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EP1966148A1 - Carboxamides - Google Patents

Carboxamides

Info

Publication number
EP1966148A1
EP1966148A1 EP06829295A EP06829295A EP1966148A1 EP 1966148 A1 EP1966148 A1 EP 1966148A1 EP 06829295 A EP06829295 A EP 06829295A EP 06829295 A EP06829295 A EP 06829295A EP 1966148 A1 EP1966148 A1 EP 1966148A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
halogen
hydrogen
haloalkyl
methyl
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Withdrawn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
EP06829295A
Other languages
German (de)
French (fr)
Inventor
Ralf Dunkel
Hans-Ludwig Elbe
Jörg Nico GREUL
Herbert Gayer
Ulrike Wachendorff-Neumann
Peter Dahmen
Arnd Voerste
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1966148A1 publication Critical patent/EP1966148A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/45—Monoamines
    • C07C211/48—N-alkylated amines
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

  • the present invention relates to novel carboxamides, several processes for their preparation and their use for controlling harmful microorganisms in crop protection and material protection.
  • X is O (oxygen) or S (sulfur)
  • M is a phenyl, thiophene, pyridine, pyrimidine, in each case monosubstituted by R 1
  • R 1 is hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl
  • R 2 is hydrogen, methyl, methylthio or trifluoromethyl
  • Q is a direct bond, C r C 4 alkylene, C 2 -C 4 alkenylene, O, S, SO, SO 2 or NR 3,
  • R 3 represents hydrogen, Ci-Cg-alkyl, Ci-C 4 - alkoxy-Ci-C 4 alkyl, C r C 4 -Alkyltiiio-C r C4-alkyl, C 2 -
  • Z represents Z 1 , Z 2 , Z 3 , Z 4 , Z 5 or Z ' 5 ,
  • Z 1 represents optionally mono- to trisubstituted, identically or differently substituted phenyl
  • Z 2 represents optionally mono- to trisubstituted, identically or differently substituted pyridinyl
  • Z 3 in each case optionally mono- or polysubstituted, identically or differently, by halogen
  • Z 4 is unsubstituted C 2 -C 20 alkyl or mono- or polysubstituted by identical or different halogen, alkylthio, alkylsulfinyl , Alkylsulfonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, haloalkoxy, haloalkylamino, halo-dialkylamino, -SiR 6 R 7 R 8 and / or C 3 -C 6 -cycloalkyl-substituted C 1 -
  • C 20 -alkyl where the cycloalkyl moiety in turn may optionally be monosubstituted or polysubstituted, identically or differently, by halogen and / or C 1 -C 4 -alkyl
  • Z 5 is in each case optionally monosubstituted or polysubstituted, identically or differently, by halogen, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, haloalkoxy, haloalkylamino, halo-dialkylamino, -SiR 6 R 7 R 8 and / or C 3 -C 6 -cycloalkyl-substituted C 2 -C 2 o-alkenyl or C 2 -C 2 o-
  • Z 6 is an optionally mono- or polysubstituted, saturated or unsaturated 3- to 7-membered ring which contains a silicon atom as ring member, in which case Q is a direct bond or C r C 4 -alkylene,
  • R 4 is hydrogen or C 1 -C 4 -alkyl
  • R 5 is hydrogen or C 4 alkyl C r, m is 0, 1, 2 or 3;
  • R 6 and R 7 are independently hydrogen, Ci-C 8 alkyl, Ci-C8-alkoxy, Ci-C4-alkoxy-Ci- C4-alkyl, Ci-C4-alkylthio-Ci-C4 - alkyl or C 1 -C 6 -haloalkyl,
  • R 8 is hydrogen, C 1 -C 8 -AlbZl, Ci-C 8 alkoxy, Ci-C 4 alkoxy-C r C 4 alkyl, C r C 4 alkylthio-CrG-alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 alkynyl, Ci-C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 - C ⁇ haloalkynyl, C 3 -C 6 -cycloalkyl, or represents in each case optionally substituted phenyl or phenylalkyl stands, or
  • M-Q-Z together represent in each case optionally monosubstituted to trisubstituted by methyl, N-2,3-dihydro-inden-4-yl, 1,3-dihydro-2-benzofuran-4-yl or 1,3-dihydro-2-benzothien-4-yl,
  • A is one of the following radicals Al to Al 9
  • Ci-C 4 haloalkyl Ci-C4 haloalkoxy or Ci-C is 4 -haloalkylthio having in each case 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-Ci-C 4 alkyl,
  • R 10 is hydrogen, halogen, cyano, C r C 4 alkyl, C 1 -C 4 -alkylthio, R ⁇ hydrogen, QC-alkyl, hydroxy-QC 4 alkyl, C 2 -C 5 alkenyl, Cs-Ce-cycloalkyl, C 1 -C 4 -
  • R 4 -alkyl or halo-QC 4 is 12 and R 13 are independently hydrogen, halogen, C 1 -C alkyl having 1 to 5 halogen atoms, R 14 is halogen, cyano or C 1 -C 4 -alkyl, or C -C 4 haloalkyl or Ci-C is 4 -haloalkoxy having 1 to 5 halogen atoms, R 15 and R 16 independently vonein ⁇ inder hydrogen, halogen, Crd-alkyl or C r C 4 -
  • Halogenoalkyl having 1 to 5 halogen atoms R 17 is hydrogen, halogen, Ci-C 4 alkyl or C r C 4 -halogenoalkyl having 1 to 5 halogen atoms,
  • R 18 is hydrogen, halogen, hydroxy, cyano, C r C 6 alkyl, C r C 4 haloalkyl, QC logenalkoxy 4 -Ha- or C ⁇ halogenoalkylthio each having 1 to 5 halogen atoms,
  • R 19 is halogen, hydroxy, cyano, Ci-C 4 alkyl, C r C 4 alkoxy, CRQ alkylthio, C 1 -C 4 -
  • Halogen atoms is,
  • R 20 is hydrogen, halogen, cyano, C 1 -C 4 -AUCyI, C 1 -C 4 -alkoxy, C r C 4 alkylthio, QC 4 - haloalkyl, QC 4 -haloalkoxy having 1 to 5 halogen atoms, QC 4 -
  • R 21 is Q-Gralkyl or Q-C ⁇ -haloalkyl having 1 to 5 halogen atoms
  • R 22 is QC 4 -alkyl
  • Q 1 is S (sulfur), SO, SO 2 or CH 2
  • p is 0, 1 or 2
  • R 22 is identical or different radicals when p is 2
  • R 23 is C r C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms
  • R 24 is 4 -halogenoalkyl having 1 to 5 halogen atoms for Ci-GrAlkyl or C
  • R 25 and R 26 independently of one another is hydrogen, halogen, amino, dC 4 alkyl or Ci-C 4 - are halogenoalkyl having 1 to 5 halogen atoms
  • R 27 4 -alkyl or Ci-C 4 haloalkyl is hydrogen, halogen, C r C with 1 to 5 halogen atoms, R 28 and R 29 are independently hydrogen, halogen, amino, nitro, Ci-C 4 alkyl or ci
  • R 30 is hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 -haloalkyl having 1 to 5 halogen atoms
  • R 31 is hydrogen, halogen, amino, Ci-C 4- alkylamino, di- (C 1 -C 4 -alkyl) amino, cyano, C 1 -C 4 -
  • R 32 represents halogen, Ci-C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms
  • R 33 is hydrogen alkyl, halogen, amino, Ci-C 4 alkylamino, di- (Ci-C 4 ) amino, cyano, C 1 -C 4 -
  • R 34 represents halogen, Ci-C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms
  • R 35 Ci-C 4 alkyl or Ci-C stands for halogen, 4 -halogenoalkyl having 1 to 5 halogen atoms
  • R 36 is hydrogen or C 1 -C 4 -alkyl
  • R 37 is 4 alkyl halogen or Ci-C
  • R 39 is hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl having 1 to 5 halogen atoms,
  • R 40 is halogen, hydroxy, C 1 -C 4 -alkyl, Cj-C 4 alkoxy, Ci-C 4 alkylthio, C r C 4 haloalkyl, Ci-C4-haloalkylthio or C 4 -haloalkoxy with each 1 to 5 halogen atoms,
  • R 41 represents hydrogen, cyano, Ci-C 4 alkyl, -C 4 -halogenoalkyl having 1 to 5 halogen atoms, QC 4 - alkoxy-Ci-C4-alkyl, hydroxy-C r C 4 alkyl, C 4 - Alkylsulfonyl, di (C r C 4 alkyl) amkosulf ⁇ nyl, Ci-C ⁇ -alkylcarbonyl or in each case optionally substituted Phmylsulfonyl or benzoyl, R 42 is hydrogen, halogen, C 1 -C 4 alkyl or Ci-C 4 -haloalkyl having 1 to 5 halogen atoms stands,
  • R 43 is hydrogen, halogen, cyano, C r C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms
  • R 44 is hydrogen, halogen, C r C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms
  • R 45 is C 1 -C 4 -alkyl.
  • X 1 is halogen or hydroxy, with cyclopropylamines of the formula (III)
  • Acid binder and optionally in the presence of a diluent.
  • novel carboxamides of the formula (I) have very good microbicidal properties and can be used for controlling unwanted microorganisms both in crop protection and in the protection of materials.
  • the compounds of the invention 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. Both the E and the Z isomers, as well as the threo and erythro, and the optical isomers, any mixtures of these isomers, as well as the possible tautomeric forms claimed.
  • the carboxamides according to the invention are generally defined by the formula (I). Preferred radical definitions of the above and below formulas are given below. These definitions apply equally to the end products of formula (I) as well as to all intermediates.
  • X is preferably O (oxygen). X is also preferably S (sulfur). M is preferably one of the following cycles
  • M particularly preferably represents a cycle selected from M-I, M-2, M-3, M-4, M-5, M-
  • M very particularly preferably represents a cycle selected from M-I, M-2, M-5, M-6, M-9,
  • M-IO and M-I l are particularly preferred for the cycle M-I.
  • M is also particularly preferred for the heterocycle M-2. M is also particularly preferred for the heterocycle M-5. M is also particularly preferred for the heterocycle M-6. M is also particularly preferred for the heterocycle M-9. M is also particularly preferred for the heterocycle M-10. M is also particularly preferred for the heterocycle M-11.
  • R is preferably hydrogen.
  • R 1 furthermore preferably represents fluorine, where fluorine is particularly preferably in the 4-, 5- or 6-position, very particularly preferably in 4- or 6-position, in particular 4- Position of Anilidrestes stands.
  • R 1 is in the event that M is MI, moreover preferably chlorine, with chlorine being particularly preferably in the 5-position of the anilide radical.
  • R 1 is in the case that M is MI, moreover preferably methyl, with methyl being particularly preferably in the 3-position of the anilide radical.
  • R 1 is furthermore preferably trifluoromethyl, trifluoromethyl being particularly preferably in the 4- or 5-position of the anilide radical.
  • R 1 is furthermore preferably chlorine, with chlorine being particularly preferably in the 5-position (M-2, M-3) or in the 3-position (M-4) stands.
  • R 1 is also preferably methyl in the case where M is M-2, M-3 or M-4, where methyl is particularly preferably in the 5-position (M-2, M-3) or in the 3-position (M-4) stands.
  • R 1 is also preferred for the case where M is M-5, M-6, M-7 or M-8
  • Fluorine with fluorine particularly preferably in the 6-position (M-5, M-6) or in the 3-position (M-7,
  • R 1 is furthermore preferably chlorine, chlorine being particularly preferably in the 6-position (M-5, M-6) or in the 3-position (M-7, M-8). R 1 is also preferred for the case where M is M-5, M-6, M-7 or M-8
  • Methyl with methyl being particularly preferred in the 4-position (M-5) or in the 3-position (M-6,
  • R 1 stands for the case that M stands for M-9, moreover preferably for methyl, with methyl being particularly preferably in the 3-position.
  • R 1 is in the case that M is M-9, moreover preferably trifluoromethyl, trifluoromethyl being particularly preferably in the 3-position.
  • R 1 stands for the case that M stands for M-12, moreover preferably for methyl, with methyl being particularly preferably in the 4-position.
  • R 1 stands for the case that M stands for M-12, moreover preferably for trifluoromethyl, where
  • Trifluoromethyl is particularly preferably in the 4-position.
  • R 1 stands for the case that M stands for M-13, moreover preferably for methyl, with methyl being particularly preferably in the 3-position.
  • R 1 stands for the case that M stands for M-13, moreover preferably for trifluoromethyl, where
  • Trifluoromethyl is particularly preferably in the 3-position.
  • R 1 stands for the case that M stands for M-14, moreover preferably for methyl, where methyl is particularly preferably in the 3-position.
  • R 1 stands for the case that M stands for M-14, moreover preferably for trifluoromethyl, trifluoromethyl being particularly preferably in the 3-position.
  • R 2 is preferably hydrogen.
  • R 2 is also preferably methyl.
  • R 2 is also preferably trifluoromethyl.
  • Q is preferably a direct bond.
  • Q furthermore Favor g t is -CH 2 -, - (CH 2) 2 -, - (CH 2) 3 -, -CH (CH 3) -, -C (CH j) 2 -, particularly Favor g for t -CH 2 -, - (CH 2 ) 2 -, -CH (CH 3 ) -.
  • Q is preferably O.
  • Q is also preferably S.
  • Q is preferably SO.
  • Q is also preferably SO 2 .
  • Q is also preferably NR 3 , more preferably NH.
  • R 3 preferably represents hydrogen, Ci-C 6 alkyl, C r C 3 alkoxy-Ci-C 3 alkyl, C r C 3 alkylthio
  • R 3 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 3 is very particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, iso- or tert-butyl, methoxymethyl or methylthiomethyl.
  • Z is preferably Z 1 .
  • Z 1 preferably represents optionally mono- to quintuply, identically or differently substituted phenyl, where the substituents are each selected from list W 1 .
  • Z 1 particularly preferably represents monosubstituted phenyl, the substituents being selected from
  • Z 1 is also particularly preferably phenyl which is monosubstituted by identical or different substituents, the substituents being selected from the list W 1 .
  • Z 1 is also particularly preferably triply, identically or differently substituted phenyl, where the substituents are selected from the list W 1 .
  • Z 1 very particularly preferably represents phenyl which is monosubstituted in the 4-position, the
  • Substituents are selected from the list W 1 .
  • Z 1 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 .
  • Z 1 very particularly preferably represents phenyl which is monosubstituted, identically or differently substituted in the 2,3-position, the substituents being selected from the list W 1 .
  • Z 1 very particularly preferably represents phenyl substituted twice, identically or differently in the 2,4-position, the substituents being selected from the list W 1 .
  • Z 1 very particularly preferably represents phenyl which is monosubstituted, identically or differently substituted in the 3,5-position, the substituents being selected from the list W 1 .
  • Z 1 very particularly preferably represents 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, carboxy, carbamoyl, thiocarbamoyl; in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 8 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-
  • 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 the groupings - (CR 4 R 5 ) m SiR 6 R 7 R 8 or -C (Q 2 ) NQ 3 , wherein Q 2 is hydrogen, hydroxy or alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms and 1 to 9 are fluorine, chlorine and / or bromine atoms or cycloalkyl having 1 to 6 carbon atoms and
  • Q 3 is hydroxy, amino, methylamino, phenyl, benzyl or each optionally substituted by cyano, hydroxy, alkoxy, alkylthio, alkylamino, dialkylamino or phenyl alkyl or alkoxy having 1 to 4 carbon atoms, or alkenyl oxy or alkynyloxy with 2 each up to 4 carbon atoms, and in each case optionally in the ring part monosubstituted to halogen, and / or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms substituted phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl or phenylalkyl, phenylalkyloxy, phenylalkylthio, or heterocyclylalkyl, with in each case 1 to 3 carbon atoms in the respective alkyl parts.
  • Q 2 is hydrogen, methyl, ethyl or trifluoromethyl and Q 3 is hydroxy, methoxy, ethoxy, propoxy or isopropoxy.
  • Z is preferably Z 2 .
  • Z 2 is preferably in each case optionally monosubstituted to trisubstituted by identical or different substituents 2-pyridinyl, 3-pyridinyl or 4-pyridinyl, where the substituents are each selected from list W 2 .
  • Z 2 is particularly preferably each monosubstituted 2-pyridinyl, 3-pyridinyl or 4-
  • Z 2 is also particularly preferably each 2-membered, identically or differently substituted 2-pyridinyl, 3-pyridinyl or 4-pyridinyl L wherein the substituents are each selected from the list W 2 .
  • Z 2 is also particularly preferably for each triply, identically or differently substituted 2-pyridinyl-3-pyridinyl or 4-pyridinyl, where the substituents are each selected from the list W 2 .
  • Z 2 very particularly preferably represents 2-pyridinyl which is monosubstituted in the 5-position or 3-pyridinyl which is substituted in the 6-position, the substituents in each case being selected from the list W 2 .
  • Z 2 very particularly preferably represents 2-pyridinyl L which is monosubstituted, identically or differently substituted in 3,5-position, the substituents from the W 2 list being selected.
  • Z 2 very particularly preferably represents twice, identically or differently, 4,6-substituted 3-pyridinyl, the substituents being selected from list W 2 .
  • Z 2 very particularly preferably represents twice, identically or differently, 3,5-substituted 4-pyridinyl, where the substituents are selected from the W 2 list.
  • R 46 and R 47 also together with the nitrogen atom to which they are attached, optionally mono- or polysubstituted by identical or different halogen or
  • R 48 is hydrogen, C r C 4 alkyl , C, -C 4 alkoxy or -NR 51 R 52
  • R 49 represents hydrogen, Ci-C 8 alkyl, Ci-C8-alkoxy, Ci-C 4 alkoxy-dC 4 alkyl, C 1 - C 4 -
  • Alkylthio-Ci-C4-alkyl or Ci-6 haloalkyl is C, where the three radicals R 49 may be the same or different in each case, R 50 is 6 -alkyl, hydrogen or C 1 -C, R 51 is hydrogen or C -C 4 -alkyl, R 52 is hydrogen or C 4 -alkyl-C,
  • R 51 and R 52 also together with the nitrogen atom to which they are attached, one optionally mono- or polysubstituted by identical or different halogen or
  • W 2 is preferably hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, allyl, propargyl, methoxy, ethoxy, n - or iso-propoxy, n-, iso-, sec- or tert-butoxy, methylthio, ethylthio, n- or iso-Propyhhio, n-, iso-, sec- or tert-butylthio, methylsulphinyl, ethylsulphinyl, n- or Iso-Propylsulphinyl, n-, iso-, sec- or tert-butylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or iso-propylsulphonyl,
  • R 46 particularly preferably represents hydrogen or methyl.
  • R 47 particularly preferably represents hydrogen or methyl.
  • R 46 and R 47 together with the nitrogen atom to which they are attached furthermore preferably form a saturated heterocycle from the series morpholine, thiomorpholine or piperazine, optionally monosubstituted to monosubstituted by identical or different fluorine, chlorine, bromine or methyl, wherein the piperazine on the second nitrogen atom may be substituted by R 50 .
  • R 48 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, n- or iso-propoxy or -NR 51 R 52 .
  • R 48 particularly preferably represents hydrogen, methyl, ethyl, methoxy, ethoxy or -NR 51 R 52 .
  • R 49 is preferably methyl, ethyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl or ethylthioethyl, where the three radicals R 49 may each be identical or different
  • R 49 particularly preferably represents methyl, methoxy, methoxymethyl or methylthiomethyl, where the three radicals R 49 may each be identical or different.
  • R 49 is very particularly preferably methyl.
  • R 50 is preferably hydrogen or C 1 -C 4 -alkyl.
  • R 50 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
  • R 51 is preferably hydrogen, methyl, ethyl, n- or isopropyl.
  • R 51 is particularly preferably hydrogen or methyl.
  • R 52 is preferably hydrogen, methyl, ethyl, n- or isopropyl.
  • R 52 particularly preferably represents hydrogen or methyl.
  • R 51 and R 52 together with the nitrogen atom to which they are attached furthermore preferably form a saturated heterocycle from the series morpholine, thiomorpholine or piperazine which is optionally monosubstituted to monosubstituted, identically or differently by fluorine, chlorine, bromine or methyl, wherein the piperazine on the second nitrogen atom may be substituted by R 50 .
  • Z is also preferably Z 3 .
  • Z 3 preferably represents in each case optionally mono- to tetrasubstituted by identical or different halogen, Ci-C 4 alkyl, -CH 2 Si (CH 3) 3 and / or -Si (CH 3) 3-substituted cycloalkyl or bi-cycloalkyl of each 3 to 10 carbon atoms.
  • Z 3 particularly g
  • Favor t in each case optionally mono- to tetrasubstituted by identical or ver ⁇ secreted by chlorine, methyl, -CH 2 Si (CH 3) 3 and / or -Si (CH 3) 3-substituted cyclopropyl, cyclopentyl, cyclohexyl, Cycloheptyl, cyclooctyl, cyclononyl, bicyclo [2.2.1] heptyl or bicyclo [2.2.2] octyl.
  • Z g is particularly preferably substituted by chlorine and methyl-substituted cyclopropyl.
  • Z is also preferably Z 4 .
  • Z 4 is Favor g t represents unsubstituted C 2 -C 2 o alkyl or mono- or polysubstituted by identical or different fluorine, chlorine, bromine, iodine, Ci-C 6 alkylthio, Ci-Ce-alkylsulfinyl, Ci-C 6 -alkylsulfonyl, Ci-C 6 -alkoxy, C, -C 6 -alkylamino, di (C, -C 6 -alkyl) amino, Ci-C ⁇ -haloalkyl thio, Ci-C ⁇ -haloalkylsulfinyl, Ci-Q haloalkylsulfonyl, Ci-C 6 haloalkoxy, Ci-C 6 - Halogenalkylamino, halogen-di (Ci-C 5 alkyl) amino, -SiR 6 R 7 R 8 and / or C 3 -C 6 cycloalkyl substituted
  • Z 4 particularly preferably represents unsubstituted C 2 -C 2 o alkyl.
  • Z 4 is also particularly preferably represents fluorine, chlorine, bromine, iodine, Ci-C 6 alkylthio, Ci-C 4 alkyl sulfinyl, Ci-C 4 alkylsulfonyl, Ci-C 4 alkoxy, Ci-C4- -Alkylammo, di (Ci-C 4 alkyl) amino, QC 4 - haloalkylthio, Ci-C4-HalogenalkylsuU ⁇ nyl, Ci-C4-haloalkylsulfonyl, Ci-C 4 -Halogenalk- oxy, Ci-C4-Halogenalkylamino, halogen-di (Ci-C4-alkyl) amino each with 1 to 9 fluorine, chlorine and / or bromine atoms, -SiR 0 R 7 R 8 , cyclopropyl, dichlorocyclopropyl, cyclobutyl, cyclopent
  • Z is also preferably Z 5 .
  • Z 5 is preferably in each case optionally monosubstituted or polysubstituted, identically or differently, by fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkoxy, C 6 alkylamino, di (Ci-C 6 alkyl) amino, Ci-C ⁇ -haloalkylthio, Ci-Ce-haloalkylsulfinyl, Ci-C ⁇ -haloalkylsulfonyl, Ci-C 6 haloalkoxy, Ci-C 6 alkylamino -Halogenal-, Halo-di (Ci-C 6 -alkyl) ammo, -SiR 6 R 7 R 8 and / or C 3 -C 6 -cycloalkyl-substi
  • Z 5 particularly preferably represents in each case optionally fluorine-, chlorine, bromine, iodine, Ci-C 6 alkylthio -Al-, C, -C 4 alkylsulfinyl, C r C 4 -Alkylsulfbnyl, C r C 4 alkoxy, Ci- C 4 alkylamino 5 di (Ci-C 4 - alkyl) amino, Ci-C 4 -HalogenaUcylthio, C r C 4 haloalkylsulfinyl, CRQ-Halogenalkylsulfbnyl,
  • Ci-C4-haloalkoxy Ci-C 4 -Halogenalkylamino, halogen-di (Ci-C 4 alkyl) amino each having 1 to 9 fluorine, chlorine and / or bromine atoms, -SiR 6 R 7 R 8, cyclopropyl , Dichlorcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted C 2 -C 2 o-alkenyl or C 2 -C 2O -AIkUIyI.
  • Z 5 very particularly preferably represents C 2 -C 20 -alkenyl or C 2 -C 2 o-alkynyl.
  • Z is also preferably Z 6 .
  • Z 6 is preferably one of the following rings
  • R 4 is preferably hydrogen or methyl.
  • R 4 particularly preferably represents hydrogen.
  • R 5 is preferably hydrogen or methyl.
  • R 5 particularly preferably represents hydrogen.
  • n is preferably 0, 1 or 2.
  • R 6 and R 7 independently of one another are preferably C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 3 -alkoxy
  • R 6 and R 7 independently of one another particularly preferably represent methyl, ethyl, methoxy, ethoxy,
  • R 6 and R 7 independently of one another very particularly preferably represent methyl, methoxy,
  • R 6 and R 7 are particularly preferably each methyl.
  • R 8 is Favor g t C r C 6 alkyl, Ci-C 6 alkoxy, Ci-Ca-alkoxy-d-Cj-alkyl, Ci-C3 alkylthio
  • R 8 is particularly preferably methyl, ethyl, n- or iso-propyl, n-, sec-, iso- or tert-butyl, methoxy, ethoxy, n- or iso-propoxy, n-, sec-, iso- or tert-butoxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthio methyl, methylthioethyl, ethylthioethyl, cyclopropyl, phenyl or benzyl.
  • R 8 most preferably represents methyl, ethyl, n- or iso-propyl, iso- or tert-butyl, methoxy, iso-propoxy, iso- or tert-butoxy, methoxymethyl, methylthiomethyl or phenyl.
  • R 8 is particularly preferably methyl, ethyl, n- or iso-propyl, iso- or tert-butyl, methoxy, iso-propoxy, iso- or tert-butoxy.
  • R 8 stands for methyl
  • MQZ are also preferably together l, l, 3-trimethyl-lH-2,3-dihydro-inden-4-yl, 1,3-dimethyl-1 H-2,3-dihydro-inden-4-yl , 1,1,3-Trimethyl-1,3-dihydro-2-benzofuran-4-yl, 1,3-dimethyl-1,3-dihydro-2-benzofuran-4-yl, 1,1,3 Trimethyl-1,3-dihydro-2-benzothien-4-yl or 1,3-dimethyl-1,3-dihydro-2-benzothien-4-yl.
  • M-Q-Z are also particularly preferably together for l, l, 3-trimethyl-lH-2,3-dihydro-inden-4-yl.
  • A is preferably one of the radicals Al, A2, A3, A4, A5, A6, A9, AlO, Al 1, A12, or A17.
  • A is particularly preferably one of the radicals
  • R 9 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-propyl, methoxy, ethoxy, Methyhhio, ethylthio, cyclopropyl, dC ⁇ haloalkyl, Ci-C 2 -HaIo- genalkoxy with in each case 1 to 5 fluorine, chlorine and / or bromine atoms, trifluoromethylthio, di-fluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl.
  • R 9 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-
  • R 9 is very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, isopropyl,
  • R 9 particularly preferably represents methyl, difluoromethyl, trifluoromethyl or 1-fluoroethyl.
  • R 10 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy,
  • R 10 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine or methyl.
  • R 10 very particularly preferably represents hydrogen, fluorine, chlorine or methyl.
  • R 11 is preferably 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 or phenyl.
  • R u particularly preferably represents hydrogen, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl.
  • R 1 ' is very particularly preferably hydrogen, methyl, trifluoromethyl or phenyl.
  • R u is particularly preferably methyl.
  • R 12 and R 13 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, methyl,
  • R 12 and R 13 are particularly preferably each hydrogen.
  • R 14 is preferably fluorine, chlorine, bromine, cyano, methyl, ethyl, C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy having in each case 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 14 particularly preferably represents fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy.
  • R 14 is very particularly preferably fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or
  • R 14 is particularly preferably methyl or trifluoromethyl.
  • R 15 and R 16 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 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, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl.
  • R 15 and R 16 are particularly preferably each hydrogen.
  • R 17 is preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or C r C 2 haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 17 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl.
  • R 17 is very particularly preferably fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl.
  • R 18 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or C 1 -C 2 -haloalkylthio, each having 1 to 5 fluorine , Chlorine and / or bromine atoms.
  • R 18 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopotyl, n-butyl, isobutyl, sec-butyl, tert-butyl, difluoromethyl, Trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio or trichloromethylthio.
  • R 18 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl.
  • R 18 is particularly preferably iodine, methyl, difluoromethyl or trifluoromethyl.
  • R 19 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 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 19 is particularly preferably fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-
  • R 19 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 20 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, Ci-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 20 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 methylsulfonyl.
  • R 20 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 20 particularly preferably represents hydrogen.
  • R 21 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or
  • R 21 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 22 is preferably methyl or ethyl.
  • R 22 is particularly preferably 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 23 is Favor g t represents methyl, EÜiyl or C, -C 2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or
  • R 23 is particularly Favor g t is methyl, ethyl, trifluoromethyl, difluoromethyl, Difluorchlor- methyl or trichloromethyl.
  • R 23 is very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R ⁇ is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or
  • R 24 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 24 is very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 25 and R 26 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino,
  • R 25 and R 26 are particularly preferably each hydrogen.
  • R 27 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 27 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 27 is very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 27 is particularly preferably methyl.
  • R 28 and R 29 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or C 1 -C 9 -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, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 28 and R 29 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine,
  • R 28 and R 29 are particularly preferably each hydrogen.
  • R 30 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 30 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 30 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 30 is particularly preferably methyl.
  • R 31 preferably represents hydrogen, fluorine, chlorine, bromine, amino, Ci-C 4 alkylamino, di (Ci-C 4 - alkyl) amino, cyano, methyl, ethyl or Ci-C 2 haloalkyl having 1 to 5 fluorine , Chlorine and / or bromine atoms.
  • R 31 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
  • R 31 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 31 particularly preferably represents amino, methylamino, dimethylamino, methyl or
  • R 32 is preferably fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 32 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,
  • R 32 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 32 particularly preferably represents methyl, trifluoromethyl or difluoromethyl.
  • R 33 preferably represents hydrogen, fluorine, chlorine, bromine, amino, Ci-C 4 alkylamino, di (Ci-C 4 - alkyl) amino, cyano, methyl, ethyl or Ci-C 2 haloalkyl having 1 to 5 fluorine , Chlorine and / or bromine atoms.
  • R 33 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 33 g anz particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
  • R 33 particularly preferably represents amino, methylamino, dimethylamino, methyl or trifluoromethyl.
  • R 34 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 34 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 34 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl
  • R 34 is particularly preferably methyl, trifluoromethyl or difluoromethyl.
  • R 35 is preferably fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl of 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 36 is preferably hydrogen, methyl or ethyl.
  • R 36 particularly preferably represents methyl.
  • R 37 is preferably fluorine, chlorine, bromine, methyl or ethyl, R 37 is particularly preferably fluorine, chlorine or methyl.
  • R 38 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or
  • R 38 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 38 is very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 38 is particularly preferred: for methyl or trifluoromethyl.
  • R 39 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 39 is particularly Favor g t represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.
  • R 40 is preferably fluorine, chlorine, bromine, iodine, hydroxy, C 1 -C 4 -alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, C r C 2 -haloalkyl or C 1 -C 2 -haloalkoxy, each having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 40 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 40 is very particularly preferably fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 41 preferably represents hydrogen, methyl, ethyl, Ci-C 2 haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, C 1 -C 2 alkoxy-Ci-C 2 alkyl, hydroxymethyl, hydroxyethyl,
  • R 41 particularly preferably represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl,
  • R 41 is very particularly preferably methyl or methoxymethyl.
  • R 42 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QC 2 -
  • R 42 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl
  • R 42 is particularly favorable for hydrogen or methyl.
  • R 43 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 43 is particularly preferably hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 43 is very particularly preferably hydrogen, methyl, difluoromethyl or trifluoromethyl.
  • R 44 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -
  • R 44 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl.
  • R 44 is very particularly preferably hydrogen.
  • R 45 is preferably methyl, ethyl, n-propyl or iso-propyl.
  • R 45 particularly preferably represents methyl or ethyl.
  • Group 4 carboxamides of the formula (Ie) in which X, R 1 , Q, Z and A have the meanings given above.
  • Bond and Z stands for Z 1 .
  • G 2 is hydrogen or methyl
  • G 3 is methyl or ethyl.
  • Z 4 is also preferably one of the groupings G1 to G8
  • G5 G6 G7 G8 particularly preferred for G3. G5 or G7.
  • Ci-C 2 o-alkyl includes the largest range defined herein for an alkyl radical.
  • this definition includes the meanings methyl, ethyl, n-, iso-propyl, n-, iso-, sec-, tert-butyl, and in each case all isomeric pentyls, hexyls, heptyls, octyls, nonyls, decyls, undecycles, dodecyls , Tridecyle, Tetradecyle, Pentadecyle, Hexadecyle, Heptadecyle, Octadecyle, Nonadecyle and Eicosyle.
  • a preferred range is C 2 -C n -alkyl such as ethyl and straight-chain or branched propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl, especially straight-chain or branched C 3 -C 10 -alkyl, such as propyl, 1 -Methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2 , 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbut
  • Alkyl which is substituted by halogen is, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl , 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 3-chloro-1-methylbutyl, 2-chloro -l-methylbutyl, 1-chlorobutyl, 3,3-dichloro-1-methylbutyl, 3-chloro-1-methylbutyl, 1-merthyl-3-trifluoro
  • the substituent -SiR 6 R 7 R 8 preferably represents the following radicals: SiMe 3 , SiMe 2 Et, SiMe 2 CHMe 2 , SiMe 2 CH 2 CHMe 2 , SiMe 2 CH 2 CMe 3 , SiMe 2 OCHMe 2 , SiMe 2 OCH 2 CHMe 2 , SiMe 2 OMe, SiMe 2 CMe 3 , SiMe 2 CH 2 CH 2 Me.
  • C 2 -C 2 o-alkenyl encompasses the largest range defined herein for an alkenyl radical.
  • this definition includes the meanings ethenyl, n-, iso-propenyl, n-, iso-, sec-, tert-butenyl, and in each case all isomeric pentenyls, hexenyls, heptenyls, octenyls, nonenyls, decenyls, undecenyls, dodecenyls, tridecenyls , Tetradecenyls, pentadecenyls, hexadecenyls, heptadecenyls, octadecenyls, nonadecenyls and eicosenyls, 1-methyl-1-propenyl, 1-ethyl-1-butenyl, 2,4-dimethyl-1-pen
  • C 2 -C 2 o-alkynyl includes the largest range defined herein for an alkynyl radical.
  • this definition includes the meanings ethynyl, n-, iso-propynyl, n-, iso-, sec-, tert-butynyl, and in each case all isomeric pentinyls, hexynyls, heptynyls, octynyls, nonynyls, decinyls, undecynyls, dodecyls, tridecinyls , Tetradecinyle, Pentadecinyle, Hexadecinyle, Heptadecinyle, Octadecinyle, Nonadecinyle and Eicosinyle.
  • 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.
  • Carbonkladogenide are generally defined by the formula (II).
  • a and X are preferably, more preferably, very particularly preferably or especially preferred for those meanings which are already preferred in connection with the description of the substances of the formula (I) according to the invention, particularly preferably for this Rest were specified.
  • X 1 is preferably fluorine, chlorine or hydroxyl, more preferably chlorine or hydroxy.
  • the carboxylic acid halides of the formula (II) are known and / or can be prepared by known processes (cf., for example, EP-A 0 545 099, JP-A 01-290662 and US 5,093,347).
  • the cyclopropylamines furthermore required for carrying out the process (a) according to the invention as starting materials are generally defined by the formula (III).
  • M, Q and Z are preferably, more preferably, very particularly preferably or particularly preferably for those meanings which are already preferred in connection with the description of the substances of the formula (I) according to the invention, particularly preferably etc. for this remainder were indicated.
  • M, Q and Z are preferably, more preferably, very particularly preferably or particularly preferably those which are important - tions, which have already been given in connection with the description of the compounds of the formula (I) according to the invention as preferred, particularly preferred, etc. for this radical.
  • the amines of the formula (V) are known (cf., for example, WO 03/070705, EP-A 0 824 099).
  • cyclopropanone derivatives which are furthermore required for carrying out the process (b) according to the invention as starting materials, such as, for example, their acetals or acetal derivatives are known synthetic chemicals.
  • Suitable diluents for carrying out process (a) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as e.g. Petroleum ether, hexane, heptane, cyclohexane,
  • Chlorobenzene dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane
  • Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole
  • Ketones such as acetone
  • Butanone methyl isobutyl ketone or cyclohexanone; Nitriles, such as acetonitrile, Pfopionitril, n- or i-
  • the process (a) according to the invention is carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor all customary inorganic or organic bases are suitable. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, lithium diisopropylamide, sodium ethylate, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, Sodium bicarbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylthiolpholine, N, N-dimethylaminopyr
  • the process (a) according to the invention is carried out in the presence of a suitable coupling reagent (if X 5 is hydroxyl).
  • a suitable coupling reagent if X 5 is hydroxyl.
  • all customary carbonyl activators are suitable. These preferably include N- [3- (dimethylamino) propyl] -N'-ethyl-carbodiimide hydrochloride, N, N'-di-sec-butyl-carbodiimide, N, N'-dicyclohexylcarbodiimide, N, N'-diisopro pylcarbodiimide, 1- (3- (dimethylamirio) propyl) -3-ethyl-carbodiimide-methiodide, 2-bromo-3-ethyl-4-methyl-thiazolium-tetrafluoroborate, N, N-bis [2-oxo-3- oxazolidinyl] phosphorodia
  • reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, one works at temperatures of 0 0 C to 150 0 C, preferably at temperatures from 2O 0 C to 110 0 C.
  • Suitable diluents for carrying out process (b) according to the invention are all inert organic solvents. These include, preferably, aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2- Diethoxyethane or anisole; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides, such as N, N-diethylformamide, N, N-dimethylacetamide, 5
  • reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, one works at temperatures of -40 0 C to 150 0 C, preferably at temperatures of 0 0 C to 100 0 C.
  • the process (b) according to the invention is stirred in the presence of a suitable acid.
  • a suitable acid all conventional inorganic or organic acids are suitable.
  • hydrochloric acid, sulfuric acid, p-toluenesulfonic acid or trifluoroacetic acid most preferably p-toluenesulfonic acid or acetic acid.
  • the acid used can optionally be used in a mixture with water.
  • the process (b) according to the invention is optionally carried out in the presence of a reducing agent.
  • a reducing agent any customary inorganic or organic reducing agents are suitable.
  • process (b) according to the invention for preparing the compounds of the formula (011) in general from 1 to 10 mol, preferably from 1 to 3 mol of [(1-ethoxycyclopropyl) oxy] (trimethyl) are employed per mole of the amine of the formula (TV).
  • the workup is carried out by conventional methods.
  • the processes (a) and (b) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to work under elevated or reduced pressure, generally between 0, 1 bar and 10 bar.
  • the substances according to the invention have a strong microbicidal action and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
  • Fungicides can be used for the control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae,
  • Blumeria species such as Blumeria graminis
  • Podosphaera species such as Podosphaera leucotricha
  • Sphaerotheca species such as Sphaerotheca fuliginea
  • Uncinula species such as Uncinula necator
  • Gymnosporangium species such as Gymnosporangium sabinae
  • Hemileia species such as Hemileia vastatrix
  • Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae
  • Puccinia species such as Puccinia recondita or Puccinia graminis
  • Uromyces species such as Uromyces appendiculatus
  • Bremia species such as Bremia lactucae
  • Peronospora species such as Peronospora pisi or P. brassicae;
  • Phytophthora species such as Phytophthora infestans
  • Plasmopara species such as Plasmopara viticola
  • Pseudoperonospora species such as Pseudoperonospora humuli or
  • Pythium species such as Pythium ultimum
  • Cladosporium species such as Cladosporium cucumerinum
  • Cochliobolus species such as Cochliobolus sativus
  • Cycloconium species such as cycloconium oleaginum
  • Diaporthe species such as Diaporthe citri;
  • Elsinoe species such as Elsinoe fawcettii
  • Gloeosporium species such as, for example, Gloeosporium laeticolor; Glomerella species, such as Glomerella cingulata;
  • Guignardia species such as Guignardia bidwelli;
  • Leptosphaeria species such as Leptosphaeria maculans
  • Magnaporthe species such as Magnaporthe grisea
  • Mycosphaerella species such as Mycosphaerella graminicola and Mycosphaerella fijiensis
  • Phaeosphaeria species such as Phaeosphaeria nodorum
  • Pyrenophora species such as, for example, Pyrenophora teres
  • Ramularia species such as Ramularia collo-cygni
  • Rhynchosporium species such as Rhynchosporium secalis
  • Septoria species such as Sqrtoria apii
  • Typhula species such as Typhula incarnata
  • Venturia species such as Vetituria inaequalis
  • Corticium species such as Corticium graminearum
  • Fusarium species such as Fusarium oxysporum
  • Gaeumannomyces species such as Gaeumaimomyces graminis;
  • Rhizoctonia species such as Rhizoctonia solani
  • Tapesia species such as Tapesia acuformis or Tapesia yallundae;
  • Thielaviopsis species such as Thielaviopsis basicola
  • Ear and panicle diseases caused by e.g.
  • Alternaria species such as Alternaria spp .
  • Aspergillus species such as Aspergillus flavus
  • Cladosporium species such as Cladosporium cladosporioides
  • Claviceps species such as Claviceps purpurea
  • Fusarium species such as Fusarium culmorum
  • Gibberella species such as Gibberella zeae
  • Monographella species such as Monographella nivalis
  • Sphacelotheca species such as Sphacelotheca reiliana
  • Tilletia species such as Tilletia caries
  • Urocystis species such as Urocystis occulta
  • Ustilago species such as Ustilago nuda
  • Aspergillus species such as Aspergillus flavus
  • Botrvtis species such as Botrytis cinerea
  • Penicillium species such as Penicillium expansum and Penicillium purpurogenum
  • Sclerotinia species such as Sclerotinia sclerotiorum
  • Verricilium species such as, for example, Verticilium alboatrum
  • Rhizoctonia species such as Rhizoctonia solani
  • Sclerotium species such as Sclerotium rolfsii
  • Nectria species such as Nectria galligena
  • Esca species such as Phaeomoniella chlamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea;
  • Botrytis species such as Botrytis cinerea
  • Rhizoctonia species such as Rhizoctonia solani
  • Hehninthosporium species such as Helminthosporium solani
  • Xanthomonas species such as Xanthomonas campestris pv. Oryzae
  • Pseudomonas species such as Pseudomonas syringae pv. Lachrymans
  • Erwinia species such as Erwinia amylovora
  • the following diseases of soybean beans can be controlled: fungal diseases on leaves, stems, pods and seeds caused by e.g. Alternaria leaf spot (Alternaria spec. Atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var.
  • Phytophthora red (Phytophthora megasperma), Brown Star Red (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 Star Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola).
  • the active compounds according to the invention also have a strong tonic effect in plants. she are therefore suitable for mobilizing plant's own defenses against attack by unwanted microorganisms.
  • plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of plants in such a way that the treated plants exhibit extensive resistance to these microorganisms with subsequent inoculation with undesired microorganisms.
  • Undesirable microorganisms in the present case are phytopathogenic fungi, bacteria and viruses.
  • 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 within which protection is induced generally extends from 1 to 28 days, preferably 1 to 14, more 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 active compounds according to the invention can be used with particularly good success for controlling cereal diseases, such as, for example, against Puccinia species and diseases in the wine, fruit and vegetable growing, such. against Botrytis, Venturia or Alternaria species.
  • the active compounds according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
  • the active compounds according to the invention may optionally also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of other active ingredients.
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Kumir plants can be plants produced by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods including the transgenic plants and including the plant varieties which can be protected or not protected by plant variety rights.
  • Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, spreading, spreading and in propagation material, in particular in seeds, further by single or multi-layer wrapping.
  • the substances according to the invention can be used to protect industrial materials against infestation and destruction by undesired microorganisms.
  • Technical materials as used herein mean non-living materials that have been prepared for use in the art.
  • technical materials to be protected from microbial alteration or destruction by the active compounds of the invention may be adhesives, glues, paper and board, textiles, leather, wood, paints and plastics, coolants and other materials that may be infested or degraded by microorganisms
  • the materials to be protected also include parts of production plants, for example cooling water circuits, which may be adversely affected by the proliferation of microorganisms.
  • technical materials which may be mentioned are preferably adhesives, glues, papers and cardboard, leather, wood, paints, coolants and heat transfer liquids, particularly preferably wood.
  • microorganisms that can cause degradation or a change in the technical materials, for example, bacteria, fungi, yeasts, algae and mucus organisms may be mentioned.
  • the active compounds according to the invention preferably act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • microorganisms of the following genera Alternaria such as Altemaria tenuis, Aspergillus such as Aspergillus niger, Chaetomium such as Chaetomium globosum, Coniophora such as Coniophora puetana, Lentinus such as Lentinus tigrinus,
  • Penicillium such as Penicillium glaucum, Polyporus such as Polyporus versicolor, Aureobasidium such as Aureobasidium puUulans, Sclerophoma such as Sclerophoma pityophila, Trichoderma such as Trichoderma viride, Escherichia such as Escherichia coli, Pseudomonas such as Pseudomonas aeruginosa, Staphylococcus such as Staphylococcus aureus.
  • the active compounds can be converted into the customary foimulations, 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 Fo ⁇ nultechniken.
  • customary foimulations 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 Fo ⁇ nulmaschineen.
  • 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.
  • 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, for example 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, as well as water.
  • 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, ashaninium oxide and silicates.
  • Suitable emulsifiers and / or foam-formers are: 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, Ligiun-Sulfitablaugen and methylcellulose.
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers can 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 A.dditives 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 active compounds according to the invention can also be used 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.
  • 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:
  • Inhibitors of nucleic acid synthesis e.g. Benalaxyl, Benalaxyl M, Bupirimate, Clozylacone, Dimethirimol, Ethirimol, Furalaxyl, Hymexazole, Mefenoxam, Metalaxyl, Metalaxyl-M, Ofurace,
  • inhibitors of mitosis and cell division e.g. Benomyl, carbendazim, diethofencarb, ethaboxam, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, zoxamide;
  • inhibitors of respiration 3.1) inhibitors of complex I of the respiratory chain: eg diflumetorim; 3.2) inhibitors of complex II of the respiratory chain: eg boscalid / nicobifen, carboxin, fenfuram, flutolanil, furametpyr, Furmecyclox, mepronil, oxycarboxine, penthiopyrad, thifluzamide;
  • inhibitors at the complex III of the respiratory chain e.g. Amisulbrom, azoxystrobin, cyazofamide, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metomino-strobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin;
  • decoupler e.g. Dinocap, fluazinam, meptyldinocap;
  • Inhibitors of ATP production e.g. Fentin acetate, Fentin chloride, Fe ⁇ tin hydroxide, Silthiofam;
  • Inhibitors of amino acid and protein biosynthesis e.g. Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil;
  • inhibitors of the signal transduction e.g. Fenpiclonil, fludioxonil, quinoxyfen;
  • Inhibitors of lipid and membrane synthesis e.g. Biphenyl, chlozolinates, edifenphos, iodocarb, Iprobenfos, iprodione, isoprothiolanes, procymidones, propamocarb, propamocarb hydrochloride, pyrazophos, tolclofos-methyl, vinclozolin;
  • Inhibitors of ergosterol biosynthesis e.g. Aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M,
  • inhibitors of cell wall synthesis e.g. Benthiavalicarb, dimethomorph, flumorph, iprovalicarb, polyoxins, polyoxorim, validamycin A;
  • Inhibitors of melanin biosynthesis e.g. Carpropamide, diclocymet, fenoxanil, phthalides, pyroquilon, tricyclazole;
  • resistance inducers e.g. Acibenzolar-S-methyl, Probenazoles, Tiadinil;
  • carbamates eg alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, azamethiphos, bendocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofiran, 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)
  • 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, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cype ⁇ nethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, empenthrin (IR-isomer), esfenvalerate, etofenprox , Fenfluthrin,
  • Oxadiazines e.g., indoxacarb
  • Acetylcholine Receptor Agonist F Antagonists 3.1 Chloronicotinyls / Neonicotinoids (eg Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitpyratn, Nithiazines, Thiacloprid, Thdamethoxam) 3.2 Nicotine, Bensultap, Cartap
  • Fiproles e.g., acetoprole, ethiprole, fipronil, vaniliprole
  • Mectins for example, abamectin, avermectin, emamectin, emamectin benzoate, ivermectin, milkmectin, milbemycin
  • diacylhydrazines e.g., chromafenozides, halofenozides, methoxyfenozides, tebufenozides
  • Benzoylureas for example bistrifluron, chlorofluazuron, difibenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, trifluoron
  • Buprofezin for example bistrifluron, chlorofluazuron, difibenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, trifluoron
  • Organotins e.g., azocyclotin, cyhexatin, feributatin oxides.
  • METTs e.g., Fenazaquiri, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
  • Site III Electron Transport Inhibitors 14.1 Acequinocyl, Fluacrypyrim 75. Microbial disruptors of insect intestinal membrane Bacillus thuringiensis strains
  • Tetronic acids eg spirodiclofen, spiromesifen
  • 16.2 Tetramic acids [eg 3- (2,5-I ) imethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate ( alias: 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
  • Octopaminergic agonists e.g., Amitraz
  • Inhibitors of magnesium-stimulated ATPase e.g., propargites
  • Agonists of the ryanodine receptor e.g., propargites
  • fumigants e.g., aluminum phosphides, methyl bromides, sulfuryl fluorides
  • Mite Growth Inhibitors eg clofentezine, etoxazole, hexythiazox
  • Amidoflumet benclothiazole, benzoximate, bifenazate, bromopropylate, buprofezin, quinomethionate, chlordimeform, chlorobenzilate, chloropicrin, clothiazoben, cycloprene, cyflumetofen, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, flufenerim, flutenzin , Gossyplure, Hydramethylone, Japonilure, Metoxadiazone, Petroleum, Piperonyl butoxide, Potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin, and the compound 3-methyl-phenyl-propylc
  • the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and yeasts, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
  • Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum Aspergillus species such as Aspergillus niger and Aspergillus fumigatus
  • Trichophyton species such as Trichophyton mentagrophytes
  • Microsporon species such as Microsporon canis and audouinii.
  • the list of these fungi is by no means
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules.
  • the application is done in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, spreading, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil. It can also be the seed of the plants to be treated.
  • the application rates can be varied within a relatively wide range, depending on the mode of administration.
  • Plant parts are the application rates of active ingredient generally between 0.1 and 0.1
  • Application rates of active ingredient generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and K ) 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-type or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant cultivars and their parts are treated.
  • transgenic plants and plant cultivars which may be obtained by genetic engineering, optionally in Combination with conventional methods were obtained (Genetically Modified Organisms) and their parts 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 spectrum of action and / or a Strengthening of the effect of the substances and agents which can be used according to the invention, better plant growth, more developed root system, higher resistance of the plant species or plant variety, increased growth of the shoots, higher plant vitality, increased tolerance to high or low temperatures, increased tolerance to drought or to water or water Soil salinity, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, larger fruits, higher plant size, greener leaf color, earlier flowering, higher quality and / or higher harvest value of the harvested products, higher sugar concentration in the fruits, higher shelf life and / or workability of the harvested products possible, which go beyond the expected effects actually.
  • superadditive superadditive
  • Preferred plants or plant varieties to be treated according to the invention include all plants which have obtained genetic material through the genetic engineering modification which gives these plants particularly advantageous traits, examples of which 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 against insects, mites, phytopathogenic fungi, bacteria and / or Vir and increased tolerance of the plants to certain herbicidal active substances.
  • transgenic plants are the important crops, such as cereals (Wheat, rice), maize, soya, potato, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus and grapes), with special emphasis on maize, soya, potato, cotton, tobacco and oilseed rape.
  • 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, CrylllA, 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
  • herbicidal active compounds for example imidazolinones, sulfonylureas, glyphosates or phosphinotricin (eg "PAT” gene
  • PAT phosphinotricin
  • the genes which confer the desired properties may also be present in combinations with one another in the transgenic plants.
  • “Bt plants” are maize varieties, cottons, soybean varieties and potato varieties sold under the trade names YIELD GARDd (US Pat. corn, cotton, soy), KnockOut® (eg corn), StarLink® (eg corn), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, 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 plant varieties developed or to be marketed in the future with these or future developed genetic traits.
  • the plants listed can be treated particularly advantageously in accordance with the invention with the compounds of the general formula (I) or the active ingredient mixtures according to the 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.
  • the determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluent; linear gradient from 10% acetonitrile to 90% acetonitrile.
  • the calibration is carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms), whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two consecutive alkanones).
  • the lambda max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • dimethylacetamide emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • the plants are then grown in a greenhouse at a temperature of about 20 ° C and relative

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Abstract

The invention relates to novel carboxamides of formula (I) wherein X, M, Q, Z and A have the meanings cited in the description. The invention also relates to several methods for producing said substances, to the use thereof for controlling undesired micro-organisms, to novel intermediate products and to the production thereof.

Description

Carboxamidecarboxamides
Die vorliegende Erfindung betrifft neue Carboxamide, mehrere Verfahren zu deren Herstellung und deren Verwendung zur Bekämpfung von schädlichen Mikroorganismen im Pflanzenschutz und Materialschutz.The present invention relates to novel carboxamides, several processes for their preparation and their use for controlling harmful microorganisms in crop protection and material protection.
Es ist bereits bekannt geworden, dass zahlreiche Carboxamide fungizide Eigenschaften besitzen (vgl. z.B. WO 03/070705, EP-A 0 545 099 und JP-A 9-132567). Die Wirksamkeit der dort beschriebenen Stoffe ist gut, lässt aber bei niedrigen Aufwandmengen in manchen Fallen zu wünschen übrig.It has already been disclosed that numerous carboxamides have fungicidal properties (cf., for example, WO 03/070705, EP-A 0 545 099 and JP-A 9-132567). The effectiveness of the substances described there is good, but leaves at low application rates in some cases to be desired.
Es wurden nun neue Carboxamide der Formel (I)There have now been new carboxamides of the formula (I)
gefunden, in welcher found in which
X für O (Sauerstoff) oder S (Schwefel) steht, M für einen jeweils einfach durch R1 substituierten Phenyl-, Thiophen-, Pyridin-, Pyrimidin-,X is O (oxygen) or S (sulfur), M is a phenyl, thiophene, pyridine, pyrimidine, in each case monosubstituted by R 1
Pyridazin oder Pyrazin-Ring oder für einen durch R2 substituierten Thiazol-Ring steht, R1 für Wasserstoff, Fluor, Chlor, Methyl, iso-Propyl, Methylthio oder Trifluormethyl steht, R2 für Wasserstoff, Methyl, Methylthio oder Trifluormethyl steht,Pyridazine or pyrazine ring or a thiazole ring substituted by R 2 , R 1 is hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl, R 2 is hydrogen, methyl, methylthio or trifluoromethyl,
Q für eine direkte Bindung, CrC4-Alkylen, C2-C4-Alkenylen, O, S, SO, SO2 oder NR3 steht, R3 für Wasserstoff, Ci-Cg-Alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, CrC4-Alkyltiiio-CrC4-alkyl, C2-Q is a direct bond, C r C 4 alkylene, C 2 -C 4 alkenylene, O, S, SO, SO 2 or NR 3, R 3 represents hydrogen, Ci-Cg-alkyl, Ci-C 4 - alkoxy-Ci-C 4 alkyl, C r C 4 -Alkyltiiio-C r C4-alkyl, C 2 -
C8-Alkenyl, C2-C8-Alkinyl, Ci-C6-Halogenalkyl, C2-C6-Halogenalkenyl, C2-C6-Halogen- alkinyl oder C3-C6-Cycloalkyl steht, Z für Z1, Z2, Z3, Z4, Z5 oder Z'5 steht,C 8 alkenyl, C 2 -C 8 alkynyl, Ci-C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, or halo-C 3 -C 6 -cycloalkyl, Z represents Z 1 , Z 2 , Z 3 , Z 4 , Z 5 or Z ' 5 ,
Z1 für gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Phenyl steht, Z2 für gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Pyridinyl steht, Z3 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen,Z 1 represents optionally mono- to trisubstituted, identically or differently substituted phenyl, Z 2 represents optionally mono- to trisubstituted, identically or differently substituted pyridinyl, Z 3 in each case optionally mono- or polysubstituted, identically or differently, by halogen,
Alkyl und/oder -(CR4R5)mSiR6R7R8 substituiertes Cycloalkyl oder Bicycloalkyl steht, Z4 für unsubstituiertes C2-C20-Alkyl oder für einfach oder mehrfach, gleich oder verschieden durch Halogen, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkoxy, Alkylamino, Dialkylamino, Halogenalkylthio, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Halogenalkoxy, Halogenal- kylamino, Halogen-dialkylamino, -SiR6R7R8 und/oder C3-C6-Cycloalkyl substituiertes C1-Alkyl and / or - (CR 4 R 5 ) m SiR 6 R 7 R 8 substituted cycloalkyl or bicycloalkyl, Z 4 is unsubstituted C 2 -C 20 alkyl or mono- or polysubstituted by identical or different halogen, alkylthio, alkylsulfinyl , Alkylsulfonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, haloalkoxy, haloalkylamino, halo-dialkylamino, -SiR 6 R 7 R 8 and / or C 3 -C 6 -cycloalkyl-substituted C 1 -
C20-Alkyl steht, wobei der Cycloalkylteil seinerseits gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen und/oder Ci-C4-Alkyl substituiert sein kann, Z5 fiir jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkoxy, Alkylamino, Dialkylamino, Halogen- alkylthio, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Halogenalkoxy, Halogenalkylamino, Halogen-dialkylamino, -SiR6R7R8 und/oder C3-C6-Cycloalkyl substituiertes C2-C2o-Alkenyl oder C2-C2o-Alkinyl steht, wobei der Cycloalkylteil seinerseits gegebenenfalls einfach oder mehrfach, gleich oder verscliieden durch Halogen und/oder d-C4-Alkyl substituiert sein kann,C 20 -alkyl, where the cycloalkyl moiety in turn may optionally be monosubstituted or polysubstituted, identically or differently, by halogen and / or C 1 -C 4 -alkyl, Z 5 is in each case optionally monosubstituted or polysubstituted, identically or differently, by halogen, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, haloalkoxy, haloalkylamino, halo-dialkylamino, -SiR 6 R 7 R 8 and / or C 3 -C 6 -cycloalkyl-substituted C 2 -C 2 o-alkenyl or C 2 -C 2 o-alkynyl, where the cycloalkyl part in turn may be mono- or polysubstituted, identical or different, by halogen and / or dC 4 - Alkyl may be substituted,
Z6 für einen gegebenenfalls einfach oder mehrfach substituierten, gesättigten oder ungesättigten 3- bis 7-gliedrigen Ring steht, welcher ein Siliziumatom als Ringglied enthält, wobei dann Q für eine direkte Bindung oder CrC4-Alkylen steht,Z 6 is an optionally mono- or polysubstituted, saturated or unsaturated 3- to 7-membered ring which contains a silicon atom as ring member, in which case Q is a direct bond or C r C 4 -alkylene,
R4 für Wasserstoff oder Ci-C4-Alkyl steht,R 4 is hydrogen or C 1 -C 4 -alkyl,
R5 für Wasserstoff oder CrC4-Alkyl steht, m für 0, 1, 2 oder 3 steht,R 5 is hydrogen or C 4 alkyl C r, m is 0, 1, 2 or 3;
R6 und R7 unabhängig voneinander für Wasserstoff, Ci-C8-Alkyl, Ci-C8-Alkoxy, Ci-C4-Alkoxy-Ci- C4-alkyl, Ci-C4-Alkylthio-Ci -C4-alkyl oder Ci-C6-Halogenalkyl stehen,R 6 and R 7 are independently hydrogen, Ci-C 8 alkyl, Ci-C8-alkoxy, Ci-C4-alkoxy-Ci- C4-alkyl, Ci-C4-alkylthio-Ci-C4 - alkyl or C 1 -C 6 -haloalkyl,
R8 für Wasserstoff, C1-C8-AIbZl, Ci-C8-Alkoxy, Ci-C4-Alkoxy-CrC4-alkyl, CrC4-Alkylthio- CrG-alkyl, C2-C8-Alkenyl, C2-C8-Alkinyl, Ci-C6-Halogenalkyl, C2-C6-Halogenalkenyl, C2- Cδ-Halogenalkinyl, C3-C6-Cycloalkyl, oder für jeweils gegebenenfalls substituiertes Phenyl oder Phenylalkyl steht, oderR 8 is hydrogen, C 1 -C 8 -AlbZl, Ci-C 8 alkoxy, Ci-C 4 alkoxy-C r C 4 alkyl, C r C 4 alkylthio-CrG-alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 alkynyl, Ci-C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 - C δ haloalkynyl, C 3 -C 6 -cycloalkyl, or represents in each case optionally substituted phenyl or phenylalkyl stands, or
M-Q-Z gemeinsam für jeweils gegebenenfalls einfach bis dreifach durch Methyl substituiertes IH- 2,3-Dihydro-inden-4-yl, l,3-Dihydro2-benzofuran-4-yl oder l,3-Dihydro2-benzothien-4-yl stehen,M-Q-Z together represent in each case optionally monosubstituted to trisubstituted by methyl, N-2,3-dihydro-inden-4-yl, 1,3-dihydro-2-benzofuran-4-yl or 1,3-dihydro-2-benzothien-4-yl,
A für einen der folgenden Reste Al bis Al 9 stehtA is one of the following radicals Al to Al 9
Al A2 A3 A4 A5Al A2 A3 A4 A5
A6 A7 A8 A9 AlO A6 A7 A8 A9 AlO
All A12 A13 A14 A15All A12 A13 A14 A15
A16 A17 A18 A19A16 A17 A18 A19
R9 für Wasserstoff. Cvano. Haloα en. Nitro. Ci-C1-AIk- vi. C-C-AU coxv. Ci-C-A1kvlthioR 9 for hydrogen. Cvano. Haloα en. Nitro. Ci-C 1 -Alk- vi. CC-AU coxv. Ci-C A1kvlthio
Cβ-Cycloalkyl, Ci-C4-Halogenalkyl, Ci-C4-Halogenalkoxy oder Ci-C4-Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen, Aminocarbonyl oder Aminocarbonyl-Ci-C4-alkyl steht,Cβ-cycloalkyl, Ci-C 4 haloalkyl, Ci-C4-haloalkoxy or Ci-C is 4 -haloalkylthio having in each case 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-Ci-C 4 alkyl,
R10 für Wasserstoff, Halogen, Cyano, CrC4-Alkyl, C1-C4-AIkOXy oder Ci-C4-Alkylthio steht, Rπ für Wasserstoff, Q-C-Alkyl, Hydroxy-Q-C4-alkyl, C2-C5-Alkenyl, Cs-Ce-Cycloalkyl, C1-C4- 4 -alkoxy or C, R 10 is hydrogen, halogen, cyano, C r C 4 alkyl, C 1 -C 4 -alkylthio, R π hydrogen, QC-alkyl, hydroxy-QC 4 alkyl, C 2 -C 5 alkenyl, Cs-Ce-cycloalkyl, C 1 -C 4 -
Alkylthio-CrC4-alkyl, Ci-C4-Alkoxy-Q-C4-alkyl, Q-Gi-Halogenalkyl, Q-C4-Halogeiialkylthio-Alkylthio-C r C 4 alkyl, Ci-C 4 alkoxy-QC 4 alkyl, Q-Gi-haloalkyl, QC 4 -Halogeiialkylthio-
CrC4-alkyl, Q-C4-Halogenalkoxy-Ci-C4-alkyl mit jeweils 1 bis 5 Halogenatomen, oder Phenyl steht,-C 4 alkyl, QC 4 haloalkoxy-Ci-C4-alkyl having in each case 1 to 5 halogen atoms, or phenyl,
R12 und R13 unabhängig voneinander für Wasserstoff, Halogen, C1-C4-AIlCyI oder Q-C4-Halogen- alkyl mit 1 bis 5 Halogenatomen steht, R14 für Halogen, Cyano oder C1-C4-AIlCyI, oder Ci-C4-Halogenalkyl oder Ci-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht, R15 und R16 unabhängig voneinϊinder für Wasserstoff, Halogen, Crd-Alkyl oder CrC4-R 4 -alkyl or halo-QC 4 is 12 and R 13 are independently hydrogen, halogen, C 1 -C alkyl having 1 to 5 halogen atoms, R 14 is halogen, cyano or C 1 -C 4 -alkyl, or C -C 4 haloalkyl or Ci-C is 4 -haloalkoxy having 1 to 5 halogen atoms, R 15 and R 16 independently voneinϊinder hydrogen, halogen, Crd-alkyl or C r C 4 -
Halogenalkyl mit 1 bis 5 Halogenatomen steht, R17 für Wasserstoff, Halogen, Ci-C4-Alkyl oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,Halogenoalkyl having 1 to 5 halogen atoms, R 17 is hydrogen, halogen, Ci-C 4 alkyl or C r C 4 -halogenoalkyl having 1 to 5 halogen atoms,
R18 für Wasserstoff, Halogen, Hydroxy, Cyano, CrC6-Alkyl, CrC4-Halogenalkyl, Q-C4-Ha- logenalkoxy oder d-C^Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen steht,R 18 is hydrogen, halogen, hydroxy, cyano, C r C 6 alkyl, C r C 4 haloalkyl, QC logenalkoxy 4 -Ha- or C ^ halogenoalkylthio each having 1 to 5 halogen atoms,
R19 für Halogen, Hydroxy, Cyano, Ci-C4-Alkyl, CrC4-Alkoxy, CrQ-Alkylthio, C1-C4-R 19 is halogen, hydroxy, cyano, Ci-C 4 alkyl, C r C 4 alkoxy, CRQ alkylthio, C 1 -C 4 -
Halogenalkyl, CrC4-Halogenalkylthio oder Ci-C4-Halogenalkoxy mit jeweils 1 bis 5Haloalkyl, C 1 -C 4 -haloalkylthio or C 1 -C 4 -haloalkoxy having in each case 1 to 5
Halogenatomen steht,Halogen atoms is,
R20 für Wasserstoff, Halogen, Cyano, C1-C4-AUCyI, C1-C4-AIkOXy, CrC4-Alkylthio, Q-C4- Halogenalkyl, Q-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen, Q-C4-R 20 is hydrogen, halogen, cyano, C 1 -C 4 -AUCyI, C 1 -C 4 -alkoxy, C r C 4 alkylthio, QC 4 - haloalkyl, QC 4 -haloalkoxy having 1 to 5 halogen atoms, QC 4 -
Alkylsulphinyl oder Q-C4-Alkylsulphonyl steht,Alkylsulphinyl or QC 4 -alkylsulphonyl,
R21 für Q-GrAlkyl oder Q-Cα-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R22 für Q-C4-Alkyl steht, Q1 für S (Schwefel), SO, SO2 oder CH2 steht, p für 0, 1 oder 2, wobei R22 für identische oder verschiedene Reste steht, wenn p für 2 steht,R 21 is Q-Gralkyl or Q-Cα-haloalkyl having 1 to 5 halogen atoms, R 22 is QC 4 -alkyl, Q 1 is S (sulfur), SO, SO 2 or CH 2 , p is 0, 1 or 2, where R 22 is identical or different radicals when p is 2,
R23 für CrC4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R24 für Ci-GrAlkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R25 und R26 unabhängig voneinander für Wasserstoff, Halogen, Amino, d-C4-Alkyl oder Ci-C4- Halogenalkyl mit 1 bis 5 Halogenatomen stehen,R 23 is C r C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms, R 24 is 4 -halogenoalkyl having 1 to 5 halogen atoms for Ci-GrAlkyl or C, R 25 and R 26 independently of one another is hydrogen, halogen, amino, dC 4 alkyl or Ci-C 4 - are halogenoalkyl having 1 to 5 halogen atoms,
R27 für Wasserstoff, Halogen, CrC4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R28 und R29 unabhängig voneinander für Wasserstoff, Halogen, Amino, Nitro, Ci-C4-Alkyl oder Ci-R 27 4 -alkyl or Ci-C 4 haloalkyl is hydrogen, halogen, C r C with 1 to 5 halogen atoms, R 28 and R 29 are independently hydrogen, halogen, amino, nitro, Ci-C 4 alkyl or ci
C4-Halogenalkyl mit 1 bis 5 Halogenatomen stehen, R30 für Wasserstoff, Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R31 für Wasserstoff, Halogen, Amino, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)amino, Cyano, Ci-C4-C 4 -haloalkyl having 1 to 5 halogen atoms, R 30 is hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 -haloalkyl having 1 to 5 halogen atoms, R 31 is hydrogen, halogen, amino, Ci-C 4- alkylamino, di- (C 1 -C 4 -alkyl) amino, cyano, C 1 -C 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,
R32 für Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R33 für Wasserstoff, Halogen, Amino, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)amino, Cyano, C1-C4-R 32 represents halogen, Ci-C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms, R 33 is hydrogen alkyl, halogen, amino, Ci-C 4 alkylamino, di- (Ci-C 4 ) amino, cyano, C 1 -C 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,
R34 für Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R35 für Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R36 für Wasserstoff oder C1-C4-AIlCyI steht, R37 für Halogen oder Ci-C4-Alkyl steht,R 34 represents halogen, Ci-C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms, R 35 Ci-C 4 alkyl or Ci-C stands for halogen, 4 -halogenoalkyl having 1 to 5 halogen atoms, R 36 is hydrogen or C 1 -C 4 -alkyl, R 37 is 4 alkyl halogen or Ci-C,
R38 für Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 38 4 -alkyl or Ci-C 4 haloalkyl having 1 stands for Ci-C to 5 halogen atoms,
R39 für Wasserstoff, Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 39 is hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl having 1 to 5 halogen atoms,
R40 für Halogen, Hydroxy, C1-C4-AIkVl, Cj-C4-Alkoxy, Ci-C4-Alkylthio, CrC4-Halogenalkyl, Ci-C4-Halogenalkylthio oder Ci-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht,R 40 is halogen, hydroxy, C 1 -C 4 -alkyl, Cj-C 4 alkoxy, Ci-C 4 alkylthio, C r C 4 haloalkyl, Ci-C4-haloalkylthio or C 4 -haloalkoxy with each 1 to 5 halogen atoms,
R41 für Wasserstoff, Cyano, Ci-C4-Alkyl, CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen, Q-C4- Alkoxy-Ci-C4-alkyl, Hydroxy-CrC4-alkyl, Ci-C4-Alkylsulfonyl, Di(CrC4-alkyl)amkosulfαnyl, Ci-Cβ-Alkylcarbonyl oder jeweils gegebenenfalls substituiertes Phmylsulfonyl oder Benzoyl steht, R42 für Wasserstoff, Halogen, d-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 41 represents hydrogen, cyano, Ci-C 4 alkyl, -C 4 -halogenoalkyl having 1 to 5 halogen atoms, QC 4 - alkoxy-Ci-C4-alkyl, hydroxy-C r C 4 alkyl, C 4 - Alkylsulfonyl, di (C r C 4 alkyl) amkosulfαnyl, Ci-Cβ-alkylcarbonyl or in each case optionally substituted Phmylsulfonyl or benzoyl, R 42 is hydrogen, halogen, C 1 -C 4 alkyl or Ci-C 4 -haloalkyl having 1 to 5 halogen atoms stands,
R43 für Wasserstoff, Halogen, Cyano, CrC4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R44 für Wasserstoff, Halogen, CrC4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R45 für C1-C4-AIlCyI steht. Weiterhin wurde gefunden, dass man Carboxamide der Formel (I) erhält, indem man (a) Carbonsäurehalogenide der Formel (II) XR 43 is hydrogen, halogen, cyano, C r C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms, R 44 is hydrogen, halogen, C r C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms, R 45 is C 1 -C 4 -alkyl. It has furthermore been found that carboxamides of the formula (I) are obtained by reacting (a) carboxylic acid halides of the formula (II) X.
. /\„l (H) in welcher, / \ "L (H) in which
A und X die oben angegebenen Bedeutungen haben,A and X have the meanings given above,
X1 für Halogen oder Hydroxy steht, mit Cyclopropylaminen der Formel (III)X 1 is halogen or hydroxy, with cyclopropylamines of the formula (III)
in welcher M, Q und Z die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Kupplungsreagenzes, gegebenenfalls in Gegenwart eines in which M, Q and Z have the meanings given above, if appropriate in the presence of a coupling reagent, if appropriate in the presence of a
Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt.Acid binder and optionally in the presence of a diluent.
Schließlich wurde gefunden, dass die neuen Carboxamide der Formel (I) sehr gute mikrobizide Eigenschaften besitzen und zur Bekämpfung unerwünschter Mikroorganismen sowohl im Pflanzen- schütz als auch im Materialschutz verwendbar sind.Finally, it has been found that the novel carboxamides of the formula (I) have very good microbicidal properties and can be used for controlling unwanted microorganisms both in crop protection and in the protection of materials.
Die erfindungsgemäßen Verbindungen 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. Es werden 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 beansprucht.The compounds of the invention 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. Both the E and the Z isomers, as well as the threo and erythro, and the optical isomers, any mixtures of these isomers, as well as the possible tautomeric forms claimed.
Die erfindungsgemäßen Carboxamide sind durch die Formel (I) allgemein definiert. Bevorzugte Restedefinitionen der vorstehenden und nachfolgend genannten Formeln sind im Folgenden angegeben. Diese Definitionen gelten für die Endprodukte der Formel (I) wie für alle Zwischenprodukte gleichermaßen.The carboxamides according to the invention are generally defined by the formula (I). Preferred radical definitions of the above and below formulas are given below. These definitions apply equally to the end products of formula (I) as well as to all intermediates.
X steht bevorzugt für O (Sauerstoff). X steht auch bevorzugt für S (Schwefel). M steht bevorzugt für einen der folgenden Cyclen X is preferably O (oxygen). X is also preferably S (sulfur). M is preferably one of the following cycles
wobei die mit „*" markierte Bindung mit dem Amid, die mit „#" markierte Bindung mit dem Rest R verknüpft ist. wherein the bond marked with "*" is linked to the amide, the bond marked "#" is linked to the radical R.
M steht besonders bevorzugt für einen Cyclus ausgewählt aus M-I, M-2, M-3, M-4, M-5, M-M particularly preferably represents a cycle selected from M-I, M-2, M-3, M-4, M-5, M-
6, M-9, M-IO und M-I l. M steht ganz besonders bevorzugt für einen Cyclus ausgewählt aus M-I, M-2, M-5, M-6, M-9,6, M-9, M-IO and M-I l. M very particularly preferably represents a cycle selected from M-I, M-2, M-5, M-6, M-9,
M-IO und M-I l. M steht insbesondere bevorzugt für den Cyclus M-I .M-IO and M-I l. M is particularly preferred for the cycle M-I.
M steht außerdem insbesondere bevorzugt für den Heterocyclus M-2. M steht außerdem insbesondere bevorzugt für den Heterocyclus M-5. M steht außerdem insbesondere bevorzugt für den Heterocyclus M-6. M steht außerdem insbesondere bevorzugt für den Heterocyclus M-9. M steht außerdem insbesondere bevorzugt für den Heterocyclus M-10. M steht außerdem insbesondere bevorzugt für den Heterocyclus M-11.M is also particularly preferred for the heterocycle M-2. M is also particularly preferred for the heterocycle M-5. M is also particularly preferred for the heterocycle M-6. M is also particularly preferred for the heterocycle M-9. M is also particularly preferred for the heterocycle M-10. M is also particularly preferred for the heterocycle M-11.
R steht bevorzugt für Wasserstoff.R is preferably hydrogen.
R1 steht für den Fall, dass M iur M-I steht, außerdem bevorzugt für Fluor, wobei Fluor beson- ders bevorzugt in 4-, 5- oder 6-Position, ganz besonders bevorzugt in 4- oder 6-Posrtion, insbesondere in 4-Position des Anilidrestes steht. R1 steht für den Fall, dass M für M-I steht, außerdem bevorzugt für Chlor, wobei Chlor besonders bevorzugt in 5-Position des Anilidrestes steht.In the case where M is MI, R 1 furthermore preferably represents fluorine, where fluorine is particularly preferably in the 4-, 5- or 6-position, very particularly preferably in 4- or 6-position, in particular 4- Position of Anilidrestes stands. R 1 is in the event that M is MI, moreover preferably chlorine, with chlorine being particularly preferably in the 5-position of the anilide radical.
R1 steht für den Fall, dass M für M-I steht, außerdem bevorzugt für Methyl, wobei Methyl besonders bevorzugt in 3-Position des Anilidrestes steht. R1 steht für dm Fall, dass M für M-I steht, außerdem bevorzugt für Trifluormethyl, wobei Triflu- ormethyl besonders bevorzugt in 4- oder 5-Position des Anilidrestes steht. R1 steht für den Fall, dass M für M-2, M-3 oder M-4 steht, außerdem bevorzugt für Chlor, wobei Chlor besonders bevorzugt in 5-Position (M-2, M-3) oder in 3-Position (M-4) steht. R1 steht für den Fall, dass M für M-2, M-3 oder M-4 steht, außerdem bevorzugt für Methyl, wobei Methyl besonders bevorzugt in 5-Position (M-2, M-3) oder in 3-Position (M-4) steht. R1 steht für den Fall, dass M für M-5, M-6, M-7 oder M-8 steht, außerdem bevorzugt fürR 1 is in the case that M is MI, moreover preferably methyl, with methyl being particularly preferably in the 3-position of the anilide radical. In the case where M is MI, R 1 is furthermore preferably trifluoromethyl, trifluoromethyl being particularly preferably in the 4- or 5-position of the anilide radical. In the case where M is M-2, M-3 or M-4, R 1 is furthermore preferably chlorine, with chlorine being particularly preferably in the 5-position (M-2, M-3) or in the 3-position (M-4) stands. R 1 is also preferably methyl in the case where M is M-2, M-3 or M-4, where methyl is particularly preferably in the 5-position (M-2, M-3) or in the 3-position (M-4) stands. R 1 is also preferred for the case where M is M-5, M-6, M-7 or M-8
Fluor, wobei Fluor besonders bevorzugt in 6-Position (M-5, M-6) oder in 3-Position (M-7,Fluorine, with fluorine particularly preferably in the 6-position (M-5, M-6) or in the 3-position (M-7,
M-8) steht. R1 steht für den Fall, dass M für M-5, M-6, M-7 oder M-8 steht, außerdem bevorzugt für Chlor, wobei Chlor besonders bevorzugt in 6-Position (M-5, M-6) oder in 3-Position (M-7, M-8) steht. R1 steht für den Fall, dass M für M-5, M-6, M-7 oder M-8 steht, außerdem bevorzugt fürM-8). In the case where M is M-5, M-6, M-7 or M-8, R 1 is furthermore preferably chlorine, chlorine being particularly preferably in the 6-position (M-5, M-6) or in the 3-position (M-7, M-8). R 1 is also preferred for the case where M is M-5, M-6, M-7 or M-8
Methyl, wobei Methyl besonders bevorzugt in 4-Position (M-5) oder in 3 -Position (M-6,Methyl, with methyl being particularly preferred in the 4-position (M-5) or in the 3-position (M-6,
M-7, M-8) steht. R1 steht für den Fall, dass M für M-9 steht, außerdem bevorzugt für Methyl, wobei Methyl besonders bevorzugt in 3-Position steht.M-7, M-8). R 1 stands for the case that M stands for M-9, moreover preferably for methyl, with methyl being particularly preferably in the 3-position.
R1 steht für den Fall, dass M für M-9 steht, außerdem bevorzugt für Trifluormethyl, wobei Trifluormethyl besonders bevorzugt in 3 -Position steht.R 1 is in the case that M is M-9, moreover preferably trifluoromethyl, trifluoromethyl being particularly preferably in the 3-position.
R1 steht für den Fall, dass M für M- 12 steht, außerdem bevorzugt für Methyl, wobei Methyl besonders bevorzugt in 4-Position steht.R 1 stands for the case that M stands for M-12, moreover preferably for methyl, with methyl being particularly preferably in the 4-position.
R1 steht für den Fall, dass M für M- 12 steht, außerdem bevorzugt für Trifluormethyl, wobeiR 1 stands for the case that M stands for M-12, moreover preferably for trifluoromethyl, where
Trifluormethyl besonders bevorzugt in 4-Position steht. R1 steht für den Fall, dass M für M-13 steht, außerdem bevorzugt für Methyl, wobei Methyl besonders bevorzugt in 3 -Position steht. R1 steht für den Fall, dass M für M-13 steht, außerdem bevorzugt für Trifluormethyl, wobeiTrifluoromethyl is particularly preferably in the 4-position. R 1 stands for the case that M stands for M-13, moreover preferably for methyl, with methyl being particularly preferably in the 3-position. R 1 stands for the case that M stands for M-13, moreover preferably for trifluoromethyl, where
Trifluormethyl besonders bevorzugt in 3 -Position steht. R1 steht für den Fall, dass M für M- 14 steht, außerdem bevorzugt für Methyl, wobei Methyl besonders bevorzugt in 3 -Position steht.Trifluoromethyl is particularly preferably in the 3-position. R 1 stands for the case that M stands for M-14, moreover preferably for methyl, where methyl is particularly preferably in the 3-position.
R1 steht für den Fall, dass M für M- 14 steht, außerdem bevorzugt für Trifluormethyl, wobei Trifluormethyl besonders bevorzugt in 3-Position steht.R 1 stands for the case that M stands for M-14, moreover preferably for trifluoromethyl, trifluoromethyl being particularly preferably in the 3-position.
R2 steht bevorzugt für Wasserstoff.R 2 is preferably hydrogen.
R2 steht außerdem bevorzugt für Methyl.R 2 is also preferably methyl.
R2 steht außerdem bevorzugt iür Trifluormethyl.R 2 is also preferably trifluoromethyl.
Q steht bevorzugt für eine direkte Bindung. Q steht außerdem bevorzugt für -CH2-, -(CH2)2-, -(CH2)3-, -CH(CH3)-, -C(CHj)2-, 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 steht außerdem bevorzugt für O. Q steht außerdem bevorzugt für S. Q steht außerdem bevorzugt füi SO . Q steht außerdem bevorzugt für SO2.Q is preferably a direct bond. Q furthermore Favor g t is -CH 2 -, - (CH 2) 2 -, - (CH 2) 3 -, -CH (CH 3) -, -C (CH j) 2 -, particularly Favor g for t -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-. In addition, Q is preferably O. Q is also preferably S. In addition, Q is preferably SO. Q is also preferably SO 2 .
Q steht außerdem bevorzugt für NR3, besonders bevorzugt für NH.Q is also preferably NR 3 , more preferably NH.
R3 steht bevorzugt für Wasserstoff, Ci-C6-Alkyl, CrC3-Alkoxy-Ci-C3-alkyl, CrC3-Alkylthio-R 3 preferably represents hydrogen, Ci-C 6 alkyl, C r C 3 alkoxy-Ci-C 3 alkyl, C r C 3 alkylthio
Ci-C3-alkyl oder C3-C6-Cycloalkyl. R3 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.C 1 -C 3 -alkyl or C 3 -C 6 -cycloalkyl. R 3 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.
R3 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, iso- oder tert-Butyl, Methoxymethyl oder Methylthiomethyl.R 3 is very particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, iso- or tert-butyl, methoxymethyl or methylthiomethyl.
Z steht bevorzugt für Z1. Z1 steht bevorzugt für gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Phenyl, wobei die Substituenten jeweils aus der Liste W1 ausgewählt sind. Z1 steht besonders bevorzugt für einfach substituiertes Phenyl, wobei die Substituenten aus derZ is preferably Z 1 . Z 1 preferably represents optionally mono- to quintuply, identically or differently substituted phenyl, where the substituents are each selected from list W 1 . Z 1 particularly preferably represents monosubstituted phenyl, the substituents being selected from
Liste W1 ausgewählt sind.List W 1 are selected.
Z1 steht auch besonders bevoreaigt für zweifach, gleich oder verschieden substituiertes Phenyl, wobei die Substituenten aus der Liste W1 ausgewählt sind.Z 1 is also particularly preferably phenyl which is monosubstituted by identical or different substituents, the substituents being selected from the list W 1 .
Z1 steht auch besonders bevorzugt für dreifach, gleich oder verschieden substituiertes Phenyl, wobei die Substituenten aus der Liste W1 ausgewählt sind. Z1 steht ganz besonders bevorzugt für einfach in 4-Position substituiertes Phenyl, wobei dieZ 1 is also particularly preferably triply, identically or differently substituted phenyl, where the substituents are selected from the list W 1 . Z 1 very particularly preferably represents phenyl which is monosubstituted in the 4-position, the
Substituenten aus der Liste W1 ausgewählt sind. Z1 steht ganz besonders bevorzugt für zweifach, gleich oder verschieden in 3,4-Position substituiertes Phenyl, wobei die Substituenten aus der Liste W1 ausgewählt sind. Z1 steht ganz besonders bevorzugt für zweifach, gleich oder verschieden in 2,3-Position substituiertes Phenyl, wobei die Substituenten aus der Liste W1 ausgewählt sind. Z1 steht ganz besonders bevorzugt für zweifach, gleich oder verschieden in 2,4-Position substituiertes Phenyl, wobei die Substituenten aus der Liste W1 ausgewählt sind. Z1 steht ganz besonders bevorzugt für zweifach, gleich oder verschieden in 3,5-Position substituiertes Phenyl, wobei die Substituenten aus der Liste W1 ausgewählt sind. Z1 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.Substituents are selected from the list W 1 . Z 1 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 . Z 1 very particularly preferably represents phenyl which is monosubstituted, identically or differently substituted in the 2,3-position, the substituents being selected from the list W 1 . Z 1 very particularly preferably represents phenyl substituted twice, identically or differently in the 2,4-position, the substituents being selected from the list W 1 . Z 1 very particularly preferably represents phenyl which is monosubstituted, identically or differently substituted in the 3,5-position, the substituents being selected from the list W 1 . Z 1 very particularly preferably represents 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, Carboxy, Carbamoyl, Thiocarb- amoyl; jeweils geradkettiges oder verzweigtes Alkyl, Hydroxyalkyl, Oxoalkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Dialkoxyalkyl, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 8 Kohlenstoffatomen; jeweils geradkettiges oder verzweigtes Alkenyl oder Alkenyloxy mit jeweils 2 bis 6 Kohlenstoffatomen; 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, Alkylcar- bonyloxy, Alkoxycarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Arylalkylaminocar- bonyl, Dialkylaminocarbonyloxy mit 1 bis 6 Kohlenstoffatomen in den jeweiligen Kohlen¬ wasserstoffketten, Alkenylcarbonyl oder Alkinylcarbonyl, mit 2 bis 6 Kohlenstoffatomen in den jeweiligen Kohlenwasserstoffketten;W 1 is halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 8 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, alkylcarboxylic bonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, carbonyl Arylalkylaminocar-, ¬ hydrocarbon chains dialkylaminocarbonyloxy having 1 to 6 carbon atoms in the respective coals, 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 Kohlenstofratomen; oder die Gruppierungen -(CR4R5)mSiR6R7R8 oder -C(Q2)=N-Q3, worin Q2 für Wasserstoff, Hydroxy oder Alkyl mit 1 bis 4 Kohlenstoffatomen, Halogenalkyl mit 1 bis 4 Kohlenstoffatomen und 1 bis 9 Fluor-, Chlor- und/oder Bromatomen 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 the groupings - (CR 4 R 5 ) m SiR 6 R 7 R 8 or -C (Q 2 ) = NQ 3 , wherein Q 2 is hydrogen, hydroxy or alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms and 1 to 9 are fluorine, chlorine and / or bromine atoms or cycloalkyl having 1 to 6 carbon atoms and
Q3 für Hydroxy, Amino, Methylamino, Phenyl, Benzyl oder für jeweils gegebenenfalls durch Cyano, Hydroxy, Alkoxy, Alkylthio, Alkylamino, Dialkylamino oder Phenyl substituiertes Alkyl oder Alkoxy mit 1 bis 4 Kohlenstoffatomen, oder für Alkenyl- oxy oder Alkinyloxy mit jeweils 2 bis 4 Kohlenstoff atomen 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 3 Kohlenstoffatomen in den jeweiligen Alkylteilen.Q 3 is hydroxy, amino, methylamino, phenyl, benzyl or each optionally substituted by cyano, hydroxy, alkoxy, alkylthio, alkylamino, dialkylamino or phenyl alkyl or alkoxy having 1 to 4 carbon atoms, or alkenyl oxy or alkynyloxy with 2 each up to 4 carbon atoms, and in each case optionally in the ring part monosubstituted to halogen, and / or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms substituted phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl or phenylalkyl, phenylalkyloxy, phenylalkylthio, or heterocyclylalkyl, with in each case 1 to 3 carbon atoms in the respective alkyl parts.
W1 steht bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t- Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Trifluormethyl, Trifluorethyl, Difluorrnethoxy, Trifluormethoxy, Difluorchlormethoxy, Trifluorethoxy, jeweils zweifach verknüpftes Difluormethylendioxy oder Tetrafluorethylendioxy, oder die Gruppierungen -CH2Si(CH3)3, -Si(CH3)3 oder -C(Q2)=N-Q3, worinW 1 is preferably fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, trifluoromethyl, trifluoroethyl, Difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, di-linked difluoromethylenedioxy or tetrafluoroethylenedioxy, or the groupings -CH 2 Si (CH 3 ) 3 , -Si (CH 3 ) 3 or -C (Q 2 ) = NQ 3 , wherein
Q2 für Wasserstoff, Methyl, Ethyl oder Trifluormethyl steht und Q3 für Hydroxy, Methoxy, Ethoxy, Propoxy oder Isopropoxy steht.Q 2 is hydrogen, methyl, ethyl or trifluoromethyl and Q 3 is hydroxy, methoxy, ethoxy, propoxy or isopropoxy.
Z steht bevorzugt für Z2. Z2 steht bevorzugt für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes 2-Pyridinyl, 3-Pyridinyl oder 4-Pyridinyl, wobei die Substituenten jeweils aus der Liste W2 ausgewählt sind. Z2 steht besonders bevorzugt für jeweils einfach substituiertes 2-Pyridinyl, 3-Pyridinyl oder 4-Z is preferably Z 2 . Z 2 is preferably in each case optionally monosubstituted to trisubstituted by identical or different substituents 2-pyridinyl, 3-pyridinyl or 4-pyridinyl, where the substituents are each selected from list W 2 . Z 2 is particularly preferably each monosubstituted 2-pyridinyl, 3-pyridinyl or 4-
Pyridinyl, wobei die Substituenten jeweils aus der Liste W2 ausgewählt sind. Z2 steht auch besonders bevorzugt für jeweils zweifach, gleich oder verschieden substituiertes 2-Pyridinyl, 3-Pyridinyl oder 4-PyridinyL wobei die Substituenten jeweils aus der Liste W2 ausgewählt sind.Pyridinyl, wherein the substituents are each selected from the list W 2 . Z 2 is also particularly preferably each 2-membered, identically or differently substituted 2-pyridinyl, 3-pyridinyl or 4-pyridinyl L wherein the substituents are each selected from the list W 2 .
Z2 steht auch besonders bevorzugt für jeweils dreifach, gleich oder verschieden substituiertes 2- PyridinyL 3-Pyridinyl oder 4-Pyridinyl, wobei die Substituenten jeweils aus der Liste W2 ausgewählt sind.Z 2 is also particularly preferably for each triply, identically or differently substituted 2-pyridinyl-3-pyridinyl or 4-pyridinyl, where the substituents are each selected from the list W 2 .
Z2 steht ganz besonders bevorzugt für einfach in 5-Position substituiertes 2-Pyridinyl oder in 6- Position substituiertes 3-Pyridinyl, wobei die Substituenten jeweils aus der Liste W2 ausgewählt sind.Z 2 very particularly preferably represents 2-pyridinyl which is monosubstituted in the 5-position or 3-pyridinyl which is substituted in the 6-position, the substituents in each case being selected from the list W 2 .
Z2 steht ganz besonders bevorzugt für zweifach, gleich oder verschieden in 3,5-Posrtion substituiertes 2-PyridinyL wobei die Substituenten aus der Liste W2 ausgewählt sind.Z 2 very particularly preferably represents 2-pyridinyl L which is monosubstituted, identically or differently substituted in 3,5-position, the substituents from the W 2 list being selected.
Z2 steht ganz besonders bevorzugt für zweifach, gleich oder verschieden in 4,6-Position substituiertes 3-Pyridinyl, wobei die Substituenten aus der Liste W2 ausgewählt sind. Z2 steht ganz besonders bevorzugt für zweifach, gleich oder verschieden in 3,5-Position substituiertes 4-Pyridinyl, wobei die Substituenten aus der Liste W2 ausgewählt sind. W2 für Wasserstoff, Halogen, Cyano, Nitro, d-C6-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C1-C4- Alkoxy, Ci-C4-Alkylthio, C,-C4-Alkylsulphinyl, Ci-C4-Alkylsulphonyl, C3-C6-Cycloalkyl; für Ci-C4-Halogenalkyl, CrC4-Halogenalkoxy, Q-Gi-Halogenalkylthio, Ci-C4-Halogenal- kylsulfinyl, d-C-Halogenalkylsulfonyl mit jeweils 1 bis 5 Halogenatomen; für -SO2NR46R47, -C(=X)R48, -Si(R49K C2-C4-Alkenylen-Si(R49)3, C2-C4-Alkinylen-Si(R49)3,Z 2 very particularly preferably represents twice, identically or differently, 4,6-substituted 3-pyridinyl, the substituents being selected from list W 2 . Z 2 very particularly preferably represents twice, identically or differently, 3,5-substituted 4-pyridinyl, where the substituents are selected from the W 2 list. W 2 is hydrogen, halogen, cyano, nitro, dC 6 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 - alkoxy, Ci-C 4 alkylthio, C, - C 4 alkylsulphinyl, C 1 -C 4 alkylsulphonyl, C 3 -C 6 cycloalkyl; for Ci-C 4 haloalkyl, C r C 4 haloalkoxy, Q-Gi-haloalkylthio, Ci-C 4 -Halogenal- kylsulfinyl, dC-halogenoalkylsulphonyl having in each case 1 to 5 halogen atoms; for -SO 2 NR 46 R 47 , -C (= X) R 48 , -Si (R 49 KC 2 -C 4 -alkenylene-Si (R 49 ) 3 , C 2 -C 4 -alkynylene-Si (R 49 3 ,
-NR46R47, -CH2-NR46R47 stehen, worin R46 für Wasserstoff, CrC4-Alkyl oder -C(=X)R48 steht, R47 für Wasserstoff, C,-C4-Alkyl oder -C(=X)R48 steht,-NR 46 R 47, -CH 2 -NR 46 R 47 are wherein R 46 is hydrogen, C r C 4 alkyl or -C (= X) R 48, R 47 represents hydrogen, C, -C 4 - Alkyl or -C (= X) R 48 ,
R46 und R47 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oderR 46 and R 47 also together with the nitrogen atom to which they are attached, optionally mono- or polysubstituted by identical or different halogen or
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 NR50 enthalten kann, R48 für Wasserstoff, CrC4-Alkyl, C,-C4-Alkoxy oder -NR51R52 steht, R49 für Wasserstoff, Ci-C8-Alkyl, Ci-C8-Alkoxy, Ci-C4-Alkoxy-d-C4-alkyl, C1-C4-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 50 , R 48 is hydrogen, C r C 4 alkyl , C, -C 4 alkoxy or -NR 51 R 52, R 49 represents hydrogen, Ci-C 8 alkyl, Ci-C8-alkoxy, Ci-C 4 alkoxy-dC 4 alkyl, C 1 - C 4 -
Alkylthio-Ci-C4-alkyl oder Ci-C6-Halogenalkyl steht, wobei die drei Reste R49 jeweils gleich oder verschieden sein können, R50 für Wasserstoff oder C1-C6-AIlCyI steht, R51 für Wasserstoff oder Ci-C4-Alkyl steht, R52 für Wasserstoff oder Ci-C4-Alkyl steht, Alkylthio-Ci-C4-alkyl or Ci-6 haloalkyl is C, where the three radicals R 49 may be the same or different in each case, R 50 is 6 -alkyl, hydrogen or C 1 -C, R 51 is hydrogen or C -C 4 -alkyl, R 52 is hydrogen or C 4 -alkyl-C,
R51 und R52 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oderR 51 and R 52 also together with the nitrogen atom to which they are attached, one optionally mono- or polysubstituted by identical or different halogen or
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 NR50 enthalten kann,Form 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 50 ,
W2 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Allyl, Propargyl, Methoxy, Ethoxy, n- oder iso- Propoxy, n-, iso-, sec- oder tert-Butoxy, Methylthio, Ethylthio, n- oder iso-Propyhhio, n-, iso-, sec- oder tert-Butylthio, Methylsulphinyl, Ethylsulphinyl, n- oder iso-Propylsulphinyl, n-, iso-, sec- oder tert-Butylsulphinyl, Methylsulphonyl, Ethylsulphonyl, n- oder iso-Pro- pylsulphonyl, n-, iso-, sec- oder tert-Butylsulphonyl, Cyclopropyl, Cyclopentyl, Cyclohexyl, Trifluormethyl, Difluormethyl, Trichlormethyl, Trifluorethyl, Trifluormethoxy, Difluormethoxy, Trichlormethoxy, Difluormethylthio, Difluorchlormethylthio, Trifluorme- thylthio, Trifluormethylsulfinyl, Trifluoπnethylsulfonyl, -SO2NMe2, -CC=X)R48, -Si(R49J3, - CH=CH-Si(R49)3, -CH2-CΗ-CH-Si(R49)3) -CH=CH-CH2-Si(R49)3, -C≡C-Si(R49)3, -CH2-W 2 is preferably hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, allyl, propargyl, methoxy, ethoxy, n - or iso-propoxy, n-, iso-, sec- or tert-butoxy, methylthio, ethylthio, n- or iso-Propyhhio, n-, iso-, sec- or tert-butylthio, methylsulphinyl, ethylsulphinyl, n- or Iso-Propylsulphinyl, n-, iso-, sec- or tert-butylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or iso-propylsulphonyl, n-, iso-, sec- or tert-butylsulphonyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl , Difluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxy, difluoromethoxy, trichloromethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, -SO 2 NMe 2 , -CC = X) R 48 , -Si (R 49 J 3 , - CH = CH-Si (R 49 ) 3 , -CH 2 -CΗ-CH-Si (R 49 ) 3) -CH = CH-CH 2 -Si (R 49 ) 3 , -C≡C-Si (R 49 ) 3 , -CH 2 -
C≡C-Si(R49)3, -C≡C-CH2-Si(R49)3, -CH2-C≡C-CH2-Si(R49)3, -NR46R47, -CH2-NR46R47. R46 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl oder -C(=X)R48.C≡C-Si (R 49 ) 3 , -C≡C-CH 2 -Si (R 49 ) 3 , -CH 2 -C≡C-CH 2 -Si (R 49 ) 3 , -NR 46 R 47 , -CH 2 -NR 46 R 47 . R 46 is preferably hydrogen, methyl, ethyl, n- or iso-propyl or -C (= X) R 48 .
R46 steht besonders bevorzugt für Wasserstoff oder Methyl.R 46 particularly preferably represents hydrogen or methyl.
R47 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl oder -C(=X)R48.R 47 is preferably hydrogen, methyl, ethyl, n- or iso-propyl or -C (= X) R 48 .
R47 steht besonders bevorzugt für Wasserstoff oder Methyl. R46 und R47 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Brom oder Methyl substituierten gesättigten Heterocyclus aus der Reihe Morpholin, Thio- morpholin oder Piperazin, wobei das Piperazin am zweiten Stickstoffatom durch R50 substituiert sein kann. R48 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, Methoxy, Ethoxy, n- oder iso-Propoxy oder -NR51R52.R 47 particularly preferably represents hydrogen or methyl. R 46 and R 47 together with the nitrogen atom to which they are attached furthermore preferably form a saturated heterocycle from the series morpholine, thiomorpholine or piperazine, optionally monosubstituted to monosubstituted by identical or different fluorine, chlorine, bromine or methyl, wherein the piperazine on the second nitrogen atom may be substituted by R 50 . R 48 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, n- or iso-propoxy or -NR 51 R 52 .
R48 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, Methoxy, Ethoxy oder -NR51R52.R 48 particularly preferably represents hydrogen, methyl, ethyl, methoxy, ethoxy or -NR 51 R 52 .
R49 steht bevorzugt für Methyl, Ethyl, Methoxy, Ethoxy, Methoxymethyl, Ethoxymethyl, Meth- oxyethyl, Ethoxyethyl, Methylthiomethyl, Ethylthiomethyl, Methylthioethyl oder Ethylthio- ethyl, wobei die drei Reste R49 jeweils gleich oder verschieden sein könnenR 49 is preferably methyl, ethyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl or ethylthioethyl, where the three radicals R 49 may each be identical or different
R49 steht besonders bevorzugt für Methyl, Methoxy, Methoxymethyl oder Methylthiomethyl, wobei die drei Reste R49 jeweils gleich oder verschieden sein können.R 49 particularly preferably represents methyl, methoxy, methoxymethyl or methylthiomethyl, where the three radicals R 49 may each be identical or different.
R49 steht ganz besonders bevorzugt für Methyl.R 49 is very particularly preferably methyl.
R50 steht bevorzugt für Wasserstoff oder Ci-C4-Alkyl. R50 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl.R 50 is preferably hydrogen or C 1 -C 4 -alkyl. R 50 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
R51 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl.R 51 is preferably hydrogen, methyl, ethyl, n- or isopropyl.
R51 steht besonders bevorzugt für Wasserstoff oder Methyl.R 51 is particularly preferably hydrogen or methyl.
R52 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl. R52 steht besonders bevorzugt für Wasserstoff oder Methyl.R 52 is preferably hydrogen, methyl, ethyl, n- or isopropyl. R 52 particularly preferably represents hydrogen or methyl.
R51 und R52 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Brom oder Methyl substituierten gesättigten Heterocyclus aus der Reihe Morpholin, Thio- morpholin oder Piperazin, wobei das Piperazin am zweiten Stickstoffatom durch R50 substi- tuiert sein kann.R 51 and R 52 together with the nitrogen atom to which they are attached furthermore preferably form a saturated heterocycle from the series morpholine, thiomorpholine or piperazine which is optionally monosubstituted to monosubstituted, identically or differently by fluorine, chlorine, bromine or methyl, wherein the piperazine on the second nitrogen atom may be substituted by R 50 .
Z steht auch bevorzugt für Z3.Z is also preferably Z 3 .
Z3 steht bevorzugt für jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Halogen, Ci-C4-Alkyl, -CH2Si(CH3)3 und/oder -Si(CH3)3 substituiertes Cycloalkyl oder Bi- cycloalkyl mit jeweils 3 bis 10 Kohlenstoffatomen. Z3 steht besonders bevorzugt für jeweils gegebenenfalls einfach bis vierfach, gleich oder ver¬ schieden durch Chlor, Methyl, -CH2Si(CH3)3 und/oder -Si(CH3)3 substituiertes Cyclopropyl, Cyclopentyl, Cyclohexyl, Cycloheptyl, Cyclooctyl, Cyclononyl, Bicyclo[2.2.1]heptyl oder Bicyclo[2.2.2]octyl. Z steht ganz besonders bevorzugt für durch Chlor und Methyl substituiertes Cyclopropyl.Z 3 preferably represents in each case optionally mono- to tetrasubstituted by identical or different halogen, Ci-C 4 alkyl, -CH 2 Si (CH 3) 3 and / or -Si (CH 3) 3-substituted cycloalkyl or bi-cycloalkyl of each 3 to 10 carbon atoms. Z 3 particularly g Favor t in each case optionally mono- to tetrasubstituted by identical or ver ¬ secreted by chlorine, methyl, -CH 2 Si (CH 3) 3 and / or -Si (CH 3) 3-substituted cyclopropyl, cyclopentyl, cyclohexyl, Cycloheptyl, cyclooctyl, cyclononyl, bicyclo [2.2.1] heptyl or bicyclo [2.2.2] octyl. Z g is particularly preferably substituted by chlorine and methyl-substituted cyclopropyl.
Z steht auch bevorzugt für Z4.Z is also preferably Z 4 .
Z4 steht bevorzugt für unsubstituiertes C2-C2o-Alkyl oder für einfach oder mehrfach, gleich oder verschieden durch Fluor, Chlor, Brom, Iod, Ci-C6-Alkylthio, Ci-Ce-Alkylsulfinyl, Ci-C6-Al- kylsulfonyl, Ci-C6-Alkoxy, C,-C6-Alkylamino, Di(C,-C6-alkyl)amino, Ci-Cβ-Halogenalkyl- thio, Ci-Cβ-Halogenalkylsulfinyl, Ci-Q-Halogenalkylsulfonyl, Ci-C6-Halogenalkoxy, Ci-C6- Halogenalkylamino, Halogen-di(Ci-C5-alkyl)amino, -SiR6R7R8 und/oder C3-C6-Cycloalkyl substituiertes Ci-C2o-Alkyl, 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.Z 4 is Favor g t represents unsubstituted C 2 -C 2 o alkyl or mono- or polysubstituted by identical or different fluorine, chlorine, bromine, iodine, Ci-C 6 alkylthio, Ci-Ce-alkylsulfinyl, Ci-C 6 -alkylsulfonyl, Ci-C 6 -alkoxy, C, -C 6 -alkylamino, di (C, -C 6 -alkyl) amino, Ci-Cβ-haloalkyl thio, Ci-Cβ-haloalkylsulfinyl, Ci-Q haloalkylsulfonyl, Ci-C 6 haloalkoxy, Ci-C 6 - Halogenalkylamino, halogen-di (Ci-C 5 alkyl) amino, -SiR 6 R 7 R 8 and / or C 3 -C 6 cycloalkyl substituted Ci- C 2 o-alkyl, where the cycloalkyl moiety in turn may optionally be monosubstituted to fourfold, identically or differently, by fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl and / or C 1 -C 4 -haloalkyl.
Z4 steht besonders bevorzugt für unsubstituiertes C2-C2o-Alkyl.Z 4 particularly preferably represents unsubstituted C 2 -C 2 o alkyl.
Z4 steht auch besonders bevorzugt für durch Fluor, Chlor, Brom, Iod, Ci-C6-Alkylthio, Ci-C4-Alkyl- sulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Alkoxy, Ci-C4-Alkylammo, Di(Ci-C4-alkyl)amino, Q-C4- Halogenalkylthio, Ci-C4-HalogenalkylsuUτnyl, Ci-C4-Halogenalkylsulfonyl, Ci-C4-Halogenalk- oxy, Ci-C4-Halogenalkylamino, Halogen-di(Ci-C4-alkyl)amino mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -SiR0R7R8, Cyclopropyl, Dichlorcyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl substituiertes Ci-C20-AIlCyI; ganz besonders bevorzugt für durch Fluor, Chlor, Methylthio, Ethylthio, n- oder iso-Prσpylthio, n-, iso-, sec-, tert-Butylthio, Pentylthio, Hexylthio, Methylsulfonyl, Ethylsulfonyl, n- oder iso-Propylsulfonyl, n-, iso-, sec-, tert-Butylsulfonyl, Methoxy, Ethoxy, n- oder iso-Propoxy, n-, iso-, sec-, tert-Butoxy, Methylamino, Ethylamino, n- oder iso-Propylamino, n-, iso-, sec-, tert-Butylamino, Dimethylamino, Diisopropylamino, Tri- fluormethylthio, Trifluormetfaoxy, -SiR6R7R8, Cyclopropyl, Dichlorcyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl substituiertes CrQzo-Alkyl.Z 4 is also particularly preferably represents fluorine, chlorine, bromine, iodine, Ci-C 6 alkylthio, Ci-C 4 alkyl sulfinyl, Ci-C 4 alkylsulfonyl, Ci-C 4 alkoxy, Ci-C4- -Alkylammo, di (Ci-C 4 alkyl) amino, QC 4 - haloalkylthio, Ci-C4-HalogenalkylsuUτnyl, Ci-C4-haloalkylsulfonyl, Ci-C 4 -Halogenalk- oxy, Ci-C4-Halogenalkylamino, halogen-di (Ci-C4-alkyl) amino each with 1 to 9 fluorine, chlorine and / or bromine atoms, -SiR 0 R 7 R 8 , cyclopropyl, dichlorocyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl-substituted Ci-C 20 -AIlCyI; very particularly preferred for by fluorine, chlorine, methylthio, ethylthio, n- or iso-Prpylthio, n-, iso-, sec-, tert-butylthio, pentylthio, hexylthio, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n- , iso-, sec-, tert-butylsulfonyl, methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec-, tert-butoxy, methylamino, ethylamino, n- or iso-propylamino, n-, iso -, sec-, tert-butylamino, dimethylamino, diisopropylamino, trifluoromethylthio, trifluorometfaoxy, -SiR 6 R 7 R 8 , cyclopropyl, dichlorocyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl-substituted CrQzo-alkyl.
Z steht auch bevorzugt für Z5.Z is also preferably Z 5 .
Z5 steht bevorzugt für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Fluor, Chlor, Brom, Iod, Ci-Q-Alkylthio, Ci-Cβ-Alkylsulfinyl, Ci-C6-Alkylsulfonyl, Ci-Cβ-Alkoxy, Ci-C6-Alkylamino, Di(Ci-C6-alkyl)amino, Ci-Cβ-Halogenalkylthio, Ci-Ce- Halogenalkylsulfinyl, Ci-Cβ-Halogenalkylsulfonyl, Ci-C6-Halogenalkoxy, Ci-C6-Halogenal- kylamino, Halogen-di(Ci-C6-alkyl)ammo, -SiR6R7R8 und/oder C3-C6-Cycloalkyl substituiertes C2-C∞-Alkenyl oder C2-C20-Alkinyl, wobei der Cycloalkylteil seinerseits gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Brom, Iod, C1-C4-AIlCyI und/oder Ci-C4-Halogenalkyl substituiert sein kann.Z 5 is preferably in each case optionally monosubstituted or polysubstituted, identically or differently, by fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkoxy, C 6 alkylamino, di (Ci-C 6 alkyl) amino, Ci-Cβ-haloalkylthio, Ci-Ce-haloalkylsulfinyl, Ci-Cβ-haloalkylsulfonyl, Ci-C 6 haloalkoxy, Ci-C 6 alkylamino -Halogenal-, Halo-di (Ci-C 6 -alkyl) ammo, -SiR 6 R 7 R 8 and / or C 3 -C 6 -cycloalkyl-substituted C 2 -C ∞ -alkenyl or C 2 -C 20 -alkynyl, wherein the cycloalkyl moiety in turn, if necessary may be monosubstituted to tetrasubstituted by identical or different fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl and / or Ci-C 4 haloalkyl.
Z5 steht besonders bevorzugt für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Iod, Ci-C6-Al- kylthio, C,-C4-Alkylsulfinyl, CrC4-Alkylsulfbnyl, CrC4-Alkoxy, Ci-C4-Alkylamino5 Di(Ci-C4- alkyl)amino, Ci-C4-HalogenaUcylthio, CrC4-Halogenalkylsulfinyl, CrQ-Halogenalkylsulfbnyl,Z 5 particularly preferably represents in each case optionally fluorine-, chlorine, bromine, iodine, Ci-C 6 alkylthio -Al-, C, -C 4 alkylsulfinyl, C r C 4 -Alkylsulfbnyl, C r C 4 alkoxy, Ci- C 4 alkylamino 5 di (Ci-C 4 - alkyl) amino, Ci-C 4 -HalogenaUcylthio, C r C 4 haloalkylsulfinyl, CRQ-Halogenalkylsulfbnyl,
Ci-C4-Halogenalkoxy, Ci-C4-Halogenalkylamino, Halogen-di(Ci-C4-alkyl)amino mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, -SiR6R7R8, Cyclopropyl, Dichlorcyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl substituiertes C2-C2o-Alkenyl oder C2-C2O-AIkUIyI. Ci-C4-haloalkoxy, Ci-C 4 -Halogenalkylamino, halogen-di (Ci-C 4 alkyl) amino each having 1 to 9 fluorine, chlorine and / or bromine atoms, -SiR 6 R 7 R 8, cyclopropyl , Dichlorcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted C 2 -C 2 o-alkenyl or C 2 -C 2O -AIkUIyI.
Z5 steht ganz besonders bevorzugt für C2-C20-Alkenyl oder C2-C2o-Alkinyl.Z 5 very particularly preferably represents C 2 -C 20 -alkenyl or C 2 -C 2 o-alkynyl.
Z steht auch bevorzugt für Z6.Z is also preferably Z 6 .
Z6 steht bevorzugt für einen der folgenden RingeZ 6 is preferably one of the following rings
— -
Si-I Si-2 Si-3 Si-4 Si-5Si-I Si-2 Si-3 Si-4 Si-5
Si-6 Si-7 Si-8 Si-9 worin R58 für Wasserstoff oder Methyl steht.Si-6Si-7Si-8Si-9 wherein R 58 is hydrogen or methyl.
R4 steht bevorzugt für Wasserstoff oder Methyl. R4 steht besonders bevorzugt für Wasserstoff.R 4 is preferably hydrogen or methyl. R 4 particularly preferably represents hydrogen.
R5 steht bevorzugt für Wasserstoff oder Methyl. R5 steht besonders bevorzugt für Wasserstoff.R 5 is preferably hydrogen or methyl. R 5 particularly preferably represents hydrogen.
m steht bevorzugt für 0, 1 oder 2.m is preferably 0, 1 or 2.
R6 und R7 stehen unabhängig voneinander bevorzugt für Ci-C6-Alkyl, Ci-C6-Alkoxy, Ci-C3-Alkoxy-R 6 and R 7 independently of one another are preferably C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 3 -alkoxy
Ci-Cs-alkyl oder Ci-C3-Allcylihio-Ci-C3-alkyl. R6 und R7 stehen unabhängig voneinander besonders bevorzugt für Methyl, Ethyl, Methoxy, Ethoxy,Ci-Cs-alkyl or Ci-C 3 -Allcylihio-Ci-C 3 -alkyl. R 6 and R 7 independently of one another particularly preferably represent methyl, ethyl, methoxy, ethoxy,
Methoxymethyl, Ethoxymethyl, MethoxyethyL, Ethoxyethyl, Methyhhiomethyl, Ethylthio- methyl, Methylthioethyl oder Ethyhhioethyl. R6 und R7 stehen unabhängig voneinander ganz besonders bevorzugt für Methyl, Methoxy,Methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthio methyl, methylthioethyl or ethylthioethyl. R 6 and R 7 independently of one another very particularly preferably represent methyl, methoxy,
Methoxymethyl oder Methylthiomethyl. R6 und R7 stehen insbesondere bevorzugt jeweils für Methyl.Methoxymethyl or methylthiomethyl. R 6 and R 7 are particularly preferably each methyl.
R8 steht bevorzugt für CrC6-Alkyl, Ci-C6-Alkoxy, Ci-Ca-Alkoxy-d-Cj-alkyl, Ci-C3-Alkylthio-R 8 is Favor g t C r C 6 alkyl, Ci-C 6 alkoxy, Ci-Ca-alkoxy-d-Cj-alkyl, Ci-C3 alkylthio
Ci-C3-alkyl, CrCβ-Cycloalkyl, Phenyl oder Benzyl. R8 steht besonders bevorzugt für Methyl, Ethyl, n- oder iso-Propyl, n-, sec-, iso- oder tert- Butyl, Methoxy, Ethoxy, n- oder iso-Propoxy, n-, sec-, iso- oder tert-Butoxy, Methoxymethyl, Ethoxymethyl, Methoxyethyl, Ethoxyethyl, Methylthiomethyl, Ethylthio- methyl, Methylthioethyl, Ethylthioethyl, Cyclopropyl, Phenyl oder Benzyl.Ci-C 3 -alkyl, CrCβ-cycloalkyl, phenyl or benzyl. R 8 is particularly preferably methyl, ethyl, n- or iso-propyl, n-, sec-, iso- or tert-butyl, methoxy, ethoxy, n- or iso-propoxy, n-, sec-, iso- or tert-butoxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthio methyl, methylthioethyl, ethylthioethyl, cyclopropyl, phenyl or benzyl.
R8 steht ganz besonders bevorzugt für Methyl, Ethyl, n- oder iso-Propyl, iso- oder tert-Butyl, Methoxy, iso-Propoxy, iso- oder tert-Butoxy, Methoxymethyl, Methylthiomethyl oder Phenyl.R 8 most preferably represents methyl, ethyl, n- or iso-propyl, iso- or tert-butyl, methoxy, iso-propoxy, iso- or tert-butoxy, methoxymethyl, methylthiomethyl or phenyl.
R8 steht insbesondere bevorzugt für Methyl, Ethyl, n- oder iso-Propyl, iso- oder tert-Butyl, Methoxy, iso-Propoxy, iso- oder tert-Butoxy.R 8 is particularly preferably methyl, ethyl, n- or iso-propyl, iso- or tert-butyl, methoxy, iso-propoxy, iso- or tert-butoxy.
R8 steht hervorgehoben für Methyl.R 8 stands for methyl.
M-Q-Z stehen auch bevorzugt gemeinsam für l,l,3-Trimethyl-lH-2,3-dihydro-inden-4-yl, 1,3-Dime- thyl- 1 H-2,3 -dihydro-inden-4-yl, 1 , 1 ,3-Trimethyl- 1 ,3 -dihydro-2-benzofuran-4-yl, 1 ,3 -Dime- thyl-l,3-dihydro-2-benzofuran-4-yl, l,l,3-Trimethyl-l,3-dihydro-2-benzothien-4-yl oder l,3-Dimethyl-l,3-dihydro-2-benzothien-4-yl.MQZ are also preferably together l, l, 3-trimethyl-lH-2,3-dihydro-inden-4-yl, 1,3-dimethyl-1 H-2,3-dihydro-inden-4-yl , 1,1,3-Trimethyl-1,3-dihydro-2-benzofuran-4-yl, 1,3-dimethyl-1,3-dihydro-2-benzofuran-4-yl, 1,1,3 Trimethyl-1,3-dihydro-2-benzothien-4-yl or 1,3-dimethyl-1,3-dihydro-2-benzothien-4-yl.
M-Q-Z stehen auch besonders bevorzugt gemeinsam für l,l,3-Trimethyl-lH-2,3-dihydro-inden-4-yl.M-Q-Z are also particularly preferably together for l, l, 3-trimethyl-lH-2,3-dihydro-inden-4-yl.
A steht bevorzugt für einen der Reste Al, A2, A3, A4, A5, A6, A9, AlO, Al 1, A12, oder A17. A steht besonders bevorzugt für einen der ResteA is preferably one of the radicals Al, A2, A3, A4, A5, A6, A9, AlO, Al 1, A12, or A17. A is particularly preferably one of the radicals
Al, A2, A4, A5, A6, A9, A] 1, A16, A17. A steht ganz besonders bevorzugt für den Rest Al . A steht außerdem ganz besonders bevorzugt für den Rest A2. A steht außerdem ganz besonders bevorzugt für den Rest A4. A steht außerdem ganz besonders bevorzugt für den Rest A5. A steht außerdem ganz besonders bevorzugt für den Rest A6. A steht außerdem ganz besonders bevorzugt für den Rest A9. A steht außerdem ganz besonders bevorzugt für den Rest All. A steht außerdem ganz besonders bevorzugt für den Rest Al 6. A steht außerdem ganz besonders bevorzugt für den Rest Al 7.Al, A2, A4, A5, A6, A9, A] 1, A16, A17. A very particularly preferably represents the radical Al. A is also very particularly preferably the radical A2. A is also very particularly preferred for the rest of A4. A is also most preferably the radical A5. A is also most preferably the radical A6. A is also most preferably the radical A9. A is also very particularly preferred for the rest of all. In addition, A very particularly preferably represents the radical Al 6. A also very particularly preferably represents the radical Al 7.
R9 steht bevorzugt für Wasserstoff, Cyano, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, iso-Propyl, Methoxy, Ethoxy, Methyhhio, Ethylthio, Cyclopropyl, d-C∑-Halogenalkyl, Ci-C2-HaIo- genalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen, Trifluormethylthio, Di- fluormethylthio, Aminocarbonyl, Aminocarbonylmethyl oder Aminocarbonylethyl. R9 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, iso-R 9 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-propyl, methoxy, ethoxy, Methyhhio, ethylthio, cyclopropyl, dC Σ haloalkyl, Ci-C 2 -HaIo- genalkoxy with in each case 1 to 5 fluorine, chlorine and / or bromine atoms, trifluoromethylthio, di-fluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl. R 9 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-
Propyl, Monofluormethyl, Monofluorethyl, Difluormethyl, Trifluormethyl, Difluorchlor- methyl, Trichlormethyl, Dictilormethyl, Cyclopropyl, Methoxy, Ethoxy, Trifluormethoxy,Propyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, dictilomethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy,
Trichlormethoxy, Methylthio, Ethylthio, Trifluormethylthio oder Difluormethylthio. R9 steht ganz besonders bevorzugt Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, iso-Propyl,Trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or difluoromethylthio. R 9 is very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, isopropyl,
Monofluormethyl, Monofluorethyl, Difluormethyl, Trifluormethyl, Difluorchlormethyl oderMonofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or
Trichlormethyl. R9 steht insbesondere bevorzugt für Methyl, Difluormethyl, Trifluormethyl oder 1-Fluorethyl.Trichloromethyl. R 9 particularly preferably represents methyl, difluoromethyl, trifluoromethyl or 1-fluoroethyl.
R10 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, Methoxy, Ethoxy,R 10 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy,
Methylthio oder Ethylthio.Methylthio or ethylthio.
R10 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod oder Methyl. R10 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor oder Methyl.R 10 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine or methyl. R 10 very particularly preferably represents hydrogen, fluorine, chlorine or methyl.
R11 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen, Hydroxymethyl, Hydroxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl oder Phenyl. Ru steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, iso-Propyl, Trifluormethyl, Difluormethyl, Hydroxymethy], Hydroxyethyl oder Phenyl.R 11 is preferably 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 or phenyl. R u particularly preferably represents hydrogen, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl.
R1 ' steht ganz besonders bevorzugt für Wasserstoff, Methyl, Trifluormethyl oder Phenyl.R 1 'is very particularly preferably hydrogen, methyl, trifluoromethyl or phenyl.
Ru steht insbesondere bevorzugt für Methyl.R u is particularly preferably methyl.
R12 und R13 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl,R 12 and R 13 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, methyl,
Ethyl oder Q^-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R12 und R13 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Difluorchlormethyl oder Trichlormethyl. R12 und R13 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor,Ethyl or Q 1 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 12 and R 13 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl. R 12 and R 13 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine,
Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl oder Trichlormethyl. R12 und R13 stehen insbesondere bevorzugt jeweils für Wasserstoff.Bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl. R 12 and R 13 are particularly preferably each hydrogen.
R14 steht bevorzugt für Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Ci-C2-Halogenalkyl oder Ci- C2-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen. R14 steht besonders bevorzugt für Fluor, Chlor, Brom, Cyano, Methyl, Trifluormethyl, Tπfluormethoxy, Difluormethoxy, Difluorchlormethoxy oder Trichlormethoxy.R 14 is preferably fluorine, chlorine, bromine, cyano, methyl, ethyl, C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy having in each case 1 to 5 fluorine, chlorine and / or bromine atoms. R 14 particularly preferably represents fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy.
R14 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Iod, Methyl, Trifluormethyl oderR 14 is very particularly preferably fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or
Trifluormethoxy. R14 steht insbesondere bevorzugt für Methyl oder Trifluormethyl.Trifluoromethoxy. R 14 is particularly preferably methyl or trifluoromethyl.
R15 und R16 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 15 and R 16 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.
R15 und R16 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Difluorchlormethyl oder Trichlormethyl.R 15 and R 16 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl.
R15 und R16 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl oder Trichlormethyl.R 15 and R 16 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl.
R15 und R16 stehen insbesondere bevorzugt jeweils für Wasserstoff.R 15 and R 16 are particularly preferably each hydrogen.
R17 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl oder CrC2-Halo- genalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 17 is preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or C r C 2 haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R17 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl oder Trifluormethyl.R 17 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl.
R17 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Iod, Methyl oder Trifluormethyl.R 17 is very particularly preferably fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl.
R18 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Hydroxy, Cyano, d-C4-Alkyl, Ci-C2-Halogenalkyl, Ci-C2-Halogenalkoxy oder Ci-C2-Halogenalkylthio mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 18 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or C 1 -C 2 -haloalkylthio, each having 1 to 5 fluorine , Chlorine and / or bromine atoms.
R18 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Hydroxy, Cyano, Methyl, Ethyl, n-Propyl, iso-Pτopyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Difluormethyl, Trifluormethyl, Difluorchlormethyl, Trichlormethyl, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy, Trichlormethoxy, Trifluormethylthio, Difluormethylthio, Difluorchlormethylthio oder Trichlormethylthio.R 18 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopotyl, n-butyl, isobutyl, sec-butyl, tert-butyl, difluoromethyl, Trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio or trichloromethylthio.
R18 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Difluor- methyl, Trifluormethyl oder Trichlormethyl.R 18 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl.
R18 steht insbesondere bevorzugt für Iod, Methyl, Difluormethyl oder Trifluormethyl.R 18 is particularly preferably iodine, methyl, difluoromethyl or trifluoromethyl.
R19 steht bevorzugt für Fluor, Chlor, Brom, Iod, Hydroxy, Cyano, Ci-C4-Alkyl, Methoxy, Ethoxy, Methyhhio, Ethylthio, Difluormethylthio, Trifluormethylthio, Ci-C2-Halogenalkyl oder Ci-C2-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen. R19 steht besonders bevorzugt für Fluor, Chlor, Brom, Iod, Hydroxy, Cyano, Methyl, Ethyl, n-R 19 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 1 to 5 fluorine, chlorine and / or bromine atoms. R 19 is particularly preferably fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-
Propyl, iso-Propyl, n-Butyl, :ιso-Butyl, sec-Butyl, tert-Butyl, Trifluormethyl, Difluormethyl,Propyl, isopropyl, n-butyl, ιso-butyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl,
Difluorchloπnethyl, Trichlormethyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Difluorme- thylthio, Trifluormethylthio, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy oder Trichlormethoxy.Difluorochloroethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy.
R19 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Iod, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 19 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R20 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Ci-C4-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. R20 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, n-Propyl, iso- Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Trifluormethyl, Difluormethyl, Difluor- chlormethyl, Trichlormethyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy, Trichlormethoxy, Methylsulphinyl oder Methyl- sulphonyl.R 20 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, Ci-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 20 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 methylsulfonyl.
R20 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. R20 steht insbesondere bevorzugt für Wasserstoff.R 20 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 20 particularly preferably represents hydrogen.
R21 steht bevorzugt für Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oderR 21 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or
Bromatomen.Bromine atoms.
R21 steht besonders bevorzugt für Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluor- chlormethyl oder Trichlormethyl.R 21 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R22 steht bevorzugt für Methyl oder Ethyl. R22 steht besonders bevorzugt für Methyl.R 22 is preferably methyl or ethyl. R 22 is particularly preferably 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. Q1 steht ganz besonders bevorzugt für S (Schwefel).Q 1 particularly preferably represents S (sulfur) or CH 2 . Q 1 very particularly preferably represents S (sulfur).
p steht bevorzugt für 0 oder 1. p steht besonders bevorzugt für 0. R23 steht bevorzugt für Methyl, EÜiyl oder C,-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oderp is preferably 0 or 1. p is particularly preferably 0. R 23 is Favor g t represents methyl, EÜiyl or C, -C 2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or
Bromatomen. R23 steht besonders bevorzugt für Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlor- methyl oder Trichlormethyl. R23 steht ganz besonders bevorzugt für Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.Bromine atoms. R 23 is particularly Favor g t is methyl, ethyl, trifluoromethyl, difluoromethyl, Difluorchlor- methyl or trichloromethyl. R 23 is very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R^ steht bevorzugt für Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oderR ^ is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or
Bromatomen. R24 steht besonders bevorzugt für Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlor- methyl oder Trichlormethyl.Bromine atoms. R 24 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R24 steht ganz besonders bevorzugt für Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 24 is very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R25 und R26 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino,R 25 and R 26 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino,
Methyl, Ethyl oder Ci-C2-Haiogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R25 und R26 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R25 und R26 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor,Methyl, ethyl or Ci-C 2 -Haiogenalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 25 and R 26 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 25 and R 26 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine,
Brom, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R25 und R26 stehen insbesondere bevorzugt jeweils für Wasserstoff.Bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 25 and R 26 are particularly preferably each hydrogen.
R27 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl oder C,-C2- Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 27 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.
R27 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 27 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R27 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R27 steht insbesondere bevorzugt für Methyl.R 27 is very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 27 is particularly preferably methyl.
R28 und R29 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Nitro, Methyl, Ethyl oder Ci-Qr-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, nitro, methyl, ethyl or C 1 -C 9 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R28 und R29 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Nitro, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R28 und R29 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor,R 28 and R 29 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 28 and R 29 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine,
Brom, Methyl, Trifluormethyi, Difluormethyl oder Trichlormethyl. R28 und R29 stehen insbesondere bevorzugt jeweils für Wasserstoff.Bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 28 and R 29 are particularly preferably each hydrogen.
R30 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder CrC2-R 30 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -
Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen,Haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,
R30 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyi, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 30 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R30 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Trifluor- methyl, Difluormethyl oder Trichlormethyl.R 30 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R30 steht insbesondere bevorzugt für Methyl.R 30 is particularly preferably methyl.
R31 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Ci-C4-Alkylamino, Di(Ci-C4- alkyl)amino, Cyano, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 31 preferably represents hydrogen, fluorine, chlorine, bromine, amino, Ci-C 4 alkylamino, di (Ci-C 4 - alkyl) amino, cyano, methyl, ethyl or Ci-C 2 haloalkyl having 1 to 5 fluorine , Chlorine and / or bromine atoms.
R31 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino,R 31 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
Dimethylamino, Cyano, Methyl, Ethyl, Trifluormethyi, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.Dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R31 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino, Dimethylamino, Methyl, Trifluormethyi, Difluormethyl oder Trichlormethyl.R 31 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R31 steht insbesondere bevorzugt für Amino, Methylamino, Dimethylamino, Methyl oderR 31 particularly preferably represents amino, methylamino, dimethylamino, methyl or
Trifluormethyi.Trifluormethyi.
R32 steht bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 32 is preferably fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R32 steht besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyi,R 32 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,
Difluormethyl, Difluorchlormethyl oder Trichlormethyl.Difluoromethyl, difluorochloromethyl or trichloromethyl.
R32 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Trifluormethyi, Difluormethyl oder Trichlormethyl. R32 steht insbesondere bevorzugt für Methyl, Trifluormethyi oder Difluormethyl.R 32 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 32 particularly preferably represents methyl, trifluoromethyl or difluoromethyl.
R33 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Ci-C4-Alkylamino, Di(Ci-C4- alkyl)amino, Cyano, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R33 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino, Dimethylamino, Cyano, Methyl, Ethyl, Trifluormethyi, Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R33 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino,R 33 preferably represents hydrogen, fluorine, chlorine, bromine, amino, Ci-C 4 alkylamino, di (Ci-C 4 - alkyl) amino, cyano, methyl, ethyl or Ci-C 2 haloalkyl having 1 to 5 fluorine , Chlorine and / or bromine atoms. R 33 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 33 g anz particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
Dimethylatnino, Methyl, Trif luormethyl, Difluormethyl oder Trichlormethyl. R33 steht insbesondere bevorzugt für Amino, Methylamino, Dimethylamino, Methyl oder Trifluormethyl.Dimethylatnino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 33 particularly preferably represents amino, methylamino, dimethylamino, methyl or trifluoromethyl.
R34 steht bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5R 34 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.
R34 steht besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlomiethyl oder Trichlormethyl.R 34 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R34 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Trifluormethyl,R 34 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl,
Difluormethyl oder Trichlormethyl. R34 steht insbesondere bevorzugt für Methyl, Trifluormethyl oder Difluormethyl.Difluoromethyl or trichloromethyl. R 34 is particularly preferably methyl, trifluoromethyl or difluoromethyl.
R35 steht bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5R 35 is preferably fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl of 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.Difluoromethyl, difluorochloromethyl or trichloromethyl.
R35 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 35 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R36 steht bevorzugt für Wasserstoff, Methyl oder Ethyl. R36 steht besonders bevorzugt für Methyl.R 36 is preferably hydrogen, methyl or ethyl. R 36 particularly preferably represents methyl.
R37 steht bevorzugt für Fluor, Chlor, Brom, Methyl oder Ethyl, R37 steht besonders bevorzugt für Fluor, Chlor oder Methyl.R 37 is preferably fluorine, chlorine, bromine, methyl or ethyl, R 37 is particularly preferably fluorine, chlorine or methyl.
R38 steht bevorzugt für Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oderR 38 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or
Bromatomen. R38 steht besonders bevorzugt für Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.Bromine atoms. R 38 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R38 steht ganz besonders bevorzugt für Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 38 is very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R38 steht insbesondere bevorzugt: für Methyl oder Trifluormethyl. R39 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Ci-C2-Halogen- alkyl mit 1 bis 5 Fluor, Chloi und/oder Bromatomen. R39 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl oder Trifluormethyl.R 38 is particularly preferred: for methyl or trifluoromethyl. R 39 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 39 is particularly Favor g t represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.
R40 steht bevorzugt für Fluor, Chlor, Brom, Iod, Hydroxy, Ci-C4-Alkyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Difluormethylthio, Trifluormethylthio, CrC2-Halogenalkyl oder Ci- C2-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 40 is preferably fluorine, chlorine, bromine, iodine, hydroxy, C 1 -C 4 -alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, C r C 2 -haloalkyl or C 1 -C 2 -haloalkoxy, each having 1 to 5 fluorine, chlorine and / or bromine atoms.
R40 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.R 40 particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R40 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Iod, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 40 is very particularly preferably fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R41 steht bevorzugt für Wasserstoff, Methyl, Ethyl, Ci-C2-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen, C1-C2-Alkoxy-Ci-C2-alkyl, Hydroxymethyl, Hydroxyethyl,R 41 preferably represents hydrogen, methyl, ethyl, Ci-C 2 haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, C 1 -C 2 alkoxy-Ci-C 2 alkyl, hydroxymethyl, hydroxyethyl,
Methylsulfonyl oder Dimethylaminosulfonyl. R41 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, Trifluormethyl, Methoxymethyl,Methylsulfonyl or dimethylaminosulfonyl. R 41 particularly preferably represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl,
Ethoxymethyl, Hydroxymethyl oder Hydroxyethyl. R41 steht ganz besonders bevorzugt für Methyl oder Methoxymethyl.Ethoxymethyl, hydroxymethyl or hydroxyethyl. R 41 is very particularly preferably methyl or methoxymethyl.
R42 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Q-C2-R 42 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QC 2 -
Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen. R42 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, EthylHaloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 42 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl
Trifluormethyl, Difluormethyl oder Trichlormethyl. R42 steht ganz besonders bevoπαigt für Wasserstoff oder Methyl.Trifluoromethyl, difluoromethyl or trichloromethyl. R 42 is particularly favorable for hydrogen or methyl.
R43 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.R 43 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R43 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, iso- Propyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 43 is particularly preferably hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R43 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Difluormethyl oder Trifluormethyl.R 43 is very particularly preferably hydrogen, methyl, difluoromethyl or trifluoromethyl.
R44 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Ci-C2-R 44 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -
Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R44 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl oder Trifluormethyl. R44 steht ganz besonders bevorzugt für Wasserstoff.Haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 44 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl. R 44 is very particularly preferably hydrogen.
R45 steht bevorzugt für Methyl, Ethyl, n-Propyl oder iso-Propyl. R45 steht besonders bevorzugt M<rthyl oder Ethyl.R 45 is preferably methyl, ethyl, n-propyl or iso-propyl. R 45 particularly preferably represents methyl or ethyl.
Bevorzugt sind solche Verbindungen der Formel (I), in welcher alle Reste jeweils die oben genannten bevorzugten Bedeutungen haben.Preference is given to those compounds of the formula (I) in which all radicals each have the abovementioned preferred meanings.
Besonders bevorzugt sind solche Verbindungen der Formel (I), in welcher alle Reste jeweils die oben genannten besonders bevorzugten Bedeutungen haben.Particular preference is given to those compounds of the formula (I) in which all radicals each have the abovementioned particularly preferred meanings.
Bevorzugt und jeweils als Teilmenge der oben genannten Verbindungen der Formel (I) zu verstehen sind folgende Gruppen von neuen Carboxamiden:The following groups of new carboxamides are to be understood as being preferred and in each case as a subset of the abovementioned compounds of the formula (I):
Gruppe 1 : Carboxamide der Formel (I-b)Group 1: Carboxamides of the formula (I-b)
in welcher X, R , Q, Z und A die oben angegebenen Bedeutungen haben. in which X, R, Q, Z and A have the meanings given above.
Gruppe 2: Carboxamide der Formel (I-c)Group 2: carboxamides of the formula (I-c)
in welcher X3 R1, Q, Z und A die oben angegebenen Bedeutungen haben. in which X 3 R 1 , Q, Z and A have the meanings given above.
Gruppe 3 : Carboxamide der Formel (I-d)Group 3: Carboxamides of the formula (I-d)
in welcher X, R1, Q, Z und A die oben angegebenen Bedeutungen haben. in which X, R 1 , Q, Z and A have the meanings given above.
Gruppe 4: Carboxamide der Formel (I-e) in welcher X, R1, Q, Z und A die oben angegebenen Bedeutungen haben.Group 4: carboxamides of the formula (Ie) in which X, R 1 , Q, Z and A have the meanings given above.
Gruppe 5 : Carboxamide der Formel (I-f)Group 5: Carboxamides of the formula (I-f)
in welcher X, R1, Q, Z und A die oben angegebenen Bedeutungen haben. in which X, R 1 , Q, Z and A have the meanings given above.
Gruppe 6: Carboxamide der Formel (I-g)Group 6: Carboxamides of the formula (I-g)
in welcher X, R2, Q, Z und A die oben angegebenen Bedeutungen haben. in which X, R 2 , Q, Z and A have the meanings given above.
Gruppe 7: 2-Halogenfuryl/thienyl-3-carboxamide der Formel (I-h)Group 7: 2-Halogenfuryl / thienyl-3-carboxamides of the formula (I-h)
in welcher X, R2, Q, Z und A die oben angegebenen Bedeutungen haben. in which X, R 2 , Q, Z and A have the meanings given above.
Bevorzugt sind Carboxamide der Formel (I) sowie der Gruppen 1 bis 7, in welcher Q für eine direktePreference is given to carboxamides of the formula (I) and groups 1 to 7, in which Q is a direct
Bindung und Z für Z1 steht.Bond and Z stands for Z 1 .
Bevorzugt sind Carboxamide der Formel (I) sowie der Gruppen 1 bis 7, in welcher Q für eine direktePreference is given to carboxamides of the formula (I) and groups 1 to 7, in which Q is a direct
Bindung und Z für Z4 steht. Z4 steht insbesondere bevorzugt für die GruppierungBond and Z stands for Z 4 . Z 4 is particularly preferred for the grouping
, worin G1 für Wasserstoff oder Methyl steht, in which G 1 is hydrogen or methyl,
G2 für Wasserstoff oder Methyl steht,G 2 is hydrogen or methyl,
G3 für Methyl oder Ethyl steht.G 3 is methyl or ethyl.
Z4 steht auch bevorzugt für eine der Gruppierungen Gl bis G8Z 4 is also preferably one of the groupings G1 to G8
Gl G2 G3 G4Gl G2 G3 G4
G5 G6 G7 G8 besonders bevorzugt für G3. G5 oder G7.G5 G6 G7 G8 particularly preferred for G3. G5 or G7.
Die Definition Ci-C2o-Alkyl umfasst den größten hierin definierten Bereich für einen Alkylrest. Im Einzelnen umfasst diese Definition die Bedeutungen Methyl, Ethyl, n-, iso-Propyl, n-, iso-, sec-, tert- Butyl, sowie jeweils alle isomeren Pentyle, Hexyle, Heptyle, Octyle, Nonyle, Decyle, Undecyle, Dodecyle, Tridecyle, Tetradecyle, Pentadecyle, Hexadecyle, Heptadecyle, Octadecyle, Nonadecyle und Eicosyle. Ein bevorzugter Bereich ist C2-Cn-Alkyl wie Ethyl und geradkettiges oder verzweigtes Propyl, Butyl, Pentyl, Hexyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl und Dodecyl, besonders geradkettiges oder verzweigtes C3-Cio-Alkyl wie Propyl, 1-Methylethyl, Butyl, 1-Methylpropyl, 2- Methylpropyl, 1,1-Dimethylethyl, n-Pentyl, 1-Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 1,2-Di- methylpropyl, 1,1-Dimethylpropyl, 2,2-Dimethylpropyl, 1-Ethylpropyl, n-Hexyl, 1-Methylpentyl, 2- Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1,2-Dimethylbutyl, 1,3-Dimethylbutyl, 2,3-Dime- thylbutyl, 1,1-Dimethylbutyl, 2,2-Dimethylbutyl, 3,3-Dimethylbutyl, 1,1,2-Trimethylpropyl, 1,2,2- Trimethylpropyl, 1-Ethylbutyl, 2-Ethylbutyl, l-Ethyl-3-methylpropyl, n-Heptyl, 1-Methylhexyl, 1- Ethylpentyl, 2-Ethylpentyl, 1-Prop)'lbutyl, Octyl, 1-Methylheptyl, 2-Methylheptyl, 1-Ethylhexyl, 2- Ethylhexyl, 1-Propylpentyl, 2-Propylpentyl, Nonyl, 1-Methyloctyl, 2-Methyloctyl, 1-Ethylheptyl, 2- Ethylheptyl, 1-Propylhexyl, 2-Propylhexyl, Decyl, 1-Methyhionyl, 2-Methylnonyl, 1-Ethyloctyl, 2- Ethyloctyl, 1-Propylheptyl und 2-Propylheptyl, insbesondere Propyl, 1-Methylethyl, Butyl, 1-Me- thylbutyl, 2-Methylbutyl, 3-Methylbutyl, 1,1-Dimethylethyl, 1,2-Dimethylbutyl, 1,3-Dimethylbutyl, Pentyl, 1-Methylbutyl, 1-Ethylpropyl, Hexyl, 3-Methylpentyl, Heptyl, 1-Methylhexyl, l-Ethyl-3-me- thylbutyl, 1-Methylheptyl, 1,2-Dimethylhexyl, 1,3-Dimethyloctyl, 4-Methyloctyl, 1, 2,2,3 -Tetrame- thylbutyl, 1,3,3-Trimethylbutyl, 1,2,3-Trimethylbutyl, 1,3-Dimethylpentyl, 1,3-Dimethylhexyl, 5- Methyl-3-hexyl, 2-Methyl-4-heptyl, 2,6-Dimethyl-4-heptyl und l-Methyl-2-cyclopropylethyl. Durch Halogen substituiertes Alkyl steht beispielsweise für Chlormethyl, Dichlormethyl, Trichlor- methyl, Fluormethyl, Difluormethyl, Trifluormethyl, Chlorfluormethyl, Dichlorfluormethyl, Chlordi- fluormethyl, 1-Fluorethyl, 2-Fluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, 2-Chlor-2-fluorethyl, 2-Chlor-2,2-difluorethyl, 2,2-Dichlor-2-fluorethyl, 2,2,2-Trichlorethyl, Pentafluorethyl, 3-Chlor-l- methylbutyl, 2-Chlor-l-methylbutyl, 1-Chlorbutyl, 3,3-Dichlor-l-methylbutyl, 3-Chlor-l- methylbutyl, l-Merthyl-3-trifluormethylbutyl, 3-Methyl-l-trifluormethylbutyl.The definition Ci-C 2 o-alkyl includes the largest range defined herein for an alkyl radical. In detail, this definition includes the meanings methyl, ethyl, n-, iso-propyl, n-, iso-, sec-, tert-butyl, and in each case all isomeric pentyls, hexyls, heptyls, octyls, nonyls, decyls, undecycles, dodecyls , Tridecyle, Tetradecyle, Pentadecyle, Hexadecyle, Heptadecyle, Octadecyle, Nonadecyle and Eicosyle. A preferred range is C 2 -C n -alkyl such as ethyl and straight-chain or branched propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl, especially straight-chain or branched C 3 -C 10 -alkyl, such as propyl, 1 -Methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2 , 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1 , 1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-ethyl-3-methylpropyl, n -Heptyl, 1-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 1-prop) 'butyl, octyl, 1-methylheptyl, 2-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 1-propylpentyl, 2-propylpentyl, nonyl, 1-Methyloctyl, 2-methyloctyl, 1-ethylheptyl, 2-ethylheptyl, 1-propylhexyl, 2-propylhexyl, Decyl, 1-methylthionyl, 2-methylnonyl, 1-ethyloctyl, 2-ethyloctyl, 1-propylheptyl and 2-propylheptyl, in particular propyl, 1-methylethyl, butyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 , 1-dimethylethyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, pentyl, 1-methylbutyl, 1-ethylpropyl, hexyl, 3-methylpentyl, heptyl, 1-methylhexyl, 1-ethyl-3-methylbutyl, 1 Methylheptyl, 1,2-dimethylhexyl, 1,3-dimethyloctyl, 4-methyloctyl, 1, 2,2,3-tetramethylbutyl, 1,3,3-trimethylbutyl, 1,2,3-trimethylbutyl, 1.3 Dimethylpentyl, 1,3-dimethylhexyl, 5-methyl-3-hexyl, 2-methyl-4-heptyl, 2,6-dimethyl-4-heptyl and 1-methyl-2-cyclopropylethyl. Alkyl which is substituted by halogen is, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl , 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 3-chloro-1-methylbutyl, 2-chloro -l-methylbutyl, 1-chlorobutyl, 3,3-dichloro-1-methylbutyl, 3-chloro-1-methylbutyl, 1-merthyl-3-trifluoromethylbutyl, 3-methyl-1-trifluoromethylbutyl.
Der Substituent -SiR6R7R8 steht bevorzugt für folgende Reste: SiMe3, SiMe2Et, SiMe2CHMe2, SiMe2CH2CHMe2, SiMe2CH2CMe3, SiMe2OCHMe2, SiMe2OCH2CHMe2, SiMe2OMe, SiMe2CMe3, SiMe2CH2CH2Me.The substituent -SiR 6 R 7 R 8 preferably represents the following radicals: SiMe 3 , SiMe 2 Et, SiMe 2 CHMe 2 , SiMe 2 CH 2 CHMe 2 , SiMe 2 CH 2 CMe 3 , SiMe 2 OCHMe 2 , SiMe 2 OCH 2 CHMe 2 , SiMe 2 OMe, SiMe 2 CMe 3 , SiMe 2 CH 2 CH 2 Me.
Die Definition C2-C2o-Alkenyl umfasst den größten hierin definierten Bereich für einen Alkenylrest. Im Einzelnen umfasst diese Definition die Bedeutungen Ethenyl, n-, iso-Propenyl, n-, iso-, sec-, tert- Butenyl, sowie jeweils alle isomeren Pentenyle, Hexenyle, Heptenyle, Octenyle, Nonenyle, Decenyle, Undecenyle, Dodecenyle, Tridecenyle, Tetradecenyle, Pentadecenyle, Hexadecenyle, Heptadecenyle, Octadecenyle, Nonadecenyle und Eicosenyle, 1 -Methyl- 1-propenyl, 1-Ethyl-l-butenyl, 2,4- Dimethyl-1 -pentenyl, 2,4-Dimethyl-2-pentenyl.The definition C 2 -C 2 o-alkenyl encompasses the largest range defined herein for an alkenyl radical. In detail, this definition includes the meanings ethenyl, n-, iso-propenyl, n-, iso-, sec-, tert-butenyl, and in each case all isomeric pentenyls, hexenyls, heptenyls, octenyls, nonenyls, decenyls, undecenyls, dodecenyls, tridecenyls , Tetradecenyls, pentadecenyls, hexadecenyls, heptadecenyls, octadecenyls, nonadecenyls and eicosenyls, 1-methyl-1-propenyl, 1-ethyl-1-butenyl, 2,4-dimethyl-1-pentenyl, 2,4-dimethyl-2-pentenyl ,
Die Definition C2-C2o-Alkinyl umfassit den größten hierin definierten Bereich für einen Alkinylrest. Im Einzelnen umfasst diese Definition die Bedeutungen Ethinyl, n-, iso-Propinyl, n-, iso-, sec-, tert- Butinyl, sowie jeweils alle isomeren Pentinyle, Hexinyle, Heptinyle, Octinyle, Noninyle, Decinyle, Undecinyle, Dodecinyle, Tridecinyle, Tetradecinyle, Pentadecinyle, Hexadecinyle, Heptadecinyle, Octadecinyle, Nonadecinyle und Eicosinyle.The definition C 2 -C 2 o-alkynyl includes the largest range defined herein for an alkynyl radical. In detail, this definition includes the meanings ethynyl, n-, iso-propynyl, n-, iso-, sec-, tert-butynyl, and in each case all isomeric pentinyls, hexynyls, heptynyls, octynyls, nonynyls, decinyls, undecynyls, dodecyls, tridecinyls , Tetradecinyle, Pentadecinyle, Hexadecinyle, Heptadecinyle, Octadecinyle, Nonadecinyle and Eicosinyle.
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 jedoch auch untereinander, also zwischen den jeweiligen Bereichen und Vorzugsbereichen beliebig kombiniert werden. Sie gelten für die Endprodukte sowie für die Vor- und Zwischenprodukte entsprechend.However, the general or preferred radical definitions or explanations given above can also be used among one another, ie between the respective ranges and Preferred areas can be combined as desired. They apply accordingly to the end products as well as to the precursors and intermediates.
Verwendet man beispielsweise 5-Fluor-l53-dimethyl-lH-pyrazol-4-carbonylchlorid und 4'-Chlor-N- cyclopropylbiphenyl-2-amin als Ausgangsstoffe sowie ein Base, so kann der Verlauf des erfindungs- gemäßen Verfahrens (a) durch folgende Reaktionsgleichung veranschaulicht werden:If, for example, 5-fluoro-L 5 3-dimethyl-1H-pyrazole-4-carbonyl chloride and 4'-chloro-N-cyclopropylbiphenyl-2-amine are used as starting materials and also a base, the course of the process according to the invention (a ) are illustrated by the following reaction equation:
Die zur Durchführung des erfindungsgemäßen Verfahrens (a) als Ausgangsstoffe benötigten Carbonsäurehalogenide sind durch die Formel (II) allgemein definiert. In dieser Formel (II) stehen A und X bevorzugt, besonders bevorzugt, ganz besonders bevorzugt bzw. insbesondere bevorzugt für diejenigen Bedeutungen, die bereits in Zusammenhang mit der Beschreibung der erfindungsgemäßen Stoffe der Formel (I) als bevorzugt, besonders bevorzugt usw. für diesen Rest angegeben wurden. X1 steht bevorzugt für Fluor, Chlor oder Hydroxy, besonders bevorzugt für Chlor oder Hydroxy.For carrying out the process (a) required as starting materials Carbonsäurehalogenide are generally defined by the formula (II). In this formula (II), A and X are preferably, more preferably, very particularly preferably or especially preferred for those meanings which are already preferred in connection with the description of the substances of the formula (I) according to the invention, particularly preferably for this Rest were specified. X 1 is preferably fluorine, chlorine or hydroxyl, more preferably chlorine or hydroxy.
Die Carbonsäurehalogenide der Foimel (II) sind bekannt und/oder lassen sich nach bekannten Verfahren herstellen (vgl. z.B. EP-A 0 545 099, JP-A 01-290662 und US 5,093,347).The carboxylic acid halides of the formula (II) are known and / or can be prepared by known processes (cf., for example, EP-A 0 545 099, JP-A 01-290662 and US 5,093,347).
Die weiterhin zur Durchfuhrung des erfindungsgemäßen Verfahrens (a) als Ausgangsstoffe benötig- ten Cyclopropylamine sind durch die Formel (HI) allgemein definiert. In dieser Formel (III) stehen M, Q und Z bevorzugt, besonders bevorzugt, ganz besonders bevorzugt bzw. insbesondere bevorzugt für diejenigen Bedeutungen, die bereits in Zusammenhang mit der Beschreibung der erfindungsgemäßen Stoffe der Formel (I) als bevorzugt, besonders bevorzugt usw. für diesen Rest angegeben wurden.The cyclopropylamines furthermore required for carrying out the process (a) according to the invention as starting materials are generally defined by the formula (III). In this formula (III), M, Q and Z are preferably, more preferably, very particularly preferably or particularly preferably for those meanings which are already preferred in connection with the description of the substances of the formula (I) according to the invention, particularly preferably etc. for this remainder were indicated.
Die Cyclopropylamine der Formel (DI) sind neu. Sie werden erhalten, indem manThe cyclopropylamines of the formula (DI) are new. They are obtained by
(b) Amine der Formel (JV) mit Cyclopropanon-Derivaten, wie z.B. deren Acetalen oder Acetalderivaten, insbesondere gemischten Alkyl-/Silyl-Acetalen, z.B. [(1-Ethoxycyclopropyl)oxy](trimethyl)silan, in Gegenwart eines Reduktionsmittels und ggf. in Gegenwart einer Säure und eines Verdünnungs- mittels umsetzt.(b) Amines of the formula (JV) with cyclopropanone derivatives, such as, for example, their acetals or acetal derivatives, in particular mixed alkyl / silyl acetals, for example [(1-ethoxycyclopropyl) oxy] (trimethyl) silane, in the presence of a reducing agent and if appropriate in the presence of an acid and a diluent by means of implements.
Die zur Durchfuhrung des erfindungsgemäßen Verfahrens (b) als Ausgangsstoffe benötigten Amine sind durch die Formel (IV) allgemein definiert, In dieser Formel (FV) stehen M, Q und Z bevorzugt, besonders bevorzugt, ganz besonders bevorzugt bzw. insbesondere bevorzugt für diejenigen Bedeu- tungen, die bereits in Zusammenhang mit der Beschreibung der erfindungsgemäßen Stoffe der Formel (I) als bevorzugt, besonders bevorzugt usw. für diesen Rest angegeben wurden.The amines required as starting materials for carrying out the process (b) according to the invention are generally defined by the formula (IV). In this formula (IV), M, Q and Z are preferably, more preferably, very particularly preferably or particularly preferably those which are important - tions, which have already been given in connection with the description of the compounds of the formula (I) according to the invention as preferred, particularly preferred, etc. for this radical.
Die Amine der Formel (V) sind bekannt (vgl. z.B. WO 03/070705, EP-A 0 824 099).The amines of the formula (V) are known (cf., for example, WO 03/070705, EP-A 0 824 099).
Die weiterhin zur Durchführung des erfindungsgemäßen Verfahrens (b) als Ausgangsstoffe benötigten Cyclopropanon-Derivate, wie z.B. deren Acetale oder Acetalderivate, sind bekannte Synthesechemikalien.The cyclopropanone derivatives, which are furthermore required for carrying out the process (b) according to the invention as starting materials, such as, for example, their acetals or acetal derivatives are known synthetic chemicals.
Als Verdünnungsmittel zur Durchführung des erfindungsgemäßen Verfahrens (a) kommen alle inerten organischen Lösungsmittel in Betracht. Hierzu gehören vorzugsweise aliphatische, alicycli- sche oder aromatische Kohlenwasserstoffe, wie z.B. Petrolether, Hexan, Heptan, Cyclohexan,Suitable diluents for carrying out process (a) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as e.g. Petroleum ether, hexane, heptane, cyclohexane,
Methylcyclohexan, Benzol, Toluol, Xylol oder Decalin; halogenierte Kohlenwasserstoffe, wie z.B.Methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, e.g.
Chlorbenzol, Dichlorbenzol, Dichlormethan, Chloroform, Tetrachlormethan, Dichlorethan oder Tri- chlorethan; Ether, wie Diethylether, Diisopropylether, Methyl-t-butylether, Methyl-t-Amylether, Di- oxan, Tetrahydrofuran, 1,2-Dimethoxyethan, 1,2-Diethoxyethan oder Anisol; Ketone, wie Aceton,Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones, such as acetone,
Butanon, Methyl-isobutylketon oder Cyclohexanon; Nitrile, wie Acetonitril, Pfopionitril, n- oder i-Butanone, methyl isobutyl ketone or cyclohexanone; Nitriles, such as acetonitrile, Pfopionitril, n- or i-
Butyronitril oder Benzonitril; Amide, wie N,N-Dimethylformamid, N,N-Dimethylacetamid, N-Butyronitrile or benzonitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-
Me&ylformanilid, N-Methylpyrrolidon oder Hexamethylphosphorsäuretriamid; deren Gemische mitMethylsilanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; their mixtures with
Wasser oder reines Wasser.Water or pure water.
Das erfindungsgemäße Verfahren (a) wird gegebenenfalls in Gegenwart eines geeigneten Säureakzeptors durchgeführt. Als solche kommen alle üblichen anorganischen oder organischen Basen infrage. Hierzu gehören vorzugsweise Erdalkalimetall- oder Alkalimetallhydride, -hydroxide, -amide, -alkoholate, -acetate, -carbonate oder -hydrogencarbonate, wie z.B. Natriumhydrid, Natriumamid, Lithiumdiisopropylamid, Natrium-inethylat, Natrium-ethylat, Kalium-tert.-butylat, Natriumhydroxid, Kaliumhydroxid, Natrium acetat, Natriumcarbonat, Kaliumcarbonat, Kaliumhydrogen- carbonat, Natriumhydrogencarbonat oder Ammoniumcarbonat, sowie tertiäre Amine, wie Trimethyl- amin, Triethylamin, Tributylamin, N,N-Dimethylanilin, N,N-Dimethyl-benzylamin, Pyridin, N- Methylpiperidin, N-Methytoiorpholin, N,N-Dύnethylaminopyridin, Diazabicyclooctan (DABCO), Diazabicyclononen (DBN) oder Diazabicycloundecen (DBU).If appropriate, the process (a) according to the invention is carried out in the presence of a suitable acid acceptor. As such, all customary inorganic or organic bases are suitable. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, lithium diisopropylamide, sodium ethylate, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, Sodium bicarbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylthiolpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO ), Diazabicyclononene (DBN) or diazabicycloundecene (DBU).
Das erfindungsgemäße Verfahren (a) wird gegebenenfalls in Gegenwart eines geeigneten Kupplungs- reagenzes durchgeführt (wenn X5 für Hydroxy steht). Als solche kommen alle üblichen Carbonyl- aktivatoren infrage. Hierzu gehören vorzugsweise N-[3-(Dimethylamino)propyl]-N'-ethyl-carbodi- imide-hydrochlorid, N,N'-Di-sec-butyl-carbodiimid, N^'-Dicyclohexylcarbodiimid, N,N'-Diisopro- pylcarbodiimid, 1 -(3-(Dimethylamirio)propyl)-3-ethyl-carbodiimid-methiodid, 2-Bromo-3 -ethyl-4- methyl-thiazolium-tetrafluoroborat, N,N-Bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride, Chlor-tripyrrolidino-phosphonium-he>cafluoφhosphat, Brom-tripyrrolidino-phosphonium-hexafluor- phosphat, O-( 1 H-Benzotriazol- 1 -yloxy)tris(dimethylamino)phosphonium-hexafluorphosphat, O-( 1 H-If appropriate, the process (a) according to the invention is carried out in the presence of a suitable coupling reagent (if X 5 is hydroxyl). As such, all customary carbonyl activators are suitable. These preferably include N- [3- (dimethylamino) propyl] -N'-ethyl-carbodiimide hydrochloride, N, N'-di-sec-butyl-carbodiimide, N, N'-dicyclohexylcarbodiimide, N, N'-diisopro pylcarbodiimide, 1- (3- (dimethylamirio) propyl) -3-ethyl-carbodiimide-methiodide, 2-bromo-3-ethyl-4-methyl-thiazolium-tetrafluoroborate, N, N-bis [2-oxo-3- oxazolidinyl] phosphorodiamidic chloride, chloro-tripyrrolidino-phosphonium he> cofluorophosphate, bromo-tripyrrolidino-phosphonium hexafluorophosphate, O- (1H-benzotriazol-1-ylxy) tris (dimethylamino) phosphonium hexafluorophosphate, O- (1H -
Benzotriazol- 1 -yl)-N,N,N ' ,N ' -tetramethyluronium-hexafluoφhosphat, O-( 1 H-Benzotriazol- 1 -yl)-Benzotriazole-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate, O- (1H-benzotriazol-1-yl) -
N,N,N',N'-bis(tetramethylen)uromum-hexafluorphosphat, O-(lH-Benzotriazol-l-yl)-N,N,N',N'-bis-N, N, N ', N'-bis (tetramethylene) uromum hexafluorophosphate, O- (1H-benzotriazol-1-yl) -N, N, N', N'-bis-
(tetramethylen)uronium-tetrafluorborat, N,N,N',N'-Bis(tetramethylen)chloruromum-tetrafluorborat, O-(7-Azabenzotriazol-l-yl)-N5N,N,N-tetramethyluromum hexafluorphosphat und 1-Hydroxybenzo- triazol. Diese Reagenzien können separat aber auch in Kombination eingesetzt werden.(tetramethylene) uronium tetrafluoroborate, N, N, N ', N'-bis (tetramethylene) chlorouromum tetrafluoroborate, O- (7-azabenzotriazol-1-yl) -N 5 N, N, N-tetramethyluromum hexafluorophosphate and Hydroxybenzotriazole. These reagents can be used separately or in combination.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens (a) in einem größeren Bereich variiert werden. Im Allgemeinen arbeitet man bei Temperaturen von O0C bis 1500C, vorzugsweise bei Temperaturen von 2O0C bis 1100C.The reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, one works at temperatures of 0 0 C to 150 0 C, preferably at temperatures from 2O 0 C to 110 0 C.
Zur Durchführung des erfindungsgernäßen Verfahrens (a) zur Herstellung der Verbindungen der Formel (I) setzt man pro Mol des Carbonsäurehalogenids der Formel 01) im Allgemeinen 0,2 bis 5 Mol, vorzugsweise 0,5 bis 2 Mol an Cyclopropylamin der Formel (III) ein. Die Aufarbeitung erfolgt nach übli chen Methoden.To carry out the process (a) for the preparation of the compounds of the formula (I), in general from 0.2 to 5 mol, preferably from 0.5 to 2 mol, of cyclopropylamine of the formula (III) are employed per mole of the carboxylic acid halide of the formula one. The work-up is carried out according to customary methods.
Als Verdünnungsmittel zur Durchführung des erfindungsgemäßen Verfahrens (b) kommen alle inerten organischen Lösungsmittel in Betracht. Hierzu gehören vorzugsweise aliphatische, alicyclische oder aromatische Kohlenwasserstoffe, wie beispielsweise Petrolether, Hexan, Heptan, Cyclohexan, Methylcyclohexan, Benzol, Toluol, Xylol oder Decalin; Ether, wie Diethylether, Diisopropylether, Methyl-t-butylether, Methyl-t-amylether, Dioxan, Tetrahydrofuran, 1,2-Dimethoxyethan, 1,2- Diethoxyethan oder Anisol; Nitrile, wie Acetonitril, Propionitril, n- oder i-Butyronitril oder Benzo- nitril; Amide, wie N,N-Dmiethylformamid, N,N-Dimethylacetamid5 N-Methylformanilid, N-Methyl- pyrrolidon oder Hexamethylphosphorsäuretriamid; Ester wie Essigsäuremethylester oder Essigsäure- ethylester; Sulfoxide, wie Dimethylsulfoxid; Sulfone, wie Sulfolan; Alkohole, wie Methanol, Ethanol, n- oder i-Propanol, n-, i-, sek- oder tert-Butanol, Ethandiol, Propan-l,2-diol, Ethoxyethanol, Methoxyethanol, Diethylenglykolmonomethylether, Diethylenglykolmonoethylether, deren Gemische mit Wasser oder reines Wasser.Suitable diluents for carrying out process (b) according to the invention are all inert organic solvents. These include, preferably, aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2- Diethoxyethane or anisole; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides, such as N, N-diethylformamide, N, N-dimethylacetamide, 5 N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters, such as methyl acetate or ethyl acetate; Sulfoxides, such as dimethylsulfoxide; Sulfones, such as sulfolane; Alcohols such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propan-l, 2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water or pure water.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens (b) in einem größeren Bereich variiert werden. Im Allgemeinen arbeitet man bei Temperaturen von -400C bis 1500C, vorzugsweise bei Temperaturen von 00C bis 1000C.The reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, one works at temperatures of -40 0 C to 150 0 C, preferably at temperatures of 0 0 C to 100 0 C.
Das erfindungsgemäße Verfahren (b) wird gegebenenfalls in Gegenwart einer geeigneten Säure durchgerührt. Als solche kommen alle üblichen anorganischen oder organischen Säuren infrage. Vor- zugsweise verwendbar sind Salzsäure, Schwefelsäure, Flusssäure, Phosphorsäure, p-Toluolsulfon- säure, Methansulfonsäure, Trifluoressigsäure oder Trichloressigsäure. Besonders bevorzugt verwendet man Salzsäure, Schwefelsäure, p-Toluolsulfonsäure oder Trifluoressigsäure, ganz besonders bevorzugt p-Toluolsulfonsäure oder Essigsäure . Die eingesetzte Säure kann gegebenenfalls in einer Mischung mit Wasser eingesetzt werden.If appropriate, the process (b) according to the invention is stirred in the presence of a suitable acid. As such, all conventional inorganic or organic acids are suitable. Preference is given to using hydrochloric acid, sulfuric acid, hydrofluoric acid, phosphoric acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoroacetic acid or trichloroacetic acid. Particular preference is given to using hydrochloric acid, sulfuric acid, p-toluenesulfonic acid or trifluoroacetic acid, most preferably p-toluenesulfonic acid or acetic acid. The acid used can optionally be used in a mixture with water.
Das erfindungsgemäße Verfahren (b) wird gegebenenfalls in Gegenwart eines Reduktionsmittels durchgeführt. Als solche kommen alle üblichen anorganischen oder organischen Reduktionsmittel infrage. Vorzugsweise verwendbar sind Metallhydride, Alkali- und Erdalkalihydride, sowie deren Borhydride, ganz besonders bevorzugt Natriumborhydrid, Natriumcyanoborhydrid, Lithiumborhydrid.The process (b) according to the invention is optionally carried out in the presence of a reducing agent. As such, all customary inorganic or organic reducing agents are suitable. Preference is given to using metal hydrides, alkali metal and alkaline earth metal hydrides, and also their borohydrides, very particularly preferably sodium borohydride, sodium cyanoborohydride, lithium borohydride.
Zur Durchführung des erfindungsgemäßen Verfahrens (b) zur Herstellung der Verbindungen der Formel 011) setzt man pro Mol des Amins der Formel (TV) im Allgemeinen 1 bis 10 Mol, vorzugsweise 1 bis 3 Mol [(1-Ethoxycyclopropyl)oxy](trimethyl)silan und 1 bis 100 Mol, vorzugsweise 1 bis 10 Mol Reduktionsmittel ein. Die Aufarbeitung erfolgt nach üblichen Methoden.For carrying out process (b) according to the invention for preparing the compounds of the formula (011), in general from 1 to 10 mol, preferably from 1 to 3 mol of [(1-ethoxycyclopropyl) oxy] (trimethyl) are employed per mole of the amine of the formula (TV). silane and 1 to 100 moles, preferably 1 to 10 moles of reducing agent. The workup is carried out by conventional methods.
Die erfindungsgemäßen Verfahren (a) und (b) werden im Allgemeinen unter Normaldruck durchgeführt. Es ist jedoch auch möglich, unter erhöhtem oder vermindertem Druck - im Allgemeinen zwischen 0, 1 bar und 10 bar - zu arbeiten. Die erfindungsgemäßen Stoffe weisen eine starke mikrobizide Wirkung auf und können zur Bekämpfung von unerwünschten Mikroorganismen, wie Pilzen und Bakterien, im Pflanzenschutz und im Materialschutz eingesetzt werden.The processes (a) and (b) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to work under elevated or reduced pressure, generally between 0, 1 bar and 10 bar. The substances according to the invention have a strong microbicidal action and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
Fungizide lassen sich Pflanzenschutz zur Bekämpfung von Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes und Deuteromycetes einsetzen.Fungicides can be used for the control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
Bakterizide lassen sich im Pflanzenschutz zur Bekämpfung von Pseudomonadaceae, Rhizobiaceae,Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae,
Enterobacteriaceae, Corynebacteriaceae und Streptomycetaceae einsetzen.Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
Beispielhaft aber nicht begrenzend seien einige Erreger von pilzlichen und bakteriellenExemplary but not limiting are some pathogens of fungal and bacterial
Erkrankungen, die unter die oben aufgezählten Oberbegriffe fallen, genannt:Diseases that fall under the above-mentioned generic terms, called:
Erkrankungen, hervorgerufen durch Erreger des Echten Mehltaus wie z.B.Diseases caused by powdery mildews such as e.g.
Blumeria-Arten, wie beispielsweise Blumeria graminis; Podosphaera-Arten, wie beispielsweise Podosphaera leucotricha;Blumeria species, such as Blumeria graminis; Podosphaera species, such as Podosphaera leucotricha;
Sphaerotheca-Arten, wie beispielsweise Sphaerotheca fuliginea;Sphaerotheca species, such as Sphaerotheca fuliginea;
Uncinula-Arten, wie beispielsweise Uncinula necator;Uncinula species, such as Uncinula necator;
Erkrankungen, hervorgerufen durch Erreger von Rostkrankheiten wie z.B. Gymnosporangium-Arten, wie beispielsweise Gymnosporangium sabinaeDiseases caused by causative agents of rust diseases, such as Gymnosporangium species, such as Gymnosporangium sabinae
Hemileia-Arten, wie beispielsweise Hemileia vastatrix;Hemileia species, such as Hemileia vastatrix;
Phakopsora-Arten, wie beispielsweise Phakopsora pachyrhizi und Phakopsora meibomiae;Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae;
Puccinia-Arten, wie beispielsweise Puccinia recondita oder Puccinia graminis;Puccinia species, such as Puccinia recondita or Puccinia graminis;
Uromyces-Arten, wie beispielsweise Uromyces appendiculatus;Uromyces species, such as Uromyces appendiculatus;
Erkrankungen, hervorgerufen durch Erreger der Gruppe der Oomyceten wie z.B.Diseases caused by pathogens of the group of Oomycetes, e.g.
Bremia-Arten, wie beispielsweise Bremia lactucae;Bremia species, such as Bremia lactucae;
Peronospora-Arten, wie beispielsweise Peronospora pisi oder P. brassicae;Peronospora species such as Peronospora pisi or P. brassicae;
Phytophthora-Arten, wie beispielsweise Phytophthora infestans; Plasmopara-Arten, wie beispielsweise Plasmopara viticola;Phytophthora species, such as Phytophthora infestans; Plasmopara species, such as Plasmopara viticola;
Pseudoperonospora-Arten, wie beispielsweise Pseudoperonospora humuli oderPseudoperonospora species, such as Pseudoperonospora humuli or
Pseudoperonospora cubensis;Pseudoperonospora cubensis;
Pythium-Arten, wie beispielsweise Pythium ultimum;Pythium species such as Pythium ultimum;
Blattfleckenkrankheiten und Blattwelken, hervorgerufen durch z.B. Ahernaria-Arten, wie beispielsweise Alternaria solani; Cercospora-Arten, wie beispielsweise Cercospora beticola;Leaf spot diseases and leaf wilt caused by eg Ahernaria species, such as Alternaria solani; Cercospora species, such as Cercospora beticola;
Cladosporium-Arten, wie beispielsweise Cladosporium cucumerinum;Cladosporium species, such as Cladosporium cucumerinum;
Cochliobolus-Arten, wie beispielsweise Cochliobolus sativusCochliobolus species, such as Cochliobolus sativus
(Konidienfortn: Drechslera, Syn: Helntiinthosporium); Colletotrichum-Arten, wie beispielsweise Colletotrichum lindemuthanium;(Konidienfortn: Drechslera, Syn: Helntiinthosporium); Colletotrichum species, such as Colletotrichum lindemuthanium;
Cycloconium-Arten, wie beispielsweise Cycloconium oleaginum;Cycloconium species such as cycloconium oleaginum;
Diaporthe-Arten, wie beispielsweise Diaporthe citri;Diaporthe species, such as Diaporthe citri;
Elsinoe-Arten, wie beispielsweise Elsinoe fawcettii;Elsinoe species, such as Elsinoe fawcettii;
Gloeosporium-Arten, wie beispielsweise Gloeosporium laeticolor; Glomerella-Arten, wie beispielsweise Glomerella cingulata;Gloeosporium species, such as, for example, Gloeosporium laeticolor; Glomerella species, such as Glomerella cingulata;
Guignardia-Arten, wie beispielsweise Guignardia bidwelli;Guignardia species, such as Guignardia bidwelli;
Leptosphaeria-Arten, wie beispielsweise Leptosphaeria maculans;Leptosphaeria species, such as Leptosphaeria maculans;
Magnaporthe-Arten, wie beispielsweise Magnaporthe grisea;Magnaporthe species, such as Magnaporthe grisea;
Mycosphaerella-Arten, wie beispielsweise Mycosphaerella graminicola und Mycosphaerella fijiensis; Phaeosphaeria-Arten, wie beispielsweise Phaeosphaeria nodorum;Mycosphaerella species, such as Mycosphaerella graminicola and Mycosphaerella fijiensis; Phaeosphaeria species, such as Phaeosphaeria nodorum;
Pyrenophora-Arten, wie beispielsweise Pyrenophora teres;Pyrenophora species, such as, for example, Pyrenophora teres;
Ramularia-Arten, wie beispielsweise Ramularia collo-cygni;Ramularia species, such as Ramularia collo-cygni;
Rhynchosporium-Arten, wie beispielsweise Rhynchosporium secalis;Rhynchosporium species, such as Rhynchosporium secalis;
Septoria-Arten, wie beispielsweise Sqrtoria apii; Typhula-Arten, wie beispielsweise Typhula incarnata;Septoria species, such as Sqrtoria apii; Typhula species, such as Typhula incarnata;
Venturia-Arten, wie beispielsweise Vetituria inaequalis;Venturia species, such as Vetituria inaequalis;
Wurzel- und Stengelkrankheiten, hervorgerufen durch z.B.Root and stem diseases caused by e.g.
Corticium-Arten, wie beispielsweise Corticium graminearum; Fusarium-Arten, wie beispielsweise Fusarium oxysporum;Corticium species, such as Corticium graminearum; Fusarium species such as Fusarium oxysporum;
Gaeumannomyces-Arten, wie beispielsweise Gaeumaimomyces graminis;Gaeumannomyces species such as Gaeumaimomyces graminis;
Rhizoctonia-Arten, wie beispielsweise Rhizoctonia solani;Rhizoctonia species, such as Rhizoctonia solani;
Tapesia-Arten, wie beispielsweise Tapesia acuformis oder Tapesia yallundae;Tapesia species such as Tapesia acuformis or Tapesia yallundae;
Thielaviopsis-Arten, wie beispielsweise Thielaviopsis basicola;Thielaviopsis species, such as Thielaviopsis basicola;
Ähren- und Rispenerkrankungen (inklusive Maiskolben), hervorgerufen durch z.B.Ear and panicle diseases (including corncob) caused by e.g.
Alternaria-Arten, wie beispielsweise Alternaria spp.;Alternaria species, such as Alternaria spp .;
Aspergillus-Arten, wie beispielsweise Aspergillus flavus;Aspergillus species, such as Aspergillus flavus;
Cladosporium-Arten, wie beispielsweise Cladosporium cladosporioides; Claviceps-Arten, wie beispielsweise Claviceps purpurea;Cladosporium species, such as Cladosporium cladosporioides; Claviceps species, such as Claviceps purpurea;
Fusarium-Arten, wie beispielsweise Fusarium culmorum; Gibberella-Arten, wie beispielsweise Gibberella zeae; Monographella-Arten, wie beispielsweise Monographella nivalis;Fusarium species such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Monographella species, such as Monographella nivalis;
Erkrankungen, hervorgerufen durch Brandpilze wie z.B. Sphacelotheca-Arten, wie beispielsweise Sphacelotheca reiliana; Tilletia-Arten, wie beispielsweise Tilletia caries; Urocystis-Arten, wie beispielsweise Urocystis occulta; Ustilago-Arten, wie beispielsweise Ustilago nuda;Diseases caused by fire fungi, e.g. Sphacelotheca species, such as Sphacelotheca reiliana; Tilletia species, such as Tilletia caries; Urocystis species, such as Urocystis occulta; Ustilago species such as Ustilago nuda;
Fruchtfaule hervorgerufen durch z.B.Fruit rot caused by e.g.
Aspergillus-Arten, wie beispielsweise Aspergillus flavus;Aspergillus species, such as Aspergillus flavus;
Botrvtis-Arten, wie beispielsweise Botrytis cinerea;Botrvtis species, such as Botrytis cinerea;
Penicillium-Arten, wie beispielsweise Penicillium expansum und Penicillium purpurogenum;Penicillium species such as Penicillium expansum and Penicillium purpurogenum;
Sclerotinia-Arten, wie beispielsweise Sclerotinia sclerotiorum; Verricilium-Arten, wie beispielsweise Verticilium alboatrum;Sclerotinia species, such as Sclerotinia sclerotiorum; Verricilium species such as, for example, Verticilium alboatrum;
Samen- und bodenbürtige Fäulen und Welken, sowie Sämlingserkrankungen, hervorgerufen durch z.B. Fusarium-Arten, wie beispielsweise Fusarium culmorum; Phytophthora Arten, wie beispielsweise Phytophthora cactorum; Pythium-Arten, wie beispielsweise Pythium ultimum;Seed and soil rots and wilts, as well as seedling diseases caused by e.g. Fusarium species such as Fusarium culmorum; Phytophthora species, such as Phytophthora cactorum; Pythium species such as Pythium ultimum;
Rhizoctonia-Arten, wie beispielsweise Rhizoctonia solani; Sclerotium-Arten, wie beispielsweise Sclerotium rolfsii;Rhizoctonia species, such as Rhizoctonia solani; Sclerotium species, such as Sclerotium rolfsii;
Krebserkrankungen, Gallen und Hexenbesen, hervorgerufen durch z.B. Nectria-Arten, wie beispielsweise Nectria galligena;Cancers, galls and witches brooms caused by e.g. Nectria species, such as Nectria galligena;
Welkeerkrankungen hervorgerufen durch z.B. Monilinia-Arten, wie beispielsweise Monilinia laxa;Wilt diseases caused by e.g. Monilinia species, such as Monilinia laxa;
Deformationen von Blättern, Blüten nrnd Früchten, hervorgerufen durch z.B. Taphrina-Arten, wie beispielsweise Taphrina deformans;Deformations of leaves, flowers and fruits caused by e.g. Taphrina species, such as Taphrina deformans;
Degenerationserkrankungen holziger pflanzen, hervorgerufen durch z.B.Degenerative diseases of woody plants, caused by e.g.
Esca-Arten, wie beispielsweise Phaeomoniella chlamydospora und Phaeoacremonium aleophilum und Fomitiporia mediterranea;Esca species such as Phaeomoniella chlamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea;
Blüten- und Samenerkrankungen, hervorgerufen durch z.B. Botrytis-Arten, wie beispielsweise Botrytis cinerea;Flower and seed diseases, caused by eg Botrytis species, such as Botrytis cinerea;
Erkrankungen von Pflanzenknollen, hervorgerufen durch z.B. Rhizoctonia-Arten, wie beispielsweise Rhizoctonia solani; Hehninthosporium-Arten, wie beispielsweise Helminthosporium solani;Diseases of plant tubers caused by e.g. Rhizoctonia species, such as Rhizoctonia solani; Hehninthosporium species, such as Helminthosporium solani;
Erkrankungen, hervorgerufen durch bakterielle Erreger wie z.B. Xanthomonas-Arten, wie beispielsweise Xanthomonas campestris pv. oryzae; Pseudomonas-Arten, wie beispielsweise Pseudomonas syringae pv. lachrymans; Erwinia-Arten, wie beispielsweise Erwinia amylovora;Diseases caused by bacterial agents such as e.g. Xanthomonas species, such as Xanthomonas campestris pv. Oryzae; Pseudomonas species, such as Pseudomonas syringae pv. Lachrymans; Erwinia species, such as Erwinia amylovora;
Bevorzugt können die folgenden Krankheiten von Soja-Bohnen bekämpft werden: Pilzkrankheiten an Blättern, Stängeln, Schoten und Samen verursacht durch z.B. 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), Pod and Stern Blight (Phomopsis sojae), 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)Preferably, the following diseases of soybean beans can be controlled: fungal diseases on leaves, stems, pods and seeds caused by e.g. 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), Pod and star Blight (Phomopsis sojae), 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)
Pilzkrankheiten an Wurzeln und der Stängelbasis verursacht durch z.B. 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 (Neocosmospora 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 (Thielaviopsis basicola).Fungal diseases on roots and stem base caused by e.g. 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 (Neocosmospora 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 Red, Star Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Star Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola).
Die erfindungsgemäßen Wirkstoffe weisen auch eine starke stärkende Wirkung in Pflanzen auf. Sie eignen sich daher zur Mobilisierung pflanzeneigener Abwehrkräfte gegen Befall durch unerwünschte Mikroorganismen.The active compounds according to the invention also have a strong tonic effect in plants. she are therefore suitable for mobilizing plant's own defenses against attack by unwanted microorganisms.
Unter pflanzenstärkenden (resistenzinduzierenden) Stoffen sind im vorliegenden Zusammenhang solche Substanzen zu verstehen, die in der Lage sind, das Abwehrsystem von Pflanzen so zu stimulieren, dass die behandelten Pflanzen bei nachfolgender Inokulation mit unerwünschten Mikroorganismen weitgehende Resistenz gegen diese Mikroorganismen entfalten.In the present context, plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of plants in such a way that the treated plants exhibit extensive resistance to these microorganisms with subsequent inoculation with undesired microorganisms.
Unter unerwünschten Mikroorganismen sind im vorliegenden Fall phytopathogene Pilze, Bakterien und Viren 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 28 Tage, vorzugsweise 1 bis 14, besonders bevorzugt 1 bis 7 Tage nach der Behandlung der Pflanzen mit den Wirkstoffen.Undesirable microorganisms in the present case are phytopathogenic fungi, bacteria and viruses. 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 within which protection is induced generally extends from 1 to 28 days, preferably 1 to 14, more 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 erfindungsgemäßen Wirkstoffe mit besonders gutem Erfolg zur Bekämpfung von Getreidekrankheiten, wie z.B. gegen Puccinia-Arten und von Krankheiten im Wein-, Obst- und Gemüseanbau, wie z.B. gegen Botrytis-, Venturia- oder Alternaria-Arten, einsetzen.In this case, the active compounds according to the invention can be used with particularly good success for controlling cereal diseases, such as, for example, against Puccinia species and diseases in the wine, fruit and vegetable growing, such. against Botrytis, Venturia or Alternaria species.
Die erfindungsgemäßen Wirkstoffe eignen sich auch zur Steigerung des Ernteertrages. Sie sind außerdem mindertoxisch und weisen eine gute Pflanzenverträglichkeit auf.The active compounds according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
Die erfindungsgemäßen Wirkstoffe können gegebenenfalls in bestimmten Konzentrationen und Aufwandmengen auch als Herbizide, zur Beeinflussung des Pflanzenwachstums, sowie zur Bekämpfung von tierischen Schädlingen verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- und Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen.The active compounds according to the invention may optionally also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of other active ingredients.
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). Kumirpflan- zen 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). Kumir plants can be plants produced by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods including the transgenic plants and including the plant varieties which can be protected or not protected by plant variety rights. Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Wirkstoffen erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, Sprühen, Verdampfen, Vernebeln, Streuen, Aufstreichen 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.
Im Materialschutz lassen sich die erfindungsgemäßen Stoffe zum Schutz von technischen Materialien gegen Befall und Zerstörung durch unerwünschte Mikroorganismen einsetzen.In the protection of materials, the substances according to the invention can be used to protect industrial materials against infestation and destruction by undesired microorganisms.
Unter technischen Materialien sind im vorliegenden Zusammenhang nichtlebende Materialien zu verstehen, die für die Verwendung in der Technik zubereitet worden sind. Beispielsweise können technische Materialien, die durch erfindungsgemäße Wirkstoffe vor mikrobieller Veränderung oder Zerstörung geschützt werden sollen, Klebstoffe, Leime, Papier und Karton, Textilien, Leder, Holz, Anstrichmittel und Kunststoffartikel, Kühlschmierstoffe und andere Materialien sein, die von Mikroorganismen befallen oder zersetzt werden können. Im Rahmen der zu schützenden Materialien seien auch Teile von Produktionsanlagen, beispielsweise Kühlwasserkreisläufe, genannt, die durch Ver- mehrung von Mikroorganismen beeinträchtigt werden können. Im Rahmen der vorliegenden Erfindung seien als technische Materialien vorzugsweise Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Anstrichmittel, Kühlschmieπnittel und Wärmeübertragungsflüssigkeiten genannt, besonders bevorzugt Holz.Technical materials as used herein mean non-living materials that have been prepared for use in the art. For example, technical materials to be protected from microbial alteration or destruction by the active compounds of the invention may be adhesives, glues, paper and board, textiles, leather, wood, paints and plastics, coolants and other materials that may be infested or degraded by microorganisms , The materials to be protected also include parts of production plants, for example cooling water circuits, which may be adversely affected by the proliferation of microorganisms. In the context of the present invention, technical materials which may be mentioned are preferably adhesives, glues, papers and cardboard, leather, wood, paints, coolants and heat transfer liquids, particularly preferably wood.
Als Mikroorganismen, die einen Abbau oder eine Veränderung der technischen Materialien bewirken können, seien beispielsweise Bakterien, Pilze, Hefen, Algen und Schleimorganismen genannt. Vorzugsweise wirken die erfindungsgemäßen Wirkstoffe gegen Pilze, insbesondere Schimmelpilze, holzverfärbende und holzzerstörende Pilze (Basidiomyceten) sowie gegen Schleimorganismen und Algen.As microorganisms that can cause degradation or a change in the technical materials, for example, bacteria, fungi, yeasts, algae and mucus organisms may be mentioned. The active compounds according to the invention preferably act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
Es seien beispielsweise Mikroorganismen der folgenden Gattungen genannt: Alternaria, wie Altemaria tenuis, Aspergillus, wie Aspergillus niger, Chaetomium, wie Chaetomium globosum, Coniophora, wie Coniophora puetana, Lentinus, wie Lentinus tigrinus,There may be mentioned, for example, microorganisms of the following genera: Alternaria such as Altemaria tenuis, Aspergillus such as Aspergillus niger, Chaetomium such as Chaetomium globosum, Coniophora such as Coniophora puetana, Lentinus such as Lentinus tigrinus,
Penicillium, wie Penicillium glaucum, Polyporus, wie Polyporus versicolor, Aureobasidium, wie Aureobasidium puUulans, Sclerophoma, wie Sclerophoma pityophila, Trichoderma, wie Trichoderma viride, Escherichia, wie Escherichia coli, Pseudomonas, wie Pseudomonas aeruginosa, Staphylococcus, wie Staphylococcus aureus.Penicillium such as Penicillium glaucum, Polyporus such as Polyporus versicolor, Aureobasidium such as Aureobasidium puUulans, Sclerophoma such as Sclerophoma pityophila, Trichoderma such as Trichoderma viride, Escherichia such as Escherichia coli, Pseudomonas such as Pseudomonas aeruginosa, Staphylococcus such as Staphylococcus aureus.
Die Wirkstoffe können in Abhängigkeit von ihren jeweiligen physikalischen und/ oder chemischen Eigenschaften in die üblichen Foimulierungen überfuhrt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Pasten, Granulate, Aerosole, Feinstverkapselungen in polymeren Stoffen und in Hüllmassen für Saatgut, sowie ULV-KaIt- und Warmnebel-Foπnulierungen.Depending on their respective physical and / or chemical properties, the active compounds can be converted into the customary foimulations, 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 Foπnulierungen.
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. Im 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 Kohlenwasserstoffe, 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, Ahaniniumoxid und Silikate. Als feste Trägerstoffe für Granulate kom- men infrage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Bims, Marmor, Sepio- lith, 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. Ligiun-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 diluent, it is also possible, for example, to use organic solvents as auxiliary solvents. [Als Ar] 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, for example 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, as well as 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, ashaninium oxide and silicates. As solid carriers for granules, Examples include crushed and fractionated natural rocks such as calcite, pumice, marble, sepiolite, dolomite and synthetic granules of inorganic and organic flours, as well as granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stems. Suitable emulsifiers and / or foam-formers are: 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, Ligiun-Sulfitablaugen and methylcellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthe- tische pulverige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine, und synthetische Phospholipide. Weitere A.dditive können mineralische und vegetabile Öle sein.Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers can 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 A.dditives 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 erfindungsgemäßen Wirkstoffe 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 Fallen erhält man dabei synergistische Effekte, d.h. die Wirksamkeit der Mischung ist größer als die Wirksamkeit der Einzelkomponenten.The active compounds according to the invention, as such or in their formulations, can also be used 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:
1) Inhibitoren der Nukleinsäuresynthese: z.B. Benalaxyl, Benalaxyl-M, Bupirimate, Clozylacon, Dimethirimol, Ethirimol, Furalaxyl, Hymexazol, Mefenoxam, Metalaxyl, Metalaxyl-M, Ofurace,1) Inhibitors of nucleic acid synthesis: e.g. Benalaxyl, Benalaxyl M, Bupirimate, Clozylacone, Dimethirimol, Ethirimol, Furalaxyl, Hymexazole, Mefenoxam, Metalaxyl, Metalaxyl-M, Ofurace,
Oxadixyl, Oxolinic acid;Oxadixyl, oxolinic acid;
2) Inhibitoren von Mitose und Zellteilung: z.B. Benomyl, Carbendazim, Diethofencarb, Ethaboxam, Fuberidazole, Pencycuron, Thiabendazole, Thiophanate-methyl, Zoxamide;2) inhibitors of mitosis and cell division: e.g. Benomyl, carbendazim, diethofencarb, ethaboxam, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, zoxamide;
3) Inhibitoren der Respiration (Atmungsketten-hihibitoren): 3.1) Inhibitoren am Komplex I der Atmungskette: z.B. Diflumetorim; 3.2) Inhibitoren am Komplex II der Atmungskette: z.B. Boscalid/Nicobifen, Carboxin, Fenfuram, Flutolanil, Furametpyr, Furmecyclox, Mepronil, Oxycarboxin, Penthiopyrad, Thifluzamide;3) inhibitors of respiration (respiratory chain inhibitors): 3.1) inhibitors of complex I of the respiratory chain: eg diflumetorim; 3.2) inhibitors of complex II of the respiratory chain: eg boscalid / nicobifen, carboxin, fenfuram, flutolanil, furametpyr, Furmecyclox, mepronil, oxycarboxine, penthiopyrad, thifluzamide;
3.3) Inhibitoren am Komplex III der Atmungskette: z.B. Amisulbrom, Azoxystrobin, Cyazofamid, Dimoxystrobin, Enestrobin, Famoxadone, Fenamidone, Fluoxastrobin, Kresoxim-methyl, Metomino- strobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Trifloxystrobin;3.3) inhibitors at the complex III of the respiratory chain: e.g. Amisulbrom, azoxystrobin, cyazofamide, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metomino-strobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin;
4) Entkoppler: z.B. Dinocap, Fluazinam, Meptyldinocap;4) decoupler: e.g. Dinocap, fluazinam, meptyldinocap;
5) Inhibotoren der ATP Produktion: z.B. Fentin acetate, Fentin chloride, Feπtin hydroxide, Silthiofam;5) Inhibitors of ATP production: e.g. Fentin acetate, Fentin chloride, Feπtin hydroxide, Silthiofam;
6) Inhibitoren der Aminosäure- und Protein-Biosynthese: z.B. Andoprim, Blasticidin-S, Cyprodinil, Kasugamycin, Kasugamycin hydrochloride hydrate, Mepanipyrim, Pyrimethanil; 7) Inhibitoren der Signahransduktion: z.B. Fenpiclonil, Fludioxonil, Quinoxyfen;6) Inhibitors of amino acid and protein biosynthesis: e.g. Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil; 7) inhibitors of the signal transduction: e.g. Fenpiclonil, fludioxonil, quinoxyfen;
8) Inhibitoren der Lipid- und Membran-Synthese: z.B. Biphenyl, Chlozolinate, Edifenphos, Iodocarb, Iprobenfos, Iprodione, Isoprothiolane, Procymidone, Propamocarb, Propamocarb hydrochloride, Pyrazophos, Tolclofos-methyl, Vinclozolin;8) Inhibitors of lipid and membrane synthesis: e.g. Biphenyl, chlozolinates, edifenphos, iodocarb, Iprobenfos, iprodione, isoprothiolanes, procymidones, propamocarb, propamocarb hydrochloride, pyrazophos, tolclofos-methyl, vinclozolin;
9) Inhibitoren der Ergosterol-Biosynthese: z.B. Aldimorph, Azaconazole, Bitertanol, Bromuconazole, Cyproconazole, Diclobutrazole, Difenoconazole, Diniconazole, Diniconazole-M,9) Inhibitors of ergosterol biosynthesis: e.g. Aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M,
Dodemorph, Dodemorph acetate, Epoxiconazole, Etaconazole, Fenarimol, Fenbuconazole, Fenhexamid, Fenpropidin, Fenpropirnorph, Fluquinconazole, Flvirprimidol, Flusilazole, Flutriafol, Furconazole, Furconazole-cis, Hexaconazole, Imazalil, Imazalil sulfate, Imibenconazole, Ipconazole, Metconazole, Myclobutanil, Naftifine, Nuarimol, Oxpoconazole, Paclobutrazol, Pefurazoate, Penconazole, Prochloraz, Propiconazole, Prothioconazole, Pyributicarb, Pyrifenox, Simeconazole, Spiroxamine, Tebuconazole, Terbinafine, Tetraconazole, Triadimefon, Triadimenol, Tridemoφh, Triflumizole, Triforine, Triticonazole., Uniconazole, Viniconazole, Voriconazole;Dodemorph, Dodemorph acetate, Epoxiconazole, Etaconazole, Fenarimol, Fenbuconazole, Fenhexamid, Fenpropidin, Fenpropirnorph, Fluquinconazole, Flvirprimidol, Flusilazole, Flutriafol, Furconazole, Furconazole-cis, Hexaconazole, Imazalil, Imazalil sulfate, Imibenconazole, Ipconazole, Metconazole, Myclobutanil, Naftifine, Nuarimol, oxpoconazole, paclobutrazole, pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole, pyributicarb, pyrifenox, simeconazole, spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon, triadimenol, tridemoφh, triflumizole, triforine, triticonazole., Uniconazole, viniconazole, voriconazole;
10) Inhibitoren der Zellwandsynthese: z.B. Benthiavalicarb, Dimethomorph, Flumorph, Iprovalicarb, Polyoxins, Polyoxorim, Validamycin A; 11) Inhibitoren der Melanin-Biosynthese: z.B. Carpropamid, Diclocymet, Fenoxanil, Phthalide, Pyroquilon, Tricyclazole;10) inhibitors of cell wall synthesis: e.g. Benthiavalicarb, dimethomorph, flumorph, iprovalicarb, polyoxins, polyoxorim, validamycin A; 11) Inhibitors of melanin biosynthesis: e.g. Carpropamide, diclocymet, fenoxanil, phthalides, pyroquilon, tricyclazole;
12) Resistenzinduktoren: z.B. Acibenzolar-S-methyl, Probenazole, Tiadinil;12) resistance inducers: e.g. Acibenzolar-S-methyl, Probenazoles, Tiadinil;
13) Verbindungen mit Multisite-Aktivität: z.B. Bordeaux Mixture, Captafol, Captan, Chlorothalonil, Copper naphthenate, Copper oxide, Copper oxychloride, Kupferzubereitungen wie z.B. Kupferhy- droxid, Kupfersulfat, Dichlofluanid, Dithianon, Dodine, Dodine free base, Ferbam, Fluorofolpet, Folpet, Guazatine, Guazatine acetate, Iminoctadine, Lninoctadine albesilate, Iminoctadine triacetate, Mancopper, Mancozeb, Maneb, Metiratn, Metiram Zinc, Oxine-Copper, Propineb, Sulphur und Schweferlzubereitungen wie z.B. Calcium polysulphide, Thiram, Tolylfluanid, Zineb, Ziram;13) Compounds with multisite activity: e.g. Bordeaux Mixture, Captafol, Captan, Chlorothalonil, Copper Naphthenate, Copper Oxide, Copper Oxychloride, Copper Preparations, e.g. Copper hydroxide, copper sulfate, dichlofluanid, dithianone, dodine, dodine free base, Ferbam, Fluorofolpet, Folpet, Guazatine, Guazatine acetate, iminoctadine, Lninoctadine albesilate, iminoctadine triacetate, Mancopper, Mancozeb, Maneb, Metiratn, Metiram Zinc, Oxine-Copper, Propineb, Sulfur and Schweferlzubereitungen such as Calcium polysulphide, thiram, tolylfluanid, zineb, ziram;
14) eine Verbindung aus der folgenden Liste: (2E)-2-(2-{[6-(3-Chlor-2-methylphenoxy)-5-fluoφyrimi- dm-4-yl]oxy}phenyl)-2-(memoκyimmo)-N-methylacetamid, (2E)-2-{2-[({[(lE)-l-(3-{[(E)-l-Fluor-2- phenyl\räyl]oxy}phenyl)ethyüden]amino}oxy)memyl]phenyl}-2-(methoxyimmo)-N-memylacetar^ 1- (4-Chloφhenyl)-2-(lH-l,2,4-triazol-] -yl)cycloheptanol, l-[(4-Methoxyphenoxy)methyl]-2,2-dime- thylpropyl-lH-imidazol-1-carboxylat, 2-(4-Chloφhenyl)-N-{2-[3-methoxy-4-(prop-2-yn-l-yloxy)- phenyljethyl} -2-(prop-2-yn- 1 -yloxy)acetamid, 2,3,5,6-Tetrachlor-4-(methylsulfonyl)pyridin, 2- Butoxy-6-iod-3-propyl-4H-chromen-4-on, 2-Chlor-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4- yi)rricotinarnid, 2-Phenylphenol vuid Salze davon, 3,4,5-Trichlorpyridin-2,6-dicarbonitril, 3,4- Dichlor-N-(2-cyanophenyl)isothiazol-5-carboxainid, 3-[5-(4-Chlorphenyl)-2,3-dimethylisoxazolidin- 3-yl]pyridin, 5-Chlor-6-(2,4J6-trifluorophenyl)-N-[(lR)-l,2,2-trimethylpropyl][l,2,4]triazolo[l,5- a]pyrimidin-7-amin, 5-Chlor-7-(4-methylpiperidin-l-yl)-6-(2,4,6-trifluorphenyl)[l,2J4]triazolo[l,5- a]pyrimidin, 5-Chlor-N-[(lR)-l,2-dimethylpropyl]-6-(2,4,6-trifluorphenyl)[l,254]triazolo[l,5- a]pyrimidin-7-amin, 8-Hydroxyquinolinsulfat, Benthiazole, Bethoxazin, Capsimycin, Carvone, Chinomethionat, Cufraneb, Cyflufenamid, Cymoxanil, Dazomet, Debacarb, Dichlorophen, Diclomezine, Dicloran, Difenzoquat, Difenzoquat Methylsulphate, Diphenylamine, Ferimzone, Flumetover, Fluopicolide, Fluoroimide, Flusulfamide, Fosetyl-Aluminium, Fosetyl-Calcium, Fosetyl- Sodium, Hexachlorobenzene, Irumamycin, Methasulfocarb, Methyl (2-chlor-5-{(lE)-N-[(6- methylpyridm-2-yl)methoxy]ethaniinidoyl}benzyl)carbamat, Methyl (2E)-2-{2-[({cyclopropyl[(4- methoxyphenyl)imino]methyl}thio)me!thyl]phenyl}-3-methoxyacrylat, Methyl l-(2,2-dimethyl-2,3- dihydro-lH-inden-1 -yl)-lH-imidazol-5-carboxylat, Methyl 3-(4-chlorphenyl)-3-{ [N-14) a compound from the following list: (2E) -2- (2 - {[6- (3-chloro-2-methylphenoxy) -5-fluoro-pyrimidin-4-yl] oxy} phenyl) -2- ( memoκyimmo) -N-methylacetamide, (2E) -2- {2 - [({[(LE) -l- (3 - {[(E) -l-fluoro-2-phenylpropyl] oxy} phenyl) ethyl ] amino} oxy) memyl] phenyl} -2- (methoxyimmo) -N-memylacetar ^ 1- (4-Chloφhenyl) -2- (lH-l, 2,4-triazol] -yl) cycloheptanol, l - [(4-methoxyphenoxy) methyl] -2,2-dimethyl-thylpropyl lH-imidazol-1- carboxylate, 2- (4-chlorophenyl) -N- {2- [3-methoxy-4- (prop-2-yn-1-yloxy) -phenyl-ethyl} -2- (prop-2-yn-1-yloxy) acetamide, 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, 2-chloro-N- (1, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl) ricotinamide, 2-phenylphenol vuide salts thereof, 3,4,5-trichloropyridine-2,6-dicarbonitrile, 3,4-dichloro-N- ( 2-cyanophenyl) isothiazole-5-carboxamide, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine, 5-chloro-6- (2,4 J 6 -trifluorophenyl) -N [(lR) -l, 2,2-trimethylpropyl] [l, 2,4] triazolo [l, 5-a] pyrimidin-7-amine, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2- J ] triazolo [l, 5-a] pyrimidine, 5-chloro-N - [(1R) -l, 2-dimethylpropyl] -6- ( 2,4,6-trifluorophenyl) [l, 2 5 4] triazolo [l, 5- a] pyrimidin-7-amine, 8-Hydroxyquinolinsulfat, Benthiazole, bethoxazin, capsimycin, carvone, chinomethionat, Cufraneb, Cyflufenami d, cymoxanil, dazomet, debacarb, dichlorophen, diclomethine, diclorane, difenzoquat, difenzoquat methylsulphate, diphenylamine, ferimzone, flumetover, fluopicolide, fluoroimide, flusulfamide, fosetyl-aluminum, fosetyl-calcium, fosetyl-sodium, hexachlorobenzene, irumamycin, methasulfocarb, methyl (2-chloro-5 - {(IE) -N - [(6-methylpyridm-2-yl) methoxy] ethaninidoyl} benzyl) carbamate, methyl (2E) -2- {2 - [({cyclopropyl [(4- methoxyphenyl) imino] methyl} thio) methyl] phenyl} -3-methoxyacrylate, methyl 1- (2,2-dimethyl-2,3-dihydro-1H-inden-1-yl) -1H-imidazole-5 carboxylate, methyl 3- (4-chlorophenyl) -3- {[N-
(isopropoxycarbonyl)valyl]amino}propanoat, Methyl isothiocyanate, Metrafenone, Mildiomycin, N- (S'^'-Dichlor-S-fluorbiphenyl^-yO-S^difluoπnethy^-l-methyl-lH-pyrazol^-carboxainid, N-(3- Ethyl-3,5,5-trimethylcyclohexyl)-3-(foπnylamino)-2-hydroxybenzamid, N-(4-Chlor-2-nitrophenyl)- N-ethyl-4-methylbenzensulfonamid, N-KS-Brom-S-chlorpyridin^-yOmethyll^^-dichlorπicotinamid, N-[l-(5-Brom-3-cωoφyridin-2-yl)ethy]]-2,4-dicωoπiicσtinaπiid, N-[l-(5-Brom-3-chlorpyridin-2- yl)ethyl]-2-fluor-4-iodnicotinamid, N-[2-(4-{[3-(4-Chloiphenyl)prop-2-yn-l-yl]oxy}-3- me1hoxyphmyl)e%l]-N2-(methylsxιlfθEiyl)valinamid, N-{(Z)-[(Cyclopropylmethoxy)imino][6-(difluor- methoxy)-2,3-difluoφhenyl]inethyl}-2-phenylacetamid, N-{2-[3-Chlor-5-(trifluormethyl)pyridin-2- yl]ethyl}-2-(trifluormethyl)benzamid, Natamycin, Nickel Dunethyldithiocarbamate, Nitrothal- isopropyl, O-{l-[(4-Methoxyphenoxy)methyl]-2,2-dimethylpropyl} lH-Imidazol-1-carbothioat, Oc- thilinone, Oxamocarb, Oxyfenthiin, Peπtachlorophenol und Salze, Phosphorsäure und ihre Salze, Piperalin, Propamocarb Fosetylate, Propanosine-Sodium, Proquinazid, Pyrrohύtrine, Quintozene, Tecloftalam, Tecnazene, Triazoxide, Trichlamide, Zarilamid.(isopropoxycarbonyl) valyl] amino} propanoate, methyl isothiocyanate, metrafenone, mildiomycin, N- (S ', -' - dichloro-S-fluorobiphenyl) -YO-S-difluoromethyl-1-methyl-1H-pyrazole-carboxamide, N - (3-ethyl-3,5,5-trimethylcyclohexyl) -3- (phenylamino) -2-hydroxybenzamide, N- (4-chloro-2-nitrophenyl) -N-ethyl-4-methylbenzenesulfonamide, N-KS-bromo -S-chloropyridine ^ -y-methyl-1'-dichloro-nicotinamide, N- [1- (5-bromo-3-cω-pyridin-2-yl) -ethyl] -2,4-dicyclo-acetic acid, N- [1- (5-bromo) 3-chloropyridin-2-yl) ethyl] -2-fluoro-4-iodo-nicotinamide, N- [2- (4 - {[3- (4-chlorophenyl) -prop-2-yn-1-yl] oxy} -3 - me1hoxyphmyl) e% 1] - N 2 - (methylsulfinyl) valinamide, N - {(Z) - [(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] ethyl} -2-phenylacetamide , N- {2- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] ethyl} -2- (trifluoromethyl) benzamide, natamycin, nickel, dimethyldithiocarbamate, nitrothal isopropyl, O- {l - [4- Methoxyphenoxy) methyl] -2,2-dimethylpropyl} lH-imidazole-1-carbothioate, o-thilinones, oxamocarb, oxyfenthiine, pentachlorophenol and the like d salts, phosphoric acid and its salts, piperine, Propamocarb Fosetylate, Propanosine sodium, Proquinazid, Pyrrohύtrine, Quintozene, Tecloftalam, Tecnazene, triazoxide, trichlamide, zarilamide.
Bakterizide:bactericides:
Bronopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamycin, Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen. Insektizide / Akarizide / Nematizide :Bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations. Insecticides / acaricides / nematicides:
1. Acetylcholinesterase (AChE) Inhibitoren1. Acetylcholinesterase (AChE) inhibitors
1.1 Carbamate (z.B. Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Azamethiphos, Bendiocarb, Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbo- fiiran, 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)1.1 carbamates (eg alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, azamethiphos, bendocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofiran, 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, Chlorfenvin- phos, Chlormephos, Chlorpyrifos (-methyl/-ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlor- fenvinphos, 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, FIu- pyrazofos, Fonofos, Foπnothion, Fosmethilan, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-salicylate, Isoxathion, Malathion, Mecarbam, Methacrifos, Me- thamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl/-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)1.2 Organophosphates (eg. Acephate., Azamethiphos, Azinphos (-methyl, -ethyl), Bromophos-ethyl, Bromfenvinfos (-methyl), Butathiofos, Cadusafos, Carbophenothion, Chloroethoxyfos, Chlorfenvinophos, Chlormephos, Chlorpyrifos (-methyl / -ethyl) , Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphone, Dialifos, Diazinon, Dichlofenthione, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos , Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flu- pyrazofos, Fonofos, Foπnothion, Fosmethilan, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-salicylate, Isoxathion, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl / -ethyl), Phenthoate, Phorates, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Pirimiphos (-methyl / -ethyl), Profenofos, Propaphos, Propetamphos, prothiofos, prothoates, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometone, triazophos, triclorfone, vamidothion)
2. Natrium-Kanal-Modulatoren / Spannungsabhängige Natrium-Kanal-Blocker2. 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, Cypeπnethrin (alpha-, beta-, theta-, zeta-), Cyphenothrin, DDT, Deltamethrin, Empenthrin (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, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypeπnethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, empenthrin (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 (lR- trans isomer), prallethrin, profuthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (IR isomer), tralomethyrin, transfluthrin, ZXI 8901, pyrethrin (pyrethrum))
2.2 Oxadiazine (z.B. Indoxacarb)2.2 Oxadiazines (e.g., indoxacarb)
3. Acetylcholin-Rezeptor-Agonistenf-Antagonisten 3.1 Chloronicotinyle/Neonicotinoide (z.B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Ni- tenpyratn, Nithiazine, Thiacloprid, Thdamethoxam) 3.2 Nicotine, Bensultap, Cartap3. Acetylcholine Receptor Agonist F Antagonists 3.1 Chloronicotinyls / Neonicotinoids (eg Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitpyratn, Nithiazines, Thiacloprid, Thdamethoxam) 3.2 Nicotine, Bensultap, Cartap
4. Acetylcholin-Rezeptor-Modulatoren4. Acetylcholine receptor modulators
4.1 Spinosyne (z.B. Spinosad)4.1 Spinosyns (e.g., spinosad)
5. GABA-gesteuerte Chlorid-Kanal-Antagonisten 5.1 Cyclodiene Organochlorine (z.B. Camphechlor, Chlordane, Endosulfan, Gamma-HCH, HCH, Heptachlor, Lindane, Methoxychlor5. GABA-Directed Chloride Channel Antagonists 5.1 Cyclodienes Organochlorines (e.g., camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
5.2 Fiprole (z.B. Acetoprole, Ethiprole, Fipronil, Vaniliprole)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. Juvenühormon-Mimetika7. Juvenile hormone mimetics
(z.B. Diofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene, Methoprene, Pyriproxifen, Triprene)(e.g., diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprenes, methoprenes, pyriproxifen, triprene)
8. Ecdysonagonisten/disruptoren 8.1 Diacylhydrazine (z.B. Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide)8. ecdysone agonists / disruptors 8.1 diacylhydrazines (e.g., chromafenozides, halofenozides, methoxyfenozides, tebufenozides)
9. Inhibitoren der Chitinbiosynthese9. Inhibitors of chitin biosynthesis
9.1 Benzoylharnstofre (z.B. Bistrifluron, Chlofluazuron, Difhibenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penfluron, Teflubenzuron, Tri- flumuron) 9.2 Buprofezin9.1 Benzoylureas (for example bistrifluron, chlorofluazuron, difibenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, trifluoron) 9.2 Buprofezin
9.3 Cyromazine9.3 Cyromazine
10. Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren10. Inhibitors of oxidative phosphorylation, ATP disruptors
10.1 Diafenthiuron10.1 Diafenthiuron
10.2 Organotine (z.B. Azocyclotin, Cyhexatin, Feributatin-oxide) 11. Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Protongradienten10.2 Organotins (e.g., azocyclotin, cyhexatin, feributatin oxides) 11. Decoupling of oxidative phosphorylation by disruption of the H proton gradient
11.1 Pyrrole (z.B. Chlorfenapyr)11.1 Pyrroles (e.g., chlorfenapyr)
11.2 Dinitrophenole (z.B. Binapacyrl, Dinobuton, Dinocap, DNOC)11.2 Dinitrophenols (e.g., binapacyrl, dinobutone, dinocap, DNOC)
12. Site-I-Elektronentransportinhibhoren12. Site I electron transport inhibitors
12.1 METTs (z.B. Fenazaquiri, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad)12.1 METTs (e.g., Fenazaquiri, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad)
12.2 Hydramethylnone12.2 Hydramethylnone
12.3 Dicofol12.3 Dicofol
13. Site-II-Elektronentransportinhibitoren 13.1 Rotenone 14. Site-III-Elektronentransportinhibitoren 14.1 Acequinocyl, Fluacrypyrim 75. Mikrobielle Disruptoren der Insektendarmmembran Bacillus thuringiensis-Stämrne13. Site II Electron Transport Inhibitors 13.1 Rotenone 14. Site III Electron Transport Inhibitors 14.1 Acequinocyl, Fluacrypyrim 75. Microbial disruptors of insect intestinal membrane Bacillus thuringiensis strains
16. Inhibitoren der Fettsynthese16. Inhibitors of fat synthesis
16.1 Tetronsäuren (z.B. Spirodiclofen, Spiromesifen) 16.2 Tetramsäuren [z.B. 3-(2,5-I)imethylphenyl)-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)]16.1 Tetronic acids (eg spirodiclofen, spiromesifen) 16.2 Tetramic acids [eg 3- (2,5-I ) imethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate ( alias: 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)18. Octopaminergic agonists (e.g., Amitraz)
19. Inhibitoren der Magnesium-stimidierten ATPase (z.B. Propargite) 20. Agonisten des Ryanodin-Rezeptors,19. Inhibitors of magnesium-stimulated ATPase (e.g., propargites) 20. Agonists of the ryanodine receptor,
20.1 Benzoesäuredicarboxamide [z.B. N2-[l,l-Dimethyl-2-(methylsulfonyl)ethyl]-3-iod-N1-[2- methyl-4-[l ,2,2,2-tetrafluor- 1 -(trifluormethyl)ethyl]phenyl]- 1 ,2-benzenedicarboxamide (CAS-Reg.- No.: 272451-65-7), Flubendiamide]20.1 Benzoic acid dicarboxamides [eg N 2 - [l, l-dimethyl-2- (methylsulphonyl) ethyl] -3-iodo-N 1 - [2-methyl-4- [l, 2,2,2-tetrafluoro-1 - ( trifluoromethyl) ethyl] phenyl] -1,2-benzenedicarboxamide (CAS Reg. No .: 272451-65-7), flubendiamide]
20.2 Anthranilamide (z.B. DPX E2.Y45 = 3-Brom-N-{4-cMor-2-methyl-6-[(methylarnino)carbonyl]- phenyl}-l-(3-chlorpyridm-2-yl)-lH-pyi-azol-5-carboxamid)20.2 Anthranilamides (eg DPX E2.Y45 = 3-bromo-N- {4-c-m-2-methyl-6 - [(methylarnino) carbonyl] -phenyl} -1- (3-chloropyridm-2-yl) -lH- pyi-azol-5-carboxamide)
21. Nereistoxin-Analoge21. Nereistoxin Analogs
(z.B. Thiocyclam hydrogen Oxalate, Thiosultap-sodium)(e.g., thiocyclam hydrogen oxalate, thiosultap-sodium)
22. Biologika, Hormone oder Pheromone22. Biologics, hormones or pheromones
(z.B. Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhizium spec., Paecilomyces spec, Thuiingiensin, Verticillium sps:c.)(e.g., Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhicon spec., Paecilomyces spec, Thuiingiensin, Verticillium sps.
23. Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen23. Active substances with unknown or non-specific mechanisms 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) 23.4 Amidoflumet, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Buprofezin, Chinome- thionat, Chlordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben, Cycloprene, Cyflumetofen, Dicyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, Flufenerim, Flutenzin, Gossyplure, Hydramethyl- none, Japonilure, Metoxadiazone, Petroleum, Piperonyl butoxide, Potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin, ferner die Verbindung 3-Methyl-phenyl-propylcarbamat (Tiαimacide Z), die Verbindung 3-(5-Chlor-3-pyridinyl)-8-(2,2,2- trifhxoremyl)-8-azabicyclo[3.2J]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.23.3 Mite Growth Inhibitors (eg clofentezine, etoxazole, hexythiazox) 23.4 Amidoflumet, benclothiazole, benzoximate, bifenazate, bromopropylate, buprofezin, quinomethionate, chlordimeform, chlorobenzilate, chloropicrin, clothiazoben, cycloprene, cyflumetofen, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, flufenerim, flutenzin , Gossyplure, Hydramethylone, Japonilure, Metoxadiazone, Petroleum, Piperonyl butoxide, Potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin, and the compound 3-methyl-phenyl-propylcarbamate (Tiαimacide Z), the compound 3- (5-chloro-3-pyridinyl) -8- (2,2,2-trifluoromethyl) -8-azabicyclo [3.2] octane-3-carbonitrile (CAS Reg. No. 185982-80- 3) and the corresponding 3-endo isomers (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.
Auch eine Mischling mit anderen bekannten Wirkstoffen, wie Herbiziden oder mit Düngemitteln und Wachstumsregulatoren, Safener bzw. Semiochemicals ist möglich.Also a hybrid with other known active substances, such as herbicides or with fertilizers and growth regulators, safeners or semiochemicals is possible.
Darüber hinaus weisen die erfindungsgemäßen Verbindungen der Formel (I) auch sehr gute antimykotische Wirkungen auf. Sie besitzen ein sehr breites antimykotisches Wirkungsspektrum, insbesondere gegen Dermatophyten und Sprosspilze, Schimmel und diphasische Pilze (z.B. gegen Candida-Spezies wie Candida albicans, Candida glabrata) sowie Epidermophyton floccosum, Aspergillus-Spezies wie Aspergillus niger und Aspergillus fumigatus, Trichophyton-Spezies wie Trichophyton mentagrophytes, Microsporon-Spezies wie Microsporon canis und audouinii. Die Aufzählung dieser Pilze stellt keinesfalls eine Beschränkung des erfassbaren mykotischen Spektrums dar, sondern hat nur erläuternden Charakter.In addition, the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and yeasts, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The list of these fungi is by no means a limitation of the detectable mycotic spectrum, but has only an explanatory character.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, 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, Bestrei- chen 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 in the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. The application is done in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, spreading, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil. It can also be the seed of the plants to be treated.
Beim Einsatz der erfindungsgemäßen Wirkstoffe als Fungizide können die Aufwandmengen je nach Applikationsart innerhalb eines größeren Bereiches variiert werden. Bei der Behandlung vonWhen using the active compounds according to the invention as fungicides, the application rates can be varied within a relatively wide range, depending on the mode of administration. In the treatment of
Pflanzenteilen liegen die Aufwandmengen an Wirkstoff im allgemeinen zwischen 0,1 undPlant parts are the application rates of active ingredient generally between 0.1 and
10.000 g/ha, vorzugsweise zwischen 10 und 1.000 g/ha. Bei der Saatgutbehandlung hegen die10,000 g / ha, preferably between 10 and 1,000 g / ha. In seed treatment, the
Aufwandmengen an Wirkstoff im allgemeinen zwischen 0,001 und 50 g pro Kilogramm Saatgut, vorzugsweise zwischen 0,01 und K) 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.Application rates of active ingredient generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and K ) 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 erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden, wie Kreuzung oder Protoplastenfusion erhaltenen Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff „Teile" bzw. „Teile von Pflanzen" oder „Pflanzenteile" wurde oben erläutert.As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild-type or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant cultivars and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars, which may be obtained by genetic engineering, optionally in Combination with conventional methods were obtained (Genetically Modified Organisms) and their parts 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, Ernährang) können durch die erfindungsgemäße Behandlung auch überadditive („synergistische") Effekte auftreten. So sind beispielsweise erniedrigte Aufwandmengen und/oder Erweiterungen des Wirkungsspektrums und/oder eine Verstärkung der Wirkung der erfindungsgemäß verwendbaren Stoffe und Mittel, besseres Pflanzenwachstum, weiter entwickeltes Wurzelsystem, höhere Beständigkeit der Pflanzenart bzw. Pflanzensorte, gesteigertes Wachstum der Schösslinge, höhere Pflanzenvitalität, 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, größere Früchte, höhere Pflanzengröße, grünere Blattfarbe, frühere Blüte, höhere Qualität und/oder höherer Emährungswert der Ernteprodukte, höhere Zuckerkonzentration in den Früchten, 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, diet), the treatment according to the invention may also give rise to superadditive ("synergistic") effects, for example reduced application rates and / or extensions of the spectrum of action and / or a Strengthening of the effect of the substances and agents which can be used according to the invention, better plant growth, more developed root system, higher resistance of the plant species or plant variety, increased growth of the shoots, higher plant vitality, increased tolerance to high or low temperatures, increased tolerance to drought or to water or water Soil salinity, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, larger fruits, higher plant size, greener leaf color, earlier flowering, higher quality and / or higher harvest value of the harvested products, higher sugar concentration in the fruits, higher shelf life and / or workability of the harvested products possible, which go beyond the expected effects actually.
Zu den bevorzugten erfindungsgeritiäß 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 Lagerfahigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehr der Pflanzen gegen tierische und mikrobielle Schädlinge, wie gegenüber Insekten, Milben, pflanzenpathogenen Pilzen, Bakterien und/oder Viren sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis), Mais, Soja, Kartoffel, 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, CrylllA, 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 Wirkstoffen, z.B. Imidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinotricin (z.B. "PAT"- Gen). Die jeweils die gewünschten Eigenschaften („Traits") verleihenden Gene können auch in Kom- binationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele für „Bt Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und Kartoffelsorten genannt, die unter den Handelsbezeichnungen YIELD GARDd) (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 Glyphosate 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. Selbst- verständlich gelten diese Aussagen auch für in der Zukunft entwickelte bzw. zukünftig auf den Markt kommende Pflanzensorten mit diesen oder zukünftig entwickelten genetischen Eigenschaften („Traits").Preferred plants or plant varieties to be treated according to the invention include all plants which have obtained genetic material through the genetic engineering modification which gives these plants particularly advantageous traits, examples of which 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 against insects, mites, phytopathogenic fungi, bacteria and / or Vir and increased tolerance of the plants to certain herbicidal active substances. Examples of transgenic plants are the important crops, such as cereals (Wheat, rice), maize, soya, potato, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus and grapes), with special emphasis on maize, soya, potato, cotton, tobacco and oilseed rape. 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, CrylllA, 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. ), the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosates or phosphinotricin (eg "PAT" gene), are particularly emphasized. The genes which confer the desired properties ("traits") may also be present in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cottons, soybean varieties and potato varieties sold under the trade names YIELD GARDd (US Pat. corn, cotton, soy), KnockOut® (eg corn), StarLink® (eg corn), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, 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 plant varieties developed or to be marketed in the future with these or future developed genetic traits.
Die aufgeführten Pflanzen können besonders vorteilhaft erfindungsgemäß mit den Verbindungen der allgemeinen Formel (I) bzw. den erfuidungsgemäßen Wirkstoffinischungen 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 in accordance with the invention with the compounds of the general formula (I) or the active ingredient mixtures according to the 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 Herstellung und die Verwendung der erfindungsgemäßen Wirkstoffe geht aus den folgenden Beispielen hervor. HerstellungsbeispieleThe preparation and the use of the active compounds according to the invention are evident from the following examples. Preparation Examples
Herstellung von Verbindung Nr. 3Preparation of compound no. 3
Zu einer Suspension bestehend aus 130.0 mg (0.7 mmol) 3-(Difluormethyl)-l-methyl-lH-pyrazol-4- carbonsäure in 5 ml Dichlormethan werden bei Raumtemperatur 70 μl (0.8 mmol) Oxalsäuredichlorid und 30 μl Dimediylformamid gegeben. Nach 2 Stunden tropft man dieses Reaktionsgemisch zu einer Lösung bestehend aus 160.0 mg (0.7 mmol) N-Cyclopropyl-2-(l,3- dimethylbutyl)anilin und 130 μl (1.0 mmol) Triethylamin in 5 ml Dichlormethan. Nach 48 Stunden Rühren bei Raumtemperatur werden 4 ml Wasser zugegeben, die organische Phase wird abgetrennt, über Magnesiumsulfat getrocknet und im Vakuum aufkonzentriert. Man erhält nach Säulenchromatographie (Gradient Cyclohexan / Essigsäureethylester) 202.0 mg (0.5 mmol, 72% der Theorie) N-cyclopropyl-3-(difluormethyl)-N-[2-(l,3-dimethylbutyl)phenyl]-l-methyl-lH-pyrazol-4- carboxamid [Log P (pH 2.3) 3.89].To a suspension consisting of 130.0 mg (0.7 mmol) of 3- (difluoromethyl) -1-methyl-lH-pyrazole-4-carboxylic acid in 5 ml of dichloromethane 70 .mu.l (0.8 mmol) of oxalic acid dichloride and 30 ul Dimediylformamid be given at room temperature. After 2 hours, this reaction mixture is added dropwise to a solution consisting of 160.0 mg (0.7 mmol) of N-cyclopropyl-2- (l, 3-dimethylbutyl) aniline and 130 .mu.l (1.0 mmol) of triethylamine in 5 ml of dichloromethane. After 48 hours of stirring at room temperature, 4 ml of water are added, the organic phase is separated, dried over magnesium sulfate and concentrated in vacuo. After column chromatography (gradient cyclohexane / ethyl acetate), 202.0 mg (0.5 mmol, 72% of theory) of N-cyclopropyl-3- (difluoromethyl) -N- [2- (l, 3-dimethylbutyl) phenyl] -l-methyl- 1H-pyrazole-4-carboxamide [Log P (pH 2.3) 3.89].
Analog diesem Beispiel sowie entsprechend den allgemeinen Beschreibungen der erfindungsgemäßen Verfahren können die in der folgenden Tabelle 1 genannten Verbindungen der Formel (I) erhalten werden.Analogously to this example and according to the general descriptions of the process according to the invention, the compounds of the formula (I) mentioned in Table 1 below can be obtained.
Tabelle 1Table 1
Herstellung von Ausgangsstoffen der Formel (III) Preparation of starting materials of the formula (III)
Beispiel αil-liExample αil-li
Zu einer Lösung bestehend aus 531.9 mg (3.0 mmol) 2-(l,3-Dimethylbutyl)anilin in 5 ml Methanol, über 1.0 g 3Ä Molekularsieb werden bei Raumtemperatur 1.7 ml (30.0 mmol) Essigsäure und 627.5 mg (3.6 mmol) [(1-Ethoxycyclopropyl)oxy](trimethyl)silan gegeben. Die Reaktionsmischung wird für 20 Minuten bei Raumtemperatur gerührt und anschließend mit 1.04 g (16.5 mmol) Natriumcyanoborhydrid versetzt. Das Reaktionsgemisch wird für 16 Stunden bei 50°C gerührt. Bei Raumtemperatur werden 10 ml Wasser zugegeben. Die Reaktionsmischung wird filtriert und das Filtrat eingeengt. Der Rückstand wird mit 10 ml 1 mol/1 Natronlauge versetzt und 3 mal mit jeweils 20 ml Diethylether extrahiert. Die organische Phase wird mit gesättigter Kochsalzlösung gewaschen, über Natriumsulfat getrocknet und im Vakuum aufkonzentriert. Man erhält nach Säulenchromatographie (Gradient Cyclohexan / Essigsäureethylester) 220.0 mg (1.0 mmol, 34 % der Theorie) N-Cyclopropyl-2-(l,3-dimethylbutyl)anilin [Log P (pH 2.3) 5.33],To a solution consisting of 531.9 mg (3.0 mmol) of 2- (l, 3-dimethylbutyl) aniline in 5 ml of methanol, over 1.0 g of 3Ä molecular sieve at room temperature 1.7 ml (30.0 mmol) of acetic acid and 627.5 mg (3.6 mmol) [( 1-Ethoxycyclopropyl) oxy] (trimethyl) silane. The reaction mixture is stirred for 20 minutes at room temperature and then admixed with 1.04 g (16.5 mmol) of sodium cyanoborohydride. The reaction mixture is stirred for 16 hours at 50.degree. At room temperature, 10 ml of water are added. The reaction mixture is filtered and the filtrate is concentrated. The residue is mixed with 10 ml of 1 mol / 1 sodium hydroxide solution and extracted 3 times with 20 ml of diethyl ether. The organic phase is washed with saturated brine, dried over sodium sulfate and concentrated in vacuo. After column chromatography (gradient cyclohexane / ethyl acetate), 220.0 mg (1.0 mmol, 34% of theory) of N-cyclopropyl-2- (1,3-dimethylbutyl) aniline [Log P (pH 2.3) 5.33] are obtained,
Analog Beispiel (III-l) sowie entsprechend den allgemeinen Beschreibungen der erfindungsgemäßen Verfahren können die in der folgenden Tabelle 2 genannten Verbindungen der Formel (III) erhalten werden.Analogously to Example (III-l) and according to the general descriptions of the process according to the invention, the compounds of the formula (III) mentioned in Table 2 below can be obtained.
Tabelle 2Table 2
Die Bestimmung der in den voranstehenden Tabellen und Herstellungsbeispielen angegebenen logP- Werte erfolgt gemäß EEC-Directive 79/831 Annex V.A8 durch HPLC (High Performance Liquid Chromatography) an einer Phasenumkehrsäule (C 18). Temperatur: 43°C.The determination of the logP values indicated in the above tables and preparation examples is carried out according to EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.
Die Bestimmung erfolgt im sauren Bereich bei pH 2.3 mit 0,1 % wässriger Phosphorsäure und Acetonitril als Eluenten; linearer Gradient von 10 % Acetonitril bis 90 % Acetonitril.The determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluent; linear gradient from 10% acetonitrile to 90% acetonitrile.
Die Eichung erfolgt mit unverzweigten Alkan-2-onen (mit 3 bis 16 Kohlenstoffatomen), deren logP- Werte bekannt sind (Bestimmung der logP-Werte anhand der Retentionszeiten durch lineare Interpolation zwischen zwei aufeinanderfolgenden Alkanonen).The calibration is carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms), whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two consecutive alkanones).
Die lambda-max-Werte wurden an Hand der UV-Spektren von 200 nm bis 400 nm in den Maxima der chromatographischen Signale ermittelt. The lambda max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
Anwendungsbeispieleapplications
Beispiel AExample A
Uromyces - Test (Bohne) / protektiv Lösungsmittel: 24,5 Gewichtsteile AcetonUromyces test (bean) / protective Solvent: 24.5 parts by weight of acetone
24,5 Gewichtsteile Dimethylacetamid Emulgator: 1 Gewichtsteil Alkylarylpolyglykolether24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
Zur Prüfung auf protektive Wirksamkeit werden junge Pflanzen mit der Wirkstoffzubereitung in der angegebenen Aufwandmenge besprüht. Nach Antrocknen des Spritzbelages werden die Pflanzen mit einer wässrigen Sporensuspension des Bohnenrosterregers Uromyces appendiculatus inokuliert und verbleiben dann 1 Tag bei ca. 200C xind 100 % relativer Luftfeuchtigkeit in einer Inkubationskabine. Die Pflanzen werden dann im Gewächshaus bei ca. 210C und einer relativen Luftfeuchtigkeit von ca. 90 % aufgestellt.To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of bean rust pathogen, Uromyces appendiculatus and then one day will remain at about 20 0 C X IND 100% relative humidity in an incubation cabinet. The plants are then placed in the greenhouse at about 21 0 C and a relative humidity of about 90%.
10 Tage nach der Inokulation erfolgt die Auswertung. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, dass kein Befall beobachtet wird.10 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
Tabelle ATable A
Uromyces - Test (Bohne) / protektivUromyces test (bean) / protective
Tabelle A Table A
Uromyces - Test (Bohne) / protektivUromyces test (bean) / protective
Beispiel BExample B
Alternaria - Test (Tomate) / protektiv Lösungsmittel: 49 Gewiclιtsteile N,N-DimethylformamidAlternaria test (tomato) / protective Solvent: 49 parts by weight N, N-dimethylformamide
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
Zur Prüfung auf protektive Wirksamkeit bespritzt man junge Tomatenpflanzen mit der Wirkstoffzubereitung in der angegebenen Aufwandmenge. 1 Tag nach der Behandlung werden die Pflanzen mit einer Sporensuspension von Alternaria solani inokuliert und stehen dann 24h bei 100 % relativer Feuchte und 200C. Anschließend stehen die Pflanzen bei 96 % relativer Luftfeuchtigkeit und einer Temperatur von 200C.To test for protective activity, young tomato plants are sprayed with the preparation of active compound in the stated application rate. One day after the treatment, the plants are inoculated with a spore suspension of Alternaria solani and then stand for 24 h at 100% relative humidity and 20 0 C. Then the plants are at 96% relative humidity and a temperature of 20 0 C.
7 Tage nach der Inokulation erfolgt die Auswertung. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, dass kein Befall beobachtet wird.7 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
Tabelle BTable B
Alternaria - Test (Tomate) / protektivAlternaria - Test (Tomato) / Protective
1000 100 Tabelle B1000 100 Table B
Alternaria - Test (Tomate) / protelrtivAlternaria - Test (Tomato) / protelrtiv
Beispiel CExample C
Pyrenophora teres - Test (Gerste) / protektiv Lösungsmittel: 50 Gewichisteile N,N-DimethylacetamidPyrenophora teres - test (barley) / protective Solvent: 50 parts by weight N, N-dimethylacetamide
Emυlgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. Zur Prüfung auf protektive Wirksamkeit werden junge Pflanzen mit der Wirkstoffzubereitung in der angegeben Aufwandmenge besprüht. Nach Antrocknen des Spritzbelages werden die Pflanzen mit einer Konidiensuspension von Pyrenophora teres besprüht. Die Pflanzen verbleiben 48 Stunden beiTo prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Pyrenophora teres. The plants remain for 48 hours
20°C und 100 % relativer Luftfeuchtigkeit in einer Inkubationskabine.20 ° C and 100% relative humidity in an incubation cabin.
Die Pflanzen werden dann in einem Gewächshaus bei einer Temperatur von ca. 20°C und relativenThe plants are then grown in a greenhouse at a temperature of about 20 ° C and relative
Luftfeuchtigkeit von ca. 80 % aufgestellt.Humidity of about 80% set up.
8 Tage nach der Inokulation erfolgt die Auswertung. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, dass kein8 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no
Befall beobachtet wird.Infestation is observed.
Tabelle CTable C
Pyrenophora teres - Test (Gerste) / protektivPyrenophora teres - test (barley) / protective

Claims

Patentansprflche Patentansprflche
1. Carboxamide der Formel (I)1. Carboxamides of the formula (I)
in welcher in which
X für O (Sauerstoff) oder S (Schwefel) steht,X is O (oxygen) or S (sulfur),
M für einen jeweils einfach durch R1 substituierten Phenyl-, Thiophen-, Pyridin-, Pyri- midin-, Pyridazin oder Pyrazin-Ring oder für einen durch R2 substituierten Thiazol- Ring steht, R1 für Wasserstoff, Fluor, Chlor, Methyl, iso-Propyl, Methylthio oder Trifluormethyl steht,M is a phenyl, thiophene, pyridine, pyrimidine, pyridazine or pyrazine ring which is in each case monosubstituted by R 1 or a thiazole ring substituted by R 2 , R 1 is hydrogen, fluorine, chlorine, methyl , iso-propyl, methylthio or trifluoromethyl,
R2 für Wasserstoff, Methyl, Methylthio oder Trifluormethyl steht, Q für eine direkte Bindung, Q-C^Alkylen, QrCrAlkenylen, O, S, SO, SO2 oder NR3 steht, R3 für Wasserstoff, d-Cg-Alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, CrC4-Alkylthio-Ci-C4- alkyl, C2-C8-Alkenyl, C2-C8-Alkinyl, Ci-C6-Halogenalkyl, C2-C6-Halogenalkenyl, C2-C6-Halogenalkiny] oder C3-C6-Cycloalkyl steht, Z für Z1, Z2, Z3, Z4, Z5 oder Z6 steht,R 2 is hydrogen, methyl, methylthio or trifluoromethyl, Q is a direct bond, QC ^ alkylene, QrCrAlkenylen, O, S, SO, SO 2 or NR 3 , R 3 is hydrogen, d-Cg-alkyl, ci C 4 -alkoxy-Ci-C 4 alkyl, C r C 4 alkylthio-Ci-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 -Halogenalkiny] or C 3 -C 6 cycloalkyl, Z is Z 1, Z 2, Z 3, Z 4, Z 5 or Z 6 is,
Z1 für gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Phenyl steht,Z 1 is optionally monounsaturated to quintuply, identically or differently substituted phenyl,
Z2 für gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertesZ 2 is optionally monosubstituted to trisubstituted by identical or different substituents
Pyridinyl steht,Pyridinyl stands,
Z3 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Alkyl und/oder -(CRV^SiR^R8 substituiertes Cycloalkyl oder Bicyclo- alkyl steht,Z 3 is in each case optionally mono- or polysubstituted, identically or differently, by halogen, alkyl and / or - (CRV ^ SiR ^ R 8 -substituted cycloalkyl or bicycloalkyl,
Z4 für unsubstituiertes C2-C2O-AIlCyI oder für einfach oder mehrfach, gleich oder verschieden durch Halogen, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkoxy, Alkylami- no, Dialkylamino, Halogenalkylthio, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Halogenalkoxy, Halogenalkylamino, Halogen-dialkylamino, -SiR6R7R8 und/oder C3- Cβ-Cycloalkyl substituiertes Ci-C2o-Alkyl steht, wobei der Cycloalkylteil seinerseits gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen und/oder Ci-C4-Alkyl substituiert sein kann, Z5 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Alkylthio, Alkylsulfϊnyl, Alkylsulfonyl, Alkoxy, Alkylamino, Dialkylami- no, Halogenalkylthio, Halogenalkylsulfmyl, Halogenalkylsulfonyl, Halogenalkoxy, Halogenalkylamino, Halogen-dialkylamino, -SiR6R7R8 und/oder C3-C6-Cycloalkyl substituiertes C2-C20-Alkenyl oder C2-C2o-Alkinyl steht, wobei der Cycloalkylteil seinerseits gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen und/oder Ci-C4-Alkyl substituiert sein kann,Z 4 is unsubstituted C 2 -C 2O -alkyl or monosubstituted or polysubstituted by identical or different halogen, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxy, alkylamines no, dialkylamino, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, haloalkoxy, Halogenalkylamino, halogen-dialkylamino , -SiR 6 R 7 R 8 and / or C 3 - Cβ-cycloalkyl substituted Ci-C 2 o-alkyl, wherein the cycloalkyl part in turn may be mono- or polysubstituted by identical or different halo and / or Ci-C 4 alkyl may be substituted Z 5 is in each case optionally monosubstituted or polysubstituted, identical or different, by halogen, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkylsulfmyl, haloalkylsulfonyl, haloalkoxy, haloalkylamino, halo-dialkylamino, -SiR 6 R 7 R 8 and / or C 3 -C 6 -cycloalkyl-substituted C 2 -C 20 -alkenyl or C 2 -C 2 o-alkynyl, where the cycloalkyl moiety in turn may be monosubstituted or polysubstituted, identically or differently, by halogen and / or C 1 -C 4 Alkyl may be substituted,
Z6 für einen gegebenenfalls einfach oder mehrfach substituierten, gesättigten oder ungesättigten 3- bis 7-gliedrigen Ring steht, welcher ein Siliziumatom als Ringglied enthält, wobei dann Q für eine direkte Bindung oder Ci-C4-Alkylen steht,Z 6 is an optionally monosubstituted or polysubstituted, saturated or unsaturated 3- to 7-membered ring which contains a silicon atom as ring member, in which case Q is a direct bond or C 1 -C 4 -alkylene,
R4 für Wasserstoff oder C,-C4-Alkyl steht,R 4 is hydrogen or C 1 -C 4 -alkyl,
R5 für Wasserstoff oder CrC4-Alkyl steht, m für O3 1, 2 oder 3 steht,R 5 is hydrogen or C 4 alkyl C r, m is O3 1, 2 or 3;
R6 und R7 unabhängig voneinander für Wasserstoff, Ci-C8-Alkyl, Ci-Cs-Alkoxy, Ci-C4- Alkoxy-Ci-C4-alkyl, Ci-C4-Alkylthio-C1-C4-alkyl oder d-C6-Halogenalkyl stehen,R 6 and R 7 are independently hydrogen, Ci-C 8 alkyl, Ci-Cs-alkoxy, Ci-C 4 - alkoxy-Ci-C4-alkyl, Ci-C 4 alkylthio-C 1 -C 4 - alkyl or dC 6 -haloalkyl,
R8 für Wasserstoff, Ci-Cg-Alkyl, CrC8-Alkoxy, CrC4-Alkoxy-C,-C4-alkyl, CrC4- Alkylthio-Ci-C4-alkyl, C2-C8-Alkenyl, C2-C8-Alkinyl, Ci-Cβ-Halogenalkyl, C2-C6- Halogenalkenyl, C2-C6-Halogenalkinyl, C3-C6-Cycloalkyl, oder für jeweils gegebenenfalls substituiertes Phenyl oder Phenylalkyl steht, oderR 8 is hydrogen, Ci-Cg-alkyl, C r C 8 alkoxy, C r C 4 alkoxy-C, -C 4 alkyl, C r C 4 - alkylthio-Ci-C 4 alkyl, C 2 - C 8 alkenyl, C 2 -C 8 alkynyl, Ci-Cβ-haloalkyl, C 2 -C 6 - haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 -cycloalkyl, or represents in each case optionally substituted phenyl or Phenylalkyl is, or
M-Q-Z gemeinsam für jeweils gegebenenfalls einfach bis dreifach durch Methyl substituiertes lH-2,3-Dihydro-inden-4-yl, l,3-Dihydro-2-benzofüran-4-yl oder 1,3- Dihydro-2-benzothien-4-yl stehen,MQZ together for each optionally monosubstituted to trisubstituted by methyl lH-2,3-dihydro-inden-4-yl, l, 3-dihydro-2-benzofüran-4-yl or 1,3-dihydro-2-benzothien-4 -yl,
A für einen der folgenden Reste Al bis Al 9 stehtA is one of the following radicals Al to Al 9
Al A2 A3 A4 A5Al A2 A3 A4 A5
A6 A7 A8 A9 AlO A6 A7 A8 A9 AlO
Al l A12 A13 A14 A15All A12 A13 A14 A15
A16 A17 A18 A19A16 A17 A18 A19
R9 für Wasserstoff, Cyaoo, Halogen, Nitro, Ci-C4-Alkyl, CrC4-Alkoxy, Ci-C4-Alkyl- thio, C3-C6-Cycloalkyl, Ci-C4-Halogenalkyl3 Ci-C4-Halogenalkoxy oder Ci-C4-HaIo- genalkylthio mit jeweils 1 bis 5 Halogenatomen, Aminocarbonyl oder Aminocar- bonyl-Ci-C4-alkyl steht, R10 für Wasserstoff, Halogen, Cyano, Ci-C4-Alkyl, Ci-C4-Alkoxy oder Ci-C4-Alkylthio steht,R 9 is hydrogen, Cyaoo, halogen, nitro, Ci-C 4 alkyl, C r C 4 alkoxy, Ci-C 4 alkyl thio, C 3 -C 6 cycloalkyl, Ci-C 4 haloalkyl Ci- 3 C 4 -haloalkoxy or C 1 -C 4 -haloalkylthio having in each case 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-C 1 -C 4 -alkyl, R 10 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio,
R11 für Wasserstoff, CrC4-Alkyl, Hydroxy-Ci-C4-alkyl, C2-C6-Alkenyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, CrC4-Halogenalkyl, Ci-C4-R 11 is hydrogen, C r C 4 alkyl, hydroxy-Ci-C 4 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl, Ci-C4-alkoxy-Ci-C 4 alkyl, C r C 4 haloalkyl, Ci-C 4 -
Halogenalkylthio-Ci-C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl mit jeweils 1 bis 5 Halogenoalkylthio-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl having in each case 1 to 5
Halogenatomen, oder Phenyl steht, R12 und R13 unabhängig voneinander für Wasserstoff, Halogen, Ci-C4-Alkyl oder Q-C4-Halogen atoms, or phenyl, R 12 and R 13 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl or QC 4 -
Halogenalkyl mit 1 bis 5 Halogenatomen steht, R14 für Halogen, Cyano oder Ci-C4-Alkyl, oder Ci-C4-Halogenalkyl oder Q-C4-HaIo- genalkoxy mit jeweils 1 bis 5 Halogenatomen steht, R15 und R16 unabhängig voneinander für Wasserstoff, Halogen, Ci-C4-Alkyl oder Q-C4-Haloalkyl having 1 to 5 halogen atoms, R 14 is halogen, cyano or Ci-C 4 alkyl, or Ci-C 4 -haloalkyl or QC 4 -HaIo- genalkoxy having in each case 1 to 5 halogen atoms, R 15 and R 16 is independent each other for hydrogen, halogen, C 1 -C 4 -alkyl or QC 4 -
Halogenalkyl mit 1 bis 5 Halogenatomen steht,Halogenoalkyl having 1 to 5 halogen atoms,
R17 für Wasserstoff, Halogen, CrC4-Alkyl oder C]-C4-Halogenalkyl mit 1 bis 5 HaIo- genatomen steht,R 17 is hydrogen, halogen, C r C is genatomen 4 -halogenoalkyl having 1 to 5 halo- 4 alkyl or C] -C,
R18 für Wasserstoff, Halogen, Hydroxy, Cyano, Ci-C6-Alkyl, Ci-C4-Halogenalkyl5 Q-R 18 is hydrogen, halogen, hydroxy, cyano, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl 5 Q-
C4-Halogenalkoxy oder Ci-C4-Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen steht,C 4 -haloalkoxy or C 1 -C 4 -haloalkylthio having in each case 1 to 5 halogen atoms,
R19 für Halogen, Hydroxy, Cyano, Q-C4-Alkyl, Ci-C4-Alkoxy, CrC4-Alkylthio, C1-C4- HalogenaUtyl, Ci-C4-Halogenalkylthio oder Ci-C4-Halogenalkoxy mit jeweils 1 bis 5R 19 is halogen, hydroxy, cyano, QC 4 alkyl, Ci-C 4 alkoxy, C r C 4 alkylthio, C 1 -C 4 - HalogenaUtyl, Ci-C4-haloalkylthio or C 4 -haloalkoxy with each 1 to 5
Halogenatomen steht, R20 für Wasserstoff, Halogen, Cyano, Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, Ci-R 20 is hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio,
C4-Halogenalkyl, Ci-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen, Ci-C4-C 4 -haloalkyl, C 1 -C 4 -haloalkoxy having in each case 1 to 5 halogen atoms, C 1 -C 4 -
Alkylsulphinyl oder Ci-C4-Alkylsulphonyl steht, R21 für Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,Alkylsulphinyl or C 1 -C 4 -alkylsulphonyl, R 21 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R22 für C,-C4-Alkyl steht,R 22 is C, -C 4 -alkyl,
Q1 für S (Schwefel), SO, SO2 oder CH2 steht, p für 0, 1 oder 2, wobei R22 für identische oder verschiedene Reste steht, wenn p für 2 steht,Q 1 is S (sulfur), SO, SO 2 or CH 2 , p is 0, 1 or 2, R 22 being identical or different radicals when p is 2,
R23 für Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 23 is C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms,
R24 fiir Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 24 fiir Ci-C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms,
R25 und R25 unabhängig voneinander für Wasserstoff, Halogen, Amino, Ci-C4-AIlCyI oderR 25 and R 25 independently of one another represent hydrogen, halogen, amino, C 1 -C 4 -alkyl or
Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen stehen, R27 für Wasserstoff, Halogen, CrC4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,Ci-C 4 haloalkyl having 1 to 5 halogen atoms, R 27 is hydrogen, halogen, C r C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms,
R28 und R29 unabhängig voneinander für Wasserstoff, Halogen, Amino, Nitro, Ci-C4-AIlCyI oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen stehen,R 28 and R 29 are independently hydrogen, halogen, amino, nitro, Ci-C 4 -alkyl or Ci-C 4 haloalkyl having 1 to 5 halogen atoms,
R30 für Wasserstoff, Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 30 is hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl having 1 to 5 halogen atoms,
R31 für Wasserstoff, Halogen, Amino, Ci-C4-Alkylamino, Di-(Ci -C4-alkyl)amino, Cyano, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 31 is hydrogen, halogen, amino, Ci-C 4 alkylamino, di- (Ci -C 4 alkyl) amino, cyano, Ci-C 4 alkyl or Ci-C 4 haloalkyl having 1 to 5 halogen atoms,
R32 für Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 32 represents halogen, Ci-C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms,
R33 für Wasserstoff, Halogen, Amino, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)amino, Cyano, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 33 is hydrogen, halogen, amino, Ci-C 4 alkylamino, di- (Ci-C 4 alkyl) amino, cyano, Ci-C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms,
R34 für Halogen, Ci-C4- Alkyl oder d-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 34 represents halogen, Ci-C 4 - is 4 -halogenoalkyl having 1 to 5 halogen atoms, alkyl or dC,
R35 für Halogen, Ci-C4- Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 35 represents halogen, Ci-C 4 - is 4 -halogenoalkyl having 1 to 5 halogen atoms, alkyl or Ci-C,
R36 für Wasserstoff oder C1-C4-AIlCyI steht,R 36 is hydrogen or C 1 -C 4 -alkyl,
R37 für Halogen oder C,-C4-Alkyl steht, R38 für Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 37 is 4 alkyl halogen or C, -C, R 38 4 -alkyl or Ci-C 4 haloalkyl having 1 stands for Ci-C to 5 halogen atoms,
R39 für Wasserstoff, Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 39 is hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl having 1 to 5 halogen atoms,
R40 für Halogen, Hydioxy, Ci-C4-Alkyl, CrC4-Alkoxy, Ci-C4-Alkylthio, C1-C4-HaIo- genalkyl, CrC4-Halogenalkylthio oder Ci-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht,R 40 is halogen, Hydioxy, Ci-C 4 alkyl, C r C 4 alkoxy, Ci-C 4 alkylthio, C 1 -C 4 -HaIo- genalkyl, -C 4 -haloalkylthio or C 4 -haloalkoxy with each 1 to 5 halogen atoms,
R41 für Wasserstoff, Cyano, Ci-C4-Alkyl, CrQ-Halogenalkyl mit 1 bis 5 Halogenatomen, Q-Q-Alkoxy-CΛ-alkyl, Hydroxy-Ci-C4-alkyl, Ci-C4-Alkylsulfonyl, Di(Ci-C4-alkyl)- aminosulfonyl, Ci-C6-Alkylcarbonyl oder jeweils gegebenenfalls substituiertes Phenylsulfonyl oder Benzoyl steht, R42 für Wasserstoff, Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R43 für Wasserstoff, Halogen, Cyano, C,-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 41 is hydrogen, cyano, C 1 -C 4 -alkyl, C 1 -C -haloalkyl having 1 to 5 halogen atoms, QQ-alkoxy-C 1 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulfonyl, di (C 1 -C 4 -alkyl) C 4 alkyl) - aminosulfonyl, Ci-C 6 alkylcarbonyl or in each case optionally substituted phenylsulfonyl or benzoyl, R 42 is hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 -haloalkyl having 1 to 5 halogen atoms . R 43 4 alkyl or Ci-C4-haloalkyl having 1 represents hydrogen, halogen, cyano, C, -C to 5 halogen atoms,
R44 für Wasserstoff, Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R45 für C,-C4-Alkyl steht.R 44 is hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl having 1 to 5 halogen atoms, R 45 is C, -C 4 alkyl.
2. Verfahren zum Herstellen von Carboxamiden der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, dass man2. A process for the preparation of carboxamides of the formula (I) according to claim 1, characterized in that
(a) Carbonsäurehalogenide der Formel (II) X(a) Carboxylic acid halides of the formula (II) X
in welcherin which
A und X die in Ansprach 1 angegebenen Bedeutungen haben,A and X have the meanings given in claim 1,
X1 für Halogen oder Hydroxy steht, mit Cyclopropylaminen der Formel (III)X 1 is halogen or hydroxy, with cyclopropylamines of the formula (III)
in welcher M, Q und Z die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Kupplungsreagenzes, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt. in which M, Q and Z have the meanings given above, if appropriate in the presence of a coupling reagent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
3. Mittel zum Bekämpfen unerwünschter Mikroorganismen, gekennzeichnet durch einen Gehalt an mindestens einem Carboxamid der Formel (I) gemäß Anspruch 1 neben Streckmitteln und/oder oberflächenaktiven Stoffen.3. A composition for controlling unwanted microorganisms, characterized by a content of at least one carboxamide of the formula (I) according to claim 1 in addition to extenders and / or surface-active substances.
4. Verwendung von Carboxamiden der Formel (I) gemäß Ansprach 1 zum Bekämpfen unerwünschter Mikroorganismen.4. Use of carboxamides of the formula (I) according to claim 1 for controlling unwanted microorganisms.
5. Verfahren zum Bekämpfen unerwünschter Mikroorganismen, dadurch gekennzeichnet, dass man Carboxamide der Formel (I) gemäß Anspruch 1 auf die Mikroorganismen und/oder deren Lebensraum ausbringt. 5. A method for controlling unwanted microorganisms, characterized in that one applies carboxamides of the formula (I) according to claim 1 to the microorganisms and / or their habitat.
6. Verfahren zum Herstellen von Mitteln zum Bekämpfen unerwünschter Mikroorganismen, dadurch gekennzeichnet, dass man Carboxamide der Formel (I) gemäß Anspruch 1 mit Streckmitteln und/oder oberflächenaktiven Stoffen vermischt.6. A process for preparing agents for controlling unwanted microorganisms, characterized in that one mixes carboxamides of the formula (I) according to claim 1 with extenders and / or surface-active substances.
7. Verwendung von Carboxamiden der Formel (I) gemäß Anspruch 1 zur Behandlung von Saatgut.7. Use of carboxamides of the formula (I) according to claim 1 for the treatment of seed.
8. Verwendung von Carboxamiden der Formel (I) gemäß Anspruch 1 zur Behandlung von transgenen Pflanzen.8. Use of carboxamides of the formula (I) according to claim 1 for the treatment of transgenic plants.
9. Verwendung von Carboxamiden der Formel (I) gemäß Anspruch 1 zur Behandlung von Saatgut transgener Pflanzen.9. Use of carboxamides of the formula (I) according to claim 1 for the treatment of seed transgenic plants.
10. Anilinderivaten der Formel (III)10. Aniline derivatives of the formula (III)
in welcher M, Q und Z die in Anspruch 1 angegebenen Bedeutungen haben. in which M, Q and Z have the meanings given in claim 1.
EP06829295A 2005-12-17 2006-12-05 Carboxamides Withdrawn EP1966148A1 (en)

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