloalkylsulfonyl with. each 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C 4 haloalkenyl, C 2 -C haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -S0 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R1 )S02R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) pN (R 1 ) S0 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
mit der Maßgabe, dass R46, R47 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 46 , R 47 do not simultaneously represent hydrogen,
R48 und R49 unabhängig voneinander für Wasserstoff, Cι-Cι2-Alkyl, Cι-Cι2-Alkoxy, Cι-CI2- Alkylthio, C Cι2-Alkylsulfjnyl,' Cj-C12-Alkylsulfonyl, Cj-Cπ-Halogenalkyl, C3-C12- Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,R 48 and R 49 independently of one another are hydrogen, Cι 2 -alkyl, Cι 2 -alkoxy, C I2 - alkylthio, C 2 Cι -Alkylsulfjnyl 'Cj-C 12 alkylsulfonyl, Cj-Cπ -haloalkyl , C 3 -C 12 cycloalkyl or for each optionally single to fourfold, identical or different by fluorine,
Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C -Alkyl, C C4-Alkoxy, C C -Al- kylthio, C1-C4-Alkylsulfϊnyl, d-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyl- oxy, (Cι-C4-Alkyl)carbonyl, (Cι-C -Alkoxy)carbonyl, Cι-C4-Halogenalkyl, C C4- Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, C C4-Halo- genalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C -Ha- logenalkenyl, C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(Rl0)=N-ORu, -SO2NR12R13, -(CH2)pNRuR13, -(CH2)pN(R )COR13, -(CH2)pN(R1 )SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,Chlorine, cyano, formyl, nitro, trimethylsilyl, -CC alkyl, CC 4 alkoxy, CC alkyl thio, C 1 -C 4 alkylsulfonyl, dC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 -alkenyloxy, (-CC 4 -alkyl) carbonyl, (-C -alkoxy) carbonyl, -C-C 4 -haloalkyl, CC 4 - haloalkoxy, -C-C 4 -haloalkylthio, -C-C 4 Haloalkylsulfinyl, CC 4 haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C haloalkenyl, C 2 -C haloalkenyloxy, each with 1 to 7 fluorine, chloro and / or bromine atoms, -C (R l0 ) = N-OR u , -SO 2 NR 12 R 13 , - (CH 2 ) p NR u R 13 , - (CH 2 ) p N (R) COR 13 , - ( CH 2 ) p N (R 1 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
mit der Maßgabe, dass R , R nicht gleichzeitig für Wasserstoff stehen,with the proviso that R, R are not simultaneously hydrogen,
R50 und R51 unabhängig voneinander für Wasserstoff, Ci-Cπ-Alkyl, Cι-Cι2-Alkoxy, d-Cι2- Alkylthio, Cj-Cι2-Alkylsulfinyl, Cι-Ci2-Alkylsulfonyl, d-Cπ-Halogenalkyl, C3-Cι2- Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C -Alkyl, Cι-C -Alkoxy, Cι-C4-Al- kylthio, C,-C4-Alkylsulfinyl, d-d-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyl- oxy, (Cι-C -Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, C C4- Halogenalkoxy, C1-C -Halogenalkylthio, Cι-C -Halogenalkylsulfinyl, Cι-C -Halo- genalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C -Ha- logenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,R 50 and R 51 independently of one another for hydrogen, Ci-Cπ-alkyl, Cι-Cι 2 alkoxy, d-Cι 2 - alkylthio, Cj-Cι 2 alkylsulfinyl, Cι-Ci 2 alkylsulfonyl, d-Cπ-haloalkyl, C 3 -C 2 - cycloalkyl or for each optionally single to quadruple, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 -Al- kylthio, C, -C 4 alkylsulfinyl, dd-alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyl oxy, (C 1 -C 4 alkyl) carbonyl, (C 1 -C 4 alkoxy) carbonyl , -C-C 4 haloalkyl, CC 4 - haloalkoxy, C 1 -C -haloalkylthio, Cι-C -haloalkylsulfinyl, Cι-C -halo genalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C ( R 10 ) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) pN (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
mit der Maßgabe, dass R50, R51 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 50 , R 51 do not simultaneously represent hydrogen,
R52 für Wasserstoff, C C12-Alkyl, d-C12-Alkoxy, Cι-C12-Alkylthio, C Ci2- Alkylsulfinyl, d-Cn-Alkylsulfonyl, Ci-Cπ-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-Alkyl, Cι-C4-Alkoxy, d- -Al- kylthio, C C4-Alkylsulfinyl, Cι-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alke- nyloxy, (d-C4-Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl, d-C4-Halogenalkyl, Ci- C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, C.-C -Ha- logenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C - Halogenalkenyl, C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substitu- iertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenenR 52 for hydrogen, CC 12 -alkyl, dC 12 -alkoxy, -C-C 12 -alkylthio, C Ci 2 - alkylsulfinyl, d-Cn-alkylsulfonyl, Ci-Cπ-haloalkyl, C 3 -Cι 2 -cycloalkyl or for each optionally simple to fourfold, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C 1 -C 4 -alkyl, C 1 -C 4 alkoxy, d- -Alkylthio, CC 4 -alkylsulfinyl, C 1 -C 4 -Alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (dC 4 -alkyl) carbonyl, (-C-C 4 -alkoxy) carbonyl, dC 4 -haloalkyl, Ci-C 4 - Halogenalkoxy, -C-C 4 -haloalkylthio, -C-C 4 -haloalkylsulfinyl, C 1 -C 9 -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C - haloalkenyl, C 2 -C -Halogenalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - ( CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 is substituted phenyl or benzyl, where R 10 to R 13 d he indicated above
Bedeutungen haben,Have meanings
R53 für Wasserstoff, Chlor, Cyano, d-Cπ-Alkyl, Cι-C12-Alkoxy, d-Cπ-Alkylthio, C Cι2-Alkylsulfinyl, Cι-Cι2-Alkylsulfonyl, Cι-Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C -Alkyl, Cι-C4-Alkoxy, Cι-C4- Alkylthio, C C4-Alkylsulfinyl, d-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (d-C4-Alkyι)carbonyl, (C C -Alkoxy)carbonyl, Cι-C4-Halogenalkyl, Cι-C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, R 53 for hydrogen, chlorine, cyano, d-Cπ-alkyl, Cι-C 12 alkoxy, d-Cπ-alkylthio, C Cι 2 -alkylsulfinyl, Cι-Cι 2 -alkylsulfonyl, Cι-Cι 2 -haloalkyl, C 3rd -Cι 2 -cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, -CC alkyl, -C-C 4 alkoxy, -CC 4 - alkylthio, CC 4 -Alkylsulfinyl, dC 4 -Alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (dC 4 -alkyl) carbonyl, (CC -alkoxy) carbonyl, -C-C 4 -haloalkyl, -C-C 4 -haloalkoxy, -C-C 4 -haloalkylthio, -C-C 4 -haloalkylsulfinyl,
Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C -Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORn, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR1 R13 substitu- iertes Phenyl oder Benzyl "steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,Haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C haloalkenyl, C 2 -C 4 haloalkenyloxy, each with 1 to 7 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 1 R 13 substituted- ized phenyl or benzyl ", where R 10 to R 13 have the meanings given above,
mit der Maßgabe, dass R52, R53 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 52 , R 53 do not simultaneously represent hydrogen,
R54 für Wasserstoff, Chlor, Cyano, C C12-Alkyl, d-C12-Alkoxy, d-Cπ-Alkylthio, C Cι2-Alkylsulfinyl, Cι-Cι2-Alkylsulfonyl, Cι-Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-Alkyl, C C4-Alkoxy, C C4-R 54 for hydrogen, chlorine, cyano, CC 12 -alkyl, dC 12 -alkoxy, d-Cπ-alkylthio, C Cι 2 -alkylsulfinyl, Cι-Cι 2 -alkylsulfonyl, Cι-Cι 2 -haloalkyl, C 3 -Cι 2 -Cycloalkyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, -C-C 4 alkyl, CC 4 alkoxy, CC 4 -
Alkylthio, Cι-C4-Alkylsulfmyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C - Alkenyloxy, (Cι-C4-Alkyl)carbonyl, (Cι-C -Alkoxy)carbonyl, Cι-C4-Halogenalkyl, Cι-C -Halogenalkoxy, Cι-C4-Halogenalkylthio, d-C4-Halogenalkylsulfinyl, Cι-C4- Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis. R13 die oben angegebenen Bedeutungen haben,Alkylthio, -C-C 4 -alkylsulfmyl, CC 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C - alkenyloxy, (-C-C 4 -alkyl) carbonyl, (-C-C -alkoxy) carbonyl, Cι- C 4 -haloalkyl, -C-C -haloalkoxy, Cι-C 4 -haloalkylthio, dC 4 -haloalkylsulfinyl, Cι-C 4 - haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C 4 - Haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to. R 13 have the meanings given above,
R55 für Wasserstoff, d-Cπ-Alkyl, d-Cι2-Alkoxy, d-d2-Alkylthio, Q-C«- Alkylsulfinyl, Cι-C12-Alkylsulfonyl, Cι-Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι'rC4-Alkyl, d-C4-Alkoxy, C C - Alkylthio, d- -Alkylsulfrnyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-R 55 for hydrogen, d-Cπ-alkyl, d-Cι 2 -alkoxy, dd 2 -alkylthio, QC «- alkylsulfinyl, Cι-C 12 -alkylsulfonyl, Cι-Cι 2 -haloalkyl, C 3 -Cι 2 cycloalkyl or in each case optionally mono- to tetrasubstituted by identical or different fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, Cι 'rC 4 alkyl, dC 4 alkoxy, C - C alkylthio, d- -Alkylsulfrnyl, CC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 -
Alkenyloxy, (Cι-C -Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, d-C4-Halogenalkoxy, Cι-C -Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, Cι-C4- Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C -Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORU, -SO2N 12R13, -(CH2)PNR12R13,Alkenyloxy, (-C-alkyl) carbonyl, (-C-C 4 -alkoxy) carbonyl, -C-C 4 -haloalkyl, dC 4 -haloalkoxy, Cι-C -haloalkylthio, Cι-C 4 -haloalkylsulfinyl, Cι-C 4 - Haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C haloalkenyl, C 2 -C 4 haloalkenyloxy, each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR U , -SO 2 N 12 R 13 , - (CH 2 ) P NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben, mit der Maßgabe, dass R54, R55 nicht gleichzeitig für Wasserstoff stehen, R56 und R57 unabhängig voneinander für Wasserstoff, Ci-Cπ-Alkyl, Cι-C12-Alkoxy, d-Cι2- Alkylthio, d-d2-Alkylsulfinyl, d-C^-Alkylsulfonyl, Cι-Cι2-Halogenalkyl, C3-C.2- Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-Alkyl, Cι-C4-Alkoxy, C C -- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above, with the proviso that R 54 , R 55 are not simultaneously hydrogen, R 56 and R 57 are independently hydrogen, Ci-Cπ-alkyl, Cι-C 12 alkoxy, d-Cι 2 - alkylthio, alkylsulfinyl dd 2, dC ^ alkylsulfonyl, Cι-Cι 2 -haloalkyl, C 3 - C. 2 - Cycloalkyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C 1 -C 4 -alkyl, C 1 -C 4 alkoxy, CC -
Alkylthio, Cι-C4-Alkylsulfinyl, Cι-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C4-Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, Cι-C -Halogenalkoxy, d-C4-Halogenalkylthio, C C -Halogenalkylsulfinyl, d-C4- Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- ■ C4-Halogenalkenyl, C -C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,Alkylthio, -CC 4 -alkylsulfinyl, -C-C 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (-C-C 4 -alkyl) carbonyl, (-C-C 4 -alkoxy) carbonyl, C 1 -C 4 -haloalkyl, C 1 -C -haloalkoxy, dC 4 -haloalkylthio, CC -haloalkylsulfinyl, dC 4 - haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - ■ C 4 - Haloalkenyl, C -C -haloalkenyloxy, each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) pN (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 are substituted phenyl or benzyl where R 10 to R 13 have the meanings given above,
mit der Maßgabe, dass R , R nicht gleichzeitig für Wasserstoff stehen,with the proviso that R, R are not simultaneously hydrogen,
R5 und R unabhängig voneinander für Wasserstoff, Cι-C_2-Alkyl, Ci-Cπ-Alkoxy, C Cι2- Alkylthio, Cι-C12-Alkylsulfinyl, C C12-Alkylsulfonyl, Ci-Cjz-Halogenalkyl, C3-d2- Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d-C4-Alkyl, C C4-Alkoxy, C C - Alkylthio, d-C4-Alkylsulfinyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (C C4-Alkyl)carbonyl,. (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, d-C4-Halogenalkylsulfinyl, Cj-C -R 5 and R independently of one another for hydrogen, C 1 -C 2 -alkyl, Ci-Cπ-alkoxy, C C 2 -alkylthio, C 1 -C 12 -alkylsulfinyl, CC 12 -alkylsulfonyl, Ci-Cjz-haloalkyl, C 3 -d 2 - Cycloalkyl or for each optionally single to quadruple, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, dC 4 -alkyl, CC 4 -alkoxy, CC - alkylthio, dC 4 -alkylsulfinyl, CC 4 -alkylsulfonyl , C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (CC 4 alkyl) carbonyl ,. (-C-C 4 alkoxy) carbonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, dC 4 haloalkylsulfinyl, Cj-C -
Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C4-Halogenalkenyl, C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlόr- und/oder Bromatomen, -C(R10)=N-ORU, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSÖ2NR12R13 substitu- iertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die oben angegebenenHaloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C 4 haloalkenyl, C 2 -C haloalkenyloxy, each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR U , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSÖ 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 are those given above
Bedeutungen haben,Have meanings
mit der Maßgabe, dass R58, R59 nicht gleichzeitig für Wasserstoff stehen, R60 für Wasserstoff, C Cι2-Alkyl, d-Cι2-Alkoxy, C Cι2-Alkylthio, C Cι2- Alkylsulfmyl, C C12-Alkylsulfonyl, Cι-Cι2-Halogenalkyl, C3-C12-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C C4-Alkyl, d-C4-Alkoxy, C C4- Alkylthio, C1-C4-Alkylsulfinyl, d-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-with the proviso that R 58 , R 59 do not simultaneously represent hydrogen, R 60 is hydrogen, Cι C 2 alkyl, d-Cι 2 alkoxy, C Cι 2 alkylthio, C Cι 2 - Alkylsulfmyl, CC 12 alkylsulfonyl, Cι-Cι 2 haloalkyl, C 3 -C 12 cycloalkyl, or for in each case optionally up to four times, identically or differently, by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, CC 4 -alkyl, dC 4 -alkoxy, CC 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, dC 4 -alkylsulfonyl , C 2 -C 4 alkenyl, C 2 -C 4 -
Alkenyloxy, (Cι-C4-Alkyl)carbonyl, (C C4-Alkoxy)carbonyl, C1-C4-Halogenalkyl, Cι-C -Halogenalkoxy, C C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfϊnyl, d-C - Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluorr, Chlor- und/oder Bromatomen, C2- C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, . -SO2NR12R13, -(CH2)PNR12R13,Alkenyloxy, (-C 4 -alkyl) carbonyl, (CC 4 -alkoxy) carbonyl, C 1 -C 4 -haloalkyl, -C-C -haloalkoxy, CC 4 -haloalkylthio, -C-C 4 -haloalkylsulfonyl, dC - haloalkylsulfonyl with in each case 1 to 9 Fluorr, chlorine and / or bromine atoms, C 2 - C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy having in each case 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10) = N-OR n ,. -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
mit der Maßgabe, dass R24 und R60 oder R31 und R60 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 24 and R 60 or R 31 and R 60 do not simultaneously represent hydrogen,
R61 für d-C12-Alkyl, d-C12-Alkoxy, d-C12-Alkylthio, d-C12-Alkylsulfinyl, Cι-d2- Alkylsulfonyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,R 61 for dC 12 -alkyl, dC 12 -alkoxy, dC 12 -alkylthio, dC 12 -alkylsulfinyl, Cι-d 2 - alkylsulfonyl, C 3 -C 2 cycloalkyl or for each optionally single to fourfold, identical or different by fluorine,
Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C C4-Alkyl, Cι-C -Alkoxy, C C4- Alkylthio, C C4-Alkylsulfinyl, d-C4-AIkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C -Alkyl)carbonyl, (d-C -Alkoxy)carbonyl, Cι-C4-Halogenalkyl, d-C -Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C -Halogenalkylsulfϊnyl, d-C - Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-Chlorine, cyano, formyl, nitro, trimethylsilyl, CC 4 alkyl, C 1 -C alkoxy, CC 4 alkylthio, CC 4 alkyl sulfinyl, dC 4 alkyl sulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 - Alkenyloxy, (-C-alkyl) carbonyl, (dC -alkoxy) carbonyl, -C-C 4 -haloalkyl, dC -haloalkoxy, Cι-C 4 -haloalkylthio, Cι-C -haloalkylsulfonyl, dC - haloalkylsulfonyl, each with 1 to 9 Fluorine, chlorine and / or bromine atoms, C 2 -
C4-Halogenalkenyl, C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNRI2R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,C 4 haloalkenyl, C 2 -C haloalkenyloxy each having 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR I2 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
T für Cyano, C C12-Alkyl, CrC12-Alkoxy, Cι-Cι2-Alkylmio, CrCι2-Alkylsulfinyl, CT for cyano, CC 12 alkyl, C r C 12 alkoxy, C 1 -C 2 alkylmio, C r C 2 alkyl sulfinyl, C
Cπ-Alkylsulfonyl, Cι-Cι2-Halogenalkyl, C3-C]2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-Alkyl, CrC4-Alkoxy, Cι-C4-Al- kylthio, d-C4-Alkylsulfinyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyl- oxy, (Cι-C4-Alkyl)carbonyl, (d-C4-Alkoxy)carbonyl, C C4-Halogenalkyl, C C - Halogenalkoxy, d-C4-Halogenall<ylthio, d- -Halogenalkylsulfϊnyl, C C -Halo- genalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C -Ha- logenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,Cπ-alkylsulfonyl, -CC 2 -haloalkyl, C 3 -C ] 2 -cycloalkyl or for each optionally optionally up to four times, identically or differently by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C 1 -C 4 -alkyl, C r C 4 alkoxy, C 1 -C 4 -Al- kylthio, dC 4 alkylsulfinyl, CC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (C 1 -C 4 alkyl) carbonyl, (dC 4 alkoxy) carbonyl, CC 4 -Halogenalkyl, CC - haloalkoxy, dC 4 -Halogenall <ylthio, d- -Halogenalkylsulfϊnyl, CC -Halogenogenalkylsulfonyl each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C -Halogenalkenyl, C 2 -C 4 haloalkenyloxy each having 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
Rw für Cj-Cis-Alkyl, Ci-Ciz-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-Alkyl, Cι-C4-Alkoxy, Cι-C4-Al- kylthio, Cι-C4-Alkylsulfinyl, Cι-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyl- oxy, (Cι-C4-Alkyl)carbonyl, (Cι-C -Alkoxy)carbonyl, Cι-C4-Halogenalkyl, Cι-C4- Halogenalkoxy, d-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, C C4-Halo- genalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Ha- logenalkenyl, C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,R w for Cj-Cis-alkyl, Ci-Ciz-haloalkyl, C 3 -Cι 2 -cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, Cι-C 4 -Alkyl, -CC 4 alkoxy, -C-C 4 -alkyl thio, -C-C 4 -alkylsulfinyl, -C-C 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy , (-CC 4 -alkyl) carbonyl, (-C -alkoxy) carbonyl, -C-C 4 -haloalkyl, -C-C 4 - haloalkoxy, dC 4 -haloalkylthio, -C-C 4 -haloalkylsulfinyl, CC 4 -halo - Genalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C haloalkenyloxy, each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 is substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
R64 für Ci-dz-Alkyl, Cι-C12-Alkoxy, CrC12-Alkylthio, C C12-Alkylsulfinyl, C C12- Alkylsulfonyl, Cι-C12-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-Alkyl, Cι-C -Alkoxy, Cι-C4-R 64 for Ci-dz-alkyl, -C-C 12 alkoxy, CrC 12 -alkylthio, CC 12 -alkylsulfinyl, CC 12 - alkylsulfonyl, -C-C 12 -haloalkyl, C 3 -C 2 -cycloalkyl or for each optionally simple up to fourfold, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C 1 -C 4 alkyl, C 1 -C alkoxy, C 1 -C 4 -
Alkylthio, Cι-C4-Alkylsulfinyl, d-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C -Alkyl)carbonyl, (C1-C -Alkoxy)carbonyl, Cι-C4-Halogenalkyl, Cι-C -Halogenalkoxy, Cι-C4-Haϊogenalkylthio, Cι-C4-Halogenalkylsulfinyl, C!-C4- Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORU, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben, R65 für d-C12-Alkyl, C,-C12-Alkylthio, d-d2-Alkylsulfmyl, d-CI2-Alkylsulfonyl, C Cι2-Halogenalkyl, C3-C12-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-Alkyl, C C4-Alkoxy, C C4- Alkylthio, Cι-C4-Alkylsulfmyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkylthio, Cι-C4-alkylsulfinyl, dC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 - alkenyloxy, (Cι-C alkyl) carbonyl, (C 1 -C -alkoxy) carbonyl, Cι -C 4 -Halogenalkyl, Cι-C -haloalkoxy, Cι-C 4 -Haϊogenalkylthio, Cι-C 4 -haloalkylsulfinyl, C ! -C 4 - haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy, each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR U , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) pN (R 12 ) COR 13 , - (CH 2 ) pN (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 is substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above, R 65 for dC 12 alkyl, C, -C 12 alkylthio, dd 2 alkylsulfmyl, dC I2 alkylsulfonyl, C C 2 haloalkyl, C 3 -C 12 cycloalkyl or for each optionally simple to fourfold, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, -CC 4 -alkyl, CC 4 -alkoxy, CC 4 -alkylthio, -C-C 4 -alkylsulfmyl, CC 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -
Alkenyloxy, (Cι-C4-Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl, C C -Halogenalkyl, Cι-C -Halogenalkoxy, Cι-C -Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, C C - Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORU, -SO2NR12R13, -(CH2)PNR12R13,Alkenyloxy, (-C-C 4 alkyl) carbonyl, (-C-C 4 alkoxy) carbonyl, CC -haloalkyl, Cι-C -haloalkoxy, Cι-C -haloalkylthio, Cι-C 4 -haloalkylsulfinyl, CC - haloalkylsulfonyl with each 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR U , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
R66 für Cι-C12-Alkyl, CrCι2-Alkylthio, d-C12-Alkylsulfinyl, d-Cι2-Alkylsulfonyl, CR 66 for C 1 -C 12 alkyl, CrC 2 alkyl thio, dC 12 alkyl sulfinyl, d 2 -C 2 alkyl sulfonyl, C
Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-Alkyl, C C4-Alkoxy, C C4- Alkylthio, Cι-C4-Alkylsulfinyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C -Alkyl)carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl,-C 2 haloalkyl, C 3 -C 2 cycloalkyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C 1 -C 4 alkyl, CC 4 alkoxy, CC 4 - Alkylthio, -CC 4 -alkylsulfinyl, CC 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 - alkenyloxy, (-C-C4-alkyl) carbonyl, (-C-C 4 -alkoxy) carbonyl, C 1 -C 4 haloalkyl,
Cι-C4-Halogenalkoxy, Cι-C -Halogenalkylthio, Cι-C -Halogenalkylsulfinyl, Cι-C4- Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C -Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben, Cι-C4-haloalkoxy, Cι-C haloalkylthio, Cι-C haloalkylsulfinyl, Cι-C 4 - haloalkylsulphonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C haloalkenyl, C 2 - C 4 haloalkenyloxy each having 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
R67 für d-Cι2-Alkyl, d-Cι2-Halogenalkyl, C3-C12-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,R 67 for d-Cι 2 alkyl, d-Cι 2 -haloalkyl, C 3 -C 12 cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different fluorine,
Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cι-C4-Alkyl, C C4-Alkoxy, Cj-C - Alkylthio, Cι-C4-Alkylsulfmyl, Cι-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4- Alkenyloxy, (Cι-C -Alkyl)carbonyl, (Cι-C -Alkoxy)carbonyl, d-C^-Halogenalkyl, d-C4-Halogenalkoxy, d-C -Halogenall<ylthio, Cι-C4-Halogenalkylsulfinyl, Cι-C4- Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C -Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -S02NR12R13, -(CH2)PNR12R13, -(CH2)pN(R1 )COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,Chlorine, cyano, formyl, nitro, trimethylsilyl, Cι-C 4 alkyl, CC 4 alkoxy, Cj-C - alkylthio, Cι-C 4 -Alkylsulfmyl, Cι-C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 - alkenyloxy, (-C -C alkyl) carbonyl, (-C -C alkoxy) carbonyl, dC ^ -haloalkyl, dC 4 -haloalkoxy, dC -haloalloyl <ylthio, Cι-C 4 -haloalkylsulfinyl, Cι -C 4 - haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C -halogenalkenyl, C 2 -C 4 -halogenalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -S0 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 1 ) COR 13 , - (CH 2 ) pN (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 Is phenyl or benzyl, where R 10 to R 13 have the meanings given above,
,68 für d-Cι2-Alkyl, Cι-C12-Alkoxy, Cι-Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,, 68 d-Cι 2 -alkyl, C 12 -alkoxy, Cι 2 -haloalkyl, C 3 -Cι 2 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different fluorine,
Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C C4-Alkyl, d-C4-Alkoxy, C C - Alkylthio, d-C4-Alkylsulfϊnyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Chlorine, cyano, formyl, nitro, trimethylsilyl, CC 4 -alkyl, dC 4 -alkoxy, CC - alkylthio, dC 4 -alkylsulfonyl, CC 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -
Alkenyloxy, (Cι-C4-Alkyl)carbonyl, (C]-C -Alkoxy)carbonyl, C C4-Halogenalkyl, Cι-C -Halogenalkoxy, d-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfϊnyl, C C - Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2- C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13,Alkenyloxy, (-C-C 4 alkyl) carbonyl, (C] -C -alkoxy) carbonyl, CC 4 -haloalkyl, -C-C -haloalkoxy, dC 4 -haloalkylthio, Cι-C 4 -haloalkylsulfonyl, CC - haloalkylsulfonyl with each 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 - C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
Q steht ganz besonders bevorzugt für einen vollständig ungesättigten 5-gliedrigenQ very particularly preferably represents a completely unsaturated 5-membered
Heterocyclus aus der ReiheHeterocycle from the series
Q steht außerdem ganz besonders bevorzugt für einen vollständig ungesättigten 5- gliedrigen Heterocyclus aus der ReiheQ also very particularly preferably represents a completely unsaturated 5-membered heterocycle from the series
steht außerdem ganz besonders bevorzugt für einen vollständig ungesättigten 5- gliedrigen Heterocyclus aus der Reihe is also very particularly preferably a fully unsaturated 5-membered heterocycle from the series
Q steht außerdem ganz besonders bevorzugt für einen vollständig ungesättigten 5- gliedrigen Heterocyclus aus der ReiheQ also very particularly preferably represents a completely unsaturated 5-membered heterocycle from the series
Q19 Q20 Q24 Q25 Q19 Q20 Q24 Q25
Q steht außerdem ganz besonders bevorzugt für. einen vollständig ungesättigten 5- gliedrigen Heterocyclus aus der ReiheQ also very particularly preferably stands for. a fully unsaturated 5-membered heterocycle from the series
Q26 Q27 Q28 Q29 Q30Q26 Q27 Q28 Q29 Q30
steht außerdem ganz besonders bevorzugt für einen vollständig ungesättigten 5- gliedrigen Heterocyclus aus der Reiheis also very particularly preferably a fully unsaturated 5-membered heterocycle from the series
Q31 Q32 Q33 Q34Q31 Q32 Q33 Q34
steht außerdem ganz besonders bevorzugt für einen vollständig ungesättigten 5- gliedrigen Heterocyclus aus der Reihe is also very particularly preferably a fully unsaturated 5-membered heterocycle from the series
Q35 Q36 Q37 Q38Q35 Q36 Q37 Q38
steht insbesondere ganz besonders bevorzugt für einen vollständig ungesättigten 5- gliedrigen Heterocyclus aus der Reiheis particularly preferably a fully unsaturated 5-membered heterocycle from the series
Q31 Q34 Q31 Q34
steht außerdem insbesondere ganz besonders bevorzu t für einen vollständig ungesättigten 5-gliedrigen Heterocyclus aus der Reiheis also particularly preferred t for a fully unsaturated 5-membered heterocycle from the series
Q35 Q38Q35 Q38
R14 und R15 stehen unabhängig voneinander bevorzugt für Wasserstoff, Chlor, Cyano, C1-C5- Alkyl, Cι-C5-Alkoxy, d-C5-Alkylthio, d-C3-Alkylsulfinyl, C C3-Alkylsulfonyl, Cι-C5-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cyclo- alkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor,R 14 and R 15 independently of one another preferably represent hydrogen, chlorine, cyano, C 1 -C 5 -alkyl, -C-C 5 alkoxy, dC 5 -alkylthio, dC 3 -alkylsulfinyl, CC 3 -alkylsulfonyl, Cι-C 5 Haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or for each optionally single to quadruple, identical or different by chlorine,
C,-C4-Alkyl, d-C4-Alkoxy, Cι-C4-Alkylthio, d- -Alkylsulfinyl, d-C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C4-Halogenalkyl, Cι-C -Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C -Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -(CH2)pN(R12)SO2R13, oder -OSÖ2NR12R13 substituiertes Phenyl oder ' Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.C, -C 4 -alkyl, dC 4 -alkoxy, Cι-C 4 -alkylthio, d- -alkylsulfinyl, dC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, Cι-C 4 -haloalkyl, Cι-C -haloalkoxy , -C-C 4 -haloalkylthio, -C-C -halo-alkylsulfinyl, -C-C 4 -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSÖ 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R14 und R15 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-R 14 and R 15 independently of one another particularly preferably represent hydrogen, chlorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neo-
Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methyl- t io, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.Pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methyl t io, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, methyl, ethyl, n-propyl, iso- Propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R14 und R15 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durchR 14 and R 15 independently of one another very particularly preferably represent hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or for each optionally single or double, identical or different
Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.Fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl.
R16 steht bevorzugt für Wasserstoff, Cyano, d-C5-Alkyl, C C5-Alkoxy, C1-C5- Alkylthio, Ci-d-Alkylsulfinyl, d-d-Alkylsulfonyl, Ci-d-Halogenalkyl mit 1 bis 9R 16 preferably represents hydrogen, cyano, dC 5 -alkyl, CC 5 -alkoxy, C 1 -C 5 -alkylthio, Ci-d-alkylsulfinyl, dd-alkylsulfonyl, Ci-d-haloalkyl with 1 to 9
Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor,Fluorine, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or for each optionally one to four times, identical or different by chlorine,
Cι-C4-Alkyl, d-C4-Alkoxy, C C4-Alkylthio, Cι-C4-Alkylsulfinyl, C C -C 1 -C 4 -alkyl, dC 4 -alkoxy, CC 4 -alkylthio, -C-C 4 -alkylsulfinyl, CC -
Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C4-Halogenalkyl, C C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, C C -Halogen- alkylsulfinyl, Cι-C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor-Alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, C 1 -C 4 -haloalkyl, CC 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, CC -haloalkylsulfinyl, Cι-C -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine
. und/oder Bromatomen, -C(R10)=N-ORU, -(CH2)pN(R12)SO2R13, oder -OSÖ2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen, and / or bromine atoms, -C (R 10 ) = N-OR U , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSÖ 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 the above
Bedeutungen haben.Have meanings.
R16 steht besonders bevorzugt für Wasserstoff, Cyano, Methyl, Ethyl, n-Propyl, iso- Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso- Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder fur jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,R 16 particularly preferably represents hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for in each case optionally up to four times, the same or different by fluorine,
Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n-Chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-
Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3,Propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 ,
-N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes-N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3
. Phenyl oder Benzyl., Phenyl or benzyl.
R16 steht. ganz besonders bevorzugt für Wasserstoff, Cyano, Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 16 stands. very particularly preferably for hydrogen, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio, trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
R17 und R19 stehen unabhängig voneinander bevorzugt für Wasserstoff, Cyano, C C5-Alkyl,R 17 and R 19 independently of one another preferably represent hydrogen, cyano, CC 5 alkyl,
Ci-d-Alkoxy, C C5-Alkylthio, d-C5-Alkylsulfinyl, Cι-C5-Alkylsulfonyl, C C5- Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, C C4-Alkoxy, d- -Alkylthio, Cι-C4-Alkylsulfinyl, d-C4-Ci-d-alkoxy, CC 5 alkylthio, dC 5 alkylsulfinyl, C 5 -C 5 alkylsulfonyl, CC 5 - haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally up to four times, identically or differently, by chlorine, -CC 4 -alkyl, CC 4 -alkoxy, d- -alkylthio, -C-C 4 -alkylsulfinyl, dC 4 -
Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C4-Halogenalkyl, d-C -Halogenalkoxy, d-C4-Halogenalkylthio, CrC4-Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenenAlkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, -C-C 4 haloalkyl, dC -haloalkoxy, dC 4 -haloalkylthio, C r C 4 -haloalkylsulfinyl, Cι-C 4 -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine - and / or bromine atoms, -C (R 10 ) = N-OR π , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 the above
Bedeutungen haben.Have meanings.
R17 und R19 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Cyano, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio,R 17 and R 19 independently of one another particularly preferably represent hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy , iso-propoxy, n-butoxy, tert-butoxy, methylthio,
Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, • -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.Ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different, by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n -Butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , • -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF3, -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R17 und R19 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Cyano, Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso- Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durchR 17 and R 19 independently of one another very particularly preferably represent hydrogen, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, iso- Propylthio, tert-butylthio, trifluoromethyl or for each optionally single or double, identical or different
Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.Fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl.
R18 steht bevorzugt für Wasserstoff, Chlor, Cyano, Cι-C5-Alkyl, Ci-d-Alkoxy, C C5- Alkylthio, C C5-Alkylsulfinyl, d-d-Alkylsulfonyl, Ci-d-Halogenalkyl mit 1 bis 9R 18 preferably represents hydrogen, chlorine, cyano, C 5 alkyl, Ci-d-alkoxy, CC 5 - alkylthio, alkylsulfinyl 5 CC, dd alkylsulfonyl, Ci-d-haloalkyl having 1 to 9
Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, d-C4-Alkoxy, d- -Alkylthio, Cι-C4-Alkylsulfιnyl, C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C -Halogenalkyl, Cι-C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, C C4-Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORπ, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.Fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally single to fourfold, the same or different by chlorine, -C 4 alkyl, dC 4 alkoxy, d- alkylthio, Cι- C 4 -Alkylsulfιnyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, Cι-C -haloalkyl, Cι-C 4 -halogenalkoxy, Cι-C 4 -haloalkylthio, CC 4 -haloalkylsulfinyl, Cι-C 4 - Haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N-OR π , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R steht besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso- Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,R particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy , n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different by fluorine,
Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.Chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R18 steht ganz besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, iso- Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 18 very particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert -Butylthio, trifluoromethyl or phenyl or benzyl, each of which is mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
R20 und R23 stehen unabhängig vonemander bevorzugt für Wasserstoff, Ci-d-Alkyl, C.-d- Alkoxy, Ci-Cs-Alkylthio, Cι-C5-Alkylsulfinyl, d-d-Alkylsulfonyl, C C5-Halogen- alkylmit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, C C4-Alkoxy, C C4-Alkylthio, C C4-Alkylsulfinyl, d-C4-R 20 and R 23 are independently vonemander preferably represents hydrogen, Ci-e-alkyl, C. -d- alkoxy, Ci-Cs-alkylthio, -C-C 5 alkylsulfinyl, dd-alkylsulfonyl, CC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally up to four times, identically or differently by chlorine, -CC 4 -alkyl, CC 4 -alkoxy, CC 4 -alkylthio, CC 4 -alkylsulfinyl, dC 4 -
Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, .Methoxycarbonyl, Ethoxycarbonyl, Cι-C4-Halogenalkyl, d-C -Halogenalkoxy, Cj-C4-Halogenalkylthio, C C4-Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenenAlkylsulfonyl, methylcarbonyl, ethylcarbonyl, .Methoxycarbonyl, ethoxycarbonyl, Cι-C 4 haloalkyl, dC haloalkoxy, Cj-C 4 haloalkylthio, CC 4-halo-alkylsulfinyl, Cι-C4-haloalkylsulfonyl having in each case 1 to 9 fluorine, Chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 the above
Bedeutungen haben.Have meanings.
R20 und R23 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-R 20 and R 23 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso -Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-
Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl. R20 und R23 stehen unabhän ig vonemander ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, . Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durchPropylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert -Butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N -OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N ( H) CH 3 substituted phenyl or benzyl. R 20 and R 23 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio,. Ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or for each, optionally single or double, the same or different
Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.Fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl.
R21 und R22 stehen unabhängig voneinander bevorzugt für Wasserstoff, Chlor, Cyano, Ci-d- Alkyl, d-d-Alkoxy, d-Cj-Alkylthio, C C5-Alkylsulfinyl, d-d-Alkylsulfonyl,R 21 and R 22 independently of one another preferably represent hydrogen, chlorine, cyano, Ci-d-alkyl, dd-alkoxy, d-Cj-alkylthio, CC 5 -alkylsulfinyl, dd-alkylsulfonyl,
Ci-d-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, d-d-Cyclo- alkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, Cι-C4-Alkoxy, C C4-Alkylthio, Cι-C4-Alkylsulfinyl, C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl,Ci-d-haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, dd-cycloalkyl or for each optionally one to four times, the same or different by chlorine, -CC 4 alkyl, -C-C 4 - Alkoxy, CC 4 alkylthio, C 1 -C 4 alkylsulfinyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,
Cι-C4-Halogenalkyl, C C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)SO2R13, oder -OS02NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.Cι-C 4 haloalkyl, CC 4 haloalkoxy, Cι-C4-haloalkylthio, Cι-C 4 alkylsulfinyl-halo, Cι-C4-haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, - C (R 10 ) = N-OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OS0 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above to have.
R21 und R22 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, ήeo- Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methyl- thio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3,R 21 and R 22 independently of one another are particularly preferably hydrogen, chlorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, eo-pentyl, methoxy, ethoxy, n -Propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally simple to fourfold, identical or different from fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 ,
-C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl. R und R22 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy,. Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch-C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl. R and R 22 independently of one another very particularly preferably represent hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy. Methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or, for each, optionally single or double, identical or different
Fluor, Chlor, Methyl, Ethyl,. iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.Fluorine, chlorine, methyl, ethyl ,. iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl.
R24 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso- Butyl, sek-Butyl, tert-Butyl oder Cyclopropyl.R 24 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or cyclopropyl.
R24 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl oder Cyclopropyl.R 24 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl or cyclopropyl.
R24 steht ganz besonders bevorzugt für Wasserstoff. Methvl oder CvclopropvlR 24 very particularly preferably represents hydrogen. Methvl or Cvclopropvl
R25 und R26 stehen unabhängig voneinander bevorzugt für Wasserstoff, Chlor, Cyano, C1-C5- Alkyl, Ci-d-Alkoxy, Ci-d-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor,R 25 and R 26 independently of one another preferably represent hydrogen, chlorine, cyano, C 1 -C 5 -alkyl, Ci-d-alkoxy, Ci-d-haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C. 3 -C 6 -cycloalkyl or for each optionally one to four times, identical or different by chlorine,
Cι-C4-Alkyl, C C -Alkoxy, d-C4-Alkylthio, C C4-Alkylsulfinyl, C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cj-C -Halogenalkyl, Cι-C4-Halogenalkoxy, d-C4-Halogenalkylthio, C C4-Halogen- alkylsulfinyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORU, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.C 1 -C 4 -alkyl, CC -alkoxy, dC 4 -alkylthio, CC 4 -alkylsulfinyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, Cj-C -haloalkyl, Cι-C 4 -haloalkoxy, dC 4 - Haloalkylthio, CC 4 haloalkylsulfinyl, CC 4 haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N-OR U , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R25 und R26 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-R 25 and R 26 independently of one another particularly preferably represent hydrogen, chlorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neo-
Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,Pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different by fluorine,
Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, . -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)S02CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.Chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 ,. -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) S0 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R25 und R26 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch ■ Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 25 and R 26 independently of one another very particularly preferably represent hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl or for each optionally phenyl or benzyl substituted once or twice, identically or differently by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
R27 steht bevorzugt für Wasserstoff, d-C5-Alkyl, Ci-d-Alkoxy, d-C5-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor,R 27 preferably represents hydrogen, dC 5 -alkyl, Ci-d-alkoxy, dC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or each optionally up to four times , same or different by chlorine,
Cι-C4-Alkyl, C C4-Alkoxy, d-C4-Alkylthio, C C4-Alkylsulfιnyl, C C4-Alkylsulfo- nyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C4-Ha- logenalkyl, C C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, C C -Halogenalkylsulfi- nyl, Cι-C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Brom- atomen, -C(R10)=N-ORπ, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertesC 1 -C 4 -alkyl, CC 4 -alkoxy, dC 4 -alkylthio, CC 4 -alkylsulfonyl, CC 4 -alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, Cι-C 4 -haloalkyl, CC 4 -haloalkoxy , -C-C 4 -haloalkylthio, CC -haloalkylsulfonyl, -C-C -haloalkylsulfonyl each with 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , - ( CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted
Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.Phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R27 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-O.CH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3,R 27 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n- Butoxy, tert-butoxy, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different by fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n - Propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = NO.CH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 ,
-N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.-N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R27 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, iso-Propyl, tert- Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 27 very particularly preferably represents hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
R28 und R30 stehen unabhängig voneinander bevorzugt für Wasserstoff, Ci-Cs-Alkyl, C1-C5-R 28 and R 30 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, C 1 -C 5 -
Alkoxy, Ci-d-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3- C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, d-GrAlkyl, Cι-C4-Alkoxy, d-C4-Alkylthio, d-C4-Alkylsulfinyl, C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl,Alkoxy, Ci-d-haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 - C 6 cycloalkyl or for each optionally optionally up to four times, identically or differently by chlorine, d-alkyl, C 1 -C 4 -Alkoxy, dC 4 -alkylthio, dC 4 -alkylsulfinyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,
Cι-C4-Halogenalkyl, C C4-Halogenalkoxy, C1-C4-Halogenalkylthio, CrC4-Halogen- alkylsulfinyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.Cι-C 4 haloalkyl, CC 4 -haloalkoxy, C 1 -C 4 haloalkylthio, C r C 4-halo-alkylsulfinyl, CC 4 haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and bromine atoms or, -C ( R 10 ) = N-OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R28 und R30 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n- Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, nrPropyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)==N-OCH3, -C(CH3)=N-OCH3,R 28 and R 30 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso -Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different, by fluorine, chlorine, Methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) == N-OCH 3 , -C (CH 3 ) = N-OCH 3 ,
-C(H)=N-OC2H5, -C(CH3)=N-OC2Hs, -N(H)S02CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.-C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H s , -N (H) S0 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R28 und R30 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff,R 28 and R 30 independently of one another very particularly preferably represent hydrogen,
Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl. R29 steht bevorzugt für Wasserstoff, Chlor, Cyano, C C5-Alkyl, C C5-Alkoxy, C C5- Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-.Cycloalkyi oder für j eweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, d-C4-Alkyl, C C -Alkoxy, Cι-C4-Alkylthio, d-C4-Alkylsulfinyl, C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C4-Halogenalkyl, C C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, Ci-Q-Halogen- alkylsulfinyl, Cι-C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes- Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.Methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, methoxy, ethoxy, iso-propoxy, tert-butoxy, trifluoromethyl or for each optionally single or double, identical or different by fluorine, chlorine, methyl, ethyl, iso Propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl. R 29 preferably represents hydrogen, chlorine, cyano, CC 5 alkyl, CC 5 alkoxy, CC 5 - haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for j sometimes optionally up to four times, identical or different, by chlorine, dC 4 alkyl, CC alkoxy, C 1 -C 4 alkylthio, dC 4 alkyl sulfinyl, CC 4 alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, Cι-C 4 -Halogenalkyl, CC 4 -haloalkoxy, -C-C 4 -haloalkylthio, Ci-Q-halogeno-alkylsulfinyl, -C-C -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted- phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R29 steht besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3,R 29 particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso- Propoxy, n-butoxy, tert-butoxy, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different by fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy , Ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 ,
-C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.-C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R29 steht ganz besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, iso-R 29 very particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, iso-
Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl. •Propyl, tert-butyl, neo-pentyl, methoxy, ethoxy, iso-propoxy, tert-butoxy, trifluoromethyl or for each optionally single or double, identical or different, by fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl , Methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl. •
R31 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso- Butyl, sek-Butyl, tert-Butyl oder Cyclopropyl, oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, d-C4-Alkoxy, . d-C4-Alkylthio, C C4-Alkylsulfinyl, • C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C -Halogenalkyl, d-Q-Halogenalkoxy, Cι-C4-Halogenalkylthio, C C -Halogen- alkylsulfinyl, d-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -(CH2)PN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenenR 31 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or cyclopropyl, or each optionally up to four times, identically or differently, by chlorine , -C-C 4 alkyl, dC 4 alkoxy,. dC 4 alkylthio, CC 4 alkylsulfinyl, • CC 4 - Alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, -C-C -haloalkyl, dQ-haloalkoxy, Cι-C 4 -haloalkylthio, CC -halo-alkylsulfinyl, dC 4 -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or Bromine atoms, -C (R 10 ) = N-OR n , - (CH 2 ) P N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 are the given above
Bedeutungen haben.Have meanings.
R31 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl oder Cyclopropyl, oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,R 31 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl or cyclopropyl, or each in each case optionally up to four times, identically or differently, by fluorine,
Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertesChlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted
Phenyl oder Benzyl.Phenyl or benzyl.
R31 steht ganz besonders bevorzugt für Wasserstoff, Methyl oder Cyclopropyl, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 31 very particularly preferably represents hydrogen, methyl or cyclopropyl, or in each case, if appropriate, once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert -Butoxy substituted phenyl or benzyl.
R32 und R34 stehen unabhängig voneinander bevorzugt für Wasserstoff, Ci-Cs-Alkyl, Ci- - Alkoxy, Ci-Cs-Alkylthio, CrC3-Alkylsulfmyl, Cι-C5-Alkylsulfonyl, d-C5-Halogen- alkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, C C4-Alkoxy, Cι-C4-Alkylthio, Cι-C4-Alkylsulfinyl, C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, C C -Halogenalkyl, Cι-C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, CrC4-Halogen- alkylsulfinyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORU, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben. R32 und R34 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl,R 32 and R 34 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, Ci- - alkoxy, Ci-Cs-alkylthio, C r C 3 -alkylsulfmyl, -C-C 5 -alkylsulfonyl, dC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally single to quadruple, the same or different by chlorine, -C 4 alkyl, CC 4 alkoxy, C 1 -C 4 -Alkylthio, -C-C 4 -alkylsulfinyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, CC -haloalkyl, -C-C 4 -haloalkoxy, Cι-C 4 -haloalkylthio, C r C 4 -haloalkylsulfinyl, CC 4 haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR U , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above. R 32 and R 34 independently of one another particularly preferably represent hydrogen, methyl,
Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy,Ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy,
Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-
Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3,Propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert -Butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N -OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 ,
-N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.-N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R32 und R34 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 32 and R 34 independently of one another very particularly preferably represent hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or phenyl substituted by fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy, optionally monosubstituted or disubstituted in each case or benzyl.
R33 steht bevorzugt für Wasserstoff, Chlor, Cyano, d-C5-Alkyl, Ci-d-Alkoxy, C C5- Alkylthio, Cι-C5-Alkylsulfinyl, d-C5-Alkylsulfonyl, d-C5-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor,R 33 preferably represents hydrogen, chlorine, cyano, dC 5 -alkyl, Ci-d-alkoxy, CC 5 - alkylthio, -C-C 5 -alkylsulfinyl, dC 5 -alkylsulfonyl, dC 5 -haloalkyl with 1 to 9 fluoro-, Chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally single to fourfold, identical or different by chlorine,
Cι-C4-Alkyl, d-C4-Alkoxy, Cι-C4-Alkylthio, Cι-C4-Alkylsulfinyl, C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, C C4-Halogenalkyl, Cι-C -Halogenalkoxy, Cι-C -Halogenalkylthio, Cι-C4-Halogen- alkylsulfmyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(RI0)=N-ORπ, -(CH2)pN(R12)S02R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.C 1 -C 4 -alkyl, dC 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, CC 4 -haloalkyl, Cι-C -halalkalkoxy, Cι-C haloalkylthio, Cι-C 4 alkylsulfmyl-halo, Cι-C π 4 haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R I0) = N-oR, - ( CH 2 ) p N (R 12 ) S0 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R33 steht besonders bevorzugt für Wasserstoff, Cyano, Methyl, Ethyl, n-Propyl, iso- Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso- Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder • für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, . -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.R 33 particularly preferably represents hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso- Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or • for each optionally one to four times, identical or different, by fluorine, chlorine, Methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso- Propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 . -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R33 steht ganz besonders bevorzugt für Wasserstoff, Cyano, Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 33 very particularly preferably represents hydrogen, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio , Trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently by fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy.
R35 und R36 stehen unabhängig voneinander bevorzugt für Wasserstoff, Ci-Cs-Alkyl, C1-C5- Alkoxy, d-Cs-Alkylthio,'d-Cs-Alkylsulfϊnyl, C.-Cs-Alkylsulfonyl, C,-C3-Halogen- alkyl mit 1 bis 9 Fluor-, Chlor- und oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, C C4-Alkoxy, C C4-Alkylsulfinyl, CrC4-Alkylsulfo- nyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C4-Ha- logenalkyl, C C4-Halogenalkoxy, C C4-Halogenalkylthio, Cι-C -Halogenalkylsulfi- nyl, Cι-C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.R 35 and R 36 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, C 1 -C 5 -alkoxy, d-Cs-alkylthio, ' d-Cs-alkylsulfonyl, C.-Cs-alkylsulfonyl, C, -C 3 -Halogen- alkyl with 1 to 9 fluorine, chlorine and or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally optionally up to four times, identically or differently by chlorine, -C-C 4 alkyl, CC 4 alkoxy . CC 4 alkylsulfinyl, C r C 4 -Alkylsulfo- nyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, Cι-C logenalkyl 4 -Ha-, CC 4 -haloalkoxy, CC 4 haloalkylthio, Cι-C -Halogenalkylsulfi- nyl, Cι -C -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R35 und R36 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy,R 35 and R 36 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy,
Ethoxy, n-Propoxy, .iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Ethoxy, n-propoxy, .iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-
Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für j eweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3,- -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.Propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or, in each case, optionally up to four times, identically or differently, by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n- Propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , - -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl ,
R35 und "R36 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl,- iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Tri- fluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 35 and " R 36 independently of one another very particularly preferably represent hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, Ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or for each optionally single or double, identical or different by fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert -Butoxy substituted phenyl or benzyl.
R37 steht bevorzugt für Wasserstoff, Ci-Cs-Alkyl, CrC5-Alkoxy, Ci-d-Alkylthio, C C5-R 37 preferably represents hydrogen, Ci-Cs-alkyl, C r C 5 -alkoxy, Ci-d-alkylthio, CC 5 -
Alkylsulfinyl, d-d-Alkylsulfonyl, d-d-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, d-Q-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, d-C4-Alkyl, Cι-C -Alkoxy, Cι-C4-Alkylthio, C C4-Alkylsulfinyl, d- - Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl,Alkylsulfinyl, dd-alkylsulfonyl, dd-haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, dQ-cycloalkyl or for each optionally one to four times, the same or different by chlorine, dC 4 alkyl, C 1 -C 4 alkoxy , -C-C 4 alkylthio, CC 4 alkylsulfinyl, d - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,
Cι-C4-Halogenalkyl, Cι-C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, C C -Halogen- alkylsulfinyl, Cι-C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)SO2R13, oder -OS02NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 4 -C 4 haloalkylthio, CC halo alkylsulfinyl, C 1 -C 4 haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, -C ( R 10 ) = N-OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OS0 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R37 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n- Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OS02N(H)CH3 substituiertes Phenyl oder Benzyl.R 37 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n- Butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally optionally up to four times, identically or differently, by fluorine, chlorine, methyl, ethyl, n -Propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio , tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N- OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OS0 2 N (H) CH 3 substituted phenyl or benzyl.
R37 steht ganz besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, iso- Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, isό-Propoxy, . tert-Butoxy substituiertes Phenyl oder Benzyl/R 37 very particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert butylthio, trifluoromethyl, or represents in each case optionally monosubstituted or disubstituted by identical or different fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, isό-propoxy. tert-butoxy substituted phenyl or benzyl /
R38 steht bevorzugt für Wasserstoff, Chlor, Cyano, Ci-Cs-Alkyl, d-C5-Alkoxy, Cι-C5- Alkylthio, Ci-d-Alkylsulfinyl, C C5-Alkylsulfonyl, d-d-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, C C4-Alkoxy, C C4-Alkylthio, C C4-Alkylsulfinyl, C C4-R 38 preferably represents hydrogen, chlorine, cyano, Ci-Cs-alkyl, dC 5 -alkoxy, Cι-C 5 -alkylthio, Ci-d-alkylsulfinyl, CC 5 -alkylsulfonyl, dd-haloalkyl with 1 to 9 fluoro-, Chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally single to quadruple, identical or different by chlorine, -C 4 alkyl, CC 4 alkoxy, CC 4 alkylthio, CC 4 alkylsulfinyl, CC 4 -
Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C -Halogenalkyl, Cι-C -Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C -Halogen- alkylsulfinyl, d-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORU, -(CH2)pN(R12)S02R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenenAlkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, -C-C -haloalkyl, Cι-C -haloalkoxy, Cι-C 4 -haloalkylthio, -C-C -haloalkylsulfinyl, dC 4 -haloalkylsulfonyl, each with 1 to 9 fluoro, chlorine - and / or bromine atoms, -C (R 10 ) = N-OR U , - (CH 2 ) p N (R 12 ) S0 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 the above
Bedeutungen haben.Have meanings.
R38 steht besonders bevorzugt für Wasserstoff, Cyano, Methyl, Ethyl, n-Propyl, iso- Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso- Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3,R 38 particularly preferably represents hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-Butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different, by fluorine, chlorine, methyl, ethyl , n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n -Butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 ,
-C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, . -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OS02N(H)CH3 substituiertes Phenyl oder Benzyl. R38 steht ganz besonders bevorzugt für Wasserstoff, Cyano, Methyl,. Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, .Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.-C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 ,. -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OS0 2 N (H) CH 3 substituted phenyl or benzyl. R 38 very particularly preferably represents hydrogen, cyano, methyl ,. Ethyl, iso-propyl, tert-butyl, neo-pentyl, methoxy, ethoxy, iso-propoxy, tert-butoxy, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or for each optionally single or double, identical or different phenyl or benzyl substituted by fluorine, chlorine, methyl, .ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy.
R39, R40 und R41 stehen unabhängig voneinander bevorzugt für Wasserstoff, Ci-Cs-Alkyl, d- Cs-Alkoxy, Ci-Cs-Alkylthio, d-C5-Allcylsulfinyl, Cι-C5-Alkylsulfonyl, Ci-d-Halo- genalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oderR 39 , R 40 and R 41 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, d-Cs-alkoxy, Ci-Cs-alkylthio, dC 5 -allcylsulfinyl, Cι-C 5 -alkylsulfonyl, Ci-d-halo - Genalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or
.für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, Cι-C4-Alkoxy, d-d-Alkylthio, C C4-Alkylsulfinyl, C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C -Halogenalkyl, Cι-C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, C C4-Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.. for each optionally single to quadruple, the same or different by chlorine, -C 4 alkyl, -C 4 alkoxy, dd-alkylthio, CC 4 -alkylsulfinyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, Cι-C haloalkyl, Cι-C4-haloalkoxy, Cι-C4-haloalkylthio, CC 4-halo-alkylsulfinyl, Cι-C4-haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , - (CH 2 ) pN (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R39, R40 und R41 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff,R 39 , R 40 and R 41 independently of one another particularly preferably represent hydrogen,
Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,Methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, Ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally single to fourfold, identical or different by fluorine,
Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertesChlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted
Phenyl oder Benzyl.Phenyl or benzyl.
R39, R40 und R41 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 39 , R 40 and R 41 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-Butoxy, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or for each optionally single or double, identical or different by fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso -Propoxy, tert-butoxy substituted phenyl or benzyl.
R42 undJR43 stehen unabhängig voneinander bevorzugt für Wasserstoff, Ci-Cs-Alkyl, C1-C5- Alkoxy, Ci-d-Alkylthio, Cι-C5-Alkylsulfinyl, C C5-Alkylsulfonyl, Ci-d-Halogen- alkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor,R 42 and JR 43 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, C 1 -C 5 -alkoxy, Ci-d-alkylthio, -C-C 5 -alkylsulfinyl, CC 5 -alkylsulfonyl, Ci-d-haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally optionally up to four times, identical or different by chlorine,
Cι-C4-Alkyl, CrC4-Alkoxy, Cι-C4-Alkylthio, Cι-C4-Alkylsulfinyl, C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C4-Halogenalkyl, Cι-C -Halogenalkoxy, C C -Halogenalkylthio, C C4-Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.C 1 -C 4 alkyl, C r C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, C 1 -C 4 -haloalkyl, Cι- C -haloalkoxy, CC -haloalkylthio, CC 4 -halo-alkylsulfinyl, -C-C 4 -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N-OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R42 und R43 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy,R 42 and R 43 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy,
Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-
Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n-Propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally single to fourfold, identically or differently by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert -Butyl, methoxy, ethoxy, n-
Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.Propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R42 und R43 stehen unabhängig vonemander ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 42 and R 43 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio, trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
R44 und R45 stehen unabhängig voneinander bevorzugt für Wasserstoff, Ci-Cs-Alkyl, C C5-R 44 and R 45 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, CC 5 -
Alkoxy, Ci-Cs-Alkylthio, Ci-Cs-Alkylsulfrnyl, Ci-d-Alkylsulfonyl, d-d-Halogen- alkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, d-C4-Alkyl, Cι-C4-Alkoxy, Cι-C4-Alkylthio, C,-C4-Alkylsulfinyl, C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl,Alkoxy, Ci-Cs-alkylthio, Ci-Cs-alkylsulfonyl, Ci-d-alkylsulfonyl, dd-haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally simple to quadruple, identical or different, by chlorine, dC 4 -alkyl, Cι-C 4 -alkoxy, Cι-C 4 -alkylthio, C, -C 4 -alkylsulfinyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,
Cι-C4-Halogenalkyl, d-C -Halogenalkoxy, C C -Halogenalkylthio, Ci-Q-Halogen- alkylsulfinyl, Cι-C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.-C-C 4 haloalkyl, dC -haloalkoxy, CC -haloalkylthio, Ci-Q-haloalkylsulfinyl, -C-C -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N -OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R44 und R45 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n- Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3,R 44 and R 45 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso -Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different, by fluorine, chlorine, Methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso- Propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 ,
-C(H)=N-OC2H5, , -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.-C (H) = N-OC 2 H 5 ,. -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , - N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R44 und R4S stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff,R 44 and R 4S independently of one another very particularly preferably represent hydrogen,
Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.Methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, methoxy, ethoxy, iso-propoxy, tert-butoxy, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
R46 und R47 stehen unabhängig voneinander bevorzugt für Wasserstoff, Ci-Cs-Alkyl, d-C5- •R 46 and R 47 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, dC 5 - •
Alkoxy, Ci-Cs-Alkylthio, Cι-C5-Alkylsulfinyl, Ci-Cs-Alkylsulfonyl, Ci-d-Halogen- alkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, d-C4-Alkyl, C C -Alkoxy, Cι-C4-Alkylthio, Cι-C4-Alkylsulfmyl, d-C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl,Alkoxy, Ci-Cs-alkylthio, -C-C 5 alkylsulfinyl, Ci-Cs-alkylsulfonyl, Ci-d-haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally single to quadruple, identical or different by chlorine, dC 4 alkyl, CC alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfmyl, dC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,
Cι-C -Halogenalkyl, Cι-C4-Hälogenalkoxy, Cι-C -Halogenalkylthio, Cι-C4-Halogen- alkylsulfinyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C R-^ -OR11, -(CH2)PN(R12)S02R13, oder -OSO2NR1 R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C haloalkylthio, C 1 -C 4 haloalkylsulfinyl, CC 4 haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, -C R - ^ -OR 11 , - (CH 2 ) P N (R 12 ) S0 2 R 13 , or -OSO 2 NR 1 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R46 und R47 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n- Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,R 46 and R 47 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso -Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different by fluorine,
• Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n-Chlorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-
Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3,Propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 ,
-C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.-C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R46 und R47 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff,R 46 and R 47 independently of one another very particularly preferably represent hydrogen,
Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, 'tert-Butoxy substituiertes Phenyl oder Benzyl.Methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, methoxy, ethoxy, iso-propoxy, tert-butoxy, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
R48 und R49 stehen unabhängig voneinander bevorzugt für Wasserstoff, d-Cs-Alkyl, CrC5-R 48 and R 49 independently of one another preferably represent hydrogen, d-Cs-alkyl, C r C 5 -
Alkoxy, Ci-Cs-Alkylthio, d-d-Alkylsulfinyl, Ci-d-Alkylsulfonyl, C C5-Halogen- alkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, C C4-Alkoxy, Cι-C4-Alkylthio, C C4-Alkylsulfinyl, C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl,Alkoxy, Ci-Cs-alkylthio, dd-alkylsulfinyl, Ci-d-alkylsulfonyl, CC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or for each optionally simple up to fourfold, identical or different by chlorine, -C 4 alkyl, CC 4 alkoxy, -C 4 alkyl thio, CC 4 alkylsulfinyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,
Cι-C4-Halogenalkyl, C C4-Halogenalkoxy, C C4-Halogenalkylthio, Cι-C4-Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.-C-C 4 haloalkyl, CC 4 -haloalkoxy, CC 4 -haloalkylthio, Cι-C 4 -haloalkylsulfinyl, Cι-C 4 -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, -C ( R 10 ) = N-OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R48 und R49 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, iso-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, n-Pentoxy, iso- Pentoxy, neo-Pentoxy, Methylthio, , Ethylthio, n-Propylthio, iso-Propylthio, n-R 48 and R 49 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, iso-pentyl, neo-pentyl, methoxy, ethoxy, n -Propoxy, iso-propoxy, n-butoxy, tert-butoxy, n-pentoxy, iso-pentoxy, neo-pentoxy, methylthio,, ethylthio, n-propylthio, iso-propylthio, n-
Butylthio, tert-Butylthio, n-Pentylthio, iso-Pentylthio, neo-Pentylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.Butylthio, tert-butylthio, n-pentylthio, iso-pentylthio, neo-pentylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different, by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n -Butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C ( H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N ( H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or - OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R48 und R49 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 48 and R 49 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio, trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
R50 und R51 stehen unabhängig voneinander bevorzugt für Wasserstoff, Ci-Cs-Alkyl, C1-C5-R 50 and R 51 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, C 1 -C 5 -
Alkoxy, Ci-Cj-Alkyltbio, C,-C5-Alkylsulfinyl, Ci-Cs-Alkylsulfonyl, C C5-Halogen- alkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, d-C4-Alkyl, Cι-C4-Alkoxy, Cι-C4-Alkylthio, d- -All-ylsulfinyl, C,-C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl,Alkoxy, Ci-Cj-alkyltbio, C, -C 5 -alkylsulfinyl, Ci-Cs-alkylsulfonyl, CC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or in each case optionally mono- to tetrasubstituted by identical or different substituents from chloro, dC 4 -alkyl, C 4 -alkoxy, C 4 alkylthio, d- -All-ylsulfinyl, C, -C 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl , Methoxycarbonyl, ethoxycarbonyl,
Cι-C4-Halogenalkyl, C C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, C C -Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)S02R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.-C-C 4 haloalkyl, CC 4 -haloalkoxy, -C-C 4 -haloalkylthio, CC -haloalkylsulfinyl, -C-C 4 -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N-OR n , - (CH 2 ) p N (R 12 ) S0 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R50 und R51 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n- Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3,R 50 and R 51 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso -Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different, by fluorine, chlorine, Methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso- Propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 ,
-C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.-C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R50 und R51 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff,R 50 and R 51 independently of one another very particularly preferably represent hydrogen,
Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.Methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, methoxy, ethoxy, iso-propoxy, tert-butoxy, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
R52 steht bevorzugt für Wasserstoff, CrC5-Alkyl, C C5-Alkoxy, Ci-Cs-Alkylthio, d-C5-R 52 preferably represents hydrogen, C r C 5 alkyl, CC 5 alkoxy, Ci-Cs-alkylthio, dC 5 -
Alkylsulfmyl, Cj-Cs-Alkylsulfonyl, CrCs-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, C C4-Alkoxy, Cι-C4-Alkylthio, d-C4-Alkylsulfinyl, d-C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl,Alkylsulfmyl, Cj-Cs-alkylsulfonyl, C r Cs-haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or for each optionally one to four times, identical or different by chlorine, Cι- C 4 -alkyl, CC 4 -alkoxy, -C-C 4 -alkylthio, dC 4 -alkylsulfinyl, dC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,
Cι-C -Halogenalkyl, C C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, C C4-Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.-C-C -haloalkyl, CC 4 -haloalkoxy, -C-C 4 -haloalkylthio, CC 4 -haloalkylsulfinyl, Cι-C 4 -haloalkylsulfonyl each with 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R52 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n- Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3,R 52 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n- Butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally optionally up to four times, identically or differently, by fluorine, chlorine, methyl, ethyl, n -Propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio , tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N- OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 ,
-N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.-N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R52 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, iso-Propyl, tert- Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio,R 52 very particularly preferably represents hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio,
Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl. R53 steht bevorzugt für Wasserstoff, Chlor, Cyano, Ci-Cs-Alkyl, d-C5-Alkoxy, C1-C5- Alkylthio, Ci-Cs-Alkylsulfinyl, Cι-C5rAlkylsulfonyl, Cι-C5-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, C C4-Alkoxy, C C4-Alkylthio, Cι-C4-Alkylsulfmyl, C C4-Ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or for each optionally single or double, identical or different by fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl. R 53 preferably represents hydrogen, chlorine, cyano, Ci-Cs-alkyl, dC 5 -alkoxy, C 1 -C 5 -alkylthio, Ci-Cs-alkylsulfinyl, -C-C 5r alkylsulfonyl, -C-C 5 -haloalkyl with 1 up to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally one to four times, identical or different by chlorine, -C 4 alkyl, CC 4 alkoxy, CC 4 alkylthio, -C-C 4 alkylsulfmyl, CC 4 -
Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C -Halogenalkyl, C]-C -Halogenalkoxy, Cι-C4-Halogenalkylthio, C C4-Halogen- alkylsulfinyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -(CH2)pN(R,2)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenenAlkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, Cι-C haloalkyl, C] -C -haloalkoxy, Cι-C4-haloalkylthio, CC 4-halo-alkylsulfinyl, CC 4 haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine - and / or bromine atoms, -C (R 10 ) = N-OR π , - (CH 2 ) p N (R , 2 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 the above
Bedeutungen haben.Have meanings.
R53 steht besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-R 53 particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso- Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-
Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3,Propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different, by fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy , Ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 ,
-C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.-C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R53 steht ganz besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, iso-R 53 very particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, iso-
Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.Propyl, tert-butyl, neo-pentyl, methoxy, ethoxy, iso-propoxy, tert-butoxy, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or for each optionally single or double, identical or different by fluorine, chlorine , Methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl.
R54 steht bevorzugt für Wasserstoff, Chlor, Cyano, Cι-C5-Alkyl, Ci-d-Alkoxy, C1-C5- Alkylthio, Cj-Cs-Alkylsulfinyl, C C5-Alkylsulfonyl, d-d-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, C C4-Alkoxy, C C -Alkylthio, Cι-C4-Alkylsulfmyl, d-C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C4-Halogenalkyl, C C4-Halogenalkoxy, C C -Halogenalkylthio, Cι-C -Halogen- alkylsulfinyl, Cι-C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORπ, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben,R 54 preferably represents hydrogen, chlorine, cyano, C 1 -C 5 -alkyl, Ci-d-alkoxy, C 1 -C 5 -alkylthio, Cj-Cs-alkylsulfinyl, CC 5 -alkylsulfonyl, dd-haloalkyl with 1 to 9 Fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally one to four times, the same or different, by chlorine, -C 4 alkyl, CC 4 alkoxy, CC alkylthio, C 4 -C 4 alkylsulfmyl, dC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, Cι -C 4 haloalkyl, CC 4 haloalkoxy, CC haloalkylthio, C 1 -C haloalkylsulfinyl, C 1 -C haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N -OR π , - (CH 2 ) pN (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above,
R54 steht besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso- Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n-R 54 particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methoxy, ethoxy, n-propoxy, iso- Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different, by fluorine, chlorine, methyl , Ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-
Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5,. -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.Propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 ,. -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R54 steht ganz besonders bevorzugt für Wasserstoff, Chlor, Cyano, Methyl, Ethyl, iso- Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durchR 54 very particularly preferably represents hydrogen, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert -Butylthio, trifluoromethyl or for each optionally single or double, identical or different by
Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.Fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl.
R55 steht bevorzugt für Wasserstoff, Ci-Cs-Alkyl, Ci-d-Alkoxy, Cι-C5-Alkylthio, C1-C5-R 55 preferably represents hydrogen, Ci-Cs-alkyl, Ci-d-alkoxy, -C-C 5 alkylthio, C 1 -C 5 -
Nlkylsulfinyl, Ci-Cs-Alkylsulfonyl, Ci-d-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, Cι-C4-Alkoxy, Cι-C4-Alkylthio, d-Q-Alkylsulfmyl, C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C -Halogenalkyl, CrC4-Halogenalkoxy, Cι-C -Halogenalkylthio, CrC -Halogen- alkylsulfinyl, d-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -(CH2)pN(RI2)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, . wobei . R10 bis R13 die- oben angegebenen Bedeutungen haben.Nlkylsulfinyl, Ci-Cs-alkylsulfonyl, Ci-d-haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally one to four times, identical or different by chlorine, Cι- C 4 alkyl, -C 4 alkoxy, -C 4 alkylthio, dQ-alkylsulfmyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, C 1 -C 4 -haloalkyl, C r C 4 -haloalkoxy, Cι -C -haloalkylthio, C r C -haloalkylsulfinyl, dC 4 -haloalkylsulfonyl each with 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , - (CH 2 ) p N (R I2 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl,. in which . R 10 to R 13 have the meanings given above.
R55 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-. Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n-R 55 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n- Butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-. Butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different by fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n -
Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, . -N(H)S02CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)S02CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.Propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3, -C (H) = N-OC 2 H 5, -C (CH 3) = N-OC 2 H 5. -N (H) S0 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) S0 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R55 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, iso-Propyl, tert- Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy," tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durchR 55 very particularly preferably represents hydrogen, methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, methoxy, ethoxy, iso-propoxy, "tert-butoxy, methylthio, ethylthio, iso-propylthio, tert-butylthio, Trifluoromethyl or for each optionally single or double, the same or different
Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.Fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl.
R56 und R57, stehen unabhängig voneinander bevorzugt für Wasserstoff, Ci-Cs-Alkyl, C1-C5- Alkoxy, Ci-Cs-Alkylthio, Ci-Cs-Alkylsulfinyl, d-C5-Alkylsulfonyl, d-C5-Halogen- alkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl. C C4-Alkoxy, ' C C4-Alkylthio, Cι-C4-Alkylsulfinyl, d-C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, , d-d-Halogenalkyl, C C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, CrC -Halogen-. alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben. R56 und R57 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl,R 56 and R 57, independently of one another, preferably represent hydrogen, Ci-Cs-alkyl, C 1 -C 5 -alkoxy, Ci-Cs-alkylthio, Ci-Cs-alkylsulfinyl, dC 5 -alkylsulfonyl, dC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or for each optionally single to quadruple, the same or different by chlorine, -CC 4 alkyl. CC 4 -alkoxy, 'CC 4 -alkylthio, -C-C 4 -alkylsulfinyl, dC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,, dd-haloalkyl, CC 4 -haloalkoxy, Cι-C 4 -haloalkylthio, C r C -Halogen-. alkylsulfinyl, -C-C 4 haloalkylsulfonyl each with 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above. R 56 and R 57 independently of one another particularly preferably represent hydrogen, methyl,
Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy,Ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy,
Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-
Propylt io, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propqxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, . -N(H)S02CH3, -N(CH3)SO2CH3,Propylt io, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 ,. -N (H) S0 2 CH 3 , -N (CH 3 ) SO 2 CH 3 ,
-N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.-N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R56 und R57 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 56 and R 57 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-Butylthio, trifluoromethyl or phenyl or benzyl, each optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy.
R58 und R59 stehen unabhängig voneinander bevorzugt für Wasserstoff, Ci-Cs-Alkyl, C1-C5- Alkoxy, Ci-Cs-Alkylthio. Ci-Cs-Alkylsulfinyl, Ci-d-Alkylsulfonyl, Ci-d-Halogen- alkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, Cι-C4-Alkoxy, Cj- -AD yl hio, Cι-C4-Alkylsulfinyl, Cι-C4-R 58 and R 59 independently of one another preferably represent hydrogen, Ci-Cs-alkyl, C 1 -C 5 -alkoxy, Ci-Cs-alkylthio. Ci-Cs-alkylsulfinyl, Ci-d-alkylsulfonyl, Ci-d-haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally simple to fourfold, identical or different from chlorine, -CC 4 -alkyl, -C-C 4 -alkoxy, Cj- -AD yl hio, -C-C 4 -alkylsulfinyl, -C-C 4 -
Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C4-Halogenalkyl, Cι-C -Halogenalkoxy, Cι-C4-Halogenalkylthio, C C4-Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenenAlkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, Cι-C4 haloalkyl, Cι-C -haloalkoxy, Cι-C4-haloalkylthio, CC 4-halo-alkylsulfinyl, Cι-C4-haloalkylsulfonyl having in each case 1 to 9 fluorine , Chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 the above
Bedeutungen haben.Have meanings.
R58 und R59 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl,R 58 and R 59 independently of one another particularly preferably represent hydrogen, methyl,
Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n- . Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl. 'Ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n- , Propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert -Butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N -OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N ( H) CH 3 substituted phenyl or benzyl. '
R58 und R59 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach Oder zweifach, gleich oder verschieden durchR 58 and R 59 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio, trifluoromethyl or, if appropriate, in each case single or double, identical or different
Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.Fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl.
R60 steht bevorzugt für Wasserstoff, C C5-Alkyl, Ci-d-Alkoxy, Cι-C5-Alkylthio, C C5- Alkylsulfinyl, Ci-d-Alkylsulfonyl, Cι-C5-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, d-d-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, CrC4-Alkoxy, Cι-C4-Alkylthio, C C4-Alkylsulfinyl, C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C -Halogenalkyl, Cι-C4-Halogenalkoxy, Cι-C -Halogenalkylthio, CrC4-Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.R 60 preferably represents hydrogen, CC 5 -alkyl, Ci-d-alkoxy, -C-C 5 -alkylthio, CC 5 - alkylsulfinyl, Ci-d-alkylsulfonyl, Cι-C 5 -haloalkyl with 1 to 9 fluorine, chlorine - And / or bromine atoms, dd-cycloalkyl or for each optionally single to quadruple, the same or different by chlorine, -C 4 alkyl, C r C 4 alkoxy, C 4 alkylthio, CC 4 alkylsulfinyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, Cι-C haloalkyl, Cι-C4-haloalkoxy, Cι-C haloalkylthio, C r C 4 alkylsulfinyl-halo, Cι-C4-haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N-OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl , wherein R 10 to R 13 have the meanings given above.
R steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n- Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3,R particularly preferably represents hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy , tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different, by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy , tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 ,
-N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.-N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R60 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, iso-Propyl, tert- Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio,R 60 very particularly preferably represents hydrogen, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio,
Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.Ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or for each optionally single or double, identical or different by fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl.
R61 steht bevorzugt für Ci-Cs-Alkyl, Cι-C5-Alkoxy, C,-C5-Alkylthio, Cι-C5- Alkylsuϊfϊnyl, Cι-C5-Alkylsulfonyl, Ci-d-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, C C4-Alkyl, Cι-C4-Alkoxy, Cι-C4-Alkylthio, Cι-C4-Alkylsulfinyl, C C4-R 61 preferably represents Ci-Cs-alkyl, -C-C 5 -alkoxy, C, -C 5 -alkylthio, -C-C 5 - alkylsulfonyl, -C-C 5 -alkylsulfonyl, Ci-d-haloalkyl with 1 to 9 fluoro -, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different substituents from chloro, CC 4 -alkyl, C 4 -alkoxy, C 4 alkylthio, Cι -C 4 alkylsulfinyl, CC 4 -
Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl,- Cι-C4-Halogenalkyl, Cι-C4-Halogenalkoxy, Cι-C -Halogenalkylthio, Cι-C4-Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenenAlkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, - Cι-C4-haloalkyl, Cι-C4-haloalkoxy, Cι-C haloalkylthio, Cι-C 4 alkylsulfinyl-halo, Cι-C4-haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or Benzyl, where R 10 to R 13 are those given above
Bedeutungen haben. R61 steht besonders bevorzugt für Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert- Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert- Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3; -N(H)S02CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.Have meanings. R 61 particularly preferably represents methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally optionally up to four times, identically or differently, by fluorine, chlorine, methyl, ethyl, n-propyl , iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert -Butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3; -N (H) S0 2 CF 3 , -N (CH 3 ) SO 2 CF3, -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R61 steht ganz besonders bevorzugt für Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 61 very particularly preferably represents methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio, trifluoromethyl or each optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy substituted phenyl or benzyl.
R62 steht bevorzugt für Cyano, Cι-C5-Alkyl, Ci-Cs-Alkoxy, d-Cs-Alkylthio, C C - Alkylsulfinyl, C C3-Alkylsulfonyl, Ci-d-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, C C4-Alkyl, CrC4-Alkoxy, Cι-C4-Alkylthio, C C4-Alkylsulfinyl, CrC4-Alkylsulfo- nyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C4-Ha- logenalkyl, C C -Halogenalkoxy, Cι-C -Halogenalkylthio, C1-C -Halogenalkylsulfi- nyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORU, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.R 62 preferably represents cyano, -CC 5 alkyl, Ci-Cs-alkoxy, d-Cs-alkylthio, CC - alkylsulfinyl, CC 3 -alkylsulfonyl, Ci-d-haloalkyl with 1 to 9 fluoro, chloro and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally single to fourfold, identical or different by chlorine, CC 4 alkyl, C r C 4 alkoxy, C 1 -C 4 alkylthio, CC 4 alkylsulfinyl, C r C 4 -alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, C 1 -C 4 -haloalkyl, CC -haloalkoxy, C 1 -C -haloalkylthio, C 1 -C -haloalkylsulfonyl, CC 4 -haloalkylsulfonyl with each 1 to 9 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N-OR U , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R62 steht besonders bevorzugt für Cyano, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n- Butoxy, tert-Butoxy,' Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n- Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3,R 62 particularly preferably represents cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n- Butoxy, tert-butoxy, 'methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different, by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n- Butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N -OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 ,
-N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl. R62 steht ganz besonders bevorzugt für Cyano, Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso- Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.-N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl. R 62 very particularly preferably represents cyano, methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio, trifluoromethyl or for phenyl or benzyl which is optionally monosubstituted or disubstituted, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
R63 steht bevorzugt für Ci-Cs-Alkyl, C C5-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, d-Qs-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor,R 63 preferably represents Ci-Cs-alkyl, CC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, d-Qs-cycloalkyl or for each optionally one to four times, identical or different by chlorine,
C C4-Alkyl, C C4-Alkoxy, C C4-Alkylthio, d-C4-Alkylsulfinyl, C C4-Alkylsulfo- nyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, d-C4-Ha- logenalkyl, C]-C4-Halogenalkoxy, C C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfi- nyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Brom- atomen, -C(R10)=N-ORπ, -(CH2)pN(R12)S02R13, oder -OSO2NR12R13 substituiertesCC 4 -alkyl, CC 4 -alkoxy, CC 4 -alkylthio, dC 4 -alkylsulfinyl, CC 4 -alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, dC 4 -haloalkyl, C] -C 4 -haloalkoxy, CC 4 haloalkylthio, Cι-C 4 -Halogenalkylsulfi- nyl, atoms, Cι-C 4 haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and / or bromine, -C (R 10) = N-oR π, - (CH 2 ) p N (R 12 ) S0 2 R 13 , or -OSO 2 NR 12 R 13 substituted
Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.Phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R63 steht besonders bevorzugt für Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, . tert- Butyl, n-Pentyl, neo-Pentyl, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,R 63 particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl,. tert-butyl, n-pentyl, neo-pentyl, trifluoromethyl, cyclopropyl or for each optionally single to fourfold, identical or different by fluorine,
Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertesChlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted
Phenyl oder Benzyl.Phenyl or benzyl.
R63 steht ganz besonders bevorzugt für Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durchR 63 very particularly preferably represents methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, trifluoromethyl or, in each case, in one or two cases, identically or differently
Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl. R64 steht bevorzugt für Cι-C5-Alkyl, Cι-C5-Alkoxy, C Cs-Alkylthio, C C ■5" Alkylsulfinyl, Cι-C5-Alkylsulfonyl, Cι-C5-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, Cι-C4-Alkoxy, Cι-C4-Alkylthio, Cι-C4-Alkylsulfmyl, d-C4-Alkylsulfo- nyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C -Ha- logenalkyl, C C -Halogenalkoxy, Cι-C -Halogeήalkylthio, d- -Halogenalkylsulfi- nyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.Fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl. R 64 is preferably Cι-C 5 -alkyl, C 5 alkoxy, C Cs-alkylthio, CC ■ 5 "alkylsulfinyl, Cι-C 5 alkylsulfonyl, Cι-C 5 haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different substituents from chlorine, Cι-C 4 -alkyl, C 4 -alkoxy, C 4 alkylthio, Cι -C 4 -Alkylsulfmyl, dC 4 -Alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, -C-C -Halogenalkyl, CC -haloalkoxy, -C-C -Halogeήalkylthio, d- -Halogenalkylsulfi- nyl, Cι-C 4 -Halogenalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R64 steht besonders bevorzugt für Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert- Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio,. n-Butylthio, tert- Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3,R 64 particularly preferably represents methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio ,. n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy , n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H5, -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 ,
-N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.-N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R64 steht ganz besonders bevorzugt für Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, .Ethoxy, iso-Propoxy, tert-Butoxy, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 64 very particularly preferably represents methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, .ethoxy, isopropoxy, tert-butoxy, methylthio, ethylthio, isopropylthio, tert-butylthio, trifluoromethyl or for phenyl or benzyl substituted in each case optionally once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy.
R65 steht bevorzugt für Ci-Cs-Alkyl. Cι-C5-Alkylthio, d-Cs-Alkylsulfrnyl, Ci-Cs- Alkylsulfonyl, Ci-d-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, C C4-Alkoxy, d- -Alkylthio, Cι-C4-Alkylsulfinyl, • C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C4-Halogenalkyl, Cι-C -Halogenalkoxy, Cι-C4-Halogenalkylthio, C C4-Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 "bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenenR 65 preferably represents Ci-Cs-alkyl. -C-C 5 alkylthio, d-Cs-alkylsulfonyl, Ci-Cs-alkylsulfonyl, Ci-d-haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally simple up to fourfold, the same or different by chlorine, -C 4 alkyl, CC 4 alkoxy, d- alkylthio, -C 4 alkyl sulfinyl, • CC 4 - Alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, Cι-C4 haloalkyl, Cι-C -haloalkoxy, Cι-C4-haloalkylthio, CC 4-halo-alkylsulfinyl, Cι-C4-haloalkylsulfonyl having in each case 1 "to 9 fluorine -, chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 are those given above
Bedeutungen haben.Have meanings.
R65 . steht besonders bevorzugt für Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert- Butyl, n-Pentyl, neo-Pentyl, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n- Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3,R 65 . particularly preferably represents methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert- Butylthio, trifluoromethyl, cyclopropyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso -Propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N -OCH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 ,
-N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.-N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R65 steht ganz besonders bevorzugt für Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 65 very particularly preferably represents methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or, in each case, optionally single or double, identical or different by fluorine, Chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl.
R66 steht bevorzugt für d-C5-Alkyl, Ci-Cs-Alkylthio, Ci-d-Alkylsulfinyl, CrC5-R 66 preferably represents dC 5 alkyl, Ci-Cs-alkylthio, Ci-d-alkylsulfinyl, C r C 5 -
Alkylsulfonyl, Ci-Cs-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Ci-d-Alkyl, C C4-Alkoxy, Cι-C4-Alkylthio, C C4-Alkylsulfinyl, CrC4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl,Alkylsulfonyl, Ci-Cs-haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl or for each optionally one to four times, identical or different by chlorine, Ci-d-alkyl, CC 4 -Alkoxy, -CC 4 -alkylthio, CC 4 -alkylsulfinyl, C r C 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,
Cι-C4-Halogenalkyl, C C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, Cι-C -Halogen- alkylsulfinyl, Cι-C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R,0)=N-ORn, -(CH2)pN(R12)S02R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben. R66 steht besonders bevorzugt für Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert- Butyl, n-Pentyl, neo-Pentyl, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n- Butylthio, tert-Butylthio, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,Cι-C 4 haloalkyl, CC 4 haloalkoxy, Cι-C4-haloalkylthio, Cι-C-halo-alkylsulfinyl, Cι-C4-haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R , 0 ) = N-OR n , - (CH 2 ) p N (R 12 ) S0 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above to have. R 66 particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, neopentyl, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different by fluorine
Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OGH3, -C(H)=N-OC2H5, -C(CH3)=N-OC2H5, -N(H)S02CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertesChlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OGH 3 , -C (H) = N-OC 2 H 5 , -C (CH 3 ) = N-OC 2 H 5 , -N (H) S0 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted
Phenyl oder Benzyl.Phenyl or benzyl.
R66 steht ganz besonders bevorzugt für Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methylthio, Ethylthio, iso-Propylthio, tert-Butylthio, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durchR 66 very particularly preferably represents methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, methylthio, ethylthio, iso-propylthio, tert-butylthio, trifluoromethyl or, in each case, in one or more instances, identically or differently
Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.Fluorine, chlorine, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl.
R67 steht bevorzugt für C C5-Alkyl, C C5-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, d-d-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, Cι-C4-Alkyl, Cι-C4-Alkoxy, Cι-C4-Alkylthio, Cι-C4-Alkylsulfinyl, Cι-C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, Cι-C -Halogenal yl, Cι-C -Halogenalkoxy, Cι-C -Halogenalkylthio, Cι-C -Halogen- alkylsulfinyl, Cι-C -Halogenalkylsulfonyl mit jeweils 1 bis' 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORU, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.R 67 preferably represents CC 5 -alkyl, CC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, dd-cycloalkyl or for in each case optionally up to four times, identically or differently by chlorine, -CC 4 - alkyl, Cι-C 4 -alkoxy, C 4 alkylthio, Cι-C4-alkylsulfinyl, Cι-C 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, Cι-C -Halogenal yl, Cι-C -haloalkoxy , -C-C -haloalkylthio, -C-C -halo-alkylsulfinyl, -C-C -haloalkylsulfonyl each having 1 to ' 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR U , - ( CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R67 steht besonders bevorzugt für Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-R 67 particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-
Butyl, n-Pentyl, neo-Pentyl, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2H5; -C(CH3)=N-OC2H5, -N(H)S02CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSQ2N(CH3)2 oder -OSO2N(H)CH3 substituiertes Phenyl oder Benzyl.Butyl, n-pentyl, neo-pentyl, trifluoromethyl, cyclopropyl or for each optionally one to four times, the same or different by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy , Ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 H 5 ; -C (CH 3 ) = N-OC 2 H 5 , -N (H) S0 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSQ 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted phenyl or benzyl.
R67 steht ganz besonders bevorzugt für Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.R 67 very particularly preferably represents methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, trifluoromethyl or, if appropriate, in each case once or twice, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert- Butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy substituted phenyl or benzyl.
R6S steht bevorzugt für Ci-Cs-Alkyl, Ci-d-Alkoxy, C C5-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, d-Ce-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Chlor, d-C4-Alkyl, C C4-Alkoxy, Cι-C4-Alkylthio, Cι-C4-Alkylsulfmyl, C C4- Alkylsulfonyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl,R 6S preferably represents Ci-Cs-alkyl, Ci-d-alkoxy, CC 5 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, d-Ce-cycloalkyl or for each optionally one to four times, the same or different from chlorine, dC 4 -alkyl, CC 4 -alkoxy, -C-C 4 -alkylthio, Cι-C 4 -alkylsulfmyl, CC 4 - alkylsulfonyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,
Cι-C -Halogenalkyl, Cι-C4-Halogenalkoxy, Cι-C4-Halogenalkylthio, C C -Halogen- alkylsulfinyl, C C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -(CH2)pN(R12)SO2R13, oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl, wobei R10 bis R13 die oben angegebenen Bedeutungen haben.C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, CC -haloalkylsulfinyl, CC -haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , - (CH 2 ) p N (R 12 ) SO 2 R 13 , or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given above.
R68 steht besonders bevorzugt für Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert- Butyl, n-Pentyl, neo-Pentyl, Methoxy, Ethoxy, n-Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Trifluormethyl, Cyclopropyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,R 68 particularly preferably represents methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, n-pentyl, neo-pentyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, trifluoromethyl, cyclopropyl or for each optionally one to four times, identical or different by fluorine,
Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, tert-Butyl, Methoxy, Ethoxy, n- Propoxy, iso-Propoxy, n-Butoxy, tert-Butoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, n-Butylthio, tert-Butylthio, -C(H)=N-OCH3, -C(CH3)=N-OCH3, -C(H)=N-OC2Hs. -C(CH3)=N-OC2H5, -N(H)SO2CH3, -N(CH3)SO2CH3, -N(H)SO2CF3, -N(CH3)SO2CF3, -OSO2N(CH3)2 oder -OSO2N(H)CH3 substituiertesChlorine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, tert-butylthio, -C (H) = N-OCH 3 , -C (CH 3 ) = N-OCH 3 , -C (H) = N-OC 2 Hs. -C ( CH 3 ) = N-OC 2 H 5 , -N (H) SO 2 CH 3 , -N (CH 3 ) SO 2 CH 3 , -N (H) SO 2 CF 3 , -N (CH 3 ) SO 2 CF 3 , -OSO 2 N (CH 3 ) 2 or -OSO 2 N (H) CH 3 substituted
Phenyl oder Benzyl.Phenyl or benzyl.
R68 steht ganz besonders bevorzugt für Methyl, Ethyl, iso-Propyl, tert-Butyl, neo-Pentyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy, Trifluormethyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, iso-Propyl, tert-Butyl, Methoxy, Ethoxy, iso-Propoxy, tert-Butoxy substituiertes Phenyl oder Benzyl.'R 68 very particularly preferably represents methyl, ethyl, isopropyl, tert-butyl, neopentyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl or for phenyl or benzyl which is optionally monosubstituted or disubstituted, identically or differently, by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy. '
Die Restedefinitionen R14 bis R68 müssen jeweils so ausgewählt werden, dass die Hetero- cyclen Ql bis Q38 mindestens einfach substituiert sind. Die möglichen Substitutionspositionen dürfen also nicht gleichzeitig für Wasserstoff stehen. Die entsprechenden Maßgaben sind im allgemeinen Teil explizit angegeben, bei der Darstellung der vorzugsweisen Definitionen aber nicht mehr wiederholt.The radical definitions R 14 to R 68 must each be selected so that the heterocycles Ql to Q38 are at least monosubstituted. The possible substitution positions must not simultaneously represent hydrogen. The corresponding requirements are explicitly stated in the general section, but are no longer repeated when the preferred definitions are presented.
Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcher R1 für Fluor steht, R2 fürAlso preferred are compounds of formula (I) in which R 1 is fluorine, R 2 is
Fluor steht und R3 für Wasserstoff steht.Is fluorine and R 3 is hydrogen.
Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcher R1 für Fluor steht, R2 fürAlso preferred are compounds of formula (I) in which R 1 is fluorine, R 2 is
Chlor steht und R3 für Wasserstoff steht. Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcher R1 für Fluor steht, R2 fürChlorine is and R 3 is hydrogen. Also preferred are compounds of formula (I) in which R 1 is fluorine, R 2 is
Wasserstoff steht und R3 für Wasserstoff steht.Is hydrogen and R 3 is hydrogen.
Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcher R1 für Chlor steht, R2 fürAlso preferred are compounds of formula (I) in which R 1 is chlorine, R 2 is
Wasserstoff steht und R3 für Wasserstoff steht.Is hydrogen and R 3 is hydrogen.
Weiterhin bevorzugt sind Verbindungen der Formel (T), in welcher R1 für Methyl steht, R2 für Wasserstoff steht und R3 für Wasserstoff steht.Also preferred are compounds of formula (T) in which R 1 is methyl, R 2 is hydrogen and R 3 is hydrogen.
Weiterhin bevorzugt sindNerbindungen der Formel (T), in welcher R1 für Chlor steht, R2 fürPreference is furthermore given to compounds of the formula (T) in which R 1 is chlorine, R 2 is
Wasserstoff steht und R3 für Fluor steht.Is hydrogen and R 3 is fluorine.
Weiterhin bevorzugt sind Verbindungen der Formel (T), in welcher A1 für Ν steht. Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcher A1 für CH steht.Also preferred are compounds of formula (T) in which A 1 represents Ν. Also preferred are compounds of formula (I) in which A 1 is CH.
Weiterhin bevorzugt sind Verbindungen der Formel (T), in welcher A2 für Ν steht.Also preferred are compounds of formula (T) in which A 2 is Ν.
Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcher A2 für CR9 steht.Also preferred are compounds of formula (I) in which A 2 is CR 9 .
Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcher A2 für CH steht.Also preferred are compounds of formula (I) in which A 2 is CH.
Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcher A1 für Ν und A2 für Ν steht.Also preferred are compounds of formula (I) in which A 1 is Ν and A 2 is Ν.
Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcher A1 für Ν und A2 für CR9 steht.Also preferred are compounds of formula (I) in which A 1 is Ν and A 2 is CR 9 .
Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcher A1 für Ν und A2 für CH steht. Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcher A1 für. CH und A2 für N steht.Also preferred are compounds of formula (I) in which A 1 is Ν and A 2 is CH. Also preferred are compounds of formula (I) in which A 1 is . CH and A 2 represents N.
Weiterhin bevorzugt sind Verbindungen der -Formel (T), in welcher A1 für CH μnd A2 fürAlso preferred are compounds of the formula (T) in which A 1 for CH μ and A 2 for
CR9 steht.CR 9 stands.
Weiterhin bevorzugt sind Verbindungen der Formel (T), in welcher A1 für CH unά A2 für CH steht.Also preferred are compounds of formula (T) in which A 1 is CH and A 2 is CH.
Weiterhin, bevorzugt sind Verbindunger. der Formel (I), va. welcherFurthermore, preferred are connectors. of formula (I), especially which one
Q für einen ungesättigten aromatischen 5-glieάπgen Heterocyclus aus der ReiheQ for an unsaturated aromatic 5-membered heterocycle from the series
Weiterhin bevorzugt sind Verbindungen der Formel (T), in welcherAlso preferred are compounds of formula (T) in which
Q f r einen ungesättigten aromatischen 5-gliedrigen Heterocyclus aus der ReiheQ for an unsaturated aromatic 5-membered heterocycle from the series
steht. stands.
Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcher Q für einen ungesättigten aromatischen 5-gliedrigen Heterocyclus aus der Reihe steht.Also preferred are compounds of formula (I) in which Q is an unsaturated aromatic 5-membered heterocycle from the series stands.
Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcher .Also preferred are compounds of formula (I) in which.
Q für einen ungesättigten aromatischen 5-gliedrigen Heterocyclus aus der ReiheQ for an unsaturated aromatic 5-membered heterocycle from the series
steht. stands.
Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcherAlso preferred are compounds of formula (I) in which
Q für einen ungesättigten aromatischen 5-gliedrigen Heterocyclus aus der ReiheQ for an unsaturated aromatic 5-membered heterocycle from the series
steht. stands.
Weiterhin bevorzugt sind Verbindungen der Formel (T), in welcherAlso preferred are compounds of formula (T) in which
Q für einen ungesättigten aromatischen 5-gliedrigen Heterocyclus aus der ReiheQ for an unsaturated aromatic 5-membered heterocycle from the series
Q31 Q32 Q33 Q34Q31 Q32 Q33 Q34
Q35 Q36 Q37 Q38 steht. Weiterhin bevorzugt sind Verbindungen der Formel (T), in welcherQ35 Q36 Q37 Q38 stands. Also preferred are compounds of formula (T) in which
A1 und A2 jeweils für CH stehen undA 1 and A 2 each represent CH and
Q für einen ungesättigten aromatischen 5-gliedrigen Heterocyclus aus der ReiheQ for an unsaturated aromatic 5-membered heterocycle from the series
Q31 Q32 Q33 Q34Q31 Q32 Q33 Q34
Q35 Q36 Q37 Q38 steht.Q35 Q36 Q37 Q38 stands.
Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcherAlso preferred are compounds of formula (I) in which
R4 für Wasserstoff, Methoxycarbonyl oder Ethoxycarbonyl steht,R 4 represents hydrogen, methoxycarbonyl or ethoxycarbonyl,
A1 und A2 jeweils für CH stehen undA 1 and A 2 each represent CH and
Q für einen ungesättigten aromatischen 5-gliedrigen Heterocyclus aus der ReiheQ for an unsaturated aromatic 5-membered heterocycle from the series
Q31 Q32 Q33 Q34Q31 Q32 Q33 Q34
Q35 Q36 Q37 Q38 steht.Q35 Q36 Q37 Q38 stands.
Weiterhin bevorzugt sind Verbindungen der Formel (T), in welcher R4 für Wasserstoff, Methoxycarbonyl oder Ethoxycarbonyl steht, A1 und A2 jeweils für CH stehen und Q für einen ungesättigten aromatischen 5-gliedrigen Heterocyclus aus der ReiheAlso preferred are compounds of formula (T) in which R 4 is hydrogen, methoxycarbonyl or ethoxycarbonyl, A 1 and A 2 are each CH and Q is an unsaturated aromatic 5-membered heterocycle from the series
Q31 Q32 Q33 Q34 Q31 Q32 Q33 Q34
Q35 Q36 Q37 Q38 steht und R62, R63, R64, R65 unabhängig vonemander für Methyl, tert-Butyl oder Trifluormethyl stehen.Q35 Q36 Q37 Q38 and R 62 , R 63 , R 64 , R 65 independently of one another represent methyl, tert-butyl or trifluoromethyl.
Weiterhin bevorzugt sind Verbindungen der Formel (I), in welcher R1 für Fluor, Chlor oder Methyl steht,Also preferred are compounds of formula (I) in which R 1 represents fluorine, chlorine or methyl,
R2 für Wasserstoff oder Fluor steht, R3 für Wasserstoff oder Fluor steht,R 2 represents hydrogen or fluorine, R 3 represents hydrogen or fluorine,
R4 für Wasserstoff, Methoxycarbonyl oder Ethoxycarbonyl steht, A1 und A2 jeweils für CH stehen und Q für einen ungesättigten aromatischen 5-gliedrigen Heterocyclus aus der ReiheR 4 represents hydrogen, methoxycarbonyl or ethoxycarbonyl, A 1 and A 2 each represent CH and Q represents an unsaturated aromatic 5-membered heterocycle from the series
Q31 Q32 Q33 Q34Q31 Q32 Q33 Q34
Q35 Q36 Q37 Q38 steht und R62, R63, R64, R65 unabhängig voneinander für Methyl, tert-Butyl oder Trifluormethyl stehen.Q35 Q36 Q37 Q38 and R 62 , R 63 , R 64 , R 65 independently of one another represent methyl, tert-butyl or trifluoromethyl.
Weiterhin bevorzugt sind Verbindungen der Formel (I-a):Also preferred are compounds of formula (I-a):
in welcher in which
R1, R2, R3, A1, A2, R5, R6, R7, R8 und Q die oben angegebenen Bedeutungen haben und dasR 1 , R 2 , R 3 , A 1 , A 2 , R 5 , R 6 , R 7 , R 8 and Q have the meanings given above and that
Kohlenstoffatom in 2-Position des 2H-Pyrrolringes R-Konfiguration besitzt. Weiterhin bevorzugt sind Verbindungen der Formeln (I-b) und (I-c):Carbon atom in the 2-position of the 2H pyrrole ring has the R configuration. Compounds of the formulas (Ib) and (Ic) are also preferred:
in welcher in which
R1, R2, R3, A1, A2, R5, R6, R7, R8 und Q die oben angegebenen Bedeutungen haben, R4 nicht für Wasserstoff steht und die beiden Substituenten in 2- und 3 -Position des 2H-Pyrrolringes jeweils eis zueinander stehen.R 1 , R 2 , R 3 , A 1 , A 2 , R 5 , R 6 , R 7 , R 8 and Q have the meanings given above, R 4 does not represent hydrogen and the two substituents in 2- and 3 - The position of the 2H pyrrole ring must be in relation to each other.
Weiterhin bevorzugt sind Verbindungen der Formeln (I-d) und (I-e):Compounds of the formulas (I-d) and (I-e) are also preferred:
in welcher in which
R1, R2, R3, A\ A2, R5, R6, R7, R8 und Q die oben angegebenen Bedeutungen haben, -R 1 , R 2 , R 3 , A \ A 2 , R 5 , R 6 , R 7 , R 8 and Q have the meanings given above,
R4 nicht für Wasserstoff steht und die beiden Substituenten in 2- und 3-Position des 2H-Pyrrolringes jeweils Irans zueinander stehen.R 4 does not represent hydrogen and the two substituents in the 2- and 3-positions of the 2H-pyrrole ring are each Iran.
Verbindungen der Formel (I-a) erhält man durch übliche Verfahren zur Racematspaltung, wie zum Beispiel durch Chromatographie der entsprechenden Racemate an einer chiralen stationären Phase. Es ist möglich, sowohl die racemischen Endprodukte oder racemische Zwischenprodukte auf diese Weise in die beiden Enantiomere zu zerlegen.Compounds of the formula (I-a) are obtained by customary processes for resolving racemates, for example by chromatography of the corresponding racemates on a chiral stationary phase. It is possible to break down both the racemic end products or racemic intermediates into the two enantiomers in this way.
Gesättigte Kohlenwasserstoffreste wie Alkyl können, auch in Verbindung mit Hetero- atomen, wie z.B. in Alkoxy, soweit möglich, jeweils geradkettig oder verzweigt sein.Saturated hydrocarbon radicals, such as alkyl, can also be used in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched.
Durch Halogen substituierte Reste, z.B. Halogenalkyl, sind einfach oder mehrfach bis zur maximal möglichen Substituentenzahl halogeniert. Bei mehrfacher Halogenierung können die Halogenatome gleich oder verschieden sein. Halogen steht dabei für Fluor, Chlor, Brom oder Iod, insbesondere für Fluor, Chlor oder Brom.Halogen substituted residues e.g. Haloalkyl, are halogenated once or several times up to the maximum possible number of substituents. In the case of multiple halogenation, the halogen atoms can be the same or different. Halogen represents fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
, Bevorzugt, besonders bevorzugt oder ganz besonders bevorzugt sind Verbindungen, welche jeweils die unter bevorzugt, besonders bevorzugt oder ganz besonders bevorzugt genannten Substituenten tragen., Preferred, particularly preferred or very particularly preferred are compounds which each carry the substituents mentioned under preferred, particularly preferred or very particularly preferred.
Gesättigte oder ungesättigte Kohleriwasserstoffreste wie Alkyl oder Alkenyl können, auch in Verbindung mit Heteroatomen, wie z.B. in Alkoxy, soweit möglich, jeweils geradkettig oder verzweigt sein.Saturated or unsaturated hydrocarbon residues such as alkyl or alkenyl can also be used in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched.
Gegebenenfalls substituierte Reste können einfach oder mehrfach substituiert sein, wobei bei Mehrfachsubstitutionen die Substituenten gleich oder verschieden sein können. Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen können jedoch auch untereinander, also zwischen den jeweiligen Bereichen und Vorzugsbereichen beliebig kombiniert werden. Sie gelten für die Endprodukte sowie für die Vor- und Zwischenprodukte entsprechend.Optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different. The general definitions or explanations of residues or explanations listed above or in preferred areas can, however, also be combined with one another as desired, that is to say between the respective areas and preferred areas. They apply accordingly to the end products as well as to the preliminary and intermediate products.
Verwendet man 5-(2,6-Difluorphenyl)-2-[2-fluor-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)phenyl]-3,4-dihydro-2H-pyrrol und 5-(4-Bromphenyl)-3-tert-butyl-l,2,4-oxadiazol als Ausgangsstoffe sowie einen Katalysator, so kann der Verlauf des erfmdungsgemäßen Verfahrens (A) durch das folgende Formelschema veranschaulicht werden. If 5- (2,6-difluorophenyl) -2- [2-fluoro-4- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolan- 2-yl) phenyl] -3,4 is used dihydro-2H-pyrrole and 5- (4-bromophenyl) -3-tert-butyl-l, 2,4-oxadiazole as starting materials and a catalyst, the course of the process (A) according to the invention can be illustrated by the following formula ,
Die bei der Durchführung des erfϊndungsgemäßen Verfahrens (A) als Ausgangsstoffe benötigten Δ^Pyrroline sind durch die Formel (11) allgemein definiert. In dieser Formel stehen R1, R2, R3, R4, A1 und R5 bevorzugt, besonders bevorzugt, ganz besonders bevorzugt bzw. insbesondere ganz besonders bevorzugt für diejenigen Bedeutungen, die bereits in Zusammenhang mit der Beschreibung der erfϊndungsgemäßen Stoffe der Formel (J) für diese Reste als bevorzugt, besonders bevorzugt etc. genannt wurden.Formula (11) provides a general definition of the Δ ^ pyrrolines required as starting materials when carrying out process (A) according to the invention. In this formula, R 1, R 2, R 3, R 4, A 1 and R 5 are preferred, particularly preferred, very particularly preferred or especially preferably has those meanings, which already in connection with the description of the inventive materials Formula (J) for these radicals have been mentioned as preferred, particularly preferred etc.
Δ^Pyrroline der Formel (H) sind bekannt und/oder lassen sich nach bekannten Verfahren herstellen (vgl; WO 98/2243S, für R4 = Wasserstoff siehe auch WO 02/46151, für R4 = Alkyl und gegebenenfalls substituiertes Aryl siehe auch DE-A 102 05 862, für R4 = Alkoxycarbonyl, (Cycloalkyl)oxycarbonyl, (Halogenalkoxy)carbonyl siehe auch WO 02/24646, siehe ebenfalls die Herstellungsbeispiele).Δ ^ pyrrolines of the formula (H) are known and / or can be prepared by known processes (cf. WO 98 / 2243S, for R 4 = hydrogen see also WO 02/46151, for R 4 = alkyl and optionally substituted aryl see also DE-A 102 05 862, for R 4 = alkoxycarbonyl, (cycloalkyl) oxycarbonyl, (haloalkoxy) carbonyl see also WO 02/24646, see also the preparation examples).
Die bei der Durchführung des erfindungsgemäßen Verfahrens (A) als Ausgangsstoffe benötigten Benzol-Derivate sind durch die Formel (ID) allgemein definiert. In dieser Formel stehen A2, R6, R7, R8 und Q bevorzugt, besonders bevorzugt, ganz besonders bevorzugt bzw. insbesondere ganz besonders bevorzugt für diejenigen Bedeutungen, die bereits in Zusammenhang mit der Beschreibung der erfindungsgemäßen Stoffe der Formel (I) für diese Reste als bevorzugt, besonders bevorzugt etc. genannt wurden.Formula (ID) provides a general definition of the benzene derivatives required as starting materials when carrying out process (A) according to the invention. In this formula, A 2 , R 6 , R 7 , R 8 and Q preferably, particularly preferably, very particularly preferably or in particular very particularly preferably represent those meanings which have already been associated with the description of the substances of the formula (I) according to the invention were mentioned as preferred, particularly preferred etc. for these radicals.
Benzol-Derivate der Formel (IH) sind teilweise bekannt und/oder können in analoger Weise zu bekannten Verbindungen herstellt werden (vgl. für Ql: Helv. Chim. Acta 1989, 72, 447-Benzene derivatives of the formula (IH) are known in some cases and / or can be prepared in an analogous manner to known compounds (cf. for Q1: Helv. Chim. Acta 1989, 72, 447-
456, J. Heterocycl. Chem. 1998, 35, 1313-1316, Pharm. Chem. J. (Engl.), 1971, 5, 401, Chem. HeterocycL Compd. (Engl.) 1984, 20,. 1319-1321, JCS Chem. Commun. 1981, 21, 1106-1107, JCS Chem. Commun. 1992, 4, 348-349, J. Am. Chem. Soc 1941, 63, 3189- 3191, Bull. Chem. Soc. Jpn. 1998, 71, 475-482; für Q2: J. Chem. Soc. 1904, 85, 1483, J. HeterocycL Chem. 2001, 38, 1197-1202, Chem. Pharm. Bull. 1985, 33, 93,7-943, Tetrahedron Lett. 1992, 3911-3914, Helv. Chim. Acta 1993, 76, 521-534, Tetrahedron Lett.456, J. Heterocycl. Chem. 1998, 35, 1313-1316, Pharm. Chem. J. (Engl.), 1971, 5, 401, Chem. HeterocycL Compd. (Engl.) 1984, 20 ,. 1319-1321, JCS Chem. Commun. 1981, 21, 1106-1107, JCS Chem. Commun. 1992, 4, 348-349, J. Am. Chem. Soc 1941, 63, 3189-3191, Bull. Chem. Soc. Jpn. 1998, 71, 475-482; for Q2: J. Chem. Soc. 1904, 85, 1483, J. HeterocycL Chem. 2001, 38, 1197-1202, Chem. Pharm. Bull. 1985, 33, 93.7-943, Tetrahedron Lett. 1992, 3911-3914, Helv. Chim. Acta 1993, 76, 521-534, Tetrahedron Lett.
1994, 3609-3612, JCS Chem. Commun. 1982, 18, 1055-1056, J. Org. Chem. 1984, 49, 3819- 3824, Synthesis 1999, 1, 61-63; für Q3: J. Org. Chem. 1970, 35, 1729, Egypt. J. Chem. 1999, 42, 491-498, J. Prakt. Chem. 1985, 327, 463-470, JCS Perkin Trans. 1 1987, 1457- 1464, JCS Perkin Trans. 1 1992, 2203-2214, Phosphorus Sulfur 1977, 3, 377, J. Org. Chem. 2001, 66, 7283-7286, J. Am. Chem. Soc. 1954, 76, 4450-4452, Synth. Commun. 1995, 25,1994, 3609-3612, JCS Chem. Commun. 1982, 18, 1055-1056, J. Org. Chem. 1984, 49, 3819-3824, Synthesis 1999, 1, 61-63; for Q3: J. Org. Chem. 1970, 35, 1729, Egypt. J. Chem. 1999, 42, 491-498, J. Prakt. Chem. 1985, 327, 463-470, JCS Perkin Trans. 1 1987, 1457-1464, JCS Perkin Trans. 1 1992, 2203-2214, Phosphorus Sulfur 1977, 3, 377, J. Org. Chem. 2001, 66, 7283-7286, J. Am. Chem. Soc. 1954, 76, 4450-4452, Synth. Commun. 1995, 25,
2449-2456, Liebigs Ann. Chem. 1988, 465-470, J. HeterocycL Chem. 1994, 31, 1005-1010; für Q4: Bull. Chem. Soc. Jpn. 1994, 67, 2187-2.194,- Liebigs Ann. Chem. 1992, 387-394; C. R. Hebd. Seances Acad. Sei. , 1953, 237, 397, Tetrahedron Lett. 1995, 1925-1928, Synthesis 1993, 10, 959-960, J. Prakt. Chem. 1983, 325, 457-462, Bioorg. Med. Chem. Lett. 1997, 7, 3101-3106, Tetrahedron Lett. 1989, 3093-3096, Bull. Soc. Chim. Fr. 1956, 1147-1150; für2449-2456, Liebigs Ann. Chem. 1988, 465-470, J. HeterocycL Chem. 1994, 31, 1005-1010; for Q4: Bull. Chem. Soc. Jpn. 1994, 67, 2187-2.194, Liebigs Ann. Chem. 1992, 387-394; C. R. Hebd. Seances Acad. Be. , 1953, 237, 397, Tetrahedron Lett. 1995, 1925-1928, Synthesis 1993, 10, 959-960, J. Prakt. Chem. 1983, 325, 457-462, Bioorg. Med. Chem. Lett. 1997, 7, 3101-3106, Tetrahedron Lett. 1989, 3093-3096, Bull. Soc. Chim. Fr. 1956, 1147-1150; For
Q5: J. HeterocycL Chem. 1993, 30, 617-622, JCS Chem. Commun. 1990, 20, 1393-1394, J. HeterocycL Chem. 1992, 29, 1401-1403, J. Indian Chem. Soc. 1987. 64, 713-715, Acta Chem. Scand. 1998, 52, 399-406, JCS Perkin Trans. 1 1991, 3245-3251, Tetrahedron 1995, 51, 1.2373-12382, Chem. HeterocycL Compd. (Engl. ) 1991, 27, 918-920, Eur. J. Med. Chem. Chim. Ther. 1992, 27, 717-722; für Q6: J. HeterocycL Chem. 1982, 19, 977-979,Q5: J. HeterocycL Chem. 1993, 30, 617-622, JCS Chem. Commun. 1990, 20, 1393-1394, J. HeterocycL Chem. 1992, 29, 1401-1403, J. Indian Chem. Soc. 1987. 64, 713-715, Acta Chem. Scand. 1998, 52, 399-406, JCS Perkin Trans. 1 1991, 3245-3251, Tetrahedron 1995, 51, 1.2373-12382, Chem. HeterocycL Compd. (Engl.) 1991, 27, 918-920, Eur. J. Med. Chem. Chim. Ther. 1992, 27, 717-722; for Q6: J. HeterocycL Chem. 1982, 19, 977-979,
Tetrahedron 1990, 46, 3515-3526, Liebigs Ann. Chem. 1989, 1145-1146, J. HeterocycL Chem. 1995, 32, 985-990, Farmaco Ed. Sei. 1988, 43, 677-692, J. Med. Chem. 1990, 33, 21- 31, Heterocycles 1993, 36, 2541-2548, J. Org. Chem. 1984, 49, 62-1 A, Synth. Commun. 1986, 16, 357-364, Bioorg. Med. Chem. Lett. 1998, 8, 2689-2694; für Q7: Bull. Chem. Soc. Jpn. 1995, 68, 1, 341-349, Bull. Soc! Chim. Fr. 1980, 2, 11-12, 552-558, J, Indian Chem.Tetrahedron 1990, 46, 3515-3526, Liebigs Ann. Chem. 1989, 1145-1146, J. HeterocycL Chem. 1995, 32, 985-990, Farmaco Ed. Be. 1988, 43, 677-692, J. Med. Chem. 1990, 33, 21-31, Heterocycles 1993, 36, 2541-2548, J. Org. Chem. 1984, 49, 62-1 A, Synth. Commun. 1986, 16, 357-364, Bioorg. Med. Chem. Lett. 1998, 8, 2689-2694; for Q7: Bull. Chem. Soc. Jpn. 1995, 68, 1, 341-349, Bull. Soc! Chim. Fr. 1980, 2, 11-12, 552-558, J, Indian Chem.
Soc. 1987, 64, 713-715, J. Chem. Res. Miniprint 1995, 8, 1901-1912, Tetrahedron 2001, 57, 22, 4767-4774, J. Org. Chem. 1997, 62, 3, 715-720, Tetrahedron 1994, 50, 26, 7849-7856, J. Org. Chem. 1986, 51, 16, 3125-3133, JCS Perkin Trans. 1 1997, 1851-1854, J. Am. Chem. Soc. 1967, 89, 3077; fürQδ: Justus Liebigs Ann. Chem. 1911,355, 100, J. Chem. Soc. C 1971, 2147-2150, J. Gen. Chem. USSR (Engl.), 1977, 47, 81-86, Biochem. J. 1936, 30, 407,Soc. 1987, 64, 713-715, J. Chem. Res. Miniprint 1995, 8, 1901-1912, Tetrahedron 2001, 57, 22, 4767-4774, J. Org. Chem. 1997, 62, 3, 715-720, Tetrahedron 1994, 50, 26, 7849-7856, J. Org. Chem. 1986, 51, 16, 3125-3133, JCS Perkin Trans. 1 1997, 1851-1854, J. Am. Chem. Soc. 1967, 89, 3077; for Qδ: Justus Liebigs Ann. Chem. 1911, 355, 100, J. Chem. Soc. C 1971, 2147-2150, J. Gen. Chem. USSR (Engl.), 1977, 47, 81-86, Biochem. J. 1936, 30, 407,
J. Am. Chem. Soc. 1993, 115, 7645-7652, Chem. Ber, i960, 93, 1208,1211, J. Gen. Chem. USSR (Engl.) 1961, 31, 1390, Chem. Ber. 1968, 101, 839, Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1967, 300, 704-708, Tetrahedron 1999, 55, 14451-14458, Chem. Ber. 1978, 111, 780- 790, J. Org. Chem. 1966, 31, 1538-1541, Farmaco Ed. Sei. 1971, 26, 276-286, J. Chem. Soc. 1963, 1332,1333, Justus Liebigs Ann. Chem. 1904, 331, 206, Justus Liebigs Ann. Chem. 1902, 320, 26, Justus Liebigs Ann. Chem. 1904, 331, 224, Justus Liebigs Ann. Chem. 1904, 331, 234, Justus Liebigs Ann. Chem. 1908, 361, 270, Synth. Commun. 1996, 26, 4289-4297, C. R. Hebd. Seances Acad. Sei. Ser. C 1968, 266, 290-292, Bull, Soc. Chim. Belg. 1977, 86, 949-952, J. HeterocycL Chem. 1974, 11, 135-137, J. Chem. Soc. C 1970, 445-448, Heterocycles 1993, 35, 909-914, J. Org. Chem. 1969, 34, 1474-1477, J. Am. Chem. Soc.J. Am. Chem. Soc. 1993, 115, 7645-7652, Chem. Ber, i960, 93, 1208, 1211, J. Gen. Chem. USSR (Engl.) 1961, 31, 1390, Chem. Ber. 1968, 101, 839, Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1967, 300, 704-708, Tetrahedron 1999, 55, 14451-14458, Chem. Ber. 1978, 111, 780-790, J. Org. Chem. 1966, 31, 1538-1541, Farmaco Ed. Be. 1971, 26, 276-286, J. Chem. Soc. 1963, 1332, 1333, Justus Liebigs Ann. Chem. 1904, 331, 206, Justus Liebigs Ann. Chem. 1902, 320, 26, Justus Liebigs Ann. Chem. 1904, 331, 224, Justus Liebigs Ann. Chem. 1904, 331, 234, Justus Liebigs Ann. Chem. 1908, 361, 270, Synth. Commun. 1996, 26, 4289-4297, CR Hebd. Seances Acad. Be. Ser. C 1968, 266, 290-292, Bull, Soc. Chim. Belg. 1977, 86, 949-952, J. HeterocycL Chem. 1974, 11, 135-137, J. Chem. Soc. C 1970, 445-448, Heterocycles 1993, 35, 909-914, J. Org. Chem. 1969, 34, 1474-1477, J. Am. Chem. Soc.
1941, 63, 1677, Helv. Chim. Acta, 1927, 10, 305, Heterocycles 1992, 33, 813-818, J. Org. Chem. 1962, 27, 4293-4300, J. Gen. Chem. USSR (Engl.) 1961, 31, 159, J. Am. Chem. Soc. 1961, 83, 2937, Can. J. Chem. 1963, 41, 2086-2092, Bull. Soc. Chim. Fr. 1975, 1371-1373; für Q9: J. Am. Chem. Soc. 1950, 72, 3843,3844, Gazz. Chim. Bai. 1957, 87, 720,724, Chem. Ber. 1960, 93, 1433-1446, BulL Soc. Chim. Fr. 1966, 2832-2845, J. Org. Chem. 1961, 26,1941, 63, 1677, Helv. Chim. Acta, 1927, 10, 305, Heterocycles 1992, 33, 813-818, J. Org. Chem. 1962, 27, 4293-4300, J. Gen. Chem. USSR (Engl.) 1961, 31, 159, J. Am. Chem. Soc. 1961, 83, 2937, Can. J. Chem. 1963, 41, 2086-2092, Bull. Soc. Chim. Fr. 1975, 1371-1373; for Q9: J. Am. Chem. Soc. 1950, 72, 3843, 3844, Gazz. Chim. Bai. 1957, 87, 720, 724, Chem. Ber. 1960, 93, 1433-1446, BulL Soc. Chim. Fr. 1966, 2832-2845, J. Org. Chem. 1961, 26,
4441-4455, J. Org. Chem. 1973, 38, 2949-2953, J. Org. Chem. 1973, 38, 2945-2948, Bull. Soc. Chim. Fr. 1966, 2381-2384, Tetrahedron Lett. 1973, 1199, Chem. HeterocycL Compd. (Engl.) 1979, 15, 501-506, Tetrahedron Lett. 1988, 6001-6004, J. Org. Chem. 1965, 30, 1892-1895, J. Org. Chem. 1969, 34, 3639, Justus Liebigs Ann. Chem. 1968, 719, 145, J. HeterocycL Chem 1972, 9, 1219-1223, J. HeterocycL Chem. 1988, 25, 1307-1310,4441-4455, J. Org. Chem. 1973, 38, 2949-2953, J. Org. Chem. 1973, 38, 2945-2948, Bull. Soc. Chim. 1966, 2381-2384, Tetrahedron Lett. 1973, 1199, Chem. HeterocycL Compd. (Engl.) 1979, 15, 501-506, Tetrahedron Lett. 1988, 6001-6004, J. Org. Chem. 1965, 30, 1892-1895, J. Org. Chem. 1969, 34, 3639, Justus Liebigs Ann. Chem. 1968, 719, 145, J. HeterocycL Chem 1972, 9, 1219-1223, J. HeterocycL Chem. 1988, 25, 1307-1310,
Tetrahedron 1990, 46, 577-586, Heterocycles 1996, 43, 1597-1600, J. Prakt. Chem. 1986, 328, 321-326, C. R. Hebd. Seances Acad. Sei. Ser. C 1968, 266, 290-292, Chem. Ber. 1959, 92, 2593-2599, DE-A 2643640, J. Chem. Res. Synop. 1995, 5, 198-199, J. HeterocycL Chem. 1994, 31, 1377-1380, Chem. Pharm. Bull. 1984, 32, 4402-4409, Bioorg. Med. Chem. Lett. 1997, 7, 2121-2124, J. Org. Chem. 1997, 62, 8325-8334, J. HeterocycL Chem. 1993,Tetrahedron 1990, 46, 577-586, Heterocycles 1996, 43, 1597-1600, J. Prakt. Chem. 1986, 328, 321-326, C. R. Hebd. Seances Acad. Be. Ser. C 1968, 266, 290-292, Chem. Ber. 1959, 92, 2593-2599, DE-A 2643640, J. Chem. Res. Synop. 1995, 5, 198-199, J. HeterocycL Chem. 1994, 31, 1377-1380, Chem. Pharm. Bull. 1984, 32, 4402-4409, Bioorg. Med. Chem. Lett. 1997, 7, 2121-2124, J. Org. Chem. 1997, 62, 8325-8334, J. HeterocycL Chem. 1993,
30, 365-371, Helv. Chim. Acta 1927, 10, 305, Heterocycles 1992, 33, 813-818, Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1967, 300, 704-708, J. Org. Chem. 1962, 27, 4293-4300, J. Am. Chem. Soc. 1961, 83, 2937, Can. J. Chem. 1963, 41, 2086-2092, BulL Soc. Chim. Fr. 1975, 1371-1373; für Q10: J. Prakt. Chem. 1935, 143, 259, 273, Angew. Chem. 1978, 90, 731-732, DE-A 1809386, J. Am. Chem. Soc. 1949, 71, 2671-2674, Bull. Soc. Chim. Fr.30, 365-371, Helv. Chim. Acta 1927, 10, 305, Heterocycles 1992, 33, 813-818, Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1967, 300, 704-708, J. Org. Chem. 1962, 27, 4293-4300, J. Am. Chem. Soc. 1961, 83, 2937, Can. J. Chem. 1963, 41, 2086-2092, BulL Soc. Chim. Fr. 1975, 1371-1373; for Q10: J. Prakt. Chem. 1935, 143, 259, 273, Angew. Chem. 1978, 90, 731-732, DE-A 1809386, J. Am. Chem. Soc. 1949, 71, 2671-2674, Bull. Soc. Chim. Fr.
1969, 1687, Tetrahedron Lett. 1998, 3287-3290, Syn. Lett. 1999, 3, 299-302, Justus Liebigs Ann. Chem. 1927, 458, 209, Chem. Ber. 1978, 111, 791-794, BulL Chem. Soc. Jpn. 2000, 73, 1861-1864, DE-A 2524048, J. Med. Chem. 1997, 40, 1347-1365, J. HeterocycL Chem. 1973, 10, 669-670, Bull. Soc. Chim. Belg. 1977, 86, 949-952, Acta Chem. Scand. 1970, 24, 3109-3115, J. HeterocycL Chem. 1986, 23, 1363-1366, Justus Liebigs Ann. Chem. 1908,1969, 1687, Tetrahedron Lett. 1998, 3287-3290, Syn. Lett. 1999, 3, 299-302, Justus Liebigs Ann. Chem. 1927, 458, 209, Chem. Ber. 1978, 111, 791-794, BulL Chem. Soc. Jpn. 2000, 73, 1861-1864, DE-A 2524048, J. Med. Chem. 1997, 40, 1347-1365, J. HeterocycL Chem. 1973, 10, 669-670, Bull. Soc. Chim. Belg. 1977, 86, 949-952, Acta Chem. Scand. 1970, 24, 3109-3115, J. HeterocycL Chem. 1986, 23, 1363-1366, Justus Liebigs Ann. Chem. 1908,
358, 169, J. HeterocycL Chem. 1990, 27, 487-495, Chem. Lett. 1988, 5, 819-822, Chem. Pharm. Bull. 1984, 32, 4402-4409, J. Org. Chem. 1961, 26, 948, Can. J. Chem. 1979, 57, 1186-1200; für Qll: Justus Liebigs Ann. Chem. 1932, 492, 283-291; für Q12: J. Chem. Soc. 1947, 96-100, J. Am. Chem. Soc. 1993, 115, 7645-7652, Tetrahedron Lett. 1999, 2657-2660, Bull. Soc. Chim. Fr. 1986, 1, 129-132, Chem. HeterocycL Compd. (Engl.) 1979, 15, 544- 548, Tetrahedron 1996, 52, 7939-7946, Monatsh. Chem. 1996, 127, 313-318, Tetrahedron Lett. 1989, 4435-4438, Synthesis 1987, 12, 1136-1138, Can. J. Chem. 1979, 57, 813-821, US 3,644,392, J. Med. Chem. 1985, 28, 1405-1413, JCS Perkin Trans. 1 1994, 239-244, J. Fluorine Chem. 1995, 74, 279-282, J. Med. Chem. 1989, 32, 575-583, J. Org. Chem. 1977, 42, 1153-1159, J. Prakt. Chem. 1991, 333, 355-360, J. Indian Chem. Soc. 1981, 58, 624-625,358, 169, J. HeterocycL Chem. 1990, 27, 487-495, Chem. Lett. 1988, 5, 819-822, Chem. Pharm. Bull. 1984, 32, 4402-4409, J. Org. Chem. 1961, 26, 948, Can. J. Chem. 1979, 57, 1186-1200; for Qll: Justus Liebigs Ann. Chem. 1932, 492, 283-291; for Q12: J. Chem. Soc. 1947, 96-100, J. Am. Chem. Soc. 1993, 115, 7645-7652, Tetrahedron Lett. 1999, 2657-2660, Bull. Soc. Chim. Fr. 1986, 1, 129-132, Chem. HeterocycL Compd. (Engl.) 1979, 15, 544- 548, Tetrahedron 1996, 52, 7939-7946, monthly. Chem. 1996, 127, 313-318, Tetrahedron Lett. 1989, 4435-4438, Synthesis 1987, 12, 1136-1138, Can. J. Chem. 1979, 57, 813-821, US 3,644,392, J. Med. Chem. 1985, 28, 1405-1413, JCS Perkin Trans. 1 1994, 239-244, J. Fluorine Chem. 1995, 74, 279 -282, J. Med. Chem. 1989, 32, 575-583, J. Org. Chem. 1977, 42, 1153-1159, J. Prakt. Chem. 1991, 333, 355-360, J. Indian Chem. Soc. 1981, 58, 624-625,
Tetrahedron 2001, 57, 3413-3418, Chem. Pharm. Bull. 1982, 30, 1722-1730; für Q13: J. Chem. Soc. 1948, 1969, J. HeterocycL Chem. 1983, 20, 1277-1281, Chem. Lett. 1983, 341- 342, Arch. Pharm. (Weinheim Ger.) 1976, 309, 391-394, DE-A 2533211, Arch. Pharm. (Weinheim Ger.) 1974, 307, 972-975, J. Chem. Soc. 1957, 4225-4227, Chem. Pharm. Bull. 1988, 36, 1669-1675, Synthesis 1995, 4, 449-452, J. Org. Chem. 1997, 62, 3480-3487, J.Tetrahedron 2001, 57, 3413-3418, Chem. Pharm. Bull. 1982, 30, 1722-1730; for Q13: J. Chem. Soc. 1948, 1969, J. HeterocycL Chem. 1983, 20, 1277-1281, Chem. Lett. 1983, 341-342, Arch. Pharm. (Weinheim Ger.) 1976, 309, 391-394, DE-A 2533211, Arch. Pharm. (Weinheim Ger.) 1974, 307, 972-975, J. Chem. Soc , 1957, 4225-4227, Chem. Pharm. Bull. 1988, 36, 1669-1675, Synthesis 1995, 4, 449-452, J. Org. Chem. 1997, 62, 3480-3487, J.
HeterocycL Chem. 1977, 14, 889-891, US 4,110,456, J. Med. Chem. 1975, 18, 895-896, DE- A 2061489, DE-A 2061515, US 4,125,530, Chem. Pharm. BulL 1986, 34, 3111-3120, Tetrahedron 1997, 53, 7237-7254, Bull. Chem. Soc. Jpn. 1998, 71, 467-474, J. Org. Chem. 2002, 67, 2699-2701, J. Med. Chem. 1999, 42, 3572-3587, Pharmazie 1992, 47, 623-626; für Q14: J. Pharm. Pharmacol. 1964, 16, 400-402, GB 1046248, Synthesis 2001, 14, 2075-2077,HeterocycL Chem. 1977, 14, 889-891, US 4,110,456, J. Med. Chem. 1975, 18, 895-896, DE-A 2061489, DE-A 2061515, US 4,125,530, Chem. Pharm. BulL 1986, 34, 3111-3120, Tetrahedron 1997, 53, 7237-7254, Bull. Chem. Soc. Jpn. 1998, 71, 467-474, J. Org. Chem. 2002, 67, 2699-2701, J. Med. Chem. 1999, 42, 3572-3587, Pharmazie 1992, 47, 623-626; for Q14: J. Pharm. Pharmacol. 1964, 16, 400-402, GB 1046248, Synthesis 2001, 14, 2075-2077,
J. Org. Chem. 2000, 65, 1516-1524, CH 566996, JCS Perkin Trans. 1 1985, 2333-2336, J. Med. Chem. 1977, 20, 563-566, Bull. Chem. Soc. Jpn. 1978, 51, 1846-1855, J. HeterocycL Chem. 1990, 27, 487-495, J. Org. Chem. 1988, 53, 129-135, J. Org. Chem. 1982, 47, 2867- 2872, Chem. Ber. 1959, 92, 550-560, Chem. Ber. 1959, 92, 329-335, Angew. Chem. 1959, 71, 753-769, Tetrahedron 1997, 53, 11355-11368; für Q15: J. HeterocycL Chem. 1983, 20,J. Org. Chem. 2000, 65, 1516-1524, CH 566996, JCS Perkin Trans. 1 1985, 2333-2336, J. Med. Chem. 1977, 20, 563-566, Bull. Chem. Soc. Jpn. 1978, 51, 1846-1855, J. HeterocycL Chem. 1990, 27, 487-495, J. Org. Chem. 1988, 53, 129-135, J. Org. Chem. 1982, 47, 2867-2872, Chem . Ber. 1959, 92, 550-560, Chem. Ber. 1959, 92, 329-335, Angew. Chem. 1959, 71, 753-769, Tetrahedron 1997, 53, 11355-11368; for Q15: J. HeterocycL Chem. 1983, 20,
1277-1281 , Monatsh. Chem. 1968, 99, 2059-2071, Terrahedron Lett. 1971, 2205, J. Org. Chem. 1978, 43, 2289, Justus Liebigs Ann. Chem. 1954, 585, 68, 79, Angew. Chem. 1959, 71, 753-757, Chem. Ber. 1962, 95, 2049-2053, Chem. Ber. 1960, 93, 723-736, BulL Soc. Chim. Belg. 1976, 85, 573-575, J. Prakt. Chem. 1991, 333, 355-360, Justus Liebigs Ann. Chem. 1971, 744, 51-64, Tetrahedron Lett. 1968, 1809, J. Med. Chem. 1985, 28, 1188-1194,1277-1281, monthly Chem. 1968, 99, 2059-2071, Terrahedron Lett. 1971, 2205, J. Org. Chem. 1978, 43, 2289, Justus Liebigs Ann. Chem. 1954, 585, 68, 79, Angew. Chem. 1959, 71, 753-757, Chem. Ber. 1962, 95, 2049-2053, Chem. Ber. 1960, 93, 723-736, BulL Soc. Chim. Belg. 1976, 85, 573-575, J. Prakt. Chem. 1991, 333, 355-360, Justus Liebigs Ann. Chem. 1971, 744, 51-64, Tetrahedron Lett. 1968, 1809, J. Med. Chem. 1985, 28, 1188-1194,
J. HeterocycL Chem. 1990, 27, 487-495, Bioorg. Med. Chem. Lett. 1999, 9, 1023-1028, Justus Liebigs Ann. Chem. 1975, 160-194, Chem. Ber. 1959, 92, 329-335, Heterocycles 1993, 35, 433-440, Biosci. Biotechnol. Biochem. 1992, 56, 161-162, J. Med. Chem. 1996, 39, 596-604, Heterocycles 1997, 44, 67-70, Bull. Chem. Soc. Jpn. 1998, 71, 467-474, Recl. Trav. Chim. Pays-Bas 1979, 98, 258-262, J. Org. Chem. 1977, 42, 1153-1159; für Q16, Q17 und Q18: Helv. Chim. Acta 1977, 60, 284-297, JCS Perkin Trans. 1 1994, 147-152, J. Org Chem. USSR (Engl.) 1978, 14, 1697-1701, Tetrahedron 1969, 25, 771-782, J. Org. Chem, 1966, 31, 3612-3615, Tetrahedron Lett. 1992, 7769-7770, Org. Prep. Proced.-Int. 1992, 24. 127-134, Synthesis 1998, 9, 1298-1304; für Q19 und Q20: Chem. HeterocycL Compd, (Engl.) 1973, 9, 1199-1201, J. Chem. Soc. C 1971, 2644-2647, Gazz. Chim. Bai. 1938, 68,. 625, 635, Gazz. Chim. Ital. 1961, 91, 1005-1022, JCS Perkin Trans. 1 1977, 2154-2157, Chem. Abstr. 1959, 53, 5185, Gazz. Chim. Ital. 1968, 98, 331-343, JCS Perkin Trans. 1 1975, 2115-2117, Gazz. Chim. Ital. 1959, 89, 1784-1793, Tetrahedron 1961, 12, 41-50, Can. J. Chem. 1970, 48, 1371-1376, Tetrahedron Lett. 1989, 3987-3990, J. Am. Chem. Soc. 1945, 67, 132, J. Am. Chem. Soc. 1931, 53, 1133-1136; für Q21: Acta Chem. Scand. 1992, 46,J. HeterocycL Chem. 1990, 27, 487-495, Bioorg. Med. Chem. Lett. 1999, 9, 1023-1028, Justus Liebigs Ann. Chem. 1975, 160-194, Chem. Ber. 1959, 92, 329-335, Heterocycles 1993, 35, 433-440, Biosci. Biotechnol. Biochem. 1992, 56, 161-162, J. Med. Chem. 1996, 39, 596-604, Heterocycles 1997, 44, 67-70, Bull. Chem. Soc. Jpn. 1998, 71, 467-474, Recl. Trav. Chim. Pays-Bas 1979, 98, 258-262, J. Org. Chem. 1977, 42, 1153-1159; for Q16, Q17 and Q18: Helv. Chim. Acta 1977, 60, 284-297, JCS Perkin Trans. 1 1994, 147-152, J. Org Chem. USSR (Engl.) 1978, 14, 1697-1701, Tetrahedron 1969, 25, 771-782, J. Org Chem, 1966, 31, 3612-3615, Tetrahedron Lett. 1992, 7769-7770, Org. Prep. Proced.-Int. 1992, 24. 127-134, Synthesis 1998, 9, 1298-1304; for Q19 and Q20: Chem. HeterocycL Compd, (Engl.) 1973, 9, 1199-1201, J. Chem. Soc. C 1971, 2644-2647, Gazz. Chim. Bai. 1938, 68,. 625, 635, Gazz. Chim. Ital. 1961, 91, 1005-1022, JCS Perkin Trans. 1 1977, 2154-2157, Chem. Abstr. 1959, 53, 5185, Gazz. Chim. Ital. 1968, 98, 331-343, JCS Perkin Trans. 1 1975, 2115-2117, Gazz. Chim. Ital. 1959, 89, 1784-1793, Tetrahedron 1961, 12, 41-50, Can. J. Chem. 1970, 48, 1371-1376, Tetrahedron Lett. 1989, 3987-3990, J. Am. Chem. Soc. 1945, 67, 132, J. Am. Chem. Soc. 1931, 53, 1133-1136; for Q21: Acta Chem. Scand. 1992, 46,
372-383, J. Org. Chem. USSR (Engl.) 1985, 21, 191-196, J. Gen. Chem. USSR (Engl.) 1963, 33, 3590-3592, Tetrahedron 1997, 53, 9657-9668, Tetrahedron Lett. 1978, 5003-5006, Chem. HeterocycL Compd. (Engl.) 1970, 6, 322-323, J. Med. Chem. 1991, 34, 2158-2165, Eur. J. Org. Chem. 1999, 11, 3117-3126, J. HeterocycL Chem. 1994, 31, 1545-1552, Synthesis 1984, 3, 250-252, J. Am. Chem. Soc. 1949, 71, 367, J. Med. Chem. 1974, 17,372-383, J. Org. Chem. USSR 1985, 21, 191-196, J. Gen. Chem. USSR (Engl.) 1963, 33, 3590-3592, Tetrahedron 1997, 53, 9657-9668, Tetrahedron Lett. 1978, 5003-5006, Chem. HeterocycL Compd. (Engl.) 1970, 6, 322-323, J. Med. Chem. 1991, 34, 2158-2165, Eur. J. Org. Chem. 1999, 11, 3117-3126, J. HeterocycL Chem. 1994, 31 , 1545-1552, Synthesis 1984, 3, 250-252, J. Am. Chem. Soc. 1949, 71, 367, J. Med. Chem. 1974, 17,
1177-1-181; für Q22: J. Indian Chem, Soc..1975, 52, 766-767, Heterocycles 1990, 31, 1115- 1127, Justus Liebigs Ann. Chem. 1976, 395-399, Tetrahedron Lett. 1981, 3305-3308, J. Am. Chem. Soc. 1934, 56, 970, Bioorg. Med. Chem. Lett. 1999, 9, 1167-1170, JCS Perkin Trans. 1 1981, 2340-2343, Chem. Ber. 1956, 89, 107-113, Helv. Chim. Acta 1978, 61, 3143-3148, J. Chem. Soc. 1947, 1656-1658, BulL Soc. Chim. Fr. 1963, 2498-2503, Helv. Chim. Acta1177-1-181; for Q22: J. Indian Chem, Soc. , 1975, 52, 766-767, Heterocycles 1990, 31, 1115-1127, Justus Liebigs Ann. Chem. 1976, 395-399, Tetrahedron Lett. 1981, 3305-3308, J. Am. Chem. Soc. 1934, 56, 970, Bioorg. Med. Chem. Lett. 1999, 9, 1167-1170, JCS Perkin Trans. 1 1981, 2340-2343, Chem. Ber. 1956, 89, 107-113, Helv. Chim. Acta 1978, 61, 3143-3148, J. Chem. Soc. 1947, 1656-1658, BulL Soc. Chim. Fr. 1963, 2498-2503, Helv. Chim. Acta
1950, 33, 1353, 1360, Gazz. Chim. Ital. 1975, 105, 1265-1271, Collect. Czech. Chem. Commun. 1993, 58, 1898-1904; für Q23: C. R. Hebd. Seances Acad. Sei. Ser. C 1967, 264, 336-339, J. Chem. Soc. 1952, 4099-4102, J. B dian Chem. Soc. 1970, 47, 323-330, Bull. Soc. Chim. Fr. 1967, 4523-4533, JCS Perkin Trans. 1 1993, 351-356, Helv. Chim. Acta 1978, 61, 3143-3148, Bull. Soc. Chim. Fr. 1967, 4523-4533, BulL Soc. Chim. Fr. 1966,1950, 33, 1353, 1360, Gazz. Chim. Ital. 1975, 105, 1265-1271, Collect. Czech. Chem. Commun. 1993, 58, 1898-1904; for Q23: C. R. Hebd. Seances Acad. Be. Ser. C 1967, 264, 336-339, J. Chem. Soc. 1952, 4099-4102, J. B dian Chem. Soc. 1970, 47, 323-330, Bull. Soc. Chim. Fr. 1967, 4523-4533, JCS Perkin Trans. 1 1993, 351-356, Helv. Chim. Acta 1978, 61, 3143-3148, Bull. Soc. Chim. Fr. 1967, 4523-4533, BulL Soc. Chim. Fr. 1966,
2857-2861; für Q24 und Q25: Heterocycles 1994, 37, 859-868, J. HeterocycL Chem. 1987, 24, 243-245, Chem. Pharm. Bull. 1968, 16, 148-159, J. HeterocycL Chem. 19.70, 7, 871-873, . Tetrahedron 1969, 25, 389-395, J. Amer. Chem. Soc. 1985, 107, 2721-2730, Aust. J. Chem. 1989, 42, 1291-1306, Synthesis 1987, 4, 349-353, Chem. Lett. 1984, 1691-1692; für Q26: J. HeterocycL Chem. 1973, 10, 611-622, Monatsh. Chem. 1926, 47, 798, Gazz. Chim. Ital.2857-2861; for Q24 and Q25: Heterocycles 1994, 37, 859-868, J. HeterocycL Chem. 1987, 24, 243-245, Chem. Pharm. Bull. 1968, 16, 148-159, J. HeterocycL Chem. 19.70, 7, 871-873. Tetrahedron 1969, 25, 389-395, J. Amer. Chem. Soc. 1985, 107, 2721-2730, Aust. J. Chem. 1989, 42, 1291-1306, Synthesis 1987, 4, 349-353, Chem. Lett. 1984, 1691-1692; for Q26: J. HeterocycL Chem. 1973, 10, 611-622, monthly. Chem. 1926, 47, 798, Gazz. Chim. Ital.
1923, 53, 641, Gazz. Chim. Ital. 1924, 54, 213, Monatsh. Chem. 1927, 48, 396, J. Prakt. Chem. 1903, 67, 492, J. HeterocycL Chem. 1983, 20, 1693-1695, Eur. J. Med. Chem. Chim. Ther. 1990, 25, 95-101, J. HeterocycL Chem. 1983, 20, 1533-1537, Russ. J. Org. Chem. 2001, 37, 1621-1628; für Q27: Indian J. Chem. 1971, 9, 642-646, J. Indian Chem. Soc. 1974, 51, 613, Farmacia (Bucharest), 1971, 19, 199,202, J. HeterocycL Chem. 1984, 21, 1225-1923, 53, 641, Gazz. Chim. Ital. 1924, 54, 213, monthly. Chem. 1927, 48, 396, J. Prakt. Chem. 1903, 67, 492, J. HeterocycL Chem. 1983, 20, 1693-1695, Eur. J. Med. Chem. Chim. Ther. 1990, 25, 95-101, J. HeterocycL Chem. 1983, 20, 1533-1537, Russ. J. Org. Chem. 2001, 37, 1621-1628; for Q27: Indian J. Chem. 1971, 9, 642-646, J. Indian Chem. Soc. 1974, 51, 613, Farmacia (Bucharest), 1971, 19, 199.202, J. HeterocycL Chem. 1984, 21, 1225-
1229, J. Bidian Chem. Soc. 1984, 61, 530-533, Indian J. Chem. Sect. B20 1981, 11, 1017- 1018, Diss. Pharm. Pharmacol. 1970, 22, 217, Chem. HeterocycL Compd. (Engl.) 1968, 4, 275, Bidian J. Chem. 1973, 11, 321-324; für Q28: Heterocycles 1993, 36, 455-472, Arch. Pharm. (Weinheim Ger.) 1990, 323, 225-227, Arch. Pharm. (Weinheim Ger.) 1990, 323, 221-223, Eur. J. Med. Chem. Chim. Ther. 1990, 25, 95-101, Monatsh. Chem. 1988, 119, 349-354, DE-A 2265212, Heterocycles 1992, 34, 315-320, J. HeterocycL Chem. 1983, 20, 1693-1695, Synthesis 1983, 6, 483-486, Chem. Ber. 1979,, 112, 1635-1649, Molecules 2001, 6, 969-978, Chem. Pharm. Bull. 19.75, 23, 955,959, Bioorg. Med. Chem. Lett, 2001, 11, 3165-3168; für Q29: J. Org. Chem. USSR (Engl.) 1988, 24, 1794-1800, Justus Liebigs Ann. Chem.1951, 574, 85-97, J. Med. Chem. 1994, 37, 125-132, DE-A 2265212, Synthesis 1983,1229, J. Bidian Chem. Soc. 1984, 61, 530-533, Indian J. Chem. Sect. B20 1981, 11, 1017-1018, Diss. Pharm. Pharmacol. 1970, 22, 217, Chem. HeterocycL Compd. (Engl.) 1968, 4, 275, Bidian J. Chem. 1973, 11, 321-324; for Q28: Heterocycles 1993, 36, 455-472, Arch. Pharm. (Weinheim Ger.) 1990, 323, 225-227, Arch. Pharm. (Weinheim Ger.) 1990, 323, 221-223, Eur. J. Med. Chem. Chim. Ther. 1990, 25, 95-101, monthly. Chem. 1988, 119, 349-354, DE-A 2265212, Heterocycles 1992, 34, 315-320, J. HeterocycL Chem. 1983, 20, 1693-1695, Synthesis 1983, 6, 483-486, Chem. Ber. 1979, 112, from 1635 to 1649, Molecules 2001, 6, 969-978, Chem. Pharm. Bull. 19.75, 23, 955.959, Bioorg. Med. Chem. Lett, 2001, 11, 3165-3168; for Q29: J. Org. Chem. USSR (Engl.) 1988, 24, 1794-1800, Justus Liebigs Ann. Chem. 1951, 574, 85-97, J. Med. Chem. 1994, 37, 125-132, DE-A 2265212, Synthesis 1983,
6, 483-486; für Q30: Eur. J. Med. Chem. Chim. Ther. 1985, 20, 257-266, J. Med. Chem. 1994, 37, 125-132, J. Med. Chem. 1971, 14, 260-262, J. Indian Chem. Soc. 1984, 61, 530- 533, J. HeterocycL Chem. 1984, 21, 1225-1229; für Q31: J. Chem. Soc. 1954, .4251, J. HeterocycL Chem. 1983, 20, 1609-1612, Collect. Czech. Chem. Commun. 1985, 50, 2722- 2729, DE-A 2426878, DE-A 2050346; für Q32: J. Phys. Chem. B105 2001, 37, 8845-8860,6, 483-486; for Q30: Eur. J. Med. Chem. Chim. Ther. 1985, 20, 257-266, J. Med. Chem. 1994, 37, 125-132, J. Med. Chem. 1971, 14, 260-262, J. Indian Chem. Soc. 1984, 61, 530-533, J. HeterocycL Chem. 1984, 21, 1225-1229; for Q31: J. Chem. Soc. 1954, .4251, J. HeterocycL Chem. 1983, 20, 1609-1612, Collect. Czech. Chem. Commun. 1985, 50, 2722-2729, DE-A 2426878, DE-A 2050346; for Q32: J. Phys. Chem. B105 2001, 37, 8845-8860,
- Chem. HeterocycL Compd. (Engl.) 1997, 33, 712-717, Bull. Soc. Chim. Fr., 1966, 153-159,- Chem. HeterocycL Compd. (Engl.) 1997, 33, 712-717, Bull. Soc. Chim. Fr., 1966, 153-159,
Agric. Biol. Chem. 1973, 37, 1465-1466, Justus Liebigs Ann. Chem. 1965, 686, 145-153; für Q33: Gazz. Chim. Ital. 1932, 62, 432-434, Indian J. Chem. Sect. B27 1988, 1-12, 793-Agric. Biol. Chem. 1973, 37, 1465-1466, Justus Liebigs Ann. Chem. 1965, 686, 145-153; for Q33: Gazz. Chim. Ital. 1932, 62, 432-434, Indian J. Chem. Sect. B27 1988, 1-12, 793-
796; für Q34: Ann. Chim. (Rome) 1957, 47, 376-384, J. Org. Chem. 1979, 44, 4160-4164, Chem. Pharm. Bull. 1992, 40, 2399-2409, Justus Liebigs Ann. Chem. 1968, 716, 156-159; für Q35: DE-A 2050346, DE-A 2242187, J. Org. Chem. 1974, 39, 962-964; für Q36: CH 426848, GB 899842, Chem. Pharm. BulL 1991, 39, 2837-2841, Tetrahedron 1976, 32, 1031- 1035; für Q37: Heterocycles 1996, 43, 2435-2442, J. Organomet. Chem. 1979, 166, 25-30, J. HeterocycL Chem. 1980, 17, 1681-1685; für Q38: J. Org. Chem. 1974, 39, 962-964, J. Org. Chem. 1980, 45, 3750-3753, J. Chem. Soc. 1960, 3234-3239).796; for Q34: Ann. Chim. (Rome) 1957, 47, 376-384, J. Org. Chem. 1979, 44, 4160-4164, Chem. Pharm. Bull. 1992, 40, 2399-2409, Justus Liebigs Ann. Chem. 1968, 716, 156-159; for Q35: DE-A 2050346, DE-A 2242187, J. Org. Chem. 1974, 39, 962-964; for Q36: CH 426848, GB 899842, Chem. Pharm. BulL 1991, 39, 2837-2841, Tetrahedron 1976, 32, 1031-1035; for Q37: Heterocycles 1996, 43, 2435-2442, J. Organomet. Chem. 1979, 166, 25-30, J. HeterocycL Chem. 1980, 17, 1681-1685; for Q38: J. Org. Chem. 1974, 39, 962-964, J. Org. Chem. 1980, 45, 3750-3753, J. Chem. Soc. 1960, 3234-3239).
Bei der Durchführung des erfindungsgemäßen Verfahrens (A) setzt man bevorzugt einen Palladium-Katalysator ein, der wiederum mit oder ohne Zusatz von weiteren Liganden verwendet werden kann. Vorzugsweise verwendet man als Katalysator PdCl2(dppf) [dppf = l,l'-Bis(diphenylphosphino)ferrocene], Pd(PPh3)4, PdCl2(PPh3)2, PdCl2(CH3CN)2, Pd2(dba)3 When carrying out process (A) according to the invention, preference is given to using a palladium catalyst which in turn can be used with or without the addition of further ligands. The catalyst used is preferably PdCl 2 (dppf) [dppf = l, l'-bis (diphenylphosphino) ferrocene], Pd (PPh 3 ) 4 , PdCl 2 (PPh 3 ) 2 , PdCl 2 (CH 3 CN) 2 , Pd 2 (dba) 3
[dba = Dibenzylidenaceton] oder Pd(OAc)2, besonders bevorzugt Pd(OAc)2.[dba = dibenzylidene acetone] or Pd (OAc) 2 , particularly preferably Pd (OAc) 2 .
. Als Liganden kommen Triarylphosphine, Trialkylphosphine oder Arsine in Frage. Vorzugsweise verwendet, man dppf, PPh3, P(tert-Bu)3, Pcy3 oder AsPh3, besonders bevorzugt dppf., Triarylphosphines, trialkylphosphines or arsines are suitable as ligands. Preferably used, dppf, PPh 3 , P (tert-Bu) 3 , Pcy 3 or AsPh 3 , particularly preferably dppf.
Als Verdünnungsmittel kommen bei der Durchführung des erfindungsgemäßen Verfahrens (A) jeweils alle üblichen inerten, organischen Solventien in Frage. Vorzugsweise verwendbar sind gegebenenfalls halogenierte aliphatische, alicyclische oder aromatische Kohlenwasserstoffe, wie Petrolether, Hexan, Heptan, Cyclohexan, Methylcyclohexan, Benzol, To- luol, Xylol oder Decalin; Chlorbenzol, Dichlorbenzol, Dichlormethan, CWoroform, Tetra- chlormethan, Dichlorethan oder Trichlorethan; Ether, wie Diethylether, Diisopropylether, Methyl-tert-butylether, Methyl-tert-amylether, Dioxan, Tetrahydrofuran, 1,2-Dimethoxy- ethan, 1,2-Diethoxyethan oder Anisol; Nitrile, wie Acetonitril, Propionitril, n- oder iso- Butyronitril oder Benzonitril; Amide, wie N,N-Dimethylformamid, N,N-Dimethylacetamid, N-Methylformanilid, N-Methylpyrrolidon oder Hexamethylphosphorsäuretriamid; Ester wie Essigsäuremethylester oder Essigsäureethylester, Sulfoxide, wie Dimethylsulfoxid oder Sul- fone, wie Sulfolan. Besonders bevorzugt verwendet man Aceton, Dimethoxyethan, Dioxan, Tetrahydrofuran, Dimethylformamid, Dimethylacetamid, Dimethylsulfoxid, Ethanol, Toluol oder gegebenenfalls Gemische dieser genannten Verdünnungsmittel.mit Wasser.Suitable diluents for carrying out process (A) according to the invention are all customary inert, organic solvents. Halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Chlorobenzene, dichlorobenzene, dichloromethane, CWoroform, tetra- chloromethane, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Nitriles, such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide or sulfones such as sulfolane. Acetone, dimethoxyethane, dioxane, tetrahydrofuran, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, ethanol, toluene or, if appropriate, mixtures of these diluents with water are particularly preferably used.
Als Base kommen bei der Durchführung der erfindungsgemäßen Verfahrens (A) alle für derartige Reaktionen üblichen anorganischen und organischen Basen in Betracht. Vorzugsweise verwendbar sind Erdalkali- oder Alkalimetallhydroxide, wie Natriumhydroxid, Calciumhydroxid, Kaliumhydroxid, oder auch Ammoniumhydroxid, Alkalimetall- carbonate, wie Natriumcarbonat, Kaliumcarbonat, Kaliumhydrogencarbonat, Natriumhydro- gencarbonat, Alkali- oder Erdalkalimetallacetate wie Natriumacetat, Kaliumacetat, Calcium- acetat, Alkalimetallfluoride, sowie tertiäre Amine, wie Trime ylamin, Triethylamin, Tri- butylamin, N,N-Dimethylanilin, Pyridin, N-Methylpiperidin, N,N-Dmιemylarnmopyridin, Diazabicyclooctan (DABCO), Diazabicyclononen (DBN) oder Diazabicycloundecen (DBU). Es ist jedoch auch möglich, ohne zusätzliches Säurebindemittel zu arbeiten, oder dieSuitable bases for carrying out process (A) according to the invention are all inorganic and organic bases customary for such reactions. Alkaline earth or alkali metal hydroxides, such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or also ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, alkali metal or alkaline earth metal acetates such as sodium acetate, potassium acetate, calcium acetal and alkali metal acetate, and alkali metal acetate, are preferably usable Tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimimylarnmopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU). However, it is also possible to work without an additional acid binder, or the
Anώikomponente in einem Überschuss einzusetzen, so dass sie gleichzeitig als Säurebindemittel fungiert. Besonders bevorzugt verwendet man Bariumhydroxid, Natriumhydroxid, Kaliumhydroxid, Trikaliumphosphat, Caesiumcarbonat, Kaliumcarbonat, Natriumcarbonat, Kaliumacetat, Triethylamin, Kalium-tert-butanolat, Caesiumfluorid oder Kaliumfluorid. Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßenUse an component in an excess so that it also acts as an acid binder. Barium hydroxide, sodium hydroxide, potassium hydroxide, tripotassium phosphate, cesium carbonate, potassium carbonate, sodium carbonate, potassium acetate, triethylamine, potassium tert-butanolate, cesium fluoride or potassium fluoride are particularly preferably used. The reaction temperatures can be carried out when carrying out the inventive
Verfahrens (A) in einem größeren Bereich variiert werden. Bn allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 140°C, vorzugsweise zwischen 20°C und 120°C, besonders bevorzugt zwischen 60°C und 100°C.Process (A) can be varied over a wide range. In general, temperatures between 0 ° C and 140 ° C, preferably between 20 ° C and 120 ° C, particularly preferably between 60 ° C and 100 ° C.
Bei der Durchführung des erfindungsgemäßen Verfahrens (A) setzt man auf 1 Mol anWhen carrying out process (A) according to the invention, the starting point is 1 mol
Verbindung der Formel (H) im allgemeinen 1 Mol oder einen leichten Überschuss einer Verbindung der Formel (JE), sowie 0,1 bis 50 Mol% eines Katalysators ein. Es ist jedoch auch möglich, die Reaktionskomponenten in anderen Verhältnissen einzusetzen. Die Aufarbeitung erfolgt nach üblichen Methoden. Bn allgemeinen verfährt man in der Weise, dass man das Reaktionsgemisch mit Wasser verdünnt und mit einem organischen Verdün- nungsmittel extrahiert. Die organische Phase wird gewaschen, getrocknet, filtriert und eingeengt. Der Rückstand wird gegebenenfalls nach üblichen . Methoden, wie Chromatographie oder Umkristallisation, von eventuell noch vorhandenen Verunreinigungen befreit.Compound of formula (H) generally 1 mol or a slight excess of a compound of formula (JE), and 0.1 to 50 mol% of a catalyst. However, it is also possible to use the reaction components in other ratios. The processing takes place according to usual methods. In general, the procedure is followed by diluting the reaction mixture with water and using an organic diluent. Extracted agent. The organic phase is washed, dried, filtered and concentrated. The residue is optionally after usual. Methods such as chromatography or recrystallization are freed of any impurities that may still be present.
Bei der Durchführung aller erfindungsgemäßen Verfahren arbeitet man im allgemeinen unter Atmosphärendruck. Es ist abier auch möglich, jeweils unter erhöhtem oder vermindertem Druck zu arbeiten.When carrying out all the processes according to the invention, the procedure is generally carried out under atmospheric pressure. Abier it is also possible to work under increased or reduced pressure.
Die Wirkstoffe eignen sich bei guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit zum Schutz von Pflanzen und Pflanzenorganen, zurWith good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility, the active ingredients are suitable for protecting plants and plant organs
Steigerung der Ernteerträge, Verbesserung der Qualität des Erntegutes und zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren und Nematoden, die in der Landwirtschaft, in Forsten, in Gärten und Freizeiteinrichtungen, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. Sie können vorzugsweise als Pflanzen- Schutzmittel eingesetzt werden. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören:Increasing crop yields, improving the quality of crops and combating animal pests, especially insects, arachnids and nematodes, which are found in agriculture, in forests, in gardens and leisure facilities, in the protection of stocks and materials, and in the hygiene sector. They can preferably be used as plant protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:
Aus der Ordnung der Isopoάa z.B. Oniscus asellus, Armadillidium vulgäre, Porcellio scaber. Aus der Ordnung der Diplopoda z.B. Blaniulus guttulatus.From the order of the Isopoάa e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the Diplopoda e.g. Blaniulus guttulatus.
Aus der Ordnung der Chilopoda z.B. Geophilus carpophagus, Scutigera spp..From the order of the Chilopoda e.g. Geophilus carpophagus, Scutigera spp ..
Aus der Ordnung der Symphyla z.B. Scutigerella imrnaculata.From the order of the Symphyla e.g. Scutigerella imrnaculata.
Aus der Ordnung der Thysanura z.B. Lepϊsma saccharina.From the order of the Thysanura e.g. Lepϊsma saccharina.
Aus der Ordnung der Collembola z.B. Onychiurus armatus. Aus der Ordnung der Orthoptera z.B. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.From the order of the Collembola e.g. Onychiurus armatus. From the order of the Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
Aus der Ordnung der Blattaria z.B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.From the order of the Blattaria e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.
Aus der Ordnung der Dermaptera z.B. Forficula auricularia. Aus der Ordnung der Isoptera z.B. Reticulitermes spp..From the order of the Dermaptera e.g. Forficula auricularia. From the order of the Isoptera e.g. Reticulitermes spp ..
Aus der Ordnung der Phthiraptera z.B. Pediculus humanus corporis, Haematopinus spp.,From the order of the Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp.,
Linognathus spp., Trichodectes spp., Damalinia spp..Linognathus spp., Trichodectes spp., Damalinia spp ..
Aus der Ordnung der Thysanoptera z.B. Hercinothrips femoralis, Thrips tabaci, Thrips pal i, FranMiniella occidentalis. Aus der Ordnung der Heteroptera z.B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.From the order of the Thysanoptera, for example Hercinothrips femoralis, Thrips tabaci, Thrips pal i, FranMiniella occidentalis. From the order of the Heteroptera, for example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
Aus der Ordnung der Homoptera z.B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopälosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp:, Psylla spp. Aus der Ordnung der Lepidoptera z.B. Pectinophora gossypiella, Bupalus piniarius,From the order of the Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phrosiphodumonum. Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp :, Psylla spp. From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius,
Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella,1 Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae. Aus der Ordnung der Coleoptera z.B. Anöbium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptino- tarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceμthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus. Aus der Ordnung der Hymenoptera z.B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. Aus der Ordnung der Diptera z.B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoder a spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.. Aus der Ordnung der Siphonaptera z.B. Xenopsylla cheopis Ceratophyllus spp.. Aus der Klasse der Arachnida z.B. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psorop- tes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp..Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxiaothpppp., Brassica. Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, 1 Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretaanaiaanaiaanaanaanaanaanaanaanaanaanaanaana pelliferous, Cacoeciaiaanaaanaiaanaana, cacoecia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae. From the order of the Coleoptera, for example, Anöbium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodalaisisy spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceμthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethus aeneuc., Ptin., Ptin psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus. From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca ., Stomoxys spp., Oestrus spp., Hypoder a spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyomyza spp., Lyliriomyza spp spp .. From the order of the Siphonaptera, for example Xenopsylla cheopis Ceratophyllus spp .. From the class of the Arachnida, for example Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta Roleusppalus, soleivppo, Bo ., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevip ,
Zu den pflanzenparasitären Nematoden gehören z.B. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp..Plant parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaph.
Die erfϊndungsgemäßen Verbindungen der Formel (T) zeichnen sich insbesondere durch eine hervorragende Wirkung gegen Raupen, Käferlarven, Spinnmilben, Blattläuse und Minierfliegen aus.The compounds of the formula (T) according to the invention are distinguished in particular by an excellent action against caterpillars, beetle larvae, spider mites, aphids and leaf miners.
Die erfindungsgemäßen Verbindungen können gegebenenfalls in bestimmten Konzentrationen bzw. Aufwandmengen auch als Herbizide und Mikrobizide, beispielsweise als Fungizide, Antimykotika und Bakterizide verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- oder Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen.If appropriate, the compounds according to the invention can also be used in certain concentrations or application rates as herbicides and microbicides, for example as fungicides, antifungals and bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
Erfmdungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden, wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommenderAccording to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring plants
Kulturpflanzen). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungsund C^timierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transge- nen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schütz- baren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischenCrop plants). Crop plants can be plants which can be obtained by conventional breeding and timing methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Under plant parts, all above-ground and underground
Teile und Organe der Pflanzen, wie Sproß, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stengel, Stämme, Blüten, Fruchtkörper, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Erntegut sowie vegetatives und generatives Vermehrungsmaterial, beispiels- weise Stecklinge, Knollen, Rhizome, Ableger und Samen. Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Wirkstoffen erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum. oder Lagerraum nach den üblichen Behandlungsmethoden,. z.B. durch Tauchen, Sprühen, Verdampfen, Ver- nebeln, Streuen, Aufstreichen, Bijizieren und bei Vermehrungsmaterial, insbesondere beiParts and organs of the plants, such as sprout, leaf, flower and root, are to be understood, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds. The treatment of the plants and parts of plants with the active compounds according to the invention takes place directly or by acting on their surroundings, living space. or storage room according to the usual treatment methods. for example by dipping, spraying, vaporizing, misting, scattering, spreading, bijicing and in the case of propagation material, in particular with
Samen, weiterhin durch ein- oder mehrschichtiges Umhüllen.Seeds, still by single or multi-layer coating.
• Die Wirkstoffe können in die üblichen Formulierungen überführt werden, wie Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-imprägnierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren Stoffen.• The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances ,
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und oder Dispergiermitteln und oder schaumerzeugenden Mitteln.These formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and or dispersants and or foam-forming agents.
Bn Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkylnaphthaline, chlorierteIf water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated
Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine,Aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins,
- z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser.- e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
Als feste Trägerstoffe kommen in Frage: z.B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Alurniniumoxid und Silikate, als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und f aktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnussschalen, Maiskolben und Tabakstängeln; als Emulgier- und/oder schaumerzeu- gende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethylen-Fettalkohol-Ether, z.B. Alkylaryl-poly- glykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Einweißhydrolysate; als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfϊtablaugen und Mefhylcellulose.The following are suitable as solid carriers: for example ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granules are possible: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming Suitable agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: eg lignin sulfate leachate and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexformige Polymere verwendet werden, wie Gummi- arabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetäbile Öle sein.Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gew.-% Wirkstoff, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
Der erfindungsgemäße Wirkstoff kann in seinen handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffen, wie -hsektiziden, Lockstoffen, Sterilantien, Bakteriziden, Akariziden, Nemati- ziden, Fungiziden, wachstumsregulierenden Stoffen oder Herbiziden vorliegen. Zu den Bi- sektiziden zählen beispielsweise Phosphorsäureester, Carbamate, Carbonsäureester, chlo- rierte Kohlenwasserstoffe, Phenylharnstoffe, durch Mikroorganismen hergestellte Stoffe u.a.The active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as hecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. The bisecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
Besonders günstige Mischpartner sind z.B. die folgenden:Particularly cheap mixing partners are e.g. the following:
Fungizide:fungicides:
2-Phenylphenol; 8-Hydroxyquinoline sulfate; Acibenzolar-S-methyl; Aldimbrph; Amido- flumet; Ampropylfos; Ampropylfos-potassium; Andoprim; Anilazine; Azaconazole;2-phenylphenol; 8-hydroxyquinoline sulfates; Acibenzolar-S-methyl; Aldimbrph; Amidoflumet; Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole;
Azoxystrobin; Benalaxyl; Benodanil; Benomyl; Benthiavalicarb-isopropyl; Benzamacril;azoxystrobin; benalaxyl; Benodanil; benomyl; Benthiavalicarb-isopropyl; Benzamacril;
Benzamacril-isobutyl; Bilanafos; Binapacryl; Biphenyl; Bitertanol; Blasticidin-S;Benzamacril-isobutyl; bilanafos; binapacryl; biphenyl; bitertanol; Blasticidin-S;
Bromuconazole; Bupirimate; Buthiobate; Butylamine; Calcium polysulfide; Capsimycin;bromuconazole; Bupirimate; Buthiobate; butylamine; Calcium polysulfide; capsimycin;
Captafol; Captan; Carbendazim; Carboxin; Carpropamid; Carvone; Chinomethionat; Chlobenthiazone; Chlorfenazole; Chloroneb; Chlorothalonil; Chlozolinate; Clozylacon; Cyazofamid; Cyflufenamid; Cymoxanil; Cyproconazole; Cyprodinil; Cyprofuram; Dagger " G; Debacarb; Dichlofluanid; Dichlone; Dichlorophen; Diclocymet; Diclomezine; Dicloran;captafol; captan; carbendazim; carboxin; carpropamid; carvones; chinomethionat; Chlobenthiazone; Chlorfenazole; chloroneb; chlorothalonil; chlozolinate; Clozylacon; cyazofamid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger " G; Debacarb; dichlofluanid; dichlone; dichlorophene; diclocymet; diclomezine; dicloran;
Diethofencarb; Difenoconazole; Diflumetorim; Dimethirimol; Dimethomorph;diethofencarb; Difenoconazole; diflumetorim; dimethirimol; dimethomorph;
Dimoxystrobin; Diniconazole; Diniconazple-M; Dinocap; Diphenylamine; Dipyrithione; Ditalimfos; Dithianon; Dodine; Drazoxolon; Edifenphos; Epoxiconazole; Ethaboxam;dimoxystrobin; diniconazole; Diniconazple-M; dinocap; diphenylamines; Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolon; edifenphos; epoxiconazole; ethaboxam;
Ethirimol; Etridiazole; Famoxadone; Fenamidone; Fenapanil; Fenarimol; Fenbuconazole;ethirimol; etridiazole; famoxadone; fenamidone; Fenapanil; fenarimol; Fenbuconazole;
Fenfuram; Fenhexamid; Fenitropan; Fenoxanil; Fenpiclonil; Fenpropidin; Fenpropimorph;fenfuram; fenhexamid; Fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph;
Ferbam; Fluazinam; Flubenzimine; Fludioxonil; Flumetover; Flumorph; Fluoromide;ferbam; fluazinam; Flubenzimine; fludioxonil; flumetover; flumorph; fluoromides;
Fluoxastrobin; Fluquinconazole; Flurprimidol; Flusilazole; Flusulfamide; Flutolanil; Flutriafol; Folpet; Fosetyl-Al; Fosetyl-sodium; Fuberidazole; Furalaxyl; Furametpyr; Furcar- banil; Furmecyclox; Guazatine; Hexachlorobenzene; Hexaconazole; Hymexazol; Bnazalil;fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcar- banil; Furmecyclox; guazatine; Hexachlorobenzene; hexaconazole; hymexazol; Bnazalil;
Bnibenconazole; Bninoctadine triacetate; Briinoctadine tris(albesilate); Iodocarb; Ipconazole;Bnibenconazole; Bninoctadine triacetate; Briinoctadine tris (albesilate); iodocarb; ipconazole;
Iprobenfos; Iprodione; Iprovalicarb; Bumamycin; Isoprothiolane; Isovaledione; Kasugamy- cin; Kresoxim-methyl; Mancozeb; Maneb; Meferimzone; Mepanipyrim; Mepronil; Meta- laxyl; Metalaxyl-M; Metconazole; Methasulfocarb; Methfüroxam; Metiram; Metomino- strobin; Metsulfovax; Mildiomycin; Myclobutanil; Myclozolin; Natamycin; Nicobifen;iprobenfos; iprodione; iprovalicarb; Bumamycin; isoprothiolane; Isovaledione; Kasugamycin; Kresoxim-methyl; mancozeb; maneb; Meferimzone; mepanipyrim; mepronil; Metaxaxyl; Metalaxyl-M; metconazole; methasulfocarb; Methfüroxam; metiram; Metomino-strobin; Metsulfovax; mildiomycin; myclobutanil; myclozoline; natamycin; nicobifen;
Nitrothal-isopropyl; Noviflumuron; Nuarimol; Ofurace; Orysastrobin; Oxadixyl; Oxolinic acid; Oxpoconazole; Oxycarboxin; Oxyfenthiin; Paclobutrazol; Pefurazoate; Penconazole;Nitro Thal-isopropyl; Noviflumuron; nuarimol; ofurace; orysastrobin; oxadixyl; Oxolinic acid; Oxpoconazole; oxycarboxin; Oxyfenthiin; paclobutrazol; Pefurazoate; penconazole;
Pencycuron; Phosdiphen; Phthalide; Picoxystrobin; Piperalin; Polyoxins; Polyoxorim; Probenazole; Prochloraz; Procymidone; Propamocarb; Propanosine-sodium; Propiconazole;pencycuron; phosdiphen; phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorim; Probenazole; prochloraz; procymidone; propamocarb; Propanosine-sodium; propiconazole;
Propineb; Proquinazid; Prothioconazole; Pyraclostrobin; Pyrazophos; Pyrifenox; Pyri- methanil; Pyroquilon; Pyroxyfur; Pyrrolnitrine; Quinconazole; Quinoxyfen; Quintozene;propineb; proquinazid; prothioconazole; pyraclostrobin; Pyrazohos; pyrifenox; Pyrimethanil; pyroquilon; Pyroxyfur; Pyrrolnitrine; Quinconazole; quinoxyfen; quintozene;
Simeconazole; Spiroxamine; Sulfur; Tebuconazole; Tecloftalam; Tecnazene; Tetcyclacis;Simeconazole; spiroxamine; Sulfur; tebuconazole; tecloftalam; Tecnazene; Tetcyclacis;
Tetraconazole; Thiabendazole; Thicyόfen; Thifluzamide; Thiophanate-methyl; Thiram; Tioxymid; Tolclofos-methyl; Tolylfluanid; Triadimefon; Triadimenol; Triazbutil; Tri- azoxide; Tricyclamide; Tricyclazole; Tridemorph; Trifloxystrobin; Triflumizole; Triforine;tetraconazole; thiabendazole; Thicyόfen; Thifluzamide; Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; Triazbutil; Tri azoxides; Tricyclamide; Tricyclazole; tridemorph; trifloxystrobin; triflumizole; triforine;
Triticonazole; Uniconazole; Validamycin A; Vinclozolin; Zineb; Ziram; Zoxamide; (2S)-N-triticonazole; Uniconazole; Validamycin A; vinclozolin; Zineb; ziram; zoxamide; (2S) -N-
[2-[4-[[3-(4-CMorphenyl)-2-propmyl]oxy]-3-memoxyphenyl]ethyl]-3-methyl-2-[(methylsul- fonyl)amino]-butanamid; l-(l-Naphthalenyl)-lH-pyrrol-2,5-dion; 2,3,5,6-Tetrachlor-4-(me- thylsulfonyl)-pyridin; 2-Ammo-4-memyl-N-phenyl-5-thiazolcarboxamid; 2-Chlor-N-(2,3-di- hydro-l,l,3-trimemyl-lH-mden-4-yl)-3-pyridmcarboxamid; 3,4,5-Trichlor-2,6-pyridindicar- bonitril; Actinovate; cis-l-(4-Chlorphenyl)-2-(lH-l,2,4-triazol-l-yl)-cycloheptanol; Methyl- l-(2,3-dihydro-2,2-dimemyl-lH-mden-l-yl)-lH-imidazol-5-carboxylat; Monokaliumcarbo- nat; N-(6-Memoxy-3-pyridinyl)-cyclopropancarboxamid; N-Butyl-8-(l,l-dimethylethyl)-l- oxaspiro[4.5]decan-3-amin; Natriumtetrathiocarbonat; sowie Kupfersalze und -Zubereitungen, wie Bordeaux mixture; Copper hydroxide; Copper naphthenate; Copper oxychloride; Copper sulfate; Cufraneb; Cuprous oxide; Mancqpper; Oxine-copper.[2- [4 - [[3- (4-CMorphenyl) -2-propmyl] oxy] -3-memoxyphenyl] ethyl] -3-methyl-2 - [(methylsulfonyl) amino] butanamide; l- (l-naphthalenyl) -lH-pyrrole-2,5-dione; 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine; 2-Ammo-4-memyl-N-phenyl-5-thiazolecarboxamide; 2-chloro-N- (2,3-di-hydro-l, l, 3-trimemyl-lH-mden-4-yl) -3-pyridmcarboxamide; 3,4,5-trichloro-2,6-pyridinedicarbonitrile; Actinovate; cis-l- (4-chlorophenyl) -2- (lH-l, 2,4-triazol-l-yl) cycloheptanol; Methyl l- (2,3-dihydro-2,2-dimemyl-lH-mden-l-yl) -I H -imidazole-5-carboxylate; Monopotassium carbonate; N- (6-Memoxy-3-pyridinyl) -cyclopropanecarboxamide; N-butyl-8- (l, l-dimethylethyl) -l-oxaspiro [4.5] decan-3-amine; sodium tetrathiocarbonate; as well as copper salts and preparations, such as Bordeaux mixture; Copper hydroxide; Copper naphthenate; Copper oxychloride; Copper sulfate; Cufraneb; Cuprous oxide; Mancqpper; Oxine-copper.
Bakterizide:bactericides:
Bronopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamycin, Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen.Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
Insektizide / Akarizide / Nematizide: .Insecticides / acaricides / nematicides:.
Abamectin, ABG-9008, Acephate, Acequinocyl, Acetamiprid, Acetoprole, Acrinalhrin, AKD-1022, AKD-3059, AKD-3088, Alanycarb, Aldicarb, Aldoxycarb, Allethrin, ethrin lR-isomers, Alpha-(_^ermethrin (Alphamethrin), Amidoflumet, Aminocarb, Amitraz, Avermectin, AZ-60541, Azadirachtin, Azamethiphos, Azinphos-methyl, Azinphos-ethyl, Azocyclotin,Abamectin, ABG-9008, Acephate, Acequinocyl, Acetamiprid, Acetoprole, Acrinalhrin, AKD-1022, AKD-3059, AKD-3088, Alanycarb, Aldicarb, Aldoxycarb, Allethrin, ethrin lR-isomers, Alpha - (_ ^ ermethrin) (Alphamethrin) (Alphamethrin) , Amidoflumet, Aminocarb, Amitraz, Avermectin, AZ-60541, Azadirachtin, Azamethiphos, Azinphos-methyl, Azinphos-ethyl, Azocyclotin,
Bacillus popilliae, Bacillus sphaericus, Bacillus sübtilis, Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillus thuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821, Baculoviren, Beauveria bassiana, Beauveria tenella, Bendiocarb, Ben- furacarb, Bensultap, Benzoximate, Beta-Cyfluthrin, Beta-Cypermethrin, Bifenazate, Bi- fenthrin, Binapacryl, Bioallethrin, Bioallethrin-S-cyclopentyl-isomer, Bioethanomethrin,Bacillus popilliae, Bacillus sphaericus, Bacillus sübtilis, Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillus thuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821, Baculoviruses, Beauveria bassiana, Beauveria tenella, Ben- furacocarboxens, Bendulocarboxens , Beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, binapacryl, bioallethrin, bioallethrin-S-cyclopentyl-isomer, bioethanomethrin,
Biopermethrin, Bioresmethrin, Bistrifluron, BPMC, Brofenprox, Bromophos-ethyl, Bromo- propylate, Bromfenvinfos (-methyl), BTG-504, BTG-505, Bufencarb, Buprofezin, Butathio- fos, Butocarboxim, Butoxycarboxim, Butylpyridaben, Cadusafos, Camphechlor, Carbaryl, Carbofuran, Carbophenothiόn, Carbosulfan, Cartap, CGA-50439, Chinomethionat, Chlordane, Chlordimeform, Chloethocarb, Chlorethoxyfos,Biopermethrin, Bioresmethrin, Bistrifluron, BPMC, Brofenprox, Bromophos-ethyl, Bromopropylate, Bromfenvinfos (-methyl), BTG-504, BTG-505, Bufencarb, Buprofezin, Butathio- fos, Butocarboxim, Butoxycarbidaben, Cadylpyridoxim, Butylpyroxaben, Butylpyroxim, Butylpyroxim, Butyl Carbaryl, Carbofuran, Carbophenothiόn, Carbosulfan, Cartap, CGA-50439, Chinomethionate, Chlordane, Chlordimeform, Chloethocarb, Chlorethoxyfos,
Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorobenzilate, Chloro- picrin, Chlorproxyfen, Chlorpyrifos-methyl, Chlorpyrifos (-ethyl), C ovaporthrin, Chroma- fenozide, Cis-Cypermethrin, Cis-Resmethrin, Cis-Permethrin, Clocythrin, Cloethocarb, Clo- fentezine, Clothianidin, Clothiazoben, Codlemone, Coumaphos, Cyanofenphos, Cyanophos, Cycloprene, Cycloprothrin, Cydia pomonella, Cyfluthrin, Cyhalothrin, Cyhexatin, Cyperme- thrin, Cyphenothrin (lR-trans-isomer), Cyromazine,Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorobenzilate, Chloropicrin, Chlorproxyfen, Chlorpyrifos-methyl, Chlorpyrifos (-ethyl), C ovaporthrin, Chroma-fenozide, Cis-Cypermethrin, Cis-Resmethrin, Clis-Permethrin, Cis-Permethrin - fentezine, Clothianidin, Clothiazoben, Codlemone, Coumaphos, Cyanofenphos, Cyanophos, Cycloprene, Cycloprothrin, Cydia pomonella, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyphenothrin (lR-trans-isomer), Cyromazine,
DDT, Deltamethrin, Demeton-S-methyl, Demeton-S-methylsulphon, Diafenthiuron, Diali- fos, Diazinon, Dichlofenthion, Dichlorvos, Dicofol, Dicrotophos, Dicyclanil, Diflübenzuron, Dimethoate, Dimethylvinphos, Dinobuton, Dinocap, Dinetofuran, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn, DOWCO-439, Eflusilanate, Emamectin, Emamectin-benzoate, Empenthrin (IR-isomer), Endosulfan, En- tomopthora spp., EPN, Esfenvalerate, Ethiofencarb, Ethiprole, Ethion, Ethoprophos, Etofen- prox, Etoxazole, Etrimfos,DDT, Deltamethrin, Demeton-S-methyl, Demeton-S-methylsulphone, Diafenthiuron, Dialifos, Diazinon, Dichlofenthion, Dichlorvos, Dicofol, Dicrotophos, Dicyclanil, Diflübenzuron, Dimethoate, Dimethylvinphos, Diobutonofol, Dinobutonof, Dinobutonof, Docusat-sodium, Dofenapyn, DOWCO-439, Eflusilanate, Emamectin, Emamectin-benzoate, Empenthrin (IR-isomer), Endosulfan, Entomopthora spp., EPN, Esfenvalerate, Ethiofencarb, Ethiprole, Ethion, Ethoprophos, Etofen-prox, Etoxazole, Etrimfos,
Famphur, Fenamiphos, Fenazaquin, Feributatin oxide, Fenfluthrin, Fenitrothion, Fenobu- carb, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fen- pyroximate, Fensulfothion, Fenthion, Fentrifanil, Fenvalerate, Fipronil, Flonicamid, Flu- acrypyrim, Fluazuron, Flubenzimine, Flübrocythrinate, Flucycloxuron, Flucythrinate, Flu- fenerim, Flufenoxuron, Flufenprox, Flimiethrin, Flupyrazofos, Flutenzin (Flufenzine), Flu- valinate, Fonofos, Formetanate, Formothion, Fosmethilan, Fosthiazate, Fubfenprox (Flu- proxyfen), Furathiocarb,Famphur, Fenamiphos, Fenazaquin, Feributatin oxide, Fenfluthrin, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fensulfothion, Fenthion, Fentrifanil, Fenronfluoronimide, Flenifluoron, Fluvaleron, Fermion , Flubenzimine, Flübrocythrinate, Flucycloxuron, Flucythrinate, Flu- fenerim, Flufenoxuron, Flufenprox, Flimiethrin, Flupyrazofos, Flutenzin (Flufenzine), Fluvalinate, Fonofos, Formetanate, Formothion, Fosmethxate, Fubhoxiazon, Fosthiaxilane, Fosthiazole, Fosti Phiazole
Gamma-HCH, Gossyplure, Grandlure, Granuloseviren, Halfenprox, Halofenozide, HCH, HCN-801, Heptenophos, Hexaflumuron, Hexythiazox, Hydramethylnone, Hydroprene, IKA-20O2, Bnidacloprid, Bmprothrin, Indoxacarb, Iodofenphos, Iprobenfos, Isazofos, Iso- fenphos, Isoprocarb, Isoxathion, Iyermectin, Japonilure, Kadethrin, Kernpolyederviren, Kinoprene, Lambda-C halothrin, Lindane, Lufenuron, rGamma-HCH, Gossyplure, Grandlure, Granuloseviren, Halfenprox, Halofenozide, HCH, HCN-801, Heptenophos, Hexaflumuron, Hexythiazox, Hydramethylnone, Hydroprene, IKA-20O2, Bnidacloprid, Bmprothrin, Isphacosphosofos, Iofenosofos, Iofen Isoprocarb, isoxathione, Iyermectin, Japonilure, Kadethrin, nuclear polyhedron viruses, Kinoprene, Lambda-C halothrin, Lindane, Lufenuron, r
Malathion, Mecarbam, Mesulfenfos, Metaldehyd, Metam-sodium, Methacrifos, Methamido- phos, Metharhizium anisopliae, Metharhizium flavoviride, Methidathion, Methiocarb, Methomyl, Methoprene, Methoxychlor, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Milbemycin, MKI-245, MON-45700, Monocrotophos, Moxi- dectin, MTI-800,Malathion, Mecarbam, Mesulfenfos, Metaldehyde, Metam-sodium, Methacrifos, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methomyl, Methoprene, Methoxychlor, Methoxyfenozide, Metolcarb, Metoxadiazone, Milbeminphinos, Milevinphinin, Mevinphinphin, MKevinphinin, Mevinphinin, Mevinphinphinin, Mevinphinphine, Mevinphinin, Mevinphinphine, Mevinphinin, 245 MON-45700, Monocrotophos, Moxidectin, MTI-800,
Naled, NC-104, NC-170, NC-184, NC-194, NC-196, Niclosamide, Nicotine, Nitenpyram, Ntthiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768, Novaluron, Noviflumuron, OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, Omethoate, Oxamyl, Oxy- demeton-methyl, Paecilomyces fumosoroseus, Parathion-methyl, Parathion (-ethyl), Permethrin (eis-, trans-),Naled, NC-104, NC-170, NC-184, NC-194, NC-196, Niclosamide, Nicotine, Nitenpyram, Ntthiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768, Novaluron, Noviflumuron, OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, Omethoate, Oxamyl, Oxydemeton-methyl, Paecilomyces fumosoroseus, Parathion-methyl, Parathion (-ethyl), Permethrin (eis -, trans-),
Petroleum, PH-6045, Phenothrin (lR-trans isomer), Phenthoate, Phorate, Phosalone, Phos- met, Phosphamidon, Phosphocarb, Phoxim, Piperonyl butoxide, Pirimicarb, Pirimiphos- methyl, Pirimiphos-ethyl, Prallethrin, Profenofos, Promecarb, Propaphos, Propargite, Pro- petamphos, Propoxur, Prothiofos, Prothoate, Protrifenbute, Pymetrozine, Pyraclofos, Pyres- methrin, Pyrelhrum, Pyridaben, Pyridalyl, Pyridaphenthion, Pyridathion, Pyrimidifen, Pyri- proxyfen,Petroleum, PH-6045, phenothrin (IR-trans isomer), phenthoate, phorate, phosalone, phosphate, phosphamidone, phosphocarb, phoxime, piperonyl butoxide, pirimicarb, pirimiphos-methyl, pirimiphos-ethyl, prallethrin, profenofos, promecarb, proppaphos , Propargite, Pro-petamphos, Propoxur, Prothiofos, Prothoate, Protrifenbute, Pymetrozine, Pyraclofos, Pyres-methrin, Pyrelhrum, Pyridaben, Pyridalyl, Pyridaphenthion, Pyridathion, Pyrimidifen, Pyri- proxyfen,
Quinalphos, Resmethrin, RH-5849, Ribavirin, RU-12457, RU-15525, S-421, S-1833, Salithion, Sebufos, SI-0009, Silafluofen, Spinosad, Spirodiclofen, Spiro- mesifen, Sulfluramid, Sulfotep, Sulprofos, SZI-121, Tau-Fluvalinate, Tebufenozide, Tebufenpyrad, Tebuprrimfos, Teflubenzuron, Tefluthrin, Temephos, Temivinphos, Terbam, Terbufos, Tetrachlorvinphos, Tetradifon, Tettamethrin, Tettamethrin (lR-isomer), Tetrasul, Theta-C^ermethrin, Thiacloprid, Thiamethoxam, Thia- pronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicärb, Thiofanox, Thiometon, Thio- sultap-sodium, Thuringiensin, Tolfenpyrad, Tralocythrin, Tralomethrin, Transfluthrin, Tri- arathene, Triazamate, Triazophos, Triazuron, Trichlophenidine, Trichlorfon, Triflumuron, Trimethacarb,Quinalphos, Resmethrin, RH-5849, Ribavirin, RU-12457, RU-15525, S-421, S-1833, Salithion, Sebufos, SI-0009, Silafluofen, Spinosad, Spirodiclofen, Spiromesifen, Sulfluramid, Sulfotep, Sulprofos, SZI-121, Tau-Fluvalinate, Tebufenozide, Tebufenpyrad, Tebuprrimfos, Teflubenzuron, Tefluthrin, Temephos, Temivinphos, Terbam, Terbufos, Tetrachlorvinphos, Tetradifon, Tettamethrin, Tettamethrin (l-tretrasmid), Tetamethrin, I-tri-isulid, thi-isia-pyrid , Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicärb, Thiofanox, Thiometon, Thiosultap-sodium, Thuringiensin, Tolfenpyrad, Tralocythrin, Tralomethrin, Transfluthrin, Tri-arathenes, Triazamate, Triazophos, Triazuron, Trichluroboron, Trichluroboron, Trichlurobon
Vamidothion, Vaniliprole, Verbutin, Verticillium lecanii, WL-108477, WL-40027, YI-5201, YI-5301, YI-5302, XMC, Xylylcarb, ZA-3274, Zeta-Cypermethrin, Zolaprofos, ZXI-8901, die Verbindung 3-Methyl-phenyl-propylcarbamat (Tsumacide Z), die Verbindung 3-(5-Cωor-3-pyridmyl)-8-(2,2,2-trifluorethyl)-8-azabicyclo[3.2.1]octan-3- carbonitril (CAS-Reg.-Nr. 185982-80-3) und das entsprechende 3-endo-Isomere (CAS-Reg.- Nr. 185984-60-5) (vgl. WO-96/37494, WO-98/25923),Vamidothion, Vaniliprole, Verbutin, Verticillium lecanii, WL-108477, WL-40027, YI-5201, YI-5301, YI-5302, XMC, Xylylcarb, ZA-3274, Zeta-Cypermethrin, Zolaprofos, ZXI-8901, the compound Methyl phenyl propyl carbamate (Tsumacide Z), the compound 3- (5-Cωor-3-pyridmyl) -8- (2,2,2-trifluoroethyl) -8-azabicyclo [3.2.1] octane-3-carbonitrile (CAS Reg.No. 185982-80-3) and the corresponding 3-endo isomer (CAS Reg.No. 185984-60-5) (see WO-96/37494, WO-98/25923 )
sowie Präparate, welche Insektizid wirksame Pflanzenextrakte, Nematoden, Pilze oder Viren enthalten.and preparations which contain insecticidal plant extracts, nematodes, fungi or viruses.
Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Herbiziden, Düngemitteln,A mixture with other known active ingredients, such as herbicides, fertilizers,
WachstamsregulatoTen, Safenern oder Semiochemicals ist möglich.Vigilance regulators, safeners or semiochemicals are possible.
Die erfindungsgemäßen Wirkstoffe können ferner beim Einsatz als Bisektizide in ihren handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit Synergisten vorliegen. Synergisten sind Verbindungen, durch die die Wirkung der Wirkstoffe gesteigert wird, ohne dass der zugesetzte Synergist selbst aktiv wirksam sein muss.When used as bisecticides, the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active.
Die erfϊndungsgemäßen Wirkstoffe können ferner beim Einsatz als Bisektizide in ihren handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischungen mit Hemmstoffen vorliegen, die einen Abbau des Wirkstoffes nach Anwendung in der Umgebung der Pflanze, auf der Oberfläche vonWhen used as bisecticides, the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in mixtures with inhibitors which break down the active compound after use in the environment of the plant, on the surface of
Pflanzenteilen oder in pflanzlichen Geweben vermindern.Reduce parts of plants or plant tissues.
Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten Anwendungsformen kann in weiten Bereichen variieren. Die Wirkstoffkonzentration der Anwendungs- formen kann von 0,0000001 bis zu 95 Gew.-% Wirkstoff, vorzugsweise zwischen 0,0001 und 1 Gew.-% liegen.The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The drug concentration of the application molds can range from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.
Die Anwendung geschieht in einer den Anwendungsformen angepassten üblichen Weise.The application takes place in a customary manner adapted to the application forms.
Bei der Anwendung gegen Hygiene- und Vorratsschädlinge zeichnet sich der Wirkstoff durch eine hervorragende Residualwirkung auf Holz und Ton sowie durch eine gute Alkalistabilität auf gekalkten Unterlagen aus.When used against hygiene pests and pests of stored products, the active substance is distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
Wie bereits oben erwähnt, können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. B einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden, wie Kreuzung oder Protoplastenfusion erhaltenen Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. Bi einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff „Teile" bzw. „Teile von Pflanzen" oder , .Pflanzenteile" wurde oben erläutert.As already mentioned above, according to the invention, all plants and their parts can be treated. In a preferred embodiment, plant species and plant cultivars and their parts occurring wildly or obtained by conventional organic breeding methods, such as crossbreeding or protoplast fusion, are treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated. The term "parts" or "parts of plants" or "plant parts" was explained above.
Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht manPlants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant varieties are understood
Pflanzen mit neuen Eigenschaften („Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken gezüchtet worden sind. Dies können Sorten, Bio- und Genotypen sein. .Plants with new traits that have been grown by conventional breeding, mutagenesis or recombinant DNA techniques. These can be varieties, bio and genotypes.
Je nach Pflanzenarten bzw. Pflanzensorten, deren Standort und WachstumsbedingungenDepending on the plant species or plant varieties, their location and growing conditions
(Böden, Klima, Vegetationsperiode, Ernährung) können durch die erfindungsgemäße Behandlung auch überadditive („synergistische") Effekte auftreten. So sind beispielsweise erniedrigte Aufwandmengen und/oder Erweiterungen des Wirkungsspektrums und/oder eine Verstärkung der Wirkung der erfindungsgemäß verwendbaren Stoffe und Mittel, besseres , Pflanzenwachstu , erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte möglich, die über die eigentlich zu erwartenden Effekte hinausgehen. Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften („Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, - erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehr der Pflanzen gegen tierische und mikrobielle Schädlinge, wie gegenüber Insekten,. Milben, pflanzenpathogenen Pilzen, Bakterien und/oder Viren sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis), Mais, Soja, Kartoffel,(Soils, climate, vegetation period, nutrition), the treatment according to the invention can also give rise to superadditive (“synergistic”) effects. For example, reduced application rates and / or widening of the activity spectrum and / or an increase in the action of the substances and agents which can be used according to the invention are better , Plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the expected effects. The preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, - increased tolerance to dryness or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or Vi ren and an increased tolerance of the plants to certain herbicidal active ingredients. The important crop plants such as cereals (wheat, rice), maize, soybeans, potatoes,
Baumwolle, Tabak, Raps sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben) erwähnt, wobei Mais, Soja, Kartoffel, Baumwolle, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften („Traits") werden besonders hervorgehoben die erhöhte Abwehr der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus Thuringiensis (z.B. durch die Gene CryΙA(a), CryIA(b), CryIA(c), CryllA, CryHIA, CryHIB2, Cry9c, Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden (im folgenden „Bt Pflanzen"). Als Eigenschaften („Traits") werden auch besonders hervorgehoben die erhöhte Abwehr von Pflanzen gegen Pilze, Bakterien und Viren durch -Systemische Akquirierte Resistenz (SAR),Cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned, whereby maize, soybeans, potatoes, cotton, tobacco and rapeseed are particularly emphasized. The traits are particularly emphasized as the plants' increased defense against insects, arachnids, nematodes and snails due to toxins that arise in the plants, especially those that are caused by the genetic material from Bacillus thuringiensis (eg by the genes CryΙA (a) , CryIA (b), CryIA (c), CryllA, CryHIA, CryHIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter “Bt plants”). The properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR),
Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine. Als Eigenschaften („Traits") werden weiterhin besonders hervorgehoben die erhöhte Toleranz der Pflanzen gegenüber bestimmten herbiziden Wirkstoffen, beispielsweise Bnidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinotricin (z.B. ,JPAT"-Gen). Die jeweils die gewünschten Eigenschaften („Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele für „Bt Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und Kartoffelsorten genannt, die unter den Handelsbezeichnungen YDELD GARD® (z.B. Mais, Baumwolle, Soja), KnockOut® (z.B. Mais), StarLink® (z.B. Mais), Bollgard® (Baumwolle), Nucotn® (Baumwolle) und NewLeaf® (Kartoffel) vertrieben werden. Als Beispiele für Herbizid-tolerante Pflanzen seien Maissorten, Baumwollsorten und Sojasorten genannt, die unter den Handelsbezeichnungen Roundup Ready® (Toleranz gegen Glyphosate z.B. Mais, Baumwolle, Soja), Liberty Link® (Toleranz gegen Phosphinotricin, z.B. Raps), MI® (Toleranz gegen Bnidazolinone) und STS® (Toleranz. gegen Sulfonyl- harnstoffe z.B. Mais) vertrieben werden. Als Herbizid resistente (konventionell auf Herbizid-Toleranz gezüchtete) Pflanzen seien auch die unter der Bezeichnung Clearfield® vertriebenen Sorten (z.B. Mais) erwähnt. Selbstverständlich gelten diese Aussagen auch für in der Zukunft entwickelte bzw. zukünftig auf den Markt kommende Pflanzensorten mit diesen oder zukünftig entwickelten genetischen Eigenschaften („Traits").Systemin, phytoalexins, elicitors as well as resistance genes and correspondingly expressed proteins and toxins. The properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example bnidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example the JPAT gene). The genes conferring the desired properties (“traits”) can also be found in combinations with one another in the transgenic plants. Examples of “Bt plants” are corn varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YDELD GARD® (eg corn , Cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). As Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties which are marketed under the trade names Roundup Ready® (tolerance against glyphosate, e.g. maize, cotton, soy), Liberty Link® (tolerance against phosphinotricin, e.g. rape), MI® (tolerance against Bnidazolinone) and STS® (tolerance to sulfonylureas such as maize). The herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
Die aufgeführten Pflanzen können besonders vorteilhaft erfindungsgemäß mit den Ver- - bindungen der allgemeinen Formel I bzw. den erfϊndungsgemäßen Wirl stoffmischungen behandelt, werden. Die bei den Wirkstoffen bzw. Mischungen oben angegebenen Vorzugsbereiche gelten auch für die Behandlung dieser Pflanzen. Besonders hervorgehoben sei die Pflanzenbehandlung mit den im vorliegenden Text speziell aufgeführtenThe plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active compound mixtures according to the invention. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with those specifically listed in this text should be particularly emphasized
Verbindungen bzw. Mischungen.Compounds or mixtures.
Die erfϊndungsgemäßen Wirkstoffe wirken nicht nur gegen Pflanzen-, Hygiene- und Vorratsschädlinge, sondern auch auf dem veterinärmedizinischen Sektor gegen tierische Parasiten (Ektoparasiten) wie Schildzecken, Lederzecken, Räudemilben, Laufmilben,The active substances according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tortoise ticks, leather ticks, space mites, running mites,
Fliegen (stechend und leckend), parasitierende Fliegenlarven, Läuse, Haarlinge, Federlinge und Flöhe. Zu diesen Parasiten gehören:Flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings and fleas. These parasites include:
Aus der Ordnung der Anoplurida z.B. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp..From the order of the Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
Aus der Ordnung der Mallophagida und den Unterordnungen Amblycerina sowie Ischnocerina z.B. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.. Aus der Ordnung Diptera und den Unterordnungen Nematocerina sowie Brachycerina z.B. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusi ulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp.,From the order of the Mallophagida and the subordinates Amblycerina and Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .. From the order Diptera and the subordinates Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusi ulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp.,
. Tabanus spp., Haematopota spp., Pbilipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,, Tabanus spp., Haematopota spp., Pbilipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,
Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp.,Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp.,
Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.. Aus der Ordnung der Siphonapterida z.B. Pulex spp., CtenocephaUdes spp., Xenopsylla spp., Ceratophyllus spp..Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp .. From the order of the Siphonapterida, for example Pulex spp., CtenocephaUdes spp., Xenopsylla spp., Ceratophyllus spp ..
Aus der Ordnung der Heteropterida z.B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.. Aus der Ordnung der . Blattarida z.B. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp..From the order of the Heteropterida e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp .. From the order of the. Blattarida e.g. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp ..
Aus der Unterklasse der Acari (Acarina) und den Ordnungen der Meta- sowie Mesostigmata z.B. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp..From the subclass of the Acari (Acarina) and the orders of the Meta and Mesostigmata e.g. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietssus spp.,. Pneumonia ., Sternostoma spp., Varroa spp ..
Aus der Ordnung der Actinedida (Prostigmata) und Acaridida (Astigmata) z.B. Acarapis spp., Cheyletiella spp., Orriithocheyletia spp., Myobia spp.,.Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.* Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp..From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Orriithocheyletia spp., Myobia spp.,. Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp. * Tyrophagus spp., Caloglyphus spp., Hypodectesichpp spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
Beispielsweise zeigen sie eine hervorragende Wirksamkeit gegen die Entwicklungsstadien von Zecken wie zum Beispiel Amblyomma hebraeum, gegen parasitierende Fliegen wie zum Beispiel gegen Lucilia cuprina, gegen Flöhe wie zum Beispiel CtenocephaUdes felisFor example, they show excellent activity against the developmental stages of ticks such as Amblyomma hebraeum, against parasitic flies such as against Lucilia cuprina, against fleas such as CtenocephaUdes felis
Die erfϊndungsgemäßen Wirkstoffe der Formel (I) eignen sich auch zur' Bekämpfung von Arthropoden, die landwirtschaftliche Nutztiere, wie z.B. Rinder, Schafe, Ziegen, Pferde, Schweine, Esel, Kamele, Büffel, Kaninchen, Hühner, Puten, Enten, Gänse, Bienen, sonstige Haustiere wie z.B. Hunde, Katzen, Stubenvögel, Aquarienfische sowie sogenannte Ver- suchstiere, wie z.B. Hamster, Meerschweinchen, Ratten und Mäuse befallen. Durch die Bekämpfung dieser Arthropoden sollen Todesfälle und Leistungsminderungen (bei Fleisch, Milch, Wolle, Häuten, Eiern, Honig usw.) vermindert werden, so dass durch den Einsatz der erfindungsgemäßen Wirkstoffe eine wirtschaftlichere und einfachere Tierhaltung möglich ist.The active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals such as Infest hamsters, guinea pigs, rats and mice. By fighting these arthropods, deaths and reduced performance (in meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.
Die Anwendung der erfindungsgemäßen Wirkstoffe geschieht im Veterinärsektor in bekannter Weise durch enterale Verabreichung in Form von beispielsweise Tabletten, Kapseln, Tränken, Drenchen, Granulaten, Pasten, Boli, des feed-through-Verfahrens, von Zäpfchen, durch parenterale Verabreichung, wie zum Beispiel durch Bijektionen (intra- muskulär, subcutan, intravenös, intraperitonal u.a.), Implantate, durch nasale Applikation, durch dermale Anwendung in Form beispielsweise des Tauchens oder Badens (Dippen), Sprühens (Spray), Aufgießens (Pour-on und Spot-on), des Waschens, des Einpuderns sowie mit Hilfe von wirkstoffhaltigen Formkörpern, wie Halsbändern, Ohrmarken,, Schwanz- marken, Gliedmaßenbändern, Halftern, Markierungsvorrichtungen usw.In the veterinary sector, the active compounds according to the invention are used in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Bijections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering, and with the aid of shaped articles containing active ingredients, such as collars, ear tags, tails marks, limb straps, holsters, marking devices, etc.
Bei der Anwendung für Vieh, Geflügel, Haustiere etc. kann man die Wirkstoffe der Formel (I) als Formulierungen (beispielsweise Pulver, Emulsionen, fließfähige Mittel), die die Wirkstoffe in einer Menge von 1 bis 80 Gew.-% enthalten, direkt oder nach 100 bis 10 000- facher Verdünnung anwenden oder sie als chemisches Bad verwenden.When used for cattle, poultry, pets, etc., the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
Außerdem wurde gefunden, dass die erfϊndungsgemäßen Verbindungen eine hohe insekti- zide Wirkung gegen Bisekten zeigen, die technische Materialien zerstören.It was also found that the compounds according to the invention show a high insecticidal action against bisects which destroy industrial materials.
Beispielhaft und vorzugsweise - ohne jedoch zu limitieren - seien die folgenden Insekten genannt:The following insects may be mentioned by way of example and preferably, but without limitation:
Käfer wie Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Ernobius mollis, Priobium carpini,Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Ernobius mollis, Priobium carpini,
Lyctus brunneus, Lyctus africanus, Lyc us planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus rninutus;Lyctus brunneus, Lyctus africanus, Lyc us planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus rninutus;
Hautflügler wie Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
Termiten wie Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
Borstenschwänze wie Lepisma saccharina.Bristle tails such as Lepisma saccharina.
Unter technischen Materialien sind im vorliegenden Zusammenhang nicht-lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere undIn the present context, technical materials are to be understood as non-living materials, such as preferably plastics, adhesives, glues, papers and
Kartone, Leder, Holz, Holzverarbeitungsprodukte und Anstrichmittel.Cardboard boxes, leather, wood, wood processing products and paints.
Ganz besonders bevorzugt handelt es sich bei dem vor Bisektenbefall zu schützenden Material um Holz und Holzverarbeitungsprodukte. Unter Holz und Holzverarbeitungsprodukten, welche durch das erfindungsgemäße Mittel bzw. dieses enthaltende Mischungen geschützt werden kann, ist beispielhaft zu verstehen:The material to be protected against bisect infestation is very particularly preferably wood and wood processing products. Wood and wood processing products that can be protected by the agent according to the invention or mixtures containing it are to be understood as examples:
Bauholz, Holzbalken, Eisenbahnschwellen, Brückenteile, Bootsstege, Holzfahrzeuge, Kisten, Paletten, Container, Telefonmasten, Holzverkleidungen, Holzfenster und -türen,Timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden panels, wooden windows and doors,
Sperrholz, Spanplatten, Tischlerarbeiten oder Holzprodukte, die ganz allgemein beim Hausbau oder in der Bautischlerei Verwendung finden.Plywood, chipboard, carpentry or wood products that are used in general in house construction or joinery.
Die Wirkstoffe können als solche, in Form von Konzentraten oder allgemein üblichen Formulierungen wie Pulver, Granulate, Lösungen, Suspensionen, Emulsionen oder Pasten angewendet werden.The active compounds can be used as such, in the form of concentrates or generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes.
Die genannten Formulierungen können in an sich bekannter Weise hergestellt werden, z.B. durch Vermischen der Wirkstoffe mit mindestens einem Lösungs- bzw. Verdünnungsmittel, Emulgator, Dispergier- und/oder Binde- oder Fixiermittel, Wasser-Repellent, gegebenenfallsThe formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, if appropriate
Sikkative und UV-Stabilisatoren und gegebenenfalls Farbstoffen und Pigmenten sowie weiteren Verarbeitungshilfsmitteln.Desiccants and UV stabilizers and, where appropriate, dyes and pigments and other processing aids.
Die zum Schutz von Holz und Holzwerkstoffen verwendeten insektiziden Mittel oder Konzentrate enthalten den erfindungsgemäßen Wirkstoff in einer Konzentration von 0,0001 bis 95 Gew.-%, insbesondere 0,001 bis 60 Gew.-%.The insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
Die Menge der eingesetzten Mittel bzw. Konzentrate ist von der Art und dem Vorkommen der B sekten und von dem Medium abhängig. Die optimale Einsatzmenge kann bei der Anwendung jeweils durch Testreihen ermittelt werden. Bn allgemeinen ist es jedoch ausreichend 0,0001 bis 20 Gew.-%, vorzugsweise 0,001 bis 10 Gew.-%, des Wirkstoffs, bezogen auf das zu schützende Material, einzusetzen.The amount of the agents or concentrates used depends on the type and occurrence of the B sects and on the medium. The optimum amount of use can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected.
Als Lösungs- und/oder Verdünnungsmittel dient ein organisch-chemisches Lösungsmittel oder Lösungsmittelgemisch und oder ein öliges oder ölartiges schwer flüchtiges organischchemisches Lösungsmittel oder Lösungsmittelgemisch und oder ein polares organischchemisches Lösungsmittel oder Lösungsmittelgemisch und/oder Wasser und gegebenenfalls einen Emulgator und/oder Netzmittel. Als organisch-chemische Lösungsmittel werden vorzugsweise ölige oder ölartige Lösungsmittel mit einer Verdunstungszahl über 35 und einem Flammpunkt oberhalb 30°C, vorzugsweise oberhalb 45°C, eingesetzt. Als derartige schwerflüchtige, wasserunlösliche, ölige und ölartige Lösungsmittel werden entsprechende Mineralöle oder deren Aromatenfraktionen oder rnineralölhaltige Lösungsmittelgemische, vorzugsweiseAn organic-chemical solvent or solvent mixture and or an oily or oil-like low-volatile organic-chemical solvent or solvent mixture and or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent are used as solvents and / or diluents. The organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C. Corresponding mineral oils or their aromatic fractions or solvent mixtures containing mineral oil are preferred as such low-volatility, water-insoluble, oily and oily solvents
Testbenzin, Petroleum und/oder Alkylbenzol verwendet.White spirit, petroleum and / or alkylbenzene used.
Vorteilhaft gelangen Mineralöle mit einem Siedebereich von 170 bis 220°C, Testbenzin mit einem Siedebereich von 170 bis 220°C, Spindelöl mit einem Siedebereich von 250 bis 350°C, Petroleum bzw. Aromaten vom Siedebereich von 160 bis 280°C, Te entinöl und dgl. zum Einsatz.Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, duck oil and the like.
Bi einer bevorzugten Ausführungsform werden flüssige aliphatische Kohlenwasserstoffe mit einem Siedebereich von 180 bis 210°C oder hochsiedende Gemische von aromatischen und aliphatischen Kohlenwasserstoffen mit einem Siedebereich von 180 bis 220°C und/oderIn a preferred embodiment, liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C and / or
Spindeöl und/oder Monochlornaphthalin, vorzugsweise o>Monochlornaphthalin, verwendet.Locker oil and / or monochloronaphthalene, preferably o> monochloronaphthalene, are used.
Die organischen schwerflüchtigen öligen oder ölartigen Lösungsmittel mit einer Verdunstungszahl über 35 und einem Flammpunkt oberhalb 30°C, vorzugsweise oberhalb 45°C, können teilweise durch leicht oder mittelflüchtige organisch-chemische Lösungsmittel ersetzt werden, mit der Maßgabe, dass das Lösungsmittelgemisch ebenfalls eine Verdunstungszahl über 35 und einen Flammpunkt oberhalb 30°C, vorzugsweise oberhalb 45°C, aufweist und dass das sel tizid-Fungizid-Gemisch in diesem Lösungsmittelgemisch löslich oder emulgierbar ist.The organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the sel tizid-fungicide mixture is soluble or emulsifiable in this solvent mixture.
Nach einer bevorzugten Ausfiihrungsform wird ein Teil des organisch-chemischen Lösungsmittel oder Lösungsmittelgemisches oder ein aliphatisches polares organischchemisches Lösungsmittel oder Lösungsmittelgemisch ersetzt. Vorzugsweise gelangen Hydroxyl- und/oder Ester- und/oder Ethergruppen enthaltende aliphatische organisch- chemische Lösungsmittel wie beispielsweise Glycolether, Ester oder dgl. zur Anwendung.According to a preferred embodiment, part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced. Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.
Als organisch-chemische Bindemittel werden im Rahmen der vorliegenden Erfindung die an sich bekannten wasserverdünnbaren und/oder in den eingesetzten organisch-chemischenIn the context of the present invention, the known organic-chemical binders are water-thinnable and / or organic-chemical binders
Lösungsmitteln löslichen oder dispergier- bzw. emulgierbaren Kunstharze und/oder bindende trocknende Öle, insbesondere Bindemittel bestehend aus oder enthaltend ein Acrylatharz, ein Vinylharz, z.B. Polyvinylacetat, Polyesterharz, Polykondensations- oder Polyadditionsharz, Polyurethanharz, Alkydharz bzw. modifiziertes Alkydharz, Phenolharz, Kohlenwasserstoffharz wie Biden-Cumaronharz, . Siliconharz, trocknende pflanzliche und/oder trocknende Öle und/oder physikalisch trocknende Bindemittel auf der Basis eines Natur- und/oder Kunstharzes verwendet.Solvent-soluble or dispersible or emulsifiable synthetic resins and / or binding drying oils, in particular binders consisting of or containing a Acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as biden-coumarone resin. Silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin are used.
Das als Bindemittel verwendete Kunstharz kann in Form einer Emulsion, Dispersion oder Lösung, eingesetzt werden. Als Bindemittel können auch Bitumen oder bituminöse Substanzen bis zu 10 Gew.-%, verwendet werden. Zusätzlich können an sich bekannte Farbstoffe, Pigmente, wasserabweisende Mittel, Geruchskorrigentien und Bihibitoren bzw.The synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and bihibitors or
Korrosionsschutzmittel und dgl. eingesetzt werden.Corrosion protection agents and the like are used.
Bevorzugt ist gemäß der Erfindung als organisch-chemische Bindemittel mindestens ein Alkydharz bzw. modifiziertes Alkydharz und/oder ein trocknendes pflanzliches Öl im Mittel oder im Konzentrat enthalten. Bevorzugt werden gemäß der Erfindung Alkydharze mit einem Ölgehalt von mehr als 45 Gew.-%, vorzugsweise 50 bis 68 Gew.-%, verwendet.According to the invention, at least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder. Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
Das erwähnte Bindemittel kann ganz oder teilweise durch ein Fixierungsmittel(gemisch) oder ein Weichmacher(gemisch) ersetzt werden. Diese Zusätze sollen einer Verflüchtigung der Wirkstoffe sowie einer Kristallisation bzw. Ausfällem vorbeugen. Vorzugsweise ersetzen sie 0,01 bis 30 % des Bindemittels (bezogen auf 100 % des eingesetztenAll or part of the binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the used
Bindemittels).Binder).
Die Weichmacher stammen aus den chemischen Klassen der Phthalsäureester wie Dibutyl-,The plasticizers come from the chemical classes of phthalic acid esters such as dibutyl,
Dioctyl- oder Benzylbutylphthalat, Phosphorsäureester wie Tributylphosphat, Adipin- säureester wie Di-(2-ethylhexyl)-adipat, Stearate wie Butylstearat oder Amylstearat, Oleate wie Butyloleat, Glycerinether oder höhermolekulare Glykolether, Glycerinester sowie p-Dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ether or higher molecular weight glycol ethers, glycerol esters and
Toluolsulfonsäureester.Toluenesulfonic.
Fixierungsmittel basieren chemisch auf Polyvinylalkylethern wie z.B. Polyvmylmethylether oder Ketonen wie Benzophenon, Ethyleribenzophenon.Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvmylmethylether or ketones such as benzophenone, ethyl dibenzophenone.
Als Lösungs- bzw. Verdünnungsmittel kommt insbesondere auch Wasser in Frage, gegebenenfalls in Mischung mit einem oder mehreren der oben genannten organischchemischen Lösungs- bzw. Verdünnungsmittel, Emulgatoren und Dispergatoren. Ein besonders effektiver Holzschutz wird durch großtechnische Bnprägnierverfahren, z.B. Vakuum, Doppelvakuum oder Druckverfahren, erzielt.Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants. A particularly effective wood preservation is achieved by industrial impregnation processes, eg vacuum, double vacuum or pressure processes.
Die anwendungsfertigen Mittel. können gegebenenfalls noch weitere Bisektizide und ge- gebenenfalls noch ein oder mehrere Fungizide enthalten.The ready-to-use means. may also contain other bisecticides and, if appropriate, one or more fungicides.
Als zusätzliche Zumischpartner kommen vorzugsweise die in der WO 94/29268 genannten Bisektizide und Fungizide in Frage. Die in diesem Dokument genannten Verbindungen sind ausdrücklicher Bestandteil der vorliegenden Anmeldung.The bisecticides and fungicides mentioned in WO 94/29268 are preferably suitable as additional admixing partners. The compounds mentioned in this document are an integral part of the present application.
Als ganz besonders bevorzugte Zumischpartner können Bisektizide, wie Chlorpyriphos, Phoxim, Silafluofin, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrin, Permethrin, IJmidacloprid, NI-25, Flufenoxuron, Hexaflumuron, Transfluthrin, Thiacloprid, Methoxy- fenozide, Triflumuron, Clothianidin, Spinosad, Tefluthrin,Bisecticides, such as chlorpyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, ijmidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, trifluoridophenone, trifluoridophenone, trifluoridophenone, trifluoridophenone, trifluoridophenone, trifluorophenol, trifluoride, trifluoride .
sowie Fungizide wie Epoxyconazole, Hexaconazole, Azaconazole, Propiconazole, Tebuco- nazole, Cyproconazole, Metconazole, Bnazalil, Dichlorfluanid, Tolylfluanid, 3-Iod-2- propinyl-butylcarbamat, N-Octyl-isothiazolin-3-on und 4,5-Dichlor-N-octylisothiazolin-3- on, sein.as well as fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, bnazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5 -N-octylisothiazolin-3-one.
Zugleich können die erfϊndungsgemäßen Verbindungen zum Schutz vor Bewuchs von Gegenständen, insbesondere von Schiffskörpern, Sieben, Netzen, Bauwerken, Kaianlagen und Signalanlagen, welche mit See- oder Brackwasser in Verbindung kommen, eingesetzt werden.At the same time, the connections according to the invention can be used to protect objects, in particular hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
Bewuchs durch sessile Oligochaeten, wie Kalkröhrenwürmer sowie durch Muscheln und Arten der Gruppe Ledamorpha (Entenmuscheln), wie verschiedene Lepas- und Scalpellum- Arten, oder durch Arten der Gruppe Balanomorpha (Seepocken), wie Baianus- oder Pollicipes-Species, erhöht den Reibungswiderstand von Schiffen und führt in der Folge durch erhöhten Energieverbrauch und darüber hinaus durch häufige Trockendockaufenthalte zu einer deutlichen Steigerung der Betriebskosten.Overgrowth by sessile oligochaetes, such as lime tube worms, and by mussels and species from the group Ledamorpha (barnacles), such as various Lepas and Scalpellum species, or by species from the group Balanomorpha (barnacles), such as Baianus or Pollicipes species, increases the frictional resistance of Ships and subsequently leads to a significant increase in operating costs due to increased energy consumption and, moreover, frequent dry dock stays.
Neben dem Bewuchs durch Algen, beispielsweise Ectocarpus sp. und Ceramium sp., kommt insbesondere dem Bewuchs durch sessile Entomostraken-Gruppen, welche unter dem Namen Cirripedia (Rankenflußkrebse) zusammengefaßt werden, besondere Bedeutung zu. Es wurde nun überraschenderweise gefunden, dass die erfindungsgemäßen Verbindungen allein oder in Kombination mit anderen W tatoffen, eine hervorragende Antifouling (Antibewuchs)-Wirkung aufweisen.In addition to the growth by algae, for example Ectocarpus sp. and Ceramium sp., vegetation by sessile Entomostraken groups, which are grouped under the name Cirripedia (tendril crayfish), is particularly important. It has now surprisingly been found that the compounds according to the invention, alone or in combination with other substances, have an excellent antifouling effect.
Durch Einsatz von erfindungsgemäßen Verbindungen allein oder in Kombination mit anderen Wirkstoffen, kann auf den Einsatz von Schwermetallen wie z.B. in Bis(trialkyl- zinn)-sulfiden, Tri-H-butylzinnlaurat, Tri-κ-butylzinnchlorid, Kupfer(I)-oxid, Triethylzinn- chlorid, Tri-n-butyl(2-phenyl-4-cUθ henoxy)-zinn, Tributylzinnoxid, Molybdändisulfϊd, Antimonoxid, polymerem Butyltitanat, Phenyl-(bispyridin)-wismutchlorid, Tri-«-butylzinn- fluorid, Manganethylenbisthiocarbamat, Zinkdimethyldithiocarbamat, Zinkethylenbisthio- carbamat, Zink- und Kupfersalze von 2-Pyridinthiol-l-oxid, Bisdimethyldithiocarbamoyl- zinkethylenbisthiocarbamat, Zinkoxid, Kupfer(I)-ethylen-bisditbiocarbamat, Kupferthio- cyanat, Kupfernaphthenat und Tributylzinnhalogeniden verzichtet werden oder die Konzen- tration dieser Verbindungen ent-scheidend reduziert werden.By using compounds according to the invention alone or in combination with other active ingredients, the use of heavy metals such as e.g. in bis (trialkyltin) sulfides, tri-H-butyltin laurate, tri-κ-butyltin chloride, copper (I) oxide, triethyltin chloride, tri-n-butyl (2-phenyl-4-cUθhenoxy) tin , tributyltin oxide, Molybdändisulfϊd, antimony oxide, polymeric butyl titanate, phenyl- (bispyridine) -wismutchlorid, tri - "- butyltin fluoride, Manganethylenbisthiocarbamat, carbamate zinc dimethyldithiocarbamate, Zinkethylenbisthio-, zinc and copper salts of 2-pyridinethiol-l-oxide, Bisdimethyldithiocarbamoyl- zinkethylenbisthiocarbamat , Zinc oxide, copper (I) ethylene bisditbiocarbamate, copper thiocyanate, copper naphthenate and tributyltin halides or the concentration of these compounds can be reduced significantly.
Die anwendungsfertigen Antifoulingfarben können gegebenenfalls noch andere Wirkstoffe, vorzugsweise Algizide, Fungizide, Herbizide, Molluskizide bzw. andere Antifouling- Wirkstoffe enthalten.The ready-to-use antifouling paints may also contain other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
Als Kombinationspartner für die erfϊndungsgemäßen Antifouling-Mittel eignen sich vorzugsweise:The following are preferably suitable as combination partners for the antifouling agents according to the invention:
Algizide wie 2-tert.-Butylarmno-4-cyclopropylamino-6-methylfhio-l,3,5-triazin, Dichloro- phen, Diuron, Endothal, Fentinacetat, Isoproturon, Methabenzthiazuron, Oxyfluorfen, Qui- noclamine und Terbutryn; Fungizide wie Benzo[b]tmophencarbonsäurecyclohexylan-id-S,S- dioxid, Dichlofluanid, Fluorfolpet, 3-Iod-2-propinyl-butylcarbarnat, Tolylfluanid und Azole wie Azaconazole, Cyproconazole, Epoxyconazole, Hexaconazole, Metconazole, Propi- conazole und Tebuconazole; Molluskizide wie Fentinacetat, Metaldehyd, Methiocarb, Niclosamid, Thiodicarb und Trimethacarb, Fe-chelate, oder herkömmliche Antifouling- Wirkstoffe wie 4,5-Dichlor-2-octyl-4-isothiazolin-3-on, Diiodmethylparatrylsulfon, 2-(N,N-Algicides such as 2-tert-butylarmno-4-cyclopropylamino-6-methylfhio-l, 3,5-triazine, dichlorophen, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn; Fungicides such as benzo [b] tmophencarbonsäurecyclohexylan-id-S, S-dioxide, dichlofluanid, Fluorfolpet, 3-iodo-2-propynyl butylcarbarnat, tolylfluanid and azoles such as azaconazole, cyproconazole, epoxyconazole, hexaconazole, conconazole, metazazole, Molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb, Fe chelates, or conventional antifouling agents such as 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulfone, 2- (N, N -
Dimemyltmocarbamoylthio)-5-nitrothiazyl, Kalium-, Kupfer-, Natrium- und Zi ksalze von 2-Pyridinthiol-l-oxid, Pyridin-triphenylboran, Tetrabutyldistannoxan, 2,3,5,6-Tetrachlor-4- (methylsulfonyl)-pyridin, 2,4,5 ,6-Tetrachloroisophthalonitril, Tetramethylthiuramdisulfid und 2,4,6-TricMorphenylmalemimid. Die verwendeten Antifouling-Mittel enthalten die erfindungsgemäßen Wirkstoff der erfindungsgemäßen Verbindungen in einer Konzentration von 0,001 bis 50 Gew.-%, insbesondere von 0,01 bis 20 Gew -%.Dimemyltmocarbamoylthio) -5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridinthiol-l-oxide, pyridine triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine , 2,4,5, 6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2,4,6-tricmorphenylmalemimide. The antifouling agents used contain the active compound according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular 0.01 to 20% by weight.
Die erfϊndungsgemäßen Antifouling-Mittel enthalten desweiteren die üblichen Bestandteile wie z.B. in Ungerer, Chem. Ind. 1985, 37, 730-732 und Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973 beschrieben.The antifouling agents according to the invention furthermore contain the usual constituents, such as in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
Antifoulmg-Anstrichmittel enthalten neben den algiziden, fungiziden, molluskiziden und er- fϊndungsgemäßen insektiziden Wirkstoffen insbesondere Bindemittel.In addition to the algicidal, fungicidal, molluscicidal and insecticidal active substances according to the invention, antifoulm paints contain in particular binders.
Beispiele für anerkannte Bindemittel sind Polyvinylchlorid in einem Lösungsmittelsystem, chlorierter Kautschuk in einem Lösungsmittelsystem, Acrylharze in einem Lösungsmittelsystem insbesondere in einem wäßrigen System, Vinylchlorid/Vinylacetat-Copolymer- Systeme .in Form wäßriger Dispersionen oder in Form von organischen Lösungsmittelsystemen, Butadien/StyroVAcrylnitrii-Kautschuke, trocknende Öle, wie Leinsamenöl, Harzester oder modifizierte Hartharze in Kombination mit Teer oder Bitumina, Asphalt sowie Epoxyverbindungen, geringe Mengen Chlorkautschuk, chloriertes Polypropylen und Vinyl- harze.Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chloride / vinyl acetate copolymer systems. In the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styroVAcrylonitrile rubbers , drying oils, such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
Gegebenenfalls enthalten Anstrichmittel auch anorganische Pigmente, organische Pigmente oder Farbstoffe, welche vorzugsweise in Seewasser unlöslich sind. Ferner können Anstrichmittel Materialien, wie Kolophonium enthalten, um eine gesteuerte Freisetzung der Wirkstoffe zu ermöglichen. Die Anstriche können ferner Weichmacher, die Theologischen Eigenschaften beeinflussende Modifϊzierungsmittel sowie andere herkömmlichePaints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in seawater. Paints may also contain materials such as rosin to enable controlled release of the active ingredients. The paints can also contain plasticizers, modifiers that influence the theological properties and other conventional ones
Bestandteile enthalten. Auch in Self-Polishing-Antifouling-Systemen können die erfϊndungsgemäßen Verbindungen oder die oben genannten Mischungen eingearbeitet werden.Components included. The compounds according to the invention or the mixtures mentioned above can also be incorporated into self-polishing antifouling systems.
Die Wirkstoffe eignen sich auch zur Bekämpfung von tierischen Schädlingen, insbesondere von Bisekten, Spinnentieren und Milben, die in geschlossenen Räumen, wie beispielsweise Wohnungen, Fabrikhallen, Büros, Fahrzeugkabinen u.a. vorkommen. Sie können zur Bekämpfung dieser Schädlinge allein oder in Kombination mit anderen Wirk- und Hilfsstoffen in Haushaltsinsektizid-Produkten verwendet werden. Sie sind gegen sensible und resistente Arten sowie gegen alle Entwicklungsstadien wirksam. Zu diesen Schädlingen gehören:The active ingredients are also suitable for controlling animal pests, in particular bisects, arachnids and mites, which occur in closed spaces, such as, for example, apartments, factory halls, offices, vehicle cabins and others. To combat these pests, they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products. You are sensitive to and resistant species and effective against all stages of development. These pests include:
Aus der Ordnung der Scorpionidea z.B. Buthus occitanus. Aus der Ordnung der Acarina z.B. Argas persicus, Argas reflexus, Bryobia ssp..From the order of the Scorpionidea e.g. Buthus occitanus. From the order of the Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp ..
Dermanyssus gallinae, Glyciphagus domesticus, Omithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.Dermanyssus gallinae, Glyciphagus domesticus, Omithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
Aus der Ordnung der Araneae z.B. Aviculariidae, Araneidae. Aus der Ordnung der Opiliones z.B. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.From the order of the Araneae e.g. Aviculariidae, Araneidae. From the order of the Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
Aus der Ordnung der Isopoda z.B. Oniscus asellus, Porcellio scaber.From the order of the Isopoda e.g. Oniscus asellus, Porcellio scaber.
Aus der Ordnung der Diplopoda z.B. Blaniulus guttulatus, Polydesmus spp..From the order of the Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..
Aus der Ordnung der Chilopoda z.B. Geophilus spp.. Aus der Ordnung der Zygentoma z.B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.From the order of the Chilopoda e.g. Geophilus spp .. From the order of the Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
Aus der Ordnung der Blattaria z.B. Blatta orientalies, Blattella germanica, Blattella asahinai,From the order of the Blattaria e.g. Blatta orientalies, Blattella germanica, Blattella asahinai,
Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa. Aus der Ordnung der Saltatoria z.B. Acheta domesticus.Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa. From the order of the Saltatoria e.g. Acheta domesticus.
Aus der Ordnung der Dermaptera z.B. Forficula auricularia.From the order of the Dermaptera e.g. Forficula auricularia.
Aus der Ordnung der Isoptera z.B. Kalotermes spp., Reticulitermes spp.From the order of the Isoptera e.g. Kalotermes spp., Reticulitermes spp.
Aus der Ordnung der Psocoptera z.B. Lepinatus spp., Liposcelis spp.From the order of the Psocoptera e.g. Lepinatus spp., Liposcelis spp.
Aus der Ordnung der Coleoptera z.B. Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius,From the order of the Coleoptera e.g. Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius,
Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
Aus der Ordnung der Diptera z.B. Aedes aegypti, Aedes aϊbopictus, Aedes taeniorhynchus,From the order of the Diptera e.g. Aedes aegypti, Aedes aϊbopictus, Aedes taeniorhynchus,
Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus,Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus,
Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga camaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga camaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.
Aus der Ordnung der Lepidoptera z.B. Achroia grisella, Galleria mellonella, Plodia inteφunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.From the order of the Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inteφunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
Aus der Ordnung der Siphonaptera z.B. CtenocephaUdes canis, CtenocephaUdes felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis. Aus der Ordnung der Hymenoptera z.B. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaόnis, Paravespula spp., Tetramorium caespitum.From the order of the Siphonaptera, for example CtenocephaUdes canis, CtenocephaUdes felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis. From the order of the Hymenoptera, for example Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaόnis, Paravespula spp., Tetramorium caespitum.
Aus der Ordnung der Anoplura z.B. Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis.From the order of the anoplura e.g. Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis.
Aus der Ordnung der Heteroptera z.B. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.From the order of the Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
Die Anwendung im Bereich der Haushaltsinsektizide erfolgt allein oder in Kombination mit anderen geeigneten Wirkstoffen wie Phosphorsäureestern, Carbamaten, Pyrethroiden, Neo- icotinoiden, Wachstumsregulatoren oder Wirkstoffen aus anderen bekannten Insektizidklassen.The application in the field of household insecticides is carried out alone or in combination with other suitable active compounds such as phosphoric acid esters, carbamates, pyrethroids, neo-icotinoids, growth regulators or active compounds from other known classes of insecticides.
Die Anwendung erfolgt in Aerosolen, drucklosen Sprühmitteln, z.B. Pump- und Zerstäuber- sprays, Nebelautomaten, Foggem, Schäumen, Gelen, Verdampferprodukten mit Verdamp- ferplättchen aus Cellulose oder Kunststoff, Flüssigverdampfern, Gel- und Membranverdampfern, propellergetriebenen Verdampfern, energielosen bzw. passiven Verdampfungssystemen, Mottenpapieren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködem oder Köderstationen.They are used in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, fog machines, foggem, foams, gels, vaporizer products with vaporizer plates made of cellulose or plastic, liquid vaporizers, gel and membrane vaporizers, propeller-driven vaporizers, energy-free or passive evaporation systems, moth papers, moth bags and moth gels, as granules or Dusts, in litter edema or bait stations.
Die Herstellung und die Verwendung der erfϊndungsgemäßen Stoffe geht aus den folgenden Beispielen hervor. The preparation and use of the substances according to the invention can be seen from the following examples.
HerstellungsbeispielePreparation Examples
Beispiel 1example 1
Unter Argon werden 0,7 g (2,47 mmol) 2-(4-Bromphenyl)-5-ethoxythiophen und 0,95 g (2,47 mmol) 5-(2,6-Difluorphenyl)-2-[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phe- nyl]-3,4-dihydro-2H-pyrrol in 30 ml absolutem Tetrahydrofuran vorgelegt. Nach Zugabe von 2,63 g (9,89 mmol) Trikaliumphosphat-Trihydrat, 11 mg (0,05 mmol) Palladium(I[)- acetat und 37 mg (0,124 mmol) 2-(Di-tert-butylphosphino)biphenyl refluxiert man 5 h, setzt dann nochmals gleiche Mengen an Palladium(TI)-acetat und 2-(Di-tertrbutylphosphino)- biphenyl zu und refluxiert diese Mischung dann weitere 10 h. Nach dem Abkühlen gießt man die Reaktionsmischung auf Wasser und extrahiert das Produkt mit Dichlormethan. Die organische Phase wird getrocknet und im Vakuum einrotiert. Man erhält 1,05 g harziges Rohprodukt, das im System Cyclohexan/Essigsäureethylester (2 : 1) an Kieselgel chro- matographiert wird.0.7 g (2.47 mmol) of 2- (4-bromophenyl) -5-ethoxythiophene and 0.95 g (2.47 mmol) of 5- (2,6-difluorophenyl) -2- [4- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolan-2-yl) phenyl] -3,4-dihydro-2H-pyrrole in 30 ml of absolute tetrahydrofuran. After adding 2.63 g (9.89 mmol) tripotassium phosphate trihydrate, 11 mg (0.05 mmol) palladium (I [) acetate and 37 mg (0.124 mmol) 2- (di-tert-butylphosphino) biphenyl refluxed 5 h, then the same amounts of palladium (TI) acetate and 2- (di-tert-butylphosphino) biphenyl are added, and the mixture is then refluxed for a further 10 h. After cooling, the reaction mixture is poured onto water and the product is extracted with dichloromethane. The organic phase is dried and evaporated in vacuo. This gives 1.05 g of a crude resinous product which is chromatographed on silica gel in the cyclohexane / ethyl acetate (2: 1) system.
Man erhält 0,22 g (19,4 % der Theorie) an 5-(2,6-Difluorρhenyl)-2-[4'-(5-ethoxy-2-thienyl)- l,r-biphenyl-4-yl]-3,4-dihydro-2H-pyrrol als hellgelbes Kristallisat mit dem Schmelzpunkt 128°C - 134°C, dem LogP (pH 2,3) = 4,88 und dem LogP (pH 7,5) = 5,84.0.22 g (19.4% of theory) of 5- (2,6-difluorophenyl) -2- [4 '- (5-ethoxy-2-thienyl) -1, r-biphenyl-4-yl ] -3,4-dihydro-2H-pyrrole as light yellow crystals with a melting point of 128 ° C - 134 ° C, the LogP (pH 2.3) = 4.88 and the LogP (pH 7.5) = 5.84 ,
Beispiel 2Example 2
Analog Beispiel 1 wird ausgehend von 2-(4-Bromphenyl)-5-methoxythiophen das 5-(2,6- Difluoφhenyl)-2-[4'-(5-methoxy-2-thienyl)-l , 1 '-biphenyl-4-yl]-3,4-dihydro-2H-pyιτol mit dem Schmelzpunkt 138°C - 142°C und dem LogP (pH 2,3) = 4,35 erhalten. Beispiel 3Analogously to Example 1, starting from 2- (4-bromophenyl) -5-methoxythiophene, the 5- (2,6-difluorophenyl) -2- [4 '- (5-methoxy-2-thienyl) -1, 1'-biphenyl -4-yl] -3,4-dihydro-2H-pyιτol with the melting point 138 ° C - 142 ° C and the LogP (pH 2.3) = 4.35. Example 3
Analog Beispiel 1 wird ausgehend von 2-(4-Bromphenyl)-5-isopropoxythioρhen das 5-(2,6- Difluoφhenyl)-2-[4'-(5-isopropoxy-2-thienyl)-l , 1 '-biphenyl-4-yl]-3,4-dihydro-2H-pyrrol mit dem Schmelzpunkt 131°C - 134°C und dem LogP (pH 2,3) = 5,20 erhalten.Analogously to Example 1, starting from 2- (4-bromophenyl) -5-isopropoxythiophene, the 5- (2,6-difluorophenyl) -2- [4 '- (5-isopropoxy-2-thienyl) -1, 1' -biphenyl -4-yl] -3,4-dihydro-2H-pyrrole with the melting point 131 ° C.-134 ° C. and the LogP (pH 2.3) = 5.20.
Beispiel 4Example 4
Unter Argonatmosphäre gibt nacheinander 3-(4-Bromphenyl)-5-trifluormethyl-l,2,4- oxadiazol (0,29 g, 1,0 mmol), 5-(2-Methylphenyl)-2-[4-(4,4,5,5-tetramethyl-l,3,2-dioxa- borolan-2-yl)phenyl]-3,4-dihydro-2H-pyrrol (II-l) (0,3 g, 0,83 mmol) gelöst in 12 ml Di- methoxyethan, l, -Bis(diphenylphosphmo)ferrocenρalladium(II)chlorid (0,018 g, Under an argon atmosphere there are successively 3- (4-bromophenyl) -5-trifluoromethyl-l, 2,4-oxadiazole (0.29 g, 1.0 mmol), 5- (2-methylphenyl) -2- [4- (4th , 4,5,5-tetramethyl-l, 3,2-dioxa-borolan-2-yl) phenyl] -3,4-dihydro-2H-pyrrole (II-l) (0.3 g, 0.83 mmol ) dissolved in 12 ml dimethoxyethane, l, bis (diphenylphosphmo) ferrocene palladium (II) chloride (0.018 g,
0,025 mmol) und Natriumcarbonat-Lösung (1,25 ml, 2 M) in ein Reaktionsgefäß, welches anschließend verschlossen wird. Das Reaktionsgemisch wird 16 h bei 80°C gerührt. Nach abgeschlossener Umsetzung wird auf Raumtemperatur abgekühlt. Man gibt 1 g Isolute RHM-N (Separtis) zu und engt ein. Der Rückstand wird über Kartuschenchromatographie (Gradient Cyclohexan/Essigsäureethylester 95:5 -> 3:2) aufgereinigt.0.025 mmol) and sodium carbonate solution (1.25 ml, 2 M) in a reaction vessel, which is then sealed. The reaction mixture is stirred at 80 ° C. for 16 h. When the reaction is complete, the mixture is cooled to room temperature. 1 g of Isolute RHM-N (Separtis) is added and the mixture is concentrated. The residue is purified by cartridge chromatography (gradient cyclohexane / ethyl acetate 95: 5 → 3: 2).
Man erhält 0,085 g (19,2 % der Theorie) an 3-{4'-[5-(2-Methylphenyl)-3,4-dihydro-2H- pyrrol-2-yl]-l,r-biphenyl-4-yl}-5-(trifluormethyl)-l,2,4-oxadiazol mit dem LogP (pH 2,3) = 3,32. . Beispiel 50.085 g (19.2% of theory) of 3- {4 '- [5- (2-methylphenyl) -3,4-dihydro-2H-pyrrol-2-yl] -l, r-biphenyl-4 is obtained -yl} -5- (trifluoromethyl) -l, 2,4-oxadiazole with the LogP (pH 2.3) = 3.32. , Example 5
Zu einer Lösung von 5-(2,6-Difluoφhenyl)-2-[2-fluor-4-(4,4,5,5-tetramethyl-l,3,2-dioxa- borolan-2-yl)phenyl]-3,4-dihydro-2H-pyrrol (JI-2) (0,40 g, 1 mmol) in 30 ml Dimethoxy- ethan gibt man nacheinander 5-(4-Bromρhenyl)-3-tert-butyl-l,2,4-oxadiazol (0,31 g, 1,1 mmol), l, -Bis(diphenylphosphmo)ferrocenpalladium(TI)chlorid (0,022 g, 0,03 mmol) und 1,5 ml einer wässrigen 2 M Natriumcarbonat-Lösung. Man lässt dieses Gemisch 16 h bei 80°C reagieren. Zur Aufarbeitung lässt man das Reaktionsgemisch abkühlen und versetzt mit Wasser/Essigsäureethylester. Die organische Phase wird abgetrennt, über Natriumsulfat getrocknet, filtriert und eingeengt. Das Rohprodukt wird mittels Säulenchromatographie an Kieselgel aufgereinigt (Gradient Methylenchlorid/Essigsäureethylester 100:0 -> 95:5).To a solution of 5- (2,6-difluorophenyl) -2- [2-fluoro-4- (4,4,5,5-tetramethyl-l, 3,2-dioxa-borolan-2-yl) phenyl] -3,4-dihydro-2H-pyrrole (JI-2) (0.40 g, 1 mmol) in 30 ml of dimethoxyethane is added in succession to 5- (4-bromophenyl) -3-tert-butyl-1,2 , 4-oxadiazole (0.31 g, 1.1 mmol), l, -bis (diphenylphosphmo) ferrocene palladium (TI) chloride (0.022 g, 0.03 mmol) and 1.5 ml of an aqueous 2 M sodium carbonate solution. This mixture is allowed to react at 80 ° C for 16 h. For working up, the reaction mixture is allowed to cool and water / ethyl acetate are added. The organic phase is separated off, dried over sodium sulfate, filtered and concentrated. The crude product is purified by column chromatography on silica gel (gradient methylene chloride / ethyl acetate 100: 0 → 95: 5).
Man erhält 0,3 g (60,3 % der Theorie) an 3-tert-Butyl-5-{4'-[5-(2,6-difiuoφhenyl)-3,4- dihydro-2H-pyrrol-2-yl]-3'-fluor-l,l'-biphenyl-4-yl}-l,2,4-oxadiazol mit dem LogP (pH 2,3) = 5,79 und dem LogP (pH 7,5) = 6,06.0.3 g (60.3% of theory) of 3-tert-butyl-5- {4 '- [5- (2,6-difiuoφhenyl) -3,4-dihydro-2H-pyrrole-2- yl] -3'-fluoro-l, l'-biphenyl-4-yl} -l, 2,4-oxadiazole with the LogP (pH 2.3) = 5.79 and the LogP (pH 7.5) = 6.06.
Beispiel 6Example 6
Zu einer Lösung von 5-(2,6-Difluoφhenyl)-2-[2-fluor-4-(4,4,5,5-tetramethyl-l,3,2-dioxa- borolan-2-yl)phenyl]-3,4-dihydro-2H-pyrrol (U-2) (0,60 g, 1,5 mmol) in 30 ml Dimethoxy- ethan gibt man nacheinander 3-(4-Bromphenyl)-5-tert-butyl-l,2,4-oxadiazol (0,46 g, 1,65 mmol), l, -Bis(diphenylphosphmo)ferrocenpalladium(π)chlorid (0,033 g,To a solution of 5- (2,6-difluorophenyl) -2- [2-fluoro-4- (4,4,5,5-tetramethyl-l, 3,2-dioxa-borolan-2-yl) phenyl] -3,4-dihydro-2H-pyrrole (U-2) (0.60 g, 1.5 mmol) in 30 ml of dimethoxyethane is added in succession to 3- (4-bromophenyl) -5-tert-butyl-l , 2,4-oxadiazole (0.46 g, 1.65 mmol), l, -Bis (diphenylphosphmo) ferrocene palladium (π) chloride (0.033 g,
0,045 mmol) und 2,25 ml einer wässrigen 2 M Natriumcarbonat-Lösung. Man lässt dieses Gemisch 16 h bei 80°C reagieren. Zur Aufarbeitung lässt man das Reaktionsgemisch abkühlen und versetzt mit Wasser/Essigsäureethylester. Die organische Phase wird abgetrennt, über Natriumsulfat getrocknet, filtriert und eingeengt. Das Rohprodukt wird mittels Säulenchromatographie an Kieselgel aufgereinigt (Gradient Methylenchlorid/Essig- säureethylester 100:0 --> 95:5). . .0.045 mmol) and 2.25 ml of an aqueous 2 M sodium carbonate solution. This mixture is allowed to react at 80 ° C for 16 h. For working up, the reaction mixture is allowed to cool and water / ethyl acetate are added. The organic phase is separated off, dried over sodium sulfate, filtered and concentrated. The raw product is purified by column chromatography on silica gel (gradient methylene chloride / ethyl acetate 100: 0 -> 95: 5). , ,
Man erhält 0,51 g (69,9 % der Theorie) an 5-tert-Butyl-3-{4'-[5-(2,6-difluoφhenyl)-3,4- dihydro-2H-ρyrrol-2-yl]-3'-fluor-l,r-biphenyl-4-yl}-l,2,4-oxadiazol mit dem LogP (pH 2,3) = 5,65 und dem LogP (pH 7,5) = 5,97.0.51 g (69.9% of theory) of 5-tert-butyl-3- {4 '- [5- (2,6-difluoφhenyl) -3,4-dihydro-2H-ρyrrol-2- yl] -3'-fluoro-l, r-biphenyl-4-yl} -l, 2,4-oxadiazole with the LogP (pH 2.3) = 5.65 and the LogP (pH 7.5) = 5 , 97th
Analog den oben aufgeführten Beispielen 1 bis 6 sowie der allgemeinen Beschreibung werden folgende Verbindungen der Formel (I-f) erhalten.The following compounds of the formula (I-f) are obtained analogously to Examples 1 to 6 listed above and the general description.
Tabelle 1Table 1
Herstellung von Ausgangsstoffen der Formel (JDProduction of starting materials of the formula (JD
Beispiel 01-1)Example 01-1)
Stufe 1step 1
Zu 62,2 g (0,61 mol) Schwefelsäure tropft man bei 0°C innerhalb von 45 min 150 ml Acetonitril zu und rührt 30 min nach. Anschließend tropft man bei ca. -5°C innerhalb von150 ml of acetonitrile are added dropwise at 0.degree. C. to 62.2 g (0.61 mol) of sulfuric acid and the mixture is subsequently stirred for 30 minutes. Then drip at about -5 ° C within
45 min eine Lösung von [2-(4-Bromphenyl)cyclopropyl](2-methylphenyl)methanon (48 g, 0,15 mol) in 300 ml Acetonitril zu und rührt für 16 h unter Erwärmung auf Raumtemperatur nach. Das Reaktionsgemisch wird in Ammoniak (150 ml)/Eiswasser (800 ml) eingerührt und dreimal mit je 400 ml Essigsäureethylester extrahiert. Die organische Phase wird abgetrennt, über Natriumsulfat getrocknet, filtriert und eingeengt. Das Rohprodukt wird mittels Flashchromatographie (Gradient Methylenchlorid/Essigsäureethylester 10:0 ■ 1:1) aufgereinigt.A solution of [2- (4-bromophenyl) cyclopropyl] (2-methylphenyl) methanone (48 g, 0.15 mol) in 300 ml of acetonitrile is added for 45 min and the mixture is stirred for 16 h while warming to room temperature. The reaction mixture is stirred into ammonia (150 ml) / ice water (800 ml) and extracted three times with 400 ml of ethyl acetate each time. The organic phase is separated off, dried over sodium sulfate, filtered and concentrated. The crude product is purified by flash chromatography purified (gradient methylene chloride / ethyl acetate 10: 1: 0 ■ 1).
Man erhält 17,2 g (33,3 % der Theorie) an N-[l-(4-Bromphenyl)-4-(2-methylphenyl)-4- oxobutyljacetamid mit dem LogP (pH 2,3) = 3,33.17.2 g (33.3% of theory) of N- [1- (4-bromophenyl) -4- (2-methylphenyl) -4-oxobutyljacetamide with LogP (pH 2.3) = 3.33 are obtained ,
Stufe 2Level 2
Zu einer Lösung aus N-[l-(4-Bromphenyl)-4-(2-methylphenyl)-4-oxobutyl]acetamid (17,6 g, 47,0 mmol) in 100 ml Ethanol werden 24 g (235 mmol) Schwefelsäure getropft. Das24 g (235 mmol) are added to a solution of N- [l- (4-bromophenyl) -4- (2-methylphenyl) -4-oxobutyl] acetamide (17.6 g, 47.0 mmol) in 100 ml of ethanol. Dropped sulfuric acid. The
Reaktionsgemisch wird anschließend unter Reflux gerührt. Nach dem Abkühlen auf Raumtemperatur rührt man das Reaktionsgemisch in Natronlauge (45%ig, 100 ml)/Eiswasser (500 ml) ein und extrahiert dreimal mit je 400 ml Essigsäureethylester. Die organische Phase wird abgetrennt, über Natriumsulfat getrocknet, filtriert und eingeengt. Das Rohprodukt wird mittels Flashchromatographie an Kieselgel (Methylenchlorid/Essigsäure- ethylester 10:1) aufgereinigt.The reaction mixture is then stirred under reflux. After cooling to room temperature, the reaction mixture is stirred into sodium hydroxide solution (45%, 100 ml) / ice water (500 ml) and extracted three times with 400 ml of ethyl acetate each time. The organic phase is separated off, dried over sodium sulfate, filtered and concentrated. The crude product is purified by means of flash chromatography on silica gel (methylene chloride / ethyl acetate 10: 1).
Man erhält 10,6 g (68,7 % der Theorie) an 2-(4-Bromphenyl)-5-(2-methylphenyl)-3,4- dihydro-2H-pyrrol mit dem LogP (pH 2,3) = 1,82 und dem LogP (pH 7,5) = 4,48.10.6 g (68.7% of theory) of 2- (4-bromophenyl) -5- (2-methylphenyl) -3,4-dihydro-2H-pyrrole are obtained with the LogP (pH 2.3) = 1.82 and the LogP (pH 7.5) = 4.48.
Stufe 3level 3
Zu einem Gemisch aus 2-(4-Bromphenyl)-5-(2-methylphenyl)-3,4-dihydro-2H-pyrrol (3,14 g, 10 mmol), 4,4,4^4^5,5,5^5'-Octamethyl-2,2"-bi-lA2-dioxaborolan (2,79 g, 11 mmol), Kaliumacetat (2,94 g, 30 mmol), l, -Bis(diphenylphosphino)ferrocen- palladium(H)chlorid (0,22 g, 0,3 mmol) und l, -Bis(diphenylphosphino)ferrocene (0,17 g, 0,3 mmol) gibt man 40 ml Dioxan und lässt für 16 h bei 100°C reagieren. Zur Aufarbeitung wird das Reaktionsgemisch mit 100 ml Wasser versetzt und zweimal mit je 100 ml Essigsäureethylester extrahiert. Die organische Phase wird abgetrennt, über Natriumsulfat getrocknet, filtriert und eingeengt. Der Rückstand wird in 30 ml Dichlormethan gelöst und mittels Flashchromatographie an Kieselgel aufgereinigt (Gradient Methylenchlorid/Essig- säureethylester 10:0 --» 9:1). Man erhält 2,3 g (62,4 % der Theorie) an •5-(2-Methylphenyl)-2-[4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)phenyl]-3,4-dihydro-2H-pyrrol mit dem LogP (pH 2,3) = 2,25 und demLogP (pH 7,5) = 4,98.To a mixture of 2- (4-bromophenyl) -5- (2-methylphenyl) -3,4-dihydro-2H-pyrrole (3.14 g, 10 mmol), 4.4.4 ^ 4 ^ 5.5 , 5 ^ 5'-octamethyl-2,2 "-bi-lA2-dioxaborolane (2.79 g, 11 mmol), potassium acetate (2.94 g, 30 mmol), l, -Bis (diphenylphosphino) ferrocene-palladium ( H) chloride (0.22 g, 0.3 mmol) and l-bis (diphenylphosphino) ferrocene (0.17 g, 0.3 mmol) are added to 40 ml of dioxane and allowed to react at 100 ° C. for 16 h. For working up, the reaction mixture is mixed with 100 ml of water and extracted twice with 100 ml of ethyl acetate, the organic phase is separated off, dried over sodium sulfate, filtered and concentrated. The residue is dissolved in 30 ml of dichloromethane and purified by means of flash chromatography on silica gel (gradient methylene chloride / Ethyl acetate 10: 0 - »9: 1). 2.3 g (62.4% of theory) of • 5- (2-methylphenyl) -2- [4- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolane-2- yl) phenyl] -3,4-dihydro-2H-pyrrole with the LogP (pH 2.3) = 2.25 and the LogP (pH 7.5) = 4.98.
Beispiel QI-2^Example QI-2 ^
Stufe 1step 1
2-Fluor-4-brombenzaldehyd (20,3 g, 100 mmol) und 2,6-Bisfluoracetophenon (15,6 g, 2-fluoro-4-bromobenzaldehyde (20.3 g, 100 mmol) and 2,6-bisfluoroacetophenone (15.6 g,
100 mmol) werden in Methanol/Wasser gelöst. Unter Rühren tropft man langsam 30 ml einer 10%igen Natronlauge zu. Der ausfallende Feststoff wird abgesaugt, mit Methanol/Wasser gewaschen und getrocknet.100 mmol) are dissolved in methanol / water. While stirring, 30 ml of a 10% sodium hydroxide solution are slowly added dropwise. The precipitated solid is filtered off, washed with methanol / water and dried.
Man erhält 30,5 g (95,6 % der Theorie) an (2E)-3-(4-Brom-2-fluoφhenyl)-l-(2,6-difluor- phenyl)-2-propen-l-on mit dem LogP (pH 2,3) = 4,18.30.5 g (95.6% of theory) of (2E) -3- (4-bromo-2-fluorophene) -l- (2,6-difluorophenyl) -2-propen-l-one are obtained with the LogP (pH 2.3) = 4.18.
Stufe 2Level 2
Unter Argon wird Kaliumcarbonat (13,8 g, 100 mmol) in Dimethylsulfoxid vorgelegt. Portionsweise wird mit Trimethylsulfoxoniumiodid (23^5 g, 250 mmol) versetzt und anschließend für 1,5 h bei Raumtemperatur nachreagieren gelassen. Anschließend tropft man eine Lösung von (2E)-3-(4-Brom-2-fluoφhenyl)-l-(2,6-difluoφhenyl)-2-propen-l-on (34 g, 100 mmol) in Dimethylsulfoxid zu und rührt für 16 h nach. Das Reaktionsgemisch wird in extrahiert. Die organische Phase wird abgetrennt, über.Natriumsulfat getrocknet, filtriert und eingeengt. Der Rückstand wird mit wenig Isopropanol angeteigt, abgesaugt und der Feststoff getrocknet.Potassium carbonate (13.8 g, 100 mmol) in dimethyl sulfoxide is introduced under argon. Trimethylsulfoxonium iodide (23 ^ 5 g, 250 mmol) is added in portions and the mixture is then left to react for 1.5 h at room temperature. A solution of (2E) -3- (4-bromo-2-fluoφhenyl) -l- (2,6-difluoφhenyl) -2-propen-l-one (34 g, 100 mmol) in dimethyl sulfoxide is then added dropwise and stir for 16 h. The reaction mixture is in extracted. The organic phase is separated off, dried over sodium sulfate, filtered and concentrated. The residue is pasted with a little isopropanol, suction filtered and the solid dried.
Man erhält 31 g (84,1 % der Theorie) an [2-(4-Brom-2-fluoφhenyl)cycl.opropyl](2,6- difluoφhenyl)methanon mit dem LogP (pH 2,3) = 4,31.31 g (84.1% of theory) of [2- (4-bromo-2-fluoφhenyl) cycl.opropyl] (2,6-difluoφhenyl) methanone are obtained with the LogP (pH 2.3) = 4.31 ,
Stufe 3level 3
Zu 39 g Schwefelsäure tropft man bei 0°C 100 ml Acetonitril zu und rührt 1 h nach. Anschließend kühlt man auf -10°C ab, tropft eine Lösung von [2-(4-Brom-2-fluoφhenyl)- cyclopropyl](2,6-difluoφhenyl)methanon (31 g, 87,3 mmol) in 380.ml Acetonitril zu und rührt für 16 h bei Raumtemperatur nach. Das Reaktionsgemisch wird in Ammoniak Eiswasser eingerührt und vom Feststoff abgesaugt. Das Filtrat wird mit Methyl- tert-butyl-ether extrahiert. Die organische Phase wird abgetrennt, über Natriumsulfat getrocknet, filtriert und eingeengt. 100 ml of acetonitrile are added dropwise to 39 g of sulfuric acid at 0 ° C. and stirring is continued for 1 h. The mixture is then cooled to -10 ° C. and a solution of [2- (4-bromo-2-fluoφhenyl) cyclopropyl] (2,6-difluoφhenyl) methanone (31 g, 87.3 mmol) in 380 ml Acetonitrile and stirred for 16 h at room temperature. The reaction mixture is stirred into ammonia ice water and suctioned off from the solid. The filtrate is extracted with methyl tert-butyl ether. The organic phase is separated off, dried over sodium sulfate, filtered and concentrated.
Man erhält 6,4 g (16,6 % der Theorie) an N-[l-(4-Brom-2-fluoφhenyl)-4-(2,6-difluor- phenyl)-4-oxobutyl]acetamid mit dem LogP (pH 2,3) = 2,74.6.4 g (16.6% of theory) of N- [l- (4-bromo-2-fluorophene) -4- (2,6-difluorophenyl) -4-oxobutyl] acetamide are obtained with the LogP (pH 2.3) = 2.74.
Stufe 4Level 4
N-[l-(4-Brom-2-fluoφhenyl)-4-(2,6-difluorophenyl)-4-oxobutyl]acetamid (36 g, 86,9 mmol) wird in 6Ν Salzsäure und Ethanol für 24 h bei 100°C gerührt. Nach dem Abkühlen gießt man auf Eis/Natronlauge und extrahiert mit Essigsäureethylester. Die organische Phase wird abgetrennt, über Natriumsulfat getrocknet, filtriert und eingeengt. Auskristallisierter Feststoff wird abgesaugt und mit Essigsäureethylester/Cyclohexan 1:10 gewaschen. Nach Einengen des Filtrates erhält man 10,0 g (30,5 % der Theorie) an 2-(4-Brom-2- fluoφhenyl)-5-(2,6-difluoφhenyl)-3,4-dihydro-2H-pyrrol.N- [l- (4-bromo-2-fluorophene) -4- (2,6-difluorophenyl) -4-oxobutyl] acetamide (36 g, 86.9 mmol) is dissolved in 6Ν hydrochloric acid and ethanol for 24 h at 100 ° C stirred. After cooling, the mixture is poured onto ice / sodium hydroxide solution and extracted with ethyl acetate. The organic phase will separated, dried over sodium sulfate, filtered and concentrated. Crystallized solid is suction filtered and washed with ethyl acetate / cyclohexane 1:10. After concentrating the filtrate, 10.0 g (30.5% of theory) of 2- (4-bromo-2-fluoφhenyl) -5- (2,6-difluoφhenyl) -3,4-dihydro-2H-pyrrole are obtained ,
Η-NMR (400 MHz, CD3CN): δ = 7,45 (m, 1 H), 7,35 (m, 2. H), 7,30 (m, 1 H), 7,10 (t, 2Η NMR (400 MHz, CD 3 CN): δ = 7.45 (m, 1 H), 7.35 (m, 2. H), 7.30 (m, 1 H), 7.10 (t , 2nd
H), 5,45 (t, 1 H), 3,10 (dd, 2 H), 2,70 (m, 1 H), 1,80 (m, 1 H) ppm. LC-MS: 355,9 [M+HfH), 5.45 (t, 1 H), 3.10 (dd, 2 H), 2.70 (m, 1 H), 1.80 (m, 1 H) ppm. LC-MS: 355.9 [M + Hf
Stufe 5Level 5
Zu einem Gemisch aus 2-(4-Brom-2-fluoφhenyl)-5-(2,6-difluoφhenyl)-3,4-dihydro-2H- pyrrol (20 g, 56,5 mmol), 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-l,3,2-dioxaborolan (15,8 g, 62,1 mmol), Kaliumacetat (16,6 g, 169,4 mmol), l, -Bis(diphenylphosphino)ferrocen- palladium(H)chlorid (1,24 g, 1,69 mmol) und l, -Bis(diphenylphosphino)ferrocene (0,94 g,To a mixture of 2- (4-bromo-2-fluoφhenyl) -5- (2,6-difluoφhenyl) -3,4-dihydro-2H-pyrrole (20 g, 56.5 mmol), 4.4.4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi-l, 3,2-dioxaborolane (15.8 g, 62.1 mmol), potassium acetate (16.6 g, 169.4 mmol), l, -Bis (diphenylphosphino) ferrocene-palladium (H) chloride (1.24 g, 1.69 mmol) and l, -Bis (diphenylphosphino) ferrocene (0.94 g,
1,69 mmol) gibt man 200 ml Dioxan und lässt für 16 h bei 100°C reagieren. Zur Aufarbeitung wird das Reaktionsgemisch mit 400 ml Wasser versetzt und zweimal mit je 300 ml Essigsäureethylester extrahiert. Die organische Phase wird abgetrennt, über Natriumsulfat getrocknet, filtriert und eingeengt. Der Rückstand wird in 100 ml Dichlormethan gelöst und mittels Flashchromatographie an Kieselgel aufgereinigt (Gradient1.69 mmol), 200 ml of dioxane are added and the mixture is left to react at 100 ° C. for 16 h. For working up, the reaction mixture is mixed with 400 ml of water and extracted twice with 300 ml of ethyl acetate. The organic phase is separated off, dried over sodium sulfate, filtered and concentrated. The residue is dissolved in 100 ml of dichloromethane and purified by means of flash chromatography on silica gel (gradient
Methylenchlorid Essigsäureethylester 10:0 -> 9:1).Methylene chloride ethyl acetate 10: 0 -> 9: 1).
Man erhält 21,2 g (89,5 % der Theorie) an 5-(2,6-Dϊfluoφhenyl)-2-[2-fluor-4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-3,4-dihydro-2H-pyrrol mit dem LogP (pH 2,3) = 4,88. 21.2 g (89.5% of theory) of 5- (2,6-Dϊfluoφhenyl) -2- [2-fluoro-4- (4,4,5,5-tetramethyl-l, 3.2) are obtained -dioxaborolan-2-yl) phenyl] -3,4-dihydro-2H-pyrrole with the LogP (pH 2.3) = 4.88.
Die Bestimmung der in den- voranstehenden Tabellen und Herstellungsbeispielen angegebenen logP-Werte erfolgt gemäß EEC-Directive 79/831 Annex V.A8 durch HPLC (High Performance Liquid Chromatography) an einer Phasenumkehrsäule (C 18). Temperatur: 43°C.The logP values given in the tables and manufacturing examples above are determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.
Die Bestimmung erfolgt im sauren Bereich bei pH 2.3 mit 0,1% wässriger Phosphorsäure und Acetonitril als Eluenten; linearer Gradient von 10% Acetonitril bis 90% Acetonitril (in den Tabellen mit a) markiert).The determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluents; linear gradient from 10% acetonitrile to 90% acetonitrile (marked with a in the tables).
Die Bestimmung erfolgt im neutralen Bereich bei pH 7.5 mit 0,01 -molare wässrigerThe determination is carried out in the neutral range at pH 7.5 with 0.01 molar aqueous
Phosphatpuffer-Lösung und Acetonitril als Eluenten; linearer Gradient von 10 % Acetonitril bis 90 % Acetonitril (in den Tabellen mit b) markiert). ■Phosphate buffer solution and acetonitrile as eluents; linear gradient from 10% acetonitrile to 90% acetonitrile (marked with b in the tables). ■
Die Eichung erfolgt mit unverzweigten Alkan-2-onen (mit 3 bis 16 Kohlenstoffatomen), deren logP-Werte bekannt sind (Bestimmung der logP-Werte anhand der Retentionszeiten durch lineare Biteφolation zwischen zwei aufeinanderfolgenden Alkanonen).The calibration is carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear bitolation between two successive alkanones).
Die lambda-max-Werte wurden an Hand der UV-Spektren von 200 um bis 400 nm in den Maxima der chromatographischen Signale ermittelt. The lambda max values were determined on the basis of the UV spectra from 200 μm to 400 nm in the maxima of the chromatographic signals.
AnwendnngsbeispieleAnwendnngsbeispiele
Beispiel AExample A
Heliothis armigera-TestHeliothis armigera test
Lösungsmittel: 7 Gewichtsteile Dimethylformamid Emulgator: 2 Gewichtsteile AlkylarylpolyglykoletherSolvent: 7 parts by weight of dimethylformamide emulsifier: 2 parts by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 GewichtsteilTo produce a suitable preparation of active compound, 1 part by weight is mixed
Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit emulgatorhaltigem Wasser auf die gewünschte Konzentration.Active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water containing emulsifier to the desired concentration.
Sojatriebe (Glycine max) werden durch Tauchen in . die Wirkstoffzubereitung der gewünschten Konzentration behandelt und mit Raupen des BaumwollkapselwurmsSoybean shoots (Glycine max) are obtained by diving in . treated the active ingredient preparation of the desired concentration and with caterpillars of the cotton capsule worm
(Heliothis armigera) besetzt, solange die Blätter noch feucht sind.(Heliothis armigera) occupied while the leaves are still moist.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Raupen abgetötet wurden; 0 % bedeutet, dass keine Raupen abgetötet wurden.After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele gute Wirksamkeit: In this test, e.g. B. the following compounds of the preparation examples have good activity:
-in- • -in- •
Tabelle ATable A
Tabelle A Table A
Beispiel BExample B
Phaedon-Larven-TestPhaedon larvae test
Lösungsmittel: 7 Gewichtsteile Dimethylformamid Emulgator: • 2 Gewichtsteile AlkylarylpolyglykoletherSolvent: 7 parts by weight of dimethylformamide emulsifier: • 2 parts by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt dasTo produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the mixture is diluted
10 Konzentrat mit emulgatorhaltigem Wasser auf die gewünschte Konzentration.10 Concentrate with water containing emulsifier to the desired concentration.
Kohlblätter (Brassica oleracea) werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt und mit Larven des Meerrettichblattkäfers (Phaedon cochleariae) besetzt, solange die Blätter noch feucht sind.Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish leaf beetle (Phaedon cochleariae) while the leaves are still moist.
■15 ■ 15
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Käferlarven abgetötet wurden; 0 % bedeutet, dass keine Käferlarven abgetötet wurden.After the desired time, the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele guteIn this test, e.g. B. the following compounds of the preparation examples are good
20 Wirksamkeit: 20 effectiveness:
Tabelle B pflanzenschädigende BisektenTable B bisect harmful plants
Phaedon-Larven-TestPhaedon larvae test
Tabelle B pflanzenschädigende Bisekten Table B bisect harmful plants
Phaedon-Larven-TestPhaedon larvae test
Beispiel CExample C
Plutella-TestPlutella Test
Lösungsmittel: 7 Gewichtsteile Dimethylformamid Emulgator: 2 Gewichtsteile AlkylarylpolyglykoletherSolvent: 7 parts by weight of dimethylformamide emulsifier: 2 parts by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit emulgatorhaltigem Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
Kohlblätter (Brassica oleracea) werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt und mit Raupen der Kohlschabe (Plutella xylostella) besetzt, solange die Blätter noch feucht sind.Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the cockroach (Plutella xylostella) while the leaves are still moist.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt: Dabei bedeutet 100 %, dass alle Raupen abgetötet wurden; 0 % bedeutet, dass keine Raupen abgetötet wurden.After the desired time, the kill is determined in%: 100% means that all the caterpillars have been killed; 0% means that no caterpillars have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele gute Wirksamkeit: In this test, e.g. B. the following compounds of the preparation examples have good activity:
Tabelle C pflanzenschädigende BisektenTable C plant-damaging bisects
Plutella-TestPlutella Test
Beispiel DExample D
Spodoptera exigua-TestSpodoptera exigua test
Lösungsmittel: 7 Gewichtsteile DimethylformamidSolvent: 7 parts by weight of dimethylformamide
Emulgator: 2 Gewichtsteile AlkylarylpolyglykoletherEmulsifier: 2 parts by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit emulgatorhaltigem Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
Kohlblätter (Brassica oleracea) werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt und mit Raupen des Heerwurms (Spodoptera exigua) besetzt, solange die Blätter noch feucht sind.Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera exigua) while the leaves are still moist.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Raupen abgetötet wurden; 0 % bedeutet, dass keine Raupen abgetötet wurden.After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele gute Wirksamkeit: In this test, e.g. B. the following compounds of the preparation examples have good activity:
Tabelle DTable D
Beispiel EExample E
Spodoptera frugiperda-TestSpodoptera frugiperda test
Lösungsmittel: 7 Gewichtsteile DimethylformamidSolvent: 7 parts by weight of dimethylformamide
Emulgator: 2 Gewichtsteile AlkylarylpolyglykoletherEmulsifier: 2 parts by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit emulgatorhaltigem Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
Kohlblätter (Brassica oleracea) werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt und mit Raupen des Heerwurms (Spodoptera frugiperda) besetzt, solange die Blätter noch feucht sind.Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera frugiperda) while the leaves are still moist.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Raupen abgetötet wurden; 0 % bedeutet, dass keine Raupen abgetötet wurden.After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele gute Wirksamkeit: In this test, e.g. B. the following compounds of the preparation examples have good activity:
Tabelle E pflanzenschädigende Bisekten Spodoptera frugiperda-TestTable E plant-damaging bisects Spodoptera frugiperda test
Beispiel FExample F
Tetranychus-Test (OP-resistent/Tauchbehandlung)Tetranychus test (OP-resistant / immersion treatment)
Lösungsmittel: 7 Gewichtsteile DimethylformamidSolvent: 7 parts by weight of dimethylformamide
Emulgator: 2 Gewichtsteile AlkylarylpolyglykoletherEmulsifier: 2 parts by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit emulgatorhaltigem Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
Bohnenpflanzen (Phaseolus vulgaris), die stark von allen Stadien der Gemeinen Spinnmilbe (Tetranychus urticae) befallen sind, werden in eine Wirkstoffaibereitung der gewünschten Konzentration getaucht.Bean plants (Phaseolus vulgaris), which are heavily infested with all stages of the common spider mite (Tetranychus urticae), are immersed in an active ingredient preparation of the desired concentration.
Nach der gewünschten Zeit wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Spmn ilben abgetötet wurden; 0 % bedeutet, dass keine Spinnmilben abgetötet wurden.After the desired time, the effect is determined in%. 100% means that all the spils have been killed; 0% means that no spider mites have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele gute Wirksamkeit: In this test, e.g. B. the following compounds of the preparation examples have good activity:
TabelleF pflanzenschädigende Milb Tetranychus-Test (OP-resistent/Tauchbehandlung)Table F plant-damaging Milb Tetranychus test (OP-resistant / immersion treatment)
Tabelle F pflanzenschädigende Milben Table F mites harmful to plants
Tetranychus-Test (OP-resistent/Tauchbehandlung)Tetranychus test (OP-resistant / immersion treatment)
Beispiel GExample G
Diabrotica balteata - Test (Larven im Boden)Diabrotica balteata test (larvae in the soil)
Grenzkonzentrations-Test / Bodeninsekten - Behandlung transgener PflanzenLimit concentration test / soil insects - treatment of transgenic plants
Lösungsmittel: 7 Gewichtsteile DimethylformamidSolvent: 7 parts by weight of dimethylformamide
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene MengeTo produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the stated amount is added
Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.Emulsifier and dilute the concentrate with water to the desired concentration.
Die Wirkstoffzubereitung wird auf den Boden gegossen. Dabei spielt die Konzentration des Wirkstoffs in der Zubereitung praktisch keine Rolle, entscheidend ist allein die Wirkstoffgewichtsmenge pro Volumeneinheit Boden, welche in ppm (mg/1) angegeben wird.The active ingredient preparation is poured onto the floor. The concentration of the active ingredient in the preparation is practically irrelevant, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm (mg / 1).
Man füllt den Boden in 0,25 1 Töpfe und lässt diese bei 20°C stehen.You fill the bottom in 0.25 1 pots and let them stand at 20 ° C.
Sofort nach dem Ansatz werden je Topf 5 vorgekeimte Maiskörner der Sorte YTELD GUARD (Warenzeichen von Monsanto Comp., USA) gelegt. Nach 2 Tagen werden in den behandelten Boden die entsprechenden Testinsekten gesetzt. Nach weiteren 7 Tagen wird der Wirkungsgrad des Wirkstoffs durch Auszählen der aufgelaufenen Maispflanzen bestimmt (1 Pflanze = 20% Wirkung). Immediately after the preparation, 5 pre-germinated maize kernels of the YTELD GUARD variety (trademark of Monsanto Comp., USA) are placed in each pot. After 2 days, the appropriate test insects are placed in the treated soil. After a further 7 days, the efficiency of the active ingredient is determined by counting the maize plants that have emerged (1 plant = 20% activity).
Beispiel HExample H
Heliothis virescens - Test (Behandlung transgener Pflanzen)Heliothis virescens - test (treatment of transgenic plants)
Lösungsmittel: 7 Gewichtsteile DimethylformamidSolvent: 7 parts by weight of dimethylformamide
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und der angegebenen Menge Emul- gator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
Sojatriebe (Glycine max) der Sorte Roundup Ready (Warenzeichen der Monsanto Comp. USA) werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt und mit der Tabakknospenraupe Heliothis virescens besetzt, solange die Blätter noch feucht sind.Soybean shoots (Glycine max) of the Roundup Ready variety (trademark of Monsanto Comp. USA) are treated by dipping into the preparation of active compound of the desired concentration and populated with the tobacco bud caterpillar Heliothis virescens while the leaves are still moist.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100%, dass alle Raupen abgetötet wurden; 0% bedeutet, dass keine Raupen abgetötet wurden. After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.

Claims

Patentansprücheclaims
Pyrroline der Formel (I)Pyrrolines of the formula (I)
in welcher in which
R1 für Halogen, Cι-C -Alkyl oder -C4-Halogenalkyl steht,R 1 represents halogen, -CC-alkyl or -C 4 haloalkyl,
R2 für Wasserstoff, Halogen, C C4-Alkyl oder CrC -Halogenalkyl steht,R 2 represents hydrogen, halogen, CC 4 alkyl or CrC haloalkyl,
R3 für Wasserstoff, Halogen oder Methyl steht,R 3 represents hydrogen, halogen or methyl,
R4 für Wasserstoff, C C6-Alkyl, (CrC6-Alkoxy)carbonyl, (C3-C6-tycloalkyl)- oxycarbonyl, (Cι- -Halogenalkoxy)carbonyl, für gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Cι-C4- Alkyl, -GrAlkoxy, C -Alkylthio, CrC4-HalogenalkyL C C4-Halogen- alkoxy und/oder Cι-C4-Halogenalkylthio substituiertes Aryl steht,R 4 for hydrogen, CC 6 alkyl, (C r C 6 alkoxy) carbonyl, (C 3 -C 6 cycloalkyl) oxycarbonyl, (C 1 -C 5 -haloalkoxy) carbonyl, for optionally single or multiple, identical or different by Halogen, cyano, nitro, C 1 -C 4 -alkyl, -Gralkoxy, C -alkylthio, C r C 4 -haloalkyL CC 4 -haloalkoxy and / or C 1 -C 4 -haloalkylthio substituted aryl,
A1 für N oder CH steht, A2 für N oder CR9 steht,A 1 represents N or CH, A 2 represents N or CR 9 ,
R5 für Wasserstoff, Halogen, C C6-Alkyl, Cι-C6-Alkoxy, -Cβ-Alkylthio, C C6-Alkylsulfϊnyl, C C6-Alkylsulfonyl, C C6-Halogenalkoxy, C C6-Halo- genalkylthio, Cι-C6-Halogenalkylsulfϊnyl oder -Ce-Halogenalkylsulfonyl steht,R 5 is hydrogen, halogen, CC 6 -alkyl, C 6 alkoxy, -Cβ alkylthio, CC 6 -Alkylsulfϊnyl, CC 6 alkylsulfonyl, CC 6 haloalkoxy, CC 6 -Halo- halogenoalkylthio, Cι-C 6 -Halogenalkylsulfϊnyl or -Ce-haloalkylsulfonyl,
R6, R7, R8 und R9 unabhängig voneinander für Wasserstoff, Halogen, Cyano, Formyl, Nitro, Tri(C C6-alkyl)silyl, Cι-C6-Alkyl, C C6-Alkoxy, C C6-R 6 , R 7 , R 8 and R 9 independently of one another for hydrogen, halogen, cyano, formyl, nitro, tri (CC 6 -alkyl) silyl, -CC 6 -alkyl, CC 6 -alkoxy, CC 6 -
Alkylthio, Cι-C6-Alkylsulfinyl5 Cι-C6-Alkylsulfonyl, C2-C6-Alkenyl, C2-C6- Alkenyloxy, (Cι-C6-Alkyl)carbonyl, (Cι-C6-Alkoxy)carbonyl, Ci-Cβ-Halo- genalkyl, Cι-C6-Halogenalkoxy, Cι-C6-Halogenalkylthio, Cι-C6-Halogen alkylsulfinyl, CrC6-Halogenalkylsulfonyl, C2-C6-Halogenalkenyl, C2-C6-Ha- logenalkenyloxy, (Cι-C6-Halogenalkyl)carbonyl, (Cι-C6-Halogenalkoxy)- carbonyl, Pentafluorthio, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 stehen,Alkylthio, Cι-C 6 alkylsulfinyl 5 Cι-C 6 alkylsulfonyl, C 2 -C 6 alkenyl, C 2 -C 6 - alkenyloxy, (Cι-C6 alkyl) carbonyl, (Cι-C6 alkoxy) carbonyl, Ci-Cβ-halo- genalkyl, Cι-C 6 haloalkoxy, Cι-C6 haloalkylthio, Cι-C6 alkylsulfinyl -halo, C r C 6 haloalkylsulfonyl, C 2 -C 6 haloalkenyl, C 2 - C 6 haloalkenyloxy, (-C 6 haloalkyl) carbonyl, (C 6 C haloalkoxy) carbonyl, pentafluorothio, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 ,
R10 für Wasserstoff, C C6-Alkyl, C2-C6-Alkenyl, C C6-Halogenalkyl, C2-C6- Halogenalkenyl oder C3-C6-Cycloalkyl steht,R 10 is hydrogen, CC 6 alkyl, C 2 -C 6 alkenyl, CC 6 haloalkyl, C 2 -C 6 - haloalkenyl or C 3 -C 6 cycloalkyl,
R11 für Wasserstoff, C C6-Alkyl, C2-C6-Alkenyl, C C6-Halogenalkyl, C2-C6- Halogenalkenyl, C3-C6-Cycloalkyl-Cι-C4-alkyl oder gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch R5 substituiertes Aryl-CI-C4- alkyl steht,R 11 is hydrogen, CC 6 alkyl, C 2 -C 6 alkenyl, CC 6 haloalkyl, C 2 -C 6 - haloalkenyl, C 3 -C 6 cycloalkyl-Cι-C 4 alkyl or optionally mono- or polysubstituted by is the same or different aryl-C 1 -C 4 -alkyl substituted by R 5 ,
R12 und R13 unabhängig voneinander für Wasserstoff, -Cδ-Alkyl, Cι-C6-Halogen- alkyl, für gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Cι-C6-Alkyl substituiertes C3-C6-Cycloalkyl, für C3-C6- Cycloalkyl-Cι-C4-alkyl oder für gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch R5 substituiertes Aryl-Cι-C4-alkyl stehen,R 12 and R 13 are independently hydrogen, -Cδ-alkyl, Cι-C6-halo-alkyl, optionally substituted singly or multiply, identically or differently, by halogen or Cι-C 6 alkyl C 3 -C 6 cycloalkyl , are C 3 -C 6 - cycloalkyl -CC 4 -alkyl or are optionally mono- or polysubstituted, identically or differently, substituted by R 5 -aryl -CC 4 -alkyl,
R12 und R13 außerdem gemeinsam für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Ci-Ce-Alkyl substituiertes C2- Q-Alkylen, (Cι-C3-Alkoxy)C1-C3-alkylen oder (C1-C3-Alkylthio)C1-C3- alkylen steht,R 12 and R 13 also together for each optionally mono- or polysubstituted, identically or differently, substituted by halogen or Ci-Ce-alkyl-substituted C 2 - Q-alkylene, (-C-C 3 alkoxy) C 1 -C 3 alkylene or ( C 1 -C 3 alkylthio) C 1 -C 3 alkylene,
p für 0, 1 oder 2 steht,p represents 0, 1 or 2,
Q für einen einfach oder mehrfach, gleich oder verschieden durch Reste aus der Liste W1 substituierten vollständig ungesättigten 5-gliedrigen Heterocyclus mit 1 bis 3 gleichen oder verschiedenen Heteroatomen aus der Reihe Stickstoff, Sauerstoff und/oder Schwefel steht, undQ represents a single or multiple, identical or different, completely unsaturated 5-membered heterocycle having 1 to 3 identical or different heteroatoms from the series nitrogen, oxygen and / or sulfur substituted by radicals from the list W 1 , and
W1 für Halogen, Cyano, -Cie-AlkyL d-C16-Alkoxy, C Cι6-Alkylthio, Cι-Cι6-W 1 for halogen, cyano, -Cie-AlkyL dC 16 -alkoxy, C Cι 6 -Alkylthio, Cι-Cι 6 -
Alkylsulfinyl, Q-Ciß-Alkylsulfonyl, Cι-C16-Halogenalkyl, d-Cie-Halogen- alkoxy, Cι-Cι6-Halogenalkylthio, C Cι6-Halogenalkylsulfinyl, C Cι6-Halo- genalkylsulfonyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Formyl, Nitro, Tri(Cι-C6-alkyl)silyl, C C6-Alkyl, d-C6-Alkoxy, d-C6-Alkylthio, d-C6-Alkylsulfinyl, C C6-Alkylsulfonyl, C2^C6-Alkenyl, C2-C6-Alkenyloxy, (Cι-C6-Alkyl)carbonyl, (C C6-Alkoxy)- carbonyl, Cι-C6-Halogenalkyl, CrC6-Halogenalkoxy, C C6-Halogenalkyl- thio, Cι-C6-Halogenalkylsulfinyl, Cι-C6-Halogenalkylsulfonyl, C2-C6-Halo- genalkenyl, . C2-C6-Halogenalkenyloxy, -C(R10)=N-ORn, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Aryl oder Aιyl-d-C -alkyl steht.Alkylsulfinyl, Q-Ci ß alkylsulfonyl, Cι-C 16 -haloalkyl, d-Cie-halo- alkoxy, Cι-Cι 6 haloalkylthio, C Cι 6 haloalkylsulfinyl, C 6 Cι -Halo- genalkylsulfonyl, C 3 -Cι 2 -Cycloalkyl or for each optionally one or more times, identical or different, by halogen, cyano, formyl, nitro, tri (-CC 6 -alkyl) silyl, CC 6 -alkyl, dC 6 -alkoxy, dC 6 -alkylthio, dC 6 -alkylsulfinyl, CC 6 -alkylsulfonyl, C 2 ^ C 6 -alkenyl, C 2 -C 6 -alkenyloxy, (-C-C 6 -alkyl) carbonyl, (CC 6 - alkoxy) - carbonyl, Cι-C 6 haloalkyl, C r C 6 haloalkoxy, CC 6 haloalkyl thio, Cι-C6 haloalkylsulfinyl, Cι-C 6 haloalkylsulfonyl, C 2 -C 6 -Halo- genalkenyl, , C 2 -C 6 haloalkenyloxy, -C (R 10 ) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted aryl or allyl-dC -alkyl.
2. Pyrroline der Formel ( ) gemäß Anspruch 1, in welcher2. Pyrrolines of formula () according to claim 1, in which
R1 für Fluor, Chlor, Brom, d-GrAlkyl oder C C4-Halogenalkyl mit 1 bis 9R 1 for fluorine, chlorine, bromine, d-alkyl or CC 4 -haloalkyl with 1 to 9
Fluor-, Chlor- und/oder Bromatomen steht, R2 für Wasserstoff, Fluor, Chlor, Brom, C C4-Alkyl oder C C -Halogenalkyl . mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen steht, R3 für Wasserstoff, Fluor, Chlor, Brom oder Methyl steht,Fluorine, chlorine and / or bromine atoms, R 2 is hydrogen, fluorine, chlorine, bromine, CC 4 -alkyl or CC -haloalkyl. with 1 to 9 fluorine, chlorine and / or bromine atoms, R 3 stands for hydrogen, fluorine, chlorine, bromine or methyl,
R4 . für Wasserstoff, Cι-C4-Alkyl, (Cι-C6-Alkoxy)carbonyl, (C3-C6-Cycloalkyl)- oxycarbonyl, (Cι-C4-Halogenalkoxy)carbonyl mit I bis 9 Fluor- und/oderR 4 . for are hydrogen, C 4 alkyl, (Cι-C 6 alkoxy) carbonyl, (C 3 -C 6 cycloalkyl) - oxycarbonyl, (Cι-C 4 haloalkoxy) carbonyl with I to 9 fluorine and / or
Chloratomen, für gegebenenfalls einfach bis vierfach, gleich oder verschie- den durch Fluor, Chlor, Brom, Iod, Cyano, Nitro, Cι-C -Alkyl, Cι-C4-Chlorine atoms, optionally up to four times, the same or different from fluorine, chlorine, bromine, iodine, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -
Alkoxy, Cι-C4-Alkylthio, Cι-C4-Halogenalkyl, Cι-C -Halogenalkoxy und/oder Cι-C -Halogenalkylthio mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Brόmatomen substituiertes Phenyl steht,Alkoxy, Cι-C 4 alkylthio, Cι-C4 haloalkyl, Cι-C -haloalkoxy and / or Cι-C haloalkylthio substituted with in each case 1 to 9 fluorine, chlorine and / or Brόmatomen phenyl,
A1 für N oder CH steht,A 1 represents N or CH,
A2 für N oder CR9 steht,A 2 represents N or CR 9 ,
R5 für Wasserstoff, Fluor, Chlor, Brom, CrC4-Alkyl, C C4-Alkoxy, C C4-R 5 for hydrogen, fluorine, chlorine, bromine, C r C 4 alkyl, CC 4 alkoxy, CC 4 -
Alkylthio, Cι-C4-Alkylsulfϊnyl, Cι-C4-Alkylsulfonyl; Cι-C4-Halogenalkoxy, Cι-C -Halogenalkylthio, C C -Halogenalkylsulfϊnyl oder d-C4-Halogen- alkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen steht,Alkylthio, -CC 4 alkylsulfonyl, -C 4 -alkyl sulfonyl; C 1 -C 4 -haloalkoxy, C 1 -C -haloalkylthio, CC -haloalkylsulfonyl or dC 4 -haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms,
R6, R7, R8 und R9 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom,R 6 , R 7 , R 8 and R 9 independently of one another for hydrogen, fluorine, chlorine, bromine,
Cyano, Formyl, Nitro, Tri(d-C4-alkyl)silyl, C,-C4-Alkyl, d-C -Alkoxy, C,- C4-Alkylthio, Cι-C4-Alkylsulfmyl, Cι-C4-Alkylsulfonyl, C2-C4-Alkenyl, C2- C -Alkenyloxy, (Cι-C -Alkyl)cafbonyl, (C C4-Alkoxy)carbonyl; d-C4-Ha- logenalkyl, d-Q-Halogenalkoxy, d-C -Halogenalkylthio, Cι-C -Halogen- alkylsulfinyl oder. Cι-C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; C2-C4-Halogenalkenyl. oder C2-C -Halogen- alkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, (C C - Halogenalkyl)carbonyl oder (C1-C -Halogenalkoxy)carbonyl, mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, Pentafluorthio, -C(R10)=N-ORn, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 stehen,Cyano, formyl, nitro, tri (dC 4 -alkyl) silyl, C, -C 4 -alkyl, dC -alkoxy, C, - C 4 -alkylthio, Cι-C 4 -alkylsulfmyl, Cι-C 4 -alkylsulfonyl, C 2 -C 4 alkenyl, C 2 - C -alkenyloxy, (-C -alkyl) cafbonyl, (CC 4 -alkoxy) carbonyl; dC 4 -haloalkyl, dQ-haloalkoxy, dC -haloalkylthio, C 1 -C -haloalkylsulfinyl or. -C -C haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms; C 2 -C 4 haloalkenyl. or C 2 -C halogen alkenyloxy, each with 1 to 7 fluorine, chlorine and / or bromine atoms, (CC - haloalkyl) carbonyl or (C 1 -C haloalkoxy) carbonyl, each with 1 to 9 fluorine, chlorine - and / or bromine atoms, pentafluorothio, -C (R 10 ) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 ,
R10 für Wasserstoff, d-Q-Alkyl, C2-C4-Alkenyl, Cι-C4-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl mit 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, Cyclopropyl, Cyclopentyl oder Cyclohexyl steht,R 10 is hydrogen, dQ-alkyl, C 2 -C 4 alkenyl, Cι-C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 -halogenoalkenyl having 1 to 7 fluorine , Chlorine and / or bromine atoms, cyclopropyl, cyclopentyl or cyclohexyl,
Rπ für Wasserstoff, d-C4-Alkyl, C2-C4-Alkenyl, C C4-Halogenalkyl mit 1 bisR π for hydrogen, dC 4 alkyl, C 2 -C 4 alkenyl, CC 4 haloalkyl with 1 to
9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl mit 1 bis 79 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl with 1 to 7
Fluor-, Chlor- und/oder Bromatomen, C3-C6-Cycloalkyl-Cι-C2-alkyl oder jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch R5 substituiertes Benzyl oder Phenylethyl steht,Fluorine, chlorine and / or bromine atoms, C3-C 6 -cycloalkyl-C 1 -C 2 -alkyl or in each case optionally up to four times, the same or differently substituted by R 5, is benzyl or phenylethyl,
R12 und R13 unabhängig voneinander für Wasserstoff, Cι-C -Alkyl, d-C4-Halogen- alkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, Q-Ce-Cycloalkyl,R 12 and R 13 independently of one another for hydrogen, -CC alkyl, dC 4 haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, Q-Ce cycloalkyl,
C3-C6-Cycloalkyl-Cι-C2-alkyl oder jeweils gegebenenfalls einfach' bis vierfach, gleich oder verschieden durch R5 substituiertes Benzyl oderC 3 -C 6 -cycloalkyl-C 2 -C 2 -alkyl or in each case optionally simply ' to fourfold, identical or differently substituted by R 5 or benzyl
Phenylethyl stehen,Phenylethyl,
R12 und R13 außerdem gemeinsam für C3-C5-Alkylen, -(CH2)2-O-(CH2)2- oder -(CH2)2-S-(CH2)2- stehen,R 12 and R 13 also together represent C 3 -C 5 alkylene, - (CH 2 ) 2 -O- (CH 2 ) 2 - or - (CH 2 ) 2 -S- (CH 2 ) 2 -,
für 0 oder 1 steht,represents 0 or 1,
für einen einfach oder mehrfach, gleich oder verschieden durch Reste aus der Liste W1 substituierten vollständig ungesättigten 5-gliedrigen Hetero- cyclus mit 1 bis 3 gleichen oder, verschiedenen Heteroatomen aus der Reihe Stickstoff, Sauerstoff und/oder Schwefel steht, undfor a single or multiple, identical or different, substituted by radicals from the list W 1 completely unsaturated 5-membered hetero- cycle with 1 to 3 identical or different heteroatoms from the series nitrogen, oxygen and / or sulfur, and
W1 für Fluor, Chlor, Brom, Cyano, Cι-Cι2-Alkyl, C C12-Alkoxy, C C12- Alkylthio, Cι-C12-Alkylsulfinyl, Ci-C -Alkylsulfonyl, Cι-C12-Halogenalkyl,W 1 for fluorine, chlorine, bromine, cyano, C 1 -C 2 alkyl, CC 12 alkoxy, CC 12 alkylthio, C 12 C alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 12 haloalkyl,
C C12-Halogenalkoxy, Cι-Cι2-Halogenalkylthio, C Cπ-Halogenalkylsul- finyl, Cι-Cι2-Halogenalkylsulfonyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Formyl, Nitro, Trimethylsilyl, d-C - Alkyl, d-GpAlkoxy, C C4-Alkylthio, C1-C4-Alkylsulfinyl, d-C4-CC 12 haloalkoxy, Cι-Cι 2 haloalkylthio, C Cπ-Halogenalkylsul- finyl, Cι-Cι 2 haloalkylsulfonyl, C 3 -Cι 2 -cycloalkyl or represents in each case optionally monosubstituted or polysubstituted by identical or different fluorine, chlorine, bromine , Cyano, formyl, nitro, trimethylsilyl, dC - alkyl, d-Gpalkoxy, CC 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, dC 4 -
Alkylsulfonyl, C2-C -Alkenyl, • C2-C4-Alkenyloxy, (Cι-C -Alkyl)carbonyl, (d-C -Alkoxy)carbonyl, d-C -Halogenalkyl, Cι-C4-Halogenalkoxy, -d-C4- Halogenalkylthio, Cι-C4-Halogenalkylsulfϊnyl, CrC4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/ oder Bromatomen, C2-C -Halogen- alkenyl, C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OS02NR12R13 substituiertes Phenyl oder Aryl-Cι-C2-alkyl steht.Alkylsulfonyl, C 2 -C alkenyl, • C 2 -C 4 alkenyloxy, (Cι-C -alkyl) carbonyl, (dC alkoxy) carbonyl, dC haloalkyl, Cι-C4-haloalkoxy, -dC 4 - halogenoalkylthio , -C-C 4 haloalkylsulfonyl, C r C 4 haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C halo alkenyl, C 2 -C haloalkenyloxy each having 1 to 7 fluorine -, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OS0 2 NR 12 R 13 substituted phenyl or aryl-C 1 -C 2 -alkyl.
Pyrroline der Formel (T) gemäß Anspruch 1, in welcherPyrrolines of formula (T) according to claim 1, in which
Q für einen vollständig ungesättigten 5-gliedrigen Heterocyclus aus der ReiheQ for a fully unsaturated 5-membered heterocycle from the series
Q31 Q32 Q33 Q34Q31 Q32 Q33 Q34
Q35 Q36 Q37 Q38 steht, worin R14 und R15 unabhängig voneinander für Wasserstoff, Chlor, Cyano, C Cι2-Q35 Q36 Q37 Q38, where R 14 and R 15 independently of one another for hydrogen, chlorine, cyano, C Cι 2 -
Alkyl, d-Cι2-Alkoxy, CrCι2-Alkylthio, CrC12-Alkylsulfmyl, CAlkyl, d-C 2 alkoxy, C r C 2 -alkylthio, C r C 12 -alkylsulfmyl, C
Ci2-Alkylsulfonyl, C d2-Halogenalkyl, C3-d2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschie- den durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, CCi2-alkylsulfonyl, C d 2 -haloalkyl, C 3 -d 2 -cycloalkyl or for each optionally optionally up to four times, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C
C4-Alkyl, CrC4-Alkoxy, d-C4-All<ylthio, C C4-Alkylsulfinyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (C,-C4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, C C -Halogenalkyl, C C -Halo- genalkoxy, CrC -Halogenalkylthio, Cι-C -Halogenalkylsulfϊnyl, C C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oderC 4 -alkyl, C r C 4 -alkoxy, dC 4 -all <ylthio, CC 4 -alkylsulfinyl, CC 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (C, -C 4 -alkyl) -carbonyl, (-CC 4 -alkoxy) carbonyl, CC -haloalkyl, CC -haloalkoxy, CrC -haloalkylthio, -C -CChaloalkylsulfonyl, CC -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and or
Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13,Bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Ansp ch 1 angegebenen Bedeutungen haben, R16 für Wasserstoff, Cyano, C Cι2-Alkyl, C Cι2-Alkoxy, d-C12- Alkylthio, d-C12-Alkylsulfinyl, C C12-Alkylsulfonyl, C Cι2-Halo- genalkyl, C3-C12-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Ci- GrAlkyl, CrC4-Alkoxy, Cι-C -Alkylthio, C C4-Alkylsulfinyl, C C4-Alkylsulfonyl, Q-C4-Alkenyl, d-C4-Alkenyloxy, (C C4-Alkyl)- carbonyl, (Cι-C -Alkoxy)carbonyl, Cι-C -Halo- genalkoxy, Cι-C4-Halogenalkylthio, C C -Halogenalkylsulfinyl, Ci-- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Ansp ch 1, R 16 for hydrogen, cyano, C 1 -C 2 alkyl, C 1 -C 2 alkoxy, dC 12 - alkylthio, dC 12 alkylsulfinyl, CC 12 alkylsulfonyl, C 1 -C 2 -Halogenoalkyl, C 3 -C 12 -cycloalkyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, Ci-GrAlkyl, C r C 4 -alkoxy, Cι- C -alkylthio, CC 4 -alkylsulfinyl, CC 4 -alkylsulfonyl, QC 4 -alkenyl, dC 4 -alkenyloxy, (CC 4 -alkyl) carbonyl, (-C-C -alkoxy) carbonyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, CC -haloalkylsulfinyl, Ci-
C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-OR", -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oderC 4 haloalkylsulfonyl, each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each having 1 to 7 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N-OR ", -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or
-OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,-OSO 2 NR 12 R 13 is substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass R14, R15, R16 nicht gleichzeitig für Wasserstoff stehen, R17 und R19 unabhängig voneinander für Wasserstoff, Cyano, Cι-Cι2-Alkyl,with the proviso that R 14 , R 15 , R 16 do not simultaneously represent hydrogen, R 17 and R 19 independently of one another for hydrogen, cyano, C 1 -C 2 alkyl,
C C12-Alkoxy, d-Ci2-Alkylthio, C.-Cι2-Alkylsulfinyl, d-C«-CC 12 alkoxy, d-Ci 2 alkylthio, C 1 -C 2 alkylsulfinyl, dC «-
Alkylsulfonyl, Ci-C -Halogenalkyl, C3-C12-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschie- den durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, CAlkylsulfonyl, Ci-C -haloalkyl, C 3 -C 12 -cycloalkyl or for each optionally optionally up to four times, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C
C4-Alkyl, CrC4-Alkoxy, d-C4-Alkylthio, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (d-Q-Alkyl)- -carbonyl, (Cj-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, Cι-C4-Halo- . genalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oderC 4 alkyl, C r C 4 alkoxy, dC 4 alkylthio, CC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (dQ-alkyl) - carbonyl, (Cj-C 4 -alkoxy) carbonyl, -C-C 4 -haloalkyl, Cι-C 4 halo. genalkoxy, Cι-C4-haloalkylthio, Cι-C 4 haloalkylsulfinyl, CC 4 haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and / or
Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13,Bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) pNR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben, R18 für Wasserstoff, Chlor, Cyano, C C12-Alkyl, C Cι2-Alkoxy, C C12- Alkylthio, Cι-C12-Alkylsulfinyl, d-da-Alkylsulfonyl, d-da-Halo- genalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C Ct-Alkyl, Ci-d-Alkoxy, d-C4-Alkylthio, d-C4-Alkylsulfinyl, d- C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (C C4-Alkyl)- carbonyl, (CrC4-Alkoxy)carbonyl, d-C-rHalogenalkyL C C4-Halo- genalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, Ci-- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Anspmch 1, R 18 for hydrogen, chlorine, cyano, CC 12 alkyl, C 1 -C 2 alkoxy, CC 12 - alkylthio, C 1 -C 12 alkylsulfinyl, d-da-alkylsulfonyl , D-da-haloalkyl, C 3 -C 2 -cycloalkyl or for each optionally one to four times, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, CC t -alkyl, Ci-d-alkoxy , dC 4 alkylthio, dC 4 alkyl sulfinyl, d C 4 alkyl sulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (CC 4 alkyl) carbonyl, (CrC 4 alkoxy) carbonyl , dC rHalogenalkyL CC genalkoxy 4 -Halo-, Cι-C4-haloalkylthio, Cι-C4-haloalkylsulfinyl, Ci
C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oderC 4 haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each having 1 to 7 fluorine, chlorine and / or bromine atoms, C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or
-OSO2NR1 R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,-OSO 2 NR 1 R 13 is substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass Rπ, R18, R19 nicht gleichzeitig für Wasserstoff stehen, R20 und R23 unabhängig voneinander für Wasserstoff, d-Cι2-AlkyVd-C12-with the proviso that R π , R 18 , R 19 do not simultaneously represent hydrogen, R 20 and R 23 independently of one another for hydrogen, d-Cι 2 -AlkyVd-C 12 -
Alkoxy, d-C12-Alkylthio, d-Cι2-Alkylsulfinyl, CrC12-Alkylsulfo- nyl, Cι-Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschie- den durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, CAlkoxy, dC 12 alkylthio, d-Cι 2 alkylsulfinyl, C r C 12 -Alkylsulfo- nyl, Cι-Cι, 3 -Cι or in each case optionally mono- to tetrasubstituted by identical or different 2 -cycloalkyl C 2 -haloalkyl the by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C
C4-Alkyl, Cι-C4-Alkoxy, C C4-Alkylthio, d-C4-Alkylsulfinyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C -Alkenyloxy, (d-Q-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, C C4-Halo- genalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfϊnyl, Ci- d-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oderC 4 alkyl, -C 4 alkoxy, CC 4 alkylthio, dC 4 alkylsulfinyl, CC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C alkenyloxy, (dQ-alkyl) carbonyl, (Cι-C 4 alkoxy) carbonyl, Cι-C 4 haloalkyl, CC genalkoxy 4 -Halo-, Cι-C4-haloalkylthio, Cι-C 4 -Halogenalkylsulfϊnyl, Ci- d-halogenoalkylsulphonyl having in each case 1 to 9 fluorine , Chlorine and / or
Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13,Bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) pNR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben, R21 und R22 unabhängig voneinander für Wasserstoff, Chlor, Cyano, C1-C12- Alkyl, d-Cι2-Alkoxy, Cι-C12-Alkylthio, d-dj-Alkylsulfinyl, C Cι2-Alkylsulfonyl, Cι-Cι2-Halogenalkyl, C3-C12-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C C4-Alkyl, C.-C4-Alkoxy, C C4-Alkylthio, C C4-Alkylsulfinyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (C.-C4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, d-d-Halo- genalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, d-- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Anspmch 1, R 21 and R 22 independently of one another for hydrogen, chlorine, cyano, C 1 -C 12 alkyl, C 1 -C 2 -alkoxy, C 1 -C 12 alkylthio, d -dj-Alkylsulfinyl, C -C 2 alkylsulfonyl, Cι-Cι 2 haloalkyl, C 3 -C 12 cycloalkyl or for each optionally simple to fourfold, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, CC 4- alkyl, C.-C 4 -alkoxy, CC 4 -alkylthio, CC 4 -alkylsulfinyl, CC 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (C.-C 4 - alkyl) - carbonyl, (Cι-C 4 alkoxy) carbonyl, Cι-C 4 haloalkyl, halo genalkoxy dd, Cι-C4-haloalkylthio, Cι-C 4 haloalkylsulfinyl, d-
C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(RI2)SO2R13, -OSO2R12 oderC 4 haloalkylsulfonyl, each having 1 to 9 fluorine, chlorine and or bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each having 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) pN (R 12 ) COR 13 , - (CH 2 ) pN (R I2 ) SO 2 R 13 , -OSO 2 R 12 or
-OSO2NRl2R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,-OSO 2 NR 12 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass R20, R21, R22, R23 nicht gleichzeitig für Wasserstoff stehen, R24 für Wasserstoff, C C6-Alkyl oder C3-C6-Cycloallyl steht,with the proviso that R 20 , R 21 , R 22 , R 23 do not simultaneously represent hydrogen, R 24 represents hydrogen, CC 6 alkyl or C 3 -C 6 cycloallyl,
R25 und R26 unabhängig voneinander für Wasserstoff, Chlor, Cyano, d-Cι2- Alkyl, Cι-C12-Alkoxy, Cι-Cι2-Halogenalkyl, C3-C12-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C C4-Alkyl, CrC4-Alkoxy, C C4-All<ylthio, C1-C4-Alkylsulfinyl, Cr C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (d-C4-Alkyl)- carbonyl, (d-C -Alkoxy)carbonyl, Cι-C4-Halogenalkyl, Ci-d-Halo- genalkoxy, Cι-C4-Halogenalkyltnio, Cι-C4-Halogenalkylsulfϊnyl, Ci-R 25 and R 26 independently of one another for hydrogen, chlorine, cyano, d -CC 2 alkyl, C 12 alkoxy, C 1 -C 2 -haloalkyl, C 3 -C 12 -cycloalkyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, CC 4 -alkyl, C r C 4 -alkoxy, CC 4 -all <ylthio, C 1 -C 4 -alkylsulfinyl, C r C 4 -alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (dC 4 alkyl) - carbonyl, (dC alkoxy) carbonyl, Cι-C 4 haloalkyl, Ci-d-halo- genalkoxy, Cι-C 4 -Halogenalkyltnio, Cι-C 4 -Halogenalkylsulfϊnyl, Ci-
C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oderC -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy, each with 1 to 7 fluorine, chlorine and or bromine atoms, -C ( R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N ( R 12 ) SO 2 R 13 , -OSO 2 R 12 or
-OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben, R27 für Wasserstoff, d-Cι2-Alkyl, C C12- Alkoxy, C Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C C4-Alkyl, d-C4-Alkoxy, d-C4-Alkylthio, d-C4-AlkylsulfinyL C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (C C4-Alkyl)- carbonyl, (C C4-Alkoxy)carbonyL d-C4-Halogenalkyl, d-C4-Halo- genalkoxy, Cι-C4-Halogenalkylthio, C C4-Halogenalkylsulfinyl, d--OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Anspmch 1, R 27 is hydrogen, C 1 -C 2 -alkyl, CC 12 - alkoxy, C 1 -C 2 -haloalkyl, C 3 -C 2 -cycloalkyl or for each optionally single to quadruple, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, CC 4 alkyl, dC 4 alkoxy, dC 4 alkylthio, dC 4 alkylsulfinyL CC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (CC 4 alkyl) carbonyl, (CC 4 alkoxy) carbonyL dC 4 haloalkyl, dC 4 haloalkoxy, Cι -C 4 haloalkylthio, CC 4 haloalkylsulfinyl, d-
C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)PN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oderC 4 haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each having 1 to 7 fluorine, chlorine and / or bromine atoms, C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) P N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or
-OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,-OSO 2 NR 12 R 13 is substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass R24, R25, R26, R27 nicht gleichzeitig für Wasserstoff stehen, R28 und R30 unabhängig voneinander für Wasserstoff, Cι-d2-Alkyl, Ci-d∑- Alkoxy, Cι-Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C *C -Alkyl, Cj-Q-Alkoxy, d-C4-Alkylthio, Cι-C4-Alkylsulfinyl, Cwith the proviso that R 24 , R 25 , R 26 , R 27 do not simultaneously represent hydrogen, R 28 and R 30 independently of one another are hydrogen, d 2 -alkyl, d Σ - alkoxy, Cι-Cι 2 -haloalkyl, C 3 -Cι 2 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different substituents Fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C * C -alkyl, Cj-Q-alkoxy, dC 4 -alkylthio, Cι-C 4 -alkylsulfinyl, C
•C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (CrC4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, d-C4-Halo- genalkoxy, d-C4-Halogenall<ylthio, Cι-C4-Halogenalkylsulfϊnyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, d-Q-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR1 R13,• C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (C r C 4 alkyl) - carbonyl, (Cι-C 4 alkoxy) carbonyl, Cι-C 4 haloalkyl, dC 4 -haloalkoxy, dC 4 -halogenall <ylthio, -C-C 4 -haloalkylsulfonyl, CC 4 -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 -haloalkenyl, dQ- Haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 1 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(RI2)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R I2 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
R29 für Wasserstoff, Chlor, Cyano, d-Cπ-Alkyl, Cι-C12-Alkoxy, C Cι2- Halogenalkyl, C3-Cj2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl,, C C4-Alkyl, C C4-Alkoxy, C C4-Alkylthio, d-d-Alkylsulfinyl, Ci-R 29 represents hydrogen, chlorine, cyano, d-Cπ-alkyl, Cι-C 12 alkoxy, C 2 Cι - haloalkyl, C 3 -CJ 2 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different fluorine, chlorine , cyano, formyl, nitro, trimethylsilyl, CC 4 alkyl, CC 4 -alkoxy, CC 4 alkylthio, dd-alkylsulfinyl, Ci-
C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (C C4-Alkyl)- carbonyl, (d-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, d-C4-Halo- genalkoxy, d-Q-Halogenalkylthio, Cι-C4-Halogenalkylsulfϊnyl, d- C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13,C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (CC 4 alkyl) - carbonyl, (dC 4 alkoxy) carbonyl, Cι-C 4 haloalkyl, dC 4 -Halo- genalkoxy, dQ haloalkylthio, Cι-C 4 -Halogenalkylsulfϊnyl, d- C4-haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy with 1 to 7 fluorine, chlorine and / or bromine atoms each, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
R31 für Wasserstoff, Cι-C6-Alkyl, C3-C6-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durchR 31 for hydrogen, -CC 6 alkyl, C 3 -C 6 cycloalkyl or for each optionally optionally up to four times, identically or differently
Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C1-C4-Alkyl, d- d-Alkoxy, Cι-C4-Alkylthio, CrC4-Alkylsulfinyl, • d-C4- Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (Cι-C4-Alkyl)car- bonyl, (C1-C4-Alkoxy)carbonyl, Ci-d-Halogenalkyl, Ci-d-Halo- genalkoxy, d-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfϊnyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13,Fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C 1 -C 4 alkyl, d- d-alkoxy, Cι-C 4 alkylthio, C r C 4 alkylsulfinyl, • dC 4 - Alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (Cι-C4 alkyl) carbonyl, (C 1 -C 4 alkoxy) carbonyl, Ci-d-haloalkyl, Ci-d- Haloalkoxy, dC 4 -haloalkylthio, -C-C4-haloalkylsulfonyl, CC 4 -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkenyloxy 1 to 7 fluorine, chlorine and / or bromine atoms each, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass R28, R29, R30, R31 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 28 , R 29 , R 30 , R 31 do not simultaneously represent hydrogen,
R32 und R34 unabhängig voneinander für Wasserstoff, Cι-C12-Alkyl, C Cι2-R 32 and R 34 independently of one another for hydrogen, C 1 -C 12 -alkyl, C 1 -C 2 -
Alkoxy, C,-C12-Alkylthio, Cj-Cπ-Alkylsulfinyl, CrC12-Alkylsulfo- nyl, Cι-Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d- Q-Alkyl, C C4-Alkoxy, C C4-Alkylthio, d-C4-Alkylsulfmyl, d-Alkoxy, C, -C 12 alkylthio, Cj-Cπ alkylsulfinyl, C r C 12 nyl -Alkylsulfo- different, Cι-Cι 2 -haloalkyl, C 3 -Cι 2 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, d- Q-alkyl, CC 4 -alkoxy, CC 4 -alkylthio, dC 4 -alkylsulfmyl, d-
Q-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (Cι-C4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, C C -Halogenalkyl, Cι-C -Halo- genalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfϊnyl, d- C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13,Q-alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (-C-C 4 -alkyl) carbonyl, (-C-C 4 -alkoxy) carbonyl, CC -haloalkyl, -C-C -halo - genalkoxy, Cι-C4-haloalkylthio, Cι-C 4 -Halogenalkylsulfϊnyl, d- C haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 -Halogenalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,- (CH 2 ) pN (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
R33 für Wasserstoff, Chlor, Cyano, d-C12-Alkyl, d-C12-Alkoxy, Cj-Cu- Alkylthio, d-C12-A-kylsulfinyl, Cι-Ci2-Alkylsulfonyl, C Cι2-Halo- genalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschie- den durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d- C4-Alkyl, CrC4-Alkoxy, d-d-Alkylthio, C1-C4-Alkylsulfmyl, d- C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C -Alkenyloxy, (C,-C4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, C C -Halo- genalkoxy, Cι-C4-Halogenalkylthio, C1-C4-Halogenalkylsulfϊnyl, d- C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oderR 33 for hydrogen, chlorine, cyano, dC 12 -alkyl, dC 12 -alkoxy, Cj-Cu-alkylthio, dC 12 -A-kylsulfinyl, Cι-Ci 2 -alkylsulfonyl, C -C 2 -halogenoalkyl, C 3 - C 2 -cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, d- C 4 -alkyl, C r C 4 -alkoxy, dd-alkylthio, C 1 -C 4 -alkylsulfmyl, d- C 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C -alkenyloxy, (C, - C 4 -alkyl) - carbonyl, (-C-C 4 -alkoxy) carbonyl, Cι-C 4 -haloalkyl, CC -halogenalkoxy, Cι-C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfonyl, d- C - Haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and or
Bromatomen, C2-C -Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13,Bromine atoms, C 2 -C haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R1 )SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 1 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass R32, R33, R34 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 32 , R 33 , R 34 do not simultaneously represent hydrogen,
R35 und R36 unabhängig voneinander für Wasserstoff, Cι-Cι2-Alkyl, C1-C12- Alkoxy, Ci-Cπ-Alkylthio, C Cι2-Alkylsulfinyl, C C12-Alkylsulfo- nyl, d-Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschie- den durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d-R 35 and R 36 independently of one another for hydrogen, C 1 -C 2 alkyl, C 1 -C 12 alkoxy, C 1 -C 4 alkylthio, C 2 -C alkylsulfinyl, CC 12 alkylsulfonyl, d-C 2 -haloalkyl , C 3 -C 2 cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, d-
C4-Alkyl, d-C4-Alkoxy, d-C4-Alkylthio, d-d-Alkylsulfinyl, d- C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (CrC4-Alkyl)- carbonyl, (C1-C4-Alkoxy)carbonyl, Cι-C -Halogenalkyl, Cι-C4-Halo- genalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, d- C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oderC 4 -alkyl, dC 4 -alkoxy, dC 4 -alkylthio, dd-alkylsulfinyl, d- C 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (C r C 4 -alkyl) - carbonyl, (C 1 -C 4 alkoxy) carbonyl, Cι-C haloalkyl, Cι-C genalkoxy 4 -Halo-, Cι-C4-haloalkylthio, Cι-C4-haloalkylsulfinyl, d-C 4 haloalkylsulfonyl with 1 to 9 fluorine, chlorine and / or
Bromatomen, C2-C -Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORU, -SO2NR12R13, -(CH2)PNR12R13,Bromine atoms, C 2 -C haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR U , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN( 12)S02R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) pN ( 12 ) S0 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass R31, R35, R36 nicht gleichzeitig für Wasserstoff stehen, R37 für Wasserstoff, d-Cι2-Alkyl, C Cι2-Alkoxy, Cι-Cι2-Alkylthio, C Cι2-Alkylsulfinyl, CrCι2-Alkylsulfonyl, C Cι2-Halogenalkyl, C3- Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschie- den durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cwith the proviso that R 31 , R 35 , R 36 do not simultaneously represent hydrogen, R 37 is hydrogen, d-Cι 2 alkyl, C 2 Cι -alkoxy, Cι 2 alkylthio, C Cι 2 alkylsulfinyl, C r Cι 2 alkylsulfonyl, C Cι 2 -haloalkyl, C 3 - Cι 2 - Cycloalkyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C
C4-Alkyl, d-C4-Alkoxy, C C4-Alkylthio, d-d-Alkylsulfinyl, C C4-Alkylsulfonyl, C2-C4-AlkenylJ C2-C4-Alkenyloxy, (CrC4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C -Halogenalkyl, C C -Halo- genalkoxy, d-d-Halogenalkylthio, CrC4-Halogenalkylsulfϊnyl, d- C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oderC 4 alkyl, dC 4 alkoxy, CC 4 alkylthio, dd-alkylsulfinyl, CC 4 alkylsulfonyl, C 2 -C 4 alkenyl J C 2 -C 4 alkenyloxy, (C r C 4 alkyl) carbonyl , (-C-C 4 -alkoxy) carbonyl, -C-C -haloalkyl, CC -haloalkoxy, dd-haloalkylthio, CrC 4 -haloalkylsulfonyl, d- C 4 -haloalkylsulfonyl, each with 1 to 9 fluoro, chloro and / or
Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13,Bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben, R38 für Wasserstoff, Chlor, Cyano, C C12-Alkyl, Ci-Cπ-Alkoxy, Cι-C12- Alkylthio, Cι-Cι2-Alkylsulfinyl, d-Cι2-Alkylsulfonyl, Cι-C12-Halo- genalkyl, C3-d2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Ci- C4-Alkyl, d-C4-Alkoxy, d-C -Alkylthio, d-C4-All<ylsulfinyl, C C4-Alkylsulfonyls C2-C4-Alkenyl, C2-C4-Alkenyloxy, (Cι-C4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, C C4-Halogenalkyl, Cι-C4-Halo- genalkoxy, C C4-Halogenalkylthio, CrC4-Halogenalkylsulfinyl, C- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Anspmch 1, R 38 for hydrogen, chlorine, cyano, CC 12 alkyl, Ci-Cπ-alkoxy, -C-C 12 - alkylthio, -C-Cι 2 -alkylsulfinyl, d-Cι 2 -Alkylsulfonyl, -C-C 12 haloalkyl, C 3 -d 2 -cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, Ci-C 4 alkyl , dC 4 -alkoxy, dC -alkylthio, dC 4 -All <ylsulfinyl, CC 4 -alkylsulfonyl s C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (Cι-C 4 -alkyl) carbonyl, ( Cι-C 4 alkoxy) carbonyl, CC 4 haloalkyl, Cι-C genalkoxy 4 -Halo-, CC 4 haloalkylthio, CrC 4 haloalkylsulfinyl, C
C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oderC 4 haloalkylsulfonyl, each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C haloalkenyloxy each having 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or
-OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,-OSO 2 NR 12 R 13 is substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass R24, R37, R38 oder R31, R37, R38 nicht gleichzeitig für Wasserstoff stehen, R39, R40 und R41 unabhängig voneinander für Wasserstoff,. CrC12-Alkyl, Cwith the proviso that R 24 , R 37 , R 38 or R 31 , R 37 , R 38 do not simultaneously represent hydrogen, R 39 , R 40 and R 41 independently of one another for hydrogen ,. C r C 12 alkyl, C
C12-Alkoxy, Cι-C13-Alkylthio, d-C12-Alkylsulfinyl, d-C12-C 12 alkoxy, C 1 -C 13 alkylthio, dC 12 alkylsulfinyl, dC 12 -
Alkylsulfonyl, Cι-Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschie- den durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, CAlkylsulfonyl, -CC 2 -haloalkyl, C 3 -C 2 -cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C
C4-Alkyl, Ci-d-Alkoxy, d-C4-Alkylthio, C C4-Alkylsulfϊnyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (d-C4-Alkyl)- carbonyl, (d-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, Ci-d-Halo- genalkoxy, Cι-C4-Halogenalkylτhio, Cι-C -Halogenalkylsulfinyl, Ci- C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oderC 4 alkyl, Ci-d-alkoxy, dC 4 alkylthio, CC 4 alkylsulfonyl, CC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (dC 4 alkyl) carbonyl (dC 4 alkoxy) carbonyl, Cι-C 4 haloalkyl, Ci-d-halo- genalkoxy, Cι-C 4 -Halogenalkylτhio, Cι-C haloalkylsulfinyl, Ci- C4-haloalkylsulfonyl having in each case 1 to 9 fluorine , Chlorine and / or
Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -SO2NR12R13, -(CH2)pNR12R13,Bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass R39, R40, R41 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 39 , R 40 , R 41 do not simultaneously represent hydrogen,
R42 und R43 unabhängig voneinander für Wasserstoff, Cι-Cι2-Alkyl, C Cι2- Alkoxy, C C12-Alkylthio, C Cι2-Alkylsulfmyl, d-C12-Alkylsulfo- nyl, Cι-Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschie- den durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, CR 42 and R 43 independently of one another are hydrogen, Cι-2 alkyl, C Cι 2 - alkoxy, CC 12 alkylthio, C 2 Cι -Alkylsulfmyl, dC 12 -Alkylsulfo- nyl, Cι-Cι 2 -haloalkyl, C 3 -Cι 2 -Cycloalkyl or for each optionally single to fourfold, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C
C4-Alkyl, Cι-C4-Alkoxy, C C -Alkylthio, Cι-C4-Alkylsulfmyl, Q- C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (d-Q-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, d-C4-Halo- genalkoxy, d-C4-Halogenalkylthio, Cι-C -Halogenalkylsulfinyl, C C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oderC 4 -alkyl, -C-C 4 alkoxy, CC -alkylthio, Cι-C 4 -alkylsulfmyl, Q- C 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (dQ-alkyl ) - carbonyl, (Cι-C 4 alkoxy) carbonyl, Cι-C 4 haloalkyl, dC genalkoxy 4 -Halo-, dC 4 haloalkylthio, Cι-C haloalkylsulfinyl, haloalkylsulfonyl CC with in each case 1 to 9 fluorine, Chlorine and / or
Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORU, -SO2NR12R13, -(CH2)pNR12R13,Bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N-OR U , -SO 2 NR 12 R 13 , - (CH 2 ) pNR 12 R 13 ,
-(CH2)pN(R1 )COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 1 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass R24, R42, R43 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 24 , R 42 , R 43 do not simultaneously represent hydrogen,
R44 und R45 unabhängig voneinander für Wasserstoff, Cι-Cι2-Alkyl, C Cι2- Alkoxy, C Cι2-Alkylthio, Cι-C12-Alkylsulfinyl, C C12-Alkylsulfo- nyl, Cι-C12-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C d-Alkyl, CrC4-Alkoxy, Cι-C4-Alkylthio, d-C4-Alkylsulfinyl, Cj- C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (C C4-Alkyl)- , carbonyl, (Ci-d-Alkox Jcarbonyl, Cι-C4-Halogenalkyl, C C4-Halo- genalkoxy, C.-d-Halogenalkylthio, d-d-Halogenall-ylsulfinyl, d-R 44 and R 45 independently of one another are hydrogen, Cι-2 alkyl, C Cι 2 - alkoxy, C 2 Cι alkylthio, Cι-C 12 alkylsulfinyl, CC 12 -Alkylsulfo- nyl, Cι-C 12 haloalkyl, C 3 -C 2 cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C d-alkyl, C r C 4 alkoxy, C 1 -C 4 alkylthio, dC 4 -alkylsulfinyl, Cj- C 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (CC 4 -alkyl) -, carbonyl, (Ci-d-Alkox Jcarbonyl, Cι-C 4 -Haloalkyl, CC 4 -haloalkoxy, C.-d-haloalkylthio, dd-haloall-ylsulfinyl, d-
C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C -Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ. -SO2NR12R13, -(CH2)-NR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OS02R12 oderC 4 haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C haloalkenyl, C 2 -C 4 haloalkenyloxy, each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π . -SO 2 NR 12 R 13 , - (CH 2 ) -NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , - OS0 2 R 12 or
-OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,-OSO 2 NR 12 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass R24, R44, R45 oder R31, R44, R45 nicht gleichzeitig für' Wasserstoff stehen,with the proviso that R 24, R 44, R 45 or R 31, R 44, R 45 are not simultaneously hydrogen,
R46 und R47 unabhängig voneinander für Wasserstoff, Cι-C12-Alkyl, CrCι - Alkoxy, Cι-C12-Alkylthio, CrCι2-All-ylsulfϊnyl, d-d∑-Alkylsulfo- nyl, CrCι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für j eweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cj- C4-Alkyl, Ci-Q-Alkoxy, CrC4-Alkylthio, C C4-Alkylsulfinyl, Cr C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (d-d-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyL C C4-Halogenalkyl, Cι-C4-Halo- genalkoxy, d-d-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, d-d-Halogenalkenyl, d-Q-Halogenalkenyloxy mit jeweils .1 bis 7 . Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -SO2NR1 R13, -(CH2)PNR12R13,R 46 and R 47 independently of one another for hydrogen, C 1 -C 12 alkyl, C r C 1 alkoxy, C 1 -C 12 alkylthio, C r C 2 2 -all-ylsulfonyl, dd ∑ -alkylsulfonyl, CrC 2 -haloalkyl , C 3 -C 2 -cycloalkyl or for each optionally optionally up to four times, identically or differently by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C 1 -C 4 -alkyl, Ci-Q-alkoxy, C r C 4 -Alkylthio, CC 4 -Alkylsulfinyl, C r C 4 -Alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (dd-alkyl) - carbonyl, (-C-C 4 -alkoxy) carbonyL CC 4 -Halogenalkyl, -C-C 4 -haloalkoxy, dd-haloalkylthio, -C-C 4 -Halogenalkylsulfinyl, C C 4 haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and or bromine atoms, dd-haloalkenyl, dQ-haloalkenyloxy each having .1 to 7. Fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , -SO 2 NR 1 R 13 , - (CH 2 ) P NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NRI2R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR I2 R 13 are substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass R46, R47 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 46 , R 47 do not simultaneously represent hydrogen,
R48 und R49 unabhängig voneinander für Wasserstoff, Cι-d2-Alkyl, C C12- Alkoxy, d-C12-Alkylthio, C Cι2-Alkylsulfinyl, d-C.2-Alkylsulfo- nyl, Cι-Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschie- den durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d-R 48 and R 49 independently of one another for hydrogen, -CC 2 alkyl, CC 12 -alkoxy, dC 12 -alkylthio, C 2 -alkyl sulfinyl, dC. 2 -Alkylsulfo- nyl, Cι-Cι 2 -haloalkyl, C 3 -Cι 2 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different to by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, d-
C4-Alkyl, d-d-Alkoxy, d-Q-Alkylthio, CrC4-Alkylsulfinyl, d- C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (Cι-C4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C -Halogenalkyl, Cι-C -Halo- genalkoxy, Cι-C -Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, Ci- Q-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oderC 4 -alkyl, dd-alkoxy, dQ-alkylthio, C r C 4 -alkylsulfinyl, d- C 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (-C-C 4 -alkyl ) - carbonyl, (-C-C 4 alkoxy) carbonyl, -C-C -haloalkyl, Cι-C -haloalkoxy, -C-C -haloalkylthio, Cι-C 4 -haloalkylsulfinyl, Ci-Q-haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or
Bromatomen, C2-C -Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Brdmatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13,Bromine atoms, C 2 -C haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) pNR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgäbe, dass R48, R49 nicht gleichzeitig für Wasserstoff stehen,with the measure that R 48 , R 49 do not simultaneously represent hydrogen,
R50 und R5 unabhängig voneinander für Wasserstoff, Cι-Ci2-Alkyl, C1-C.2-R 50 and R 5 independently of one another for hydrogen, C 1 -C 2 alkyl, C 1 -C. 2 -
Alkoxy, Cι-Cι2-Alkylthio, C Cι2-Alkylsulfmyl, CrCι2-Alkylsulfo- nyl, d-Cι2-HalogenaIkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d- Q-Alkyl, C C4-Alkoxy, d-d-Alkylthio, C C4-Alkylsulfinyl, d- C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C -Alkenyloxy, (C C4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, Cι-C -Halo- genalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfϊnyl, Cj- C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2jpNR12R13,Alkoxy, Cι- 2 alkylthio, C Cι 2 -alkylsulfmyl, C r Cι 2 -alkylsulfonyl, d-Cι 2 -HalogenaIkyl, C 3 -Cι 2 cycloalkyl or for each optionally simple to fourfold, identical or different by Fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, d- Q-alkyl, CC 4 -alkoxy, dd-alkylthio, CC 4 -alkylsulfinyl, d- C 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C -alkenyloxy, (CC 4 -alkyl) carbonyl, (-C-C 4 -alkoxy) carbonyl, -C-C 4 -haloalkyl, Cι-C - halo genalkoxy, Cι-C4-haloalkylthio, Cι-C 4 -Halogenalkylsulfϊnyl, CJ-C4-haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl, C 2 - C 4 haloalkenyloxy each having 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 j p NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass R50, R51 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 50 , R 51 do not simultaneously represent hydrogen,
R52 für Wasserstoff, Ci-Cπ-AlkyL C Cι2-Alkoxy, C Cι2-Alkylthio, C C12-Alkylsulfinyl, d-C12-Alkylsulfonyl, Cι-Cι2-Halogenalkyl, C3-R 52 for hydrogen, Ci-Cπ-AlkyL C Cι 2 alkoxy, C Cι 2 alkylthio, CC 12 alkylsulfinyl, dC 12 alkylsulfonyl, Cι -C 2 haloalkyl, C 3 -
Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cj- C4-Alkyl, C C4-Alkoxy, d-d-Alkylthio, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C -Alkenyloxy, (d-C4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, d-C4-Halo- genalkoxy, Cι-C4-Halogenalkylthio, Cj-C4-Halogenalkylsulfinyl, Ct- C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-HalogenalkenyL C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen,C 2 -cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C 1 -C 4 -alkyl, CC 4 -alkoxy, dd-alkylthio, CC 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C -alkenyloxy, (dC 4 -alkyl) carbonyl, (-C-C 4 -alkoxy) carbonyl, -C-C 4 -haloalkyl, dC 4 -halo - genalkoxy, Cι-C4-haloalkylthio, Cj-C 4 haloalkylsulfinyl, C t - C 4 haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl C 2 -C 4 -haloalkenyloxy, each with 1 to 7 fluorine, chlorine and / or bromine atoms,
-C(R10)=N-ORU, -SO2NR12R13, -(CH2)PNR12R13,-C (R 10 ) = N-OR U , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Ansprach 1 angegebenen Bedeutungen haben, R53 für Wasserstoff, Chlor, Cyano, C Cι2-Alkyl, CrC12-Alkoxy, C Cι2-- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in spoke 1, R 53 represents hydrogen, chlorine, cyano, Cι C 2 alkyl, C r C 12 alkoxy, C 2 Cι -
Alkylthio, Cι-Cι2-Alkylsulfinyl, Cι-Cι2-Alkylsulfonyl, C Cι2-Halo- genalkyl, C3-d2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C C4-Alkyl, C C4-Alkoxy, C C4-Alkylthio, Cι-C4-Alkylsulfinyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (C C4-Alkyl)- carbonyl, (d-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, Cι-C4-Halo- genalkoxy, Cι-C4-Halogenalkylthio, d-d-Halogenall-ylsulfϊnyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, C2-C4-Halogenalkenyl, d-d-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -SO2NR12R13, -(CH2)PNR12R13,Alkylthio, -CC 2 alkylsulfinyl, -C 2 -alkylsulfonyl, C 2 -C -haloalkyl, C 3 -d 2 -cycloalkyl or for each optionally optionally up to four times, identically or differently, by fluorine, chlorine, cyano, formyl , Nitro, trimethylsilyl, CC 4 alkyl, CC 4 alkoxy, CC 4 alkylthio, C 1 -C 4 alkylsulfinyl, C C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (CC 4 alkyl) - carbonyl, (dC 4 alkoxy) carbonyl, Cι-C4 haloalkyl, Cι-C 4 - Haloalkoxy, -C-C 4 haloalkylthio, dd-haloall-ylsulfonyl, CC 4 haloalkylsulfonyl each with 1 to 9 fluorine, chlorine and or bromine atoms, C 2 -C 4 haloalkenyl, dd-haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 ,
-(CH2)pN(R1 )COR13, -(CH2)PN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,- (CH 2 ) pN (R 1 ) COR 13 , - (CH 2 ) P N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass R52, R53 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 52 , R 53 do not simultaneously represent hydrogen,
R54 für Wasserstoff, Chlor, Cyano, d-C12-Alkyl, d-C12-Alkoxy, d-Cι2- Alkylthio, C C12-Alkylsulfinyl, CπdrAlkylsulfonyl, d-Cπ-Halo- genalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Ci- C4-Alkyl, d-C4-Alkoxy, d-C -Alkylthio, Cι-C4-Alkylsulfinyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (Cι-C4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, Cι-C4-Halo- genalkoxy, Cι-C -Halogenalkylthio, Cι-C4-Halogenalkylsulfϊnyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, d-d-Halogenalkenyl, d-Q-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen,R 54 for hydrogen, chlorine, cyano, dC 12 -alkyl, dC 12 -alkoxy, d-Cι 2 - alkylthio, CC 12 -alkylsulfinyl, CπdrAlkylsulfonyl, d-Cπ-haloalkyl, C 3 -Cι 2 -cycloalkyl or for each optionally up to four times, identically or differently, by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C 1 -C 4 -alkyl, dC 4 -alkoxy, dC -alkylthio, -CC 4 -alkylsulfinyl, CC 4 -alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (Cι-C4 alkyl) - carbonyl, (Cι-C 4 alkoxy) carbonyl, Cι-C4 haloalkyl, Cι-C4 -halo - Genalkoxy, -C-C-haloalkylthio, -C-C 4 -haloalkylsulfonyl, CC 4 -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and or bromine atoms, dd-haloalkenyl, dQ-haloalkenyloxy, each with 1 to 7 fluoro, chlorine - and / or bromine atoms,
-C(R10)=N-ORn, -SO2NR12R13, -(CH2)PNR12R13,-C (R 10 ) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Ansprach 1 angegebenen Bedeutungen haben, R55 für Wasserstoff, Cι-C12-Alkyl, d-C12-Alkoxy, Cι-CJ2-Alkylthio, C,-- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in spoke 1, R 55 for hydrogen, -CC 12 -alkyl, dC 12 -alkoxy, -C-C J2 -alkylthio, C, -
Cι2-Alkylsulfinyl, Cι-Cι2-Alkylsulfonyl, Cι-C]2-Halogenalkyl, C3- Ci2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d- Q-Alkyl, C,-C4-Alkoxy, d-C4-Alkylthio, Cι-C4-Alkylsulfinyl, Cj- C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (C C4-Alkyl)- carbonyl, (d-C4-Alkoxy)cafbonyl, CrC4-Halogenalkyl, C C4-Halo- genalkoxy,"Cι-C4-Halogenalkylthio, CrC4-Halogenalkylsulffnyl, d- C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C -Halogenalkenyl, d-d-Halogenalkenyloxy mit jeweils 1 "bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13,Cι 2 alkylsulfinyl, Cι-Cι 2 alkylsulfonyl, Cι-C] 2 haloalkyl, C 3 - Ci 2 cycloalkyl, or represents in each case optionally mono- to tetrasubstituted by identical or different fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl , d- Q-alkyl, C, -C 4 alkoxy, dC 4 alkylthio, Cι-C 4 alkylsulfinyl, Cj- C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (CC 4 alkyl) carbonyl, (dC 4 alkoxy) cafbonyl, C r C 4 haloalkyl, CC 4 halo genalkoxy, "-C-C 4 haloalkylthio, C r C 4 haloalkylsulfonyl, d- C 4 haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C haloalkenyl, dd-haloalkenyloxy each with 1 " to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Ansprach 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in spoke 1,
mit der Maßgabe, dass R54, R55 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 54 , R 55 do not simultaneously represent hydrogen,
R56 und R57 unabhängig voneinander für Wasserstoff, Cι-d2-Alkyl, C1-C.2- Alkoxy, C C12-Alkylthio, Cι-Cι2-Alkylsulfinyl, d-Cι2-Alkylsulfo- nyl, Ci-Cπ-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Ci- Q-Alkyl, Cι-C4-Alkoxy, C1-C -Alkylthio, d-Q-Alkylsulfinyl, Cx- C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (d-C4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, Ci-Q-Halogenalkyl, d-C4-Halo- genalkoxy, Cι-C4-Halogenalkylthio, C C4-Halogenalkylsulfinyl, d- C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen,R 56 and R 57 independently of one another for hydrogen, -CC 2 alkyl, C 1 -C. 2 - alkoxy, CC 12 alkylthio, -C 2 -C alkylsulfinyl, d -C 2 alkylsulfonyl, Ci-Cπ-haloalkyl, C 3 -C 2 -cycloalkyl or for each optionally simple to fourfold, identical or different by Fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, Ci-Q-alkyl, -C-C 4 alkoxy, C 1 -C alkylthio, dQ-alkylsulfinyl, C x - C 4 alkylsulfonyl, C 2 -C 4 - Alkenyl, C 2 -C 4 alkenyloxy, (dC 4 alkyl) - carbonyl, (Cι-C 4 -alkoxy) carbonyl, Ci-Q-haloalkyl, dC 4 -halogenalkoxy, Cι-C 4 -haloalkylthio, CC 4 -Halogenalkylsulfinyl, d- C -Halogenalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy, each with 1 to 7 fluorine, chloro and / or bromine atoms,
-C(R10)=N-ORπ, -SO2NR12R13, . -(CH2)pNR12R13,-C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 ,. - (CH 2 ) pNR 12 R 13 ,
-(CH2)pN(R12)C0R13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Anspmch 1 angegebenen Bedeutungen haben,- (CH 2 ) pN (R 12 ) C0R 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in Claim 1,
mit der Maßgabe, dass R , R nicht gleichzeitig für Wasserstoff stehen,with the proviso that R, R are not simultaneously hydrogen,
R58 und R59 unabhängig voneinander für Wasserstoff, Cι-C12-Alkyl, Cι-Cι2- Alkoxy, d-dz-Alkylthio, Cι-Cι2-Alkylsulfϊnyl, Cj-Cπ-Alkylsulfo- nyl, Cι-Ci2-Halogenalkyl, C3-Ci2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl,. C C4-Alkyl,. CrC4-Alkoxy, d-C4-Alkylthio, d-C4-Alkylsulfinyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (Cι-C4-Alkyl carbonyl, (Cι-C4-Alkoxy)carbonyl, C C -Halogenalkyl, d-C4-Halo- genalkoxy, Cι-C -Halogenalkylthio, Cι-C -Halogenalkylsulfϊnyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyϊ, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder , Bromatomen, -C(R10)=N-ORπ, -S02NR12R13, -(CH2)pNR12R13,R 58 and R 59 independently of one another for hydrogen, C 1 -C 12 alkyl, C 1 -C 2 alkoxy, d-dz-alkylthio, C 1 -C 2 alkylsulfonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 2 - Haloalkyl, C 3 -Ci 2 cycloalkyl or for in each case optionally up to four times, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl ,. CC 4 alkyl ,. C r C 4 alkoxy, dC 4 alkylthio, dC 4 alkylsulfinyl, CC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (C 1 -C 4 alkyl carbonyl, (Cι- C 4 -alkoxy) carbonyl, CC -haloalkyl, dC 4 -haloalkoxy, -C-C -haloalkylthio, -C-C -haloalkylsulfonyl, CC 4 -haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 -Halogenalkenyϊ, C 2 -C 4 -Halogenalkenyloxy each with 1 to 7 fluorine, chlorine and / or, bromine atoms, -C (R 10 ) = N-OR π , -S0 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl stehen, wobei R10 bis R13 die in Ansprach 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in spoke 1,
mit der Maßgabe, dass R58, R59 nicht gleichzeitig für Wasserstoff stehen,with the proviso that R 58 , R 59 do not simultaneously represent hydrogen,
R60 für Wasserstoff, CrCι2-Alkyl, C.-Cι2-Alkoxy, d-C^-Alkylthio, d- C12-Alkylsulfinyl, C Cι2-Alkylsulfonyl, Cι-Cι2-Halogenalkyl, C3- Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Ci- C4-Alkyl, d-C4-Alkoxy, d-C4-Alkylthio, d-Q-Alkylsulfinyl, d- C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (d-C4-Alkyl)- carbonyl, (C1-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, C.-CrHalo- genalkoxy, d-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfϊnyl, d- R R 60 is hydrogen, Cι C 2 alkyl, C.-Cι 2 alkoxy, dC ^ alkylthio, dC 12 alkylsulfinyl, C Cι 2 alkylsulfonyl, Cι-Cι 2 -haloalkyl, C 3 - Cι 2 -Cycloalkyl or for each optionally single to quadruple, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C 1 -C 4 -alkyl, dC 4 -alkoxy, dC 4 -alkylthio, dQ-alkylsulfinyl, d- C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (dC 4 alkyl) - carbonyl, (C 1 -C 4 alkoxy) carbonyl, Cι-C 4 haloalkyl, C.- CrHalogenalkoxy, dC 4 -haloalkylthio, -C-C 4 -haloalkylsulfonyl, d-
Q-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, d-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR1 R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oderQ-haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, dC 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each having 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 1 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or
-OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Ansprach 1 angegebenen Bedeutungen haben,-OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in spoke 1,
mit der Maßgabe, dass R24 und R60 oder R31 und R60 nicht gleichzeitig für Wasserstoff stehen, R61 für d-Cπ-Alkyl, C C12-Alkoxy, Cj-Cπ-Alkylthio, d-dz-Alkylsul- fmyl, Cι-Cι2-Alkylsulfonyl, Cι-C12-Halogenalkyl, C -C12-Cycloalkyl oder , ■ für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschie- den durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Cwith the proviso that R 24 and R 60 or R 31 and R 60 do not simultaneously represent hydrogen, R 61 for d-Cπ-alkyl, CC 12 -alkoxy, Cj-Cπ-alkylthio, d-dz-alkylsul- fmyl, Cι-Cι 2 alkylsulfonyl, Cι-C 12 haloalkyl, C -C 12 cycloalkyl or, ■ for each, if necessary, up to four times, the same or different from fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, C
Q-AΪkyl, CrC4-Alkoxy, Cι-C4-Alkylthio, C C4-Alkylsulfinyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (d-C4-Alkyl)- carbonyl, (C.-C4-Alkoxy)carbonyl, Cι-C -Halogenalkyl, Cι-C4-Halo- genalkoxy, Cι-C4-Halogenalkylthio, Cι-C4-Halogenalkylsulfinyl, C C -Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oderQ-AΪkyl, C r C 4 -alkoxy, Cι-C 4 -alkylthio, CC 4 -alkylsulfinyl, CC 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (dC 4 -alkyl) -, (C.-C 4 alkoxy) carbonyl, Cι-C genalkoxy 4 -Halo- carbonyl Cι-C haloalkyl, Cι-C4-haloalkylthio, Cι-C 4 haloalkylsulfinyl, haloalkylsulfonyl, each with 1 to CC 9 fluorine, chlorine and / or
Bromatomen, C2-C4-Halogenalkenyl, C2-C -Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORn, -SO2NR12R13, -(CH2)pNR1 R13,Bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR n , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 1 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Ansprach 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in spoke 1,
R62 für Cyano, Crd2-Alkyl, Cι-Cι2-Alkoxy, d-Cι2-Alkylthio, C C12- Alkylsulfinyl, CrCι2-Alkylsulfonyl, . d-Cπ-Halogenalkyl, C3-CJ2- Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d- C4-Alkyl, Ci-d-Alkoxy, d-C^Alkylthio, Cι-C4-Alkylsulfϊnyl, C C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (C.-C4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, C C4-Halo- genalkoxy, Cι-C4-Halogenalkylthio, d-C4-Halogenall<ylsulfϊnyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen, C2-C -Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13,R 62 for cyano, C r d 2 alkyl, C 1 -C 2 alkoxy, d C 2 alkyl thio, CC 12 - alkylsulfinyl, C r C 2 alkylsulfonyl,. d-Cπ-haloalkyl, C 3 -C J2 -cycloalkyl or for each optionally one to four times, identical or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, d- C 4 -alkyl, Ci-d-alkoxy, dC ^ alkylthio, Cι-C 4 alkylsulfonyl, CC 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (C.-C 4 alkyl) carbonyl, (Cι-C 4 - alkoxy) carbonyl, Cι-C 4 haloalkyl, CC 4 -Halo- genalkoxy, Cι-C4-haloalkylthio, dC 4 -Halogenall <ylsulfϊnyl, CC 4 haloalkylsulfonyl having in each case 1 to 9 fluorine, chlorine and or bromine atoms, C 2 -C haloalkenyl, C 2 -C 4 haloalkenyloxy each having 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Ansprach 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in spoke 1,
R63 für d-Cι2-Alkyl, C C12-Halogenalkyl, C3-C12-Cycloalkyl oder für j eweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C C4-Alkyl, . CrC4-Alkoxy, d-C4-Alkylthio, C C4-Alkylsulfinyl, Cr C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (C C4-Alkyl)- carbonyl, (C C4-Alkoxy)carbonyl, Cι-C4-Halogenalkyl, Cι-C -Halo- genalkoxy, Cι-C -Halogenalkylthio, d-C4-Halogenallylsulfinyl, C d-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13,R 63 for d -CC 2 alkyl, CC 12 haloalkyl, C 3 -C 12 cycloalkyl or for in each case optionally up to four times, identically or differently, by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, CC 4 -alkyl,. C r C 4 alkoxy, dC 4 alkylthio, CC 4 alkylsulfinyl, C r C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (CC 4 alkyl) carbonyl, ( CC 4 -alkoxy) carbonyl, -C-C 4 -haloalkyl, -C-C -haloalkoxy, -C-C -haloalkylthio, dC 4 -haloallylsulfinyl, C d-haloalkylsulfonyl, each with 1 to 9 fluoro, chloro and / or Bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OS02R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Ansprach 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OS0 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in spoke 1,
R64 für CrC12-Alkyl, C C12-Alkoxy, Cι-C12-Alkylthio, d-C12-Alkyl- sulfinyl, Cι-Cι2-Alkylsulfonyl, Cι-Cι2-Halogenalkyl, C3-C.2-Cyclo- alkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d- C4-Alkyl, C C4-Alkoxy, C C4-Alkylthio, d-C -Alkylsulfinyl, CR 64 is C r C 12 alkyl, CC 12 -alkoxy, C 12 alkylthio, dC 12 alkyl sulfinyl, Cι-Cι 2 alkylsulfonyl, Cι-Cι 2 -haloalkyl, C 3 -C. 2- cycloalkyl or, in each case, optionally up to four times, identically or differently, by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, d-C 4 -alkyl, CC 4 -alkoxy, CC 4 -alkylthio, dC -alkylsulfinyl, C
C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (d-C4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, d-C -Halogenalkyl, Cι-C4-Halo- genalkoxy, Cι-C4-Halogenalkylthio, CrC4-Halogenalkylsulfϊnyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13,C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, (dC 4 alkyl) carbonyl, (C 1 -C 4 alkoxy) carbonyl, dC haloalkyl, C 1 -C 4 halo - Genalkoxy, -C-C 4 haloalkylthio, CrC 4 haloalkylsulfonyl, CC 4 haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy 1 to 7 fluorine, chlorine and / or bromine atoms each, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Anspruch 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in claim 1,
R65 für d-C12-Alkyl, C,-Cι2-Alkylthio, Cι-Cι2-Alkylsulfinyl, d-C12- Alkylsulfonyl, Cι-C12-Halogenalkyl, C3-Ci2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschie- den durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Ci- C4-Alkyl, C C4-Alkoxy, C C -Alkylthio, C1-C4-Alkylsulfmyl, Cr C4-Alkylsulfonyl, C2-C -Alkenyl, C2-C4-Alkenyloxy, (Cι-C4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, C C4-Halogenalkyl, Ci-d-Halo- genalkoxy, Cι-C4-Halogenalkylthio, d-C4-Ha1ogenalkylsulfϊnyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oderR 65 for dC 12 alkyl, C 1 -C 2 alkylthio, C 1 -C 2 alkylsulfinyl, dC 12 alkylsulfonyl, C 1 -C 12 haloalkyl, C 3 -Ci 2 cycloalkyl or for in each case optionally up to four times, the same or different from fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, Ci C 4 -alkyl, CC 4 -alkoxy, CC -alkylthio, C 1 -C 4 -alkylsulfmyl, C r C 4 -alkylsulfonyl, C 2 -C -alkenyl, C 2 -C 4 -alkenyloxy, (-Cι-C 4 - Alkyl) - carbonyl, (-C-C 4 alkoxy) carbonyl, CC 4 -haloalkyl, Ci-d-haloalkoxy, Cι-C 4 -haloalkylthio, dC 4 -Ha1ogenalkylsulfϊnyl, CC 4 -haloalkylsulfonyl, each with 1 to 9 fluorine -, chlorine and / or
Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)pNR12R13,Bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) p NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Ansprach 1 angegebenen Bedeutungen haben,- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in spoke 1,
R66 für C Cι2-Alkyl, C C12-Alkylthio, d-C12-Alkylsulfinyl, d-d2- Alkylsulfonyl, Cι-Cι2-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, C C -Alkyl, CrC4-Alkoxy, Cι-C4-Alkylthio, CrC4-Alkylsulfinyl, C d-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (CrC4-Alkyl)- carbonyl, (Cι-C -Alkoxy)carbonyl, Cι-C4-Halogenalkyl, d-C4-Halo- genalkoxy, Cι-C4-Halogenalkylthio, d-Q-Halogenalkyls finyl, d-R 66 is C 2 Cι alkyl, CC 12 alkylthio, dC 12 alkylsulfinyl, dd 2 - alkylsulfonyl, Cι-Cι 2 -haloalkyl, C 3 -Cι 2 -cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different substituents Fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, CC-alkyl, C r C 4 -alkoxy, Cι-C 4 -alkylthio, C r C 4 -alkylsulfinyl, C d-alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 alkenyloxy, (C r C 4 alkyl) - carbonyl, (Cι-C -alkoxy) carbonyl, Cι-C 4 haloalkyl, dC genalkoxy 4 -Halo-, Cι-C4-haloalkylthio, dQ -Halogenalkyls finyl, d-
C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomeή, C2-C -Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORU, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)„N(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oderC 4 haloalkylsulfonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C haloalkenyl, C 2 -C 4 haloalkenyloxy, each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR U , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) „N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or
-OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Ansprach 1 angegebenen Bedeutungen haben,-OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in spoke 1,
>67 für d-Cι2-Alkyl, d-C12-Halogenalkyl, C3-Cι2-Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, Ci- C -Alkyl, CrC4-Alkoxy, Cι-C4-Alkylthio, Cι-C4-Alkylsulfinyl, C C -Alkylsulfonyl, C2-C -Alkenyl, C2-C4-Alkenyloxy, (CrC4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, C C4-Halogenalkyl, Cι-C4-Halo- genalkoxy, C C4-Halogenalkylthio, d- C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils .1 . bis 7 Fluor-, Chlor- und/oder Brpmatomen, -C(R10)=N-ORU, -SO2NR12R13, -(CH2)PNR12R13, -(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder> 67 for d -CC 2 alkyl, dC 12 -haloalkyl, C 3 -C 2 -cycloalkyl or for each optionally single to quadruple, the same or different by fluorine, chlorine, cyano, formyl, nitro, trimethylsilyl, Ci-C - alkyl, C r C 4 -alkoxy, C 4 alkylthio, Cι-C4-alkylsulfinyl, alkylsulfonyl CC, C 2 -C alkenyl, C 2 -C 4 alkenyloxy, (C r C 4 alkyl) carbonyl, (-C 4 -alkoxy) carbonyl, CC 4 -haloalkyl, -C-C 4 haloalkoxy, CC 4 -haloalkylthio, d- C 4 haloalkylsulfonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each having .1. up to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR U , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 , - (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or
-OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Ansprach 1 angegebenen Bedeutungen haben,-OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in spoke 1,
R68 für Cι-C12-Alkyl, C Cι2-Alkoxy, Cι-Cι2-Halogenalkyl, C3-C12- Cycloalkyl oder für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Cyano, Formyl, Nitro, Trimethylsilyl, d- Q-Alkyl, d-Q-Alkoxy, C C4-Alkylthio, d-C4-Alkylsulfinyl, d- C4-Alkylsulfonyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, (C C4-Alkyl)- carbonyl, (Cι-C4-Alkoxy)carbonyl, d-C4-Halogenalkyl, Cι-C4-Halo- genälkoxy, Cι-C4-Halogenalkylthio, C1-C4-Halogenalkylsulfinyl, C C4-Halogenalkylsulfonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, C2-C4-Halogenalkenyl, C2-C4-Halogenalkenyloxy mit jeweils 1 bis 7 Fluor-, Chlor- und/oder Bromatomen, -C(R10)=N-ORπ, -SO2NR12R13, -(CH2)PNR12R13,R 68 for Cι-C 12 alkyl, C 2 Cι -alkoxy, Cι 2 haloalkyl, C 3 -C 12 - cycloalkyl or represents in each case optionally mono- to tetrasubstituted by identical or different fluorine, chlorine, cyano, formyl, Nitro, trimethylsilyl, d-Q-alkyl, dQ-alkoxy, CC 4 -alkylthio, dC 4 -alkylsulfinyl, d- C 4 -alkylsulfonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, (CC 4 -Alkyl) - carbonyl, (-C-C 4 -alkoxy) carbonyl, dC 4 -haloalkyl, -C-C 4 -halo-genälkoxy, -C-C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, CC 4 -haloalkylsulfonyl with 1 to 9 fluorine, chlorine and / or bromine atoms each, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkenyloxy each with 1 to 7 fluorine, chlorine and / or bromine atoms, -C (R 10 ) = N-OR π , -SO 2 NR 12 R 13 , - (CH 2 ) P NR 12 R 13 ,
-(CH2)pN(R12)COR13, -(CH2)pN(R12)SO2R13, -OSO2R12 oder -OSO2NR12R13 substituiertes Phenyl oder Benzyl steht, wobei R10 bis R13 die in Ansprach 1 angegebenen Bedeutungen haben.- (CH 2 ) p N (R 12 ) COR 13 , - (CH 2 ) p N (R 12 ) SO 2 R 13 , -OSO 2 R 12 or -OSO 2 NR 12 R 13 substituted phenyl or benzyl, where R 10 to R 13 have the meanings given in spoke 1.
4. Pyrroline der Formel ( gemäß Anspruch 1, in welcher4. Pyrrolines of the formula (according to claim 1, in which
A1 und A2 jeweils für CH stehen.A 1 and A 2 each represent CH.
5. Verfahren zum Herstellen von Verbindungen der Formel (I) gemäß Ansprach 1, dadurch gekennzeichnet, dass man5. A process for the preparation of compounds of formula (I) according spoke 1, characterized in that
A) Δ^Pyrroline der Formel (H) in welcher R1, R2, R3, R4, A1 und R5 die in Ansprach 1 angegebenen Bedeutungen haben,A) Δ ^ pyrrolines of the formula (H) in which R 1 , R 2 , R 3 , R 4 , A 1 and R 5 have the meanings given in spoke 1,
mit Benzol-Derivaten der Formel (TU)with benzene derivatives of the formula (TU)
in welcher A2, R6, R7, R8 und Q die in Ansprach 1 angegebenen in which A 2 , R 6 , R 7 , R 8 and Q are those given in spoke 1
Bedeutungen haben undHave meanings and
X1 für Brom, Iod oder -OSO2CF3 steht,X 1 represents bromine, iodine or -OSO 2 CF 3 ,
in Gegenwart eines Katalysators und in Gegenwart eines Verdünnungsmittels umsetzt.in the presence of a catalyst and in the presence of a diluent.
6. Sc dlmgsbel---mpfungsmittel, gekennzeichnet durch einen Gehalt an mindestens einer Verbindung der Formel (I) gemäß Ansprach 1 neben Stteckmitteln und/oder oberflächenaktiven Stoffen.6. Sc dlmgsbel --- vaccine, characterized by a content of at least one compound of formula (I) according to spoke 1 in addition to plugging agents and / or surface-active substances.
7. Verwendung von Verbindungen der Formel (T) gemäß Ansprach 1 zur Bekämpfung von Schädlingen.7. Use of compounds of the formula (T) according to spoke 1 for combating pests.
8. Verfahren zur Bekämpfung von Schädlingen, dadurch gekennzeichnet, dass man Verbindungen der Formel (I) gemäß Anspruch 1 auf Schädlinge und/oder ihren Lebensraum einwirken lässt.8. A method for controlling pests, characterized in that compounds of the formula (I) according to Claim 1 are allowed to act on pests and / or their habitat.
9. Verfahren zur Herstellung von Schädlmgsbel<--inpfungsmitteln, dadurch gekennzeichnet, dass man Verbindungen der Formel (I) gemäß Ansprach 1 mit Streckmitteln und/oder oberflächenaktiven Stoffen vermischt. 9. A process for the preparation of pesticide inoculants, characterized in that compounds of the formula (I) according to Claim 1 are mixed with extenders and / or surface-active substances.
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CN1684960B (en) 2010-05-26
KR20050062546A (en) 2005-06-23
WO2004031176A2 (en) 2004-04-15
MXPA05003064A (en) 2005-05-27
CO5700822A2 (en) 2006-11-30
BR0314757A (en) 2005-07-26
US7297797B2 (en) 2007-11-20
CN1684960A (en) 2005-10-19
DE10243939A1 (en) 2004-04-01
JP2006511480A (en) 2006-04-06
ZA200502355B (en) 2006-05-31
US20060142343A1 (en) 2006-06-29
WO2004031176A3 (en) 2004-06-17

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