EP1966148A1 - Carboxamides - Google Patents

Carboxamides

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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Withdrawn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)
English (en)
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
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1966148A1 publication Critical patent/EP1966148A1/fr
Withdrawn legal-status Critical Current

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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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

L'invention concerne de nouveaux carboxamides de la formule (I) où X, M, Q, Z et A sont tels que définis dans la description, plusieurs procédés de production de ces matières et leur utilisation pour lutter contre les micro-organismes indésirables, ainsi que de nouveaux produits intermédiaires et leur production.
EP06829295A 2005-12-17 2006-12-05 Carboxamides Withdrawn EP1966148A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005060467A DE102005060467A1 (de) 2005-12-17 2005-12-17 Carboxamide
PCT/EP2006/011649 WO2007068373A1 (fr) 2005-12-17 2006-12-05 Carboxamides

Publications (1)

Publication Number Publication Date
EP1966148A1 true EP1966148A1 (fr) 2008-09-10

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EP06829295A Withdrawn EP1966148A1 (fr) 2005-12-17 2006-12-05 Carboxamides

Country Status (6)

Country Link
US (1) US7820708B2 (fr)
EP (1) EP1966148A1 (fr)
JP (1) JP2009519911A (fr)
AR (1) AR058384A1 (fr)
DE (1) DE102005060467A1 (fr)
WO (1) WO2007068373A1 (fr)

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DE10347090A1 (de) 2003-10-10 2005-05-04 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
DE102005009458A1 (de) * 2005-03-02 2006-09-07 Bayer Cropscience Ag Pyrazolylcarboxanilide
DE102005025989A1 (de) * 2005-06-07 2007-01-11 Bayer Cropscience Ag Carboxamide
DE102005035300A1 (de) 2005-07-28 2007-02-01 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
DE102005060468A1 (de) * 2005-12-17 2007-06-21 Bayer Cropscience Ag Thienylpyridylcarboxamide
DE102005060464A1 (de) * 2005-12-17 2007-06-28 Bayer Cropscience Ag Pyrazolylcarboxamide
RU2516290C2 (ru) 2007-08-27 2014-05-20 Басф Се Пиразольные соединения и их использование в способе борьбы с беспозвоночными вредителями, в способе защиты материала размножения растений, в способе лечения или защиты животных от инвазии или инфицирования, в материале размножения растений и сельскохозяйственные композиции, содержащие пиразольные соединения
CN102223798A (zh) * 2008-09-24 2011-10-19 巴斯夫欧洲公司 用于防治无脊椎动物害虫的吡唑化合物
EA020661B1 (ru) 2008-09-24 2014-12-30 Басф Се Пиразольные соединения для борьбы с беспозвоночными вредителями
CN102317259B (zh) * 2009-02-17 2015-12-02 拜尔农科股份公司 杀真菌n-(苯基环烷基)羧酰胺，n-(苄基环烷基)羧酰胺和硫代羧酰胺衍生物
JP2012532176A (ja) 2009-07-06 2012-12-13 ビーエーエスエフ ソシエタス・ヨーロピア 無脊椎動物系害虫防除用ピリダジン化合物
WO2011003793A1 (fr) 2009-07-06 2011-01-13 Basf Se Composés pyridazine destinés à la lutte contre les nuisibles invertébrés
WO2011009804A2 (fr) 2009-07-24 2011-01-27 Basf Se Composés dérivés de pyridine pour la lutte contre des animaux nuisibles invertébrés
WO2011117198A2 (fr) 2010-03-23 2011-09-29 Basf Se Composés de pyridazine pour contrôler des organismes invertébrés nuisibles
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KR102227271B1 (ko) 2013-04-15 2021-03-12 에프엠씨 코포레이션 살진균성 아미드
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Also Published As

Publication number Publication date
US7820708B2 (en) 2010-10-26
US20090176844A1 (en) 2009-07-09
WO2007068373A1 (fr) 2007-06-21
DE102005060467A1 (de) 2007-06-21
AR058384A1 (es) 2008-01-30
JP2009519911A (ja) 2009-05-21

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