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EP2321262A1 - Insecticides 4-phényl-1h-pyrazoles - Google Patents

Insecticides 4-phényl-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Withdrawn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)
English (en)
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 EP09777596A priority Critical patent/EP2321262A1/fr
Priority to EP11165244A priority patent/EP2374791A1/fr
Publication of EP2321262A1 publication Critical patent/EP2321262A1/fr
Withdrawn legal-status Critical Current

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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

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Abstract

La présente invention porte sur de nouveaux 4-phényl-1H-pyrazoles et sur leur utilisation en tant qu'insecticides et/ou parasiticides, ainsi que sur des procédés pour leur préparation, et sur des produits contenant des phénylpyrazoles de ce type.
EP09777596A 2008-08-14 2009-08-01 Insecticides 4-phényl-1h-pyrazoles Withdrawn EP2321262A1 (fr)

Priority Applications (2)

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EP09777596A EP2321262A1 (fr) 2008-08-14 2009-08-01 Insecticides 4-phényl-1h-pyrazoles
EP11165244A EP2374791A1 (fr) 2008-08-14 2009-08-01 4-Phényle-1H-pyrazoles insecticides

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EP08162378 2008-08-14
PCT/EP2009/005587 WO2010017902A1 (fr) 2008-08-14 2009-08-01 Insecticides 4-phényl-1h-pyrazoles
EP09777596A EP2321262A1 (fr) 2008-08-14 2009-08-01 Insecticides 4-phényl-1h-pyrazoles

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US20110190365A1 (en) 2011-08-04
IL210758A0 (en) 2011-03-31
CA2733958A1 (fr) 2010-02-18
MX2011001601A (es) 2011-03-29
CO6341618A2 (es) 2011-11-21
WO2010017902A1 (fr) 2010-02-18
KR20110044900A (ko) 2011-05-02
EP2374791A1 (fr) 2011-10-12
SV2011003838A (es) 2011-05-20
AU2009281457A1 (en) 2010-02-18
ECSP11010822A (es) 2011-03-31
JP2011530548A (ja) 2011-12-22
CN102186809A (zh) 2011-09-14
CR20110080A (es) 2011-05-27

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