EP2321262A1 - Insecticidal 4-phenyl-1h-pyrazoles - Google Patents

Insecticidal 4-phenyl-1h-pyrazoles

Info

Publication number
EP2321262A1
EP2321262A1 EP09777596A EP09777596A EP2321262A1 EP 2321262 A1 EP2321262 A1 EP 2321262A1 EP 09777596 A EP09777596 A EP 09777596A EP 09777596 A EP09777596 A EP 09777596A EP 2321262 A1 EP2321262 A1 EP 2321262A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
hcooh
log
haloalkyl
cyano
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Withdrawn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
EP09777596A
Other languages
German (de)
French (fr)
Inventor
Stefan Werner
Klaus-Helmut Müller
Hans-Georg Schwarz
Tetsuya Murata
Klaus Raming
Ulrich Görgens
Angela Becker
Eva-Maria Franken
Eiichi Shimojo
Katsuhiko Shibuya
Ulrich Ebbinghaus-Kintscher
Teruyuki Ichihara
Masashi Ataka
Olga Malsam
Arnd Voerste
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
Original Assignee
Bayer CropScience AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP11165244A priority Critical patent/EP2374791A1/en
Priority to EP09777596A priority patent/EP2321262A1/en
Publication of EP2321262A1 publication Critical patent/EP2321262A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/10—Hydrazines
    • C07C243/22—Hydrazines having nitrogen atoms of hydrazine groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings

Definitions

  • the present invention relates to novel 4-phenyl-1H-pyrazoles and their use as insecticides and / or parasiticides and to processes for their preparation and to compositions containing such phenylpyrazoles.
  • EP 846 686 describes 4-phenyl-1H-pyrazoles (A) which have parasiticidal, insecticidal and nematicidal activity.
  • the definitions of the substituents R 3 , R 5 and R 7 are defined as follows:
  • R is halogen
  • R 5 H Ci. 6- alkyl, optionally substituted by one or more halogen atoms,
  • Ci- 6 alkoxy optionally substituted with one or more halogen atoms, or SF 5;
  • R 7 is halogen
  • R is halogen, alkyl, haloalkyl, alkoxy or dialkylamino
  • WO 2007/048734 describes 5-aminopyrazoles (C) for controlling phytopathogenic harmful fungi.
  • the definitions of the substituents R 3 , R 4 and R 5 are defined as follows:
  • R 3, R 4, R 5 are independently hydrogen, halogen, cyano, hydroxy, mercapto, C 1 - Cio-alkyl, C r 0 Ci haloalkyl, C 3 -C 8 cycloalkyl, C 2 -C 10 - alkenyl, C 2 -C ] 0 alkynyl, C r C 6 alkoxy, C r C 6 alkylthio, C, -C 6 alkoxy C r C 6 alkyl, NR A R B , phenyl, phenoxy or phenylthio
  • R A , R B are hydrogen or C, -C 6 alkyl
  • the present invention relates to novel 4-phenyl-1H-pyrazoles of the formula (I)
  • a 1 and A 2 are independently nitrogen or CR 4 ;
  • W 1 and W 2 are independently oxygen or sulfur
  • R 6 , R 6 ' , R 6 " , R 6'” and R 7 are as defined below;
  • Q J is C (R 1 i 0 ⁇ TR> 1 "K) XNTR ⁇ > 8 5 DR9 y ;
  • Q 4 for cyano (where R 1 is not amino), nitro, amino, COOH, COOR 12 , fluorine (if R 3 is other than chlorine), chlorine (if R 3 is different from chlorine, COOH, CH 2 CH 2 OMe and OMe), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 , S (O) 2 R 12 or S (O) 2 NR 8 R 9 stands;
  • R 1 is hydrogen, halogen, alkylsulfanyl, alkylsulfmyl, alkylsulfonyl, cyano, amino, Z 16 or NR 13 R 14 ;
  • R 2 is hydrogen, halogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, alkylsulfanylalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylsulfanylalkyl, haloalkylsulfinylalkyl, haloalkylsulfonylalkyl, cycloalkylalkyl, phenylalkyl, heteroarylalkyl, heterocyclylalkyl, phenyl, or arylhaloalkyl, haloalkyloxyhaloalkyloxyhaloalkyl, heterocyclyl, alkylsulfanyl, alkylsulfmyl, alkylsulfonyl
  • a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano
  • an alkanediyl radical bonded to phenyl, heteroaryl or heterocyclyl is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy or cyano.
  • R 3 is halogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkylcarbonyloxyalkyl, alkylsulfanylalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, hydroxy, Z 16 , alkoxy, acylamino, alkoxycarbonylamino, alkenyloxy, alkynyloxy, cycloalkylalkoxy, haloalkoxy, alkylsulfanyl, haloalkylsulfanyl, Alkylsulfmyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, carboxyl, aminocarbonyl, aminothio
  • R 5 is hydrogen or alkyl
  • R 6 , R 6 , R 6 , R 6 independently of one another represent hydrogen, amino, hydroxyl, mercapto,
  • a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano;
  • a heterocyclyl radical is optionally substituted by -OH / OO, -SH / SS, -NH 2 , halogen, alkyl, haloalkyl,
  • a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano;
  • R 6 , R 6 , R 6 , R 6 and R 7 together represent optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N-alkyl- at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
  • R 8 and R 9 are independently hydrogen, alkyl, haloalkyl, alkenyl
  • a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano;
  • R 8 / R 9 together for optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N-alkyl- at the beginning (or at the end) or within the hydrocarbon chain are interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
  • R 10 and R 11 are independently hydrogen, alkyl, haloalkyl or cyano
  • R 12 is alkyl or haloalkyl
  • a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano;
  • R 15 and R 16 are independently alkyl or
  • the compounds of the formula (I) according to the invention have very good insecticidal and parasiticidal properties and can be used in crop protection, veterinary hygiene, household and material protection for controlling undesired pests, such as insects, endo- or ectoparasites.
  • Halogen substituted radicals e.g. Haloalkyl
  • Halogen substituted radicals are halogenated once or several times up to the maximum possible number of substituents.
  • the halogen atoms may be the same or different.
  • Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
  • heteroatoms e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
  • Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different.
  • the 4-phenyl-1H-pyrazoles according to the invention are generally defined by formula (I).
  • Preferred, particularly preferred, very particularly preferred and particularly preferred radical definitions of the above and below named formers are given below. These definitions apply equally to the end products of formula (I) as well as to all intermediates.
  • a 1 and A 2 independently of one another each preferably nitrogen, CH, C-halogen, C- (C, -C 6 haloalkyl), C (C r C 6 alkoxy), C-cyano or C (C -C 6 -alkyl);
  • a 1 and A 2 independently of one another particularly preferably represent nitrogen, CH, C-halogen or C- (C r C 4 -haloalkyl);
  • a 1 and A 2 independently of one another very particularly preferably represent nitrogen or CH;
  • a 1 and A 2 are particularly preferably nitrogen; or
  • a 1 is particularly preferably nitrogen and A 2 is particularly preferably CH; or
  • a 1 is particularly preferably CH and A 2 particularly preferably nitrogen;
  • G 1 , G 2 , G 3 , G 4 , G 5 are preferably hydrogen or a combination of
  • Substituents independently selected from: halogen, C 1 -C 6 -alkyl, C 2 -C O - alkenyl, C 2 - C 6 alkynyl, C, -C 6 haloalkyl, SF 5, hydroxy, C r C 6 alkoxy, C r C 6 alkoxy-Ci-C 6 alkyl, C 1 -C 6 - alkoxy-C r C 6 alkoxy, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkyl C, C 6 alkoxy, C r C 6 haloalkoxy, Q-Ce-haloalkoxyCrCe alkyl, C r C 6 alkylsulfanyl, C 1 -C 6 - haloalkylsulfanyl, CRQ-alkylsulfinyl,
  • G 1 , G 2 , G 3 , G 4 , G 5 particularly preferably represent hydrogen or a combination of up to three substituents, independently of one another, selected from: halogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl , C 2 -C 4 alkynyl, C r C 4 haloalkyl, SF 5, hydroxy, C 1 -C 4 -AJkOXy, C 1 -C 4 -alkoxy-C 1 -C 4 alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 alkoxy, C 3 -C 4 cycloalkyl, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 3 -C 4 - alkoxy cycloalkyl-C r C 4, C r C 4 haloalkoxy, Ci-C4-haloalkoxy-C r C 4 alkyl,
  • G 1 , G 2 , G, G 4 , G 5 very particularly preferably represent a 3-substitution, 4-substitution, 3,4-disubstitution, 3,5-disubstitution or 3,4,5-trisubstitution, where the substituents G 1 , G 2 ,
  • G 3 , G 4 and G 5 are independently selected from: hydrogen, halogen, QC 2 -
  • Dialkylamino C 1 -C 2 -alkylsulfonylamino, C 1 -C 2 -dialkylsulfonylamino;
  • G 1 , G 2 , G 3 , G 4 , G 5 are especially preferred for 2-chlorine substitution, 3-chloro substitution, 3-bromosubstitution, 3-fluoro substitution, 4-bromosubstitution, 4-chloro substitution, 3,4-dichloro substitution , 3,4-difluorus substitution, 3-chloro-4-fluoro-substitution, 3-fluoro-4-chloro-substitution, 3-fluoro-5-chloro-substitution, S-chloro-S-trifluoromethyl-substitution, 3, 5 -dichloro-substitution,
  • Q 1 is preferably one of the heterocyclic groups listed below;
  • Q 1 particularly preferably represents one of the heterocyclic groups listed below;
  • (Z 24 ) Q 1 very particularly preferably represents one of the heterocyclic groups listed below;
  • Q ! is especially preferred for one of the heterocyclic groups listed below;
  • W 1 is preferably oxygen or sulfur
  • W 1 very particularly preferably represents oxygen
  • W 2 is preferably oxygen or sulfur
  • W 2 is very particularly preferably oxygen
  • R 6 , R 6 ' , R 6 " , R 6" and R 7 are as defined below;
  • Q 2 is preferably C (O) NR 8 R 9 ;
  • Q 3 is preferably C (R 10 R 1 ⁇ NR 8 R 9 ;
  • Q 4 is preferably cyano (where R 1 is not amino), COOH, COOR 12 , fluorine (if R 3 is other than chlorine), chlorine (if R 3 is other than chlorine, COOH, CH 2 CH 2 OMe and OMe is), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 , S (O) 2 R 12 or S (O) 2 NR 8 R 9 ;
  • Q 4 particularly preferably represents cyano (where R 1 is not amino), COOH, COOMe, COOEt, fluorine (if R 3 is other than chlorine), chlorine (if R 3 is different from chlorine, COOH, CH 2 CH 2 OMe and OMe), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 , S (O) 2 R 12 or S (O) 2 NR 8 R 9 ;
  • Q 4 is very particularly preferably cyano (where R 1 is not amino), COOH,
  • Q 4 is preferably cyano (where R 1 is not amino), COOH, COOMe, COOEt, fluorine (if R 3 is other than chlorine), bromine, iodine, SR 12 (where R 1 is not amino, if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 ;
  • R 1 preferably represents hydrogen, halogen, Ci-C4-alkylsulfanyl, C r C 4 alkylsulfinyl, C r C 4 alkylsulfonyl, Z 16, amino or NR 13 R 14;
  • R 1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, Z 16 , amino or NR 13 R 14 ;
  • R 1 very particularly preferably represents chlorine, bromine, iodine, Z 16 , amino or NR 13 R 14 ;
  • R 1 particularly preferably represents amino or NR 13 R 14 ;
  • R 2 preferably represents hydrogen, halogen, C r C 6 alkyl, C] -C6 haloalkyl, C r C 6 - alkoxy-C r C 6 alkyl, Ci-Cs-haloalkoxy CpC ⁇ -alkyl, C r C 6 alkoxy-C r C 6 haloalkyl, C r C 6 -alkyl sulfanyl-Ci-C 6 alkyl, CRQ-alkylsulfinyl CRCE-alkyl, C r C 6 alkylsulfonyl-Ci-C 6 alkyl, C 1 -C 6 - haloalkylsulfanyl-C r C 6 alkyl, C, -C 6 haloalkylsulfinyl-C, -C 6 alkyl, C r C 6 haloalkylsulfonyl-C r C 6 alkyl, C 3 -C
  • R 2 particularly preferably represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, -C 4 alkoxy-C r C 4 alkyl, C 1 -C 4 haloalkoxy-C 1 -C 4 - alkyl, C r C 4 alkoxy-Ci-C4-haloalkyl, CpC 4 - alkylsulfanyl-C
  • R 2 very particularly preferably represents fluorine, chlorine, bromine, iodine, Ci-C 4 -alkoxy-C 1 -C 4 - alkyl, C M-alkyl, aryl-Ci-C 4 haloalkyl, C r C 6 alkylsulfanyl , C r C 6 alkylsulfinyl, C r C 6 - alkylsulfonyl or C ⁇ haloalkyl;
  • R 2 is particularly preferably Ci_ 2 haloalkyl
  • R 3 is preferably halogen, C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C r C 6 - haloalkyl, C 3 -C 6 cycloalkyl, C r C 6 - alkoxy-Ci-C 6 alkyl, Ci-C6 alkylcarbonyloxy-Ci-C 6 alkyl, C 1 - C 6 alkylsulfanyl-C r C 6 alkyl, CrC ⁇ -alkylsulfinyl-CrC ⁇ -alkyl, C r C 6 -alkylsulfonyl-C 1 -C 6 alkyl, hydroxy, Ci-C 6 alkoxy, CrC ⁇ acylamino, Ci-C 6 alkoxycarbonylamino, C 2 -C 6 alkenyloxy, C 2 - C 6 alkynyloxy, C 3 -C 6 -cycloalky
  • R 3 particularly preferably represents halogen, C r C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 - alkynyl,
  • R 3 very particularly preferably represents halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, cyclopropyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 2 -alkylcarbonyloxy-C, -C 2 -alkyl, C r C 2 alkyl sulfanyl-C, -C 2 alkyl, Ci-Cralkyl-Ci-CrAlkylsulfinyl, C r C 4 alkylsulfonyl-C r C 2 alkyl, C 1 -C 2 - alkoxy , C 2 -acylamino, Ci-C alkoxy 2 alkoxycarbonylamino, cyclopropyl-C] -C 2, C 2 -HaIo- alkoxy, C r C 2 alkylsulphanyl, C r C 2 -Hal
  • R 3 especially preferably represents fluorine, chlorine, bromine, iodine, Ci-C 2 alkyl, C 2 - haloalkyl, Ci-C 2 -Haloalkylsulfanyl, C] -C 2 haloalkylsulfinyl, C 2 or -Haloalkyls ⁇ üfonyl cyano;
  • R 4 is preferably hydrogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, halogen or C 1 -C 6 -alkoxy;
  • R 4 particularly preferably represents hydrogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -
  • R 4 very particularly preferably represents hydrogen, fluorine, chlorine, bromine or iodine; R 4 is particularly preferably hydrogen;
  • R 5 is preferably hydrogen or Ci. 6- alkyl
  • R 5 particularly preferably represents hydrogen or C M -alkyl
  • R 5 is very particularly preferably hydrogen or C ] -3- alkyl
  • R 5 is particularly preferably hydrogen, methyl or ethyl
  • R 6 , R 6 ' , R 6 " , R 6 independently of one another preferably represent hydrogen, amino, hydroxyl, mercapto, nitro, cyano, carboxyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 - alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C r C 6 alkoxy, C r C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C r C 6 alkoxycarbonyl, Ci-C 6 alkylsulfanyl, Ci-C 6 -Haloalkylsulfanyl, QC 6 - alkylsulphinyl, C r C 6 haloalkylsulfinyl, Ci-C 6 alkylsulfonyl, QQ-
  • a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, nitro or cyano;
  • C 6 alkylsulfonyl C 1 -C 6 monoalkylamino, C 1 -C 6 dialkylamino, nitro or cyano; and a tied to phenyl, heteroaryl or heterocyclyl alkanediyl radical optionally mono- or polysubstituted by halogen, C r C 6 alkyl, QC 6 haloalkyl, QC 6 alkoxy or cyano.
  • R 6 , R 6 , R 6 , R 6 independently of one another particularly preferably represent hydrogen, amino, hydroxyl, mercapto, nitro, cyano, carboxyl, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 - Q-alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C r C 4 alkoxy, QC 4 haloalkoxy, C 2 -C 4 -alkenyl oxy, C 2 -C 4 alkynyloxy , C r C 4 alkoxycarbonyl, C r C 4 alkylsulphanyl, C r C 4 -Haloalkylsulfanyl, Q- C 4 alkylsulfinyl, Ci-C 4 -Haloalkylsulfmyl, Ci-C 4 alkylsulfonyl, Ci-C4
  • R 6 , R 6 , R 6 , R 6 are very particularly preferably each independently hydrogen, amino, cyano, fluorine, chlorine, bromine, iodine, C r C 2 alkyl, C r C 2 haloalkyl, C r C 2 Alkoxy, C 1 -C 2 haloalkoxy, phenyl or heteroaryl;
  • a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, nitro or cyano.
  • R 6, R 6, R 6, R 6 independently of one another particularly preferably represent hydrogen, amino, cyano, fluorine, chlorine, methyl, ethyl, C r C 2 haloalkyl, methoxy, ethoxy or C 1 -C 2 - haloalkoxy;
  • R 7 preferably represents hydrogen, amino, hydroxy, cyano, Ci-C 6 alkyl, C 1 -C 6 -
  • R 6 , R 6 , R 6 , R 6 and R 7 together represent optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -NC 1 -C 6 -alkyl-, at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl having in each case 2 to 5 carbon atoms;
  • R 7 particularly preferably represents hydrogen, amino, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -
  • C 4 haloalkyl C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C r C 4 alkoxy, C 2 -Q-alkenyloxy,
  • R 6 , R 6 , R 6 , R 6 and R 7 together represent optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N-Ci-C 4 -alkyl- at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
  • R 7 very particularly preferably represents hydrogen, amino, hydroxy, cyano, CpC 2 - alkyl, C r C 2 haloalkyl, cyclopropyl, C r C 2 alkoxy, C r C 2 alkoxycarbonyl, C, -C 2 -alkylcarbonyl C 1 -C 2 -alkylaminocarbonyl, C 1 -C 2 -dialkylaminocarbonyl, phenyl, phenyl-QQ-alkyl or heteroaryl-C 1 -C 2 -alkyl;
  • a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, nitro or cyano; and an alkanediyl radical attached to phenyl or heteroaryl is optionally mono- or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy or cyano and
  • two adjacent radicals R 6 / R 6 , R 6 / R 7 or R 7 / R 7 together for optionally substituted and / or optionally substituted by oxygen or sulfur or a grouping of the series -S (O) -, -SO 2 -, -NH- or -N-C] -C 2 alkyl- at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or
  • R 7 is particularly preferably represents hydrogen, amino, cyano, Ci-C 2 alkyl, C r C 2 - haloalkyl or Ci-C 2 alkoxy;
  • R 8 and R 9 are preferably and independently of one another are hydrogen, Ci-C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkenyl (optionally substituted by halogen, Ci-C 6 alkyl, QC 6 - haloalkyl or cyano), C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl (the cycle may optionally be mono- or polysubstituted by Ci-C substituted by halogen, 6 -haloalkyl, Ci-C 6 alkyl or fused to an aromatic or heteroaromatic), C 3 -C 6 -cycloalkyl-C 6 -alkyl (optionally mono- or polysubstituted at the cycle by halogen, C r C 6 haloalkyl, Ci-C 6 alkyl or fused to a aromatic or heteroaromatic , optionally mono- 6 alkyl moiety at the C) -C or polysubsti
  • a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, nitro or cyano;
  • C 6 alkylsulfonyl C 1 -C 6 monoalkylamino, C 1 -C 6 dialkylamino, nitro or cyano; and a tied to phenyl, heteroaryl or heterocyclyl alkanediyl radical optionally mono- or Ci-C 6 alkyl, Ci-C polysubstituted by halogen, 6 -haloalkyl, C r C 6 alkoxy or cyano and
  • R 8 / R 9 together represent optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N-Ci-Q-alkyl at the beginning (or at the end) or within the Hydrocarbon chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
  • R 8 and R 9 are particularly preferred and are independently hydrogen, C] -C 4 - alkyl, Ci-Q-haloalkyl, C 2 -C 4 alkenyl (optionally substituted by halogen, Ci-C 4 alkyl, C r C 4 haloalkyl or cyano), C 2 -C 4 alkynyl, C 3 -C 5 cycloalkyl (the cycle may optionally be mono- or polysubstituted by halogen, Ci-C4-haloalkyl, Ci-C 4 alkyl or condensed to an aromatic or heteroaromatic), C 3 -C 5 -cycloalkyl-Ci-C 4 -alkyl (optionally mono- or polysubstituted by halogen, Ci-C 4 haloalkyl, Ci-C 4 -alkyl or fused to a Aromatics or heteroaromatics, on the C] -C 4 -alkyl part optionally mono- or polysubstit
  • C 4 alkylsulfonyl C 1 -C 4 monoalkylamino, C 1 -C 4 dialkylamino, nitro or cyano; and a tied to phenyl, heteroaryl or heterocyclyl alkanediyl radical optionally mono- or polysubstituted by halogen, C) -C 4 -alkyl, Ci-C 4 haloalkyl, C] -C 4 alkoxy or cyano and
  • R 8 / R 9 together represent optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N-Ci-C 4 -alkyl - at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
  • R 8 and R 9 are most preferably and independently hydrogen, Ci-C 4 alkyl, C] -C 4 haloalkyl, C 3 -C 5 cycloalkyl (optionally mono- or on cycle polysubstituted by halogen, C C 2 -C 10 -alkyl, C 1 -C 2 -alkyl or fused to an aromatic or heteroaromatic radical), C 3 -C 5 -cycloalkyl-C 1 -C 2 -alkyl (optionally substituted one or more times by halogen, C 1 -
  • a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, nitro or cyano; and a phenyl or heteroaryl bound Alkandiy-R is optionally mono- or polysubstituted by halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C] -C 2 alkoxy or cyano and
  • R 8 / R 9 together represent optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -,
  • R 8 and R 9 are especially preferred and are independently hydrogen, Q- C4 alkyl, C, -C 4 haloalkyl, C 3 -C 5 cycloalkyl, C 3 -C 5 cycloalkyl-C r C 2 - alkyl, C 3 -C 5 -cyclohaloalkyl-Ci-C 2 -alkyl, C 3 -C 4 -Halocycloalkyl, methylsulfanyl-C r C 3 alkyl, methylsulfinyl-Ci-cralkyl, methylsulfonyl-Ci-C 3 -alkyl , Phenylmethyl (optionally substituted on the aromatic mono- or polysubstituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, on the methyl part optionally mono- or polysubstituted by methyl, ethyl,
  • Propyl, methoxy or trifluoromethyl) or pyrimidylmethyl (optionally mono- or polysubstituted on the pyrimidyl dur fluorine, chlorine, bromine, methyl, ethyl, Trifluoromethyl, methoxy, cyano or nitro, on the methyl part optionally mono- or polysubstituted by methyl, ethyl, propyl, iso-propyl, methoxy or trifluoromethyl);
  • R 10 and R 11 are preferably and independently of one another hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or cyano;
  • R 10 and R 11 are particularly preferably and independently of one another hydrogen, C r
  • R 10 and R 11 very particularly preferably independently of one another hydrogen, C r C 2 alkyl or C r C 2 haloalkyl;
  • R 10 and R 11 are particularly preferably hydrogen
  • R 12 is preferably C r C 6 alkyl or C r C 6 haloalkyl
  • R 12 particularly preferably represents Ci-C 4 alkyl or C 1 -C 4 -HaIOaIlCyI;
  • R 12 very particularly preferably represents C 1 -C 4 -alkyl
  • R 12 is particularly preferably methyl or ethyl
  • R 13 and R 14 preferably and independently of one another represent hydrogen, Ci-C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci-C 6 alkoxy C r C 6 alkyl, C, -C 6 alkylcarbonyl-Cr
  • Haloalkylcarbonyl C 2 -C 6 -alkenylcarbonyl, C 2 -C 6 -alkynylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, Q-
  • a phenyl or heteroaryl radical optionally mono- or Ci-C polysubstituted by halogen, 6 alkyl, dC 6 haloalkyl, C r C 6 alkoxy, nitro or cyano;
  • R 15 and R 16 are independently alkyl or
  • R 15 and R 16 together represent optionally substituted and / or optionally substituted by oxygen or sulfur or a grouping of the series -S (O) -, -SO 2 -, -NH- or -N-alkyl- at the beginning (resp. at the end) or within the hydrocarbyl chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
  • a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 4 -alkyl, QQ-haloalkyl, QQ-alkoxy, nitro or cyano;
  • R 15 and R 16 are independently alkyl or
  • R 15 and R 16 together represent optionally substituted and / or optionally substituted by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N- Alkyl- at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
  • R 13 and R 14 very particularly preferably independently of one another hydrogen, C 1 -C 2 -alkyl, Ci-C 2 haloalkyl, Ci-CrAlkoxy-QC ⁇ alkyl, C r C 2 alkylsulfonyl, C, -C 2- alkylcarbonyl, C 1 -C 2 -haloalkylcarbonyl, C 1 -C 2 -alkoxycarbonyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl, phenylC r C 2 -alkyl, heteroaryl-C r is C 2 -alkyl, phenylcarbonyl, heteroarylcarbonyl, phenyl-C ! -C 2 -alkylcarbonyl, phenoxycarbonyl or phenyl-C 1 -C 2 -alkoxycarbonyl
  • a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, nitro or cyano; and one on
  • Phenyl or heteroaryl bonded alkanediyl radical optionally mono- or polysubstituted by halogen, C r C 2 alkyl, Ci-C 2 haloalkyl, CpC 2 -Akoxy or cyano
  • R 15 and R 16 are independently alkyl or
  • R 15 and R 16 together represent optionally substituted and / or optionally substituted by oxygen or sulfur or a grouping of the series -S (O) -, -SO 2 -, -NH- or -N-alkyl- at the beginning (resp. at the end) or within the hydrocarbyl chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
  • the compounds of the formula (I) can be subdivided into the compounds of the formula (II), (HI), (IV) and (V), depending on their substituent R 1 :
  • G 1 "5 , R 2 , R 13 , R 14 , and M have the meanings given above, but R 13 and R 14 are not simultaneously hydrogen and
  • R 17 is halogen, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl or cyano.
  • a 1 1 -2 Z and Q have the meanings given above, R 13 and R 14 but not simultaneously are hydrogen and
  • R 17 is halogen, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl or cyano.
  • the invention relates in one embodiment to compounds of the formula (H-A)
  • G 1 , G 2 and G 3 independently represent hydrogen, halogen, methyl or CF 3 ;
  • G 4 and G 5 are hydrogen
  • R 2 represents fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C r C 4 alkyl, aryl-C r C 4 - haloalkyl, CRQ-alkylsulfanyl, C 1 - C 6 is alkylsulfinyl, C 1 -C 6 alkylsulfonyl or C 1 -C 4 haloalkyl;
  • R 3 is fluoro, chloro, bromo, iodo, C 1-2 alkyl, d. 2 haloalkyl, C r C 2 haloalkylsulfanyl, C r C 2 haloalkylsulfonyl, C 1 -C 2 haloalkylsulfinyl or cyano and
  • the invention relates to compounds according to embodiment 2, in which Q 1 stands for Z 3 , Z 7 , Z 15 , Z 16 , Z 17 , Z 1S , Z 21 , Z 22 , Z 23 or Z 24 ;
  • R 6 , R 6 ' , R 6 " , R 6'" are hydrogen, amino, cyano, fluorine, chlorine, methyl, ethyl, C 1 -C 2 -haloalkyl, methoxy, ethoxy or C 1 -C 2 -haloalkoxy; and
  • R 7 is hydrogen, amino, cyano, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 2 -alkoxy.
  • the invention relates to compounds according to embodiment 3, in which Q 1 is Z 16 or Z 3 .
  • the invention relates to compounds according to embodiment 1, in which Q stands for Q 2 .
  • R 8 and R 9 are independently hydrogen, C r C 4 - alkyl, Ci-C 4 haloalkyl , C 3 -C 5 cycloalkyl (the cycle may optionally be mono- or polysubstituted by halogen, C) -C 2 -haloalkyl, C) -C 2 alkyl or fused to a aromatic or heteroaromatic), C 3 -C 5 - Cycloalkyl-C 1 -C 2 -alkyl (optionally substituted one or more times by halogen, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkyl on the cycle or fused to an aromatic or heteroaromatic radical, on the C r C 2 -alkyl part, if appropriate mono- or polysubstituted by halogen, C r C 2 alkyl, C r C
  • R 8 and R 9 are independently hydrogen, C r C 4 alkyl, Ci-C 4 haloalkyl, C 3 -C 4 - cycloalkyl, C 3 -C 4 halocycloalkyl, C 3 -C 5 cycloalkyl-Ci-C 2 alkyl, C 3 -C 5 halocycloalkyl-Ci-C 2 - alkyl, methylsulfinyl-C r C 3 alkyl, methylsulfanyl-C r C 3 - alkyl, methylsulfonyl-C r C 3 -alkyl, phenylmethyl (optionally monosubstituted or polysubstituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, optionally substituted one or more times by methyl on the methyl part
  • the invention relates to compounds according to embodiment 1, in which Q stands for Q 3 .
  • the invention relates to compounds according to embodiment 8, in which Q 3 is C (R 10 R n ) NR 8 R 9 ; R 10 and R 11 are independently hydrogen, C 1 -C 2 - alkyl or Ci-C 2 haloalkyl, and R 8 and R 9 are independently hydrogen, C 1 -C 4 - alkyl, Ci-C 4 haloalkyl , C 3 -C 5 cycloalkyl (optionally mono- or polysubstituted at the cycle by halogen, Ci-C 2 haloalkyl, C 1 -C 2 -alkyl or fused to a aromatic or heteroaromatic), C 3 -C 5 cycloalkyl -C-C 2 -alkyl (optionally mono- or polysubstituted at the cycle by halogen, Ci-C 2 haloalkyl, C r C 2 alkyl or fused to a aromatic or heteroaromatic, the Ci-C 2 alkyl moiety may optional
  • the invention relates to compounds according to embodiment 9 in which R 8 and R 9 are each independently hydrogen, Ci-C 2 alkyl, Ci-C 2 haloalkyl, C 3 -C 5 - cycloalkyl, C 3 -C 5 -cycloalkyl-C r C 2 -alkyl, C 3 -C 5 -HaIoCyClOaIlCyI, C 3 -C 5 -Halocycloalkyl-Ci-C 2 - alkyl, methylsulfmyl-C, -C 3 -alkyl, methylsulfanyl-C, -C 3 alkyl, methylsulfonyl CPCS-alkyl, phenyl-Ci-C 2 alkyl, heteroaryl-Ci-C 2 alkyl, C r C 2 dialkylaminocarbonyl, C 1 -C 2 - alkylaminocarbonyl, C r C 2 .
  • the invention relates to compounds according to embodiment 1, in which Q is Q 4 .
  • the invention relates to compounds according to embodiment 11 in which Q 4 is cyano (where R 1 is not amino), nitro, amino, COOH, COOR 12 , fluorine (if R 3 is other than chlorine), chloro ( if R 3 is other than chloro, COOH, CH 2 CH 2 OMe and OMe), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 and R 12 for dC 4 alkyl or C r C 4 haloalkyl.
  • the invention relates to compounds according to embodiment 12 wherein Q 4 is cyano (where R 1 is other than amino), COOH, COOMe, COOEt, fluorine (if R 3 is other than chlorine), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 .
  • the invention relates to compounds of the formula (EU-A)
  • G 1 , G 2 and G 3 independently represent hydrogen, halogen, methyl or CF 3 ;
  • G 4 and G 5 are hydrogen
  • R 2 represents fluorine, chlorine, bromine, iodine, Ci-C4 alkoxy-C, -C 4 alkyl, C, -C 4 alkyl, aryl-C, -C 4 - haloalkyl, C r C 6 alkylsulfanyl , C r C 6 -Alkylsulfmyl, C r C 6 alkylsulfonyl or C, -C 4 haloalkyl;
  • a 1 and A 2 are independently N or CH;
  • R 3 is fluoro, chloro, bromo, iodo, C 1-2 -alkyl, d -2 -haloalkyl, C r C 2 -haloalkylsulfanyl, C 1 - C 2 -haloalkylsulfonyl, C 1 -C 2 -haloalkylsulfinyl or cyano;
  • R 13 and R 14 are each independently hydrogen, methyl, ethyl, propyl, iso-propyl, methylcarbonyl, methoxycarbonyl, trifluoromethylcarbonyl, methylsulfanyl, trifluoromethylsulfanyl, benzyl or pyridylmethyl, but R 13 and R 14 are not simultaneously hydrogen, and
  • the invention relates to compounds according to embodiment 14, in which Q stands for Q 1 .
  • the invention relates to compounds according to embodiment 15 in which Q 1 is Z 3 , Z 7 , Z 15 , Z 16 , Z 17 , Z 18 , Z 21 , Z 22 , Z 23 or Z 24 ;
  • R 6 , R 6 ' , R 6 " , R 6'" are hydrogen, amino, cyano, fluorine, chlorine, methyl, ethyl, C] -C 2 haloalkyl, methoxy, ethoxy or C 1 -C 2 haloalkoxy and
  • R 7 is hydrogen, amino, cyano, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 2 -alkoxy.
  • the invention relates to compounds according to embodiment 14, in which Q is Q 2 .
  • the invention relates to compounds according to embodiment 18, in which Q 2 is C (O) NR 8 R 9 ; and R 8 and R 9 are independently hydrogen, C 1 -C 4 - alkyl, Ci-C optionally mono- or 4 haloalkyl, C 3 -C 5 cycloalkyl (at cycle polysubstituted by halogen, Ci-C 2 - Haloalkyl, C 1 -C 2 -alkyl or fused to an aromatic or heteroaromatic radical), C 3 -C 5 -cycloalkyl-C 1 -C 2 -alkyl (optionally mono- or polysubstituted by halogen, C] -C 2 - at the cycle Haloalkyl, Ci-C 2 alkyl or fused to an aromatic or heteroaromatic, the CrC 2 alkyl optionally mono- or polysubstituted by halogen, C r C 2 alkyl, C r C 2 haloalkyl, C r
  • the invention relates to compounds according to embodiment 19, in which R 8 and R 9 are each independently hydrogen, Ci-CrAlkyl, Ci-Gj-haloalkyl, C 3 -C 4 - cycloalkyl, C 3 -C 4 halocycloalkyl, C 3 -C 5 -cycloalkyl-C r C 2 -alkyl !
  • the invention relates to compounds according to embodiment 14, in which Q is Q 3 .
  • the invention relates to compounds according to embodiment 21 in which Q 3 is C (R 10 R 1 -NR 8 R 9 ; R 10 and R 11 are each independently hydrogen, C 1 -C 2 -alkyl or C 2 haloalkyl, and R 8 and R 9 are independently hydrogen, C 1 -C 4 - alkyl, Ci-C 4 haloalkyl, C 3 -C 4 cycloalkyl (optionally mono- or polysubstituted at the cycle by halogen, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkyl or fused to an aromatic or heteroaromatic radical), C 3 -C 4 -cycloalkyl-C 1 -C 2 -alkyl (optionally substituted one or more times by halogen on the cycle, C r C 2 haloalkyl, Ci-C 2 alkyl or fused optionally mono- or polysubstituted by halogen, C 1 -C 2 -
  • the invention relates to compounds according to embodiment 22, in which R 8 and R 9 are independently hydrogen, C 1 -C 2 -alkyl, C r C 2 haloalkyl, C 3 -C 5 - cycloalkyl, C 3 - C 5 -Cycloalkyl-QC 2 -alkyl, Q-Cs-Halocycloalkyl, C 3 -C 5 -Halocycloalkyl-QC 2 -alkyl, methylsulfinyl-QC 3 -alkyl, methylsulfanyl-C r C 3 -alkyl, methylsulfonyl-C r C 3 alkyl, phenyl-QC 2 -alkyl, heteroaryl-C] -C 2 alkyl, C 1 -C 2 dialkylaminocarbonyl, QC 2 alkylamino carbonyl, Ci-C 2 -Haloalkylaminocarbonyl, Ci-C
  • the invention relates to compounds according to embodiment 24 in which Q 4 is cyano (where R 1 is other than amino), nitro, amino, COOH, COOR 12 , fluorine (if R 3 is other than chlorine), chloro ( if R 3 is other than chloro, COOH, CH 2 CH 2 OMe and OMe), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 and R 12 is QC 4 alkyl or QC 4 haloalkyl.
  • the invention relates to compounds according to embodiment 25 in which Q 4 is cyano (where R 1 is other than amino), COOH, COOMe, COOEt, fluorine (if R 3 is other than chlorine), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 .
  • the invention relates to compounds of the formula (FV-A)
  • G 1 , G 2 and G 3 independently represent hydrogen, halogen, methyl or CF 3 ;
  • G 4 and G 5 are hydrogen
  • R 2 represents fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C r C 4 alkyl, Aiyi-C 1 -C 4 - haloalkyl, C r C 6 alkylsulfanyl , Q-Ce-alkylsulfinyl, Cj-Q-alkylsulfonyl or C 1 -C 4 haloalkyl;
  • a 1 and A 2 are independently N or CH;
  • R 3 represents fluorine, chlorine, bromine, iodine, C 1-2 alkyl, C ⁇ haloalkyl, C r C 2 -Haloalkylsulfanyl, C 1 - C 2 haloalkylsulfonyl, C] -C 2 -Haloalkylsulf ⁇ nyl or cyano;
  • R 17 is halogen, alkylsulfanyl, alkylsulfmyl, alkylsulfonyl or cyano and
  • Q stands for Q 1 , Q 2 , Q 3 or Q 4 .
  • the invention relates to compounds according to embodiment 27, in which Q is Q 1 .
  • the invention relates to compounds according to embodiment 28 in which Q 1 is Z 3 , Z 7 , Z 15 , Z 16 , Z 17 , Z 18 , Z 21 , Z 22 , Z 23 or Z 24 ;
  • R 6 , R 6 ' , R 6 " , R 6'" are hydrogen, amino, cyano, fluorine, chlorine, methyl, ethyl, C 1 -C 2 -HaIOaIlCyI, methoxy, ethoxy or C 1 -C 2 - haloalkoxy and
  • R 7 is hydrogen, amino, cyano, QQ-alkyl, C r C 2 -haloalkyl or C 1 -C 2 -alkoxy.
  • the invention relates to compounds according to embodiment 29, in which Q 1 is Z 16 or Z 3 .
  • the invention relates to compounds according to embodiment 27 in which Q is Q 2 .
  • the invention relates to compounds according to embodiment 31 in which Q 2 is C (O) NR 8 R 9, and R 8 and R 9 are each independently hydrogen, Ci-C 4 - alkyl, C 1 -C 4 - Haloalkyl, C 3 -C 5 -cycloalkyl (optionally mono- or polysubstituted by halogen, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkyl or fused to an aromatic or heteroaromatic radical on the cycle, C 3 -C 5 -cycloalkyl -C-C 2 alkyl (the cycle may optionally be mono- or polysubstituted by halogen, Ci-C 2 haloalkyl, Ci-C 2 -alkyl or fused to a aromatic or heteroaromatic, the Ci-C 2 alkyl moiety may optionally be mono- or polysubstituted by halogen,
  • the invention relates to compounds according to embodiment 32 in which R 8 and R 9 are each independently hydrogen, Ci-C 4 alkyl, C] -C 4 haloalkyl, C 3 -C 4 - cycloalkyl, C 3 - C 4 halocycloalkyl, C 3 -C 5 cycloalkyl-Ci-C 2 alkyl, C 3 -C 5 halocycloalkyl-Ci-C 2 - alkyl, d-Cs-Methylalkylsulfinyl-alkyl, Methylalkylsulfanyl-C 3 - alkyl, methylalkylsulfonyl-C r C 3 -alkyl, phenyhnethyl (optionally mono- or polysubstituted by at least one of fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro on the
  • the invention relates to compounds according to embodiment 27, in which Q stands for Q 3 .
  • the invention relates to compounds according to embodiment 34 in which Q 3 is C (R 1 V) NR 8 R 9 ; R 10 and R 11 are independently hydrogen, C r C 2 - alkyl or Ci-C 2 haloalkyl, and R 8 and R 9 are independently hydrogen, QC 4 - alkyl, Ci-C 4 haloalkyl, C 3 - C 4 -cycloalkyl (optionally one or more times at the cycle substituted by halogen, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkyl or fused to an aromatic or heteroaromatic radical), C 3 -C 4 -cycloalkyl-C 1 -C 2 -alkyl (optionally substituted one or more times at the cycle by Halogen, Ci-C 2 -haloalkyl, Ci-C 2 -alkyl or condensed on an aromatics or heteroaromatics, on the Ci-C 2 -alkyl part if necessary mono
  • the invention relates to compounds according to embodiment 35, in which R 8 and R 9 are each independently hydrogen, Ci-C 2 alkyl, C 1 -C 2 -HaIOaIlCyI, C 3 -C 5 - cycloalkyl, C 3 - C 5 cycloalkyl C r C 2 alkyl, C 3 C 5 halocycloalkyl, C 3 C 5 halocycloalkyl QC 2 alkyl, methylsulfmyl C r C 3 alkyl, methylsulfanyl C r C 3 alkyl , methylsulfonyl-C 1 -C 3 alkyl, phenyl-Ci-C 2 alkyl, heteroaryl-Ci-C 2 alkyl, Ci-C2 dialkylaminocarbonyl, QC 2 alkylamino carbonyl, Ci-C 2 -Haloalkylaminocarbonyl, Ci-C 2 alkylsulfon
  • the invention relates to compounds according to embodiment 27, in which Q stands for Q 4 .
  • the invention relates to compounds according to embodiment 37 in which Q 4 is cyano (where R 1 is other than amino), nitro, amino, COOH, COOR 12 , fluorine (if R 3 is other than chlorine), chloro ( if R 3 is different from chlorine, COOH, CH 2 CH 2 OMe and OMe), bromine, iodine, SR 12 (where R 1 does not represent amino, when R 12 is alkyl), S (O) R I2 or S (O) 2 R 12, and R 12 is C r C 4 Alkyl or C, -C 4 haloalkyl.
  • the invention relates to compounds according to embodiment 38 in which Q 4 is cyano (where R 1 is other than amino), COOH, COOMe, COOEt, fluorine (if R 3 is other than chlorine), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 .
  • the invention relates to compounds of the formula (V-A)
  • G 1 , G 2 and G 3 independently represent hydrogen, halogen, methyl or CF 3 ;
  • G 4 and G 5 are hydrogen
  • R 2 is fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C r C 4 -alkyl, ArVl-C 1 -C 4 -haloalkyl, C r C 6 -alkylsulfanyl , C r C 6 -Alkylsulfmyl, C r C 6 alkylsulfonyl or C 1 -C 4 haloalkyl;
  • a 1 and A 2 are independently N or CH;
  • R 3 represents fluorine, chlorine, bromine, iodine, C 1-2 alkyl, C ⁇ haloalkyl, Ci-C 2 -Haloalkylsulfanyl, C 1 - C 2 haloalkylsulfonyl, C 1 -C 2 haloalkylsulfinyl or cyano and
  • Q stands for Q 1 , Q 2 , Q 3 or Q 4 .
  • the invention relates to compounds according to embodiment 41 in which Q 1 is Z 3 , Z 7 , Z 15 , Z 16 , Z 17 , Z 18 , Z 21 , Z 22 , Z 23 or Z 24 ;
  • R 6, R 6 ', R 6', R 6 '' represents hydrogen, amino, cyano, fluorine, chlorine, methyl, ethyl, -C 2 haloalkyl, methoxy, ethoxy or C 1 -C 2 - Haloalkoxy and
  • R 7 is hydrogen, amino, cyano, Ci-C 2 alkyl, C r C 2 haloalkyl or Q-C 2 alkoxy.
  • the invention relates to compounds according to embodiment 42, in which Q 1 is Z 16 or Z 3 .
  • the invention relates to compounds according to embodiment 40 in which Q is Q 2 .
  • the invention relates to compounds according to embodiment 44 in which Q 2 is C (O) NR 8 R 9 and R 8 and R 9 are each independently hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 - Haloalkyl, C 3 -C 5 -cycloalkyl (optionally mono- or polysubstituted by halogen, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkyl or fused to an aromatic or heteroaromatic radical on the cycle, C 3 -C 5 -cycloalkyl -C r C 2 alkyl (the cycle may optionally be mono- or polysubstituted by halogen, Ci-C 2 haloalkyl, Ci-C 2 alkyl or fused to a aromatic or heteroaromatic, the Ci-C 2 alkyl moiety may optionally be mono- or polysubstituted by halogen, C r C 2 alkyl, C r C 2
  • the invention relates to compounds according to embodiment 45, in which R 8 and R 9 are each independently hydrogen, Ci-C 4 alkyl, C r C 4 haloalkyl, C 3 -C 4 - cycloalkyl, C 3 -C 4 -Halocycloalkyl, C 3 -C 5 -cycloalkyl-C, -C 2 -alkyl, C 3 -C 5 -Halocycloalkyl-Ci-C 2 - alkyl, methylalkylsulfmyl-C r C 3 -alkyl, methylalkylsulfanyl-C, -C 3 -alkyl, methylalkylsulfonyl-C, - C 3 -alkyl, phenylmethyl (optionally mono- or polysubstituted on the aromatic by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano
  • the invention relates to compounds according to embodiment 47 in which Q 3 is C (R 10 R U ) NR 8 R 9 ; R 10 and R 11 are independently hydrogen, QC 2 - alkyl or Ci-C 2 haloalkyl, and R 8 and R 9 are independently hydrogen, QC 4 - alkyl, Ci-C 4 haloalkyl, C 3 -C 4 -Cycloalkyl (at the cycle optionally mono- or polysubstituted by halogen, C r C 2 haloalkyl, Ci-C 2 alkyl or fused to an aromatic or heteroaromatic), C 3 -C 4 cycloalkyl-Ci-C 2 alkyl (optionally mono- or polysubstituted by halogen, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkyl or fused to an aromatic or heteroaromatic radical on the cycle, if appropriate mono- or polysubstituted by halogen,
  • the invention relates to compounds according to embodiment 48 wherein R 8 and R 9 are independently hydrogen, QC 2 alkyl, QC 2 haloalkyl, C 3 -C 5 cycloalkyl, C r C 5 cycloalkyl QC 2- alkyl, QQ-halocycloalkyl, QC 5 -halocycloalkyl-QC 2 -alkyl, methylsulfinyl-QC 3 -alkyl, methylsulfanyl-C r C 3 -alkyl, methylsulfonyl-C 1 -C 3 -alkyl, phenyl-Ci-C 2 alkyl, heteroaryl-QC 2 alkyl, Ci-C2 dialkylaminocarbonyl, QQ-alkylamino carbonyl, C 2 -Haloalkylaminocarbonyl, QC 2 alkylsulfonyl, C r C 2 alkylcarbonyl, QC
  • the invention relates to compounds according to embodiment 50 in which Q 4 is cyano (where R 1 is not amino), nitro, amino, COOH, COOR 12 , fluorine (if R 3 is other than chlorine), chloro ( if R 3 is other than chloro, COOH, CH 2 CH 2 OMe and OMe), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 and R 12 is C r C 4 alkyl or C r C 4 haloalkyl.
  • the invention relates to compounds according to embodiment 51 in which Q 4 is cyano (where R 1 is other than amino), COOH, COOMe, COOEt, fluorine (if R 3 is other than chlorine), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 .
  • the present invention also relates to the use of the compounds of the formula (T) for controlling animal pests, where the radicals are as defined above.
  • the present invention also provides the use of the compounds of the formula (I) for combating animal pests, wherein M is M 1 , Q is Q 4 , Q 4 is hydrogen and all other radicals are as defined above, with the proviso in that A 1 and A 2 are not simultaneously nitrogen.
  • the present invention also provides the use of the compounds of the formula (I) for controlling animal pests, wherein wherein M is M 1 , R 3 is hydrogen and all other radicals are as defined above, with the proviso that A 1 and A 2 does not simultaneously stand for nitrogen.
  • the compounds according to the invention can be prepared in the manner mentioned below or analogously thereto.
  • V ⁇ condenses, wherein initially hydrazones of the formula (VDT) arise as an intermediate and the reaction takes place at a higher reaction time and higher temperature, the ring closure to the aminopyrazole of the formula (TI).
  • acids can be added as a catalyst, wherein inorganic acids such as hydrochloric acid and organic acids such as sulfonic acids or acetic acid may be suitable.
  • ketonitriles, their tautomers or hydrates of the formulas (VI-A), (VI-B) or (VI-C) first with a chlorinating agent, for example phosphoryl chloride, phosphorus pentachloride, thionyl chloride, phosgene, chlorine or oxalyl chloride, optionally in an inert diluted organic solvent, converted to chloroacrylonitriles (VI-F), wherein the reaction in the temperature range from -20 0 C to 120 0 C can be performed.
  • a chlorinating agent for example phosphoryl chloride, phosphorus pentachloride, thionyl chloride, phosgene, chlorine or oxalyl chloride, optionally in an inert diluted organic solvent, converted to chloroacrylonitriles (VI-F), wherein the reaction in the temperature range from -20 0 C to 120 0 C can be performed.
  • condensation is carried out with aryl or heteroaryl-hydrazines of the formula (VIT) in a suitable organic solvent in the presence of basic auxiliary reagents, eg alcoholates or nitrogen bases, wherein the reaction in the temperature range from -20 0 C to 120 0 C are performed can.
  • basic auxiliary reagents eg alcoholates or nitrogen bases
  • ketonitriles may be present in tautomeric forms (VI-A) and (VI-B) and as hydrate (VI-C).
  • the starting compounds may also be used in the form of their salts, e.g.
  • the ketonitriles can be used in the form of their alkali metal salts.
  • the aminoacrylonitriles may be present in the tautomeric forms (VI-D) and (VI-E).
  • the starting compounds may also be used in the form of their salts, e.g.
  • the aminoacrylonitriles can be used in the form of their alkali metal salts.
  • Ketonitriles of the formula (VI-A, VI-B and VI-C) can be prepared by known methods. Such methods are described in: J. Amer. Chem. Soc. 1950, 72, 5409-5413; Tetrahedron 2007, 63 (47), 11626-11635, Org. Lett. 2007, 9 (18), 3575-3578, J. Med. Chem. 2007, 50 (2), 399-403, Bioorg. Med. Chem. Lett. 2006, 16 (3), 695-700.
  • Chloroacrylonitriles of the formula (VI-F) can be prepared by known methods. Such methods are described in: J. Org Chem (USSR) 1981, 1441, JP 08-208620, J. Med. Chem. 2005, 48 (22), 6843-6854, Nucleosides, Nucleotides Nucleic Acids 2004, 23 (5), 805-812, J. Med. Chem. 2001, 44 (3), 350-361.
  • Aryl, pyridyl and Pyrimidinylhydrazine of formula (VTI) are commercially available in part or can be prepared by methods known in the art, such as in process (H), produced.
  • amidation, acylation and substitution reactions required for the construction of Q 1'3 are carried out by methods known to the person skilled in the art, as described, for example, in processes (F), (G) and (J) and can be carried out either at the end of the synthesis frequency or preferably at the stage of suitable intermediates.
  • LG halogen, alkylsulfonyl, boronic acid or boronic acid ester
  • the intermediates (DC) are prepared by process (A) with hydrazine hydrate:
  • 1-H-aminopyrazoles of the formula (EX) are reacted with aryl halides, heteroaryl halides, arylalkylsulfones, heteroarylalkylsulfones, arylboronic esters, heteroarylboronic acids, arylboronic esters or heteroarylboronic esters (LG-M) in the presence of a base and possibly a copper or iron salt and a ligand in a suitable organic solvent, wherein preferably a particular isomer, the aminopyrazole of the formula (I) is formed.
  • ketonitriles may be present in tautomeric forms (VI-A) and (VI-B) and as hydrate (VI-C).
  • the starting compounds may also be used in the form of their salts, e.g.
  • the ketonitriles can be used in the form of their alkali metal salts.
  • the aminoacrylonitriles may be present in the tautomeric forms (VI-D) and (VI-E).
  • the starting compounds may also be used in the form of their salts, e.g.
  • the aminoacrylonitriles can be used in the form of their alkali metal salts.
  • ketonitriles of the formula (VI-A, VI-B and VI-C) can be prepared by known methods: J. Amer. Chem. Soc. 1950, 72, 5409-5413; Tetrahedron 2007, 63 (47), 11626-11635; Org. Lett. 2007, 9 (18), 3575-3578; J. Med. Chem. 2007, 50 (2), 399-403, Bioorg. Med. Chem. Lett. 2006, 16 (3), 695-700.
  • the acrylonitriles of the formula (VI-D and VI-E) can be prepared by known methods: J. Med. Chem. 2006, 49, 3332-3344
  • the chloroacrylonitriles of the formula (VI-F) can be prepared by known methods: J. Org. Chem. (USSR) 1981, 1441 JP 08208620, J. Med. Chem., 2005, 48 (22), 6843-6854, Nucleosides , Nucleotides and Nucleic Acids, 2004, 23 (5), 805-812, J. Med. Chem., 2001, 44 (3), 350-361
  • aryl and heteroaryl compounds LG-M are commercially available or can be prepared by methods known to those skilled in the art.
  • G 1 , G 2 , G 3 , G 4 , G 5 , R 1 and R 2 are as defined above, with the proviso that R 1 is not amino.
  • R 13 is CH 2 R 5
  • G, 1-5, r R, 2, r R> 13, r R> 14 and M may have the meanings given above, but R 13 "and JDR 14 are not both simultaneously hydrogen; LG is halogen or alkylsulfonyl.
  • compounds of the formula (ff) are reacted with one or two alkylating agents, acylating agents or sulfonylating agents R 13 -LG or R 14 -LG, where by monosubstitution and disubstitution aminopyrazoles of the formula (ffla) or (HIb) arise.
  • Suitable alkylating agents are alkyl bromides, alkyl dibromides, alkyl iodides, alkyl diiodides, dialkyl sulfates and alkyl sulfonates.
  • the acylating agents used are carboxylic anhydrides and carbonyl chlorides, and sulfonyl chlorides are sulfonyl chlorides.
  • the mono-N-substituted aminopyrazoles of the formula (IIIa) can be obtained by reductive amination from the aminopyrazoles of the formula (ff), an aldehyde and a reducing agent, for example hydrogen in the presence of a hydrogenation catalyst, alkali metal borohydrides or borane.
  • compounds of formula (ffla) can be obtained by reacting compounds of formula (II) to amidines of formula (Iffc) or imidoesters of formula (Iffd), followed by a reduction step.
  • R " alkylsulfanyl
  • R 17 is halogen or alkylsulfanyl.
  • suitable sources of nitrosyl species are alkali nitrites plus acids and esters of nitrous acid, eg butyl nitrite and tert-butyl nitrite.
  • metal halides and organic halides for example bromoform or iodoform can be used.
  • 5-halopyrazoles can be converted to 5-aminopyrazoles of the formula (DI) with cyanides, for example CuCN in suitable solvents, for example NMP under heat in 5-cyanopyrazoles of the formula (IVb) or with amines in suitable solvents, where R 13 or R 14 is not hydrogen.
  • cyanides for example CuCN in suitable solvents, for example NMP under heat in 5-cyanopyrazoles of the formula (IVb) or with amines in suitable solvents, where R 13 or R 14 is not hydrogen.
  • thioethers can in the presence of a suitable oxidizing agent, for example with H 2 O 2 , sodium periodate, tert-butyl hypochlorite, calcium hypochlorite Ca (OCl) 2 , sodium chlorite NaClO 2 , sodium hypochlorite NaOCl, peracids or O 2 and catalytic cerium ammonium nitrate to 5-Alkylsulf ⁇ nylpyrazolen the formula (IVd) and 5-Alkylsulfonylpyrazolen of formula (IVe) are oxidized.
  • a suitable oxidizing agent for example with H 2 O 2 , sodium periodate, tert-butyl hypochlorite, calcium hypochlorite Ca (OCl) 2 , sodium chlorite NaClO 2 , sodium hypochlorite NaOCl, peracids or O 2 and catalytic cerium ammonium nitrate to 5-Alkylsulf ⁇ nylpyra
  • N-substituted aminopyrazoles of the formula (III) is described in: DE 3520327, WO 2005/023776
  • G 1 "5 , R 1 , R 2 and M have the meanings given above and LG is bromine, iodine or alkylsulfonyl.
  • the bromides or iodides of formula (XI) can be prepared by known methods described e.g. in: WO 2005/11292, Chemistry of Heterocyclic Compounds (New York, NY, United States), 2005, 41 (1), 105-110, Bioorg. & Med. Chem. 2004, 12 (12), 3345-3355, Bioorg. Med. Chem. Lett. 2004, 14, 4949, J. Med. Chem. 1977, 20 (12), 1562-1569
  • boronic acids or boronic esters of the formula (Xu) are in part commercially available or they can be easily prepared by known methods. This is described for example in: WO 99/64428.
  • the present invention also relates to compounds of the formulas (XI-A) or (XI-B)
  • R 1 , R 2 , R 3 , A 1 , A 2 and Q are as defined above and LG is chloro, bromo, iodo or alkylsulfonyl.
  • inventive method (F) for preparing the compounds of formula (IA-Ql) or (IBQ 1) are compounds of formula (XIII-A) or (XHI-B) with N-heterocycles in the presence of a base and possibly one Copper or iron salt and a ligand in a suitable organic solvent to form a compound of formula (IA-Ql) or (IBQ 1) is formed.
  • R 1 , R ⁇ R 3 , R ⁇ R% R, A 1 and A 1 have the meanings given above.
  • DCC N, N'-dicyclohexylcarbodiimide
  • DIC diisopropylcarbodiimide
  • EDC N-ethyl-N '- (3-dimethylaminopropyl) carbodiimide HCl
  • a benzotriazole such as HOBt (1-hydroxybenzotriazole) or azabenzotriazole such as HOAt ( 7-aza-1-hydroxybenzotriazole).
  • R 12 and M have the meanings given above;
  • the amines (XVI) are prepared by methods known to the person skilled in the art, for. B. in a sequence of diazotization and reduction, converted into the corresponding hydrazines (see, for example J. Med Chem 1993, 36 (11) pp 1529-1538 and WO 2006/081034).
  • hydrazines of the general formula (VE) are in part commercially available (for example ethyl-4-hydrazinylbenzenecarboxylate or methyl-4-hydrazinyl-2-methoxybenzenecarboxylate).
  • Amines of the formula (XVI) are in part commercially available or can be prepared by methods known to those skilled in the art, for example by saponification of compounds of the formula (XTV) or reduction of compounds of the formula (XV).
  • the present invention also provides compounds of the formula (VII-A) or (VE-B)
  • R, R, R, R, A and A have the meanings given above;
  • Activation may be via acid chlorides, mixed anhydrides, pentafluorophenyl esters or with the aid of substituted carbodiimides, e.g.
  • substituted carbodiimides e.g.
  • DCC N, N'-dicyclohexylcarbodiimide
  • DIC diisopropylcarbodiimide
  • EDC N-ethyl-N '- (3-dimethylaminopropyl) carbodiimide HCl
  • a benzotriazole such as HOBt (1-hydroxybenzotriazole) or azabenzotriazole such as HOAt (7-aza-l-hydroxybenzotriazole) take place.
  • the present invention also provides compounds of the formulas (X-A) or (X-B)
  • Methyl 4-amino-2-methylbenzoate (5.0 g, 30 mmol) is initially charged in water (25 mL), combined with concentrated hydrochloric acid (50 mL) and stirred at room temperature for 30 min.
  • the reaction mixture is cooled to 0 ° C. and a solution of sodium nitrite (2.72 g, 39.3 mmol) in water (25 mL) is slowly added dropwise.
  • the mixture is stirred for one hour at 0 0 C and then added dropwise at 0 0 C tin ( ⁇ ) chloride dihydrate (20.5 g, 90.8 mmol) in concentrated hydrochloric acid (100 mL) was added.
  • the precipitate is filtered off with suction, washed with water and dried.
  • the application rate of the active compounds according to the invention in the treatment of parts of plants, eg leaves, is from 0.1 to 10,000 g / ha, preferably from 10 to 1,000 g / ha, particularly preferably from 50 to 300 g / ha (when used by pouring or dropping the Application rate can even be reduced, especially when inert substrates such as rockwool or perlite are used); in the Seed treatment of 2 to 200 g per 100 kg of seed, preferably from 3 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, most preferably from 2.5 to 12.5 g per 100 kg of seed; in the soil treatment from 0.1 to 10,000 g / ha, preferably from 1 to 5,000 g / ha.
  • These application rates are given by way of example only and not by way of limitation within the meaning of the invention.
  • the active compounds according to the invention are suitable for plant tolerance, favorable warm-blood toxicity and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs which are found in agriculture, horticulture, livestock, forests, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Anoplura e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.
  • arachnids e.g. Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp.
  • Eriophyes spp. Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp. Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.
  • Gastropoda e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.
  • helminths from the class of helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp , Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Lo
  • protozoa such as Eimeria
  • Eimeria protozoa
  • Heliopeltis spp. Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp. Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.
  • Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp ..
  • Orthoptera e.g. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
  • siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis.
  • Symphyla e.g. Scutigerella immaculata.
  • Thysanoptera e.g. Basothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
  • Thysanura e.g. Lepisma saccharina.
  • the plant parasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.
  • the compounds according to the invention may also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as anti-MLO agents (Mycoplasma -like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, active ingredients. impregnated synthetic materials, fertilizers and micro-encapsulants in polymeric materials.
  • customary formulations such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, active ingredients. impregnated synthetic materials, fertilizers and micro-encapsulants in polymeric materials.
  • formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • Excipients which can be used are those which are suitable for imparting special properties to the composition itself and / or preparations derived therefrom (for example spray liquor, seed dressing), such as certain technical properties and / or specific biological properties.
  • Typical auxiliaries are: extenders, solvents and carriers.
  • polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (also fats and oils) and (poly) ethers, the simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulfones and sulfoxides (such as dimethylsulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • ketones
  • organic solvents can also be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl sulfoxide, and water.
  • Suitable carriers are:
  • Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates;
  • suitable dispersants are non-ionic and / or ionic substances, e.g.
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations.
  • Dyes such as inorganic pigments such as 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.
  • Other additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present.
  • the active ingredient according to the invention can be used in its commercial formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers, semiochemicals or else with agents to improve plant properties.
  • active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers, semiochemicals or else with agents to improve plant properties.
  • the active compounds according to the invention can be present as insecticides in their commercial formulations and in the forms of use prepared from these formulations in admixture with synergists.
  • Synergists are compounds which increase the effect of the active ingredients without the added synergist itself having to be active.
  • the active compounds according to the invention can furthermore, when used as insecticides, be present in their commercial formulations and in the forms of use prepared from these formulations in mixtures with inhibitors which reduce degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant tissues ,
  • the active substance content of the application forms prepared from the commercial formulations can vary within wide ranges.
  • the total active ingredient concentration or the active ingredient concentration of the individual active substances of the use forms is in the range of 0.00000001 to 97 wt .-% active ingredient, preferably in the range of 0.0000001 to 97 wt .-%, particularly preferably in the range of 0.000001 to 83 wt. -% or 0.000001 to 5 wt .-% and most preferably in the range of 0.0001 to 1 wt.%.
  • the application is done in a custom forms adapted to the application.
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants produced by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or Combinations of these methods can be obtained, including transgenic plants and including those protected by plant breeders' rights or non-protectable plant varieties.
  • Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, by way of example leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, atomizing, spreading, brushing, injecting and in propagating material, in particular in seeds, further by single or multilayer coating.
  • plants which can be treated according to the invention mention may be made of the following: cotton, flax, grapevine, fruits, vegetables, such as Rosaceae sp. (for example, pome fruits such as apple and pear, but also drupes such as apricots, cherries, almonds and peaches and soft fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp.
  • Rosaceae sp. for example, pome fruits such as apple and pear, but also drupes such as apricots, cherries, almonds and peaches and soft fruits such as strawberries
  • Rosaceae sp. for example, pome fruits such as apple and pear
  • Rubiaceae sp. for example, coffee
  • Theaceae sp. Sterculiceae sp.
  • Rutaceae sp. for example, lemons, organs and grapefruit
  • Solanaceae sp. for example tomatoes
  • Liliaceae sp. Asteraceae sp.
  • Umbelliferae sp. for example, Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceae sp. leek, onion), Papilionaceae sp.
  • Main crops such as Gramineae sp. (for example corn, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example, white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes and rapeseed, mustard, horseradish and cress), Fabacae sp. (for example, bean, peanuts), Papilionaceae sp. (for example, soybean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example, sugar beet, fodder beet, Swiss chard, beet); Useful plants and ornamental plants in the garden and forest; and each genetically modified species of these plants.
  • Gramineae sp. for example corn, turf, cereals such as wheat, rye, rice,
  • the active compounds according to the invention are suitable for the treatment of seed.
  • the active compounds according to the invention mentioned above is preferred or particularly preferred.
  • This is how much of the damage is caused by pests caused damage to Kultu ⁇ planzen already by the infestation of the seed during storage and after the introduction of the seed into the soil and during and immediately after the germination of the plants.
  • This phase is particularly critical, as the roots and shoots of the growing plant are particularly sensitive and even minor damage can lead to the death of the entire plant. There is therefore a particular interest in protecting the seed and the germinating plant by the use of suitable agents.
  • the present invention therefore also relates, in particular, to a method for protecting seeds and germinating plants from the infestation of pests by treating the seed with an active ingredient according to the invention.
  • the invention also relates to the
  • the invention on seed which has been treated with an active ingredient according to the invention for protection against pests.
  • the invention also relates to seed in which an active compound of the formula I are applied as a constituent of a coating or as a further layer or further layers in addition to a coating.
  • One of the advantages of the present invention is that because of the particular systemic properties of some of the active ingredients of the invention, the treatment of the seed with these agents not only protects the seed itself but also the resulting plants after emergence from pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • the active compounds according to the invention can be used in particular also in transgenic seed, the resulting from this seed Plants are capable of expressing a pest-directed protein.
  • certain pests can already be controlled by the expression of the insecticidal protein, for example, and additionally protected against damage by the active compounds according to the invention.
  • the active compounds according to the invention are suitable for the protection of seed of any plant variety as already mentioned above, which is used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are corn, peanut, canola, rapeseed, poppy, soybean, cotton, turnip (eg sugarbeet and fodder beet), rice, millet, wheat, barley, oats, rye, sunflower, tobacco, potatoes or vegetables ( eg tomatoes, cabbage).
  • the inventive active ingredients are also suitable for the treatment of seed of fruit plants and vegetables as already mentioned above. Of particular importance is the treatment of the seeds of maize, soya, cotton, wheat and canola or rapeseed.
  • transgenic seed with an active ingredient according to the invention is of particular importance.
  • the heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. and whose gene product shows activity against corn borer and / or corn rootworm. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
  • the active ingredient according to the invention is applied to the seed alone or in a suitable formulation.
  • the seed is treated in a condition that is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
  • the amount of the applied according to the invention active ingredient and / or other additives is chosen so that the germination of the seed is not affected or the resulting plant is not damaged. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates.
  • the agents according to the invention can be applied directly, ie without containing further components and without being diluted. In general, it is preferable to apply the agents to the seed in the form of a suitable formulation.
  • Suitable formulations and methods for seed treatment are known to those skilled in the art and are described, for example, in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002 / 028186 A2.
  • the active compounds which can be used according to the invention can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.
  • formulations are prepared in a known manner by mixing the active ingredients with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water.
  • conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water.
  • Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, CI. Pigment Red 112 and CI. Solvent Red 1 known dyes.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are alkylnaphthalene sulfonates such as diisopropyl or diisobutylnaphthalene sulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds.
  • Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • defoamers all foam-inhibiting substances customary for the formulation of agrochemical active ingredients can be present in the seed dressing formulations which can be used according to the invention.
  • foam-inhibiting substances customary for the formulation of agrochemical active ingredients can be present in the seed dressing formulations which can be used according to the invention.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
  • Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly dispersed silicic acid.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
  • Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, pp. 401-412).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds, including seed of transgenic plants. In this case, additional synergistic effects may occur in interaction with the substances formed by expression.
  • the seed dressing formulations which can be used according to the invention or the preparations prepared therefrom by the addition of water
  • all mixing devices customarily usable for the dressing can be considered.
  • the seed is placed in a mixer which adds either desired amount of seed dressing formulations either as such or after prior dilution with water and mixes until evenly distributed the formulation on the seed.
  • a drying process follows.
  • the treatment method of the invention may be used for the treatment of genetically modified organisms (GMOs), e.g. As plants or seeds are used.
  • GMOs genetically modified organisms
  • Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
  • heterologous gene essentially refers to a gene which is provided or assembled outside the plant and which, when introduced into the nuclear genome, chloroplast genome or hypochondriacal genome, imparts new or improved agronomic or other properties to the transformed plant Expressing protein or polypeptide or that it is downregulating or shutting down another gene present in the plant or other genes present in the plant (for example by antisense technology, cosuppression technology or RNAi technology [RNA Interference]).
  • a heterologous gene present in the genome is also referred to as a transgene.
  • a transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
  • Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material conferring on these plants particularly advantageous, useful features (whether obtained by breeding and / or biotechnology).
  • Plants and plant varieties which are also preferably treated according to the invention are resistant to one or more biotic stressors, i. H. These plants have an improved defense against animal and microbial pests such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.
  • Plants and plant varieties which can also be treated according to the invention are those plants which are resistant to one or more abiotic stress factors.
  • Abiotic stress conditions may include, for example, drought, cold and heat conditions, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients, or avoidance of shade.
  • Plants and plant varieties which can also be treated according to the invention are those plants which are characterized by increased yield properties.
  • An increased yield can in these plants z. B. based on improved plant physiology, improved plant growth and improved plant development, such as water efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination and accelerated Abreife.
  • the yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for hybrid seed production, seedling vigor, plant size, endemic number and spacing, root growth, seed size, fruit size, Pod size, pod or ear number, number of seeds per pod or ear, seed mass, increased seed filling, decreased seed drop, decreased Pod popping and stability.
  • Other yield-related traits include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction of nontoxic compounds, improved processability, and improved shelf life.
  • Plants which can be treated according to the invention are hybrid plants which already express the properties of the heterosis or the hybrid effect, which generally leads to higher yield, higher vigor, better health and better resistance to biotic and abiotic stress factors.
  • Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner).
  • the hybrid seed is typically harvested from the male sterile plants and sold to propagators.
  • Pollen sterile plants can sometimes be produced (eg in maize) by delaving (i.e., mechanically removing male genitalia or male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome.
  • cytoplasmic male sterility have been described, for example, for Brassica species (WO 1992/005251, WO 1995/009910, WO 1998/27806, WO 2005/002324, WO 2006/021972 and US 6,229,072).
  • pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering.
  • a particularly convenient means of producing male-sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens. The fertility can then be restorated by expression of a ribonuclease hernmer such as barstar in the tapetum cells (eg WO 1991/002069).
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering which can be treated according to the invention are herbicidally tolerant plants, ie plants that have been tolerated to one or more given herbicides. Such plants can either be through genetic transformation or through Selection of plants containing a mutation conferring such herbicide tolerance.
  • Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H. Plants tolerant to the herbicide glyphosate or its salts.
  • glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS).
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • AroA gene mutant CT7 of the bacterium Sahnonella typhimurium (Comai et al., Science (1983), 221, 370-371), the bacterium Agrobacterium sp. (Barry et al., Curr Topics Plant Physiol.
  • Glyphosate-tolerant plants can also be obtained by expressing a gene coding for a glyphosate oxidoreductase enzyme as described in US 5,776,760 and US 5,463,175. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in, e.g. As WO 2002/036782, WO 2003/092360, WO 2005/012515 and WO 2007/024782 is encoded. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above-mentioned genes, as described, for example, in WO 2001/024615 or WO 2003/013226.
  • herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate. Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition.
  • an effective detoxifying enzyme is, for example, an enzyme encoding a phosphinotricin acetyltransferase (such as the bar or pat protein of Streptomyces species).
  • Plants expressing an exogenous phosphinotricin acetyltransferase are described, for example, in US 5,561,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 and US 7,112,665.
  • hydroxyphenylpyruvate dioxygenase HPPD
  • HPPD hydroxyphenylpyruvate dioxygenase
  • the hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate.
  • Plants that are tolerant to HPPD inhibitors can be encoded with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant HPPD enzyme according to WO 1996/038567, WO 1999/024585 and WO 1999/024586, be transformed.
  • Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 1999/034008 and WO 2002/36787.
  • the tolerance of plants to HPPD inhibitors can also be improved by transforming plants in addition to a gene coding for an HPPD-tolerant enzyme with a gene coding for a prephenate dehydrogenase enzyme, as described in WO 2004 / 024928 is described.
  • ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides.
  • ALS also known as acetohydroxy acid synthase, AHAS
  • AHAS acetohydroxy acid synthase
  • plants which are tolerant to imidazolinone and / or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding, as for example for the soybean in US 5,084,082, for rice in WO 1997/41218, for the sugar beet in US 5,773,702 and WO 1999/057965, for salad in US 5,198,599 or for the sunflower in WO 2001/065922.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering which can also be treated according to the invention are insect-resistant transgenic plants, ie plants which are resistant to attack by certain target insects were made resistant. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance.
  • insect-resistant transgenic plant includes any plant containing at least one transgene comprising a coding sequence encoding:
  • an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof such as the insecticidal crystal proteins described by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature, online at: http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal parts thereof, e.g. Proteins of the cry protein classes CrylAb, CrylAc, CrylF, Cry2Ab, Cry3Ae or Cry3Bb or insecticidal parts thereof; or
  • a crystal protein from Bacillus thuringiensis or a part thereof which is insecticidal in the presence of a second, different crystal protein than Bacillus thuringiensis or a part thereof, such as the binary toxin consisting of the crystal proteins Cy34 and Cy35 (Moellenbeck et al., Nat Biotechnol. (2001), 19, 668-72; Schnepf et al., Applied Environment Microb. (2006), 71, 1765-1774); or
  • an insecticidal hybrid protein comprising parts of two different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the
  • Proteins of 1) above or a hybrid of the proteins of 2) above e.g.
  • a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin consisting of the proteins VIPlA and VIP2A (WO 1994/21795); or
  • a hybrid insecticidal protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or
  • amino acids have been replaced with another amino acid to achieve higher insecticidal activity against a target insect species and / or to broaden the spectrum of the corresponding target insect species and / or due to changes induced in the coding DNA during cloning or transformation (preserving the coding for an insecticidal protein), such as the protein VIP3Aa in cotton event COT 102.
  • insect-resistant transgenic plants in the present context also include any plant comprising a combination of genes encoding the proteins of any of the above classes 1 to 8.
  • an insect-resistant plant contains more than one transgene encoding a protein of any one of the above 1 to 8 in order to extend the spectrum of the corresponding target insect species or to delay the development of resistance of the insects to the plants by use different proteins which are insecticidal for the same target insect species, but have a different mode of action, such as binding to different receptor binding sites in the insect.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are tolerant of abiotic stressors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such stress resistance. Particularly useful plants with stress tolerance include the following:
  • a Plants which contain a transgene capable of reducing the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or plants, as described in WO 2000/004173 or EP 04077984.5 or EP 06009836.5 is described.
  • b Plants which contain a stress tolerance-promoting transgene capable of reducing the expression and / or activity of the PARG-encoding genes of the plants or plant cells, as described, for example, in WO 2004/090140;
  • Plants containing a stress tolerance-promoting transgene encoding a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthesis pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid nucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase, as described e.g. As described in EP 04077624.7 or WO 2006/133827 or PCT / EP07 / 002433.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering which can also be treated according to the invention have a changed amount, quality and / or storability of the harvested product and / or altered characteristics of certain components of the harvested product, such as:
  • Transgenic plants which synthesize a modified starch with respect to their physicochemical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of the side chains, the viscosity behavior, the gel strength, the starch grain size and / or starch grain morphology is altered in comparison to the synthesized starch in wild-type plant cells or plants, so that this modified starch is better suited for certain applications.
  • transgenic plants which synthesize a modified starch are described, for example, in EP 0571427, WO 1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581, WO 1996/27674, WO 1997/11188, WO 1997/26362, WO 1997/32985, WO 1997/42328, WO 1997/44472, WO 1997/45545, WO 1998/27212, WO 1998/40503, WO 99/58688, WO 1999/58690, WO 1999/58654, WO 2000/008184, WO 2000/008185, WO 2000/28052, WO 2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO 2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927,
  • Examples are plants which produce polyfructose, in particular of the inulin and levan type, as described in EP 0663956, WO 1996/001904, WO 1996/021023, WO 1998/039460 and WO 1999/024593, plants which are alpha-1 To produce 4-glucans, as described in WO 1995/031553, US 2002/031826, US 6,284,479, US 5,712,107, WO 1997/047806, WO 1997/047807, WO 1997/047808 and WO 2000/14249, plants which alpha-1, 6-branched alpha-1,4-glucans, as described in WO 2000/73422, and plants producing alternan, as described in WO 2000/047727, EP 06077301.7, US 5,908,975 and EP 0728213 is.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering, which can also be treated according to the invention, are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; these include:
  • plants such as cotton plants, which contain an altered form of rsw2 or rsw3 homologous nucleic acids, as described in WO 2004/053219;
  • plants such as cotton plants having increased expression of sucrose phosphate synthase as described in WO 2001/017333;
  • plants such as cotton plants in which the timing of the passage control of the Plasmodesmen is changed at the base of the fiber cell, z.
  • plants By down-regulating the fiber-selective ⁇ -l, 3-glucanase, as described in WO 2005/017157;
  • plants such as cotton plants with modified reactivity fibers, e.g. By expression of the N-acetylglucosamine transferase gene, including nodC, and chitin synthase genes, as described in WO 2006/136351.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering which can also be treated according to the invention are plants such as oilseed rape or related Brassica plants with altered oil composition properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; these include:
  • plants such as rape plants producing oil of high oleic acid content, as described, for example, in US 5,969,169, US 5,840,946 or US 6,323,392 or US 6,063,947;
  • plants such as oilseed rape plants which produce low linolenic acid oil, as described in US 6,270,828, US 6,169,190 or US 5,965,755.
  • plants such as oilseed rape plants which produce oil with a low saturated fatty acid content, such as e.g. As described in US 5,434,283.
  • transgenic plants which can be treated according to the invention are plants having one or more genes which code for one or more toxins, the transgenic plants sold under the following tradenames: YTELD GARD® (for example corn, cotton, Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example corn), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato).
  • YTELD GARD® for example corn, cotton, Soybeans
  • KnockOut® for example corn
  • BiteGard® for example maize
  • BT-Xtra® for example corn
  • StarLink® for example maize
  • Bollgard® cotton
  • Nucotn® cotton
  • Nucotn 33B® cotton
  • NatureGard® for example corn
  • Protecta® and NewLeaf® pota
  • Herbicide-tolerant crops to be mentioned are, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready® (glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example rapeseed) , IMI® (imidazolinone tolerance) and SCS® (sylphonylurea tolerance), for example corn.
  • Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).
  • transgenic plants which can be treated according to the invention are plants, the transformation events, or a combination of transformation events, for example, in the files of various national or regional authorities (see, for example, http://gmoinfo.jrc.it/gmp_browse.aspx and http://www.agbios.com/dbase.php).
  • the active compounds of the invention not only against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ecto- and endoparasites) such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice , Hair pieces, featherlings and fleas.
  • animal parasites ecto- and endoparasites
  • ticks ecto- and endoparasites
  • leather ticks such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice , Hair pieces, featherlings and fleas.
  • flies stinging and licking
  • parasitic fly larvae such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice , Hair pieces, featherlings and fleas.
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
  • Trimenopon spp. Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp , Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp.,
  • Morellia spp. Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,
  • siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
  • heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
  • Actinedida Prostigmata
  • Acaridida eg Acarapis spp.
  • Cheyletiella spp. Cheyletiella spp., Ornitrocheyletia 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.
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice.
  • arthropods are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice.
  • the use of the active compounds according to the invention takes place in the veterinary sector and in animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boilies, the feed-through process, suppositories, by parenteral administration, as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying, pouring (pour-on and spot-on ), washing, powdering and with the aid of active substance-containing moldings, such as collars, ear tags, tail marks, limb bands, holsters, marking devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boilies, the feed-through process, suppositories
  • parenteral administration as by injections (intr
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active ingredients in an amount of from 1 to 80% by weight, directly or apply after 100 to 10,000 times dilution or use as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • the compounds according to the invention have a high insecticidal activity against insects which destroy industrial materials.
  • insects By way of example and preferably without limiting however, the following insects are mentioned:
  • 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;
  • Non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
  • the ready-to-use agents may optionally contain further insecticides and optionally one or more fungicides.
  • the compounds according to the invention can be used to protect against fouling of objects, in particular hulls, sieves, nets, structures, quay systems and signal systems, which come into contact with seawater or brackish water.
  • the compounds according to the invention can be used alone or in combinations with other active substances as antifouling agents.
  • the active compounds are also suitable for controlling animal pests in household, hygiene and storage protection, in particular of insects, arachnids and mites, which are used in closed rooms, such as apartments, factory buildings, offices, vehicle cabins u.a. occurrence. They can be used to control these pests, alone or in combination with other active ingredients and adjuvants in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
  • Acarina for example, Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones e.g. Pseudoscorpiones chelifer, Pseudosco ⁇ iones cheiridium, Opiliones phalangium.
  • Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
  • Diptera e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys Calcitrans, Tipula paludosa.
  • Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuligrnosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
  • Application is in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • Pump and atomizer sprays misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • I-A-Ql-026 log P (HCOOH): 3.37
  • I-A-Ql-027 log P (HCOOH): 4.07
  • I-A-Ql-028 log P (HCOOH): 2.65
  • I-A-Ql-029 log P (HCOOH): 2.65
  • I-A-Ql-030 log P (HCOOH): 2.92
  • I-A-Ql-031 log P (HCOOH): 3.60
  • I-A-Ql-032 log P (HCOOH): 3.28
  • I-A-Ql-033 log P (HCOOH): 3.30
  • I-A-Ql-034 log P (HCOOH): 3.10
  • IA-Ql-035 log P (HCOOH): 2.80
  • IA-Ql-036 log P (HCOOH): 3.24
  • IA-Ql-037 log P (HCOOH): 3.33
  • I-A-Ql-038 log P (HCOOH): 3.33 I-A-Ql-039: log P (HCOOH): 2.89 I-A-Ql-040: log P (HCOOH): 3.44
  • I-A-Ql-041 log P (HCOOH): 3.19
  • I-A-Ql-042 log P (HCOOH): 2.84
  • I-A-Ql-043 log P (HCOOH): 3.61
  • I-A-Ql-044 log P (HCOOH): 3.10
  • I-A-Ql-045 log P (HCOOH): 2.64
  • I-A-Ql-046 log P (HCOOH): 3.24
  • I-A-Ql-047 log P (HCOOH): 2.64
  • I-A-Ql-048 log P (HCOOH): 2.39
  • I-A-Ql-049 log P (HCOOH): 4.11
  • I-A-Ql-053 log P (HCOOH): 2.66
  • I-A-Ql-054 log P (HCOOH): 2.18
  • I-A-Ql-055 log P (HCOOH): 2.47 o
  • I-A-Ql-056 log P (HCOOH): 2.80
  • I-A-Ql-057 log P (HCOOH): 2.35
  • I-A-Ql-058 log P (HCOOH): 2.11
  • I-A-Ql-059 log P (HCOOH): 2.30
  • I-A-Ql-060 log P (HCOOH): 2.27
  • I-A-Ql-061 log P (HCOOH): 2.29
  • I-A-Ql-062 log P (HCOOH): 3.09 I-A-Ql-063: log P (HCOOH): 3.53 I-A-Ql-064: log P (HCOOH): 3.31
  • I-A-Ql-068 log P (HCOOH): 4.32
  • I-A-Ql-069 log P (HCOOH): 4.14
  • I-A-Ql-070 log P (HCOOH): 4.10
  • IA-Ql-071 log P (HCOOH): 4.84
  • IA-Ql-072 log P (HCOOH): 4.82
  • IA-Ql-073 i og p (HCOOH): 4.51
  • I-A-Ql-074 log P (HCOOH): 4.33 I-A-Ql-075: log P (HCOOH): 3.28 I-A-Ql-076: log P (HCOOH): 2.98
  • IA-Ql-077 log P (HCOOH): 4.05
  • IA-Ql-078 log P (HCOOH): 4.83
  • IA-Ql-079 log P (HCOOH): 4.28
  • I-A-Ql-080 log P (HCOOH): 4.64
  • I-A-Ql-081 log P (HCOOH): 4.28
  • I-A-Ql-082 log P (HCOOH): 4.34
  • I-A-QI-083 log P (HCOOH): 3.84
  • I-A-QI-084 log P (HCOOH): 4.70
  • I-A-Ql-085 log P (HCOOH): 4.45
  • I-A-Ql-086 log P (HCOOH): 4.57 I-A-Ql-087: log P (HCOOH): 3.78 I-A-Ql-088: log P (HCOOH): 3.06
  • IA-Q2-004 IH NMR (CDC13). 3.86-4.16 (m, 2H), 7.34-7.42 (m, 3H), 7.86-8.02 (m, 3H), 8.15-8.17 ( m, 1H)
  • I-A-Q2-029 log P (HCOOH): 3.24
  • I-A-Q2-030 log P (HCOOH): 3.68
  • I-A-Q2-031 log P (HCOOH): 3.33
  • IA-Q2-032 log P (HCOOH): 3.63 IA-Q2-033: log P (HCOOH): 4.51 IA-Q2-034: log P (HCOOH): 1.94 IA-Q2 035: log P (HCOOH): 4.23 IA-Q2-036: log P (HCOOH): 3.68 IA-Q2-037: log P (HCOOH): 2.42
  • I-A-Q2-038 log P (HCOOH): 3.11 I-A-Q2-039: log P (HCOOH): 3.94 I-A-Q2-040: log P (HCOOH): 4.57
  • I-A-Q2-041 log P (HCOOH): 3.94
  • I-A-Q2-042 log P (HCOOH): 2.93
  • I-A-Q2-043 log P (HCOOH): 5.65
  • I-A-Q2-044 log P (HCOOH): 3.42
  • I-A-Q2-045 log P (HCOOH): 5.85
  • I-A-Q2-046 log P (HCOOH): 4.51
  • I-A-Q2-047 log P (HCOOH): 4.94
  • I-A-Q2-048 log P (HCOOH): 4.70
  • I-A-Q2-049 log P (HCOOH): 4.28
  • I-A-Q2-050 log P (HCOOH): 4.64 I-A-Q2-051: log P (HCOOH): 3.06 I-A-Q2-052: log P (HCOOH): 2.34
  • I-A-Q2-053 log P (HCOOH): 2.04
  • I-A-Q2-054 log P (HCOOH): 2.31
  • I-A-Q2-055 log P (HCOOH): 5.79 o
  • I-A-Q2-056 log P (HCOOH): 3.93
  • I-A-Q2-057 log P (HCOOH): 2.72
  • I-A-Q2-058 log P (HCOOH): 1.94
  • I-A-Q2-059 log P (HCOOH): 3.63
  • I-A-Q2-060 log P (HCOOH): 4.34
  • I-A-Q2-061 log P (HCOOH): 4.45
  • I-A-Q2-062 log P (HCOOH): 3.94
  • I-A-Q2-063 log P (HCOOH): 3.11
  • I-A-Q2-064 log P (HCOOH): 6.44
  • I-A-Q2-068 log P (HCOOH): 5.35
  • I-A-Q2-069 log P (HCOOH): 4.83
  • I-A-Q2-070 log P (HCOOH): 5.25
  • I-A-Q2-071 log P (HCOOH): 4.95
  • I-A-Q2-072 log P (HCOOH): 5.22
  • I-A-Q2-073 log P (HCOOH): 4.35
  • I-A-Q2-074 log P (HCOOH): 2.76
  • I-A-Q2-075 log P (HCOOH): 3.94
  • I-A-Q2-076 log P (HCOOH): 2.89
  • IA-Q2-077 log P (HCOOH): 4.17
  • IA-Q2-078 log P (HCOOH): 2.94
  • IA-Q2-079 log P (HCOOH): 3.37
  • I-A-Q2-080 log P (HCOOH): 2.38
  • I-A-Q2-081 log P (HCOOH): 3.58
  • I-A-Q2-082 log P (HCOOH): 2.46
  • I-A-Q2-083 log P (HCOOH): 3.68
  • I-A-Q2-084 log P (HCOOH): 3.89
  • I-A-Q2-085 log P (HCOOH): 3.47
  • I-A-Q2-086 log P (HCOOH): 3.68
  • I-A-Q2-087 log P (HCOOH): 2.80
  • I-A-Q2-088 log P (HCOOH): 2.99
  • I-A-Q2-089 log P (HCOOH): 3.89
  • I-A-Q2-090 log P (HCOOH): 4.11
  • I-A-Q2-091 log P (HCOOH): 3.09
  • I-A-Q2-095 log P (HCOOH): 4.51
  • I-A-Q2-096 log P (HCOOH): 5.35
  • I-A-Q2-097 log P (HCOOH): 4.64
  • I-A-Q2-098 log P (HCOOH): 4.36
  • I-A-Q2-099 log P (HCOOH): 5.42
  • I-A-Q2-100 log P (HCOOH): 4.96
  • I-A-Q2-101 log P (HCOOH): 4.71
  • I-A-Q2-102 log P (HCOOH): 4.06
  • I-A-Q2-103 log P (HCOOH): 5.19
  • I-A-Q2-104 log P (HCOOH): 4.46
  • I-A-Q2-105 log P (HCOOH): 3.61
  • I-A-Q2-106 log P (HCOOH): 4.30
  • I-A-Q2-110 log P (HCOOH): 2.69
  • I-A-Q2-111 log P (HCOOH): 4.17
  • I-A-Q2-112 log P (HCOOH): 4.34
  • I-A-Q2-133 log P (HCOOH): 4.44
  • I-A-Q2-134 log P (HCOOH): 3.11
  • I-A-Q2-135 log P (HCOOH): 4.06
  • I-A-Q2-136 log P (HCOOH): 3.80
  • I-A-Q2-137 log P (HCOOH): 3.40
  • I-A-Q2-138 log P (HCOOH): 4.21
  • IA-Q2-139 log P (HCOOH): 4.25
  • IA-Q2-140 log P (HCOOH): 3.93
  • IA-Q2-141 log P (HCOOH): 4.21
  • I-A-Q2-142 log P (HCOOH): 3.77
  • I-A-Q2-143 log P (HCOOH): 2.59
  • I-A-Q2-144 log P (HCOOH): 3.93
  • I-A-Q2-145 log P (HCOOH): 4.34
  • I-A-Q2-146 log P (HCOOH): 4.54
  • I-A-Q2-147 log P (HCOOH): 3.47
  • I-A-Q2-148 log P (HCOOH): 4.12 I-A-Q2-149: log P (HCOOH): 4.15 I-A-Q2-150: log P (HCOOH): 4.65
  • I-A-Q2-151 log P (HCOOH): 4.06
  • I-A-Q2-152 log P (HCOOH): 4.45
  • I-A-Q2-153 log P (HCOOH): 3.89
  • I-A-Q2-157 log P (HCOOH): 3.51
  • I-A-Q2-158 log P (HCOOH): 2.85
  • I-A-Q2-159 log P (HCOOH): 3.65
  • I-A-Q2-160 log P (HCOOH): 3.23
  • I-A-Q2-161 log P (HCOOH): 3.37
  • I-A-Q2-162 log P (HCOOH): 3.51
  • I-A-Q2-163 log P (HCOOH): 3.13
  • I-A-Q2-164 log P (HCOOH): 3.27
  • I-A-Q2-165 log P (HCOOH): 2.72
  • I-A-Q2-166 log P (HCOOH): 3.84 I-A-Q2-167: log P (HCOOH): 3.19 I-A-Q2-168: log P (HCOOH): 2.61
  • I-A-Q2-172 log P (HCOOH): 3.73 I-A-Q2-173: log P (HCOOH): 3.11 I-A-Q2-174: log P (HCOOH): 2.50
  • I-A-Q2-175 log P (HCOOH): 3.47
  • I-A-Q2-176 log P (HCOOH): 2.89
  • I-A-Q2-177 log P (HCOOH): 2.27
  • I-A-Q2-178 log P (HCOOH): 3.89
  • I-A-Q2-179 log P (HCOOH): 3.24
  • I-A-Q2-180 log P (HCOOH): 2.61
  • IA-Q2-181 log P (HCOOH): 2.98
  • IA-Q2-182 log P (HCOOH): 3.33
  • IA-Q2-183 log P (HCOOH): 3.11
  • I-A-Q2-184 log P (HCOOH): 2.76
  • I-A-Q2-185 log P (HCOOH): 2.14
  • I-A-Q2-186 log P (HCOOH): 2.42
  • I-A-Q2-190 log P (HCOOH): 3.15 I-A-Q2-191: log P (HCOOH): 2.57 I-A-Q2-192: log P (HCOOH): 2.89
  • I-A-Q2-193 log P (HCOOH): 3.42
  • I-A-Q2-194 log P (HCOOH): 3.37
  • I-A-Q2-195 log P (HCOOH): 2.96
  • I-A-Q2-202 log P (HCOOH): 4.22
  • I-A-Q2-203 log P (HCOOH): 3.77
  • I-A-Q2-204 log P (HCOOH): 4.22
  • I-A-Q2-205 log P (HCOOH): 4.17
  • I-A-Q2-206 log P (HCOOH): 4.29
  • I-A-Q2-207 log P (HCOOH): 4.83
  • I-A-Q2-208 log P (HCOOH): 3.19
  • I-A-Q2-209 log P (HCOOH): 3.02
  • I-A-Q2-210 log P (HCOOH): 4.28
  • I-A-Q2-211 log P (HCOOH): 2.89
  • I-A-Q2-212 log P (HCOOH): 2.27
  • I-A-Q2-213 log P (HCOOH): 4.89
  • I-A-Q2-214 log P (HCOOH): 4.45
  • I-A-Q2-215 log P (HCOOH): 4.76
  • I-A-Q2-216 log P (HCOOH): 2.57
  • I-A-Q2-217 log P (HCOOH): 4.70
  • I-A-Q2-218 log P (HCOOH): 3.33
  • I-A-Q2-219 log P (HCOOH): 4.05
  • I-A-Q2-220 log P (HCOOH): 4.11
  • I-A-Q2-221 log P (HCOOH): 4.51
  • I-A-Q2-222 log P (HCOOH): 4.76
  • IA-Q2-223 log P (HCOOH): 4.45
  • IA-Q2-224 log P (HCOOH): 3.78
  • IA-Q2-225 log P (HCOOH): 4.57
  • I-A-Q2-226 log P (HCOOH): 2.50
  • I-A-Q2-227 log P (HCOOH): 4.40
  • I-A-Q2-228 log P (HCOOH): 3.78
  • I-A-Q2-229 log P (HCOOH): 4.05
  • I-A-Q2-230 log P (HCOOH): 4.89
  • I-A-Q2-231 log P (HCOOH): 2.69
  • I-A-Q2-232 log P (HCOOH): 4.95
  • I-A-Q2-233 log P (HCOOH): 4.40
  • I-A-Q2-234 log P (HCOOH): 2.38
  • I-A-Q2-235 log P (HCOOH): 4.95
  • I-A-Q2-236 log P (HCOOH): 4.51
  • I-A-Q2-237 log P (HCOOH): 4.76
  • I-A-Q2-241 log P (HCOOH): 4.89
  • I-A-Q2-242 log P (HCOOH): 5.29
  • I-A-Q2-243 log P (HCOOH): 3.78
  • I-A-Q2-244 log P (HCOOH): 3.68 I-A-Q2-245: log P (HCOOH): 3.89 I-A-Q2-246: log P (HCOOH): 5.02
  • I-A-Q2-247 log P (HCOOH): 4.57
  • I-A-Q2-248 log P (HCOOH): 4.34
  • I-A-Q2-249 log P (HCOOH): 4.28
  • I-A-Q2-250 log P (HCOOH): 3.68
  • I-A-Q2-251 log P (HCOOH): 3.84
  • I-A-Q2-252 log P (HCOOH): 3.02
  • I-A-Q2-256 log P (HCOOH): 4.64
  • I-A-Q2-257 log P (HCOOH): 5.22
  • I-A-Q2-258 log P (HCOOH): 3.47
  • I-A-Q2-259 log P (HCOOH): 3.33 I-A-Q2-260: log P (HCOOH): 3.33 I-A-Q2-261: log P (HCOOH): 4.76
  • I-A-Q2-262 log P (HCOOH): 3.28
  • I-A-Q2-263 log P (HCOOH): 5.08
  • I-A-Q2-264 log P (HCOOH): 1.99
  • IA-Q2-265 log P (HCOOH): 3.63
  • IA-Q2-266 log P (HCOOH): 4.89
  • IA-Q2-267 log P (HCOOH): 6.14
  • I-A-Q2-268 log P (HCOOH): 4.45 I-A-Q2-269: log P (HCOOH): 4.57 I-A-Q2-270: log P (HCOOH): 3.84
  • I-A-Q2-271 log P (HCOOH): 4.45 I-A-Q2-272: log P (HCOOH): 3.24 I-A-Q2-273: log P (HCOOH): 2.98
  • I-A-Q2-274 log P (HCOOH): 4.95
  • I-A-Q2-275 log P (HCOOH): 4.47
  • I-A-Q2-276 log P (HCOOH): 4.50
  • I-A-Q2-277 log P (HCOOH): 4.56
  • I-A-Q2-278 log P (HCOOH): 4.30
  • I-A-Q2-279 log P (HCOOH): 4.43
  • I-A-Q2-283 log P (HCOOH): 4.12
  • I-A-Q2-284 log P (HCOOH): 4.32
  • I-A-Q2-285 log P (HCOOH): 4.95
  • I-A-Q2-286 log P (HCOOH): 4.89
  • I-A-Q2-287 log P (HCOOH): 5.33
  • I-A-Q2-288 log P (HCOOH): 4.40
  • I-A-Q2-289 log P (HCOOH): 4.95
  • I-A-Q2-290 log P (HCOOH): 4.00
  • I-A-Q2-291 log P (HCOOH): 3.84
  • I-A-Q2-292 log P (HCOOH): 3.53
  • I-A-Q2-293 log P (HCOOH): 3.11
  • I-A-Q2-294 log P (HCOOH): 4.95
  • I-A-Q2-298 log P (HCOOH): 4.64 I-A-Q2-299: log P (HCOOH): 4.51 I-A-Q2-300: log P (HCOOH): 5.40
  • I-A-Q2-301 log P (HCOOH): 3.75 I-A-Q2-302: log P (HCOOH): 3.61 I-A-Q2-303: log P (HCOOH): 3.70
  • I-A-Q2-304 log P (HCOOH): 4.00
  • I-A-Q2-305 log P (HCOOH): 3.75
  • I-A-Q2-306 log P (HCOOH): 3.24
  • IA-Q2-307 log P (HCOOH): 3.27
  • IA-Q2-308 log P (HCOOH): 3.23
  • IA-Q2-309 log P (HCOOH): 3.65
  • I-A-Q2-310 log P (HCOOH): 3, 70 I-A-Q2-311: log P (HCOOH): 3.27 I-A-Q2-312: log P (HCOOH): 3.42
  • I-A-Q2-313 log P (HCOOH): 3.85 I-A-Q2-314: log P (HCOOH): 3.65 I-A-Q2-315: log P (HCOOH): 3.37
  • I- ⁇ -Q2-316 log P (HCOOH): 3.65 I-A-Q2-317: log P (HCOOH): 3.32 I-A-Q2-318: log P (HCOOH): 4.23
  • I-A-Q2-319 log P (HCOOH): 2.80
  • I-A-Q2-320 log P (HCOOH): 3.23
  • I-A-Q2-321 log P (HCOOH): 4.00
  • I-A-Q2-325 log P (HCOOH): 2.85
  • I-A-Q2-326 log P (HCOOH): 2.51
  • I-A-Q2-327 log P (HCOOH): 2.73
  • I-A-Q2-328 log P (HCOOH): 2.48 I-A-Q2-329: log P (HCOOH): 2.59 I-A-Q2-330: log P (HCOOH): 3.12
  • I-A-Q2-331 log P (HCOOH): 2.85 I-A-Q2-332: log P (HCOOH): 2.59 I-A-Q2-333: log P (HCOOH): 2.59
  • I-A-Q2-334 log P (HCOOH): 2.59
  • I-A-Q2-335 log P (HCOOH): 3.04
  • I-A-Q2-336 log P (HCOOH): 2.76
  • I-A-Q2-340 log P (HCOOH): 3.56
  • I-A-Q2-341 log P (HCOOH): 3.46
  • I-A-Q2-342 log P (HCOOH): 3.85
  • I-A-Q2-343 log P (HCOOH): 4.57 I-A-Q2-344: log P (HCOOH): 2.84 I-A-Q2-345: log P (HCOOH): 2.69
  • I-A-Q2-346 log P (HCOOH): 2.80
  • I-A-Q2-347 log P (HCOOH): 3.11
  • I-A-Q2-348 log P (HCOOH): 2.84
  • IA-Q2-349 log P (HCOOH): 2.04
  • IA-Q2-350 log P (HCOOH): 2.34
  • IA-Q2-351 log P (HCOOH): 2.27
  • I-A-Q2-352 log P (HCOOH): 2.76 I-A-Q2-353: log P (HCOOH): 2.84 I-A-Q2-354: log P (HCOOH): 2.31
  • I-A-Q2-355 log P (HCOOH): 2.50
  • I-A-Q2-356 log P (HCOOH): 2.93
  • I-A-Q2-357 log P (HCOOH): 2.72
  • I-A-Q2-358 log P (HCOOH): 2.80
  • I-A-Q2-359 log P (HCOOH): 2.34
  • I-A-Q2-360 log P (HCOOH): 3.47
  • I-A-Q2-361 log P (HCOOH): 1.91
  • I-A-Q2-362 log P (HCOOH): 2.27
  • I-A-Q2-363 log P (HCOOH): 3.19
  • I-A-Q2-367 log P (HCOOH): 1.59
  • I-A-Q2-368 log P (HCOOH): 1.79
  • I-A-Q2-369 log P (HCOOH): 1.52
  • I-A-Q2-370 log P (HCOOH): 1.64
  • I-A-Q2-371 log P (HCOOH): 1,
  • I-A-Q2-372 log P (HCOOH): 1.61
  • I-A-Q2-373 log P (HCOOH): 1.64
  • I-A-Q2-374 log P (HCOOH): 1.66
  • I-A-Q2-375 log P (HCOOH): 2.04
  • I-A-Q2-376 log P (HCOOH): 1.79 I-A-Q2-377: log P (HCOOH): 2.80 I-A-Q2-378 log P (HCOOH): 2.61
  • I-A-Q2-382 log P (HCOOH): 2.84
  • I-A-Q2-383 log P (HCOOH): 3.94
  • I-A-Q2-384 log P (HCOOH): 4.53
  • I-A-Q2-385 log P (HCOOH): 4.60
  • I-A-Q2-386 log P (HCOOH): 3.77
  • I-A-Q2-387 log P (HCOOH): 4.32
  • I-A-Q2-388 log P (HCOOH): 3.37
  • I-A-Q2-389 log P (HCOOH): 4.35
  • I-A-Q2-390 log P (HCOOH): 3.41
  • IA-Q2-391 log P (HCOOH): 3.57 IA-Q2-392: log P (HCOOH): 3.51 IA-Q2-393: log P (HCOOH): 4.82
  • I-A-Q2-394 log P (HCOOH): 3.70 I-A-Q2-395: log P (HCOOH): 4.43 I-A-Q2-396: log P (HCOOH): 4.59
  • I-A-Q2-397 log P (HCOOH): 4.69
  • I-A-Q2-398 log P (HCOOH): 3.59
  • I-A-Q2-399 log P (HCOOH): 5.26
  • I-A-Q2-400 log P (HCOOH): 4.36
  • I-A-Q2-401 log P (HCOOH): 4.93
  • I-A-Q2-402 log P (HCOOH): 3.89
  • I-A-Q2-403 log P (HCOOH): 4.34
  • I-A-Q2-404 log P (HCOOH): 4.81
  • I-A-Q2-405 log P (HCOOH): 4.84
  • I-A-Q2-410 log P (HCOOH): 3.94
  • I-A-Q2-411 log P (HCOOH): 3.17
  • I-A-Q2-412 log P (HCOOH): 3.29
  • I-A-Q2-413 log P (HCOOH): 3.37
  • I-A-Q2-414 log P (HCOOH): 2.72
  • I-A-Q2-415 log P (HCOOH): 2.71
  • I-A-Q2-416 log P (HCOOH): 3.81 I-A-Q2-417: log P (HCOOH): 3.13 I-A-Q2-418: log P (HCOOH): 3.22
  • I-A-Q2-419 log P (HCOOH): 2.68 I-A-Q2-420: log P (HCOOH): 2.81 I-A-Q2-421: log P (HCOOH): 2.53
  • I-A-Q3-021 log P (HCOOH): 4.48
  • I-A-Q3-022 log P (HCOOH): 4.12
  • I-A-Q3-023 log P (HCOOH): 3.70
  • IA-Q4-006 IH NMR (CDCl3) 8.27-8.23 (m, 1H), 8.20-8.17 (m, 1H), 8.15-8.11 (m, 2 H), 7.44-7.43 (m, 1H), 7.37-7.37 (m, 2H)
  • I-A-Q4-009 for spectroscopic data see protocol under general synthesis instructions
  • I-A-Q4-010 for spectroscopic data see protocol under general synthesis instructions
  • I-A-Q4-011 for spectroscopic data see protocol under general synthesis procedure
  • I-A-Q4-012 spectroscopic data see protocol under general synthetic procedure 5
  • I-A-Q4-013 For spectroscopic data see protocol under general synthesis procedure
  • I-A-Q4-014 log P (HCOOH): 5.76
  • I-A-Q4-015 log P (HCOOH): 3.47
  • I-A-Q4-016 log P (HCOOH): 5.76
  • I-A-Q4-017 log P (HCOOH): 6.71
  • I-A-Q4-018 log P (HCOOH): 6.50
  • I-A-Q4-019 log P (HCOOH): 3.94
  • I-A-Q4-020 log P (HCOOH): 5.22
  • I-A-Q4-021 log P (HCOOH): 4.70
  • I-A-Q4-022 log P (HCOOH): 5.22
  • I-A-Q4-023 log P (HCOOH): 4.57
  • I-A-Q4-024 log P (HCOOH): 5.36
  • I-A-Q4-025 log P (HCOOH): 5.51
  • I-A-Q4-026 log P (HCOOH): 5.02
  • I-A-Q4-027 log P (HCOOH): 5.73
  • I-A-Q4-028 log P (HCOOH): 5.64
  • I-A-Q4-029 log P (HCOOH): 4.05
  • I-A-Q4-030 log P (HCOOH): 4.57
  • I-A-Q4-031 log P (HCOOH): 3.78
  • I-A-Q4-032 log P (HCOOH): 3.89
  • I-A-Q4-033 log P (HCOOH): 3.84
  • I-A-Q4-034 log P (HCOOH): 4.40
  • I-A-Q4-035 log P (HCOOH): 3.78
  • I-A-Q4-036 log P (HCOOH): 3.58
  • I-A-Q4-037 log P (HCOOH): 4.05
  • IA-Q4-038 log P (HCOOH): 3.84
  • IA-Q4-039 log P (HCOOH): 4.40
  • IA-Q4-040 log P (HCOOH): 5.29
  • I-A-Q4-041 log P (HCOOH): 4.95
  • I-A-Q4-042 log P (HCOOH): 5.22
  • I-A-Q4-043 log P (HCOOH): 5.44
  • I-A-Q4-044 log P (HCOOH): 5.02
  • I-A-Q4-045 log P (HCOOH): 4.11
  • I-A-Q4-046 log P (HCOOH): 4.46
  • I-A-Q4-047 log P (HCOOH): 4.95
  • I-A-Q4-048 log P (HCOOH): 5.02
  • I-A-Q4-049 log P (HCOOH): 4.51
  • I-A-Q4-050 log P (HCOOH): 4.64
  • I-A-Q4-051 log P (HCOOH): 5.29
  • I-A-Q4-052 log P (HCOOH): 5.02

Abstract

The present invention relates to novel 4-phenyl-1H-pyrazoles and to the use thereof as insecticides and/or parasiticides and to a method for the production thereof and to compositions that contain such phenylpyrazoles.

Description

Insektizide 4-Phenyl-lH-pyrazole Insecticides 4-phenyl-1H-pyrazoles
Die vorliegende Erfindung betrifft neue 4-Phenyl-lH-pyrazole und ihre Verwendung als Insektizide und/oder Parasitizide sowie Verfahren zu ihrer Herstellung und Mittel, die solche Phenylpyrazole enthalten.The present invention relates to novel 4-phenyl-1H-pyrazoles and their use as insecticides and / or parasiticides and to processes for their preparation and to compositions containing such phenylpyrazoles.
In der EP 846686 werden 4-Phenyl-lH-pyrazole (A) beschrieben, die parasitizide, Insektizide und nematizide Wirkung aufweisen. Die Definitionen der Substituenten R3, R5 und R7 sind wie folgt festgelegt:EP 846 686 describes 4-phenyl-1H-pyrazoles (A) which have parasiticidal, insecticidal and nematicidal activity. The definitions of the substituents R 3 , R 5 and R 7 are defined as follows:
R Halogen;R is halogen;
R5 H, Ci.6-Alkyl, gegebenenfalls substituiert mit einem oder mehreren Halogenatomen,R 5 H, Ci. 6- alkyl, optionally substituted by one or more halogen atoms,
Ci-6-Alkoxy, gegebenenfalls substituiert mit einem oder mehreren Halogenatomen, oder SF5;Ci- 6 alkoxy optionally substituted with one or more halogen atoms, or SF 5;
R7 Halogen.R 7 is halogen.
Li der WO 2008/077483 werden Pyrimidinylpyrazole (B) beschrieben, die insektizide und/oder ppaarraassiittiizziiddee Wirkung aufweisen. Die Definitionen der Substituenten R3 und n sind wie folgt festgelegt:Li WO 2008/077483 pyrimidinylpyrazoles (B) are described which have insecticidal and / or ppaarraassiittiizziiddee effect. The definitions of the substituents R 3 and n are defined as follows:
R Halogen, Alkyl, Haloalkyl, Alkoxy oder DialkylaminoR is halogen, alkyl, haloalkyl, alkoxy or dialkylamino
n 0 oder 1 Meegalla et al. beschreiben die Synthese und insektizide Aktivität von 3-Thiomethyl-4- (hetero)aryl-5-amino-l-phenylpyrazolen als GABA-Kanal-Blocker (Bioorganic & Medicinal Chemistry Letters (2004), 14, 4949-4953).n 0 or 1 Meegalla et al. describe the synthesis and insecticidal activity of 3-thiomethyl-4- (hetero) aryl-5-amino-1-phenylpyrazoles as GABA channel blockers (Bioorganic & Medicinal Chemistry Letters (2004), 14, 4949-4953).
In der WO 2007/048734 werden 5-Aminopyrazole (C) zur Bekämpfung von pflanzenpathogenen Schadpilzen beschrieben. Die Definitionen der Substituenten R3, R4 und R5 sind wie folgt festgelegt:WO 2007/048734 describes 5-aminopyrazoles (C) for controlling phytopathogenic harmful fungi. The definitions of the substituents R 3 , R 4 and R 5 are defined as follows:
R3, R4, R5 unabhängig voneinander Wasserstoff, Halogen, Cyano, Hydroxy, Mercapto, C1- Cio-Alkyl, CrCi0-Halogenalkyl, C3-C8-Cycloalkyl, C2-C10- Alkenyl, C2-C]0-Alkinyl, CrC6-Alkoxy, CrC6-Alkylthio, C,-C6-Alkoxy-CrC6-alkyl, NRARB, Phenyl, Phenoxy oder PhenylthioR 3, R 4, R 5 are independently hydrogen, halogen, cyano, hydroxy, mercapto, C 1 - Cio-alkyl, C r 0 Ci haloalkyl, C 3 -C 8 cycloalkyl, C 2 -C 10 - alkenyl, C 2 -C ] 0 alkynyl, C r C 6 alkoxy, C r C 6 alkylthio, C, -C 6 alkoxy C r C 6 alkyl, NR A R B , phenyl, phenoxy or phenylthio
RA, RB Wasserstoff oder C,-C6-AlkylR A , R B are hydrogen or C, -C 6 alkyl
Gegenstand der vorliegenden Erfindung sind neue 4-Phenyl-lH-pyrazole der Formel (I),The present invention relates to novel 4-phenyl-1H-pyrazoles of the formula (I)
in welcherin which
M für eine der nachstehend aufgeführten Gruppierungen steht: M stands for one of the groupings listed below:
Hieraus ergeben sich 4-Phenyl-lH-pyrazole der Formel (I-A) und (I-B),This results in 4-phenyl-lH-pyrazoles of the formula (I-A) and (I-B),
in welcher in which
A1 und A2 unabhängig voneinander für Stickstoff oder C-R4 stehen;A 1 and A 2 are independently nitrogen or CR 4 ;
G1, G2, G3, G4 und G5 für Wasserstoff oder einen Substituenten stehen, unabhängig voneinander ausgewählt aus: Halogen, Alkyl, Alkenyl, Alkinyl, Haloalkyl, SF5, Hydroxy, Alkoxy, Alkoxyalkyl, Alkoxyalkoxy, Cycloalkyl, Alkenyloxy, Alkinyloxy, Cycloalkylalkoxy, Haloalkoxy, Haloalkoxyalkyl, Alkylsulfanyl, Haloalkylsulfanyl, Alkylsulfinyl, Haloalkylsulfinyl, Alkylsul- fonyl, Haloalkylsulfonyl, Cyano, Alkylcarbonyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Trialkylsilyl, Nitro, Amino, Alkylamino, Dialkylamino, Alkylsulfonylamino, Dialkylsulfonylamino, -CR5=NO- R5, -CR5=NO-Haloalkyl oder Formyl, wobei vicinale Alkyl-, Haloalkyl, Alkoxy- und/oder Haloalkoxygruppen zusammen mit den Kohlenstoffatomen, an die sie gebunden sind, ein fünf- bis sechsgliedriges cyclisches System bilden können, das 0 bis 2 Sauerstoffatome enthält, und dessen Alkylanteil gegebenenfalls mit einem oder mehreren Fluoratomen substituiert sein kann;G 1 , G 2 , G 3 , G 4 and G 5 are hydrogen or a substituent independently selected from: halogen, alkyl, alkenyl, alkynyl, haloalkyl, SF 5 , hydroxy, alkoxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, alkenyloxy , Alkynyloxy, cycloalkylalkoxy, haloalkoxy, haloalkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, carboxyl, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, trialkylsilyl, nitro, amino, alkylamino, dialkylamino , Alkylsulfonylamino, dialkylsulfonylamino, -CR 5 = NO-R 5 , -CR 5 = NO-haloalkyl or formyl, wherein vicinal alkyl, haloalkyl, alkoxy and / or haloalkoxy groups together with the carbon atoms to which they are attached, a five - can form to six-membered cyclic system containing 0 to 2 oxygen atoms, and its alkyl moiety optionally with one or more fluorato may be substituted;
Q für einen Substituenten steht, ausgewählt aus Q1, Q2, Q3 oder Q4;Q is a substituent selected from Q 1 , Q 2 , Q 3 or Q 4 ;
Q1 für eine der nachstehend aufgeführten heterocyclischen Gruppierungen steht;Q 1 is one of the heterocyclic groupings listed below;
(Z1) (Z2) (Z=) (Z4) (Z5) (Z 1 ) (Z 2 ) (Z =) (Z 4 ) (Z 5 )
(Z6) (Z7) (Z8) (Z9) (Z10) (Z 6 ) (Z 7 ) (Z 8 ) (Z 9 ) (Z 10 )
(Z") (Z12) (Z13) (Z14) (Z15) (Z ") (Z 12 ) (Z 13 ) (Z 14 ) (Z 15 )
(Z16) (Z17) (Z18) (Z19) (Z20) (Z 16 ) (Z 17 ) (Z 18 ) (Z 19 ) (Z 20)
(Z21) (Z22) (Z23) (Z24)(Z 21 ) (Z 22) (Z 23) (Z 24 )
wobeiin which
W1 und W2 unabhängig voneinander für Sauerstoff oder Schwefel stehen,W 1 and W 2 are independently oxygen or sulfur,
undand
R6, R6', R6", R6'" und R7 die unten stehende Bedeutung haben;R 6 , R 6 ' , R 6 " , R 6'" and R 7 are as defined below;
Q" für C(W K)xNTRD8D R 9" steht;Q "stands for C (WK) xNTRD 8 DR 9";
QJ für C(R 1i0υTR> 1"K)XNTRΓ> 85DR9y steht;Q J is C (R 1 i 0 υ TR> 1 "K) XNTRΓ> 8 5 DR9 y ;
Q4 für Cyano (wobei R1 nicht für Amino steht), Nitro, Amino, COOH, COOR12, Fluor (falls R3 verschieden von Chlor ist), Chlor (falls R3 verschieden von Chlor, COOH, CH2CH2OMe und OMe ist), Brom, Iod, SR12 (wobei R1 nicht für Amino steht, falls R12 für Alkyl steht), S(O)R12, S(O)2R12 oder S(O)2NR8R9 steht;Q 4 for cyano (where R 1 is not amino), nitro, amino, COOH, COOR 12 , fluorine (if R 3 is other than chlorine), chlorine (if R 3 is different from chlorine, COOH, CH 2 CH 2 OMe and OMe), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 , S (O) 2 R 12 or S (O) 2 NR 8 R 9 stands;
R1 für Wasserstoff, Halogen, Alkylsulfanyl, Alkylsulfmyl, Alkylsulfonyl, Cyano, Amino, Z16 oder NR13R14 steht;R 1 is hydrogen, halogen, alkylsulfanyl, alkylsulfmyl, alkylsulfonyl, cyano, amino, Z 16 or NR 13 R 14 ;
R2 für Wasserstoff, Halogen, Alkyl, Alkenyl, Alkinyl, Haloalkyl, Cycloalkyl, Hydroxy- alkyl, Alkoxyalkyl, Haloalkoxyalkyl, Alkoxyhaloalkyl, Alkylsulfanylalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Haloalkylsulfanylalkyl, Haloalkylsulfinylalkyl, Haloalkylsulfonylalkyl Cyclo- alkylalkyl, Phenylalkyl, Heteroarylalkyl, Heterocyclylalkyl, Phenyl, oder auch für Arylhaloalkyl, Haloalkyloxyhaloalkyloxyhaloalkyl, Heterocyclyl, Alkylsulfanyl, Alkylsulfmyl, Alkylsulfonyl oder steht;R 2 is hydrogen, halogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, alkylsulfanylalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylsulfanylalkyl, haloalkylsulfinylalkyl, haloalkylsulfonylalkyl, cycloalkylalkyl, phenylalkyl, heteroarylalkyl, heterocyclylalkyl, phenyl, or arylhaloalkyl, haloalkyloxyhaloalkyloxyhaloalkyl, heterocyclyl, alkylsulfanyl, alkylsulfmyl, alkylsulfonyl or;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen, Alkyl, Haloalkyl, Alkoxy, Alkylsulfanyl, Alkylsulfmyl, Alkylsulfonyl, Monoalkylamino, Dialkylarnino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy oder Cyano.where a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano; a heterocyclyl radical is optionally substituted by -OH / = O, -SH / SS, -NH 2 , halogen, alkyl, haloalkyl, alkoxy, alkylsulfanyl, alkylsulfmyl, alkylsulfonyl, monoalkylamino, dialkylamino, nitro or cyano; and an alkanediyl radical bonded to phenyl, heteroaryl or heterocyclyl is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy or cyano.
R3 für Halogen, Alkyl, Alkenyl, Alkinyl, Haloalkyl, Cycloalkyl, Alkoxyalkyl, Alkylcarbonyloxyalkyl, Alkylsulfanylalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Hydroxy, Z16, Alkoxy, Acylamino, Alkoxycarbonylamino, Alkenyloxy, Alkinyloxy, Cycloalkylalkoxy, HaIo- alkoxy, Alkylsulfanyl, Haloalkylsulfanyl, Alkylsulfmyl, Haloalkylsulfinyl, Alkylsulfonyl, Haloalkylsulfonyl, Cyano, Alkylcarbonyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Alkylsulfonyl- aminocarbonyl, Trialkylsilyl, Nitro, Amino, Alkylamino, Dialkylamino, Alkylsulfonylamino, Dialkylsulfonylamino, -CR5=NO-R5, -CR5=NO-Haloalkyl oder Formyl steht;R 3 is halogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkylcarbonyloxyalkyl, alkylsulfanylalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, hydroxy, Z 16 , alkoxy, acylamino, alkoxycarbonylamino, alkenyloxy, alkynyloxy, cycloalkylalkoxy, haloalkoxy, alkylsulfanyl, haloalkylsulfanyl, Alkylsulfmyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, carboxyl, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonylaminocarbonyl, trialkylsilyl, nitro, amino, alkylamino, dialkylamino, alkylsulfonylamino, dialkylsulfonylamino, -CR 5 = NO- R 5 is -CR 5 = NO-haloalkyl or formyl;
R4 für Wasserstoff, Cyano, Nitro, Alkyl, Haloalkyl, Halogen oder Alkoxy steht;R 4 is hydrogen, cyano, nitro, alkyl, haloalkyl, halogen or alkoxy;
R5 für Wasserstoff oder Alkyl steht;R 5 is hydrogen or alkyl;
R6, R6 , R6 , R6 unabhängig voneinander für Wasserstoff, Amino, Hydroxy, Mercapto,R 6 , R 6 , R 6 , R 6 independently of one another represent hydrogen, amino, hydroxyl, mercapto,
Nitro, Cyano, Carboxyl, Halogen, Alkyl, Haloalkyl, Alkenyl, Alkinyl, Cycloalkyl, Alkoxy, Haloalkoxy, Alkenyloxy, Alkinyloxy, Alkoxycarbonyl, Alkylsulfanyl, Haloalkylsulfanyl,Nitro, cyano, carboxyl, halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, alkoxycarbonyl, alkylsulfanyl, haloalkylsulfanyl,
Alkylsulfmyl, Haloalkylsulfinyl, Alkylsulfonyl, Haloalkylsulfonyl, Aminocarbonyl, Aminothio- carbonyl, CR5=NO-R5, -CR5=NO-Haloalkyl, Formyl, Alkylamino, Dialkylamino, Phenyl, Heteroaryl, Heteroarylalkyl oder Heterocyclylalkyl stehen;Alkylsulfmyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aminocarbonyl, aminothio carbonyl, CR 5 = NO-R 5 , -CR 5 = NO-haloalkyl, formyl, alkylamino, dialkylamino, phenyl, heteroaryl, heteroarylalkyl or heterocyclylalkyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =O, -SH / =S, -NH2, Halogen, Alkyl, Haloalkyl,where a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano; a heterocyclyl radical is optionally substituted by -OH / OO, -SH / SS, -NH 2 , halogen, alkyl, haloalkyl,
Alkoxy, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl, Monoalkylamino, Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy oder Cyano;Alkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, monoalkylamino, dialkylamino, nitro or cyano; and an alkanediyl radical attached to phenyl, heteroaryl or heterocyclyl is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy or cyano;
R7 für Wasserstoff, Amino, Hydroxy, Cyano, Alkyl, Haloalkyl, Alkenyl, Alkinyl, Cyclo- alkyl, Alkoxy, Alkenyloxy, Alkinyloxy, Alkoxycarbonyl, Alkylcarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Phenyl, Phenylalkyl, Heteroarylalkyl oder Heterocyclylalkyl steht;R 7 is hydrogen, amino, hydroxy, cyano, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkenyloxy, alkynyloxy, alkoxycarbonyl, alkylcarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, phenyl, phenylalkyl, heteroarylalkyl or heterocyclylalkyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen, Alkyl, Haloalkyl,where a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano; a heterocyclyl radical is optionally substituted by -OH / = O, -SH / SS, -NH 2 , halogen, alkyl, haloalkyl,
Alkoxy, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl, Monoalkylamino, Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy oder Cyano undAlkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, monoalkylamino, dialkylamino, nitro or cyano; and an alkanediyl radical attached to phenyl, heteroaryl or heterocyclyl optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy or cyano and
wobei gegebenenfalls zwei benachbarte Reste aus R6, R6 , R6 , R6 und R7 zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-, -SO2-, -NH- oder -N-Alkyl- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstoffkette unterbrochenes Alkandiyl oder Alkendiyl mit jeweils 2 bis 5 Kohlenstoffatomen stehen;where appropriate two adjacent radicals of R 6 , R 6 , R 6 , R 6 and R 7 together represent optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N-alkyl- at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
R8 und R9 unabhängig voneinander für Wasserstoff, Alkyl, Haloalkyl, AlkenylR 8 and R 9 are independently hydrogen, alkyl, haloalkyl, alkenyl
(gegebenenfalls substituiert durch Halogen, Alkyl, Haloalkyl oder Cyano), Alkinyl, Cycloalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Haloalkyl, Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten), Cycloalkylalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Haloalkyl, Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten, am Alkylteil gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Alkyl, Haloalkyl, Alkoxy oder Cyano), Cycloalkylcarbonylheterocyclyl, Alkyloxy- carbonylheterocyclyl, Alkylsulfϊnylalkyl, Alkylsulfanylalkyl, Alkylsulfonylalkyl, Hydroxyalkyl, Heterocyclylcarbonylalkyl, Heteroarylcarbonylaminoalkyl, Haloalkoxyalkyl, Alkylthiocarbonyl, Dialkylaminocarbonyl, Alkylaminocarbonyl, Haloalkylaminocarbonyl, Alkoxy, Alkenyloxy, Alkinyloxy, Alkoxyalkyl, Alkylcarbonylalkyl, C(R10R1 ')CR5=NO-R5, Alkylsulfonyl, Alkyl- carbonyl, Haloalkylcarbonyl, Alkenylcarbonyl, Alkinylcarbonyl, Cycloalkylcarbonyl, Alkoxy- carbonyl, Alkenyloxycarbonyl, Alkinyloxycarbonyl, Alkoxyalkylcarbonyl, Phenylsulfonyl, Phenyl, Heteroaryl, Heterocyclyl, Phenylalkyl, Heteroarylalkyl, Heterocyclylalkyl, Phenylcarbonyl, Heteroarylcarbonyl, Heterocyclylcarbonyl, Phenylalkylcarbonyl, Heteroarylalkylcarbonyl, Heterocyclylalkylcarbonyl, Phenoxycarbonyl oder Phenylalkoxycarbonyl stehen;(optionally substituted by halogen, alkyl, haloalkyl or cyano), alkynyl, cycloalkyl (optionally mono- or polysubstituted by halogen, haloalkyl, alkyl or fused to an aromatic or heteroaromatic radical), cycloalkylalkyl (optionally mono- or polysubstituted on the cycle by halogen, haloalkyl, alkyl or fused to an aromatic or heteroaromatic, the alkyl part optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy or cyano), Cycloalkylcarbonylheterocyclyl, alkyloxycarbonylheterocyclyl, Alkylsulfϊnylalkyl, Alkylsulfanylalkyl, Alkylsulfonylalkyl, hydroxyalkyl, Heterocyclylcarbonylalkyl, Heteroarylcarbonylaminoalkyl, haloalkoxyalkyl, alkylthiocarbonyl, Dialkylaminocarbonyl, alkylaminocarbonyl, haloalkylaminocarbonyl, alkoxy, alkenyloxy, alkynyloxy, alkoxyalkyl, alkylcarbonylalkyl, C (R 10 R 1 ') CR 5 = NO-R 5 , alkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, Alkenyloxycarbonyl, alkynyloxycarbonyl, alkoxyalkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl, heterocyclyl, phenylalkyl, heteroarylalkyl, heterocyclylalkyl, phenylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, phenylalkylcarbonyl, heteroarylalkylcarbonyl, heterocyclylalkylcarbonyl, phenoxycarbonyl or phenylalkoxycarbonyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen, Alkyl, Haloalkyl,where a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano; a heterocyclyl radical is optionally substituted by -OH / = O, -SH / SS, -NH 2 , halogen, alkyl, haloalkyl,
Alkoxy, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl, Monoalkylamino, Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy oder Cyano undAlkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, monoalkylamino, dialkylamino, nitro or cyano; and an alkanediyl radical attached to phenyl, heteroaryl or heterocyclyl optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy or cyano and
wobei gegebenenfalls R8 / R9 zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-, -SO2-, -NH- oder -N-Alkyl- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstoffkette unterbrochenes Alkandiyl oder Alkendiyl mit jeweils 2 bis 5 Kohlenstoffatomen stehen;where appropriate, R 8 / R 9 together for optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N-alkyl- at the beginning (or at the end) or within the hydrocarbon chain are interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
R10 und R11 unabhängig voneinander für Wasserstoff, Alkyl, Haloalkyl oder Cyano stehen;R 10 and R 11 are independently hydrogen, alkyl, haloalkyl or cyano;
R12 für Alkyl oder Haloalkyl steht;R 12 is alkyl or haloalkyl;
R13 und R14 unabhängig voneinander für Wasserstoff, Alkyl, Haloalkyl, Alkenyl, Alkinyl, Alkoxyalkyl, Alkylcarbonylalkyl, C(R10R11^=NO-R5, Alkylsulfonyl, Alkylcarbonyl, Haloalkylcarbonyl, Alkenylcarbonyl, Alkinylcarbonyl, Cycloalkylcarbonyl, Alkoxycarbonyl, Alkenyloxy- carbonyl, Alkinyloxycarbonyl, Alkoxyalkylcarbonyl, Phenylsulfonyl, Phenyl, Heteroaryl, Heterocyclyl, Phenylalkyl, Heteroarylalkyl, Heterocyclylalkyl, Phenylcarbonyl, Heteroarylcarbonyl, Heterocyclylcarbonyl, Phenylalkylcarbonyl, Heteroarylalkylcarbonyl, Heterocyclylalkylcarbonyl, Phenoxycarbonyl oder Phenylalkoxycarbonyl stehen;R 13 and R 14 are independently hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, alkoxyalkyl, alkylcarbonylalkyl, C (R 10 R 11 ^ = NO-R 5 , alkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, alkenyloxy - carbonyl, alkynyloxycarbonyl, alkoxyalkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl, heterocyclyl, phenylalkyl, heteroarylalkyl, heterocyclylalkyl, phenylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, phenylalkylcarbonyl, heteroarylalkylcarbonyl, heterocyclylalkylcarbonyl, phenoxycarbonyl or phenylalkoxycarbonyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen, Alkyl, Haloalkyl,where a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano; a heterocyclyl radical is optionally substituted by -OH / = O, -SH / SS, -NH 2 , halogen, alkyl, haloalkyl,
Alkoxy, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl, Monoalkylamino, Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy oder CyanoAlkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, monoalkylamino, dialkylamino, nitro or cyano; and an alkanediyl radical bonded to phenyl, heteroaryl or heterocyclyl is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy or cyano
oderor
R13 und R14 als Imin die Gruppierung =CR5-NR15R16 oder =CR5-OR12 bilden;R 13 and R 14 as imine form the grouping = CR 5 -NR 15 R 16 or = CR 5 -OR 12 ;
R15 und R16 unabhängig voneinander für Alkyl stehen oderR 15 and R 16 are independently alkyl or
R15 und R16 zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-, -SO2-, -NH- oder — N- Alkyl- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstoffkette unterbrochenes Alkandiyl oder Alkendiyl mit jeweils 2 bis 5 Kohlenstoffatomen stehen;R 15 and R 16 together for optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N-alkyl- at the beginning (or am End) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
und die Verbindungen der allgemeinen Formel (I) außerdem N-Oxide, Salze, Tautomere, Diastereomere und optische Isomere umfassen.and the compounds of general formula (I) further include N-oxides, salts, tautomers, diastereomers and optical isomers.
Schließlich wurde gefunden, dass die erfindungsgemäßen Verbindungen der Formel (I) sehr gute insektizide und parasitizide Eigenschaften besitzen und sich im Pflanzenschutz, in der Veterinärhygiene, im Haushalt und im Materialschutz zur Bekämpfung unerwünschter Schädlinge, wie Insekten, Endo- oder Ektoparasiten, verwenden lassen.Finally, it has been found that the compounds of the formula (I) according to the invention have very good insecticidal and parasiticidal properties and can be used in crop protection, veterinary hygiene, household and material protection for controlling undesired pests, such as insects, endo- or ectoparasites.
Durch Halogen substituierte Reste, z.B. Haloalkyl, 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 radicals, e.g. Haloalkyl, are halogenated once or several times up to the maximum possible number of substituents. For multiple halogenation, the halogen atoms may be the same or different. Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
Gesättigte oder ungesättigte Kohlenwasserstoffreste 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 radicals, such as alkyl or alkenyl, may also be used in conjunction with heteroatoms, e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
Gegebenenfalls substituierte Reste können einfach oder mehrfach substituiert sein, wobei bei Mehrfachsubstitutionen die Substituenten gleich oder verschieden sein können.Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different.
Die erfindungsgemäßen 4-Phenyl-lH-pyrazole sind durch Formel (I) allgemein definiert. Bevorzugte, besonders bevorzugte, ganz besonders bevorzugte und insbesonders bevorzugte Restedefinitionen der vorstehenden und nachfolgend genannten Formern sind im Folgenden angegeben. Diese Definitionen gelten für die Endprodukte der Formel (I) wie für alle Zwischenprodukte gleichermaßen. A1 und A2 stehen unabhängig voneinander bevorzugt jeweils für Stickstoff, C-H, C-Halogen, C- (C,-C6-Haloalkyl), C-(CrC6-Alkoxy), C-Cyano oder C-(C,-C6-Alkyl);The 4-phenyl-1H-pyrazoles according to the invention are generally defined by formula (I). Preferred, particularly preferred, very particularly preferred and particularly preferred radical definitions of the above and below named formers are given below. These definitions apply equally to the end products of formula (I) as well as to all intermediates. A 1 and A 2 independently of one another each preferably nitrogen, CH, C-halogen, C- (C, -C 6 haloalkyl), C (C r C 6 alkoxy), C-cyano or C (C -C 6 -alkyl);
A1 und A2 stehen unabhängig voneinander besonders bevorzugt für Stickstoff, C-H, C-Halogen oder C-(CrC4-Haloalkyl);A 1 and A 2 independently of one another particularly preferably represent nitrogen, CH, C-halogen or C- (C r C 4 -haloalkyl);
A1 und A2 stehen unabhängig voneinander ganz besonders bevorzugt für Stickstoff oder C-H;A 1 and A 2 independently of one another very particularly preferably represent nitrogen or CH;
A1 und A2 stehen insbesondere bevorzugt für C-H; oderA 1 and A 2 are particularly preferably CH; or
A1 und A2 stehen insbesonders bevorzugt für Stickstoff; oderA 1 and A 2 are particularly preferably nitrogen; or
A1 steht insbesonders bevorzugt für Stickstoff und A2 insbesonders bevorzugt für C-H; oderA 1 is particularly preferably nitrogen and A 2 is particularly preferably CH; or
A1 steht insbesonders bevorzugt für C-H und A2 insbesonders bevorzugt für Stickstoff;A 1 is particularly preferably CH and A 2 particularly preferably nitrogen;
G1, G2, G3, G4, G5 stehen bevorzugt für Wasserstoff oder eine Kombination vonG 1 , G 2 , G 3 , G 4 , G 5 are preferably hydrogen or a combination of
Substituenten, unabhängig voneinander ausgewählt aus: Halogen, C1-C6-AIlCyI, C2-CO- Alkenyl, C2- C6-Alkinyl, C,-C6-Haloalkyl, SF5, Hydroxy, CrC6-Alkoxy, CrC6-Alkoxy-Ci-C6-alkyl, C1-C6- Alkoxy-CrC6-alkoxy, C3-C6-Cycloalkyl, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, C3-C6-Cycloalkyl- C,-C6-alkoxy, CrC6-Haloalkoxy, Q-Ce-Haloalkoxy-CrCe-alkyl, CrC6-Alkylsulfanyl, C1-C6- Haloalkylsulfanyl, CrQ-Alkylsulfinyl, Ci-Q-Haloalkylsulfinyl, CrC6-Alkylsulfonyl, C1-C6- Haloalkylsulfonyl, Cyano, Ci-C6-Alkylcarbonyl, C]-C6-Alkoxycarbonyl, Ci-C6-Alkoxycarbonyl- CpCβ-alkyl, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, CrCe-Alkylaminocarbonyl, Ci-C6- Dialkylaminocarbonyl, C1-C6-TrIaUCyIsHyI, Nitro, Amino, CrCβ-Alkylamino, Ci-C6-Dialkylamino, CrC6-Alkylsulfonylamino, d-Cβ-Dialkylsulfonylamino, -CR5=NO-CrC6-Alkyl, -CR5=NO-Halo- CrC6-alkyl oder Formyl, wobei vicinale Ci-C6-Alkyl-, C]-C6-Haloalkyl, C1-C6-AIkOXy- und/oder C]-C6-Haloalkoxygruppen zusammen mit den Kohlenstoffatomen, an die sie gebunden sind, ein fünf- bis sechsgliedriges cyclisches System bilden können, das 0 bis 2 Sauerstoffatome enthält, und dessen Alkandiyl-Rest gegebenenfalls mit einem oder mehreren Fluoratomen substituiert sein kann;Substituents independently selected from: halogen, C 1 -C 6 -alkyl, C 2 -C O - alkenyl, C 2 - C 6 alkynyl, C, -C 6 haloalkyl, SF 5, hydroxy, C r C 6 alkoxy, C r C 6 alkoxy-Ci-C 6 alkyl, C 1 -C 6 - alkoxy-C r C 6 alkoxy, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkyl C, C 6 alkoxy, C r C 6 haloalkoxy, Q-Ce-haloalkoxyCrCe alkyl, C r C 6 alkylsulfanyl, C 1 -C 6 - haloalkylsulfanyl, CRQ-alkylsulfinyl, Ci-Q-haloalkylsulfinyl, C r C 6 alkylsulfonyl, C 1 -C 6 - haloalkylsulfonyl, cyano, Ci-C6 alkylcarbonyl, C] -C6 alkoxycarbonyl, Ci-C 6 alkoxycarbonyl CpCβ-alkyl, carboxyl, aminocarbonyl, aminothiocarbonyl, CRCE-alkylaminocarbonyl, Ci-C 6 - alkylaminocarbonyl, C 1 -C 6 -TrIaUCyIsHyI, nitro, amino, CrCβ alkylamino, Ci-C 6 dialkylamino, C r C 6 alkylsulfonylamino, d-Cβ-Dialkylsulfonylamino, -CR 5 = NO-C r C 6 -alkyl, -CR 5 = NO-halo-C r C 6 alkyl or formyl, where vicinal Ci-C 6 alkyl, C] -C 6 haloalkyl, C 1 -C 6 -Aikoxy- and / or C] -C 6 -haloalkoxy groups together with the carbon atoms to which they are attached, can form a five- to six-membered cyclic system containing 0 to 2 oxygen atoms, and its alkanediyl radical optionally with one or may be substituted by a plurality of fluorine atoms;
G1, G2, G3, G4, G5 stehen besonders bevorzugt für Wasserstoff oder eine Kombination von bis zu drei Substituenten, unabhängig voneinander ausgewählt aus: Halogen, C]-C4-Alkyl, C2-C4- Alkenyl, C2-C4-Alkinyl, CrC4-Haloalkyl, SF5, Hydroxy, C1-C4-AJkOXy, C1-C4-AIkOXy-C1 -C4-alkyl, C1-C4-Alkoxy-C1-C4-alkoxy, C3-C4-Cycloalkyl, C2-C4-Alkenyloxy, C2-C4-Alkinyloxy, C3-C4- Cycloalkyl-CrC4-alkoxy, CrC4-Haloalkoxy, Ci-C4-Haloalkoxy-CrC4-alkyl, C,-C4-Alkylsulfanyl, CrC4-Haloalkylsulfanyl, C1-C4-Alkylsulfmyl, CrC4-Haloalkylsulfmyl, C1-C4-Alkylsulfonyl, C,- C4-Haloalkylsulfonyl, Cyano, C1-C4-Alkylcarbonyl, CrC4-Alkoxycarbonyl, C1-C4- Alkoxycarbonyl-Ci-C4-alkyl, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Cj-C4- Alkylaminocarbonyl, Ci-C4-Dialkylaminocarbonyl, CrC4-Trialkylsilyl, Nitro, Amino, Ci-C4- Alkylamino, CrC4-Dialkylamino, C]-C4-Aßcylsulfonylamino, Ci-C4-Dialkylsulfonylamino, -CR5=NO-CrC4-Alkyl, -CR5=NO-Halo-CrC4-alkyl oder Formyl, wobei vicinale Cj-C4-Alkyl-, C,- C4-Haloalkyl, C]-C4-Alkoxy- und/oder C]-C4-Haloalkoxygruppen zusammen mit den Kohlenstoffatomen, an die sie gebunden sind, ein fünf- bis sechsgliedriges cyclisches System bilden können, das 0 bis 2 Sauerstoffatome enthält, und dessen Alkandiyl-Rest gegebenenfalls mit einem oder mehreren Fluoratomen substituiert sein kann;G 1 , G 2 , G 3 , G 4 , G 5 particularly preferably represent hydrogen or a combination of up to three substituents, independently of one another, selected from: halogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl , C 2 -C 4 alkynyl, C r C 4 haloalkyl, SF 5, hydroxy, C 1 -C 4 -AJkOXy, C 1 -C 4 -alkoxy-C 1 -C 4 alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 alkoxy, C 3 -C 4 cycloalkyl, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 3 -C 4 - alkoxy cycloalkyl-C r C 4, C r C 4 haloalkoxy, Ci-C4-haloalkoxy-C r C 4 alkyl, C, -C 4 -alkylsulfanyl, C r C 4 -Haloalkylsulfanyl, C 1 -C 4 -Alkylsulfmyl, C r C 4 -Haloalkylsulfmyl , C 1 -C 4 alkylsulfonyl, C, - C 4 haloalkylsulfonyl, cyano, C 1 -C 4 alkylcarbonyl, C r C 4 alkoxycarbonyl, C 1 -C 4 - Alkoxycarbonyl-Ci-C 4 alkyl, carboxyl, aminocarbonyl, aminothiocarbonyl, Ci-C 4 - alkylaminocarbonyl, Ci-C4-dialkylaminocarbonyl, C r C 4 trialkylsilyl, nitro, amino, Ci-C 4 - alkylamino, C r C 4 dialkylamino, C] -C 4 -Aßcylsulfonylamino, Ci-C 4 -Dialkylsulfonylamino, -CR 5 = NO-C r C 4 -alkyl, -CR 5 = NO-halo-C r C 4 alkyl or formyl, wherein vicinal Cj-C 4 alkyl, C, - C 4 haloalkyl, C] -C 4 alkoxy and / or C] -C 4 haloalkoxy groups together with the carbon atoms to which they are attached, a five- to can form a six-membered cyclic system which contains 0 to 2 oxygen atoms, and whose alkanediyl radical may optionally be substituted by one or more fluorine atoms;
G1, G2, G, G4, G5 stehen ganz besonders bevorzugt für eine 3 -Substitution, 4-Substitution, 3,4-Disubstitution, 3,5-Disubstitution oder 3,4,5-Trisubstitution, wobei die Substituenten G1, G2,G 1 , G 2 , G, G 4 , G 5 very particularly preferably represent a 3-substitution, 4-substitution, 3,4-disubstitution, 3,5-disubstitution or 3,4,5-trisubstitution, where the substituents G 1 , G 2 ,
G3, G4 und G5 unabhängig voneinander ausgewählt werden aus: Wasserstoff, Halogen, Q-C2-G 3 , G 4 and G 5 are independently selected from: hydrogen, halogen, QC 2 -
Alkyl, d-C2-Haloalkyl, CrC2-Alkoxy, CrC2-Alkoxy-C,-C2-alkyl, Q-C2-Alkoxy-Cj-C2-alkoxy, C3-Alkyl, alkoxy dC 2 haloalkyl, C r C 2 alkoxy, C r C 2 alkoxy-C, -C 2 alkyl, QC 2 alkoxy-Cj-C 2, C 3 -
C6-Cycloalkyl-CrC2-alkoxy, CrC2-Haloalkoxy, CrC2-Alkylsulfanyl, Q-C2-Haloalkylsulfanyl, Q-C 6 -cycloalkyl-C r C 2 -alkoxy, C r C 2 -haloalkoxy, C r C 2 -alkylsulfanyl, QC 2 -haloalkylsulfanyl, Q-
C2-Alkylsulfinyl, Ci-C2-Haloalkylsulfmyl, C1-C2-Alkylsulfonyl, C1-C2-Haloalkylsulfonyl, Cyano, Ci-Ca-Alkylcarbonyl, C]-C2-Alkoxycarbonyl, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Q-C 2 alkylsulfinyl, C 1 -C 2 -haloalkylsulfmyl, C 1 -C 2 -alkylsulfonyl, C 1 -C 2 -haloalkylsulfonyl, cyano, C 1 -C -alkylcarbonyl, C 1 -C 2 -alkoxycarbonyl, carboxyl, aminocarbonyl, aminothiocarbonyl, Q-
C2-Alkylaminocarbonyl, Ci-C2-Dialkylaminocarbonyl, Nitro, Amino, Ci-C2-Alkylamino, Q-C2-C 2 alkylaminocarbonyl, C 1 -C 2 dialkylaminocarbonyl, nitro, amino, C 1 -C 2 -alkylamino, QC 2 -
Dialkylamino, Ci-C2-Alkylsulfonylamino, Ci-C2-Dialkylsulfonylamino;Dialkylamino, C 1 -C 2 -alkylsulfonylamino, C 1 -C 2 -dialkylsulfonylamino;
G1, G2, G3, G4, G5 stehen insbesonders bevorzugt für eine 2-Chlorsubstitution, 3-Chlor- substitution, 3-Bromsubstitution, 3 -Fluorsubstitution, 4-Bromsubstitution, 4-Chlorsubstitution, 3,4- Dichlorsubstitution, 3,4-Difluorsubstitution, 3-Chlor-4-fluorsubstitution, 3-Fluor-4-chlorsubsti- tution, 3-Fluor-5-chlorsubstitution, S-Chlor-S-trifluormethylsubstitution, 3, 5 -Dichlorsubstitution,G 1 , G 2 , G 3 , G 4 , G 5 are especially preferred for 2-chlorine substitution, 3-chloro substitution, 3-bromosubstitution, 3-fluoro substitution, 4-bromosubstitution, 4-chloro substitution, 3,4-dichloro substitution , 3,4-difluorus substitution, 3-chloro-4-fluoro-substitution, 3-fluoro-4-chloro-substitution, 3-fluoro-5-chloro-substitution, S-chloro-S-trifluoromethyl-substitution, 3, 5 -dichloro-substitution,
3,5-Dimethylsubstitution oder 3,5-Bistrifluormethylsubstitution;3,5-dimethyl substitution or 3,5-bistrifluoromethyl substitution;
Q1 steht bevorzugt für eine der nachstehend aufgeführten heterocyclischen Gruppierungen;Q 1 is preferably one of the heterocyclic groups listed below;
(Z3) (Z4) (Z5) (Z6) (Z7) (Z 3 ) (Z 4 ) (Z 5 ) (Z 6 ) (Z 7 )
(Z8) (Z9) (Z10) (Z13) (Z14) (Z 8 ) (Z 9 ) (Z 10 ) (Z 13 ) (Z 14 )
(Z15) (Z16) (Z") (Z18) (Z19)(Z 15 ) (Z 16 ) (Z ") (Z 18 ) (Z 19 )
(Z21) (Z22) (Z23) (Z24)(Z 21 ) (Z 22) (Z 23) (Z 24 )
Q1 steht besonders bevorzugt für eine der nachstehend aufgeführten heterocyclischen Gruppierungen;Q 1 particularly preferably represents one of the heterocyclic groups listed below;
(Z3) (Z7) (Z13) (Z14) (Z15) (Z 3 ) (Z 7 ) (Z 13 ) (Z 14 ) (Z 15 )
(Z16)(Z 16 )
(Z17) (Z1β) (Z19) (Z21)(Z 17 ) (Z 1β) (Z 19 ) (Z21)
(Z22) (Z23) (Z 22) ( Z 23)
(Z24) Q1 steht ganz besonders bevorzugt für eine der nachstehend aufgeführten heterocyclischen Gruppierungen;(Z 24 ) Q 1 very particularly preferably represents one of the heterocyclic groups listed below;
(Z3) (Z?) (Z15) (ZU) (Z") ( Z 3) (Z?) (Z15) (TO) (Z ")
(Z18) (Z21) (Z22) (Z23) (224)(Z 18 ) ( Z 21) ( Z 22) ( Z 23) (224)
Q! steht insbesonders bevorzugt für eine der nachstehend aufgeführten heterocyclischen Gruppierungen;Q ! is especially preferred for one of the heterocyclic groups listed below;
(Z3) (Z16)(Z 3 ) (Z 16 )
wobeiin which
W1 bevorzugt für Sauerstoff oder Schwefel steht;W 1 is preferably oxygen or sulfur;
W1 ganz besonders bevorzugt für Sauerstoff steht;W 1 very particularly preferably represents oxygen;
W2 bevorzugt für Sauerstoff oder Schwefel steht;W 2 is preferably oxygen or sulfur;
W2 ganz besonders bevorzugt für Sauerstoff steht; undW 2 is very particularly preferably oxygen; and
R6, R6', R6", R6 " und R7 die unten stehende Bedeutung haben;R 6 , R 6 ' , R 6 " , R 6" and R 7 are as defined below;
Q2 steht bevorzugt für C(O)NR8R9; Q3 steht bevorzugt für C(R10R1 ^NR8R9;Q 2 is preferably C (O) NR 8 R 9 ; Q 3 is preferably C (R 10 R 1 ^ NR 8 R 9 ;
Q4 steht bevorzugt für Cyano (wobei R1 nicht für Amino steht), COOH, COOR12, Fluor (falls R3 verschieden von Chlor ist), Chlor (falls R3 verschieden von Chlor, COOH, CH2CH2OMe und OMe ist), Brom, Iod, SR12 (wobei R1 nicht für Amino steht, falls R12 für Alkyl steht), S(O)R12, S(O)2R12 oder S(O)2NR8R9;Q 4 is preferably cyano (where R 1 is not amino), COOH, COOR 12 , fluorine (if R 3 is other than chlorine), chlorine (if R 3 is other than chlorine, COOH, CH 2 CH 2 OMe and OMe is), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 , S (O) 2 R 12 or S (O) 2 NR 8 R 9 ;
Q4 steht besonders bevorzugt für Cyano (wobei R1 nicht für Amino steht), COOH, COOMe, COOEt, Fluor (falls R3 verschieden von Chlor ist ), Chlor (falls R3 verschieden von Chlor, COOH, CH2CH2OMe und OMe ist), Brom, Iod, SR12 (wobei R1 nicht für Amino steht, falls R12 für Alkyl steht), S(O)R12, S(O)2R12 oder S(O)2NR8R9;Q 4 particularly preferably represents cyano (where R 1 is not amino), COOH, COOMe, COOEt, fluorine (if R 3 is other than chlorine), chlorine (if R 3 is different from chlorine, COOH, CH 2 CH 2 OMe and OMe), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 , S (O) 2 R 12 or S (O) 2 NR 8 R 9 ;
Q4 steht ganz besonders bevorzugt für Cyano (wobei R1 nicht für Amino steht), COOH,Q 4 is very particularly preferably cyano (where R 1 is not amino), COOH,
COOMe, COOEt, Fluor (falls R3 verschieden von Chlor ist), Brom, Iod, SR12 (wobei R1 nicht für Amino steht, falls R12 für Alkyl steht), S(O)R12, S(O)2R12 oder S(O)2NR8R9;COOMe, COOEt, fluorine (if R 3 is other than chlorine), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 , S (O) 2 R 12 or S (O) 2 NR 8 R 9 ;
Q4 steht insbesondere bevorzugt für Cyano (wobei R1 nicht für Amino steht), COOH, COOMe, COOEt, Fluor (falls R3 verschieden von Chlor ist), Brom, Iod, SR12 (wobei R1 nicht für Amino steht, falls R12 für Alkyl steht), S(O)R12 oder S(O)2R12;In particular, Q 4 is preferably cyano (where R 1 is not amino), COOH, COOMe, COOEt, fluorine (if R 3 is other than chlorine), bromine, iodine, SR 12 (where R 1 is not amino, if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 ;
R1 steht bevorzugt für Wasserstoff, Halogen, Ci-C4-Alkylsulfanyl, CrC4-Alkylsulfinyl, CrC4-Alkylsulfonyl, Z16, Amino oder NR13R14;R 1 preferably represents hydrogen, halogen, Ci-C4-alkylsulfanyl, C r C 4 alkylsulfinyl, C r C 4 alkylsulfonyl, Z 16, amino or NR 13 R 14;
R1 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Z16, Amino oder NR13R14;R 1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, Z 16 , amino or NR 13 R 14 ;
R1 steht ganz besonders bevorzugt für Chlor, Brom, Iod, Z16, Amino oder NR13R14;R 1 very particularly preferably represents chlorine, bromine, iodine, Z 16 , amino or NR 13 R 14 ;
R1 steht insbesondere bevorzugt für Amino oder NR13R14;R 1 particularly preferably represents amino or NR 13 R 14 ;
R2 steht bevorzugt für Wasserstoff, Halogen, CrC6-Alkyl, C]-C6-Haloalkyl, CrC6- Alkoxy-CrC6-alkyl, Ci-Cs-Haloalkoxy-CpCβ-alkyl, CrC6-Alkoxy-CrC6-haloalkyl, CrC6-Alkyl- sulfanyl-Ci-C6-alkyl, CrQ-Alkylsulfinyl-CrCe-alkyl, CrC6-Alkylsulfonyl-Ci-C6-alkyl, C1-C6- Haloalkylsulfanyl-CrC6-alkyl, C,-C6-Haloalkylsulfinyl-C,-C6-alkyl, CrC6-Haloalkylsulfonyl-Cr C6-alkyl, C3-C6-Cycloalkyl-C,-C6-alkyl, Phenyl-CrC6-alkyl, Heteroaryl-Q-Ce-alkyl, Hetero-C3-C6- cyclyl-Ci-C6-alkyl, Aryl-CrC6-haloalkyl, CrC6-Haloalkyloxy-CrC6-haloalkyloxy-Ci-C6-haloalkyl, C3-C6-Heterocyclyl, CrC6-Alkylsulfanyl, C,-C6-Alkylsulfinyl, CrC6-Alkylsulfonyl oder Phenyl;R 2 preferably represents hydrogen, halogen, C r C 6 alkyl, C] -C6 haloalkyl, C r C 6 - alkoxy-C r C 6 alkyl, Ci-Cs-haloalkoxy CpCβ-alkyl, C r C 6 alkoxy-C r C 6 haloalkyl, C r C 6 -alkyl sulfanyl-Ci-C 6 alkyl, CRQ-alkylsulfinyl CRCE-alkyl, C r C 6 alkylsulfonyl-Ci-C 6 alkyl, C 1 -C 6 - haloalkylsulfanyl-C r C 6 alkyl, C, -C 6 haloalkylsulfinyl-C, -C 6 alkyl, C r C 6 haloalkylsulfonyl-C r C 6 alkyl, C 3 -C 6 -Cycloalkyl-C, -C 6 -alkyl, phenyl-C r C 6 -alkyl, heteroaryl-Q-Ce-alkyl, hetero-C 3 -C 6 - cyclyl-Ci-C 6 -alkyl, aryl-C r C 6 -haloalkyl, C r C 6 -Haloalkyloxy-C r C 6 -haloalkyloxy-Ci-C 6 haloalkyl, C 3 -C 6 heterocyclyl, C r C 6 alkylsulfanyl, C, -C 6 alkylsulfinyl, C r C 6 alkylsulfonyl or phenyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, CrC6-Alkyl, CrC6-Haloalkyl, CrC6-Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen, Ci-Q-Alkyl, CrC6-Haloalkyl, C,-C6-Alkoxy, CrC6-Alkylsulfanyl, Ci-C6-Alkylsulfinyl, Ci-Cβ-Alkylsulfonyl, Ci-C6-Monoalkylamino, Ci-Cβ-Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C6-Alkyl, CrC6-Haloalkyl, C1-C6-wherein a phenyl or heteroaryl optionally mono- or polysubstituted by halogen, C r C 6 alkyl, C r C 6 haloalkyl, C r C 6 alkoxy, nitro or cyano; one Heterocyclylrest is optionally substituted by -OH / = 0, -SH / = S, -NH 2 , halogen, Ci-Q-alkyl, C r C 6 haloalkyl, C, -C 6 alkoxy, C r C 6 alkylsulfanyl C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -monoalkylamino, C 1 -C 6 -dialkylamino, nitro or cyano; and a mono- or bound to phenyl, heteroaryl or heterocyclyl alkanediyl radical optionally polysubstituted by halogen, Ci-C 6 alkyl, C r C 6 haloalkyl, C 1 -C 6 -
Alkoxy oder Cyano;Alkoxy or cyano;
R2 steht besonders bevorzugt für Wasserstoff, Halogen, Ci-C4-Alkyl, Ci-C4-Haloalkyl, CrC4-Alkoxy-CrC4-alkyl, C1-C4-Haloalkoxy-C1-C4-alkyl, CrC4-Alkoxy-Ci-C4-haloalkyl, CpC4- Alkylsulfanyl-C|-C4-alkyl, Ci-C4-Alkylsulfinyl-C1-C4-alkyl, C1-C4-Alkylsulfonyl-CrC4-alkyl, C1- C4-Haloalkylsulfanyl-Ci-C4-alkyl, C1-C4-Haloalkylsulfinyl-C1-C4-alkyl, CrC4-Haloalkylsulfonyl- CrC4-alkyl, C3-C4-Cycloalkyl-CrC4-alkyl, Phenyl-CrC4-alkyl, Heteroaryl-Ci-C4-alkyl, Hetero-C3- C4-cyclyl-CrC4-alkyl, Aryl-CrC4-haloalkyl, Ci-C4-Haloalkyloxy-CrC4-haloalkyloxy-CrC4- haloalkyl, C3-C4-Heterocyclyl, C1-C4-Alkylsulfanyl, CrC4-Alkylsulfinyl, CrC4-Alkylsulfonyl oder Phenyl;R 2 particularly preferably represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, -C 4 alkoxy-C r C 4 alkyl, C 1 -C 4 haloalkoxy-C 1 -C 4 - alkyl, C r C 4 alkoxy-Ci-C4-haloalkyl, CpC 4 - alkylsulfanyl-C | -C 4 alkyl, C 4 alkylsulfinyl-C 1 -C 4 alkyl, C 1 -C 4 - alkylsulfonyl-C r C 4 alkyl, C 1 - C 4 -Haloalkylsulfanyl-Ci-C 4 alkyl, C 1 -C 4 haloalkylsulfinyl-C 1 -C 4 alkyl, C r C 4 C r C -Haloalkylsulfonyl- 4- alkyl, C 3 -C 4 -cycloalkyl-C r C 4 -alkyl, phenyl-C r C 4 -alkyl, heteroaryl-Ci-C 4 -alkyl, hetero-C 3 - C 4 -cyclyl-C r C 4 alkyl, aryl-C r C 4 haloalkyl, Ci-C4 -Haloalkyloxy-C r C 4 -haloalkyloxy-C r C 4 - haloalkyl, C 3 -C 4 heterocyclyl, C 1 -C 4 alkylsulfanyl, C r C 4 alkylsulfinyl, C r C 4 alkylsulfonyl or phenyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, CrC4-Alkyl, Ci-C4-Haloalkyl, CrC4-Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen, C1-C4-Alkyl, CrC4-Haloalkyl, C,-C4-Alkoxy, Ci-C4-Alkylsulfanyl, Ci-C4-Alkylsulfmyl, C1- C4-Alkylsulfonyl, CrQ-Monoalkylarnino, C1-C4-Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, CrC4-Alkyl, C]-C4-Haloalkyl, Ci-C4-Alkoxy oder Cyano.wherein a phenyl or heteroaryl optionally mono- or polysubstituted by halogen, C r C 4 alkyl, Ci-C 4 haloalkyl, C r C 4 alkoxy, nitro or cyano; a heterocyclyl radical optionally substituted by -OH / = 0, -SH / = S, -NH2, halogen, C 1 -C 4 alkyl, C r C 4 haloalkyl, C, -C 4 alkoxy, C 4 alkylsulfanyl, Ci-C4 -Alkylsulfmyl, C 1 - C 4 alkylsulfonyl, CRQ-Monoalkylarnino, C 1 -C 4 dialkylamino, nitro or cyano; and a tied to phenyl, heteroaryl or heterocyclyl alkanediyl moiety is optionally mono- or polysubstituted by halogen, C r C 4 alkyl, C] -C 4 haloalkyl, Ci-C 4 alkoxy or cyano.
R2 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Iod, Ci-C4-AIkOXy-C1-C4- alkyl, CM-Alkyl, Aryl-Ci-C4-haloalkyl, CrC6-Alkylsulfanyl, CrC6-Alkylsulfinyl, CrC6- Alkylsulfonyl oder C^-Haloalkyl;R 2 very particularly preferably represents fluorine, chlorine, bromine, iodine, Ci-C 4 -alkoxy-C 1 -C 4 - alkyl, C M-alkyl, aryl-Ci-C 4 haloalkyl, C r C 6 alkylsulfanyl , C r C 6 alkylsulfinyl, C r C 6 - alkylsulfonyl or C ^ haloalkyl;
R2 steht insbesonders bevorzugt für Ci_2-Haloalkyl;R 2 is particularly preferably Ci_ 2 haloalkyl;
R3 steht bevorzugt für Halogen, CrC6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, CrC6- Haloalkyl, C3-C6-Cycloalkyl, CrC6-Alkoxy-Ci-C6-alkyl, Ci-C6-Alkylcarbonyloxy-Ci-C6-alkyl, C1- C6-Alkylsulfanyl-CrC6-alkyl, CrCβ-Alkylsulfinyl-CrCβ-alkyl, CrC6-Alkylsulfonyl-C1-C6-alkyl, Hydroxy, Ci-C6-Alkoxy, CrCδ-Acylamino, Ci-C6-Alkoxycarbonylamino, C2-C6-Alkenyloxy, C2- C6-Alkinyloxy, C3-C6-Cycloalkyl-CrC6-alkoxy, Ci-C6-Haloalkoxy, CrC6-Alkylsulfanyl, C1-C6- Haloalkylsulfanyl, CrC6-Alkylsulfinyl, CrQ-Haloalkylsulfinyl, CrC6-Alkylsulfonyl, CrC6- Haloalkylsulfonyl, Cyano, CrC6-Alkylcarbonyl, CrC6-Alkoxycarbonyl, d-C6-Alkoxycarbonyl- Ci-C6-alkyl, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, CrCβ-Alkylaminocarbonyl, Ci-C6- Dialkylaminocarbonyl, Ci-Cg-Alkylsulfonylaminocarbonyl, Ci-Cδ-Trialkylsilyl, Nitro, Amino, Cr Cδ-Alkylaπüno, Ci-C6-Dialkylamino, Ci-Cβ-Alkylsulfonylamino, Ci-Cβ-Dialkylsulfonylamino, - CR5=NO-R5, -CR5=NO-Halo-CrC6-alkyl, Z16 oder Formyl;R 3 is preferably halogen, C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C r C 6 - haloalkyl, C 3 -C 6 cycloalkyl, C r C 6 - alkoxy-Ci-C 6 alkyl, Ci-C6 alkylcarbonyloxy-Ci-C 6 alkyl, C 1 - C 6 alkylsulfanyl-C r C 6 alkyl, CrCβ-alkylsulfinyl-CrCβ-alkyl, C r C 6 -alkylsulfonyl-C 1 -C 6 alkyl, hydroxy, Ci-C 6 alkoxy, CrC δ acylamino, Ci-C 6 alkoxycarbonylamino, C 2 -C 6 alkenyloxy, C 2 - C 6 alkynyloxy, C 3 -C 6 -cycloalkyl-C r C 6 alkoxy, Ci-C 6 haloalkoxy, C r C 6 alkylsulfanyl, C 1 -C 6 - haloalkylsulfanyl, C r C 6 alkylsulfinyl, CRQ-haloalkylsulfinyl, C r C 6 alkylsulfonyl, C r C 6 - haloalkylsulfonyl, cyano, C r C 6 alkylcarbonyl, C r C 6 alkoxycarbonyl, dC 6 alkoxycarbonyl Ci-C 6 alkyl, carboxyl, aminocarbonyl, aminothiocarbonyl, CrCβ-alkylaminocarbonyl, Ci-C 6 - dialkylaminocarbonyl, Ci-Cg-alkylsulphonylaminocarbonyl, C δ trialkylsilyl, nitro, amino, Cr C δ -Alkylaπüno, Ci-C 6- dialkylamino, Ci-Cβ-alkylsulfonylamino, Ci-Cβ-dialkylsulfonylamino, - CR 5 = NO-R 5 , -CR 5 = NO-halo-C r C 6 -alkyl, Z 16 or formyl;
R3 steht besonders bevorzugt für Halogen, CrC4-Alkyl, C2-C4-Alkenyl, C2-C4- Alkinyl,R 3 particularly preferably represents halogen, C r C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 - alkynyl,
CrC4-Haloalkyl, C3-C4-Cycloalkyl, CrC4-Alkoxy-Ci-C4-alkyl, C1-C4-Alkylcarbonyloxy-C1-C4- alkyl, CrC4-Alkylsulfanyl-CrC4-alkyl, C,-C4-Alkylsulfinyl-CrC4-alkyl, C,-C4-Alkylsulfonyl-Cr C4-alkyl, Hydroxy, Ci-C4-Alkoxy, CrC4-Acylamino, Ci-C4-Alkoxycarbonylamino, C2-C4-Alkenyl- oxy, C2-C4-Alkinyloxy, C3-C4-Cycloalkyl-Ci-C4-alkoxy, CrC4-Haloalkoxy, C1-C4-Alkylsulfanyl, Ci-C4-Haloalkylsulfanyl, CrC4-Alkylsulfmyl, C1-C4-Haloalkylsulfinyl, C1-C4-Alkylsulfonyl, Cr C4-Haloalkylsulfonyl, Cyano, Ci-C4-Alkylcarbonyl, Ci-C4-Alkoxycarbonyl, Ci-C4-Alkoxy- carbonyl-Ci-C4-alkyl, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Ci-C4-Alkylaminocarbonyl, Ci-Ct-Dialkylaminocarbonyl, Ci-C4-Alkylsulfonylaminocarbonyl, Ci-C4-Trialkylsilyl, Nitro, Amino, Ci-C4-Alkylamino, C]-C4-Dialkylamino, CrC4-Alkylsulfonylamino, Ci-C4-Dialkyl- sulfonylamino, -CR5=NO-R5, -CR5=NO-Halo-CrC4-alkyl, Z16 oder Formyl;C r C 4 haloalkyl, C 3 -C 4 cycloalkyl, C r C 4 alkoxy-Ci-C 4 alkyl, C 1 -C 4 alkylcarbonyloxy-C 1 -C 4 - alkyl, C r C 4 - alkylsulfanyl-C r C 4 alkyl, C, -C 4 alkylsulfinyl-C r C 4 alkyl, C, -C alkyl 4 alkylsulfonyl-C r C 4, hydroxy, Ci-C 4 alkoxy, C r C 4 -acylamino, C 1 -C 4 -alkoxycarbonylamino, C 2 -C 4 -alkenyl-oxy, C 2 -C 4 -alkynyloxy, C 3 -C 4 -cycloalkyl-C 1 -C 4 -alkoxy, C r C 4 - haloalkoxy, C 1 -C 4 alkylsulfanyl, Ci-C4 -Haloalkylsulfanyl, C r C 4 -Alkylsulfmyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C r C 4 haloalkylsulfonyl, cyano, C -C 4 alkylcarbonyl, Ci-C 4 alkoxycarbonyl, Ci-C 4 alkoxy carbonyl-Ci-C 4 alkyl, carboxyl, aminocarbonyl, aminothiocarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C t dialkylaminocarbonyl, C -Alkylsulfonylaminocarbonyl -C 4, C 4 trialkylsilyl, nitro, amino, Ci-C 4 alkylamino, C] -C 4 dialkylamino, C r C 4 alkylsulfonylamino, Ci-C 4 dialkyl sulfonylamino, -CR 5 = NO-R 5 , -CR 5 = NO-halo-C r C 4 -alkyl, Z 16 or For myl;
R3 steht ganz besonders bevorzugt für Halogen, Ci-C2-Alkyl, Ci-C2-Haloalkyl, Cyclopropyl, Ci-C2-Alkoxy-Ci-C2-alkyl, Ci-C2-Alkylcarbonyloxy-C,-C2-alkyl, CrC2-Alkyl- sulfanyl-C,-C2-alkyl, Ci-CrAlkylsulfinyl-Ci-Cralkyl, CrC4-Alkylsulfonyl-CrC2-alkyl, C1-C2- Alkoxy, Ci-C2-Acylamino, Ci-C2-Alkoxycarbonylamino, Cyclopropyl-C]-C2-alkoxy, Ci-C2-HaIo- alkoxy, CrC2-Alkylsulfanyl, CrC2-Haloalkylsulfanyl, CrC2-Alkylsulfmyl, CrC2-Haloalkylsul- finyl, C,-C2-Alkylsulfonyl, CrC2-Haloalkylsulfonyl, Cyano, CrC2-Alkylcarbonyl, C,-C2-Alkoxy- carbonyl, C]-C2-Alkoxycarbonyl-Ci-C2-alkyl, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Cr C2-Alkylaminocarbonyl, Ci-C2-Dialkylaminocarbonyl, Ci-C2-Alkylsulfonylaminocarbonyl, C]-C2- Trialkylsilyl, Nitro, Amino, Ci-C2-Alkylamino, Ci-C2-Dialkylamino, Ci-C2-Alkylsulfonylamino, Ci-C2-Dialkylsulfonylamino, -CR5=NO-R5, -CR5=NO-Halo-Ci-C2-alkyl, Z16 oder Formyl;R 3 very particularly preferably represents halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, cyclopropyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 2 -alkylcarbonyloxy-C, -C 2 -alkyl, C r C 2 alkyl sulfanyl-C, -C 2 alkyl, Ci-Cralkyl-Ci-CrAlkylsulfinyl, C r C 4 alkylsulfonyl-C r C 2 alkyl, C 1 -C 2 - alkoxy , C 2 -acylamino, Ci-C alkoxy 2 alkoxycarbonylamino, cyclopropyl-C] -C 2, C 2 -HaIo- alkoxy, C r C 2 alkylsulphanyl, C r C 2 -Haloalkylsulfanyl, C r C 2 -Alkylsulfmyl, C r C 2 -Haloalkylsul- finyl, C, -C 2 alkylsulfonyl, C r C 2 haloalkylsulfonyl, cyano, C r C 2 alkylcarbonyl, C, -C 2 alkoxy carbonyl, C] -C 2 -alkoxycarbonyl-Ci-C 2 alkyl, carboxyl, aminocarbonyl, aminothiocarbonyl, C r C 2 alkylaminocarbonyl, Ci-C 2 dialkylaminocarbonyl, Ci-C 2 -Alkylsulfonylaminocarbonyl, C] -C 2 - trialkylsilyl, nitro, Amino, C 1 -C 2 -alkylamino, C 1 -C 2 -dialkylamino, C 1 -C 2 -alkylsulfonylamino, C 1 -C 2 -dialkylsulfonylamino, -CR 5 = NO-R 5 , -CR 5 = NO-halo-C 1 -C 4 2- alkyl, Z 16 or formyl;
R3 steht insbesonders bevorzugt für Fluor, Chlor, Brom, Iod, Ci-C2-Alkyl, Ci-C2- Haloalkyl, Ci-C2-Haloalkylsulfanyl, C]-C2-Haloalkylsulfinyl, Ci-C2-Haloalkylsιüfonyl oder Cyano;R 3 especially preferably represents fluorine, chlorine, bromine, iodine, Ci-C 2 alkyl, C 2 - haloalkyl, Ci-C 2 -Haloalkylsulfanyl, C] -C 2 haloalkylsulfinyl, C 2 or -Haloalkylsιüfonyl cyano;
R4 steht bevorzugt für Wasserstoff, Cyano, Nitro, Ci-C6-Alkyl, Ci-Cβ-Haloalkyl, Halogen oder Ci-Cβ-Alkoxy;R 4 is preferably hydrogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, halogen or C 1 -C 6 -alkoxy;
R4 steht besonders bevorzugt für Wasserstoff, Cyano, Nitro, Ci-C4-Alkyl, Ci-C4-R 4 particularly preferably represents hydrogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -
Haloalkyl, Halogen oder Ci-C4-Alkoxy;Haloalkyl, halogen or C 1 -C 4 -alkoxy;
R4 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom oder Iod; R4 steht insbesondere bevorzugt für Wasserstoff;R 4 very particularly preferably represents hydrogen, fluorine, chlorine, bromine or iodine; R 4 is particularly preferably hydrogen;
R5 steht bevorzugt für Wasserstoff oder Ci.6-Alkyl;R 5 is preferably hydrogen or Ci. 6- alkyl;
R5 steht besonders bevorzugt für Wasserstoff oder CM-Alkyl;R 5 particularly preferably represents hydrogen or C M -alkyl;
R5 steht ganz besonders bevorzugt für Wasserstoff oder C]-3-Alkyl;R 5 is very particularly preferably hydrogen or C ] -3- alkyl;
R5 steht insbesonders bevorzugt für Wasserstoff, Methyl oder Ethyl;R 5 is particularly preferably hydrogen, methyl or ethyl;
R6, R6', R6 ", R6 stehen unabhängig voneinander bevorzugt für Wasserstoff, Amino, Hydroxy, Mercapto, Nitro, Cyano, Carboxyl, Halogen, C]-C6-Alkyl, Ci-C6-Haloalkyl, C2-C6- Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, CrC6-Alkoxy, CrC6-Haloalkoxy, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, CrC6-Alkoxycarbonyl, Ci-C6-Alkylsulfanyl, Ci-C6-Haloalkylsulfanyl, Q-C6- Alkylsulfinyl, CrC6-Haloalkylsulfinyl, Ci-C6-Alkylsulfonyl, Q-Q-Haloalkylsulfonyl, Amino- carbonyl, Aminothiocarbonyl, CR5=NO-Q-C6-alkyl, -CR^NO-Halo-Q-Q-alkyl, Formyl, Q-C6- Alkylamino, Ci-C6-Dialkylamino, Phenyl, Heteroaryl, Heteroaryl-Q-C6-alkyl oder Hetero-C3-C6- cyclyl-Ci-C6-alkyl;R 6 , R 6 ' , R 6 " , R 6 independently of one another preferably represent hydrogen, amino, hydroxyl, mercapto, nitro, cyano, carboxyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 - alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C r C 6 alkoxy, C r C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C r C 6 alkoxycarbonyl, Ci-C 6 alkylsulfanyl, Ci-C 6 -Haloalkylsulfanyl, QC 6 - alkylsulphinyl, C r C 6 haloalkylsulfinyl, Ci-C 6 alkylsulfonyl, QQ-haloalkylsulfonyl, amino carbonyl , Aminothiocarbonyl, CR 5 = NO-QC 6 -alkyl, -CR ^ NO-halo-QQ-alkyl, formyl, QC 6 - alkylamino, Ci-C 6 -dialkylamino, phenyl, heteroaryl, heteroaryl-QC 6 -alkyl or hetero -C 3 -C 6 -cyclyl-C 1 -C 6 -alkyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C6-Alkyl, Q-C6-Haloalkyl, Ci-C6-Alkoxy, Nitro oder Cyano; einwhere a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, nitro or cyano; one
Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen,Heterocyclyl optionally substituted by -OH / = 0, -SH / = S, -NH 2 , halogen,
CrC6-Alkyl, Ci-C6-Haloalkyl, CrC6-Alkoxy, CrC6-Alkylsulfanyl, C,-C6-Alkylsulfinyl, C1-C r C 6 alkyl, Ci-C 6 haloalkyl, C r C 6 alkoxy, C r C 6 alkylsulfanyl, C, -C 6 alkylsulfinyl, C 1 -
C6-Alkylsulfonyl, Ci-C6-Monoalkylamino, Ci-C6-Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, CrC6-Alkyl, Q-C6-Haloalkyl, Q-C6-Alkoxy oder Cyano.C 6 alkylsulfonyl, C 1 -C 6 monoalkylamino, C 1 -C 6 dialkylamino, nitro or cyano; and a tied to phenyl, heteroaryl or heterocyclyl alkanediyl radical optionally mono- or polysubstituted by halogen, C r C 6 alkyl, QC 6 haloalkyl, QC 6 alkoxy or cyano.
R6, R6 , R6 , R6 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Amino, Hydroxy, Mercapto, Nitro, Cyano, Carboxyl, Halogen, C]-C4-Alkyl, Ci-C4-Haloalkyl, C2- Q-Alkenyl, C2-C4-Alkinyl, C3-C4-Cycloalkyl, CrC4-Alkoxy, Q-C4-Haloalkoxy, C2-C4-Alkenyl- oxy, C2-C4-Alkinyloxy, CrC4-Alkoxycarbonyl, CrC4-Alkylsulfanyl, CrC4-Haloalkylsulfanyl, Q- C4-Alkylsulfinyl, Ci-C4-Haloalkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Haloalkylsulfonyl, Amino- carbonyl, Aminothiocarbonyl, CR5=NO-CrC4-alkyl, -CR5=NO-Halo-CrC4-alkyl, Formyl, CrC4- Alkylamino, C1-C4-Dialkylamino, Phenyl, Heteroaryl, Heteroaryl-CrC4-alkyl oder Hetero-C3-C4- cyclyl-CrC4-alkyl;R 6 , R 6 , R 6 , R 6 independently of one another particularly preferably represent hydrogen, amino, hydroxyl, mercapto, nitro, cyano, carboxyl, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 - Q-alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C r C 4 alkoxy, QC 4 haloalkoxy, C 2 -C 4 -alkenyl oxy, C 2 -C 4 alkynyloxy , C r C 4 alkoxycarbonyl, C r C 4 alkylsulphanyl, C r C 4 -Haloalkylsulfanyl, Q- C 4 alkylsulfinyl, Ci-C 4 -Haloalkylsulfmyl, Ci-C 4 alkylsulfonyl, Ci-C4-haloalkylsulfonyl, amino- carbonyl, aminothiocarbonyl, CR 5 = NO-C r C 4 -alkyl, -CR 5 = NO-halo-C r C 4 alkyl, formyl, C r C 4 - alkylamino, C 1 -C 4 dialkylamino, Phenyl, heteroaryl, heteroarylC r C 4 alkyl or hetero C 3 -C 4 cyclyl C r C 4 alkyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C4-Alkyl, Ci-C4-Haloalkyl, Ci-C4-Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen, Ci-C-Alkyl, C,-C4-Haloalkyl, CrC4-Alkoxy, C,-C4-Alkylsulfanyl, CrC4-Alkylsulfmyl, C1- C4-Alkylsulfonyl, C]-C4-Monoalkylamino, Ci-C4-Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C4-Alkyl, Q-Q-Haloalkyl, Ci-C4-Alkoxy oder Cyano.where a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, nitro or cyano; one Is heterocyclyl optionally substituted by -OH / = 0, -SH / = S, -NH2, halogen, Ci-C-alkyl, C, -C 4 haloalkyl, C r C 4 alkoxy, C, -C 4 - alkylsulfanyl, C r C 4 -Alkylsulfmyl, C 1 - C 4 alkylsulfonyl, C] -C 4 monoalkylamino, Ci-C4 dialkylamino, nitro or cyano; and one attached to phenyl, heteroaryl or heterocyclyl alkanediyl radical optionally mono- or polysubstituted by halogen, Ci-C 4 alkyl, QQ-haloalkyl, Ci-C 4 alkoxy or cyano.
R6, R6 , R6 , R6 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Amino, Cyano, Fluor, Chlor, Brom, Iod, CrC2-Alkyl, CrC2-Haloalkyl, CrC2-Alkoxy, C1-C2- Haloalkoxy, Phenyl oder Heteroaryl;R 6 , R 6 , R 6 , R 6 are very particularly preferably each independently hydrogen, amino, cyano, fluorine, chlorine, bromine, iodine, C r C 2 alkyl, C r C 2 haloalkyl, C r C 2 Alkoxy, C 1 -C 2 haloalkoxy, phenyl or heteroaryl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C2-Alkyl, Ci-C2-Haloalkyl, Ci-C2-Alkoxy, Nitro oder Cyano.where a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, nitro or cyano.
R6, R6 , R6 , R6 stehen unabhängig voneinander insbesonders bevorzugt für Wasserstoff, Amino, Cyano, Fluor, Chlor, Methyl, Ethyl, CrC2-Haloalkyl, Methoxy, Ethoxy oder C1-C2- Haloalkoxy;R 6, R 6, R 6, R 6 independently of one another particularly preferably represent hydrogen, amino, cyano, fluorine, chlorine, methyl, ethyl, C r C 2 haloalkyl, methoxy, ethoxy or C 1 -C 2 - haloalkoxy;
R7 steht bevorzugt für Wasserstoff, Amino, Hydroxy, Cyano, Ci-C6-Alkyl, C1-C6-R 7 preferably represents hydrogen, amino, hydroxy, cyano, Ci-C 6 alkyl, C 1 -C 6 -
Haloalkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, C1-C6-AIkOXy, C2-C6-Alkenyloxy, C2- C6-Alkinyloxy, CrC6-Alkoxycarbonyl, CrC6-Alkylcarbonyl, CrCe-Alkylaminocarbonyl, C1-C6- Dialkylaminocarbonyl, Phenyl, Phenyl-CrC6-alkyl, Heteroaryl-Ci-C6-alkyl oder Hetero-C3-C6- cyclyl-CrC6-alkyl;Haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, -C 6 alkoxycarbonyl, C r C 6 alkylcarbonyl, CRCE alkylaminocarbonyl, C 1 -C 6 - alkylaminocarbonyl, phenyl, phenyl-C r C 6 -alkyl, heteroaryl-C 6 alkyl or hetero-C 3 -C 6 - cyclyl-C r C 6 -alkyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, C1-C6-AIlCyI, C1-C6-HaIOaIkVl, C1-C6-AIkOXy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen, C1-C6-AIkVl, CrC6-Haloalkyl, CrC6-Alkoxy, Ci-C6-Alkylsulfanyl, CrC6-Alkylsulfmyl, C1- C6-Alkylsulfonyl, CrCό-Monoalkylamino, CrQ-Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, C1-C6-AIlCyI, CrC6-Haloalkyl, Ci-C6-Alkoxy oder Cyano undwhere a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -HaIOaIkVl, C 1 -C 6 -alkoxy, nitro or cyano; a heterocyclyl radical optionally substituted by -OH / = 0, -SH / = S, -NH 2, halogen, C 1 -C 6 -alkyl, C r C 6 haloalkyl, C r C 6 alkoxy, Ci-C 6 alkylsulphanyl, C r C 6 -Alkylsulfmyl, C 1 - C 6 alkylsulfonyl, CrC ό monoalkylamino, CRQ dialkylamino, nitro or cyano; and a tied to phenyl, heteroaryl or heterocyclyl alkanediyl radical optionally mono- or polysubstituted by halogen, C 1 -C 6 -alkyl, C r C 6 haloalkyl, Ci-C 6 alkoxy or cyano and
wobei gegebenenfalls zwei benachbarte Reste aus R6, R6 , R6 , R6 und R7 zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-, -SO2-, -NH- oder -N-C1-C6-AIlCyI- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstoffkette unterbrochenes Alkandiyl oder Alkendiyl mit jeweils 2 bis 5 Kohlenstoffatomen stehen; R7 steht besonders bevorzugt für Wasserstoff, Amino, Hydroxy, Cyano, Ci-C4-Alkyl, C\-where appropriate two adjacent radicals of R 6 , R 6 , R 6 , R 6 and R 7 together represent optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -NC 1 -C 6 -alkyl-, at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl having in each case 2 to 5 carbon atoms; R 7 particularly preferably represents hydrogen, amino, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -
C4-Haloalkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C4-Cycloalkyl, CrC4-Alkoxy, C2-Q-Alkenyloxy,C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C r C 4 alkoxy, C 2 -Q-alkenyloxy,
C2-C4-Alkinyloxy, C,-C4-Alkoxycarbonyl, CrC4-Alkylcarbonyl, CrC4-Alkylaminocarbonyl, Q-C 2 -C 4 alkynyloxy, C, -C 4 alkoxycarbonyl, C r C 4 alkylcarbonyl, C r C 4 alkylaminocarbonyl, Q
C4-Dialkylaminocarbonyl, Phenyl, Phenyl-CrC4-alkyl, Heteroaryl-Ci-C4-alkyl oder Hetero-C3-C4- cyclyl-CrC4-alkyl; C4 dialkylaminocarbonyl, phenyl, phenyl-C r C 4 alkyl, heteroaryl-Ci-C4-alkyl or hetero-C 3 -C 4 - cyclyl-C r C 4 alkyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C4-Alkyl, Ci-C4-Haloalkyl, Ci-C4-Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen, C1-C4-AIlCyI, CrC4-Haloalkyl, C1-C4-AIkOXy, Q-Gt-Alkylsulfanyl, CrC4-Alkylsulfmyl, CrC4-Alkylsulfonyl, Ci-C4-Monoalkylamino, Ci-C4-Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C4-Alkyl, Ci-C4-Haloalkyl, Ci-C4- Alkoxy oder Cyano undwhere a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, nitro or cyano; a heterocyclyl radical optionally substituted by -OH / = 0, -SH / = S, -NH 2, halogen, C 1 -C 4 -alkyl, C r C 4 haloalkyl, C 1 -C 4 -alkoxy, QG t - alkylsulfanyl, C r C 4 -Alkylsulfmyl, C r C 4 alkylsulfonyl, Ci-C4-monoalkylamino, Ci-C 4 dialkylamino, nitro or cyano; and one attached to phenyl, heteroaryl or heterocyclyl alkanediyl radical optionally mono- or polysubstituted by halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 - alkoxy or cyano and
wobei gegebenenfalls zwei benachbarte Reste aus R6, R6 , R6 , R6 und R7 zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-, -SO2-, -NH- oder -N- Ci-C4-Alkyl- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstoffkette unterbrochenes Alkandiyl oder Alkendiyl mit jeweils 2 bis 5 Kohlenstoffatomen stehen;where appropriate two adjacent radicals of R 6 , R 6 , R 6 , R 6 and R 7 together represent optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N-Ci-C 4 -alkyl- at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
R7 steht ganz besonders bevorzugt für Wasserstoff, Amino, Hydroxy, Cyano, CpC2- Alkyl, CrC2-Haloalkyl, Cyclopropyl, CrC2-Alkoxy, CrC2-Alkoxycarbonyl, C,-C2-Alkylcarbonyl, Ci-C2-Alkylaminocarbonyl, Ci-C2-Dialkylaminocarbonyl, Phenyl, Phenyl-Q-Q-alkyl oder Heteroaryl-Ci -C2-alkyl;R 7 very particularly preferably represents hydrogen, amino, hydroxy, cyano, CpC 2 - alkyl, C r C 2 haloalkyl, cyclopropyl, C r C 2 alkoxy, C r C 2 alkoxycarbonyl, C, -C 2 -alkylcarbonyl C 1 -C 2 -alkylaminocarbonyl, C 1 -C 2 -dialkylaminocarbonyl, phenyl, phenyl-QQ-alkyl or heteroaryl-C 1 -C 2 -alkyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C2-Alkyl, C]-C2-Haloalkyl, Ci-C2-Alkoxy, Nitro oder Cyano; und ein an Phenyl oder Heteroaryl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, C]-C2-Alkyl, Cj-C2-Haloalkyl, Ci-C2-Alkoxy oder Cyano undwhere a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, nitro or cyano; and an alkanediyl radical attached to phenyl or heteroaryl is optionally mono- or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy or cyano and
wobei gegebenenfalls zwei benachbarte Reste R6 / R6, R6 / R7 oder R7 / R7 zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-, -SO2-, -NH- oder -N- C]-C2-Alkyl- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstoffkette unterbrochenes Alkandiyl oderwhere appropriate, two adjacent radicals R 6 / R 6 , R 6 / R 7 or R 7 / R 7 together for optionally substituted and / or optionally substituted by oxygen or sulfur or a grouping of the series -S (O) -, -SO 2 -, -NH- or -N-C] -C 2 alkyl- at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or
Alkendiyl mit jeweils 2 bis 4 Kohlenstoffatomen stehen; R7 steht insbesondere bevorzugt für Wasserstoff, Amino, Cyano, Ci-C2-Alkyl, CrC2- Haloalkyl oder Ci-C2-Alkoxy;Alkenediyl each having 2 to 4 carbon atoms; R 7 is particularly preferably represents hydrogen, amino, cyano, Ci-C 2 alkyl, C r C 2 - haloalkyl or Ci-C 2 alkoxy;
R8 und R9 stehen bevorzugt und unabhängig voneinander für Wasserstoff, Ci-C6-Alkyl, Cr C6-Haloalkyl, C2-C6-Alkenyl (gegebenenfalls substituiert durch Halogen, Ci-C6-Alkyl, Q-C6- Haloalkyl oder Cyano), C2-C6-Alkinyl, C3-C6-Cycloalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C6-Haloalkyl, Ci-C6-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten), C3-C6-Cycloalkyl-Ci-C6-alkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, CrC6-Haloalkyl, Ci-C6-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten, am C)-C6-Alkylteil gegebenenfalls ein- oder mehrfach substituiert durch Halogen, CrC6-Alkyl, Ci-C6-Haloalkyl, CrC6-Alkoxy oder Cyano), C3-C6-Cycloalkyl- carbonyl-C3-C6-heterocyclyl, Ci-C6-Alkyloxycarbonyl-C3-C6-heterocyclyl, Ci-Cβ-Alkylsulfinyl-Ci- C6-alkyl, C,-C6-Alkylsulfanyl-CrC6-alkyl, Ci-C6-Alkylsulfonyl-Ci-C6-alkyl, Hydroxy-d-Ce-alkyl, C3-C6-Heterocyclylcarbonyl-Ci-C6-alkyl, Heteroarylcarbonylamino-CrQ-alkyl, Ci-C6-HaIo- alkoxy-Ci-C6-alkyl, Ci-Cβ-Alkylthiocarbonyl, CrQ-Dialkylaminocarbonyl, Q-Cβ-Alkylamino- carbonyl, Ci-C6-Haloallcylaminocarbonyl, Ci-C6-Alkoxy, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, Cr Cβ-Alkoxy-Ci-Cβ-alkyl, C,-C6-Alkylcarbonyl-C,-C6-alkyl, C(R10Rn)CR5=NO-Ci-C6-Alkyl, CrC6- Alkylsulfonyl, Ci-Cg-Alkylcarbonyl, Ci-Cβ-Haloalkylcarbonyl, C2-C6-Alkenylcarbonyl, C2-C6- Alkinylcarbonyl, C3-C6-Cycloalkylcarbonyl, Ci-C6-Alkoxycarbonyl, C2-C6- Alkenyloxycarbonyl, C2-C6-Alkinyloxycarbonyl, Ci-C6-Alkoxyalkylcarbonyl, Phenylsulfonyl, Phenyl, Heteroaryl, Hetero-C3-C6-cyclyl, Phenyl-CrC6-alkyl, Heteroaryl-CrC6-alkyl, Hetero-C3-C6-cyclyl-CrC6-alkyl, Phenylcarbonyl, Heteroarylcarbonyl, Hetero-C3-C6-cyclylcarbonyl, Phenyl-Ci-Cö-alkylcarbonyl, Heteroaryl-Ci-C^alkylcarbonyl, Hetero-C3-C6-cyclyl-Ci-C6-alkylcarbonyl, Phenoxycarbonyl oder Phenyl-Ci-C6-alkoxycarbonyl;R 8 and R 9 are preferably and independently of one another are hydrogen, Ci-C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkenyl (optionally substituted by halogen, Ci-C 6 alkyl, QC 6 - haloalkyl or cyano), C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl (the cycle may optionally be mono- or polysubstituted by Ci-C substituted by halogen, 6 -haloalkyl, Ci-C 6 alkyl or fused to an aromatic or heteroaromatic), C 3 -C 6 -cycloalkyl-C 6 -alkyl (optionally mono- or polysubstituted at the cycle by halogen, C r C 6 haloalkyl, Ci-C 6 alkyl or fused to a aromatic or heteroaromatic , optionally mono- 6 alkyl moiety at the C) -C or polysubstituted by halogen, C r C 6 alkyl, Ci-C 6 haloalkyl, C r C 6 alkoxy or cyano), C 3 -C 6 cycloalkyl carbonyl-C 3 -C 6 heterocyclyl, C 6 alkyloxycarbonyl C 3 -C 6 heterocyclyl, Ci-Cβ-alkylsulfinyl-Ci- C6 alkyl, C, -C 6 alkylsulfanyl-C r C 6 alkyl, C 1 -C 6 -alkylsulfonyl-C 1 -C 6 -alkyl, hydroxy-C 1 -C 6 -alkyl, C 3 -C 6 -Heterocyclylcarbonyl-Ci-C 6 alkyl, heteroarylcarbonylamino-CRQ-alkyl, Ci-C 6 alkoxy -HaIo--Ci-C 6 alkyl, Ci-Cβ-alkylthiocarbonyl, CRQ-dialkylaminocarbonyl, Q-Cβ alkylamino- carbonyl, Ci-C 6 -Haloallcylaminocarbonyl, Ci-C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C r Cβ-alkoxy-Ci-Cβ-alkyl, C, - C 6 alkylcarbonyl-C, -C 6 alkyl, C (R 10 R n) CR 5 = NO-Ci-C 6 alkyl, C r C 6 - alkylsulfonyl, Ci-Cg-alkylcarbonyl, Ci-Cβ-haloalkylcarbonyl , C 2 -C 6 alkenylcarbonyl, C 2 -C 6 - alkynylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 6 alkoxycarbonyl, C 2 -C 6 - alkenyloxycarbonyl, C 2 -C 6 -alkynyloxycarbonyl, Ci- C 6 alkoxyalkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl, heteroC 3 -C 6 -cyclyl, phenylC r C 6 alkyl, heteroarylC r C 6 alkyl, hetero C 3 -C 6 cycloalkyl r C 6 alkyl, phenylcarbonyl, heteroarylcarbonyl, hetero-C 3 -C 6 -cyclylcarbonyl, phenyl-Ci-C ö alkylcarbonyl, heteroaryl-Ci-C ^ alkylcarbonyl, hetero-C 3 -C 6 -cyclyl-Ci-C 6- alkylcarbonyl, phenoxy carbonyl or phenyl-C 1 -C 6 -alkoxycarbonyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, C]-C6-Alkyl, Ci-C6-Haloalkyl, Ci-C6-Alkoxy, Nitro oder Cyano; einwhere a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, nitro or cyano; one
Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen,Heterocyclyl optionally substituted by -OH / = 0, -SH / = S, -NH 2 , halogen,
C1-C6-AIkVl, CrC6-Haloalkyl, C1-C6-AIkOXy, CrC6-Alkylsulfanyl, CrC6-Alkylsulfmyl, C,-C 1 -C 6 -alkyl, C r C 6 haloalkyl, C 1 -C 6 -alkoxy, C r C 6 alkylsulfanyl, C r C 6 -Alkylsulfmyl, C, -
C6-Alkylsulfonyl, Ci-C6-Monoalkylamino, Ci-C6-Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C6-Alkyl, Ci-C6-Haloalkyl, CrC6-Alkoxy oder Cyano undC 6 alkylsulfonyl, C 1 -C 6 monoalkylamino, C 1 -C 6 dialkylamino, nitro or cyano; and a tied to phenyl, heteroaryl or heterocyclyl alkanediyl radical optionally mono- or Ci-C 6 alkyl, Ci-C polysubstituted by halogen, 6 -haloalkyl, C r C 6 alkoxy or cyano and
wobei gegebenenfalls R8 / R9 zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-, -SO2-, -NH- oder -N-Ci-Q-Alkyl- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstofflcette unterbrochenes Alkandiyl oder Alkendiyl mit jeweils 2 bis 5 Kohlenstoffatomen stehen;where appropriate R 8 / R 9 together represent optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N-Ci-Q-alkyl at the beginning (or at the end) or within the Hydrocarbon chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
R8 und R9 stehen besonders bevorzugt und unabhängig voneinander für Wasserstoff, C]-C4- Alkyl, Ci-Q-Haloalkyl, C2-C4-Alkenyl (gegebenenfalls substituiert durch Halogen, Ci-C4-Alkyl, CrC4-Haloalkyl oder Cyano), C2-C4-Alkinyl, C3-C5-Cycloalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C4-Haloalkyl, Ci-C4-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten), C3-C5-Cycloalkyl-Ci-C4-alkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C4-Haloalkyl, Ci-C4-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten, am C]-C4-Alkylteil gegebenenfalls ein- oder mehrfach substituiert durch Halogen, C1-C4-AIlCyI, CrC4-Haloalkyl, CrC4-AJkoxy oder Cyano), CrC4-Alkylsulfmyl-Ci- C4-alkyl, CrC4-Alkylsulfanyl-CrC4-alkyl, CrC4-Alkylsulfonyl-CrC4-alkyl, C,-C4-Haloalkoxy-Cr C4-alkyl, Ci-C4-Alkylthiocarbonyl, C]-C4-Dialkylaminocarbonyl, C1-C4-Alkylaminocarbonyl, Q- C4-Haloalkylaminocarbonyl, Ci-C4-Alkoxy, C2-C4-Alkenyloxy, C2-C4-Alkinyloxy, CrQ-Alkoxy- CrC4-alkyl, Ci-C4-Alkylcarbonyl-C,-C4-alkyl, C(R10Rn)CR5=NO-CrC4-Alkyl, CrC4-Alkyl- sulfonyl, CrC4-Alkylcarbonyl, CrC4-Haloalkylcarbonyl, C2-C4-Alkenylcarbonyl, C2-C4-Alkinyl- carbonyl, C3-C4-Cycloalkylcarbonyl, Ci-C4-Alkoxycarbonyl, C2-C4-Alkenyloxycarbonyl, C2-C4- Alkinyloxycarbonyl, Ci-C4-Alkoxyalkylcarbonyl, Phenylsulfonyl, Phenyl, Heteroaryl, Hetero-C3- C4-cyclyl, Phenyl-CrC4-alkyl, Heteroaryl-CrC4-alkyl, Hetero-C3-C4-cyclyl-CrC4-alkyl, Phenyl- carbonyl, Heteroarylcarbonyl, Hetero-C3-C4-cyclylcarbonyl, Phenyl-Ci-C4-alkylcarbonyl, Hetero- aryl-Ci-C4-alkylcarbonyl, Hetero-C3-C4-cyclyl-Ci-C4-alkylcarbonyl, Phenoxycarbonyl oder Phenyl- Ci -C4-alkoxycarbonyl;R 8 and R 9 are particularly preferred and are independently hydrogen, C] -C 4 - alkyl, Ci-Q-haloalkyl, C 2 -C 4 alkenyl (optionally substituted by halogen, Ci-C 4 alkyl, C r C 4 haloalkyl or cyano), C 2 -C 4 alkynyl, C 3 -C 5 cycloalkyl (the cycle may optionally be mono- or polysubstituted by halogen, Ci-C4-haloalkyl, Ci-C 4 alkyl or condensed to an aromatic or heteroaromatic), C 3 -C 5 -cycloalkyl-Ci-C 4 -alkyl (optionally mono- or polysubstituted by halogen, Ci-C 4 haloalkyl, Ci-C 4 -alkyl or fused to a Aromatics or heteroaromatics, on the C] -C 4 -alkyl part optionally mono- or polysubstituted by halogen, C 1 -C 4 -alkyl, C r C 4 -haloalkyl, C r C 4 -alkoxy or cyano), C r C 4 Alkylsulfmyl-Ci- C 4 -alkyl, C r C 4 -alkylsulfanyl-C r C 4 -alkyl, C r C 4 -alkylsulfonyl-C r C 4 -alkyl, C, -C 4 -haloalkoxy-C r C 4 alkyl, Ci-C 4 alkylthiocarbonyl, C] -C 4 -dialkylaminocarbonyl, C 1 -C 4 -Alkyla minocarbonyl, Q- C 4 -Haloalkylaminocarbonyl, Ci-C 4 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, CRQ alkoxy C r C 4 alkyl, Ci-C4-alkylcarbonyl C, -C 4 alkyl, C (R 10 R n) CR 5 = NO-C r C 4 alkyl, C r C 4 alkyl sulfonyl, C r C 4 alkylcarbonyl, C r C 4 haloalkylcarbonyl, C 2 -C 4 alkenylcarbonyl, C 2 -C 4 alkynyl carbonyl, C 3 -C 4 cycloalkyl-carbonyl, Ci-C 4 alkoxycarbonyl, C 2 -C 4 -alkenyloxycarbonyl, C 2 -C 4 - alkynyloxycarbonyl, C -C 4 -Alkoxyalkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl, heterocyclo-C 3 - C 4 -cyclyl, phenyl-C r C 4 alkyl, heteroaryl-C r C 4 alkyl, hetero-C 3 -C 4 -cyclyl- C r C 4 alkyl, phenyl carbonyl, heteroarylcarbonyl, hetero-C 3 -C 4 -cyclylcarbonyl, phenyl-Ci-C4-alkylcarbonyl, hetero- aryl-Ci-C4-alkylcarbonyl, hetero-C 3 -C 4 -cyclyl-Ci-C4-alkylcarbonyl, phenoxycarbonyl or phenyl-Ci-C4 alkoxycarbonyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C4-Alkyl, Ci-C4-Haloalkyl, Ci-C4-Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen, C,-C4-Alkyl, C,-C4-Haloalkyl, CrC4-Alkoxy, Ci-C4-Alkylsulfanyl, CrC4-Alkylsulfmyl, Cr where a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, nitro or cyano; a heterocyclyl radical optionally substituted by -OH / = 0, -SH / = S, -NH2, halogen, C, -C 4 alkyl, C, -C 4 haloalkyl, C r C 4 alkoxy, Ci-C 4- alkylsulfanyl, C r C 4 -alkylsulfmyl, C r
C4-Alkylsulfonyl, Ci-C4-Monoalkylamino, Ci-C4-Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, C)-C4-AIlCyI, Ci-C4-Haloalkyl, C]-C4-Alkoxy oder Cyano undC 4 alkylsulfonyl, C 1 -C 4 monoalkylamino, C 1 -C 4 dialkylamino, nitro or cyano; and a tied to phenyl, heteroaryl or heterocyclyl alkanediyl radical optionally mono- or polysubstituted by halogen, C) -C 4 -alkyl, Ci-C 4 haloalkyl, C] -C 4 alkoxy or cyano and
wobei gegebenenfalls R8 / R9 zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-, -SO2-, -NH- oder -N-Ci -C4- Alkyl- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstoffkette unterbrochenes Alkandiyl oder Alkendiyl mit jeweils 2 bis 5 Kohlenstoffatomen stehen; R8 und R9 stehen ganz besonders bevorzugt und unabhängig voneinander für Wasserstoff, Ci-C4-Alkyl, C]-C4-Haloalkyl, C3-C5-Cycloalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Haloalkyl, C]-C2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten), C3-C5-Cycloalkyl-Ci-C2-alkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Haloalkyl, Ci-C2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten, am Ci-C2-Alkylteil gegebenenfalls ein- oder mehrfach substituiert durch Halogen, CrC2-Alkyl, CrC2-Haloalkyl, Ci-C2-Alkoxy oder Cyano), CrC2-Alkylsulfinyl-Cr C3-alkyl, d-QrAlkylsulfanyl-Ci-Cj-alkyl, C,-C2-Alkylsulfonyl-C1-C3-alkyl, Phenyl-C1-C4-alkyl, Heteroaryl-Ci-C4-alkyl, Ci-C4-Dialkylaminocarbonyl, C1-C4-Alkylaminocarbonyl, Ci-C4-HaIo- alkylaminocarbonyl, Ci-C2-Alkylsulfonyl, Ci-C2-Alkylcarbonyl, Ci-C2-Haloalkylcarbonyl, C3-C5- Cycloalkylcarbonyl, Ci-C2-Alkoxycarbonyl, Ci-C2-Alkoxy-Ci-C2-alkylcarbonyl, Phenylsulfonyl, Phenyl, Heteroaryl, Hetero-C3-C5-cyclyl, Phenylcarbonyl, Heteroarylcarbonyl, Hetero-C3-C5- cyclylcarbonyl, Phenyl-Ci-C2-alkylcarbonyl, Hetero-C3-C5-cyclyl- C1-C2-alkylcarbonyl, Phenoxycarbonyl oder Phenyl-Ci-C2-alkoxycarbonyl stehen;where appropriate, R 8 / R 9 together represent optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N-Ci-C 4 -alkyl - at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms; R 8 and R 9 are most preferably and independently hydrogen, Ci-C 4 alkyl, C] -C 4 haloalkyl, C 3 -C 5 cycloalkyl (optionally mono- or on cycle polysubstituted by halogen, C C 2 -C 10 -alkyl, C 1 -C 2 -alkyl or fused to an aromatic or heteroaromatic radical), C 3 -C 5 -cycloalkyl-C 1 -C 2 -alkyl (optionally substituted one or more times by halogen, C 1 -C 5 -alkyl on the cycle C 2 haloalkyl, Ci-C 2 alkyl or fused to a aromatic or heteroaromatic, optionally mono- 2 alkyl moiety on the C-C or poly-substituted by halogen, C r C 2 alkyl, C r C 2 haloalkyl, C -C 2 alkoxy or cyano), C r C 2 alkylsulfinyl-C r C 3 alkyl, d-Qr alkylsulfanyl-C 1 -C 12 alkyl, C 1 -C 2 alkylsulfonyl C 1 -C 3 alkyl, phenyl -C 1 -C 4 alkyl, heteroaryl-Ci-C4-alkyl, Ci-C4-dialkylaminocarbonyl, C 1 -C 4 alkylaminocarbonyl, Ci-C 4 -HaIo- alkylaminocarbonyl, Ci-C 2 alkylsulfonyl, C -C 2 alkylcarbonyl, Ci-C 2 haloalkylcarbonyl, C 3 -C 5 - Cycloalkylc arbonyl, C 1 -C 2 -alkoxycarbonyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl, hetero-C 3 -C 5 -cyclyl, phenylcarbonyl, heteroarylcarbonyl, hetero-C 3 -C 5 cyclylcarbonyl, phenyl-Ci-C 2 -alkylcarbonyl, -Alkoxycarbonyl hetero-C 3 -C 5 -cyclyl- C 1 -C 2 alkylcarbonyl, phenoxycarbonyl or phenyl-C 2;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C2-Alkyl, Ci-C2-Haloalkyl, Ci-C2-Alkoxy, Nitro oder Cyano; und ein an Phenyl oder Heteroaryl gebundener Alkandiy-Rrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C4-Alkyl, Ci-C4-Haloalkyl, C]-C2-Alkoxy oder Cyano undwhere a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, nitro or cyano; and a phenyl or heteroaryl bound Alkandiy-R is optionally mono- or polysubstituted by halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C] -C 2 alkoxy or cyano and
wobei gegebenenfalls R8 / R9 zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-,where appropriate R 8 / R 9 together represent optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -,
-SO2-, -NH- oder -N-Ci -C4- Alkyl- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstoffkette unterbrochenes Alkandiyl oder Alkendiyl mit jeweils 2 bis 5 Kohlenstoffatomen stehen;-SO 2 -, -NH- or -N-Ci-C 4 -alkyl- at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
R8 und R9 stehen insbesonders bevorzugt und unabhängig voneinander für Wasserstoff, Q- C4-Alkyl, C,-C4-Haloalkyl, C3-C5-Cycloalkyl, C3-C5-Cycloalkyl-CrC2-alkyl, C3-C5-Cyclohalo- alkyl-Ci-C2-alkyl, C3-C4-Halocycloalkyl, Methylsulfanyl-CrC3-alkyl, Methylsulfinyl-Ci-Cralkyl, Methylsulfonyl-Ci-C3-alkyl, Phenylmethyl (am Aromaten gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso- Propyl, Methoxy oder Trifluormethyl), Pyridylmethyl (am Pyridyl gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso-Propyl, Methoxy oder Trifluormethyl) oder Pyrimidylmethyl (am Pyrimidyl gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso-Propyl, Methoxy oder Trifluormethyl);R 8 and R 9 are especially preferred and are independently hydrogen, Q- C4 alkyl, C, -C 4 haloalkyl, C 3 -C 5 cycloalkyl, C 3 -C 5 cycloalkyl-C r C 2 - alkyl, C 3 -C 5 -cyclohaloalkyl-Ci-C 2 -alkyl, C 3 -C 4 -Halocycloalkyl, methylsulfanyl-C r C 3 alkyl, methylsulfinyl-Ci-cralkyl, methylsulfonyl-Ci-C 3 -alkyl , Phenylmethyl (optionally substituted on the aromatic mono- or polysubstituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, on the methyl part optionally mono- or polysubstituted by methyl, ethyl, propyl, iso-propyl, methoxy or trifluoromethyl), pyridylmethyl (optionally mono- or polysubstituted on the pyridyl by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, optionally mono- or polysubstituted by methyl, ethyl, propyl, iso in the methyl part. Propyl, methoxy or trifluoromethyl) or pyrimidylmethyl (optionally mono- or polysubstituted on the pyrimidyl dur fluorine, chlorine, bromine, methyl, ethyl, Trifluoromethyl, methoxy, cyano or nitro, on the methyl part optionally mono- or polysubstituted by methyl, ethyl, propyl, iso-propyl, methoxy or trifluoromethyl);
R10 und R11 stehen bevorzugt und unabhängig voneinander für Wasserstoff, Ci-C6-Alkyl, Ci- C6-Haloalkyl oder Cyano;R 10 and R 11 are preferably and independently of one another hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or cyano;
R10 und R11 stehen besonders bevorzugt und unabhängig voneinander für Wasserstoff, Cr R 10 and R 11 are particularly preferably and independently of one another hydrogen, C r
C4-Alkyl, Ci-Q-Haloalkyl oder Cyano;C 4 alkyl, Ci-Q-haloalkyl or cyano;
R10 und R11 stehen ganz besonders bevorzugt und unabhängig voneinander für Wasserstoff, CrC2-Alkyl oder CrC2-Haloalkyl;R 10 and R 11 very particularly preferably independently of one another hydrogen, C r C 2 alkyl or C r C 2 haloalkyl;
R10 und R11 stehen insbesonders bevorzugt für Wasserstoff;R 10 and R 11 are particularly preferably hydrogen;
R12 steht bevorzugt für CrC6-Alkyl oder CrC6-Haloalkyl;R 12 is preferably C r C 6 alkyl or C r C 6 haloalkyl;
R12 steht besonders bevorzugt für Ci-C4-Alkyl oder C1-C4-HaIOaIlCyI;R 12 particularly preferably represents Ci-C 4 alkyl or C 1 -C 4 -HaIOaIlCyI;
R12 steht ganz besonders bevorzugt für Ci-C4-Alkyl;R 12 very particularly preferably represents C 1 -C 4 -alkyl;
R12 steht insbesonders bevorzugt für Methyl oder Ethyl;R 12 is particularly preferably methyl or ethyl;
R13 und R14 stehen bevorzugt und unabhängig voneinander für Wasserstoff, Ci-C6-Alkyl, Cr C6-Haloalkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Ci-C6-Alkoxy-CrC6-alkyl, C,-C6-Alkylcarbonyl-CrR 13 and R 14 preferably and independently of one another represent hydrogen, Ci-C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci-C 6 alkoxy C r C 6 alkyl, C, -C 6 alkylcarbonyl-Cr
Cg-alkyl, C(R10R1 ^CR^NO-d-Q-Alkyl, C,-C6-Alkylsulfonyl, CrC6-Alkylcarbonyl, Q-C6-Cg-alkyl, C (R 10 R 1 ^ CR ^ NO-dQ-alkyl, C, -C 6 alkylsulfonyl, C r C 6 alkylcarbonyl, QC 6 -
Haloalkylcarbonyl, C2-C6-Alkenylcarbonyl, C2-C6-Alkinylcarbonyl, C3-C6-Cycloalkylcarbonyl, Q-Haloalkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 2 -C 6 -alkynylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, Q-
Cß-Alkoxycarbonyl, C2-C6-Alkenyloxycarbonyl, C2-C6-Alkinyloxycarbonyl, Q -C6-AIkOXy-Ci-C6- alkylcarbonyl, Phenylsulfonyl, Phenyl, Heteroaryl, Hetero-C3-C6-cyclyl, Phenyl-CrC6-alkyl, Heteroaryl-C]-C6-alkyl, Hetero-C3-C6-cyclyl-Ci-C6-alkyl, Phenylcarbonyl, Heteroarylcarbonyl,C ß alkoxycarbonyl, C 2 -C 6 alkenyloxycarbonyl, C 2 -C 6 -alkynyloxycarbonyl, Q-C6-alkoxy-Ci-C 6 - alkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl, heterocyclo-C 3 -C 6 -cyclyl , phenyl-C r C 6 -alkyl, heteroaryl-C] to C 6 alkyl, hetero-C 3 -C 6 -cyclyl-Ci-C 6 alkyl, phenylcarbonyl, heteroarylcarbonyl,
Hetero-C3-C6-cyclylcarbonyl, Phenyl- Ci-Cδ-alkylcarbonyl, Heteroaryl-Ci-Q-alkylcarbonyl,Hetero-C 3 -C 6 -cyclylcarbonyl, phenyl Ci-C δ alkylcarbonyl, heteroaryl-Ci-Q-alkylcarbonyl,
Hetero-C3-C6-cyclyl-Ci-C6-alkylcarbonyl, Phenoxycarbonyl oder Phenyl-CrC6-alkoxycarbonyl;Hetero-C 3 -C 6 -cyclyl-Ci-C 6 alkylcarbonyl, phenoxycarbonyl or phenyl-C r C 6 alkoxycarbonyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C6-Alkyl, d-C6-Haloalkyl, CrC6-Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen,wherein a phenyl or heteroaryl radical optionally mono- or Ci-C polysubstituted by halogen, 6 alkyl, dC 6 haloalkyl, C r C 6 alkoxy, nitro or cyano; a heterocyclyl radical is optionally substituted by -OH / = O, -SH / SS, -NH 2 , halogen,
CrC6-Alkyl, C,-C6-Haloalkyl, CrC6-Alkoxy, Ci-C6-Alkylsulfanyl, CrC6-Alkylsulfmyl, C,- C5-Alkylsulfonyl, C]-C6-Monoalkylamino, Ci-C6-Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, CrC6-Alkyl, Ci-C6-Haloalkyl, Ci-C6-Alkoxy oder Cyano oderC r C 6 alkyl, C, -C 6 haloalkyl, C r C 6 alkoxy, Ci-C6 alkylsulfanyl, C r C 6 -Alkylsulfmyl, C, - C 5 alkylsulfonyl, C] -C6 - Monoalkylamino, C 1 -C 6 dialkylamino, nitro or cyano; and one attached to phenyl, heteroaryl or heterocyclyl alkanediyl radical optionally mono- or polysubstituted by halogen, C r C 6 alkyl, Ci-C 6 haloalkyl, Ci-C 6 alkoxy or cyano or
R13 und R14 bilden als Imin die Gruppierung =CR5-NR15R16 oder =CR5-OR12;R 13 and R 14 form as imine the grouping = CR 5 -NR 15 R 16 or = CR 5 -OR 12 ;
R15 und R16 stehen unabhängig voneinander für Alkyl oderR 15 and R 16 are independently alkyl or
R15 und R16 stehen zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-, -SO2-, -NH- oder -N- Alkyl- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstoffkette unterbrochenes Alkandiyl oder Alkendiyl mit jeweils 2 bis 5 Kohlenstoffatomen;R 15 and R 16 together represent optionally substituted and / or optionally substituted by oxygen or sulfur or a grouping of the series -S (O) -, -SO 2 -, -NH- or -N-alkyl- at the beginning (resp. at the end) or within the hydrocarbyl chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
R13 und R14 stehen besonders bevorzugt und unabhängig voneinander für Wasserstoff, C1- C4-Alkyl, CrC4-Haloalkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, Ci-C4-Alkoxy-CrC4-alkyl, CrC4-Alkyl- carbonyl-d-Q-alkyl, C(R10R11)CR5=NO-CrC4-Alkyl, CrC4-Alkylsulfonyl, CrC4-Alkylcarbonyl, Ci-C4-Haloalkylcarbonyl, C2-C4- Alkenylcarbonyl, C2-C4-Alkinylcarbonyl, C3-C4-Cycloalkyl- carbonyl, Ci-C4-Alkoxycarbonyl, C2-C4-Alkenyloxycarbonyl, C2-C4-Alkinyloxycarbonyl, C1-C4- Alkoxy-CrC4-alkylcarbonyl, Phenylsulfonyl, Phenyl, Heteroaryl, Hetero-C3-C4-cyclyl, Phenyl-Ci- C4-alkyl, Heteroaryl-C]-C4-alkyl, Hetero-C3-C4-cyclyl-Ci-C4-alkyl, Phenylcarbonyl, Heteroaryl- carbonyl, Hetero-C3-C4-cyclylcarbonyl, Phenyl-Ci-C4-alkylcarbonyl, Heteroaryl-C]-C4-alkyl- carbonyl, Hetero-C3-C4-cyclyl-CrC4-alkylcarbonyl, Phenoxycarbonyl oder Phenyl-Ci-C4-alkoxy- carbonyl stehen;R 13 and R 14 are particularly preferred and are independently hydrogen, C 1 - C 4 alkyl, C r C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Ci-C 4 - AlkoxyC r C 4 alkyl, C r C 4 alkylcarbonyldQalkyl, C (R 10 R 11 ) CR 5 = NO-C r C 4 alkyl, C r C 4 alkylsulphonyl, C r C 4 alkylcarbonyl, Ci-C 4 haloalkylcarbonyl, C 2 -C 4 - alkenylcarbonyl, C 2 -C 4 -alkynylcarbonyl, C 3 -C 4 cycloalkyl carbonyl, Ci-C 4 alkoxycarbonyl, C 2 -C 4 Alkenyloxycarbonyl, C 2 -C 4 alkynyloxycarbonyl, C 1 -C 4 alkoxyC r C 4 alkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl, hetero C 3 -C 4 cycloalkyl, phenyl-C 1 -C 4 alkyl , heteroaryl-C] -C4 alkyl, hetero-C 3 -C 4 -cyclyl-Ci-C 4 alkyl, phenylcarbonyl, heteroaryl, carbonyl, hetero-C 3 -C 4 -cyclylcarbonyl, phenyl-Ci-C4- -C 4 r are alkylcarbonyl, heteroaryl-C] -C 4 alkyl carbonyl, hetero-C 3-C -cyclyl C 4 alkylcarbonyl, phenoxycarbonyl or phenyl-Ci-C 4 alkoxy carbonyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C4-Alkyl, Q-Q-Haloalkyl, Q-Q-Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =O, -SH / =S, -NH2, Halogen,where a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 4 -alkyl, QQ-haloalkyl, QQ-alkoxy, nitro or cyano; a heterocyclyl radical is optionally substituted by -OH / = O, -SH / SS, -NH 2 , halogen,
C1-C4-AIlCyI, CrC4-Haloalkyl, C,-C4-Alkoxy, C1-C4-Alkylsulfanyl, CrC4-Alkylsulfinyl, C1- C4-Alkylsulfonyl, Ci-C4-Monoalkylamino, Ci-C4-Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, CrC4-Alkyl, C1-C4-HaIOaUCyI, Ci-C4-Alkoxy oder CyanoC 1 -C 4 -alkyl, C r C 4 haloalkyl, C, -C 4 alkoxy, C 1 -C 4 -alkylsulfanyl, C r C 4 alkylsulfinyl, C 1 - C 4 alkylsulfonyl, Ci-C 4 Monoalkylamino, C 1 -C 4 dialkylamino, nitro or cyano; and one attached to phenyl, heteroaryl or heterocyclyl alkanediyl radical optionally mono- or polysubstituted by halogen, C r C 4 alkyl, C 1 -C 4 -HaIOaUCyI, Ci-C 4 alkoxy or cyano
oderor
R13 und R14 bilden als Imin die Gruppierung =CR5-NR15R16 oder =CR5-OR12;R 13 and R 14 form as imine the grouping = CR 5 -NR 15 R 16 or = CR 5 -OR 12 ;
R15 und R16 stehen unabhängig voneinander für Alkyl oderR 15 and R 16 are independently alkyl or
R15 und R16 stehen zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-, -SO2-, -NH- oder -N- Alkyl- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstoffkette unterbrochenes Alkandiyl oder Alkendiyl mit jeweils 2 bis 5 Kohlenstoffatomen;R 15 and R 16 together represent optionally substituted and / or optionally substituted by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N- Alkyl- at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
R13 und R14 stehen ganz besonders bevorzugt und unabhängig voneinander für Wasserstoff, C1-C2-AIlCyI, Ci-C2-Haloalkyl, Ci-CrAlkoxy-Q-C∑-alkyl, CrC2-Alkylsulfonyl, C,-C2-Alkyl- carbonyl, Ci-C2-Haloalkylcarbonyl, Ci-C2-Alkoxycarbonyl, Ci-C2-Alkoxy-CrC2-alkylcarbonyl, Phenylsulfonyl, Phenyl, Heteroaryl, Phenyl-CrC2-alkyl, Heteroaryl-CrC2-alkyl, Phenylcarbonyl, Heteroarylcarbonyl, Phenyl-C!-C2-alkylcarbonyl, Phenoxycarbonyl oder Phenyl-Ci-C2- alkoxycarbonyl;R 13 and R 14 very particularly preferably independently of one another hydrogen, C 1 -C 2 -alkyl, Ci-C 2 haloalkyl, Ci-CrAlkoxy-QC Σ alkyl, C r C 2 alkylsulfonyl, C, -C 2- alkylcarbonyl, C 1 -C 2 -haloalkylcarbonyl, C 1 -C 2 -alkoxycarbonyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl, phenylC r C 2 -alkyl, heteroaryl-C r is C 2 -alkyl, phenylcarbonyl, heteroarylcarbonyl, phenyl-C ! -C 2 -alkylcarbonyl, phenoxycarbonyl or phenyl-C 1 -C 2 -alkoxycarbonyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C2-Alkyl, Ci-C2-Haloalkyl, Ci-C2-Alkoxy, Nitro oder Cyano; und ein anwhere a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, nitro or cyano; and one on
Phenyl oder Heteroaryl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, CrC2-Alkyl, Ci-C2-Haloalkyl, CpC2-AIkOXy oder CyanoPhenyl or heteroaryl bonded alkanediyl radical optionally mono- or polysubstituted by halogen, C r C 2 alkyl, Ci-C 2 haloalkyl, CpC 2 -Akoxy or cyano
oderor
R13 und R14 bilden als Imin die Gruppierung =CR5-NR15R16 oder =CR5-OR12;R 13 and R 14 form as imine the grouping = CR 5 -NR 15 R 16 or = CR 5 -OR 12 ;
R15 und R16 stehen unabhängig voneinander für Alkyl oderR 15 and R 16 are independently alkyl or
R15 und R16 stehen zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-, -SO2-, -NH- oder -N- Alkyl- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstoffkette unterbrochenes Alkandiyl oder Alkendiyl mit jeweils 2 bis 5 Kohlenstoffatomen;R 15 and R 16 together represent optionally substituted and / or optionally substituted by oxygen or sulfur or a grouping of the series -S (O) -, -SO 2 -, -NH- or -N-alkyl- at the beginning (resp. at the end) or within the hydrocarbyl chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
R13 und R14 stehen insbesonders bevorzugt und unabhängig voneinander für Wasserstoff,R 13 and R 14 are particularly preferably and independently of one another hydrogen,
Methyl, Ethyl, Propyl, iso-Propyl, Methylcarbonyl, Methoxycarbonyl, Trifluormethylcarbonyl, Methylsulfanyl, Trifluormethylsulfanyl, Benzyl oder Pyridylmethyl.Methyl, ethyl, propyl, iso-propyl, methylcarbonyl, methoxycarbonyl, trifluoromethylcarbonyl, methylsulfanyl, trifluoromethylsulfanyl, benzyl or pyridylmethyl.
Die Verbindungen der Formel (I) lassen sich in Abhängigkeit von ihrem Substituenten R1 in die Verbindungen der Formel (II), (HI), (IV) und (V) unterteilen: The compounds of the formula (I) can be subdivided into the compounds of the formula (II), (HI), (IV) and (V), depending on their substituent R 1 :
wobeiin which
G1"5, R2, R13, R14, und M die oben angegebenen Bedeutungen haben, R13 und R14 aber nicht gleichzeitig für Wasserstoff stehen undG 1 "5 , R 2 , R 13 , R 14 , and M have the meanings given above, but R 13 and R 14 are not simultaneously hydrogen and
R17 für Halogen, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl oder Cyano steht.R 17 is halogen, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl or cyano.
Hieraus ergeben sich 4-Phenyl-lH-pyrazole der Formeln (II-A), (H-B), (IH-A), (HI-B), (IV-A), (IV- B), (V-A) und (V-B),This results in 4-phenyl-lH-pyrazoles of the formulas (II-A), (HB), (IH-A), (HI-B), (IV-A), (IV-B), (VA) and (VB),
wobeiin which
G -.1'-°5, n R2z, r R> 33, τ R> 1133, τ R> 114", A A 11-2Z und Q die oben angegebenen Bedeutungen haben, R13 und R14 aber nicht gleichzeitig für Wasserstoff stehen undG -.1'- ° 5, n R2 z , r R> 3 3 , τ R> 1 1 3 3 , τ R> 1 1 4 ", A A 1 1 -2 Z and Q have the meanings given above, R 13 and R 14 but not simultaneously are hydrogen and
R17 für Halogen, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl oder Cyano steht.R 17 is halogen, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl or cyano.
Die Erfindung betrifft in einer Ausführungsform 1 Verbindungen der Formel (H-A)The invention relates in one embodiment to compounds of the formula (H-A)
wobeiin which
G1, G2 und G3 unabhängig voneinander für Wasserstoff, Halogen, Methyl oder CF3 stehen;G 1 , G 2 and G 3 independently represent hydrogen, halogen, methyl or CF 3 ;
G4 und G5 für Wasserstoff stehen;G 4 and G 5 are hydrogen;
R2 für Fluor, Chlor, Brom, Iod, C1-C4-AIkOXy-C1-C4-AIlCyI, CrC4-Alkyl, Aryl-CrC4- haloalkyl, CrQ-Alkylsulfanyl, C1 -C6- Alkylsulfinyl, C, -C6- Alkylsulfonyl oder C1-C4 Haloalkyl steht;R 2 represents fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C r C 4 alkyl, aryl-C r C 4 - haloalkyl, CRQ-alkylsulfanyl, C 1 - C 6 is alkylsulfinyl, C 1 -C 6 alkylsulfonyl or C 1 -C 4 haloalkyl;
A1 und A2 unabhängig voneinander für N oder CH stehen;A 1 and A 2 are independently N or CH;
R3 für Fluor, Chlor, Brom, Iod, C1-2-Alkyl, d.2-Haloalkyl, CrC2-Haloalkylsulfanyl, Cr C2-Haloalkylsulfonyl, Ci-C2-Haloalkylsulfinyl oder Cyano steht undR 3 is fluoro, chloro, bromo, iodo, C 1-2 alkyl, d. 2 haloalkyl, C r C 2 haloalkylsulfanyl, C r C 2 haloalkylsulfonyl, C 1 -C 2 haloalkylsulfinyl or cyano and
Q für Q1, Q2, Q3 oder Q4 steht. In einer Ausfiihrungsform 2 betrifft die Erfindung Verbindungen gemäß Ausführungsform 1, in denen Q für Q1 steht.Q stands for Q 1 , Q 2 , Q 3 or Q 4 . In an embodiment 2, the invention relates to compounds according to embodiment 1, in which Q stands for Q 1 .
In einer Ausführungsform 3 betrifft die Erfindung Verbindungen gemäß Ausführungsform 2, in denen Q1 für Z3, Z7, Z15, Z16, Z17, Z1S, Z21, Z22, Z23 oder Z24 steht; R6, R6', R6", R6'" für Wasserstoff, Amino, Cyano, Fluor, Chlor, Methyl, Ethyl, Ci-C2-Haloalkyl, Methoxy, Ethoxy oder Ci-C2- Haloalkoxy stehen; und R7 für Wasserstoff, Amino, Cyano, Ci-C2-Alkyl, C]-C2-Haloalkyl oder Ci- C2-Alkoxy steht.In an embodiment 3, the invention relates to compounds according to embodiment 2, in which Q 1 stands for Z 3 , Z 7 , Z 15 , Z 16 , Z 17 , Z 1S , Z 21 , Z 22 , Z 23 or Z 24 ; R 6 , R 6 ' , R 6 " , R 6'" are hydrogen, amino, cyano, fluorine, chlorine, methyl, ethyl, C 1 -C 2 -haloalkyl, methoxy, ethoxy or C 1 -C 2 -haloalkoxy; and R 7 is hydrogen, amino, cyano, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 2 -alkoxy.
In einer Ausführungsform 4 betrifft die Erfindung Verbindungen gemäß Ausführungsform 3, in denen Q1 für Z16 oder Z3 steht.In an embodiment 4, the invention relates to compounds according to embodiment 3, in which Q 1 is Z 16 or Z 3 .
In einer Ausführungsform 5 betrifft die Erfindung Verbindungen gemäß Ausführungsform 1, in denen Q für Q2 steht.In an embodiment 5, the invention relates to compounds according to embodiment 1, in which Q stands for Q 2 .
In einer Ausführungsform 6 betrifft die Erfindung Verbindungen gemäß Ausführungsform 5, in denen Q2 für C(O)NR8R9 steht und R8 und R9 unabhängig voneinander für Wasserstoff, CrC4- Alkyl, Ci-C4-Haloalkyl, C3-C5-Cycloalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, C)-C2-Haloalkyl, C)-C2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten), C3-C5-Cycloalkyl-Ci-C2-alkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, C]-C2-Haloalkyl, Ci-C2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten, am CrC2-Alkylteil gegebenenfalls ein- oder mehrfach substituiert durch Halogen, CrC2-Alkyl, CrC2-Haloalkyl, CrC2-Alkoxy oder Cyano), CrC2-Alkylsuliϊnyl-Cr C3-alkyl, Ci-C3-Alkylsulfanyl-C,-C3-alkyl, Ci-CrAlkylsulfonyl-Q-Cj-alkyl, Phenyl-CrC4-alkyl oder Heteroaryl -Ci-C4-alkyl stehen; wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, C1-C2-AIlCyI, C]-C2-Haloalkyl, C]-C2-Alkoxy, Nitro oder Cyano; und ein an Phenyl oder Heteroaryl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C4-Alkyl, Ci-C4-Haloalkyl, Ci-C2-Alkoxy oder Cyano.In an embodiment 6 of the invention relates to compounds according to embodiment 5, wherein Q 2 is C (O) NR 8 R 9, and R 8 and R 9 are independently hydrogen, C r C 4 - alkyl, Ci-C 4 haloalkyl , C 3 -C 5 cycloalkyl (the cycle may optionally be mono- or polysubstituted by halogen, C) -C 2 -haloalkyl, C) -C 2 alkyl or fused to a aromatic or heteroaromatic), C 3 -C 5 - Cycloalkyl-C 1 -C 2 -alkyl (optionally substituted one or more times by halogen, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkyl on the cycle or fused to an aromatic or heteroaromatic radical, on the C r C 2 -alkyl part, if appropriate mono- or polysubstituted by halogen, C r C 2 alkyl, C r C 2 haloalkyl, C r C 2 alkoxy or cyano), C r C 2 -Alkylsuliϊnyl Cr-C 3 alkyl, C 3 - Alkylsulfanyl-C, -C 3 -alkyl, C 1 -C 6 -alkylsulfonyl-Q-C 1 -alkyl, phenylC r C 4 -alkyl or heteroaryl-C 1 -C 4 -alkyl; wherein a phenyl or heteroaryl optionally mono- or polysubstituted by halogen, C 1 -C 2 -alkyl, C] -C 2 haloalkyl, C] -C 2 alkoxy, nitro or cyano; and a bound on phenyl or heteroaryl alkanediyl radical optionally mono- or Ci-C 4 alkyl, Ci-C polysubstituted by halogen, 4 haloalkyl, Ci-C 2 alkoxy or cyano.
In einer Ausführungsform 7 betrifft die Erfindung Verbindungen gemäß Ausführungsform 6, in denen R8 und R9 unabhängig voneinander für Wasserstoff, CrC4-Alkyl, Ci-C4-Haloalkyl, C3-C4- Cycloalkyl, C3-C4-Halocycloalkyl, C3-C5-Cycloalkyl-Ci-C2-alkyl, C3-C5-Halocycloalkyl-Ci-C2- alkyl, Methylsulfinyl-CrC3-alkyl, Methylsulfanyl-CrC3-alkyl, Methylsulfonyl-CrC3-alkyl, Phenylmethyl (am Aromaten gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifiuormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso-Propyl, Methoxy oder Trifiuormethyl), Pyridylmethyl (am Pyridyl gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso-Propyl, Methoxy oder Trifluormethyl) oder Pyrimidylmethyl (am Pyrimidyl gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso- Propyl, Methoxy oder Trifluormethyl) stehen.In an embodiment 7 of the invention relates to compounds according to embodiment 6, in which R 8 and R 9 are independently hydrogen, C r C 4 alkyl, Ci-C 4 haloalkyl, C 3 -C 4 - cycloalkyl, C 3 -C 4 halocycloalkyl, C 3 -C 5 cycloalkyl-Ci-C 2 alkyl, C 3 -C 5 halocycloalkyl-Ci-C 2 - alkyl, methylsulfinyl-C r C 3 alkyl, methylsulfanyl-C r C 3 - alkyl, methylsulfonyl-C r C 3 -alkyl, phenylmethyl (optionally monosubstituted or polysubstituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, optionally substituted one or more times by methyl on the methyl part , Ethyl, propyl, iso-propyl, methoxy or trifluoromethyl), pyridylmethyl (pyridyl optionally mono- or polysubstituted by Fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, on the methyl part optionally mono- or polysubstituted by methyl, ethyl, propyl, iso-propyl, methoxy or trifluoromethyl) or pyrimidylmethyl (pyrimidyl optionally on or polysubstituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, on the methyl part optionally mono- or polysubstituted by methyl, ethyl, propyl, iso-propyl, methoxy or trifluoromethyl).
In einer Ausführungsform 8 betrifft die Erfindung Verbindungen gemäß Ausführungsform 1, in denen Q für Q3 steht.In an embodiment 8, the invention relates to compounds according to embodiment 1, in which Q stands for Q 3 .
In einer Ausfuhrungsform 9 betrifft die Erfindung Verbindungen gemäß Ausführungsform 8, in denen Q3 für C(R10Rn)NR8R9 steht; R10 und R11 unabhängig voneinander für Wasserstoff, C1-C2- Alkyl oder Ci-C2-Haloalkyl stehen und R8 und R9 unabhängig voneinander für Wasserstoff, C1-C4- Alkyl, Ci-C4-Haloalkyl, C3-C5-Cycloalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Haloalkyl, C1-C2-AIlCyI oder kondensiert an einen Aromaten oder Heteroaromaten), C3-C5-Cycloalkyl-Ci-C2-alkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Haloalkyl, CrC2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten, am Ci-C2-Alkylteil gegebenenfalls ein- oder mehrfach substituiert durch Halogen, CrC2-Alkyl, CrC2-Haloalkyl, CrC2-Alkoxy oder Cyano), CrC2-Alkylsulfmyl-C,- C3-alkyl, C1-C2-Alkylsulfanyl-C1-C3-alkyl, CrC2-Alkylsulfonyl-Ci-C3-alkyl, Phenyl-CrC4-alkyl, Heteroaryl-Ci-C4-alkyl, Ci-Q-Dialkylaminocarbonyl, Ci-C4-Alkylaminocarbonyl, C1-C4-HaIo- alkylaminocarbonyl, CrC2-Alkylsulfonyl, Ci-C2-Alkylcarbonyl, Ci-C2-Haloalkylcarbonyl, C3-C5- Cycloalkylcarbonyl, CrC2-Alkoxycarbonyl, Ci-C2-Alkoxy-CrC2-alkylcarbonyl, Phenylsulfonyl, Phenyl, Heteroaryl, Hetero-C3-C5-cyclyl, Phenylcarbonyl, Heteroarylcarbonyl, Hetero-C3-C5- cyclylcarbonyl, Phenyl-Ci-C2-alkylcarbonyl, Heteroaryl-Ci-C2-alkylcarbonyl, Hetero-C3-C5-cyclyl- C]-C2-alkylcarbonyl, Phenoxycarbonyl oder Phenyl-Ci-C2-alkoxycarbonyl stehen; wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, C1- C2-Alkyl, Ci-C2-Haloalkyl, Ci-C2-Alkoxy, Nitro oder Cyano; und ein an Phenyl oder Heteroaryl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, C1- C4-Alkyl, C,-C4-Haloalkyl, CrC2-Alkoxy oder Cyano.In one embodiment 9, the invention relates to compounds according to embodiment 8, in which Q 3 is C (R 10 R n ) NR 8 R 9 ; R 10 and R 11 are independently hydrogen, C 1 -C 2 - alkyl or Ci-C 2 haloalkyl, and R 8 and R 9 are independently hydrogen, C 1 -C 4 - alkyl, Ci-C 4 haloalkyl , C 3 -C 5 cycloalkyl (optionally mono- or polysubstituted at the cycle by halogen, Ci-C 2 haloalkyl, C 1 -C 2 -alkyl or fused to a aromatic or heteroaromatic), C 3 -C 5 cycloalkyl -C-C 2 -alkyl (optionally mono- or polysubstituted at the cycle by halogen, Ci-C 2 haloalkyl, C r C 2 alkyl or fused to a aromatic or heteroaromatic, the Ci-C 2 alkyl moiety may optionally be mono- or polysubstituted by halogen, C r C 2 alkyl, C r C 2 haloalkyl, C r C 2 alkoxy or cyano), C r C 2 -Alkylsulfmyl-C, - C 3 alkyl, C 1 -C 2 alkylsulfanyl-C 1 -C 3 alkyl, C r C 2 alkylsulfonyl-Ci-C 3 alkyl, phenyl-C r C 4 alkyl, heteroaryl-Ci-C4-alkyl, Ci-Q-dialkylaminocarbonyl, C C 4 alkylaminocarbonyl, C 1 -C 4 -haloalkylaminocarbonyl, C r C 2 -alk ylsulfonyl, Ci-C2 alkylcarbonyl, Ci-C 2 haloalkylcarbonyl, C 3 -C 5 - cycloalkylcarbonyl, C r C 2 alkoxycarbonyl, Ci-C 2 alkoxy-C r C 2 alkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl , Hetero-C 3 -C 5 -cyclyl, phenylcarbonyl, heteroarylcarbonyl, hetero-C 3 -C 5 -cycloylcarbonyl, phenyl-C 1 -C 2 -alkylcarbonyl, heteroaryl-C 1 -C 2 -alkylcarbonyl, hetero-C 3 -C 5 -cyclyl- -alkoxycarbonyl C] -C 2 alkylcarbonyl, phenoxycarbonyl or phenyl-C 2; where a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, nitro or cyano; and a bound on phenyl or heteroaryl alkanediyl radical optionally mono- or polysubstituted by halogen, C 1 - C 4 alkyl, C, -C 4 haloalkyl, C r C 2 alkoxy or cyano.
In einer Ausführungsform 10 betrifft die Erfindung Verbindungen gemäß Ausfuhrungsform 9, in denen R8 und R9 unabhängig voneinander für Wasserstoff, Ci-C2-Alkyl, Ci-C2-Haloalkyl, C3-C5- Cycloalkyl, C3-C5-Cycloalkyl-CrC2-alkyl, C3-C5-HaIoCyClOaIlCyI, C3-C5-Halocycloalkyl-Ci-C2- alkyl, Methylsulfmyl-C,-C3-alkyl, Methylsulfanyl-C,-C3-alkyl, Methylsulfonyl-CpCs-alkyl, Phenyl-Ci-C2-alkyl, Heteroaryl-Ci-C2-alkyl, CrC2-Dialkylaminocarbonyl, C1 -C2- Alkylaminocarbonyl, CrC2-Haloalkylaminocarbonyl, CrC2-Alkylsulfonyl, C]-C2-Alkylcarbonyl, C1-C2-HaIo- alkylcarbonyl, C3-C5-Cycloalkylcarbonyl, Ci-C2-Alkoxycarbonyl, Phenylsulfonyl, Phenylcarbonyl, Heteroarylcarbonyl, Hetero-C3-C5-cyclylcarbonyl, Phenyl-Ci-C2-alkylcarbonyl, Heteroaryl-Ci-C2- alkylcarbonyl, Hetero-C3-C5-cyclyl-Ci-C2-alkylcarbonyl oder Phenoxycarbonyl stehen; wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Cj- C2-Alkyl, Ci-C2-Haloalkyl, Ci-C2-Alkoxy, Nitro oder Cyano; und ein an Phenyl oder Heteroaryl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Cr C4-Alkyl, Ci-C4-Haloalkyl, CrC2-Alkoxy oder Cyano.In one embodiment 10, the invention relates to compounds according to embodiment 9 in which R 8 and R 9 are each independently hydrogen, Ci-C 2 alkyl, Ci-C 2 haloalkyl, C 3 -C 5 - cycloalkyl, C 3 -C 5 -cycloalkyl-C r C 2 -alkyl, C 3 -C 5 -HaIoCyClOaIlCyI, C 3 -C 5 -Halocycloalkyl-Ci-C 2 - alkyl, methylsulfmyl-C, -C 3 -alkyl, methylsulfanyl-C, -C 3 alkyl, methylsulfonyl CPCS-alkyl, phenyl-Ci-C 2 alkyl, heteroaryl-Ci-C 2 alkyl, C r C 2 dialkylaminocarbonyl, C 1 -C 2 - alkylaminocarbonyl, C r C 2 -Haloalkylaminocarbonyl, -C 2 alkylsulfonyl, C] -C 2 alkylcarbonyl, C 1 -C 2 -HaIo- alkylcarbonyl, C 3 -C 5 -cycloalkylcarbonyl, C 1 -C 2 -alkoxycarbonyl, phenylsulfonyl, phenylcarbonyl, heteroarylcarbonyl, hetero-C 3 -C 5 -cycloylcarbonyl, phenyl-C 1 -C 2 -alkylcarbonyl, heteroaryl-C 1 -C 2 -alkylcarbonyl , Hetero-C 3 -C 5 -cyclyl-C 1 -C 2 -alkylcarbonyl or phenoxycarbonyl; where a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, nitro or cyano; and a bound on phenyl or heteroaryl alkanediyl radical optionally mono- or polysubstituted by halogen, C r C 4 alkyl, Ci-C 4 haloalkyl, C r C 2 alkoxy or cyano.
In einer Ausführungsform 11 betrifft die Erfindung Verbindungen gemäß Ausführungsform 1, in denen Q für Q4 steht.In an embodiment 11, the invention relates to compounds according to embodiment 1, in which Q is Q 4 .
In einer Ausfuhrungsform 12 betrifft die Erfindung Verbindungen gemäß Ausführungsform 11, in denen Q4 für Cyano (wobei R1 nicht für Amino steht), Nitro, Amino, COOH, COOR12, Fluor (falls R3 verschieden von Chlor ist), Chlor (falls R3 verschieden von Chlor, COOH, CH2CH2OMe und OMe ist), Brom, Iod, SR12 (wobei R1 nicht für Amino steht, falls R12 für Alkyl steht), S(O)R12oder S(O)2R12 steht und R12 für d-C4-Alkyl oder CrC4-Haloalkyl steht.In one embodiment 12, the invention relates to compounds according to embodiment 11 in which Q 4 is cyano (where R 1 is not amino), nitro, amino, COOH, COOR 12 , fluorine (if R 3 is other than chlorine), chloro ( if R 3 is other than chloro, COOH, CH 2 CH 2 OMe and OMe), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 and R 12 for dC 4 alkyl or C r C 4 haloalkyl.
In einer Ausführungsform 13 betrifft die Erfindung Verbindungen gemäß Ausführungsform 12, in denen Q4 für Cyano (wobei R1 nicht für Amino steht), COOH, COOMe, COOEt, Fluor (falls R3 verschieden von Chlor ist), Brom, Iod, SR12 (wobei R1 nicht für Amino steht, falls R12 für Alkyl steht), S(O)R12oder S(O)2R12 steht.In one embodiment 13, the invention relates to compounds according to embodiment 12 wherein Q 4 is cyano (where R 1 is other than amino), COOH, COOMe, COOEt, fluorine (if R 3 is other than chlorine), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 .
In einer Ausführungsform 14 betrifft die Erfindung Verbindungen der Formel (EU- A)In one embodiment 14, the invention relates to compounds of the formula (EU-A)
wobeiin which
G1, G2 und G3 unabhängig voneinander für Wasserstoff, Halogen, Methyl oder CF3 stehen;G 1 , G 2 and G 3 independently represent hydrogen, halogen, methyl or CF 3 ;
G4 und G5 für Wasserstoff stehen;G 4 and G 5 are hydrogen;
R2 für Fluor, Chlor, Brom, Iod, Ci-C4-Alkoxy-C,-C4-Alkyl, C,-C4-Alkyl, Aryl-C,-C4- haloalkyl, CrC6-Alkylsulfanyl, CrC6-Alkylsulfmyl, CrC6-Alkylsulfonyl oder C,-C4 Haloalkyl steht; A1 und A2 unabhängig voneinander für N oder CH stehen;R 2 represents fluorine, chlorine, bromine, iodine, Ci-C4 alkoxy-C, -C 4 alkyl, C, -C 4 alkyl, aryl-C, -C 4 - haloalkyl, C r C 6 alkylsulfanyl , C r C 6 -Alkylsulfmyl, C r C 6 alkylsulfonyl or C, -C 4 haloalkyl; A 1 and A 2 are independently N or CH;
R3 für Fluor, Chlor, Brom, Iod, C1-2-AIlCyI, d-2-Haloalkyl, CrC2-Haloalkylsulfanyl, C1- C2-Haloalkylsulfonyl, Ci-C2-Haloalkylsulfinyl oder Cyano steht;R 3 is fluoro, chloro, bromo, iodo, C 1-2 -alkyl, d -2 -haloalkyl, C r C 2 -haloalkylsulfanyl, C 1 - C 2 -haloalkylsulfonyl, C 1 -C 2 -haloalkylsulfinyl or cyano;
R13 und R14 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, Propyl, iso-Propyl, Methylcarbonyl, Methoxycarbonyl, Trifluormethylcarbonyl, Methylsulfanyl, Trifluormethylsul- fanyl, Benzyl oder Pyridyhnethyl stehen, R13 und R14 aber nicht gleichzeitig für Wasserstoff stehen, undR 13 and R 14 are each independently hydrogen, methyl, ethyl, propyl, iso-propyl, methylcarbonyl, methoxycarbonyl, trifluoromethylcarbonyl, methylsulfanyl, trifluoromethylsulfanyl, benzyl or pyridylmethyl, but R 13 and R 14 are not simultaneously hydrogen, and
Q für Q1, Q2, Q3 oder Q4 steht.Q stands for Q 1 , Q 2 , Q 3 or Q 4 .
In einer Ausfuhrungsform 15 betrifft die Erfindung Verbindungen gemäß Ausführungsform 14, in denen Q für Q1 steht.In one embodiment 15, the invention relates to compounds according to embodiment 14, in which Q stands for Q 1 .
In einer Ausführungsform 16 betrifft die Erfindung Verbindungen gemäß Ausführungsform 15, in denen Q1 für Z3, Z7, Z15, Z16, Z17, Z18, Z21, Z22, Z23 oder Z24 steht; R6, R6', R6", R6'" für Wasserstoff, Amino, Cyano, Fluor, Chlor, Methyl, Ethyl, C]-C2-Haloalkyl, Methoxy, Ethoxy oder C1-C2- Haloalkoxy stehen und R7 für Wasserstoff, Amino, Cyano, Ci-C2-Alkyl, Ci-C2-Haloalkyl oder C1- C2-Alkoxy steht.In one embodiment 16, the invention relates to compounds according to embodiment 15 in which Q 1 is Z 3 , Z 7 , Z 15 , Z 16 , Z 17 , Z 18 , Z 21 , Z 22 , Z 23 or Z 24 ; R 6 , R 6 ' , R 6 " , R 6'" are hydrogen, amino, cyano, fluorine, chlorine, methyl, ethyl, C] -C 2 haloalkyl, methoxy, ethoxy or C 1 -C 2 haloalkoxy and R 7 is hydrogen, amino, cyano, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 2 -alkoxy.
In einer Ausführungsform 17 betrifft die Erfindung Verbindungen gemäß Ausführungsform 16, in denen Q1 für Z16 oder Z3 steht.In an embodiment 17, the invention relates to compounds according to embodiment 16, in which Q 1 is Z 16 or Z 3 .
In einer Ausführungsform 18 betrifft die Erfindung Verbindungen gemäß Ausführungsform 14, in denen Q für Q2 steht.In an embodiment 18, the invention relates to compounds according to embodiment 14, in which Q is Q 2 .
In einer Ausführungsform 19 betrifft die Erfindung Verbindungen gemäß Ausführungsform 18, in denen Q2 für C(O)NR8R9 steht; und R8 und R9 unabhängig voneinander für Wasserstoff, C1-C4- Alkyl, Ci-C4-Haloalkyl, C3-C5-Cycloalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Haloalkyl, Ci-C2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten), C3-C5-Cycloalkyl-C1-C2-alkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, C]-C2-Haloalkyl, Ci-C2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten, am CrC2-Alkylteil gegebenenfalls ein- oder mehrfach substituiert durch Halogen, CrC2-Alkyl, CrC2-Haloalkyl, CrC2-Alkoxy oder Cyano), CrC2-Alkylsulfmyl-Cr C3-alkyl, C1-C2-Alkylsulfanyl-Ci-C3-alkyl, CrC^Alkylsulfonyl-d-Cralkyl, Phenyl-CrC4-alkyl oder Heteroaryl -C]-C4-alkyl stehen; wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C2-Alkyl, CrC2-Haloalkyl, CrC2-Alkoxy, Nitro oder Cyano; und ein an Phenyl oder Heteroaryl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, CrC4-Alkyl, CrQ-Haloalkyl, Ci-C2-Alkoxy oder Cyano.In an embodiment 19, the invention relates to compounds according to embodiment 18, in which Q 2 is C (O) NR 8 R 9 ; and R 8 and R 9 are independently hydrogen, C 1 -C 4 - alkyl, Ci-C optionally mono- or 4 haloalkyl, C 3 -C 5 cycloalkyl (at cycle polysubstituted by halogen, Ci-C 2 - Haloalkyl, C 1 -C 2 -alkyl or fused to an aromatic or heteroaromatic radical), C 3 -C 5 -cycloalkyl-C 1 -C 2 -alkyl (optionally mono- or polysubstituted by halogen, C] -C 2 - at the cycle Haloalkyl, Ci-C 2 alkyl or fused to an aromatic or heteroaromatic, the CrC 2 alkyl optionally mono- or polysubstituted by halogen, C r C 2 alkyl, C r C 2 haloalkyl, C r C 2 alkoxy or cyano), C r C 2 alkylsulfmylC r C 3 alkyl, C 1 -C 2 alkylsulfanyl-Ci-C 3 alkyl, CrC ^ alkylsulfonyl-d-cralkyl, phenyl-C r C 4 alkyl or Heteroaryl -C] -C 4 alkyl; wherein a phenyl or heteroaryl radical optionally mono- or Ci-C polysubstituted by halogen, 2 alkyl, C r C 2 haloalkyl, C r C 2 alkoxy, nitro or cyano; and an alkanediyl radical attached to phenyl or heteroaryl, if appropriate or polysubstituted by halogen, C r C 4 alkyl, CrQ haloalkyl, Ci-C 2 alkoxy or cyano.
In einer Ausführungsform 20 betrifft die Erfindung Verbindungen gemäß Ausführungsform 19, in denen R8 und R9 unabhängig voneinander für Wasserstoff, Ci-CrAlkyl, Ci-Gj-Haloalkyl, C3-C4- Cycloalkyl, C3-C4-Halocycloalkyl, C3-C5-Cycloalkyl-CrC2-alkyl! C3-C5-Halocycloalkyl-Ci-C2- alkyl, Metoylalkylsulfinyl-CrQ-alkyl, Methylalkylsulfanyl-CrCralkyl, Methylalkylsulfonyl-Cr C3-alkyl, Phenylmethyl (am Aromaten gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso-Propyl, Methoxy oder Trifluormethyl), Pyridylmethyl (am Pyridyl gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso-Propyl, Methoxy oder Trifluormethyl) oder Pvrirnidylmethyl (am Pyrimidyl gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso-Propyl, Methoxy oder Trifluormethyl) stehen.In one embodiment 20, the invention relates to compounds according to embodiment 19, in which R 8 and R 9 are each independently hydrogen, Ci-CrAlkyl, Ci-Gj-haloalkyl, C 3 -C 4 - cycloalkyl, C 3 -C 4 halocycloalkyl, C 3 -C 5 -cycloalkyl-C r C 2 -alkyl ! C 3 -C 5 -Halocycloalkyl-Ci-C 2 - alkyl, Metoylalkylsulfinyl-CrQ-alkyl, methylalkylsulfanyl-CrCralkyl, methylalkylsulfonyl-C r C 3 alkyl, phenylmethyl (optionally aromatically mono- or polysubstituted by fluorine, chlorine, bromine , Methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, on the methyl part optionally mono- or polysubstituted by methyl, ethyl, propyl, iso-propyl, methoxy or trifluoromethyl), pyridylmethyl (pyridyl optionally mono- or polysubstituted by fluorine, Chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, on the methyl part optionally mono- or polysubstituted by methyl, ethyl, propyl, iso-propyl, methoxy or trifluoromethyl) or pvrirnidylmethyl (optionally substituted one or more times on the pyrimidyl by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, on the methyl part optionally mono- or polysubstituted by methyl, ethyl, propyl, iso-propyl, methoxy or Tr ifluoromethyl).
In einer Ausführungsform 21 betrifft die Erfindung Verbindungen gemäß Ausführungsform 14, in denen Q für Q3 steht.In an embodiment 21, the invention relates to compounds according to embodiment 14, in which Q is Q 3 .
In einer Ausfuhrungsform 22 betrifft die Erfindung Verbindungen gemäß Ausfuhrungsform 21, in denen Q3 für C(R10R1 ^NR8R9 steht; R10 und R11 unabhängig voneinander für Wasserstoff, C1-C2- Alkyl oder Ci-C2-Haloalkyl stehen und R8 und R9 unabhängig voneinander für Wasserstoff, C1-C4- Alkyl, Ci-C4-Haloalkyl, C3-C4-Cycloalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Haloalkyl, Ci-C2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten), C3-C4-Cycloalkyl-Ci-C2-alkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, CrC2-Haloalkyl, Ci-C2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten, am C]-C2-Alkylteil gegebenenfalls ein- oder mehrfach substituiert durch Halogen, C1-C2-AIkVl, C1-C2-HaIOaIlCyI, CrC2-Alkoxy oder Cyano), C1-C2-Alkylsulfmyl-C1- C2-alkyl, Ci-Cz-Alkylsulfanyl-Q-Cralkyl, C1-C2-Alkylsulfonyl-C1-C2-alkyl, Phenyl-CrC4-alkyl, Heteroaryl-d-Gi-alkyl, C1-C4-Dialkylaminocarbonyl, C1-C4-Alkylaminocarbonyl, C1-C4-HaIo- alkylaminocarbonyl, C]-C2-Alkylsulfonyl, CrQ-Alkylcarbonyl, CrC2-Haloalkylcarbonyl, C3-C5- Cycloalkylcarbonyl, C]-C2-Alkoxycarbonyl, Ci -C2-AIkOXy-C1 -C2-alkylcarbonyl, Phenylsulfonyl, Phenyl, Heteroaryl, Hetero-C3-C5-cyclyl, Phenylcarbonyl, Heteroarylcarbonyl, Hetero-C3-C5- cyclylcarbonyl, Phenyl-C1-C2-alkylcarbonyl, Heteroaryl-Ci-C2-alkylcarbonyl, Hetero-C3-C5-cyclyl- Ci-C2-alkylcarbonyl, Phenoxycarbonyl oder Phenyl-Ci-C2-alkoxycarbonyl stehen; wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Q- C2-Alkyl, Ci-C2-Haloalkyl, C1-C2-AIkOXy, Nitro oder Cyano; und ein an Phenyl oder Heteroaryl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Q- C4-Alkyl, d-Q-Haloalkyl, CrC2-Alkoxy oder Cyano.In one embodiment 22, the invention relates to compounds according to embodiment 21 in which Q 3 is C (R 10 R 1 -NR 8 R 9 ; R 10 and R 11 are each independently hydrogen, C 1 -C 2 -alkyl or C 2 haloalkyl, and R 8 and R 9 are independently hydrogen, C 1 -C 4 - alkyl, Ci-C 4 haloalkyl, C 3 -C 4 cycloalkyl (optionally mono- or polysubstituted at the cycle by halogen, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkyl or fused to an aromatic or heteroaromatic radical), C 3 -C 4 -cycloalkyl-C 1 -C 2 -alkyl (optionally substituted one or more times by halogen on the cycle, C r C 2 haloalkyl, Ci-C 2 alkyl or fused optionally mono- or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 to an aromatic or heteroaromatic, the C] -C 2 -alkyl moiety - HaIOaIlCyI, C r C 2 alkoxy or cyano), C 1 -C 2 -Alkylsulfmyl-C 1 - C 2 alkyl, Ci-Cz-alkylsulfanyl-Q-Cralkyl, C 1 -C 2 -alkylsulfonyl-C 1 -C 2 -alkyl, phenyl-C r C 4 -al kyl, heteroaryl-d-Gi-alkyl, C 1 -C 4 -dialkylaminocarbonyl, C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -haloalkylaminocarbonyl, C] -C 2 -alkylsulfonyl, C 1 -C -alkylcarbonyl, C r C 2 haloalkylcarbonyl, C 3 -C 5 - cycloalkylcarbonyl, C] -C 2 alkoxycarbonyl, Ci -C 2 -alkoxy-C 1 -C 2 alkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl, heterocyclo-C 3 -C 5 - cyclyl, phenylcarbonyl, heteroarylcarbonyl, hetero-C 3 -C 5 - cyclylcarbonyl, phenyl-C 1 -C 2 alkylcarbonyl, heteroaryl-Ci-C2-alkylcarbonyl, hetero-C 3 -C 5 -cyclyl- Ci-C 2 - alkylcarbonyl, phenoxycarbonyl or phenyl-C 1 -C 2 -alkoxycarbonyl; being a Phenyl or heteroaryl optionally mono- or polysubstituted by halogen, Q-C 2 alkyl, Ci-C 2 haloalkyl, C 1 -C 2 -alkoxy, nitro or cyano; and a bound on phenyl or heteroaryl alkanediyl radical optionally mono- or polysubstituted by halogen, Q-C 4 alkyl, dQ-haloalkyl, C r C 2 alkoxy or cyano.
In einer Ausführungsform 23 betrifft die Erfindung Verbindungen gemäß Ausführungsform 22, in denen R8 und R9 unabhängig voneinander für Wasserstoff, C1-C2-AIlCyI, CrC2-Haloalkyl, C3-C5- Cycloalkyl, C3-C5-Cycloalkyl-Q-C2-alkyl, Q-Cs-Halocycloalkyl, C3-C5-Halocycloalkyl-Q-C2- alkyl, Methylsulfinyl-Q-C3-alkyl, Methylsulfanyl-CrC3-alkyl, Methylsulfonyl-CrC3-alkyl, Phenyl-Q-C2-alkyl, Heteroaryl-C]-C2-alkyl, C1-C2-Dialkylaminocarbonyl, Q-C2-Alkylamino- carbonyl, Ci-C2-Haloalkylaminocarbonyl, Ci-C2-Alkylsulfonyl, Ci-C2-Alkylcarbonyl, Q-C2-HaIo- alkylcarbonyl, C3-C5-Cycloalkylcarbonyl, Ci-C2-Alkoxycarbonyl, Phenylsulfonyl, Phenylcarbonyl, Heteroarylcarbonyl, Hetero-C3-C5-cyclylcarbonyl, Phenyl-C]-C2-alkylcarbonyl, Heteroaryl-Q-C2- alkylcarbonyl, Hetero-C3-C5-cyclyl-Ci-C2-alkylcarbonyl oder Phenoxycarbonyl stehen; wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Q- C2-Alkyl, Ci-C2-Haloalkyl, Ci-C2-Alkoxy, Nitro oder Cyano; und ein an Phenyl oder Heteroaryl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Q- C4-Alkyl, Q-C4-Haloalkyl, Q-Q-Alkoxy oder Cyano. In einer Ausführungsform 24 betrifft die Erfindung Verbindungen gemäß Ausführungsform 14, in denen Q für Q4 steht.In one embodiment 23, the invention relates to compounds according to embodiment 22, in which R 8 and R 9 are independently hydrogen, C 1 -C 2 -alkyl, C r C 2 haloalkyl, C 3 -C 5 - cycloalkyl, C 3 - C 5 -Cycloalkyl-QC 2 -alkyl, Q-Cs-Halocycloalkyl, C 3 -C 5 -Halocycloalkyl-QC 2 -alkyl, methylsulfinyl-QC 3 -alkyl, methylsulfanyl-C r C 3 -alkyl, methylsulfonyl-C r C 3 alkyl, phenyl-QC 2 -alkyl, heteroaryl-C] -C 2 alkyl, C 1 -C 2 dialkylaminocarbonyl, QC 2 alkylamino carbonyl, Ci-C 2 -Haloalkylaminocarbonyl, Ci-C 2 alkylsulfonyl, Ci-C 2 alkylcarbonyl, QC 2 -HaIo- alkylcarbonyl, C 3 -C 5 cycloalkyl-carbonyl, Ci-C2 alkoxycarbonyl, phenylsulfonyl, phenylcarbonyl, heteroarylcarbonyl, hetero-C 3 -C 5 -cyclylcarbonyl, phenyl-C] - C 2 alkylcarbonyl, heteroarylQC 2 alkylcarbonyl, hetero C 3 -C 5 cycloalkylC 2 -C 2 alkylcarbonyl or phenoxycarbonyl; where a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, Q-C 2 alkyl, Ci-C 2 haloalkyl, Ci-C 2 alkoxy, nitro or cyano; and an alkanediyl radical bonded to phenyl or heteroaryl is optionally mono- or polysubstituted by halogen, Q-C 4 -alkyl, QC 4 -haloalkyl, QQ-alkoxy or cyano. In an embodiment 24, the invention relates to compounds according to embodiment 14, in which Q is Q 4 .
In einer Ausführungsform 25 betrifft die Erfindung Verbindungen gemäß Ausführungsform 24, in denen Q4 für Cyano (wobei R1 nicht für Amino steht), Nitro, Amino, COOH, COOR12, Fluor (falls R3 verschieden von Chlor ist), Chlor (falls R3 verschieden von Chlor, COOH, CH2CH2OMe und OMe ist), Brom, Iod, SR12 (wobei R1 nicht für Amino steht, falls R12 für Alkyl steht), S(O)R12oder S(O)2R12 steht und R12 für Q-C4-Alkyl oder Q-C4-Haloalkyl steht.In one embodiment 25, the invention relates to compounds according to embodiment 24 in which Q 4 is cyano (where R 1 is other than amino), nitro, amino, COOH, COOR 12 , fluorine (if R 3 is other than chlorine), chloro ( if R 3 is other than chloro, COOH, CH 2 CH 2 OMe and OMe), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 and R 12 is QC 4 alkyl or QC 4 haloalkyl.
In einer Ausführungsform 26 betrifft die Erfindung Verbindungen gemäß Ausführungsform 25, in denen Q4 für Cyano (wobei R1 nicht für Amino steht), COOH, COOMe, COOEt, Fluor (falls R3 verschieden von Chlor ist), Brom, Iod, SR12 (wobei R1 nicht für Amino steht, falls R12 für Alkyl steht), S(O)R12oder S(O)2R12 steht.In one embodiment 26, the invention relates to compounds according to embodiment 25 in which Q 4 is cyano (where R 1 is other than amino), COOH, COOMe, COOEt, fluorine (if R 3 is other than chlorine), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 .
In einer Ausführungsform 27 betrifft die Erfindung Verbindungen der Formel (FV-A) In an embodiment 27, the invention relates to compounds of the formula (FV-A)
wobeiin which
G1, G2 und G3 unabhängig voneinander für Wasserstoff, Halogen, Methyl oder CF3 stehen;G 1 , G 2 and G 3 independently represent hydrogen, halogen, methyl or CF 3 ;
G4 und G5 für Wasserstoff stehen;G 4 and G 5 are hydrogen;
R2 für Fluor, Chlor, Brom, Iod, C1-C4-AIkOXy-C1-C4-AIlCyI, CrC4-Alkyl, AIyI-C1-C4- haloalkyl, CrC6-Alkylsulfanyl, Q-Ce-Alkylsulfinyl, Cj-Q-Alkylsulfonyl oder C1-C4 Haloalkyl steht;R 2 represents fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C r C 4 alkyl, Aiyi-C 1 -C 4 - haloalkyl, C r C 6 alkylsulfanyl , Q-Ce-alkylsulfinyl, Cj-Q-alkylsulfonyl or C 1 -C 4 haloalkyl;
A1 und A2 unabhängig voneinander für N oder CH stehen;A 1 and A 2 are independently N or CH;
R3 für Fluor, Chlor, Brom, Iod, C1-2-Alkyl, C^-Haloalkyl, CrC2-Haloalkylsulfanyl, C1- C2-Haloalkylsulfonyl, C]-C2-Haloalkylsulfϊnyl oder Cyano steht;R 3 represents fluorine, chlorine, bromine, iodine, C 1-2 alkyl, C ^ haloalkyl, C r C 2 -Haloalkylsulfanyl, C 1 - C 2 haloalkylsulfonyl, C] -C 2 -Haloalkylsulfϊnyl or cyano;
R17 für Halogen, Alkylsulfanyl, Alkylsulfmyl, Alkylsulfonyl oder Cyano steht undR 17 is halogen, alkylsulfanyl, alkylsulfmyl, alkylsulfonyl or cyano and
Q für Q1, Q2, Q3 oder Q4 steht.Q stands for Q 1 , Q 2 , Q 3 or Q 4 .
In einer Ausführungsform 28 betrifft die Erfindung Verbindungen gemäß Ausführungsform 27, in denen Q für Q1 steht.In an embodiment 28, the invention relates to compounds according to embodiment 27, in which Q is Q 1 .
In einer Ausführungsform 29 betrifft die Erfindung Verbindungen gemäß Ausführungsform 28, in denen Q1 für Z3, Z7, Z15, Z16, Z17, Z18, Z21, Z22, Z23 oder Z24 steht; R6, R6', R6", R6'" für Wasserstoff, Amino, Cyano, Fluor, Chlor, Methyl, Ethyl, C1-C2-HaIOaIlCyI, Methoxy, Ethoxy oder C1-C2- Haloalkoxy stehen und R7 für Wasserstoff, Amino, Cyano, Q-Q-Alkyl, CrC2-Haloalkyl oder C1- C2-Alkoxy steht.In an embodiment 29, the invention relates to compounds according to embodiment 28 in which Q 1 is Z 3 , Z 7 , Z 15 , Z 16 , Z 17 , Z 18 , Z 21 , Z 22 , Z 23 or Z 24 ; R 6 , R 6 ' , R 6 " , R 6'" are hydrogen, amino, cyano, fluorine, chlorine, methyl, ethyl, C 1 -C 2 -HaIOaIlCyI, methoxy, ethoxy or C 1 -C 2 - haloalkoxy and R 7 is hydrogen, amino, cyano, QQ-alkyl, C r C 2 -haloalkyl or C 1 -C 2 -alkoxy.
In einer Ausführungsform 30 betrifft die Erfindung Verbindungen gemäß Ausführungsform 29, in denen Q1 für Z16 oder Z3 steht.In one embodiment 30, the invention relates to compounds according to embodiment 29, in which Q 1 is Z 16 or Z 3 .
In einer Ausführungsfoπn 31 betrifft die Erfindung Verbindungen gemäß Ausführungsform 27, in denen Q für Q2 steht. In einer Ausfuhrungsform 32 betrifft die Erfindung Verbindungen gemäß Ausführungsform 31, in denen Q2 für C(O)NR8R9 steht und R8 und R9 unabhängig voneinander für Wasserstoff, Ci-C4- Alkyl, C1-C4-HaIOaIlCyI, C3-C5-Cycloalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Haloalkyl, Ci-C2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten), C3-C5-Cycloalkyl-Ci-C2-alkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Haloalkyl, Ci-C2-AIlCyI oder kondensiert an einen Aromaten oder Heteroaromaten, am Ci-C2-Alkylteil gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Alkyl, CrC2-Haloalkyl, Ci-C2-Alkoxy oder Cyano), Ci-C2-Alkylsulfinyl-C,- C3-alkyl, C1-C2-Alkylsulfanyl-C1-C3-alkyl, C,-C2-Alkylsulfonyl-C,-C3-alkyl, Phenyl-CrC4-alkyl oder Heteroaryl -C]-C4-alkyl stehen; wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C2-Alkyl, Ci-C2-Haloalkyl, Ci-C2-Alkoxy, Nitro oder Cyano; und ein an Phenyl oder Heteroaryl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C4-Alkyl, CrC4-Haloalkyl, C]-C2-Alkoxy oder Cyano.In one embodiment, the invention relates to compounds according to embodiment 27 in which Q is Q 2 . In one embodiment 32, the invention relates to compounds according to embodiment 31 in which Q 2 is C (O) NR 8 R 9, and R 8 and R 9 are each independently hydrogen, Ci-C 4 - alkyl, C 1 -C 4 - Haloalkyl, C 3 -C 5 -cycloalkyl (optionally mono- or polysubstituted by halogen, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkyl or fused to an aromatic or heteroaromatic radical on the cycle, C 3 -C 5 -cycloalkyl -C-C 2 alkyl (the cycle may optionally be mono- or polysubstituted by halogen, Ci-C 2 haloalkyl, Ci-C 2 -alkyl or fused to a aromatic or heteroaromatic, the Ci-C 2 alkyl moiety may optionally be mono- or polysubstituted by halogen, Ci-C 2 alkyl, C r C 2 haloalkyl, Ci-C 2 alkoxy or cyano), C 2 alkylsulfinyl-C, - C 3 alkyl, C 1 -C 2 -Alkylsulfanyl-C 1 -C 3 -alkyl, C 1 -C 2 -alkylsulfonyl-C, C 3 -alkyl, phenylC r C 4 -alkyl or heteroarylC] C 4 -alkyl; where a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, nitro or cyano; and a bound on phenyl or heteroaryl alkanediyl radical optionally mono- or Ci-C polysubstituted by halogen, 4 alkyl, C r C 4 haloalkyl, C] -C 2 alkoxy or cyano.
In einer Ausführungsform 33 betrifft die Erfindung Verbindungen gemäß Ausführungsform 32, in denen R8 und R9 unabhängig voneinander für Wasserstoff, Ci-C4-Alkyl, C]-C4-Haloalkyl, C3-C4- Cycloalkyl, C3-C4-Halocycloalkyl, C3-C5-Cycloalkyl-Ci-C2-alkyl, C3-C5-Halocycloalkyl-Ci-C2- alkyl, Methylalkylsulfinyl-d-Cs-alkyl, Methylalkylsulfanyl-Ci-C3-alkyl, Methylalkylsulfonyl-Cr C3-alkyl, Phenyhnethyl (am Aromaten gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso-Propyl, Methoxy oder Trifluormethyl), Pyridylmethyl (am Pyridyl gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso-Propyl, Methoxy oder Trifluormethyl) oder Pyrimidylmethyl (am Pyrimidyl gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso-Propyl, Methoxy oder Trifluormethyl) stehen.In one embodiment 33, the invention relates to compounds according to embodiment 32 in which R 8 and R 9 are each independently hydrogen, Ci-C 4 alkyl, C] -C 4 haloalkyl, C 3 -C 4 - cycloalkyl, C 3 - C 4 halocycloalkyl, C 3 -C 5 cycloalkyl-Ci-C 2 alkyl, C 3 -C 5 halocycloalkyl-Ci-C 2 - alkyl, d-Cs-Methylalkylsulfinyl-alkyl, Methylalkylsulfanyl-C 3 - alkyl, methylalkylsulfonyl-C r C 3 -alkyl, phenyhnethyl (optionally mono- or polysubstituted by at least one of fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro on the methyl part, optionally mono- or polysubstituted by methyl , Ethyl, propyl, isopropyl, methoxy or trifluoromethyl), pyridylmethyl (optionally mono- or polysubstituted on the pyridyl by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, optionally one or more times on the methyl part substituted by methyl, ethyl, propyl, iso-propyl, methoxy or trifluoromethyl) or the like R pyrimidylmethyl (pyrimidyl optionally mono- or polysubstituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, on the methyl part optionally mono- or polysubstituted by methyl, ethyl, propyl, iso-propyl, methoxy or trifluoromethyl).
In einer Ausführungsform 34 betrifft die Erfindung Verbindungen gemäß Ausführungsforrn 27, in denen Q für Q3 steht.In an embodiment 34, the invention relates to compounds according to embodiment 27, in which Q stands for Q 3 .
In einer Ausführungsform 35 betrifft die Erfindung Verbindungen gemäß Ausführungsform 34, in denen Q3 für C(R1V)NR8R9 steht; R10 und R11 unabhängig voneinander für Wasserstoff, CrC2- Alkyl oder Ci-C2-Haloalkyl stehen und R8 und R9 unabhängig voneinander für Wasserstoff, Q-C4- Alkyl, Ci-C4-Haloalkyl, C3-C4-Cycloalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Haloalkyl, Ci-C2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten), C3-C4-Cycloalkyl-Ci-C2-alkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Haloalkyl, Ci-C2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten, am Ci-C2-Alkylteil gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Alkyl, d-C2-Haloalkyl, Ci-C2-Alkoxy oder Cyano), Q-C2-Alkylsulfinyl-Q- C2-alkyl, CrC2-Alkylsulfanyl-CrC2-alkyl, CrC2-Alkylsulfonyl-CrC2-alkyl, Phenyl-C]-C4-alkyl, Heteroaryl-Ci-C4-alkyl, Ci-C4-Dialkylaminocarbonyl, Q-Q-Alkylaminocarbonyl, Q-C4-HaIo- alkylaminocarbonyl, C]-C2-Alkylsulfonyl, C1-C2-Alkylcarbonyl, Q-C2-Haloalkylcarbonyl, C3-C5- Cycloalkylcarbonyl, Ci-C2-Alkoxycarbonyl, Ci-C2-Alkoxy-Ci-C2-alkylcarbonyl, Phenylsulfonyl, Phenyl, Heteroaryl, Hetero-C3-C5-cyclyl, Phenylcarbonyl, Heteroarylcarbonyl, Hetero-Q-C5- cyclylcarbonyl, Phenyl-Ci-C2-alkylcarbonyl, Heteroaryl-CrC2-alkylcarbonyl, Hetero-C3-C5-cyclyl- Q-C2-alkylcarbonyl, Phenoxycarbonyl oder Phenyl-C]-C2-alkoxycarbonyl stehen; wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Q- C2-Alkyl, Ci-C2-Haloalkyl, Ci-C2-Alkoxy, Nitro oder Cyano; und ein an Phenyl oder Heteroaryl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Q- C4-Alkyl, Q-C4-Haloalkyl, CrC2-Alkoxy oder Cyano.In one embodiment 35, the invention relates to compounds according to embodiment 34 in which Q 3 is C (R 1 V) NR 8 R 9 ; R 10 and R 11 are independently hydrogen, C r C 2 - alkyl or Ci-C 2 haloalkyl, and R 8 and R 9 are independently hydrogen, QC 4 - alkyl, Ci-C 4 haloalkyl, C 3 - C 4 -cycloalkyl (optionally one or more times at the cycle substituted by halogen, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkyl or fused to an aromatic or heteroaromatic radical), C 3 -C 4 -cycloalkyl-C 1 -C 2 -alkyl (optionally substituted one or more times at the cycle by Halogen, Ci-C 2 -haloalkyl, Ci-C 2 -alkyl or condensed on an aromatics or heteroaromatics, on the Ci-C 2 -alkyl part if necessary mono- or polysubstituted by halogen, Ci-C 2 -alkyl, dC 2 -Haloalkyl , Ci-C 2 alkoxy or cyano), QC 2 alkylsulfinyl-QC 2 -alkyl, C r C 2 -alkylsulfanyl-C r C 2 alkyl, C r C 2 alkylsulfonyl-C r C 2 alkyl , phenyl-C] -C4 alkyl, heteroaryl-Ci-C4-alkyl, Ci-C4-dialkylaminocarbonyl, QQ-alkylaminocarbonyl, QC 4 -HaIo- alkylaminocarbonyl, C] -C 2 alkylsulfonyl, C 1 -C 2- alkylcarbonyl, QC 2 -haloalkylcarbonyl, C 3 -C 5 -cycloalkylcarbonyl, C 1 -C 2 -alkoxycarbonyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl, hetero-C 3 -C 5 -cyclyl, phenylcarbonyl, heteroarylcarbonyl, hetero-QC 5 - cyclylcarbonyl, Phe nyl-Ci-C 2 -alkylcarbonyl, heteroaryl-C r C 2 -alkylcarbonyl, hetero-C 3 -C 5 -cyclyl-QC 2 -alkylcarbonyl, phenoxycarbonyl or phenyl-C] -C 2 -alkoxycarbonyl; where a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, Q-C 2 alkyl, Ci-C 2 haloalkyl, Ci-C 2 alkoxy, nitro or cyano; and a bound on phenyl or heteroaryl alkanediyl radical optionally mono- or polysubstituted by halogen, QC 4 alkyl, QC 4 haloalkyl, C r C 2 alkoxy or cyano.
In einer Ausführungsform 36 betrifft die Erfindung Verbindungen gemäß Ausführungsform 35, in denen R8 und R9 unabhängig voneinander für Wasserstoff, Ci-C2-Alkyl, C1-C2-HaIOaIlCyI, C3-C5- Cycloalkyl, C3-C5-Cycloalkyl-CrC2-alkyl, C3-C5-Halocycloalkyl, C3-C5-Halocycloalkyl-Q-C2- alkyl, Methylsulfmyl-CrC3-alkyl, Methylsulfanyl-CrC3-alkyl, Methylsulfonyl-C1-C3-alkyl, Phenyl-Ci-C2-alkyl, Heteroaryl-Ci-C2-alkyl, Ci-C2-Dialkylaminocarbonyl, Q-C2-Alkylamino- carbonyl, Ci-C2-Haloalkylaminocarbonyl, Ci-C2-Alkylsulfonyl, Ci-C2-Alkylcarbonyl, Q-C2-HaIo- alkylcarbonyl, C3-C5-Cycloalkylcarbonyl, C1-C2-Alkoxycarbonyl, Phenylsulfonyl, Phenylcarbonyl, Heteroarylcarbonyl, Hetero-C3-C5-cyclylcarbonyl, Phenyl-Ci-C2-alkylcarbonyl, Heteroaryl-Q-C2- alkylcarbonyl, Hetero-C3-C5-cyclyl-Ci-C2-alkylcarbonyl oder Phenoxycarbonyl stehen; wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Q- C2-Alkyl, Ci-C2-Haloalkyl, Q-C2-Alkoxy, Nitro oder Cyano; und ein an Phenyl oder Heteroaryl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Q- C4-Alkyl, Q-C4-Haloalkyl, Q-C2-Alkoxy oder Cyano.In one embodiment 36, the invention relates to compounds according to embodiment 35, in which R 8 and R 9 are each independently hydrogen, Ci-C 2 alkyl, C 1 -C 2 -HaIOaIlCyI, C 3 -C 5 - cycloalkyl, C 3 - C 5 cycloalkyl C r C 2 alkyl, C 3 C 5 halocycloalkyl, C 3 C 5 halocycloalkyl QC 2 alkyl, methylsulfmyl C r C 3 alkyl, methylsulfanyl C r C 3 alkyl , methylsulfonyl-C 1 -C 3 alkyl, phenyl-Ci-C 2 alkyl, heteroaryl-Ci-C 2 alkyl, Ci-C2 dialkylaminocarbonyl, QC 2 alkylamino carbonyl, Ci-C 2 -Haloalkylaminocarbonyl, Ci-C 2 alkylsulfonyl, Ci-C2 alkylcarbonyl, QC 2 -HaIo- alkylcarbonyl, C 3 -C 5 cycloalkyl-carbonyl, C 1 -C 2 alkoxycarbonyl, phenylsulfonyl, phenylcarbonyl, heteroarylcarbonyl, hetero-C 3 -C 5 -cyclylcarbonyl, phenyl-Ci-C 2 -alkylcarbonyl, heteroaryl-QC 2 - alkylcarbonyl, hetero-C 3 -C 5 -cyclyl-Ci-C 2 -alkylcarbonyl or phenoxycarbonyl; wherein a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, Q-C 2 alkyl, Ci-C 2 haloalkyl, QC 2 alkoxy, nitro or cyano; and an alkanediyl radical attached to phenyl or heteroaryl is optionally mono- or polysubstituted by halogen, Q-C 4 -alkyl, QC 4 -haloalkyl, QC 2 -alkoxy or cyano.
In einer Ausfϋhrungsform 37 betrifft die Erfindung Verbindungen gemäß Ausführungsform 27, in denen Q für Q4 steht.In an embodiment 37, the invention relates to compounds according to embodiment 27, in which Q stands for Q 4 .
In einer Ausführungsform 38 betrifft die Erfindung Verbindungen gemäß Ausführungsform 37, in denen Q4 für Cyano (wobei R1 nicht für Amino steht), Nitro, Amino, COOH, COOR12, Fluor (falls R3 verschieden von Chlor ist), Chlor (falls R3 verschieden von Chlor, COOH, CH2CH2OMe und OMe ist), Brom, Iod, SR12 (wobei R1 nicht für Amino steht, falls R12 für Alkyl steht), S(O)RI2oder S(O)2R12 steht und R12 für CrC4-Alkyl oder C,-C4-Haloalkyl steht.In one embodiment 38, the invention relates to compounds according to embodiment 37 in which Q 4 is cyano (where R 1 is other than amino), nitro, amino, COOH, COOR 12 , fluorine (if R 3 is other than chlorine), chloro ( if R 3 is different from chlorine, COOH, CH 2 CH 2 OMe and OMe), bromine, iodine, SR 12 (where R 1 does not represent amino, when R 12 is alkyl), S (O) R I2 or S (O) 2 R 12, and R 12 is C r C 4 Alkyl or C, -C 4 haloalkyl.
In einer Ausführungsform 39 betrifft die Erfindung Verbindungen gemäß Ausführungsfoπn 38, in denen Q4 für Cyano (wobei R1 nicht für Amino steht), COOH, COOMe, COOEt, Fluor (falls R3 verschieden von Chlor ist), Brom, Iod, SR12 (wobei R1 nicht für Amino steht, falls R12 für Alkyl steht), S(O)R12oder S(O)2R12 steht.In one embodiment 39, the invention relates to compounds according to embodiment 38 in which Q 4 is cyano (where R 1 is other than amino), COOH, COOMe, COOEt, fluorine (if R 3 is other than chlorine), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 .
In einer Ausführungsform 40 betrifft die Erfindung Verbindungen der Formel (V-A)In an embodiment 40, the invention relates to compounds of the formula (V-A)
wobeiin which
G1, G2 und G3 unabhängig voneinander für Wasserstoff, Halogen, Methyl oder CF3 stehen;G 1 , G 2 and G 3 independently represent hydrogen, halogen, methyl or CF 3 ;
G4 und G5 für Wasserstoff stehen;G 4 and G 5 are hydrogen;
R2 für Fluor, Chlor, Brom, Iod, C1-C4-AIkOXy-C1-C4-AIkVl, CrC4-Alkyl, ArVl-C1-C4- haloalkyl, CrC6-Alkylsulfanyl, CrC6-Alkylsulfmyl, CrC6-Alkylsulfonyl oder C1-C4 Haloalkyl steht;R 2 is fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C r C 4 -alkyl, ArVl-C 1 -C 4 -haloalkyl, C r C 6 -alkylsulfanyl , C r C 6 -Alkylsulfmyl, C r C 6 alkylsulfonyl or C 1 -C 4 haloalkyl;
A1 und A2 unabhängig voneinander für N oder CH stehen;A 1 and A 2 are independently N or CH;
R3 für Fluor, Chlor, Brom, Iod, C1-2-Alkyl, C ^-Haloalkyl, Ci-C2-Haloalkylsulfanyl, C1- C2-Haloalkylsulfonyl, C1-C2-Haloalkylsulfinyl oder Cyano steht undR 3 represents fluorine, chlorine, bromine, iodine, C 1-2 alkyl, C ^ haloalkyl, Ci-C 2 -Haloalkylsulfanyl, C 1 - C 2 haloalkylsulfonyl, C 1 -C 2 haloalkylsulfinyl or cyano and
Q für Q1 , Q2, Q3 oder Q4 steht.Q stands for Q 1 , Q 2 , Q 3 or Q 4 .
In einer Ausführungsform 41 betrifft die Erfindung Verbindungen gemäß Ausführungsform 40, in denen Q für Q1 steht.In one embodiment 41, the invention relates to compounds according to embodiment 40, in which Q is Q 1 .
In einer Ausführungsform 42 betrifft die Erfindung Verbindungen gemäß Ausführungsform 41, in denen Q1 für Z3, Z7, Z15, Z16, Z17, Z18, Z21, Z22, Z23 oder Z24 steht; R6, R6', R6", R6'" für Wasserstoff, Amino, Cyano, Fluor, Chlor, Methyl, Ethyl, CrC2-Haloalkyl, Methoxy, Ethoxy oder C1-C2- Haloalkoxy stehen und R7 für Wasserstoff, Amino, Cyano, Ci-C2-Alkyl, CrC2-Haloalkyl oder Q- C2-Alkoxy steht.In one embodiment 42, the invention relates to compounds according to embodiment 41 in which Q 1 is Z 3 , Z 7 , Z 15 , Z 16 , Z 17 , Z 18 , Z 21 , Z 22 , Z 23 or Z 24 ; R 6, R 6 ', R 6', R 6 '' represents hydrogen, amino, cyano, fluorine, chlorine, methyl, ethyl, -C 2 haloalkyl, methoxy, ethoxy or C 1 -C 2 - Haloalkoxy and R 7 is hydrogen, amino, cyano, Ci-C 2 alkyl, C r C 2 haloalkyl or Q-C 2 alkoxy.
In einer Ausführungsform 43 betrifft die Erfindung Verbindungen gemäß Ausführungsform 42, in denen Q1 für Z16 oder Z3 steht.In one embodiment 43, the invention relates to compounds according to embodiment 42, in which Q 1 is Z 16 or Z 3 .
In einer Ausführungsform 44 betrifft die Erfindung Verbindungen gemäß Ausführungsform 40, in denen Q für Q2 steht.In one embodiment 44, the invention relates to compounds according to embodiment 40 in which Q is Q 2 .
In einer Ausführungsform 45 betrifft die Erfindung Verbindungen gemäß Ausführungsform 44, in denen Q2 für C(O)NR8R9 steht und R8 und R9 unabhängig voneinander für Wasserstoff, C1-C4- Alkyl, Ci-C4-Haloalkyl, C3-C5-Cycloalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Haloalkyl, Ci-C2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten), C3-C5-Cycloalkyl-CrC2-alkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Haloalkyl, Ci-C2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten, am Ci-C2-Alkylteil gegebenenfalls ein- oder mehrfach substituiert durch Halogen, CrC2-Alkyl, CrC2-Haloalkyl, C,-C2-Alkoxy oder Cyano), CrC2-Alkylsulfmyl-Cr C3-alkyl, CrCz-Alkylsulfanyl-Ci-Gj-alkyl, C1-C2-Alkylsulfonyl-C1-C3-alkyl, Phenyl-CrC4-alkyl oder Heteroaryl -Ci-C4-alkyl stehen; wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C2-Alkyl, Ci-C2-Haloalkyl, Ci-C2-Alkoxy, Nitro oder Cyano; und ein an Phenyl oder Heteroaryl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Ci-C4-Alkyl, Q-d-Haloalkyl, Ci-C2-Alkoxy oder Cyano.In one embodiment 45, the invention relates to compounds according to embodiment 44 in which Q 2 is C (O) NR 8 R 9 and R 8 and R 9 are each independently hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 - Haloalkyl, C 3 -C 5 -cycloalkyl (optionally mono- or polysubstituted by halogen, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkyl or fused to an aromatic or heteroaromatic radical on the cycle, C 3 -C 5 -cycloalkyl -C r C 2 alkyl (the cycle may optionally be mono- or polysubstituted by halogen, Ci-C 2 haloalkyl, Ci-C 2 alkyl or fused to a aromatic or heteroaromatic, the Ci-C 2 alkyl moiety may optionally be mono- or polysubstituted by halogen, C r C 2 alkyl, C r C 2 haloalkyl, C, -C 2 alkoxy or cyano), C r C 2 -Alkylsulfmyl-C r C 3 alkyl, CrCz-alkylsulfanyl-Ci G 1 is alkyl, C 1 -C 2 alkylsulfonylC 1 -C 3 alkyl, phenylC r C 4 alkyl or heteroarylCi-C 4 alkyl; where a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, nitro or cyano; and an alkanediyl radical bonded to phenyl or heteroaryl is optionally mono- or polysubstituted by halogen, C 1 -C 4 -alkyl, Q 1 -haloalkyl, C 1 -C 2 -alkoxy or cyano.
In einer Ausführungsform 46 betrifft die Erfindung Verbindungen gemäß Ausführungsform 45, in denen R8 und R9 unabhängig voneinander für Wasserstoff, Ci-C4-Alkyl, CrC4-Haloalkyl, C3-C4- Cycloalkyl, C3-C4-Halocycloalkyl, C3-C5-Cycloalkyl-C,-C2-alkyl, C3-C5-Halocycloalkyl-Ci-C2- alkyl, Methylalkylsulfmyl-CrC3-alkyl, Methylalkylsulfanyl-C,-C3-alkyl, Methylalkylsulfonyl-C,- C3-alkyl, Phenylmethyl (am Aromaten gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso-Propyl, Methoxy oder Trifluormethyl), Pyridylmethyl (am Pyridyl gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso-Propyl, Methoxy oder Trifluormethyl) oder Pyrimidylmethyl (am Pyrimidyl gegebenenfalls ein- oder mehrfach substituiert durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Cyano oder Nitro, am Methylteil gegebenenfalls ein- oder mehrfach substituiert durch Methyl, Ethyl, Propyl, iso-Propyl, Methoxy oder Trifluormethyl) stehen. In einer Ausführungsform 47 betrifft die Erfindung Verbindungen gemäß Ausführungsform 40, in denen Q für Q3 steht.In one embodiment 46, the invention relates to compounds according to embodiment 45, in which R 8 and R 9 are each independently hydrogen, Ci-C 4 alkyl, C r C 4 haloalkyl, C 3 -C 4 - cycloalkyl, C 3 -C 4 -Halocycloalkyl, C 3 -C 5 -cycloalkyl-C, -C 2 -alkyl, C 3 -C 5 -Halocycloalkyl-Ci-C 2 - alkyl, methylalkylsulfmyl-C r C 3 -alkyl, methylalkylsulfanyl-C, -C 3 -alkyl, methylalkylsulfonyl-C, - C 3 -alkyl, phenylmethyl (optionally mono- or polysubstituted on the aromatic by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, optionally one or more times on the methyl part substituted by methyl, ethyl, propyl, iso-propyl, methoxy or trifluoromethyl), pyridylmethyl (pyridyl optionally mono- or polysubstituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, on the methyl part optionally - or polysubstituted by methyl, ethyl, propyl, iso-propyl, methoxy or trifluoromethyl) or pyrimidylmethyl (optionally mono- or polysubstituted on the pyrimidyl by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, cyano or nitro, on the methyl part optionally mono- or polysubstituted by methyl, ethyl, propyl, iso-propyl, methoxy or trifluoromethyl). In one embodiment 47, the invention relates to compounds according to embodiment 40 in which Q is Q 3 .
In einer Ausführungsform 48 betrifft die Erfindung Verbindungen gemäß Ausführungsform 47, in denen Q3 für C(R1ORU)NR8R9 steht; R10 und R11 unabhängig voneinander für Wasserstoff, Q-C2- Alkyl oder Ci-C2-Haloalkyl stehen und R8 und R9 unabhängig voneinander für Wasserstoff, Q-C4- Alkyl, Ci-C4-Haloalkyl, C3-C4-Cycloalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, CrC2-Haloalkyl, Ci-C2-Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten), C3-C4-Cycloalkyl-Ci-C2-alkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Haloalkyl, Ci-C2-AIlCyI oder kondensiert an einen Aromaten oder Heteroaromaten, am Ci-C2-Alkylteil gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Ci-C2-Alkyl, Q-C2-Haloalkyl, C,-C2-Alkoxy oder Cyano), Q-C2-Alkylsulfinyl-Q- C2-alkyl, C1-C2-Alkylsulfanyl-C,-C2-alkyl, CrC2-Alkylsulfonyl-Ci-C2-alkyl, Phenyl-Ci-C4-alkyl, Heteroaryl-Ci-C4-alkyl, Ci-C4-Dialkylaminocarbonyl, Ci-C4-Alkylaminocarbonyl, Q-C4-HaIo- alkylaminocarbonyl, Ci-C2-Alkylsulfonyl, Ci-C2-Alkylcarbonyl, C]-C2-Haloalkylcarbonyl, C3-C5- Cycloalkylcarbonyl, Ci-C2-Alkoxycarbonyl, Ci-C2-Alkoxy-Ci-C2-alkylcarbonyl, Phenylsulfonyl, Phenyl, Heteroaryl, Hetero-C3-Q-cyclyl, Phenylcarbonyl, Heteroarylcarbonyl, Hetero-Q-Q- cyclylcarbonyl, Phenyl-Ci-C2-alkylcarbonyl, Heteroaryl-Ci-C2-alkylcarbonyl, Hetero-C3-C5-cyclyl- Ci-C2-alkylcarbonyl, Phenoxycarbonyl oder Phenyl-Ci-C2-alkoxycarbonyl stehen; wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Q- C2-Alkyl, Ci-C2-Haloalkyl, CrC2-Alkoxy, Nitro oder Cyano; und ein an Phenyl oder Heteroaryl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Q- C4-Alkyl, Q-C4-Haloalkyl, Q-C2-Alkoxy oder Cyano.In an embodiment 48, the invention relates to compounds according to embodiment 47 in which Q 3 is C (R 10 R U ) NR 8 R 9 ; R 10 and R 11 are independently hydrogen, QC 2 - alkyl or Ci-C 2 haloalkyl, and R 8 and R 9 are independently hydrogen, QC 4 - alkyl, Ci-C 4 haloalkyl, C 3 -C 4 -Cycloalkyl (at the cycle optionally mono- or polysubstituted by halogen, C r C 2 haloalkyl, Ci-C 2 alkyl or fused to an aromatic or heteroaromatic), C 3 -C 4 cycloalkyl-Ci-C 2 alkyl (optionally mono- or polysubstituted by halogen, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkyl or fused to an aromatic or heteroaromatic radical on the cycle, if appropriate mono- or polysubstituted by halogen, C 1 -alkyl on the C 1 -C 2 -alkyl part C 2 alkyl, QC 2 haloalkyl, C 1 -C 2 alkoxy or cyano), QC 2 alkylsulfinyl-Q-C 2 alkyl, C 1 -C 2 alkylsulfanylC, C 2 alkyl, C r C 2 alkylsulfonyl-Ci-C 2 alkyl, phenyl-Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl, Ci-C4-dialkylaminocarbonyl, Ci-C4-alkylaminocarbonyl, QC 4 -HaIo - Alkylaminocarbonyl, Ci-C 2 -alkylsulfonyl, Ci-C 2 -alk ylcarbonyl, C 1 -C 2 -haloalkylcarbonyl, C 3 -C 5 -cycloalkylcarbonyl, C 1 -C 2 -alkoxycarbonyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl, heteroC 3 - Q-cyclyl, phenylcarbonyl, heteroarylcarbonyl, hetero-QQ-cyclylcarbonyl, phenyl-Ci-C 2 -alkylcarbonyl, heteroaryl-Ci-C 2 -alkylcarbonyl, hetero-C 3 -C 5 -cyclyl-Ci-C 2 -alkylcarbonyl, phenoxycarbonyl or phenyl-Ci-C 2 alkoxycarbonyl; wherein a phenyl or heteroaryl optionally mono- or polysubstituted by halogen, Q-C2 alkyl, Ci-C 2 haloalkyl, C r C 2 alkoxy, nitro or cyano; and an alkanediyl radical attached to phenyl or heteroaryl is optionally mono- or polysubstituted by halogen, Q-C 4 -alkyl, QC 4 -haloalkyl, QC 2 -alkoxy or cyano.
In einer Ausführungsform 49 betrifft die Erfindung Verbindungen gemäß Ausführungsform 48, in denen R8 und R9 unabhängig voneinander für Wasserstoff, Q-C2-Alkyl, Q-C2-Haloalkyl, C3-C5- Cycloalkyl, CrC5-Cycloalkyl-Q-C2-alkyl, Q-Q-Halocycloalkyl, Q-C5-Halocycloalkyl-Q-C2- alkyl, Methylsulfinyl-Q-C3-alkyl, Methylsulfanyl-CrC3-alkyl, Methylsulfonyl-C1-C3-alkyl, Phenyl-Ci-C2-alkyl, Heteroaryl-Q-C2-alkyl, Ci-C2-Dialkylaminocarbonyl, Q-Q-Alkylamino- carbonyl, Ci-C2-Haloalkylaminocarbonyl, Q-C2-Alkylsulfonyl, CrC2-Alkylcarbonyl, Q-C2-HaIo- alkylcarbonyl, C3-C5-Cycloalkylcarbonyl, Q-C2-Alkoxycarbonyl, Phenylsulfonyl, Phenylcarbonyl, Heteroarylcarbonyl, Hetero-C3-C5-cyclylcarbonyl, Phenyl-C]-C2-alkylcarbonyl, Heteroaryl-Q-Q- alkylcarbonyl, Hetero-C3-C5-cyclyl-Ci-C2-alkylcarbonyl oder Phenoxycarbonyl stehen; wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Q- C2-Alkyl, Q-C2-Haloalkyl, Q-C2-Alkoxy, Nitro oder Cyano; und ein an Phenyl oder Heteroaryl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Q- QrAlkyl, Q-C4-Haloalkyl, Q-C2-Alkoxy oder Cyano. In einer Ausfuhrungsform 50 betrifft die Erfindung Verbindungen gemäß Ausführungsform 40, in denen Q für Q4 steht.In one embodiment 49, the invention relates to compounds according to embodiment 48 wherein R 8 and R 9 are independently hydrogen, QC 2 alkyl, QC 2 haloalkyl, C 3 -C 5 cycloalkyl, C r C 5 cycloalkyl QC 2- alkyl, QQ-halocycloalkyl, QC 5 -halocycloalkyl-QC 2 -alkyl, methylsulfinyl-QC 3 -alkyl, methylsulfanyl-C r C 3 -alkyl, methylsulfonyl-C 1 -C 3 -alkyl, phenyl-Ci-C 2 alkyl, heteroaryl-QC 2 alkyl, Ci-C2 dialkylaminocarbonyl, QQ-alkylamino carbonyl, C 2 -Haloalkylaminocarbonyl, QC 2 alkylsulfonyl, C r C 2 alkylcarbonyl, QC 2 -HaIo- alkylcarbonyl, C 3 -C 5 -cycloalkylcarbonyl, QC 2 -alkoxycarbonyl, phenylsulfonyl, phenylcarbonyl, heteroarylcarbonyl, hetero-C 3 -C 5 -cycloylcarbonyl, phenylC] -C 2 -alkylcarbonyl, heteroarylQQ-alkylcarbonyl, heteroC 3 -C 5 -cyclyl-C 1 -C 2 -alkylcarbonyl or phenoxycarbonyl; where a phenyl or heteroaryl radical is optionally monosubstituted or polysubstituted by halogen, Q-C 2 -alkyl, QC 2 -haloalkyl, QC 2 -alkoxy, nitro or cyano; and an alkanediyl radical bonded to phenyl or heteroaryl is optionally monosubstituted or polysubstituted by halogen, Q-QrAlkyl, QC 4 -haloalkyl, QC 2 -alkoxy or cyano. In one embodiment 50, the invention relates to compounds according to embodiment 40, in which Q stands for Q 4 .
In einer Ausführungsform 51 betrifft die Erfindung Verbindungen gemäß Ausführungsform 50, in denen Q4 für Cyano (wobei R1 nicht für Amino steht), Nitro, Amino, COOH, COOR12, Fluor (falls R3 verschieden von Chlor ist), Chlor (falls R3 verschieden von Chlor, COOH, CH2CH2OMe und OMe ist), Brom, Iod, SR12 (wobei R1 nicht für Amino steht, falls R12 für Alkyl steht), S(O)R12oder S(O)2R12 steht und R12 für CrC4-Alkyl oder CrC4-Haloalkyl steht.In one embodiment 51, the invention relates to compounds according to embodiment 50 in which Q 4 is cyano (where R 1 is not amino), nitro, amino, COOH, COOR 12 , fluorine (if R 3 is other than chlorine), chloro ( if R 3 is other than chloro, COOH, CH 2 CH 2 OMe and OMe), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 and R 12 is C r C 4 alkyl or C r C 4 haloalkyl.
In einer Ausführungsform 52 betrifft die Erfindung Verbindungen gemäß Ausführungsform 51 , in denen Q4 für Cyano (wobei R1 nicht für Amino steht), COOH, COOMe, COOEt, Fluor (falls R3 verschieden von Chlor ist), Brom, Iod, SR12 (wobei R1 nicht für Amino steht, falls R12 für Alkyl steht), S(O)R12oder S(O)2R12 steht.In one embodiment 52, the invention relates to compounds according to embodiment 51 in which Q 4 is cyano (where R 1 is other than amino), COOH, COOMe, COOEt, fluorine (if R 3 is other than chlorine), bromine, iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 or S (O) 2 R 12 .
Gegenstand der vorliegenden Erfindung ist auch die Verwendung der Verbindungen der Formel (T) zur Bekämpfung tierischer Schädlinge, wobei die Reste wie oben definiert sind.The present invention also relates to the use of the compounds of the formula (T) for controlling animal pests, where the radicals are as defined above.
Gegenstand der vorliegenden Erfindung ist auch die Verwendung der Verbindungen der Formel (I) zur Bekämpfung tierischer Schädlinge, wobei M für M1 steht, Q für Q4 steht, Q4 für Wasserstoff steht und alle anderen Reste wie oben definiert sind, mit der Maßgabe, dass A1 und A2 nicht gleichzeitig für Stickstoff stehen.The present invention also provides the use of the compounds of the formula (I) for combating animal pests, wherein M is M 1 , Q is Q 4 , Q 4 is hydrogen and all other radicals are as defined above, with the proviso in that A 1 and A 2 are not simultaneously nitrogen.
Gegenstand der vorliegenden Erfindung ist auch die Verwendung der Verbindungen der Formel (I) zur Bekämpfung tierischer Schädlinge, wobei wobei M für M1 steht, R3 für Wasserstoff steht und alle anderen Reste wie oben definiert sind, mit der Maßgabe, dass A1 und A2 nicht gleichzeitig für Stickstoff stehen.The present invention also provides the use of the compounds of the formula (I) for controlling animal pests, wherein wherein M is M 1 , R 3 is hydrogen and all other radicals are as defined above, with the proviso that A 1 and A 2 does not simultaneously stand for nitrogen.
Die erfindungsgemäßen Verbindungen können in unten genannter oder hierzu analoger Weise hergestellt werden.The compounds according to the invention can be prepared in the manner mentioned below or analogously thereto.
Verfahren (A)Procedure (A)
Verbindungen der Formel (H) werden z.B. nach folgendem Verfahren (A) synthetisiert: Compounds of the formula (H) are synthesized, for example, by the following process (A):
wobeiin which
G1"5, R2 und M die oben angegebenen Bedeutungen haben;G 1 "5 , R 2 and M have the meanings given above;
Beim Verfahren (A) zur Herstellung der Verbindungen der Formel (II) werden Ketonitrile, deren Tautomere oder Hydrate der Formeln (VI-A), (VI-B) bzw. (VI-C) oder Aminoacrylonitrile und deren Tautomere der Formeln (VI-D) und (IV-E) mit Aryl- oder Heteroaryl-Hydrazinen der FormelIn the process (A) for the preparation of the compounds of formula (II) are ketonitriles, their tautomers or hydrates of the formulas (VI-A), (VI-B) or (VI-C) or aminoacrylonitriles and their tautomers of the formulas (VI D) and (IV-E) with aryl or heteroaryl-hydrazines of the formula
(Vπ) kondensiert, wobei zunächst Hydrazone der Formel (VDT) als Intermediat entstehen und bei längerer Reaktionszeit und höherer Temperatur der Ringschluss zum Aminopyrazol der Formel (TI) erfolgt. Dabei können Säuren als Katalysator zugesetzt werden, wobei anorganische Säuren wie Salzsäure und organische Säuren wie Sulfonsäuren oder Essigsäure geeignet sein können. Alternativ werden Ketonitrile, deren Tautomere oder Hydrate der Formeln (VI-A), (VI-B) bzw. (VI-C) zunächst mit einem Chlorierungsmittel, z.B. Phosphorylchlorid, Phosphorpentachlorid, Thionylchlorid, Phosgen, Chlor oder Oxalylchlorid, gegebenenfalls in einem inerten organischen Lösungsmittel verdünnt, zu Chloracrylnitrilen (VI-F) umgesetzt, wobei die Reaktion im Temperaturbereich von -20 0C bis 1200C durchgeführt werden kann. In einem anschließenden Schritt erfolgt die Kondensation mit Aryl oder Heteroaryl-Hydrazinen der Formel (VIT) in einem geeigneten organischen Lösungsmittel in Gegenwart von basischen Hilfsreagentien, z.B. Alkoholaten oder Stickstoffbasen, wobei die Reaktion im Temperaturbereich von -20 0C bis 1200C durchgeführt werden kann.(Vπ) condenses, wherein initially hydrazones of the formula (VDT) arise as an intermediate and the reaction takes place at a higher reaction time and higher temperature, the ring closure to the aminopyrazole of the formula (TI). In this case, acids can be added as a catalyst, wherein inorganic acids such as hydrochloric acid and organic acids such as sulfonic acids or acetic acid may be suitable. Alternatively, ketonitriles, their tautomers or hydrates of the formulas (VI-A), (VI-B) or (VI-C) first with a chlorinating agent, for example phosphoryl chloride, phosphorus pentachloride, thionyl chloride, phosgene, chlorine or oxalyl chloride, optionally in an inert diluted organic solvent, converted to chloroacrylonitriles (VI-F), wherein the reaction in the temperature range from -20 0 C to 120 0 C can be performed. In a subsequent step, the condensation is carried out with aryl or heteroaryl-hydrazines of the formula (VIT) in a suitable organic solvent in the presence of basic auxiliary reagents, eg alcoholates or nitrogen bases, wherein the reaction in the temperature range from -20 0 C to 120 0 C are performed can.
Synthesemethoden strukturverwandter Aminopyrazolen ist bekannt und wird beispielsweise in J. Med. Chem. 2006, 14(6), 1785-1791; Eur. J. Med. Chem. 2005, 40, 922-927; J. Chem. Res. Synopses 1985, 5, 198-199; J. Mol. Cat. A 2006, 258(1-2), 371-375; J. Med. Chem. 2006, 49, 3332-3344; Bioorg. Med. Chem. 2006, 14(6), 1785-1791; Eur. J. Med. Chem. 2005, 40(9), 922- 927; Tetrahedron 2004, 60(4), 901-906; J. Heterocyclic Chem. 1975, 12(5), 899-901, Molecular Div. 2003, 7(2-4), 161-164; DE -A-2643640; und US 3,041,342 beschrieben.Synthetic methods of structurally related aminopyrazoles are known and described, for example, in J. Med. Chem. 2006, 14 (6), 1785-1791; Eur. J. Med. Chem. 2005, 40, 922-927; J. Chem. Res. Synopses 1985, 5, 198-199; J. Mol. Cat. A 2006, 258 (1-2), 371-375; J. Med. Chem. 2006, 49, 3332-3344; Bioorg. Med. Chem. 2006, 14 (6), 1785-1791; Eur. J. Med. Chem. 2005, 40 (9), 922-927; Tetrahedron 2004, 60 (4), 901-906; J. Heterocyclic Chem. 1975, 12 (5), 899-901, Molecular Div. 2003, 7 (2-4), 161-164; DE-A-2643640; and US 3,041,342.
Die Ketonitrile können in den tautomeren Formen (VI-A) und (VI-B) und als Hydrat (VI-C) vorliegen. Die Ausgangsverbindungen können auch in Form ihrer Salze eingesetzt werden, z.B. können die Ketonitrile in Form ihrer Alkalisalze verwendet werden.The ketonitriles may be present in tautomeric forms (VI-A) and (VI-B) and as hydrate (VI-C). The starting compounds may also be used in the form of their salts, e.g. For example, the ketonitriles can be used in the form of their alkali metal salts.
Die Aminoacrylnitrile können in den tautomeren Formen (VI-D) und (VI-E) vorliegen. Die Ausgangsverbindungen können auch in Form ihrer Salze eingesetzt werden, z.B. können die Aminoacrylnitrile in Form ihrer Alkalisalze verwendet werden.The aminoacrylonitriles may be present in the tautomeric forms (VI-D) and (VI-E). The starting compounds may also be used in the form of their salts, e.g. For example, the aminoacrylonitriles can be used in the form of their alkali metal salts.
Ketonitrile der Formel (VI-A, VI-B und VI-C) lassen sich nach bekannten Methoden herstellen. Solche Methoden sind beschrieben in: J. Amer. Chem. Soc. 1950, 72, 5409-5413; Tetrahedron 2007, 63(47), 11626-11635, Org. Lett. 2007, 9(18), 3575-3578, J. Med. Chem. 2007, 50(2), 399- 403, Bioorg. Med. Chem. Lett. 2006, 16(3), 695-700.Ketonitriles of the formula (VI-A, VI-B and VI-C) can be prepared by known methods. Such methods are described in: J. Amer. Chem. Soc. 1950, 72, 5409-5413; Tetrahedron 2007, 63 (47), 11626-11635, Org. Lett. 2007, 9 (18), 3575-3578, J. Med. Chem. 2007, 50 (2), 399-403, Bioorg. Med. Chem. Lett. 2006, 16 (3), 695-700.
Acrylonitrile der Formel (VI-D und VI-E) lassen sich nach bekannten Methoden herstellen. Solche Methoden beschrieben in: J. Med. Chem. 2006, 49, 3332-3344.Acrylonitriles of the formula (VI-D and VI-E) can be prepared by known methods. Such methods are described in: J. Med. Chem. 2006, 49, 3332-3344.
Chloracrylnitrile der Formel (VI-F) lassen sich nach bekannten Methoden herstellen. Solche Methoden beschrieben in: J. Org Chem (UdSSR) 1981, 1441, JP 08-208620, J. Med. Chem. 2005, 48(22), 6843-6854, Nucleosides, Nucleotides Nucleic Acids 2004, 23(5), 805-812, J. Med. Chem. 2001, 44(3), 350-361. Aryl-, Pyridyl- und Pyrimidinylhydrazine der Formel (VTI) sind zum Teil kommerziell verfügbar oder lassen sich nach dem Fachmann bekannten Methoden, wie z.B. im Verfahren (H) beschrieben, herstellen.Chloroacrylonitriles of the formula (VI-F) can be prepared by known methods. Such methods are described in: J. Org Chem (USSR) 1981, 1441, JP 08-208620, J. Med. Chem. 2005, 48 (22), 6843-6854, Nucleosides, Nucleotides Nucleic Acids 2004, 23 (5), 805-812, J. Med. Chem. 2001, 44 (3), 350-361. Aryl, pyridyl and Pyrimidinylhydrazine of formula (VTI) are commercially available in part or can be prepared by methods known in the art, such as in process (H), produced.
Die zum Aufbau von Q1'3 benötigten Amidierungs-, Acylierungs- und Substitutionsreaktionen werden nach dem Fachmann bekannten Methoden, wie z.B. in den Verfahren (F), (G) und (J) beschrieben, durchgeführt und können entweder am Ende der Synthesefrequenz oder bevorzugt auf der Stufe von geeigneten Intermediaten erfolgen.The amidation, acylation and substitution reactions required for the construction of Q 1'3 are carried out by methods known to the person skilled in the art, as described, for example, in processes (F), (G) and (J) and can be carried out either at the end of the synthesis frequency or preferably at the stage of suitable intermediates.
Verfahren (B)Method (B)
Erfindungsgemäße Verbindungen der Formel (I) werden z.B. nach folgendem Verfahren (B) synthetisiert:Compounds of the formula (I) according to the invention are e.g. synthesized by the following procedure (B):
wobei in which
LG = Halogen, Alkylsulfonyl, Boronsäure oder BoronsäureesterLG = halogen, alkylsulfonyl, boronic acid or boronic acid ester
Die Zwischenprodukte (DC) werden nach Verfahren (A) mit Hydrazinhydrat hergestellt: The intermediates (DC) are prepared by process (A) with hydrazine hydrate:
reagenz reagent
Beim Verfahren (B) werden 1-H-Aminopyrazole der Formel (EX) mit Arylhalogeniden, Heteroarylhalogeniden, Arylalkylsulfonen Heteroarylalkylsulfonen, Arylboronsänren, Heteroaryl- boronsäuren, Arylboronsäureestern oder Heteroarylboronsäureestern (LG-M) in Gegenwart einer Base und eventuell eines Kupfer- oder Eisensalzes und eines Liganden in einem geeigneten organischen Lösungsmitteln umgesetzt, wobei bevorzugt ein bestimmtes Isomer, das Aminopyrazol der Formel (I), gebildet wird.In process (B), 1-H-aminopyrazoles of the formula (EX) are reacted with aryl halides, heteroaryl halides, arylalkylsulfones, heteroarylalkylsulfones, arylboronic esters, heteroarylboronic acids, arylboronic esters or heteroarylboronic esters (LG-M) in the presence of a base and possibly a copper or iron salt and a ligand in a suitable organic solvent, wherein preferably a particular isomer, the aminopyrazole of the formula (I) is formed.
Die Synthese strukturverwandter Aminopyrazolen der Formel (IX) ist allgemein bekannt und wird beschrieben in: DE-A 2643640, Bioorg. Med. Chem. Lett. 2004, 14, 3669, Bioorg. Med. Chem. 2000, 8(1), 181-190, J. Comb. Chem. 2007, 9(3), 507-512, J. Med. Chem. 2004, 47(24), 5872- 5893, EP-A-269859, J. Prakt. Chem. 1979, 321(2), 341-344,The synthesis of structurally related aminopyrazoles of the formula (IX) is generally known and is described in: DE-A 2643640, Bioorg. Med. Chem. Lett. 2004, 14, 3669, Bioorg. Chem. Chem. 2000, 8 (1), 181-190, J. Comb. Chem., 2007, 9 (3), 507-512, J. Med. Chem. 2004, 47 (24), 5872-5893, EP-A-269859, J. Prakt. Chem. 1979, 321 (2), 341-344,
Die Cu- und Fe-katalysierte Arylierung von Pyrazolen ist bekannt und wird beschrieben in: J. Org. Chem. 2004, 69(17), 5578-5587, Angew. Chem. Int. Ed. 2007, 46, 934-936, Bioorg. Med. Chem. Lett. 2007, 17(15), 4303-4307, IN 178903, Bioorg. Med. Chem. 2007, 17(2), 354-357, J. Med. Chem. 2004, 47(19), 4645-4648.The Cu- and Fe-catalyzed arylation of pyrazoles is known and described in: J. Org. Chem. 2004, 69 (17), 5578-5587, Angew. Chem. Int. Ed. 2007, 46, 934-936, Bioorg. Med. Chem. Lett. 2007, 17 (15), 4303-4307, IN 178903, Bioorg. Med. Chem. 2007, 17 (2), 354-357, J. Med. Chem. 2004, 47 (19), 4645-4648.
Die Synthese von Aminopyrazolen durch nukleophile Aromaten- und Heteroaromatensubstitution ist bekannt und wird beschrieben in: J. Med. Chem. 2004, 47, 2995-3008, IP 2007-169575, Synth. Commun. 2006, 36(11), 1601-1612, Can. J. Chem. 1988, 66(3), 420-428.The synthesis of aminopyrazoles by nucleophilic aromatic and heteroaromatic substitution is known and described in: J. Med. Chem. 2004, 47, 2995-3008, IP 2007-169575, Synth. Commun. 2006, 36 (11), 1601-1612, Can. J. Chem. 1988, 66 (3), 420-428.
Die Ketonitrile können in den tautomeren Formen (VI-A) und (VI-B) und als Hydrat (VI-C) vorliegen. Die Ausgangsverbindungen können auch in Form ihrer Salze eingesetzt werden, z.B. können die Ketonitrile in Form ihrer Alkalisalze verwendet werden.The ketonitriles may be present in tautomeric forms (VI-A) and (VI-B) and as hydrate (VI-C). The starting compounds may also be used in the form of their salts, e.g. For example, the ketonitriles can be used in the form of their alkali metal salts.
Die Aminoacrylnitrile können in den tautomeren Formen (VI-D) und (VI-E) vorliegen. Die Ausgangsverbindungen können auch in Form ihrer Salze eingesetzt werden, z.B. können die Aminoacrylnitrile in Form ihrer Alkalisalze verwendet werden.The aminoacrylonitriles may be present in the tautomeric forms (VI-D) and (VI-E). The starting compounds may also be used in the form of their salts, e.g. For example, the aminoacrylonitriles can be used in the form of their alkali metal salts.
Die Ketonitrile der Formel (VI-A, VI-B und VI-C) lassen sich nach bekannten Methoden herstellen: J. Amer. Chem. Soc. 1950, 72, 5409-5413; Tetrahedron 2007, 63(47), 11626-11635; Org. Lett. 2007, 9(18), 3575-3578; J. Med. Chem. 2007, 50(2), 399-403, Bioorg. Med. Chem. Lett. 2006, 16(3), 695-700.The ketonitriles of the formula (VI-A, VI-B and VI-C) can be prepared by known methods: J. Amer. Chem. Soc. 1950, 72, 5409-5413; Tetrahedron 2007, 63 (47), 11626-11635; Org. Lett. 2007, 9 (18), 3575-3578; J. Med. Chem. 2007, 50 (2), 399-403, Bioorg. Med. Chem. Lett. 2006, 16 (3), 695-700.
Die Acrylonitrile der Formel (VI-D und VI-E) lassen sich nach bekannten Methoden herstellen: J. Med. Chem. 2006, 49, 3332-3344The acrylonitriles of the formula (VI-D and VI-E) can be prepared by known methods: J. Med. Chem. 2006, 49, 3332-3344
Die Chloracrylnitrile der Formel (VI-F) lassen sich nach bekannten Methoden herstellen: J. Org. Chem. (UdSSR) 1981, 1441 JP 08208620 , J. Med. Chem., 2005, 48(22), 6843-6854, Nucleosides, Nucleotides and Nucleic Acids, 2004, 23(5), 805-812, J. Med. Chem., 2001, 44(3), 350-361The chloroacrylonitriles of the formula (VI-F) can be prepared by known methods: J. Org. Chem. (USSR) 1981, 1441 JP 08208620, J. Med. Chem., 2005, 48 (22), 6843-6854, Nucleosides , Nucleotides and Nucleic Acids, 2004, 23 (5), 805-812, J. Med. Chem., 2001, 44 (3), 350-361
Die Aryl- und Heteroarylverbindungen LG-M sind zum Teil kommerziell verfügbar oder lassen sich nach dem Fachmann bekannten Methoden herstellen.Some of the aryl and heteroaryl compounds LG-M are commercially available or can be prepared by methods known to those skilled in the art.
Die zum Aufbau von Q1"3 benötigten Amidierungs-, Acylierungs und Substitutionsreaktionen werden nach dem Fachmann bekannten Methoden, wie z.B. in den Verfahren (F), (G) und (I) beschrieben, durchgeführt und können entweder am Ende der Synthesefrequenz oder bevorzugt auf der Stufe von geeigneten Intermediaten erfolgen. Gegenstand der vorliegenden Erfindung sind auch Verbindungen der Formel (DC)The amidation, acylation and substitution reactions required for the construction of Q 1 "3 are carried out by methods known to those skilled in the art, as described, for example, in processes (F), (G) and (I) and can be either at the end of the synthesis frequency or preferred at the level of suitable intermediates. The present invention also relates to compounds of the formula (DC)
wobei G1, G2, G3, G4, G5, R1 und R2 wie oben definiert sind, mit der Maßgabe, dass R1 nicht für Amino steht.wherein G 1 , G 2 , G 3 , G 4 , G 5 , R 1 and R 2 are as defined above, with the proviso that R 1 is not amino.
Verfahren (C)Method (C)
Erfindungsgemäße Verbindungen der Formel (HIa, mb, Ute und DId) lassen sich nach dem Verfahren (C) synthetisieren:Compounds of the formula (IIIa, mb, Ute and DId) according to the invention can be synthesized by process (C):
wobei hier being here
R13 für CH2R5 stehtR 13 is CH 2 R 5
wobeiin which
G ,1-5 , r R,2 , r R> 13 , r R> 14 und M die oben angegebenen Bedeutungen haben können, R 13 „ u„nd J D R 14 aber nicht beide gleichzeitig für Wasserstoff stehen; LG für Halogen oder Alkylsulfonyl steht.G, 1-5, r R, 2, r R> 13, r R> 14 and M may have the meanings given above, but R 13 "and JDR 14 are not both simultaneously hydrogen; LG is halogen or alkylsulfonyl.
Beim erfindungsgemäßen Verfahren (C) zur Herstellung der Verbindungen der Formel (EIa) und (Hb) werden Verbindungen der Formel (ff) mit einem oder zwei Alkylierungsmitteln, Acylierungsmitteln oder Sulfonylierungsrnitteln R13-LG bzw. R14-LG umgesetzt, wobei durch Monosubstitution und Disubstitution Aminopyrazole der Formel (ffla) bzw. (HIb) entstehen. Geeignete Alkylierungsmittel sind Alkylbromide, Alkyldibromide, Alkyliodide, Alkyldiiodide, Dialkylsulfate und Alkylsulfonate. Als Acylierungsmittel werden Carbonsäureanhydride und Carbonsäurechloride, als Sulfonylierungsmittel Sulfonylchloride verwendet. Alternativ können die einfach N-substituierten Aminopyrazole der Formel (HIa) durch reduktive Aminierung aus den Aminopyrazolen der Formel (ff), einem Aldehyd und einem Reduktionsmittel, z.B. Wasserstoff in Gegenwart eines Hydrierkatalysators, Alkaliborhydriden oder Boran erhalten werden.In the process (C) according to the invention for the preparation of the compounds of the formula (EIa) and (Hb), compounds of the formula (ff) are reacted with one or two alkylating agents, acylating agents or sulfonylating agents R 13 -LG or R 14 -LG, where by monosubstitution and disubstitution aminopyrazoles of the formula (ffla) or (HIb) arise. Suitable alkylating agents are alkyl bromides, alkyl dibromides, alkyl iodides, alkyl diiodides, dialkyl sulfates and alkyl sulfonates. The acylating agents used are carboxylic anhydrides and carbonyl chlorides, and sulfonyl chlorides are sulfonyl chlorides. Alternatively, the mono-N-substituted aminopyrazoles of the formula (IIIa) can be obtained by reductive amination from the aminopyrazoles of the formula (ff), an aldehyde and a reducing agent, for example hydrogen in the presence of a hydrogenation catalyst, alkali metal borohydrides or borane.
Alternativ können Verbindungen der Formel (ffla) durch Umsetzung von Verbindungen der Formel (II) zu Amidinen der Formel (Iffc) oder Imidoestern der Formel (Iffd), gefolgt von einem Reduktionsschritt, erhalten werden.Alternatively, compounds of formula (ffla) can be obtained by reacting compounds of formula (II) to amidines of formula (Iffc) or imidoesters of formula (Iffd), followed by a reduction step.
Die Alkylierung von strukturverwandten Aminopyrazolen wird beschrieben in:, WO 2006/000312, WO 2005/09312, WO 2005/023761, WO 2004/099156The alkylation of structurally related aminopyrazoles is described in: WO 2006/000312, WO 2005/09312, WO 2005/023761, WO 2004/099156
Die reduktive Aminierung von strukturverwandten Aminopyrazolen wird beschrieben in: J. Med. Chem. 2002, 45(14), 2994-3008, WO 2002/010153, Tetrahedron Lett. 2001, 42(21), 3587-3590The reductive amination of structurally related aminopyrazoles is described in: J. Med. Chem. 2002, 45 (14), 2994-3008, WO 2002/010153, Tetrahedron Lett. 2001, 42 (21), 3587-3590
Die Acylierung von strukturverwandten Aminopyrazolen wird beschrieben in:, J. Med. Chem. 2006, 49(11), 3332-3344, J. Med. Chem. 2007, 50(21), 5161-5167, Bioorg. Med. Chem. 2006, 14(22), 7501-7511, Org. Biomol. Chem. 2004, 2(11), 1603-1611.The acylation of structurally related aminopyrazoles is described in: J. Med. Chem. 2006, 49 (11), 3332-3344, J. Med. Chem. 2007, 50 (21), 5161-5167, Bioorg. Med. Chem. 2006, 14 (22), 7501-7511, Org. Biomol. Chem. 2004, 2 (11), 1603-1611.
Die Sulfonylierung von strukturverwandten Aminopyrazolen wird beschrieben in:, Acta Poloniae Pharmaceutica 2003, 60(1), 51-60, Biochemistry 2003, 42(21), 6363-6369, J. Med. Chem. 2001, 44(22), 3622-3631.The sulfonylation of structurally related aminopyrazoles is described in: Acta Poloniae Pharmaceutica 2003, 60 (1), 51-60, Biochemistry 2003, 42 (21), 6363-6369, J. Med. Chem. 2001, 44 (22), 3622 -3631.
Die Synthese von strukturverwandten Iminen der Formel (Iffc) wird beschrieben in:, Tetrahedron 2006, 62(24), 5617-5625, Tetrahedron 1987, 53(18), 4185-4193.The synthesis of structurally related imines of the formula (Iffc) is described in: Tetrahedron 2006, 62 (24), 5617-5625, Tetrahedron 1987, 53 (18), 4185-4193.
Die Synthese von strukturverwandten Amidinen (Iffc) und Imidoestern (DId) und deren Reduktion wird beschrieben in: WO 2005/060749.The synthesis of structurally related amidines (Iffc) and imidoesters (DId) and their reduction is described in: WO 2005/060749.
Verfahren (D) Erfindungsgemäße Verbindungen der Formel (ET) und (IVa bis IVe) werden z.B. nach Verfahren (D) synthetisiert:Method (D) Compounds of the formula (ET) and (IVa to IVe) according to the invention are synthesized, for example, by process (D):
R" = AlkylsulfanylR "= alkylsulfanyl
1 Oxidations- äquivalent1 oxidation equivalent
(IVe) (IVd) (IVc)(IVe) (IVd) (IVc)
1 Oxidations- äquivalent1 oxidation equivalent
wobeiin which
G , R , R , R , R und M die oben beschriebenen Bedeutungen haben;G, R, R, R, R and M have the meanings described above;
R17 für Halogen oder Alkylsulfanyl steht.R 17 is halogen or alkylsulfanyl.
Beim erfindungsgemäßen Verfahren (D) zur Herstellung der Verbindungen der Formel (HI) und (IV) werden Aminopyrazole der Formel (IT) mit Nitrosylspezies in Gegenwart von geeigneten Halogeniden umgesetzt, wobei nach der Bildung eines Diazo-Intermediates ein 5-Halogenpyrazol der Formel (IVa, R17 = Halogen) entsteht. Geeignete Quellen für Nitrosylspezies sind Alkalinitrite plus Säuren sowie Ester der salpetrigen Säure, z.B. Butylnitrit und tert-Butylnitrit. Als Halogenide können Metallhalogenide sowie organische Halogenide, z.B. Bromoform oder Iodoform verwendet werden. Diese 5-Halogenpyrazole können mit Cyaniden, z.B. CuCN in geeigneten Lösungsmitteln, z.B. NMP unter Hitzezufuhr in 5-Cyanopyrazole der Formel (IVb) oder mit Aminen in geeigneten Lösungsmitteln in 5-Aminopyrazole der Formel (DI), umgewandelt werden, wobei R13 oder R14 ungleich Wasserstoff ist. Die Umsetzung der Diazo-Intermediate mit Alkylsulfanylquellen, z.B. Dialkyldisulfiden führt zu 5-Alkylsulfanylpyrazolen der Formel (IVa, R17 = Alkylsulfanyl). Diese Thioether können in Gegenwart eines geeigneten Oxidationsmittels, z.B. mit H2O2, Natriumperiodat, tert.-Butylhypochlorit, Calciumhypochlorit Ca(OCl)2, Natriumchlorit NaClO2, Natriumhypochlorit NaOCl, Persäuren oder O2 und katalytischem Cerammoniumnitrat zu 5- Alkylsulfϊnylpyrazolen der Formel (IVd) und 5-Alkylsulfonylpyrazolen der Formel (IVe) oxidiert werden.In the process (D) according to the invention for preparing the compounds of the formula (HI) and (IV), aminopyrazoles of the formula (IT) are reacted with nitrosyl species in the presence of suitable halides, a 5-halopyrazole of the formula (III) being formed after the formation of a diazo intermediate. IVa, R 17 = halogen) is formed. Suitable sources of nitrosyl species are alkali nitrites plus acids and esters of nitrous acid, eg butyl nitrite and tert-butyl nitrite. As halides metal halides and organic halides, for example bromoform or iodoform can be used. These 5-halopyrazoles can be converted to 5-aminopyrazoles of the formula (DI) with cyanides, for example CuCN in suitable solvents, for example NMP under heat in 5-cyanopyrazoles of the formula (IVb) or with amines in suitable solvents, where R 13 or R 14 is not hydrogen. The implementation of the diazo intermediates with Alkylsulfanylquellen, eg Dialkyl disulfides lead to 5-alkylsulfanylpyrazoles of the formula (IVa, R 17 = alkylsulfanyl). These thioethers can in the presence of a suitable oxidizing agent, for example with H 2 O 2 , sodium periodate, tert-butyl hypochlorite, calcium hypochlorite Ca (OCl) 2 , sodium chlorite NaClO 2 , sodium hypochlorite NaOCl, peracids or O 2 and catalytic cerium ammonium nitrate to 5-Alkylsulfϊnylpyrazolen the formula (IVd) and 5-Alkylsulfonylpyrazolen of formula (IVe) are oxidized.
Die Synthese von strukturverwandten 5-Halogen- und 5-Alkylsulfanylpyrazolen wird beschrieben in, WO 2003/074492, J. Heterocycl. Chem. 1987, 24, 267-270, GB 2149402A, J. Med. Chem. 2006, 49, 1562-1575.The synthesis of structurally related 5-halo and 5-alkylsulfanylpyrazoles is described in WO 2003/074492, J. Heterocycl. Chem. 1987, 24, 267-270, GB 2149402A, J. Med. Chem. 2006, 49, 1562-1575.
Die Synthese von strukturverwandten 5-Cyanopyrazolen wird beschrieben in:, J. Med. Chem. 2006, 49, 1562-1575The synthesis of structurally related 5-cyanopyrazoles is described in: J. Med. Chem. 2006, 49, 1562-1575
Die Synthese von N-substituierten Aminopyrazolen der Formel (IH) wird beschrieben in:, DE 3520327, WO 2005/023776The synthesis of N-substituted aminopyrazoles of the formula (III) is described in: DE 3520327, WO 2005/023776
Die Oxidation von Thioethern wird beschrieben in :, J. March „Advanced Organic Chemistry" 4. Auflage, John Wiley & Sons, 1992, S. 1202 und die dort zitierte LiteraturThe oxidation of thioethers is described in:, J. March "Advanced Organic Chemistry" 4th Edition, John Wiley & Sons, 1992, p. 1202 and the literature cited therein
Verfahren (E)Procedure (E)
Erfindungsgemäße Verbindungen der Formel (I) werden z.B. auch nach folgendem Verfahren (E) synthetisiert:Compounds of the formula (I) according to the invention are e.g. also synthesized according to the following process (E):
wobei G1"5, R1, R2 und M die oben angegebenen Bedeutungen haben und LG für Brom, Iod oder Alkylsulfonyl steht.wherein G 1 "5 , R 1 , R 2 and M have the meanings given above and LG is bromine, iodine or alkylsulfonyl.
Beim erfindungsgemäßen Verfahren (E) zur Herstellung der Verbindungen der Formel (I) werden Bromide oder Iodide der Formel (XI) mit Boronsäuren oder Boronsäureestern der Formel (Xu) in Gegenwart von geeigneten Palladium-Katalysatoren, Liganden und Basen (Suzuki-Reaktion) im Temperaturbereich von -20 0C bis 1200C in geeigneten Lösungsmitteln zur Reaktion gebracht.In the process (E) according to the invention for the preparation of the compounds of the formula (I) are bromides or iodides of the formula (XI) with boronic acids or boronic esters of the formula (Xu) in Presence of suitable palladium catalysts, ligands and bases (Suzuki reaction) in the temperature range from -20 0 C to 120 0 C in suitable solvents reacted.
Die Bromide oder Iodide der Formel (XI) lassen sich nach bekannten Methoden herstellen, beschrieben z.B. in:, WO 2005/11292 , Chemistry of Heterocyclic Compounds (New York, NY, United States), 2005, 41(1), 105-110, Bioorg. & Med. Chem. 2004, 12(12), 3345-3355, Bioorg. Med. Chem. Lett. 2004, 14, 4949, J. Med. Chem. 1977, 20(12), 1562-1569The bromides or iodides of formula (XI) can be prepared by known methods described e.g. in: WO 2005/11292, Chemistry of Heterocyclic Compounds (New York, NY, United States), 2005, 41 (1), 105-110, Bioorg. & Med. Chem. 2004, 12 (12), 3345-3355, Bioorg. Med. Chem. Lett. 2004, 14, 4949, J. Med. Chem. 1977, 20 (12), 1562-1569
Die Boronsäuren oder Boronsäureester der Formel (Xu) sind zum Teil kommerziell verfügbar oder sie sind nach bekannten Methoden leicht herstellbar. Dies ist beispielsweise beschrieben in:, WO 1999/64428.The boronic acids or boronic esters of the formula (Xu) are in part commercially available or they can be easily prepared by known methods. This is described for example in: WO 99/64428.
Gegenstand der vorliegenden Erfindung sind auch Verbindungen der Formeln (XI-A) oder (XI-B)The present invention also relates to compounds of the formulas (XI-A) or (XI-B)
wobei R1, R2, R3, A1, A2 und Q wie oben definiert sind und LG für Chlor, Brom, Iod oder Alkylsulfonyl steht. wherein R 1 , R 2 , R 3 , A 1 , A 2 and Q are as defined above and LG is chloro, bromo, iodo or alkylsulfonyl.
Verfahren (DProcedure (D
Erfindungsgemäße Verbindungen der Formel (I-A) und (I-B) mit Q = Q1 werden z.B. nach folgendem Verfahren (F) synthetisiert:Compounds of the formula (IA) and (IB) according to the invention having Q = Q 1 are synthesized, for example, by the following process (F):
(XIII-A) oder Fe-SaIz, (I-A-Q1)(XIII-A) or Fe-SaIz, (IAQ 1 )
Ligand ligand
(XIII-B) oder Fe-SaIz, (I-B-Q1)(XIII-B) or Fe-SaIz, (IBQ 1 )
Ligandligand
wobeiin which
G1'5, R1, R2, R3, A1 und A2 die oben angegebenen Bedeutungen haben und LG = Halogen, Alkylsulfonyl, Boronsäure oder Boronsäureester bedeutet.G 1'5 , R 1 , R 2 , R 3 , A 1 and A 2 have the meanings given above and LG = halogen, alkylsulfonyl, boronic acid or boronic acid ester.
Beim erfϊndungsgemäßen Verfahren (F) zur Herstellung der Verbindungen der Formel (I-A-Ql) bzw. (I-B-Q 1) werden Verbindungen der Formel (XIII-A) bzw. (XHI-B) mit N-Heterocyclen in Gegenwart einer Base und eventuell eines Kupfer- oder Eisensalzes und eines Liganden in einem geeigneten organischen Lösungsmittel umgesetzt wobei eine Verbindung der Formel (I-A-Ql) bzw. (I-B-Q 1) gebildet wird.In the inventive method (F) for preparing the compounds of formula (IA-Ql) or (IBQ 1) are compounds of formula (XIII-A) or (XHI-B) with N-heterocycles in the presence of a base and possibly one Copper or iron salt and a ligand in a suitable organic solvent to form a compound of formula (IA-Ql) or (IBQ 1) is formed.
Die Cu -katalysierte Arylierung von Heterocyclen wie Triazolen wird beschrieben in: J. Org. Chem. 2007, 72(22), 8535, J. Am. Chem. Soc. 2007, 129 (45), 13879, J. Org. Chem. 2007, 72 (8), 2737, Angew. Chem. 2007, 46 (6), 934.The Cu-catalyzed arylation of heterocycles such as triazoles is described in: J. Org. Chem. 2007, 72 (22), 8535, J. Am. Chem. Soc. 2007, 129 (45), 13879, J. Org. Chem. 2007, 72 (8), 2737, Angew. Chem. 2007, 46 (6), 934.
Die Arylierung von Heterocyclen wie Triazolen durch nukleophile Substitution wird beschrieben in: Bioorg. Med. Chem. Lett. 2007, 17(24), 6707, J. Heterocycl. Chem. 2007, 44 (6), 1323, Chem. Pharm. Bull. 2005, 53 (7), 764.The arylation of heterocycles such as triazoles by nucleophilic substitution is described in: Bioorg. Med. Chem. Lett. 2007, 17 (24), 6707, J. Heterocycl. Chem. 2007, 44 (6), 1323, Chem. Pharm. Bull. 2005, 53 (7), 764.
Verfahren (G)Method (G)
Erfindungsgemäße Verbindungen der Formel (I- A) und (I-B) mit Q = Q2 werden z.B. nach folgendem Verfahren (G) synthetisiert:Compounds of the formula (I-A) and (IB) according to the invention having Q = Q 2 are synthesized, for example, by the following process (G):
Q' = COOR12 Q* = COOH Hydrolyse Q '= COOR 12 Q * = COOH hydrolysis
(I-B-Q«) (I-B-Q«) (I-B-Q2)(I-B-Q ") (I-B-Q") (I-B-Q2)
Q« = COOR" Q4 = COOH wobeiQ «= COOR" Q 4 = COOH where
G , R1, R\ R3, R\ R% R , A1 und A1 die oben angegebenen Bedeutungen haben.G, R 1 , R \ R 3 , R \ R% R, A 1 and A 1 have the meanings given above.
Beim erfindungsgemäßen Verfahren (G) zur Herstellung der Verbindungen (I-A-Q2) bzw. (I-B- Q2) werden Verbindungen der Formel (I-A-Q4) bzw. (I-B-Q4) [Q4 = Ester] nach dem Fachmann bekannten Methoden zu (I-A-Q4) bzw. (I-B-Q4) [Q4 = COOH] hydrolysiert und dann mit Hilfe eines Aktivierungsreagenzes mit einem primären oder sekundären Amin HNR8R9 in Amide der Formehl (I-A-Q2) bzw. (I-B-Q2) umgewandelt. Die Aktivierung kann über Säurechloride, gemischte Anhydride, Pentafluorphenylester oder mit Hilfe von substituierten Carbodiimiden, z. B. DCC (N, N'-Dicyclohexylcarbodiimid), DIC (Diisopropylcarbodiimid) oder EDC (N-Ethyl-N'-(3- dimethylaminopropyl)carbodiimid HCl), und einem Benzotriazol wie HOBt (1- Hydroxybenzotriazol) oder Azabenzotriazol wie HOAt (7-Aza-l-hydroxybenzotriazol) erfolgen.In the process (G) according to the invention for preparing the compounds (IA-Q2) or (IB-Q2), compounds of the formula (IA-Q4) or (IB-Q4) [Q4 = ester] are obtained by methods known to the person skilled in the art ( IA-Q4) or (IB-Q4) [Q4 = COOH] and then converted into amides of the molding compound (IA-Q2) or (IB-Q2) with the aid of an activating reagent with a primary or secondary amine HNR 8 R 9 , Activation may be via acid chlorides, mixed anhydrides, pentafluorophenyl esters or with the aid of substituted carbodiimides, e.g. DCC (N, N'-dicyclohexylcarbodiimide), DIC (diisopropylcarbodiimide) or EDC (N-ethyl-N '- (3-dimethylaminopropyl) carbodiimide HCl), and a benzotriazole such as HOBt (1-hydroxybenzotriazole) or azabenzotriazole such as HOAt ( 7-aza-1-hydroxybenzotriazole).
Verfahrenswege zur Herstellung von IntermediatenProcedures for the production of intermediates
Verfahren (BDMethod (BD
Zwischenprodukte der Formel (VH) werden z.B. nach folgendem Verfahren (H) synthetisiert:Intermediates of formula (VH) are e.g. synthesized by the following procedure (H):
,1,1
(XV)(XV)
wobeiin which
R12 und M die oben angegebenen Bedeutungen haben; Beim erfindungsgemäßen Verfahren (H) zur Herstellung der Hydrazine (VIT) werden die Amine (XVI) nach dem Fachmann bekannten Methoden, z. B. in einer Sequenz aus Diazotierung und Reduktion, in die entsprechenden Hydrazine umgewandelt (vgl. z.B. J. Med. Chem 1993, 36 (11) S. 1529-1538 und WO 2006/081034). Hydrazine der allgemeinen Formel (VE) sind darüberhinaus zum Teil kommerziell verfügbar (z.B. Ethyl-4-hydrazinylbenzolcarboxylat oder Methyl-4- hydrazinyl-2-methoxybenzolcarboxylat). Amine der Formel (XVI) sind zum Teil kommerziell verfügbar oder lassen sich nach dem Fachmann bekannten Methoden herstellen, z.B. durch Verseifung von Verbindungen der Formel (XTV) oder Reduktion von Verbindungen der Formel (XV).R 12 and M have the meanings given above; In the process (H) according to the invention for the preparation of hydrazines (VIT), the amines (XVI) are prepared by methods known to the person skilled in the art, for. B. in a sequence of diazotization and reduction, converted into the corresponding hydrazines (see, for example J. Med Chem 1993, 36 (11) pp 1529-1538 and WO 2006/081034). Moreover, hydrazines of the general formula (VE) are in part commercially available (for example ethyl-4-hydrazinylbenzenecarboxylate or methyl-4-hydrazinyl-2-methoxybenzenecarboxylate). Amines of the formula (XVI) are in part commercially available or can be prepared by methods known to those skilled in the art, for example by saponification of compounds of the formula (XTV) or reduction of compounds of the formula (XV).
Gegenstand der vorliegenden Erfidnung sind auch Verbindungen der Formel (VII-A) oder (VE-B)The present invention also provides compounds of the formula (VII-A) or (VE-B)
wobei A , 1 , A A 2 , D R3 und Q wie oben definiert sind. wherein A, 1, AA 2, D R3 and Q are as defined above.
Verfahren (J)Procedure (J)
Zwischenprodukte der Formel (X-A)/(X-B) und (XVI- A)/(XVI-B) werden z.B. nach folgendem Verfahren (J) synthetisiert:Intermediates of formula (X-A) / (X-B) and (XVI-A) / (XVI-B) are e.g. synthesized by the following method (J):
Q4 = COOR12 Q4 = COOH Q4 = COOR12 Q4 = COOH Q4 = COORi2 Q4 = COOH Q 4 = COOR 12 Q 4 = COOH Q 4 = COOR 12 Q 4 = COOH Q 4 = COOR i 2 Q 4 = COOH
wobeiin which
R , R , R , R , A und A die oben angegebenen Bedeutungen haben;R, R, R, R, A and A have the meanings given above;
Beim erfindungsgemässen Verfahren (J) zur Herstellung der Verbindungen (X-A)/(X-B)) und (XVI-A)/(XVI-B) werden Verbindungen der Formel (X-A-Q4/X-B-Q4) bzw. (XVI-A-Q4)/(XVI- B-Q4) (Q4 = Ester) nach dem Fachmann bekannten Methoden hydrolysiert (Q4 = COOH) und dann mit Hilfe eines Aktivierungsreagenzes mit einem primären oder sekundären Amin HNR8R9 in Amide der Formern (X-A-Q2)/(X-B-Q2) und (XVI-A-Q2)/(XVI-B-Q2) umgewandelt. Die Aktivierung kann über Säurechloride, gemischte Anhydride, Pentafluorphenylester oder mit Hilfe von substituierten Carbodiimiden, z. B. DCC (N, N'-Dicyclohexylcarbodiimid), DIC (Diisopro- pylcarbodiimid) oder EDC (N-Ethyl-N'-(3-dimethylaminopropyl)carbodiimid HCl), und einem Benzotriazol wie HOBt (1-Hydroxybenzotriazol) oder Azabenzotriazol wie HOAt (7-Aza-l- hydroxybenzotriazol) erfolgen.In the process (J) according to the invention for preparing the compounds (XA) / (XB)) and (XVI-A) / (XVI-B), compounds of the formula (XA-Q4 / XB-Q4) or (XVI-A) Q4) / (XVI-B-Q4) (Q 4 = ester) hydrolyzed by methods known in the art (Q 4 = COOH) and then with the aid of an activating reagent with a primary or secondary amine HNR 8 R 9 in amides of the formers (XA -Q2) / (XB-Q2) and (XVI-A-Q2) / (XVI-B-Q2). Activation may be via acid chlorides, mixed anhydrides, pentafluorophenyl esters or with the aid of substituted carbodiimides, e.g. For example, DCC (N, N'-dicyclohexylcarbodiimide), DIC (diisopropylcarbodiimide) or EDC (N-ethyl-N '- (3-dimethylaminopropyl) carbodiimide HCl), and a benzotriazole such as HOBt (1-hydroxybenzotriazole) or azabenzotriazole such as HOAt (7-aza-l-hydroxybenzotriazole) take place.
Gegenstand der vorliegenden Erfindung sind auch Verbindungen der Formeln (X-A) oder (X-B)The present invention also provides compounds of the formulas (X-A) or (X-B)
wobei A , A , R und Q wie oben definiert sind und LG für Halogen steht. Synthesevorschrift zur Herstellung von Verbindungen der Formel (I-A/B-Ql mit R1 = NH?) mittels nukleophiler Substitution wherein A, A, R and Q are as defined above and LG is halogen. Synthesis instructions for the preparation of compounds of the formula (IA / B-Ql with R 1 = NH?) By means of nucleophilic substitution
5-[5-Amino-4-(3-chlor-5-trifluormethylphenyl)-3-trifluormethylpyrazol-l-yl]-2- fluorbenzonitril5- [5-Amino-4- (3-chloro-5-trifluoromethylphenyl) -3-trifluoromethylpyrazol-1-yl] -2-fluorobenzonitrile
(I-A-Q4-009)(I-A-Q4-009)
Zu einer Lösung von 2-(3-Chlor-5-trifluormethylphenyl)-4,4,4-trifluor-3-oxobutyronitril (250 mg, 0,79 mmol) in Toluol (5 mL) wird 2-Fluor-5-hydrazinobenzonitril (120 mg, 0,79 mmol) und eine Spatelspitze p-Toluolsulfonsäure hinzugefügt. Das Reaktionsgefäß wird verschlossen und in einem CEM Discover Mikrowellenreaktor 12 min bei 170 0C gerührt. Das Lösungsmittel wird im Vakuum entfernt. Reinigung mittels Chromatographie über Kieselgel mit Cyclohexan/Ethylacetat 8/1 liefert 5-[5-Amino-4-(3-chlor-5-trifluormethylphenyl)-3-trifluormethylpyrazol-l -yl]-2-fluor- benzonitril (265 mg, 0,59 mmol, 72 %).To a solution of 2- (3-chloro-5-trifluoromethylphenyl) -4,4,4-trifluoro-3-oxobutyronitrile (250 mg, 0.79 mmol) in toluene (5 mL) becomes 2-fluoro-5-hydrazinobenzonitrile (120 mg, 0.79 mmol) and a spatula tip of p-toluenesulfonic acid added. The reaction vessel is closed and stirred in a CEM Discover microwave reactor at 170 ° C. for 12 minutes. The solvent is removed in vacuo. Purification by chromatography on silica gel with cyclohexane / ethyl acetate 8/1 affords 5- [5-amino-4- (3-chloro-5-trifluoromethylphenyl) -3-trifluoromethylpyrazol-1-yl] -2-fluoro-benzonitrile (265 mg, 0.59 mmol, 72%).
log P (HCOOH): 4,54log P (HCOOH): 4.54
1H NMR (DMSO-d6): 8,18, (dd, 1 H, J = 5,6 und 2,8 Hz), 8,01 (ddd, 1 H, J = 9,2 und 4,8 und 2,8 Hz), 7,78 (s, 1 H), 7,71 (d, 1 H, J = 9,2 Hz), 7,67 (s, 1 H), 7,59 (s, 1 H), 5,86 (s, 2 H) 1 H NMR (DMSO-d6): 8.18, (dd, 1H, J = 5.6 and 2.8 Hz), 8.01 (ddd, 1H, J = 9.2 and 4.8 and 2.8 Hz), 7.78 (s, 1H), 7.71 (d, 1H, J = 9.2 Hz), 7.67 (s, 1H), 7.59 (s, 1 H), 5.86 (s, 2H)
5-[5-Amino-4-(3-chlor-5-trifluormethylphenyl)-3-trifluormethylpyrazol-l-yl]-2- [l,2,4]triazol-l-ylbenzonitril (I-A-Ql-001) 5- [5-Amino-4- (3-chloro-5-trifluoromethylphenyl) -3-trifluoromethylpyrazol-1-yl] -2- [l, 2,4] triazol-1-ylbenzonitrile (IA-Ql-001)
Zu einer Lösung von 5-[5-Amino-4-(3-chlor-5-trifluormethylphenyl)-3-trifluormethylpyrazol-l-yl]- 2-fluorbenzonitril (100 mg, 0,22 mmol) in DMF (2 mL) werden 1 ,2,4-Triazol (18 mg, 0,27 mmol) und Kaliumcarbonat (37 mg, 0,27 mmol) hinzugefügt. Das Reaktionsgemisch wird 15 min bei 90 0C gerührt, auf Raumtemperatur abgekühlt, auf Wasser (5 mL) gegossen und mit Ethylacetat (5 mL) extrahiert. Die organische Phase wird mit Wasser (5 mL) gewaschen, über Natriumsulfat getrocknet und einrotiert. Reinigung mittels Chromatographie über Kieselgel mit Cyclohexan/Ethylacetat 2/1 bis 1/1 liefert 5-[5-Amino-4-(3-chlor-5-trifluormethylphenyl)-3- trifluormethylpyrazol-l-yl]-2-[l,2,4]triazol-l-ylbenzonitril (50 mg, 0,10 mmol, 45 %).To a solution of 5- [5-amino-4- (3-chloro-5-trifluoromethylphenyl) -3-trifluoromethylpyrazol-1-yl] -2-fluorobenzonitrile (100 mg, 0.22 mmol) in DMF (2 mL). Add 1, 2,4-triazole (18 mg, 0.27 mmol) and potassium carbonate (37 mg, 0.27 mmol). The reaction mixture is stirred for 15 min at 90 0 C, cooled to room temperature, poured onto water (5 mL) and extracted with ethyl acetate (5 mL). The organic phase is washed with water (5 mL), dried over sodium sulfate and concentrated by rotary evaporation. Purification by chromatography on silica gel with cyclohexane / ethyl acetate 2/1 to 1/1 gives 5- [5-amino-4- (3-chloro-5-trifluoromethylphenyl) -3-trifluoromethylpyrazol-1-yl] -2- [l, 2,4] triazol-1-ylbenzonitrile (50 mg, 0.10 mmol, 45%).
log P(HCOOH): 3,92log P (HCOOH): 3.92
1H NMR (DMSO-d6): 9,19 (s, 1 H), 8,36 (s, 1 H), 8,33 (d, 1 H, J = 2,4 Hz), 8,15 (dd, 1 H, J = 8,8 und 2,4 Hz), 8,05 (d, I H1 J = 8,8 Hz), 7,80 (s, 1 H), 7,69 (s, 1 H), 7,61 (s, 1 H), 5,98 (s, 2 H) 1 H NMR (DMSO-d6): 9.19 (s, 1H), 8.36 (s, 1H), 8.33 (d, 1H, J = 2.4 Hz), 8.15 ( dd, 1 H, J = 8.8 and 2.4 Hz), 8.05 (d, IH 1 J = 8.8 Hz), 7.80 (s, 1 H), 7.69 (s, 1 H), 7.61 (s, 1H), 5.98 (s, 2H)
5- [5-Amino-4-(3-chlor-5-trifluormethyIphenyl)-3-trifluormethylpyr azol- l-yl] -2-(5-oxo-4,5- dihydro[l,2,4]triazol-l-yl)benzonitril (I-A-Ql-002)5- [5-amino-4- (3-chloro-5-trifluoromethylphenyl) -3-trifluoromethylpyrazol-1-yl] -2- (5-oxo-4,5-dihydro [1,2,4] triazole) l-yl) benzonitrile (IA-Ql-002)
Zu einer Lösung von 5-[5-Amino-4-(3-chlor-5-trifluormethylphenyl)-3-trifluormethylpyrazol-l-yl]- 2-fluorbenzonitril (50 mg, 0,11 mmol) in DMF (2 mL) werden 2,4-Dihydro[l,2,4]triazol-3-on (11 mg, 0,13 mmol) und Kaliumcarbonat (18 mg, 0,13 mmol) hinzugefügt. Das Reaktionsgemisch wird 15 min bei 80 0C gerührt, auf Raumtemperatur abgekühlt, auf Wasser (5 mL) gegossen und mit Ethylacetat (5 mL) extrahiert. Die organische Phase wird mit Wasser (5 mL) gewaschen, über Natriumsulfat getrocknet und einrotiert. Reinigung mittels Chromatographie über Kieselgel mit Cyclohexan/Ethylacetat 1/2 bis 1/3 liefert 5-[5-Airdno-4-(3-cMor-5-trifluormethylphenyl)-3- trifluormethylpyrazol-l-yl]-2-(5-oxo-4,5-dihydro[l,2,4]triazol-l-yl)benzonitril (8 mg, 0,016 mmol, 12 %).To a solution of 5- [5-amino-4- (3-chloro-5-trifluoromethylphenyl) -3-trifluoromethylpyrazol-1-yl] -2-fluorobenzonitrile (50 mg, 0.11 mmol) in DMF (2 mL). For example, 2,4-dihydro [l, 2,4] triazol-3-one (11 mg, 0.13 mmol) and potassium carbonate (18 mg, 0.13 mmol) are added. The reaction mixture is stirred for 15 min at 80 0 C, cooled to room temperature, poured onto water (5 mL) and extracted with ethyl acetate (5 mL). The organic phase is washed with water (5 mL), dried over sodium sulfate and concentrated by rotary evaporation. Purification by chromatography on silica gel with Cyclohexane / ethyl acetate 1/2 to 1/3 provides 5- [5-aminomono-4- (3-c-Mor-5-trifluoromethylphenyl) -3-trifluoromethylpyrazol-1-yl] -2- (5-oxo-4,5- dihydro [1,2,4] triazol-1-yl) benzonitrile (8 mg, 0.016 mmol, 12%).
1Og P (HCOOH): 3,451Og P (HCOOH): 3.45
1H NMR (DMSO-d6): 8,28 (d, 1 H, J = 2,3 Hz), 8,24 (d, 1 H, J = 1,2 Hz), 8,12 (dd, 1 H, J = 8,8 und 2,4 Hz), 7,87 (d, 1 H, J = 8,8 Hz), 7,79 (s, 1 H), 7,69 (s, 1 H), 7,60 (s, 1 H), 5,96 (s, 2 H) 1 H NMR (DMSO-d6): 8.28 (d, 1 H, J = 2.3 Hz), 8.24 (d, 1 H, J = 1.2 Hz), 8.12 (dd, 1 H, J = 8.8 and 2.4 Hz), 7.87 (d, 1H, J = 8.8 Hz), 7.79 (s, 1H), 7.69 (s, 1H) , 7.60 (s, 1H), 5.96 (s, 2H)
Synthesevorschrift zur Herstellung von Verbindungen der Formel (I-A/B-Ol mit R1 = NH?) mittels HydrazinenSynthesis instructions for the preparation of compounds of the formula (IA / B-Ol with R 1 = NH?) By means of hydrazines
5-Amino-2-[l,2,4]triazol-l-yl-benzonitril5-Amino-2- [l, 2,4] triazol-l-yl-benzonitrile
[l,2,4]Triazol (10,1 g, 73,5 mmol) wird in NMP (50 mL) vorgelegt und mit Kaliumcarbonat (30,5 g, 220 mmol) versetzt. Nachdem 10 min bei Raumtemperatur gerührt wurde, gibt man 5-Amino-2- fluorbenzonitril (10,0 g, 73,5 mmol) hinzu und rührt 5h bei 170 0C nach. Das Reaktionsgemisch wird abgekühlt und in Wasser (800 mL) gegossen. Absaugen des Niederschlages und Nachwaschen mit Wasser liefert 5-Amino-2-[l,2,4]triazol-l-yl-benzonitril (7,50 g, 40,5 mmol, 53 %), das ohne weitere Reinigung im nächsten Schritt eingesetzt wird.[l, 2,4] Triazole (10.1 g, 73.5 mmol) is initially charged in NMP (50 mL) and potassium carbonate (30.5 g, 220 mmol) is added. After stirring for 10 min at room temperature, 5-amino-2-fluorobenzonitrile (10.0 g, 73.5 mmol) are added and stirred for 5 h at 170 0 C after. The reaction mixture is cooled and poured into water (800 mL). Suction of the precipitate and washing with water yields 5-amino-2- [l, 2,4] triazol-1-yl-benzonitrile (7.50 g, 40.5 mmol, 53%), which without further purification in the next step is used.
log P (HCOOH): 1,01log P (HCOOH): 1.01
IHNMR (DMSO-d6): 8,82 (s, 1 H), 8,16 (s, 1 H), 7,37 (d, 1 H, J = 8,4 Hz), 7,03 (d, 1 H, J = 2,8 Hz), 6,97 (dd, 1 H, J = 8,8 und 2,4 Hz), 5,85 (s, 2 H)IHNMR (DMSO-d6): 8.82 (s, 1H), 8.16 (s, 1H), 7.37 (d, 1H, J = 8.4Hz), 7.03 (d, 1 H, J = 2.8 Hz), 6.97 (dd, 1 H, J = 8.8 and 2.4 Hz), 5.85 (s, 2 H)
5-Hydrazino-2-[l,2,4]triazol-l-yl-benzonitril (VII-A-103) 5-Amino-2-[l,2,4]triazol-l-yl-benzonitril (5,0 g, 27,0 mmol) wird in Wasser (25 mL) vorgelegt, mit konzentrierter Salzsäure (50 mL) versetzt und mit mittlerer Rührgeschwindigkeit bei Raumtemperatur gerührt. Das Reaktionsgemisch wird auf 0 0C abgekühlt und mit einer Lösung von Natriumnitrit (3,73 g, 54,0 mmol) in Wasser (25 mL) versetzt. Es wird 1 h bei 0 0C nachgerührt, bevor eine Lösung von Zinn(II)chloriddihydrat (18,3 g, 81,0 mmol) in konzentrierter Salzsäure (100 mL) hinzugetropft wird. Nach vollständiger Zugabe wird 30 min bei 0 0C gerührt, auf Raumtemperatur erwärmt und weitere 1,5 h gerührt. Das Reaktionsgemisch wird unter Eiskühlung mit konzentrierter Natronlauge alkalisch gestellt, mit Ethylacetat versetzt und über Celite abgesaugt. Die organische Phase wird über Natriumsulfat getrocknet und einrotiert. Kristallisation des Rückstandes aus Methanol liefert 5-Hydrazino-2-[l,2,4]triazol-l-yl-benzonitril (1,2 g, 6,0 mmol, 22 %).5-Hydrazino-2- [l, 2,4] triazol-1-yl-benzonitrile (VII-A-103) 5-Amino-2- [l, 2,4] triazol-l-yl-benzonitrile (5.0 g, 27.0 mmol) is initially charged in water (25 mL), treated with concentrated hydrochloric acid (50 mL) and washed with medium stirring speed stirred at room temperature. The reaction mixture is cooled to 0 ° C. and admixed with a solution of sodium nitrite (3.73 g, 54.0 mmol) in water (25 mL). The mixture is stirred for 1 h at 0 0 C before a solution of tin (II) chloride dihydrate (18.3 g, 81.0 mmol) is added dropwise in concentrated hydrochloric acid (100 mL). After complete addition, the mixture is stirred for 30 min at 0 0 C, warmed to room temperature and stirred for a further 1.5 h. The reaction mixture is made alkaline with concentrated sodium hydroxide solution under ice-cooling, treated with ethyl acetate and filtered with suction through Celite. The organic phase is dried over sodium sulfate and concentrated by rotary evaporation. Crystallization of the residue from methanol affords 5-hydrazino-2- [l, 2,4] triazol-1-yl-benzonitrile (1.2 g, 6.0 mmol, 22%).
1H NMR (DMSO-d6): 8,84 (s, 1 H), 8,17 (s, 1 H), 7,46 (s, 1 H), 7,43 (d, 1 H, J = 8,8 Hz), 7,23 (d, 1 H, J = 2,4 Hz), 7,13 (dd, 1 H, J = 9,2 und 2,8 Hz), 4,20 (, 2 H) 1 H NMR (DMSO-d6): 8.84 (s, 1H), 8.17 (s, 1H), 7.46 (s, 1H), 7.43 (d, 1H, J = 8.8 Hz), 7.23 (d, 1 H, J = 2.4 Hz), 7.13 (dd, 1 H, J = 9.2 and 2.8 Hz), 4.20 (, 2 H)
Synthesevorschrift zur Herstellung von Verbindungen der Formel (I-A/B-02 mit R1 = NH?) mittels HydrazinenSynthesis instructions for the preparation of compounds of the formula (IA / B-02 with R 1 = NH?) By means of hydrazines
4-Hydrazino-2-methylbenzoesäuremethylester (VTI-A-008)4-hydrazino-2-methylbenzoic acid methyl ester (VTI-A-008)
4-Acetamido-2-methylbenzoesäure (46 g, 238 mmol) wird in Methanol (460 mL) vorgelegt und mit konzentrierter Schwefelsäure (63 g, 643 mmol) versetzt. Das Reaktionsgemisch wird 3 h zum Refluxieren erhitzt, abgekühlt, vorsichtig auf Eiswasser gegossen und mit 5N Natronlauge alkalisch gestellt. Extraktion mit Ethylacetat, Trocknen der organischen Phase über Natriumsulfat und Entfernen des Lösungsmittels im Vakuum liefert 4-Amino-2-methylbenzoesäureethylester (38,3 g, 232 mmol, 94 %), der ohne weitere Reinigung im nächsten Schritt eingesetzt wird.4-Acetamido-2-methylbenzoic acid (46 g, 238 mmol) is initially charged in methanol (460 mL) and treated with concentrated sulfuric acid (63 g, 643 mmol). The reaction mixture is heated for 3 h to reflux, cooled, poured cautiously on ice water and made alkaline with 5N sodium hydroxide solution. Extraction with ethyl acetate, drying of the organic phase over sodium sulfate and removal of the solvent in vacuo provides ethyl 4-amino-2-methylbenzoate (38.3 g, 232 mmol, 94%), which is used in the next step without further purification.
4-Amino-2-methylbenzoesäuremethylester (5,0 g, 30 mmol) wird in Wasser (25 mL) vorgelegt, mit konzentrierter Salzsäure (50 mL) versetzt und 30 min bei Raumtemperatur gerührt. Das Reaktionsgemisch wird auf 0 0C abgekühlt und eine Lösung von Natriumnitrit (2,72 g, 39,3 mmol) in Wasser (25 mL) wird langsam zugetropft. Man rührt eine Stunde bei 0 0C nach und tropft dann bei 0 0C Zinn(π)chlorid-Dihydrat (20,5 g, 90,8 mmol) in konzentrierter Salzsäure (100 mL) hinzu. Es wird zunächst 30 min bei 0 0C und dann 1,5 h bei Raumtemperatur nachgerührt. Das Reaktionsgemisch wird mit Wasser (50 mL) verdünnt, der Niederschlag wird abfiltriert und mit wenig Wasser gewaschen. Das Filtrat wird in Eiswasser gegossen, mit halbkonzentrierter Natronlauge auf pH 8-9 eingestellt und zweimal mit Dichloπnethan extrahiert. Die organischen Phasen werden vereint und über Natriumsulfat getrocknet. Entfernen des Lösungsmittels im Vakuum liefert 4-Hydrazino-2-methylbenzoesäuremethylester (4,1 g, 22,8 mmol, 70 %), der ohne weitere Reingung im nächsten Schritt eingesetzt wird.Methyl 4-amino-2-methylbenzoate (5.0 g, 30 mmol) is initially charged in water (25 mL), combined with concentrated hydrochloric acid (50 mL) and stirred at room temperature for 30 min. The reaction mixture is cooled to 0 ° C. and a solution of sodium nitrite (2.72 g, 39.3 mmol) in water (25 mL) is slowly added dropwise. The mixture is stirred for one hour at 0 0 C and then added dropwise at 0 0 C tin (π) chloride dihydrate (20.5 g, 90.8 mmol) in concentrated hydrochloric acid (100 mL) was added. It is first stirred for 30 min at 0 0 C and then for 1.5 h at room temperature. The reaction mixture is diluted with water (50 mL), the precipitate is filtered off and washed with a little water. The filtrate is poured into ice-water, adjusted to pH 8-9 with half-concentrated sodium hydroxide solution and extracted twice with dichloromethane. The organic phases are combined and dried over sodium sulfate. Removal of the solvent in vacuo yields 4-hydrazino-2-methylbenzoic acid methyl ester (4.1 g, 22.8 mmol, 70%), which is used in the next step without further purification.
log P (HCOOH): 0,40log P (HCOOH): 0.40
1H NMR (DMSO-d6): 7,67 (d, 1 H, J = 8,8 Hz), 7,19 (s, 1 H), 6,61-6,58 (m, 2 H), 4,03 (s, 2 H), 3,71 (s, 3 H), 2,44 (s, 3 H) 1 H NMR (DMSO-d6): 7.67 (d, 1 H, J = 8.8 Hz), 7.19 (s, 1 H), 6.61-6.58 (m, 2 H), 4.03 (s, 2H), 3.71 (s, 3H), 2.44 (s, 3H)
4-[5-Amino-4-(3,5-dichlorphenyl)-3-trifluormethylpyrazol-l-yl]-2- methylbenzoesäuremethylesterMethyl 4- [5-amino-4- (3,5-dichlorophenyl) -3-trifluoromethylpyrazol-1-yl] -2-methylbenzoate
(I-A-Q4-011)(I-A-Q4-011)
Eine Lösung von 3-Chlor-2-(3,5-dichloφhenyl)-4,4,4-trifluorbut-2-ennitril (100 mg, 0,24 mmol) in Ethanol (3 mL) wird mit 4-Hydrazino-2-methylbenzoesäuremethylester (43 mg, 0,24 mmol) und Triethylamin (24 mg, 0,24 mmol) versetzt und über Nacht bei 80 0C gerührt. Das Reaktionsgemisch wird auf Raumtemperatur abgekühlt, auf Wasser (5 mL) gegossen und mit Ethylacetat (5 mL) extrahiert. Die organische Phase wird mit Wasser (5 mL) gewaschen, über Natriumsulfat getrocknet und einrotiert. Reinigung mittels Chromatographie über Kieselgel mit Cyclohexan/Ethylacetat 6/1 liefert 4-[5-Amino-4-(3,5-dichlorphenyl)-3-trifluormethylpyrazol-l- yl]-2-methylbenzoesäuremethylester (55 mg, 0,12 mmol, 52 %).A solution of 3-chloro-2- (3,5-dichloro-phenyl) -4,4,4-trifluorobut-2-enenitrile (100 mg, 0.24 mmol) in ethanol (3 mL) is treated with 4-hydrazino-2 Methyl methyl benzoate (43 mg, 0.24 mmol) and triethylamine (24 mg, 0.24 mmol) and stirred at 80 0 C overnight. Cool the reaction mixture to room temperature, pour onto water (5 mL) and extract with ethyl acetate (5 mL). The organic phase is washed with water (5 mL), dried over sodium sulfate and concentrated by rotary evaporation. Purification by chromatography on silica gel with cyclohexane / ethyl acetate 6/1 affords 4- [5-amino-4- (3,5-dichlorophenyl) -3-trifluoromethylpyrazol-1-yl] -2-methylbenzoic acid methyl ester (55 mg, 0.12 mmol , 52%).
log P (HCOOH): 5,08log P (HCOOH): 5.08
1H NMR (DMSO-d6): 7,96 (d, 1 H, J = 8,4 Hz), 7,59-7,55 (m, 2 H), 7,53 (t, 1 H, J = 2,0 Hz), 7,34 (d, 2 H, J = 2,0 Hz), 5,70 (s, 2 H), 3,87 (s, 3 H), 2,60 (s, 3 H) ^[S-Amino^-CSjS-dichlorpheny^-S-trifluormethylpyrazol-l-yll-Z-methylbenzoesäure (I-A- Q4-010) 1 H NMR (DMSO-d6): 7.96 (d, 1H, J = 8.4Hz), 7.59-7.55 (m, 2H), 7.53 (t, 1H, J = 2.0 Hz), 7.34 (d, 2H, J = 2.0 Hz), 5.70 (s, 2H), 3.87 (s, 3H), 2.60 (s, 3H) ^ [S-Amino] -CSjS-dichlorophenyl] -S-trifluoromethylpyrazol-1-yl-Z-methylbenzoic acid (IA-Q4-010)
4-[5-Amino-4-(3,5-dichlorphenyl)-3-trifluormethylpyrazol-l-yl]-2-methylbenzoesäuremethylester (300 mg, 0,51 mmol) wird in Wasser (10 mL) und Ethanol (10 mL) vorgelegt und mit Natriumhydroxid (200 mg, 5,1 mmol) versetzt. Das Reaktionsgemisch wird zwei Tage bei Raumtemperatur gerührt, in Wasser (50 mL) gegossen, mit 2N Salzsäure sauer gestellt (pH3-4), zweimal mit Ethylacetat extrahiert und über Natriumsulfat getrocknet. Einrotieren des Lösungsmittels liefert 4-[5-Amino-4-(3,5-dichlθφhenyl)-3-trifluormethylpyrazol-l-yl]-2-methyl- benzoesäure in quantitativer Ausbeute.Methyl 4- [5-amino-4- (3,5-dichlorophenyl) -3-trifluoromethylpyrazol-1-yl] -2-methylbenzoate (300 mg, 0.51 mmol) is dissolved in water (10 mL) and ethanol (10 mL ) and treated with sodium hydroxide (200 mg, 5.1 mmol). The reaction mixture is stirred for two days at room temperature, poured into water (50 mL), acidified with 2N hydrochloric acid (pH 3-4), extracted twice with ethyl acetate and dried over sodium sulfate. Centrifugation of the solvent affords 4- [5-amino-4- (3,5-dichloro-phenyl) -3-trifluoromethyl-pyrazol-1-yl] -2-methyl-benzoic acid in quantitative yield.
log P (HCOOH): 4,04log P (HCOOH): 4.04
1H NMR (DMSO-d6): 7,97 (d, 1 H, J = 8,4 Hz), 7,55-7,52 (m, 3 H), 7,34 (d, 2 H, J = 2,0 Hz), 5,68 (s, 2 H), 2,61 (s, 3 H) 1 H NMR (DMSO-d6): 7.97 (d, 1H, J = 8.4Hz), 7.55-7.52 (m, 3H), 7.34 (d, 2H, J = 2.0 Hz), 5.68 (s, 2H), 2.61 (s, 3H)
4-[5-Amino-4-(3,5-dichlorphenyl)-3-trifluormethylpyrazol-l-yl]-2-methyl-N-pyridin-2- ylmethylbenzamid (I-A-Q2-012)4- [5-Amino-4- (3,5-dichlorophenyl) -3-trifluoromethylpyrazol-1-yl] -2-methyl-N-pyridin-2-ylmethylbenzamide (I-A-Q2-012)
Eine Lösung von 2-Aminomethylpyridin (25 mg, 0,23 mmol) in DMF (1 mL) wird mit einer Lösung aus 4-[5-Amino-4-(3,5-dichlθφhenyl)-3-trifluormethylpyrazol-l-yl]-2-methylbenzoesäureA solution of 2-aminomethylpyridine (25 mg, 0.23 mmol) in DMF (1 mL) is treated with a solution of 4- [5-amino-4- (3,5-dichloro-phenyl) -3-trifluoromethyl-pyrazol-1-yl ] -2-methylbenzoic
(100 mg, 0,23 mmol), l-Ethyl-3-[3-dimethylaminopropyl]carbodiimid Hydrochlorid (58 mg, 0,30 mmol), 1-Hydroxy-lH-benzotriazol (41 mg, 0,30 mmol) und Triethylamin (28 mg, 0,28 mmol) in DMF (4 mL) versetzt und über Nacht bei Raumtemperatur gerührt. Das Reaktionsgemisch wird mit Wasser (5 mL) versetzt, zweimal mit Ethylacetat (je 5 mL) extrahiert, mit NaHCO3-LSg (5 mL) und NaCl-Lsg (5 mL) gewaschen, über Natriumsulfat getrocknet und einrotiert. Reinigung durch Säulenchromatographie über Kieselgel mit Cyclohexan/Ethylacetat 1/2 bis 1/3 liefert 4-[5-Amino- 4-(3,5-dichlorphenyl)-3-trifluormethylpyrazol-l-yl]-2-methyl-N-pyridin-2-ylmethylbenzamid (75 mg, 0,14 mmol, 61%).(100 mg, 0.23 mmol), 1-ethyl-3- [3-dimethylaminopropyl] carbodiimide hydrochloride (58 mg, 0.30 mmol), 1-hydroxy-1H-benzotriazole (41 mg, 0.30 mmol) and triethylamine (28 mg, 0.28 mmol) in DMF (4 mL) and stirred overnight at room temperature. The reaction mixture is combined with water (5 mL), extracted twice with ethyl acetate (5 mL each time), washed with NaHCO 3 -LSg (5 mL) and NaCl solution (5 mL), dried over sodium sulfate and concentrated by rotary evaporation. Purification by column chromatography on silica gel with cyclohexane / ethyl acetate 1/2 to 1/3 affords 4- [5-amino-4- (3,5-dichlorophenyl) -3-trifluoromethylpyrazol-1-yl] -2-methyl-N-pyridine -2-ylmethylbenzamide (75 mg, 0.14 mmol, 61%).
log P (HCOOH): 3,35log P (HCOOH): 3.35
1H NMR (DMSO-d6): 8,71 (t, 1 H, J = 5,6 Hz), 8,52 (d, 1 H, J = 4,0 Hz), 7,78 (td, 1 H, J = 8,0 und 2,0 Hz), 7,60 (d, 1 H, J = 8,0 Hz), 7,53 (t, 1 H, J = 2,0 Hz), 7,50-7,47 (m, 2 H), 7,40 (d, 1 H, J = 7,6 Hz), 7,34 (d, 2 H, J = 2,0 Hz), 7,26 (dd, 1 H, J = 7,6 und 5,6 Hz), 5,59 (s, 2 H), 4,58 (d, 2 H, J = 6,0 Hz), 2,46 (s, 3 H) 1 H NMR (DMSO-d6): 8.71 (t, 1 H, J = 5.6 Hz), 8.52 (d, 1 H, J = 4.0 Hz), 7.78 (td, 1 H, J = 8.0 and 2.0 Hz), 7.60 (d, 1 H, J = 8.0 Hz), 7.53 (t, 1 H, J = 2.0 Hz), 7, 50-7.47 (m, 2H), 7.40 (d, 1H, J = 7.6Hz), 7.34 (d, 2H, J = 2.0Hz), 7.26 ( dd, 1 H, J = 7.6 and 5.6 Hz), 5.59 (s, 2H), 4.58 (d, 2H, J = 6.0 Hz), 2.46 (s, 3H)
Svnthesevorschrift zur Herstellung von Verbinduneen der Formel (I-A/B-O2 mit R1 = NH?) mittels N-Arylierung von PyrazolenSynthesis for the preparation of Verbinduneen of formula (IA / B-O2 with R 1 = NH?) By N-arylation of pyrazoles
4-[5-Amino-4-(3,4-dichlorphenyl)-3-(trifluormethyl)-lH-pyrazol-l-yl]-2-methylbenzoesäure- ethylester (I-A-Q4-013)Ethyl 4- [5-amino-4- (3,4-dichlorophenyl) -3- (trifluoromethyl) -1H-pyrazol-1-yl] -2-methylbenzoate (I-A-Q4-013)
4-(3,4-Dichlorphenyl)-3-(trifluormethyl)-lH-pyrazol-5-amin (70 %ig) (1,94 g, 6,55 mmol) werden in Toluol (39 mL) unter Argon vorgelegt, mit Ethyl-4-iod-2-methylbenzoat (90 %ig) (1,90 g), Kaliumcarbonat (3,10 g), Kupfer(I)iodid (62 mg) und trans-Dimethylamino-cyclohexan (186 mg) versetzt und 16 Stunden bei 1100C unter Argon gerührt.4- (3,4-dichlorophenyl) -3- (trifluoromethyl) -1H-pyrazole-5-amine (70%) (1.94 g, 6.55 mmol) is placed in toluene (39 mL) under argon, with ethyl 4-iodo-2-methylbenzoate (90%) (1.90g), potassium carbonate (3.10g), copper (I) iodide (62mg) and trans -dimethylamino-cyclohexane (186mg) and stirred at 110 0 C under argon for 16 hours.
Das Reaktionsgemisch wird einrotiert, in Wasser (20 mL) und Ethylacetat (39 mL) aufgenommen, mit konz. HCl auf pH= 1 gestellt, die org. Phase abgetrennt, die wässrige Phase nochmals mit Ethylacetat (30 mL) extrahiert, die vereinigten organischen Phasen über Natriumsulfat getrocknet und einrotiert. Nach Extraktion von organischen Verunreinigungen mit Hexan verbleibt ein brauner Feststoff. Reinigung mittels HPLC liefert 4-[5-Amino-4-(3,4-dichlorphenyl)-3- (trifluormethyl)-lH-pyrazol-l-yl]-2-methylbenzoesäureethylester (630 mg, 24 %)) log P (HCOOH): 5,24The reaction mixture is concentrated by rotary evaporation, taken up in water (20 ml) and ethyl acetate (39 ml), treated with conc. HCl adjusted to pH = 1, the org. Phase separated, the aqueous phase extracted again with ethyl acetate (30 mL), the combined organic phases dried over sodium sulfate and concentrated by rotary evaporation. After extraction of organic impurities with hexane, a brown solid remains. Purification by HPLC affords ethyl 4- [5-amino-4- (3,4-dichlorophenyl) -3- (trifluoromethyl) -1H-pyrazol-1-yl] -2-methylbenzoate (630 mg, 24%)). log P (HCOOH): 5.24
1H NMR (DMSO-d6): 1.35 (t, 3 H); 2.56 (s, 3 H); 4.34 (q, 2 H); 5.62 (br. s, 2 H); 7.32 (dd, 1 H); 7.54-7.59 (m, 3 H); 7.67 (d, 1 H); 7.95 (d, 1 H) 1 H NMR (DMSO-d6): 1.35 (t, 3H); 2.56 (s, 3H); 4.34 (q, 2H); 5.62 (brs s, 2 H); 7.32 (dd, 1H); 7.54-7.59 (m, 3H); 7.67 (d, 1H); 7.95 (d, 1H)
4-[5-Amino-4-(3,4-dichlorphenyl)-3-(trifluormethyl)-lH-pyrazol-l-yl]-2-methylbenzoesäure4- [5-Amino-4- (3,4-dichlorophenyl) -3- (trifluoromethyl) -lH-pyrazol-l-yl] -2-methylbenzoic acid
(I-A-Q4-012)(I-A-Q4-012)
4-[5-Amino-4-(3,4-dichloφhenyl)-3-(trifluormethyl)-lH-pyrazol-l-yl]-2- methylbenzoesäureethylester (600 mg) werden in Isopropanol (9 mL) und IN -Natronlauge (6 mL) zwei Tage bei 20 0C gerührt.Ethyl 4- [5-amino-4- (3,4-dichloro-phenyl) -3- (trifluoromethyl) -1H-pyrazol-1-yl] -2-methylbenzoate (600 mg) is dissolved in isopropanol (9 mL) and IN-sodium hydroxide (6 mL) for two days at 20 0 C stirred.
Das Isopropanol wird im Vakuum abrotiert, die wässrige Phase mit konzentrierter Salzsäure auf pH = 1 gestellt. Der ausgefallene Niederschlag wird abgesaugt, mit Wasser gewaschen und getrocknet.The isopropanol is evaporated in vacuo, the aqueous phase with concentrated hydrochloric acid to pH = 1. The precipitate is filtered off with suction, washed with water and dried.
Man erhält 4-[5 - Amino-4-(3 ,4-dichlorphenyl)-3 -(trifluormethyl)- 1 H-pyrazol- 1 -yl] -2-methylbenzol- carbonsäure (495 mg, 86 %) als gelblichen Feststoff, Gehalt HPLC: 98.8 %.4- [5-Amino-4- (3,4-dichlorophenyl) -3- (trifluoromethyl) -1H-pyrazol-1-yl] -2-methylbenzene-carboxylic acid (495 mg, 86%) as a yellowish solid , Content HPLC: 98.8%.
log P (HCOOH): 3,92log P (HCOOH): 3.92
1H NMR (DMSO-d6): 2.61 (s, 3 H); 5.61 (br. S, 2 H); 7.32 (dd, 1 H); 7.52-7.56 (m, 3 H); 7.67 (d, 1 H); 7.96 (d, 1 H) 1 H NMR (DMSO-d6): 2.61 (s, 3H); 5.61 (br. S, 2 H); 7.32 (dd, 1H); 7.52-7.56 (m, 3H); 7.67 (d, 1H); 7.96 (d, 1H)
Svnthesevorschrift zur Herstellung von Verbindungen der Formel (I-A/B-02 mit R1 = DSynthesis for the preparation of compounds of formula (IA / B-02 with R 1 = D
4-[4-(3,5-Dichlorphenyl)-5-iod-3-trifluormethylpyrazol-l-yl]-2-methyl-N-pyridin-2-ylmethyl- benzamid (I-A-Q2-025) 4- [4- (3,5-dichlorophenyl) -5-iodo-3-trifluoromethylpyrazol-1-yl] -2-methyl-N-pyridin-2-ylmethylbenzamide (IA-Q2-025)
Eine Lösung von 4-[5-Amino-4-(3,5-dichlθφhenyl)-3-trifluormethylpyrazol-l-yl]-2-methyl-N- pyridin-2-ylmethylbenzamid (80 mg, 0,15 mmol) in Chloroform (1 mL) wird mit Iodoform (121 mg, 0,31 mmol) versetzt. Zu dem Reaktionsgemisch wird langsam tert-Butylnitrit (35 mg, 0,34 mmol) hinzugetropft und es wird über Nacht bei Raumtemperatur rühren gelassen. Reinigung mittels Chromatographie über Kieselgel mit Cyclohexan/Ethylacetat 1/1 liefert 4-[4-(3,5-A solution of 4- [5-amino-4- (3,5-dichloro-phenyl) -3-trifluoromethylpyrazol-1-yl] -2-methyl-N-pyridin-2-ylmethylbenzamide (80 mg, 0.15 mmol) in Chloroform (1 mL) is added with iodoform (121 mg, 0.31 mmol). To the reaction mixture is slowly added dropwise tert-butyl nitrite (35 mg, 0.34 mmol) and allowed to stir overnight at room temperature. Purification by chromatography on silica gel with cyclohexane / ethyl acetate 1/1 gives 4- [4- (3.5-
Dichloφhenyl)-5-iod-3-trifluormethylpyrazol-l-yl]-2-methyl-N-pyridin-2-ylmethylbenzamid (45 mg, 0,071 mmol, 46%). Leichte Verunreinigungen an 4-[4-(3,5-Dichloφhenyl)-3-trifluor- methylpyrazol-l-yl]-2-methyl-N-pyridin-2-ylmethylbenzamid können mittels HPLC entfernt werden.Dichloro-phenyl) -5-iodo-3-trifluoromethylpyrazol-1-yl] -2-methyl-N-pyridin-2-ylmethylbenzamide (45mg, 0.071mmol, 46%). Slight impurities of 4- [4- (3,5-dichloro-phenyl) -3-trifluoromethyl-pyrazol-1-yl] -2-methyl-N-pyridin-2-ylmethylbenzamide can be removed by HPLC.
log P (HCOOH): 4,29log P (HCOOH): 4.29
1H NMR (DMSO-d6): 8,85 (t, 1 H, J = 5,8 Hz), 8,52 (d, 1 H, J = 4,0 Hz), 7,78 (td, 1 H, J = 8,0 und 2,0 Hz), 7,71 (t, 1 H, J = 2,0 Hz), 7,64 (d, (1 H, J = 8,8 Hz), 7,53-7,50 (m, 2 H), 7,45 (d, 2 H, J = 1,6 Hz), 7,42 (d, 1 H, J = 8,0 Hz), 7,27 (dd, I H1 J = 6,4 und 5,2 Hz), 4,58 (d, 2 H, J = 6,0 Hz), Me unter DMSO-d6 Signal 1 H NMR (DMSO-d6): 8.85 (t, 1 H, J = 5.8 Hz), 8.52 (d, 1 H, J = 4.0 Hz), 7.78 (td, 1 H, J = 8.0 and 2.0 Hz), 7.71 (t, 1 H, J = 2.0 Hz), 7.64 (d, (1 H, J = 8.8 Hz), 7 , 53-7.50 (m, 2H), 7.45 (d, 2H, J = 1.6 Hz), 7.42 (d, 1H, J = 8.0 Hz), 7.27 (dd, IH 1 J = 6.4 and 5.2 Hz), 4.58 (d, 2 H, J = 6.0 Hz), Me under DMSO-d6 signal
Svnthesevorschrift zur Herstellung von Verbindungen der Formel (I-A/B-O2 mit R1 = Br)Synthesis instructions for the preparation of compounds of the formula (IA / B-O 2 where R 1 = Br)
4-[5-Brom-4-(3,5-dichlorphenyl)-3-trifluormethylpyrazol-l-yl]-2-methyl-N-(2,2,2-trifluor-l- methylethyl)benzamid (I-A-Q2-024)4- [5-Bromo-4- (3,5-dichlorophenyl) -3-trifluoromethylpyrazol-1-yl] -2-methyl-N- (2,2,2-trifluoro-1-methylethyl) -benzamide (IA-Q2 -024)
Zu einer Lösung von 4-[5-Amino-4-(3,5-dichlθφhenyl)-3-trifluormethylpyrazol-l-yl]-2-methyl-N- (2,2,2-trifluor-l-methylethyl)benzamid (200 mg, 0,38 mmol) in Bromoform (0,5 mL) wird langsam tert-Butylnitrit (86 mg, 0,84 mmol) hinzugetropft und es wird über Nacht bei Raumtemperatur rühren gelassen. Reinigung mittels Chromatographie über Kieselgel mit Cyclohexan/Ethylacetat 1/1 liefert 4-[5-Brom-4-(3,5-dichlorphenyl)-3-trifluormethylpyrazol-l -yl]-2-methyl-N-(2,2,2- trifluor-l-methylethyl)benzamid (62 mg, 0,11 mmol, 24 %).To a solution of 4- [5-amino-4- (3,5-dichloro-phenyl) -3-trifluoromethyl-pyrazol-1-yl] -2-methyl-N- (2,2,2-trifluoro-1-methylethyl) -benzamide (200 mg, 0.38 mmol) in bromoform (0.5 mL) becomes slow Tert-butyl nitrite (86 mg, 0.84 mmol) is added dropwise and allowed to stir overnight at room temperature. Purification by chromatography on silica gel with cyclohexane / ethyl acetate 1/1 gives 4- [5-bromo-4- (3,5-dichlorophenyl) -3-trifluoromethylpyrazol-1-yl] -2-methyl-N- (2,2, 2-trifluoro-1-methylethyl) benzamide (62mg, 0.11mmol, 24%).
log P (HCOOH): 5,53log P (HCOOH): 5.53
1H NMR (DMSO-d6): 8,90 (d, 1 H, J = 8,8 Hz), 7,72 (t, I H1 J = 2,0 Hz), 7,57-7,54 (m, 3 H), 7,50 (d, 2 H, J = 2,0 Hz), 4,84-4,78 (m, 1 H), 2,43 (s, 3 H), 1,34 (d, 3 H, J = 6,4 Hz) 1 H NMR (DMSO-d6): 8.90 (d, 1 H, J = 8.8 Hz), 7.72 (t, IH 1 J = 2.0 Hz), 7.57-7.54 ( m, 3H), 7.50 (d, 2H, J = 2.0Hz), 4.84-4.78 (m, 1H), 2.43 (s, 3H), 1.34 (d, 3H, J = 6.4 Hz)
Allgemeine Synthesevorschrift zur Herstellung von Verbindungen der Formel α-A/B-O2 mit R1 = CDGeneral procedure for the preparation of compounds of the formula α-A / B-O2 with R 1 = CD
4-[5-Chlor-4-(3,5-dichlorphenyl)-3-trifluormethylpyrazol-l-yl]-2-methyl-N-(2,2,2-trifluor-l- methylethyl)benzamid (I-A-Q2-022)4- [5-Chloro-4- (3,5-dichlorophenyl) -3-trifluoromethylpyrazol-1-yl] -2-methyl-N- (2,2,2-trifluoro-1-methylethyl) -benzamide (IA-Q2 -022)
Eine Lösung von tert-Butylnitrit (24 mg, 0,23 mmol) in Acetonitril (2 mL) wird mit Kupfer(π)chlorid (31 mg, 0,23 mmol) und (4-[5-Amino-4-(3,5-dichlorphenyl)-3- trifluormethylpyrazol-l-yl]-2-methyl-N-(2,2,2-trifluor-l-methylethyl)benzamid (80 mg, 0,15 mmol) versetzt und 30 min bei 80 0C rühren gelassen und dann einrotiert. Reinigung mittels Chromatoographie über Kieselgel mit Cyclohexan/Ethylacetat 1/1 lliefert 4-[5-Chlor-4-(3,5- dichloφhenyl)-3-trifluormethylpyrazol-l-yl]-2-methyl-N-(2,2,2-trifluor-l-methylethyl)benzamid (30 mg, 0,055 mmol, 33 %).A solution of tert-butyl nitrite (24 mg, 0.23 mmol) in acetonitrile (2 mL) is added copper (π) chloride (31 mg, 0.23 mmol) and 4- [5-amino-4- (3 , 5-dichlorophenyl) -3-trifluoromethylpyrazol-1-yl] -2-methyl-N- (2,2,2-trifluoro-1-methylethyl) -benzamide (80 mg, 0.15 mmol) and stirring at 80 ° for 30 min 0 C and then allowed to stir for cleaning evaporated. Chromatoographie means over silica gel with cyclohexane / ethyl acetate 1/1 lliefert 4- [5-chloro-4- (3,5-dichloφhenyl) -3-trifluoromethyl-pyrazol-l-yl] -2-methyl N- (2,2,2-trifluoro-1-methylethyl) benzamide (30 mg, 0.055 mmol, 33%).
log P (HCOOH): 5,59log P (HCOOH): 5.59
1H NMR (DMSO-d6): 8,88 (d, 1 H, J = 8,4 Hz), 7,72 (t, 1 H, J = 1,8 Hz), 7,59-7,55 (m, 3 H), 7,52 (d, 2 H, J = 2,0 Hz), 4,84-4,78 (m, 1 H), 2,43 (s, 3 H), 1,34 (d, 3 H, J = 6,4 Hz) Svnthesevorschrift zur Herstellung von Verbindungen der Formel (T-A/B-Q2 mit R1 = SMe und SOMe) 1 H NMR (DMSO-d6): 8.88 (d, 1H, J = 8.4Hz), 7.72 (t, 1H, J = 1.8Hz), 7.59-7.55 (m, 3H), 7.52 (d, 2H, J = 2.0Hz), 4.84-4.78 (m, 1H), 2.43 (s, 3H), 1, 34 (d, 3 H, J = 6.4 Hz) Synthesis instructions for the preparation of compounds of the formula (TA / B-Q2 where R 1 = SMe and SOMe)
4-[4-(3,5-Dichlorphenyl)-5-methylsulfanyl-3-trifluormethylpyrazol-l-yl]-2-methyl-N-(2,2,2- trifluor-l-methylethyl)benzamid (I-A-Q2-027)4- [4- (3,5-dichlorophenyl) -5-methylsulfanyl-3-trifluoromethylpyrazol-1-yl] -2-methyl-N- (2,2,2-trifluoro-1-methylethyl) -benzamide (IA-Q2 -027)
Zu einer Lösung von 4-[5-Arnino-4-(3,5-dichlθφhenyl)-3-trifluormethylpyrazol-l-yl]-2-methyl-N- (2,2,2-trifluor-l-methylethyl)benzamid (100 mg, 0,19 mmol) in Chloroform (1 mL) wird Dimethyldisulfid (36 mg, 0,38 mmol) hinzugefügt. Das Reaktionsgemisch wird langsam mit tert- Butylnitrit (29 mg, 0,29 mmol), 3 min zum Refluxieren gebracht, abgekühlt, auf Wasser (5 mL) gegossen und mit Ethylacetat (5 mL) extrahiert. Die organische Phase wird mit Wasser (5 mL) gewaschen, über Natriumsulfat getrocknet und einrotiert. Reinigung mittels Chromatographie über Kieselgel mit Cyclohexan/Ethylacetat 8/1 liefert 4-[4-(3,5-Dichlorphenyl)-5-methylsulfanyl-3- trifluormethylpyrazol-l-yl]-2-methyl-N-(2,2,2-trifiuor-l-methylethyl)benzamid (43 mg, 0,77 mmol, 39 %).To a solution of 4- [5-amino-4- (3,5-dichloro-phenyl) -3-trifluoromethyl-pyrazol-1-yl] -2-methyl-N- (2,2,2-trifluoro-1-methylethyl) -benzamide (100 mg, 0.19 mmol) in chloroform (1 mL) is added dimethyl disulfide (36 mg, 0.38 mmol). The reaction mixture is slowly brought to reflux with tert-butylnitrite (29 mg, 0.29 mmol), 3 min, cooled, poured onto water (5 mL) and extracted with ethyl acetate (5 mL). The organic phase is washed with water (5 mL), dried over sodium sulfate and concentrated by rotary evaporation. Purification by chromatography on silica gel with cyclohexane / ethyl acetate 8/1 affords 4- [4- (3,5-dichlorophenyl) -5-methylsulfanyl-3-trifluoromethylpyrazol-1-yl] -2-methyl-N- (2,2, 2-trifluoro-1-methylethyl) benzamide (43 mg, 0.77 mmol, 39%).
log P (HCOOH): 5,48log P (HCOOH): 5.48
1H NMR (DMSO-d6): 8,87 (d, 1 H, J = 8,8 Hz), 7,69 (t, 1 H, J = 1,8 Hz), 7,58-7,51 (m, 3 H), 7,50 (d, 2 H, J = 2,0 Hz), 4,84-4,77 (m, 1 H), 2,43 (s, 3 H), 2,04 (s, 3 H), 1,34 (d, 3 H, J = 6,4 Hz) 1 H NMR (DMSO-d6): 8.87 (d, 1 H, J = 8.8 Hz), 7.69 (t, 1 H, J = 1.8 Hz), 7.58-7.51 (m, 3H), 7.50 (d, 2H, J = 2.0Hz), 4.84-4.77 (m, 1H), 2.43 (s, 3H), 2, 04 (s, 3 H), 1.34 (d, 3 H, J = 6.4 Hz)
4-[4-(3,5-Dichlorphenyl)-5-methansulfinyl-3-trifluormethylpyrazol-l-yl]-2-methyl-N- pyridin-2-ylmethylbenzamid (I-A-Q2-063)4- [4- (3,5-dichlorophenyl) -5-methanesulfinyl-3-trifluoromethylpyrazol-1-yl] -2-methyl-N-pyridin-2-ylmethylbenzamide (I-A-Q2-063)
Zu einer Lösung von 4-[4-(3,5-Dichlθφhenyl)-5-methansulfanyl-3-trifluormethylpyrazol-l-yl]-2- methyl-N-pyridin-2-ylmethylbenzamid (50 mg, 0,09 mmol) in Dichlormethan (1 mL) gibt man m- Chlorperbenzoesäure (29 mg, 0,12 mmol) und rührt über Nacht. Das Reaktionsgemisch wird mit Wasser gewaschen, die organische Phase über Natriumsulfat getrocknet und einrotiert. Reinigung mittels Chromatographie über Kieselgel mit Cyclohexan/Ethylacetat 9/1 liefert 4-[4-(3,5- Dichloφhenyl)-5-methansulfanyl-3-trifluormethylpyrazol-l-yl]-2-methyl-N-pyridin-2- ylmethylbenzamid (20 mg, 0,035 mmol, 39%). To a solution of 4- [4- (3,5-dichloro-phenyl) -5-methanesulfanyl-3-trifluoromethylpyrazol-1-yl] -2-methyl-N-pyridin-2-ylmethylbenzamide (50 mg, 0.09 mmol) in dichloromethane (1 mL) is added m-chloroperbenzoic acid (29 mg, 0.12 mmol) and stirred overnight. The reaction mixture is washed with water, the organic phase dried over sodium sulfate and concentrated by rotary evaporation. Purification by chromatography on silica gel with cyclohexane / ethyl acetate 9/1 affords 4- [4- (3,5-dichloro-phenyl) -5-methanesulfanyl-3-trifluoromethyl-pyrazol-1-yl] -2-methyl-N-pyridin-2-ylmethylbenzamide (20 mg, 0.035 mmol, 39%).
1Og P (HCOOH): 3,111Og P (HCOOH): 3.11
1H NMR (DMSO-d6): 8,54 (d, 1 H, J = 4,8 Hz), 7,77 (td, 1 H, J = 7,6 und 2,0 Hz), 7,66-7,48 (m, 7 H), 7,41 (d, I H1 J = 8,0 Hz), 7,26 (dd, 7,2 und 4,8 Hz), 4,66 (d, 2 H, J = 6,0 Hz), 2,65 (s, 3 H), 2,50 (s, 3 H) 1 H NMR (DMSO-d6): 8.54 (d, 1 H, J = 4.8 Hz), 7.77 (td, 1 H, J = 7.6 and 2.0 Hz), 7.66 -7.48 (m, 7H), 7.41 (d, IH 1 J = 8.0 Hz), 7.26 (dd, 7.2 and 4.8 Hz), 4.66 (d, 2 H, J = 6.0 Hz), 2.65 (s, 3H), 2.50 (s, 3H)
Synthesevorschrift zur Herstellung von Verbindungen der Formel (I-A/B-02 mit R1 = NH und A1 = A2 = N)Synthesis protocol for the preparation of compounds of the formula (IA / B-02 where R 1 = NH and A 1 = A 2 = N)
2- [5-Amino-4-(3,5-dichlorphenyl)-3-trifluormethylpyrazol-l-yl] -4-trifluormethylpyrimidin- 5-carbonsäure(pyridin-2-ylmethyl)amid (I-A-Q2-020)2- [5-Amino-4- (3,5-dichlorophenyl) -3-trifluoromethylpyrazol-1-yl] -4-trifluoromethyl-pyrimidine-5-carboxylic acid (pyridin-2-ylmethyl) -amide (I-A-Q2-020)
Eine Lösung von 2-CUor-4-trifluoπnethylpyrirnidin-5-carbonsäurechlorid (300 mg, 1,23 mmol) in Dichlormethan (3 mL) wird mit N-Ethyldiisopropylamin (174 mg, 1,35 mmol) und 2- Aminornethylpyridin (140 mg, 1,29 mmol) in THF (2 mL) versetzt und über Nacht bei Raumtemperatur gerührt. Entfernen des Lösungsmittels im Vakuum liefert 650 mg Rohprudukt, wovon 95 mg in DMF (2 mL) gelöst und mit 4-(3,5-Dichloφhenyl)-5-trifluormethyl-2H-pyrazol-3- ylamin (107 mg, 0,36 mmol) und Kaliumcarbonat (58 mg, 0,42 mmol) versetzt werden. Es wird 1,5 h bei 100 0C gerührt, auf Raumtemperatur abgekühlt, auf Wasser (5 mL) gegossen und mit Ethylacetat (5 mL) extrahiert. Die organische Phase wird mit Wasser (5 mL) gewaschen, über Natriumsulfat getrocknet und einrotiert. Reinigung mittels Chromatographie über Kieselgel mit Cyclohexan/Ethylacetat 3/1 liefert 2-[5-Amino-4-(3,5-dichloφhenyl)-3-trifluormethylpyrazol-l- yl]-4-trifluormethylpyrimidin-5-carbonsäure(pyridin-2-ylmethyl)amid (55 mg, 0,095 mmol, 53 %).A solution of 2-Cu-4-trifluoromethylpyrirnidine-5-carboxylic acid chloride (300 mg, 1.23 mmol) in dichloromethane (3 mL) is treated with N-ethyldiisopropylamine (174 mg, 1.35 mmol) and 2-aminomethylpyridine (140 mg , 1.29 mmol) in THF (2 mL) and stirred overnight at room temperature. Removal of the solvent in vacuo yields 650 mg of crude product, of which 95 mg is dissolved in DMF (2 mL) and treated with 4- (3,5-dichloro-phenyl) -5-trifluoromethyl-2H-pyrazol-3-ylamine (107 mg, 0.36 mmol) and potassium carbonate (58 mg, 0.42 mmol) are added. It is stirred for 1.5 h at 100 0 C, cooled to room temperature, poured onto water (5 mL) and extracted with ethyl acetate (5 mL). The organic phase is washed with water (5 mL), dried over sodium sulfate and concentrated by rotary evaporation. Purification by chromatography on silica gel with Cyclohexane / ethyl acetate 3/1 provides 2- [5-amino-4- (3,5-dichloro-phenyl) -3-trifluoromethyl-pyrazol-1-yl] -4-trifluoromethyl-pyrimidine-5-carboxylic acid (pyridin-2-ylmethyl) -amide (55 mg, 0.095 mmol, 53%).
log P (HCOOH): 3,54log P (HCOOH): 3.54
1H NMR (DMSO-d6): 9,30 (s, 1 H), 9,27 (t, 1 H, J = 6,0 Hz), 8,54 (d, 1 H, J = 4,8 Hz), 7,80 (td, 1 H, J = 7,8 und 2,0 Hz), 7,57 (t, 1 H, J = 1,8 Hz), 7,42 (d, 1 H, J = 7,6 Hz), 7,37 (d, 2 H, J = 1,6 Hz), 7,30 (dd, 1 H, J = 6,4 und 3,6 Hz), 7,00 (s, 2 H), 4,62 (d, 2 H, J = 5,6 Hz) 1 H NMR (DMSO-d6): 9.30 (s, 1H), 9.27 (t, 1H, J = 6.0 Hz), 8.54 (d, 1H, J = 4.8 Hz), 7.80 (td, 1 H, J = 7.8 and 2.0 Hz), 7.57 (t, 1 H, J = 1.8 Hz), 7.42 (d, 1 H, J = 7.6 Hz), 7.37 (d, 2H, J = 1.6 Hz), 7.30 (dd, 1H, J = 6.4 and 3.6 Hz), 7.00 ( s, 2 H), 4.62 (d, 2 H, J = 5.6 Hz)
Svnthesevorschrift zur Herstellung von Verbindungen der Formel (I-A/B-Q2 mit R1 = EDSynthesis for the preparation of compounds of formula (IA / B-Q2 with R 1 = ED
4-(4-Iod-3-trifluormethylpyrazol-l-yl)-2-trifluormethylbenzoesäureethylester (XI-A-OOl)Ethyl 4- (4-iodo-3-trifluoromethylpyrazol-1-yl) -2-trifluoromethylbenzoate (XI-A-OOl)
Eine Lösung von 4-Fluor-2-trifluormethylbenzoesäureethylester (2,00 g, 8,47 mmol) in DMF (30 mL) wird mit 4-Iod-3-trifluormethyl-lH-pyrazol (2,22 g, 8,47 mmol) und Kaliumcarbonat (1,40 g, 10,2 mmol) versetzt und 1 h bei 60 0C gerührt. Das Reaktionsgemisch wird mit Ethylacetat verdünnt, mit Wasser und gesättigter Kochsalzlösung gewaschen, über Magnesiumsulfat getrocknet und im Vakuum eingeengt. Reinigung mittels Chromatographie über Kieselgel liefert 4- (4-Iod-3-trifluormethylpyrazol-l-yl)-2-trifluormethylbenzoesäureethylester (3,65 g, 7,63 mmol,A solution of ethyl 4-fluoro-2-trifluoromethylbenzoate (2.00 g, 8.47 mmol) in DMF (30 mL) is treated with 4-iodo-3-trifluoromethyl-lH-pyrazole (2.22 g, 8.47 mmol ) and potassium carbonate (1.40 g, 10.2 mmol) and stirred at 60 0 C for 1 h. The reaction mixture is diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. Purification by chromatography on silica gel gives ethyl 4- (4-iodo-3-trifluoromethylpyrazol-1-yl) -2-trifluoromethylbenzoate (3.65 g, 7.63 mmol,
1H NMR (CDC13): 1,41 (t, 3 H, J = 7,1 Hz), 4,43 (q, 2 H, J = 7,1 Hz), 7,92-7,99 (m, 2 H), 8,08 (s, 1 H), 8,14-8,14 (m, 1 H). 1 H NMR (CDC13): 1.41 (t, 3H, J = 7.1Hz), 4.43 (q, 2H, J = 7.1Hz), 7.92-7.99 (m , 2H), 8.08 (s, 1H), 8.14-8.14 (m, 1H).
4-[4-(3,5-Dichlorphenyl)-3-trifluormethylpyrazol-l-yl]-2-trifluormethylbenzoesäure- ethylester4- [4- (3,5-dichlorophenyl) -3-trifluoromethylpyrazol-1-yl] -2-trifluoromethylbenzoic acid ethyl ester
(I-A-Q4-001) (IA-Q4-001)
Eine Lösung von 4-(4-Iod-3-trifluormethylpyrazol-l-yl)-2-trifluormethylbenzoesäureethylester (1,00 g, 2,09 mmol) in DME (10 mL) wird mit 3,5-Dichlorphenylboronsäure (0,60 g, 3,14 mmol), und Natriumcarbonat (0,69 g, 6,48 mmol) in Wasser (2 mL) versetzt. Das Reaktionsgefäss wird entgasst und mit Stickstoff befüllt. Tetrakis(triphenylphosphin)palladium (0,73 g, 0,63 mmol) wird hinzugefügt und das Reaktionsgemisch wird 9 h bei 85 0C gerührt. Nach dem Abkühlen wird es auf Wasser gegossen und mit Ethylacetat extrahiert. Die organische Phase wird mit Wasser und gesättigter Kochsalzlösung gewaschen, über Magnesiumsulfat getrocknet und einrotiert. Reinigung mittels Chromatographie über Kieselgel liefert 4-[4-(3,5-Dichloφhenyl)-3-trifluormethylpyrazol- l-yl]-2-trifluormethylbenzoesäureethylester (0,30 g, 0,60 mmol, 29%).A solution of ethyl 4- (4-iodo-3-trifluoromethylpyrazol-1-yl) -2-trifluoromethylbenzoate (1.00 g, 2.09 mmol) in DME (10 mL) is treated with 3,5-dichlorophenylboronic acid (0.60 g, 3.14 mmol), and sodium carbonate (0.69 g, 6.48 mmol) in water (2 mL). The reaction vessel is degassed and filled with nitrogen. Tetrakis (triphenylphosphine) palladium (0.73 g, 0.63 mmol) is added and the reaction is stirred at 85 ° C. for 9 h. After cooling, it is poured onto water and extracted with ethyl acetate. The organic phase is washed with water and saturated brine, dried over magnesium sulfate and concentrated by rotary evaporation. Purification by chromatography over silica gel afforded 4- [4- (3,5-dichloro-phenyl) -3-trifluoromethylpyrazol-1-yl] -2-trifluoromethylbenzoic acid, ethyl ester (0.30 g, 0.60 mmol, 29%).
1H NMR (CDC13): 1,42 (t, 3 H, J = 7,1 Hz), 4,44 (q, 2 H, J = 7,1 Hz), 7,37-7,42 (m, 3 H), 8,00-8,01 (m, 2 H), 8,14-8,15 (m, 2 H) 1 H NMR (CDC13): 1.42 (t, 3H, J = 7.1 Hz), 4.44 (q, 2H, J = 7.1 Hz), 7.37-7.42 (m , 3H), 8.00-8.01 (m, 2H), 8.14-8.15 (m, 2H)
4-[4-(3,5-Dichlorphenyl)-3-trifluormethylpyrazoI-l-yl]-2-trifluormethylbenzoesäure (I-A-Q4-002)4- [4- (3,5-dichlorophenyl) -3-trifluoromethylpyrazol-1-yl] -2-trifluoromethylbenzoic acid (I-A-Q4-002)
Eine Lösung von 4-[4-(3,5-Dichlorphenyl)-3-trifluormethylpyrazol-l-yl]-2-trifluormethyl- benzoesäureethylester (300 mg, 0,60 mmol) in Ethanol (10 mL) wird mit Natriumhydroxid (48 mg, 1,2 mmol) in Wasser (10 mL) versetzt und über Nacht bei Raumtemperatur gerührt. Das organische Lösungsmittel wird im Vakuum entfernt und der wässrige Rückstand mit verdünnter Salzsäure behandelt. Abiϊltrieren des gebildeten Niederschlags und Trocknen bei 50 0C unter vermindertem Druck liefert 4-[4-(3,5-Dichloφhenyl)-3-trifluormethylpyrazol-l-yl]-2-trifluor- methylbenzoesäure (259 mg, 0,53 mmol, 88 %). ^^-(S^-DichlorphenyO-S-trifluormethylpyrazol-l-yll-N-Cl^^-trifluorethyl)-!- trifluormethylbenzamid (I-A-Q2-002)A solution of ethyl 4- [4- (3,5-dichlorophenyl) -3-trifluoromethylpyrazol-1-yl] -2-trifluoromethylbenzoate (300 mg, 0.60 mmol) in ethanol (10 mL) is washed with sodium hydroxide (48 mg, 1.2 mmol) in water (10 mL) and stirred overnight at room temperature. The organic solvent is removed in vacuo and the aqueous residue treated with dilute hydrochloric acid. Abiϊltrieren of the formed precipitate, and drying at 50 0 C under reduced pressure yields 4- [4- (3,5-Dichloφhenyl) -3-trifluoromethyl-pyrazol-l-yl] -2-trifluoro methyl benzoic acid (259 mg, 0.53 mmol, 88%). ^^ - (S-Dichloro-phenyl-O-S-trifluoromethyl-pyrazol-1-yl-N-Cl ^ -trifluoroethyl) -l-trifluoromethylbenzamide (IA-Q2-002)
Eine Lösung von 4-[4-(3,5-Dichloφhenyl)-3-trifluormethylpyrazol-l-yl]-2-trifluormethyl-benzoe- säure (130 mg, 0,28 mmol) in DMF (10 mL) wird mit 2,2,2-Trifluorethylamin (40 mg, 0,41 mmol), und l-Ethyl-3-[3-dimethylaminopropyl]carbodiimid Hydrochlorid (60 mg, 0,33 mmol) versetzt. Das Reaktionsgemisch wird 8 h bei Raumtemperatur gerührt, mit tert-Butylmethylether verdünnt, mit Wasser und gesättigter Kochsalzlösung gewaschen, über Magnesiumsulfat getrocknet und das Lösungsmittel im Vakuum entfernt. Reinigung mittels Chromatographie über Kieselgel liefert 4- [4-(3,5-Dichloφhenyl)-3-trifluormethylpyrazol-l-yl]-N-(2,2,2-trifluorethyl)-2-trifluormethylbenz- amid (100 mg, 0,18 mmol, 66 %).A solution of 4- [4- (3,5-dichloro-phenyl) -3-trifluoromethylpyrazol-1-yl] -2-trifluoromethyl-benzoic acid (130 mg, 0.28 mmol) in DMF (10 mL) is added with 2 , 2,2-trifluoroethylamine (40 mg, 0.41 mmol), and 1-ethyl-3- [3-dimethylaminopropyl] carbodiimide hydrochloride (60 mg, 0.33 mmol). The reaction mixture is stirred at room temperature for 8 h, diluted with tert-butyl methyl ether, washed with water and saturated brine, dried over magnesium sulfate and the solvent removed in vacuo. Purification by chromatography on silica gel provides 4- [4- (3,5-dichloro-phenyl) -3-trifluoromethylpyrazol-1-yl] -N- (2,2,2-trifluoroethyl) -2-trifluoromethylbenzamide (100 mg, 0 , 18 mmol, 66%).
log P (pH2): 5.16log P (pH2): 5.16
log P (pH7,5): 5.14log P (pH 7.5): 5.14
1H NMR (CDC13): 4,10-4,14 (m, 2 H), 6,33-6,35 (m, 1 H), 7,34-7,40 (m, 3 H), 7,59-7,67 (m, I H), 7,86-8,15 (m, 3 H). 1 H NMR (CDC13): 4.10-4.14 (m, 2H), 6.33-6.35 (m, 1H), 7.34-7.40 (m, 3H), 7 , 59-7.67 (m, IH), 7.86-8.15 (m, 3H).
Die Bestimmung der angegebenen log P-Werte erfolgte gemäß EEC-Direktive 79/831 Annex V.A8 durch HPLC (High Performance Liquid Chromatography) an einer Phasenumkehrsäule (C 18).The determination of the indicated log P values was carried out according to EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase inversion column (C 18).
Agilent 1100 LC-System; 50*4,6 Zorbax Eclipse Plus C18 1,8 microm; Eluent A: Acetonitril (0,1 % Ameisensäure); Eluent B: Wasser (0,09 % Ameisensäure); linearer Gradient von 10 % Acetonitril bis 95 % Acetonitril in 4,25 min, dann 95% Acetonitril für weitere 1,25 min; Ofentemperatur 55 0C; Fluß:2,0 mL/minAgilent 1100 LC system; 50 * 4.6 Zorbax Eclipse Plus C18 1.8 microm; Eluent A: acetonitrile (0.1% formic acid); Eluent B: water (0.09% formic acid); linear gradient from 10% acetonitrile to 95% acetonitrile in 4.25 min, then 95% acetonitrile for a further 1.25 min; Oven temperature 55 0 C; Flow: 2.0 mL / min
Beim Einsatz der erfindungsgemäßen Wirkstoffe als Insektizide und Akarizide können die Aufwandmengen je nach Applikationsart innerhalb eines größeren Bereiches variiert werden. Die Aufwandmenge der erfϊndungsgemäßen Wirkstoffe beträgt bei der Behandlung von Pflanzenteilen, z.B. Blättern von 0,1 bis 10.000 g/ha, bevorzugt von 10 bis 1.000 g/ha, besonders bevorzugt von 50 bis 300g/ha (bei Anwendung durch Gießen oder Tropfen kann die Aufwandmenge sogar verringert werden, vor allem wenn inerte Substrate wie Steinwolle oder Perlit verwendet werden); bei der Saatgutbehandlung von 2 bis 200 g pro 100 kg Saatgut, bevorzugt von 3 bis 150 g pro 100 kg Saatgut, besonders bevorzugt von 2,5 bis 25 g pro 100 kg Saatgut, ganz besonders bevorzugt von 2,5 bis 12,5 g pro 100 kg Saatgut; bei der Bodenbehandlung von 0,1 bis 10.000 g/ha, bevorzugt von 1 bis 5.000 g/ha. Diese Aufwandmengen seien nur beispielhaft und nicht limitierend im Sinne der Erfindung genannt.When using the active compounds according to the invention as insecticides and acaricides, the application rates can be varied within a substantial range, depending on the mode of administration. The application rate of the active compounds according to the invention in the treatment of parts of plants, eg leaves, is from 0.1 to 10,000 g / ha, preferably from 10 to 1,000 g / ha, particularly preferably from 50 to 300 g / ha (when used by pouring or dropping the Application rate can even be reduced, especially when inert substrates such as rockwool or perlite are used); in the Seed treatment of 2 to 200 g per 100 kg of seed, preferably from 3 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, most preferably from 2.5 to 12.5 g per 100 kg of seed; in the soil treatment from 0.1 to 10,000 g / ha, preferably from 1 to 5,000 g / ha. These application rates are given by way of example only and not by way of limitation within the meaning of the invention.
Die erfindungsgemäßen Wirkstoffe können eingesetzt werden, um Pflanzen innerhalb eines gewissen Zeitraumes nach der Behandlung gegen den Befall durch die genannten tierischen Schädlinge zu schützen. Der Zeitraum, innerhalb dessen Schutz herbeigeführt wird, erstreckt sich im Allgemeinen auf 1 bis 28 Tage, bevorzugt auf 1 bis 14 Tage, besonders bevorzugt auf 1 bis 10 Tage, ganz besonders bevorzugt auf 1 bis 7 Tage nach der Behandlung der Pflanzen mit den Wirkstoffen bzw. auf bis zu 200 Tage nach einer Saatgutbehandlung.The active compounds according to the invention can be used to protect plants within a certain period of time after treatment against infestation by said animal pests. The period of time within which protection is afforded generally ranges from 1 to 28 days, preferably from 1 to 14 days, more preferably from 1 to 10 days, most preferably from 1 to 7 days after treatment of the plants with the active ingredients or up to 200 days after seed treatment.
Die erfindungsgemäßen Wirkstoffe eignen sich bei guter Pflanzenverträglichkeit, günstiger Warm- blütertoxizität und guter Umweltverträglichkeit zum Schutz von Pflanzen und Pflanzenorganen, zur Steigerung der Ernteerträge, Verbesserung der Qualität des Erntegutes und zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren, Helminthen, Nematoden und Mollusken, die in der Landwirtschaft, im Gartenbau, bei der Tierzucht, in Forsten, in Gärten und Freizeiteinrichtungen, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. Sie können vorzugsweise als Pflanzenschutzmittel eingesetzt werden. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören:The active compounds according to the invention are suitable for plant tolerance, favorable warm-blood toxicity and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs which are found in agriculture, horticulture, livestock, forests, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The above mentioned pests include:
Aus der Ordnung der Anoplura (Phthiraptera) z.B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp..From the order of the Anoplura (Phthiraptera) e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.
Aus der Klasse der Arachnida z.B. Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.From the class of arachnids, e.g. Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp. , Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp. Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.
Aus der Klasse der Bivalva z.B. Dreissena spp..From the class of bivalva, e.g. Dreissena spp ..
Aus der Ordnung der Chilopoda z.B. Geophilus spp., Scutigera spp.. Aus der Ordnung der Coleoptera z.B. Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zea- landica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lacbαiosteπia consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Popillia japonica, Premnotrypes spp., Psylliodes chryso- cephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp..From the order of Chilopoda eg Geophilus spp., Scutigera spp. From the order Coleoptera eg Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp., Attagenus spp. Bruchidius obtectus, Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lacbαiosteπia consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Popillia japonica, Premnotrypes spp., P sylliodes chrysoccephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Starchus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp. Zabrus spp ..
Aus der Ordnung der Collembola z.B. Onycbiurus armatus.From the order of Collembola e.g. Onycbiurus armatus.
Aus der Ordnung der Dermaptera z.B. Forficula auricularia.From the order of the Dermaptera e.g. Forficula auricularia.
Aus der Ordnung der Diplopoda z.B. Blaniulus guttulatus.From the order of diplopoda e.g. Blaniulus guttulatus.
Aus der Ordnung der Diptera z.B. Aedes spp., Anopheles spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fannia spp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp.. Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanus spp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.From the order of Diptera e.g. Aedes spp., Anopheles spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fannia spp. Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp. Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp. Tabanus spp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.
Aus der Klasse der Gastropoda z.B. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp..From the class Gastropoda, e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.
Aus der Klasse der Helminthen z.B. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp, Strongyloides fiielleborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.From the class of helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp , Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp, Strongyloides fiielleborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.
Weiterhin lassen sich Protozoen, wie Eimeria, bekämpfen.Furthermore, protozoa, such as Eimeria, can be combated.
Aus der Ordnung der Heteroptera z.B. Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.From the order of Heteroptera, e.g. Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp. Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp. Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.
Aus der Ordnung der Homoptera z.B. Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon firagaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Pere- grinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Tri- aleurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii. Aus der Ordnung der Hymenoptera z.B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp..From the order of Homoptera eg Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon firagaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp. Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striate llus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis , Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp , Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Tri- aleurodes vaporariorum, Trioza spp., Typhl ocyba spp., Unaspis spp., Viteus vitifolii. From the order of Hymenoptera eg Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
Aus der Ordnung der Isopoda z.B. Armadillidium vulgäre, Oniscus asellus, Porcellio scaber.From the order of isopods e.g. Armadillidium vulgaris, Oniscus asellus, Porcellio scaber.
Aus der Ordnung der Isoptera z.B. Reticulitermes spp., Odontotermes spp..From the order of Isoptera e.g. Reticulitermes spp., Odontotermes spp.
Aus der Ordnung der Lepidoptera z.B. Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Caφocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, La- phygma spp., Lithocolletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp..From the order of Lepidoptera e.g. Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus pinarius, Cacoecia podana, Capua reticulana, Caφocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp , Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, La phygma spp., Lithocolletis blancardella, Lithophane antennata , Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp. , Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp ..
Aus der Ordnung der Orthoptera z.B. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.From the order of Orthoptera e.g. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
Aus der Ordnung der Siphonaptera z.B. Ceratophyllus spp., Xenopsylla cheopis.From the order of siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis.
Aus der Ordnung der Symphyla z.B. Scutigerella immaculata.From the order of Symphyla e.g. Scutigerella immaculata.
Aus der Ordnung der Thysanoptera z.B. Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp..From the order of Thysanoptera e.g. Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
Aus der Ordnung der Thysanura z.B. Lepisma saccharina.From the order of Thysanura e.g. Lepisma saccharina.
Zu den pflanzenparasitären Nematoden gehören z.B. Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.. Die erfindungsgemäßen Verbindungen können gegebenenfalls in bestimmten Konzentrationen bzw. Aufwandmengen auch als Herbizide, Safener, Wachstumsregulatoren oder Mittel zur Verbesserung der Pflanzeneigenschaften oder als Mikrobizide, beispielsweise als Fungizide, Antimykotika, Bakterizide, Virizide (einschließlich Mittel gegen Viroide) oder als Mittel gegen MLO (Mycoplasma-like-organism) und RLO (Rickettsia-like-organism) verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- oder Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen.The plant parasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp. If appropriate, the compounds according to the invention may also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as anti-MLO agents (Mycoplasma -like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
Die Wirkstoffe können in die üblichen Formulierungen überführt werden, wie Lösungen, Emulsionen, Spritzpulver, wasser- und ölbasierte Suspensionen, Pulver, Stäubemittel, Pasten, lös- liehe Pulver, lösliche Granulate, Streugranulate, Suspensions-Emulsions-Konzentrate, Wirkstoffimprägnierte Naturstoffe, Wirkstoff-imprägnierte synthetische Stoffe, Düngemittel sowie Feinst- verkapselungen in polymeren Stoffen.The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, active ingredients. impregnated synthetic materials, fertilizers and micro-encapsulants in polymeric materials.
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. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung.These formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents. The preparation of the formulations is carried out either in suitable systems or before or during use.
Als Hilfsstoffe können solche Stoffe Verwendung finden, die geeignet sind, dem Mittel selbst oder und/oder davon abgeleitete Zubereitungen (z.B. Spritzbrühen, Saatgutbeizen) besondere Eigenschaften zu verleihen, wie bestimmte technische Eigenschaften und/oder auch besondere biologische Eigenschaften. Als typische Hilfsmittel kommen in Frage: Streckmittel, Lösemittel und Trägerstoffe.Excipients which can be used are those which are suitable for imparting special properties to the composition itself and / or preparations derived therefrom (for example spray liquor, seed dressing), such as certain technical properties and / or specific biological properties. Typical auxiliaries are: extenders, solvents and carriers.
Als Streckmittel eignen sich z.B. Wasser, polare und unpolare organische chemische Flüssigkeiten z.B. aus den Klassen der aromatischen und nicht-aromatischen Kohlenwasserstoffe (wie Paraffine, Alkylbenzole, Alkylnaphthaline, Chlorbenzole), der Alkohole und Polyole (die ggf. auch substituiert, verethert und/oder verestert sein können), der Ketone (wie Aceton, Cyclohexanon), Ester (auch Fette und Öle) und (poly-)Ether, der einfachen und substituierten Amine, Amide, Lactame (wie N-Alkylpyrrolidone) und Lactone, der Sulfone und Sulfoxide (wie Dimethyl- sysulfoxid).As extender, e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (also fats and oils) and (poly) ethers, the simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulfones and sulfoxides (such as dimethylsulfoxide).
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösemittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösemittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, 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 Dimethylsulfoxid, sowie Wasser.In the case of using water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl sulfoxide, and water.
Als Trägerstoffe kommen in Frage:Suitable carriers are:
z.B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Papier, Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethylen- Fettalkohol-Ether, z.B. Alkylaryl-polyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel kommen in Frage nicht-ionische und/oder ionische Stoffe, z.B. aus den Klassen der Alkohol-POE- und/oder POP-Ether, Säure- und/oder POP- POE- Ester, Alkyl-Aryl- und/oder POP- POE-Ether, Fett- und/oder POP- POE-Addukte, POE- und/oder POP-Polyol Derivate, POE- und/oder POP-Sorbitan- oder-Zucker-Addukte, Alky- oder Aryl- Sulfate, Sulfonate und Phosphate oder die entsprechenden PO-Ether-Addukte. Ferner geeignete Oligo- oder Polymere, z.B. ausgehend von vinylischen Monomeren, von Acrylsäure, aus EO und/oder PO allein oder in Verbindung mit z.B. (poly-) Alkoholen oder (poly-) Aminen. Ferner können Einsatz finden Lignin und seine Sulfonsäure-Derivate, einfache und modifizierte Cellulosen, aromatische und/oder aliphatische Sulfonsäuren sowie deren Addukte mit Formaldehyd.e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are non-ionic and / or ionic substances, e.g. from the classes of alcohol POE and / or POP ethers, acid and / or POP POE esters, alkyl aryl and / or POP POE ethers, fatty and / or POP POE adducts, POE and / or POP polyol derivatives, POE and / or POP sorbitol or sugar adducts, alkyl or aryl sulfates, sulfonates and phosphates or the corresponding PO ether adducts. Further suitable oligo- or polymers, e.g. starting from vinylic monomers, from acrylic acid, from EO and / or PO alone or in combination with e.g. (poly) alcohols or (poly) amines. Furthermore, find use lignin and its sulfonic acid derivatives, simple and modified celluloses, aromatic and / or aliphatic sulfonic acids and their adducts with formaldehyde.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexföπnige Polymere verwendet werden, wie Gummi- arabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospholipide.Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations.
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. Weitere Additive können Duftstoffe, mineralische oder vegetabile gegebenenfalls modifizierte Öle, Wachse und Nährstoffe (auch Spurennährstoffe), wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink sein.Dyes such as inorganic pigments such as 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. Other additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Weiterhin enthalten sein können Stabilisatoren wie Kältestabilisatoren, Konservierungsmittel, Oxidationsschutzmittel, Lichtschutzmittel oder andere die chemische und / oder physikalische Stabilität verbessernde Mittel.Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present.
Der erfindungsgemäße Wirkstoff kann in seinen handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffen wie Insektiziden, Lockstoffen, Sterilantien, Bakteriziden, Akariziden, Nematiziden, Fungiziden, wachstumsregulierenden Stoffen, Herbiziden, Safenern, Düngemitteln, Semiochemicals oder auch mit Mitteln zur Verbesserung der Pflanzeneigenschaften vorliegen.The active ingredient according to the invention can be used in its commercial formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers, semiochemicals or else with agents to improve plant properties.
Die erfϊndungsgemäßen Wirkstoffe können ferner beim Einsatz als Insektizide 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.In addition, the active compounds according to the invention can be present as insecticides in their commercial formulations and in the forms of use prepared from these formulations in admixture with synergists. Synergists are compounds which increase the effect of the active ingredients without the added synergist itself having to be active.
Die erfϊndungsgemäßen Wirkstoffe können ferner beim Einsatz als Insektizide 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 von Pflanzenteilen oder in pflanzlichen Geweben vermindern.The active compounds according to the invention can furthermore, when used as insecticides, be present in their commercial formulations and in the forms of use prepared from these formulations in mixtures with inhibitors which reduce degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant tissues ,
Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten Anwendungsformen kann in weiten Bereichen variieren. Die Gesamtwirkstoffkonzentration oder die Wirkstoffkonzentration der Einzelwirkstoffe der Anwendungsformen liegt im Bereich von 0,00000001 bis 97 Gew.-% Wirkstoff, vorzugsweise im Bereich von 0,0000001 bis 97 Gew.-%, besonders bevorzugt im Bereich von 0,000001 bis 83 Gew.-% oder 0,000001 bis 5 Gew.-% und ganz besonders bevorzugt im Bereich von 0,0001 bis 1 Gew. %.The active substance content of the application forms prepared from the commercial formulations can vary within wide ranges. The total active ingredient concentration or the active ingredient concentration of the individual active substances of the use forms is in the range of 0.00000001 to 97 wt .-% active ingredient, preferably in the range of 0.0000001 to 97 wt .-%, particularly preferably in the range of 0.000001 to 83 wt. -% or 0.000001 to 5 wt .-% and most preferably in the range of 0.0001 to 1 wt.%.
Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise.The application is done in a custom forms adapted to the application.
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 vorkommender Kulturpflanzen). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen, wie Sproß, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stengel, Stämme, Blüten, Fruchtkörper, Früchte und Saatgut sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Erntegut sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Saatgut.According to the invention, all plants and parts of plants can be treated. In this context, plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants produced by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or Combinations of these methods can be obtained, including transgenic plants and including those protected by plant breeders' rights or non-protectable plant varieties. Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, by way of example leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
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, Vernebeln, Streuen, Aufstreichen, Injizieren und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch ein- oder mehrschichtiges Umhüllen.The treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, atomizing, spreading, brushing, injecting and in propagating material, in particular in seeds, further by single or multilayer coating.
Als Pflanzen, welche erfindungsgemäß behandelt werden können, seien folgende erwähnt: Baumwolle, Flachs, Weinrebe, Obst, Gemüse, wie Rosaceae sp. (beispielsweise Kernfrüchte wie Apfel und Birne, aber auch Steinfrüchte wie Aprikosen, Kirschen, Mandeln und Pfirsiche und Beerenfrüchte wie Erdbeeren), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (beispielsweise Bananenbäume und -plantagen), Rubiaceae sp. (beispielsweise Kaffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (beispielsweise Zitronen, Organen und Grapefruit); Solanaceae sp. (beispielsweise Tomaten), Liliaceae sp., Asteraceae sp. (beispielsweise Salat), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (beispielsweise Gurke), Alliaceae sp. (beispielsweise Lauch, Zwiebel), Papilionaceae sp. (beispielsweise Erbsen); Hauptnutzpflanzen, wie Gramineae sp. (beispielsweise Mais, Rasen, Getreide wie Weizen, Roggen, Reis, Gerste, Hafer, Hirse und Triticale), Asteraceae sp. (beispielsweise Sonnenblume), Brassicaceae sp. (beispielsweise Weißkohl, Rotkohl, Brokkoli, Blumenkohl, Rosenkohl, Pak Choi, Kohlrabi, Radieschen sowie Raps, Senf, Meerrettich und Kresse), Fabacae sp. (beispielsweise Bohne, Erdnüsse), Papilionaceae sp. (beispielsweise Sojabohne), Solanaceae sp. (beispielsweise Kartoffeln), Chenopodiaceae sp. (beispielsweise Zuckerrübe, Futterrübe, Mangold, Rote Rübe); Nutzpflanzen und Zierpflanzen in Garten und Wald; sowie jeweils genetisch modifizierte Arten dieser Pflanzen.As plants which can be treated according to the invention, mention may be made of the following: cotton, flax, grapevine, fruits, vegetables, such as Rosaceae sp. (for example, pome fruits such as apple and pear, but also drupes such as apricots, cherries, almonds and peaches and soft fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example, banana trees and plantations), Rubiaceae sp. (for example, coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example, lemons, organs and grapefruit); Solanaceae sp. (for example tomatoes), Liliaceae sp., Asteraceae sp. (for example, lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceae sp. leek, onion), Papilionaceae sp. (for example, peas); Main crops, such as Gramineae sp. (for example corn, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example, white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes and rapeseed, mustard, horseradish and cress), Fabacae sp. (for example, bean, peanuts), Papilionaceae sp. (for example, soybean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example, sugar beet, fodder beet, Swiss chard, beet); Useful plants and ornamental plants in the garden and forest; and each genetically modified species of these plants.
Insbesondere eignen sich die erfindungsgemäßen Wirkstoffe zur Behandlung von Saatgut. Bevorzugt sind dabei die vorstehend als bevorzugt oder besonders bevorzugt genannten erfindungsgemäßen Wirkstoffe zu nennen. So entsteht ein großer Teil des durch Schädlinge verursachten Schadens an Kultuφflanzen bereits durch den Befall des Saatguts während der Lagerung und nach dem Einbringen des Saatguts in den Boden sowie während und unmittelbar nach der Keimung der Pflanzen. Diese Phase ist besonders kritisch, da die Wurzeln und Sprosse der wachsenden Pflanze besonders empfindlich sind und bereits ein geringer Schaden zum Absterben der ganzen Pflanze führen kann. Es besteht daher ein insbesondere großes Interesse daran, das Saatgut und die keimende Pflanze durch den Einsatz geeigneter Mittel zu schützen.In particular, the active compounds according to the invention are suitable for the treatment of seed. Preference is given to mention the active compounds according to the invention mentioned above as being preferred or particularly preferred. This is how much of the damage is caused by pests caused damage to Kultuφplanzen already by the infestation of the seed during storage and after the introduction of the seed into the soil and during and immediately after the germination of the plants. This phase is particularly critical, as the roots and shoots of the growing plant are particularly sensitive and even minor damage can lead to the death of the entire plant. There is therefore a particular interest in protecting the seed and the germinating plant by the use of suitable agents.
Die Bekämpfung von Schädlingen durch die Behandlung des Saatguts von Pflanzen ist seit langem bekannt und ist Gegenstand ständiger Verbesserungen. Dennoch ergeben sich bei der Behandlung von Saatgut eine Reihe von Problemen, die nicht immer zufrieden stellend gelöst werden können. So ist es erstrebenswert, Verfahren zum Schutz des Saatguts und der keimenden Pflanze zu entwickeln, die das zusätzliche Ausbringen von Pflanzenschutzmitteln nach der Saat oder nach dem Auflaufen der Pflanzen überflüssig machen. Es ist weiterhin erstrebenswert, die Menge des eingesetzten Wirkstoffs dahingehend zu optimieren, dass das Saatgut und die keimende Pflanze vor dem Befall durch Schädlinge bestmöglich geschützt werden, ohne jedoch die Pflanze selbst durch den eingesetzten Wirkstoff zu schädigen. Insbesondere sollten Verfahren zur Behandlung von Saatgut auch die intrinsischen insektiziden Eigenschaften transgener Pflanzen einbeziehen, um einen optimalen Schutz des Saatguts und auch der keimenden Pflanze bei einem minimalen Aufwand an Pflanzenschutzmitteln zu erreichen.The control of pests by the treatment of the seed of plants has long been known and is the subject of constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that can not always be satisfactorily resolved. Thus, it is desirable to develop methods of protecting the seed and the germinating plant, which eliminate the need for additional crop protection after sowing or after emergence of the plants. It is also desirable to optimize the amount of active ingredient used in such a way that the seed and the germinating plant are best protected against attack by pests, but without damaging the plant itself by the active ingredient used. In particular, methods for treating seed should also include the intrinsic insecticidal properties of transgenic plants in order to achieve optimum protection of the seed and also of the germinating plant with a minimum of pesticides.
Die vorliegende Erfindung bezieht sich daher insbesondere auch auf ein Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen, indem das Saatgut mit einem erfindungsgemäßen Wirkstoff behandelt wird. Die Erfindung bezieht sich ebenfalls auf dieThe present invention therefore also relates, in particular, to a method for protecting seeds and germinating plants from the infestation of pests by treating the seed with an active ingredient according to the invention. The invention also relates to the
Verwendung der erfindungsgemäßen Wirkstoffe zur Behandlung von Saatgut zum Schutz desUse of the active ingredients according to the invention for the treatment of seed for the protection of the
Saatguts und der daraus entstehenden Pflanze vor Schädlingen. Weiterhin bezieht sich dieSeeds and the resulting plant from pests. Furthermore, the refers
Erfindung auf Saatgut, welches zum Schutz vor Schädlingen mit einem erfindungsgemäßen Wirkstoff behandelt wurde. Die Erfindung bezieht sich auch auf Saatgut, bei dem ein Wirkstoff der Formel I als Bestandteil einer Umhüllung oder als weitere Schicht oder weitere Schichten zusätzlich zu einer Umhüllung aufgebracht sind.Invention on seed which has been treated with an active ingredient according to the invention for protection against pests. The invention also relates to seed in which an active compound of the formula I are applied as a constituent of a coating or as a further layer or further layers in addition to a coating.
Einer der Vorteile der vorliegenden Erfindung ist es, dass aufgrund der besonderen systemischen Eigenschaften einiger der erfindungsgemäßen Wirkstoffe die Behandlung des Saatguts mit diesen Wirkstoffen nicht nur das Saatgut selbst, sondern auch die daraus hervorgehenden Pflanzen nach dem Auflaufen vor Schädlingen schützt. Auf diese Weise kann die unmittelbare Behandlung der Kultur zum Zeitpunkt der Aussaat oder kurz danach entfallen.One of the advantages of the present invention is that because of the particular systemic properties of some of the active ingredients of the invention, the treatment of the seed with these agents not only protects the seed itself but also the resulting plants after emergence from pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
Ebenso ist es als vorteilhaft anzusehen, dass die erfindungsgemäßen Wirkstoffe insbesondere auch bei transgenem Saatgut eingesetzt werden können, wobei die aus diesem Saatgut hervorgehenden Pflanzen zur Expression eines gegen Schädlinge gerichteten Proteins befähigt sind. Durch die Behandlung solchen Saatguts mit den erfmdungsgemäßen Wirkstoffen können bestimmte Schädlinge bereits durch die Expression des z.B. insektiziden Proteins kontrolliert werden, und zusätzlich durch die erfϊndungsgemäßen Wirkstoffen vor Schäden bewahrt werden.Likewise, it is to be regarded as advantageous that the active compounds according to the invention can be used in particular also in transgenic seed, the resulting from this seed Plants are capable of expressing a pest-directed protein. By treating such seeds with the active compounds according to the invention, certain pests can already be controlled by the expression of the insecticidal protein, for example, and additionally protected against damage by the active compounds according to the invention.
Die erfmdungsgemäßen Wirkstoffe eignen sich zum Schutz von Saatgut jeglicher Pflanzensorte wie bereits vorstehend genannt, die in der Landwirtschaft, im Gewächshaus, in Forsten oder im Gartenbau eingesetzt wird. Insbesondere handelt es sich dabei um Saatgut von Mais, Erdnuss, Canola, Raps, Mohn, Soja, Baumwolle, Rübe (z.B. Zuckerrübe und Futterrübe), Reis, Hirse, Weizen, Gerste, Hafer, Roggen, Sonnenblume, Tabak, Kartoffeln oder Gemüse (z.B. Tomaten, Kohlgewächs). Die erfmdungsgemäßen Wirkstoffe eignen sich ebenfalls zur Behandlung des Saatguts von Obstpflanzen und Gemüse wie vorstehend bereits genannt. Besondere Bedeutung kommt der Behandlung des Saatguts von Mais, Soja, Baumwolle, Weizen und Canola oder Raps zu.The active compounds according to the invention are suitable for the protection of seed of any plant variety as already mentioned above, which is used in agriculture, in the greenhouse, in forests or in horticulture. In particular, these are corn, peanut, canola, rapeseed, poppy, soybean, cotton, turnip (eg sugarbeet and fodder beet), rice, millet, wheat, barley, oats, rye, sunflower, tobacco, potatoes or vegetables ( eg tomatoes, cabbage). The inventive active ingredients are also suitable for the treatment of seed of fruit plants and vegetables as already mentioned above. Of particular importance is the treatment of the seeds of maize, soya, cotton, wheat and canola or rapeseed.
Wie vorstehend bereits erwähnt, kommt auch der Behandlung von transgenem Saatgut mit einem erfindungsgemäßen Wirkstoff eine besondere Bedeutung zu. Dabei handelt es sich um das Saatgut von Pflanzen, die in der Regel zumindest ein heterologes Gen enthalten, das die Expression eines Polypeptids mit insbesondere insektiziden Eigenschaften steuert. Die heterologen Gene in transgenem Saatgut können dabei aus Mikroorganismen wie Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus oder Gliocladium stammen. Die vorliegende Erfindung eignet sich besonders für die Behandlung von transgenem Saatgut, das zumindest ein heterologes Gen enthält, das aus Bacillus sp. stammt und dessen Genprodukt Wirksamkeit gegen Maiszünsler und/oder Maiswurzel-Bohrer zeigt. Besonders bevorzugt handelt es sich dabei um ein heterologes Gen, das aus Bacillus thuringiensis stammt.As already mentioned above, the treatment of transgenic seed with an active ingredient according to the invention is of particular importance. These are the seeds of plants, which as a rule contain at least one heterologous gene which controls the expression of a polypeptide with in particular insecticidal properties. The heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. and whose gene product shows activity against corn borer and / or corn rootworm. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
Im Rahmen der vorliegenden Erfindung wird der erfϊndungsgemäße Wirkstoff alleine oder in einer geeigneten Formulierung auf das Saatgut aufgebracht. Vorzugsweise wird das Saatgut in einem Zustand behandelt, in dem so stabil ist, dass keine Schäden bei der Behandlung auftreten. Im Allgemeinen kann die Behandlung des Saatguts zu jedem Zeitpunkt zwischen der Ernte und der Aussaat erfolgen. Üblicherweise wird Saatgut verwendet, das von der Pflanze getrennt und von Kolben, Schalen, Stängeln, Hülle, Wolle oder Fruchtfleisch befreit wurde.In the context of the present invention, the active ingredient according to the invention is applied to the seed alone or in a suitable formulation. Preferably, the seed is treated in a condition that is so stable that no damage occurs during the treatment. In general, the treatment of the seed can be done at any time between harvesting and sowing. Usually, seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
Im Allgemeinen muss bei der Behandlung des Saatguts darauf geachtet werden, dass die Menge des auf das Saatgut aufgebrachten erfmdungsgemäßen Wirkstoffs und/oder weiterer Zusatzstoffe so gewählt wird, dass die Keimung des Saatguts nicht beeinträchtigt bzw. die daraus hervorgehende Pflanze nicht geschädigt wird. Dies ist vor allem bei Wirkstoffen zu beachten, die in bestimmten Aufwandmengen phytotoxische Effekte zeigen können. Die erfindungsgemäßen Mittel können unmittelbar aufgebracht werden, also ohne weitere Komponenten zu enthalten und ohne verdünnt worden zu sein. In der Regel ist es vorzuziehen, die Mittel in Form einer geeigneten Formulierung auf das Saatgut aufzubringen. Geeignete Formulierungen und Verfahren für die Saatgutbehandlung sind dem Fachmann bekannt und werden z.B. in den folgenden Dokumenten beschrieben: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 Al, WO 2002/080675 Al, WO 2002/028186 A2.In general, care must be taken in the treatment of the seed that the amount of the applied according to the invention active ingredient and / or other additives is chosen so that the germination of the seed is not affected or the resulting plant is not damaged. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates. The agents according to the invention can be applied directly, ie without containing further components and without being diluted. In general, it is preferable to apply the agents to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art and are described, for example, in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002 / 028186 A2.
Die erfindungsgemäß verwendbaren Wirkstoffe können in die üblichen Beizmittel-Formulierungen überfuhrt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Slurries oder andere Hüllmassen für Saatgut, sowie ULV-Formulierungen.The active compounds which can be used according to the invention can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, indem man die Wirkstoffe mit üblichen Zusatzstoffen vermischt, wie zum Beispiel übliche Streckmittel sowie Lösungs- oder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, Gibberelline und auch Wasser.These formulations are prepared in a known manner by mixing the active ingredients with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water.
Als Farbstoffe, die in den erfϊndungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle für derartige Zwecke üblichen Farbstoffe in Betracht. Dabei sind sowohl in Wasser wenig lösliche Pigmente als auch in Wasser lösliche Farbstoffe verwendbar. Als Beispiele genannt seien die unter den Bezeichnungen Rhodamin B, CI. Pigment Red 112 und CI. Solvent Red 1 bekannten Farbstoffe.Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, CI. Pigment Red 112 and CI. Solvent Red 1 known dyes.
Als Netzmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalin-Sulfonate, wie Diisopropyl- oder Diisobutylnaphthalin-Sulfonate.Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably usable are alkylnaphthalene sulfonates such as diisopropyl or diisobutylnaphthalene sulfonates.
Als Dispergiermittel und/oder Emulgatoren, die in den erfindungsgemäß verwendbaren Beizmittel- Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen nichtionischen, anionischen und kationischen Dispergiermittel in Betracht. Vorzugsweise verwendbar sind nichtionische oder anionische Dispergiermittel oder Gemische von nichtionischen oder anionischen Dispergiermitteln. Als geeignete nichtionische Dispergiermittel sind insbesondere Ethylenoxid-Propylenoxid Blockpolymere, Alkylphenolpolyglykolether sowie Tristryrylphenolpolyglykolether und deren phosphatierte oder sulfatierte Derivate zu nennen. Ge- eignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Polyacrylsäuresalze und Arylsulfonat-Formaldehydkondensate. AIs Entschäumer können in den erfϊndungsgemäß verwendbaren Beizmittel-Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen schaumhemmenden Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und Magnesiumstearat.Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates. As defoamers, all foam-inhibiting substances customary for the formulation of agrochemical active ingredients can be present in the seed dressing formulations which can be used according to the invention. Preferably usable are silicone defoamers and magnesium stearate.
Als Konservierungsmittel können in den erfϊndungsgemäß verwendbaren Beizmittel- Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und Benzylalkoholhemiformal.Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
Als sekundäre Verdickungsmittel, die in den erfmdungsgemaß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulosederivate, Acrylsäure- derivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure.Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly dispersed silicic acid.
Als Kleber, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle üblichen in Beizmitteln einsetzbaren Bindemittel in Frage. Vorzugsweise genannt seien Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose.Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
Als Gibberelline, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen vorzugsweise die Gibberelline Al, A3 (= Gibberellinsäure), A4 und A7 infrage, besonders bevorzugt verwendet man die Gibberellinsäure. Die Gibberelline sind bekannt (vgl. R. Wegler „Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel", Bd. 2, Springer Verlag, 1970, S. 401-412).Suitable gibberellins which may be present in the seed dressing formulations which can be used according to the invention are preferably the gibberellins Al, A3 (= gibberellic acid), A4 and A7, particularly preferably gibberellic acid. The gibberellins are known (see R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekungsmittel", Vol. 2, Springer Verlag, 1970, pp. 401-412).
Die erfindungsgemäß verwendbaren Beizmittel-Formulierungen können entweder direkt oder nach vorherigem Verdünnen mit Wasser zur Behandlung von Saatgut der verschiedensten Art, auch von Saatgut transgener Pflanzen, eingesetzt werden. Dabei können im Zusammenwirken mit den durch Expression gebildeten Substanzen auch zusätzliche synergistische Effekte auftreten.The seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds, including seed of transgenic plants. In this case, additional synergistic effects may occur in interaction with the substances formed by expression.
Zur Behandlung von Saatgut mit den erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder den daraus durch Zugabe von Wasser hergestellten Zubereitungen kommen alle üblicherweise für die Beizung einsetzbaren Mischgeräte in Betracht. Im einzelnen geht man bei der Beizung so vor, dass man das Saatgut in einen Mischer gibt, die jeweils gewünschte Menge an Beizmittel-Formulierungen entweder als solche oder nach vorherigem Verdünnen mit Wasser hinzufügt und bis zur gleichmäßigen Verteilung der Formulierung auf dem Saatgut mischt. Gegebenenfalls schließt sich ein Trocknungsvorgang an.For the treatment of seed with the seed dressing formulations which can be used according to the invention or the preparations prepared therefrom by the addition of water, all mixing devices customarily usable for the dressing can be considered. Specifically, in the pickling procedure, the seed is placed in a mixer which adds either desired amount of seed dressing formulations either as such or after prior dilution with water and mixes until evenly distributed the formulation on the seed. Optionally, a drying process follows.
Das erfindungsgemäße Behandlungsverfahren kann für die Behandlung von genetisch modifizierten Organismen (GMOs), z. B. Pflanzen oder Samen, verwendet werden. Genetisch modifizierte Pflanzen (oder transgene Pflanzen) sind Pflanzen, bei denen ein heterologes Gen stabil in das Genom integriert worden ist. Der Begriff "heterologes Gen" bedeutet im wesentlichen ein Gen, das außerhalb der Pflanze bereitgestellt oder assembliert wird und das bei Einführung in das Zellkerngenom, das Chloroplastengenom oder das Hypochondriengenom der transformierten Pflanze dadurch neue oder verbesserte agronomische oder sonstige Eigenschaften verleiht, daß es ein interessierendes Protein oder Polypeptid exprimiert oder daß es ein anderes Gen, das in der Pflanze vorliegt bzw. andere Gene, die in der Pflanze vorliegen, herunterreguliert oder abschaltet (zum Beispiel mittels Antisense-Technologie, Cosuppressionstechnologie oder RNAi-Technologie [RNA Interference]). Ein heterologes Gen, das im Genom vorliegt, wird ebenfalls als Transgen bezeichnet. Ein Transgen, das durch sein spezifisches Vorliegen im Pflanzengenom definiert ist, wird als Transformations- bzw. transgenes Event bezeichnet.The treatment method of the invention may be used for the treatment of genetically modified organisms (GMOs), e.g. As plants or seeds are used. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The term "heterologous gene" essentially refers to a gene which is provided or assembled outside the plant and which, when introduced into the nuclear genome, chloroplast genome or hypochondriacal genome, imparts new or improved agronomic or other properties to the transformed plant Expressing protein or polypeptide or that it is downregulating or shutting down another gene present in the plant or other genes present in the plant (for example by antisense technology, cosuppression technology or RNAi technology [RNA Interference]). A heterologous gene present in the genome is also referred to as a transgene. A transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
Zu Pflanzen und Pflanzensorten, die vorzugsweise erfindungsgemäß behandelt werden, zählen alle Pflanzen, die über Erbgut verfügen, das diesen Pflanzen besonders vorteilhafte, nützliche Merkmale verleiht (egal, ob dies durch Züchtung und/oder Biotechnologie erzielt wurde).Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material conferring on these plants particularly advantageous, useful features (whether obtained by breeding and / or biotechnology).
Pflanzen und Pflanzensorten, die ebenfalls vorzugsweise erfindungsgemäß behandelt werden, sind gegen einen oder mehrere biotische Streßfaktoren resistent, d. h. diese Pflanzen weisen eine verbesserte Abwehr gegen tierische und mikrobielle Schädlinge wie Nematoden, Insekten, Milben, phytopathogene Pilze, Bakterien, Viren und/oder Viroide auf.Plants and plant varieties which are also preferably treated according to the invention are resistant to one or more biotic stressors, i. H. These plants have an improved defense against animal and microbial pests such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.
Pflanzen und Pflanzensorten, die ebenfalls erfindungsgemäß behandelt werden können, sind solche Pflanzen, die gegen einen oder mehrere abiotische Streßfaktoren resistent sind. Zu den abiotischen Streßbedingungen können zum Beispiel Dürre, Kälte- und Hitzebedingungen, osmotischer Streß, Staunässe, erhöhter Bodensalzgehalt, erhöhtes Ausgesetztsein an Mineralien, Ozonbedingungen, Starklichtbedingungen, beschränkte Verfügbarkeit von Stickstoffnährstoffen, beschränkte Verfügbarkeit von Phosphornährstoffen oder Vermeidung von Schatten zählen.Plants and plant varieties which can also be treated according to the invention are those plants which are resistant to one or more abiotic stress factors. Abiotic stress conditions may include, for example, drought, cold and heat conditions, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients, or avoidance of shade.
Pflanzen und Pflanzensorten, die ebenfalls erfindungsgemäß behandelt werden können, sind solche Pflanzen, die durch erhöhte Ertragseigenschaften gekennzeichnet sind. Ein erhöhter Ertrag kann bei diesen Pflanzen z. B. auf verbesserter Pflanzenphysiologie, verbessertem Pflanzenwuchs und verbesserter Pflanzenentwicklung, wie Wasserverwertungseffizienz, Wasserhalteeffizienz, verbesserter Stickstoffverwertung, erhöhter Kohlenstoffassimilation, verbesserter Photosynthese, verstärkter Keimkraft und beschleunigter Abreife beruhen. Der Ertrag kann weiterhin durch eine verbesserte Pflanzenarchitektur (unter Streß- und nicht-Streß-Bedingungen) beeinflußt werden, darunter frühe Blüte, Kontrolle der Blüte für die Produktion von Hybridsaatgut, Keimpflanzenwüchsigkeit, Pfianzengröße, Intemodienzahl und -abstand, Wurzelwachstum, Samengröße, Fruchtgröße, Schotengröße, Schoten- oder Ährenzahl, Anzahl der Samen pro Schote oder Ähre, Samenmasse, verstärkte Samenfüllung, verringerter Samenausfall, verringertes Schotenplatzen sowie Standfestigkeit. Zu weiteren Ertragsmerkmalen zählen Samenzusammensetzung wie Kohlenhydratgehalt, Proteingehalt, Ölgehalt und Ölzusammensetzung, Nährwert, Verringerung der nährwidrigen Verbindungen, verbesserte Verarbeitbarkeit und verbesserte Lagerfähigkeit.Plants and plant varieties which can also be treated according to the invention are those plants which are characterized by increased yield properties. An increased yield can in these plants z. B. based on improved plant physiology, improved plant growth and improved plant development, such as water efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination and accelerated Abreife. The yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for hybrid seed production, seedling vigor, plant size, endemic number and spacing, root growth, seed size, fruit size, Pod size, pod or ear number, number of seeds per pod or ear, seed mass, increased seed filling, decreased seed drop, decreased Pod popping and stability. Other yield-related traits include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction of nontoxic compounds, improved processability, and improved shelf life.
Pflanzen, die erflndungsgemäß behandelt werden können, sind Hybridpflanzen, die bereits die Eigenschaften der Heterosis bzw. des Hybrideffekts exprimieren, was im allgemeinen zu höherem Ertrag, höherer Wüchsigkeit, besserer Gesundheit und besserer Resistenz gegen biotische und abiotische Streßfaktoren führt. Solche Pflanzen werden typischerweise dadurch erzeugt, daß man eine ingezüchtete pollensterile Elternlinie (den weiblichen Kreuzungspartner) mit einer anderen ingezüchteten pollenfertilen Elternlinie (dem männlichen Kreuzungspartner) kreuzt. Das Hybridsaatgut wird typischerweise von den pollensterilen Pflanzen geerntet und an Vermehrer verkauft. Pollensterile Pflanzen können manchmal (z. B. beim Mais) durch Entfahnen (d. h. mechanischem Entfernen der männlichen Geschlechtsorgane bzw. der männlichen Blüten), produziert werden; es ist jedoch üblicher, daß die Pollensterilität auf genetischen Determinanten im Pflanzengenom beruht. In diesem Fall, insbesondere dann, wenn es sich bei dem gewünschten Produkt, da man von den Hybridpflanzen ernten will, um die Samen handelt, ist es üblicherweise günstig, sicherzustellen, daß die Pollenfertilität in Hybridpflanzen, die die für die Pollensterilität verantwortlichen genetischen Determinanten enthalten, völlig restoriert wird. Dies kann erreicht werden, indem sichergestellt wird, daß die männlichen Kreuzungspartner entsprechende Fertilitätsrestorergene besitzen, die in der Lage sind, die Pollenfertilität in Hybridpflanzen, die die genetischen Determinanten, die für die Pollensterilität verantwortlich sind, enthalten, zu restorieren. Genetische Determinanten für Pollensterilität können im Cytoplasma lokalisiert sein. Beispiele für cytoplasmatische Pollensterilität (CMS) wurden zum Beispiel für Brassica-Arten beschrieben (WO 1992/005251, WO 1995/009910, WO 1998/27806, WO 2005/002324, WO 2006/021972 und US 6,229,072). Genetische Determinanten für Pollensterilität können jedoch auch im Zellkerngenom lokalisiert sein. Pollensterile Pflanzen können auch mit Methoden der pflanzlichen Biotechnologie, wie Gentechnik, erhalten werden. Ein besonders günstiges Mittel zur Erzeugung von pollensterilen Pflanzen ist in WO 89/10396 beschrieben, wobei zum Beispiel eine Ribonuklease wie eine Barnase selektiv in den Tapetumzellen in den Staubblättern exprimiert wird. Die Fertilität kann dann durch Expression eines Ribonukleasehernmers wie Barstar in den Tapetumzellen restoriert werden (z. B. WO 1991/002069).Plants which can be treated according to the invention are hybrid plants which already express the properties of the heterosis or the hybrid effect, which generally leads to higher yield, higher vigor, better health and better resistance to biotic and abiotic stress factors. Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner). The hybrid seed is typically harvested from the male sterile plants and sold to propagators. Pollen sterile plants can sometimes be produced (eg in maize) by delaving (i.e., mechanically removing male genitalia or male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome. In this case, especially when the desired product, as one wants to harvest from the hybrid plants, is the seeds, it is usually beneficial to ensure that the pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility , completely restored. This can be accomplished by ensuring that the male crossing partners possess appropriate fertility restorer genes capable of restoring pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility. Genetic determinants of pollen sterility may be localized in the cytoplasm. Examples of cytoplasmic male sterility (CMS) have been described, for example, for Brassica species (WO 1992/005251, WO 1995/009910, WO 1998/27806, WO 2005/002324, WO 2006/021972 and US 6,229,072). However, genetic determinants of pollen sterility may also be localized in the nuclear genome. Pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering. A particularly convenient means of producing male-sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens. The fertility can then be restorated by expression of a ribonuclease hernmer such as barstar in the tapetum cells (eg WO 1991/002069).
Pflanzen oder Pflanzensorten (die mit Methoden der Pflanzenbiotechnologie, wie der Gentechnik, erhalten werden), die erfindungsgemäß behandelt werden können, sind herbizidtolerante Pflanzen, d. h. Pflanzen, die gegenüber einem oder mehreren vorgegebenen Herbiziden tolerant gemacht worden sind. Solche Pflanzen können entweder durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Herbizidtoleranz verleiht, erhalten werden.Plants or plant varieties (obtained by methods of plant biotechnology, such as genetic engineering) which can be treated according to the invention are herbicidally tolerant plants, ie plants that have been tolerated to one or more given herbicides. Such plants can either be through genetic transformation or through Selection of plants containing a mutation conferring such herbicide tolerance.
Herbizidtolerante Pflanzen sind zum Beispiel glyphosatetolerante Pflanzen, d. h. Pflanzen, die gegenüber dem Herbizid Glyphosate oder dessen Salzen tolerant gemacht worden sind. So können zum Beispiel glyphosatetolerante Pflanzen durch Transformation der Pflanze mit einem Gen, das für das Enzym 5-Enolpyruvylshikimat-3-phosphatsynthase (EPSPS) kodiert, erhalten werden. Beispiele für solche EPSPS-Gene sind das AroA-Gen (Mutante CT7) des Bakterium Sahnonella typhimurium (Comai et al., Science (1983), 221, 370-371), das CP4-Gen des Bakteriums Agrobacterium sp. (Barry et al., Curr. Topics Plant Physiol. (1992), 7, 139-145), die Gene, die für eine EPSPS aus der Petunie (Shah et al., Science (1986), 233, 478-481), für eine EPSPS aus der Tomate (Gasser et al., J. Biol. Chem. (1988), 263, 4280-4289) oder für eine EPSPS aus Eleusine (WO 2001/66704) kodieren. Es kann sich auch um eine mutierte EPSPS handeln, wie sie zum Beispiel in EP-A 0837944, WO 2000/066746, WO 2000/066747 oder WO 2002/026995 beschrieben ist. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, daß man ein Gen exprimiert, das für ein Glyphosate-Oxidoreduktase-Enzym, wie es in US 5,776,760 und US 5,463,175 beschrieben ist, kodiert. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, daß man ein Gen exprimiert, das für ein Glyphosate-acetyltransferase-Enzym, wie es in z. B. WO 2002/036782, WO 2003/092360, WO 2005/012515 und WO 2007/024782 beschrieben ist, kodiert. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, daß man Pflanzen, die natürlich vorkommende Mutationen der oben erwähnten Gene, wie sie zum Beispiel in WO 2001/024615 oder WO 2003/013226 beschrieben sind, enthalten, selektiert.Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H. Plants tolerant to the herbicide glyphosate or its salts. Thus, for example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Sahnonella typhimurium (Comai et al., Science (1983), 221, 370-371), the bacterium Agrobacterium sp. (Barry et al., Curr Topics Plant Physiol. (1992), 7, 139-145), the genes that are useful for EPSPS from the petunia (Shah et al., Science (1986), 233, 478-481). , for an EPSPS from the tomato (Gasser et al., J. Biol. Chem. (1988), 263, 4280-4289) or for an EPSPS from Eleusine (WO 2001/66704) encode. It can also be a mutated EPSPS, as described, for example, in EP-A 0837944, WO 2000/066746, WO 2000/066747 or WO 2002/026995. Glyphosate-tolerant plants can also be obtained by expressing a gene coding for a glyphosate oxidoreductase enzyme as described in US 5,776,760 and US 5,463,175. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in, e.g. As WO 2002/036782, WO 2003/092360, WO 2005/012515 and WO 2007/024782 is encoded. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above-mentioned genes, as described, for example, in WO 2001/024615 or WO 2003/013226.
Sonstige herbizidresistente Pflanzen sind zum Beispiel Pflanzen, die gegenüber Herbiziden, die das Enzym Glutaminsynthase hemmen, wie Bialaphos, Phosphinotricin oder Glufosinate, tolerant gemacht worden sind. Solche Pflanzen können dadurch erhalten werden, daß man ein Enzym exprimiert, das das Herbizid oder eine Mutante des Enzyms Glutaminsynthase, das gegenüber Hemmung resistent ist, entgiftet. Solch ein wirksames entgiftendes Enzym ist zum Beispiel ein Enzym, das für ein Phosphinotricin-acetyltransferase kodiert (wie zum Beispiel das bar- oder pat- Protein aus Streptomyces-Arten). Pflanzen, die eine exogene Phosphinotricin-acetyltransferase exprimieren, sind zum Beispiel in US 5,561,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 und US 7,112,665 beschrieben.Other herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate. Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition. Such an effective detoxifying enzyme is, for example, an enzyme encoding a phosphinotricin acetyltransferase (such as the bar or pat protein of Streptomyces species). Plants expressing an exogenous phosphinotricin acetyltransferase are described, for example, in US 5,561,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 and US 7,112,665.
Weitere herbizidtolerante Pflanzen sind auch Pflanzen, die gegenüber den Herbiziden, die das Enzym Hydroxyphenylpyruvatdioxygenase (HPPD) hemmen, tolerant gemacht worden sind. Bei den Hydroxyphenylpyruvatdioxygenasen handelt es sich um Enzyme, die die Reaktion, in der para-Hydroxyphenylpyruvat (HPP) zu Homogentisat umgesetzt wird, katalysieren. Pflanzen, die gegenüber HPPD-Hemmern tolerant sind, können mit einem Gen, das für ein natürlich vorkommendes resistentes HPPD-Enzym kodiert oder einem Gen, das für ein mutiertes HPPD- Enzym gemäß WO 1996/038567, WO 1999/024585 und WO 1999/024586 kodiert, transformiert werden. Eine Toleranz gegenüber HPPD-Hemmern kann auch dadurch erzielt werden, daß man Pflanzen mit Genen transformiert, die für gewisse Enzyme kodieren, die die Bildung von Homogentisat trotz Hemmung des nativen HPPD-Enzyms durch den HPPD-Hemmer ermöglichen. Solche Pflanzen und Gene sind in WO 1999/034008 und WO 2002/36787 beschrieben. Die Toleranz von Pflanzen gegenüber HPPD-Hemmern kann auch dadurch verbessert werden, daß man Pflanzen zusätzlich zu einem Gen, das für ein HPPD-tolerantes Enzym kodiert, mit einem Gen transformiert, das für ein Prephenatdehydrogenase-Enzym kodiert, wie dies in WO 2004/024928 beschrieben ist.Further herbicide-tolerant plants are also plants tolerant to the herbicides which inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD). The hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate. Plants that are tolerant to HPPD inhibitors, can be encoded with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant HPPD enzyme according to WO 1996/038567, WO 1999/024585 and WO 1999/024586, be transformed. Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 1999/034008 and WO 2002/36787. The tolerance of plants to HPPD inhibitors can also be improved by transforming plants in addition to a gene coding for an HPPD-tolerant enzyme with a gene coding for a prephenate dehydrogenase enzyme, as described in WO 2004 / 024928 is described.
Weitere herbizidresistente Pflanzen sind Pflanzen, die gegenüber Acetolactatsynthase (ALS)- Hemmern tolerant gemacht worden sind. Zu bekannten ALS-Hemmern zählen zum Beispiel Sulfonylharnstoff, Imidazolinon, Triazolopyrimidine, Pyrimidinyloxy(thio)benzoate und/oder Sulfonylaminocarbonyltriazolinon-Herbizide. Es ist bekannt, daß verschiedene Mutationen im Enzym ALS (auch als Acetohydroxysäure-Synthase, AHAS, bekannt) eine Toleranz gegenüber unterschiedlichen Herbiziden bzw. Gruppen von Herbiziden verleihen, wie dies zum Beispiel bei Tranel und Wright, Weed Science (2002), 50, 700-712, jedoch auch in US 5,605,011, US 5,378,824, US 5,141,870 und US 5,013,659, beschrieben ist. Die Herstellung von sulfonylharnstofftoleranten Pflanzen und imidazolinontoleranten Pflanzen ist in US 5,605,011; US 5,013,659; US 5,141,870; US 5,767,361; US 5,731,180; US 5,304,732; US 4,761,373; US 5,331,107; US 5,928,937; und US 5,378,824; sowie in der internationalen Veröffentlichung WO 1996/033270 beschrieben. Weitere imidazolinontolerante Pflanzen sind auch in z. B. WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351 und WO 2006/060634 beschrieben. Weitere sulfonylharnstoff- und imidazolinontolerante Pflanzen sind auch in z.B. WO 2007/024782 beschrieben.Other herbicide-resistant plants are plants that have been tolerated to acetolactate synthase (ALS) inhibitors. Examples of known ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides. It is known that various mutations in the enzyme ALS (also known as acetohydroxy acid synthase, AHAS) confer tolerance to different herbicides or groups of herbicides, as described, for example, by Tranel and Wright, Weed Science (2002), 50, 700-712, but also in US 5,605,011, US 5,378,824, US 5,141,870 and US 5,013,659. The preparation of sulfonylurea tolerant plants and imidazolinone tolerant plants is described in US 5,605,011; US 5,013,659; US 5,141,870; US 5,767,361; US 5,731,180; US 5,304,732; US 4,761,373; US 5,331,107; US 5,928,937; and US 5,378,824; as well as in international publication WO 1996/033270. Other imidazolinontolerante plants are also in z. WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351 and WO 2006/060634. Other sulfonylurea and imidazolinone tolerant plants are also disclosed in e.g. WO 2007/024782 described.
Weitere Pflanzen, die gegenüber Imidazolinon und/oder Sulfonylharnstoff tolerant sind, können durch induzierte Mutagenese, Selektion in Zellkulturen in Gegenwart des Herbizids oder durch Mutationszüchtung erhalten werden, wie dies zum Beispiel für die Sojabohne in US 5,084,082, für Reis in WO 1997/41218, für die Zuckerrübe in US 5,773,702 und WO 1999/057965, für Salat in US 5,198,599 oder für die Sonnenblume in WO 2001/065922 beschrieben ist.Other plants which are tolerant to imidazolinone and / or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding, as for example for the soybean in US 5,084,082, for rice in WO 1997/41218, for the sugar beet in US 5,773,702 and WO 1999/057965, for salad in US 5,198,599 or for the sunflower in WO 2001/065922.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls erfϊndungsgemäß behandelt werden können, sind insektenresistente transgene Pflanzen, d.h. Pflanzen, die gegen Befall mit gewissen Zielinsekten resistent gemacht wurden. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Insektenresistenz verleiht, erhalten werden.Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated according to the invention are insect-resistant transgenic plants, ie plants which are resistant to attack by certain target insects were made resistant. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance.
Der Begriff "insektenresistente transgene Pflanze" umfaßt im vorliegenden Zusammenhang jegliche Pflanze, die mindestens ein Transgen enthält, das eine Kodiersequenz umfaßt, die für folgendes kodiert:The term "insect-resistant transgenic plant" as used herein includes any plant containing at least one transgene comprising a coding sequence encoding:
1) ein insektizides Kristallprotein aus Bacillus thuringiensis oder einen insektiziden Teil davon, wie die insektiziden Kristallproteine, die von Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, von Crickmore et al. (2005) in der Bacillus thuringiensis- Toxinnomenklatur aktualisiert, online bei: http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), zusammengestellt wurden, oder insektizide Teile davon, z.B. Proteine der Cry-Proteinklassen CrylAb, CrylAc, CrylF, Cry2Ab, Cry3Ae oder Cry3Bb oder insektizide Teile davon; oder1) an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof, such as the insecticidal crystal proteins described by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature, online at: http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal parts thereof, e.g. Proteins of the cry protein classes CrylAb, CrylAc, CrylF, Cry2Ab, Cry3Ae or Cry3Bb or insecticidal parts thereof; or
2) ein Kristallprotein aus Bacillus thuringiensis oder einen Teil davon, der in Gegenwart eines zweiten, anderen Kristallproteins als Bacillus thuringiensis oder eines Teils davon insektizid wirkt, wie das binäre Toxin, das aus den Kristallproteinen Cy34 und Cy35 besteht (Moellenbeck et al., Nat. Biotechnol. (2001), 19, 668-72; Schnepf et al., Applied Environm. Microb. (2006), 71, 1765-1774); oder2) a crystal protein from Bacillus thuringiensis or a part thereof which is insecticidal in the presence of a second, different crystal protein than Bacillus thuringiensis or a part thereof, such as the binary toxin consisting of the crystal proteins Cy34 and Cy35 (Moellenbeck et al., Nat Biotechnol. (2001), 19, 668-72; Schnepf et al., Applied Environment Microb. (2006), 71, 1765-1774); or
3) ein insektizides Hybridprotein, das Teile von zwei unterschiedlichen insektiziden Kristallproteinen aus Bacillus thuringiensis umfaßt, wie zum Beispiel ein Hybrid aus den3) an insecticidal hybrid protein comprising parts of two different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the
Proteinen von 1) oben oder ein Hybrid aus den Proteinen von 2) oben, z. B. das Protein CrylA.105, das von dem Mais-Event MON98034 produziert wird (WO 2007/027777); oderProteins of 1) above or a hybrid of the proteins of 2) above, e.g. The protein CrylA.105 produced by the corn event MON98034 (WO 2007/027777); or
4) ein Protein gemäß einem der Punkte 1) bis 3) oben, in dem einige, insbesondere 1 bis 10, Aminosäuren durch eine andere Aminosäure ersetzt wurden, um eine höhere insektizide Wirksamkeit gegenüber einer Zielinsektenart zu erzielen und/oder um das Spektrum der entsprechenden Zielinsektenarten zu erweitern und/oder wegen Veränderungen, die in die Kodier- DNA während der Klonierung oder Transformation induziert wurden, wie das Protein Cry3Bb 1 in Mais-Events MON863 oder MON88017 oder das Protein Cry3A im Mais-Event MIR 604; oder4) a protein according to any of items 1) to 3) above, in which some, in particular 1 to 10, amino acids have been replaced by another amino acid in order to achieve a higher insecticidal activity against a target insect species and / or the spectrum of the corresponding To expand target insect species and / or due to changes induced in the coding DNA during cloning or transformation, such as the protein Cry3Bb 1 in maize events MON863 or MON88017 or the protein Cry3A in the maize event MIR 604; or
5) ein insektizides sezerniertes Protein aus Bacillus thuringiensis oder Bacillus cereus oder einen insektiziden Teil davon, wie die vegetativ wirkenden insektentoxischen Proteine5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus or an insecticidal part thereof, such as the vegetative insecticidal proteins
(vegetative insekticidal proteins, VIP), die unter http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/vip.html angeführt sind, z. B. Proteine der Proteinklasse VIP3Aa; oder(vegetative insecticidal proteins, VIP), which are under http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/vip.html are listed, for. B. Proteins of protein class VIP3Aa; or
6) ein sezerniertes Protein aus Bacillus thuringiensis oder Bacillus cereus, das in Gegenwart eines zweiten sezernierten Proteins aus Bacillus thuringiensis oder B. cereus insektizid wirkt, wie das binäre Toxin, das aus den Proteinen VIPlA und VIP2A besteht (WO 1994/21795); oder6) a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin consisting of the proteins VIPlA and VIP2A (WO 1994/21795); or
7) ein insektizides Hybridprotein, das Teile von verschiedenen sezernierten Proteinen von Bacillus thuringiensis oder Bacillus cereus umfaßt, wie ein Hybrid der Proteine von 1) oder ein Hybrid der Proteine von 2) oben; oder7) a hybrid insecticidal protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or
8) ein Protein gemäß einem der Punkte 1) bis 3) oben, in dem einige, insbesondere 1 bis8) a protein according to any one of items 1) to 3) above, in which some, in particular 1 to
10, Aminosäuren durch eine andere Aminosäure ersetzt wurden, um eine höhere insektizide Wirksamkeit gegenüber einer Zielinsektenart zu erzielen und/oder um das Spektrum der entsprechenden Zielinsektenarten zu erweitern und/oder wegen Veränderungen, die in die Kodier- DNA während der Klonierung oder Transformation induziert wurden (wobei die Kodierung für ein insektizides Protein erhalten bleibt), wie das Protein VIP3Aa im Baumwoll-Event COT 102.10, amino acids have been replaced with another amino acid to achieve higher insecticidal activity against a target insect species and / or to broaden the spectrum of the corresponding target insect species and / or due to changes induced in the coding DNA during cloning or transformation (preserving the coding for an insecticidal protein), such as the protein VIP3Aa in cotton event COT 102.
Natürlich zählt zu den insektenresistenten transgenen Pflanzen im vorliegenden Zusammenhang auch jegliche Pflanze, die eine Kombination von Genen umfaßt, die für die Proteine von einer der oben genannten Klassen 1 bis 8 kodieren. In einer Ausführungsform enthält eine insektenresistente Pflanze mehr als ein Transgen, das für ein Protein nach einer der oben genannten 1 bis 8 kodiert, um das Spektrum der entsprechenden Zielinsektenarten zu erweitern oder um die Entwicklung einer Resistenz der Insekten gegen die Pflanzen dadurch hinauszuzögern, daß man verschiedene Proteine einsetzt, die für dieselbe Zielinsektenart insektizid sind, jedoch eine unterschiedliche Wirkungsweise, wie Bindung an unterschiedliche Rezeptorbindungsstellen im Insekt, aufweisen.Of course, insect-resistant transgenic plants in the present context also include any plant comprising a combination of genes encoding the proteins of any of the above classes 1 to 8. In one embodiment, an insect-resistant plant contains more than one transgene encoding a protein of any one of the above 1 to 8 in order to extend the spectrum of the corresponding target insect species or to delay the development of resistance of the insects to the plants by use different proteins which are insecticidal for the same target insect species, but have a different mode of action, such as binding to different receptor binding sites in the insect.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls erfmdungsgemäß behandelt werden können, sind gegenüber abiotischen Streßfaktoren tolerant. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Streßresistenz verleiht, erhalten werden. Zu besonders nützlichen Pflanzen mit Streßtoleranz zählen folgende:Plants or plant varieties (obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are tolerant of abiotic stressors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such stress resistance. Particularly useful plants with stress tolerance include the following:
a. Pflanzen, die ein Transgen enthalten, das die Expression und/oder Aktivität des Gens für die Poly(ADP-ribose)polymerase (PARP) in den Pflanzenzellen oder Pflanzen zu reduzieren vermag, wie dies in WO 2000/004173 oder EP 04077984.5 oder EP 06009836.5 beschrieben ist. b. Pflanzen, die ein streßtoleranzforderndes Transgen enthalten, das die Expression und/oder Aktivität der für PARG kodierenden Gene der Pflanzen oder Pflanzenzellen zu reduzieren vermag, wie dies z.B. in WO 2004/090140 beschrieben ist;a. Plants which contain a transgene capable of reducing the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or plants, as described in WO 2000/004173 or EP 04077984.5 or EP 06009836.5 is described. b. Plants which contain a stress tolerance-promoting transgene capable of reducing the expression and / or activity of the PARG-encoding genes of the plants or plant cells, as described, for example, in WO 2004/090140;
c. Pflanzen, die ein streßtoleranzforderndes Transgen enthalten, das für ein in Pflanzen funktionelles Enzym des Nicotinamidadenindinukleotid-Salvage-Biosynthesewegs kodiert, darunter Nicotinamidase, Nicotinatphosphoribosyltransferase, Nicotinsäuremono-nukleotidadenyl- transferase, Nicotinamidadenindinukleotidsynthetase oder Nicotinamid-phosphoribosyltransferase, wie dies z. B. in EP 04077624.7 oder WO 2006/133827 oder PCT/EP07/002433 beschrieben ist.c. Plants containing a stress tolerance-promoting transgene encoding a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthesis pathway, including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid nucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase, as described e.g. As described in EP 04077624.7 or WO 2006/133827 or PCT / EP07 / 002433.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls erfindungsgemäß behandelt werden können, weisen eine veränderte Menge, Qualität und/oder Lagerfähigkeit des Ernteprodukts und/oder veränderte Eigenschaften von bestimmten Bestandteilen des Ernteprodukts auf, wie zum Beispiel:Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated according to the invention have a changed amount, quality and / or storability of the harvested product and / or altered characteristics of certain components of the harvested product, such as:
1) Transgene Pflanzen, die eine modifizierte Stärke synthetisieren, die bezüglich ihrer chemisch-physikalischen Eigenschaften, insbesondere des Amylosegehalts oder des Amylose/Amylopektin- Verhältnisses, des Verzweigungsgrads, der durchschnittlichen Kettenlänge, der Verteilung der Seitenketten, des Viskositätsverhaltens, der Gelfestigkeit, der Stärkekorngröße und/oder Stärkekornmorphologie im Vergleich mit der synthetisierten Stärke in Wildtyppflanzenzellen oder -pflanzen verändert ist, so daß sich diese modifizierte Stärke besser für bestimmte Anwendungen eignet. Diese transgenen Pflanzen, die eine modifizierte Stärke synthetisieren, sind zum Beispiel in EP 0571427, WO 1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581, WO 1996/27674, WO 1997/11188, WO 1997/26362, WO 1997/32985, WO 1997/42328, WO 1997/44472, WO 1997/45545, WO 1998/27212, WO 1998/40503, WO 99/58688, WO 1999/58690, WO 1999/58654, WO 2000/008184, WO 2000/008185, WO 2000/28052, WO 2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO 2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823, WO 2000/22140, WO 2006/063862, WO 2006/072603, WO 2002/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP 07090009.7, WO 2001/14569, WO 2002/79410, WO 2003/33540, WO 2004/078983, WO 2001/19975, WO 1995/26407, WO 1996/34968, WO 1998/20145, WO 1999/12950, WO 1999/66050, WO 1999/53072, US 6,734,341, WO 2000/11192, WO 1998/22604, WO 1998/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US 5,824,790, US 6,013,861, WO 1994/004693, WO 1994/009144, WO 1994/11520, WO 1995/35026 bzw. WO 1997/20936 beschrieben. 2) Transgene Pflanzen, die Nichtstärkekohlenhydratpolymere synthetisieren, oder Nichtstärkekohlenhydratpolymere, deren Eigenschaften im Vergleich zu Wildtyppflanzen ohne genetische Modifikation verändert sind. Beispiele sind Pflanzen, die Polyfructose, insbesondere des Inulin- und Levantyps, produzieren, wie dies in EP 0663956, WO 1996/001904, Wo 1996/021023, WO 1998/039460 und WO 1999/024593 beschrieben ist, Pflanzen, die alpha- 1,4- Glucane produzieren, wie dies in WO 1995/031553, US 2002/031826, US 6,284,479, US 5,712,107, WO 1997/047806, WO 1997/047807, WO 1997/047808 und WO 2000/14249 beschrieben ist, Pflanzen, die alpha- 1 ,6-verzweigte alpha- 1,4-Glucane produzieren, wie dies in WO 2000/73422 beschrieben ist, und Pflanzen, die Alternan produzieren, wie dies in WO 2000/047727, EP 06077301.7, US 5,908,975 und EP 0728213 beschrieben ist.1) Transgenic plants which synthesize a modified starch with respect to their physicochemical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of the side chains, the viscosity behavior, the gel strength, the starch grain size and / or starch grain morphology is altered in comparison to the synthesized starch in wild-type plant cells or plants, so that this modified starch is better suited for certain applications. These transgenic plants which synthesize a modified starch are described, for example, in EP 0571427, WO 1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581, WO 1996/27674, WO 1997/11188, WO 1997/26362, WO 1997/32985, WO 1997/42328, WO 1997/44472, WO 1997/45545, WO 1998/27212, WO 1998/40503, WO 99/58688, WO 1999/58690, WO 1999/58654, WO 2000/008184, WO 2000/008185, WO 2000/28052, WO 2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO 2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823, WO 2000/22140, WO 2006/063862, WO 2006/072603, WO 2002/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP 07090009.7, WO 2001/14569, WO 2002/79410, WO 2003/33540, WO 2004/078983, WO 2001/19975, WO 1995/26407, WO 1996/34968, WO 1998/20145, WO 1999/12950, WO 1999/66050, WO 1999/53072, US Pat. No. 6,734,341, WO 2000/11192, WO 1998/2 2604, WO 1998/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US 5,824,790, US 6,013,861, WO 1994/004693, WO 1994/009144, WO 1994/11520, WO 1995/35026 and WO, respectively 1997/20936. 2) Transgenic plants that synthesize non-starch carbohydrate polymers or non-starch carbohydrate polymers whose properties are altered compared to wild-type plants without genetic modification. Examples are plants which produce polyfructose, in particular of the inulin and levan type, as described in EP 0663956, WO 1996/001904, WO 1996/021023, WO 1998/039460 and WO 1999/024593, plants which are alpha-1 To produce 4-glucans, as described in WO 1995/031553, US 2002/031826, US 6,284,479, US 5,712,107, WO 1997/047806, WO 1997/047807, WO 1997/047808 and WO 2000/14249, plants which alpha-1, 6-branched alpha-1,4-glucans, as described in WO 2000/73422, and plants producing alternan, as described in WO 2000/047727, EP 06077301.7, US 5,908,975 and EP 0728213 is.
3) Transgene Pflanzen, die Hyaluronan produzieren, wie dies zum Beispiel in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, JP 2006/304779 und WO 2005/012529 beschrieben ist.3) Transgenic plants producing hyaluronan, as described, for example, in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, JP 2006/304779 and WO 2005/012529.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls erfindungsgemäß behandelt werden können, sind Pflanzen wie Baumwollpflanzen mit veränderten Fasereigenschaften. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solche veränderten Fasereigenschaften verleiht, erhalten werden; dazu zählen:Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; these include:
a) Pflanzen wie Baumwollpflanzen, die eine veränderte Form von Cellulosesynthasegenen enthalten, wie dies in WO 1998/000549 beschrieben ist,a) plants, such as cotton plants, which contain an altered form of cellulose synthase genes, as described in WO 1998/000549,
b) Pflanzen wie Baumwollpflanzen, die eine veränderte Form von rsw2- oder rsw3- homologen Nukleinsäuren enthalten, wie dies in WO 2004/053219 beschrieben ist;b) plants, such as cotton plants, which contain an altered form of rsw2 or rsw3 homologous nucleic acids, as described in WO 2004/053219;
c) Pflanzen wie Baumwollpflanzen mit einer erhöhten Expression der Saccharosephosphatsynthase, wie dies in WO 2001/017333 beschrieben ist;c) plants such as cotton plants having increased expression of sucrose phosphate synthase as described in WO 2001/017333;
d) Pflanzen wie Baumwollpflanzen mit einer erhöhten Expression derd) plants such as cotton plants with an increased expression of
Saccharosesynthase, wie dies in WO 02/45485 beschrieben ist;Sucrose synthase as described in WO 02/45485;
e) Pflanzen wie Baumwollpflanzen bei denen der Zeitpunkt der Durchlaßsteuerung der Plasmodesmen an der Basis der Faserzelle verändert ist, z. B. durch Herunterregulieren der faserselektiven ß-l,3-Glucanase, wie dies in WO 2005/017157 beschrieben ist; f) Pflanzen wie Baumwollpflanzen mit Fasern mit veränderter Reaktivität, z. B. durch Expression des N-Acetylglucosamintransferasegens, darunter auch nodC, und von Chitinsynthasegenen, wie dies in WO 2006/136351 beschrieben ist.e) plants such as cotton plants in which the timing of the passage control of the Plasmodesmen is changed at the base of the fiber cell, z. By down-regulating the fiber-selective β-l, 3-glucanase, as described in WO 2005/017157; f) plants such as cotton plants with modified reactivity fibers, e.g. By expression of the N-acetylglucosamine transferase gene, including nodC, and chitin synthase genes, as described in WO 2006/136351.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls erfindungsgemäß behandelt werden können, sind Pflanzen wie Raps oder verwandte Brassica-Pflanzen mit veränderten Eigenschaften der Ölzusammensetzung. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solche veränderten Öleigenschaften verleiht, erhalten werden; dazu zählen:Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated according to the invention are plants such as oilseed rape or related Brassica plants with altered oil composition properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; these include:
a) Pflanzen wie Rapspflanzen, die Öl mit einem hohen Ölsäuregehalt produzieren, wie dies zum Beispiel in US 5,969,169, US 5,840,946 oder US 6,323,392 oder US 6,063, 947 beschrieben ist;a) plants such as rape plants producing oil of high oleic acid content, as described, for example, in US 5,969,169, US 5,840,946 or US 6,323,392 or US 6,063,947;
b) Pflanzen wie Rapspflanzen, die Öl mit einem niedrigen Linolensäuregehalt produzieren, wie dies in US 6,270828, US 6,169,190 oder US 5,965,755 beschrieben ist.b) plants such as oilseed rape plants which produce low linolenic acid oil, as described in US 6,270,828, US 6,169,190 or US 5,965,755.
c) Pflanzen wie Rapspflanzen, die Öl mit einem niedrigen gesättigten Fettsäuregehalt produzieren, wie dies z. B. in US 5,434,283 beschrieben ist.c) plants such as oilseed rape plants which produce oil with a low saturated fatty acid content, such as e.g. As described in US 5,434,283.
Besonders nützliche transgene Pflanzen, die erfindungsgemäß behandelt werden können, sind Pflanzen mit einem oder mehreren Genen, die für ein oder mehrere Toxine kodieren, sind die transgenen Pflanzen, die unter den folgenden Handelsbezeichnungen angeboten werden: YTELD GARD® (zum Beispiel Mais, Baumwolle, Sojabohnen), KnockOut® (zum Beispiel Mais), BiteGard® (zum Beispiel Mais), BT-Xtra® (zum Beispiel Mais), StarLink® (zum Beispiel Mais), Bollgard® (Baumwolle), Nucotn® (Baumwolle), Nucotn 33B® (Baumwolle), NatureGard® (zum Beispiel Mais), Protecta® und NewLeaf® (Kartoffel). Herbizidtolerante Pflanzen, die zu erwähnen sind, sind zum Beispiel Maissorten, Baumwollsorten und Sojabohnensorten, die unter den folgenden Handelsbezeichnungen angeboten werden: Roundup Ready® (Glyphosatetoleranz, zum Beispiel Mais, Baumwolle, Sojabohne), Liberty Link® (Phosphinotricintoleranz, zum Beispiel Raps), IMI® (Imidazolinontoleranz) und SCS® (Sylfonylharnstofftoleranz), zum Beispiel Mais. Zu den herbizidresistenten Pflanzen (traditionell auf Herbizidtoleranz gezüchtete Pflanzen), die zu erwähnen sind, zählen die unter der Bezeichnung Clearfield® angebotenen Sorten (zum Beispiel Mais).Particularly useful transgenic plants which can be treated according to the invention are plants having one or more genes which code for one or more toxins, the transgenic plants sold under the following tradenames: YTELD GARD® (for example corn, cotton, Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example corn), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato). Herbicide-tolerant crops to be mentioned are, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready® (glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example rapeseed) , IMI® (imidazolinone tolerance) and SCS® (sylphonylurea tolerance), for example corn. Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).
Besonders nützliche transgene Pflanzen, die erfindungsgemäß behandelt werden können, sind Pflanzen, die Transformations-Events, oder eine Kombination von Transformations-Events, enthalten und die zum Beispiel in den Dateien von verschiedenen nationalen oder regionalen Behörden angeführt sind (siehe zum Beispiel http://gmoinfo.jrc.it/gmp_browse.aspx und http://www.agbios.com/dbase.php).Particularly useful transgenic plants which can be treated according to the invention are plants, the transformation events, or a combination of transformation events, for example, in the files of various national or regional authorities (see, for example, http://gmoinfo.jrc.it/gmp_browse.aspx and http://www.agbios.com/dbase.php).
Die erfindungsgemäßen Wirkstoffe wirken nicht nur gegen Pflanzen-, Hygiene- und Vorratsschädlinge, sondern auch auf dem veterinärmedizinischen Sektor gegen tierische Parasiten (Ekto- und Endoparasiten) wie Schildzecken, Lederzecken, Räudemilben, Laufmilben, Fliegen (stechend und leckend), parasitierende Fliegenlarven, Läuse, Haarlinge, Federlinge und Flöhe. Zu diesen Parasiten gehören:The active compounds of the invention not only against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ecto- and endoparasites) such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice , Hair pieces, 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..From the order of Mallophagida and suborders Amblycerina and Ischnocerina, for example. 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., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp.,From the order Diptera and the suborders Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp , Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp.,
Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia 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..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., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp..From the order of siphonapterida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
Aus der Ordnung der Heteropterida z.B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp..From the order of the heteropterid e.g. 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 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.. Aus der Ordnung der Actinedida (Prostigmata) und Acaridida (Astigmata) z.B. Acarapis spp., Cheyletiella spp., Ornithocheyletia 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 subclass of Acari (Acarina) and the orders of meta and mesostigmata eg 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 order of Actinedida (Prostigmata) and Acaridida (Astigmata) eg Acarapis spp., Cheyletiella spp., Ornithocheyletia 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.
Die erfindungsgemäßen 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 Versuchstiere, 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 controlling arthropods which are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice. By controlling these arthropods deaths and reductions in performance (in meat, milk, wool, hides, eggs, honey, etc.) are reduced, so that a more economical and easier animal husbandry is possible by the use of the active compounds according to the invention.
Die Anwendung der erfindungsgemäßen Wirkstoffe geschieht im Veterinärsektor und bei der Tierhaltung in bekannter Weise durch enterale Verabreichung in Form von beispielsweise Tabletten, Kapseln, Tränken, Drenchen, Granulaten, Pasten, BoIi, des feed-through- Verfahrens, von Zäpfchen, durch parenterale Verabreichung, wie zum Beispiel durch Injektionen (intramuskulär, 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, Schwanzmarken, Gliedmaßenbändern, Halftern, Markierungsvorrichtungen usw.The use of the active compounds according to the invention takes place in the veterinary sector and in animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boilies, the feed-through process, suppositories, by parenteral administration, as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying, pouring (pour-on and spot-on ), washing, powdering and with the aid of active substance-containing moldings, such as collars, ear tags, tail marks, limb bands, 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.In the application for livestock, 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 ingredients in an amount of from 1 to 80% by weight, directly or apply after 100 to 10,000 times dilution or use as a chemical bath.
Außerdem wurde gefunden, daß die erfϊndungsgemäßen Verbindungen eine hohe insektizide Wirkung gegen Insekten zeigen, die technische Materialien zerstören.In addition, it has been found that the compounds according to the invention have a high insecticidal activity against insects which destroy industrial materials.
Beispielhaft und vorzugsweise - ohne jedoch zu limitieren - seien die folgenden Insekten genannt:By way of example and preferably without limiting however, the following insects are mentioned:
Käfer wie Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinodems minutus;Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinodem's minutus;
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 like Lepisma saccharina.
Unter technischen Materialien sind im vorliegenden Zusammenhang nicht-lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Holzverarbeitungsprodukte und Anstrichmittel.Technical materials in the present context are non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
Die anwendungsfertigen Mittel können gegebenenfalls noch weitere Insektizide und gegebenenfalls noch ein oder mehrere Fungizide enthalten.The ready-to-use agents may optionally contain further insecticides and optionally one or more fungicides.
Hinsichtlich möglicher zusätzlicher Zumischpartner sei auf die oben genannten Insektizide und Fungizide verwiesen.With regard to possible additional admixing partners, reference is made to the above-mentioned insecticides and fungicides.
Zugleich können die erfindungsgemäßen 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 compounds according to the invention can be used to protect against fouling of objects, in particular hulls, sieves, nets, structures, quay systems and signal systems, which come into contact with seawater or brackish water.
Weiter können die erfmdungsgemäßen Verbindungen allein oder in Kombinationen mit anderen Wirkstoffen als Antifouling-Mittel eingesetzt werden.Furthermore, the compounds according to the invention can be used alone or in combinations with other active substances as antifouling agents.
Die Wirkstoffe eignen sich auch zur Bekämpfung von tierischen Schädlingen im Haushalts-, Hygiene- und Vorratsschutz, insbesondere von Insekten, 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 compounds are also suitable for controlling animal pests in household, hygiene and storage protection, in particular of insects, arachnids and mites, which are used in closed rooms, such as apartments, factory buildings, offices, vehicle cabins u.a. occurrence. They can be used to control these pests, alone or in combination with other active ingredients and adjuvants in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
Aus der Ordnung der Scorpionidea z.B. Buthus occitanus.From the order of Scorpionidea e.g. Buthus occitanus.
Aus der Ordnung der Acarina z.B. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.From the order of Acarina, for example, Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
Aus der Ordnung der Araneae z.B. Aviculariidae, Araneidae.From the order of the Araneae e.g. Aviculariidae, Araneidae.
Aus der Ordnung der Opiliones z.B. Pseudoscorpiones chelifer, Pseudoscoφiones cheiridium, Opiliones phalangium.From the order of Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscoφiones cheiridium, Opiliones phalangium.
Aus der Ordnung der Isopoda z.B. Oniscus asellus, Porcellio scaber.From the order of isopods e.g. Oniscus asellus, Porcellio scaber.
Aus der Ordnung der Diplopoda z.B. Blaniulus guttulatus, Polydesmus spp..From the order of diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..
Aus der Ordnung der Chilopoda z.B. Geophilus spp..From the order of Chilopoda e.g. Geophilus spp ..
Aus der Ordnung der Zygentoma z.B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.From the order of Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
Aus der Ordnung der Blattaria z.B. Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.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.From the order of 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 Isoptera e.g. Kalotermes spp., Reticulitermes spp.
Aus der Ordnung der Psocoptera z.B. Lepinatus spp., Liposcelis spp.From the order of 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, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.From the order of 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.
Aus der Ordnung der Diptera z.B. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.From the order of Diptera e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys Calcitrans, Tipula paludosa.
Aus der Ordnung der Lepidoptera z.B. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella. Aus der Ordnung der Siphonaptera z.B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.From the order of Lepidoptera eg Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella. From the order of the Siphonaptera, for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
Aus der Ordnung der Hymenoptera z.B. Camponotus herculeanus, Lasius fuligrnosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.From the order of Hymenoptera e.g. Camponotus herculeanus, Lasius fuligrnosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
Aus der Ordnung der Anoplura z.B. Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix, Phthirus pubis.From the order of the Anoplura e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix, Phthirus pubis.
Aus der Ordnung der Heteroptera z.B. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.From the order of 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- nicotinoiden, 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 ingredients such as phosphoric acid esters, carbamates, pyrethroids, neonicotinoids, growth regulators or active compounds from other known classes of insecticides.
Die Anwendung erfolgt in Aerosolen, drucklosen Sprühmitteln, z.B. Pump- und Zerstäubersprays, Nebelautomaten, Foggern, Schäumen, Gelen, Verdampferprodukten mit Verdampferplättchen aus Cellulose oder Kunststoff, Flüssigverdampfern, Gel- und Membranverdampfern, propellergetriebenen Verdampfern, energielosen bzw. passiven Verdampfungssystemen, Mottenpapieren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködern oder Köderstationen.Application is in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
SvnthesebeispieleSvnthesebeispiele
Folgende Abkürzungen werden in den nachfolgenden Tabellen verwendet:The following abbreviations are used in the following tables:
2-Pyr 3-Pyr 4-Pyr 2-Pyrm 2-Pyrz TFiPr HFiPr2-Pyr 3-Pyr 4-Pyr 2-Pyrm 2-Pyrz TFiPr HFiPr
Η-NMR-Daten (400 MHz., interner Standard: Tetramethylsilan δ = 0.00 ppm; s = Singulett, br. s = breites Singulett, d = Dublett, dd = Doppeldublett, m = Multiple«, q = Quartett, t = Triplett) Tabelle 1Η-NMR data (400 MHz, internal standard: tetramethylsilane δ = 0.00 ppm; s = singlet, br. S = broad singlet, d = doublet, dd = double doublet, m = multiple, q = quartet, t = triplet ) Table 1
Gemäß den oben angegebenen allgemeinen Methoden lassen sich die in der folgenden Tabelle angegebenen Verbindungen der Formel (I- A mit Q = Q1) herstellen.According to the general methods given above, it is possible to prepare the compounds of the formula (I-A where Q = Q 1 ) shown in the table below.
o O
Charakteristische Daten für Synthesebeispiele:Characteristic data for synthesis examples:
I-A-Q 1-001: spektroskopische Daten siehe Protokoll unter allgemeinen SynthesevorschriftenI-A-Q 1-001: For spectroscopic data see protocol under general procedure
I-A-Ql-002: spektroskopische Daten siehe Protokoll unter allgemeinen SynthesevorschriftenI-A-Ql-002: For spectroscopic data see protocol under general procedure
5 I-A-Ql-023: log P (HCOOH): 2,76 I-A-Ql-024: log P (HCOOH): 3,90 I-A-Ql-025: log P (HCOOH): 3,025 I-A-Ql-023: log P (HCOOH): 2.76 I-A-Ql-024: log P (HCOOH): 3.90 I-A-Ql-025: log P (HCOOH): 3.02
I-A-Ql-026: log P (HCOOH): 3,37 I-A-Ql-027: log P (HCOOH): 4,07 I-A-Ql-028: log P (HCOOH): 2,65I-A-Ql-026: log P (HCOOH): 3.37 I-A-Ql-027: log P (HCOOH): 4.07 I-A-Ql-028: log P (HCOOH): 2.65
I-A-Ql-029: log P (HCOOH): 2,65 I-A-Ql-030: log P (HCOOH): 2,92 I-A-Ql-031: log P (HCOOH): 3,60I-A-Ql-029: log P (HCOOH): 2.65 I-A-Ql-030: log P (HCOOH): 2.92 I-A-Ql-031: log P (HCOOH): 3.60
I-A-Ql-032: log P (HCOOH): 3,28 I-A-Ql-033: log P (HCOOH): 3,30 I-A-Ql-034: log P (HCOOH): 3,10I-A-Ql-032: log P (HCOOH): 3.28 I-A-Ql-033: log P (HCOOH): 3.30 I-A-Ql-034: log P (HCOOH): 3.10
I-A-Ql-035: log P (HCOOH): 2,80 I-A-Ql-036: log P (HCOOH): 3,24 I-A-Ql-037: log P (HCOOH): 3,33 IA-Ql-035: log P (HCOOH): 2.80 IA-Ql-036: log P (HCOOH): 3.24 IA-Ql-037: log P (HCOOH): 3.33
I-A-Ql-038: log P (HCOOH): 3,33 I-A-Ql-039: log P (HCOOH): 2,89 I-A-Ql-040: log P (HCOOH): 3,44I-A-Ql-038: log P (HCOOH): 3.33 I-A-Ql-039: log P (HCOOH): 2.89 I-A-Ql-040: log P (HCOOH): 3.44
I-A-Ql-041: log P (HCOOH): 3,19 I-A-Ql-042: log P (HCOOH): 2,84 I-A-Ql-043: log P (HCOOH): 3,61I-A-Ql-041: log P (HCOOH): 3.19 I-A-Ql-042: log P (HCOOH): 2.84 I-A-Ql-043: log P (HCOOH): 3.61
I-A-Ql-044: log P (HCOOH): 3,10 I-A-Ql-045: log P (HCOOH): 2,64 I-A-Ql-046: log P (HCOOH): 3,24I-A-Ql-044: log P (HCOOH): 3.10 I-A-Ql-045: log P (HCOOH): 2.64 I-A-Ql-046: log P (HCOOH): 3.24
I-A-Ql-047: log P (HCOOH): 2,64 I-A-Ql-048: log P (HCOOH): 2,39 I-A-Ql-049: log P (HCOOH): 4,11I-A-Ql-047: log P (HCOOH): 2.64 I-A-Ql-048: log P (HCOOH): 2.39 I-A-Ql-049: log P (HCOOH): 4.11
5 I-A-Ql-050: log P (HCOOH): 4,34 I-A-Ql-051: log P (HCOOH): 2,27 I-A-Ql-052: log P (HCOOH): 2,435 I-A-Ql-050: log P (HCOOH): 4.34 I-A-Ql-051: log P (HCOOH): 2.27 I-A-Ql-052: log P (HCOOH): 2.43
I-A-Ql-053: log P (HCOOH): 2,66 I-A-Ql-054: log P (HCOOH): 2,18 I-A-Ql-055: log P (HCOOH): 2,47 oI-A-Ql-053: log P (HCOOH): 2.66 I-A-Ql-054: log P (HCOOH): 2.18 I-A-Ql-055: log P (HCOOH): 2.47 o
OOOO
I-A-Ql-056: log P (HCOOH): 2,80 I-A-Ql-057: log P (HCOOH): 2,35 I-A-Ql-058: log P (HCOOH): 2,11I-A-Ql-056: log P (HCOOH): 2.80 I-A-Ql-057: log P (HCOOH): 2.35 I-A-Ql-058: log P (HCOOH): 2.11
I-A-Ql-059: log P (HCOOH): 2,30 I-A-Ql-060: log P (HCOOH): 2,27 I-A-Ql-061: log P (HCOOH): 2,29I-A-Ql-059: log P (HCOOH): 2.30 I-A-Ql-060: log P (HCOOH): 2.27 I-A-Ql-061: log P (HCOOH): 2.29
I-A-Ql-062: log P (HCOOH): 3,09 I-A-Ql-063: log P (HCOOH): 3,53 I-A-Ql-064: log P (HCOOH): 3,31I-A-Ql-062: log P (HCOOH): 3.09 I-A-Ql-063: log P (HCOOH): 3.53 I-A-Ql-064: log P (HCOOH): 3.31
10 I-A-Ql-065: log P (HCOOH): 3,33 I-A-Ql-066: log P (HCOOH): 2,14 I-A-Ql-067: log P (HCOOH): 3,9710 I-A-Ql-065: log P (HCOOH): 3.33 I-A-Ql-066: log P (HCOOH): 2.14 I-A-Ql-067: log P (HCOOH): 3.97
I-A-Ql-068: log P (HCOOH): 4,32 I-A-Ql-069: log P (HCOOH): 4,14 I-A-Ql-070: log P (HCOOH): 4,10I-A-Ql-068: log P (HCOOH): 4.32 I-A-Ql-069: log P (HCOOH): 4.14 I-A-Ql-070: log P (HCOOH): 4.10
I-A-Ql-071: log P (HCOOH): 4,84 I-A-Ql-072: log P (HCOOH): 4,82 I-A-Ql-073: iog p (HCOOH): 4,51IA-Ql-071: log P (HCOOH): 4.84 IA-Ql-072: log P (HCOOH): 4.82 IA-Ql-073: i og p (HCOOH): 4.51
I-A-Ql-074: log P (HCOOH): 4,33 I-A-Ql-075: log P (HCOOH): 3,28 I-A-Ql-076: log P (HCOOH): 2,98I-A-Ql-074: log P (HCOOH): 4.33 I-A-Ql-075: log P (HCOOH): 3.28 I-A-Ql-076: log P (HCOOH): 2.98
I-A-Ql-077: log P (HCOOH): 4,05 I-A-Ql-078: log P (HCOOH): 4,83 I-A-Ql-079: log P (HCOOH): 4,28 IA-Ql-077: log P (HCOOH): 4.05 IA-Ql-078: log P (HCOOH): 4.83 IA-Ql-079: log P (HCOOH): 4.28
I-A-Ql-080: log P (HCOOH): 4,64 I-A-Ql-081: log P (HCOOH): 4,28 I-A-Ql-082: log P (HCOOH): 4,34I-A-Ql-080: log P (HCOOH): 4.64 I-A-Ql-081: log P (HCOOH): 4.28 I-A-Ql-082: log P (HCOOH): 4.34
I-A-Ql-083: log P (HCOOH): 3,84 I-A-Ql-084: log P (HCOOH): 4,70 I-A-Ql-085: log P (HCOOH): 4,45I-A-QI-083: log P (HCOOH): 3.84 I-A-QI-084: log P (HCOOH): 4.70 I-A-Ql-085: log P (HCOOH): 4.45
I-A-Ql-086: log P (HCOOH): 4,57 I-A-Ql-087: log P (HCOOH): 3,78 I-A-Ql-088: log P (HCOOH): 3,06I-A-Ql-086: log P (HCOOH): 4.57 I-A-Ql-087: log P (HCOOH): 3.78 I-A-Ql-088: log P (HCOOH): 3.06
I-A-Ql-089: log P (HCOOH): 3,53 I-A-Ql-090: log P (HCOOH): 3,47 I-A-Ql-091: log P (HCOOH): 4,17I-A-QI-089: log P (HCOOH): 3.53 I-A-Ql-090: log P (HCOOH): 3.47 I-A-Ql-091: log P (HCOOH): 4.17
5 I-A-Ql-092: log P (HCOOH): 4,40 I-A-Ql-093: log P (HCOOH): 4,005 I-A-QI-092: log P (HCOOH): 4.40 I-A-QI-093: log P (HCOOH): 4.00
O VOO VO
Tabelle 2Table 2
Gemäß den oben angegebenen allgemeinen Methoden lassen sich die in der folgenden Tabelle angegebenen Verbindungen der Formel (I-A mit Q = Q2) 10 herstellen.According to the general methods given above, it is possible to prepare the compounds of the formula (IA with Q =Q 2 ) 10 which are listed in the following table.
(I-A-Q2) (IAQ 2 )
U) U>U) U>
Charakteristische Daten für Svnthesebeispiele: I-A-Q2-001: log P (pH2). 4,02 log P (pH7,5): 4,74Characteristic Data for Synthesis Examples: I-A-Q2-001: log P (pH2). 4.02 log P (pH 7.5): 4.74
5 IH NMR (CDC13) 4,78 (d, 2 H, J = 4,6 Hz), 7,22-7,42 (m, 6 H), 7,72-7,78 (m, 2 H), 8,00-8,02 (m, 1 H), 8,11-8,13 (m, 2 H), 8,53 (d, 1 H, J = 4,8 Hz)5HM NMR (CDC13) 4.78 (d, 2H, J = 4.6Hz), 7.22-7.42 (m, 6H), 7.72-7.78 (m, 2H) , 8.00-8.02 (m, 1H), 8.11-8.13 (m, 2H), 8.53 (d, 1H, J = 4.8Hz)
I-A-Q2-002: spektroskopische Daten siehe Protokoll unter allgemeinen SynthesevorschriftenI-A-Q2-002: For spectroscopic data see protocol under general procedure
I-A-Q2-003: IH NMR (CDC13)- 4,81 (d, 2 H, J = 4,6 Hz), 7,28-7,39 (m, 7 H), 1,17>-1,1% (m, 2 H), 8,11-8,17 (m, 2 H), 8,45-8,54 (m, 2 H) I-A-Q2-004: IH NMR (CDC13). 3,86-4,16 (m, 2 H), 7,34-7,42 (m, 3 H), 7,86-8,02 (m, 3 H), 8,15-8,17 (m, 1 H)IA-Q2-003: IH NMR (CDC13) - 4.81 (d, 2H, J = 4.6 Hz), 7.28-7.39 (m, 7H), 1.17> -1, 1% (m, 2H), 8.11-8.17 (m, 2H), 8.45-8.54 (m, 2H) IA-Q2-004: IH NMR (CDC13). 3.86-4.16 (m, 2H), 7.34-7.42 (m, 3H), 7.86-8.02 (m, 3H), 8.15-8.17 ( m, 1H)
I-A-Q2-005: IH NMR (CDC13) 1,43 (d, 3 H, J = 3,5 Hz), 4,86-4,91 (m, 1 H), 6,13-6,20 (m, 1 H), 7,34-7,40 (m, 3 H), 7,59-7,67 (m, 1 H), 7,86-8,15 (m, 3 H) 10 I-A-Q2-006: IH NMR (CDC13): 1,45 (d, 3 H, J = 7,1 Hz), 4,88-4,93 (m, 1 H), 7,36 (t, 1 H, J = 1,8 Hz), 7,74-7,76 (m, 3 H), 8,23-8,29 (m, 4 H), 9,17 (s, 1 H) I-A-Q2-008: IH NMR (CDC13)- 4,79 (d, 2 H, J = 4,9 Hz), 7,43-7,77 (m, 9 H), 7,95-8,54 (m, 4 H)IA-Q2-005: IH NMR (CDC13) 1.43 (d, 3H, J = 3.5 Hz), 4.86-4.91 (m, 1H), 6.13-6.20 ( m, 1H), 7.34-7.40 (m, 3H), 7.59-7.67 (m, 1H), 7.86-8.15 (m, 3H) 10 IA Q2-006: IH NMR (CDC13): 1.45 (d, 3H, J = 7.1 Hz), 4.88-4.93 (m, 1H), 7.36 (t, 1H, J = 1.8 Hz), 7.74-7.76 (m, 3H), 8.23-8.29 (m, 4H), 9.17 (s, 1H) IA-Q2-008 : IH NMR (CDC13) - 4.79 (d, 2H, J = 4.9Hz), 7.43-7.77 (m, 9H), 7.95-8.54 (m, 4H )
I-A-Q2-009: IH NMR (CDC13): 4,77 (d, 2 H, J = 4,8 Hz), 7,22-7,42 (m, 3 H), 7,72-7,78 (m, 2 H), 7,93-7,95 (m, 3 H), 8,03-8,05 (m, 1 H), 8,14-8,14 (m, 1 H), 8,27-8,31 (m, 1 H), 8,52 (d, 1 H, J = 4,6 Hz) IA-Q2-009: IH NMR (CDC13): 4.77 (d, 2H, J = 4.8Hz), 7.22-7.42 (m, 3H), 7.72-7.78 (m, 2H), 7.93-7.95 (m, 3H), 8.03-8.05 (m, 1H), 8.14-8.14 (m, 1H), 8 , 27-8.31 (m, 1H), 8.52 (d, 1H, J = 4.6 Hz)
I-A-Q2-010: IH NMR (CDC13): 4,10-4,14 (m, 2 H), 6,33-6,35 (m, 1 H), 7,71 (d, I H1 J = 8,4 Hz), 7,92-7,95 (m, 3 H), 8,03-8,05 (m, 1 H), 8,14-8,14 (m, 1IA-Q2-010: IH NMR (CDC13): 4.10-4.14 (m, 2H), 6.33-6.35 (m, 1H), 7.71 (d, IH 1 J = 8.4 Hz), 7.92-7.95 (m, 3H), 8.03-8.05 (m, 1H), 8.14-8.14 (m, 1
H), 8,27 (s, 1 H)H), 8.27 (s, 1H)
I-A-Q2-011: log P (HCOOH): 4,54I-A-Q2-011: log P (HCOOH): 4.54
IH NMR (DMS0-d6): 8,77 (d, 1 H, J = 8.8 Hz), 7,95 (s, 1 H), 7,53 (t, 1 H, J = 2,0 Hz), 7,52-7,49 (m, 2 H), 7,34 (d, 2 H, J = 2,0 Hz), 5,58 (s, 5 2 H), 4,84-4,78 (m, 1 H), 2,42 (s, 3 H), 1,34 (d, 3 H, J = 7,2 Hz)IH NMR (DMS0-d6): 8.77 (d, 1H, J = 8.8Hz), 7.95 (s, 1H), 7.53 (t, 1H, J = 2.0Hz), 7.52 (d, 2H, J = 2.0Hz), 5.58 (s, 5H 2), 4.84-4.78 (m, 2H), 4.84-4.78 ( m, 1H), 2.42 (s, 3H), 1.34 (d, 3H, J = 7.2Hz)
I-A-Q2-012: spektroskopische Daten siehe Protokoll unter allgemeinen SynthesevorschriftenI-A-Q2-012: For spectroscopic data see protocol under general procedure
I-A-Q2-013: log P (HCOOH): 3,59I-A-Q2-013: log P (HCOOH): 3.59
I-A-Q2-014: log P (HCOOH): 4,34I-A-Q2-014: log P (HCOOH): 4.34
IH NMR (DMS0-d6): 8,86 (t, 1 H, J = 6,4 Hz), 7,54-7,49 (m, 4 H), 7,34 (d, 2 H, J = 2,0 Hz), 5,59 (s, 2 H), 4,12-4,04 (m, 1 H), 2,43 (s, 3 H)IH NMR (DMSO-d6): 8.86 (t, 1H, J = 6.4Hz), 7.54-7.49 (m, 4H), 7.34 (d, 2H, J = 2.0 Hz), 5.59 (s, 2H), 4.12-4.04 (m, 1H), 2.43 (s, 3H)
10 I-A-Q2-015: log P (HCOOH): 3,7010 I-A-Q2-015: log P (HCOOH): 3.70
IH NMR (DMS0-d6): 8,55-8,52 (m, 2 H), 7,77 (td, 1 H, J = 7,6 und 2,0 Hz), 7,54 (d, 1 H, J = 8,8 Hz), 7,53 (t, 1 H, J = 2,0 Hz), 7,49-7,47 (m, 2 H), 7,46 (d, 1 H, J = 7,6 Hz), 7,34 (d, 2 H, J = 2,0 Hz), 7,25 (dd, I H1 J = 7,6 und 4,8 Hz), 5,58 (s, 2 H), 5,22-5,12 (m, 1 H), 2,41 (s, 3 H),IH NMR (DMSO-d6): 8.55-8.52 (m, 2H), 7.77 (td, 1H, J = 7.6 and 2.0 Hz), 7.54 (d, 1 H, J = 8.8 Hz), 7.53 (t, 1 H, J = 2.0 Hz), 7.49-7.47 (m, 2 H), 7.46 (d, 1 H, J = 7.6 Hz), 7.34 (d, 2 H, J = 2.0 Hz), 7.25 (dd, IH 1 J = 7.6 and 4.8 Hz), 5.58 (s , 2H), 5.22-5.12 (m, 1H), 2.41 (s, 3H),
1,51 (d, 3 H, J = 6,8 Hz)1.51 (d, 3H, J = 6.8 Hz)
I-A-Q2-016: log P (HCOOH): 4,79I-A-Q2-016: log P (HCOOH): 4.79
15 IH NMR (DMSO-d6): 8.59 (d, 1 H, J = 7,6 Hz), 7,53 (t, 1 H, J = 2,0 Hz), 7,49-7,21 (m, 10 H), 5,54 (s, 2 H), 5,19-5,14 (m, 1 H), 2,38 (s, 3 H),15 H NMR (DMSO-d6): 8.59 (d, 1 H, J = 7.6 Hz), 7.53 (t, 1 H, J = 2.0 Hz), 7.49-7.21 (m , 10H), 5.54 (s, 2H), 5.19-5.14 (m, 1H), 2.38 (s, 3H),
1,48 (d, 3 H, J = 6,8 Hz) 1.48 (d, 3H, J = 6.8 Hz)
I-A-Q2-017: log P (HCOOH): 4,04I-A-Q2-017: log P (HCOOH): 4.04
IH NMR (DMSO-d6): 8,55 (t, 1 H, J = 5,8 Hz), 7,53 (t, 1 H, J = 2,0 Hz), 7,53-7,47 (m, 3 H), 7,34 (d, 2 H, J = 2,0 Hz), 6,12 (tt, 1 H, J = 56,0 und 3,8 Hz), 5,59 (s, 2 H), 3,73-3,63 (m, 2 H), 2,43 (s, 3 H)IH NMR (DMSO-d6): 8.55 (t, 1H, J = 5.8Hz), 7.53 (t, 1H, J = 2.0Hz), 7.53-7.47 ( m, 3 H), 7.34 (d, 2 H, J = 2.0 Hz), 6.12 (tt, 1 H, J = 56.0 and 3.8 Hz), 5.59 (s, 2H), 3.73-3.63 (m, 2H), 2.43 (s, 3H)
I-A-Q2-018: log P (HCOOH): 3,56I-A-Q2-018: log P (HCOOH): 3.56
IH NMR (DMSO-d6): 8,77 (d, 2 H, J = 5,2 Hz), 8,59 (t, 1 H, J = 5,8 Hz), 7,62 (d, I H1 J = 8,8 Hz), 7,53 (t, I H1 J = 2,0 Hz), 7,52-7,48 (m, 2 H), 7,40 (t, 1 H, J = 4,8 Hz), 7,35 (d, 2 H, J = 1,6 Hz), 5,59 (s, 2 H), 4,66 (d, 2 H, J = 6,0 Hz), Me unter DMSO-SignalIH NMR (DMSO-d6): 8.77 (d, 2H, J = 5.2Hz), 8.59 (t, 1H, J = 5.8Hz), 7.62 (d, IH 1 J = 8.8 Hz), 7.53 (t, IH 1 J = 2.0 Hz), 7.52-7.48 (m, 2H), 7.40 (t, 1H, J = 4 , 8 Hz), 7.35 (d, 2H, J = 1.6 Hz), 5.59 (s, 2H), 4.66 (d, 2H, J = 6.0 Hz), Me under DMSO signal
I-A-Q2-019: log P (HCOOH): 4,57I-A-Q2-019: log P (HCOOH): 4.57
OOOO
1H NMR (DMS0-d6): 1.36 (d, 3 H); 2.42 (s, 3 H); 4.81 (m, 1 H); 5.51 (br. s, 2 H); 7.32 (dd, 1 H); 7.47-7.57 (m, 4 H); 7.67 (d, 1 H); 7.70 (br. d, l H) 1 H NMR (DMSO-d6): 1.36 (d, 3H); 2.42 (s, 3H); 4.81 (m, 1H); 5.51 (brs s, 2 H); 7.32 (dd, 1H); 7.47-7.57 (m, 4H); 7.67 (d, 1H); 7.70 (br d, l H)
10 I-A-Q2-020: spektroskopische Daten siehe Protokoll unter allgemeinen Synthesevorschriften10 I-A-Q2-020: For spectroscopic data see protocol under general procedure
I-A-Q2-021: log P (HCOOH): 3,48I-A-Q2-021: log P (HCOOH): 3.48
IH NMR (DMSO-d6): 8,85 (d, I H1 J = 8,8 Hz), 8,69 (s, 1 H), 8,51 (d, I H1 J = 4,8 Hz), 7,75 (td, 1 H, J = 7,6 und 1,6 Hz), 7,54 (s, 1 H), 7,40IH NMR (DMSO-d6): 8.85 (d, IH 1 J = 8.8 Hz), 8.69 (s, 1 H), 8.51 (d, IH 1 J = 4.8 Hz), 7.75 (td, 1H, J = 7.6 and 1.6 Hz), 7.54 (s, 1H), 7.40
(d, 1 H, J = 7,6 Hz), 7,31 (d, 2 H, J = 2,0 Hz), 7,25 (dd, 1 H, J = 7,6 und 5,6 Hz), 5,14-5,09 (dd, 1 H), 1,45 (d, 3 H, J = 6,8 Hz)(d, 1 H, J = 7.6 Hz), 7.31 (d, 2 H, J = 2.0 Hz), 7.25 (dd, 1 H, J = 7.6 and 5.6 Hz ), 5.14-5.09 (dd, 1H), 1.45 (d, 3H, J = 6.8Hz)
I-A-Q2-022: spektroskopische Daten siehe Protokoll unter allgemeinen SynthesevorschriftenI-A-Q2-022: For spectroscopic data see protocol under general procedure
15 I-A-Q2-023: log P (HCOOH): 4,91 15 IA-Q2-023: log P (HCOOH): 4.91
IH NMR (DMS0-d6): 8,85 (t, 1 H, J = 5,6 Hz), 8,52 (d, 1 H, J = 4,0 Hz), 7,79 (td, 1 H, J = 7,6 und 1,6 Hz), 7,72 (t, 1 H, J = 1,8 Hz), 7,64 (d,IH NMR (DMSO-d6): 8.85 (t, 1H, J = 5.6Hz), 8.52 (d, 1H, J = 4.0Hz), 7.79 (td, 1H , J = 7.6 and 1.6 Hz), 7.72 (t, 1 H, J = 1.8 Hz), 7.64 (d,
1 H, J = 8,4 Hz), 7,58-7,53 (m, 2 H), 7,50 (d, 2 H, J = 2,0 Hz), 7,42 (d, 1 H, J = 8,0 Hz), 7,28 (dd, I H1 J = 6,8 und 5,6 Hz), 4,58 (d, 2 H, J =1H, J = 8.4Hz), 7.58-7.53 (m, 2H), 7.50 (d, 2H, J = 2.0Hz), 7.42 (d, 1H , J = 8.0 Hz), 7.28 (dd, IH 1 J = 6.8 and 5.6 Hz), 4.58 (d, 2 H, J =
6,0 Hz), 2,47 (s, 3 H)6.0 Hz), 2.47 (s, 3 H)
I-A-Q2-024: spektroskopische Daten siehe Protokoll unter allgemeinen SynthesevorschriftenI-A-Q2-024: For spectroscopic data see protocol under general synthetic procedure
5 I-A-Q2-02S: spektroskopische Daten siehe Protokoll unter allgemeinen Synthesevorschriften5 I-A-Q2-02S: For spectroscopic data see protocol under general synthetic prescriptions
I-A-Q2-026: log P (HCOOH): 5,44I-A-Q2-026: log P (HCOOH): 5.44
IH NMR (DMS0-d6): 8.90 (d, 1 H, J = 8,8 Hz), 7,71 (t, I H1 J = 2,0 Hz), 7,54-7,52 (m, 3 H), 7,45 (d, 2 H, J = 2,0 Hz), 4,85-4,79 (m, 1 H), ^ 2,43 (s, 3 H), 1 ,34 (d, 3 H, J = 7,2 Hz) $IH NMR (DMS0-d6): 8.90 (d, 1 H, J = 8.8 Hz), 7.71 (t, IH 1 J = 2.0 Hz), 7.54-7.52 (m, 3 H), 7.45 (d, 2H, J = 2.0Hz), 4.85-4.79 (m, 1H), 2.43 (s, 3H), 1.34 (i.e. , 3 H, J = 7.2 Hz) $
I-A-Q2-027: spektroskopische Daten siehe Protokoll unter allgemeinen SynthesevorschriftenI-A-Q2-027: For spectroscopic data see protocol under general procedure
10 I-A-Q2-028: log P (HCOOH): 4,3510 I-A-Q2-028: log P (HCOOH): 4.35
IH NMR (DMS0-d6): 8,83 (t, 1 H, J = 5,6 Hz), 8,52 (d, 1 H, J = 4,0 Hz), 7,78 (td, 1 H, J = 7,6 und 2,0 Hz), 7,69 (t, 1 H, J = 2,0 Hz), 7,63 (d, 1 H, J = 8,0 Hz), 7,58-7,55 (m, 2 H), 7,50 (d, 2 H1 J = 2,0 Hz), 7,41 (d, 1 H, J = 8,0 Hz), 7,27 (dd, 1 H, J = 6,8 und 5,2 Hz), 4,58 (d, 2 H1 J =IH NMR (DMSO-d6): 8.83 (t, 1H, J = 5.6Hz), 8.52 (d, 1H, J = 4.0Hz), 7.78 (td, 1H , J = 7.6 and 2.0 Hz), 7.69 (t, 1 H, J = 2.0 Hz), 7.63 (d, 1 H, J = 8.0 Hz), 7.58 -7.55 (m, 2 H), 7.50 (d, 2H 1 J = 2.0 Hz), 7.41 (d, 1 H, J = 8.0 Hz), 7.27 (dd , 1 H, J = 6.8 and 5.2 Hz), 4.58 (d, 2 H 1 J =
5,6 Hz), 2,47 (s, 3 H), 2,04 (s, 3 H)5.6 Hz), 2.47 (s, 3H), 2.04 (s, 3H)
I-A-Q2-029: log P (HCOOH): 3,24 I-A-Q2-030: log P (HCOOH): 3,68 I-A-Q2-031: log P (HCOOH): 3,33I-A-Q2-029: log P (HCOOH): 3.24 I-A-Q2-030: log P (HCOOH): 3.68 I-A-Q2-031: log P (HCOOH): 3.33
15 I-A-Q2-032: log P (HCOOH): 3,63 I-A-Q2-033: log P (HCOOH): 4,51 I-A-Q2-034: log P (HCOOH): 1,94 I-A-Q2-035: log P (HCOOH): 4,23 I-A-Q2-036: log P (HCOOH): 3,68 I-A-Q2-037: log P (HCOOH): 2,42 15 IA-Q2-032: log P (HCOOH): 3.63 IA-Q2-033: log P (HCOOH): 4.51 IA-Q2-034: log P (HCOOH): 1.94 IA-Q2 035: log P (HCOOH): 4.23 IA-Q2-036: log P (HCOOH): 3.68 IA-Q2-037: log P (HCOOH): 2.42
I-A-Q2-038: log P (HCOOH): 3,11 I-A-Q2-039: log P (HCOOH): 3,94 I-A-Q2-040: log P (HCOOH): 4,57I-A-Q2-038: log P (HCOOH): 3.11 I-A-Q2-039: log P (HCOOH): 3.94 I-A-Q2-040: log P (HCOOH): 4.57
I-A-Q2-041: log P (HCOOH): 3,94 I-A-Q2-042: log P (HCOOH): 2,93 I-A-Q2-043: log P (HCOOH): 5,65I-A-Q2-041: log P (HCOOH): 3.94 I-A-Q2-042: log P (HCOOH): 2.93 I-A-Q2-043: log P (HCOOH): 5.65
I-A-Q2-044: log P (HCOOH): 3,42 I-A-Q2-045: log P (HCOOH): 5,85 I-A-Q2-046: log P (HCOOH): 4,51I-A-Q2-044: log P (HCOOH): 3.42 I-A-Q2-045: log P (HCOOH): 5.85 I-A-Q2-046: log P (HCOOH): 4.51
I-A-Q2-047: log P (HCOOH): 4,94 I-A-Q2-048: log P (HCOOH): 4,70 I-A-Q2-049: log P (HCOOH): 4,28I-A-Q2-047: log P (HCOOH): 4.94 I-A-Q2-048: log P (HCOOH): 4.70 I-A-Q2-049: log P (HCOOH): 4.28
5 I-A-Q2-050: log P (HCOOH): 4,64 I-A-Q2-051: log P (HCOOH): 3,06 I-A-Q2-052: log P (HCOOH): 2,345 I-A-Q2-050: log P (HCOOH): 4.64 I-A-Q2-051: log P (HCOOH): 3.06 I-A-Q2-052: log P (HCOOH): 2.34
I-A-Q2-053: log P (HCOOH): 2,04 I-A-Q2-054: log P (HCOOH): 2,31 I-A-Q2-055: log P (HCOOH): 5,79 oI-A-Q2-053: log P (HCOOH): 2.04 I-A-Q2-054: log P (HCOOH): 2.31 I-A-Q2-055: log P (HCOOH): 5.79 o
I-A-Q2-056: log P (HCOOH): 3,93 I-A-Q2-057: log P (HCOOH): 2,72 I-A-Q2-058: log P (HCOOH): 1 ,94I-A-Q2-056: log P (HCOOH): 3.93 I-A-Q2-057: log P (HCOOH): 2.72 I-A-Q2-058: log P (HCOOH): 1.94
I-A-Q2-059: log P (HCOOH): 3,63 I-A-Q2-060: log P (HCOOH): 4,34 I-A-Q2-061: log P (HCOOH): 4,45I-A-Q2-059: log P (HCOOH): 3.63 I-A-Q2-060: log P (HCOOH): 4.34 I-A-Q2-061: log P (HCOOH): 4.45
I-A-Q2-062: log P (HCOOH): 3,94 I-A-Q2-063: log P (HCOOH): 3,11 I-A-Q2-064: log P (HCOOH): 6,44I-A-Q2-062: log P (HCOOH): 3.94 I-A-Q2-063: log P (HCOOH): 3.11 I-A-Q2-064: log P (HCOOH): 6.44
10 I-A-Q2-065: log P (HCOOH): 2,72 I-A-Q2-066: log P (HCOOH): 5,15 I-A-Q2-067: log P (HCOOH): 4,6510 I-A-Q2-065: log P (HCOOH): 2.72 I-A-Q2-066: log P (HCOOH): 5.15 I-A-Q2-067: log P (HCOOH): 4.65
I-A-Q2-068: log P (HCOOH): 5,35 I-A-Q2-069: log P (HCOOH): 4,83 I-A-Q2-070: log P (HCOOH): 5,25I-A-Q2-068: log P (HCOOH): 5.35 I-A-Q2-069: log P (HCOOH): 4.83 I-A-Q2-070: log P (HCOOH): 5.25
I-A-Q2-071: log P (HCOOH): 4,95 I-A-Q2-072: log P (HCOOH): 5,22 I-A-Q2-073: log P (HCOOH): 4,35I-A-Q2-071: log P (HCOOH): 4.95 I-A-Q2-072: log P (HCOOH): 5.22 I-A-Q2-073: log P (HCOOH): 4.35
I-A-Q2-074: log P (HCOOH): 2,76 I-A-Q2-075: log P (HCOOH): 3,94 I-A-Q2-076: log P (HCOOH): 2,89I-A-Q2-074: log P (HCOOH): 2.76 I-A-Q2-075: log P (HCOOH): 3.94 I-A-Q2-076: log P (HCOOH): 2.89
I-A-Q2-077: log P (HCOOH): 4,17 I-A-Q2-078: log P (HCOOH): 2,94 I-A-Q2-079: log P (HCOOH): 3,37 IA-Q2-077: log P (HCOOH): 4.17 IA-Q2-078: log P (HCOOH): 2.94 IA-Q2-079: log P (HCOOH): 3.37
I-A-Q2-080: log P (HCOOH): 2,38 I-A-Q2-081: log P (HCOOH): 3,58 I-A-Q2-082: log P (HCOOH): 2,46I-A-Q2-080: log P (HCOOH): 2.38 I-A-Q2-081: log P (HCOOH): 3.58 I-A-Q2-082: log P (HCOOH): 2.46
I-A-Q2-083: log P (HCOOH): 3,68 I-A-Q2-084: log P (HCOOH): 3,89 I-A-Q2-085: log P (HCOOH): 3,47I-A-Q2-083: log P (HCOOH): 3.68 I-A-Q2-084: log P (HCOOH): 3.89 I-A-Q2-085: log P (HCOOH): 3.47
I-A-Q2-086: log P (HCOOH): 3,68 I-A-Q2-087: log P (HCOOH): 2,80 I-A-Q2-088: log P (HCOOH): 2,99I-A-Q2-086: log P (HCOOH): 3.68 I-A-Q2-087: log P (HCOOH): 2.80 I-A-Q2-088: log P (HCOOH): 2.99
I-A-Q2-089: log P (HCOOH): 3,89 I-A-Q2-090: log P (HCOOH): 4,11 I-A-Q2-091: log P (HCOOH): 3,09I-A-Q2-089: log P (HCOOH): 3.89 I-A-Q2-090: log P (HCOOH): 4.11 I-A-Q2-091: log P (HCOOH): 3.09
5 I-A-Q2-092: log P (HCOOH): 3,27 I-A-Q2-093: log P (HCOOH): 4,00 I-A-Q2-094: log P (HCOOH): 2,765 I-A-Q2-092: log P (HCOOH): 3.27 I-A-Q2-093: log P (HCOOH): 4.00 I-A-Q2-094: log P (HCOOH): 2.76
I-A-Q2-095: log P (HCOOH): 4,51 I-A-Q2-096: log P (HCOOH): 5,35 I-A-Q2-097: log P (HCOOH): 4,64I-A-Q2-095: log P (HCOOH): 4.51 I-A-Q2-096: log P (HCOOH): 5.35 I-A-Q2-097: log P (HCOOH): 4.64
I-A-Q2-098: log P (HCOOH): 4,36 I-A-Q2-099: log P (HCOOH): 5,42 I-A-Q2-100: log P (HCOOH): 4,96I-A-Q2-098: log P (HCOOH): 4.36 I-A-Q2-099: log P (HCOOH): 5.42 I-A-Q2-100: log P (HCOOH): 4.96
I-A-Q2-101: log P (HCOOH): 4,71 I-A-Q2-102: log P (HCOOH): 4,06 I-A-Q2-103: log P (HCOOH): 5,19I-A-Q2-101: log P (HCOOH): 4.71 I-A-Q2-102: log P (HCOOH): 4.06 I-A-Q2-103: log P (HCOOH): 5.19
I-A-Q2-104: log P (HCOOH): 4,46 I-A-Q2-105: log P (HCOOH): 3,61 I-A-Q2-106: log P (HCOOH): 4,30I-A-Q2-104: log P (HCOOH): 4.46 I-A-Q2-105: log P (HCOOH): 3.61 I-A-Q2-106: log P (HCOOH): 4.30
10 I-A-Q2-107: log P (HCOOH): 2,95 I-A-Q2-108: log P (HCOOH): 3,80 I-A-Q2-109: log P (HCOOH): 4,3510 I-A-Q2-107: log P (HCOOH): 2.95 I-A-Q2-108: log P (HCOOH): 3.80 I-A-Q2-109: log P (HCOOH): 4.35
I-A-Q2-110: log P (HCOOH): 2,69 I-A-Q2-111: log P (HCOOH): 4,17 I-A-Q2-112: log P (HCOOH): 4,34I-A-Q2-110: log P (HCOOH): 2.69 I-A-Q2-111: log P (HCOOH): 4.17 I-A-Q2-112: log P (HCOOH): 4.34
I-A-Q2-133: log P (HCOOH): 4,44 I-A-Q2-134: log P (HCOOH): 3,11 I-A-Q2-135: log P (HCOOH): 4,06I-A-Q2-133: log P (HCOOH): 4.44 I-A-Q2-134: log P (HCOOH): 3.11 I-A-Q2-135: log P (HCOOH): 4.06
I-A-Q2-136: log P (HCOOH): 3,80 I-A-Q2-137: log P (HCOOH): 3,40 I-A-Q2-138: log P (HCOOH): 4,21I-A-Q2-136: log P (HCOOH): 3.80 I-A-Q2-137: log P (HCOOH): 3.40 I-A-Q2-138: log P (HCOOH): 4.21
I-A-Q2-139: log P (HCOOH): 4,25 I-A-Q2-140: log P (HCOOH): 3,93 I-A-Q2-141: log P (HCOOH): 4,21 IA-Q2-139: log P (HCOOH): 4.25 IA-Q2-140: log P (HCOOH): 3.93 IA-Q2-141: log P (HCOOH): 4.21
I-A-Q2-142: log P (HCOOH): 3,77 I-A-Q2-143: log P (HCOOH): 2,59 I-A-Q2-144: log P (HCOOH): 3,93I-A-Q2-142: log P (HCOOH): 3.77 I-A-Q2-143: log P (HCOOH): 2.59 I-A-Q2-144: log P (HCOOH): 3.93
I-A-Q2-145: log P (HCOOH): 4,34 I-A-Q2-146: log P (HCOOH): 4,54 I-A-Q2-147: log P (HCOOH): 3,47I-A-Q2-145: log P (HCOOH): 4.34 I-A-Q2-146: log P (HCOOH): 4.54 I-A-Q2-147: log P (HCOOH): 3.47
I-A-Q2-148: log P (HCOOH): 4,12 I-A-Q2-149: log P (HCOOH): 4,15 I-A-Q2-150: log P (HCOOH): 4,65I-A-Q2-148: log P (HCOOH): 4.12 I-A-Q2-149: log P (HCOOH): 4.15 I-A-Q2-150: log P (HCOOH): 4.65
I-A-Q2-151: log P (HCOOH): 4,06 I-A-Q2-152: log P (HCOOH): 4,45 I-A-Q2-153: log P (HCOOH): 3,89I-A-Q2-151: log P (HCOOH): 4.06 I-A-Q2-152: log P (HCOOH): 4.45 I-A-Q2-153: log P (HCOOH): 3.89
5 I-A-Q2-154: log P (HCOOH): 3,75 I-A-Q2-155: log P (HCOOH): 4,11 I-A-Q2-156: log P (HCOOH): 3,895 I-A-Q2-154: log P (HCOOH): 3.75 I-A-Q2-155: log P (HCOOH): 4.11 I-A-Q2-156: log P (HCOOH): 3.89
I-A-Q2-157: log P (HCOOH): 3,51 I-A-Q2-158: log P (HCOOH): 2,85 I-A-Q2-159: log P (HCOOH): 3,65I-A-Q2-157: log P (HCOOH): 3.51 I-A-Q2-158: log P (HCOOH): 2.85 I-A-Q2-159: log P (HCOOH): 3.65
•C- K)• C- K)
I-A-Q2-160: log P (HCOOH): 3,23 I-A-Q2-161: log P (HCOOH): 3,37 I-A-Q2-162: log P (HCOOH): 3,51I-A-Q2-160: log P (HCOOH): 3.23 I-A-Q2-161: log P (HCOOH): 3.37 I-A-Q2-162: log P (HCOOH): 3.51
I-A-Q2-163: log P (HCOOH): 3,13 I-A-Q2-164: log P (HCOOH): 3,27 I-A-Q2-165: log P (HCOOH): 2,72I-A-Q2-163: log P (HCOOH): 3.13 I-A-Q2-164: log P (HCOOH): 3.27 I-A-Q2-165: log P (HCOOH): 2.72
I-A-Q2-166: log P (HCOOH): 3,84 I-A-Q2-167: log P (HCOOH): 3,19 I-A-Q2-168: log P (HCOOH): 2,61I-A-Q2-166: log P (HCOOH): 3.84 I-A-Q2-167: log P (HCOOH): 3.19 I-A-Q2-168: log P (HCOOH): 2.61
10 I-A-Q2-169: log P (HCOOH): 3,78 I-A-Q2-170: log P (HCOOH): 3,15 I-A-Q2-171: log P (HCOOH): 2,5310 I-A-Q2-169: log P (HCOOH): 3.78 I-A-Q2-170: log P (HCOOH): 3.15 I-A-Q2-171: log P (HCOOH): 2.53
I-A-Q2-172: log P (HCOOH): 3,73 I-A-Q2-173: log P (HCOOH): 3,11 I-A-Q2-174: log P (HCOOH): 2,50I-A-Q2-172: log P (HCOOH): 3.73 I-A-Q2-173: log P (HCOOH): 3.11 I-A-Q2-174: log P (HCOOH): 2.50
I-A-Q2-175: log P (HCOOH): 3,47 I-A-Q2-176: log P (HCOOH): 2,89 I-A-Q2-177: log P (HCOOH): 2,27I-A-Q2-175: log P (HCOOH): 3.47 I-A-Q2-176: log P (HCOOH): 2.89 I-A-Q2-177: log P (HCOOH): 2.27
I-A-Q2-178: log P (HCOOH): 3,89 I-A-Q2-179: log P (HCOOH): 3,24 I-A-Q2-180: log P (HCOOH): 2,61I-A-Q2-178: log P (HCOOH): 3.89 I-A-Q2-179: log P (HCOOH): 3.24 I-A-Q2-180: log P (HCOOH): 2.61
I-A-Q2-181: log P (HCOOH): 2,98 I-A-Q2-182: log P (HCOOH): 3,33 I-A-Q2-183: log P (HCOOH): 3,11 IA-Q2-181: log P (HCOOH): 2.98 IA-Q2-182: log P (HCOOH): 3.33 IA-Q2-183: log P (HCOOH): 3.11
I-A-Q2-184: log P (HCOOH): 2,76 I-A-Q2-185: log P (HCOOH): 2,14 I-A-Q2-186: log P (HCOOH): 2,42I-A-Q2-184: log P (HCOOH): 2.76 I-A-Q2-185: log P (HCOOH): 2.14 I-A-Q2-186: log P (HCOOH): 2.42
I-A-Q2-187: log P (HCOOH): 3,42 I-A-Q2-188: log P (HCOOH): 3,78 I-A-Q2-189: log P (HCOOH): 3,53I-A-Q2-187: log P (HCOOH): 3.42 I-A-Q2-188: log P (HCOOH): 3.78 I-A-Q2-189: log P (HCOOH): 3.53
I-A-Q2-190: log P (HCOOH): 3,15 I-A-Q2-191: log P (HCOOH): 2,57 I-A-Q2-192: log P (HCOOH): 2,89I-A-Q2-190: log P (HCOOH): 3.15 I-A-Q2-191: log P (HCOOH): 2.57 I-A-Q2-192: log P (HCOOH): 2.89
I-A-Q2-193: log P (HCOOH): 3,42 I-A-Q2-194: log P (HCOOH): 3,37 I-A-Q2-195: log P (HCOOH): 2,96I-A-Q2-193: log P (HCOOH): 3.42 I-A-Q2-194: log P (HCOOH): 3.37 I-A-Q2-195: log P (HCOOH): 2.96
5 I-A-Q2-196: log P (HCOOH): 2,84 I-A-Q2-197: log P (HCOOH): 2,76 I-A-Q2-198: log P (HCOOH): 5,405 I-A-Q2-196: log P (HCOOH): 2.84 I-A-Q2-197: log P (HCOOH): 2.76 I-A-Q2-198: log P (HCOOH): 5.40
I-A-Q2-199: log P (HCOOH): 3,48 I-A-Q2-200: log P (HCOOH): 4,82 I-A-Q2-201 : log P (HCOOH): 5, 11I-A-Q2-199: log P (HCOOH): 3.48 I-A-Q2-200: log P (HCOOH): 4.82 I-A-Q2-201: log P (HCOOH): 5.11
OJOJ
I-A-Q2-202: log P (HCOOH): 4,22 I-A-Q2-203: log P (HCOOH): 3,77 I-A-Q2-204: log P (HCOOH): 4,22I-A-Q2-202: log P (HCOOH): 4.22 I-A-Q2-203: log P (HCOOH): 3.77 I-A-Q2-204: log P (HCOOH): 4.22
I-A-Q2-205: log P (HCOOH): 4,17 I-A-Q2-206: log P (HCOOH): 4,29 I-A-Q2-207: log P (HCOOH): 4,83I-A-Q2-205: log P (HCOOH): 4.17 I-A-Q2-206: log P (HCOOH): 4.29 I-A-Q2-207: log P (HCOOH): 4.83
I-A-Q2-208: log P (HCOOH): 3,19 I-A-Q2-209: log P (HCOOH): 3,02 I-A-Q2-210: log P (HCOOH): 4,28I-A-Q2-208: log P (HCOOH): 3.19 I-A-Q2-209: log P (HCOOH): 3.02 I-A-Q2-210: log P (HCOOH): 4.28
10 I-A-Q2-211: log P (HCOOH): 2,89 I-A-Q2-212: log P (HCOOH): 2,27 I-A-Q2-213: log P (HCOOH): 4,8910 I-A-Q2-211: log P (HCOOH): 2.89 I-A-Q2-212: log P (HCOOH): 2.27 I-A-Q2-213: log P (HCOOH): 4.89
I-A-Q2-214: log P (HCOOH): 4,45 I-A-Q2-215: log P (HCOOH): 4,76 I-A-Q2-216: log P (HCOOH): 2,57I-A-Q2-214: log P (HCOOH): 4.45 I-A-Q2-215: log P (HCOOH): 4.76 I-A-Q2-216: log P (HCOOH): 2.57
I-A-Q2-217: log P (HCOOH): 4,70 I-A-Q2-218: log P (HCOOH): 3,33 I-A-Q2-219: log P (HCOOH): 4,05I-A-Q2-217: log P (HCOOH): 4.70 I-A-Q2-218: log P (HCOOH): 3.33 I-A-Q2-219: log P (HCOOH): 4.05
I-A-Q2-220: log P (HCOOH): 4,11 I-A-Q2-221: log P (HCOOH): 4,51 I-A-Q2-222: log P (HCOOH): 4,76I-A-Q2-220: log P (HCOOH): 4.11 I-A-Q2-221: log P (HCOOH): 4.51 I-A-Q2-222: log P (HCOOH): 4.76
I-A-Q2-223: log P (HCOOH): 4,45 I-A-Q2-224: log P (HCOOH): 3,78 I-A-Q2-225: log P (HCOOH): 4,57 IA-Q2-223: log P (HCOOH): 4.45 IA-Q2-224: log P (HCOOH): 3.78 IA-Q2-225: log P (HCOOH): 4.57
I-A-Q2-226: log P (HCOOH): 2,50 I-A-Q2-227: log P (HCOOH): 4,40 I-A-Q2-228: log P (HCOOH): 3,78I-A-Q2-226: log P (HCOOH): 2.50 I-A-Q2-227: log P (HCOOH): 4.40 I-A-Q2-228: log P (HCOOH): 3.78
I-A-Q2-229: log P (HCOOH): 4,05 I-A-Q2-230: log P (HCOOH): 4,89 I-A-Q2-231: log P (HCOOH): 2,69I-A-Q2-229: log P (HCOOH): 4.05 I-A-Q2-230: log P (HCOOH): 4.89 I-A-Q2-231: log P (HCOOH): 2.69
I-A-Q2-232: log P (HCOOH): 4,95 I-A-Q2-233: log P (HCOOH): 4,40 I-A-Q2-234: log P (HCOOH): 2,38I-A-Q2-232: log P (HCOOH): 4.95 I-A-Q2-233: log P (HCOOH): 4.40 I-A-Q2-234: log P (HCOOH): 2.38
I-A-Q2-235: log P (HCOOH): 4,95 I-A-Q2-236: log P (HCOOH): 4,51 I-A-Q2-237: log P (HCOOH): 4,76I-A-Q2-235: log P (HCOOH): 4.95 I-A-Q2-236: log P (HCOOH): 4.51 I-A-Q2-237: log P (HCOOH): 4.76
5 I-A-Q2-238: log P (HCOOH): 3,78 I-A-Q2-239: log P (HCOOH): 4,17 I-A-Q2-240: log P (HCOOH): 4,705 I-A-Q2-238: log P (HCOOH): 3.78 I-A-Q2-239: log P (HCOOH): 4.17 I-A-Q2-240: log P (HCOOH): 4.70
I-A-Q2-241: log P (HCOOH): 4,89 I-A-Q2-242: log P (HCOOH): 5,29 I-A-Q2-243: log P (HCOOH): 3,78I-A-Q2-241: log P (HCOOH): 4.89 I-A-Q2-242: log P (HCOOH): 5.29 I-A-Q2-243: log P (HCOOH): 3.78
•fc-• fc-
I-A-Q2-244: log P (HCOOH): 3,68 I-A-Q2-245: log P (HCOOH): 3,89 I-A-Q2-246: log P (HCOOH): 5,02I-A-Q2-244: log P (HCOOH): 3.68 I-A-Q2-245: log P (HCOOH): 3.89 I-A-Q2-246: log P (HCOOH): 5.02
I-A-Q2-247: log P (HCOOH): 4,57 I-A-Q2-248: log P (HCOOH): 4,34 I-A-Q2-249: log P (HCOOH): 4,28I-A-Q2-247: log P (HCOOH): 4.57 I-A-Q2-248: log P (HCOOH): 4.34 I-A-Q2-249: log P (HCOOH): 4.28
I-A-Q2-250: log P (HCOOH): 3,68 I-A-Q2-251: log P (HCOOH): 3,84 I-A-Q2-252: log P (HCOOH): 3,02I-A-Q2-250: log P (HCOOH): 3.68 I-A-Q2-251: log P (HCOOH): 3.84 I-A-Q2-252: log P (HCOOH): 3.02
10 I-A-Q2-253: log P (HCOOH): 4,40 I-A-Q2-254: log P (HCOOH): 3,58 I-A-Q2-255: log P (HCOOH): 4,4010 I-A-Q2-253: log P (HCOOH): 4.40 I-A-Q2-254: log P (HCOOH): 3.58 I-A-Q2-255: log P (HCOOH): 4.40
I-A-Q2-256: log P (HCOOH): 4,64 I-A-Q2-257: log P (HCOOH): 5,22 I-A-Q2-258: log P (HCOOH): 3,47I-A-Q2-256: log P (HCOOH): 4.64 I-A-Q2-257: log P (HCOOH): 5.22 I-A-Q2-258: log P (HCOOH): 3.47
I-A-Q2-259: log P (HCOOH): 3,33 I-A-Q2-260: log P (HCOOH): 3,33 I-A-Q2-261: log P (HCOOH): 4,76I-A-Q2-259: log P (HCOOH): 3.33 I-A-Q2-260: log P (HCOOH): 3.33 I-A-Q2-261: log P (HCOOH): 4.76
I-A-Q2-262: log P (HCOOH): 3,28 I-A-Q2-263: log P (HCOOH): 5,08 I-A-Q2-264: log P (HCOOH): 1,99I-A-Q2-262: log P (HCOOH): 3.28 I-A-Q2-263: log P (HCOOH): 5.08 I-A-Q2-264: log P (HCOOH): 1.99
I-A-Q2-265: log P (HCOOH): 3,63 I-A-Q2-266: log P (HCOOH): 4,89 I-A-Q2-267: log P (HCOOH): 6,14 IA-Q2-265: log P (HCOOH): 3.63 IA-Q2-266: log P (HCOOH): 4.89 IA-Q2-267: log P (HCOOH): 6.14
I-A-Q2-268: log P (HCOOH): 4,45 I-A-Q2-269: log P (HCOOH): 4,57 I-A-Q2-270: log P (HCOOH): 3,84I-A-Q2-268: log P (HCOOH): 4.45 I-A-Q2-269: log P (HCOOH): 4.57 I-A-Q2-270: log P (HCOOH): 3.84
I-A-Q2-271: log P (HCOOH): 4,45 I-A-Q2-272: log P (HCOOH): 3,24 I-A-Q2-273: log P (HCOOH): 2,98I-A-Q2-271: log P (HCOOH): 4.45 I-A-Q2-272: log P (HCOOH): 3.24 I-A-Q2-273: log P (HCOOH): 2.98
I-A-Q2-274: log P (HCOOH): 4,95 I-A-Q2-275: log P (HCOOH): 4,47 I-A-Q2-276: log P (HCOOH): 4,50I-A-Q2-274: log P (HCOOH): 4.95 I-A-Q2-275: log P (HCOOH): 4.47 I-A-Q2-276: log P (HCOOH): 4.50
I-A-Q2-277: log P (HCOOH): 4,56 I-A-Q2-278: log P (HCOOH): 4,30 I-A-Q2-279: log P (HCOOH): 4,43I-A-Q2-277: log P (HCOOH): 4.56 I-A-Q2-278: log P (HCOOH): 4.30 I-A-Q2-279: log P (HCOOH): 4.43
5 I-A-Q2-280: log P (HCOOH): 3,96 I-A-Q2-281: log P (HCOOH): 3,97 I-A-Q2-282: log P (HCOOH): 5,255 I-A-Q2-280: log P (HCOOH): 3.96 I-A-Q2-281: log P (HCOOH): 3.97 I-A-Q2-282: log P (HCOOH): 5.25
I-A-Q2-283: log P (HCOOH): 4,12 I-A-Q2-284: log P (HCOOH): 4,32 I-A-Q2-285: log P (HCOOH): 4,95I-A-Q2-283: log P (HCOOH): 4.12 I-A-Q2-284: log P (HCOOH): 4.32 I-A-Q2-285: log P (HCOOH): 4.95
4*.4 *.
I-A-Q2-286: log P (HCOOH): 4,89 I-A-Q2-287: log P (HCOOH): 5,33 I-A-Q2-288: log P (HCOOH): 4,40I-A-Q2-286: log P (HCOOH): 4.89 I-A-Q2-287: log P (HCOOH): 5.33 I-A-Q2-288: log P (HCOOH): 4.40
I-A-Q2-289: log P (HCOOH): 4,95 I-A-Q2-290: log P (HCOOH): 4,00 I-A-Q2-291: log P (HCOOH): 3,84I-A-Q2-289: log P (HCOOH): 4.95 I-A-Q2-290: log P (HCOOH): 4.00 I-A-Q2-291: log P (HCOOH): 3.84
I-A-Q2-292: log P (HCOOH): 3,53 I-A-Q2-293: log P (HCOOH): 3,11 I-A-Q2-294: log P (HCOOH): 4,95I-A-Q2-292: log P (HCOOH): 3.53 I-A-Q2-293: log P (HCOOH): 3.11 I-A-Q2-294: log P (HCOOH): 4.95
10 I-A-Q2-295: log P (HCOOH): 5,27 I-A-Q2-296: log P (HCOOH): 5,14 I-A-Q2-297: log P (HCOOH): 4,9510 I-A-Q2-295: log P (HCOOH): 5.27 I-A-Q2-296: log P (HCOOH): 5.14 I-A-Q2-297: log P (HCOOH): 4.95
I-A-Q2-298: log P (HCOOH): 4,64 I-A-Q2-299: log P (HCOOH): 4,51 I-A-Q2-300: log P (HCOOH): 5,40I-A-Q2-298: log P (HCOOH): 4.64 I-A-Q2-299: log P (HCOOH): 4.51 I-A-Q2-300: log P (HCOOH): 5.40
I-A-Q2-301: log P (HCOOH): 3,75 I-A-Q2-302: log P (HCOOH): 3,61 I-A-Q2-303: log P (HCOOH): 3,70I-A-Q2-301: log P (HCOOH): 3.75 I-A-Q2-302: log P (HCOOH): 3.61 I-A-Q2-303: log P (HCOOH): 3.70
I-A-Q2-304: log P (HCOOH): 4,00 I-A-Q2-305: log P (HCOOH): 3,75 I-A-Q2-306: log P (HCOOH): 3,24I-A-Q2-304: log P (HCOOH): 4.00 I-A-Q2-305: log P (HCOOH): 3.75 I-A-Q2-306: log P (HCOOH): 3.24
I-A-Q2-307: log P (HCOOH): 3,27 I-A-Q2-308: log P (HCOOH): 3,23 I-A-Q2-309: log P (HCOOH): 3,65 IA-Q2-307: log P (HCOOH): 3.27 IA-Q2-308: log P (HCOOH): 3.23 IA-Q2-309: log P (HCOOH): 3.65
I-A-Q2-310 : log P (HCOOH) : 3 ,70 I-A-Q2-311: log P (HCOOH): 3,27 I-A-Q2-312: log P (HCOOH): 3,42I-A-Q2-310: log P (HCOOH): 3, 70 I-A-Q2-311: log P (HCOOH): 3.27 I-A-Q2-312: log P (HCOOH): 3.42
I-A-Q2-313: log P (HCOOH): 3,85 I-A-Q2-314: log P (HCOOH): 3,65 I-A-Q2-315: log P (HCOOH): 3,37I-A-Q2-313: log P (HCOOH): 3.85 I-A-Q2-314: log P (HCOOH): 3.65 I-A-Q2-315: log P (HCOOH): 3.37
I-Ä-Q2-316: log P (HCOOH): 3,65 I-A-Q2-317: log P (HCOOH): 3,32 I-A-Q2-318: log P (HCOOH): 4,23I-λ-Q2-316: log P (HCOOH): 3.65 I-A-Q2-317: log P (HCOOH): 3.32 I-A-Q2-318: log P (HCOOH): 4.23
I-A-Q2-319: log P (HCOOH): 2,80 I-A-Q2-320: log P (HCOOH): 3,23 I-A-Q2-321: log P (HCOOH): 4,00I-A-Q2-319: log P (HCOOH): 2.80 I-A-Q2-320: log P (HCOOH): 3.23 I-A-Q2-321: log P (HCOOH): 4.00
5 I-A-Q2-322: log P (HCOOH): 4,34 I-A-Q2-323: log P (HCOOH): 4,32 I-A-Q2-324: log P (HCOOH): 2,305 I-A-Q2-322: log P (HCOOH): 4.34 I-A-Q2-323: log P (HCOOH): 4.32 I-A-Q2-324: log P (HCOOH): 2.30
I-A-Q2-325: log P (HCOOH): 2,85 I-A-Q2-326: log P (HCOOH): 2,51 I-A-Q2-327: log P (HCOOH): 2,73I-A-Q2-325: log P (HCOOH): 2.85 I-A-Q2-326: log P (HCOOH): 2.51 I-A-Q2-327: log P (HCOOH): 2.73
I-A-Q2-328: log P (HCOOH): 2,48 I-A-Q2-329: log P (HCOOH): 2,59 I-A-Q2-330: log P (HCOOH): 3,12I-A-Q2-328: log P (HCOOH): 2.48 I-A-Q2-329: log P (HCOOH): 2.59 I-A-Q2-330: log P (HCOOH): 3.12
I-A-Q2-331: log P (HCOOH): 2,85 I-A-Q2-332: log P (HCOOH): 2,59 I-A-Q2-333: log P (HCOOH): 2,59I-A-Q2-331: log P (HCOOH): 2.85 I-A-Q2-332: log P (HCOOH): 2.59 I-A-Q2-333: log P (HCOOH): 2.59
I-A-Q2-334: log P (HCOOH): 2,59 I-A-Q2-335: log P (HCOOH): 3,04 I-A-Q2-336: log P (HCOOH): 2,76I-A-Q2-334: log P (HCOOH): 2.59 I-A-Q2-335: log P (HCOOH): 3.04 I-A-Q2-336: log P (HCOOH): 2.76
10 I-A-Q2-337: log P (HCOOH): 3,80 I-A-Q2-338: log P (HCOOH): 3,65 I-A-Q2-339: log P (HCOOH): 3,2710 I-A-Q2-337: log P (HCOOH): 3.80 I-A-Q2-338: log P (HCOOH): 3.65 I-A-Q2-339: log P (HCOOH): 3.27
I-A-Q2-340: log P (HCOOH): 3,56 I-A-Q2-341: log P (HCOOH): 3,46 I-A-Q2-342: log P (HCOOH): 3,85I-A-Q2-340: log P (HCOOH): 3.56 I-A-Q2-341: log P (HCOOH): 3.46 I-A-Q2-342: log P (HCOOH): 3.85
I-A-Q2-343: log P (HCOOH): 4,57 I-A-Q2-344: log P (HCOOH): 2,84 I-A-Q2-345: log P (HCOOH): 2,69I-A-Q2-343: log P (HCOOH): 4.57 I-A-Q2-344: log P (HCOOH): 2.84 I-A-Q2-345: log P (HCOOH): 2.69
I-A-Q2-346: log P (HCOOH): 2,80 I-A-Q2-347: log P (HCOOH): 3,11 I-A-Q2-348: log P (HCOOH): 2,84I-A-Q2-346: log P (HCOOH): 2.80 I-A-Q2-347: log P (HCOOH): 3.11 I-A-Q2-348: log P (HCOOH): 2.84
I-A-Q2-349: log P (HCOOH): 2,04 I-A-Q2-350: log P (HCOOH): 2,34 I-A-Q2-351: log P (HCOOH): 2,27 IA-Q2-349: log P (HCOOH): 2.04 IA-Q2-350: log P (HCOOH): 2.34 IA-Q2-351: log P (HCOOH): 2.27
I-A-Q2-352: log P (HCOOH): 2,76 I-A-Q2-353: log P (HCOOH): 2,84 I-A-Q2-354 : log P (HCOOH) : 2,31I-A-Q2-352: log P (HCOOH): 2.76 I-A-Q2-353: log P (HCOOH): 2.84 I-A-Q2-354: log P (HCOOH): 2.31
I-A-Q2-355: log P (HCOOH): 2,50 I-A-Q2-356: log P (HCOOH): 2,93 I-A-Q2-357: log P (HCOOH): 2,72I-A-Q2-355: log P (HCOOH): 2.50 I-A-Q2-356: log P (HCOOH): 2.93 I-A-Q2-357: log P (HCOOH): 2.72
I-A-Q2-358: log P (HCOOH): 2,80 I-A-Q2-359: log P (HCOOH): 2,34 I-A-Q2-360: log P (HCOOH): 3,47I-A-Q2-358: log P (HCOOH): 2.80 I-A-Q2-359: log P (HCOOH): 2.34 I-A-Q2-360: log P (HCOOH): 3.47
I-A-Q2-361: log P (HCOOH): 1,91 I-A-Q2-362: log P (HCOOH): 2,27 I-A-Q2-363: log P (HCOOH): 3,19I-A-Q2-361: log P (HCOOH): 1.91 I-A-Q2-362: log P (HCOOH): 2.27 I-A-Q2-363: log P (HCOOH): 3.19
5 I-A-Q2-364: log P (HCOOH): 3,53 I-A-Q2-365: log P (HCOOH): 2,27 I-A-Q2-366: log P (HCOOH): 1,915 I-A-Q2-364: log P (HCOOH): 3.53 I-A-Q2-365: log P (HCOOH): 2.27 I-A-Q2-366: log P (HCOOH): 1.91
I-A-Q2-367: log P (HCOOH): 1 ,59 I-A-Q2-368: log P (HCOOH): 1,79 I-A-Q2-369: log P (HCOOH): 1 ,52I-A-Q2-367: log P (HCOOH): 1.59 I-A-Q2-368: log P (HCOOH): 1.79 I-A-Q2-369: log P (HCOOH): 1.52
-^ -^- ^ - ^
I-A-Q2-370: log P (HCOOH): 1,64 I-A-Q2-371: log P (HCOOH): l,ϊ I-A-Q2-372: log P (HCOOH): 1,61I-A-Q2-370: log P (HCOOH): 1.64 I-A-Q2-371: log P (HCOOH): 1, ϊ I-A-Q2-372: log P (HCOOH): 1.61
I-A-Q2-373: log P (HCOOH): 1 ,64 I-A-Q2-374: log P (HCOOH): 1 ,66 I-A-Q2-375: log P (HCOOH): 2,04I-A-Q2-373: log P (HCOOH): 1.64 I-A-Q2-374: log P (HCOOH): 1.66 I-A-Q2-375: log P (HCOOH): 2.04
I-A-Q2-376: log P (HCOOH): 1,79 I-A-Q2-377: log P (HCOOH): 2,80 I-A-Q2-378 log P (HCOOH): 2,61I-A-Q2-376: log P (HCOOH): 1.79 I-A-Q2-377: log P (HCOOH): 2.80 I-A-Q2-378 log P (HCOOH): 2.61
10 I-A-Q2-379: log P (HCOOH): 2,20 I-A-Q2-380: log P (HCOOH): 2,53 I-A-Q2-381 : log P (HCOOH): 2,4610 I-A-Q2-379: log P (HCOOH): 2.20 I-A-Q2-380: log P (HCOOH): 2.53 I-A-Q2-381: log P (HCOOH): 2.46
I-A-Q2-382: log P (HCOOH): 2,84 I-A-Q2-383: log P (HCOOH): 3,94 I-A-Q2-384: log P (HCOOH): 4,53I-A-Q2-382: log P (HCOOH): 2.84 I-A-Q2-383: log P (HCOOH): 3.94 I-A-Q2-384: log P (HCOOH): 4.53
I-A-Q2-385: log P (HCOOH): 4,60 I-A-Q2-386: log P (HCOOH): 3,77 I-A-Q2-387: log P (HCOOH): 4,32I-A-Q2-385: log P (HCOOH): 4.60 I-A-Q2-386: log P (HCOOH): 3.77 I-A-Q2-387: log P (HCOOH): 4.32
I-A-Q2-388: log P (HCOOH): 3,37 I-A-Q2-389: log P (HCOOH): 4,35 I-A-Q2-390: log P (HCOOH): 3,41I-A-Q2-388: log P (HCOOH): 3.37 I-A-Q2-389: log P (HCOOH): 4.35 I-A-Q2-390: log P (HCOOH): 3.41
I-A-Q2-391: log P (HCOOH): 3,57 I-A-Q2-392: log P (HCOOH): 3,51 I-A-Q2-393: log P (HCOOH): 4,82 IA-Q2-391: log P (HCOOH): 3.57 IA-Q2-392: log P (HCOOH): 3.51 IA-Q2-393: log P (HCOOH): 4.82
I-A-Q2-394: log P (HCOOH): 3,70 I-A-Q2-395: log P (HCOOH): 4,43 I-A-Q2-396: log P (HCOOH): 4,59I-A-Q2-394: log P (HCOOH): 3.70 I-A-Q2-395: log P (HCOOH): 4.43 I-A-Q2-396: log P (HCOOH): 4.59
I-A-Q2-397: log P (HCOOH): 4,69 I-A-Q2-398: log P (HCOOH): 3,59 I-A-Q2-399: log P (HCOOH): 5,26I-A-Q2-397: log P (HCOOH): 4.69 I-A-Q2-398: log P (HCOOH): 3.59 I-A-Q2-399: log P (HCOOH): 5.26
I-A-Q2-400: log P (HCOOH): 4,36 I-A-Q2-401: log P (HCOOH): 4,93 I-A-Q2-402: log P (HCOOH): 3,89I-A-Q2-400: log P (HCOOH): 4.36 I-A-Q2-401: log P (HCOOH): 4.93 I-A-Q2-402: log P (HCOOH): 3.89
I-A-Q2-403: log P (HCOOH): 4,34 I-A-Q2-404: log P (HCOOH): 4,81 I-A-Q2-405: log P (HCOOH): 4,84I-A-Q2-403: log P (HCOOH): 4.34 I-A-Q2-404: log P (HCOOH): 4.81 I-A-Q2-405: log P (HCOOH): 4.84
5 I-A-Q2-407: log P (HCOOH): 5,15 I-A-Q2-408: log P (HCOOH): 3,68 I-A-Q2-409: log P (HCOOH): 3,385 I-A-Q2-407: log P (HCOOH): 5.15 I-A-Q2-408: log P (HCOOH): 3.68 I-A-Q2-409: log P (HCOOH): 3.38
I-A-Q2-410: log P (HCOOH): 3,94 I-A-Q2-411: log P (HCOOH): 3,17 I-A-Q2-412: log P (HCOOH): 3,29I-A-Q2-410: log P (HCOOH): 3.94 I-A-Q2-411: log P (HCOOH): 3.17 I-A-Q2-412: log P (HCOOH): 3.29
-S-. OO-S. OO
I-A-Q2-413: log P (HCOOH): 3,37 I-A-Q2-414: log P (HCOOH): 2,72 I-A-Q2-415: log P (HCOOH): 2,71I-A-Q2-413: log P (HCOOH): 3.37 I-A-Q2-414: log P (HCOOH): 2.72 I-A-Q2-415: log P (HCOOH): 2.71
I-A-Q2-416: log P (HCOOH): 3,81 I-A-Q2-417: log P (HCOOH): 3,13 I-A-Q2-418: log P (HCOOH): 3,22I-A-Q2-416: log P (HCOOH): 3.81 I-A-Q2-417: log P (HCOOH): 3.13 I-A-Q2-418: log P (HCOOH): 3.22
I-A-Q2-419: log P (HCOOH): 2,68 I-A-Q2-420: log P (HCOOH): 2,81 I-A-Q2-421: log P (HCOOH): 2,53I-A-Q2-419: log P (HCOOH): 2.68 I-A-Q2-420: log P (HCOOH): 2.81 I-A-Q2-421: log P (HCOOH): 2.53
10 I-A-Q2-422: log P (HCOOH): 3,41 I-A-Q2-423: log P (HCOOH): 3,55 I-A-Q2-424: log P (HCOOH): 2,7510 I-A-Q2-422: log P (HCOOH): 3.41 I-A-Q2-423: log P (HCOOH): 3.55 I-A-Q2-424: log P (HCOOH): 2.75
I-A-Q2-425: log P (HCOOH): 2,99 IA-Q2-425: log P (HCOOH): 2.99
Tabelle 3Table 3
Gemäß den oben angegebenen allgemeinen Methoden lassen sich die in der folgenden Tabelle angegebenen Verbindungen der Formel (I-A mit Q = Q ) herstellenAccording to the general methods given above, the compounds of the formula (I-A with Q = Q) given in the following table can be prepared
I-A-Q3-021: log P (HCOOH): 4,48 I-A-Q3-022: log P (HCOOH): 4,12 I-A-Q3-023: log P (HCOOH): 3,70I-A-Q3-021: log P (HCOOH): 4.48 I-A-Q3-022: log P (HCOOH): 4.12 I-A-Q3-023: log P (HCOOH): 3.70
I-A-Q3-024: log P (HCOOH): 3,85 IA-Q3-024: log P (HCOOH): 3.85
Tabelle 4Table 4
Gemäß den oben angegebenen allgemeinen Methoden lassen sich die in der folgenden Tabelle angegebenen Verbindungen der Formel (I-A mit Q = Q4) herstellen.According to the general methods given above, the compounds of the formula (IA with Q = Q 4 ) given in the following table can be prepared.
Charakteristische Daten für Synthesebeispiele:Characteristic data for synthesis examples:
I-A-Q4-001: spektroskopische Daten siehe Protokoll unter allgemeinen SynthesevorschriftenI-A-Q4-001: For spectroscopic data see protocol under general procedure
I-A-Q4-002: spektroskopische Daten siehe Protokoll unter allgemeinen SynthesevorschriftenI-A-Q4-002: For spectroscopic data see protocol under general procedure
5 I-A-Q4-003: IH NMR (CDC13) 8,26-8,18 (m, 2 H), 8,04-7,97 (m, 5 H), 4,44 (q, 2 H, J = 7,1 Hz), 1,42 (t, 3 H, J = 7,1 Hz)5 IA-Q4-003: IH NMR (CDC13) 8.26-8.18 (m, 2H), 8.04-7.97 (m, 5H), 4.44 (q, 2H, J = 7.1 Hz), 1.42 (t, 3 H, J = 7.1 Hz)
I-A-Q4-005: IH NMR (CDC13) 8,22 (d, IH, J = 2,2 Hz), 8,15 (d, 1 H, J = 0,9 Hz), 8,03 (dd, 1 H, J = 8,4 und 2,2 Hz), 7,94-7,91 (m, 1 H), 7,42-7,36 (m, 3 H), 1,58 (s, 9 H)IA-Q4-005: IH NMR (CDC13) 8.22 (d, IH, J = 2.2 Hz), 8.15 (d, 1 H, J = 0.9 Hz), 8.03 (dd, 1 H, J = 8.4 and 2.2 Hz), 7.94-7.91 (m, 1H), 7.42-7.36 (m, 3H), 1.58 (s, 9 H)
I-A-Q4-006: IH NMR (CDC13) 8,27-8,23 (m, 1 H), 8,20-8,17 (m, 1 H), 8,15-8,11 (m, 2 H), 7,44-7,43 (m, 1 H), 7,37-7,37 (m, 2 H)IA-Q4-006: IH NMR (CDCl3) 8.27-8.23 (m, 1H), 8.20-8.17 (m, 1H), 8.15-8.11 (m, 2 H), 7.44-7.43 (m, 1H), 7.37-7.37 (m, 2H)
I-A-Q4-007: IH NMR (CDC13) 7,92-7,87 (m, 1 H), 7,75-7,73 (m, 1 H), 7,66-7,61 (m, 1 H), 7,34-7,29 (m, 3 H), 6,84 (t, 1 H, J = 8,7 Hz), 4,37-4,25 (m, 2 H)IA-Q4-007: IH NMR (CDCl3) 7.92-7.87 (m, 1H), 7.75-7.73 (m, 1H), 7.66-7.61 (m, 1 H), 7.34-7.29 (m, 3H), 6.84 (t, 1H, J = 8.7Hz), 4.37-4.25 (m, 2H)
10 I-A-Q4-008: IH NMR (CDC13) 8,25 (d, 1 H, J = 0,5 Hz), 8,16 (s, 1 H), 8,02 (s, 1 H), 7,97 (d, 2 H, J = 1,3 Hz), 7,44 (d, 2 H, J = 1,8 Hz), 7,32-7,30 (m, 1 H), 4,43 (q, 2 H J = 7,1 Hz), 1,41 (t, 3 H, J = 8,6 Hz) 10 IA-Q4-008: IH NMR (CDC13) 8.25 (d, 1H, J = 0.5 Hz), 8.16 (s, 1H), 8.02 (s, 1H), 7 , 97 (d, 2H, J = 1.3Hz), 7.44 (d, 2H, J = 1.8Hz), 7.32-7.30 (m, 1H), 4.43 (q, 2 HJ = 7.1 Hz), 1.41 (t, 3 H, J = 8.6 Hz)
I-A-Q4-009: spektroskopische Daten siehe Protokoll unter allgemeinen Synthesevorschriften I-A-Q4-010: spektroskopische Daten siehe Protokoll unter allgemeinen Synthesevorschriften I-A-Q4-011: spektroskopische Daten siehe Protokoll unter allgemeinen SynthesevorschriftenI-A-Q4-009: for spectroscopic data see protocol under general synthesis instructions I-A-Q4-010: for spectroscopic data see protocol under general synthesis instructions I-A-Q4-011: for spectroscopic data see protocol under general synthesis procedure
I-A-Q4-012: spektroskopische Daten siehe Protokoll unter allgemeinen Synthesevorschriften 5 I-A-Q4-013: spektroskopische Daten siehe Protokoll unter allgemeinen SynthesevorschriftenI-A-Q4-012: spectroscopic data see protocol under general synthetic procedure 5 I-A-Q4-013: For spectroscopic data see protocol under general synthesis procedure
I-A-Q4-014: log P (HCOOH): 5,76 I-A-Q4-015: log P (HCOOH): 3,47 I-A-Q4-016: log P (HCOOH): 5,76I-A-Q4-014: log P (HCOOH): 5.76 I-A-Q4-015: log P (HCOOH): 3.47 I-A-Q4-016: log P (HCOOH): 5.76
I-A-Q4-017: log P (HCOOH): 6,71 I-A-Q4-018: log P (HCOOH): 6,50 I-A-Q4-019: log P (HCOOH): 3,94I-A-Q4-017: log P (HCOOH): 6.71 I-A-Q4-018: log P (HCOOH): 6.50 I-A-Q4-019: log P (HCOOH): 3.94
I-A-Q4-020: log P (HCOOH): 5,22 I-A-Q4-021: log P (HCOOH): 4,70 I-A-Q4-022: log P (HCOOH): 5,22I-A-Q4-020: log P (HCOOH): 5.22 I-A-Q4-021: log P (HCOOH): 4.70 I-A-Q4-022: log P (HCOOH): 5.22
I-A-Q4-023: log P (HCOOH): 4,57 I-A-Q4-024: log P (HCOOH): 5,36 I-A-Q4-025: log P (HCOOH): 5,51I-A-Q4-023: log P (HCOOH): 4.57 I-A-Q4-024: log P (HCOOH): 5.36 I-A-Q4-025: log P (HCOOH): 5.51
10 I-A-Q4-026: log P (HCOOH): 5,02 I-A-Q4-027: log P (HCOOH): 5,73 I-A-Q4-028: log P (HCOOH): 5,6410 I-A-Q4-026: log P (HCOOH): 5.02 I-A-Q4-027: log P (HCOOH): 5.73 I-A-Q4-028: log P (HCOOH): 5.64
I-A-Q4-029: log P (HCOOH): 4,05 I-A-Q4-030: log P (HCOOH): 4,57 I-A-Q4-031: log P (HCOOH): 3,78I-A-Q4-029: log P (HCOOH): 4.05 I-A-Q4-030: log P (HCOOH): 4.57 I-A-Q4-031: log P (HCOOH): 3.78
I-A-Q4-032: log P (HCOOH): 3,89 I-A-Q4-033: log P (HCOOH): 3,84 I-A-Q4-034: log P (HCOOH): 4,40I-A-Q4-032: log P (HCOOH): 3.89 I-A-Q4-033: log P (HCOOH): 3.84 I-A-Q4-034: log P (HCOOH): 4.40
I-A-Q4-035: log P (HCOOH): 3,78 I-A-Q4-036: log P (HCOOH): 3,58 I-A-Q4-037: log P (HCOOH): 4,05I-A-Q4-035: log P (HCOOH): 3.78 I-A-Q4-036: log P (HCOOH): 3.58 I-A-Q4-037: log P (HCOOH): 4.05
I-A-Q4-038: log P (HCOOH): 3,84 I-A-Q4-039: log P (HCOOH): 4,40 I-A-Q4-040: log P (HCOOH): 5,29 IA-Q4-038: log P (HCOOH): 3.84 IA-Q4-039: log P (HCOOH): 4.40 IA-Q4-040: log P (HCOOH): 5.29
I-A-Q4-041: log P (HCOOH): 4,95 I-A-Q4-042: log P (HCOOH): 5,22 I-A-Q4-043: log P (HCOOH): 5,44I-A-Q4-041: log P (HCOOH): 4.95 I-A-Q4-042: log P (HCOOH): 5.22 I-A-Q4-043: log P (HCOOH): 5.44
I-A-Q4-044: log P (HCOOH): 5,02 I-A-Q4-045: log P (HCOOH): 4,11 I-A-Q4-046: log P (HCOOH): 4,46I-A-Q4-044: log P (HCOOH): 5.02 I-A-Q4-045: log P (HCOOH): 4.11 I-A-Q4-046: log P (HCOOH): 4.46
I-A-Q4-047: log P (HCOOH): 4,95 I-A-Q4-048: log P (HCOOH): 5,02 I-A-Q4-049: log P (HCOOH): 4,51I-A-Q4-047: log P (HCOOH): 4.95 I-A-Q4-048: log P (HCOOH): 5.02 I-A-Q4-049: log P (HCOOH): 4.51
I-A-Q4-050: log P (HCOOH): 4,64 I-A-Q4-051: log P (HCOOH): 5,29 I-A-Q4-052: log P (HCOOH): 5,02I-A-Q4-050: log P (HCOOH): 4.64 I-A-Q4-051: log P (HCOOH): 5.29 I-A-Q4-052: log P (HCOOH): 5.02
5 I-A-Q4-053: log P (HCOOH): 4,89 I-A-Q4-054: log P (HCOOH): 4,64 I-A-Q4-055: log P (HCOOH): 4,835 I-A-Q4-053: log P (HCOOH): 4.89 I-A-Q4-054: log P (HCOOH): 4.64 I-A-Q4-055: log P (HCOOH): 4.83
I-A-Q4-056: log P (HCOOH): 3,84 I-A-Q4-057: log P (HCOOH): 4,45 I-A-Q4-058: log P (HCOOH): 5,44I-A-Q4-056: log P (HCOOH): 3.84 I-A-Q4-057: log P (HCOOH): 4.45 I-A-Q4-058: log P (HCOOH): 5.44
OOOO
I-A-Q4-059: log P (HCOOH): 5,81 I-A-Q4-060: log P (HCOOH): 5,02 I-A-Q4-061: log P (HCOOH): 3,58I-A-Q4-059: log P (HCOOH): 5.81 I-A-Q4-060: log P (HCOOH): 5.02 I-A-Q4-061: log P (HCOOH): 3.58
I-A-Q4-062: log P (HCOOH): 5,97 I-A-Q4-063: log P (HCOOH): 4,66 I-A-Q4-064: log P (HCOOH): 4,23I-A-Q4-062: log P (HCOOH): 5.97 I-A-Q4-063: log P (HCOOH): 4.66 I-A-Q4-064: log P (HCOOH): 4.23
I-A-Q4-085: log P (HCOOH): 4,57 I-A-Q4-086: log P (HCOOH): 4,93 I-A-Q4-087: log P (HCOOH): 3,79I-A-Q4-085: log P (HCOOH): 4.57 I-A-Q4-086: log P (HCOOH): 4.93 I-A-Q4-087: log P (HCOOH): 3.79
10 I-A-Q4-088: log P (HCOOH): 3,28 I-A-Q4-089: log P (HCOOH): 3,69 I-A-Q4-090: log P (HCOOH): 3,4210 I-A-Q4-088: log P (HCOOH): 3.28 I-A-Q4-089: log P (HCOOH): 3.69 I-A-Q4-090: log P (HCOOH): 3.42
I-A-Q4-091: log P (HCOOH): 3,29 I-A-Q4-092: log P (HCOOH): 3,06 I-A-Q4-093: log P (HCOOH): 3,39I-A-Q4-091: log P (HCOOH): 3.29 I-A-Q4-092: log P (HCOOH): 3.06 I-A-Q4-093: log P (HCOOH): 3.39
I-A-Q4-094: log P (HCOOH): 3,31 I-A-Q4-095: log P (HCOOH): 3,44 I-A-Q4-096: log P (HCOOH): 3,20I-A-Q4-094: log P (HCOOH): 3.31 I-A-Q4-095: log P (HCOOH): 3.44 I-A-Q4-096: log P (HCOOH): 3.20
I-A-Q4-097: log P (HCOOH): 2,ϊ I-A-Q4-098: log P (HCOOH): 3,35 I-A-Q4-099: log P (HCOOH): 3,32I-A-Q4-097: log P (HCOOH): 2, ϊ I-A-Q4-098: log P (HCOOH): 3.35 I-A-Q4-099: log P (HCOOH): 3.32
I-A-Q4-100: log P (HCOOH): 3,32 I-A-Q4-101: log P (HCOOH): 2,94 I-A-Q4-102: log P (HCOOH): 5,94 IA-Q4-100: log P (HCOOH): 3.32 IA-Q4-101: log P (HCOOH): 2.94 IA-Q4-102: log P (HCOOH): 5.94
I-A-Q4-103: log P (HCOOH): 4,44 I-A-Q4-104: log P (HCOOH): 5,07 I-A-Q4-105: log P (HCOOH): 5,25I-A-Q4-103: log P (HCOOH): 4.44 I-A-Q4-104: log P (HCOOH): 5.07 I-A-Q4-105: log P (HCOOH): 5.25
I-A-Q4-106: log P (HCOOH): 4,68 I-A-Q4-107: log P (HCOOH): 4,45 I-A-Q4-109: log P (HCOOH): 4,77I-A-Q4-106: log P (HCOOH): 4.68 I-A-Q4-107: log P (HCOOH): 4.45 I-A-Q4-109: log P (HCOOH): 4.77
I-A-Q4-110: log P (HCOOH): 4,49 I-A-Q4-111: log P (HCOOH): 4,77 I-A-Q4-112: log P (HCOOH): 5,21I-A-Q4-110: log P (HCOOH): 4.49 I-A-Q4-111: log P (HCOOH): 4.77 I-A-Q4-112: log P (HCOOH): 5.21
I-A-Q4-113: log P (HCOOH): 4,78 I-A-Q4-114: log P (HCOOH): 4,84 I-A-Q4-115: log P (HCOOH): 4,22I-A-Q4-113: log P (HCOOH): 4.78 I-A-Q4-114: log P (HCOOH): 4.84 I-A-Q4-115: log P (HCOOH): 4.22
5 I-A-Q4-116: log P (HCOOH): 3,91 I-A-Q4-117: log P (HCOOH): 3,96 I-A-Q4-118: log P (HCOOH): 4,935 I-A-Q4-116: log P (HCOOH): 3.91 I-A-Q4-117: log P (HCOOH): 3.96 I-A-Q4-118: log P (HCOOH): 4.93
I-A-Q4-119: log P (HCOOH): 4,71 I-A-Q4-120: log P (HCOOH): 4,11 I-A-Q4-121: log P (HCOOH): 3,07I-A-Q4-119: log P (HCOOH): 4.71 I-A-Q4-120: log P (HCOOH): 4.11 I-A-Q4-121: log P (HCOOH): 3.07
I-A-Q4-122: log P (HCOOH): 4,69 I-A-Q4-123: log P (HCOOH): 4,41I-A-Q4-122: log P (HCOOH): 4.69 I-A-Q4-123: log P (HCOOH): 4.41
Tabelle 5Table 5
10 Gemäß den oben angegebenen allgemeinen Methoden lassen sich die in der folgenden Tabelle angegebenen Verbindungen der Formel (I-B mit Q = Q ) herstellenIn accordance with the general methods given above, it is possible to prepare the compounds of the formula (I-B where Q = Q) shown in the table below
(I-B-Q1) (IBQ 1 )
Tabelle 6Table 6
Gemäß den oben angegebenen allgemeinen Methoden lassen sich die in der folgenden Tabelle angegebenen Verbindungen der Formel (I-B mit Q = Q2) herstellenAccording to the general methods given above, the compounds of the formula (IB where Q = Q 2 ) given in the following table can be prepared
I-B-Q2-001: log P (HCOOH): 4,74 I-B-Q2-021: log P (HCOOH): 4,58 I-B-Q2-022: log P (HCOOH): 3,54I-B-Q2-001: log P (HCOOH): 4.74 I-B-Q2-021: log P (HCOOH): 4.58 I-B-Q2-022: log P (HCOOH): 3.54
I-B-Q2-023: log P (HCOOH): 4,57 I-B-Q2-024: log P (HCOOH): 4,20 IB-Q2-023: log P (HCOOH): 4.57 IB-Q2-024: log P (HCOOH): 4.20
Tabelle 7Table 7
Gemäß den oben angegebenen allgemeinen Methoden lassen sich die in der folgenden Tabelle angegebenen Verbindungen der Formel (I-B mit Q = Q3) herstellen.According to the general methods given above, the compounds of the formula (IB where Q = Q 3 ) given in the following table can be prepared.
Tabelle 8Table 8
Gemäß den oben angegebenen allgemeinen Methoden lassen sich die in der folgenden Tabelle angegebenen Verbindungen der Formel (I-B mit Q = Q4) herstellen.According to the general methods given above, the compounds of the formula (IB where Q = Q 4 ) given in the following table can be prepared.
I-B-Q4-021: log P (HCOOH): 4,12I-B-Q4-021: log P (HCOOH): 4.12
OO OO
Tabelle 9Table 9
Gemäß den oben angegebenen allgemeinen Methoden lassen sich die in der folgenden Tabelle angegebenen Hydrazine der Formel (VII-A) herstellen.According to the general methods given above, the hydrazines of the formula (VII-A) given in the following table can be prepared.
Charakteristische Daten für Synthesebeispiele:Characteristic data for synthesis examples:
VÜ-A-008: spektroskopische Daten siehe Protokoll unter allgemeinen SynthesevorschriftenVÜ-A-008: For spectroscopic data see protocol under general procedure
VII-A-103: spektroskopische Daten siehe Protokoll unter allgemeinen SynthesevorschriftenVII-A-103: For spectroscopic data see protocol under general procedure
Tabelle 10Table 10
Gemäß den oben angegebenen allgemeinen Methoden lassen sich die in der folgenden Tabelle angegebenen Hydrazine der Formel (VII-B) herstellen.According to the general methods given above, the hydrazines of the formula (VII-B) given in the following table can be prepared.
(VII-B) (VII-B)
Tabelle 11Table 11
Gemäß den oben angegebenen allgemeinen Methoden lassen sich die in der folgenden Tabelle angegebenen Verbindungen der Formel (DC) herstellenAccording to the general methods given above, the compounds of the formula (DC) given in the following table can be prepared
Charakteristische Daten für Svnthesebeispiele:Characteristic Data for Synthesis Examples:
IX-021: log P (HCOOH) 2,91IX-021: log P (HCOOH) 2.91
1H NMR (DMS0-d6) δ = 12,32 (s, 1 H), 7,45 (s, 1 H), 7,25 (s, 2 ), 5,32 (s, 2 H) ppm IX-38: log P (HCOOH) 2 80 1 H NMR (DMSO-d6) δ = 12.32 (s, 1H), 7.45 (s, 1H), 7.25 (s, 2), 5.32 (s, 2H) ppm IX -38: log P (HCOOH) 2 80
1H NMR (DMS0-d6) δ = 5 27 (br s, 2H), 7 25 (dd, IH), 7 46 (d, IH), 7 61 (d, IH) ppm IX-201: log P (HCOOH) 2 33 1 H NMR (DMSO-d6) δ = 5 27 (br s, 2H), 7 25 (dd, IH), 7 46 (d, IH), 7 61 (d, IH) ppm IX-201: log P ( HCOOH) 2 33
LX-202: log P (HCOOH) 2 16LX-202: log P (HCOOH) 2 16
IX-203: log P (HCOOH) 2 98 IX-204: log P (HCOOH): 2.79IX-203: log P (HCOOH) 2 98 IX-204: log P (HCOOH): 2.79
1H NMR (DMSO-d6): δ = 1.99 (s, 3H); 7.32 (d, IH); 7.47 (d, IH); 7.67 (s, IH); 9.98 (s, IH, NH); 13.53 (s, IH, NH) ppm 1 H NMR (DMSO-d6): δ = 1.99 (s, 3H); 7.32 (d, IH); 7.47 (d, IH); 7.67 (s, IH); 9.98 (s, IH, NH); 13.53 (s, IH, NH) ppm
Tabelle 12Table 12
Gemäß den oben angegebenen allgemeinen Methoden lassen sich die in der folgenden Tabelle angegebenen Verbindungen der Formel (XI-A) herstellen According to the general methods given above, the compounds of the formula (XI-A) given in the following table can be prepared
OOOO
OOOO
Charakteristische Daten für Svnthesebeispiele;Characteristic Data for Synthesis Examples;
Η-NMR-Daten (400 MHz., interner Standard: Tetramethylsilan δ = 0.00 ppm; s = Singulett, br. s = breites Singulett, d = Dublett, dd = Doppeldublett, m =Η-NMR data (400 MHz, internal standard: tetramethylsilane δ = 0.00 ppm; s = singlet, br. S = broad singlet, d = doublet, dd = double doublet, m =
Multiple«, q = Quartett, t = Triplett)Multiple, q = quartet, t = triplet)
XI-A-001 : spektroskopische Daten siehe Protokoll unter allgemeinen SynthesevorschriftenXI-A-001: For spectroscopic data see protocol under general synthetic procedures
5 XI-A-018: log P (HCOOH): 3.605 XI-A-018: log P (HCOOH): 3.60
1H NMR (DMSO-(Io): δ = 1.35 (t, 3H); 4.36 (q, 2H); 5.88 (br. s, 2H); 7.74 (d, 2H); 8.10 (d, 2H) ppm 1 H NMR (DMSO- (Io): δ = 1.35 (t, 3H); 4.36 (q, 2H); 5.88 (br, s, 2H); 7.74 (d, 2H); 8.10 (d, 2H) ppm
XI-A-038: log P (HCOOH): 2,38 ∞XI-A-038: log P (HCOOH): 2.38 ∞
1H NMR (DMSO-d6): δ = 4.70 (br. s, 2H); 7.68 (d, 2H); 8.15 (d, 2H) ppm 1 H NMR (DMSO-d6): δ = 4.70 (br.s, 2H); 7.68 (d, 2H); 8.15 (d, 2H) ppm
XI-A-042: log P (HCOOH): 3.52XI-A-042: log P (HCOOH): 3.52
10 1H NMR (CD3CN): δ = 1.37 (t, 3H); 4.38 (q, 2H); 4.71 (br.s, 2H); 7.68 (d, 2H); 8.14 (d, 2H) ppm10 1 H NMR (CD 3 CN): δ = 1.37 (t, 3H); 4.38 (q, 2H); 4.71 (br.s, 2H); 7.68 (d, 2H); 8.14 (d, 2H) ppm
XI-A-043: log P (HCOOH): 2.34XI-A-043: log P (HCOOH): 2.34
1H NMR (CD3CN): δ = 4.70 (br.s, 2H); 7.68 (d, 2H); 8.15 (d, 2H) ppm 1 H NMR (CD 3 CN): δ = 4.70 (br.s, 2H); 7.68 (d, 2H); 8.15 (d, 2H) ppm
XI-A-044: log P (HCOOH): 3.66XI-A-044: log P (HCOOH): 3.66
1H NMR (DMSO-d6): δ = 1.35 (t, 3H); 4.34 (q, 2H); 5.70 (br.s, 2H); 7.73 (d, 2H); 8.09 (d, 2H) ppm 1 H NMR (DMSO-d6): δ = 1.35 (t, 3H); 4.34 (q, 2H); 5.70 (br.s, 2H); 7.73 (d, 2H); 8.09 (d, 2H) ppm
XI-A-045: log P (HCOOH): 2.47XI-A-045: log P (HCOOH): 2.47
1H NMR (DMS0-d6): δ = 5.69 (br.s, 2H); 7.70 (d, 2H); 8.07 (d, 2H); 12.9 (br. s, IH) ppm 1 H NMR (DMSO-d6): δ = 5.69 (br.s, 2H); 7.70 (d, 2H); 8.07 (d, 2H); 12.9 (br s, IH) ppm
XI-A-046: 1H NMR (CD3CN): δ = 2.89 (d,3H); 4.66 (br. s, 2H); 6.95 (br. S, IH); 7.63 (d, 2H); 7.92 (d, 2H) ppmXI-A-046: 1 H NMR (CD 3 CN): δ = 2.89 (d, 3H); 4.66 (brs s, 2H); 6.95 (br, S, IH); 7.63 (d, 2H); 7.92 (d, 2H) ppm
XI-A-047: 1H NMR (CD3CN): δ = 2.99 (br. s, 6H); 4.66 (br. s, 2H); 7.53-7.60 (m, 4H) ppmXI-A-047: 1 H NMR (CD 3 CN): δ = 2.99 (br, s, 6H); 4.66 (brs s, 2H); 7.53-7.60 (m, 4H) ppm
5 XI-A-048: 1H NMR (CD3CN): δ = 1.20 (t, 3H); 3.40 (m, 2H); 4.66 (br.s, 2H); 6.99 (br. s, IH); 7.62 (d, 2H); 7.93 (d, 2H) ppm5 XI-A-048: 1 H NMR (CD 3 CN): δ = 1.20 (t, 3H); 3.40 (m, 2H); 4.66 (br.s, 2H); 6.99 (br s, IH); 7.62 (d, 2H); 7.93 (d, 2H) ppm
XI-A-049: 1H NMR (CD3CN): S = 0.96 (t, 3H); 1.62 (m, 2H); 3.33 (m, 2H); 4.66 (br. s, 2H); 6.99 (br. s, IH); 7.62 (d, 2H); 7.93 (d, 2H) ppm OOXI-A-049: 1 H NMR (CD 3 CN): S = 0.96 (t, 3H); 1.62 (m, 2H); 3.33 (m, 2H); 4.66 (brs s, 2H); 6.99 (br s, IH); 7.62 (d, 2H); 7.93 (d, 2H) ppm OO
XI-A-050: 1H NMR (CD3CN): δ = 1.24 (d, 6H); 4.19 (m, IH); 4.66 (br.s, 2H); 6.80 (br. s, IH); 7.62 (d, 2H); 7.93 (d, 2H) ppm ^XI-A-050: 1 H NMR (CD 3 CN): δ = 1.24 (d, 6H); 4.19 (m, IH); 4.66 (br.s, 2H); 6.80 (br s, IH); 7.62 (d, 2H); 7.93 (d, 2H) ppm ^
XI-A-OSl: 1H NMR (CD3CN): δ = 0.62 (m, 2H); 0.76 (m, 2H); 2.86 (m, IH); 4.68 (br. s, 2H); 7.06 (br. s, IH); 7.62 (d, 2H); 7.90 (d, 2H) ppmXI-A-OSI: 1 H NMR (CD 3 CN): δ = 0.62 (m, 2H); 0.76 (m, 2H); 2.86 (m, IH); 4.68 (brs s, 2H); 7.06 (brs s, IH); 7.62 (d, 2H); 7.90 (d, 2H) ppm
XI-A-052: 1H NMR (CD3CN): δ = 1.43 (d, 3H); 4.82 (br. s, 2H); 4.93 (m, IH); 7.40 (br. d, IH); 7.68 (d, 2H); 7.99 (d, 2H) ppmXI-A-052: 1 H NMR (CD 3 CN): δ = 1.43 (d, 3H); 4.82 (brs s, 2H); 4.93 (m, IH); 7.40 (br d, IH); 7.68 (d, 2H); 7.99 (d, 2H) ppm
10 XI-A-053: 1H NMR (CD3CN): δ = 1.44 (s, 9H); 4.80 (br. s, 2H); 6.70 (br. s, IH); 7.60 (d, 2H); 7.91 (d, 2H) ppm10 XI-A-053: 1 H NMR (CD 3 CN): δ = 1.44 (s, 9H); 4.80 (brs s, 2H); 6.70 (brs s, IH); 7.60 (d, 2H); 7.91 (d, 2H) ppm
XI-A-054: 1H NMR (CD3CN): δ = 0.96 (s, 9H); 1.15 (d, 3H); 4.05 (m, IH); 4.80 (br. s, 2H); 6.78 (br. d, IH); 7.63 (d, 2H); 7.94 (d, 2H) ppmXI-A-054: 1 H NMR (CD 3 CN): δ = 0.96 (s, 9H); 1.15 (d, 3H); 4.05 (m, IH); 4.80 (brs s, 2H); 6.78 (br d, IH); 7.63 (d, 2H); 7.94 (d, 2H) ppm
XI-A-055: 1H NMR (CD3CN): δ = 4.71 (br. s, 2H); 7.35 (m, IH); 7.73 (d, 2H); 8.10 (d, 2H); 8.14 (m, IH); 8.34 (m, IH); 8.85 (br., 2H) ppmXI-A-055: 1 H NMR (CD 3 CN): δ = 4.71 (br.s, 2H); 7.35 (m, IH); 7.73 (d, 2H); 8.10 (d, 2H); 8.14 (m, IH); 8.34 (m, IH); 8.85 (br., 2H) ppm
XI-A-056: 1H NMR (CD3CN): δ = 4.68 (d, 2H); 4.82 (br. s, 2H); 7.29 (m, IH); 7.40 (d, IH); 7.67 (d, 2H); 7.77 (m, IH); 7.88 (br. m, IH); 8.02 (d, 2H);XI-A-056: 1 H NMR (CD 3 CN): δ = 4.68 (d, 2H); 4.82 (brs s, 2H); 7.29 (m, IH); 7.40 (d, IH); 7.67 (d, 2H); 7.77 (m, IH); 7.88 (br, m, IH); 8.02 (d, 2H);
8.53 (m, IH) ppm 8.53 (m, IH) ppm
XI-A-057: 1H NMR (DMS0-d6): δ = 2.82 (d, 3H); 5.80 (br. s, 2H); 7.66 (d, 2H); 7.98 (d, 2H); 8.37 (br. s, IH) ppmXI-A-057: 1 H NMR (DMS0-d6): δ = 2.82 (d, 3H); 5.80 (brs s, 2H); 7.66 (d, 2H); 7.98 (d, 2H); 8.37 (br s, IH) ppm
XI-A-058: 1H NMR (DMS0-d6): δ = 2.98 (s, 6H); 5.80 (br. s, 2H); 7.54-7.63 (m, 4H) ppmXI-A-058: 1 H NMR (DMS0-d6): δ = 2.98 (s, 6H); 5.80 (brs s, 2H); 7.54-7.63 (m, 4H) ppm
XI-A-059: l1τHτ T NvTMH zTRn ( mDuMcSA0-d J6_:\).: δ 5 = _ 11. i15 c T i 3.3 n2 ( /m, i 2τHτ\);. 5 c. a7n9 ( /ibr. s, i 2τHτ\);. 7.6 _:5c / (dJ, i 2τHτ\);. a 7. n9n9 / (dJ, ^ 2τHτ\);. / (Tbr. * t, i IτHτ\) _ ppm -XI-A-059: l 1 τHτ T NvTMH zTRn (mDuMcSA0-d J6 _: \) .: δ 5 = _ 11. i15 c T i 3.3 n2 (/ m, i 2τHτ \) ;. 5 c. a7n9 (/ ibr. s, i 2τHτ \) ;. 7.6 _: 5c / (dJ, i 2τHτ \) ;. a 7. n9n9 / (dJ, ^ 2τHτ \) ;. / (Tbr. * T, i τHτ \) _ ppm -
XI-A-060: 1H NMR (DMS0-d6): δ = 0.91 (t, 3H); 1.57 (m, 2H); 3.25 (m, 2H); 5.79 (br. s, 2H); 7.65 (d, 2H); 8.00 (d, 2H); 8.38 (br. t, IH) ppmXI-A-060: 1 H NMR (DMSO-d6): δ = 0.91 (t, 3H); 1.57 (m, 2H); 3.25 (m, 2H); 5.79 (brs s, 2H); 7.65 (d, 2H); 8.00 (d, 2H); 8.38 (br.t, IH) ppm
5 XI-A-061: 1H NMR (DMS0-d6): δ = 1.20 (d, 6H); 4.12 (m, IH); 5.78 (br. s, 2H); 7.64 (d, 2H); 8.00 (d, 2H); 8.15 (br. d, IH) ppm5 XI-A-061: 1 H NMR (DMS0-d6): δ = 1.20 (d, 6H); 4.12 (m, IH); 5.78 (brs s, 2H); 7.64 (d, 2H); 8.00 (d, 2H); 8.15 (br d, IH) ppm
XI-A-062: 1H NMR (DMS0-d6): δ = 0.60 (m, 2H); 0.71 (m, 2H); 2.90 (m, IH); 5.79 (br. s, 2H); 7.64 (d, 2H); 7.97 (d, 2H); 8.38 (br. s, IH) ppm oo XI-A-063: 1H NMR (DMSO-d6): δ = 1.39 (d, 3H); 4.88 (m, IH); 5.81 (br. s, 2H); 7.70 (d, 2H); 8.05 (d, 2H); 8.82 (br. d, IH) ppm TXI-A-062: 1 H NMR (DMS0-d6): δ = 0.60 (m, 2H); 0.71 (m, 2H); 2.90 (m, IH); 5.79 (brs s, 2H); 7.64 (d, 2H); 7.97 (d, 2H); 8:38 (br s, IH.) Ppm oo XI-A-063: 1 H NMR (DMSO-d6): δ = 1:39 (d, 3H); 4.88 (m, IH); 5.81 (brs s, 2H); 7.70 (d, 2H); 8.05 (d, 2H); 8.82 (br d, IH) ppm T
XI-A-064: 1H NMR (DMSO-d6): δ = 1.40 (s, 9H); 5.76 (br. s, 2H); 7.62 (d, 2H); 7.67 (br. s, IH); 7.96 (d, 2H) ppmXI-A-064: 1 H NMR (DMSO-d6): δ = 1:40 (s, 9H); 5.76 (brs s, 2H); 7.62 (d, 2H); 7.67 (brs s, IH); 7.96 (d, 2H) ppm
XI-A-065: 1H NMR (DMSO-d6): δ = 0.92 (s, 9H); 1.11 (d, 3H); 4.01 (m, IH); 5.78 (br. s, 2H); 7.64 (d, 2H); 7.87 (br. d, IH); 8.01 (d, 2H) ppmXI-A-065: 1 H NMR (DMSO-d6): δ = 0.92 (s, 9H); 1.11 (d, 3H); 4.01 (m, IH); 5.78 (brs s, 2H); 7.64 (d, 2H); 7.87 (br d, IH); 8.01 (d, 2H) ppm
10 XI-A-066: 1H NMR (DMSO-d6): δ = 5.7-6.0 (br. Signal, 2H); 7.55 (m, IH); 7.78 (d, 2H); 8.17 (d, 2H); 8.34 (m, IH); 8.40 (m, IH); 9.06 (br. s, IH); 10.62 (s, IH) ppm10 XI-A-066: 1 H NMR (DMSO-d6): δ = 5.7-6.0 (br, signal, 2H); 7.55 (m, IH); 7.78 (d, 2H); 8.17 (d, 2H); 8.34 (m, IH); 8.40 (m, IH); 9.06 (brs s, IH); 10.62 (s, IH) ppm
XI-A-067: 1H NMR (DMSO-d6): δ = 4.61 (d, 2H); 5.82 (br. s, 2H); 7.25 (m, IH); 7.34 (m, IH); 7.67 (d, 2H); ~ 7.5 (m, IH); 8.08 (d, 2H); 8.51 (m, IH); 9.03 (br. t, IH) ppmXI-A-067: 1 H NMR (DMSO-d6): δ = 4.61 (d, 2H); 5.82 (brs s, 2H); 7.25 (m, IH); 7.34 (m, IH); 7.67 (d, 2H); ~ 7.5 (m, IH); 8.08 (d, 2H); 8.51 (m, IH); 9.03 (br t, IH) ppm
XI-A-068: 1H NMR (DMSO-d6): δ = 2.82 (d, 3H); 5.62 (br. s, 2H); 7.64 (d, 2H); 7.98 (d, 2H); 8.36 (br. s, IH) ppmXI-A-068: 1 H NMR (DMSO-d6): δ = 2.82 (d, 3H); 5.62 (brs s, 2H); 7.64 (d, 2H); 7.98 (d, 2H); 8.36 (br s, IH) ppm
15 XI-A-069: 1H NMR (DMSO-d6): δ = 2.98 (s, 6H); 5.63 (br. s, 2H); 7.53-7.73 (m, 4H) ppm 15 XI-A-069: 1 H NMR (DMSO-d6): δ = 2.98 (s, 6H); 5.63 (brs s, 2H); 7.53-7.73 (m, 4H) ppm
XI-A-070: 1H NMR (DMS0-d6): δ = 1.15 (t, 3H); 3.32 (m, 2H); 5.61 (br. s, 2H); 7.64 (d, 2H); 7.99 (d, 2H); 8.39 (br. s, IH) ppmXI-A-070: 1 H NMR (DMS0-d6): δ = 1.15 (t, 3H); 3.32 (m, 2H); 5.61 (brs s, 2H); 7.64 (d, 2H); 7.99 (d, 2H); 8.39 (br s, IH) ppm
XI-A-071: 1H NMR (DMSO-dδ): δ = 0.91 (t, 3H); 1.55 (m, 2H); 3.26 (m, 2H); 5.61 (br. s, 2H); 7.64 (d, 2H); 7.99 (d, 2H); 8.38 (br. t, IH) ppmXI-A-071: 1 H NMR (DMSO-dδ): δ = 0.91 (t, 3H); 1.55 (m, 2H); 3.26 (m, 2H); 5.61 (brs s, 2H); 7.64 (d, 2H); 7.99 (d, 2H); 8.38 (br.t, IH) ppm
XI-A-072: 1H NMR (DMSO-d6): δ = 1.19 (d, 6H); 4.12 (m, IH); 5.60 (br. s, 2H); 7.63 (d, 2H); 8.00 (d, 2H); 8.15 (br. d, IH) ppmXI-A-072: 1 H NMR (DMSO-d6): δ = 1.19 (d, 6H); 4.12 (m, IH); 5.60 (brs s, 2H); 7.63 (d, 2H); 8.00 (d, 2H); 8.15 (br d, IH) ppm
XI-A-073: 1H NMR (DMSO-d6): δ = 0.61 (m, 2H); 0.71 (m, 2H); 2.89 (m, IH); 5.61 (br. s, 2H); 7.63 (d, 2H); 7.97 (d, 2H); 8.37 (br. s, IH) ppmXI-A-073: 1 H NMR (DMSO-d6): δ = 0.61 (m, 2H); 0.71 (m, 2H); 2.89 (m, IH); 5.61 (brs s, 2H); 7.63 (d, 2H); 7.97 (d, 2H); 8.37 (br s, IH) ppm
5 XI-A-074: 1H NMR (DMSO-d6): δ = 1.39 (d, 3H); 4.87 (m, IH); 5.64 (br. s, 2H); 7.68 (d, 2H); 8.05 (d, 2H); 8.82 (br. s, IH) ppm5 XI-A-074: 1 H NMR (DMSO-d6): δ = 1:39 (d, 3H); 4.87 (m, IH); 5.64 (brs s, 2H); 7.68 (d, 2H); 8.05 (d, 2H); 8.82 (brs s, IH) ppm
XI-A-075: 1H NMR (DMSO-d6): δ = 1.40 (s, 9H); 5.58 (br. s, 2H); 7.60 (d, 2H); 7.66 (br. s, IH); 7.96 (d, 2H) ppmXI-A-075: 1 H NMR (DMSO-d6): δ = 1.40 (s, 9H); 5.58 (brs s, 2H); 7.60 (d, 2H); 7.66 (brs s, IH); 7.96 (d, 2H) ppm
OOOO
XI-A-076: 1H NMR (DMSO-d6): δ = 0.92 (s, 9H); 1.11 (d, 3H); 4.01 (m, IH); 7.62 (d, 2H); 7.86 (br. d, IH); 8.00 (d, 2H) ppmXI-A-076: 1 H NMR (DMSO-d6): δ = 0.92 (s, 9H); 1.11 (d, 3H); 4.01 (m, IH); 7.62 (d, 2H); 7.86 (br d, IH); 8.00 (d, 2H) ppm
XI-A-077: 1H NMR (DMSO-d6): δ = 5.68 (br. s, 2H); 6.9 (m, IH); 6.98 (m, IH); 7.39 (m, IH); 7.75 (d, 2H); 8.15 (d, 2H); 8.33 (m, IH); 10.40 (s, IH) ppmXI-A-077: 1 H NMR (DMSO-d6): δ = 5.68 (br s., 2H); 6.9 (m, IH); 6.98 (m, IH); 7.39 (m, IH); 7.75 (d, 2H); 8.15 (d, 2H); 8.33 (m, IH); 10.40 (s, IH) ppm
XI-A-078: 1H NMR (DMSO-d6): δ = 4.60 (d, 2H); 5.64 (br. d, 2H); 7.25 (m, IH); 7.34 (m, IH); 7.67 (d, 2H); 7.74 (m, IH); 8.07 (d, 2H); 8.50 (m, IH);XI-A-078: 1 H NMR (DMSO-d6): δ = 4.60 (d, 2H); 5.64 (br d, 2H); 7.25 (m, IH); 7.34 (m, IH); 7.67 (d, 2H); 7.74 (m, IH); 8.07 (d, 2H); 8.50 (m, IH);
10 9.03 (br. t, IH) ppm10 9.03 (br.t, IH) ppm
XI-A-079: log P (HCOOH): 2.80 XI-A-080: log P (HCOOH): 1,97 XI-A-081: log P (HCOOH): 2,76XI-A-079: log P (HCOOH): 2.80 XI-A-080: log P (HCOOH): 1.97 XI-A-081: log P (HCOOH): 2.76
XI-A-082: log P (HCOOH): 3,52 XI-A-083: log P (HCOOH): 3,48 XI-A-084: log P (HCOOH): 3,53XI-A-082: log P (HCOOH): 3.52 XI-A-083: log P (HCOOH): 3.48 XI-A-084: log P (HCOOH): 3.53
XI-A-085: log P (HCOOH): 1 ,95 XI-A-086: log P (HCOOH): 2,54 XI-A-087: log P (HCOOH): 2,58XI-A-085: log P (HCOOH): 1.95 XI-A-086: log P (HCOOH): 2.54 XI-A-087: log P (HCOOH): 2.58
XI-A-088: log P (HCOOH): 2,63 XI-A-089: log P (HCOOH): 2,45 XI-A-090: log P (HCOOH): 1 ,42 XI-A-088: log P (HCOOH): 2.63 XI-A-089: log P (HCOOH): 2.45 XI-A-090: log P (HCOOH): 1.42
XI-A-090: log P (HCOOH): 2,99 XI-A-091: log P (HCOOH): 1,94 XI-A-092: log P (HCOOH): 3,03XI-A-090: log P (HCOOH): 2.99 XI-A-091: log P (HCOOH): 1.94 XI-A-092: log P (HCOOH): 3.03
XI-A-093: log P (HCOOH): 1,98 XI-A-094: log P (HCOOH): 3,08 XI-A-095: log P (HCOOH): 2,03XI-A-093: log P (HCOOH): 1.98 XI-A-094: log P (HCOOH): 3.08 XI-A-095: log P (HCOOH): 2.03
OO OO OO OO
- -- -
Tabelle 15Table 15
Gemäß den oben angegebenen allgemeinen Methoden lassen sich die in der folgenden Tabelle angegebenen Verbindungen der Formel (XI-B) herstellen.According to the general methods given above, the compounds of the formula (XI-B) given in the following table can be prepared.
Biologische BeispieleBiological examples
Beispiel AExample A
Phaedon Cochleariae-Test (PHAECO Spritzbehandlung)Phaedon Cochleariae Test (PHAECO Spray Treatment)
Lösungsmittel: 78,0 Gewichtsteile AcetonSolvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid1.5 parts by weight of dimethylformamide
Emulgator: 0,5 Gewichtsteile AlkylarylpolyglykoletherEmulsifier: 0.5 part 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 prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
Chinakohlblattscheiben (Brassica pekinensis) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Larven des Meerrettichblattkäfers (Phaedon cochleariae) besetzt.Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Käferlarven abgetötet wurden; 0 % bedeutet, dass keine Käferlarven abgetötet wurden.After 7 days, the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von > 80 % bei einer Aufwandmenge von 500 g/ha: I-A-Q 1-001, 1-A-Q 1-002, 1-A-Q2-011, 1-A-Q2- 012, I-A-Q2-013, I-A-Q2-014, I-A-Q2-015, I-A-Q2-016, I-A-Q2-017, I-A-Q2-018, I-A-Q2-019, I- A-Q2-020, I-A-Q2-022, I-A-Q2-023, I-A-Q2-024, I-A-Q2-025, I-A-Q2-026, I-A-Q2-027,I-A-Q2- 028, I-A-Q2-029, I-A-Q2-030, I-A-Q2-032, I-A-Q2-033, I-A-Q2-034, I-A-Q2-035, I-A-Q2-037, I- ^In this test, z. For example, the following compounds of the Preparation Examples have an effect of> 80% at a rate of 500 g / ha: IAQ 1-001, 1-AQ 1-002, 1-A-Q2-011, 1-A-Q2-012, IA-Q2-013, IA-Q2-014, IA-Q2-015, IA-Q2-016, IA-Q2-017, IA-Q2-018, IA-Q2-019, I-A-Q2-020, IA-Q2-022, IA-Q2-023, IA-Q2-024, IA-Q2-025, IA-Q2-026, IA-Q2-027, IA-Q2-028, IA-Q2-029, IA Q2-030, IA-Q2-032, IA-Q2-033, IA-Q2-034, IA-Q2-035, IA-Q2-037, I- ^
A-Q2-039, I-A-Q2-040, I-A-Q2-041, I-A-Q2-042, I-A-Q2-044, I-A-Q2-046, I-A-Q2-047, I-A-Q2- 048, I-A-Q2-049, I-A-Q2-050, I-A-Q2-O51, I-A-Q2-052, I-A-Q2-053, I-A-Q2-054, I-A-Q2-055, I- A-Q2-056, I-A-Q2-057, I-A-Q2-058, I-A-Q2-059, I-A-Q2-060, I-A-Q2-061, I-A-Q2-062, I-A-Q2- 065, I-A-Q2-066, I-A-Q2-069, I-A-Q2-073, I-A-Q2-079, I-A-Q2-080, I-A-Q2-083, I-A-Q2-084, I- A-Q2-085, I-A-Q2-086, I-A-Q2-087, I-A-Q2-088, I-A-Q2-089, I-A-Q2-090, I-A-Q2-092, I-A-Q2- 095, I-A-Q2-096, I-A-Q2-098, I-A-Q2-109, I-A-Q2-110, I-A-Q2-111, I-A-Q2-112, I-A-Q2-133, I- A-Q2-134, I-A-Q2-135, I-A-Q2-136, I-A-Q2-137, I-A-Q2-138, I-A-Q2-139, I-A-Q2-140, I-A-Q2- 141, I-A-Q2-144, I-A-Q2-145, I-A-Q2-147, I-A-Q2-149, I-A-Q2-150, I-A-Q2-151, I-A-Q2-152, I- A-Q2-153, I-A-Q2-154, I-A-Q2-155, I-A-Q2-157, I-A-Q2-159, I-A-Q2-160, I-A-Q2-162, I-A-Q2- 165, I-A-Q2-166, I-A-Q2-167, I-A-Q2-169, I-A-Q2-170, I-A-Q2-171, I-A-Q2-172, I-A-Q2-174, I- A-Q2-175, I-A-Q2-176, I-A-Q2-180, I-A-Q2-182, I-A-Q2-183, I-A-Q2-188, I-A-Q2-202, I-A-Q2- 2035 1-A-Q2-205, 1-A-Q2-207, 1-A-Q2-209, 1-A-Q2-210,I-A-Q2-211, 1-A-Q2-213, 1-A-Q2-214, I-A- Q2-215, 1-A-Q2-216, 1-A-Q2-217, 1-A-Q2-218, 1-A-Q2-219, 1-A-Q2-220, 1-A-Q2-221, 1-A-Q2-222, I-A-Q2-223, 1-A-Q2-224, 1-A-Q2-225, 1-A-Q2-226, 1-A-Q2-227, I-A-Q2-228, 1-A-Q2-229, I-A-Q2- 230, I-A-Q2-233, I-A-Q2-234, I-A-Q2-236, I-A-Q2-237, I-A-Q2-238, I-A-Q2-239, I-A-Q2-240, I- A-Q2-241, I-A-Q2-242, I-A-Q2-244, I-A-Q2-246, I-A-Q2-247, I-A-Q4-009, I-A-Q4-011, I-A-Q4- 040, I-A-Q4-042, I-A-Q4-048, 1-A-Q4-058, 1-A-Q4-102.A-Q2-039, IA-Q2-040, IA-Q2-041, IA-Q2-042, IA-Q2-044, IA-Q2-046, IA-Q2-047, IA-Q2-048, IA- Q2-049, IA-Q2-050, IA-Q2-O51, IA-Q2-052, IA-Q2-053, IA-Q2-054, IA-Q2-055, I-A-Q2-056, IA- Q2-057, IA-Q2-058, IA-Q2-059, IA-Q2-060, IA-Q2-061, IA-Q2-062, IA-Q2-065, IA-Q2-066, IA-Q2- 069, IA-Q2-073, IA-Q2-079, IA-Q2-080, IA-Q2-083, IA-Q2-084, I-A-Q2-085, IA-Q2-086, IA-Q2- 087, IA-Q2-088, IA-Q2-089, IA-Q2-090, IA-Q2-092, IA-Q2-095, IA-Q2-096, IA-Q2-098, IA-Q2-109, IA-Q2-110, IA-Q2-111, IA-Q2-112, IA-Q2-133, I-A-Q2-134, IA-Q2-135, IA-Q2-136, IA-Q2-137, IA-Q2-138, IA-Q2-139, IA-Q2-140, IA-Q2-141, IA-Q2-144, IA-Q2-145, IA-Q2-147, IA-Q2-149, IA- Q2-150, IA-Q2-151, IA-Q2-152, I-A-Q2-153, IA-Q2-154, IA-Q2-155, IA-Q2-157, IA-Q2-159, IA- IA-Q2-166, IA-Q2-167, IA-Q2-169, IA-Q2-170, IA-Q2-171, IA-Q2- 172, IA-Q2-174, I-A-Q2-175, IA-Q2-176, IA-Q2-180, IA-Q2-182, IA-Q2-183, IA-Q2-188, IA-Q2- 202, IA-Q2-203 5 1-A-Q2-205, 1-A-Q2-207, 1-A-Q2-209, 1-A-Q2-210, IA-Q2-211, 1-A- Q2-213, 1 -A-Q2-214, IA-Q2-215, 1-A-Q2-216, 1-A-Q2-217, 1-A-Q2-218, 1-A-Q2-219, 1-A-Q2 -220, 1-A-Q2-221, 1-A-Q2-222, IA-Q2-223, 1-A-Q2-224, 1-A-Q2-225, 1-A-Q2-226, 1 -A-Q2-227, IA-Q2-228, 1-A-Q2-229, IA-Q2-230, IA-Q2-233, IA-Q2-234, IA-Q2-236, IA-Q2-237 , IA-Q2-238, IA-Q2-239, IA-Q2-240, I-A-Q2-241, IA-Q2-242, IA-Q2-244, IA-Q2-246, IA-Q2-247 , IA-Q4-009, IA-Q4-011, IA-Q4-040, IA-Q4-042, IA-Q4-048, 1-A-Q4-058, 1-A-Q4-102.
Eine Wirkung von 83 % bei einer Aufwandmenge von 500 g/ha zeigte bei diesem Test z. B. die folgende Verbindung der Herstellungsbeispiele: I-A-Ql-089.An effect of 83% at an application rate of 500 g / ha showed in this test z. For example, the following compound of Preparation Examples: I-A-Ql-089.
Eine Wirkung von 100 % bei einer Aufwandmenge von 500 g/ha zeigten bei diesem Test z. B. die folgenden Verbindungen der Herstellungsbeispiele: I-A-Ql-087, 1-A-Ql-090, 1-A-Ql-091, 1-A-Q2- 407, 1-A-Q2-412, 1-A-Q2-414, 1-A-Q2-415, 1-A-Q2-417, 1-A-Q2-419, 1-A-Q2-420, 1-A-Q2-421.An effect of 100% at an application rate of 500 g / ha showed in this test z. For example, the following compounds of Preparation Examples: IA-QI-087, 1-A-Ql-090, 1-A-Ql-091, 1-A-Q2-407, 1-A-Q2-412, 1-A Q2-414, 1-A-Q2-415, 1-A-Q2-417, 1-A-Q2-419, 1-A-Q2-420, 1-A-Q2-421.
Beispiel BExample B
Spodoptera frugiperda-Test (SPODFR Spritzbehandlung)Spodoptera frugiperda test (SPODFR spray treatment)
Lösungsmittel: 78,0 Gewichtsteile AcetonSolvent: 78.0 parts by weight of acetone
1 ,5 Gewichtsteile Dimethylformamid1.5 parts by weight of dimethylformamide
Emulgator: 0,5 Gewichtsteile AlkylarylpolyglykoletherEmulsifier: 0.5 part 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 prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. ^ _
Maisblattscheiben (Zea mays) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Raupen des Heerwurms (Spodoptera frugiperda) besetzt.Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperda).
Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Raupen abgetötet wurden; 0 % bedeutet, dass keine Raupe abgetötet wurde.After 7 days, the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von > 80 % bei einer Aufwandmenge von 500 g/ha: I-A-Q 1-001, 1-A-Q2-011, 1-A-Q2-012, 1-A-Q2- 014, I-A-Q2-015, I-A-Q2-017, I-A-Q2-018, 1-A-Q2-019, I-A-Q2-020, I-A-Q2-023, I-A-Q2-030, I- A-Q2-033, I-A-Q2-035, I-A-Q2-039, I-A-Q2-044, I-A-Q2-048, I-A-Q2-052, I-A-Q2-053, I-A-Q2- 054, I-A-Q2-055, I-A-Q2-058, I-A-Q2-060, 1-A-Q2-061, I-A-Q2-062, I-A-Q2-107, I-A-Q2-110, I- A-Q2-133, I-A-Q2-141, I-A-Q2-147, I-A-Q2-155, I-A-Q2-160, I-A-Q2-166, I-A-Q2-202, I-A-Q2- 207, I-A-Q2-217, I-A-Q2-218, I-A-Q2-219, I-A-Q2-220, I-A-Q2-221, I-A-Q2-223, I-A-Q2-224, I- A-Q2-227, I-A-Q2-230, I-A-Q2-231, I-A-Q2-236, I-A-Q2-238, I-A-Q2-239, I-A-Q2-240, I-A-Q2- 242, I-A-Q2-244, I-A-Q2-246, I-A-Q4-009, I-A-Q4-014, I-A-Q4-016, 1-A-Q4-040, I-A-Q4-041, I- A-Q4-042, I-A-Q4-043, I-A-Q4-048, I-A-Q4-051, I-A-Q4-053, I-A-Q4-058, I-A-Q4-102, DC-021, EK-038.In this test, z. For example, the following compounds of the Preparation Examples have an effect of> 80% at a rate of 500 g / ha: IAQ 1-001, 1-A-Q2-011, 1-A-Q2-012, 1-A-Q2-014 , IA-Q2-015, IA-Q2-017, IA-Q2-018, 1-A-Q2-019, IA-Q2-020, IA-Q2-023, IA-Q2-030, I-A-Q2 -033, IA-Q2-035, IA-Q2-039, IA-Q2-044, IA-Q2-048, IA-Q2-052, IA-Q2-053, IA-Q2-054, IA-Q2-055 , IA-Q2-058, IA-Q2-060, 1-A-Q2-061, IA-Q2-062, IA-Q2-107, IA-Q2-110, I-A-Q2-133, IA-Q2 -141, IA-Q2-147, IA-Q2-155, IA-Q2-160, IA-Q2-166, IA-Q2-202, IA-Q2-207, IA-Q2-217, IA-Q2-218 , IA-Q2-219, IA-Q2-220, IA-Q2-221, IA-Q2-223, IA-Q2-224, I-A-Q2-227, IA-Q2-230, IA-Q2-231 , IA-Q2-236, IA-Q2-238, IA-Q2-239, IA-Q2-240, IA-Q2-242, IA-Q2-244, IA-Q2-246, IA-Q4-009, IA -Q4-014, IA-Q4-016, 1-A-Q4-040, IA-Q4-041, I-A-Q4-042, IA-Q4-043, IA-Q4-048, IA-Q4-051 , IA-Q4-053, IA-Q4-058, IA-Q4-102, DC-021, EK-038.
Eine Wirkung von 83 % bei einer Aufwandmenge von 500 g/ha zeigte bei diesem Test z. B. die folgende Verbindung der Herstellungsbeispiele: I-A-Q2-409.An effect of 83% at an application rate of 500 g / ha showed in this test z. For example, the following compound of Preparation Examples: I-A-Q2-409.
Eine Wirkung von 100 % bei einer Aufwandmenge von 500 g/ha zeigten bei diesem Test z. B. die folgenden Verbindungen der Herstellungsbeispiele: I-A-Q 1 -091 , 1-A-Q2-407.An effect of 100% at an application rate of 500 g / ha showed in this test z. For example, the following compounds of Preparation Examples: I-A-Q 1 -091, 1-A-Q2-407.
Beispiel CExample C
Myzus persicae-Test (MYZUPE Spritzbehandlung)Myzus persicae test (MYZUPE spray treatment)
Lösungsmittel: 78,0 Gewichtsteile Aceton 1,5 Gewichtsteile DimethylformamidSolvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide
Emulgator: 0,5 Gewichtsteile AlkylarylpolyglykoletherEmulsifier: 0.5 part 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. ^ 87To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. ^ 87
Chinakohlblattscheiben (Brassica pekinensis), die von allen Stadien der Grünen Pfirsichblattlaus (Myzus persicae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt.Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
Nach 6 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden.After 6 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von > 80 % bei einer Aufwandmenge von 500 g/ha: I-A-Q2-053, 1-A-Q2-133, 1-A-Q2-134, I-A-Q2- 0192, 1-A-Q4-088, 1-A-Q4-089.In this test, z. For example, the following compounds of the Preparation Examples have an effect of> 80% at a rate of 500 g / ha: IA-Q2-053, 1-A-Q2-133, 1-A-Q2-134, IA-Q2-0192, 1-A-Q4-088, 1-A-Q4-089.
Eine Wirkung von 90 % bei einer Aufwandmenge von 500 g/ha zeigte bei diesem Test z. B. die folgende Verbindung der Herstellungsbeispiele: I-A-Ql-089.An effect of 90% at an application rate of 500 g / ha showed in this test z. For example, the following compound of Preparation Examples: I-A-Ql-089.
Beispiel DExample D
Tetranychus-Test, OP-resistent (TETRUR Spritzbehandlung)Tetranychus test, surgical-resistant (TETRUR spray treatment)
Lösungsmittel: 78,0 Gewichtsteile Aceton 1,5 Gewichtsteile DimethylformamidSolvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide
Emulgator: 0,5 Gewichtsteile AlkylarylpolyglykoletherEmulsifier: 0.5 part 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 prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
Bohnenblattscheiben (Phaseolus vulgaris), die von allen Stadien der Gemeinen Spinnmilbe (Tetranychus urticae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt.Bean leaf discs (Phaseolus vulgaris) infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
Nach der gewünschten Zeit wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Spinnmilben abgetötet wurden; 0 % bedeutet, dass keine Spinnmilben abgetötet wurden.After the desired time, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von > 80 % bei einer Aufwandmenge von 500 g/ha: I-A-Q2-012, 1-A-Q2-015, 1-A-Q2-020, 1-A-Q2- 035, I-A-Q2-040, I-A-Q2-041, I-A-Q2-048, I-A-Q2-051, I-A-Q2-052, I-A-Q2-055, I-A-Q2-060, I- A-Q2-112, I-A-Q4-058. ^In this test, z. For example, the following compounds of the Preparation Examples have an effect of> 80% at a rate of 500 g / ha: IA-Q2-012, 1-A-Q2-015, 1-A-Q2-020, 1-A-Q2 035, IA-Q2-040, IA-Q2-041, IA-Q2-048, IA-Q2-051, IA-Q2-052, IA-Q2-055, IA-Q2-060, I-A-Q2- 112, IA-Q4-058. ^
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von > 80 % bei einer Aufwandmenge von 100 g/ha: Nr. I-A-Q2-046, 1-A-Q2-110, 1-A-Q2-202, 1-A- Q2-214, 1-A-Q2-216, 1-A-Q2-219, 1-A-Q2-220, 1-A-Q2-223, 1-A-Q2-224, 1-A-Q2-227, 1-A-Q2-229, I-A-Q2-231, 1-A-Q2-239, 1-A-Q2-240, 1-A-Q2-247In this test, z. Example, the following compounds of the preparation examples an effect of> 80% at an application rate of 100 g / ha: No. IA-Q2-046, 1-A-Q2-110, 1-A-Q2-202, 1-A Q2-214, 1-A-Q2-216, 1-A-Q2-219, 1-A-Q2-220, 1-A-Q2-223, 1-A-Q2-224, 1-A-Q2- 227, 1-A-Q2-229, IA-Q2-231, 1-A-Q2-239, 1-A-Q2-240, 1-A-Q2-247
Beispiel EExample E
Lucilia cuprina-Test (LUCICU)Lucilia cuprina test (LUCICU)
Lösungsmittel: DimethylsulfoxidSolvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with water to the desired concentration.
Gefäße, die Pferdefleisch enthalten, das mit der Wirkstoffzubereitung der gewünschten Konzentration behandelt wurde, werden mit Lucilia cuprina Larven besetzt.Vessels containing horsemeat treated with the preparation of active compound of the desired concentration are infested with Lucilia cuprina larvae.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Larven abgetötet wurden; 0 % bedeutet, dass keine Larven abgetötet wurden.After the desired time the kill is determined in%. 100% means that all larvae have been killed; 0% means that no larvae have been killed.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von > 80 % bei einer Aufwandmenge von 100 ppm: I-A-Q 1-001, 1-A-Q2-002, 1-A-Q2-005, 1-A-Q2- 010, I-A-Q2-011, I-A-Q2-012, I-A-Q2-014, I-A-Q2-015, I-A-Q2-017, I-A-Q2-018, I-A-Q2-019, I- A-Q2-023, 1-A-Q2-134, 1-A-Q2-141, 1-A-Q2-147, 1-A-Q2-149, 1-A-Q2-152.In this test, z. For example, the following compounds of the Preparation Examples have an effect of> 80% at a rate of 100 ppm: IAQ 1-001, 1-A-Q2-002, 1-A-Q2-005, 1-A-Q2-010, IA -Q2-011, IA-Q2-012, IA-Q2-014, IA-Q2-015, IA-Q2-017, IA-Q2-018, IA-Q2-019, I-A-Q2-023, 1 -A-Q2-134, 1-A-Q2-141, 1-A-Q2-147, 1-A-Q2-149, 1-A-Q2-152.
Beispiel FExample F
Musca domestica-Test (MUSCDO)Musca domestica test (MUSCDO)
Lösungsmittel: DimethylsulfoxidSolvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. ^ 9 005587To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with water to the desired concentration. ^ 9 005587
Gefäße, die einen Schwamm enthalten, der mit der Wirkstoffzubereitung der gewünschten Konzentration behandelt wurde, werden mit Musca domestica Adulten besetzt.Vessels containing a sponge treated with the preparation of active compound of the desired concentration are mated with Musca domestica adults.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Fliegen abgetötet wurden; 0 % bedeutet, dass keine Fliegen abgetötet wurden.After the desired time the kill is determined in%. 100% means that all flies have been killed; 0% means that no flies have been killed.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von > 80 % bei einer Aufwandmenge von 100 ppm: I-A-Q2-002, 1-A-Q2-005, 1-A-Q2-011, 1-A-Q2- 014, 1-A-Q2-017, 1-A-Q2-018.In this test, z. Example, the following compounds of the preparation examples an effect of> 80% at a rate of 100 ppm: IA-Q2-002, 1-A-Q2-005, 1-A-Q2-011, 1-A-Q2-014, 1-A-Q2-017, 1-A-Q2-018.
Beispiel GExample G
Ctenocephalides felis; oral (CTECFE)Ctenocephalides felis; oral (CTECFE)
Lösungsmittel: 1 Gewichtsteil DimethylsulfoxidSolvent: 1 part by weight of dimethyl sulfoxide
Zwecks Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 2 Gewichtsteile Wirkstoff mit der angegebenen Menge Lösungsmittel. Ein Teil des Konzentrats wird mit citiriertem Rinderblut verdünnt und die gewünschte Konzentration hergestellt.For the preparation of a suitable preparation of active compound, 2 parts by weight of active compound are mixed with the stated amount of solvent. A portion of the concentrate is diluted with citrated bovine blood and the desired concentration produced.
20 nüchterne adulte Flöhe {Ctenocephalides felis) werden in eine Kammer eingesetzt, die oben und unten mit Gaze verschlossen ist. Auf die Kammer wird ein Metalizylinder gestellt, dessen Unterseite mit Parafilm verschlossen ist. Der Zylinder enthält die Blut- Wirkstoffzubereitung, die von den Flöhen durch die Parafilmmembran aufgenommen werden kann.20 fasting adult fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom. A metal cylinder is placed on the chamber, the underside of which is sealed with parafilm. The cylinder contains the blood-drug preparation that can be absorbed by the fleas through the parafilm membrane.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Flöhe abgetötet wurden; 0 % bedeutet, dass kein Floh abgetötet wurde.After the desired time the kill is determined in%. 100% means that all fleas have been killed; 0% means that no flea has been killed.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von > 80 % bei einer Aufwandmenge von 100 ppm: I-A-Q 1-001, 1-A-Q2-011, 1-A-Q2-012, I-A- Q2-014, 1-A-Q2-015, 1-A-Q2-016, 1-A-Q2-017, 1-A-Q2-018, 1-A-Q2-023, 1-A-Q2-134In this test, z. For example, the following compounds of the Preparation Examples have an effect of> 80% at a rate of 100 ppm: IAQ 1-001, 1-A-Q2-011, 1-A-Q2-012, IA-Q2-014, 1-A -Q2-015, 1-A-Q2-016, 1-A-Q2-017, 1-A-Q2-018, 1-A-Q2-023, 1-A-Q2-134
Beispiel HExample H
Boophilus microplus -Test (BOOPMI Injektion)Boophilus microplus test (BOOPMI injection)
Lösungsmittel: Dimethylsulfoxid ^Solvent: dimethyl sulfoxide ^
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with water to the desired concentration.
Die Wirkstofflösung wird in das Abdomen (Boophilus microplus) injiziert, die Tiere werden in Schalen überführt und in einem klimatisierten Raum aufbewahrt. Die Wirkungskontrolle erfolgt auf Ablage fertiler Eier.The drug solution is injected into the abdomen (Boophilus microplus), the animals are transferred to trays and stored in an air-conditioned room. The effect control takes place on storage of fertile eggs.
Nach der gewünschten Zeit wird die Wirkung in % bestimmt. Dabei bedeutet 100%, dass keine Zecke fertile Eier gelegt hat.After the desired time, the effect is determined in%. 100% means that no ticks have laid fertile eggs.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von > 80 % bei einer Aufwandmenge von 20 μg/Tier: I- A-Q 1-001, 1-A-Q2-002, 1-A-Q2-005, 1-A- Q2-010, 1-A-Q2-011, 1-A-Q2-012, 1-A-Q2-014, 1-A-Q2-015, 1-A-Q2-016, 1-A-Q2-017, 1-A-Q2-018, I-A-Q2-019, 1-A-Q2-022, 1-A-Q2-023, 1-A-Q2-024, 1-A-Q2-026, 1-A-Q2-134, 1-A-Q2-141, 1-A-Q2- 147, 1-A-Q2-149, 1-A-Q2-150, 1-A-Q2-152, 1-A-Q2-195.In this test, z. For example, the following compounds of the Preparation Examples have an effect of> 80% at an application rate of 20 μg / animal: I-AQ 1-001, 1-A-Q2-002, 1-A-Q2-005, 1-A-Q2 -010, 1-A-Q2-011, 1-A-Q2-012, 1-A-Q2-014, 1-A-Q2-015, 1-A-Q2-016, 1-A-Q2-017 , 1-A-Q2-018, IA-Q2-019, 1-A-Q2-022, 1-A-Q2-023, 1-A-Q2-024, 1-A-Q2-026, 1-A -Q2-134, 1-A-Q2-141, 1-A-Q2-147, 1-A-Q2-149, 1-A-Q2-150, 1-A-Q2-152, 1-A-Q2 -195.
Beispiel IExample I
Spodoptera litura Larven - TestSpodoptera litura larvae - test
Lösungsmittel: 3 Gewichtsanteile DimethylformamidSolvent: 3 parts by weight of dimethylformamide
Emulgator: 1 Gewichtsanteil PolyoxyethylenalkylphenyletherEmulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether
Zur Herstellung eines geeigneten Wirkstoffs wird ein Gewichtsanteil Wirkstoff mit der oben angegebenen Menge Lösungsmittel enthaltend die oben angegeben Menge Emulgator gemischt und die Mischung wird mit Wasser auf die vorgeschriebene Konzentration verdünnt.To prepare a suitable active ingredient, one part by weight of active compound is mixed with the above-mentioned amount of solvent containing the above-mentioned amount of emulsifier and the mixture is diluted with water to the prescribed concentration.
Blätter der Süßkartoffel werden in die mit Wasser auf die vorgeschriebene Konzentration verdünnte Probenlösung eingetaucht und, nachdem die sich auf den Blättern niedergeschlagene Lösung an der Luft getrocknet ist, werden die so behandelten Blätter in eine Laborschale von 9 cm Durchmesser gegeben, in die dann 10 sich im dritten Stadium befindlichen Spodoptera litura Larven übertragen werden. Die Schale wird dann in einen temperaturkontrollierten Raum bei 25°C gestellt, gefolgt von der Zugabe von Süßkartoffelblättern zu der Schale am zweiten und vierten Tag und der Ermittlung der Zahl der toten Insekten nach 7 Tagen, woraus das insektizide Verhältnis berechnet wird. ^Leaves of the sweet potato are dipped in the sample solution diluted with water to the prescribed concentration, and after the solution deposited on the leaves is air-dried, the thus-treated leaves are placed in a laboratory dish of 9 cm in diameter, into which third-order Spodoptera litura larvae are transmitted. The dish is then placed in a temperature controlled room at 25 ° C followed by the addition of sweet potato leaves to the dish on the second and fourth day and the count of dead insects after 7 days, from which the insecticidal ratio is calculated. ^
Die Ergebnisse sind die Mittelwerte von zwei Laborschalen pro Gruppe in diesem Test.The results are the mean values of two laboratory dishes per group in this test.
Verbindungen I-A-Q4-001 und I-A-Q4-006 zeigten bei einer Wirkstoffkonzentration von 500 ppm eine 80 %ige Abtötung der Insektenlarven.Compounds I-A-Q4-001 and I-A-Q4-006 showed an 80% kill of insect larvae at 500 ppm drug concentration.
Verbindungen I-A-Q2-001, I-A-Q2-002, I-A-Q2-003, I-A-Q2-005, I-A-Q2-006, und I-A-Q2-010 zeigten bei einer Wirkstoffkonzentration von 500 ppm eine 100 %ige Abtötung der Insektenlarven.Compounds IA-Q2-001, IA-Q2-002, IA-Q2-003, IA-Q2-005, IA-Q2-006, and IA-Q2-010 exhibited a 100% kill of the drug at a drug concentration of 500 ppm insect larvae.
Beispiel JExample J
Aulacophora femoralis - Test (Sprühtest)Aulacophora femoralis - test (spray test)
Lösungsmittel: 3 Gewichtsanteile DimethylformamidSolvent: 3 parts by weight of dimethylformamide
Emulgator: 1 Gewichtsanteil PolyoxyethylenalkylphenyletherEmulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether
Zur Herstellung einer geeigneten Formulierung eines Wirkstoffs wird ein Gewichtsanteil des Wirkstoffs mit der genannten Menge an Lösungsmittel enthaltend die genannte Menge an Emulgator gemischt und die Mischung wird mit Wasser auf eine vorgegebene Konzentration verdünnt.To prepare a suitable formulation of an active ingredient, one part by weight of the active ingredient is mixed with said amount of solvent containing said amount of emulsifier, and the mixture is diluted with water to a predetermined concentration.
Gurkenblätter werden in eine verdünnte wässrige Lösung eines Wirkstoffs in der vorgegebenen Konzentration, die in gleicher Weise wie im oben beschriebenen Test hergestellt wurde, eingetaucht, luftgetrocknet und in eine Plastikschale mit sterilisierter schwarzer Erde gegeben. In diese Schale werden 5 Aulacophora femoralis Larven, die sich im zweiten Stadium befinden, übertragen. Die Schale wird dann in einen temperaturkontrollierten Raum bei 25°C gestellt. Nach 7 Tagen wird die Zahl der toten Larven gezählt, um die Sterberate zu berechnen.Cucumber leaves are dipped in a dilute aqueous solution of an active ingredient in the predetermined concentration prepared in the same manner as in the test described above, air-dried and placed in a plastic dish with sterilized black soil. 5 Aulacophora femoralis larvae, which are in the second stage, are transferred to this shell. The dish is then placed in a temperature controlled room at 25 ° C. After 7 days, the number of dead larvae is counted to calculate the mortality rate.
Verbindungen I-A-Q2-002, I-A-Q2-005 und I-A-Q2-010 zeigten bei einer Konzentration der aktiven Verbindung von 500 ppm eine 100 %ige Abtötung der Insekten. Compounds I-A-Q2-002, I-A-Q2-005 and I-A-Q2-010 exhibited 100% killing of the insects at a concentration of the active compound of 500 ppm.

Claims

Patentansprüche: claims:
1. Verbindungen der Formel (I)1. Compounds of the formula (I)
in welcherin which
M für eine der nachstehend aufgeführten Gruppierungen steht:M stands for one of the groupings listed below:
A1 und A2 unabhängig voneinander für Stickstoff oder C-R4 stehen;A 1 and A 2 are independently nitrogen or CR 4 ;
G1, G2, G3, G4 und G5 für Wasserstoff oder einen Substituenten stehen, unabhängig voneinander ausgewählt aus: Halogen, Alkyl, Alkenyl, Alkinyl, Haloalkyl, SF5, Hydroxy, Alkoxy, Alkoxyalkyl, Alkoxyalkoxy, Cycloalkyl, Alkenyloxy, Alkinyloxy, Cycloalkyl- alkoxy, Haloalkoxy, Haloalkoxyalkyl, Alkylsulfanyl, Haloalkylsulfanyl, Alkylsulfϊnyl, Haloalkylsulfinyl, Alkylsulfonyl, Haloalkylsulfonyl, Cyano, Alkylcarbonyl, Alkoxy- carbonyl, Alkoxycarbonylalkyl, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Alkyl- aminocarbonyl, Dialkylaminocarbonyl, Trialkylsilyl, Nitro, Amino, Alkylamino, Dialkyl- amino, Alkylsulfonylamino, Dialkylsulfonylamino, -CR5=NO-R5, -CR5=NO-Haloalkyl oder Formyl, wobei vicinale Alkyl-, Haloalkyl, Alkoxy- und/oder Haloalkoxygruppen zusammen mit den Kohlenstoffatomen, an die sie gebunden sind, ein fünf- bis sechsgliedriges cyclisches System bilden können, das 0 bis 2 Sauerstoffatome enthält, und dessen Alkylanteil gegebenenfalls mit einem oder mehreren Fluoratomen substituiert sein kann;G 1 , G 2 , G 3 , G 4 and G 5 are hydrogen or a substituent independently selected from: halogen, alkyl, alkenyl, alkynyl, haloalkyl, SF 5 , hydroxy, alkoxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, alkenyloxy , Alkinyloxy, cycloalkylalkoxy, haloalkoxy, haloalkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, carboxyl, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, trialkylsilyl, nitro, amino , Alkylamino, dialkylamino, alkylsulfonylamino, dialkylsulfonylamino, -CR 5 = NO-R 5 , -CR 5 = NO-haloalkyl or formyl, wherein vicinal alkyl, haloalkyl, alkoxy and / or haloalkoxy groups together with the carbon atoms to which they are bonded, can form a five- to six-membered cyclic system containing 0 to 2 oxygen atoms, and its alkyl moiety optionally with one or more Fl uoratomen can be substituted;
Q für einen Substituenten steht, ausgewählt aus Q1, Q2, Q3 oder Q4;Q is a substituent selected from Q 1 , Q 2 , Q 3 or Q 4 ;
Q1 für eine der nachstehend aufgeführten heterocyclischen Gruppierungen steht; Q 1 is one of the heterocyclic groupings listed below;
(Z6) (Z7) (Z8) (Z9) (Z10)(Z 6 ) (Z 7 ) (Z 8 ) (Z 9 ) (Z 10 )
(Z16) (Z") (Z18) (Z19) (Z20) (Z 16 ) (Z ") (Z18) (Z 19) (Z 20)
(Z21) (Z22) (Z23) (Z24) wobei(Z 21 ) (Z 22 ) (Z 23 ) (Z 24 ) where
W1 und W2 unabhängig voneinander für Sauerstoff oder Schwefel stehen, undW 1 and W 2 are independently oxygen or sulfur, and
R6, R6', R6", R6'" und R7 die unten stehende Bedeutung haben;R 6 , R 6 ' , R 6 " , R 6'" and R 7 are as defined below;
Q2 für C(W)NR8R" steht; ^ ^ _Q 2 is C (W) NR 8 R "; ^ ^ _
Q3 für C(R10R1 ^NR8R9 steht;Q 3 is C (R 10 R 1 ^ NR 8 R 9 ;
Q4 für Cyano (wobei R1 nicht für Amino steht), Nitro, Amino, COOH, COOR12, Fluor (falls R3 verschieden von Chlor ist), Chlor (falls R3 verschieden von Chlor, COOH, CH2CH2OMe und OMe ist), Brom Iod, SR12 (wobei R1 nicht für Amino steht, falls R12 für Alkyl steht), S(O)R12, S(O)2R12 oder S(O)2NR8R9 steht;Q 4 for cyano (where R 1 is not amino), nitro, amino, COOH, COOR 12 , fluorine (if R 3 is other than chlorine), chlorine (if R 3 is different from chlorine, COOH, CH 2 CH 2 OMe and OMe), bromine iodine, SR 12 (where R 1 is not amino if R 12 is alkyl), S (O) R 12 , S (O) 2 R 12 or S (O) 2 NR 8 R 9 stands;
R1 für Wasserstoff, Halogen, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl, Cyano, Amino, Z16 oder NR13R14 steht;R 1 is hydrogen, halogen, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, cyano, amino, Z 16 or NR 13 R 14 ;
R2 für Wasserstoff, Halogen, Alkyl, Alkenyl, Alkinyl, Haloalkyl, Cycloalkyl, Hydroxyalkyl, Alkoxyalkyl, Haloalkoxyalkyl, Alkoxyhaloalkyl, Alkylsulfanylalkyl, Alkyl- sulfinylalkyl, Alkylsulfonylalkyl, Haloalkylsulfanylalkyl, Haloalkylsulfinylalkyl, Haloalkyl- sulfonylalkyl Cycloalkylalkyl, Phenylalkyl, Heteroarylalkyl, Heterocyclylalkyl, Arylhalo- alkyl, Haloalkyloxyhaloalkyloxyhaloalkyl, Heterocyclyl, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl oder Phenyl steht;R 2 is hydrogen, halogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, alkylsulfanylalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylsulfanylalkyl, haloalkylsulfinylalkyl, haloalkylsulfonylalkyl, cycloalkylalkyl, phenylalkyl, heteroarylalkyl, heterocyclylalkyl, arylhaloalkyl alkyl, haloalkyloxyhaloalkyloxyhaloalkyl, heterocyclyl, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl or phenyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen, Alkyl, Haloalkyl,where a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano; a heterocyclyl radical is optionally substituted by -OH / = O, -SH / SS, -NH 2 , halogen, alkyl, haloalkyl,
Alkoxy, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl, Monoalkylamino, Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy oder Cyano.Alkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, monoalkylamino, dialkylamino, nitro or cyano; and an alkanediyl radical bonded to phenyl, heteroaryl or heterocyclyl is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy or cyano.
R3 für Halogen, Alkyl, Alkenyl, Alkinyl, Haloalkyl, Cycloalkyl, Alkoxyalkyl, Alkyl- carbonyloxyalkyl, Alkylsulfanylalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Hydroxy, Z16, Alkoxy, Acylamino, Alkoxycarbonylamino, Alkenyloxy, Alkinyloxy, Cycloalkylalkoxy, Haloalkoxy, Alkylsulfanyl, Haloalkylsulfanyl, Alkylsulfinyl, Haloalkylsulfinyl, Alkylsul- fonyl, Haloalkylsulfonyl, Cyano, Alkylcarbonyl, Alkoxycarbonyl, Alkoxycarbonylalkyl,R 3 is halogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkylcarbonyloxyalkyl, alkylsulfanylalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, hydroxy, Z 16 , alkoxy, acylamino, alkoxycarbonylamino, alkenyloxy, alkynyloxy, cycloalkylalkoxy, haloalkoxy, alkylsulfanyl, haloalkylsulfanyl, Alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl,
Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Alkylaminocarbonyl, Dialkylamino- carbonyl, Alkylsulfonylaminocarbonyl, Trialkylsilyl, Nitro, Amino, Alkylamino, Dialkylamino, Alkylsulfonylamino, Dialkylsulfonylamino, -CR5=NO-R5, -CR5=NO-Haloalkyl oder Formyl steht;Carboxyl, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonylaminocarbonyl, trialkylsilyl, nitro, amino, alkylamino, dialkylamino, alkylsulfonylamino, dialkylsulfonylamino, -CR 5 = NO-R 5 , -CR 5 = NO-haloalkyl or formyl;
R4 für Wasserstoff, Cyano, Nitro, Alkyl, Haloalkyl, Halogen oder Alkoxy steht;R 4 is hydrogen, cyano, nitro, alkyl, haloalkyl, halogen or alkoxy;
R5 für Wasserstoff oder Alkyl steht; ^ _R 5 is hydrogen or alkyl; ^ _
R6, R6 , R6 , R6 unabhängig voneinander für Wasserstoff, Amino, Hydroxy, Mercapto, Nitro, Cyano, Carboxyl, Halogen, Alkyl, Haloalkyl, Alkenyl, Alkinyl, Cycloalkyl, Alkoxy, Haloalkoxy, Alkenyloxy, Alkinyloxy, Alkoxycarbonyl, Alkylsulfanyl, HaIo- alkylsulfanyl, Alkylsulfinyl, Haloalkylsulfinyl, Alkylsulfonyl, Haloalkylsulfonyl, Axnino- carbonyl, Aminothiocarbonyl, CR5=NO-R5, -CR5=NO-Haloalkyl, Formyl, Alkylamino,R 6 , R 6 , R 6 , R 6, independently of one another, represent hydrogen, amino, hydroxyl, mercapto, nitro, cyano, carboxyl, halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, alkoxycarbonyl, Alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, axinocarbonyl, aminothiocarbonyl, CR 5 = NO-R 5 , -CR 5 = NO-haloalkyl, formyl, alkylamino,
Dialkylamino, Phenyl, Heteroaryl, Heteroarylalkyl oder Heterocyclylalkyl stehen;Dialkylamino, phenyl, heteroaryl, heteroarylalkyl or heterocyclylalkyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen, Alkyl, Haloalkyl, Alkoxy, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl, Monoalkylamino, Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy oder Cyano;where a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano; a heterocyclyl radical is optionally substituted by -OH / = O, -SH / SS, -NH 2 , halogen, alkyl, haloalkyl, alkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, monoalkylamino, dialkylamino, nitro or cyano; and an alkanediyl radical bonded to phenyl, heteroaryl or heterocyclyl is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy or cyano;
R7 für Wasserstoff, Amino, Hydroxy, Cyano, Alkyl, Haloalkyl, Alkenyl, Alkinyl, Cycloalkyl, Alkoxy, Alkenyloxy, Alkinyloxy, Alkoxycarbonyl, Alkylcarbonyl,R 7 is hydrogen, amino, hydroxyl, cyano, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkenyloxy, alkynyloxy, alkoxycarbonyl, alkylcarbonyl,
Alkylaminocarbonyl, Dialkylaminocarbonyl, Phenyl, Phenylalkyl, Heteroarylalkyl oder Heterocyclylalkyl steht;Alkylaminocarbonyl, dialkylaminocarbonyl, phenyl, phenylalkyl, heteroarylalkyl or heterocyclylalkyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =O, -SH / =S, -NH2, Halogen, Alkyl, Haloalkyl,where a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano; a heterocyclyl radical is optionally substituted by -OH / OO, -SH / SS, -NH 2 , halogen, alkyl, haloalkyl,
Alkoxy, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl, Monoalkylamino, Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy oder Cyano undAlkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, monoalkylamino, dialkylamino, nitro or cyano; and an alkanediyl radical attached to phenyl, heteroaryl or heterocyclyl optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy or cyano and
wobei gegebenenfalls zwei benachbarte Reste aus R6, R6 , R6 , R6 und R7 zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-, -SO2-, -NH- oder -N-Alkyl- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstoffkette unterbrochenes Alkandiyl oder Alkendiyl mit jeweils 2 bis 5 Kohlenstoffatomen stehen;where appropriate two adjacent radicals of R 6 , R 6 , R 6 , R 6 and R 7 together represent optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N-alkyl- at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
R8 und R9 unabhängig voneinander für Wasserstoff, Alkyl, Haloalkyl, AlkenylR 8 and R 9 are independently hydrogen, alkyl, haloalkyl, alkenyl
(gegebenenfalls substituiert durch Halogen, Alkyl, Haloalkyl oder Cyano), Alkinyl, Cycloalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Haloalkyl, Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten), ^ _(optionally substituted by halogen, alkyl, haloalkyl or cyano), alkynyl, cycloalkyl (optionally mono- or polysubstituted by halogen, haloalkyl, alkyl or fused to an aromatic or heteroaromatic radical on the cycle, ^ _
Cycloalkylalkyl (am Cyclus gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Haloalkyl, Alkyl oder kondensiert an einen Aromaten oder Heteroaromaten, am Alkylteil gegebenenfalls ein- oder mehrfach substituiert durch Halogen, Alkyl, Haloalkyl, Alkoxy oder Cyano), Cycloalkylcarbonylheterocyclyl, Alkyloxycarbonylheterocyclyl, Alkylsulfinyl- alkyl, Alkylsulfanylalkyl, Alkylsulfonylalkyl, Hydroxyalkyl, Heterocyclylcarbonylalkyl,Cycloalkylalkyl (optionally mono- or polysubstituted by halogen, haloalkyl, alkyl or fused to an aromatic or heteroaromatic radical on the cycle, optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy or cyano on the alkyl part), cycloalkylcarbonylheterocyclyl, alkyloxycarbonylheterocyclyl, alkylsulfinyl alkyl, alkylsulfanylalkyl, alkylsulfonylalkyl, hydroxyalkyl, heterocyclylcarbonylalkyl,
Heteroarylcarbonylaminoalkyl, Haloalkoxyalkyl, Alkylthiocarbonyl, Dialkylaminocarbonyl, Alkylaminocarbonyl, Haloalkylaminocarbonyl Alkoxy, Alkenyloxy, Alkinyloxy, Alkoxy- alkyl, Alkylcarbonylalkyl, C(R10Rn)CR5=NO-R5, Alkylsulfonyl, Alkylcarbonyl, Haloalkyl- carbonyl, Alkenylcarbonyl, Alkinylcarbonyl, Cycloalkylcarbonyl, Alkoxycarbonyl, Alkenyl- oxycarbonyl, Alkinyloxycarbonyl, Alkoxyalkylcarbonyl, Phenylsulfonyl, Phenyl, Hetero- aryl, Heterocyclyl, Phenylalkyl, Heteroarylalkyl, Heterocyclylalkyl, Phenylcarbonyl, Heteroarylcarbonyl, Heterocyclylcarbonyl, Phenylalkylcarbonyl, Heteroarylalkylcarbonyl, Heterocyclylalkylcarbonyl, Phenoxycarbonyl oder Phenylalkoxycarbonyl stehen;Heteroarylcarbonylaminoalkyl, haloalkoxyalkyl, alkylthiocarbonyl, dialkylaminocarbonyl, alkylaminocarbonyl, haloalkylaminocarbonylalkoxy, alkenyloxy, alkynyloxy, alkoxyalkyl, alkylcarbonylalkyl, C (R 10 R n ) CR 5 = NO-R 5 , alkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, Cycloalkylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, alkoxyalkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl, heterocyclyl, phenylalkyl, heteroarylalkyl, heterocyclylalkyl, phenylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, phenylalkylcarbonyl, heteroarylalkylcarbonyl, heterocyclylalkylcarbonyl, phenoxycarbonyl or phenylalkoxycarbonyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =O, -SH / =S, -NH2, Halogen, Alkyl, Haloalkyl,where a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano; a heterocyclyl radical is optionally substituted by -OH / OO, -SH / SS, -NH 2 , halogen, alkyl, haloalkyl,
Alkoxy, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl, Monoalkylamino, Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy oder Cyano undAlkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, monoalkylamino, dialkylamino, nitro or cyano; and an alkanediyl radical attached to phenyl, heteroaryl or heterocyclyl optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy or cyano and
wobei gegebenenfalls R8 / R9 zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-, -SO2-, -NH- oder -N-Alkyl- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstoffkette unterbrochenes Alkandiyl oder Alkendiyl mit jeweils 2 bis 5 Kohlenstoffatomen stehen;where appropriate, R 8 / R 9 together for optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N-alkyl- at the beginning (or at the end) or within the hydrocarbon chain are interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
R10 und R11 unabhängig voneinander für Wasserstoff, Alkyl, Haloalkyl oder Cyano stehen;R 10 and R 11 are independently hydrogen, alkyl, haloalkyl or cyano;
R12 für Alkyl oder Haloalkyl steht;R 12 is alkyl or haloalkyl;
R13 und R14 unabhängig voneinander für Wasserstoff, Alkyl, Haloalkyl, Alkenyl, Alkinyl, Alkoxyalkyl, Alkylcarbonylalkyl, C(R10R1 ^CR^NO-R5, Alkylsulfonyl, Alkyl- carbonyl, Haloalkylcarbonyl, Alkenylcarbonyl, Alkinylcarbonyl, Cycloalkylcarbonyl,R 13 and R 14 independently of one another represent hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, alkoxyalkyl, alkylcarbonylalkyl, C (R 10 R 1 ^ CR 1 NO-R 5 , alkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl,
Alkoxycarbonyl, Alkenyloxycarbonyl, Alkinyloxycarbonyl, Alkoxyalkylcarbonyl, Phenylsulfonyl, Phenyl, Heteroaryl, Heterocyclyl, Phenylalkyl, Heteroarylalkyl, Heterocyclylalkyl, Phenylcarbonyl, Heteroarylcarbonyl, Heterocyclylcarbonyl, Phenylalkylcarbonyl, _Alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, alkoxyalkylcarbonyl, phenylsulfonyl, phenyl, heteroaryl, heterocyclyl, phenylalkyl, heteroarylalkyl, heterocyclylalkyl, phenylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, phenylalkylcarbonyl, _
Heteroarylalkylcarbonyl, Heterocyclylalkylcarbonyl, Phenoxycarbonyl oder Phenylalkoxy- carbonyl stehen;Heteroarylalkylcarbonyl, heterocyclylalkylcarbonyl, phenoxycarbonyl or phenylalkoxycarbonyl;
wobei ein Phenyl- oder Heteroarylrest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy, Nitro oder Cyano; ein Heterocyclylrest gegebenenfalls substituiert ist durch -OH / =0, -SH / =S, -NH2, Halogen, Alkyl, Haloalkyl,where a phenyl or heteroaryl radical is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano; a heterocyclyl radical is optionally substituted by -OH / = O, -SH / SS, -NH 2 , halogen, alkyl, haloalkyl,
Alkoxy, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl, Monoalkylamino, Dialkylamino, Nitro oder Cyano; und ein an Phenyl, Heteroaryl oder Heterocyclyl gebundener Alkandiyl-Rest gegebenenfalls ein- oder mehrfach substituiert ist durch Halogen, Alkyl, Haloalkyl, Alkoxy oder CyanoAlkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, monoalkylamino, dialkylamino, nitro or cyano; and an alkanediyl radical bonded to phenyl, heteroaryl or heterocyclyl is optionally mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy or cyano
oderor
R13 und R14 als Imin die Gruppierung =CR5-NR15R16 oder =CR5-OR12 bilden;R 13 and R 14 as imine form the grouping = CR 5 -NR 15 R 16 or = CR 5 -OR 12 ;
R15 und R16 unabhängig voneinander für Alkyl stehen oderR 15 and R 16 are independently alkyl or
R15 und R16 zusammen für gegebenenfalls substituiertes und/oder gegebenenfalls durch Sauerstoff oder Schwefel oder eine Gruppierung aus der Reihe -S(O)-, -SO2-, -NH- oder -N- Alkyl- am Anfang (bzw. am Ende) oder innerhalb der Kohlenwasserstoffkette unterbrochenes Alkandiyl oder Alkendiyl mit jeweils 2 bis 5 Kohlenstoffatomen stehen;R 15 and R 16 together for optionally substituted and / or optionally by oxygen or sulfur or a grouping from the series -S (O) -, -SO 2 -, -NH- or -N-alkyl- at the beginning (or am End) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl each having 2 to 5 carbon atoms;
und die Verbindungen der allgemeinen Formel (!) außerdem N-Oxide, Salze, Tautomere, Diastereomere und optische Isomere umfassen.and the compounds of general formula (I) further include N-oxides, salts, tautomers, diastereomers and optical isomers.
2. Verbindungen der Formel (DC)2. Compounds of the formula (DC)
wobei G1, G2, G3, G4, G5, R1 und R2 wie in Anspruch 1 definiert sind, mit der Maßgabe, dass R1 nicht für Amino steht.wherein G 1 , G 2 , G 3 , G 4 , G 5 , R 1 and R 2 are as defined in claim 1, with the proviso that R 1 is not amino.
3. Verbindungen der Formeln (XI-A) oder (XI-B) - -3. Compounds of the formulas (XI-A) or (XI-B) - -
wobei R1, R2, R3, A1, A2 und Q wie in Anspruch 1 definiert sind und LG für Chlor, Brom, Iod oder Alkylsulfonyl steht. wherein R 1 , R 2 , R 3 , A 1 , A 2 and Q are as defined in claim 1 and LG is chloro, bromo, iodo or alkylsulfonyl.
4. Verbindungen der Formel (VII-A) oder (VE-B)4. Compounds of the formula (VII-A) or (VE-B)
wobei A1, A2, R3 und Q wie in Anspruch 1 definiert sind, Q aber ungleich Z8 ist wenn A1 gleich Stickstoff und A2 gleich CH. wherein A 1 , A 2 , R 3 and Q are as defined in claim 1, but Q is other than Z 8 when A 1 is nitrogen and A 2 is CH.
5. Verwendung von Verbindungen der Formel (I) gemäß Anspruch 1 zur Bekämpfung tierischer Schädlinge.5. Use of compounds of the formula (I) according to claim 1 for controlling animal pests.
6. Verwendung von Verbindungen der Formel (I) zur Bekämpfung tierischer Schädlinge, wobei M für M1 steht, Q für Q4 steht, Q4 für Wasserstoff steht und alle anderen Reste wie in Anspruch 1 definiert sind, mit der Maßgabe, dass A1 und A2 nicht gleichzeitig für Stickstoff stehen.Use of compounds of formula (I) for controlling animal pests, wherein M is M 1 , Q is Q 4 , Q 4 is hydrogen and all other radicals are as defined in claim 1, provided that A 1 and A 2 are not simultaneously nitrogen.
7. Verwendung von Verbindungen der Formel (I) zur Bekämpfung tierischer Schädlinge, wobei M für M1 steht, R3 für Wasserstoff steht und alle anderen Reste wie oben definiert sind, mit der Maßgabe, dass A1 und A2 nicht gleichzeitig für Stickstoff stehen.7. Use of compounds of the formula (I) for controlling animal pests, wherein M is M 1 , R 3 is hydrogen and all other radicals are as defined above, with the proviso that A 1 and A 2 are not simultaneously nitrogen stand.
8. Verwendung von Verbindungen der Formeln (XI-A) oder (XI-B) gemäß Anspruch 3 zur Bekämpfung tierischer Schädlinge.8. Use of compounds of the formulas (XI-A) or (XI-B) according to claim 3 for controlling animal pests.
9. Verfahren zur Bekämpfung tierischer Schädlinge, dadurch gekennzeichnet, dass man Verbindungen der Formel (I) gemäß Anspruch 1 auf tierische Schädlinge und/oder deren Lebensraum und/oder Saatgut einwirken lässt. 9. A method for controlling animal pests, which comprises allowing compounds of the formula (I) according to claim 1 to act on animal pests and / or their habitat and / or seed.
0. Verfahren zur Herstellung agrochemischer Zusammensetzungen, dadurch gekennzeichnet, dass man Verbindungen der Formel (I) gemäß Anspruch 1 mit Streckmitteln und/oder oberflächenaktiven Stoffen vermischt. 0. A process for the preparation of agrochemical compositions, which comprises mixing compounds of the formula (I) according to claim 1 with extenders and / or surface-active substances.
EP09777596A 2008-08-14 2009-08-01 Insecticidal 4-phenyl-1h-pyrazoles Withdrawn EP2321262A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP11165244A EP2374791A1 (en) 2008-08-14 2009-08-01 Insecticidal 4-phenyl-1H pyrazoles
EP09777596A EP2321262A1 (en) 2008-08-14 2009-08-01 Insecticidal 4-phenyl-1h-pyrazoles

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP08162378 2008-08-14
EP09777596A EP2321262A1 (en) 2008-08-14 2009-08-01 Insecticidal 4-phenyl-1h-pyrazoles
PCT/EP2009/005587 WO2010017902A1 (en) 2008-08-14 2009-08-01 Insecticidal 4-phenyl-1h-pyrazoles

Publications (1)

Publication Number Publication Date
EP2321262A1 true EP2321262A1 (en) 2011-05-18

Family

ID=40085429

Family Applications (2)

Application Number Title Priority Date Filing Date
EP09777596A Withdrawn EP2321262A1 (en) 2008-08-14 2009-08-01 Insecticidal 4-phenyl-1h-pyrazoles
EP11165244A Withdrawn EP2374791A1 (en) 2008-08-14 2009-08-01 Insecticidal 4-phenyl-1H pyrazoles

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP11165244A Withdrawn EP2374791A1 (en) 2008-08-14 2009-08-01 Insecticidal 4-phenyl-1H pyrazoles

Country Status (18)

Country Link
US (1) US20110190365A1 (en)
EP (2) EP2321262A1 (en)
JP (1) JP2011530548A (en)
KR (1) KR20110044900A (en)
CN (1) CN102186809A (en)
AU (1) AU2009281457A1 (en)
BR (1) BRPI0918430A2 (en)
CA (1) CA2733958A1 (en)
CL (1) CL2011000285A1 (en)
CO (1) CO6341618A2 (en)
CR (1) CR20110080A (en)
EC (1) ECSP11010822A (en)
IL (1) IL210758A0 (en)
MX (1) MX2011001601A (en)
PE (1) PE20110672A1 (en)
RU (1) RU2011109066A (en)
SV (1) SV2011003838A (en)
WO (1) WO2010017902A1 (en)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010020522A1 (en) 2008-08-22 2010-02-25 Syngenta Participations Ag Insecticidal compounds
EP2488030B1 (en) 2009-10-12 2015-01-07 Bayer CropScience AG 1-(pyrid-3-yl)-pyrazoles and 1-(pyrimid-5-yl)-pyrazoles as pest controllers
JP5823398B2 (en) * 2009-10-12 2015-11-25 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ Novel amides and thioamides as pesticides
CN102834390B (en) * 2009-11-11 2014-11-12 拜尔农作物科学股份公司 Novel diazinylpyrazolyl compounds
RU2017144535A (en) 2010-03-30 2019-02-18 Версеон Корпорейшн MULTI-DISPLACED AROMATIC COMPOUNDS AS THROMBINE INHIBITORS
AR083431A1 (en) 2010-06-28 2013-02-27 Bayer Cropscience Ag HETEROCICLICAL COMPOUNDS AS PESTICIDES
JPWO2012102387A1 (en) * 2011-01-27 2014-07-03 日産化学工業株式会社 Pyrazole derivatives and pest control agents
CN103958496B (en) 2011-11-21 2017-05-24 巴斯夫欧洲公司 Process for preparing N-substituted 1H-pyrazole-5-carboxylate compounds and derivatives thereof
MX2014013430A (en) 2012-05-04 2015-04-14 Basf Se Substituted pyrazole-containing compounds and their use as pesticides.
ES2834959T3 (en) 2012-12-06 2021-06-21 Celgene Quanticel Res Inc Histone demethylase inhibitors
CN105073735B (en) 2013-02-06 2018-08-14 拜耳作物科学股份公司 The pyrazole derivatives that halogen as pest control agent replaces
EP2968297B1 (en) 2013-03-15 2018-09-26 Verseon Corporation Multisubstituted aromatic compounds as serine protease inhibitors
MX2015011567A (en) * 2013-03-15 2016-04-25 Verseon Corp Halogenopyrazoles as inhibitors of thrombin.
EP3066080B1 (en) * 2013-11-05 2018-05-09 Bayer CropScience Aktiengesellschaft Novel compounds for combating arthropods
CA2935646A1 (en) 2014-01-03 2015-07-09 Bayer Animal Health Gmbh Novel pyrazolyl-heteroarylamides as pesticides
WO2015105129A1 (en) * 2014-01-10 2015-07-16 旭硝子株式会社 Ethereal oxygen-containing perfluoroalkyl group-substituted pyrazole compound and production method therefor
SG11201701940UA (en) 2014-09-17 2017-04-27 Verseon Corp Pyrazolyl-substituted pyridone compounds as serine protease inhibitors
CN107108514A (en) * 2015-01-13 2017-08-29 先正达参股股份有限公司 Harmful organism active heterocycles derivative is killed with sulfur-bearing substituent
CA2977993A1 (en) 2015-02-27 2016-09-01 Verseon Corporation Substituted pyrazole compounds as serine protease inhibitors
HUE054503T2 (en) 2015-12-16 2021-09-28 Nippon Soda Co Arylazole compound and pest control agent
AU2017257755B2 (en) * 2016-04-25 2021-05-06 Duke University Benzoylglycine derivatives and methods of making and using same
CN109983003B (en) * 2016-12-19 2022-06-03 日本曹达株式会社 Diaryl pyrazole compound and pest control agent
AU2019387370A1 (en) * 2018-11-30 2021-06-10 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof
CN115710195A (en) * 2021-08-22 2023-02-24 华东理工大学 Trifluoroolefin compound with nematicidal activity and preparation method and application thereof
WO2023118434A1 (en) * 2021-12-22 2023-06-29 Globachem Nv Pesticidally active amide compounds

Family Cites Families (209)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL253320A (en) 1959-07-03
DE2633992A1 (en) * 1975-08-08 1978-02-09 Schering Ag Antiinflammatory (1,4)-diphenyl-(3)-alkyl-carboxy-pyrazole - prepd. by treating corresp. (3)-halide with a cyanide, and opt. hydrolysing or reducing
FR2326421A1 (en) 1975-09-30 1977-04-29 Ugine Kuhlmann NEW TRIFLUOROMETHYL-3-ARYL-4 AMINO-5 PYRAZOLES AND THEIR APPLICATION AS DIAZOTABLE BASES FOR THE SYNTHESIS OF COLORING MATTERS
US4272417A (en) 1979-05-22 1981-06-09 Cargill, Incorporated Stable protective seed coating
US4245432A (en) 1979-07-25 1981-01-20 Eastman Kodak Company Seed coatings
US5136868A (en) * 1983-11-04 1992-08-11 Fmc Corporation Herbicidal 1-aryl-4-substituted-1,4-dihydro-5h-tetrazol-5-ones and sulfur analogs thereof
IL73419A (en) 1983-11-07 1988-02-29 Lilly Co Eli 1h-pyrazole-4-(thio)carboxamide derivatives,their preparation and herbicidal compositions containing them
US5304732A (en) 1984-03-06 1994-04-19 Mgi Pharma, Inc. Herbicide resistance in plants
US4761373A (en) 1984-03-06 1988-08-02 Molecular Genetics, Inc. Herbicide resistance in plants
US5331107A (en) 1984-03-06 1994-07-19 Mgi Pharma, Inc. Herbicide resistance in plants
US4743291A (en) * 1984-10-31 1988-05-10 Fmc Corporation Herbicidal aryl triazolinones
DE3520327A1 (en) 1985-06-07 1986-12-11 Bayer Ag, 5090 Leverkusen 5-AMINO-4-CYANO-1-PYRIDYL-PYRAZOLE
DE3765449D1 (en) 1986-03-11 1990-11-15 Plant Genetic Systems Nv PLANT CELLS RESISTED BY GENE TECHNOLOGY AND RESISTANT TO GLUTAMINE SYNTHETASE INHIBITORS.
US5273894A (en) 1986-08-23 1993-12-28 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5276268A (en) 1986-08-23 1994-01-04 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5637489A (en) 1986-08-23 1997-06-10 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5378824A (en) 1986-08-26 1995-01-03 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5013659A (en) 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5605011A (en) 1986-08-26 1997-02-25 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US4824834A (en) 1986-10-31 1989-04-25 Otsuka Pharmaceutical Company, Limited Pyrazolotriazine compounds
US4808430A (en) 1987-02-27 1989-02-28 Yazaki Corporation Method of applying gel coating to plant seeds
US5638637A (en) 1987-12-31 1997-06-17 Pioneer Hi-Bred International, Inc. Production of improved rapeseed exhibiting an enhanced oleic acid content
GB8810120D0 (en) 1988-04-28 1988-06-02 Plant Genetic Systems Nv Transgenic nuclear male sterile plants
US5084082A (en) 1988-09-22 1992-01-28 E. I. Du Pont De Nemours And Company Soybean plants with dominant selectable trait for herbicide resistance
US6013861A (en) 1989-05-26 2000-01-11 Zeneca Limited Plants and processes for obtaining them
DE3921144A1 (en) 1989-06-28 1991-01-10 Hoechst Ag DEGRADABLE POLYMER BLOCKS
DE3922493A1 (en) 1989-07-08 1991-01-17 Bayer Ag PROCESS FOR PREPARING WAESSEN DISPERSIONS OF POLYURETHANES AND THEIR USE AS COATING AGENTS FOR ANY SUBSTRATE
ES2161681T3 (en) 1989-08-10 2001-12-16 Aventis Cropscience Nv PLANTS WITH MODIFIED FLOWERS.
US5908810A (en) 1990-02-02 1999-06-01 Hoechst Schering Agrevo Gmbh Method of improving the growth of crop plants which are resistant to glutamine synthetase inhibitors
US5739082A (en) 1990-02-02 1998-04-14 Hoechst Schering Agrevo Gmbh Method of improving the yield of herbicide-resistant crop plants
CA2123715A1 (en) 1990-04-04 1991-10-05 Raymond S. C. Wong Production of improved rapeseed exhibiting a reduced saturated fatty acid content
US5198599A (en) 1990-06-05 1993-03-30 Idaho Resarch Foundation, Inc. Sulfonylurea herbicide resistance in plants
ES2173077T3 (en) 1990-06-25 2002-10-16 Monsanto Technology Llc PLANTS THAT TOLERATE GLYPHOSATE.
FR2667078B1 (en) 1990-09-21 1994-09-16 Agronomique Inst Nat Rech DNA SEQUENCE GIVING MALE CYTOPLASMIC STERILITY, MITOCHONDRIAL, MITOCHONDRIA AND PLANT CONTAINING THE SAME, AND PROCESS FOR THE PREPARATION OF HYBRIDS.
DE4104782B4 (en) 1991-02-13 2006-05-11 Bayer Cropscience Gmbh Novel plasmids containing DNA sequences that cause changes in carbohydrate concentration and carbohydrate composition in plants, as well as plants and plant cells containing these plasmids
US5731180A (en) 1991-07-31 1998-03-24 American Cyanamid Company Imidazolinone resistant AHAS mutants
ES2085031T3 (en) 1991-08-05 1996-05-16 Bio Tech Resources FERMENTATION PROCEDURE TO PRODUCE NATAMYCIN.
US6270828B1 (en) 1993-11-12 2001-08-07 Cargrill Incorporated Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability
US5305523A (en) 1992-12-24 1994-04-26 International Business Machines Corporation Method of direct transferring of electrically conductive elements into a substrate
DE4227061A1 (en) 1992-08-12 1994-02-17 Inst Genbiologische Forschung A polyfructane sucrase DNA sequence from Erwinia Amylovora
GB9218185D0 (en) 1992-08-26 1992-10-14 Ici Plc Novel plants and processes for obtaining them
DE69233352T2 (en) 1992-10-14 2004-10-07 Syngenta Ltd PLANTS AND METHOD FOR THEIR PRODUCTION
GB9223454D0 (en) 1992-11-09 1992-12-23 Ici Plc Novel plants and processes for obtaining them
SG71103A1 (en) 1993-01-21 2000-03-21 Matsushita Electric Ind Co Ltd Information recording medium and method of fabricating the same
EP0609022A3 (en) 1993-01-25 1995-08-23 Matsushita Electric Ind Co Ltd Image encoding apparatus.
CZ290301B6 (en) 1993-03-25 2002-07-17 Novartis Ag Pesticidal proteins, strains containing the pesticidal proteins, nucleotide sequences encoding them and plants transformed thereby
WO1994024849A1 (en) 1993-04-27 1994-11-10 Cargill, Incorporated Non-hydrogenated canola oil for food applications
DE4323804A1 (en) 1993-07-15 1995-01-19 Siemens Ag Method and device for controlling an m-pulse inverter arrangement, consisting of a master inverter and at least one slave inverter
EP0710654A4 (en) * 1993-07-23 1996-08-28 Green Cross Corp Triazole derivative and pharmaceutical use thereof
WO1995004826A1 (en) 1993-08-09 1995-02-16 Institut Für Genbiologische Forschung Berlin Gmbh Debranching enzymes and dna sequences coding them, suitable for changing the degree of branching of amylopectin starch in plants
DE4330960C2 (en) 1993-09-09 2002-06-20 Aventis Cropscience Gmbh Combination of DNA sequences that enable the formation of highly amylose-containing starch in plant cells and plants, processes for producing these plants and the modified starch that can be obtained therefrom
WO1995009910A1 (en) 1993-10-01 1995-04-13 Mitsubishi Corporation Gene that identifies sterile plant cytoplasm and process for preparing hybrid plant by using the same
AU692791B2 (en) 1993-10-12 1998-06-18 Agrigenetics, Inc. Brassica napus variety AG019
BR9408286A (en) 1993-11-09 1997-08-26 Du Pont Construction of recombinant DNA plant fructose production method dextran production method alternan production method potato plant method of increasing fructan levels in seed and soybean plants
CA2186399C (en) 1994-03-25 2001-09-04 David Cooke Method for producing altered starch from potato plants
RU2201963C2 (en) 1994-05-18 2003-04-10 Плант Тек Биотехнологи Гмбх Форшунг Унд Энтвиклунг DNA SEQUENCE (VARIANTS, RECOMBINANT DNA, PROTEIN, METHOD OF PROTEIN PREPARING, METHOD OF MICROORGANISM PREPARING, METHOD OF FUNGUS CELL PREPARING, METHOD OF PREPARING LINEAR α-1,4-GLUCANES AND/OR FRUCTOSE AND METHOD OF PREPARING LINEAR α-1,4-GLUCANES AND/OR FRUCTOSE IN VITRO
US5824790A (en) 1994-06-21 1998-10-20 Zeneca Limited Modification of starch synthesis in plants
JPH10507622A (en) 1994-06-21 1998-07-28 ゼネカ・リミテッド New plants and how to get them
NL1000064C1 (en) 1994-07-08 1996-01-08 Stichting Scheikundig Onderzoe Production of oligosaccharides in transgenic plants.
DE4441408A1 (en) 1994-11-10 1996-05-15 Inst Genbiologische Forschung DNA sequences from Solanum tuberosum encoding enzymes involved in starch synthesis, plasmids, bacteria, plant cells and transgenic plants containing these sequences
DE4447387A1 (en) 1994-12-22 1996-06-27 Inst Genbiologische Forschung Debranching enzymes from plants and DNA sequences encoding these enzymes
US6057494A (en) 1995-01-06 2000-05-02 Centrum Voor Plantenveredelings-En Reproduktieonderzoek DNA sequences encoding carbohydrate polymer synthesizing enzymes and method for producing transgenic plants
JPH08208620A (en) 1995-02-03 1996-08-13 Takeda Chem Ind Ltd Aminopyrazole derivative, its production and use
DE19509695A1 (en) 1995-03-08 1996-09-12 Inst Genbiologische Forschung Process for the preparation of a modified starch in plants, and the modified starch isolatable from the plants
US5853973A (en) 1995-04-20 1998-12-29 American Cyanamid Company Structure based designed herbicide resistant products
PL186091B1 (en) 1995-04-20 2003-10-31 American Cyanamid Co Products resistant to herbicides designed on the basis of structure
DK0826061T3 (en) 1995-05-05 2007-09-24 Nat Starch Chem Invest Enhancements to or related to plant starch compositions
FR2734842B1 (en) 1995-06-02 1998-02-27 Rhone Poulenc Agrochimie DNA SEQUENCE OF A HYDROXY-PHENYL PYRUVATE DIOXYGENASE GENE AND OBTAINING PLANTS CONTAINING A HYDROXY-PHENYL PYRUVATE DIOXYGENASE GENE, TOLERANT TO CERTAIN HERBICIDES
US5712107A (en) 1995-06-07 1998-01-27 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
US6284479B1 (en) 1995-06-07 2001-09-04 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
GB9513881D0 (en) 1995-07-07 1995-09-06 Zeneca Ltd Improved plants
FR2736926B1 (en) 1995-07-19 1997-08-22 Rhone Poulenc Agrochimie 5-ENOL PYRUVYLSHIKIMATE-3-PHOSPHATE SYNTHASE MUTEE, CODING GENE FOR THIS PROTEIN AND PROCESSED PLANTS CONTAINING THIS GENE
WO1997011188A1 (en) 1995-09-19 1997-03-27 Planttec Biotechnologie Gmbh Plants which synthesise a modified starch, process for the production thereof and modified starch
GB9524938D0 (en) 1995-12-06 1996-02-07 Zeneca Ltd Modification of starch synthesis in plants
DE19601365A1 (en) 1996-01-16 1997-07-17 Planttec Biotechnologie Gmbh Nucleic acid molecules from plants encoding enzymes involved in starch synthesis
DE19608918A1 (en) 1996-03-07 1997-09-11 Planttec Biotechnologie Gmbh Nucleic Acid Molecules Encoding New Debranching Enzymes from Maize
US5773704A (en) 1996-04-29 1998-06-30 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Herbicide resistant rice
DE19618125A1 (en) 1996-05-06 1997-11-13 Planttec Biotechnologie Gmbh Nucleic acid molecules that encode new potato debranching enzymes
DE19619918A1 (en) 1996-05-17 1997-11-20 Planttec Biotechnologie Gmbh Nucleic acid molecules encoding soluble starch synthases from maize
CA2256461C (en) 1996-05-29 2012-07-24 Hoechst Schering Agrevo Gmbh Nucleic acid molecules encoding enzymes from wheat which are involved in starch synthesis
JP2000512348A (en) 1996-06-12 2000-09-19 パイオニア ハイ―ブレッド インターナショナル，インコーポレイテッド A substitute for modified starch in papermaking.
WO1997047808A1 (en) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substitutes for modified starch in paper manufacture
CA2257621C (en) 1996-06-12 2003-02-04 Pioneer Hi-Bred International, Inc. Substitutes for modified starch in paper manufacture
US5876739A (en) 1996-06-13 1999-03-02 Novartis Ag Insecticidal seed coating
AUPO069996A0 (en) 1996-06-27 1996-07-18 Australian National University, The Manipulation of plant cellulose
US5850026A (en) 1996-07-03 1998-12-15 Cargill, Incorporated Canola oil having increased oleic acid and decreased linolenic acid content
US5773702A (en) 1996-07-17 1998-06-30 Board Of Trustees Operating Michigan State University Imidazolinone herbicide resistant sugar beet plants
GB9623095D0 (en) 1996-11-05 1997-01-08 Nat Starch Chem Invest Improvements in or relating to starch content of plants
US6232529B1 (en) 1996-11-20 2001-05-15 Pioneer Hi-Bred International, Inc. Methods of producing high-oil seed by modification of starch levels
GB9625045D0 (en) 1996-11-30 1997-01-22 Pfizer Ltd Parasiticidal compounds
DE19653176A1 (en) 1996-12-19 1998-06-25 Planttec Biotechnologie Gmbh New maize nucleic acid molecules and their use to produce a modified starch
CA2193938A1 (en) 1996-12-24 1998-06-24 David G. Charne Oilseed brassica containing an improved fertility restorer gene for ogura cytoplasmic male sterility
US5981840A (en) 1997-01-24 1999-11-09 Pioneer Hi-Bred International, Inc. Methods for agrobacterium-mediated transformation
DE19708774A1 (en) 1997-03-04 1998-09-17 Max Planck Gesellschaft Enzymes encoding nucleic acid molecules which have fructosyl polymerase activity
DE19709775A1 (en) 1997-03-10 1998-09-17 Planttec Biotechnologie Gmbh Nucleic acid molecules encoding corn starch phosphorylase
JPH10330359A (en) * 1997-03-31 1998-12-15 Nippon Bayeragrochem Kk Phenylacetylene derivative and herbicide
GB9718863D0 (en) 1997-09-06 1997-11-12 Nat Starch Chem Invest Improvements in or relating to stability of plant starches
DE19749122A1 (en) 1997-11-06 1999-06-10 Max Planck Gesellschaft Enzymes encoding nucleic acid molecules that have fructosyl transferase activity
FR2770854B1 (en) 1997-11-07 2001-11-30 Rhone Poulenc Agrochimie DNA SEQUENCE OF A GENE OF HYDROXY-PHENYL PYRUVATE DIOXYGENASE AND PRODUCTION OF PLANTS CONTAINING SUCH A GENE, HERBICIDE TOLERANT
FR2772789B1 (en) 1997-12-24 2000-11-24 Rhone Poulenc Agrochimie PROCESS FOR THE ENZYMATIC PREPARATION OF HOMOGENTISATE
AU3478499A (en) 1998-04-09 1999-11-01 E.I. Du Pont De Nemours And Company Starch r1 phosphorylation protein homologs
DE19820608A1 (en) 1998-05-08 1999-11-11 Hoechst Schering Agrevo Gmbh New nucleic acid encoding isoamylase from wheat and related transgenic plants producing starch with altered properties
DE19820607A1 (en) 1998-05-08 1999-11-11 Hoechst Schering Agrevo Gmbh New enzyme with starch synthase activity, useful for producing starch for foods and packaging materials
AU4261099A (en) 1998-05-13 1999-11-29 Planttec Biotechnologie Gmbh Transgenic plants with a modified activity of a plastidial adp/atp translocator
DE19821614A1 (en) 1998-05-14 1999-11-18 Hoechst Schering Agrevo Gmbh Sugar beet mutants which are tolerant to sulfonylurea herbicides
NZ502612A (en) 1998-06-10 2001-06-29 Boulder Scient Co Synthesis of aryl boronic acids
US6635756B1 (en) 1998-06-15 2003-10-21 National Starch And Chemical Investment Holding Corporation Starch obtainable from modified plants
US6693185B2 (en) 1998-07-17 2004-02-17 Bayer Bioscience N.V. Methods and means to modulate programmed cell death in eukaryotic cells
DE19836099A1 (en) 1998-07-31 2000-02-03 Hoechst Schering Agrevo Gmbh Nucleic acid molecules coding for a β-amylase, plants which synthesize a modified starch, process for the preparation of the plants, their use and the modified starch
DE19836098A1 (en) 1998-07-31 2000-02-03 Hoechst Schering Agrevo Gmbh Plants that synthesize a modified starch, process for producing the plants, their use and the modified starch
EP1108040A2 (en) 1998-08-25 2001-06-20 Pioneer Hi-Bred International, Inc. Plant glutamine: fructose-6-phosphate amidotransferase nucleic acids
HUP0103414A3 (en) 1998-09-02 2005-12-28 Bayer Bioscience Gmbh Nucleic acid molecules encoding an amylosucrase
DE19924342A1 (en) 1999-05-27 2000-11-30 Planttec Biotechnologie Gmbh Genetically modified plant cells and plants with increased activity of an amylosucrase protein and a branching enzyme
JP2002527068A (en) 1998-10-09 2002-08-27 プランテック バイオテクノロジー ゲーエムベーハー フォーシュング アンド エンテゥウィックラング Nucleic acid molecule encoding a branching enzyme from a genus Neisseria and method for producing α-1,6-branched α-1,4-glucan
CN100408687C (en) 1998-11-09 2008-08-06 拜尔生物科学有限公司 Nucleic acid molecules from rice and their use for the prodn. of modified starch
US6503904B2 (en) 1998-11-16 2003-01-07 Syngenta Crop Protection, Inc. Pesticidal composition for seed treatment
US6531648B1 (en) 1998-12-17 2003-03-11 Syngenta Participations Ag Grain processing method and transgenic plants useful therein
DE19905069A1 (en) 1999-02-08 2000-08-10 Planttec Biotechnologie Gmbh Alternansucrase encoding nucleic acid molecules
US6323392B1 (en) 1999-03-01 2001-11-27 Pioneer Hi-Bred International, Inc. Formation of brassica napus F1 hybrid seeds which exhibit a highly elevated oleic acid content and a reduced linolenic acid content in the endogenously formed oil of the seeds
EP1173580A1 (en) 1999-04-29 2002-01-23 Syngenta Limited Herbicide resistant plants
CN1359423A (en) 1999-04-29 2002-07-17 辛甄塔有限公司 Herbicide resistant plants
DE19926771A1 (en) 1999-06-11 2000-12-14 Aventis Cropscience Gmbh Nucleic acid molecules from wheat, transgenic plant cells and plants and their use for the production of modified starch
DE19937348A1 (en) 1999-08-11 2001-02-22 Aventis Cropscience Gmbh Nucleic acid molecules from plants encoding enzymes involved in starch synthesis
DE19937643A1 (en) 1999-08-12 2001-02-22 Aventis Cropscience Gmbh Transgenic cells and plants with altered activity of the GBSSI and BE proteins
AU7647000A (en) 1999-08-20 2001-03-19 Basf Plant Science Gmbh Increasing the polysaccharide content in plants
US6423886B1 (en) 1999-09-02 2002-07-23 Pioneer Hi-Bred International, Inc. Starch synthase polynucleotides and their use in the production of new starches
US6472588B1 (en) 1999-09-10 2002-10-29 Texas Tech University Transgenic cotton plants with altered fiber characteristics transformed with a sucrose phosphate synthase nucleic acid
GB9921830D0 (en) 1999-09-15 1999-11-17 Nat Starch Chem Invest Plants having reduced activity in two or more starch-modifying enzymes
AR025996A1 (en) 1999-10-07 2002-12-26 Valigen Us Inc NON-TRANSGENIC PLANTS RESISTANT TO HERBICIDES.
CA2401093A1 (en) 2000-03-09 2001-09-13 Monsanto Technology Llc Methods for making plants tolerant to glyphosate and compositions thereof
WO2001065922A2 (en) 2000-03-09 2001-09-13 E. I. Du Pont De Nemours And Company Sulfonylurea-tolerant sunflower plants
MXPA03000982A (en) 2000-07-31 2005-02-25 Nihon Nohyaku Co Ltd Pyrazole derivatives, pest controllers containing the same as the active ingredient and process for their production.
EP1325136A1 (en) 2000-09-29 2003-07-09 Syngenta Limited Herbicide resistant plants
US6660690B2 (en) 2000-10-06 2003-12-09 Monsanto Technology, L.L.C. Seed treatment with combinations of insecticides
US6734340B2 (en) 2000-10-23 2004-05-11 Bayer Cropscience Gmbh Monocotyledon plant cells and plants which synthesise modified starch
FR2815969B1 (en) 2000-10-30 2004-12-10 Aventis Cropscience Sa TOLERANT PLANTS WITH HERBICIDES BY METABOLIC BYPASS
PL366144A1 (en) 2000-10-30 2005-01-24 Maxygen, Inc. Novel glyphosate n-acetyltransferase (gat) genes
EP1349446B1 (en) 2000-12-08 2013-01-23 Commonwealth Scientific And Industrial Research Organisation Modification of sucrose synthase gene expression in plant tissue and uses therefor
DE10108480A1 (en) * 2001-02-22 2002-09-05 Bayer Ag Pyrazolylpyrimidine
IL157723A0 (en) * 2001-03-15 2004-03-28 Basf Ag 5-phenylpyrimidine, methods and intermediate products for the production thereof and use of the same for controlling pathogenic fungi
US20020134012A1 (en) 2001-03-21 2002-09-26 Monsanto Technology, L.L.C. Method of controlling the release of agricultural active ingredients from treated plant seeds
WO2002079410A2 (en) 2001-03-30 2002-10-10 Basf Plant Science Gmbh Glucan chain length domains
WO2002101059A2 (en) 2001-06-12 2002-12-19 Bayer Cropscience Gmbh Transgenic plants synthesising high amylose starch
AU2002322435A1 (en) 2001-08-09 2003-02-24 Cibus Genetics Non-transgenic herbicide resistant plants
US7169982B2 (en) 2001-10-17 2007-01-30 Basf Plant Science Gmbh Starch
DE10208132A1 (en) 2002-02-26 2003-09-11 Planttec Biotechnologie Gmbh Process for the production of maize plants with an increased leaf starch content and their use for the production of maize silage
DK1483246T3 (en) 2002-03-05 2006-04-10 Bayer Cropscience Sa 5-Substituted alkylaminopyrazole derivatives as pesticides
AU2003234328A1 (en) 2002-04-30 2003-11-17 Pioneer Hi-Bred International, Inc. Novel glyphosate-n-acetyltransferase (gat) genes
FR2844142B1 (en) 2002-09-11 2007-08-17 Bayer Cropscience Sa TRANSFORMED PLANTS WITH ENHANCED PRENYLQUINON BIOSYNTHESIS
WO2004040012A2 (en) 2002-10-29 2004-05-13 Basf Plant Science Gmbh Compositions and methods for identifying plants having increased tolerance to imidazolinone herbicides
US20040110443A1 (en) 2002-12-05 2004-06-10 Pelham Matthew C. Abrasive webs and methods of making the same
AU2003293991B2 (en) 2002-12-19 2009-01-22 Bayer Intellectual Property Gmbh Plant cells and plants which synthesize a starch with an increased final viscosity
JP2006521099A (en) 2003-03-07 2006-09-21 ビーエーエスエフ プラント サイエンス ゲーエムベーハー Promotion of amylose production in plants
AU2004227111B2 (en) 2003-04-09 2009-05-28 Bayer Cropscience Nv. Methods and means for increasing the tolerance of plants to stress conditions
EP1620557A2 (en) 2003-04-29 2006-02-01 Pioneer Hi-Bred International, Inc. Novel glyphosate-n-acetyltransferase (gat) genes
JP4601611B2 (en) 2003-05-01 2010-12-22 ブリストル−マイヤーズ スクイブ カンパニー Aryl-substituted pyrazole-amide compounds useful as kinase inhibitors
CA2526480A1 (en) 2003-05-22 2005-01-13 Syngenta Participations Ag Modified starch, uses, methods for production thereof
PL1633875T3 (en) 2003-05-28 2012-12-31 Basf Se Wheat plants having increased tolerance to imidazolinone herbicides
EP1493328A1 (en) 2003-07-04 2005-01-05 Institut National De La Recherche Agronomique Method of producing double low restorer lines of brassica napus having a good agronomic value
US7081110B2 (en) 2003-07-17 2006-07-25 The Procter & Gamble Company Applicator having an indented fingergrip with raised portions
WO2005012263A1 (en) * 2003-07-24 2005-02-10 Pharmagene Laboratories Limited 5-ht2b receptor antagonists
WO2005012529A1 (en) 2003-07-31 2005-02-10 Toyo Boseki Kabushiki Kaisha Plant producing hyaluronic acid
GB0317907D0 (en) 2003-07-31 2003-09-03 Koninkl Philips Electronics Nv Switchable 2D/3D display
AU2004264444B2 (en) 2003-08-15 2008-12-11 Commonwealth Scientific And Industrial Research Organisation (Csiro) Methods and means for altering fiber characteristics in fiber-producing plants
UY38692A (en) 2003-08-29 2020-06-30 Instituto Nac De Tecnologia Agropecuaria METHOD TO CONTROL WEEDS IN RICE PLANTS WITH INCREASED TOLERANCE FOR THE HERBICIDE IMIDAZOLINONE AND SULFONYLURÉA
ZA200601794B (en) 2003-09-04 2007-04-25 Bayer Cropscience Sa Pesticidal 5-substituted-oxyalkylamino-1-arylpyrazole derivatives
EP1670787B1 (en) 2003-09-11 2012-05-30 iTherX Pharma, Inc. Cytokine inhibitors
WO2005030941A1 (en) 2003-09-30 2005-04-07 Bayer Cropscience Gmbh Plants with increased activity of a class 3 branching enzyme
EP1687417B9 (en) 2003-09-30 2011-03-30 Bayer CropScience AG Plants with reduced activity of a class 3 branching enzyme
GB0329314D0 (en) 2003-12-18 2004-01-21 Pfizer Ltd Substituted arylpyrazoles
AR048024A1 (en) 2004-03-05 2006-03-22 Bayer Cropscience Gmbh PLANTS WITH INCREASED ACTIVITY OF DIFFERENT ENZYMES FOSFORILANTES DEL ALMIDON
ATE541042T1 (en) 2004-03-05 2012-01-15 Bayer Cropscience Ag PLANTS WITH REDUCED ACTIVITY OF THE STARCH PHOSPHORYLATING ENZYME PHOSPHOGLUCAN-WATER DIKINASE
AR048025A1 (en) 2004-03-05 2006-03-22 Bayer Cropscience Gmbh PLANTS WITH INCREASED ACTIVITY OF AN ALMIDON FOSFORILING ENZYME
AR048026A1 (en) 2004-03-05 2006-03-22 Bayer Cropscience Gmbh PROCEDURES FOR THE IDENTIFICATION OF PROTEINS WITH ENZYMATIC ACTIVITY FOSFORILADORA DE ALMIDON
US7432082B2 (en) 2004-03-22 2008-10-07 Basf Ag Methods and compositions for analyzing AHASL genes
MXPA06014761A (en) 2004-06-16 2007-03-26 Basf Plant Science Gmbh Polynucleotides encoding mature ahasl proteins for creating imidazolinone-tolerant plants.
DE102004029763A1 (en) 2004-06-21 2006-01-05 Bayer Cropscience Gmbh Plants that produce amylopectin starch with new properties
MX2007000159A (en) 2004-06-26 2007-10-10 Bayer Cropscience Sa Pesticidal n-phenylpyrazole derivatives.
BRPI0513981A (en) 2004-07-30 2008-05-20 Basf Agrochemical Products Bv plant, seed, methods for controlling weeds in the vicinity of a sunflower plant and a transformed plant, for increasing ahas activity in a plant, for producing a herbicide resistant plant, for enhancing herbicide tolerance in a tolerant plant the herbicide, to select a transformed plant cell, to increase the herbicide resistance of a plant, and to combat undesirable vegetation, isolated polynucleotide molecule, expression cassette, non-human host cell, transformation vector, plant cell transformed and isolated polypeptide
CA2575500A1 (en) 2004-08-04 2006-02-09 Basf Plant Science Gmbh Monocot ahass sequences and methods of use
PT1786908E (en) 2004-08-18 2010-04-29 Bayer Cropscience Ag Plants with increased plastidic activity of r3 starch-phosphorylating enzyme
AU2005276075B2 (en) 2004-08-26 2010-08-26 National Dairy Development Board A novel cytoplasmic male sterility system for Brassica species and its use for hybrid seed production in Indian oilseed mustard Brassica juncea
PL1805312T3 (en) 2004-09-23 2009-12-31 Bayer Ip Gmbh Methods and means for producing hyaluronan
AR051690A1 (en) 2004-12-01 2007-01-31 Basf Agrochemical Products Bv MUTATION INVOLVED IN THE INCREASE OF TOLERANCE TO IMIDAZOLINONE HERBICIDES IN PLANTS
EP1672075A1 (en) 2004-12-17 2006-06-21 Bayer CropScience GmbH Transformed plant expressing a dextransucrase and synthesizing a modified starch
CA2592116A1 (en) 2004-12-23 2006-08-03 Deciphera Pharmaceuticals, Llc Anti-inflammatory medicaments
EP1679374A1 (en) 2005-01-10 2006-07-12 Bayer CropScience GmbH Transformed plant expressing a mutansucrase and synthesizing a modified starch
JP2006304779A (en) 2005-03-30 2006-11-09 Toyobo Co Ltd Plant producing hexosamine in high productivity
EP1707632A1 (en) 2005-04-01 2006-10-04 Bayer CropScience GmbH Phosphorylated waxy potato starch
EP1710315A1 (en) 2005-04-08 2006-10-11 Bayer CropScience GmbH High phosphate starch
ES2331022T3 (en) 2005-06-15 2009-12-18 Bayer Bioscience N.V. METHODS TO INCREASE THE RESISTANCE OF PLANTS TO HYPOXIC CONDITIONS.
MX2008000097A (en) 2005-06-24 2008-03-19 Bayer Bioscience Nv Methods for altering the reactivity of plant cell walls.
AR054174A1 (en) 2005-07-22 2007-06-06 Bayer Cropscience Gmbh OVERPRINTING OF ALMIDON SYNTHEASE IN VEGETABLES
AU2006283504B2 (en) 2005-08-24 2011-08-25 E. I. Du Pont De Nemours And Company Compositions providing tolerance to multiple herbicides and methods of use thereof
WO2007027777A2 (en) 2005-08-31 2007-03-08 Monsanto Technology Llc Nucleotide sequences encoding insecticidal proteins
CA2624973C (en) 2005-10-05 2016-01-19 Bayer Cropscience Ag Production of hyaluronan from plants transgenic for hyaluronan synthase, gfat and udp-glucose dehydrogenase
CN101297041A (en) 2005-10-05 2008-10-29 拜尔作物科学股份公司 Plants with an increased production of hyaluronan II
PL1951878T3 (en) 2005-10-05 2015-07-31 Bayer Ip Gmbh Plants with increased hyaluronan production
EP1780208A1 (en) * 2005-10-28 2007-05-02 Basf Aktiengesellschaft Use of 5-amino pyrazoles for fighting plant pathogenic fungi, new 5-amino pyrazoles, method for their production and agents containing them
CA2629314A1 (en) * 2005-11-12 2007-05-24 Boehringer Ingelheim International Gmbh Tec kinase inhibitors
EP1956013B1 (en) * 2005-11-30 2016-04-13 Fujifilm RI Pharma Co., Ltd. Diagnostic and remedy for disease caused by amyloid aggregation and/or deposition
JP2007169575A (en) 2005-12-26 2007-07-05 Fujifilm Corp Organic nanoparticle dispersion composition, pigment nanoparticle dispersion composition, colored photosensitive resin composition, polymer film and photosensitive resin transfer material using the same, and color filter and liquid crystal display using them
JP2009538298A (en) * 2006-05-26 2009-11-05 アークル インコーポレイテッド Novel lapachone compounds and methods of use thereof
ES2381215T3 (en) * 2006-10-19 2012-05-24 Signal Pharmaceuticals Llc Heteroaryl compounds, their compositions and methods of treatment with them
DE102007003036A1 (en) * 2006-12-20 2008-06-26 Bayer Cropscience Ag Pyrimidinylpyrazole
ATE544758T1 (en) * 2006-12-29 2012-02-15 Abbott Gmbh & Co Kg CARBOXAMIDE COMPOUNDS AND THEIR USE AS CALPAIN INHIBITORS
CA2674530C (en) * 2007-01-12 2014-09-16 Banyu Pharmaceutical Co., Ltd. Spirochromanon derivatives
KR101502959B1 (en) * 2007-04-11 2015-03-16 깃세이 야쿠힌 고교 가부시키가이샤 5-membered heterocyclic derivative and use thereof for medical purposes
US20080255203A1 (en) * 2007-04-12 2008-10-16 Abbott Laboratories Heterocyclic compounds and their methods of use

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2010017902A1 *

Also Published As

Publication number Publication date
PE20110672A1 (en) 2011-09-25
BRPI0918430A2 (en) 2015-11-24
CN102186809A (en) 2011-09-14
CO6341618A2 (en) 2011-11-21
WO2010017902A1 (en) 2010-02-18
SV2011003838A (en) 2011-05-20
RU2011109066A (en) 2013-03-20
CR20110080A (en) 2011-05-27
US20110190365A1 (en) 2011-08-04
ECSP11010822A (en) 2011-03-31
MX2011001601A (en) 2011-03-29
IL210758A0 (en) 2011-03-31
CL2011000285A1 (en) 2011-06-10
AU2009281457A1 (en) 2010-02-18
KR20110044900A (en) 2011-05-02
CA2733958A1 (en) 2010-02-18
JP2011530548A (en) 2011-12-22
EP2374791A1 (en) 2011-10-12

Similar Documents

Publication Publication Date Title
EP2321262A1 (en) Insecticidal 4-phenyl-1h-pyrazoles
EP2583556B1 (en) Heterocyclic compounds as pest controllers
US8324390B2 (en) Tetrazole-substituted anthranilamides as pesticides
KR101732924B1 (en) Anthranilic acid diamide derivatives with hetero-aromatic and hetero-cyclic substituents
US8980886B2 (en) Anthranilic acid derivatives
US8791139B2 (en) Anthranilic diamide derivatives
EP2582695B1 (en) Anthranilic acid diamide derivatives with cyclical side chains
EP2558460B1 (en) Triazol-substituted anthranilic acid amides as pesticides
EP2092824A1 (en) Heterocyclyl pyrimidines

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20110314

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK SM TR

AX Request for extension of the european patent

Extension state: AL BA RS

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

DAX Request for extension of the european patent (deleted)
18D Application deemed to be withdrawn

Effective date: 20110526