EP1890540A2 - Carboxamides - Google Patents

Carboxamides

Info

Publication number
EP1890540A2
EP1890540A2 EP06743073A EP06743073A EP1890540A2 EP 1890540 A2 EP1890540 A2 EP 1890540A2 EP 06743073 A EP06743073 A EP 06743073A EP 06743073 A EP06743073 A EP 06743073A EP 1890540 A2 EP1890540 A2 EP 1890540A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
methyl
chlorine
fluorine
haloalkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP06743073A
Other languages
German (de)
French (fr)
Inventor
Ralf Dunkel
Hans-Ludwig Elbe
Herbert Gayer
Jörg Nico GREUL
Ulrike Wachendorff-Neumann
Peter Dahmen
Ingo Wetcholowsky
Haruko Sawada
Hiroyuki Hadano
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
Publication of EP1890540A2 publication Critical patent/EP1890540A2/en
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles

Definitions

  • the present invention relates to known carboxamides and their use for controlling unwanted microorganisms.
  • A is optionally substituted aryl or an aromatic or non-aromatic, 5- or 6-membered carbocyclic or heterocyclic ring having 1 to 3 heteroatoms, which may be O, N or S, and the carbocycle or heterocycle is 1, 2 or 3
  • Substitu - Can carry ducks which are selected from alkyl, halogen, haloalkyl, alkylthio, alkylsulfinyl or
  • Alkylsulfonyl are selected,
  • R 1 represents hydrogen, C, -C 8 alkyl, C r C 6 alkylsulfinyl, C r C 6 alkylsulfonyl, C 1 -C 4 -alkoxy-C 1 -C 4 - alkyl, C 3 -C 8 cycloalkyl ; C r C 6 haloalkyl, C r C 4 haloalkylthio, C r C 4 haloalkyl sulfinyl, C r C 4 -haloalkylsulfonyl, halo-Ci-C 4 -alkoxy-C r C 4 alkyl, C 3 -C 8 -halogeno-cycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, FOmVyI-C 1 -C 3 - alkyl, (Ci-C 3 alkyl) carbonyl-C r C 3 alkyl
  • Cycloalkyl carbonyl; (Ci-C 6 haloalkyl) carbonyl, (C r C 6 haloalkoxy) carbonyl, (Ci-
  • C 6 haloalkylthio) carbonyl (halo-Ci-C 4 -alkoxy-C r C 4 alkyl) carbonyl, (C 3 -C 6 -HaIo- genalkenyloxy) carbonyl, (C 3 -C 6 haloalkynyloxy) carbonyl, (C 3 -C 8 -halocycloalkyl) - carbonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; or -CH 2 -C ⁇ C-R "A ,
  • R IA is hydrogen, C r C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 -
  • Cycloalkyl (C 1 -C 4 -alkoxy) carbonyl, (C 3 -C 6 -alkenyloxy) carbonyl, (C 3 -C 6 -alkynyloxy) -carbonyl or cyano,
  • R 2 is hydrogen, C r C 8 alkyl, C r C 8 alkoxy, C r C 4 alkoxy-C, -C 4 alkyl, C 3 -C 8 cycloalkyl; Ci-C ö haloalkyl, Cj-Q-haloalkoxy, halo-Ci-C4-alkoxy-Ci-C 4 alkyl, C 3 -C 8 -HaIo- gencycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms stands,
  • R 3 and R 4 are each independently hydrogen, C r C 8 alkyl, C r C 4 alkoxy-Ci-C 4 alkyl, C 3 -C 8 cycloalkyl; C, -C 8 -haloalkyl, halo-Ci-C 4 alkyl alkoxy-Ci-C 4, C 3 -C 8 cycloalkyl-halo with in each case 1 to 9 fluorine, chlorine and / or bromine atoms,
  • R 3 and R 4 together with the nitrogen atom to which they are attached, form a saturated heterocycle having 5 to 8 ring atoms which is optionally monosubstituted or polysubstituted, identically or differently by halogen or C 1 -C 4 -alkyl, where the heterocycle 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain
  • R 5 and R 6 are independently hydrogen, C r C 8 alkyl, C 3 -C 8 cycloalkyl; C r C 8-halo, C 3 -C 8 halocycloalkyl are alkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, R 5 and R 6 furthermore together with the nitrogen atom to which they are attached form a optionally mono- or polysubstituted, identically or differently, by halogen or C 1 -C 4 -alkyl-substituted saturated heterocycle having 5 to 8 ring atoms, wherein the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 , R 7 is hydrogen or C 1 -C 6 -alkyl,
  • R 8 represents hydrogen, fluorine, Chlorine, methyl, isopropyl, methylthio or trifluoromethyl
  • R 8 "8 is hydrogen, fluorine, chlorine, C r C 4 alkyl or C, -C 4 haloalkyl
  • Q is a direct bond
  • R 9 is hydrogen, C r C 8 alkyl, Ci-C4-alkoxy-Ci-C 4 alkyl, C 1 -C 4 alkylthio-C, -C 4 -allcyl, C 2 -C 8
  • Each R is optionally substituted phenyl, cycloalkyl or bicycloalkyl; or unsubstituted C 2 -C 2 o is alkyl or optionally substituted Ci-C2o-alkyl,
  • the carboxamides of the formula (I) may optionally be used as mixtures of various possible isomeric forms, in particular of stereoisomers, such as. B. E and Z, threo and erythro, and optical isomers, but optionally also of tautomers.
  • Formula (I) includes both the E and Z isomers, as well as the threo and erythro, as well as the optical isomers, any mixtures of these isomers, as well as the possible tautomeric forms.
  • the carboxamides which can be used according to the invention are generally defined by the formula (I). Preferred radical definitions are given below.
  • A is preferably one of the following radicals Al to Al
  • R 12 represents hydrogen, cyano, halogen, nitro, C r C 4 alkyl, C r C 4 -alkoxy, Ci-C 4 alkylthio, C 3 -C 6 -
  • Cycloalkyl, Ci-C 4 haloalkyl, Ci-C4-haloalkoxy or C r C is 4 -haloalkylthio having in each case 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-Ci-C 4 alkyl, R 13 is hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio,
  • R 14 represents hydrogen, Ci-Q-alkyl, hydroxy-Ci-C 4 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl, C 1 -C 4 -
  • R 15 and R 16 are independently hydrogen, halogen, Ci-C 4 alkyl or C r C 4 -halogenoalkyl having 1 to 5 halogen atoms
  • R 17 is halogen, cyano or C r C 4 alkyl
  • Ci-C 4 haloalkyl or Ci-C is 4 -haloalkoxy having 1 to 5 halogen atoms
  • R 18 and R 19 are independently hydrogen, halogen, CRQ alkyl or C r C 4 -halogenoalkyl having 1 to 5 halogen atoms,
  • R 20 is hydrogen, halogen, C r C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms
  • R 21 is hydrogen, halogen, hydroxy, cyano, Ci-C 6 alkyl, C r C 4 - haloalkyl, Ci-C 4 logenalkoxy -Ha- or QQ-halogenoalkylthio each having 1 to 5 halogen atoms
  • R 22 is halogen, hydroxy, cyano, C r C 4 alkyl, C r C 4 alkoxy, C, -C 4 Alkylthio, C 1 -C 4 -
  • Halogen atoms, R 23 is hydrogen, halogen, cyano, C r C 4 alkyl, C r C 4 alkoxy, C r C 4 alkylthio, C 1 -C 4 -
  • R 24 is C 1 -C 4 -alkyl or QQ-haloalkyl having 1 to 5 halogen atoms
  • R 25 is C 1 -C -alkyl
  • Q 1 is S (sulfur), SO, SO 2 or CH 2
  • p is 0, 1 or 2 wherein R 25 is identical or different radicals when p is 2
  • R 26 is CrQ-alkyl or C r C 4 -haloalkyl having 1 to 5 halogen atoms
  • R 27 is CrQ-alkyl or C r C 4 -halogenoalkyl having 1 to 5 halogen atoms
  • R 28 and R 29 are independently hydrogen, halogen, amino, C r C 4 alkyl or CpC 4 -
  • Halogenoalkyl having 1 to 5 halogen atoms
  • R 30 4 alkyl or Cj-Q-haloalkyl represents hydrogen, halogen, C r C with 1 to 5 halogen atoms, R 31 and R 32 independently of one another represent hydrogen, halogen, amino, nitro, C 1 -C 4 -alkyl or
  • R 33 is hydrogen, halogen, C r C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms
  • R 34 is hydrogen, halogen, amino, QC 4 - Alkylamino, di- (QC 4 -alkyl) amino, cyano, QC 4 -
  • R 35 is halogen, QC 4 alkyl or QC 4 -haloalkyl having 1 to 5 halogen atoms
  • R 36 is hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di- (QC 4 -alkyl) amino, cyano, QC 4 -
  • R 37 is 4 -halogenoalkyl having 1 to 5 halogen atoms, halogen, QQ-alkyl or Ci-C
  • R 38 is halogen, QC 4 alkyl or QC 4 - halogenoalkyl having 1 to 5 halogen atoms
  • R 39 is hydrogen or C r C 4 alkyl
  • R 40 is 4 alkyl or halogen QC
  • R 41 is C 4 alkyl or C] -C 4 -halogenoalkyl having 1 to 5 halogen atoms
  • R 42 is hydrogen, halogen, QC 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms
  • R 43 represents halogen, hydroxyl, C r C 4 alkyl, C, -C 4 alkoxy, C, -C 4 alkylthio, C r C 4 haloalkyl, C 1 -
  • R 44 represents hydrogen, cyano, Ci-C 4 alkyl, QQ-halogenoalkyl having 1 to 5 halogen atoms, QC 4 - alkoxy-QC 4 alkyl, hydroxyC r C 4 alkyl, C r C 4 alkylsulfonyl, di (QC 4 alkyl) aminosulfonyl,
  • R 45 is hydrogen, halogen, QC 4 alkyl or QC is 4 -halogenoalkyl having 1 to 5 halogen atoms
  • R 46 is hydrogen, halogen, cyano, alkyl or QQ QC 4 -haloalkyl having 1 to 5 halogen atoms
  • R 47 represents hydrogen, halogen, QQ-alkyl or QC 4 -haloalkyl having 1 to 5 halogen atoms
  • R 48 is QC 4 alkyl.
  • A17 or A18 A very particularly preferably represents one of the radicals
  • A is particularly preferably the radical A 1.
  • A is more particularly preferably the radical A2.
  • A is also particularly preferred for the remainder A4.
  • A is moreover preferably the radical A5.
  • A is moreover preferably the radical A6.
  • A is moreover preferably the radical A9.
  • A is moreover preferably the radical Al 1.
  • A is moreover preferably the radical A 16.
  • A is moreover preferably the radical A 18.
  • R 1 preferably represents hydrogen, C, -C 6 alkyl, C r C 4 alkylsulfinyl, C r C 4 alkylsulfonyl, C, - C 3 alkoxy-C r C 3 alkyl, C 3 -C 6 - cycloalkyl; C r C 4 -haloalkyl, C r C 4 -haloalkylthio, C, -
  • -CH 2 -CH CH-R 1 ⁇
  • R 1 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, n-, iso-, sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, Trifluoromethyl, trichloromethyl, trifluoroethy
  • R 1 A is preferably hydrogen, C r C 4 alkyl, C r C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 -
  • R IA particularly preferably represents hydrogen, methyl or ethyl.
  • R 2 preferably represents hydrogen, C r C 6 alkyl, C, -C 4 alkoxy, C r C 3 alkoxy-C r C 3 alkyl, C 3 - C 6 cycloalkyl; Ci-C 4 haloalkyl, Ci-C4 haloalkoxy, halogen-C r C 3 alkoxy-C
  • R 2 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, tert-butyl, methoxy, ethoxy, n- or iso-propoxy, tert-butoxy, methoxymethyl, cyclopropyl; Trifluoromethyl, trifluoromethoxy.
  • R 3 and R 4 independently of one another preferably represent hydrogen, Ci-C ⁇ alkyl, Ci-C 3 alkoxy-C) - C 3 alkyl, C 3 -C 6 cycloalkyl; C r C 4 haloalkyl, halo-C, -C 3 alkoxy-C r C 3 alkyl, C 3 -C 6 -
  • Halogencycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 3 and R 4 also form, together with the nitrogen atom to which they are bonded, preferably one to four times, identically or differently, by halogen or
  • R 3 and R 4 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.
  • R 3 and R 4 together with the nitrogen atom to which they are attached, moreover preferably form an optionally monosubstituted to quadruple, identical or different, by fluorine,
  • Thiomorpholine or piperazine wherein the piperazine on the second nitrogen atom may be substituted by R 7 .
  • R 5 and R 6 independently of one another preferably represent hydrogen, C r C 6 alkyl, C 3 -C 6 cycloalkyl; C 1 -C 4 -haloalkyl, C 1 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 5 and R 6 also form, together with the nitrogen atom to which they are bonded, preferably a saturated heterocycle having 5 or 6 ring atoms which is optionally mono- or polysubstituted, identically or differently by halogen or C 1 -C 4 -alkyl, where the heterocycle 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain.
  • R 5 and R 6 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxyethyl.
  • R 5 and R 6 together with the nitrogen atom to which they are attached moreover preferably form a saturated heterocycle from the series morpholine, thiomorpholine or piperazine, optionally monosubstituted to trisubstituted, identically or differently by fluorine, chlorine, bromine or methyl the piperazine may be substituted on the second nitrogen atom by R 7 .
  • R 7 is preferably hydrogen or C 1 -C 4 -alkyl.
  • R 7 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
  • M is preferably one of the following cycles
  • M-14 M-15 M-16 M-17 wherein the bond marked with "*" is linked to the amide M is particularly preferably a ring selected from MI, M-7, M-12, M-14, M -15 or
  • M very particularly preferably represents the ring M-1.
  • M is also very particularly preferably the ring M-7.
  • M is also most preferably the ring M-12.
  • M is also most preferably ring M-14.
  • M is also very particularly preferred for the ring M-15.
  • M is also most preferably the ring M-17.
  • M is 0, 1 or 2.
  • n is 0, 1, 2, 3 or 4.
  • r is 0 or 1.
  • R 8 is preferably hydrogen.
  • R 8 is in the case that M is MI, moreover preferably fluorine, fluorine being particularly preferably in the 4-, 5- or 6-position, most preferably in the 4- or 6-position, in particular in the 4-position ,
  • R 8 is for the case that M is MI, moreover preferably chlorine, chlorine being particularly preferably in the 4- or 6-position.
  • R 8 is for the case that M stands for MI, furthermore preferably for methyl, wherein methyl is particularly preferably in the 3-position.
  • R 8 is for the case that M stands for MI, furthermore preferably for trifluoromethyl, where
  • Trifluoromethyl is particularly preferably in the 4- or 6-position.
  • R 8 is furthermore preferably fluorine, with fluorine being particularly preferably in the 6-position (M-2, M-3) or in the 3-position (M-4, M-5).
  • R 8 is also preferably chlorine in the case where M is M-2, M-3, M-4 or M-5, chlorine being particularly preferably in the 6-position (M-2, M-3) or in the 3-position (M-4, M-5).
  • R 8 is also preferably methyl in the case where M stands for M-2, M-3, M-4 or M-5, where methyl is particularly preferably in the 4-position (M-2) or in the 3-position (M-3,
  • R 8 stands for the case that M stands for M-6, moreover preferably for methyl, with methyl being particularly preferably in the 3-position.
  • R 8 stands for the case that M stands for M-6, moreover preferably for trifluoromethyl, trifluoromethyl being particularly preferably in the 3-position.
  • R 8 is also for the case that M is M-7, M-8 or M-9, also preferably chlorine, wherein
  • Chlorine is particularly preferably in the 5-position (M-7, M-8) or in the 3-position (M-9).
  • R 8 is also preferably methyl in the case where M is M-7, M-8 or M-9, with methyl being particularly preferably in the 5-position (M-7, M-8) or in the 3-position (M-9) stands.
  • R 8 B is preferably fluorine, chlorine, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-
  • Q is preferably a direct bond.
  • Q furthermore preferably represents -CH 2 -, - (CH 2 ) 2 -, - (CH 2 ) 3 -, -CH (CH 3 ) -, -C (CH 3 ) T , particularly preferably -CH 2 -, - (CH 2 ) 2 -, -CH (CH 3 ) -.
  • Q is also preferably SO.
  • Q is also preferably SO 2 .
  • Q is also preferably NR 9 , more preferably NH.
  • R 9 preferably represents hydrogen, C r C 6 alkyl, dCj-alkoxy-Ci-Cralkyl, C, -C 3 alkylthio-C r
  • R 9 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, sec-, iso- or tert-butyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl or cyclopropyl.
  • R 9 is very particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, iso- or tert-butyl, methoxymethyl or methylthiomethyl.
  • R is preferably phenyl which may be monosubstituted to trisubstituted by identical or different substituents, the substituents being selected from the list W 1 .
  • R is particularly preferably monosubstituted phenyl, wherein the substituents from the
  • R is also particularly preferably phenyl which is monosubstituted, identically or differently substituted, the substituents being selected from the list W 1 .
  • R is also particularly preferably triply, identically or differently substituted phenyl, where the substituents are selected from list W 1 .
  • R is very particularly preferably phenyl which is monosubstituted in the 4-position, where the
  • Substituents are selected from the list W 1 .
  • R very particularly preferably represents phenyl which is monosubstituted, identically or differently substituted in the 3,4-position, the substituents being selected from the list W 1 .
  • R very particularly preferably represents phenyl which is monosubstituted, identically or differently substituted in the 2,4-position, the substituents being selected from the list W 1 .
  • R very particularly preferably represents phenyl monosubstituted, identically or differently substituted in the 3,5-position, the substituents being selected from the list W 1 .
  • R is very particularly preferably phenyl which is triply, identically or differently substituted in the 2,4,6-position, the substituents being selected from the list W 1 .
  • W 1 is halogen, cyano, nitro, amino, hydroxy, formyl, carboxyl, carbamoyl, thiocarbamoyl; in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl,
  • Cycloalkyl or cycloalkyloxy each having 3 to 6 carbon atoms; in each case optionally monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, oxo, methyl, trifluoromethyl or ethyl, in each case doubly linked alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms; or a grouping -C (Q ') NQ 2 , wherein Q 1 is hydrogen, hydroxy, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms or cycloalkyl of 1 to 6 carbon atoms and
  • Q 2 is hydroxy, amino, methylamino, phenyl, benzyl or each optionally substituted by halogen, cyano, hydroxy, alkoxy, alkylthio, alkylamino, dialkylamino or
  • Q 1 is hydrogen, methyl, ethyl, trifluoromethyl or cyclopropyl and Q 2 is hydroxy, methoxy, ethoxy, propoxy or isopropoxy.
  • R furthermore preferably represents cycloalkyl or bicycloalkyl which is optionally monosubstituted to monosubstituted, identically or differently by C 1 -C 4 -alkyl and in each case has 3 to 10 carbon atoms.
  • R is moreover particularly preferably cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, bicyclo [2.2.1] heptyl or bicyclo [2.2.2] octyl.
  • R is also preferably unsubstituted C 2 -C 2 o-alkyl or mono- or polysubstituted by identical or different fluorine, chlorine, bromine, iodine and / or C 3 -C 6 -cycloalkyl-substituted Ci-C 2 o-alkyl in which the cycloalkyl moiety in turn may optionally be monosubstituted, identical or different by fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl and / or C 1 -C 4 -
  • Haloalkyl may be substituted.
  • R is also particularly preferably unsubstituted C 2 -C 2 o-alkyl.
  • R is furthermore particularly preferably chlorine, cyclopropyl, dichlorocyclopropyl,
  • R 12 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, C r C 2 -haloalkyl, C 1 -C 2 -haloalkoxy with in each case 1 to 5 fluorine, chlorine and / or bromine atoms, trifluoromethylthio, di-fluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl.
  • R 12 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, dichloromethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, Methylthio, ethylthio, trifluoromethylthio or difluoromethylthio.
  • R 12 is very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, isopropyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or
  • R 12 is particularly preferably methyl, difluoromethyl, trifluoromethyl or 1-fluoroethyl.
  • R 13 is preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio.
  • R 13 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine or methyl.
  • R 13 very particularly preferably represents hydrogen, fluorine, chlorine or methyl.
  • R 14 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl,
  • R 14 particularly preferably represents hydrogen, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl.
  • R 14 very particularly preferably represents hydrogen, methyl, trifluoromethyl or phenyl.
  • R 14 is particularly preferably methyl.
  • R 15 and R 16 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, methyl,
  • R 15 and R 16 are particularly preferably each hydrogen.
  • R> 17 is preferably fluorine, chlorine, bromine, cyano, methyl, ethyl, C r C 2 -haloalkyl or C r C 2 haloalkoxy having in each case 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 17 particularly preferably represents fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl,
  • R 17 is very particularly preferably fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or trifluoromethoxy.
  • R 17 is particularly preferably methyl.
  • R 17 is particularly preferably trifluoromethyl.
  • R 18 and R 19 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 18 and R 19 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 18 and R 19 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl.
  • R 18 and R 19 are particularly preferably each hydrogen.
  • R 20 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 20 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or
  • R 20 is very particularly preferably methyl.
  • R 20 particularly preferably represents trifluoromethyl.
  • R 21 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, C 1 -C 4 -alkyl, Q-C 2 -haloalkyl, C 2 -haloalkoxy or C 2 -haloalkylthio having in each case 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 21 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, n-buryl, isobutyl, sec-butyl, tert-butyl, difluoromethyl, Trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio or trichloromethylthio.
  • R 21 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl.
  • R 21 is particularly preferably iodine. Methyl. Difluoromethyl or trifluoromethyl.
  • R 22 is preferably fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C 1 -C 4 -alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy, in each case with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 22 particularly preferably represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl,
  • Difluorochloromethyl trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy.
  • R 22 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, di-fluoromethyl or trichloromethyl.
  • R 23 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, C r C 4 alkyl, methoxy, ethoxy, methylthio, ethylthio, Ci-C 2 haloalkyl or Ci-C2 haloalkoxy, each with 1 to 5 Fluorine, chlorine and / or bromine atoms, C 1 -C 2 -alkylsulphinyl or C 1 -C 2 -alkylsulphonyl.
  • R 23 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, Methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulphinyl or methylsulphonyl.
  • R 23 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, methylsulphinyl or methylsulphonyl ,
  • R 23 is particularly preferably hydrogen.
  • R 24 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 24 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 25 is preferably methyl or ethyl.
  • R 25 particularly preferably represents methyl.
  • Q 1 is preferably S (sulfur), SO 2 or CH 2 .
  • Q 1 particularly preferably represents S (sulfur) or CH 2 .
  • Q 1 very particularly preferably represents S (sulfur).
  • p is preferably 0 or 1. p is particularly preferably 0.
  • R 26 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or
  • R 26 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 26 is very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 27 is preferably methyl, ethyl or C] -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or
  • R 27 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 27 is very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 28 and R 29 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 28 and R 29 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 28 and R 29 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 28 and R 29 are particularly preferably each hydrogen.
  • R 30 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 30 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 30 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 30 is particularly preferably methyl.
  • R 31 and R 32 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or C ⁇ -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 31 and R 32 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, Bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 31 and R 32 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine,
  • R 31 and R 32 are particularly preferably each hydrogen.
  • R 33 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 33 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 33 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl,
  • R 33 is particularly preferably methyl.
  • R 34 is preferably hydrogen, fluorine, chlorine, bromine, amino, C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, cyano, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, Chlorine and / or bromine atoms.
  • R 34 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 34 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
  • R 34 particularly preferably represents amino, methylamino, dimethylamino, methyl or
  • R 35 is preferably fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl having 1 to 5
  • R 35 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,
  • R 35 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 35 particularly preferably represents methyl, trifluoromethyl or difluoromethyl.
  • R 36 preferably represents hydrogen, fluorine, chlorine, bromine, amino, C r C 4 alkylamino, di (C 1 -C 4 - alkyl) amino, cyano, methyl, ethyl or C 2 haloalkyl having 1 to 5 fluorine, Chlorine and / or bromine atoms.
  • R 36 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 36 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 36 particularly preferably represents amino, methylamino, dimethylamino, methyl or trifluoromethyl.
  • R 37 is preferably fluorine, chlorine, bromine, methyl, ethyl or C r C 2 haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 37 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,
  • R 37 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl,
  • R 37 is particularly preferably methyl. Trifluoromethyl or difluoromethyl.
  • R 38 is preferably fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl having 1 to 5
  • Fluorine, chlorine and / or bromine atoms Fluorine, chlorine and / or bromine atoms.
  • R 38 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 38 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl
  • R 39 is preferably hydrogen, methyl or ethyl.
  • R 39 particularly preferably represents methyl.
  • R 40 is preferably fluorine, chlorine, bromine, methyl or ethyl.
  • R 40 particularly preferably represents fluorine, chlorine or methyl.
  • R 41 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or
  • R 41 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 41 very particularly preferably represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 41 is particularly preferably methyl or trifluoromethyl.
  • R 42 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 42 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.
  • R 43 is preferably fluorine, chlorine, bromine, iodine, hydroxyl, C 1 -C 4 -alkyl, methoxy, ethoxy,
  • R 43 particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 43 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl,
  • R 44 preferably represents hydrogen, methyl, ethyl, Ci-C 2 haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, Ci-C 2 alkoxy-C r C 2 alkyl, hydroxymethyl, hydroxyethyl, methylsulfonyl or dimethylaminosulfonyl.
  • R 44 particularly preferably represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or hydroxyethyl.
  • R 44 is very particularly preferably methyl or methoxymethyl.
  • R 45 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 45 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 45 is very particularly preferably hydrogen or methyl.
  • R 46 is preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, iso-propyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 46 is particularly preferably hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 46 very particularly preferably represents hydrogen, methyl, difluoromethyl or trifluoromethyl.
  • R 47 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 47 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or
  • R 47 is very particularly preferably hydrogen.
  • R 48 is preferably methyl, ethyl, n-propyl or iso-propyl.
  • R 48 is particularly preferably methyl or ethyl.
  • Penthiopyrad (known from EP-A 0 737 682) of the formula
  • C 1 -C 20 -alkyl encompasses the largest range defined herein for an alkyl radical.
  • this definition includes the meanings methyl, ethyl, n-, iso-propyl, n-, iso-, sec-, tert-
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
  • heteroatoms e.g. in alkoxy
  • doubly bonded hydrocarbon radicals such as alkylene (alkanediyl) may be straight-chain or branched as far as possible.
  • dialkylamino also includes an unsymmetrically alkyl-substituted amino group, such as e.g. Methyl ethylamino.
  • Halogen substituted radicals e.g. Haloalkyl
  • Halogen substituted radicals are halogenated singly or multiply.
  • the halogen atoms may be the same or different.
  • Halogen stands for fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
  • the substances according to the invention have a strong microbicidal activity and can be used for controlling certain rust fungi, such as soybean rust and coffee rust, in crop protection.
  • the following diseases of soybean plants can be controlled: Alternaria leaf spot (Alternaria spec. Atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. Truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Dandelion leaf leaf (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye leaf spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina trifolii) Phyllostica Leaf Spot (Phyllosticta sojaecola), Powdery Mildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rh
  • Rust Phakopsora pachyrhizi
  • Scab Sphaceloma glycines
  • Stemphylium Leaf Blight Stemphylium bo- tryosum
  • Target Spot Corynespora cassiicola
  • Black Root Red Calonectria crotalariae
  • Charcoal Red Macrophomina phaseolina
  • Fusarium Blight or Wiit Root Red
  • Pod and Collar red Fusarium oxysporum, Fusarium orthoceras, Fusarium semi- titectum, Fusarium equiseti
  • Mycoleptodiscus root red Mycoleptodiscus terrestris
  • Neocosmospora Neocosmopspora vasinfecta
  • Pod and Star Blight Dia- porthe phaseolorum
  • Star Canker Diaporthe phaseolorum var.
  • Undesirable microorganisms in the present case are the organisms mentioned above.
  • the substances according to the invention can therefore be used to protect plants within a certain period of time after the treatment against the infestation by the said pathogens.
  • the period of time within which protection is afforded generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients.
  • the good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of aboveground plant parts, of plant and seed, and the soil.
  • the carboxamides of the formula (I) can be used to combat soy diseases, for example against Phakopsora species, with particularly good results.
  • the carboxamides of the formula (I) are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
  • 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 which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including plant varieties which can or can not be protected by plant variety rights.
  • Under plant parts everyone should Above-ground and underground parts and organs of the plants, such as shoot, leaf, flower and root are understood, with examples of leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes are listed.
  • 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, vaporizing, atomizing, spreading, spreading and in propagation material, in particular in seeds, further by single or multi-layer wrapping.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, ultrafine encapsulations in polymeric substances and in seed coating compositions, as well as ULV -KaIt- and warm mist formulations.
  • customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, ultrafine encapsulations in polymeric substances and in seed coating compositions, as well as ULV -KaIt- and warm mist formulations.
  • formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents, liquefied gases under pressure and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • organic solvents as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg petroleum fractions, 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 dimethylformamide and dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons such
  • liquefied gaseous diluents or carriers are meant those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Suitable solid carriers are: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates.
  • solid carriers for granules are: for example, broken and fractionated natural rocks such as calcite, pumice, marble, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.
  • Emulsifying and / or foam-forming agents are suitable: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates.
  • Suitable dispersants are: for example lignin-sulphite liquors and methylcellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers may be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids.
  • Other additives may be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.
  • the carboxamides of the formula (I) can be used as such or in their formulations also in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides, so as to obtain e.g. to broaden the spectrum of action or to prevent development of resistance. In many cases synergistic effects, i. E. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Fungicides are suitable as mixed partners: Fungicides:
  • Acetylcholinesterase (AChE) inhibitors 1.1 carbamates (eg alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, azamethiphos, bendocarb, benfuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxime, carbaryl, carbofiirane, carbosulfan, chloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilane, ethiofencarb, fenobucarb, fenothiocarb, Formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb
  • organophosphates eg acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chloroethoxyfos, chlorfenvinphos, chlormephos, chlo ⁇ yrifos (-methyl / -ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphone, Dialifos, Diazinon, Dichlofenthione, Dichlorvos / DDVP, Dicrotophos, Dimethoates, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitro
  • Pyrethroids eg acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, biotethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlorovaporthrin, cis-cypermethrin , Cis-resmethrin, cis-permethrin, clocthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, pentan-in (IR-isomer), esfenvalerate , Etofenprox, fenfluthrin, fen
  • Oxadiazines e.g., indoxacarb
  • chloronicotinyls / neonicotinoids for example, acetamiprid, clothianidin, dinotefiran, imidacloprid, nitrepyram, nithiazines, thiacloprid, thiamethoxam
  • Nicotine Bensultap, Cartap
  • Mectins for example, abamectin, avermectin, emamectin, emamectin benzoate, ivermectin, milkmectin, milbemycin
  • Juvenile hormone mimetics e.g., diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprenes, methoprenes, pyriproxifen, triprenes
  • Diacylhydrazines e.g., Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide
  • Diflubenzuron Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penflurone, Teflubenzuron, Triflumuron
  • Bistrifluron Chlofluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penflurone, Teflubenzuron, Triflumuron
  • Cyromazines 10. Inhibitors of oxidative phosphorylation, ATP disruptors
  • Organotin e.g., azocyclotin, cyhexatin, fenbutatin oxides
  • METI's e.g., Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
  • Tetronic acids e.g., spirodiclofen, spiromesifen
  • 16.2 tetramic acids [e.g. 3- (2,5-Dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (also known as: Carbonic acid, 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl ester, CAS Reg.
  • Carboxamides e.g., flonicamid
  • fumigants e.g., aluminum phosphides, methyl bromides, sulfuryl fluorides
  • mite growth inhibitors e.g., clofentezine, etoxazole, hexythiazox
  • the active compounds can be used as such, in the form of their formulations or the formulations prepared therefrom. - Forms such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules are used.
  • the application is done in a conventional manner, for example by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or the active ingredient preparation or the active ingredient itself in the Inject soil. It can also be the seed of the plants to be treated.
  • the application rates of active ingredient can be varied within a relatively wide range, depending on the mode of application.
  • the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the application rates of active ingredient are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • plants and their parts can be treated.
  • wild species or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • plant varieties and their parts are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term “parts” or “parts of plants” or “plant parts” has been explained above.
  • Plant varieties are understood to be plants having new traits which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques, which may be varieties, breeds, biotypes and genotypes.
  • the treatment according to the invention may also give rise to superadditive ("synergistic") effects, for example reduced application rates and / or extensions of the activity spectrum and / or a Enhancement of the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water. or soil salt content, increased flowering power, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the actual expected effects.
  • superadditive for example reduced application rates and / or extensions of the activity spectrum and / or a Enhancement of the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water. or soil salt content, increased flowering power, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life
  • the preferred plants or plant cultivars to be treated according to the invention include all plants which have obtained genetic material by the genetic engineering modification which gives these plants particularly advantageous valuable properties ("traits") Examples of such properties are better plant growth. increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances.
  • microbial pests such as insects, mites, phytopathogenic fungi, bacteria and / or viruses
  • transgenic plants include the important crops, such as cereals (wheat, rice), maize, soya, potato, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with maize, soya Potato, cotton, tobacco and oilseed rape are particularly emphasized.
  • Traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins produced in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryllA, CryHIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) in the plants (hereinafter "Bt plants”). Traits also highlight the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • genes conferring the desired properties may also be present in combinations with one another in the transgenic plants
  • Examples of "3t plants” are corn, cotton, soy and potato varieties sold under the trade names YDELD GARD® (eg maize , Cotton, soybean), KnockOut® (eg corn), StarLink® (eg corn), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato).
  • herbicide tolerant plants are maize varieties, cotton varieties and Soya varieties known under the trade names Roundup Ready® (tolerance to glyphosate eg maize, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance to imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Herbicide-resistant (conventionally grown on herbicide tolerance) plants are also the varieties marketed under the name Clearfield® (eg corn) mentioned. Of course, these statements also apply to future or future marketed plant varieties with these or future developed genetic traits.
  • the plants listed can be treated particularly advantageously according to the invention with the compounds of general formula (I) or the Wirkstoffrnischungen invention.
  • the preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants.
  • Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
  • Soybeans (variety: Enrei) were cultivated in plastic containers of 7.5 cm diameter. For the seedlings which had reached the 2.3 leaf stage, 6 ml of the test substance (preparation as described above) were sprayed per 3 containers. One day after spraying, the leaves were inoculated with a urediniosporen suspension (1 x 10 5 urediniospores / ml) of Phakopsora pachyrhizi. Fourteen days after inoculation, the severity of infestation per vessel was evaluated and the efficiency calculated. Phytotoxicity was also controlled.

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Abstract

Disclosed is the use of carboxamides of formula (I), wherein A, R<SUP>1</SUP>, M, Q, and R have the meanings indicated in the description, for controlling certain rust fungi, such as soybean rust or coffee rust, in crop protection.

Description

Carboxamidecarboxamides
Die vorliegende Erfindung betrifft bekannte Carboxamide und deren Verwendung zur Bekämpfung von unerwünschten Mikroorganismen.The present invention relates to known carboxamides and their use for controlling unwanted microorganisms.
Es ist bereits bekannt, dass zahlreiche Carboxamide fungizide Eigenschaften besitzen (vgl. z.B. WO 04/103975, WO 04/103953, WO 03/070705, WO 03/010149, WO 02/059086, EP-A 0 824 099, EP-A 0 737 682, EP-A 0 591 699, EP-A 0 589 301, EP-A 0 545 099, DE-A 24 09 011, DE-A 20 06 472, JP- A 2001-302605, JP-A 10-251240, JP-A 8-176112, JP-A 8-92223 und JP-A 53-72823). So sind bereits zahlreiche Carboxamide und deren Verwendung gegen Puccinia- Arten, wie beispielsweise Puccinia recondita oder Uromyces-Arten, wie beispielsweise Uromyces appendiculatus, bekannt geworden. Die Wirksamkeit dieser Stoffe ist gut, lässt aber in manchen Fällen, z.B. bei niedrigen Aufwandmengen zu wünschen übrig. Es wurde nun gefunden, dass diese Carboxamide auch Wirkung gegen andere Rostarten, wie beispielsweise den erst kürzlich aufgekommenen Sojabohnenrost, Phakopsora-Arten, wie beispielsweise Phakopsora sojae, Phakopsora pachyrhizi, Phakopsora vignae, Uredo sojae, Uromyces sojae, aber auch gegen weitere Rostarten, wie beispielsweise den Kaffeerost, Helileia vastarix, zeigen.It is already known that numerous carboxamides have fungicidal properties (cf., for example, WO 04/103975, WO 04/103953, WO 03/070705, WO 03/010149, WO 02/059086, EP-A 0 824 099, EP-A 0 737 682, EP-A 0 591 699, EP-A 0 589 301, EP-A 0 545 099, DE-A 24 09 011, DE-A 20 06 472, JP-A 2001-302605, JP-A 10 -251240, JP-A 8-176112, JP-A 8-92223 and JP-A 53-72823). Thus, numerous carboxamides and their use against Puccinia species, such as, for example, Puccinia recondita or Uromyces species, such as, for example, Uromyces appendiculatus, have become known. The efficacy of these substances is good, but in some cases, e.g. to be desired at low application rates. It has now been found that these carboxamides also have an effect against other types of rust, such as the so-called soybean rust, Phakopsora species such as Phakopsora sojae, Phakopsora pachyrhizi, Phakopsora vignae, Uredo sojae, Uromyces sojae, but also against other types of rust, such as For example, the coffee roast, Helileia vastarix show.
Es wurde nun gefunden, dass sich Carboxamide der Formel (I)It has now been found that carboxamides of the formula (I)
in welcher, in which,
A für gegebenenfalls substituiertes Aryl oder einen aromatischen oder nicht aromatischen, 5- oder 6-gliedrigen carbocyclischen oder heterocyclischen Ring mit 1 bis 3 Heteroatomen, welche O, N oder S sein können, steht und der Carbo- oder Heterocyclus 1, 2 oder 3 Substitu- enten tragen kann, welche aus Alkyl, Halogen, Halogenalkyl, Alkylthio, Alkylsulfinyl oderA is optionally substituted aryl or an aromatic or non-aromatic, 5- or 6-membered carbocyclic or heterocyclic ring having 1 to 3 heteroatoms, which may be O, N or S, and the carbocycle or heterocycle is 1, 2 or 3 Substitu - Can carry ducks which are selected from alkyl, halogen, haloalkyl, alkylthio, alkylsulfinyl or
Alkylsulfonyl ausgewählt sind,Alkylsulfonyl are selected,
R1 für Wasserstoff, C,-C8-Alkyl, CrC6-Alkylsulfinyl, CrC6-Alkylsulfonyl, C1-C4-AIkOXy-C1-C4- alkyl, C3-C8-Cycloalkyl; CrC6-Halogenalkyl, CrC4-Halogenalkylthio, CrC4-Halogenalkyl- sulfinyl, CrC4-Halogenalkylsulfonyl, Halogen-Ci-C4-alkoxy-CrC4-alkyl, C3-C8-Halogen- cycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, FOmVyI-C1-C3- alkyl, (Ci-C3-Alkyl)carbonyl-CrC3-alkyl, (C,-C3-Alkoxy)carbonyl-C,-C3-alkyl; Halogen-(Cr C3-alkyl)carbonyl-CrC3-alkyl, Halogen-ζCi-Cralkoxy^arbonyl-CrCralkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (CrC8-Alkyl)carbonyl, (C,-C8-Alkoxy)carbonyl, (CrC8-Alkylthio)carbonyl, (C,-C4-Alkoxy-R 1 represents hydrogen, C, -C 8 alkyl, C r C 6 alkylsulfinyl, C r C 6 alkylsulfonyl, C 1 -C 4 -alkoxy-C 1 -C 4 - alkyl, C 3 -C 8 cycloalkyl ; C r C 6 haloalkyl, C r C 4 haloalkylthio, C r C 4 haloalkyl sulfinyl, C r C 4 -haloalkylsulfonyl, halo-Ci-C 4 -alkoxy-C r C 4 alkyl, C 3 -C 8 -halogeno-cycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, FOmVyI-C 1 -C 3 - alkyl, (Ci-C 3 alkyl) carbonyl-C r C 3 alkyl, (C, -C 3 -alkoxy) carbonyl-C, -C 3 alkyl; Halo (C r C 3 alkyl) carbonyl-3 CrC alkyl, halo-ζCi-Cralkoxy ^ arbonyl-CrCralkyl, each with 1 to 13 fluorine, chlorine and / or bromine atoms; (C r -C 8 -alkyl) carbonyl, (C, -C 8 alkoxy) carbonyl, (C r C 8 alkylthio) carbonyl, (C, -C 4 alkoxy
CrC4-alkyl)carbonyl, (C3-C6-Alkenyloxy)carbonyl, (C3-C6-Alkinyloxy)carbonyl, (C3-C8-C r C 4 alkyl) carbonyl, (C 3 -C 6 alkenyloxy) carbonyl, (C 3 -C 6 alkynyloxy) carbonyl, (C 3 -C 8 -
Cycloalkyl)carbonyl; (Ci-C6-Halogenalkyl)carbonyl, (CrC6-Halogenalkoxy)carbonyl, (Ci-Cycloalkyl) carbonyl; (Ci-C 6 haloalkyl) carbonyl, (C r C 6 haloalkoxy) carbonyl, (Ci-
C6-Halogenalkylthio)carbonyl, (Halogen-Ci-C4-alkoxy-CrC4-alkyl)carbonyl, (C3-C6-HaIo- genalkenyloxy)carbonyl, (C3-C6-Halogenalkinyloxy)carbonyl, (C3-C8-Halogencycloalkyl)- carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -CH2-C≡C-R''A,C 6 haloalkylthio) carbonyl, (halo-Ci-C 4 -alkoxy-C r C 4 alkyl) carbonyl, (C 3 -C 6 -HaIo- genalkenyloxy) carbonyl, (C 3 -C 6 haloalkynyloxy) carbonyl, (C 3 -C 8 -halocycloalkyl) - carbonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; or -CH 2 -C≡C-R "A ,
-CH2-CH=CH-R1^, -CH=C=CH-R1 A, -C(=O)C(=O)R2, -CONR3R4 oder -CH2NR5R6 steht,-CH 2 -CH = CH-R 1 ^, -CH = C = CH-R 1 A , -C (= O) C (= O) R 2 , -CONR 3 R 4 or -CH 2 NR 5 R 6 stands,
RI A für Wasserstoff, CrC6-Alkyl, CrC6-Halogenalkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C7-R IA is hydrogen, C r C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 -
Cycloalkyl, (Ci-C4-Alkoxy)carbonyl, (C3-C6-Alkenyloxy)carbonyl, (C3-C6-Alkinyloxy)- carbonyl oder Cyano steht,Cycloalkyl, (C 1 -C 4 -alkoxy) carbonyl, (C 3 -C 6 -alkenyloxy) carbonyl, (C 3 -C 6 -alkynyloxy) -carbonyl or cyano,
R2 für Wasserstoff, CrC8-Alkyl, CrC8-Alkoxy, CrC4-Alkoxy-C,-C4-alkyl, C3-C8-Cycloalkyl; Ci-Cö-Halogenalkyl, Cj-Q-Halogenalkoxy, Halogen-Ci-C4-alkoxy-Ci-C4-alkyl, C3-C8-HaIo- gencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen steht,R 2 is hydrogen, C r C 8 alkyl, C r C 8 alkoxy, C r C 4 alkoxy-C, -C 4 alkyl, C 3 -C 8 cycloalkyl; Ci-C ö haloalkyl, Cj-Q-haloalkoxy, halo-Ci-C4-alkoxy-Ci-C 4 alkyl, C 3 -C 8 -HaIo- gencycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms stands,
R3 und R4 unabhängig voneinander jeweils für Wasserstoff, CrC8-Alkyl, CrC4-Alkoxy-Ci-C4-alkyl, C3-C8-Cycloalkyl; C,-C8-Halogenalkyl, Halogen-Ci-C4-alkoxy-Ci-C4-alkyl, C3-C8-Halogen- cycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,R 3 and R 4 are each independently hydrogen, C r C 8 alkyl, C r C 4 alkoxy-Ci-C 4 alkyl, C 3 -C 8 cycloalkyl; C, -C 8 -haloalkyl, halo-Ci-C 4 alkyl alkoxy-Ci-C 4, C 3 -C 8 cycloalkyl-halo with in each case 1 to 9 fluorine, chlorine and / or bromine atoms,
R3 und R4 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Ci-C4-Alkyl substituierten gesättigten Heterocyclus mit 5 bis 8 Ringatomen bilden, wobei der Hetero- cyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR7 enthalten kann,R 3 and R 4 together with the nitrogen atom to which they are attached, form a saturated heterocycle having 5 to 8 ring atoms which is optionally monosubstituted or polysubstituted, identically or differently by halogen or C 1 -C 4 -alkyl, where the heterocycle 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain
R5 und R6 unabhängig voneinander für Wasserstoff, CrC8-Alkyl, C3-C8-Cycloalkyl; CrC8-Halogen- alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen, R5 und R6 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Ci-C4-Alkyl substituierten gesättigten Heterocyclus mit 5 bis 8 Ringatomen bilden, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR7 enthalten kann, R7 für Wasserstoff oder C,-C6-Alkyl steht,R 5 and R 6 are independently hydrogen, C r C 8 alkyl, C 3 -C 8 cycloalkyl; C r C 8-halo, C 3 -C 8 halocycloalkyl are alkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, R 5 and R 6 furthermore together with the nitrogen atom to which they are attached form a optionally mono- or polysubstituted, identically or differently, by halogen or C 1 -C 4 -alkyl-substituted saturated heterocycle having 5 to 8 ring atoms, wherein the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 , R 7 is hydrogen or C 1 -C 6 -alkyl,
M für einen jeweils einfach durch R8 substituierten Phenyl- oder Thiophen-Ring oder für jeweils einfach bis vierfach durch R8"8 substituiertes C3-C6-Cycloalkyl oder C3-C6-Cycloalkenyl, R8 für Wasserstoff, Fluor, Chlor, Methyl, iso-Propyl, Methylthio oder Trifluormethyl steht, R8"8 für Wasserstoff, Fluor, Chlor, CrC4-Alkyl oder C,-C4-Haloalkyl steht, Q für eine direkte Bindung, CrC4-Alkylen, C2-C4-Alkenylen, O, S, SO, SO2 oder NR9 steht, R9 für Wasserstoff, CrC8-Alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, C1-C4-Alkylthio-C,-C4-allcyl, C2-C8- Alkenyl, C2-C8-Alkinyl, CrC6-HalogenalkyI, C2-C6-Halogenalkenyl, C2-C6-Halogenalkinyl oder C3-C6-Cycloalkyl steht,M for each simply by R 8 substituted phenyl or thiophene ring, or represents in each case monosubstituted to tetrasubstituted by R 8 "8-substituted C 3 -C 6 -cycloalkyl or C 3 -C 6 -cycloalkenyl, R 8 represents hydrogen, fluorine, Chlorine, methyl, isopropyl, methylthio or trifluoromethyl, R 8 "8 is hydrogen, fluorine, chlorine, C r C 4 alkyl or C, -C 4 haloalkyl, Q is a direct bond, C r C 4 Alkylene, C 2 -C 4 alkenylene, O, S, SO, SO 2 or NR 9 , R 9 is hydrogen, C r C 8 alkyl, Ci-C4-alkoxy-Ci-C 4 alkyl, C 1 -C 4 alkylthio-C, -C 4 -allcyl, C 2 -C 8 - alkenyl, C 2 -C 8 alkynyl, C r C 6 -HalogenalkyI, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl or C 3 -C 6 cycloalkyl,
R für jeweils gegebenenfalls substituiertes Phenyl, Cycloalkyl oder Bicycloalkyl; oder für unsubstituiertes C2-C2o-Alkyl oder für gegebenenfalls substituiertes Ci-C2o-Alkyl steht,Each R is optionally substituted phenyl, cycloalkyl or bicycloalkyl; or unsubstituted C 2 -C 2 o is alkyl or optionally substituted Ci-C2o-alkyl,
zur Bekämpfung von bestimmten Rostpilzen, wie Sojabohnenrost und Kaffeerost, im Pflanzenschutz verwenden lassen.to control certain rust fungi, such as soybean rust and coffee rust, use in plant protection.
Die Verbindungen der Formel (I) sind bekannt.The compounds of the formula (I) are known.
Die Carboxamide der Formel (I) können gegebenenfalls als Mischungen verschiedener möglicher isomerer Formen, insbesondere von Stereoisomeren, wie z. B. E- und Z-, threo- und erythro-, sowie optischen Isomeren, gegebenenfalls aber auch von Tautomeren vorliegen. Formel (I) schließt sowohl die E- als auch die Z-Isomeren, wie auch die threo- und erythro-, sowie die optischen Isomeren, beliebige Mischungen dieser Isomeren, sowie die möglichen tautomeren Formen ein.The carboxamides of the formula (I) may optionally be used as mixtures of various possible isomeric forms, in particular of stereoisomers, such as. B. E and Z, threo and erythro, and optical isomers, but optionally also of tautomers. Formula (I) includes both the E and Z isomers, as well as the threo and erythro, as well as the optical isomers, any mixtures of these isomers, as well as the possible tautomeric forms.
Die erfindungsgemäß verwendbaren Carboxamide sind durch die Formel (I) allgemein definiert. Bevorzugte Restedefinitionen sind im Folgenden angegeben.The carboxamides which can be used according to the invention are generally defined by the formula (I). Preferred radical definitions are given below.
A steht bevorzugt für einen der folgenden Reste Al bis Al 9A is preferably one of the following radicals Al to Al
Al A2 A3 A4 A5Al A2 A3 A4 A5
All A12 A13 A14 A15All A12 A13 A14 A15
A16 A17 A18 A19 in welchen A16 A17 A18 A19 in which
R12 für Wasserstoff, Cyano, Halogen, Nitro, CrC4-Alkyl, CrC4-AIkoxy, Ci-C4-Alkylthio, C3-C6-R 12 represents hydrogen, cyano, halogen, nitro, C r C 4 alkyl, C r C 4 -alkoxy, Ci-C 4 alkylthio, C 3 -C 6 -
Cycloalkyl, Ci-C4-Halogenalkyl, Ci-C4-Halogenalkoxy oder CrC4-Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen, Aminocarbonyl oder Aminocarbonyl-Ci-C4-alkyl steht, R13 für Wasserstoff, Halogen, Cyano, C,-C4-Alkyl, C,-C4-Alkoxy oder C,-C4-Alkylthio steht,Cycloalkyl, Ci-C 4 haloalkyl, Ci-C4-haloalkoxy or C r C is 4 -haloalkylthio having in each case 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-Ci-C 4 alkyl, R 13 is hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio,
R14 für Wasserstoff, Ci-Q-Alkyl, Hydroxy-Ci-C4-alkyl, C2-C6-Alkenyl, C3-C6-Cycloalkyl, C1-C4-R 14 represents hydrogen, Ci-Q-alkyl, hydroxy-Ci-C 4 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl, C 1 -C 4 -
Alkylthio-CrC4-alkyl, CrC4-Alkoxy-Ci-C4-alkyl, CrC4-Halogenalkyl, C,-C4-Halogenalkylthio-Alkylthio-C r C 4 alkyl, C r C 4 alkoxy-Ci-C 4 alkyl, C r C 4 haloalkyl, C, -C 4 -haloalkylthio
CrC4-alkyl, Ci-C4-Halogenalkoxy-CrC4-alkyl mit jeweils 1 bis 5 Halogenatomen, oder Phenyl steht, R15 und R16 unabhängig voneinander für Wasserstoff, Halogen, Ci-C4-Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R17 für Halogen, Cyano oder CrC4-Alkyl, oder Ci-C4-Halogenalkyl oder Ci-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht,C r C 4 alkyl, Ci-C4-haloalkoxy-C r C 4 -alkyl having 1 to 5 halogen atoms, or phenyl, R 15 and R 16 are independently hydrogen, halogen, Ci-C 4 alkyl or C r C 4 -halogenoalkyl having 1 to 5 halogen atoms, R 17 is halogen, cyano or C r C 4 alkyl, or Ci-C 4 haloalkyl or Ci-C is 4 -haloalkoxy having 1 to 5 halogen atoms,
R18 und R19 unabhängig voneinander für Wasserstoff, Halogen, CrQ-Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 18 and R 19 are independently hydrogen, halogen, CRQ alkyl or C r C 4 -halogenoalkyl having 1 to 5 halogen atoms,
R20 für Wasserstoff, Halogen, CrC4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R21 für Wasserstoff, Halogen, Hydroxy, Cyano, Ci-C6-Alkyl, CrC4-Halogenalkyl, Ci-C4-Ha- logenalkoxy oder Q-Q-Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen steht, R22 für Halogen, Hydroxy, Cyano, CrC4-Alkyl, CrC4-Alkoxy, C,-C4-Alkylthio, C1-C4-R 20 is hydrogen, halogen, C r C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms, R 21 is hydrogen, halogen, hydroxy, cyano, Ci-C 6 alkyl, C r C 4 - haloalkyl, Ci-C 4 logenalkoxy -Ha- or QQ-halogenoalkylthio each having 1 to 5 halogen atoms, R 22 is halogen, hydroxy, cyano, C r C 4 alkyl, C r C 4 alkoxy, C, -C 4 Alkylthio, C 1 -C 4 -
Halogenalkyl, Ci-C4-Halogenalkylthio oder CpQ-Halogenalkoxy mit jeweils 1 bis 5Haloalkyl, Ci-C 4 haloalkylthio or CpQ-haloalkoxy each having 1 to 5
Halogenatomen steht, R23 für Wasserstoff, Halogen, Cyano, CrC4-Alkyl, CrC4-Alkoxy, CrC4-Alkylthio, C1-C4-Halogen atoms, R 23 is hydrogen, halogen, cyano, C r C 4 alkyl, C r C 4 alkoxy, C r C 4 alkylthio, C 1 -C 4 -
Halogenalkyl, CrC4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen, C1-C4- Alkylsulphinyl oder C1-C4-Alkylsulphonyl steht,Haloalkyl, C r C 4 haloalkoxy, each having 1 to 5 halogen atoms, C 1 -C 4 - alkylsulphinyl or C 1 -C 4 alkylsulphonyl,
R24 für C]-C4-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R25 für CrQ-Alkyl steht, Q1 für S (Schwefel), SO, SO2 oder CH2 steht, p für 0, 1 oder 2, wobei R25 für identische oder verschiedene Reste steht, wenn p für 2 steht, R26 für CrQ-Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R27 für CrQ-Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R28 und R29 unabhängig voneinander für Wasserstoff, Halogen, Amino, CrC4-Alkyl oder CpC4-R 24 is C 1 -C 4 -alkyl or QQ-haloalkyl having 1 to 5 halogen atoms, R 25 is C 1 -C -alkyl, Q 1 is S (sulfur), SO, SO 2 or CH 2 , p is 0, 1 or 2, wherein R 25 is identical or different radicals when p is 2, R 26 is CrQ-alkyl or C r C 4 -haloalkyl having 1 to 5 halogen atoms, R 27 is CrQ-alkyl or C r C 4 -halogenoalkyl having 1 to 5 halogen atoms, R 28 and R 29 are independently hydrogen, halogen, amino, C r C 4 alkyl or CpC 4 -
Halogenalkyl mit 1 bis 5 Halogenatomen stehen,Halogenoalkyl having 1 to 5 halogen atoms,
R30 für Wasserstoff, Halogen, CrC4-Alkyl oder Cj-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R31 und R32 unabhängig voneinander für Wasserstoff, Halogen, Amino, Nitro, Q-C4-Alkyl oder Q-R 30 4 alkyl or Cj-Q-haloalkyl represents hydrogen, halogen, C r C with 1 to 5 halogen atoms, R 31 and R 32 independently of one another represent hydrogen, halogen, amino, nitro, C 1 -C 4 -alkyl or
C4-Halogenalkyl mit 1 bis 5 Halogenatomen stehen, R33 für Wasserstoff, Halogen, CrC4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R34 für Wasserstoff, Halogen, Amino, Q-C4-Alkylamino, Di-(Q-C4-alkyl)amino, Cyano, Q-C4-C for 4 -halogenoalkyl having 1 to 5 halogen atoms, R 33 is hydrogen, halogen, C r C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms, R 34 is hydrogen, halogen, amino, QC 4 - Alkylamino, di- (QC 4 -alkyl) amino, cyano, QC 4 -
Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,Is alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R35 für Halogen, Q-C4-Alkyl oder Q-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R36 für Wasserstoff, Halogen, Amino, Ci-C4-Alkylamino, Di-(Q-C4-alkyl)amino, Cyano, Q-C4-R 35 is halogen, QC 4 alkyl or QC 4 -haloalkyl having 1 to 5 halogen atoms, R 36 is hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di- (QC 4 -alkyl) amino, cyano, QC 4 -
Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R37 für Halogen, Q-Q-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R38 für Halogen, Q-C4-Alkyl oder Q-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R39 für Wasserstoff oder CrC4-Alkyl steht, R40 für Halogen oder Q-C4-Alkyl steht,Alkyl or C r -C 4 -halogenoalkyl having 1 to 5 halogen atoms, R 37 is 4 -halogenoalkyl having 1 to 5 halogen atoms, halogen, QQ-alkyl or Ci-C, R 38 is halogen, QC 4 alkyl or QC 4 - halogenoalkyl having 1 to 5 halogen atoms, R 39 is hydrogen or C r C 4 alkyl, R 40 is 4 alkyl or halogen QC,
R41 für Ci-C4-Alkyl oder C]-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R42 für Wasserstoff, Halogen, Q-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R43 für Halogen, Hydroxy, CrC4-Alkyl, C,-C4-Alkoxy, C,-C4-Alkylthio, CrC4-Halogenalkyl, C1-R 41 is C 4 alkyl or C] -C 4 -halogenoalkyl having 1 to 5 halogen atoms, R 42 is hydrogen, halogen, QC 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms, R 43 represents halogen, hydroxyl, C r C 4 alkyl, C, -C 4 alkoxy, C, -C 4 alkylthio, C r C 4 haloalkyl, C 1 -
C4-Halogenalkylthio oder C]-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht, R44 für Wasserstoff, Cyano, Ci-C4-Alkyl, Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen, Q-C4- Alkoxy-Q-C4-alkyl, Hydroxy-CrC4-alkyl, CrC4-Alkylsulfonyl, Di(Q-C4-alkyl)aminosulfonyl,C 4 haloalkylthio or C] -C 4 -haloalkoxy having 1 to 5 halogen atoms, R 44 represents hydrogen, cyano, Ci-C 4 alkyl, QQ-halogenoalkyl having 1 to 5 halogen atoms, QC 4 - alkoxy-QC 4 alkyl, hydroxyC r C 4 alkyl, C r C 4 alkylsulfonyl, di (QC 4 alkyl) aminosulfonyl,
Q-C6-Alkylcarbonyl oder jeweils gegebenenfalls substituiertes Phenylsulfonyl oder Benzoyl steht, R45 für Wasserstoff, Halogen, Q-C4-Alkyl oder Q-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R46 für Wasserstoff, Halogen, Cyano, Q-Q-Alkyl oder Q-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R47 für Wasserstoff, Halogen, Q-Q-Alkyl oder Q-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,QC 6 alkylcarbonyl or optionally substituted phenylsulfonyl or benzoyl, R 45 is hydrogen, halogen, QC 4 alkyl or QC is 4 -halogenoalkyl having 1 to 5 halogen atoms, R 46 is hydrogen, halogen, cyano, alkyl or QQ QC 4 -haloalkyl having 1 to 5 halogen atoms, R 47 represents hydrogen, halogen, QQ-alkyl or QC 4 -haloalkyl having 1 to 5 halogen atoms,
R48 für Q-C4-Alkyl steht.R 48 is QC 4 alkyl.
A steht besonders bevorzugt für einen der Reste Al, A2, A3, A4, A5, A6, A9, AlO, Al l, A12,A particularly preferably represents one of the radicals Al, A2, A3, A4, A5, A6, A9, AlO, Al, A12,
A17 oder A18. A steht ganz besonders bevorzugt für einen der ResteA17 or A18. A very particularly preferably represents one of the radicals
Al, A2, A4, A5, A6, A9, Al 1, A16, A17, A18. A steht insbesondere bevorzugt für den Rest A 1.Al, A2, A4, A5, A6, A9, A1, A16, A17, A18. A is particularly preferably the radical A 1.
A steht außerdem insbesondere bevorzugt für den Rest A2. A steht außerdem insbesondere bevorzugt für den Rest A4.A is more particularly preferably the radical A2. A is also particularly preferred for the remainder A4.
A steht außerdem insbesondere bevorzugt für den Rest A5.A is moreover preferably the radical A5.
A steht außerdem insbesondere bevorzugt für den Rest A6.A is moreover preferably the radical A6.
A steht außerdem insbesondere bevorzugt für den Rest A9. A steht außerdem insbesondere bevorzugt für den Rest Al l .A is moreover preferably the radical A9. A is moreover preferably the radical Al 1.
A steht außerdem insbesondere bevorzugt für den Rest A 16.A is moreover preferably the radical A 16.
A steht außerdem insbesondere bevorzugt für den Rest A 18.A is moreover preferably the radical A 18.
R1 steht bevorzugt für Wasserstoff, C,-C6-Alkyl, CrC4-Alkylsulfinyl, CrC4-Alkylsulfonyl, C,- C3-Alkoxy-CrC3-alkyl, C3-C6-Cycloalkyl; CrC4-Halogenalkyl, CrC4-Halogenalkylthio, C,-R 1 preferably represents hydrogen, C, -C 6 alkyl, C r C 4 alkylsulfinyl, C r C 4 alkylsulfonyl, C, - C 3 alkoxy-C r C 3 alkyl, C 3 -C 6 - cycloalkyl; C r C 4 -haloalkyl, C r C 4 -haloalkylthio, C, -
C4-Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, Halogen-Ci-C3-alkoxy-CrC3-aIkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Ci-C3-alkyl, (Ci-C3-Alkyl)carbonyl-CrC3-alkyl, (C,-C3-Alkoxy)carbonyl-CrC3- alky 1 ; Halogen-(C i -C3-alkyl)carbony 1-C1 -C3-alky 1, Halogen-(C i -C3-alkoxy)carbony 1-C1 -C3-aI- kyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen;C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, halogeno-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C 3 alkyl, (Ci-C 3 alkyl) carbonyl-C r C 3 alkyl, (C, -C 3 -alkoxy) carbonyl-C r C 3 - alky 1; Halogen (C i -C 3 alkyl) carbonyl 1-C 1 -C 3 alky 1, halo (C i -C 3 alkoxy) carbonyl 1-C 1 -C 3 -alkyl with in each case 1 to 13 fluorine, chlorine and / or bromine atoms;
(Ci-C6-Alkyl)carbonyl, (CrC4-Alkoxy)carbonyl, (CrC4-Alkylthio)carbonyl, (CrC3-Alkoxy- CrC3-alkyl)carbonyl, (C3-C4-Alkenyloxy)carbonyl, (C3-C4-Alkinyloxy)carbonyl, (C3-C6- Cycloalkyl)carbonyl; (CrC4-Halogenalkyl)carbonyl, (C]-C4-Halogenalkoxy)carbonyl, (Cp C4-Halogenalkylthio)carbony 1, (Halogen-C i -C3-alkoxy-C i -C3-alkyl)carbony 1, (C3-C4-HaIo- genalkenyloxy)carbonyl, (C3-C4-Halogenalkinyloxy)carbonyl, (C3-C6-Halogencycloalkyl)- carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -CH2-C≡C-RI A,(Ci-C 6 alkyl) carbonyl, (C r C 4 alkoxy) carbonyl, (C r C 4 -alkylthio) carbonyl, (C r C 3 alkoxy C r C 3 alkyl) carbonyl, (C 3 -C 4 alkenyloxy) carbonyl, (C 3 -C 4 alkynyloxy) carbonyl, (C 3 -C 6 cycloalkyl) carbonyl; (C r C 4 haloalkyl) carbonyl, (C] -C 4 -haloalkoxy) carbonyl, (Cp C 4 haloalkylthio) carbonyl 1, (halo-C i -C 3 alkoxy-C i -C 3 alkyl) carbonyl 1, (C 3 -C 4 -halogenealkenyloxy) carbonyl, (C 3 -C 4 -haloalkynyloxy) carbonyl, (C 3 -C 6 -halocycloalkyl) -carbonyl having in each case 1 to 9 fluorine, chlorine and / or or bromine atoms; or -CH 2 -C≡CR IA ,
-CH2-CH=CH-R1^, -CH=C=CH-R1 A, -C(=O)C(=O)R2, -CONR3R4 oder -CH2NR5R6.-CH 2 -CH = CH-R 1 ^, -CH = C = CH-R 1 A , -C (= O) C (= O) R 2 , -CONR 3 R 4 or -CH 2 NR 5 R 6 ,
R1 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Pentyl oder Hexyl, Methylsulfinyl, Ethylsulfinyl, n- oder iso-Propylsulfinyl, n-, iso-, sec- oder tert-Butylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder iso-Propylsulfo- nyl, n-, iso-, sec- oder tert-Butylsulfonyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl, Trifluormethyl, Trichlormethyl, Tri- fluorethyl, Difluormethylthio, Difluorchlormethylthio, Trifluormethylthio, Trifluormethyl- sulfinyl, Trifluormethylsulfonyl, Trifluormethoxymethyl; Formyl, -CH2-CHO, -(CH2VCHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -(CHz)2-CO-CH3,R 1 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, n-, iso-, sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, Trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trifluoromethoxymethyl; Formyl, -CH 2 -CHO, - (CH 2 VCHO, -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 , -CH 2 -CO-CH (CH 3 ) 2 , - (CHz 2 -CO-CH 3 ,
-(CH2)2-CO-CH2CH3, -(CH2)2-CO-CH(CH3)2, -CH2-CO2CH3, -CH2-CO2CH2CH3, -CH2-CO2CH(CH3)2, -(CH2)2-CO2CH3, -(CH2)Z-CO2CH2CH3, -(CU2)2-CO2CU(CU3)2, -CH2-CO-CF3, -CH2-CO-CCl3, -CH2-CO-CH2CF3, -CH2-CO-CH2CCI3, -(CH2)z-CO-CH2CF3, -(CHz)2-CO-CH2CCl3, -CH2-CO2CH2CF3, -CH2-CO2CF2CF3, -CH2-CO2CH2CCl3, -CH2-CO2CCl2CCl3, -(CH2^-CO2CH2CF3, -(CH2)2-CO2CF2CF3, -(CH2)2-CO2CH2CC13,- (CH 2 ) 2 -CO-CH 2 CH 3 , - (CH 2 ) 2 -CO-CH (CH 3 ) 2 , -CH 2 -CO 2 CH 3 , -CH 2 -CO 2 CH 2 CH 3 , -CH 2 -CO 2 CH (CH 3 ) 2 , - (CH 2 ) 2 -CO 2 CH 3 , - (CH 2 ) Z -CO 2 CH 2 CH 3 , - (CU 2 ) 2 -CO 2 CU ( CU 3 ) 2 , -CH 2 -CO-CF 3 , -CH 2 -CO-CCl 3 , -CH 2 -CO-CH 2 CF 3 , -CH 2 -CO-CH 2 CCI 3 , - (CH 2 ) z-CO-CH 2 CF 3 , - (CH 2 ) 2 -CO-CH 2 CCl 3 , -CH 2 -CO 2 CH 2 CF 3 , -CH 2 -CO 2 CF 2 CF 3 , -CH 2 -CO 2 CH 2 CCl 3 , -CH 2 -CO 2 CCl 2 CCl 3 , - (CH 2) -CO 2 CH 2 CF 3 , - (CH 2 ) 2 -CO 2 CF 2 CF 3 , - (CH 2 ) 2 - CO 2 CH 2 CC1 3 ,
-(CH2)2-CO2CC12CC13; Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, iso-Propylcarbonyl, tert-Butylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, iso-Propoxycarbonyl, tert-Butoxycarbonyl, Methylthio- carbonyl, Ethylthiocarbonyl, iso-Propylthiocarbonyl, tert-Butylthiocarbonyl, Methoxymethyl- carbonyl, Ethoxymethylcarbonyl, Cyclopropylcarbonyl; Trifluormethylcarbonyl, Trifluorme- thoxycarbonyl, Trifluormethylthiocarbonyl, oder -CH2-C≡C-R1 A, -CH2-CH=CH-R1 A,- (CH 2 ) 2 -CO 2 CC 1 2 CC 1 3 ; Methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso-propylcarbonyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, tert-butoxycarbonyl, methylthio-carbonyl, ethylthiocarbonyl, isopropylmethylcarbonyl, tert-butylthiocarbonyl, methoxymethylcarbonyl, ethoxymethylcarbonyl, cyclopropylcarbonyl; Trifluoromethylcarbonyl, trifluoromethoxycarbonyl, trifluoromethylthiocarbonyl, or -CH 2 -C≡CR 1 A , -CH 2 -CH = CH-R 1 A ,
-CH=C=CH-R1 A, -C(=O)C(=O)R2, -CONR3R4 oder -CH2NR5R6.-CH = C = CH-R 1 A , -C (= O) C (= O) R 2 , -CONR 3 R 4 or -CH 2 NR 5 R 6 .
R1 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Methoxymethyl, Methoxymethyl- carbonyl, Ethoxymethylcarbonyl, Formyl, -CH2-C≡CH, -CH2-CH=CH2, -CH=C=CH2,R 1 very particularly preferably represents hydrogen, methyl, methoxymethyl, methoxymethylcarbonyl, ethoxymethylcarbonyl, formyl, -CH 2 -C≡CH, -CH 2 -CH =CH 2 , -CH = C =CH 2 ,
-CH2-CHO, -(CH2)Z-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CHrCO-CHtCH^, -C(O)CHO, -C(O)C(O)CH3, -C(O)C(O)CH2OCH3, -C(O)CO2CH3,-CH 2 -CHO, - (CH 2 ) Z-CHO, -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 , -CHrCO-CHtCH ^ , -C (O) CHO, -C (O) C (O) CH 3, -C (O) C (O) CH 2 OCH 3, -C (O) CO 2 CH 3,
-C(O)CO2CH2CH3.-C (O) CO 2 CH 2 CH 3 .
R1 A steht bevorzugt für Wasserstoff, CrC4-Alkyl, CrC4-Halogenalkyl, C2-C4-Alkenyl, C2-C4-R 1 A is preferably hydrogen, C r C 4 alkyl, C r C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 -
Alkinyl, C3-C6-Cycloalkyl, (CrC4-Alkoxy)carbonyl, oder Cyano. RI A steht besonders bevorzugt für Wasserstoff, Methyl oder Ethyl.Alkynyl, C 3 -C 6 cycloalkyl, (C r C 4 alkoxy) carbonyl, or cyano. R IA particularly preferably represents hydrogen, methyl or ethyl.
R2 steht bevorzugt für Wasserstoff, CrC6-Alkyl, C,-C4-Alkoxy, CrC3-Alkoxy-CrC3-alkyl, C3- C6-Cycloalkyl; Ci-C4-Halogenalkyl, Ci-C4-Halogenalkoxy, Halogen-CrC3-alkoxy-C|-C3- alkyl, C3-C6-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen. R2 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, tert-Butyl, Methoxy, Ethoxy, n- oder iso-Propoxy, tert-Butoxy, Methoxymethyl, Cyclopropyl; Trifluor- methyl, Trifluormethoxy.R 2 preferably represents hydrogen, C r C 6 alkyl, C, -C 4 alkoxy, C r C 3 alkoxy-C r C 3 alkyl, C 3 - C 6 cycloalkyl; Ci-C 4 haloalkyl, Ci-C4 haloalkoxy, halogen-C r C 3 alkoxy-C | -C 3 - alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms. R 2 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, tert-butyl, methoxy, ethoxy, n- or iso-propoxy, tert-butoxy, methoxymethyl, cyclopropyl; Trifluoromethyl, trifluoromethoxy.
R3 und R4 stehen unabhängig voneinander bevorzugt für Wasserstoff, Ci-Cβ-Alkyl, Ci-C3-Alkoxy-C)- C3-alkyl, C3-C6-Cycloalkyl; CrC4-Halogenalkyl, Halogen-C,-C3-alkoxy-CrC3-alkyl, C3-C6-R 3 and R 4 independently of one another preferably represent hydrogen, Ci-Cβ alkyl, Ci-C 3 alkoxy-C) - C 3 alkyl, C 3 -C 6 cycloalkyl; C r C 4 haloalkyl, halo-C, -C 3 alkoxy-C r C 3 alkyl, C 3 -C 6 -
Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen.Halogencycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
R3 und R4 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Halogen oderR 3 and R 4 also form, together with the nitrogen atom to which they are bonded, preferably one to four times, identically or differently, by halogen or
Ci-C4-Alkyl substituierten gesättigten Heterocyclus mit 5 oder 6 Ringatomen, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff,C 1 -C 4 -alkyl-substituted saturated heterocycle having 5 or 6 ring atoms, where the heterocycle contains 1 or 2 further non-adjacent heteroatoms from the series oxygen,
Schwefel oder NR7 enthalten kann.May contain sulfur or NR 7 .
R3 und R4 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl; Trifluormethyl, Trichlormethyl, Trifluorethyl, Trifluormethoxymethyl. R3 und R4 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, besonders bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,R 3 and R 4 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl. R 3 and R 4 , together with the nitrogen atom to which they are attached, moreover preferably form an optionally monosubstituted to quadruple, identical or different, by fluorine,
Chlor, Brom oder Methyl substituierten gesättigten Heterocyclus aus der Reihe Morpholin,Chloro, bromo or methyl substituted saturated heterocycle from the series morpholine,
Thiomorpholin oder Piperazin, wobei das Piperazin am zweiten Stickstoffatom durch R7 sub- stituiert sein kann.Thiomorpholine or piperazine, wherein the piperazine on the second nitrogen atom may be substituted by R 7 .
R5 und R6 stehen unabhängig voneinander bevorzugt für Wasserstoff, CrC6-Alkyl, C3-C6-Cycloalkyl; Ci-C4-Halogenalkyl, CrCβ-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen.R 5 and R 6 independently of one another preferably represent hydrogen, C r C 6 alkyl, C 3 -C 6 cycloalkyl; C 1 -C 4 -haloalkyl, C 1 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
R5 und R6 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, bevorzugt einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder C)- C4-Alkyl substituierten gesättigten Heterocyclus mit 5 oder 6 Ringatomen, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR7 enthalten kann.R 5 and R 6 also form, together with the nitrogen atom to which they are bonded, preferably a saturated heterocycle having 5 or 6 ring atoms which is optionally mono- or polysubstituted, identically or differently by halogen or C 1 -C 4 -alkyl, where the heterocycle 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain.
R5 und R6 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl; Trifiuormethyl, Trichlormethyl, Trifluorethyl, Trifiuormethoxyrnethyl.R 5 and R 6 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxyethyl.
R5 und R6 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, besonders bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Brom oder Methyl substituierten gesättigten Heterocyclus aus der Reihe Morpholin, Thiomorpholin oder Piperazin, wobei das Piperazin am zweiten Stickstoffatom durch R7 substituiert sein kann.R 5 and R 6 together with the nitrogen atom to which they are attached moreover preferably form a saturated heterocycle from the series morpholine, thiomorpholine or piperazine, optionally monosubstituted to trisubstituted, identically or differently by fluorine, chlorine, bromine or methyl the piperazine may be substituted on the second nitrogen atom by R 7 .
R7 steht bevorzugt für Wasserstoff oder CrC4- Alkyl.R 7 is preferably hydrogen or C 1 -C 4 -alkyl.
R7 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl.R 7 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
M steht bevorzugt für einen der folgenden CyclenM is preferably one of the following cycles
M-14 M-15 M-16 M-17 wobei die mit „*" markierte Bindung mit dem Amid verknüpft ist. M steht besonders bevorzugt für einen Ring ausgewählt aus M-I, M-7, M- 12, M-14, M-15 oderM-14 M-15 M-16 M-17 wherein the bond marked with "*" is linked to the amide M is particularly preferably a ring selected from MI, M-7, M-12, M-14, M -15 or
M-17.M-17th
M steht ganz besonders bevorzugt für den Ring M- 1. M steht außerdem ganz besonders bevorzugt für den Ring M-7. M steht außerdem ganz besonders bevorzugt für den Ring M- 12. M steht außerdem ganz besonders bevorzugt für den Ring M-14. M steht außerdem ganz besonders bevorzugt für den Ring M-15. M steht außerdem ganz besonders bevorzugt für den Ring M- 17. m steht für 0, 1 oder 2. n steht für 0, 1 , 2, 3, oder 4. r steht für 0 oder 1.M very particularly preferably represents the ring M-1. M is also very particularly preferably the ring M-7. M is also most preferably the ring M-12. M is also most preferably ring M-14. M is also very particularly preferred for the ring M-15. M is also most preferably the ring M-17. M is 0, 1 or 2. n is 0, 1, 2, 3 or 4. r is 0 or 1.
R8 steht bevorzugt für Wasserstoff.R 8 is preferably hydrogen.
R8 steht für den Fall, dass M für M-I steht, außerdem bevorzugt für Fluor, wobei Fluor besonders bevorzugt in 4-, 5- oder 6-Position, ganz besonders bevorzugt in 4- oder 6-Position, insbesondere in 4-Position steht.R 8 is in the case that M is MI, moreover preferably fluorine, fluorine being particularly preferably in the 4-, 5- or 6-position, most preferably in the 4- or 6-position, in particular in the 4-position ,
R8 steht für den Fall, dass M für M-I steht, außerdem bevorzugt für Chlor, wobei Chlor besonders bevorzugt in 4- oder 6-Position steht.R 8 is for the case that M is MI, moreover preferably chlorine, chlorine being particularly preferably in the 4- or 6-position.
R8 steht für den Fall, dass M für M-I steht, außerdem bevorzugt für Methyl, wobei Methyl besonders bevorzugt in 3-Position steht. R8 steht für den Fall, dass M für M-I steht, außerdem bevorzugt für Trifluormethyl, wobeiR 8 is for the case that M stands for MI, furthermore preferably for methyl, wherein methyl is particularly preferably in the 3-position. R 8 is for the case that M stands for MI, furthermore preferably for trifluoromethyl, where
Trifluormethyl besonders bevorzugt in 4- oder 6-Position steht. R8 steht für den Fall, dass M für M-2, M-3, M-4 oder M-5 steht, außerdem bevorzugt für Fluor, wobei Fluor besonders bevorzugt in 6-Position (M-2, M-3) oder in 3-Position (M-4, M-5) steht. R8 steht für den Fall, dass M für M-2, M-3, M-4 oder M-5 steht, außerdem bevorzugt für Chlor, wobei Chlor besonders bevorzugt in 6-Position (M-2, M-3) oder in 3-Position (M-4, M-5) steht. R8 steht für den Fall, dass M für M-2, M-3, M-4 oder M-5 steht, außerdem bevorzugt für Methyl, wobei Methyl besonders bevorzugt in 4-Position (M-2) oder in 3-Position (M-3,Trifluoromethyl is particularly preferably in the 4- or 6-position. In the case where M is M-2, M-3, M-4 or M-5, R 8 is furthermore preferably fluorine, with fluorine being particularly preferably in the 6-position (M-2, M-3) or in the 3-position (M-4, M-5). R 8 is also preferably chlorine in the case where M is M-2, M-3, M-4 or M-5, chlorine being particularly preferably in the 6-position (M-2, M-3) or in the 3-position (M-4, M-5). R 8 is also preferably methyl in the case where M stands for M-2, M-3, M-4 or M-5, where methyl is particularly preferably in the 4-position (M-2) or in the 3-position (M-3,
M-4, M-5) steht.M-4, M-5).
R8 steht für den Fall, dass M für M-6 steht, außerdem bevorzugt für Methyl, wobei Methyl besonders bevorzugt in 3-Position steht. R8 steht für den Fall, dass M für M-6 steht, außerdem bevorzugt für Trifluormethyl, wobei Tri- fluormethyl besonders bevorzugt in 3-Position steht. R8 steht für den Fall, dass M für M-7, M-8 oder M-9 steht, außerdem bevorzugt für Chlor, wobeiR 8 stands for the case that M stands for M-6, moreover preferably for methyl, with methyl being particularly preferably in the 3-position. R 8 stands for the case that M stands for M-6, moreover preferably for trifluoromethyl, trifluoromethyl being particularly preferably in the 3-position. R 8 is also for the case that M is M-7, M-8 or M-9, also preferably chlorine, wherein
Chlor besonders bevorzugt in 5-Position (M-7, M-8) oder in 3-Position (M-9) steht. R8 steht für den Fall, dass M für M-7, M-8 oder M-9 steht, außerdem bevorzugt für Methyl, wobei Methyl besonders bevorzugt in 5-Position (M-7, M-8) oder in 3-Position (M-9) steht.Chlorine is particularly preferably in the 5-position (M-7, M-8) or in the 3-position (M-9). R 8 is also preferably methyl in the case where M is M-7, M-8 or M-9, with methyl being particularly preferably in the 5-position (M-7, M-8) or in the 3-position (M-9) stands.
R8 B steht bevorzugt für Fluor, Chlor, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-R 8 B is preferably fluorine, chlorine, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-
B Buuttyyll,, TTririfflluuoorrmmeetthhyyll ooddeerr DDiifflluuoorrmmeetthhyyll, wobei die Reste R8 B gleich oder verschieden sein können, wenn m bzw. n größer als 1 sind.B Buuttyyll ,, TTririfflluoroorrmmeetthhyyll ooddeerr DDiifflluoroorrmmeetthhyyll, where the radicals R 8 B may be the same or different when m or n is greater than 1.
Q steht bevorzugt für eine direkte Bindung.Q is preferably a direct bond.
Q steht außerdem bevorzugt für -CH2-, -(CHz)2-, -(CH2)3-, -CH(CH3)-, -C(CH3)T, besonders bevorzugt für -CH2-, -(CH2)2-, -CH(CH3)-. Q steht außerdem bevorzugt für -CH=CH-, -CH2-CH=CH-, -CH(CH3)-CH=CH-, besonders bevorzugt für -CH=CH-, -CH2-CH=CH-.Q furthermore preferably represents -CH 2 -, - (CH 2 ) 2 -, - (CH 2 ) 3 -, -CH (CH 3 ) -, -C (CH 3 ) T , particularly preferably -CH 2 -, - (CH 2 ) 2 -, -CH (CH 3 ) -. Q is also preferably -CH = CH-, -CH 2 -CH = CH-, -CH (CH 3 ) -CH = CH-, more preferably -CH = CH-, -CH 2 -CH = CH-.
Q steht außerdem bevorzugt für O.Q is also preferred for O.
Q steht außerdem bevorzugt für S.Q is also preferred for S.
Q steht außerdem bevorzugt für SO. Q steht außerdem bevorzugt für SO2.Q is also preferably SO. Q is also preferably SO 2 .
Q steht außerdem bevorzugt für NR9, besonders bevorzugt für NH.Q is also preferably NR 9 , more preferably NH.
R9 steht bevorzugt für Wasserstoff, CrC6-Alkyl, d-C-j-Alkoxy-Ci-Cralkyl, C,-C3-Alkylthio-Cr R 9 preferably represents hydrogen, C r C 6 alkyl, dCj-alkoxy-Ci-Cralkyl, C, -C 3 alkylthio-C r
C3-alkyl oder C3-C6-Cycloalkyl. R9 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, sec-, iso- oder tert-Butyl, Methoxymethyl, Ethoxymethyl, Methoxyethyl, Ethoxyethyl, Methylthiome- thyl, Ethylthiomethyl, Methylthioethyl, Ethylthioethyl oder Cyclopropyl. R9 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, iso- oder tert-Butyl, Methoxymethyl oder Methylthiomethyl.C 3 alkyl or C 3 -C 6 cycloalkyl. R 9 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, sec-, iso- or tert-butyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl or cyclopropyl. R 9 is very particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, iso- or tert-butyl, methoxymethyl or methylthiomethyl.
R steht bevorzugt für gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Phenyl, wobei die Substituenten aus der Liste W1 ausgewählt sind. R steht besonders bevorzugt für einfach substituiertes Phenyl, wobei die Substituenten aus derR is preferably phenyl which may be monosubstituted to trisubstituted by identical or different substituents, the substituents being selected from the list W 1 . R is particularly preferably monosubstituted phenyl, wherein the substituents from the
Liste W1 ausgewählt sind. R steht auch besonders bevorzugt für zweifach, gleich oder verschieden substituiertes Phenyl, wobei die Substituenten aus der Liste W1 ausgewählt sind. R steht auch besonders bevorzugt für dreifach, gleich oder verschieden substituiertes Phenyl, wobei die Substituenten aus der Liste W1 ausgewählt sind. R steht ganz besonders bevorzugt für einfach in 4-Position substituiertes Phenyl, wobei dieList W 1 are selected. R is also particularly preferably phenyl which is monosubstituted, identically or differently substituted, the substituents being selected from the list W 1 . R is also particularly preferably triply, identically or differently substituted phenyl, where the substituents are selected from list W 1 . R is very particularly preferably phenyl which is monosubstituted in the 4-position, where the
Substituenten aus der Liste W1 ausgewählt sind. R steht ganz besonders bevorzugt für zweifach, gleich oder verschieden in 3,4-Position substituiertes Phenyl, wobei die Substituenten aus der Liste W1 ausgewählt sind. R steht ganz besonders bevorzugt für zweifach, gleich oder verschieden in 2,4-Position substituiertes Phenyl, wobei die Substituenten aus der Liste W1 ausgewählt sind. R steht ganz besonders bevorzugt für zweifach, gleich oder verschieden in 3,5-Position substituiertes Phenyl, wobei die Substituenten aus der Liste W1 ausgewählt sind.Substituents are selected from the list W 1 . R very particularly preferably represents phenyl which is monosubstituted, identically or differently substituted in the 3,4-position, the substituents being selected from the list W 1 . R very particularly preferably represents phenyl which is monosubstituted, identically or differently substituted in the 2,4-position, the substituents being selected from the list W 1 . R very particularly preferably represents phenyl monosubstituted, identically or differently substituted in the 3,5-position, the substituents being selected from the list W 1 .
R steht ganz besonders bevorzugt für dreifach, gleich oder verschieden in 2,4,6-Position substituiertes Phenyl, wobei die Substituenten aus der Liste W1 ausgewählt sind.R is very particularly preferably phenyl which is triply, identically or differently substituted in the 2,4,6-position, the substituents being selected from the list W 1 .
W1 steht für Halogen, Cyano, Nitro, Amino, Hydroxy, Formyl, Carboxyl, Carbamoyl, Thiocarb- amoyl; jeweils geradkettiges oder verzweigtes Alkyl, Hydroxyalkyl, Oxoalkyl, Alkoxy, Alkoxyalkyl,W 1 is halogen, cyano, nitro, amino, hydroxy, formyl, carboxyl, carbamoyl, thiocarbamoyl; in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl,
Alkylthioalkyl, Dialkoxyalkyl, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 8Alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8
Kohlenstoffatomen; jeweils geradkettiges oder verzweigtes Alkenyl oder Alkenyloxy mit jeweils 2 bis 6 Kohlen- Stoffatomen; jeweils geradkettiges oder verzweigtes Halogenalkyl, Halogenalkoxy, Halogenalkylthio, Halogenalkylsulfinyl oder Halogenalkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiedenen Halogenatomen; jeweils geradkettiges oder verzweigtes Halogenalkenyl oder Halogenalkenyloxy mit jeweils 2 bis 6 Kohlenstoffatomen und 1 bis 11 gleichen oder verschiedenen Halogenatomen; jeweils geradkettiges oder verzweigtes Alkylamino, Dialkylamino, Alkylcarbonyl, Alkyl- carbonyloxy, Alkoxycarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Arylalkylamino- carbonyl, Dialkylaminocarbonyloxy mit 1 bis 6 Kohlenstoffatomen in den jeweiligen Kohlenwasserstoffketten, Alkenylcarbonyl oder Alkinylcarbonyl, mit 2 bis 6 Kohlenstoff- atomen in den jeweiligen Kohlenwasserstoffketten;Carbon atoms; in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms; in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; in each case straight-chain or branched haloalkenyl or haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkylaminocarbonyloxy having 1 to 6 carbon atoms in the respective hydrocarbon chains, alkenylcarbonyl or alkynylcarbonyl having 2 to 6 carbon atoms in the respective hydrocarbon chains ;
Cycloalkyl oder Cycloalkyloxy mit jeweils 3 bis 6 Kohlenstoffatomen; jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Oxo, Methyl, Trifluormethyl oder Ethyl substituiertes, jeweils zweifach verknüpftes Alkylen mit 3 oder 4 Kohlenstoffatomen, Oxyalkylen mit 2 oder 3 Kohlenstoffatomen oder Dioxyalkylen mit 1 oder 2 Kohlenstoffatomen; oder eine Gruppierung -C(Q')=N-Q2, worin Q1 für Wasserstoff, Hydroxy, Alkyl mit 1 bis 4 Kohlenstoffatomen, Halogenalkyl mit 1 bis 4 Kohlenstoffatomen und 1 bis 9 gleichen oder verschiedenen Halogenatomen oder Cycloalkyl mit 1 bis 6 Kohlenstoffatomen steht undCycloalkyl or cycloalkyloxy each having 3 to 6 carbon atoms; in each case optionally monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, oxo, methyl, trifluoromethyl or ethyl, in each case doubly linked alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms; or a grouping -C (Q ') = NQ 2 , wherein Q 1 is hydrogen, hydroxy, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms or cycloalkyl of 1 to 6 carbon atoms and
Q2 für Hydroxy, Amino, Methylamino, Phenyl, Benzyl oder für jeweils gegebenenfalls durch Halogen, Cyano, Hydroxy, Alkoxy, Alkylthio, Alkylamino, Dialkylamino oderQ 2 is hydroxy, amino, methylamino, phenyl, benzyl or each optionally substituted by halogen, cyano, hydroxy, alkoxy, alkylthio, alkylamino, dialkylamino or
Phenyl substituiertes Alkyl oder Alkoxy mit 1 bis 4 Kohlenstoffatomen, oder für Alkenyloxy oder Alkinyloxy mit jeweils 2 bis 4 Kohlenstoffatomen steht, sowie jeweils gegebenenfalls im Ringteil einfach bis dreifach durch Halogen, und/oder geradkettiges oder verzweigtes Alkyl oder Alkoxy mit 1 bis 4 Kohlenstoffatomen substituier- tes Phenyl, Phenoxy, Phenylthio, Benzoyl, Benzoylethenyl, Cinnamoyl, Heterocyclyl oderPhenyl-substituted alkyl or alkoxy having 1 to 4 carbon atoms, or alkenyloxy or alkynyloxy having in each case 2 to 4 carbon atoms, and in each case optionally in the ring part monosubstituted to trisubstituted by halogen, and / or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms - phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl or
Phenylalkyl, Phenylalkyloxy, Phenylalkylthio, oder Heterocyclylalkyl, mit jeweils 1 bis 3 Kohlenstoffatomen in den jeweiligen Alkylteilen.Phenylalkyl, phenylalkyloxy, phenylalkylthio, or heterocyclylalkyl, each having 1 to 3 carbon atoms in the respective alkyl moieties.
W1 steht bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Methoxy, Ethoxy, n- oder iso-Propoxy, Trifluormethyl, Trifluorethyl, Difluor- methoxy, Trifluormethoxy, Difluorchlormethoxy, Trifluorethoxy, jeweils zweifach verknüpftes Difluormethylendioxy oder Tetrafluorethylendioxy, oder eine Gruppierung -C(Q')=N-Q2, worinW 1 is preferably fluorine, chlorine, bromine, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxy, ethoxy, n- or iso-propoxy, trifluoromethyl, trifluoroethyl, Difluor- methoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, in each case doubly linked difluoromethylenedioxy or tetrafluoroethylenedioxy, or a grouping -C (Q ') = NQ 2 , in which
Q1 für Wasserstoff, Methyl, Ethyl, Trifluormethyl oder Cyclopropyl steht und Q2 für Hydroxy, Methoxy, Ethoxy, Propoxy oder Isopropoxy steht.Q 1 is hydrogen, methyl, ethyl, trifluoromethyl or cyclopropyl and Q 2 is hydroxy, methoxy, ethoxy, propoxy or isopropoxy.
R steht außerdem bevorzugt für gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Ci-C4-Alkyl substituiertes Cycloalkyl oder Bicycloalkyl mit jeweils 3 bis 10 Kohlenstoffatomen.R furthermore preferably represents cycloalkyl or bicycloalkyl which is optionally monosubstituted to monosubstituted, identically or differently by C 1 -C 4 -alkyl and in each case has 3 to 10 carbon atoms.
R steht außerdem besonders bevorzugt für Cyclopentyl, Cyclohexyl, Cycloheptyl, Cyclooctyl, Cyclononyl, Bicyclo[2.2.1]heptyl oder Bicyclo[2.2.2]octyl.R is moreover particularly preferably cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, bicyclo [2.2.1] heptyl or bicyclo [2.2.2] octyl.
R steht außerdem bevorzugt für unsubstituiertes C2-C2o-Alkyl oder für einfach oder mehrfach, gleich oder verschieden durch Fluor, Chlor, Brom, Iod und/oder C3-C6-Cycloalkyl substituiertes Ci-C2o-Alkyl steht, wobei der Cycloalkylteil seinerseits gegebenenfalls einfach bis vier- fach, gleich oder verschieden durch Fluor, Chlor, Brom, Iod, CrC4-Alkyl und/oder Ci-C4-R is also preferably unsubstituted C 2 -C 2 o-alkyl or mono- or polysubstituted by identical or different fluorine, chlorine, bromine, iodine and / or C 3 -C 6 -cycloalkyl-substituted Ci-C 2 o-alkyl in which the cycloalkyl moiety in turn may optionally be monosubstituted, identical or different by fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl and / or C 1 -C 4 -
Halogenalkyl substituiert sein kann.Haloalkyl may be substituted.
R steht außerdem besonders bevorzugt für unsubstituiertes C2-C2o-Alkyl.R is also particularly preferably unsubstituted C 2 -C 2 o-alkyl.
R steht außerdem besonders bevorzugt für durch Chlor, Cyclopropyl, Dichlorcyclopropyl,R is furthermore particularly preferably chlorine, cyclopropyl, dichlorocyclopropyl,
Cyclobutyl, Cyclopentyl oder Cyclohexyl substituiertes Ci-C2o-Alkyl. R12 steht bevorzugt für Wasserstoff, Cyano, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, iso-Propyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Cyclopropyl, CrC2-Halogenalkyl, Ci-C2-HaIo- genalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen, Trifluormethylthio, Di- fluormethylthio, Aminocarbonyl, Aminocarbonylmethyl oder Aminocarbonylethyl. R12 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, iso- Propyl, Monofluormethyl, Monofluorethyl, Difluormethyl, Trifluormethyl, Difluorchlor- methyl, Trichlormethyl, Dichlormethyl, Cyclopropyl, Methoxy, Ethoxy, Trifluormethoxy, Trichlormethoxy, Methylthio, Ethylthio, Trifluormethylthio oder Difluormethylthio.Cyclobutyl, cyclopentyl or cyclohexyl substituted Ci-C 2 o-alkyl. R 12 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, C r C 2 -haloalkyl, C 1 -C 2 -haloalkoxy with in each case 1 to 5 fluorine, chlorine and / or bromine atoms, trifluoromethylthio, di-fluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl. R 12 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, dichloromethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, Methylthio, ethylthio, trifluoromethylthio or difluoromethylthio.
R12 steht ganz besonders bevorzugt Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, iso-Propyl, Monofluormethyl, Monofluorethyl, Difluormethyl, Trifluormethyl, Difluorchlormethyl oderR 12 is very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, isopropyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or
Trichlormethyl.Trichloromethyl.
R12 steht insbesondere bevorzugt für Methyl, Difluormethyl, Trifluormethyl oder 1 -Fluorethyl.R 12 is particularly preferably methyl, difluoromethyl, trifluoromethyl or 1-fluoroethyl.
R13 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, Methoxy, Ethoxy, Methylthio oder Ethylthio.R 13 is preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio.
R13 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod oder Methyl.R 13 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine or methyl.
R13 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor oder Methyl.R 13 very particularly preferably represents hydrogen, fluorine, chlorine or methyl.
R14 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, C]-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen, Hydroxymethyl, Hydroxyethyl, Cyclopropyl,R 14 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl,
Cyclopentyl, Cyclohexyl oder Phenyl.Cyclopentyl, cyclohexyl or phenyl.
R14 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, iso-Propyl, Trifluormethyl, Difluormethyl, Hydroxymethyl, Hydroxyethyl oder Phenyl.R 14 particularly preferably represents hydrogen, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl.
R14 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Trifluormethyl oder Phenyl. R14 steht insbesondere bevorzugt für Methyl.R 14 very particularly preferably represents hydrogen, methyl, trifluoromethyl or phenyl. R 14 is particularly preferably methyl.
R15 und R16 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl,R 15 and R 16 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, methyl,
Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R15 und R16 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Difluorchlormethyl oder Trichlormethyl. R15 und R16 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor,Ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 15 and R 16 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl. R 15 and R 16 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine,
Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl oder Trichlormethyl. R15 und R16 stehen insbesondere bevorzugt jeweils für Wasserstoff.Bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl. R 15 and R 16 are particularly preferably each hydrogen.
R > 17 steht bevorzugt für Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, CrC2-Halogenalkyl oder Cr C2-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen. R17 steht besonders bevorzugt für Fluor, Chlor, Brom, Cyano, Methyl, Trifluormethyl,R> 17 is preferably fluorine, chlorine, bromine, cyano, methyl, ethyl, C r C 2 -haloalkyl or C r C 2 haloalkoxy having in each case 1 to 5 fluorine, chlorine and / or bromine atoms. R 17 particularly preferably represents fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl,
Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy oder Trichlormethoxy. R17 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Iod, Methyl, Trifluormethyl oder Trifluormethoxy.Trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy. R 17 is very particularly preferably fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or trifluoromethoxy.
R17 steht insbesondere bevorzugt für Methyl.R 17 is particularly preferably methyl.
R17 steht insbesondere bevorzugt für Trifluormethyl.R 17 is particularly preferably trifluoromethyl.
R18 und R19 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 18 and R 19 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R18 und R19 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Difluorchlormethyl oder Trichlor- methyl.R 18 and R 19 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl.
R18 und R19 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl oder Trichlormethyl.R 18 and R 19 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl.
R18 und R19 stehen insbesondere bevorzugt jeweils für Wasserstoff.R 18 and R 19 are particularly preferably each hydrogen.
R20 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R20 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl oderR 20 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 20 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or
Trifluormethyl.Trifluoromethyl.
R20 steht ganz besonders bevorzugt für Methyl. R20 steht insbesondere bevorzugt für Trifluormethyl.R 20 is very particularly preferably methyl. R 20 particularly preferably represents trifluoromethyl.
R21 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Hydroxy, Cyano, C1-C4-AIkVl, Q- C2-Halogenalkyl, Ci-C2-Halogenalkoxy oder Ci-C2-Halogenalkylthio mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 21 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, C 1 -C 4 -alkyl, Q-C 2 -haloalkyl, C 2 -haloalkoxy or C 2 -haloalkylthio having in each case 1 to 5 fluorine, chlorine and / or bromine atoms.
R21 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Hydroxy, Cyano, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Buryl, iso-Butyl, sec-Butyl, tert-Butyl, Difluormethyl, Trifluor- methyl, Difluorchlormethyl, Trichlormethyl, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy, Trichlormethoxy, Trifluormethylthio, Difluormethylthio, Difiuorchlormethylthio oder Trichlormethylthio.R 21 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, n-buryl, isobutyl, sec-butyl, tert-butyl, difluoromethyl, Trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio or trichloromethylthio.
R21 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Difluormethyl, Trifluormethyl oder Trichlormethyl. R21 steht insbesondere bevorzugt für Iod. Methyl. Difluormethyl oder Trifluormethyl . R22 steht bevorzugt für Fluor, Chlor, Brom, Iod, Hydroxy, Cyano, Ci-C4-Alkyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Difluormethylthio, Trifluormethylthio, Ci-C2-Halogenalkyl oder Cr C2-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 21 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl. R 21 is particularly preferably iodine. Methyl. Difluoromethyl or trifluoromethyl. R 22 is preferably fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C 1 -C 4 -alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy, in each case with 1 to 5 fluorine, chlorine and / or bromine atoms.
R22 steht besonders bevorzugt für Fluor, Chlor, Brom, Iod, Hydroxy, Cyano, Methyl, Ethyl, n- Propyl, iso-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Trifluormethyl, Difluormethyl,R 22 particularly preferably represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl,
Difluorchlormethyl, Trichlormethyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Difluormethylthio, Trifluormethylthio, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy oder Tri- chlormethoxy.Difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy.
R22 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Iod, Methyl, Trifluormethyl, Di- fluormethyl oder Trichlormethyl.R 22 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, di-fluoromethyl or trichloromethyl.
R23 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, CrC4-Alkyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Ci-C2-Halogenalkyl oder Ci-C2-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen, Ci-C2-Alkylsulphinyl oder Ci-C2-Alkylsulphonyl. R23 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, n-Propyl, iso- Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl, Trichlormethyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy, Trichlormethoxy, Methylsulphinyl oder Methylsulphonyl.R 23 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, C r C 4 alkyl, methoxy, ethoxy, methylthio, ethylthio, Ci-C 2 haloalkyl or Ci-C2 haloalkoxy, each with 1 to 5 Fluorine, chlorine and / or bromine atoms, C 1 -C 2 -alkylsulphinyl or C 1 -C 2 -alkylsulphonyl. R 23 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, Methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulphinyl or methylsulphonyl.
R23 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, n-Propyl, iso- Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Trifluormethyl, Difluormethyl, Trichlormethyl, Methylsulphinyl oder Methylsulphonyl.R 23 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, methylsulphinyl or methylsulphonyl ,
R23 steht insbesondere bevorzugt für Wasserstoff.R 23 is particularly preferably hydrogen.
R24 steht bevorzugt für Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 24 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R24 steht besonders bevorzugt für Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 24 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R25 steht bevorzugt für Methyl oder Ethyl. R25 steht besonders bevorzugt für Methyl.R 25 is preferably methyl or ethyl. R 25 particularly preferably represents methyl.
Q1 steht bevorzugt für S (Schwefel), SO2 oder CH2.Q 1 is preferably S (sulfur), SO 2 or CH 2 .
Q1 steht besonders bevorzugt für S (Schwefel) oder CH2.Q 1 particularly preferably represents S (sulfur) or CH 2 .
Q1 steht ganz besonders bevorzugt für S (Schwefel).Q 1 very particularly preferably represents S (sulfur).
p steht bevorzugt für 0 oder 1. p steht besonders bevorzugt für 0.p is preferably 0 or 1. p is particularly preferably 0.
R26 steht bevorzugt für Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oderR 26 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or
Bromatomen. R26 steht besonders bevorzugt für Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlor- methyl oder Trichlormethyl.Bromine atoms. R 26 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R26 steht ganz besonders bevorzugt für Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 26 is very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R27 steht bevorzugt für Methyl, Ethyl oder C]-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oderR 27 is preferably methyl, ethyl or C] -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or
Bromatomen. R27 steht besonders bevorzugt für Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlor- methyl oder Trichlormethyl.Bromine atoms. R 27 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R27 steht ganz besonders bevorzugt für Methyl, Trifluormethyl, Difluormethyl oder Trichlor- methyl.R 27 is very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R28 und R29 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 28 and R 29 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R28 und R29 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 28 and R 29 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R28 und R29 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 28 and R 29 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R28 und R29 stehen insbesondere bevorzugt jeweils für Wasserstoff.R 28 and R 29 are particularly preferably each hydrogen.
R30 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl oder C1-C2- Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 30 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R30 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R30 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 30 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 30 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R30 steht insbesondere bevorzugt für Methyl.R 30 is particularly preferably methyl.
R31 und R32 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Nitro, Methyl, Ethyl oder Ci-C∑-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 31 and R 32 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or C Σ -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R31 und R32 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Nitro, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Tri- chlormethyl. R31 und R32 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor,R 31 and R 32 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, Bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 31 and R 32 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine,
Brom, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R31 und R32 stehen insbesondere bevorzugt jeweils für Wasserstoff.Bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 31 and R 32 are particularly preferably each hydrogen.
R33 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 33 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R33 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluorme- thyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 33 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R33 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Trifluormethyl,R 33 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl,
Difluormethyl oder Trichlormethyl. R33 steht insbesondere bevorzugt für Methyl.Difluoromethyl or trichloromethyl. R 33 is particularly preferably methyl.
R34 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Ci-C4-Alkylamino, Di(C1-C4- alkyl)amino, Cyano, Methyl, Ethyl oder d-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 34 is preferably hydrogen, fluorine, chlorine, bromine, amino, C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, cyano, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, Chlorine and / or bromine atoms.
R34 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino, Dimethylamino, Cyano, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 34 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R34 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino,R 34 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
Dimethylamino, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R34 steht insbesondere bevorzugt für Amino, Methylamino, Dimethylamino, Methyl oderDimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 34 particularly preferably represents amino, methylamino, dimethylamino, methyl or
Trifluormethyl.Trifluoromethyl.
R35 steht bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5R 35 is preferably fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl having 1 to 5
Fluor, Chlor und/oder Bromatomen. R35 steht besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl,Fluorine, chlorine and / or bromine atoms. R 35 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,
Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R35 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R35 steht insbesondere bevorzugt für Methyl, Trifluormethyl oder Difluormethyl.Difluoromethyl, difluorochloromethyl or trichloromethyl. R 35 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 35 particularly preferably represents methyl, trifluoromethyl or difluoromethyl.
R36 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, CrC4-Alkylamino, Di(C1-C4- alkyl)amino, Cyano, Methyl, Ethyl oder d-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. - -R 36 preferably represents hydrogen, fluorine, chlorine, bromine, amino, C r C 4 alkylamino, di (C 1 -C 4 - alkyl) amino, cyano, methyl, ethyl or C 2 haloalkyl having 1 to 5 fluorine, Chlorine and / or bromine atoms. - -
R36 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino, Dimethylamino, Cyano, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 36 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R36 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino, Dimethylamino, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 36 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R36 steht insbesondere bevorzugt für Amino, Methylamino, Dimethylamino, Methyl oder Trifluormethyl.R 36 particularly preferably represents amino, methylamino, dimethylamino, methyl or trifluoromethyl.
R37 steht bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 37 is preferably fluorine, chlorine, bromine, methyl, ethyl or C r C 2 haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R37 steht besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl,R 37 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,
Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R37 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Trifluormethyl,Difluoromethyl, difluorochloromethyl or trichloromethyl. R 37 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl,
Difluormethyl oder Trichlormethyl. R37 steht insbesondere bevorzugt für Methyl. Trifluormethyl oder Difluormethyl.Difluoromethyl or trichloromethyl. R 37 is particularly preferably methyl. Trifluoromethyl or difluoromethyl.
R38 steht bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5R 38 is preferably fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl having 1 to 5
Fluor, Chlor und/oder Bromatomen.Fluorine, chlorine and / or bromine atoms.
R38 steht besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 38 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R38 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Trifluormethyl,R 38 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl,
Difluormethyl oder Trichlormethyl.Difluoromethyl or trichloromethyl.
R39 steht bevorzugt für Wasserstoff, Methyl oder Ethyl. R39 steht besonders bevorzugt für Methyl.R 39 is preferably hydrogen, methyl or ethyl. R 39 particularly preferably represents methyl.
R40 steht bevorzugt für Fluor, Chlor, Brom, Methyl oder Ethyl. R40 steht besonders bevorzugt für Fluor, Chlor oder Methyl.R 40 is preferably fluorine, chlorine, bromine, methyl or ethyl. R 40 particularly preferably represents fluorine, chlorine or methyl.
R41 steht bevorzugt für Methyl, Ethyl oder C,-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oderR 41 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or
Bromatomen.Bromine atoms.
R41 steht besonders bevorzugt für Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 41 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R41 steht ganz besonders bevorzugt für Methyl, Trifluormethyl, Difluormethyl oder Trichlor- methyl.R 41 very particularly preferably represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R41 steht insbesondere bevorzugt für Methyl oder Trifluormethyl. R42 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder C,-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 41 is particularly preferably methyl or trifluoromethyl. R 42 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R42 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl oder Trifluormethyl.R 42 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.
R43 steht bevorzugt für Fluor, Chlor, Brom, Iod, Hydroxy, Ci-C4-Alkyl, Methoxy, Ethoxy,R 43 is preferably fluorine, chlorine, bromine, iodine, hydroxyl, C 1 -C 4 -alkyl, methoxy, ethoxy,
Methylthio, Ethylthio, Difϊuormethylthio, Trifluormethylthio, CrC2-Halogenalkyl oder Cr Methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, C r C 2 -haloalkyl or C r
C2-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen.C 2 haloalkoxy having in each case 1 to 5 fluorine, chlorine and / or bromine atoms.
R43 steht besonders bevorzugt für Fluor, Chlor, Brom, Iod, Methyl, Ethyl, n-Propyl, iso-Propyl, n- Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R43 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Iod, Methyl, Trifluormethyl,R 43 particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 43 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl,
Difluormethyl oder Trichlormethyl.Difluoromethyl or trichloromethyl.
R44 steht bevorzugt für Wasserstoff, Methyl, Ethyl, Ci-C2-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen, Ci-C2-Alkoxy-CrC2-alkyl, Hydroxymethyl, Hydroxyethyl, Methylsulfonyl oder Dimethylaminosulfonyl.R 44 preferably represents hydrogen, methyl, ethyl, Ci-C 2 haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, Ci-C 2 alkoxy-C r C 2 alkyl, hydroxymethyl, hydroxyethyl, methylsulfonyl or dimethylaminosulfonyl.
R44 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, Trifluormethyl, Methoxymethyl, Ethoxymethyl, Hydroxymethyl oder Hydroxyethyl. R44 steht ganz besonders bevorzugt für Methyl oder Methoxymethyl.R 44 particularly preferably represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or hydroxyethyl. R 44 is very particularly preferably methyl or methoxymethyl.
R45 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen.R 45 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R45 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 45 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R45 steht ganz besonders bevorzugt für Wasserstoff oder Methyl.R 45 is very particularly preferably hydrogen or methyl.
R46 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Methyl, Ethyl, iso-Propyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen. R46 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, iso- Propyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 46 is preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, iso-propyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 46 is particularly preferably hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R46 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Difluormethyl oder Trifluormethyl.R 46 very particularly preferably represents hydrogen, methyl, difluoromethyl or trifluoromethyl.
R47 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R47 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl oderR 47 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 47 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or
Trifluormethyl. R47 steht ganz besonders bevorzugt für Wasserstoff.Trifluoromethyl. R 47 is very particularly preferably hydrogen.
R48 steht bevorzugt für Methyl, Ethyl, n-Propyl oder iso-Propyl. R48 steht besonders bevorzugt Methyl oder Ethyl.R 48 is preferably methyl, ethyl, n-propyl or iso-propyl. R 48 is particularly preferably methyl or ethyl.
Bevorzugt sind solche Verbindungen der Formel (I), in welcher alle Reste jeweils die oben genannten bevorzugten Bedeutungen haben. Besonders bevorzugt sind solche Verbindungen der Formel (I), in welcher alle Reste jeweils die oben genannten besonders bevorzugten Bedeutungen haben.Preference is given to those compounds of the formula (I) in which all radicals each have the abovementioned preferred meanings. Particular preference is given to those compounds of the formula (I) in which all radicals each have the abovementioned particularly preferred meanings.
Hervorgehobene Verbindungen der Formel (I) sind im Folgenden genannt:Highlighted compounds of the formula (I) are mentioned below:
(1) N-[2-(l,3-Dimethylbutyl)phenyl]-l,3-dimethyl-lH-pyrazol-4-carboxamid (bekannt aus JP-A 10-251240) der Formel(1) N- [2- (1,3-dimethylbutyl) phenyl] -1,3-dimethyl-1H-pyrazole-4-carboxamide (known from JP-A 10-251240) of the formula
(2) N-[2-( 1 ,3-Dimethylbutyl)phenyl]-5-fluor- 1 ,3-dimethyl- lH-pyrazol-4-carboxamid (bekannt aus WO 03/010149) der Formel(2) N- [2- (1, 3-Dimethylbutyl) phenyl] -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (known from WO 03/010149) of the formula
(3) N-P^l^-DimethylburyOpheny^-S-chlor-l^-dimethyl-lH-pyrazoM-carboxamid (bekannt aus JP-A 10-251240) der Formel (3) NP 1-10 dimethylburyophenyl-S-chloro-1-dimethyl-1H-pyrazole-M-carboxamide (known from JP-A 10-251240) of the formula
(4) 3-(Difluormethyl)-N-[2-( 1 ,3-dimethylbutyl)phenyI]- 1 -methyl- 1 H-pyrazol-4-carboxamid der Formel (4) 3- (Difluoromethyl) -N- [2- (1, 3-dimethylbutyl) phenyl] -1-methyl-1H-pyrazole-4-carboxamide of the formula
(5) 3-(Trifluormethyl)-N-[2-(l ,3-dimethylbutyl)phenyl]-5-fluor- 1 -methyl- lH-pyrazol-4-carbox- amid (bekannt aus WO 2004/067515) der Formel(5) 3- (Trifluoromethyl) -N- [2- (1,3-dimethylbutyl) phenyl] -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (known from WO 2004/067515) of formula
(6) 3-(Trifluormethyl)-N-[2-(l,3-dimethylbutyl)phenyl]-5-chlor-l-methyl-lH-pyrazol-4-carbox- amid (bekannt aus JP-A 10-251240) der Formel (6) 3- (Trifluoromethyl) -N- [2- (1,3-dimethylbutyl) phenyl] -5-chloro-1-methyl-1H-pyrazole-4-carboxamide (known from JP-A 10-251240 ) of the formula
(7) l,3-Dimethyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazol-4-carboxamid der Formel(7) 1,3-Dimethyl-N- [2- (1,3,3-trimethylbutyl) phenyl] -1H-pyrazole-4-carboxamide of the formula
(8) 5-Fluor-l,3-dimethyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazol-4-carboxamid (bekannt aus WO 03/010149) der Formel (8) 5-Fluoro-1,3-dimethyl-N- [2- (1,3,3-trimethylbutyl) phenyl] -1H-pyrazole-4-carboxamide (known from WO 03/010149) of the formula
(9) 3-(Difluormethyl)-l-methyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazol-4-carboxamid der Formel(9) 3- (Difluoromethyl) -1-methyl-N- [2- (1,3,3-trimethylbutyl) phenyl] -1H-pyrazole-4-carboxamide of the formula
( 10) 3-(Trifluormethyl)- 1 -methyl-N-[2-( 1 ,3,3-trimethylbutyl)phenyl]- 1 H-pyrazol-4-carboxamid der Formel . - -(10) 3- (Trifluoromethyl) -1-methyl-N- [2- (1,3,3-trimethylbutyl) phenyl] -1 H -pyrazole-4-carboxamide of the formula , - -
(1 1) 3-(Trifluormethyl>5-fluor- 1 -methyl-N-[2-( 1 ,3 ,3-trimethylbutyl)phenyl]- 1 H-pyrazol-4- carboxamid (bekannt aus WO 2004/067515) der Formel(1 1) 3- (trifluoromethyl) -5-fluoro-1-methyl-N- [2- (1,3,3-trimethyl-butyl) -phenyl] -1-H-pyrazole-4-carboxamide (known from WO 2004/067515) the formula
( 12) 3-(Trifluormethy l>5-chlor- 1 -methyl-N-[2-( 1 ,3 ,3-trimethylbutyl)phenyl]- 1 H-pyrazol-4- carboxamid der Formel(12) 3- (trifluoromethyl) 5-chloro-1-methyl-N- [2- (1,3,3-trimethylbutyl) phenyl] -1 H -pyrazole-4-carboxamide of the formula
(13) N-[2-(l,3-Dimethylbutyl)phenyl]-2-iodbenzamid (bekannt aus WO 2004/005242) der Formel(13) N- [2- (1,3-dimethylbutyl) phenyl] -2-iodobenzamide (known from WO 2004/005242) of the formula
(14) 2-Iod-N-[2-(l,3,3-trimethylbutyl)phenyl]benzamid (bekannt aus WO 2004/005242) der Formel (14) 2-iodo-N- [2- (1,3,3-trimethylbutyl) phenyl] benzamide (known from WO 2004/005242) of the formula
(15) N-[2-(l,3-Dimethylbutyl)phenyl]-2-(trifluormethyl)benzamid (bekannt aus WO 2004/005242) der Formel(15) N- [2- (1,3-dimethylbutyl) phenyl] -2- (trifluoromethyl) benzamide (known from WO 2004/005242) of the formula
(16) 2-(Trifluormethyl)-N-[2-(l,3,3-trimethylbutyl)phenyl]benzamid (bekannt aus WO 2004/005242) der Formel (16) 2- (trifluoromethyl) -N- [2- (1,3,3-trimethylbutyl) phenyl] benzamide (known from WO 2004/005242) of the formula
( 17) Boscalid (bekannt aus DE-A 195 31 813 ) der Formel(17) Boscalid (known from DE-A 195 31 813) of the formula
(18) l-Methyl-3-trifluormethyl-lH-pyrazol-4-carbonsäure-(3-p-tolyl-thiophen-2-yl)-amid (bekannt aus EP-A 0 737 682) der Formel(18) 1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (3-p-tolyl-thiophen-2-yl) -amide (known from EP-A 0 737 682) of the formula
( 19) Penthiopyrad (bekannt aus EP-A 0 737 682) der Formel(19) Penthiopyrad (known from EP-A 0 737 682) of the formula
(20) N-[2-( 1 ,3-Dimethylbutyl)phenyl]- 1 -methyl-4-(trifluormethyl)- 1 H-pyrrol-3-carboxamid (bekannt aus WO 02/38542) der Formel(20) N- [2- (1, 3-Dimethylbutyl) phenyl] -1-methyl-4- (trifluoromethyl) -1 H -pyrrole-3-carboxamide (known from WO 02/38542) of the formula
(21 ) N-(3',4'-Dichlor-5-fluor-l , 1 '-biphenyl-2-yl)-3-(difluormethyl> 1 -methyl-lH-pyrazol-4- carboxamid (bekannt aus WO 03/070705) der Formel(21) N- (3 ', 4'-dichloro-5-fluoro-1,1'-biphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide (known from WO 03/070705) of the formula
(22) 3-(Difluorme%l>N- {3'-fluor-44(£Hmethoxyimino)methyl]- 1 , 1 '-biphenyl-2-yl } - 1 -methyl- lH-pyrazol-4-carboxamid (bekannt aus WO 02/08197) der Formel (22) 3- (Difluoromethyl) -1- (3'-fluoro-44 (1H-methoxyimino) methyl] -1,1'-biphenyl-2-yl} -1-methyl-1H-pyrazole-4-carboxamide ( known from WO 02/08197) of the formula
(23) 3-(Trifluormethyl)-N- {3'-fluor-4'-[(E)-(methoxyimino)methyl]- 1 , 1 '-biphenyl-2-yl } - 1 -methy 1- lH-pyrazol-4-carboxamid (bekannt aus WO 02/08197) der Formel(23) 3- (trifluoromethyl) -N- {3'-fluoro-4 '- [(E) - (methoxyimino) methyl] -1,1'-biphenyl-2-yl} -1-methy1-lH- pyrazole-4-carboxamide (known from WO 02/08197) of the formula
(24) N-(3',4'-Dichlor- 1 , 1 '-biphenyl-2-yl)-5-fluor- 1 ,3-dimethyl- 1 H-pyrazol-4-carboxamid (bekannt aus WO 00/14701) der Formel(24) N- (3 ', 4'-dichloro-1,1'-biphenyl-2-yl) -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (known from WO 00 / 14701) of the formula
(25) N-(4'-Chlor-3'-fluor- 1 , 11-biphenyl-2-yl>2-methyl-4-(trifluormethyl> 1 ,3-thiazol-5-carboxamid (bekannt aus WO 03/066609) der Formel (25) N- (4'-chloro-3'-fluoro-1, 1 1-biphenyl-2-yl> 2-methyl-4- (trifluoromethyl> 1, 3-thiazol-5-carboxamide (known from WO 03 / 066609) of the formula
(26) N-(4'-Chlor- 1 , 1 '-biphenyl-2-yl)-4-(difluormethyl)-2-methyl- 1 ,3-thiazol-5-carboxamid (bekannt aus WO 03/066610) der Formel - -(26) N- (4'-chloro-1,1'-biphenyl-2-yl) -4- (difluoromethyl) -2-methyl-1,3-thiazole-5-carboxamide (known from WO 03/066610) the formula - -
(27) N-(4'-Brom- 1 , 1 '-biphenyl-2-yl)-4-(difluormethyl)-2-methyl- 1 ,3-thiazol-5-carboxamid (bekannt aus WO 03/066610) der Formel(27) N- (4'-Bromo-1,1'-biphenyl-2-yl) -4- (difluoromethyl) -2-methyl-1,3-thiazole-5-carboxamide (known from WO 03/066610) the formula
(28) 4-(Difluormethyl>2-methyl-N-[4'-(trifluormethyl> 1 , 1 -biphenyl-2-yl]- 1 ,3-thiazol-5- carboxamid (bekannt aus WO 03/066610) der Formel(28) 4- (Difluoromethyl) -2-methyl-N- [4 '- (trifluoromethyl) -1,3-biphenyl-2-yl] -1,3-thiazole-5-carboxamide (known from WO 03/066610) formula
(29) N-(4'-Iod- 1 , 1 '-biphenyl-2-yl>4-(difluormethyl)-2-methyl- 1 ,3-thiazol-5-carboxamid (bekannt aus WO 03/066610) der Formel(29) N- (4'-iodo-1,1'-biphenyl-2-yl) -4- (difluoromethyl) -2-methyl-1,3-thiazole-5-carboxamide (known from WO 03/066610) of formula
(30) N-(4'-Chlor-3'-fluor- 1 , 1 '-biphenyl-2-yl>2-methyi-4-(difluormethy I)-1 ,3-thiazol-5-carboxamid (bekannt aus WO 03/066610) der Formel(30) N- (4'-Chloro-3'-fluoro-1, 1'-biphenyl-2-yl> 2-methyl-4- (difluoromethyl) -1,3-thiazole-5-carboxamide (known from WO 03/066610) of the formula
- - - -
(31 ) Tiadinil (bekannt aus US 6,616,054) der Formel(31) Tiadinil (known from US 6,616,054) of the formula
(32) N-[2-(l,3-Dimethylbutyl)phenyl]-l-methyl-4-(trifluormethyl)-lH-pyrrol-3-carboxamid (bekannt aus WO 02/38542) der Formel(32) N- [2- (1,3-dimethylbutyl) phenyl] -1-methyl-4- (trifluoromethyl) -1H-pyrrole-3-carboxamide (known from WO 02/38542) of the formula
(33) N-(4'-Chlorbiphenyl-2-yl)-3-iod-l-methyl-lH-pyrazol-4-carboxamid (bekannt aus WO 2004/103975) der Formel(33) N- (4'-Chlorobiphenyl-2-yl) -3-iodo-1-methyl-1H-pyrazole-4-carboxamide (known from WO 2004/103975) of the formula
(34) 4-(Difluormethyl)-N-[3'-fluor-4l-(trifluormethyl)biphenyl-2-yl]-2-methyl-l,3-thiazol-5- carboxamid (bekannt aus WO 03/066610) der Formel(34) 4- (Difluoromethyl) -N- [3'-fluoro-4 l - (trifluoromethyl) biphenyl-2-yl] -2-methyl-1,3-thiazole-5-carboxamide (known from WO 03/066610 ) of the formula
(35) 3-(Difluormethyl)-N-[2-(3,3-dimethylbutyl)phenyl]-l-methyl-lH-pyrazol-4-carboxamid (bekannt aus WO 2005/042494) der Formel(35) 3- (Difluoromethyl) -N- [2- (3,3-dimethylbutyl) phenyl] -1-methyl-1H-pyrazole-4-carboxamide (known from WO 2005/042494) of the formula
(36) N-[2-(3,3-Dimethylbutyl)phenyl]-5-fluor-l,3-dimethyl-lΗ-pyrazol-4-carboxamid (bekannt aus WO 2005/042494) der Formel (36) N- [2- (3,3-Dimethylbutyl) phenyl] -5-fluoro-1,3-dimethyl-1-pyrazole-4-carboxamide (known from WO 2005/042494) of the formula
(37) N-[3'-Fluor-4'-(trifluormethyl)biphenyl-2-yl]-3-iod-l-methyI-lH-pyrazol-4-carboxamid (bekannt aus WO 2004/103975) der Formel(37) N- [3'-Fluoro-4 '- (trifluoromethyl) biphenyl-2-yl] -3-iodo-1-methyl-1H-pyrazole-4-carboxamide (known from WO 2004/103975) of the formula
(38) 3-(Difluormethyl)-N-[2-(l,3-dimethylbutyl)-4-fluorphenyl]-l-methyl-lH-pyrazol-4- carboxamid (bekannt aus WO 2005/042492) der Formel(38) 3- (Difluoromethyl) -N- [2- (1,3-dimethylbutyl) -4-fluorophenyl] -1-methyl-1H-pyrazole-4-carboxamide (known from WO 2005/042492) of the formula
(39) 4-(Difluormethyl)-2-methyl-N-{2-[2-(trimethylsilyl)ethyl]-3-thienyl}-l,3-thiazol-5- carboxamid(39) 4- (Difluoromethyl) -2-methyl-N- {2- [2- (trimethylsilyl) ethyl] -3-thienyl} -1,3-thiazole-5-carboxamide
Hervorgehoben sind Verbindungen der Formel (I), in welcher R1 für Wasserstoff steht. Hervorgehoben sind Verbindungen der Formel (I), in welcher R1 für Formyl steht. Hervorgehoben sind außerdem Verbindungen der Formel (I), in welcher R1 für -C(=O)C(=O)R2 steht, wobei R2 die oben angegebenen Bedeutungen hat.Emphasis is given to compounds of the formula (I) in which R 1 is hydrogen. Emphasis is given to compounds of the formula (I) in which R 1 is formyl. Also highlighted are compounds of the formula (I) in which R 1 is -C (= O) C (= O) R 2 , where R 2 has the meanings given above.
Die Definition C]-C2o-Alkyl umfasst den größten hierin definierten Bereich für einen Alkylrest. ImThe definition C 1 -C 20 -alkyl encompasses the largest range defined herein for an alkyl radical. in the
Einzelnen umfasst diese Definition die Bedeutungen Methyl, Ethyl, n-, iso-Propyl, n-, iso-, sec-, tert-Specifically, this definition includes the meanings methyl, ethyl, n-, iso-propyl, n-, iso-, sec-, tert-
Butyl, sowie jeweils alle isomeren Pentyle, Hexyle, Heptyle, Octyle, Νonyle, Decyle, Undecyle, Dodecyle, Tridecyle, Tetradecyle, Pentadecyle, Hexadecyle, Heptadecyle, Octadecyle, Νonadecyle und Eicosyle. Hierunter bevorzugt sind die Bedeutungen Methyl, Ethyl, n-, iso-Propyl, n-, iso-, sec-, tert-Butyl, n-Pentyl, 1-Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 1 ,2-Dimethylpropyl, 2,2-Dime- thylpropyl, n-Hexyl, 1-Methylpentyl, 4-Methylpentyl, 1,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1,2,2- Trimethylpropyl, n-Heptyl, 1-Methylhexyl, 5-Methylhexyl, 1 ,4-Dimethylpentyl, 4,4-Dimethylpentyl, 1,3,3-Trimethylbutyl, 1 ,2,3-Trimethylbutyl.Butyl, and in each case all isomeric pentyls, hexyls, heptyls, octyls, Νonyle, Decyle, Undecyle, dodecyls, Tridecyle, Tetradecyle, Pentadecyle, Hexadecyle, Heptadecyle, Octadecyle, Νonadecyle and eicosyls. Preferred among these are the meanings methyl, ethyl, n-, iso-propyl, n-, iso-, sec-, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 2-dimethylpropyl , 2,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 4-methylpentyl, 1,3-dimethylbutyl, 3,3-dimethylbutyl, 1,2,2-trimethylpropyl, n-heptyl, 1-methylhexyl, 5 -Methylhexyl, 1, 4-dimethylpentyl, 4,4-dimethylpentyl, 1,3,3-trimethylbutyl, 1, 2,3-trimethylbutyl.
Gesättigte oder ungesättigte Kohlenwasserstoffreste wie Alkyl oder Alkenyl können, auch in Verbindung mit Heteroatomen, wie z.B. in Alkoxy, soweit möglich, jeweils geradkettig oder verzweigt sein. Ebenfalls können doppelt gebundene Kohlenwasserstoffreste wie Alkylen (Alkandiyl) soweit mög- lieh jeweils geradkettig oder verzweigt sein.Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, may also be used in conjunction with heteroatoms, e.g. in alkoxy, as far as possible, in each case straight-chain or branched. Likewise, doubly bonded hydrocarbon radicals such as alkylene (alkanediyl) may be straight-chain or branched as far as possible.
Gegebenenfalls substituierte Reste können einfach oder mehrfach substituiert sein, wobei bei Mehrfachsubstitutionen die Substituenten gleich oder verschieden sein können. So schließt die Definition Dialkylamino auch eine unsymmetrisch durch Alkyl substituierte Aminogruppe wie z.B. Methyl-ethylamino ein.Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different. Thus, the definition of dialkylamino also includes an unsymmetrically alkyl-substituted amino group, such as e.g. Methyl ethylamino.
Durch Halogen substituierte Reste, wie z.B. Halogenalkyl, sind einfach oder mehrfach halogeniert. Bei mehrfacher Halogenierung können die Halogenatome gleich oder verschieden sein. Halogen steht dabei für Fluor, Chlor, Brom und Iod, insbesondere für Fluor, Chlor und Brom.Halogen substituted radicals, e.g. Haloalkyl, are halogenated singly or multiply. For multiple halogenation, the halogen atoms may be the same or different. Halogen stands for fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen können zwischen den jeweiligen Bereichen und Vorzugsbereichen beliebig kombiniert werden. Sie gelten für die Endprodukte sowie für die Vor- und Zwischenprodukte entsprechend.The general or preferred radical definitions or explanations given above can be combined as desired between the respective ranges and preferred ranges. They apply accordingly to the end products as well as to the precursors and intermediates.
Die erfindungsgemäßen Stoffe weisen eine starke mikrobizide Wirkung auf und können zur Bekämpfung von bestimmten Rostpilzen, wie Sojabohnenrost und Kaffeerost, im Pflanzenschutz eingesetzt werden.The substances according to the invention have a strong microbicidal activity and can be used for controlling certain rust fungi, such as soybean rust and coffee rust, in crop protection.
Bevorzugt können die folgenden Krankheiten von Soja-Pflanzen bekämpft werden: Alternaria leaf spot (Alternaria spec. atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye Leaf spot (Cercospora sojina), Leptosphaerulina Leaf Spot (Leptosphaerulina trifolii), Phyllostica Leaf Spot (Phyllosticta sojaecola), Powdery Mildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rhizoctonia Aerial, Foliage, and Web Blight (Rhizoctonia solani), - -Preferably, the following diseases of soybean plants can be controlled: Alternaria leaf spot (Alternaria spec. Atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. Truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Dandelion leaf leaf (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye leaf spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina trifolii) Phyllostica Leaf Spot (Phyllosticta sojaecola), Powdery Mildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rhizoctonia Aerial, Foliage, and Web Blight (Rhizoctonia solani), - -
Rust (Phakopsora pachyrhizi), Scab (Sphaceloma glycines), Stemphylium Leaf Blight (Stemphylium bo- tryosum), Target Spot (Corynespora cassiicola), Black Root Rot (Calonectria crotalariae), Charcoal Rot (Macrophomina phaseolina), Fusarium Blight or WiIt, Root Rot, and Pod and Collar Rot (Fusarium oxy- sporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Rot (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Stern Blight (Dia- porthe phaseolorum), Stern Canker (Diaporthe phaseolorum var. caulivora), Phytophthora Rot (Phytoph- thora megasperma), Brown Stern Rot (Phialophora gregata), Pythium Rot (Pythium aphanidermatum, Pythium irreguläre, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Rot, Stern Decay, and Damping-Off (Rhizoctonia solani), Sclerotinia Stern Decay (Sclerotinia sclerotio- rum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Rot (Thielaviopsis basicola). Besonders bevorzugt ist die Verwendung der Carboxamide der Formel (I) zur Bekämpfung von Phakopsora pachyrhizi.Rust (Phakopsora pachyrhizi), Scab (Sphaceloma glycines), Stemphylium Leaf Blight (Stemphylium bo- tryosum), Target Spot (Corynespora cassiicola), Black Root Red (Calonectria crotalariae), Charcoal Red (Macrophomina phaseolina), Fusarium Blight or Wiit, Root Red, and Pod and Collar red (Fusarium oxysporum, Fusarium orthoceras, Fusarium semi- titectum, Fusarium equiseti), Mycoleptodiscus root red (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Star Blight (Dia- porthe phaseolorum), Star Canker (Diaporthe phaseolorum var. Caulivora), Phytophthora red (Phytophthora megasperma), Brown red star (Phialophora gregata), Pythium red (Pythium aphanidermatum, Pythium irregular, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia root red, Star decay , and Damping Off (Rhizoctonia solani), Sclerotinia Stern Decay (Sclerotinia sclerotium rum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola). Particularly preferred is the use of the carboxamides of the formula (I) for controlling Phakopsora pachyrhizi.
Unter unerwünschten Mikroorganismen sind im vorliegenden Fall die oben genannten Organismen zu verstehen. Die erfindungsgemäßen Stoffe können also eingesetzt werden, um Pflanzen innerhalb eines gewissen Zeitraumes nach der Behandlung gegen den Befall durch die genannten Schaderreger zu schützen. Der Zeitraum, innerhalb dessen Schutz herbeigeführt wird, erstreckt sich im allgemeinen von 1 bis 10 Tage, vorzugsweise 1 bis 7 Tage nach der Behandlung der Pflanzen mit den Wirkstoffen.Undesirable microorganisms in the present case are the organisms mentioned above. The substances according to the invention can therefore be used to protect plants within a certain period of time after the treatment against the infestation by the said pathogens. The period of time within which protection is afforded generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients.
Die gute Pflanzenverträglichkeit der Wirkstoffe in den zur Bekämpfung von Pflanzenkrankheiten notwendigen Konzentrationen erlaubt eine Behandlung von oberirdischen Pflanzenteilen, von Pflanz- und Saatgut, und des Bodens.The good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of aboveground plant parts, of plant and seed, and the soil.
Dabei lassen sich die Carboxamide der Formel (I) mit besonders gutem Erfolg zur Bekämpfung von Soja-Krankheiten, wie beispielsweise gegen Phakopsora-Arten einsetzen.In this case, the carboxamides of the formula (I) can be used to combat soy diseases, for example against Phakopsora species, with particularly good results.
Die Carboxamide der Formel (I) eignen sich auch zur Steigerung des Ernteertrages. Sie sind außerdem mindertoxisch und weisen eine gute Pflanzenverträglichkeit auf.The carboxamides of the formula (I) are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden, wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sorten- schutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen, wie Spross, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stängel, Stämme, Blüten, Fruchtkörper, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Erntegut sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen.According to the invention, all plants and parts of plants can be treated. In this context, plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including plant varieties which can or can not be protected by plant variety rights. Under plant parts everyone should Above-ground and underground parts and organs of the plants, such as shoot, leaf, flower and root are understood, with examples of leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes are listed. The plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Wirkstoffen erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, Sprühen, Verdampfen, Vernebeln, Streuen, Aufstreichen und bei Vermehrungsmaterial, insbesondere bei Samen, weiterhin durch ein- oder mehrschichtiges Umhüllen.The treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, spreading, spreading and in propagation material, in particular in seeds, further by single or multi-layer wrapping.
Die Wirkstoffe können in Abhängigkeit von ihren jeweiligen physikalischen und/ oder chemischen Eigenschaften in die üblichen Formulierungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Pasten, Granulate, Aerosole, Feinstverkapselungen in polymeren Stoffen und in Hüllmassen für Saatgut, sowie ULV-KaIt- und Warmnebel-Formulierungen.Depending on their respective physical and / or chemical properties, the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, ultrafine encapsulations in polymeric substances and in seed coating compositions, as well as ULV -KaIt- and warm mist formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen und/ oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Ln Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungs- mittel verwendet werden. Als flüssige Lösungsmittel kommen im Wesentlichen infrage: Aromaten, wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasser- Stoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, Alkohole, wie Butanol oder Glycol sowie deren Ether und Ester, Ketone, wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser. Mit verflüssigten gasförmigen Streckmitteln oder Trägerstoffen sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z.B. Aerosol- Treibgase, wie Halogenkohlenwasserstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid. Als feste Trägerstoffe kommen infrage: z.B. natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate. Als feste Trägerstoffe für Granulate kommen infrage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Bims, Marmor, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnussschalen, Maiskolben und Tabakstängel. Als Emulgier und/oder schaumerzeugende Mittel kommen infrage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäureester, Polyoxyethylen-Fettalkoholether, z.B. Alkylaryl- polyglycolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate. Als Dispergiermittel kommen infrage: z.B. Lignin-Sulfitablaugen und Methylcellulose.These formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents. In the case of the use of water as extender, it is also possible, for example, to use organic solvents as auxiliary solvents. Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg petroleum fractions, 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 dimethylformamide and dimethyl sulfoxide, and water. By liquefied gaseous diluents or carriers are meant those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates. As solid carriers for granules are: for example, broken and fractionated natural rocks such as calcite, pumice, marble, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks. When Emulsifying and / or foam-forming agents are suitable: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates. Suitable dispersants are: for example lignin-sulphite liquors and methylcellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine, und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers may be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids. Other additives may be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Spurennährstoffe, wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.
Die Carboxamide der Formel (I) können als solche oder in ihren Formulierungen auch in Mischung mit bekannten Fungiziden, Bakteriziden, Akariziden, Nematiziden oder Insektiziden verwendet werden, um so z.B. das Wirkungsspektrum zu verbreitern oder Resistenzentwicklungen vorzubeugen. In vielen Fällen erhält man dabei synergistische Effekte, d.h. die Wirksamkeit der Mischung ist größer als die Wirksamkeit der Einzelkomponenten.The carboxamides of the formula (I) can be used as such or in their formulations also in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides, so as to obtain e.g. to broaden the spectrum of action or to prevent development of resistance. In many cases synergistic effects, i. E. the effectiveness of the mixture is greater than the effectiveness of the individual components.
Als Mischpartner kommen zum Beispiel folgende Verbindungen infrage: Fungizide:For example, the following compounds are suitable as mixed partners: Fungicides:
2-Phenylphenol; 8-Hydroxyquinoline Sulfate; Acibenzolar-S-methyl; Aldimorph; Amidoflumet; Ampro- pylfos; Ampropylfos-potassium; Andoprim; Anilazine; Azaconazole; Azoxystrobin; Benalaxyl; Be- nodanil; Benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; Bilanafos; Bina- pacryl; Biphenyl; Bitertanol; Blasticidin-S; Boscalid; Bromuconazole; Bupirimate; Buthiobate; Butyl- amine; Calcium polysulfide; Capsimycin; Captafol; Captan; Carbendazim; Carboxin; Carpropamid; Carvone; Chinomethionat; Chlobenthiazone; Chlorfenazole; Chloroneb; Chlorothalonil; Chlozolinate; Clozylacon; Cyazofamid; Cyflufenamid; Cymoxanil; Cyproconazole; Cyprodinil; Cyprofuram; Dagger G; Debacarb; Dichlofluanid; Dichlone; Dichlorophen; Diclocymet; Diclomezine; Dicloran; Di- ethofencarb; Difenoconazole; Diflumetorim; Dimethirimol; Dimethomoφh; Dimoxystrobin; Dinicon- azole; Diniconazole-M; Dinocap; Diphenylamine; Dipyrithione; Ditalimfos; Dithianon; Dodine; Dra- zoxolon; Edifenphos; Epoxiconazole; Ethaboxam; Ethirimol; Etridiazole; Famoxadone; Fenamidone; Fenapanil; Fenarimol; Fenbuconazole; Fenfliram; Fenhexamid; Fenitropan; Fenoxanil; Fenpiclonil; Fenpropidin; Fenpropimoφh; Ferbam; Fluazinam; Flubenzimine; Fludioxonil; Flumetover, Flumoφh; Fluoromide; Fluoxastrobin; Fluquinconazole; Flurprimidol; Flusilazole; Flusulfamide; Flutolanil; Flutriafol; Folpet; Fosetyl-Al; Fosetyl-sodium; Fuberidazole; Furalaxyl; Furametpyr; Furcarbanil; Furmecyclox; Guazatine; Hexachlorobenzene; Hexaconazole; Hymexazol; Imazalil; Imibenconazole; Iminoctadine triacetate; Iminoctadine tris(albesilate); Iodocarb; Ipconazole; Iprobenfos; Iprodione; Iprovalicarb; Irumamycin; Isoprothiolane; Isovaledione; Kasugamycin; Kresoxim-methyl; Mancozeb; Maneb; Meferimzone; Mepanipyrim; Mepronil; Metalaxyl; Metalaxyl-M; Metconazole; Metha- sulfocarb; Methfuroxam; Metiram; Metominostrobin; Metsulfovax; Mildiomycin; Myclobutanil; Myclozolin; Natamycin; Nicobifen; Nitrothal-isopropyl; Noviflumuron; Nuarimol; Ofurace; Orysa- strobin; Oxadixyl; Oxolinic acid; Oxpoconazole; Oxycarboxin; Oxyfenthiin; Paclobutrazol; Pefura- zoate; Penconazole; Pencycuron; Phosdiphen; Phthalide; Picoxystrobin; Piperalin; Polyoxins; PoIy- oxorim; Probenazole; Prochloraz; Procymidone; Propamocarb; Propanosine-sodium; Propiconazole; Propineb; Proquinazid; Prothioconazole; Pyraclostrobin; Pyrazophos; Pyrifenox; Pyrimethanil; Pyro- quilon; Pyroxyfiir; Pyrrolnitrine; Quinconazole; Quinoxyfen; Quintozene; Simeconazole; Spiroxamine; Sulfur; Tebuconazole; Tecloftalam; Tecnazene; Tetcyclacis; Tetraconazole; Thiabendazole; Thicyofen; Thifluzamide; Thiophanate-methyl; Thiram; Tioxymid; Tolclofos-methyl; Tolylfluanid; Triadimefon; Triadimenol; Triazbutil; Triazoxide; Tricyclamide; Tricyclazole; Tridemorph; Trifloxystrobin; Triflu- mizole; Triforine; Triticonazole; Uniconazole; Validamycin A; Vinclozolin; Zineb; Ziram; Zoxamide; (2S)-N-[2-[4-[[3-(4-Chloφhenyl>2-propnyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulfo- nyl)amino]-butanamid; 1 -( 1 -Naphthalinyl)- 1 H-pyrrol-2,5-dion; 2,3,5,6-Tetrachlor-4-(methylsulfonyl)- pyridin; 2-Amino-4-methyl-N-phenyl-5-thiazolcarboxamid; 2-Chlor-N-(2,3-dihydro-l,l,3-trimethyl-lH- inden-4-yl)-3-pyridincarboxamid; 3,4,5-Trichlor-2,6-pyridindicarbonitril; Actinovate; cis-l-(4-Chlor- phenyl>2-( 1 H- 1 ,2,4-triazol-l -yl>cycloheptanol; Methyl 1 -(2,3-dihydro-2,2-dimethyl- 1 H-inden- 1 -yl> lH-imidazol-5-carboxylat; Monokaliumcarbonat; N-(6-Methoxy-3-pyridinyl)-cyclopropancarboxamid; N-Butyl-8-( 1 , 1 -dimethylethyl)-l -oxaspiro[4.5]decan-3-amin; Natriumtetrathiocarbonat; sowie Kupfersalze und -Zubereitungen, wie Bordeaux mixture; Copper hydroxide; Copper naphthe- nate; Copper oxychloride; Copper Sulfate; Cufraneb; Cuprous oxide; Mancopper; Oxine-copper.2-phenylphenol; 8-hydroxyquinoline sulfates; Acibenzolar-S-methyl; aldimorph; amidoflumet; Amphropolys; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; Nodanil; benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; bilanafos; Bipacryl; biphenyl; bitertanol; Blasticidin-S; boscalid; bromuconazole; Bupirimate; Buthiobate; Butylamines; Calcium polysulfides; capsimycin; captafol; captan; carbendazim; carboxin; carpropamid; carvones; chinomethionat; Chlobenthiazone; Chlorfenazole; chloroneb; chlorothalonil; chlozolinate; Clozylacon; cyazofamid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; Diclomezine; dicloran; Diethofencarb; Difenoconazole; diflumetorim; dimethirimol; Dimethomoφh; dimoxystrobin; Diniconazoles; Diniconazole-M; dinocap; diphenylamines; Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolone; edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole; famoxadone; fenamidone; Fenapanil; fenarimol; Fenbuconazole; Fenfliram; fenhexamid; Fenitropan; fenoxanil; fenpiclonil; fenpropidin; Fenpropimoφh; ferbam; fluazinam; Flubenzimine; fludioxonil; Flumetov, Flumoφh; fluoromides; fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil; Furmecyclox; guazatine; Hexachlorobenzene; hexaconazole; hymexazol; imazalil; Imibenconazole; Iminoctadine triacetate; Iminoctadine tris (albesilate); iodocarb; ipconazole; iprobenfos; iprodione; iprovalicarb; Irumamycin; isoprothiolane; Isovaledione; kasugamycin; Kresoxim-methyl; mancozeb; maneb; Meferimzone; mepanipyrim; mepronil; metalaxyl; Metalaxyl-M; metconazole; Methasulfocarb; Methfuroxam; metiram; metominostrobin; Metsulfovax; mildiomycin; myclobutanil; myclozoline; natamycin; nicobifen; Nitro Thal-isopropyl; Noviflumuron; nuarimol; ofurace; Orysazrobin; oxadixyl; Oxolinic acid; Oxpoconazole; oxycarboxin; Oxyfenthiin; paclobutrazol; Pefura- zoates; penconazole; pencycuron; phosdiphen; phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorime; Probenazole; prochloraz; procymidone; propamocarb; Propanosine-sodium; propiconazole; propineb; proquinazid; prothioconazole; pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; Pyroquilon; Pyroxyfiir; Pyrrolnitrine; Quinconazole; quinoxyfen; quintozene; Simeconazole; spiroxamine; Sulfur; tebuconazole; tecloftalam; Tecnazene; Tetcyclacis; tetraconazole; thiabendazole; Thicyofen; Thifluzamide; Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; Triazbutil; triazoxide; Tricyclamide; Tricyclazole; tridemorph; trifloxystrobin; Triflicane; triforine; triticonazole; Uniconazole; Validamycin A; vinclozolin; Zineb; ziram; zoxamide; (2S) -N- [2- [4 - [[3- (4-chlorophenyl) 2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2 - [(methylsulfonyl) amino] - butanamide; 1 - (1-naphthalenyl) -1-H-pyrrole-2,5-dione; 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine; 2-amino-4-methyl-N-phenyl 5-thiazolecarboxamide; 2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide; 3,4,5-trichloro-2,6 actinovate; cis-1- (4-chlorophenyl> 2- (1H-1,2,4-triazol-1-yl>cycloheptanol; methyl 1- (2,3-dihydro-2,2-) -pyridine dicarbonitrile; dimethyl-1H-inden-1-yl>1H-imidazole-5-carboxylate; monopotassium carbonate; N- (6-methoxy-3-pyridinyl) -cyclopropanecarboxamide; N-butyl-8- (1, 1-dimethyl-ethyl) -l -oxaspiro [4.5] decane-3-amine; sodium tetrathiocarbonate; and copper salts and preparations such as Bordeaux mixture; Copper hydroxide; Copper naphthenate; Copper oxychloride; Copper sulphate; Cufraneb; Cuprous oxide; Mancopper; Oxine copper.
Bakterizide:bactericides:
Bronopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamycin, Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen.Bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
Insektizide / Akarizide / Nematizide:Insecticides / acaricides / nematicides:
1. Acetylcholinesterase (AChE) Inhibitoren 1.1 Carbamate (z.B. Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Azamethiphos, Bendiocarb, Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofiiran, Carbosulfan, Chloethocarb, Coumaphos, Cyanofenphos, Cyanophos, Dimetilan, Ethiofencarb, Fenobucarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC, Xylylcarb)1. Acetylcholinesterase (AChE) inhibitors 1.1 carbamates (eg alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, azamethiphos, bendocarb, benfuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxime, carbaryl, carbofiirane, carbosulfan, chloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilane, ethiofencarb, fenobucarb, fenothiocarb, Formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb)
1.2 Organophosphate (z.B. Acephate, Azamethiphos, Azinphos (-methyl, -ethyl), Bromophos-ethyl, Bromfenvinfos (-methyl), Butathiofos, Cadusafos, Carbophenothion, Chlorethoxyfos, Chlorfen- vinphos, Chlormephos, Chloφyrifos (-methyl/-ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphon, Dialifos, Diazinon, Dichlofenthion, Dichlorvos/DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupy- razofos, Fonofos, Formothion, Fosmethilan, F osthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-salicylate, Isoxathion, Malathion, Mecarbam, Methacrifos, Metha- midophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Para- thion (-methyV-ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Pirimiphos (-methyl/-ethyl), Profenofos, Propaphos, Propetamphos, Prothiofos, Prothoate, Pyraclofos, Pyridaphenthion, Pyridathion, Quinalphos, Sebufos, Sulfotep, Sulprofos, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon, Vamidothion) 2. Natrium-Kanal-Modulatoren /Spannungsabhängige Natrium-Kanal-Blocker1.2 organophosphates (eg acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chloroethoxyfos, chlorfenvinphos, chlormephos, chloφyrifos (-methyl / -ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphone, Dialifos, Diazinon, Dichlofenthione, Dichlorvos / DDVP, Dicrotophos, Dimethoates, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazofos, Fonofos, Formothion, Fosmethilane, F osthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-salicylate, Isoxathion, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyV-ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Pirimiphos (-methyl / -ethyl), Profenofos, Propaphos, P ropetamphos, prothiofos, prothoates, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometone, triazophos, triclorfone, vamidothion) 2. Sodium-channel modulators / voltage-dependent sodium channel blockers
2.1 Pyrethroide (z.B. Acrinathrin, Allethrin (d-cis-trans, d-trans), Beta-Cyfluthrin, Bifenthrin, Bio- allethrin, Bioallethrin-S-cyclopentyl-isomer, Bioethanomethrin, Biopermethrin, Bioresmethrin, ChIo- vaporthrin, Cis-Cypermethrin, Cis-Resmethrin, Cis-Permethrin, Clocythrin, Cycloprothrin, Cyflu- thrin, Cyhalothrin, Cypermethrin (alpha-, beta-, theta-, zeta-), Cyphenothrin, DDT, Deltamethrin, Em- penthrin (lR-isomer), Esfenvalerate, Etofenprox, Fenfluthrin, Fenpropathrin, Fenpyrithrin, Fen- valerate, Flubrocythrinate, Flucythrinate, Flufenprox, Flumethrin, Fluvalinate, Fubfenprox, Gamma- Cyhalothrin, Imiprothrin, Kadethrin, Lambda-Cyhalothrin, Metofluthrin, Permethrin (eis-, trans-), Phenothrin (lR-trans isomer), Prallethrin, Profluthrin, Protrifenbute, Pyresmethrin, Resmethrin, RU 15525, Silafluofen, Tau-Fluvalinate, Tefluthrin, Terallethrin, Tetramethrin (lR-isomer), Tralome- thrin, Transfluthrin, ZXI 8901, Pyrethrins (pyrethrum))2.1 Pyrethroids (eg acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, biotethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlorovaporthrin, cis-cypermethrin , Cis-resmethrin, cis-permethrin, clocthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, pentan-in (IR-isomer), esfenvalerate , Etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalate, flubrocythrinates, flucythrinates, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis-, trans-), phenothhrin ( IR trans isomer), prallethrin, profuthrin, protrifenbutene, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (IR isomer), tralomoterine, transfluthrin, ZXI 8901, pyrethrin (pyrethrum))
2.2 Oxadiazine (z.B. Indoxacarb)2.2 Oxadiazines (e.g., indoxacarb)
3. Acetylcholin-Rezeptor-AgonistenZ-Antagonisten3. Acetylcholine receptor agonist Z antagonists
3.1 Chloronicotinyle/Neonicotinoide (z.B. Acetamiprid, Clothianidin, Dinotefiiran, Imidacloprid, Ni- tenpyram, Nithiazine, Thiacloprid, Thiamethoxam) 3.2 Nicotine, Bensultap, Cartap3.1 chloronicotinyls / neonicotinoids (for example, acetamiprid, clothianidin, dinotefiran, imidacloprid, nitrepyram, nithiazines, thiacloprid, thiamethoxam) 3.2 Nicotine, Bensultap, Cartap
4. Acetylcholin-Rezeptor-Modulatoren 4.1 Spinosyne (z.B. Spinosad)4. Acetylcholine receptor modulators 4.1 Spinosyn (eg spinosad)
5. GABA-gesteuerte Chlorid-Kanal-Antagonisten5. GABA-driven chloride channel antagonists
5.1 Cyclodiene Organochlorine (z.B. Camphechlor, Chlordane, Endosulfan, Gamma-HCH, HCH, Heptachlor, Lindane, Methoxychlor 5.2 Fiprole (z.B. Acetoprole, Ethiprole, Fipronil, Vaniliprole)5.1 Cyclodienes Organochlorines (e.g., camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor 5.2 Fiproles (e.g., acetoprole, ethiprole, fipronil, vaniliprole)
6. Chlorid-Kanal-Aktivatoren6. Chloride Channel Activators
6.1 Mectine (z.B. Abamectin, Avermectin, Emamectin, Emamectin-benzoate, Ivermectin, Milbe- mectin, Milbemycin)6.1 Mectins (for example, abamectin, avermectin, emamectin, emamectin benzoate, ivermectin, milkmectin, milbemycin)
7. Juvenilhormon-Mimetika (z.B. Diofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene, Methoprene, Pyriproxifen, Triprene) S. Ecdysonagonisten/disruptoren7. Juvenile hormone mimetics (e.g., diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprenes, methoprenes, pyriproxifen, triprenes) S. ecdysone agonists / disruptors
8.1 Diacylhydrazine (z.B. Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide) 9. Inhibitoren der Chitinbiosynthese 9.1 Benzoylharnstoffe (z.B. Bistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penfluron, Teflubenzuron, Tri- flumuron)8.1 Diacylhydrazines (e.g., Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide) 9. Inhibitors of Chitin Biosynthesis 9.1 Benzoylureas (e.g., Bistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penflurone, Teflubenzuron, Triflumuron)
9.2 Buprofezin9.2 Buprofezin
9.3 Cyromazine 10. Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren9.3 Cyromazines 10. Inhibitors of oxidative phosphorylation, ATP disruptors
10.1 Diafenthiuron10.1 Diafenthiuron
10.2 Organotine (z.B. Azocyclotin, Cyhexatin, Fenbutatin-oxide)10.2 Organotin (e.g., azocyclotin, cyhexatin, fenbutatin oxides)
11. Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Protongradienten 11.1 Pyrrole (z.B. Chlorfenapyr) 11.2 Dinitrophenole (z.B. Binapacyrl, Dinobuton, Dinocap, DNOC)11. Decoupling of Oxidative Phosphorylation by Breaking H Proton Gradient 11.1 Pyrroles (e.g., Chlorfen Apyr) 11.2 Dinitrophenols (e.g., Binapacyrl, Dinobutone, Dinocap, DNOC)
12. Site-I-Elektronentransportinhibitoren12. Site I electron transport inhibitors
12.1 METI's (z.B. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad)12.1 METI's (e.g., Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad)
12.2 Hydramethylnone12.2 Hydramethylnone
12.3 Dicofol 13. Site-II-Elektronentransportinhibitoren12.3 Dicofol 13. Site II Electron Transport Inhibitors
13.1 Rotenone13.1 Rotenone
14. Site-III-Elektronentransportinhibitoren14. Site III Electron Transport Inhibitors
14.1 Acequinocyl, Fluacrypyrim14.1 Acequinocyl, Fluacrypyrim
75. Mikrobielle Disruptoren der Insektendarmmembran Bacillus thuringiensis-Stämme75. Microbial disruptors of insect gut membrane Bacillus thuringiensis strains
16. Inhibitoren der Fettsynthese - -16. Inhibitors of fat synthesis - -
16.1 Tetronsäuren (z.B. Spirodiclofen, Spiromesifen)16.1 Tetronic acids (e.g., spirodiclofen, spiromesifen)
16.2 Tetramsäuren [z.B. 3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-l-azaspiro[4.5]dec-3-en-4-yl ethyl carbonate (alias: Carbonic acid, 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-l-azaspiro[4.5]dec-3-en-4- yl ethyl ester, CAS-Reg.-No.: 382608-10-8) and Carbonic acid, cis-3-(2,5-dimethylphenyl)-8- methoxy-2-oxo-l-azaspiro[4.5]dec-3-en-4-yl ethyl ester (CAS-Reg.-No.: 203313-25-1)]16.2 tetramic acids [e.g. 3- (2,5-Dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (also known as: Carbonic acid, 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl ester, CAS Reg. No .: 382608-10-8) and carbonic acid, cis-3 ( 2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl ester (CAS Reg. No .: 203313-25-1)]
17. Carboxamide (z.B. Flonicamid)17. Carboxamides (e.g., flonicamid)
18. Oktopaminerge Agonisten (z.B. Amitraz) 19. Inhibitoren der Magnesium-stimulierten A TPase18. Octopaminergic agonists (e.g., amitraz) 19. Inhibitors of magnesium-stimulated A TPase
(z.B. Propargite)(e.g., propargite)
20. Phthalamide20. phthalamides
(z.B. N2-[ 1 , 1 -Dimethyl-2T(methylsulfonyl)ethyl]-3-iod-N1-[2-methyl-4-[ 1 ,2,2,2-tetrafluor- 1 -(trifluor- methyl)ethyl]phenyl]-l,2-benzenedicarboxamide (CAS-Reg.-No.: 272451-65-7)) 21. Nereistoxin-Analoge(eg N 2 - [1, 1-dimethyl-2 T (methylsulfonyl) ethyl] -3-iodo-N 1 - [2-methyl-4- [1, 2,2,2-tetrafluoro-1 - (trifluoro-) methyl) ethyl] phenyl] -l, 2-benzenedicarboxamide (CAS Reg. No .: 272451-65-7)) 21. Nereistoxin analogs
(z.B. Thiocyclam hydrogen Oxalate, Thiosultap-sodium)(e.g., thiocyclam hydrogen oxalate, thiosultap-sodium)
22. Bioϊogika, Hormone oder Pheromone22. Bioϊogika, hormones or pheromones
(z.B. Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhizium spec, Paecilomyces spec, Thuringiensin, Verticillium spec.) 23. Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen(e.g., azadirachtin, bacillus spec, beauveria spec, codlemone, metarrhicon spec, paecilomyces spec, thuringiensin, verticillium spec.) 23. Active agents with unknown or nonspecific modes of action
23.1 Begasungsmittel (z.B. Aluminium phosphide, Methyl bromide, Sulfuryl fluoride)23.1 fumigants (e.g., aluminum phosphides, methyl bromides, sulfuryl fluorides)
23.2 Selektive Fraßhemmer (z.B. Cryolite, Flonicamid, Pymetrozine)23.2 Selective feeding inhibitors (e.g., cryolites, flonicamid, pymetrozines)
23.3 Milbenwachstumsinhibitoren (z.B. Clofentezine, Etoxazole, Hexythiazox)23.3 mite growth inhibitors (e.g., clofentezine, etoxazole, hexythiazox)
23.4 Amidoflumet, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Buprofezin, Chinomethi- onat, Chlordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben, Cycloprene, Dicyclanil, Fenoxa- crim, Fentrifanil, Flubenzimine, Flufenerim, Flutenzin, Gossyplure, Hydramethylnone, Japonilure, Metoxadiazone, Petroleum, Piperonyl butoxide, Potassium oleate, Pyridalyl, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin23.4 Amidoflumet, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Buprofezin, Chinomethionate, Chlordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben, Cycloprene, Dicyclanil, Fenoxa- crim, Fentrifanil, Flubenzimine, Flufenerim, Flotenzin, Gossyplure, Hydramethylnone, Japonilure, Metoxadiazone, Petroleum , Piperonyl butoxide, Potassium oleate, Pyralidyl, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin
ferner die Verbindung 3-Methyl-phenyl-propylcarbamat (Tsumacide Z), die Verbindung 3-(5-Chlor-3- pyridinyl>8-(2,2,2-trifluorethyl>8-azabicyclo[3.2.1]octan-3-carbonitril (CAS-Reg.-Nr. 185982-80-3) und das entsprechende 3-endo-Isomere (CAS-Reg.-Nr. 185984-60-5) (vgl. WO 96/37494, WO 98/25923), sowie Präparate, welche insektizid wirksame Pflanzenextrakte, Nematoden, Pilze oder Viren enthalten.the compound 3-methylphenyl-propylcarbamate (Tsumacide Z), the compound 3- (5-chloro-3-pyridinyl> 8- (2,2,2-trifluoroethyl> 8-azabicyclo [3.2.1] octane-3) carbonitrile (CAS Reg. No. 185982-80-3) and the corresponding 3-endo isomer (CAS Reg. No. 185984-60-5) (see WO 96/37494, WO 98/25923 ), as well as preparations containing insecticidal plant extracts, nematodes, fungi or viruses.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwen- - - dungsformen, wie gebrauchsfertige Lösungen, Suspensionen, Spritzpulver, Pasten, lösliche Pulver, Stäubemittel und Granulate angewendet werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Verspritzen, Versprühen, Verstreuen, Verstäuben, Verschäumen, Bestreichen usw. Es ist ferner möglich, die Wirkstoffe nach dem Ultra-Low-Volume- Verfahren auszubringen oder die Wirkstoffzubereitung oder den Wirkstoff selbst in den Boden zu injizieren. Es kann auch das Saatgut der Pflanzen behandelt werden.The active compounds can be used as such, in the form of their formulations or the formulations prepared therefrom. - Forms such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules are used. The application is done in a conventional manner, for example by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or the active ingredient preparation or the active ingredient itself in the Inject soil. It can also be the seed of the plants to be treated.
Beim Einsatz der Carboxamide der Formel (I) als Fungizide können die Aufwandmengen je nach Applikationsart innerhalb eines größeren Bereiches variiert werden. Bei der Behandlung von Pflan- zenteilen liegen die Aufwandmengen an Wirkstoff im allgemeinen zwischen 0,1 und 10.000 g/ha, vorzugsweise zwischen 10 und 1.000 g/ha. Bei der Saatgutbehandlung liegen die Aufwandmengen an Wirkstoff im allgemeinen zwischen 0,001 und 50 g pro Kilogramm Saatgut, vorzugsweise zwischen 0,01 und 10 g pro Kilogramm Saatgut. Bei der Behandlung des Bodens liegen die Aufwandmengen an Wirkstoff im allgemeinen zwischen 0,1 und 10.000 g/ha, vorzugsweise zwischen 1 und 5.000 g/ha.When using the carboxamides of the formula (I) as fungicides, the application rates can be varied within a relatively wide range, depending on the mode of application. In the treatment of plant parts, the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the seed treatment, the application rates of active ingredient are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
Wie bereits oben erwähnt, können erfϊndungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausfuhrungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden, wie Kreuzung oder Protoplastenfusion erhaltenen Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausfuhrungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff „Teile" bzw. „Teile von Pflanzen" oder „Pflanzenteile" wurde oben erläutert.As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild species or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant varieties and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above.
Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften („Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken gezüchtet worden sind. Dies können Sorten, Rassen, Bio- und Genotypen sein.It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. Plant varieties are understood to be plants having new traits which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques, which may be varieties, breeds, biotypes and genotypes.
Je nach Pflanzenarten bzw. Pflanzensorten, deren Standort und Wachstumsbedingungen (Böden, Klima, Vegetationsperiode, Ernährung) können durch die erfindungsgemäße Behandlung auch überadditive („synergistische") Effekte auftreten. So sind beispielsweise erniedrigte Aufwandmengen und/oder Erweiterungen des Wirkungsspektrums und/oder eine Verstärkung der Wirkung der erfin- dungsgemäß verwendbaren Stoffe und Mittel, besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte möglich, die über die eigentlich zu erwartenden Effekte hinausgehen.Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, nutrition), the treatment according to the invention may also give rise to superadditive ("synergistic") effects, for example reduced application rates and / or extensions of the activity spectrum and / or a Enhancement of the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water. or soil salt content, increased flowering power, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the actual expected effects.
Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften („Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehr der Pflanzen gegen tierische und mikrobielle Schädlinge, wie gegenüber Insekten, Milben, pflanzenpathogenen Pilzen, Bakterien und/oder Viren sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Wie- zen, Reis), Mais, Soja, Kartoffel, Baumwolle, Tabak, Raps sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben) erwähnt, wobei Mais, Soja, Kartoffel, Baumwolle, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften („Traits") werden besonders hervorgehoben die erhöhte Abwehr der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus Thuringiensis (z.B. durch die Gene CryΙA(a), CryIA(b), CryΙA(c), CryllA, CryHIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden (im Folgenden „Bt Pflanzen"). Als Eigenschaften („Traits") werden auch besonders hervorgehoben die erhöhte Abwehr von Pflanzen gegen Pilze, Bakterien und Viren durch Systemische Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine. Als Eigenschaften („Traits") werden weiterhin besonders hervorgehoben die erhöhte Toleranz der Pflanzen gegenüber bestimmten herbiziden Wirk- Stoffen, z.B. Imidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinotricin (z.B. "PAT"- Gen). Die jeweils die gewünschten Eigenschaften („Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele für ,3t Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und Kartoffelsorten genannt, die unter den Handelsbezeichnungen YDELD GARD® (z.B. Mais, Baumwolle, Soja), KnockOut® (z.B. Mais), StarLink® (z.B. Mais), Bollgard® (Baumwolle), Nucoton® (Baumwolle) und NewLeaf® (Kartoffel) vertrieben werden. Als Beispiele für Herbizid tolerante Pflanzen seien Maissorten, Baumwollsorten und Sojasorten genannt, die unter den Handelsbezeichnungen Roundup Ready® (Toleranz gegen Glypho- sate z.B. Mais, Baumwolle, Soja), Liberty Link® (Toleranz gegen Phosphinotricin, z.B. Raps), IMI® (Toleranz gegen Imidazolinone) und STS® (Toleranz gegen Sulfonylharnstoffe z.B. Mais) vertrieben werden. Als Herbizid resistente (konventionell auf Herbizid-Toleranz gezüchtete) Pflanzen seien auch die unter der Bezeichnung Clearfield® vertriebenen Sorten (z.B. Mais) erwähnt. Selbstverständlich gelten diese Aussagen auch für in der Zukunft entwickelte bzw. zukünftig auf den Markt kommende Pflanzensorten mit diesen oder zukünftig entwickelten genetischen Eigenschaften („Traits").The preferred plants or plant cultivars to be treated according to the invention include all plants which have obtained genetic material by the genetic engineering modification which gives these plants particularly advantageous valuable properties ("traits") Examples of such properties are better plant growth. increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances. Examples of transgenic plants include the important crops, such as cereals (wheat, rice), maize, soya, potato, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with maize, soya Potato, cotton, tobacco and oilseed rape are particularly emphasized. Traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins produced in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (eg by the genes CryΙA (a) , CryIA (b), CryΙA (c), CryllA, CryHIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) in the plants (hereinafter "Bt plants"). Traits also highlight the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. ) are particularly emphasized the increased tolerance of the plants to certain herbicidal active substances, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene). The genes conferring the desired properties ("traits") may also be present in combinations with one another in the transgenic plants Examples of "3t plants" are corn, cotton, soy and potato varieties sold under the trade names YDELD GARD® (eg maize , Cotton, soybean), KnockOut® (eg corn), StarLink® (eg corn), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide tolerant plants are maize varieties, cotton varieties and Soya varieties known under the trade names Roundup Ready® (tolerance to glyphosate eg maize, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance to imidazolinone) and STS® (tolerance to sulfonylureas eg corn). Herbicide-resistant (conventionally grown on herbicide tolerance) plants are also the varieties marketed under the name Clearfield® (eg corn) mentioned. Of course, these statements also apply to future or future marketed plant varieties with these or future developed genetic traits.
Die aufgeführten Pflanzen können besonders vorteilhaft erfindungsgemäß mit den Verbindungen der allgemeinen Formel (I) bzw. den erfindungsgemäßen Wirkstoffrnischungen behandelt werden. Die bei den Wirkstoffen bzw. Mischungen oben angegebenen Vorzugsbereiche gelten auch für die Behandlung dieser Pflanzen. Besonders hervorgehoben sei die Pflanzenbehandlung mit den im vorliegenden Text speziell aufgeführten Verbindungen bzw. Mischungen.The plants listed can be treated particularly advantageously according to the invention with the compounds of general formula (I) or the Wirkstoffrnischungen invention. The preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants. Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
Die Verwendung der Carboxamide der Formel (I) geht aus den folgenden Beispielen hervor. The use of the carboxamides of the formula (I) is evident from the following examples.
Anwendungsbeispieleapplications
Beispiel AExample A
Sojabohnen-Rost Kontrolltest/SprayapplikationSoybean rust control test / spray application
Vorbereitung der Testsubstanzen:Preparation of the test substances:
5 Gewichtsteile an Carboxamid der Formel (I), 142,4 Gewichtsteile Aceton und 7,5 Gewichtesteile Emulgator (Polyoxyethylen-alkyl-phenyl-ether) werden gemischt und mit Wasser auf die gewünschte Konzentration eingestellt.5 parts by weight of carboxamide of the formula (I), 142.4 parts by weight of acetone and 7.5 parts by weight of emulsifier (polyoxyethylene-alkyl-phenyl-ether) are mixed and adjusted to the desired concentration with water.
Testmethode:Test Method:
Sojabohnen (Sorte: Enrei) wurden in Plastikgefäßen von 7,5 cm Durchmesser kultiviert. Zu den Setzlingen, die das 2.3 Blattstadium erreicht hatten, wurden je 3 Gefäßen 6 ml der Testsubstanz (Vorbe- reitung wie oben beschrieben) gesprüht. Ein Tag nach dem Besprühen wurden die Blätter mit einer Urediniosporen-Suspension (1 x 105 Urediniosporen/ml) von Phakopsora pachyrhizi inokuliert. 14 Tage nach der Inokulation wurde die Stärke des Befalls je Gefäß bewertet und der Wirkungsgrad berechnet. Phytotoxicity wurde ebenfalls kontrolliert. Soybeans (variety: Enrei) were cultivated in plastic containers of 7.5 cm diameter. For the seedlings which had reached the 2.3 leaf stage, 6 ml of the test substance (preparation as described above) were sprayed per 3 containers. One day after spraying, the leaves were inoculated with a urediniosporen suspension (1 x 10 5 urediniospores / ml) of Phakopsora pachyrhizi. Fourteen days after inoculation, the severity of infestation per vessel was evaluated and the efficiency calculated. Phytotoxicity was also controlled.
Tabelle ATable A
Sojabohnen-Rost Kontrolltest/SprayapplikationSoybean rust control test / spray application
- - - -
Tabelle ATable A
Sojabohnen-Rost Kontrolltest/SprayapplikationSoybean rust control test / spray application

Claims

PatentansprücbePatent claims
Verwendung von Carboxamiden der Formel (I)Use of carboxamides of formula (I)
in welcher, in which,
A für gegebenenfalls substituiertes Aryl oder einen aromatischen oder nicht aromatischen, 5- oder 6-gliedrigen carbocyclischen oder heterocyclischen Ring mit 1 bis 3 Heteroatomen, welche O, N oder S sein können, steht und der Carbo- oder Heterocyclus 1, 2 oder 3 Substituenten tragen kann, welche aus Alkyl, Halogen, Halogenalkyl, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl ausgewählt sind,A represents optionally substituted aryl or an aromatic or non-aromatic, 5- or 6-membered carbocyclic or heterocyclic ring with 1 to 3 heteroatoms, which can be O, N or S, and the carbo- or heterocycle has 1, 2 or 3 substituents can carry, which are selected from alkyl, halogen, haloalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl,
R1 für Wasserstoff, C,-C8-Alkyl, CrC6-Alkylsulfinyl, CrC6-Alkylsulfonyl, C,-C4- Alkoxy-C,-C4-alkyl, C3-C8-Cycloalkyl; C,-C6-Halogenalkyl, CrC4-Halogenalkylthio, Ci-C4-Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, Halogen-Ci-C4-alkoxy-Ci- C4-alkyl, C3-Cg-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Brom- atomen; Formyl, Formyl-CrC3-alkyl, (CrC3-Alkyl)carbonyl-Ci-C3-alkyl, (CrC3-R 1 for hydrogen, C,-C 8 -alkyl, C r C 6 -alkylsulfinyl, C r C 6 -alkylsulfonyl, C,-C 4 -alkoxy-C,-C 4 -alkyl, C 3 -C 8 -cycloalkyl ; C,-C 6 -haloalkyl, C r C 4 -haloalkylthio, Ci-C 4 -haloalkylsulfinyl, Ci-C 4 -haloalkylsulfonyl, halogen-Ci-C 4 -alkoxy-Ci- C 4 -alkyl, C 3 -Cg- Halogencycloalkyl, each with 1 to 9 fluorine, chlorine and/or bromine atoms; Formyl, formyl-CrC 3 -alkyl, (C r C 3 -alkyl)carbonyl-Ci-C 3 -alkyl, (C r C 3 -
Alkoxy)carbonyl-CrC3-alkyl; Halogen-(Ci-C3-alkyl)carbonyl-CrC3-alkyl, Halogen- (Ci-C3-alkoxy)carbonyl-C|-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (Ci-C8-Alkyl)carbonyl, (Ci-C8-Alkoxy)carbonyl, (CrC8-Alkylthio)carbonyl, (C1-C4- Alkoxy-C]-C4-alkyl)carbonyl, (C3-C6-Alkenyloxy)carbonyl, (C3-Q-Alkinyloxy)carbo- nyl, (C3-Cg-Cycloalkyl)carbonyl; (Ci-C6-Halogenalkyl)carbonyl, (Ci-C6-Halogenalk- oxy)carbonyl, (Ci-C6-Halogenalkylthio)carbonyl, (Halogen-CrC4-alkoxy-Ci-C4-alkyl)- carbonyl, (C3-C6-Halogenalkenyloxy)carbonyl, (C3-C6-Halogenalkinyloxy)carbonyl, (C3-Cg-Halogencycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Brom- atomen; oder -CH2-C≡C-R1 A, -CH2-CH=CH-R1 A, -CH=C=CH-R1 A, -C(=O)C(=O)R2,alkoxy)carbonyl-C r C 3 alkyl; Halogen-(Ci-C 3 -alkyl)carbonyl-C r C 3 -alkyl, halogen-(Ci-C 3 -alkoxy)carbonyl-C|-C 3 -alkyl with 1 to 13 fluoro-, chloro- and/or or bromine atoms; (Ci-C 8 -alkyl)carbonyl, (Ci-C 8 -alkoxy)carbonyl, (C r C 8 -alkylthio)carbonyl, (C 1 -C 4 -alkoxy-C]-C 4 -alkyl)carbonyl, ( C 3 -C 6 -alkenyloxy)carbonyl, (C 3 -Q-alkynyloxy)carbonyl, (C 3 -Cg-cycloalkyl)carbonyl; (Ci-C 6 -haloalkyl)carbonyl, (Ci-C 6 -haloalk-oxy)carbonyl, (Ci-C 6 -haloalkylthio)carbonyl, (halogen-C r C 4 -alkoxy-Ci-C 4 -alkyl)- carbonyl, (C 3 -C6-haloalkenyloxy)carbonyl, (C 3 -C 6 -haloalkynyloxy)carbonyl, (C 3 -Cg-halocycloalkyl)carbonyl, each with 1 to 9 fluorine, chlorine and/or bromine atoms; or -CH 2 -C≡CR 1 A , -CH 2 -CH=CH-R 1 A , -CH=C=CH-R 1 A , -C(=O)C(=O)R 2 ,
-CONR3R4 oder -CH2NR5R6 steht,-CONR 3 R 4 or -CH 2 NR 5 R 6 stands,
R1 A für Wasserstoff, CrC6-Alkyl, CrC6-Halogenalkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3- C7-Cycloalkyl, (CrC4-Alkoxy)carbonyl, (C3-C6-Alkenyloxy)carbonyl, (C3-C6-AIkJ- nyloxy)carbonyl oder Cyano steht, R2 für Wasserstoff, C,-C8-Alkyl, CrC8-Alkoxy, CrC4-Alkoxy-CrC4-alkyl, C3-C8-R 1 A for hydrogen, C r C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 - C 7 cycloalkyl, (C r C 4 - Alkoxy)carbonyl, (C 3 -C 6 -alkenyloxy)carbonyl, (C 3 -C 6 -AlkJ- nyloxy)carbonyl or cyano, R 2 is hydrogen, C,-C 8 -alkyl, C r C 8 -alkoxy , C r C 4 -alkoxy-C r C 4 -alkyl, C 3 -C 8 -
Cycloalkyl; CrC6-Halogenalkyl, CrCβ-Halogenalkoxy, Halogen-CrC4-alkoxy-Ci- C4-alkyl, Cs-Cg-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen steht, - -cycloalkyl; C r C 6 -haloalkyl, CrCβ-haloalkoxy, halogen-C r C 4 -alkoxy-Ci-C 4 -alkyl, Cs-Cg-halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, - -
R3 und R4 unabhängig voneinander jeweils für Wasserstoff, Q-Cg-Alkyl, Ci-C4-Alkoxy-Ci-C4- alkyl, C3-C8-Cycloalkyl; CrCrHalogenalkyl, Halogen-CrC4-alkoxy-Ci-C4-alkyl, C3- Cg-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,R 3 and R 4 independently each represent hydrogen, Q-Cg-alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 -cycloalkyl; C r C r haloalkyl, halogen-C r C 4 -alkoxy-Ci-C 4 -alkyl, C 3 -Cg-halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms,
R3 und R4 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen ge- gebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Q-R 3 and R 4 also together with the nitrogen atom to which they are bonded, optionally single or multiple, identical or different, by halogen or Q-
C4-Alkyl substituierten gesättigten Heterocyclus mit 5 bis 8 Ringatomen bilden, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus derC 4 -alkyl substituted saturated heterocycle with 5 to 8 ring atoms, the heterocycle having 1 or 2 further, non-adjacent heteroatoms from the
Reihe Sauerstoff, Schwefel oder NR7 enthalten kann,Series may contain oxygen, sulfur or NR 7 ,
R5 und R6 unabhängig voneinander für Wasserstoff, CrC8-Alkyl, C3-C8-Cycloalkyl; C1-C8- Halogenalkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oderR 5 and R 6 independently represent hydrogen, C r C 8 alkyl, C 3 -C 8 cycloalkyl; C 1 -C 8 - haloalkyl, C 3 -C 8 -halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or
Bromatomen stehen,bromine atoms stand,
R5 und R6 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Cp C4-Alkyl substituierten gesättigten Heterocyclus mit 5 bis 8 Ringatomen bilden, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus derR 5 and R 6 also, together with the nitrogen atom to which they are bonded, form a saturated heterocycle with 5 to 8 ring atoms, optionally substituted once or more, identically or differently by halogen or Cp C 4 alkyl, the heterocycle being 1 or 2 further, non-adjacent heteroatoms from the
Reihe Sauerstoff, Schwefel oder NR7 enthalten kann,Series may contain oxygen, sulfur or NR 7 ,
R7 für Wasserstoff oder CrC6-Alkyl steht,R 7 represents hydrogen or C r C 6 alkyl,
M für einen jeweils einfach durch R8 substituierten Phenyl- oder Thiophen-Ring oder für jeweils einfach bis vierfach durch R8"8 substituiertes C3-C6-Cycloalkyl oder C3-C6- Cycloalkenyl,M for a phenyl or thiophene ring, each monosubstituted by R 8 or for C 3 -C 6 -cycloalkyl or C 3 -C 6 -cycloalkenyl each monosubstituted to fourfold by R 8"8 ,
R8 für Wasserstoff, Fluor, Chlor, Methyl, iso-Propyl, Methylthio oder Trifluormethyl steht,R 8 represents hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl,
R8"8 für Wasserstoff, Fluor, Chlor, CrC4-Alkyl oder CrC4-Haloalkyl steht,R 8"8 represents hydrogen, fluorine, chlorine, C r C 4 -alkyl or C r C 4 -haloalkyl,
Q für eine direkte Bindung, CrC4-Alkylen, C2-C4-Alkenylen, O, S, SO, SO2 oder NR9 steht,Q represents a direct bond, C r C 4 -alkylene, C 2 -C 4 -alkenylene, O, S, SO, SO 2 or NR 9 ,
R9 für Wasserstoff, CrC8-Alkyl, CrC4-Alkoxy-Ci-C4-alkyl, C,-C4-Alkylthio-CrC4- alkyl, C2-C8-Alkenyl, C2-C8-Alkinyl, Ci-C6-Halogenalkyl, C2-C6-Halogenalkenyl, C2- C6-Halogenalkinyl oder C3-C6-Cycloalkyl steht,R 9 for hydrogen, C r C 8 -alkyl, C r C 4 -alkoxy-Ci-C 4 -alkyl, C,-C 4 -alkylthio-C r C 4 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, Ci-C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl or C 3 -C 6 -cycloalkyl,
R für jeweils gegebenenfalls substituiertes Phenyl, Cycloalkyl oder Bicycloalkyl; oder für unsubstituiertes C2-C2o-Alkyl oder für gegebenenfalls substituiertes Ci-C2o-Alkyl steht,R represents optionally substituted phenyl, cycloalkyl or bicycloalkyl; or represents unsubstituted C 2 -C 2 o-alkyl or optionally substituted C 2 -C 2 o-alkyl,
zur Bekämpfung von bestimmten Rostpilzen, wie Sojabohnenrost und Kaffeerost, im Pflanzenschutz.to combat certain rust fungi, such as soybean rust and coffee rust, in plant protection.
Verwendung von Carboxamiden der Formel (I) gemäß Anspruch 1, worin A für einen der folgenden Reste Al bis A 19 Use of carboxamides of the formula (I) according to claim 1, in which A represents one of the following radicals Al to A 19
A16 A17 A18 A19 steht, R1 für Wasserstoff, CrC6-Alkyl, C,-C4-Alkylsulfinyl, C,-C4-Alkylsulfonyl, CrC3-Alkoxy-A16 A17 A18 A19 stands , R 1 is hydrogen, C r C 6 -alkyl, C,-C 4 -alkylsulfinyl, C,-C 4 -alkylsulfonyl, C r C 3 -alkoxy-
CrC3-alkyl, C3-C6-Cycloalkyl; CrC4-Halogenalkyl, CrC4-Halogenalkylthio, C,-C4- Halogenalkylsulfinyl, CrC4-Halogenalkylsulfonyl, Halogen-CrC3-alkoxy-Ci-C3-alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Ci-C3-alkyl, (CrC3-Alkyl)carbonyl-C,-Cralkyl, (CrC3-Alkoxy)car- bonyl-d-C3-alkyl; Halogen-(CrC3-alkyl)carbonyl-C1-C3-alkyl, Halogen-(CrC3-alk- oxy)carbonyl-CrC3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (CrC6-Alkyl)carbonyl, (CrC4-Alkoxy)carbonyl, (CrC4-Alkylthio)carbonyl, (C,-C3- Alkoxy-C)-C3-alkyl)carbonyl, (C3-C4-Alkenyloxy)carbonyl, (C3-C4-Alkinyloxy)car- bonyl, (C3-C6-Cycloalkyl)carbonyl; (Ci-C4-Halogenalkyl)carbonyl, (Ci-C4-Halogen- alkoxy)carbonyl, (CrC4-Halogenalkylthio)carbonyI, (Halogen-C| -C3-alkoxy-CrC3- alkyl)carbonyl, (C3-C4-Halogenalkenyloxy)carbonyl, (C3-C4-Halogenalkinyloxy)car- bonyl, (C3-C6-Halogencycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -CH2-OC-R1 "A, -CH2-CH=CH-R1 A, -CH=C=CH-R1 "A, -C(=O)C(=O)R2, -CONR3R4 oder -CH2NR5R6 steht, R1 A für Wasserstoff, CrC4-Alkyl, C,-C4-Halogenalkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C r C 3 alkyl, C 3 -C 6 cycloalkyl; C r C 4 -haloalkyl, C r C 4 -haloalkylthio, C,-C 4 - haloalkylsulfinyl, C r C 4 -haloalkylsulfonyl, halogen-C r C 3 -alkoxy-Ci-C 3 -alkyl, C 3 -C 8 -Halogencycloalkyl, each with 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-Ci-C 3 -alkyl, (C r C 3 -alkyl)carbonyl-C,-C r alkyl, (C r C 3 -alkoxy)carbonyl-dC 3 -alkyl; Halogen-(C r C 3 -alkyl)carbonyl-C 1 -C 3 -alkyl, halogen-(C r C 3 -alk-oxy)carbonyl-C r C3-alkyl each with 1 to 13 fluorine, chlorine and /or bromine atoms; (C r C 6 -alkyl)carbonyl, (C r C 4 -alkoxy)carbonyl, (C r C 4 -alkylthio)carbonyl, (C,-C 3 -alkoxy-C)-C 3 -alkyl)carbonyl, ( C 3 -C 4 -alkenyloxy)carbonyl, (C 3 -C 4 -alkynyloxy)carbonyl, (C 3 -C 6 -cycloalkyl)carbonyl; (Ci-C 4 -haloalkyl)carbonyl, (Ci-C 4 -halo-alkoxy)carbonyl, (C r C 4 -haloalkylthio)carbonyI, (halogen-C| -C 3 -alkoxy-C r C 3 -alkyl) carbonyl, (C 3 -C 4 -haloalkenyloxy)carbonyl, (C 3 -C 4 -haloalkynyloxy)carbonyl, (C 3 -C 6 -halocycloalkyl)carbonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms ; or -CH 2 -OC-R 1 "A , -CH 2 -CH=CH-R 1 A , -CH=C=CH-R 1 "A , -C(=O)C(=O)R 2 , -CONR 3 R 4 or -CH 2 NR 5 R 6 , R 1 A is hydrogen, C r C 4 alkyl, C,-C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 - Alkynyl, C3 -
C6-Cycloalkyl, (Ci-C4-Alkoxy)carbonyl, oder Cyano steht,C 6 -cycloalkyl, (Ci-C 4 -alkoxy)carbonyl, or cyano,
R2 für Wasserstoff, C,-C6-Alkyl, CrC4-Alkoxy, Ci-C3-Alkoxy-CrC3-alkyl, C3-C6- Cycloalkyl; CrC4-Halogenalkyl, Ci-C4-Halogenalkoxy, Halogen-Ci-Cs-alkoxy-Cp C3-alkyl, C3-C6-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Brom- atomen steht, - -R 2 is hydrogen, C,-C 6 alkyl, C r C 4 alkoxy, Ci-C 3 alkoxy-C r C 3 alkyl, C 3 -C 6 cycloalkyl; C r C 4 -haloalkyl, Ci-C 4 -haloalkoxy, halogen-Ci-Cs-alkoxy-Cp C 3 -alkyl, C 3 -C 6 -halocycloalkyl, each with 1 to 9 fluoro-, chloro- and/or bromo- atoms stands, - -
R3 und R4 unabhängig voneinander für Wasserstoff, Ci-Cδ-Alkyl, CrC3-Alkoxy-Ci-C3-alkyl, C3-C6-Cycloalkyl; CrC4-Halogenalkyl, Halogen-Ci-C3-alkoxy-CrC3-alkyl, C3-C6- Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,R 3 and R 4 independently represent hydrogen, Ci-C δ -alkyl, C r C 3 -alkoxy-Ci-C 3 -alkyl, C 3 -C 6 -cycloalkyl; C r C 4 -haloalkyl, halogen-Ci-C 3 -alkoxy-C r C 3 -alkyl, C 3 -C 6 - halogencycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms,
R3 und R4 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Halogen oder Ci-C4- Alkyl substituierten gesättigten Heterocyclus mit 5 oder 6 Ringatomen bilden, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR7 enthalten kann,R 3 and R 4 also, together with the nitrogen atom to which they are bonded, form a saturated heterocycle with 5 or 6 ring atoms, optionally mono- to quadruple-substituted, identically or differently substituted by halogen or Ci-C 4 -alkyl, the heterocycle being 1 or Can contain 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 ,
R5 und R6 unabhängig voneinander für Wasserstoff, CrC6-Alkyl, C3-C6-Cycloalkyl; C1-C4- Halogenalkyl, C3-C6-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,R 5 and R 6 independently represent hydrogen, C r C 6 alkyl, C 3 -C 6 cycloalkyl; C 1 -C 4 - haloalkyl, C 3 -C 6 -halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms,
R5 und R6 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Q- Gt-Alkyl substituierten gesättigten Heterocyclus mit 5 oder 6 Ringatomen bilden, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR7 enthalten kann,R 5 and R 6 also, together with the nitrogen atom to which they are bonded, form a saturated heterocycle with 5 or 6 ring atoms, optionally substituted once or more, identically or differently by halogen or Q-G t -alkyl, the heterocycle being 1 or Can contain 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 ,
R7 für Wasserstoff oder Ci-C4-Alkyl steht,R 7 represents hydrogen or Ci-C 4 alkyl,
M für einen der folgenden Cyclen stehtM stands for one of the following cycles
M-I M-7 M-8 M-9 M- 12 M-13M-I M-7 M-8 M-9 M-12 M-13
M-14 M-15 M-16 M"17 wobei die mit „*" markierte Bindung mit dem Amid verknüpft ist, m für 0, 1 oder 2 steht, n für O, 1, M-14 M-15 M-16 M" 17 where the bond marked "*" is linked to the amide, m is 0, 1 or 2, n is O, 1,
2, 3, oder 4 steht, r für 0 oder 1 steht,2, 3, or 4 stands for r stands for 0 or 1,
R8 für Wasserstoff, Fluor, Chlor, Methyl oder Trifluormethyl steht,R 8 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
R 8-B für Fluor, Chlor, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Trifluormethyl oder Difiuormethyl steht, wobei die Reste R8 B gleich oder verschieden sein können, wenn m bzw. n größer als 1 sind, für eine direkte Bindung, für -CH2-, -(CHz)2-, -(CH2)3-, -CH(CH3)-, -C(CH3V, -CH=CH-, -CH2-CH=CH-, -CH(CH3>CH=CH-, O, S, SO, SO2, NR9 steht, R9 für Wasserstoff, CrC6-Alkyl, CrC3-Alkoxy-C,-C3-alkyl, C-Ca-Alkylthio-C-Cj- alkyl oder C3-C6-Cycloalkyl steht, R für gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Phenyl steht, wobei die Substituenten aus der Liste W1 ausgewählt sind, W1 steht für Halogen, Cyano, Nitro, Amino, Hydroxy, Formyl, Carboxyl, Carbamoyl,R 8-B represents fluorine, chlorine, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, trifluoromethyl or difluoromethyl, where the radicals R 8 B can be the same or different, if m or n are greater than 1, for a direct bond, for -CH 2 -, -(CHz) 2 -, -(CH 2 ) 3 -, -CH(CH 3 )-, -C(CH 3 V , -CH=CH-, -CH 2 -CH=CH-, -CH(CH 3 >CH=CH-, O, S, SO, SO 2 , NR 9 stands, R 9 is hydrogen, C r C 6 -alkyl, CrC3-alkoxy-C, -C 3 -alkyl, C-Ca-alkylthio-C-Cj-alkyl or C 3 -C 6 -cycloalkyl, R is optionally simple to represents five times, identically or differently substituted phenyl, the substituents being selected from the list W 1 , W 1 represents halogen, cyano, nitro, amino, hydroxy, formyl, carboxyl, carbamoyl,
Thiocarbamoyl; jeweils geradkettiges oder verzweigtes Alkyl, Hydroxyalkyl, Oxoalkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Dialkoxyalkyl, Alkylthio, Alkylsulfinyl oder Alkyl- sulfonyl mit jeweils 1 bis 8 Kohlenstoffatomen; jeweils geradkettiges oder verzweigtes Alkenyl oder Alkenyloxy mit jeweils 2 bis 6thiocarbamoyl; each straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl, each with 1 to 8 carbon atoms; each straight-chain or branched alkenyl or alkenyloxy, each with 2 to 6
Kohlenstoffatomen; jeweils geradkettiges oder verzweigtes Halogenalkyl, Halogenalkoxy, Halogenalkyl- thio, Halogenalkylsulfinyl oder Halogenalkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiedenen Halogenatomen; jeweils geradkettiges oder verzweigtes Halogenalkenyl oder Halogenalkenyloxy mit jeweils 2 bis 6 Kohlenstoffatomen und 1 bis 11 gleichen oder verschiedenen Halogenatomen; jeweils geradkettiges oder verzweigtes Alkylamino, Dialkylamino, Alkylcarbonyl, Alkylcarbonyloxy, Alkoxycarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Arylalkylaminocarbonyl, Dialkylaminocarbonyloxy mit 1 bis 6 Kohlenstoffatomen in den jeweiligen Kohlenwasserstoffketten, Alkenylcarbonyl oder Alkinylcarbonyl, mit 2 bis 6 Kohlenstoffatomen in den jeweiligen Kohlenwasserstoffketten; Cycloalkyl oder Cycloalkyloxy mit jeweils 3 bis 6 Kohlenstoffatomen; jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Oxo, Methyl, Trifluormethyl oder Ethyl substituiertes, jeweils zweifach verknüpftes Alkylen mit 3 oder 4 Kohlenstoffatomen, Oxyalkylen mit 2 oder 3 Kohlenstoffatomen oder Dioxyalkylen mit 1 oder 2 Kohlenstoffatomen; oder eine Gruppierung -CCQ'^N-Q2, worin Q1 für Wasserstoff, Hydroxy, Alkyl mit 1 bis 4 Kohlenstoffatomen, Halogen- alkyl mit 1 bis 4 Kohlenstoffatomen und 1 bis 9 gleichen oder verschiedenencarbon atoms; each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl, each with 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; each straight-chain or branched haloalkenyl or haloalkenyloxy, each with 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylalkyllaminocarbonyl, dialkylaminocarbonyloxy with 1 to 6 carbon atoms in the respective hydrocarbon chains, alkenylcarbonyl or alkynylcarbonyl, with 2 to 6 carbon atoms in the respective hydrocarbon chains; cycloalkyl or cycloalkyloxy, each having 3 to 6 carbon atoms; each optionally mono- to quadruple-substituted, identically or differently substituted by fluorine, chlorine, oxo, methyl, trifluoromethyl or ethyl, doubly linked alkylene with 3 or 4 carbon atoms, oxyalkylene with 2 or 3 carbon atoms or dioxyalkylene with 1 or 2 carbon atoms; or a group -CCQ'^NQ 2 , where Q 1 represents hydrogen, hydroxy, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different
Halogenatomen oder Cycloalkyl mit 1 bis 6 Kohlenstoffatomen steht und Q2 für Hydroxy, Amino, Methylamino, Phenyl, Benzyl oder für jeweils gegebenenfalls durch Halogen, Cyano, Hydroxy, Alkoxy, Alkylthio, Alkylamino, Dialkylamino oder Phenyl substituiertes Alkyl oder Alkoxy mit 1 bis 4 Kohlenstoffatomen, oder für Alkenyloxy oder Alkinyloxy mit jeweils 2 bisHalogen atoms or cycloalkyl with 1 to 6 carbon atoms and Q 2 represents hydroxy, amino, methylamino, phenyl, benzyl or alkyl or alkoxy with 1 to 4, each optionally substituted by halogen, cyano, hydroxy, alkoxy, alkylthio, alkylamino, dialkylamino or phenyl Carbon atoms, or for alkenyloxy or alkynyloxy, each with 2 to
4 Kohlenstoffatomen steht, sowie jeweils gegebenenfalls im Ringteil einfach bis dreifach durch Halogen, und/oder geradkettiges oder verzweigtes Alkyl oder Alkoxy mit 1 bis 4 Kohlenstoffatomen substituiertes Phenyl, Phenoxy, Phenylthio, Benzoyl, Benzoylethenyl, Cinnamoyl, Heterocyclyl oder Phenylalkyl, Phenylalkyloxy, Phenylalkylthio, oder Heterocyclylalkyl, mit jeweils 1 bis 34 carbon atoms, and phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl or phenylalkyl, phenylalkyloxy, phenylalkylthio, or heterocyclylalkyl, optionally substituted in the ring part once to three times by halogen, and/or straight-chain or branched alkyl or alkoxy with 1 to 4 carbon atoms 1 to 3 each
Kohlenstoffatomen in den jeweiligen Alkylteilen,carbon atoms in the respective alkyl parts,
R außerdem für gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Cp C4-Alkyl substituiertes Cycloalkyl oder Bicycloalkyl mit jeweils 3 bis 10 Kohlenstoffatomen steht, R außerdem für unsubstituiertes C2-C2o-Alkyl oder für einfach oder mehrfach, gleich oder verschieden durch Fluor, Chlor, Brom, Iod und/oder Cß-Cβ-Cycloalkyl substituiertes CrC2o-Alkyl steht, wobei der Cycloalkylteil seinerseits gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Brom, Iod, Ci-C4-Alkyl und/oder Ci-C4-Halogenalkyl substituiert sein kann, R12 für Wasserstoff, Cyano, Halogen, Nitro, CrC4-Alkyl, CrC4-Alkoxy, CrC4-Alkyl- thio, C3-C6-Cycloalkyl, CrC4-Halogenalkyl, CrC4-Halogenalkoxy oder C-C4-HaIo- genalkylthio mit jeweils 1 bis 5 Halogenatomen, Aminocarbonyl oder Aminocar- bonyl-CrC4-alkyl steht,R also represents cycloalkyl or bicycloalkyl, each with 3 to 10 carbon atoms, which is optionally substituted once to four times, identically or differently by Cp C 4 alkyl, R also represents unsubstituted C 2 -C 2 o-alkyl or is substituted once or more, identically or differently C r C 2 o-alkyl substituted by fluorine, chlorine, bromine, iodine and/or C ß -Cβ-cycloalkyl, whereby the cycloalkyl part in turn optionally has one to four times, the same or different, by fluorine, chlorine, bromine, iodine, Ci- C 4 alkyl and/or Ci-C 4 haloalkyl can be substituted, R 12 is hydrogen, cyano, halogen, nitro, C r C 4 alkyl, C r C 4 alkoxy, C r C 4 alkylthio , C 3 -C 6 -cycloalkyl, C r C 4 -haloalkyl, C r C 4 -haloalkoxy or CC 4 -haloalkylthio, each with 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-C r C 4 -alkyl,
R13 fiir Wasserstoff, Halogen, Cyano, C,-C4-Alkyl, C,-C4-Alkoxy oder CrC4-Alkylthio steht,R 13 represents hydrogen, halogen, cyano, C,-C 4 -alkyl, C,-C 4 -alkoxy or C r C 4 -alkylthio,
R14 für Wasserstoff, C,-C4-Alkyl, Hydroxy-Ci-C4-alkyl, C2-C6-Alkenyl, C3-C6-Cycloalkyl,R 14 is hydrogen, C,-C 4 alkyl, hydroxy-Ci-C 4 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl,
CrC4-Alkylthio-CrC4-alkyl, CrC4-Alkoxy-Ci-C4-alkyl, CrC4-Halogenalkyl, C-C4-C r C 4 -alkylthio-C r C 4 -alkyl, C r C 4 -alkoxy-Ci-C 4 -alkyl, CrC 4 -haloalkyl, CC 4 -
Halogenalkylthio-CrC4-alkyl, C-C4-Halogenalkoxy-C-C4-alkyl mit jeweils 1 bis 5Haloalkylthio-C r C 4 -alkyl, CC 4 -haloalkoxy-CC 4 -alkyl with 1 to 5 each
Halogenatomen, oder Phenyl steht, R15 und R16 unabhängig voneinander für Wasserstoff, Halogen, CrC4-Alkyl oder C-C4-HaIo- genalkyl mit 1 bis 5 Halogenatomen steht, R17 für Halogen, Cyano oder CrC4-Alkyl, oder CrC4-Halogenalkyl oder CrC4-Halogen- alkoxy mit jeweils 1 bis 5 Halogenatomen steht,halogen atoms, or phenyl, R 15 and R 16 independently represent hydrogen, halogen, C r C 4 -alkyl or CC 4 -haloalkyl with 1 to 5 halogen atoms, R 17 represents halogen, cyano or C r C 4 - alkyl, or C r C 4 -haloalkyl or C r C 4 -haloalkoxy, each with 1 to 5 halogen atoms,
R18 und R19 unabhängig voneinander für Wasserstoff, Halogen, Ci-C4-Alkyl oder C-C4- Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 18 and R 19 independently represent hydrogen, halogen, Ci-C 4 -alkyl or CC 4 - haloalkyl with 1 to 5 halogen atoms,
R20 für Wasserstoff, Halogen, Ci-C4-Alkyl oder C)-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 20 represents hydrogen, halogen, Ci-C 4 alkyl or C)-C 4 haloalkyl with 1 to 5 halogen atoms,
R21 für Wasserstoff, Halogen, Hydroxy, Cyano, C,-C6-Alkyl, C,-C4-Halogenalkyl, C-C4- Halogenalkoxy oder Q-Q-Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen steht, R22 für Halogen, Hydroxy, Cyano, CrC4-Alkyl, CrC4-Alkoxy, C,-C4-Alkylthio, C1-C4- Halogenalkyl, Ci-C4-Halogenalkylthio oder Ci-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht,R 21 represents hydrogen, halogen, hydroxy, cyano, C,-C 6 -alkyl, C,-C 4 -haloalkyl, CC 4 -haloalkoxy or QQ-haloalkylthio, each with 1 to 5 halogen atoms, R 22 for halogen, hydroxy, cyano, C r C 4 alkyl, C r C 4 alkoxy, C,-C 4 alkylthio, C 1 -C 4 haloalkyl, Ci-C 4 haloalkylthio or Ci-C 4 -Haloalkoxy, each with 1 to 5 halogen atoms,
R23 fiir Wasserstoff, Halogen, Cyano, CrC4-Alkyl, Ci-C4-Alkoxy, C,-C4-Alkylthio, Cr C4-Halogenalkyl, CrC4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen, CrC4-R 23 for hydrogen, halogen, cyano, C r C 4 -alkyl, Ci-C 4 -alkoxy, C,-C 4 -alkylthio, C r C 4 -haloalkyl, C r C 4 -haloalkoxy, each with 1 to 5 halogen atoms , C r C 4 -
Alkylsulphinyl oder Ci-C4-Alkylsulphonyl steht,alkylsulphinyl or Ci-C 4 -alkylsulphonyl,
R24 fiir CrC4-Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R25 fiir C,-C4-Alkyl steht, Q1 fiir S (Schwefel), SO, SO2 oder CH2 steht, p fiir 0, 1 oder 2, wobei R25 für identische oder verschiedene Reste steht, wenn p fiir 2 steht,R 24 represents C r C 4 alkyl or C r C 4 haloalkyl with 1 to 5 halogen atoms, R 25 represents C,-C 4 alkyl, Q 1 represents S (sulfur), SO, SO 2 or CH 2 stands, p stands for 0, 1 or 2, where R 25 stands for identical or different residues when p stands for 2,
R26 fiir C]-C4-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R27 fiir C]-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R28 und R29 unabhängig voneinander für Wasserstoff, Halogen, Amino, CrC4-Alkyl oder Cr Q-Halogenalkyl mit 1 bis 5 Halogenatomen stehen,R 26 represents C]-C 4 -alkyl or QQ-haloalkyl with 1 to 5 halogen atoms, R 27 represents C]-C 4 -alkyl or Ci-C 4 -haloalkyl with 1 to 5 halogen atoms, R 28 and R 29 independently represent hydrogen, halogen, amino, C r C 4 alkyl or C r Q haloalkyl with 1 to 5 halogen atoms,
R30 für Wasserstoff, Halogen, d-C4-Alkyl oder C,-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R31 und R32 unabhängig voneinander für Wasserstoff, Halogen, Amino, Nitro, CrC4-Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen stehen, R33 fiir Wasserstoff, Halogen, CrC4-Alkyl oder C,-C4-Halogenalkyl mit 1 bis 5R 30 represents hydrogen, halogen, dC 4 alkyl or C,-C 4 haloalkyl with 1 to 5 halogen atoms, R 31 and R 32 independently represent hydrogen, halogen, amino, nitro, C r C 4 alkyl or C r represents C 4 -haloalkyl with 1 to 5 halogen atoms, R 33 represents hydrogen, halogen, C r C 4 -alkyl or C,-C 4 -haloalkyl with 1 to 5
Halogenatomen steht, R34 für Wasserstoff, Halogen, Amino, CrC4-Alkylamino, Di-(CrC4-alkyl)amino, Cyano,halogen atoms, R 34 represents hydrogen, halogen, amino, C r C 4 -alkylamino, di-(C r C 4 -alkyl)amino, cyano,
CrC4-Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R35 für Halogen, CrC4-Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R36 fiir Wasserstoff, Halogen, Amino, Ci-C4-Alkylamino, Di-(C rC4-alkyl)amino, Cyano,C r C 4 -alkyl or C r C 4 -haloalkyl with 1 to 5 halogen atoms, R 35 is halogen, C r C 4 -alkyl or C r C 4 -haloalkyl with 1 to 5 halogen atoms, R 36 is hydrogen, Halogen, amino, Ci-C 4 -alkylamino, di-(C r C 4 -alkyl)amino, cyano,
CrC4-Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R37 fiir Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R38 für Halogen, Ci-C4-Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R39 fiir Wasserstoff oder C,-C4-Alkyl steht, R40 fiir Halogen oder CrC4-Alkyl steht,C r C 4 alkyl or C r C 4 haloalkyl with 1 to 5 halogen atoms, R 37 represents halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl with 1 to 5 halogen atoms, R 38 represents halogen, Ci-C 4 -alkyl or C r C 4 -haloalkyl with 1 to 5 halogen atoms, R 39 represents hydrogen or C,-C 4 -alkyl, R 40 represents halogen or C r C 4 -alkyl,
R41 für CrC4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R42 für Wasserstoff, Halogen, CrQ-Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 41 is C r C 4 alkyl or Ci-C 4 haloalkyl with 1 to 5 halogen atoms, R 42 is hydrogen, halogen, C r Q alkyl or C r C 4 haloalkyl with 1 to 5 halogen atoms,
R43 für Halogen, Hydroxy, d-C4-Alkyl, C,-C4-Alkoxy, C,-C4-Alkylthio, C,-C4-Halogen- alkyl, Q-Gi-Halogenalkylthio oder Ci-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht, R44 für Wasserstoff, Cyano, CrC4-Alkyl, C]-C4-Halogenalkyl mit 1 bis 5 Halogenatomen, Hydroxy-C,-C4-alkyl, CrC4-Alkylsulfonyl, Di(C,-C4-alkyl> aminosulfonyl, Q-Cö-Alkylcarbonyl oder jeweils gegebenenfalls substituiertes Phenylsulfonyl oder Benzoyl steht, R45 für Wasserstoff, Halogen, CrC4-Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 43 for halogen, hydroxy, dC 4 -alkyl, C,-C 4 -alkoxy, C,-C 4 -alkylthio, C,-C 4 -halo-alkyl, Q-Gi-haloalkylthio or Ci-C 4 -haloalkoxy each with 1 to 5 halogen atoms, R 44 for hydrogen, cyano, C r C 4 alkyl, C]-C 4 haloalkyl with 1 to 5 halogen atoms, Hydroxy-C,-C 4 -alkyl, C r C 4 -alkylsulfonyl, di(C,-C 4 -alkyl> aminosulfonyl, QC ö -alkylcarbonyl or in each case optionally substituted phenylsulfonyl or benzoyl, R 45 is hydrogen, halogen, C r C 4 -alkyl or C r C 4 -haloalkyl with 1 to 5 halogen atoms,
R46 für Wasserstoff, Halogen, Cyano, CrC4-Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 46 represents hydrogen, halogen, cyano, C r C 4 alkyl or C r C 4 haloalkyl with 1 to 5 halogen atoms,
R47 für Wasserstoff, Halogen, CrC4-Alkyl oder C,-C4-Halogenalkyl mit 1 bis 5 HaIo- genatomen steht,R 47 represents hydrogen, halogen, C r C 4 alkyl or C,-C 4 haloalkyl with 1 to 5 halogen atoms,
R48 für Ci-C4-Alkyl steht.R 48 represents Ci-C 4 alkyl.
3. Verwendung von Carboxamiden der Formel (I) gemäß Anspruch 1 oder 2, worin3. Use of carboxamides of the formula (I) according to claim 1 or 2, wherein
A für einen der Reste Al, A2, A3, A4, A5, A6, A9, AlO, Al l, A12, A17 oder A18 steht, R1 für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Pen- tyl oder Hexyl, Methylsulfinyl, Ethylsulfϊnyl, n- oder iso-Propylsulfinyl, n-, iso-, sec- oder tert-Butylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder iso-Propylsulfonyl, n-, iso-, sec- oder tert-Butylsulfonyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl, Trifluormethyl, Trichlormethyl, Trifluorethyl, Difluormethylthio, Difluorchlormethylthio, Trifluormethylthio, Tri- fluormethylsulfinyl, Trifluormethylsulfonyl, Trifluormethoxymethyl; Formyl, -CH2-CHO, -(CH2)2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CHj)2, -(CH2)Z-CO-CH3, -(CH2)2-CO-CH2CH3, -(CH2)z-CO-CH(CH3)2, -CH2-CO2CH3, -CH2-CO2CH2CH3, -CH2-CO2CH(CH3)2, -(CHz)2-CO2CH3, -(CHs)2-CO2CH2CH3, -(CH2)2-CO2CH(CH3)2, -CH2-CO-CF3, -CH2-CO-CCl3, -CH2-CO-CH2CF3,A represents one of the radicals Al, A2, A3, A4, A5, A6, A9, AlO, Al l, A12, A17 or A18, R 1 represents hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfonyl, n- or iso-propylsulfinyl, n-, iso-, sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl , n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trifluoromethoxymethyl; Formyl, -CH 2 -CHO, -(CH 2 ) 2 -CHO, -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 , -CH 2 -CO-CH(CHj) 2 , - (CH 2 ) Z -CO-CH 3 , -(CH 2 ) 2 -CO-CH 2 CH 3 , -(CH 2 )z-CO-CH(CH 3 ) 2 , -CH 2 -CO 2 CH 3 , -CH 2 -CO 2 CH 2 CH 3 , -CH 2 -CO 2 CH(CH 3 ) 2 , -(CHz) 2 -CO 2 CH 3 , -(CHs) 2 -CO 2 CH 2 CH 3 , -( CH 2 ) 2 -CO 2 CH(CH 3 ) 2 , -CH 2 -CO-CF 3 , -CH 2 -CO-CCl 3 , -CH 2 -CO-CH 2 CF 3 ,
-CH2-CO-CH2CCl3, -(CHz)2-CO-CH2CF3, -(CH2)2-CO-CH2CC13, -CH2-CO2CH2CF3, -CH2-CO2CF2CF3, -CH2-CO2CH2CCl3, -CH2-CO2CCl2CCl3, -(CH2^-CO2CH2CF3, -(CH2)Z-CO2CF2CF3, -(CH2)Z-CO2CH2CCl3, -(CHZ)2-COZCCI2CCI3; Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, iso-Propylcarbonyl, tert-Butyl- carbonyl, Methoxycarbonyl, Ethoxycarbonyl, iso-Propoxycarbonyl, tert--CH 2 -CO-CH 2 CCl 3 , -(CHz) 2 -CO-CH 2 CF 3 , -(CH 2 ) 2 -CO-CH 2 CC1 3 , -CH 2 -CO 2 CH 2 CF 3 , - CH 2 -CO 2 CF 2 CF 3 , -CH 2 -CO 2 CH 2 CCl 3 , -CH 2 -CO 2 CCl 2 CCl 3 , -(CH 2 ^-CO 2 CH 2 CF 3 , -(CH 2 ) Z -CO 2 CF 2 CF 3 , -(CH 2 ) Z -CO 2 CH 2 CCl 3 , -(CHZ) 2 -COZCCI 2 CCI 3 ;methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso-propylcarbonyl, tert-butyl- carbonyl, methoxycarbonyl, ethoxycarbonyl, iso-propoxycarbonyl, tert-
Butoxycarbonyl, Methylthiocarbonyl, Ethylthiocarbonyl, iso-Propylthiocarbonyl, tert-Butylthiocarbonyl, Methoxymethylcarbonyl, Ethoxymethylcarbonyl, Cyclopro- pylcarbonyl; Trifluormethylcarbonyl, Trifluormethoxycarbonyl, Trifiuorme- thylthiocarbonyl, oder -CH2-C≡C-R1 A, -CH2-CH=CH-R1 "A, -CH=C=CH-R1 "A, -C(=O)C(=O)R2, -CONR3R4 oder -CH2NR5R6 steht,butoxycarbonyl, methylthiocarbonyl, ethylthiocarbonyl, isopropylthiocarbonyl, tert-butylthiocarbonyl, methoxymethylcarbonyl, ethoxymethylcarbonyl, cyclopropylcarbonyl; Trifluoromethylcarbonyl, trifluoromethoxycarbonyl, trifluoromethylthiocarbonyl, or -CH 2 -C≡CR 1 A , -CH 2 -CH=CH-R 1 "A , -CH=C=CH-R 1 "A , -C(=O) C(=O)R 2 , -CONR 3 R 4 or -CH 2 NR 5 R 6 stands,
R1 A für Wasserstoff, Methyl oder Ethyl steht, R2 für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, tert-Butyl, Methoxy, Ethoxy, n- oder iso-Propoxy, tert-Butoxy, Methoxymethyl, Cyclopropyl; Trifluormethyl, Tri- fluormethoxy steht,R 1 A represents hydrogen, methyl or ethyl, R 2 is hydrogen, methyl, ethyl, n- or iso-propyl, tert-butyl, methoxy, ethoxy, n- or iso-propoxy, tert-butoxy, methoxymethyl, cyclopropyl; Trifluoromethyl, trifluoromethoxy stands,
R3 und R4 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxy- ethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl; Trifluormethyl, Trichlormethyl, Tri- fluorethyl, Trifluormethoxymethyl stehen,R 3 and R 4 independently represent hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxy-ethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl,
R3 und R4 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Brom oder Methyl substituierten gesättigten Heterocyclus aus der Reihe Morpholin,R 3 and R 4 also, together with the nitrogen atom to which they are bonded, a saturated heterocycle from the series morpholine which is optionally mono- to quadruple-substituted, identically or differently, by fluorine, chlorine, bromine or methyl,
Thiomorpholin oder Piperazin bilden, wobei das Piperazin am zweiten Stickstoffatom durch R7 substituiert sein kann,Thiomorpholine or piperazine form, where the piperazine can be substituted by R 7 on the second nitrogen atom,
R5 und R6 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl; Trifluormethyl, Trichlormethyl,R 5 and R 6 independently represent hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl,
Trifluorethyl, Trifluormethoxymethyl stehen,trifluoroethyl, trifluoromethoxymethyl,
R5 und R6 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Brom oder Methyl substituierten gesättigten Heterocyclus aus der Reihe Morpholin, Thiomorpholin oder Piperazin bilden, wobei das Piperazin am zweitenR 5 and R 6 also, together with the nitrogen atom to which they are bonded, form a saturated heterocycle from the series morpholine, thiomorpholine or piperazine, which is optionally substituted once to four times, identically or differently by fluorine, chlorine, bromine or methyl, where the piperazine on the second
Stickstoffatom durch R7 substituiert sein kann,Nitrogen atom can be substituted by R 7 ,
R7 für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl steht,R 7 represents hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl,
M für einen Ring ausgewählt aus M- 1 , M-7, M- 12, M- 14, M- 15 oder M- 17 steht, m für 0 oder 1 steht, n für 0, 1 oder 2 steht, r für 0 oder 1 steht,M represents a ring selected from M-1, M-7, M-12, M-14, M-15 or M-17, m represents 0 or 1, n represents 0, 1 or 2, r represents 0 or 1 stands,
R8 für Wasserstoff steht,R 8 stands for hydrogen,
R8 für den Fall, dass M für M-I steht, außerdem für Fluor in 4-, 5- oder 6-Position steht,R 8 in the case that M stands for MI, also stands for fluorine in the 4th, 5th or 6th position,
R8 für den Fall, dass M für M-I steht, außerdem für Chlor oder Trifluormethyl in 4- oder 6-Position_steht,R 8 in the case that M stands for MI and also stands for chlorine or trifluoromethyl in the 4- or 6-position,
R8 für den Fall, dass M für M-I steht, außerdem für Methyl in 3-Position steht,R 8 in the case that M stands for MI and also stands for methyl in the 3-position,
R8 für den Fall, dass M für M-2, M-3, M-4 oder M-5 steht, außerdem für Fluor oder Chlor in 6-Position (M-2, M-3) oder in 3-Position (M-A, M-5) steht,R 8 in the event that M stands for M-2, M-3, M-4 or M-5, also for fluorine or chlorine in the 6-position (M-2, M-3) or in the 3-position ( MA, M-5) stands,
R8 ffüürr ddeenn FFaallll,, ddaassss MM ffüürr MM--22,, MM--33,, MM--44 ooddeerr MM--55 sstteehhtt, außerdem für Methyl in 4- Position (M-2) oder in 3-Position (M-3, M-4, M-5) steht, - -R 8 for ddeenn FFaallll,, ddaassss MM for MM--22,, MM--33,, MM--44 ooddeerr MM--55 sstteehhtt, also for methyl in 4-position (M-2) or in 3-position (M-3, M-4, M-5) stands, - -
R8 für den Fall, dass M für M-6 steht, außerdem für Methyl oder Trifluormethyl in 3-R 8 in the case that M stands for M-6, also for methyl or trifluoromethyl in 3-
Position steht, R8 für den Fall, dass M für M-7, M-8 oder M-9 steht, außerdem für Chlor oder Methyl in 5-Position (M-7, M-8) oder in 3-Position (M-9) steht, R8'B für Fluor, Chlor, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Trifluormethyl oder Difluormethyl steht, wobei die Reste R8 B gleich oder verschieden sein können, wenn m bzw. n größer als 1 sind, Q für eine direkte Bindung, -CH2-, -(CHj)2-, -CH(CH3)-, -CH=CH-, -CH2-CH=CH-, O,Position stands, R 8 in the case that M stands for M-7, M-8 or M-9, also for chlorine or methyl in the 5-position (M-7, M-8) or in the 3-position (M -9), R 8'B represents fluorine, chlorine, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, trifluoromethyl or difluoromethyl, where the radicals R 8 B are the same or can be different if m or n are greater than 1, Q for a direct bond, -CH 2 -, -(CHj) 2 -, -CH(CH 3 )-, -CH=CH-, -CH 2 -CH=CH-, O,
S, SO, SO2, NR9, R9 für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, sec-, iso- oder tert-Butyl,S, SO, SO 2 , NR 9 , R 9 for hydrogen, methyl, ethyl, n- or iso-propyl, n-, sec-, iso- or tert-butyl,
Methoxymethyl, Ethoxymethyl, Methoxyethyl, Ethoxyethyl, Methylthiomethyl,Methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl,
Ethylthiomethyl, Methylthioethyl, Ethylthioethyl oder Cyclopropyl steht,Ethylthiomethyl, methylthioethyl, ethylthioethyl or cyclopropyl,
R für einfach in 4-Position, zweifach, gleich oder verschieden in 3,4-Position, 2,4-R for single in 4-position, double, same or different in 3.4-position, 2.4-
Position oder 3,5-Position, oder dreifach, gleich oder verschieden in 2,4,6-Position substituiertes Phenyl, wobei die Substituenten jeweils aus der Liste W1 ausgewählt sind, steht,position or 3,5-position, or three times, identically or differently substituted phenyl in the 2,4,6-position, where the substituents are each selected from the list W 1 ,
W1 für Fluor, Chlor, Brom, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert- Butyl, Methoxy, Ethoxy, n- oder iso-Propoxy, Trifluormethyl, Trifluorethyl, Difluor- methoxy, Trifluormethoxy, Difluorchlormethoxy, Trifluorethoxy, jeweils zweifach verknüpftes Difluormethylendioxy oder Tetrafluorethylendioxy, oder eine Gruppierung -C(Q')=N-Q2 steht, worinW 1 for fluorine, chlorine, bromine, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxy, ethoxy, n- or iso-propoxy, trifluoromethyl, trifluoroethyl, difluoro- methoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, each doubly linked difluoromethylenedioxy or tetrafluoroethylenedioxy, or a group -C(Q')=NQ 2 in which
Q1 für Wasserstoff, Methyl, Ethyl, Trifluormethyl oder Cyclopropyl steht und Q2 für Hydroxy, Methoxy, Ethoxy, Propoxy oder Isopropoxy steht, R für Cyclopentyl, Cyclohexyl, Cycloheptyl, Cyclooctyl, Cyclononyl, Bicyclo[2.2.1]- heptyl oder Bicyclo[2.2.2]octyl steht,Q 1 represents hydrogen, methyl, ethyl, trifluoromethyl or cyclopropyl and Q 2 represents hydroxy, methoxy, ethoxy, propoxy or isopropoxy, R represents cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, bicyclo[2.2.1]-heptyl or bicyclo [2.2.2]octyl stands,
R außerdem für unsubstituiertes C2-C20-Alkyl oder für durch Chlor, Cyclopropyl, Di- chlorcyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl substituiertes Ci-C20- Alkyl steht,R also represents unsubstituted C 2 -C 20 alkyl or Ci-C 20 alkyl substituted by chlorine, cyclopropyl, dichlorocyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
R12 für Wasserstofϊ, Cyano, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, iso-Propyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Cyclopropyl, C,-C2-Halogenalkyl, Q-C2-R 12 for hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, C,-C 2 -haloalkyl, QC 2 -
Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen, Trifluor- methylthio, Difluormethylthio, Aminocarbonyl, Aminocarbonylmethyl oder Amino- carbonylethyl steht,Haloalkoxy, each with 1 to 5 fluorine, chlorine and/or bromine atoms, trifluoromethylthio, difluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl,
R13 für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, Methoxy, Ethoxy, Methylthio oder Ethylthio steht, R14 fiir Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, C,-C2-Halogenalkyl mit 1 bis 5R 13 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio, R 14 for hydrogen, methyl, ethyl, n-propyl, iso-propyl, C,-C 2 -haloalkyl with 1 to 5
Fluor, Chlor und/oder Bromatomen, Hydroxymethyl, Hydroxyethyl, Cyclopropyl,Fluorine, chlorine and/or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl,
Cyclopentyl, Cyclohexyl oder Phenyl steht,Cyclopentyl, cyclohexyl or phenyl is,
R15 und R16 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen stehen,R 15 and R 16 independently represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or Ci-C 2 -haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms,
R17 für Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, d-C2-Halogenalkyl oder C1-C2-R 17 for fluorine, chlorine, bromine, cyano, methyl, ethyl, dC 2 -haloalkyl or C 1 -C 2 -
Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen steht, R18 und R19 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oderHalogenalkoxy, each with 1 to 5 fluorine, chlorine and/or bromine atoms, R 18 and R 19 independently represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or
Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen stehen, R20 für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder C,-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht, R21 für Wasserstoff, Fluor, Chlor, Brom, Iod, Hydroxy, Cyano, CrCrAIkyl, C1-C2-Ci-C 2 haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms, R 20 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C,-C 2 haloalkyl with 1 to 5 fluorine, chlorine and/or or bromine atoms, R 21 represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, C r C r Alkyl, C 1 -C 2 -
Halogenalkyl, CrC2-Halogenalkoxy oder Ci-C2-Halogenalkylthio mit jeweils 1 bis 5Haloalkyl, C r C 2 -haloalkoxy or Ci-C 2 -haloalkylthio, each with 1 to 5
Fluor, Chlor und/oder Bromatomen steht, R22 für Fluor, Chlor, Brom, Iod, Hydroxy, Cyano, d-C4-Alkyl, Methoxy, Ethoxy, Me- thylthio, Ethylthio, Difluormethylthio, Trifluormethylthio, CrC2-Halogenalkyl oderFluorine, chlorine and/or bromine atoms, R 22 represents fluorine, chlorine, bromine, iodine, hydroxy, cyano, dC 4 -alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, C r C 2 -haloalkyl or
Ci-C2-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen steht, R23 für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Ci-C4-Alkyl, Methoxy, Ethoxy,Ci-C 2 -haloalkoxy, each with 1 to 5 fluorine, chlorine and/or bromine atoms, R 23 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, Ci-C 4 -alkyl, methoxy, ethoxy,
Methylthio, Ethylthio, CrC2-Halogenalkyl oder Ci-C2-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen, CrC2-Alkylsulphinyl oder CrC2-Alkyl- sulphonyl steht, R24 für Methyl, Ethyl oder C,-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oderMethylthio, ethylthio, C r C 2 -haloalkyl or Ci-C 2 -haloalkoxy, each with 1 to 5 fluorine, chlorine and / or bromine atoms, C r C 2 -alkylsulphinyl or C r C 2 -alkyl-sulphonyl, R 24 is Methyl, ethyl or C,-C 2 haloalkyl with 1 to 5 fluorine, chlorine and/or
Bromatomen steht, R25 für Methyl oder Ethyl steht, Q1 für S (Schwefel), SO2 oder CH2 steht, p für 0 oder 1 steht,represents bromine atoms, R 25 represents methyl or ethyl, Q 1 represents S (sulfur), SO 2 or CH 2 , p represents 0 or 1,
R26 für Methyl, Ethyl oder C,-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oderR 26 for methyl, ethyl or C,-C 2 haloalkyl with 1 to 5 fluorine, chlorine and/or
Bromatomen steht,bromine atoms,
R27 für Methyl, Ethyl oder C,-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht,R 27 represents methyl, ethyl or C,-C 2 -haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms,
R28 und R29 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Amino, Methyl,R 28 and R 29 independently represent hydrogen, fluorine, chlorine, bromine, amino, methyl,
Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen stehen, R30 für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl oder C,-C2-Halogenalkyl mitEthyl or Ci-C 2 haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms, R 30 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or C,-C 2 haloalkyl
1 bis 5 Fluor, Chlor und/oder Bromatomen steht, R31 und R32 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Amino, Nitro, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen stehen,1 to 5 fluorine, chlorine and/or bromine atoms, R 31 and R 32 independently represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or Ci-C 2 haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms,
R33 für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder C,-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht,R 33 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C,-C 2 -haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms,
R34 für Wasserstoff, Fluor, Chlor, Brom, Amino, Q-Q-Alkylamino, Di(Q-C4- alkyl)amino, Cyano, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht,R 34 represents hydrogen, fluorine, chlorine, bromine, amino, QQ-alkylamino, di(QC 4 -alkyl)amino, cyano, methyl, ethyl or C r C 2 -haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms ,
R35 für Fluor, Chlor, Brom, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht,R 35 represents fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms,
R36 für Wasserstoff, Fluor, Chlor, Brom, Amino, CrC4-Alkylamino, Di(Q-C4- alkyl)amino, Cyano, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht,R 36 for hydrogen, fluorine, chlorine, bromine, amino, C r C 4 -alkylamino, di(QC 4 -alkyl)amino, cyano, methyl, ethyl or Ci-C 2 -haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms,
R37 für Fluor, Chlor, Brom, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht,R 37 represents fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms,
R38 für Fluor, Chlor, Brom, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5 Fluor,R 38 for fluorine, chlorine, bromine, methyl, ethyl or C r C 2 haloalkyl with 1 to 5 fluorine,
Chlor und/oder Bromatomen steht, R39 für Wasserstoff, Methyl oder Ethyl steht, R40 für Fluor, Chlor, Brom, Methyl oder Ethyl steht, R41 für Methyl, Ethyl oder C,-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oderChlorine and/or bromine atoms, R 39 represents hydrogen, methyl or ethyl, R 40 represents fluorine, chlorine, bromine, methyl or ethyl, R 41 represents methyl, ethyl or C,-C 2 haloalkyl with 1 to 5 fluorine , chlorine and/or
Bromatomen steht, R42 für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht,represents bromine atoms, R 42 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms,
R43 für Fluor, Chlor, Brom, Iod, Hydroxy, Q-C4-Al-CyI, Methoxy, Ethoxy, Methylthio, Ethylthio, Difluormethylthio, Trifluormethylthio, C,-C2-Halogenalkyl oder Q-C2-R 43 for fluorine, chlorine, bromine, iodine, hydroxy, QC 4 -Al-CyI, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, C,-C 2 -haloalkyl or QC 2 -
Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen steht, R44 für Wasserstoff, Methyl, Ethyl, C,-C2-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen, Q-C2-Alkoxy-Q-C2-alkyl, Hydroxymethyl, Hydroxyethyl, Methylsulfonyl oder Dimethylaminosulfonyl steht, R45 für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Q-C2-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen steht, R46 für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Methyl, Ethyl, iso-Propyl oder Q-Haloalkoxy, each with 1 to 5 fluorine, chlorine and/or bromine atoms, R 44 is hydrogen, methyl, ethyl, C,-C 2 haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms, QC 2 -alkoxy- QC 2 -alkyl, hydroxymethyl, hydroxyethyl, methylsulfonyl or dimethylaminosulfonyl, R 45 is hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QC 2 -haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms, R 46 for hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, iso-propyl or Q-
C2-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen steht, R47 für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Q-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht,C 2 -haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms, R 47 stands for hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QC 2 -haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms ,
R48 für Methyl, Ethyl, n-Propyl oder iso-Propyl steht. - -R 48 represents methyl, ethyl, n-propyl or iso-propyl. - -
4. Verwendung von Carboxamiden der Formel (I) gemäß Anspruch 1, 2 oder 3, ausgewählt aus4. Use of carboxamides of the formula (I) according to claim 1, 2 or 3, selected from
( 1 ) N-[2-( 1 ,3-Dimethylbutyl)phenyl]- 1 ,3-dimethyl- 1 H-pyrazol-4-carboxamid(1) N-[2-(1,3-Dimethylbutyl)phenyl]-1,3-dimethyl-1H-pyrazole-4-carboxamide
(2) N-[2-( 1 ,3-Dimethylbutyl)phenyl]-5-fluor- 1 ,3-dimethyl- 1 H-pyrazol-4-carboxamid (3) N-[2-( 1 ,3-Dimethylbutyl)phenyl]-5-chlor-l ,3-dimethyl- lH-pyrazol-4-carboxamid(2) N-[2-(1,3-Dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (3) N-[2-(1,3-Dimethylbutyl )phenyl]-5-chloro-l,3-dimethyl-lH-pyrazole-4-carboxamide
(4) 3-(Difluormethyl)-N-[2-( 1 ,3-dimethylbutyl)phenyl]- 1 -methyl- lH-pyrazol-4-carboxamid(4) 3-(Difluoromethyl)-N-[2-(1,3-dimethylbutyl)phenyl]-1-methyl-1H-pyrazole-4-carboxamide
(5) 3-(Trifluormethyl)-N-[2-( 1 ,3-dimethylbutyl)phenyl]-5-fluor- 1 -methyl- 1 H-pyrazol-4- carboxamid(5) 3-(Trifluoromethyl)-N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide
(6) 3-(Trifluormethyl>N-[2-(l,3-dimethylbutyl)phenyl]-5-chlor-l-methyl-lH-pyrazol-4- carboxamid(6) 3-(Trifluoromethyl>N-[2-(l,3-dimethylbutyl)phenyl]-5-chloro-l-methyl-lH-pyrazole-4-carboxamide
(7) l,3-Dimethyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazol-4-carboxamid(7) l,3-Dimethyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazole-4-carboxamide
(8) 5-Fluor-l,3-dimethyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazol-4-carboxamid(8) 5-Fluoro-1,3-dimethyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide
(9) 3-(Difluormethyl>l-methyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazol-4-carb- oxamid (9) 3-(Difluoromethyl>l-methyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazole-4-carboxamide
(10) 3-(Trifluormethyl)-l-methyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazol-4- carboxamid(10) 3-(Trifluoromethyl)-l-methyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazole-4-carboxamide
(11) 3-(Trifluormethyl)-5-fluor-l-methyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazol- 4-carboxamid(11) 3-(Trifluoromethyl)-5-fluoro-l-methyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazole-4-carboxamide
( 12) 3-(Trifluormethyl)-5-chlor-l -methyl-N-[2-( 1 ,3,3-trimethylbutyI)phenyl]- lH-pyrazol- 4-carboxamid(12) 3-(Trifluoromethyl)-5-chloro-l-methyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-lH-pyrazole-4-carboxamide
(13) N-[2-( 1 ,3-Dimethylbutyl)phenyl]-2-iodbenzamid(13) N-[2-(1,3-dimethylbutyl)phenyl]-2-iodobenzamide
( 14) 2-Iod-N-[2-( 1 ,3 ,3-trimethylbutyl)phenyl]benzamid(14) 2-Iodo-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide
(15) N-[2-(l,3-Dimethylbutyl)phenyl]-2-(trifluormethyl)benzamid(15) N-[2-(1,3-dimethylbutyl)phenyl]-2-(trifluoromethyl)benzamide
( 16) 2-(Trifluormethyl)-N-[2-( 1 ,3 ,3-trimethylbutyl)phenyl]benzamid (16) 2-(Trifluoromethyl)-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide
(17) Boscalid(17) Boscalid
(18) l-Methyl-3-trifluormethyl-lΗ-pyrazol-4-carbonsäure-(3-p-tolyl-thiophen-2-yl)-amid(18) l-Methyl-3-trifluoromethyl-lΗ-pyrazole-4-carboxylic acid (3-p-tolyl-thiophen-2-yl)amide
(19) Penthiopyrad(19) Penthiopyrad
(20) N-[2-(l ,3-Dimethylbutyl)phenyl]- 1 -methyl-4-(trifluormethyl)- 1 H-pyrrol-3-carboxamid(20) N-[2-(l,3-dimethylbutyl)phenyl]-1-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxamide
(21 ) N-(3',4'-Dichlor-5-fluor- 1 , 1 '-biphenyl-2-yl)-3-(difluormethyl> 1 -methyl- 1 H-pyrazol-4- carboxamid(21) N-(3',4'-Dichloro-5-fluoro-1,1'-biphenyl-2-yl)-3-(difluoromethyl>1-methyl-1H-pyrazole-4-carboxamide
(22) 3-(Difluormethyl)-N- {3'-fluor-4'-[(£)-(methoxyimino)methyl]- 1 , 1 '-biphenyl-2-yl}- 1 - methyl- lH-pyrazol-4-carboxamid(22) 3-(Difluoromethyl)-N-{3'-fluoro-4'-[(£)-(methoxyimino)methyl]-1,1'-biphenyl-2-yl}-1-methyl-1H-pyrazole -4-carboxamide
(23) 3-(Trifluormethyl)-N-{3'-fluor-41-[(£)-(methoxyimino)methyl]-l,l1-biphenyl-2-yl}-l- methyl- 1 H-pyrazol-4-carboxamid (23) 3-(Trifluoromethyl)-N-{3'-fluoro-4 1 -[(£)-(methoxyimino)methyl]-l,l 1 -biphenyl-2-yl}-l-methyl- 1 H- pyrazole-4-carboxamide
(24) N^'^'-Dichlor-l.l'-biphenyl^-yl^S-fluor-l^-dimethyl-lH-pyrazol^-carboxamid - -(24) N^'^'-dichloro-l.l'-biphenyl^-yl^S-fluoro-l^-dimethyl-lH-pyrazole^-carboxamide - -
(25) N-(4'-Chlor-3'-fluor- 1 , 1 '-biphenyl-2-yl>2-methyl-4-(trifluormethyl)- 1 ,3-thiazol-5- carboxamid(25) N-(4'-Chloro-3'-fluoro-1,1'-biphenyl-2-yl>2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxamide
(26) N-(4'-Chlor- 1 , 1 '-biphenyl-2-yl)-4-(difluormethyl)-2-methyl- 1 ,3-thiazol-5-carboxamid(26) N-(4'-Chloro-1,1'-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide
(27) N-(4'-Brom- 1 , 1 '-biphenyl-2-yl)-4-(difluormethyl)-2-methyl- 1 ,3-thiazol-5-carboxamid (27) N-(4'-Bromo-1,1'-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide
(28) 4-(Difluormethyl>2-methyl-N-[4'-(trifluormethyl)- 1 , 1 '-biphenyl-2-yl]- 1 ,3-thiazoI-5- carboxamid(28) 4-(Difluoromethyl>2-methyl-N-[4'-(trifluoromethyl)-1,1'-biphenyl-2-yl]-1,3-thiazoI-5-carboxamide
(29) N-(4'-Iod- 1 , 1 '-biphenyl-2-yl)-4-(difluormethyl)-2-methyl- 1 ,3-thiazol-5-carboxamid(29) N-(4'-iodo-1,1'-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide
(30) N-(4'-Chlor-3'-fluor- 1 , 1 '-biphenyl-2-yl)-2-methyl-4-(difluormethyl)- 1 ,3-thiazol-5- carboxamid (30) N-(4'-Chloro-3'-fluoro-1,1'-biphenyl-2-yl)-2-methyl-4-(difluoromethyl)-1,3-thiazole-5-carboxamide
(31) Tiadinil(31) Tiadinil
(32) N-[2-(l,3-Dimethylbutyl)phenyl]-l-methyl-4-(trifluormethyl)-lH-pyrrol-3- carboxamid(32) N-[2-(l,3-dimethylbutyl)phenyl]-l-methyl-4-(trifluoromethyl)-lH-pyrrole-3-carboxamide
(33) N-(4'-Chlorbipheny l-2-yl)-3 -iod- 1 -methyl- 1 H-pyrazol-4-carboxamid(33) N-(4'-Chlorbipheny l-2-yl)-3 -iodo- 1 -methyl- 1 H-pyrazole-4-carboxamide
(34) 4-(Difluormethyl>N-[3l-fluor-4'-(trifluormethyl)biphenyl-2-yl]-2-methyl-l,3-thiazol- 5-carboxamid(34) 4-(Difluoromethyl>N-[3 l -fluoro-4'-(trifluoromethyl)biphenyl-2-yl]-2-methyl-l,3-thiazole-5-carboxamide
(35) 3-(Difluormethyl)-N-[2-(3,3-dimethylbutyl)phenyl]-l-methyl-lH-pyrazol-4- carboxamid(35) 3-(Difluoromethyl)-N-[2-(3,3-dimethylbutyl)phenyl]-l-methyl-lH-pyrazole-4-carboxamide
(36) N-[2-(3 ,3-Dimethylbutyl)phenyl]-5-fluor- 1 ,3-dimethyl- 1 H-pyrazol-4-carboxamid (37) N-[3'-Fluor-4'-(trifluormethyl)biphenyl-2-yl]-3-iod-l-methyl-lH-pyrazol-4-carboxamid (38) 3-(Difluormethyl)-N-[2-( 1 ,3-dimethylbutyl)-4-fluoφhenyl]- 1 -methyl- 1 H-pyrazol-4- carboxamid (39) 4-(Difluormethyl>2-methyl-N-{2-[2-(trimethylsilyl)ethyl]-3-thienyl}-l,3-thiazol-5- carboxamid(36) N-[2-(3,3-Dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (37) N-[3'-fluoro-4'- (trifluoromethyl)biphenyl-2-yl]-3-iodo-l-methyl-lH-pyrazole-4-carboxamide (38) 3-(difluoromethyl)-N-[2-(1,3-dimethylbutyl)-4-fluoroφhenyl ]- 1 -methyl- 1 H-pyrazole-4-carboxamide (39) 4-(difluoromethyl>2-methyl-N-{2-[2-(trimethylsilyl)ethyl]-3-thienyl}-l,3-thiazole -5- carboxamide
Verwendung von Carboxamiden der Formel (I) gemäß Anspruch 4, ausgewählt ausUse of carboxamides of the formula (I) according to claim 4, selected from
(2) N-[2-( 1 ,3-Dimethylbutyl)phenyl]-5-fluor- 1 ,3-dimethyl- lH-pyτazol-4-carboxamid (5) 3-(Trifluormethyl)-N-[2-(l,3-dimethylbutyl)phenyl]-5-fluor-l-methyl-lH-pyrazol-4- carboxamid(2) N-[2-(1,3-Dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyτazol-4-carboxamide (5) 3-(Trifluoromethyl)-N-[2-( l,3-dimethylbutyl)phenyl]-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide
(8) 5-Fluor- 1 ,3-dimethyl-N-[2-( 1 ,3,3-trimethylbutyl)phenyl]- 1 H-pyrazol-4-carboxamid (11) 3-(Trifluormethyl)-5-fluor-l-methyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazol-(8) 5-fluoro-1,3-dimethyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide (11) 3-(trifluoromethyl)-5-fluoro -l-methyl-N-[2-(l,3,3-trimethylbutyl)phenyl]-lH-pyrazole-
4-carboxamid4-carboxamide
(13) N-[2-(l,3-Dimethylbutyl)phenyl]-2-iodbenzamid(13) N-[2-(1,3-dimethylbutyl)phenyl]-2-iodobenzamide
( 14) 2-Iod-N-[2-( 1 ,3 ,3-trimethylbutyl)phenyl]benzamid(14) 2-Iodo-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide
( 15) N-[2-( 1 ,3-Dimethylbutyl)phenyl]-2-(trifluormethyl)benzamid (16) 2-(Trifluormethyl)-N-[2-(l,3,3-trimethylbutyl)phenyl]benzamid (21 ) N-(3',4'-Dichlor-5-fluor- 1 , 1 '-biphenyl-2-yl)-3-(difluormethyl> 1 -methyl- 1 H-pyrazol-4- carboxamid(15) N-[2-(1,3-dimethylbutyl)phenyl]-2-(trifluoromethyl)benzamide (16) 2-(trifluoromethyl)-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide (21) N-(3',4'-Dichloro-5-fluoro-1,1'-biphenyl-2-yl)-3-(difluoromethyl>1-methyl-1H-pyrazole-4-carboxamide
(22) 3-(Difluormethyl)-N-{3l-fluor-4l-[(£)-(methoxyimino)methyl]- 1 , 1 '-biphenyl-2-yl}- 1 - methyl- lH-pyrazol-4-carboxamid (23) 3-(Trifluormethyl>N- { 3'-fluor-4'-[(£)-(methoxyimino)rnethyl]- 1 , 1 '-biphenyl-2-yl} - 1 - methyl- lH-pyrazol-4-carboxamid(22) 3-(Difluoromethyl)-N-{3 l -fluoro-4 l -[(£)-(methoxyimino)methyl]- 1, 1 '-biphenyl-2-yl}- 1 -methyl-1H-pyrazole -4-carboxamide (23) 3-(Trifluoromethyl>N- { 3'-fluoro-4'-[(£)-(methoxyimino)rnethyl]- 1 , 1 '-biphenyl-2-yl} - 1 - methyl- lH-pyrazole-4-carboxamide
(24) N-(3',4'-Dichlor-l , 1 '-biphenyl-2-yl)-5-fluor- 1 ,3-dimethyl- lH-pyrazol-4-carboxamid(24) N-(3',4'-dichloro-l,1'-biphenyl-2-yl)-5-fluoro-1,3-dimethyl-lH-pyrazole-4-carboxamide
(25) N-(4'-Chlor-3'-fluor-l , r-biphenyl-2-yl)-2-methyl-4-(trifluormethyl)-l ,3-thiazol-5- carboxamid (26) N-(4'-Chlor- 1 , 1 '-biphenyl-2-yl)-4-(difluormethyl>2-methyl- 1 ,3-thiazol-5-carboxamid(25) N-(4'-Chloro-3'-fluoro-l,r-biphenyl-2-yl)-2-methyl-4-(trifluoromethyl)-l,3-thiazole-5-carboxamide (26) N -(4'-Chloro-1,1'-biphenyl-2-yl)-4-(difluoromethyl>2-methyl-1,3-thiazole-5-carboxamide
(27) N-(4'-Brom- 1 , 1 '-biphenyl-2-yl)-4-(difluormethyl)-2-methyl- 1 ,3-thiazol-5-carboxamid(27) N-(4'-Bromo-1,1'-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide
(28) 4-(Difluormethyl)-2-methyl-N-[4'-(trifluormethyl)- 1 , 1 '-biphenyl-2-yl]- 1 ,3-thiazol-5- carboxamid(28) 4-(Difluoromethyl)-2-methyl-N-[4'-(trifluoromethyl)-1,1'-biphenyl-2-yl]-1,3-thiazol-5-carboxamide
(29) N-(4'-Iod-l,l'-biphenyl-2-yl)-4-(difluormethyl)-2-methyl-l,3-thiazol-5-carboxamid (30) N-(4'-Chlor-3'-fluor- 1 , 1 '-biphenyl-2-yl)-2-methyl-4-(difluormethyl)-l ,3-thiazol-5- carboxamid(29) N-(4'-iodo-l,l'-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-l,3-thiazole-5-carboxamide (30) N-(4' -Chloro-3'-fluoro-1, 1'-biphenyl-2-yl)-2-methyl-4-(difluoromethyl)-1,3-thiazole-5-carboxamide
(33) N-(4'-Chlorbiphenyl-2-yl)-3-iod- 1 -methyl- lH-pyrazol-4-carboxamid(33) N-(4'-Chlorobiphenyl-2-yl)-3-iodo-1-methyl-1H-pyrazole-4-carboxamide
(34) 4-(Difluormethyl)-N-[3'-fluor-4'-(trifluormethyl)biphenyl-2-yl]-2-methyl-l,3-thiazol- 5-carboxamid (35) 3-(Difluormethyl)-N-[2-(3,3-dimethylbutyl)phenyl]-l-methyl-lH-pyrazol-4- carboxamid(34) 4-(Difluoromethyl)-N-[3'-fluoro-4'-(trifluoromethyl)biphenyl-2-yl]-2-methyl-1,3-thiazole-5-carboxamide (35) 3-(Difluoromethyl )-N-[2-(3,3-dimethylbutyl)phenyl]-l-methyl-lH-pyrazole-4-carboxamide
(36) N-[2-(3,3-Dimethylbutyl)phenyl]-5-fluor-l,3-dimethyl-lH-pyrazol-4-carboxamid(36) N-[2-(3,3-Dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide
(37) N-[3'-Fluor-4'-(trifluormethyl)biphenyl-2-yl]-3-iod-l-methyl-lH-pyrazol-4- carboxamid (37) N-[3'-Fluoro-4'-(trifluoromethyl)biphenyl-2-yl]-3-iodo-l-methyl-lH-pyrazole-4-carboxamide
(38) 3-(Difluormethyl)-N-[2-(l,3-dimethylbutyl)-4-fluoφhenyl]-l-methyl-lH-pyrazol-4- carboxamid(38) 3-(Difluoromethyl)-N-[2-(1,3-dimethylbutyl)-4-fluoroφhenyl]-l-methyl-1H-pyrazole-4-carboxamide
(39) 4-(Difluormethyl)-2-methyl-N-{2-[2-(trimethylsilyl)ethyl]-3-thienyl}-l,3-thiazol-5- carboxamid(39) 4-(Difluoromethyl)-2-methyl-N-{2-[2-(trimethylsilyl)ethyl]-3-thienyl}-1,3-thiazole-5-carboxamide
6. Verfahren zum Bekämpfen von Krankheiten von Soja-Pflanzen, dadurch gekennzeichnet, dass man die Soja-Pflanzen mit Carboxamiden der Formel (I) gemäß einem der Ansprüche 1 , 2, 3, 4, oder 5 behandelt.6. A method for combating diseases of soy plants, characterized in that the soy plants are treated with carboxamides of the formula (I) according to one of claims 1, 2, 3, 4, or 5.
7. Verfahren gemäß Anspruch 6 zum Bekämpfen von Krankheiten von transgenen Soja-Pflanzen. 7. Method according to claim 6 for controlling diseases of transgenic soy plants.
8. Verfahren gemäß Anspruch 6 zur Bekämpfung von Alternaria leaf spot (Alternaria spec. atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight8. The method according to claim 6 for combating Alternaria leaf spot (Alternaria spec. atrans tenuissima), anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight
(Drechslera glycini), Frogeye Leaf spot (Cercospora sojina), Leptosphaerulina Leaf Spot (Leptosphaerulina trifolii), Phyllostica Leaf Spot (Phyllosticta sojaecola), Powdery Mildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rhizoctonia Aerial, Foliage, and Web Blight (Rhizoctonia solani), Rust (Phakopsora pachyrhizi), Scab (Sphaceloma glycines), Stemphylium Leaf Blight (Stemphylium botryosum), Target Spot(Drechslera glycini), Frogeye Leaf spot (Cercospora sojina), Leptosphaerulina Leaf Spot (Leptosphaerulina trifolii), Phyllostica Leaf Spot (Phyllosticta sojaecola), Powdery Mildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rhizoctonia Aerial, Foliage, and Web Blight (Rhizoctonia solani), Rust (Phakopsora pachyrhizi), Scab (Sphaceloma glycines), Stemphylium Leaf Blight (Stemphylium botryosum), Target Spot
(Corynespora cassiicola), Black Root Rot (Calonectria crotalariae), Charcoal Rot (Macrophomina phaseolina), Fusarium Blight or WiIt, Root Rot, and Pod and Collar Rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Rot (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Stern Blight (Diaporthe phaseolorum), Stern Canker (Diaporthe phaseolorum var. caulivora), Phytophthora Rot (Phytophthora megasperma), Brown Stern Rot (Phialophora gregata), Pythium Rot (Pythium aphanidermatum, Pythium irreguläre, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Rot, Stern Decay, and Damping-Off (Rhizoctonia solani), Sclerotinia Stern Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Rot(Corynespora cassiicola), Black Root Red (Calonectria crotalariae), Charcoal Red (Macrophomina phaseolina), Fusarium Blight or WiIt, Root Red, and Pod and Collar Red (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Red (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Star Blight (Diaporthe phaseolorum), Star Canker (Diaporthe phaseolorum var. caulivora), Phytophthora Red (Phytophthora megasperma), Brown Star Red (Phialophora gregata), Pythium Red (Pythium aphanidermatum , Pythium irregular, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Rot, Stern Decay, and Damping-Off (Rhizoctonia solani), Sclerotinia Stern Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Rot
(Thielaviopsis basicola). (Thielaviopsis basicola).
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